Title of Invention

PYRROLOPYRIMIDINECARBOXAMIDES

Abstract The compounds of formula (I) wherein R1, R21, R22, R23, R24, Y and R3 have the meanings as given in the description, the salts thereof, the N-oxides of the compounds and the salts thereof and the stereoisomers of the compounds, the salts, the N-oxides of the compounds and the N-oxides of the salts thereof are effective inhibitors of the type 5 phosphodiesterase.
Full Text FORM 2
THE PATENTS ACT, 1970 (39 of 1970)
&
THE PATENS RULES, 2003
COMPLETE SPECIFICATION
[See section 10, Rule 13]
PYRROLOPYRIMIDINECARBOXAMIDES:
NYCOMED GMBH, A CORPORATION ORGANIZED AND EXISTING UNDER THE LAWS OF GERMANY, WHOSE ADDRESS IS BYK-GULDEN-STR., 2, 78467 KONSTANZ, GERMANY.
THE FOLLOWING SPECIFICATION
PARTICULARLY DESCRIBES THE INVENTION AND THE MANNER IN WHICH IT IS TO BE PERFORMED.

Description
Pyrrolopyrlmidinecarboxamides
Field of application of the invention
The invention relates to pyrrolopyrimidinecarboxamide compounds, processes for their preparation, pharmaceutical compositions comprising said compounds and the use thereof in the treatment or prophylaxis of diseases.
Description of the invention
It has now been found that the pyrrolopyrimidinecarboxamide compounds, which are described in detail befow, have surprising and advantageous properties.
The invention relates to compounds of formula (I)

wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroa!koxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyI, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy, or R22 and R23 combine to form a group -O-CH2-O-, R24 is hydrogen,

Y is -(CH2)„-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6,
R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41.
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is pptionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7. -C(O)-NR8R9 or NH2,
R7 Is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionalily substrtuted by72, or 1-4C-a1koxy, which is optionally substituted by R73 R71 is 1 -4C-alkoxy or hyd roxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen, R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, which is optionally substituted by R92,
R91 is 1-4C-alkoxy or hydroxy,
R92 is 1-4C-alkoxy or hydroxy,
salts thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
1-4C-Alkyl is a straight-chain or branched alkyl group having 1 to 4 carbon atoms. Examples are methyl, ethyl, n-propyl, iso-propyl, n-butyt, iso-butyl, sec-butyl afd tert-butyl.
Halogen includes fluorine, chlorine, bromine and iodine. In case of R22 and/or R23 being halogen, fluorine is preferred.
3-6C-Cycloa!kyl is a cycloalkyi group having 3 to 6 carbon atom^, examples of which include the cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl group. In case of R3 being 3-6C-cydoalkyl, cyclohexyl is preferred.
1-4C-Alkoxy represents a group which, in addition to the oxygen atom, contains a straight-chain or branched alkyl moiety having 1 to 4 carbon atoms. Examples are methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, sec-butoxy and tert-butoxy.

1-4C-Fluoroalkoxy represents a group which, in addition to the oxygen atom, contains a straight-chain or branched alkyl moiety having 1 to 4 carbon atoms, wherein one or more of the hydrogen atoms of the alkyl moiety are replaced by fluorine. Examples include, but are not limited to, a trifluoromefhoxy, difluoromethoxy, fluoromethoxy, perfluoroethoxy, 1,1,1-trifluoro-2-fluoroethoxy, 1,1,1-trifluoroethoxy, 1,1-difluoro-2,2-difluoroethoxy, 1,1-difluoro-2-fluoroethoxy, 1,1-difluoroethoxy, 1-fluoro-2.2-difluoroethoxy, 1-fluoro-2-fluoroethoxy, 1-fluoroethoxy, 2,2-difluoroethoxy, 2-fluoroethoxy, n-perfluoropropoxy, and n-perfluorobutoxy group.
The group -C(O)-1-4C-alkyl represents a group which, in addition to the carbonyl group -C{0)-, contains a straight-chain or branched alkyl moiety having 1 to 4 carbon atoms, Examples are methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, iso-propylcarbonyl, n-butylcarbonyl, Iso-butylcarbonyl, sec-butylcarbonyl and tert-butylcarbonyl.
The group -C(O)-3-6C-cyctoalkyl represents a group which, in addition to the carbonyl group -C(O)-, contains a cycloalkyl group having 3 to 6 carbon atoms. Examples are cyclopropylcarbonyl, cydobutylcarbonyl, cyclopentylcarbonyl and cyclohexylcarbonyl.
The group -C(O)-O-1-4C-alkyl represents a group which, in addition to the oxycarbonyl group -C(O)-O-, contains a straight-chain or branched alkyl moiety having 1 to 4 carbon atoms. Examples are methyloxycarbonyl, ethyloxycarbonyl, n-propyloxycarbonyl, iso-propyloxycarbonyl, n-butyloxycartjonyl, iso-butyloxycarbonyt, sec-butyloxycarbonyl and tert-butyloxycarbonyl.
The 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and optionally one oxygen atom Includes, but is not limited to, azetidinyl, oxazetidinyl, pyrrolidlnyl, oxazolidinyl, piperidinyl, morpholinyl, azepanyl and oxazepanyl, in particular azetidinyl, 1,3-oxazetidlnyl, pyrrolidlnyl, 1,3-oxazolidinyl, piperidinyl, morpholinyl, azepanyl and 1,3-oxazepanyl, preferably azetidin-3-yl, pyrrolidin-3-yl, morpholin-2-yl, piperidin-3-yl and plperidin-4-yl.
In a preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycloalkyl or 2-4C-alkyl which is optionally substituted by R11,
R11 Is 1-4C-alkoxy or hydroxy,
R21 Is hydrogen,
R22 Is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C-
alkyl. or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy, R24 Is hydrogen,
Y is -(CH2)n-,

n is 0 or 1,
R3 is a 4- to 6-imembered saturated heterocyclic ring containing one nitrogen atom and optionally one oxygen atom, said heterocydic ring being optionally substituted by R4,
R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C'aikyl group is Optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-aikoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof arid a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-aIkoxy, hydroxy, i-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alky), 1-4C-alkoxy, hydroxy or 1-4C-fluoroa)koxy,
or R22 and R23 combine to form a group -O-CHz-O-,
R24 is hydrogen,
Y is -(CH2)n
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O0)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloa!kyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH;, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy,

R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, which is optionally
substituted by R92, R91 is 1-4C-alkoxy or hydroxy, R92 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof,
In a further preferred embodiment, the irivention relates !o compounds of formula (I), wherein
R1 is 1-4C-a[kyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, l-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl. or R21 and R22 combine to form a group -O-CHj-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C{0}-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-aikoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alky[, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C~alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen, R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, which is optionally
substituted by R92,

R91 is 1-4C-alkoxy or hydroxy,
R92 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compounci or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
(n a further preferred embodfment, the invention relates to compounds of formula (I), wherein
R1 Is 3-4C-alkyl which is optionally substituted by R11,
R11 is methoxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-alkyl,
or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C-cycloalkyl group substituted by R6.
R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalky(, wherein the 3-6C-cycloa)kyl group is optionally substituted fay R42, or -C(O)-0-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-a1kyl, which is cpljonally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-aJkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkDxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compxjund or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.

In a further preferred embodiment, the invention relates to compounds of formula (I), wtierein
R1 is -CH2-3-6C-cycloalkyl or 1 -4C-atkyl whicti is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy, or R22 and R23 combine to form a group -O-CH2-O-, R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to 6-membered saturated heterocyclic ring containing one nitrogen atom, said heterocyclic ring being optionally substituted by R4,
R4 is -C(O)-H, -C(O)-1-4C-aikyl, wherein the 1-4C-alky) group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound.
the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 Is -CH2-3-4C-cycloalkyl or 2-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy, or R22 and R23 combine to fomi a group -O-CH2-O-, R24 is hydrogen,
Y is -(CH2)„-,
n is 0 or 1,
R3 is a 4- to 6-memb8red saturated heterocyclic ring containing one nitrogen atom, said heterocyclic ring being substituted by R4,

R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C{O}-3-6C-cydoalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C{O)-O-1-4C-a)kyi, wherein the 1-4C-alkyt group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-a[koxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cydoalkyl or 2-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, hafogen, -1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O}-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy. hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 3-6C-cycloalkyl group substituted by R6, R6 is -NH-C(O}-R7, -C{O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloa!kyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-aIkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen, R9 is 1-4C-aIkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, which is optionally
substituted by R92, R91 is 1-4C-alkoxy or hydroxy, R92' is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (1), wherein R1 is -CH2-3-4C-cydoalkyl or 2-4C-alkyl which is optionally substituted by R11,

R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C-
or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
R24 is hydrogen,
Y is -(CH2),-,
n is 0 or 1,
R3 is a cyclohexyl group substituted by R6,
R6 is -NH-C{O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen, R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, which is optionally
substituted by R92, R91 is 1-4C-alkoxy or hydroxy, R92 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (1), wherein
R1 is -CH2-S-eC-cycloalkyI or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alhyl, 1-4C-a)koxy, hydroxy, 1-4C-fluoroa)koxy or-C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyi, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)„-,
n is 0 or 1,
R3 is a 4- to 6-membered saturated heterocyclic ring containing one nitrogen atom and one
oxygen atom, said heterocyclic ring being optionally substituted by R4,

R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-aikoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycloalkyl or 2-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-afkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-f(uoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y (s -(CH2),-,
n is 0 or 1,
R3 is a 4- to 6-membered saturated heterocyclic ring containing one nitrogen atom and one
oxygen atom, said heterocyclic ring being substituted by R4, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or-C(O)-0'1-4C-alkyl, wherein the 1-4C-alkyl group is optionaUy substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-a)koxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11, R11 is 1-4C-alkoxy or hydroxy, R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fIuoroalkoxy or -C(O)-1-4C-alkyt,

or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alko)(y, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n,
n Is 0 or 1,
R3 is a 5- to 6-membered saturated heterocyclic ring containing one nitrogen atom, said heterocyclic ring being substituted by R4,
R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-a(koxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wher-ein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-aikoxy, hydroxy or 1-4C-fluoroalkoxy, or R22 and R23 combine to form a group -O-CH3-O-, R24 is hydrogen,
Y is -(CH2)„-,
n is 0 or 1,
R3 is a 5-membered saturated heterocyclic ring containing one nitrogen atom, said heterocyclic ring being substituted by R4,
R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,

a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer oi the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-aikyl which is optionally substituted by R11.
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyL 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyt, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -{CH2)n,
n is 0 or 1,
R3 is a 6-menibered saturated tieterocyclic ring containing one nitrogen atom, said
heterocyclic ring being substituted by R4, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-a)kyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyt, wherein the 3-6C-cydoalkyl group is optionally substituted by R42,
or -C(O)O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-a(kOKy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy,
a salt thereof, an M-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,

R3 is a 6-nnembered saturated heterocyclic ring containing one nitrogen atom and one oxygen atom, said heterocyclic ring being substituted by R4,
R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxIde of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or !-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1'4C-alkoxy, hydroxy or -C(O)-1-4C-alkyl,
or R21 and R22 combine to form a group -O-CH2-O-.
R23 is hydrogen, halogen, 1-4C-alky), 1-4C-alkoxy or hydroxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 3-6C-cycloalkyl group substituted by R6,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalky!, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1'4C-alkoxy or hydroxy, R8 is hydrogen, R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, which is optionally
substituted by R92, R91 is 1-4C-alkoxy or hydroxy, R92 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof,
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein

R1 is -CH2-3-6C-cycloa!kyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-a!kyl, 1-4C-alkoxy, hydroxy or -C(O)-1-4C-alky!,
or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy or hydroxy,
or R22 and R23 combine to form a group -O-CH2-O-.
R24 is hydrogen,
Y Is -(CH2)n-,
n is 0 or 1,
R3 is a cyclohexyl group substituted by R6,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NHj,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
oplionally substituted by R72, or 1-4C-alkoxy. which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y Is -(CH2)„-,
n is 0,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6,

R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cyctoalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NHj,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73,
R71 is 1-4C-alkoxy or hydroxy,
R72 is 1'4C-alkoxy or hydroxy,
R73 is 1-4C-alkQxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyi, which is optionally substituted by R91, or 3-6C-cycloaikyl, which is optionally substituted by R92,
R91 is 1-4C-alkoxy or hydroxy,
R92 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
Rl 1 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)„-,
n is 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,

R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7, 'C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cydoalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen, R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, which is optionally
substituted by R92, R91 is 1-4C-alkoxy or hydroxy, R92 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, tfie salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (1), wherein
R1 is -CH2-3-6C-cydoalkyl or 1 -4C-a]kyj which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl. or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy, R24 is hydrogen,
Y is -{CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cydoalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-atkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkDxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,

R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73,
R71 is 1-4C-alkoxy or hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-aikoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionaliy substituted by R91, or 3-6C'Cycloalkyi, which is optionaliy substituted by R92,
R91 is 1-4C-alkoxy or hydroxy,
R92 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the salt, (he N-oxide of the compound or the N-oxide of the salt thereof.
(n a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1 -4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C'alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C'a!kyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NRBR9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyI, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,

R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, which is optionally
substituted by R92, R91 is 1 -4C-al koxy or hyd roxy, R92 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyi or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21, R22, R23 and R24 are each hydrogen,
Y is -(CHj),-,
n is 0 or 1,
R3 is a 4- to 7-membereti saturated heterocyclc ring containing one nitogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxyor hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-a!kyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy, R21 is hydrogen,

R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C-
alkyl,
or R21 and R22 combine to form a group -O-CH2-O-,
R23 is 1-4C-alkoxy,
R24 is hydrogen,
Y is -(CH2)n,-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-a}koxy or hydroxy, R42 is 1 -4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NHj, R7 is hydrogen, 1-4C-alkyi, which is optionally substituted by R71, 3-6C-cycloa!kyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-aikoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the f^l-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CHz-3-6C-cycloalkyl or 1-4C-alkyI which is optionally substituted by Rl 1,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C-
alkyl,
or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydroxy,
R24 is hydrogen,
Y is -{CHj)„-,

n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl wtierein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)1-4C-
alkyl,
or R21 and R22 combine to form a group -O-CH2-O-,
R23 is 1-4C-fluoroalkoxy,
R24 is hydrogen,
Y is '{CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycioalkyl group substituted by R6,

R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alky] group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 . is-NH-C(O)-R7,-C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73,
R71 is 1-4C-alkoxy or hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1 -4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is halogen,
R23 is 1-4C-alkoxy,
R24 is hydrogen,
Y is -(CH2)n.-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,

R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy. R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the connpound or the N-oxide of the salt thereof.
in a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3'6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is-C(O)-1-4C-alkyl,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-R8R9 or NH2,
R7 is hydrogen, 1-4C-alkyi, which is optionally substituted by R71, 3-6C-cycfcialkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,

a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (1), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is halogen,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
R24 is hydrogen,
Y is -{CH2)„-,
n is 0or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalky! group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkQxy or hydroxy, R8 is hydrogen,
R9 Is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 fs 1-4C-atkaxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein R1 is -CH2-3-6C-cycloalkyi or 1-4C-alkyl which is optionally substituted by R11, R11 is 1-4C-alkoxy or hydroxy, R21 is hydrogen, R22 is 1-4C-alkoxy,

R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
R24 is hydrogen,
Y is -(CH2),-,
n is 0 or 1,
R3 is a 4- fo 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C-cycloalkyl group substituted by R6, R4 is 'C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-a!ky( group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R4t is 1-4C-a(koxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7. 'C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydroxy,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fiuoroalkoxy,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0orl,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6,

R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R4r -C(O)-3-6C-cycloalkyl wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alKyl group is optionaily substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 Is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alky[, which is optionally substituted by R71, 3-6C-cycloalkyl, which is optionally substituted by R72. or 1-4C-alkoxy, which is optionally substituted by R73,
R71 is 1-4C-alkoxy or hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R7 3 is 1 -4C-a Ikoxy or hyd roxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the sait, (he N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is1-4C-fluoroalkoxy,
R23 is hydrogen, halogen, l-4C-aikyi, 1-4C-alkoxy, hydroxy or 1-4C-f!uoroalkoxy,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalky! group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyt group is optionally substituted by R43, R41 is 1 -4C-alkoxy or hyd roxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,

R7 is hydrogen, 1-4C-alkyl, which is optionaliy substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy. R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cyc!oalkyl, R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxideof the compound or thesalt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
tn a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is 1-4C-alkoxy,
R23 is halogen,
R24 is hydrogen,
Y is -(CH2)n-,
n is0or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cydoalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alky!, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cydoalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group Is optionally substituted by R43, R41 is 1-4C-a/koxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or ISIH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which Is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,

a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which Is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is 1-4C-alkyl,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
R24 is hydrogen,
Y is -{CH2)„-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom said heterocyclic ring being optionally susitituted by R4, or a
3-6C-cydoalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cyc!oalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42.
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2. R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 IS 1-4C-a(kyl, which is optionally substituted by R91, or 3-6C-cycloalkyt, R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the sail, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11.
R11 is 1-4C-alkoxy or hydroxy,
R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen,

R24 is hydrogen,
Y is -(CHa)r,-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 Is -C(O)-H, -C(O)-1-4C-alkyl wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl. wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy, R6 Is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cydoalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 Is 1-4C-alkoxy or hydroxy, R73 Is 1-4C-alkoxy or hydroxy, R8 is hydrogen, R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, which is optionally
substituted by R92, R91 is 1-4C-alkoxy or hydroxy, R92 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 Is -CH2-3-6C-cycloalkyl or 1 -4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl,
or R21 and R22 combine to form a group -O-CH2-O-,
R23 is halogen,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,

R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C-cycloalkyl group substituted by R6,
R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group Is optionally substituted by R41, -C(O)-3-6C-cycioalkyl wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7. -C(O)-NR8R9 or NHz,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is optionally substituted by R72, or 1-4C-alkoxy, which Is optionally substituted by R73,
R71 Is 1-4C-alkoxy or hydroxy,
R72 ts 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which Is optionally substituted by R91, or 3-6C-cycloatkyl,
R91 Is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 Is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1 -4C-aIkoxy or hyd roxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroaIkoxy or -C(O)-1-4C-
alkyl,
or R21 and R22 combine to form a group -O-CH2-O-,
R23 and R24 are hydrogen,
Y is -(CH2)N,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-t-4C-alkyl, wherein the 1-4C-a(kyi group is optionally substituted by R41,
-C(O)-3-6C-cydoalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy,

R42 IS 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycioalkyl, R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is fluorine,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
R24 is hydrogen,
Y is -{CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-metnbered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycfoalkyl, wherein the 3-6C-cyc\oalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-aikoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy,

R8 is hydrogen,
R9 is 1-4C-alkyl. which is optionally substituted by R91, or 3-6C-cycloalkyl.
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof
In a further preferred embodiment, the invention relates to compounds of formula (1), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is methoxy,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
R24 is hydrogen,
Y is -(CH2)„-,
n is0or1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloa!kyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C{0}-3-6C-cyclQalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group Is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-a[koxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cydoalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (1), wherein R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,

R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is methyl,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
R24 is hydrogen,
Y is -(CH2),-,
n is Dor 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C-cycloalkyl group substituted by R6,
R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-aIkyi, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkDxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NHa,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73,
R71 is 1-4C-aikoxyor hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is methylcarbonyl,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fiuoroalkoxy,
R24 is hydrogen,
Y is -(CH2)„-,
n is 0 or 1,

R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C-cycloalkyl group substituted by R6,
R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl. wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1 -4 C-a!koxy or hyd roxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is optionally substituted by R72, or 1-4C-alkoxy, which Is optionally substituted by R73,
R71 is 1-4C-alkoxy or hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
in a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CHz-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl,
or R21 and R22 combine to form a group -O-CH2-O-,
R23 is fluorine,
R24 is hydrogen,
Y is -(CH2)„-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C{0}-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,

R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkcxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1'4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73. R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1'4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1'4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the sait, the Noxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1 -4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl,
or R21 and R22 combine to form a group -O-CH2-O-,
R23 is methoxy,
R24 is hydrogen,
Y is -(CH2)n,
n is0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73,

R71 is 1-4C-alkoxy or hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R8 Is hydrogen,
R9 is 1-4C-alkyl which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-a[koxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I) wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alky! which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is methoxy,
R23 is fluorine,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C-cycloalkyl group substituted by R6,
R4 is -C(O)-H, -C(O)-1 -4C-alkyl, wherein the 1 -4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cydoalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-a[kyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.

In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is fluorine,
R23 is methoxy,
R24 is hydrogen,
Y is -(CH2)n,-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyi, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 (s 1-4C-a)koxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R 71 is 1 -4C-alkoxy or hyd roxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,

R23 is hydrogen, halogen, 1-4C-alkyl. 1-4C-alkoxy, hydroxy or 1-4C-f]uoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6,. R4 is -C(O)-H,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted fay R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1~4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkaxy, hydroxy, 1-4C-fluoroa)koxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4G-alkyl, 1-4C-atkQxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -{CH2),-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, R41 is 1 -4C-al koxy or hyd roxy,

R6 Is -NH-C(O)-R7, -C(O)-NR8R9 or NH,,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R7I is 1-4C-alkoxy or hydroxy, R72 Is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred emtxxiiment, the invention relates to compounds of formula (I), wherein
R1 IS -CH2-3-6C-cycloalkyl or 1 -4C-alkyl which is optionally substiuted by R11,
Rl 1 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 Is hydrogen, halogen. 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to fomi a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 Is -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group Is optionally substituted by
R42,
R42 is 1-4C-a)koxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen, R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cyctoalkyl,
39
^2 0 SEP im

R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is 'CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-aikyi, 1-4C-alkoxy, hydroxy, 1-4C-fluoroa!koxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyt, 1-4C-alkQxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n,,-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-O-1-4C-alkyl wherein the 1-4C-alkyl group is optionally substituted by R43, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3'6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which Is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-aikoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein R1 is -CH2-3-6C-cycloalkyl or 1 -4C-alkyl which is optionally substituted by R11, R11 is 1 -4C-al koxy or hydroxy, R21 is hydrogen,

R22 is hydrogen, halogen, 1-4G-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroa!koxy or-C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6,
R4 is-C(O)-O'1-4C-alkyl,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-eC-cycioa!kyi, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof
In a further preferred embodiment, the invention relates to compounds of formula {I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-.
R24 is hydrogen,
Y is -(CH2)n-
n is 0 or 1,

R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C-cycloalkyl group substituted by R6,
R4 is -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
R41 is 1-4C-alkoxy,
R6 is -NH-C(O)-R7. -C(O)NR8R9 or NH2,
R7 is hydrogen, 1-4C'alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73,
R71 is 1-4C-alkoxy or hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof
In a further preferred embodiment, the invention relates to compounds of formula {!), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkQxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkaxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen. 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fiuoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n„-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-2-4C-alkyl, wherein the 2-4C-alkyl group is optionally substituted by R41, R41 is methoxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy,

R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a sait thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
a/kyl, or R21 and R22 combine to form a group -O-CHa-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fiuoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n,-,
n is0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-2-4C-alkyl, wherein the 2-4C-alkyl group is optionally substituted by R41, R41 is hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof
In a further preferred embodiment, the invention relates to compounds of formula (1), wherein

R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxyor hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CHj-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2),-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-cyclQprQpyl, wherein the cyclopropy! group is optionally substituted by R42, R42 is 1-4C-alkoxy,
R6 is -NH-C(O)-R7. -C(O)-NR8R9 or NH2, R7 Is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1 -4C-al koxy or hyd roxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-a/kyl, which is optionally substituted by R91, or 3-6C-cyc(oalkyl, R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C-
alkyl, or R21 and R22 combine to fomn a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alky!, 1-4C^lkoxy, hydroxy or 1-4C-fluoroalkoxy, or R22 and R23 combine to form a group -O-CH2-O-, R24 is hydrogen,

Y is -(CH2),-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C-cycloalkyl group substituted by R6,
R4 is -C(O)-cyclopropyl, wherein the cyclopropyl group is optionally substituted by R42,
R42 is methoxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73,
R71 is 1-4C-alkoxy or hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R6 is hydpogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3'6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (1), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkQxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, Of R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2},-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optk>nally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-cyclopropyl, wherein the cyclopropyl group is optionally substituted by R42, R42 is hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH;,

R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
Rll is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyi, 1-4C-alkoxy, hydroxy, 1-4C-f!uoroalkoxy or-C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CHj-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-aikoxy. hydroxy or 1-4C-fluoroalkoxy.
or R22 and R23 combine to form a group -O-CHj-O-,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group sutJstituted by R6, R4 -C(O)-O-1-4C-alkyl, which is optionally substituted by R43, R43 is 1-2C-alkoxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2. R7 is hydrogen, 1-4C-a!kyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1 -4C-alkoxy or hyd roxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,

a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alky1, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)„-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4. or a
3-6C-cycloalkyl group substituted by R6, R4 -C(O)-O-1-4C-alkyl, which Is optionally substituted by R43, R43 is methoxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-a[koxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkQxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1 -4C-a Ikoxy or hyd roxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy, R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C-alkyl,

or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 -C(O)-O-1-4C-alkyl, which is optionally substituted by R43, R43 is hydroxy,
R6 is -NH-C(O)-R7, -C{0}-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted tJy R71, 3-6C-cycloalkyl, which is
optionatiy substituted by R72, or 1-4C-aikaxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxtde of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, hafogen, 1-4C-a(kyl, 1-4C-aikoxy, hydroxy, 1-4C-fluoroalkoxyor-C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-aikoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)„-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6,

R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-a!koxy or hydroxy,
R6 fs 'NH-C(O)-R7,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73,
R71 is 1-4C-alkoxy or hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-atkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyf, or R21 and R22 combine to form a group -0-CHj-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)N-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclfc ring contairring one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alky!, wherein the 1-4C-a!kyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alky! group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-a)koxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -C(O)-NR8R9, R8 is hydrogen,

R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
Rl is -CH2-3-6C-cycloalkyl or 1-4C-alky) which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C'
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkaxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)„-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7,
R7 is 1-2C-alkyl, which is optionally substituted by R71, R71 is 1-2C-alkoxy, RQ is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-a!koxy or hydroxy,
a salt thereof, an N-oxide of the "compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,

R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C' alkyl,
or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy. hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n,
n is0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C-cycloalkyl group substituted by R5,
R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7,
R7 is 1-2C-alkyl, which is optionally substituted by R71,
R71 is hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the coinpound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-afkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alky!, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CHj-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)N,

n is 0 or 1,
R3 is a 4- to 7-niembered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43. R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7,
R7 is cyclopropyl, which is optionally substituted by R72. R72 is 1-2C-alkoxy, R8 is hydrogen,
R9 is 1-4C-alkyl. which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy, or R22 and R23 combine to form a group -O-CH2-O-, R24 is hydrogen,
Y is -(CH2)n-,
n is0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1'4C-a]ky], wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy,

R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7.
R7 is cyclopropyl, which is optionally substituted by R72.
R72 is hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof
In a further preferred embodiment, the invention relates to compourids of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkox'/or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-U4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-G(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, R7 is 1-2C-alkoxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,

a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the NnDxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (1), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-a)kyl, 1-4C-a)koxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n-.
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalky!, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-2C-alkyl, wherein the 1-2C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)N R8R9 or N H2. R7 is 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is optionally
substituted by R72, or 1-2C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxrde of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,

R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-atkyl. 1-4C-alkoxy, hydroxy, l-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CHa-O-,
R23 is hydrogen, halogen, 1-4C-alkyl 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)„-,
n is 0 or 1,
R3 is a 4- to 7'membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl wherein the 1-4C-alkyl group is optionally substituted by R41,
or -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by
R42, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is 1-4C-alkyl, which is optionally substituted by R71, or.3-6C-cycloalkyl, which is optionally
substituted by R72, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R8 IS hydrogen,
R9 is 1-4C-a1kyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,
salts thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, l-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy, or R22 and R23 combine to form a group -O-CH2-O-,

R24 is hydrogen,
Y is -(CH2)n.-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalky! group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-a(kyl, wherein the 1-4C-a[kyl group is optionally substituted by R41,
-C(O)-3-6C-cydoalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7 or -C(O)-NR8R9, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,
salts thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxIde of the salt thereof.
In a further preferred emtXMdiment, the invention relates to compounds of formula (I), wherein
R1 is -CHa-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
Fi23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen.
Y is -(CH2)„-,
n is 0 or 1,

R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl wherein the 1-4C-alkyl group is optionally substituted by R41,
or -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by
R42,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7 or -C(O)-NR8R9,
R7 is 1-4C-alkyl, which is optionally substituted by R71, or 3-6C-cycloa1kyl, which is optionally
substituted by R72, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R6 iS hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,
salts thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (1), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group ~O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy, or R22 and R23 combine to form a group -O-CH2-O-, R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy,

R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -C(O)-NR8R9,
R8 is hydrogen,
R9 is 1-2C-alkyl, which is optionally substituted by R91,
R91 is 1-2C-alkoxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-a!kyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-atkoxy, hydroxy, 1-4C-fluoroalkaxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2).-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cyclQalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyi group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-aikoxy or hydroxy, R6 is -C(O)-NR8R9, R8 is hydrogen,
R9 is 1-2C-alkyl, which is optionally substituted by R91, R91 is hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred emtxxdiment, the invention relates to compounds of formula (1), wherein

R1 is -CH2-3-6C-cyclaalkyl or 1-4C-alkyl which (s optionally substituted by R11,
R11 is 1-4C'alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl. 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or 'C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CHz-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -{CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C{0}-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-a!koxy or hydroxy, R6 is -C(O)-NR8R9, R8 is hydrogen, R9 is cyclopropyl,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the rnv'ention relates to compounds of formula (I), wherein
R1 is -CH5-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C{0}-1-4C-
alky!, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a gnaup -O-CH2-O-,
R24 is hydrogen,
Y is -(CHOn-,
n is 0 or 1,

R3 is a 4- to 6-membered saturated heterocyclic ring containing one nitrogen atom and optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, wherein R4, if present, is bonded to said nitrogen atom.
R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyr wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a.stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof,
In a further preferred embodiment, the invention relates to compounds of formula (1), wherein
R1 is -CH2-3-8C-cycloalkyl or 1 -4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl. or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CHi-O-,
R24 is hydrogen,
Y is -(CH2)n,
n is 0 or 1,
R3 is a 4- to 6-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being substituted by R4 at said nitrogen
atom, R4 is -C(O)-H. -C(O)-1-4C-a!ky), wherein the 1-4C-alky) group is opt'ionai}y substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein R1 is -CH2-3-4C-cycloalkyl or 2-4C-alkyl which is optionally substituted by R11,

R11 is 1-4C-alkoxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy, or R22 and R23 combine to form a group -O-CH2-O-, R24 is hydrogen,
Y is '(CH2)n-,
n is0 or 1,
R3 is a 4- to 6-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being substituted by R4 at said nitrogen atom,
R4 is -C(O)-H, -C{O}-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cydoalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxyor hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-aikoxy or hydroxy,
salts thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred emljodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycloalkyl,
R21 is hydrogen,
R22 is hydrogen,
R23 is hydrogen,
R24 is hydrogen,
Y is -(CH2)n,-,
n is 0,
R3 is a 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being optionally substituted by R4, or a cyclohexyl group substituted by R6,
R4 is -C(O)-1-2C-alkyl, wherein the 1-2C^lkyl group is optionally substituted by R41, -C(O)-cyclopropyl or -C(O)-O-1 -4C-alkyl,
R41 is hydroxy,
R6 is -NH-C(O)-R7 or NH2,

R7 is 1-2C-alkyl, which is optionally substituted by R71, cyclopropyl, which is optionally
substituted by R72, or 1-2C-alkoxy, which is optionally substituted by R73, R71 is 1-2C-alkoxy or hydroxy, R72 is hydroxy, R73 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the Invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycloalkyl,
R21 is hydrogen,
R22 is hydrogen,
R23 is 1-4C-alkoxy,
R24 Is hydrogen,
Y is -(CH2)„-,
n is 0,
R3 is a 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being optionally substituted by R4, or a cyclohexyl group substituted by
R6, R4 is -C(O)-1-2C-alkyl, wherein the 1-2C-alkyl group is optionally substituted by R41, -C(O)-
cyclopropyl, wherein cyclopropyl group is optionally substituted by R42, -C(O)-O-1-4C-
alkyl, R41 is 1-2C-alkoxy or hydroxy, R42 is hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is 1-2C'alkyl, which is optionally substituted by R71, cyclopropyl. which is optionally
substituted by R72, or 1-4C-alkoxy, R71 is 1-2C-alkoxy or hydroxy, R72 is hydroxy, R8 is hydrogen,
R9 is 1-2C-alkyl, which is optionally substituted by R91, or cyclopropyl, R91 is 1-2C-alkoxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycloalkyl,
R21 is hydrogen,

R22 is halogen, R23 is 1-4C-alkoxy, R24 is hydrogen,
Y is -(CH2},-,
n is 0,
R3 is a 5- to 6-membered saturated heterocyclic nng containing one nitrogen atom, said
heterocyclic ring being optionally substituted by R4, or a cyclohexyl group substituted by
R6, R4 is -C(O)-1 -2C-alkyl, wherein the 1 -2C-alkyl group is optionally substituted by R41, -C(O)-
cyclopropyl, wherein the cyclopropyl group is optionally substituted fay R42, or -C(O)-O-1-
4C-alkyl, R41 is 1-2C-alkoxy or hydroxy, R42 is hydroxy, R6 is -Nl-I-C(O)-R7 or NH2, R7 is 1-2C-alkyl, which is optionally substituted by R71, cyclopropyl, which is optionally
substituted by R72, or 1-4C-alkoxy, R71 is 1-2C-alkoxy or hydroxy. R72 is hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound. the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycloalkyl
R21 is hydrogen,
R22 is-C(O)~1-4C-alkyl,
R23 is hydrogen,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0,
R3 is a 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being optionally substituted by R4, R4 is -C(O)-1-2C-alkyl, wherein the 1-2C-alkyl group is optionally substituted by R41, R41 is 1-2C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein R1 is -CH2-3-4C-cycloalkyl,

R21 is hydrogen, R22 is halogen, R23 is hydrogen, R24 is hydrogen,
Y is -{CH2),-,
n is 0,
R3 is a 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being optionally substituted by R4, or a cyclohexyl group substituted by R6,
R4 is -C(O)-1-2C-alkyl, wherein the 1-2C-alkyl group is optionally substituted by R41, or -C(O)-0-1-4C-alkyl,
R41 is 1-2C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is 1-2C-alkyl, which is optionally substituted by R71, or 1-4C-aikoxy,
R71 is 1-2C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-2C-alkyl, which is optionally substituted by R91, or cyciopropyl,
R91 is 1-2C-alkoxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
(n a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycloalkyl,
R21 is hydrogen,
R22 is MC-alkoxy,
R23 is hydrogen,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0,
R3 is a 6-membered saturated heterocyclic ring containing one nitrogen atonrt, said
heterocyclic ring being optionally substituted by R4, or a cyclohexyl group substituted by
R6, R4 is -C(O)-1-2C-a!kyl, wherein the 1-2C-alkyl group is optionally substituted by R41, -C(O)-
cyclopropyl, wherein the cyciopropyl group is optionally substituted by R42, or -C(O)-O-1-
4C-alkyl, R41 is 1-2C-alkoxy or hydroxy, R42 is hydroxy, R6 is -NH-C(O)-R7 or NH2,

R7 is 1-2C-alkyl which is optionally substituted by R71, cyctopropyl, which is optionally
substituted by R72, or 1-4C-alkoxy, R71 is 1-2C-alkoxy or hydroxy, R72 is hydroxy,
a salt thereof, an N-oxIde of the compound or Ihe salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycloalkyl,
R21 is hydrogen,
R22 is 1-4C-ftuoroalkoxy,
R23 is hydrogen,
R24 is hydrogen,
Y is -(CH2)N,
n is 0,
R3 Is a 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being optionally substituted by R4, or a cyclohexyl group substituted Jby
R6, R4 is -C(O)-1-2C-alkyl, wherein the 1-2C-alkyl group Is optionally substituted by R41, -C(O)
cyclopropyl, wherein the cyclopropyl group is optionally substituted by R42, or -C(O)-O-1-
4C-alkyl, R41 is 1-2C-alkoxy or hydroxy, R42 is hydroxy, R6 is-NH-C(O)-R7 or NH2, R7 is 1-2C-alkyl, which is optionally substituted by R71, cyclopropyl, which Is optionally
substituted by R72, or 1-4C-alkoxy, R71 is 1-2C-alkoxy or hydroxy, R72 Is hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycIoalkyl,
R21 is hydrogen,
R22 is 1-4C-alkoxy,
R23 is halogen,
R24 is hydrogen,
Y is -(CH2)n-,

n is 0,
R3 is a 5- to 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being optionally substituted by R4, R4 is -C(O)~1-2C-alkyl, wherein the 1-2C-alkyl group is optionally substituted by R41, or -C(O)-
0-1-4C-alkyl, R41 is 1-2C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycloalky;,
R21 is hydrogen,
R22 is 1-4C-alkyl,
R23 is hydrogen,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0,
R3 is a 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being optionally substituted by R4, or a cyclohexyl group substituted by
R6, R4 is -C(O)-1-2C-alkyl, wherein the 1-2C-alkyl group is optionally substituted by R41, -C(O)-
cyclopropyl, wherein the cyclopropyl group is optionally substituted by R42, or -C(O)-O-1-
4C-alkyl, R41 is 1-2C-alkoxy or hydroxy, R42 is hydroxy, R6 is -NH-C(O)-R7, or NH2, R7 is 1-2C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is optionally
substituted by R72, or 1-4C-alkoxy, R71 is 1-2C-alkoxy or hydroxy, R72 is hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycloalkyl,
R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen,
R24 is hydrogen,

Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to 6-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
cyclohexyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-2C-alky), wherein the 1-2C-alkyl group is optionally substituted by R41,
-C(O)-cyclohexyl, wherein the cyclohexy! group is optionally substituted by R42, or-C(O)-
0-1-4C-alkyl, R41 is 1-2C-alkoxy or hydroxy, R42 is hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is 1-2C-alky!, which is optionally substituted by R71, cyclopropyl, which is optionally
substituted by R72, or 1-4C-alkoxy, R71 is 1-2C-alkoxy or hydroxy, R72 is hydroxy, R8 is hydrogen,
R9 is 1-2C-alkyl, which is optionally substituted by R91, or cyclopropyl R91 is 1-2C'alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof
In a further preferred embodiment, the invention relates to compounds of formula (1), wherein
R1 is -CH2-3-4C-cycloalkyl,
R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen,
R24 is hydrogen,
Y is -(CH2),-,
n is 0,
R3 is a.4- to 6-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
cyclohexyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-2C-alkyi, wherein the 1-2C-alkyl group is optionally substituted by R41,
-C(O)-cyclopropyl, wherein the cyclopropyl group is optionally substituted by R42, or -C(O)-
0-1-4C-alkyl, R41 is 1-2C-alkoxy or hydroxy, R42 is hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,

R7 is 1-2C-alkyl, which is optionally substituted by R71, cyclopropyl, which is optionally
substituted by R72, or 1-4C-alkoxy, R71 is 1-2C-alkoxy or hydroxy, R72 is hydroxy, R8 is hydrogen,
R9 is 1-2C-alkyl, which is optionally substituted by R91, or cyclopropyl, Rgi is 1-2C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 Is -CH2-3-4C-cycloalkyl,
R21 and R22 combine to form a group -O-CHj-O-,
R23 is hydrogen,
R24 is hydrogen,
Y is -(CH2)n-,
n is 1,
R3 is a 5- to 6-membered saturated heterocyclic ring containing one nitrogen atom and optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4,
R4 is -C(O)-H, -C(O)-1-2C-alkyl, wherein the 1-2C-alkyl group is optionally substituted by R41, -C(O)-cyclopropyl, wherein the cyclopropyl group is optionally substituted by R42, or 'C(O)-0-1-4C-alkyl,
R41 Is 1-2C-alkoxy or hydroxy,
R42 Is hydroxy,
a salt thereof, an N-oxIde of the compound or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
R1 is -CH2-3-4C-cycloalkyl,
R21 is hydrogen,
R22 is halogen,
R23 Is 1-4C-alkoxy,
R24 Is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 5- to 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being substituted by R4, R4 is -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, R41 is 1-4C-alkoxy or hydroxy,

salts thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycloalkyl,
R21 is hydrogen,
R22 is hydrogen,
R23 is halogen,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0,
R3 is a 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being optionally substituted by R4, or a cyclohexyl group substituted by
R6, R4 is -C(O)-1-2C-alkyl, wherein the 1-2C-alkyi group is optionally substituted by R41, or -C(O)-
0-1-4C-alkyl, R41 is 1-2C-alkoxy or hydroxy, R6 is -NH-C(O)-R7 or NH2, R7 is 1-2C-alkyl, which is optionally substituted by R71, cyclopropyl, which is optionally
substituted by R72, or 1-4C-a!koxy, R71 is 1-2C-al koxy or hydroxy, R72 is hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
in a further preferred emtxidiment, the invention relates to compounds of formula (I), wherein
R1 1 -4C-a)kyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy, or R22 and R23 combine to form a group -O-CH2-O-R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,

R3 is a 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being optionally substituted by R4, R4 is -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, R41 is 1-2C-alkoxy or hydroxy,
a salt thereof, an N~oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof
In a further preferred embodiment, the invention relates to compounds of formula (1), wherein
R1 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C-
alkyl. or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy, or R22 and R23 combine to form a group -O-CH2-O-R24 is hydrogen,
Y is -(CH2)n-,
n is 0,
R3 is a 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being optionally substituted by R4, R4 is -C(O)-1-2C-alkyl, wherein the 1-2C-alky! group is optionally substituted by R41, R41 is 1-2C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof
in a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)~1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-aikoxy, hydroxy or 1-4C-fluoroalkoxy, or R22 and R23 combine to form a group -O-CH2-O-R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,

R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C-cycloalkyl group substituted by R6,
R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4G-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alKoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73,
R71 is 1-4C-alkoxy or hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 3-4C-alkyl,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroa[koxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluQroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-
R24 is hydrogen,
Y is -(CH2)„-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,

R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-atkoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1 -4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy. which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the oxide of the compound or the N-oxide of the salt thereof
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 3-4C-alkyl,
R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C'fluoroaIkoxy,
R24 is hydrogen,
Y is -(CH2)n,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring contairiing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4. or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41.
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH3, R7 is hydrogen. 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cydoalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,

R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 Is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxIde of the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (1), wherein
R1 3-4C-alkyl,
R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen,
R24 is hydrogen,
Y is -(CH2)n,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4,or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group Is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R7i, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73,
R71 is 1-4C-alkoxy or hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4G-alkyl, which is optionally substituted by R91, or 3-eC-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof and a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
In a further preferred emtxxiiment, the invention relates to compounds of formula (I), wherein R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11, R11 is 1-4C-aikoxy or hydroxy, R21 is hydrogen,

R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl. or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH3-O-,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O- 1-4C'alkyl, wherein the 1-4C-atkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH;, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen, R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, which is optionally
substituted by R92, R91 is 1-4C-alkoxy or hydroxy, R92 is 1-4C-alkoxy or hydroxy, salts thereof, and stereoisomers of the compounds and the salts thereof.
In a preferred emtxxJiment, the invention relates to compounds of formula {I), wherein
R1 is -CH2-3-4C-cycloalkyl or 2-4C-alkyl which is optionally substituted by R11,
R11 is 1 -4C-alkoxy or hyd roxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group ~O-CH2-O-, R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,

R24 is hydrogen,
Y is -(CH2),-,
n is 0 or 1,
R3 is a 4- to 6-membered saturated heterocyclic ring containing one nitrogen atom and optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4,
R4 is -C(O)-H, •C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
(n a further preferred embodiment, (he invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycloalkyl
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-aikoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n-.
n is 0 or 1,
R3 is a 4- to 7-member6d saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4,ora
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-5C-cyc)oalkyl, wherein the 3-6C-cycloalky) group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy,

R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, which is optionally
substituted by R92, R91 is 1-4C-alkoxy or hydroxy, R92 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoraalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group 'O-CH2-O-,
R23 is hydrogen, halogen, 1'4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -{CH2)n-,
n Is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-a[koxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen, R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, which is optionally
substituted by R92,

R91 is 1-4C-alkoxy or hydroxy, R92 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is 3-4C-alkyl which is optionally substituted by R11,
R11 Ismethoxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally sutastituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,

R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl. 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CHj-O-,
R23 is hydrogen, halogen, 1'4C'alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -{CH2)„-,
n is 0 or 1,
R3 is a 4- to 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being optionally substituted by R4, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycJoalkyl, wherein the 3-6C-cydoalky1 group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycloalkyl or 2-4C-alkyl which is optionally substituted by R11.
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-f1uoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2),.,
n is 0 or 1,
R3 is a 4- to 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being substituted by R4, R4 is -C(O)-H, -C(O)-1-4C-alky), wherein the 1-4C-alkyl group is optionady substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy,

R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycloalkyl or 2-4C-alkyl which is optionally substituted by R11,
R11 is 1 -4C-aIkoxy or hyd roxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy. hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n.,
n is 0 or 1,
R3 is a 3-6C-cycloalkyl group substituted by R6, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyi, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen, R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, which is optionally
substituted by R92, R91 is 1-4C-alkoxy or hydroxy, R92 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycloalkyl or 2-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-, R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,

R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a cyclohexyl group substituted by R6.
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloa!kyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen, R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, which is optionally
substituted by R92, R91 is 1-4C-alkaKy or hydroxy. R92 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cydoalkyl or 1-4C-a!kyl which is optionally substituted by R11,
R11 is 1-4C-a!koxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy^r 1-4C-fIuoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to 6-membered saturated heterocyclic ring containing one nitrogen atom and one
oxygen atom, said hsterocyclic ring being optionally substituted by R4, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1 -4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.

In a further preferred embodiment, the Invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycloalkyl or 2-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C-alkyl,
or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fliJoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to 6-membered saturated heterocyclic ring containing one nitrogen atom and one oxygen atom, said heterocyclic ring being substituted by R4,
R4 is -C(O)H, -C(O)-1-4C-alkyl, wherein the 1-4C-alky! group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloatkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred emtxxiiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 5- to 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being substituted by R4,

R4 is -C(O)-H, -CCO)-1-4C-alkyl. wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cydoalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
aikyl, or R21 and R22 combine to form a group -O-CH2-O-.
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 5-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being substituted by R4, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloa!kyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen. 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-f!uoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-, R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy Or 1-4C-fIuoroalkoxy,

or R22 and R23 combine to form a group -O-CH2-O-R24 is hydrogen,
Y is -(CH2)n.-,
n is 0 or 1,
R3 Is a 6-membered saturated heterocyclic ring containing one nitrogen atom, said heterocyclic ring being substituted by R4,
R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl wherein the 3-6C-cyclDalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-aJkyl group is optionally substituted by R43,
R41 is 1-4C-a!koxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloa!kyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy,. hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy, or R22 and R23 combine to form a group -O-CH2-O-, R24 is hydrogen,
Y is -(CH.)n-,
n is 0 or 1,
R3 is a 6-membered saturated heterocyclic ring containing one nitrogen atom and one oxygen atom, said heterocyclic ring being substituted by R4,
R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalky), wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,

R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, l-4C-alkoxy, hydroxy or -C(O)-1-4C-alkyl,
or R21 and R22 combine to form a group -O-CH2-O-,
R23 Is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy or hydroxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 3-6C-cycloalkyl group substituted by R6,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen, R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cyclQalkyl, which is optionally
substituted by R92, R91 is 1-4C-alkoxy or hydroxy, R92 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred emtxxJiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyI which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or -C(O)-1-4C-alkyl,
or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxyor hydroxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -{CH2)n-,
n is 0 or 1,
R3 is a cyclohexyl group substituted by R6, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73,

R71 is 1-4C-alkoxy or hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1 -4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1'4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)'1-4C-
alky], or R21 and R22 combine to form a group -O-CH2-O-.
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy. hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)„-,
n is 0,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-a[kyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-a!koxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)~NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen, R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, which is optionally
substituted by R92,

R91 is 1-4C-alkoxy or hydroxy, R92 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fIuoroalkoxy or -C(O)-1-4C-
alkyl. or R21 and R22 combine to form a group -0-CH2-0-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy, or R22 and R23 combine to form a group -O-CH2-O-, R24 is hydrogen,
Y is -(CH2)n-,
n is 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycioafkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-a)kyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 Is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen, R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C'Cycloalkyl, which is optionally
substituted by R92, R91 is 1-4C-alkoxy or hydroxy, R92 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.

In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cyc!oalkyl or 1-4C-aikyi which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen. 1-4C-alkyN 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-aIky) group is optionally substituted by R41,
-C(O)-3-6C-cydoalkyl wherein the 3-6C-cycloalkyt group is optionally substituted by R42,
or -C{O)-0-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen, R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, which Is optionally
substituted by R92, R91 is 1-4C-alkoxy or hydroxy, R92 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (1), wherein
R1 is -CH2-3-6C-cycloalkyl or 1 -4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,

R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NHa,
R7 is hydrogen, 1-4C-alkyl, which is optionaily substituted by R71, 3-6C-cyctoalkyl, which is
oplionally substituted by R72, or 1'4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen, R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, which is optionally
substituted by R92, R91 is 1-4C-alkoxy or hydroxy, R92 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21, R22, R23 and R24 are each hydrogen,
Y is -(CH2)n-.
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1'4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl. wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy,

R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-aikoxy or hydroxy,
R6 is -NH'C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-a!kyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-a(kyl, 1-4C-afkoxy, hydroxy, 1-4C-f(uoroalkoxy or -C(O)-1-4C-
alkyl,
or R21 and R22 combine to form a group -O-CH2-O-,
R23 is 1-4C-alkoxy,
R24 is hydrogen,
Y is -(CH2)n,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy,

R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fIuoroalkoxy or-C(O)-1-4C-
alkyl,
or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydroxy,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, 'C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C~alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyI, R91 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein

R1 is -CH2-3-6C-cycloalkyt or 1-4C-alkyl which Is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-, R23 is 1-4C-fluoroalkoxy, R24 is hydrogen,
Y is -{CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C'Cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyj group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or N H;, R7. is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycIoalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, . R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CHa-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is halogen,
R23 is 1-4C-alkoxy,
R24 is hydrogen,
Y is -(CH2)n-,

n is 0 or 1,
R3 is a 4- to 7-niertibered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-a!kyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl. wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1 -4C-alkoxy or hyd roxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is Optionally substituted by R73, nz 1 is 1 -4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is -C(O)-1-4C-alkyl,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C{0}-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C{0}-3-6C-cydoalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy,

R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4 C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (1), wherein
R1 is -CH2-3-dC-cycloalky or 1 -4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is halogen,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroaikoxy,
R24 is hydrogen,
Y is -{CH2)„-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyI, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 rs 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alky!, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen, R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,

R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (1), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is 1-4C-alkoxy,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cydoalkyl, wherein the 3-6C-cyc(oalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-aIkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydroxy,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,

R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4' to 7-membered saturated heferocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C-cydoalkyl group substituted by R6,
R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloa!ky!, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
.R7 is hydrogen, 1-4C-alkyl, which is optinally substituted by R71, 3-6C-cycloalkyl, which is optionally substituted by R72, or 1-4C-atkoxy, which is optionally substituted by R73,
R71 is 1-4C-alkoxy or hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (!), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is 1-4C-fluoroalkoxy,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
R24 is hydrogen,
Y is -(CHa)„-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C-cycloalkyl group substituted by R6,
R4 is -C(O)-H, -C(O)-1-4C-atkyl, wherein the 1-4C-alky! group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or-C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,

R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionatly substituted by R73,
R71 is 1-4C-alkoxy or hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycIoalkyl,
R91 is 1 -4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-a!koxy or hydroxy,
R21 is hydrogen,
R22 is 1-4C-alkoxy,
R23 is halogen,
R24 is hydrogen,
Y is -(CH2)n,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cydoatkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 Is 1 -4C-al koxy or hyd roxy, R42 is 1 -4C-al koxy or hyd roxy, R43 is 1 -4C-a)koxy or hydroxy, R6 is -NH-C(O)-R7. -C(O)-NR8R9 or NH2, R7 is hydrogen. 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-aikoxy or hydroxy,

R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cyc(oalkyl or 1-4C-a(kyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is 1-4C-alkyl.
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
R24 is hydrogen,
Y is -{CH2)n-.
n is 0 or 1,
R3 is a 4- to 7-menibered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R4l,
-C(O)-3-6C-cydoalky!, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1 -4 C-a)koxy or hyd roxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR6R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 and R22 combine to form a group -O-CHz-O-,

R23 is hydrogen,
R24 is hydrogen,
Y is -(CH2)n^-,
n is 0 or 1,
R3 is a 4- to 7-mernbered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cydoalkyl group is optionally substituted by R42,
or 'C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-a[koxy or hydroxy, R8 is hydrogen, R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, which is optionally
substituted by R92, R91 is 1 -4C-alkoxy or hydroxy, R92 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CHa-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C{0>-1-4C-
alkyl,
or R21 and R22 combine to form a group -O-CH2-O-,
R23 is halogen,
R24 is hydrogen,
Y is -(CH2)„-,
n is 0 or 1,

R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C-cycloalkyl group substituted by R6,
R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cydoalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is optionally substituted by R72, or 1-4C-aikoxy, which is optionally substituted by R73,
R71 is 1-4C-alkoxy or hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 Is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4 C-a/koxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroaIkoxy or-C(O)-1-4C-
alkyl,
or R21 and R22 combine to form a group -O-CH2-O-,
R23 and R24 are hydrogen,
Y is -(CH2)n^-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy,

R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2.
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof
In a further preferred embodiment, the invention relates to compounds of formula (I),.wherein
R1 is -CH2-3-6C-cyc[oalky! or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is fluorine,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
R24 is hydrogen,
Y is -{CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4. or a
3-6C-cycJoalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NHs, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-atkoxy, which is optionally substituted by R73, R71 is 1-4C-a!koxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen, R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,

R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alky! which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is methoxy,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C'alkoxy, hydroxy or 1'4C-fluoroalkoxy,
R24 is hydrogen,
Y is -(CH2)n,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted fay R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cydoalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O'1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1 -4C-alkoxy or hyd roxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloa!kyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred emtx)diment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is methyl,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,

R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-member6d saturated heterocyclic ring containing one nitrogen atom and
optionaily one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C-cycloalkyl group substituted by R6,
R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycioalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyt, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1'4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen,1-4Calkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is optionally substituted by P72, or 1'4C-alkoxy, which is optionally substituted by R73,
R71 is 1-4C-alkoxy or hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycioalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is methylcarbonyl,
R23 is hydrogen, halogen, 1-4C-a[kyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
R24 is hydrogen,
Y is -{CH2}n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C-cycloalkyl group substituted by R6,
R4 is -C(O)-H, -C(O)-1-4C-a!kyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cyctoalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,

R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73,
R71 is 1-4C-alkoxy or hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycIoalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl.
or R21 and R22 combine to form a group -O-CH2-O-,
R23 is fluorine,
R24 is hydrogen,
Y is -(CH2),-.
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C{0>-3-6C-cydoalkyl, wherein the 3-6C-cycloa(ky[ group is optionally substituted by R42.
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
"optionally substituted by R72, or 1-4C-alkoxy, which Is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy,

R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (1), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl,
or R21 and R22 combine to form a group -O-CH2-O-,
R23 is methoxy,
R24 is hydrogen,
Y rs -(CH2)„-,
n Is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group Is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein tbe 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which Is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.

In a further preferred embodiment, the invention relates to compounds of formula (/), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is melhoxy,
R23 is fluorine,
R24 is hydrogen,
Y is -(CH2}n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycfoafkyf, wherein the 3-6C-cycfoafl or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-aikoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyi, which is
optionally substituted by R72, or 1-4C-atkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-a!koxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen',
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is fluorine,
R23 is methoxy,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,

R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C-cycioalkyl group substituted by R6,
R4 is 'C(O)-H. -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1'4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloaIkyi, which is optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73,
R71 is 1-4C-alkoxy or hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloaiky(,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CHa-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CHa}„-.
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, R6 is -NH-C(O)-R7, -C{0}-NR8R9 or NH2,

R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-a!koxy, which is optionally substituted by R73, R71 is 1-4C-aikoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalky!, R91 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C'alkoxy, hydroxy or 1-4C-f1uoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -{CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-1-4C-alkyl, wherein the 1-4C-aIkyi group is optionally substituted by R41, R41 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-a!koxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-a!kyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.

In a further preferred embodiment, the invention relates to compounds of formula (1), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)„-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by
R42, R42 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-aIkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C-
alkyt, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy, or R22 and R23 combine to form a group -O-CH2-O-,

R24 is hydrogen,
Y is -(CH2)„-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C{0}-0-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R43 is 1~4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2. R7 is hydrogen, 1-4C-a!kyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-a!koxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-afkyl, which is optionally substituted by R91, or 3-6C-cycloalkyf, R91 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred emtxxjiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1 -4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -{CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optrcinally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is-C(O)-O-1-4C-alkyl, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2. R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73,

R71 is 1-4C-alkoxy or hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-a!koxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
oplionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cydoalkyl group substituted by R6, R4 is -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, R41 is1-4C-alkoxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-a!koxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (1), wherein R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,

R11 is 1-4C-alkoxy or hydroxy.
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyt, 1-4C-alkoxy, hydroxy, 1-4C-1luoroatkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy, or R22 and R23 combine to form a group -O-CH2-O-, R24 is hydrogen,
Y is -(CH2)n-.
n is 0 or 1,
R3 is a 4- (o 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C-cydoalkyl group substituted by R6,
R4 is -C(O)-2-4C-alkyl, wherein (he 2-4C-alkyl group is opdonaffy substituted by R41,
R41 is methoxy,
R6 is -NH-C(O)-R7. -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73,
R71 is 1-4C-alkoxy or hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1 -4 C-alkoxy or hyd roxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, l-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-a!koxy, hydroxy or 1-4C-fluoroalkoxy, or R22 and R23 combine to form a group -O-CH2-O-, R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,

R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C-cycloalkyl group substituted by R6,
R4 is -C(O)-2-4C-alkyl, wherein the 2-4C-alkyl group is optionally substituted by R41,
R41 is hydroxy,
R6 is -NH-C(O)R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-a}kyl. which is optionally substituted by R71, 3'6C-cycloalkyl, which is optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73,
R71 is 1-4C-alkoxy or hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy.
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -{CH2k,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-cyclopropyl, wherein the cyclopropyl group is optionally substituted by R42, R42 is 1-4C-alkoxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy,

R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycIoalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, hatogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-f(uoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
y is-(CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-cydopropyl, wherein the cyclopropyl group is optionally substituted by R42, R42 is methoxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkDxy or hydroxy, R72 is 1 -4C-alkoxy or hydroxy, R73 is 1 -4C-alkDxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula {I), wherein
R1 is -CH2-3-6C-cycloa!kyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy, R21 is hydrogen,

R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)„-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cydoalkyl group substituted by R6, R4 is -C(O)-cyclopropyl, wherein the cyclopropyl group is optionally substituted by R42, R42 is hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalky!, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 Is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-aJkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -0-CHa-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,

R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C-cydoalkyl group substituted by R6,
R4 -C(O)-O-1-4C-alkyl, which is optionally substituted by R43,
R43 is 1-2C-alkoxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73,
R71 ts 1-4C-alkoxy or hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1 -4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(0V1-4C-
alkyl. or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is KCH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by RB, R4 -C(O)-O-1-4C-alkyl, which is optionally substituted by R43, R43 is methoxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydnoxy, R72 is 1-4C-alkoxy or hydroxy,

R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloa!kyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluQroalkoxy or -C(O)-1-4C-
alkyl. or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-a)kyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroa)koxy,
or R22 and R23 combine-to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -{CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cydoalkyl group substituted by R6, R4 -C(O)-O-1 -4C-alkyl, which is optionally substituted by R43, R43 is hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-60cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein R1 is -CH2-3-6C-cycloalkyl or 1 -4C-alkyl which is optionally substituted by R11, R11 is 1 -4C-alkoxy or hydroxy, R21 is hydrogen,

R22 is hydrogen, halogen, 1-4C-alkyl 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-aIkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)N,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atonn, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycioalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-a!koxy or hydroxy,
R21 Is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-aIkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2),-,
n is 0 or 1,

R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C-cycloalkyl group substituted by R6,
R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-a!kyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-a!koxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-a!koxy or hydroxy,
R6 is -C(O)-NR8R9,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1 -4C-a (koxy or hyd roxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-a[kyl, 1-4C-alkoxy. hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CHrO-,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-a)kyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, R7 is 1-2C-alkyl, which is optionally substituted by R71,

R71 Is 1-2C-aIkoxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
in a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloa!kyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy.
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-a!ky!, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyJ, 1-4C-alkoxy, hydroxy or 1-4C-f(uoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2V,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycIoalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7,
R7 is 1-2C-alkyl, which is optionally substituted by R71, R71 is hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11, R11 is 1-4C-alkoxy or hydroxy,

R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n,-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalky) group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cyctoalkyl, wherein the 3'6C-cycioalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7,
R7 is cydopropyl, which is optionally substituted by R72, R72 is 1-2C-alkoxy, R8 is hydrogen,
R9 is 1 -4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycioalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CHz-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 ar?d R23 combir?e to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,

R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C-cycloalkyl group substituted by R6,
R4 is -C{O}-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is l-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7,
R7 is cyclopropyl, which is optionally substituted by R72,
R72 is hydroxy,
R8 is hydrogen,
R9 IS V4C-alkyl. which 'is optionaViy substituted by R91, or 3-6C-cycloalkyl
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl. 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CHs-O-,
R24 is hydrogen,
Y is -(CH2)„-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cydoalkyl group substituted by R6, R4 is -C(O)-H, 'C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42.
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy,

R6 is -NH-C(O)-R7,
R7 is 1-2C-alkoxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1'4C-alky) which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluorQalkoxy or -C(O)-1-4C-alkyl,
or R21 and R22 combine to form a group -O-CH2-O-,
R23 is fiydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -{CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C-cycloalky} group substituted by R6,
R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyI group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-2C-alkyl, wherein the 1-2C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7. -C(O)-NR8R9 or NH2, R7 is 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is optionally
substituted by R72, or 1-2C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy, salts thereof, and stereoisomers of the compounds and the salts thereof.

In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 rs 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroaikoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -0-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4~ to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
or -C(O)-3'6C-cyc)oalkyl, wherein the 3-6C-cycloalky) group is optionally substituted by
R42, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is 1-4C-alkyl, which is optionally substituted by R71, or 3-6C-cycloalkyl, which is optionally
substituted by R72, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy, salts thereof, and stereoisomers of the compounds and the salts thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,

R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is-{CH2),-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C~cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl, wherein the 3'6C'Cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 IS f-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7 or -C(O)-NR8R9, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy, salts thereof, and stereoisomers of the compounds and the salts thereof.
In a further preferred embodiment, the invention relates to compounds of formula (1), wherein
R1 is -CH£-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1.4C-fluoroalkoxy or-C(O)-1-4C-
alkyl. or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,

R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cydoalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyt group is optionally substituted by R41,
or -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by
R42, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7 or -C(O)-NR8R9, R7 is 1-4C-alkyl, which is optionally substituted by R71, or 3-6C-cyctoalkyl, which is optionally
substituted by R72, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, RS is hydrogen,
R9 is 1-4C-alky!, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy, salts thereof, and stereoisomers of the compounds and the salts thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cyctoalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C'alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O',
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)„-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, sard heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyi group is optionally substituted by R41,
-C(O)-3-6C~cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy,

R43 is 1-4C-alkoxy or hydroxy,
R6 is -C(O)-NR8R9,
R8 is hydrogen,
R9 is 1-2C-alkyl, which is optionally substituted by R91,
R91 is 1-2C~alkoxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (1), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-afkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -0-CH2-O-,
R24 is hydrogen,
Y is -(CH,}„-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cydoalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -C(O)-NR8R9,
R8 is hydrogen,
R9 is 1-2C-alkyl, which is optionally substituted by R91, R91 is hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (1), wherein R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11, R11 is 1-4C-alkoxy or hydroxy, R21 is hydrogen,

R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyi group is optionally substituted by R43, R41 Is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -C(O)-NR8R9, R8 is hydrogen, R9 is cyclopropyl, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1 -4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -(CH2)n^-,
n is 0 or 1,
R3 is a 4- to 6-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4,
wherein R4, if present, is bonded to said nitrogen atom,

R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy.
R42 is 1-4C-alkDxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-a(kyl. 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-,
R24 is hydrogen,
Y is -{CH2)„-,
n is 0 or 1,
R3 is a 4- to 6-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being substituted by R4 at said nitrogen
atom, R4 is -C(O)-H, -C{0}-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycloalkyl or 2-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy,
R2t is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
. alkyl, or R21 and R22 combine to form a group -O-CH2-O-,

R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy. or R22 and R23 combine to form a group -O-CH2-O-, R24 is hydrogen,
Y is -(CH2)„-,
n is 0 or 1,
R3 is a 4- fo 6-membered saturated heterocyctic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being substituted by R4 at said nitrogen atom,
R4 is -C(O)-H. -C(O)-1-4C-alkyl. wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
salts thereof, and stereoisomers of the compounds and the salts thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2.-3-4C-cycloalkyl,
R21 is hydrogen,
R22 is hydrogen,
R23 is hydrogen,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0,
R3 is a 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being optionally substituted by R4, or a cyclohexyl group substituted by
R6, R4 is -C(O)-1-2C-alkyl, wherein the 1-2C-alkyl group is optionally substituted by R41, -C(O)-
cycloprcipyl or-C(O)-O-1-4C-alkyl, R41 is hydroxy, R6 is -NH-C(O)-R7 or NH2, R7 is 1-2C-alkyl, which is optionally substituted by R71, cyclopropy/, which is optionaHy
substituted by R72, or 1-2C-alkoxy, which is optionally substituted by R73, R71 is 1-2C-alkoxy or hydroxy, R72 is hydroxy, R73 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.

In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycloalkyl,
R21 is hydrogen,
R22 is hydrogen,
R23 is 1-4C-alkoxy.
R24 is hydrogen,
Y is -{CH2)n-,
n is 0,
R3 is a 6-memb&red saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being optionally substituted by R4, or a cyclohexyl group substituted by
R6, R4 is -C(O)-1-2C-alkyl, wherein the 1-2C-alkyl group is optionally substituted by R41, -C(O)-
cyclopropyl, wherein cyclopropyl group is optionally substituted by R42, -C(O)-O-1-4C-
alkyl, R41 is 1-2C-a)koxy or hydroxy, R42 is hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is 1-2C-alkyl, which is opfionaKy substituted fay R71, cyclopropyf, which is optionally
substituted by R72, or 1-4C-alkoxy, R71 is 1-2C-alkoxy or hydroxy, R72 is hydroxy, R8 is hydrogen,
R9 is 1-2C-alkyl, which is optionally substituted by R91, or cyclopropyl, R91 is 1-2C-alkoxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycloalkyl,
R21 is hydrogen,
R22 is halogen,
R23 is 1-4C-aikoxy,
R24 is hydrogen,
Y is -(CH,),-,
n is 0,
R3 is a 5- to 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being optionally substituted by R4, or a cyclohexyl group substituted by R6,

R4 is -C(O)-1-2C-alkyl, wherein the 1-2C-alkyl group is optionally substituted by R41, -C(O)-cyclopropyl, wherein the cyclopropyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl,
R41 is 1-2C-alkoxy or hydroxy,
R42 is hydroxy,
R6 is -NH-C(O)-R7 or NH2,
R7 is 1'2C-alkyl, which is optionally substituted by R71, cyclopropyl, which is optionally substituted by R72, or 1-4C-alkoxy,
R71 is 1-2C-alkoxy or hydroxy,
R72 is hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycloa!kyl,
R21 is hydrogen,
R22 is -C(O)-1-4C-alkyl,
R23 is hydrogen,
R24 is hydrogen,
Y is -{CH2)n-,
n is 0,
R3 Is a 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being optionally substituted by R4, R4 is -C(O)-1-2C-alkyl, wherein the 1-2C-alkyl group is optionally substituted by R41, R41 is 1-2C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (1), wherein
R1 is -CH2-3-4C-cycloalkyl,
R21 is hydrogen,
R22 is halogen,
R23 is hydrogen,
R24 is hydrogen,
Y is -(CH2)n-.
n is 0,
R3 is a 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being optionally substituted by R4, or a cyclohexyl group substituted by R6,

R4 is -C(O)-1-2C-alkyl, wherein the 1-2C-alkyl group is optionally substituted by R41. or -C(O)-
0-1-4C-alkyl, R41 is 1-2C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is 1-2C-alkyl which is optionally substituted by R71, or 1-4C-alkoxy, R71 is 1-2C-alkoxy or hydroxy, R8 Is hydrogen,
R9 is 1-2C-alkyl, which is optionally substituted by R91, or cyclopropyl, R91 is 1-2C-alkoxy, a salt thereof, or a stereoisomer of the compound or the salt thereof
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 Is -CH2--3-4C-cycloalkyl,
R21 is hydrogen,
R22 is 1-4C~alkoxy,
R23 is hydrogen,
R24 is hydrogen,
Y is -{CH2V,
n isO,
R3 is a 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being optionally substituted by R4, or a cyclohexyl group substituted by
R6, R4 is -C(O)-1-2C-alkyl, wherein the 1-2C-alkyl group is optionally substituted by R41, -C(O)-
cyclopropyl, wherein the cyclopropyl group is optionally substituted by R42, or -C(O)-O-1-
4C-alkyl, R41 Is 1-2C~alkoxy or hydroxy, R42 Is hydroxy, R6 is -NH-C(O)-R7 or NH2, R7 is 1-2C~alkyl, which is optionally substituted by R71, cyclopropyl, which is optionally
substituted by R72, or 1-4C-alkoxy, R71 is 1-2C-alkoxy or hydroxy, R72 is hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred emtradiment, the invention relates to compounds of formula ((}, wherein
R1 is -CH2-3-4C-cycloal kyl,
R21 is hydrogen,
R22 is 1-4C-fluoroalkoxy,

R23 is hydrogen, R24 is hydrogen,
Y is -{CH2)n-,
n is 0,
R3 is a 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being optionally substituted by R4, or a cyclohexyl group substituted by
R6, R4 is -C(O)-1-2C-alkyl, wherein the 1-2C-alkyl group is optionally substituted by R41, -C(O)-
cyclopropyl, wherein the cyclopropyl group is optionally substituted by R42, or -C(O)-O-1-
4C-alkyl, R41 is 1-2C-alkoxy or hydroxy, R42 is hydroxy, R6 is -NH-C(O)-R7 or NH;, R7 is 't-2C-alkyl, which is optionally substituted by R71, cyclopropyl, which is optionally
substituted by R72, or 1-4C-alkoxy, R71 is 1-2C-alkoxy or hydroxy, R72 is hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (1), wherein
R1 is -CH2-3-4C-cycloalkyl,
R21 is hydrogen,
R22 is 1-4C-alkoxy,
R23 is halogen,
R24 is hydrogen,
Y is -(CH2)n,
n is 0,
R3 is a 5- to 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being optionally substituted by R4, R4 is -C(O)-1-2C-alkyl, wherein the 1-2C-alkyl group is optionally substituted by R41, or -C(O)-
0-1-4C-alkyl, R41 is 1-2C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH5-3-4C-cycloalkyl,
R21 is hydrogen. R22 .is 1-4C-alkyl,

R23 is hydrogen,
R24 is hydrogen,
Y is -(CH2),n-,
n is 0,
R3 is a 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being optionally substituted by R4, or a cyclohexyl group substituted by
R6, R4 is -C(O)-1-2C-alkyl, wherein the 1-2C-alkyl group is optionally substituted by R41, -C(O)-
cyclopropyl, wherein the cyclopropyl group is optionally substituted by R42, or -C(O)-O-1-
4C-alkyl, R41 is 1-2C-alkoxy or hydroxy, R42 is hydroxy, R6 is -NH-C(O)-R7, or NH, R7 is 1-2C-alkyl, which is optionally substituted by R71, 3-6C'Cycloalkyl, which is optionally
substituted by R72, or 1-4C-alkoxy, R71 is 1-2C-alkoxy or hydroxy, R72 is hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycloalkyl,
R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen,
R24 is hydrogen,
Y is -{CH2)n-,
n is 0 or 1,
R3 is a 4- to 6-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionaily substituted by R4, or a
cyclohexyl group substituted by R6, R4 IS -C(O)-H, 'C(O)-1-2C-alkyf. wherein the 1-2C-alkyl group is optionaily substituted by R41,
-C(O)-cyclohexyl, wherein the cyclohexyl group is optionally substituted by R42, or -C(O)-
0-1-4C-alkyl, R41 is 1-2C-alkoxy or hydroxy, R42 is hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH;, R7 is 1-2C-alkyl, which is optionally substituted by R71, cyclopropyl, which is optionally
substituted by R72, or 1-4C-a[koxy, R71 is 1-2C-alkoxy or hydroxy,

R72 is hydroxy,
R8 is hydrogen,
R9 is 1-2C-alkyl, which is optionally substituted by R91, or cydopropyl,
R91 is 1-2C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred emtxsdiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycloalkyl,
R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen,
R24 is hydrogen,
Y is -(CH2)n-,
n is 0,
R3 is a 4- to 6-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
cyctohexyl group substituted by R6, R.4 is -C(O)-H, -C(O)-1-2C-alkyl, wherein the 1-2C-alkyl group is optionally substituted by R41,
-C(O)-cyclopropyl, wherein the cyclopropyi group is optionally substituted by R42, or -C(O)-
0-1-4C-alkyl, R41 is 1-2C-alkoxy or hydroxy, R42 is hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is 1-2C-alkyl, which is optionally substituted by R71, cyclopropyi, which is optionally
substituted by R72, or 1-4C-alkoxy, R71 is 1-2C-alkoxy or hydroxy, R72 is hydroxy, R8 is hydrogen,
R9 is 1-2C-alkyl, which is optionally substituted by R91, or cyclopropyi, R91 is 1-2C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycloalkyl,
R21 and R22 combine to fomn a group -O-CH2-O-,
R23 is hydrogen,
R24 is hydrogen,
Y is -(CH2)„-,
n is 1,

R3 is a 5- to 6-membered saturated heterocyclic ring containing one nitrogen atom and optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4,
R4 is -C(O)-H, -C(O)-1-2C-alkyl wherein the 1-2C-alkyl group is optionally substituted by R41, -C(O)-cyclopropyl, wherein the cyclopropyl group is optionally substituted by R42, or -C(O)-0-1-4 C-alkyl
R41 is 1-2C~alkoxy or hydroxy,
R42 is hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
R1 ts-CH2-3-4C-cycloalkyl,
R21 is hydrogen,
R22 is halogen,
R23 is 1-4C-alkoxy,
R24 is hydrogen,
Y is -(CH2)n,-,
n is 0 or 1,
R3 is a 5- to 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being substituted by R4, R4 is -C(O)-1-4C-alkyl, wherein the 1-4C-alkyi group is optionally substituted by R41, R41 is 1-4C-alkoxy or hydroxy, salts thereof, and stereoisomers of the compounds and the salts thereof,
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 is -CH2-3-4C-cycioalkyl,
R21 is hydrogen,
R22 is hydrogen,
R23 is halogen,
R24 is hydrogen,
Y is -(CH2)n,-,
n is 0,
R3 is a 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being optionally substituted by R4, or a cyclohexyl group substituted by R6,
R4 is -C(O)-1-2C-alkyl, wherein the 1-2C-alky! group is optionally substituted by R41, or -C(O)-0-1-4C-alkyl,
R41 is 1-2C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7 or NH2,

R7 is 1-2C-alkyl which is optionally substituted by R71, cyclopropyt, which is optionally
substituted by R72, or 1-4C-alkoxy, R71 is 1-2C-alkoxy or hydroxy, R72 is hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
(n a further preferred embodiment, the invention relates to compounds of fbrmuia (i), wherein
R1 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-
R24 is hydrogen,
Y is -(CH2)„-,
n is 0 or 1,
R3 is a 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being optionally substituted by R4, R4 is -C(O)- 1-4C-alkyl, wherein the 1-4C-alkyl group is optiortally substitufed by R41, R41 is 1-2C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred emtodiment, the invention relates to compounds of formula (I), wherein
R1 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CHa-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy ov 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-
R24 is hydrogen,
Y is -(CH2),-
n is 0,
R3 is a 6-membered saturated heterocyclic ring containing one nitrogen atom, said
heterocyclic ring being optionally substituted by R4.

R4 is -C(O)-1-2C-alkyl, wherein the 1-2C-alkyl group is optionally substituted by R41,
R41 is 1-2C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen. 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-
R24 is hydrogen,
Y is -(CH2)n,-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof
In a further preferred emtxxiiment, the invention relates to compounds of formula (I), wherein R1 3-4C-alkyl,

R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl, or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-
R24 is hydrogen.
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to /-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4. or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C -C(O)-3-6C~cycloalkyl, wherein the 3-6C-cycfoalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C'alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2, R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloatkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73,
R71 is 1-4C-alkoxy or hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalky), R91 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 3-4C-alkyl,
R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alky), 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
R24 is hydrogen.
Y is -(CH2)n-,
n is 0 or 1,

R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a 3-6C-cycloalkyl group substituted by R6,
R4 is -C(O)-H. -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-aikoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73,
R71 is 1-4C-alkoxy or hydroxy,
R72 is l-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), wherein
R1 3-4C-alkyl,
R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen,
R24 is hydrogen,
Y is -CCH^)„-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6, R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-a!kyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy, R42 is 1-4C-alkoxy or hydroxy, R43 is 1-4C-alkoxy or hydroxy, R6 is -N H-C(O)-R7, -C(O)-N R8R9 or N H2,

R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is
optionally substituted by R72, or 1-4C-aikoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy, R72 is 1-4C-alkoxy or hydroxy, R73 is 1-4C-alkoxy or hydroxy, R8 is hydrogen,
R9 is 1-4C-alkyi, which is optionally substituted by R91, or 3-6C-cycloalkyl, R91 is 1-4C-alkoxy or hydroxy, a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the invention relates to compounds of formula (I), selected from 4-{5-CycIopropylmethoxy-1,3-benzodioxoi-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylicacid (1-propionyl-piperidin-4-y[)-amid; 4-({1-[4-{5-Cyclopropy!methoxy-ben2o[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrinnldin-7-yl]-methanoyl}-amino}-piperidine-1-carboxylic acid ethyl ester; 4-(5-Cyc!opropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-methoxy-acetyl)-piperidin-4-yl]-amide; trans-4-(5-Cyclopropyimethoxy-benzoI1,3]droxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4- acetylamino-cyclohexyl)-amide; trans-4-{5-Cyclopropy!methoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4- [(1-cyclopropyl-methanoyl)-amino]-cyclohexyl}-amide; trans-[4-{{1-[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]-methanoyl}-amino)-cyclohexyl]-carbamic acid ethyl ester; cis-4-(5-Cyclopropy(methoxy-benzo[1,3]dioxol-4-y()-5H-pyrrolo[3,2-dIpyriniidJne-7-carboxylic acid (4- acetylamino-cyclohexyl)-amide; cis-4-(5-Cyclopropylmethoxy-benzo[1,3]dioxoi-4-yl)-5H-pyrrolo[3,2-dlpyrimidine-7-carboxylic acid {4- [(l-cyclopropyl-methanoyl)-amino]-cyclohexyl}-amide; cis-4-(5-Cyclopropy!methoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4~{2-methoxy-ethanoylamino)-cycloh6xyi]-amide; cis-[4~({1-[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]-methanoyl}-amino)-cyclohexylj-carbamic acid ethyl ester; 4-(5-Cyclopropylmethoxy-benzo[l,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid
amide; 4-(5-Cyclopropytmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ({S)-1-acety!-pyrrolidin-3-yl)-amide; 4-(5-Cyciopropylmethoxy-benzo[1,3]dioxol-4'yl)-5H-pyrrolo(3,2-d]pyrimidine-7-carboxylic acid [(S)-1-(1-cyclopropyl-methanoyl)-pyrrolidln-3-yl]-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxoi-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(S)-1-(2-methoxy-ethanoyi)-pyrrolidin-3-yl]-amide; (S)-3-({1-[4-{5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]-methanoyl}-anfiino)-pyrrolidine-1-carboxylic acid ethyl ester; 4-{5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrroio[3,2-c/]pyrimidine-7-carboxylic acid (1-formyl-piperidin-4-ylmethyl)-amide; 4-(5-Cyclopropylmetboxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d)pyrimidine-7-carboxylic acid (1-acetyl-piperidin-4-ylmethyl)-amide: 4-(5-Cyc(opropylmethoxy-benzo[1.3Jdioxol-4-yl)-5H-pyrro(o[3,2-d]pyrimidine-7-carboxylic acid (1-(1-cyclopropyl-methanoyl)-piperidin-4-ylmethyl]-amide; 4-{5-Cyclopropylmethoxy-b6nzo[1,3]dioxol-4-yl)-5H-pyrrolo(3,2-d]pyrimidine-7-carboxylic acid [1-(2-methoxy-ethanoyl)-p!peridin-4-ylmethyl]-amide; 4-[{{1-(4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c/lpyrimidin-7-yl]-methanoyl}-amino)-methyl]-piperidine-1-carboxylrc acid ethyl ester; 4-(5-Cyclopropylrnethoxy-ben2o[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrirnidine-7-carboxylic acid (1-forrriyi-piperidin-3-ylmetiiyl)-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-propionyl-piperidin-3-ylmeihyl)-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-y[)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-(2-metboxy-acetyl)-piperJdin-3-ylmethy)]-amJde; 3-({[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-methyl)-piperidine-1-carboxylic acid ethyl ester; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-formyl-pyrrolidin-3-ylmethyl)-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrroloI3,2-d]pyrimidine-7-carboxylic acid [1-{2-nnethoxy-acetyl)-pyrrolidin-3-ylmethyl]-amide; 3-({[4-{5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c^pyrimidine-7-carbonyt]-amino)-methyl)-pyrrolidine-1-carboxylic acid ethyl ester; 4-{5-Cyclopropy(methoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-cf]pyrimidine-7-carboxylic acid (4-fonnyl-morpholin-2-ylmethyl)-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxo!-4-yi)-5H-pyrrolo[3,2-c(lpyrimidine-7-carboxylic acid {4-propionyl-morpholin-2-ylmethyl)-amide; 4-{5-CyclopropylnDethoxy-benzo[1.3]dioxol-4-yl)-5H-pyrrolo[3,2-c(]pyrimidine-7-carboxylic acid [4-(2-methoxy-acetyl)-morpholin-2-ylmethyl]-annide; 2-{{[4-(5-Cyclopropylmethoxy-ben2o[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-methyl)-morpholine-4-carboxylic acid ethyl ester; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5W-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-acetyl-azetidin-3-yl)-amide; 4-{5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pynmidine-7-carbaxylic acid (1-propionyl-azetidin-3-yl)-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-methoxy-ethanoyl)-azettdJn-3-ylJ-annide; 3-({1-[4-{5-Cydopropylmefhoxy-benzo['(,3]dioxoi-4-yl)-5W-pyrro(o[3,2-c(jpyrimidin-7-yl]-methanoyl}-amino)-azetidlne-1-carboxylic acid ethyl ester; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidlne-7-carboxylic acid (1-formyl-piperidin-4-yl)-amide; 4-(5-CyclQpropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c(|pyrimidine-

7-carboxylic acid ((S)-1 -propiony)-piperidin-3-yl)-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl>5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(S)-1-(2-methoxy-ethanoyl)-piperidin-3-yl]-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3ldioxol-4-yl)-5H-pyrroto[3,2-c/|pyrimidine-7-carboxylic acid ((S)-1-acety(-piperidin-3-yl)-amide; 4-(5-Cyciopropylmethoxy-benzo[1,3]dioxo(-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ((R)-1-propionyl-piperidin-3-yl)-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxoi-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [{R)-1-(2-nnethoxy-etlianoyl)-piperidin-3-yl]-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5rt-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ((R)-1-acetyl-piperidin-3-yl)-amide; trans-4-{5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrro!o[3,2-d]pyrimidine-7-carboxylic acid [4-(2-m6thoxy-acetylamino)-cyclohexyl]-amide: tran5-4-(2-Cyclopropylmethoxy-4-methoxy-phenyi)-5H-pyrrolo[3,2-dlpyrimidine-7-carboxylic acid {4-acetylamino-cyclohexyl)-amide; trans-4-{2-Cyclopropyinnethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(cyclopropanecarbonyl-amino)-cycloliexyl]-amide; tfans-4-(2-CyclopropylmethQxy-4-nnethoxy-plienyi)-5H-pyrrolol3,2-d]pyrimidine-7-carboxylic acid [4-(2-melhoxy-acetylamino)-cyclohexyl]-amide; trans-(4-{I4-(2-Cyclopropylmethoxy-4-rriethoxy-phenyl)-5H-pyrrolo[3,2-dlpyrimidine-7-carbonyl]-amino}-cyc!ohexyl)-carbamic acid ethyl ester; cis-4-{2-Cyclopropylmetlioxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4-acety!amino-cyclohexyl)-amide; cis-4-(2-Cyclopropytmethoxy-4-methoxy-phenyl)-5>y-pyrrolo[3,2-c')pyrimid(ne-7-carboxy)icacid [4-{cyclopropanecarbonyl-amino)-cycloliexyl]-amide; cis~4-(2-Cyclopropylmethoxy-4-methoxy-pheny!)-5H-pyrrolo[3,2-tf]pyrimidine-7-carboxylic acid [4-(2-methoxy-acetylamino)-cycloliexyl]-amtde; cis-{4-{[4-(2-Cyclopropylmethoxy-4-metfioxy-phenyl)-5H-pyrralo[3,2-alpyrimtdine-7-carbonyl]-amfno}-cyclohexyl)-carbamic acid etiiyl ester; 4-(2-Cyclopropylmethoxy-4-methoxy-plienyl)-5H-pyrrQ!o[3,2-c/ipyrimidine-7-carboxyiic acid (1-acetyl-piperidin-4-yl)-amide; 4-{2-Cyclopropylnnethoxy-4-metiioxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(1~cyc(opropyl-methanoyl)-p[peridin-4-yl]-amide; 4-{2-Cyclopropylmethoxy-4-methoxy-ptienyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-methoxy-etlianoyl)-piperidin-4-yl]-amide; 4-({1-[4-(2-Cyclopropylmethoxy-4-methioxy-phenyi)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]-inetlianoyl}-amino)-piperidine-1-carboxylic acid ethyl ester; trans-4-{2-Cyclop ropy lmethoxy-5-m ethoxy-phe ny l)-5H-py rrolo[3,2-d] py rim id i ne-7-ca rboxy lie acid (4-acetylamino-cyclohexyi)-amide; trans-4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyIic acid [4-(cyclopropanecarbonyl-amino)-cyclohexyl]-amide; trans-4-{2-Cyc!opropylnnethoxy-5-methoxy-phenyl}-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(2-methoxy-acetylamino)-cyclohexyl]-amide; trans-{4-{[4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-cyciohexyl)-carbamic acid ethyl ester; cis-4-{2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-c/ipyrimidine-7-carboxylic acid (4-acetylamino-cyclohexyl)-amide; cis-4-{2-Cyclopropytmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(cyclopropanecarbonyl-amino)-cyclohexyl]-annJde; cis-4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(2-methoxy-acetylamino)-cyclohexy!]-amide; cts-(4-{[4-{2-Cyclopropylnnethoxy-5-met)ioxy-phenyl)-5H-

pyrrolo[3,2-d]pyrimidine-7-carbonylI-amino}-cyclohexyl)-carbamic acid ethyl ester; 4-{2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-acetyl-piperidin-4-yl)-annide; 4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {1-cyclopropanecarbonyl-piperidin-4-yl)-amide; 4-(2-Cyclopropylinethoxy-5-nnethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1 -(2-methoxy-acetyl)-piperidin-4-yl]-amtde;4-{[4-(2-Cyclopropylniefhoxy-5-me(hoxy-pheny(}-5W-pyrro(o[3,2-c(]pyrimidine-7-carbony(J-amino}-piperidine-1-carboxylic acid ethyl ester'; cis-4-(2'Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-dlpyriinidine-7-carboxylic acid (4-acetylamino-cyclohexyl)-amide; cis-4-(2-Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-dlpyrimidine-7-carboxylic acid [4-(2-methoxy-acetylamino)-cydohexyl]-amide; cis-(4-{[4-(2-Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-c(]pyrimidine-7-carbQnylJ-annino}-cyclohexyi)-carbamic acid ethyl ester; trans-4-(2-Cyclopropylniethoxy-4-flu oro-phenyl}-5H- pyrrolo[3,2-d]py rim id irfe-7-cartx)xy lie acid (4-acetylamino-cyclohexyl)-amide; trans-4-(2-Cyclopropylnnethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-c(]pyrimidine-7-carboxylfc acid [4-(2-methoxy-acety(amino)-cyclohexyl]-amide; trans-(4-{[4-(2-Cyciopropy(methoxy-4-fluoro-phenyl)-5H-pyrro!o[3,2-c(]pyrimidine-7-carbonyl]-amino}-cyclohexyl)-carbannic acid ethyl ester; 4-(2-Cyclopropylmethaxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-c(|pyrimidine-7-carboxylic acid (1-acetyl-pi peridin-4-yl)-am ideter; 4-(2-Cyclopropylm ethoxy-4-fIuoro-phenyl)-5H-pyrrolo[3,2-c^pyrimidine-7-carboxylic acid (1-propionyl-piperidin-4-yl)-amide; 4-(2-Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-a]pyrimidJne-7-carboxylic acid [1-(2-methoxy-acetyl)-piperfdin-4-yl]-amide; 4-(2-Cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2-d)pyrimidine-7-carboxylic acid (1-acetyl-piperidin-4-yl)-amide; 4-(2-Cyclopropylifnethoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-prop(ony(-prperid(n-4-yl)-afnide; 4-(2-Cyclopropy(methoxy-5-nuoro-pheny/)-5(4-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-melhoxy-acetyl)-piperidin-4-yl]-amtde; trans-4-(2-Cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2-c(]pyrimidine-7-carbioxylicacid (4-acetylamino-cyclohexyl)~amide; lrans-4-{2-Cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrro!o[3,2-d]pyrlmidine-7-carboxylic acid {4-propionylamino-cyclohexyl)-amide; trans-4-{2-Cyclopropylmethoxy-5-fluoro-phenyl)-5W-pyrrolo[3,2-d]pyrimidine-7-carboxyticacrd [4-(2-rTiethoxy-acetylamino)-cyclohexyl]-amide; trans-4-(2-Cyclopropylinethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-acetylamino-cyclohexyl)-amide; trans-4-(2-Cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-cf)pyrimidine-7-carboxylic acid [4-{2-methoxy-acetylamJno)-cyclohexy)]-amide; trans-(4-{[4-(2-Cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-c(]pyrimidine-7-carbonyl]-aniino}-cyclohexyl)-carbamic acid ethyl ester; trans-4-(2-Cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyllc acid (4-(cyc(opropanecarbonyl-am[no)-cyclohexy(]-amide; 4-(2-Cyclopropy[methoxy-phenyl)-5H-pyrrolo[3,2-<: acid ethyl ester> 144
2 0 SEP 2010

4-(2-Cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-methoxy-ethanoyl)-piperidin-4-yl]-amide; 4-(2-Cyclopropylmethoxy-4-fluoro-5-rnethoxy-phenyl)-5H-pyrrolo[3,2-c^pyrimidine-7-carboxylic acid (1-acetyl-piperidin-4-yl)-amide; 4-(2-Cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {(R)-1-acetyl-piperidin-3-yl)-amide; 4-(2-Cyc!opropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ((R)-1-propionyl-piperidin-3-yl)-amide; 4-(2-Cyctopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1-(2-methoxy-acetyl)-piperid(n-3-yl]-amide; 4-(2-Cyclopropylmelhoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ({R)-1-acetyl-pyrrolidin-3-yl)-amide; 4-(2-Cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ((R)-1-propionyl-pyrrolidin-3-yl)-amide; 4-(2-Cyclopropylmethoxy-4-fluoro-5-methoxy-plienyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyiic acid [{R)-1 -{2-methoxy-acetyl)-pyrrolidin-3-y!]-amide; trans-4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-acetylamino-cyclohexyl)-am(de; (rans-4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl}-5W-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(2-methoxy-acetylamino)-cyclohexyl]-amide; 4-(2-Cyclopropylmethoxy-5-fluoro-4-niethoxy-phenyl)-5H-pyrrolo[3,2-c(jpyrimidine-7-carboxylic acid {1-acetyl-piperidin-4-yi)-annide; 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-methoxy-etlianoyl)-piperidin-4-yl]-amide; 4-{2-CyclopropyImethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-propionyi-piperidin-4-yi)-amide; 4-(2-Cyclopropylmethoxy-5-fluoro-4-metiioxy-plienyl)-5H-pyrroto[3,2-d]pyrimidine-7-carboxylic acid ((R)-1-propronyl-piperid(n-3-yl)-amide; 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl}-5H-pyrrolo[3,2-c(|pyrimidine-7-carboxylic acid [(R)-1-{2-methoxy-ethanoyl)-piperidin-3-yl]-amide; 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {(R)-1-acetyl-piperidin-3-yl}-amide; 4-(2-Cyclopropylnnethoxy-5-fiuoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ({S)-1-propionyl-piperidin-3-yl)-amide; 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-pheny!)-5H-py rrolo[3,2-d] py rim id i ne-7-carboxy I ic acid [(S)-1 -(2-m ethoxy-ethanoy l)-piperidin-3-yl]-am id e; 4-(2-Cyclopropylmethoxy-5'fiuoro-4-methoxy-phenyl )-5H-pyrrolo[3,2-d]pyrimidine-7-carboxy\ic acid ((S)-1-acetyl-piperidin-3-yl)-amide; 4-(2-Cyclopropylrnethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrclo[3,2-d]pyrimidine-7-carboxylic acid ((R)-1-acetyl-pyrrolidin-3-yl}-amide; 4-(2-Cyclopropylnnethoxy-5-fluoro-4-methoxy-phenyl}-5H-pyrrolo[3,2-c(|pyrirriidine-7-carboxylic acid ((R)-1-propionyl-pyrrolidin-3-yl)-amide; 4-(2-Cyclopropylmethoxy-5-fluoro-4-nnethoxy-phenyl)-5H-pyrrolo[3,2-c^pyrimidine-7-carboxyllcacid [(R)-1-(2-methoxy-acetyl)-pyrrolidin-3-yl]-amide; trans-4-(2-Cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrrolo[3,2-(flpyrimidine-7-carboxylic acid (4-acety)amino-cyc)ohej
7-carboxylic acid (1-acetyl-piperidin-4-yl)-amide; 4-(2-Cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrro(o[3,2-d]pyrimidine-7-carboxylic acid [1-(2-methoxy-acety()-piperidin-4-yl|-amide; 4-{[4-(2-Cyclopropyimethoxy-5-methyl-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbQnyl]-amino}-piperidine-1-carboxylic acid ethyl ester; trans-4-{5-Cyclobutylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxy(ic acid (4-acety(amino-cyc(ohexyl}-amide; trans-4-(5-Cyc!obuty(nnethoxy-benzo[1,3]dioxol-4-yl}-5H-pyrro!o[3,2-d]pyrimidine-7-carboxylic acid [4-(cyclopropanecarbonyl-amino)-cyclohexyl]-amide; trans-4-(5-Cyclobutylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(2-me(hoxy-ethanoy(amino)-cyclohexyl]-amide; 4-(5-Cyclobutylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyllc acid {1-acetyl-piperidin-4-yl)-amide; 4-(5-Cyclobutylmetlioxy-benzo[1,3]dioxol-4-yl)-5H-pyrroto[3,2-d]pyrimidine-7-carboxylic acid [1-(1-cyclopropy(-methanoyl)-pipertdrn-4-y(]-afntde; 4-(5-Cyc(obutylmethoxy-benza[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-methoxy-ethanoyl)-piperidin-4-yl]-amide; 4-{{1-[4-(5-Cyclobutylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c(Ipyrimfd(n-7-yl)-methanoyl}-amino)-piperidine-1-carboxylic acid ethyl ester; 4-(5-Ethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d)pyrimidine-7-carboxylic acid {1-propionyl-piperidin-4-yl)-amide; 4-{[4-(5-Ethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d)pyrinnidine-7-carbonyl]-arritno}-piperidine-1-carboxylic acid ethyl ester; 4-(5-Ethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrroto[3,2-dlpyrinnidine-7-carboxylic acid [1-(2-mettioxy-acetyl)-piperidin-4-yl]-amide; 4-(5-Ethoxy-ben2o[1,3]dioxol-4-yl)-5H-pyrroio[3,2-d]pyrimidine-7-carboxylic acid ((R)-1-propionyl-pyrrolidin-3-yl)-amide;(R)-3-{[4-(5-Ethoxy-benzo[1,3Jd(oxol-4-yl)-5H-pyrrolo(3,2-d]pyrimidine-7-carbonyl]-amino}-pyrro!idine-1-carboxylic acid ethyl ester; 4-(5~Ethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ((R)-1-(2-methoxy-acetyl)-pyrrolidin-amide; 4-{5-Propoxy-benzo(1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyllc acid (1'proplonyl-piperidin-4-yl)-amide; 4-{[4-(5-Propoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo(3,2-cOpyrimidine-7-carbonyl]-amino}-piperidinB-1-carboxylic acid ethyl ester; 4-(5-Propoxy-benzoI1,3]dioxol-4-yl)-5H-pyrrolo[3,2-cOpyrimidine-7-carboxyllc acid ((R)-1-propionyl-pyrrolidin-3-y))-amide; (R)-3-{f4-(5-Propoxy-benzo[1,3)dioxol-4-yl)-5H-pyrro[o[3,2-d]pyrimidine-7-carbonyl]-amino}-pyrrolidine-1-carboxylic acid ethyl ester; 4-(5-Propoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R>-1 -(2-m ethoxy-acetyl)-pyrroiidin-3-yl]-amide; 4-(5-Butoxy-benzo11,3]d ioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyiic acid (1-propionyl-piperidin-4-yl)-amide; 4-{[4-(5-Butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}~piperidine-1-carboxyiic acid ethyl ester; 4-{5-Butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-formyi-piperidin-4-yl)-annide; 4-(5-Butoxy-benzo[1,3Idtoxol-4-yl)-5H-pyrroio[3,2-d]pyrimidine-7-carboxylic acid (1-propionyl-piperidin-3-yl)-amide; 3-{[4-(5-Butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-piperidine-1-carboxyiic acid ethyl ester; 4-(5-Butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-methoxy-acetyl}-plperidin-3-yi]-amide; 4-(5-ButQxy-benzo[1,3]dioxol-4-yl}-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ((R)-1-propionyl-pyrrolidin-3-yl)-amide; (R)-3-{[4-(5-Butoxy-benzo['1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d)pyrinnidine-7-carbonyl]-

amino}-pyrrolidine-1-carboxylic acid ethyl ester; cis-4-(4-Methoxy-2-(2-methoxy-ethioxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4-acetylamino-cyclohexyl)-amide; cis-4-[4-Methioxy' 2-{2-metiioxy-ethoxy)-plienyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyiicacid [4-(cyclopropanecarbonyl-amino)-cyclohexyt]-amide; cis-4-[4-methoxy-2-{2-methoxy-ethoxy}-plienyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxytic acid [4-(2-methoxy-acetylamino)-cyclohexyl]-amide; trans-4-[4-Methoxy-2-{2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-acetylamino-cyclohexyl)-amide; trans-4-[4-Methoxy-2-(2-methoxy-ettioxy)-phenyi]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-{cyclopropanecarbonyl-amino)-cyclohiexyl]-amide: trans-4-[4-IVlethoxy-2-(2-methoxy-ethoxy}-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(2-methoxy-acety(amino)-cyclohexyl]-amide; 4-[4-Methoxy-2-(2-methoxy-ethoxy)-phenyiI-5H-pyrrolo[3,2-dIpyritnidine-7-carboxylic acid (1-acetyl-piperidin-4-yl)-amide; 4-[4-IVlethoxy-2-(2-methoxy-ethoxy)-phenyl}-5H-pyrrolo[3,2-d]pyrimidine-7-carboxytic acid {1-cyclopropanecarbonyl-piperidin-4-yl)-amide; 4-[4-Methoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylrc acid (1-(2-methoxy-acetyl)-piperidin-4-yl]-amide; trans-4-[5-(2-Methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4-acetylamino-cyclohexyl)-atnide; trans-4-(5-(2-Melhoxy-elhoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyiic acid (4-acetylamino-cyclohexyl)-amide; trans-4-[5-(2-Methoxy-ethoxy)-benzo[13]dioxol-4-yl]-5H-pyrrofo[3,2-d]pyrimidine-7-carboxylic acid [4-(2-methoxy-acetylamino)-cyclohexyl]-amide; cis-4-[5-{2-Methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-acetylamino-cyclohexyl)-amide; cis-4-{5-{2-iV1ethoxy-ethoxy)-ben2o[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-acetylamino-cyclohexyl)-amide; cis-4-[5-(2-Methoxy-ethoxy)-benzo(1,3]dioxol-4-yl]-5H-pyrralo[3,2-d]pyrimidine-7-carboxylic acid [4-(2-methoxy-acetylamino)-cyclohexyl]-amide; cis-[4-({4-[5-(2-Methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5/7-pyrrolo[3,2-d]pyriniidine-7-carbonyl}-amino)-cyclohexyl]-carbamic acid etiiyl ester; 4-[5-(2-Mettioxy-ethoxy)-ben20[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d)pyrimidine-7-carboxylic acid (1-acetyl-piperidin-4-yl>-amide; 4-[5-(2-Methoxy-ethoxy)-benzo[1,3]dioxo!-4-yl]-5H-pyrro!o[3,2-cf]pyrimidine-7-carboxylic acid {1 -cyclopropanecarbonyl-piperidin-4-yl)-amide; 4-[5-(2-Methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d]pyrinnidine-7-carboxylic acid [1-(2-melhoxy-acetyl)-piperidin-4-yl]-annide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-cflpyrimidine-7-carboxylic acid [1-(2-hydroxy-ethanoyl)-piperidin-4-yl]-amide; trans-[4-({1-[4-(5-Cyclopropylmethoxy-benzo(1,3]dioxol-4-yl)-5H-pyrrolo[3,2-dipyrimidine-7-carboxylic acid [4-(2-hydroxy-elhanoylamlno)-cyctohexyl]-amide; tra ns-[4-({1 -[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-py rrolo[3,2-d] pyrimidine-7-carboxylic acid [4-((S)-2-hydroxy-propanoylamino)-cyclohexylI-amide; cis-[4-({1-[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxoi-4-yl>-5H-pyrrolo[3,2-cqpyrimidine-7-carboxylic acid [4-{2-hydroxy-ethanoylamino)-cyclohexyl]-amtde; cis-[4-({1-[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-((S)-2-liydroxy-propanoylamino)-cyclohexyl}-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyiic acid [1-((S)-2-hydroxy-propanoyl)-piperidin-4-yl)-amide; trans-4-{5-Cyclopropylnnethoxy-

benzo[1,3)dioxol-4-y!)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4-[(1 -hydroxy-cyclopropanecarbonyl}-amino]-cyclohexyl}-annide; cis-4-(5-Cyclopropylnfiethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrinnidine-7-carhoxylic acid {4-[(1-hydroxy-cyclopropanecarbonyl)-amino]-cyclohexyl}-amide; 4-(5-Cyc!opropylmethoxy-benzo[1,3Jdioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {1-[1-(1-hydroxy-cyclopropyl)-methanoyl]-piperidin-4-yl}-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1-(2-hydroxy-ethanoyl)-pyrrolidin-3-yl]-ainide; 4-(5-CyclopropylfDethoxy-benzo(1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1-((S)-2-hydroxy-propanoyl)-pyrrolidin-3-yl]-annide; 4-(5-CyclopropylmeHioxy-benzo[1,3]dioxoI-4-yl)-5H-pymolo[3,2-d]pyrlmidine-7-carboxylic acid {(R)-1-[1-(1-hydroxy-cyclopropyl)-methanoyl]-pyrrolidin-3-yl}-amide; 4-(5-Cyclopropyimethoxy-benzoI1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(S)-1-(2-hydroxy-ethanoyl)-pyrrolidin-3-yl)-amide; 4'{5-Cyclopropylrnethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo(3,2-d}pyrlmidine-7-carboxylic acid [(S)-1-{(S)-2-hydroxy-propanoyl)-pyrrolldin-3-yi]-amide; 4-{5-Cyclopropylmeflnoxy-ben2o[1,3]d ioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-earboxylic acid {(S)-1 -[1 -(1 -hydroxy-cyclopropyl)-methanoyl]-pyrrolidin-3-yl}-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxoi-4-yl)-5H-pyrrolo[3,2-c(]pyrimidlne-7-carboxylic acid I1-(2-hydroxy-etlianoyl)-piperidin-4-ylmethyl]-amide; 4-(5-Cyclopropy!methoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-cf]pyrimidine-7-carboxylic acid [1-{(S)-2-hydroxy-propanoyl)-piperidJn-4-ylmethyl]-amide; 4-(5-Cyclopropyimethoxy-benzo[1,3]dioxol-4-yl)-5H-py rrolo[3,2-d] py rim id ine-7-carboxyl icacid{1-[1-{1-hyd roxy-cyclopro py I )-m etha noy l]-piperid i n-4-ylmethyl}-amide; 4-(5-CyclopropylmethQxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-hydroxy-acetyl)-piperidln-3-ylmethyl]-am(de; 4-(5-Cyclopropylmethoxy-ben2o[1,3]dioxot-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1 -{{S}-2-hydroxy-propionyl)-piperidin-3-ylmethyl]-amide;4-(5-Cyclopropylnnethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-{2-hydroxy-acetyl)-pyrrolidin-3-ylmethyl]-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrro!o[3,2-d]pyrimidine-7-carboxylic acid [1-{(S)-2-hydroxy-proptonyl)-pyrrolidin-3-ylmethylI-amide; 4-(5-Cycloprapylmethoxy-benzo[1,3]dloxol~4-yt)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-{2-hydroxy-acetyl}-morpholin-2-ylmethyi]-amide; 4-{5-Cyclopropylmethoxy-benzo(1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-({S)-2-hydroxy-propionyl)-nnorpholin-2-yl]methyl]-amide;4-(5~Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrroto[3.2-d]pyrimidine-7-carboxyl(C acid [1-(2-hydroxy-ethanoyl)-azetrdin-3-yl]-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d}pyrimidine-7-carboxylic acid [1-((S)-2-hydroxy-propanoyl)-azetidin-3-ylI-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrQlo[3,2-d]pyrimidine-7-carboxylic acid [(S)-1-{(S)-2-hydroxy-propanoyi)-piperidin-3-yl]-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3Idioxol-4-yl>5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1-({S)-2-hydroxy-propanoyl)-piperidin-3-yll-amide; Irans-4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-{2-hydroxy-acetylamino)-cyclohexyl]-amide; trans-4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-((S)-2-hydroxy-propionylamino)-cyclohexyl]-anfiide; trans-4-{2-Cyclopropylmethoxy-4-

methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4-[( 1 -hydroxy-cyclopropanecarbonyl)-amino]-cyclohexyl}-amide; cis-4-(2-Cyclopropylmethoxy-4-methoxy-phenyi)-5H-pyrrolo[3,2-c/lpyrin(iidine-7-carboxylic acid [4-(2-hydroxy-acetylamino)-cyclohexyl]-amide; cis-4-(2-Cyc[opropylmethoxy-4-methoxy'phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-((S}-2-hydroxy-propionylamino)-cyclohexyl]-amide; cis-4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrQlo[3,2-d]pyrimidine-7-carboxylic acid {4-[(1 -hydroxy-cyclopropanecarbony])-annino]-cyclohexyl]-am(de;4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrra/o[3,2-c(|pyrimfd(ne-7-carboxylic acid [1'(2-hydroxy-etlianoyl)-piperidin-4-yi]-amide; 4-(2-CyclopropylmeHioxy-4-methoxy-phenyl)-5H-pyrrolo(3,2-d)pyrimidine-7-carboxylic acid [1-((S)-2-hydroxy-propanoyl)-piperidin-4-yi]-amide; 4-(2-Cyclopropylmelhoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {1-[1-{1'hydroxy-cyclopropyl)-fnefhanoyi)-piperidin-4-yl}-amide; cis-4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(2-hydroxy-acetylamino)-cyclohexyl]-amide; cis-4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylrc acid {4-[(1-hydroxy-cyclopropanecarbany()-amrno]-cyclohexyl}-amrde; trans-4-(2-Cyclopropylmethoxy-5-nnethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4-[(1-hydroxy-cydopropanecarbonyl)-amino]-cyclohexyl}-amide; 4-(2-Cyclopropylmethoxy-5-methoxy-phenyl}-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-hydroxy-acetyl>-piperidin-4-yl]-amide; 4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxy1icacid [1-((S)-2-hydroxy-propionyl)-piperidin-4-yl]-amide; 4-(2-Cyclopropylmethoxy-5-methoxy-phenyt)-5H-pyrrolo[3,2-c(] pyrim id i ns-7-carboxy lie acid [ 1 -(1 -hydroxy-cyclop ropaneca rbonyl)-pi peri d in-4-yl]-amrde; cts-4-(2-Cyclopropy/methoxy-4-fluoro-phenyl)-5H-pyfrolo[3,2-C3]pyrimidine-7-carboxylic acid [4-(2-hydroxy-acetylamino)-cyclohexyl]-amide; cis-4-(2-Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-{(S)-2-hydroxy-propionylamino)-cyclohexyl]-amide; cis-4-(2-Cyclopropylmethoxy-4-fiuoro-pheny]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4-[{1-liydroxy-cydopropanecarbonyl)-amino]-cyclohexyl}-amide; trans-4-(2-Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyllc acid [4-(2-hydroxy-acetylamino)-cydohexyl]-amide; trans-4-(2-CyclopropyInnethoxy-4-fluoro-phenyi)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxy)ic acid [4-((S)-2-hydroxy-propronylamino)-cyclohexyl]-amide; trarts-4-(2-Cyctopropylmethoxy-4-fluoro-pheny I )-5H-py rrolo[3,2-d]py rim id i ne-7-ca rboxylic acid {4-[( 1 -hydroxy-cyclopropa n ecarbony I)-amino]-cyclohexyl}-amide; 4-(2-Cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyllc acid [1-(2-hydroxy-acetyl)-piperidin-4-yl]-amide; 4-(2-Cyclopropylmethoxy-5-fiuoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-({S)-2-hydroxy-propionyi)-piperidin-4-yl]-amide; trans-4-(2-CycIopropylmethoxy-5-fiuoro-plienyl)-5H-pyrrolo[3,2-tf|pyrimidine-7-carboxylic acid [4-{2-hydroxy-acetylamino)-cyclohexyl]-amide; trans-4-(2-Cyc!opropylmethoxy-4-fluoro-phenyl)-5H-pyrro)o[3,2-f/|pyrimidine-7-carboxy)icacid [4-((S)-2-hydroxy-propJonylamino)-cyciohexyl]-amide; trans-4-(2-Cyclopropylmethoxy~phBnyi)-5H-pyrrQlo[3,2-c^pyiiniidine-7-carboxylic acid [4-(2-hydroxy-acetylamino)-cyclohexyl]-amide; trans-4-(2-Cyciopropylmethoxy-phenyl)-5H-pyrroio[3,2-d]pyrimidine-7-carboxyiicacid [4-((S)-2-hydroxy-propionylamino)-cyclohexyl]-amide;

trans-4-{2-Cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-cy]pyrimidine-7-carboxylic acid {4-[{1-hydroxy-cyclopropanecarbonyl)-amino]-cyclohexyl}-amide; 4-(2-Cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-((S)-2-hydroxy-proptonyl)-piperidin-4-yl]-amide; 4-(2~ Cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-((S)-2-hydroxy-propionyl)-piperidin-4-yl]-amide; 4-{2-Cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrroIo[3,2-d]pyrimidine-7-carboxyiicacid ({R)-1-(2-hydroxy-acetyl)-piperidin-3-yl)-amide; 4-(2-Cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1-({S)-2-hydroxy-propionyl)-piperidin-3-yl]-amide; 4-(2-Cyclopropylnnethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1-(2-hydroxy-acetyl)-pyrrolidin-3-ylI-amide; 4-(2-Cyclopropylifriethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrro[o[3,2-d]pyrim!dine-7-carboxylic acid [(R)-1-((S)-2-hydroxy-propionyl)-pyrrolidin-3-yl]-amide; tran3-4-{2-Cyclopropylmethoxy-5-fluoro-4-methoxy~phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4~ (2-hydroxy-acetylamino)-cyclohexyl]-amJde; trans-4-(2-Cyclopropylmethoxy-5-fluoro4-methoxy-phenyl)-5H-pyfrolo[3,2-dlpyrimidrne-7-carboxyltc acid [4-((S)-2-liydroxy-propionylamino)-cyclohexyl]-amide; trans-4-{2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4-[(1-hydroxy-cyclopropanecarbonyl)-amino]-cyclohexyl}-amide; 4-(2-Cyclopropylmethoxy-5-fiuoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-cf|pyrimidine-7-carboxylic acid [ 1 -(2-hydroxy-ethanoyl)-piperidin-4-yl)-amide; 4-(2-Cyclopropy)methoxy-5'fiuoro-4-methoxy~ phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-((S)-2-hydroxy-propanoyl)-piperidin-4-yl]-amide; 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H~pyrrolo[3,2-d]pyrinnidine-7-carboxylic acid {1-[1-(1-hydroxy-cyclopropyl)-nnethanoyl]-piperidin-4-yl}-annide; 4-(2-cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(S)-1-((S)-2-hydroxy-propanoyl}-piperidin-3-yl]-amide; 4-(2-Cyclopropylmethoxy-5-fliJora-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1-((S)-2-hydroxy-propanoyl)-p)peridin-3-yl]-amide; 4-(2-Cyclopropy(methoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-c(|pyrimldine-7-carboxylic acid [(R)-1-(2-hydroxy-acetyl)-pyrrolidin-3-yl]-amide; 4-(2-Cyclopropylmethoxy-5--fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1-((S>-2-hydroxy-propionyl)-pyrrolidln-3-yl]-amide; trans-4-(2-Cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrrolot3,2-d]pyrimidine-7-carboxylic acid [4-(2-hydroxy-acetylamino)-cyclohexyl]-amtde; trans4-(2-Cyc!opropylmethoxy-5-methyl-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-((S)-2-hydroxy-propionylamino)-cyclohexyl]-amide; trans-4-(2-Cyclopropylnnethoxy-5-methyl-pheny])-5H-pyrrolo[3,2-d|pyrim id i ne-7-carboxyIic acid {4-[( 1 -hyd roxy-cyclopropanecarbonyl)-am ino]-cyclohexyl}-amide;4-{2-Cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-{2-hydroxy-acetyl)-piperidin-4-yl]-amide; 4-(2-Cyclopropylmelhoxy-5-metliyl-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-((S)-2-hydroxy-propionyl)-piperidin-4-yl]-amide; 4-(2-Cyclopropylmethoxy-5-methyl-plienyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(1-hydroxy-cyclopropanecarbonyl)-piperidin-4-yl]-amide; 4-(5-Ethoxy-benzo[1,3]dtoxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-({S}-2-hydroxy-propionyl)-piperidin-4-yl]-amide; 4-{5-

Ethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrinnidine-7-carboxylic acid [(R)-1-((S)-2-hydroxy-propionyl)-pyrrolidin-3-yl]-amide; 4-(5-Propoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-((S)-2-hydroxy-propionyl)-piperidin-4-yl]-amide; 4-(5-Propoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [{R)-1-{(S)-2-hydroxy-propionyl)-pyrrolidin-3-y!]-amide; 4-(5-Butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimldine-7-carboxylic acid [1-((S)-2-hydroxy-propionyl)-piperidin-4-yl]-amide; 4-(5-Butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1-({S)-2-liydroxy-propionyl)-pyrrolidin-3-yl]-amide; trans-4-[4-Methoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-Garboxylicacid [4-(2-hydroxy-acetylamino)-cyclohexyl]-amide; trans-4-[4-Methoxy-2-(2-m6thoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxy((c acid (4-((S}-2-hydroxy-proplonylamino)-cyc(ohexy(]-annide;frans-4-[4-iVlethoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4-[(1-hydroxy-cyclopropanecarbonyl)-amino]-cyclohexyl}-amide; cis-4-[4-Methoxy-2-{2-methoxy-ethoxy)-phenyl]-5H'pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4-[{1-hydroxy-cyclopropanecarbonyl)-aminoj-cydohexyl]-arride; 4-[4-Methoxy-2-(2-methoxy-ethoxy)-phenyl)-5H'-pylrolo[3,2-d]pyrimldine-7-carboxylic acid [1-{1-hydroxy-cyclopropanecarbonyl)-piperidin-4-yl]-amide; trans-4-[5-{2-Methoxy-ethoxy)-benzo(1,3]dioxol-4-y)]-5H-pyrrolo[3,2-d]pyrimldine-7-carboxylic acid [4-(2-hydroxy-acelylamino}-cyclohexyl]-amide; cis-4-[5-(2-Methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-c(lpyrJmidine-7-carboxylic acid [4-(2-hydroxy-acetylamino)-cyc)ohexy)]-amide, cis-4-(5-(2-Methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-cf]pyrimidine-7-carboxylic acid [4-((S)-2-hydraxy-propionylannino)-cycioli8xyl]-amide; 4-[5-(2-Methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-c(]pyrimidine-7-carboxyllc acid [1-((S)-2-hydroxy-propionyl)-pipendin-4-yl]-arnide; 4-(5-Acetyl-2-cyclopnopylmethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrinnidine-7-carboxylic acid [1 -{(S)-2-hydroxy-propanoyl)-piperidin-4-yl]-amide; 4-(5-Acetyl-2-cyclopropylmethoxy-plienyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-nnethoxy-acetyl)-piperidin-4-yl]-amide; 4-(5-Acetyl-2-cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-djpyrimidine-7-carboxylic acid (1-acetyl-piperidin-4-yl>-amide;4-(5-Acetyl-2-cyclopropy)methoxy-4-methyl-plienyl)-5H-pyrrolo[3,2-cOpyrimidine-7-carboxylic acid [1-((S)-2-hydroxy-propionyl)-piperidin-4-yl)-amide; 4-(5-Acetyl-2-cyclopropy1methoxy-4-methyl-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-acetyi-piperidin-4-yi)-amide; trans-4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrroio[3,2-d]pyrimidine-7-carboxylic acid [4-{2-methoxy-ethylcarbamoyl)-cyclohexyl]-amide; tran&-4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-cydopropylcarbamoyl-cyclohexyl)-amide; trans-4-(2-Cyclopropylnnethoxy-4-methoxy-phenyl)-5H-pyrrolo(3,2-d|pyrimidine-7-carboxylic acid (4-cyclopropylcarbamoyl-cyclohexyl)-am!de; trans-4-(2-Cy clopropy lmethoxy-4-m ethoxy-pheny I )-5H-pyrrolo[3,2-d] py rim id i ne-7-carboxylic acid [4-(2-methoxy-ethy(carbamoyi)-cyc[ohexylI-amide; trans-4-(2-Cyc(opropylmethoxy-5-fluoro-phenyl)-5H-pyrro!o[3,2-d]pyrimidine-7-carboxy!ic acid {4-cyclopropylcarbannoyl-cyclohexyl)-amide; trans-4-(2-Cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2-dIpyriniidine-7-carboxylic acid [4-{2-methoxy-ethyIcarba moyl)-cyclohexyl]-ann ide; trans-4-(5-Cyclo butylmethoxy-benzo[1,3]d ioxol-4-yl )-5H-

pyrrolo[3,2-d|pyrinnidine-7-carboxylic acid [4-(2-methoxy-ethylcarbamoyl)-cyclohexyl]-amide; trans-4-(5-Cyclobutylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrinnidine-7-carboxylic acid (4-cyclopropylcarbamoyl-cydohexyl)-amide; 4-(2-Cyclopropylmethoxy-5-fiuoro-4-hydroxy-phenyl}-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {1 -acetyl-pip6ridin-4-yl)-amide; 4-(2-Cyclopropylmethoxy-5-fluoro-4-hydroxy-phenyl)-5H-pyrro!o[3,2-d]pyrimidine-7-carboxylic acid (1-propionyl-piperidin-4-yl)-amide; 4-[2-Cydopropylmethoxy-4-(1,1-difluoro-methoxy)-5-fluoro-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-Garboxy)ic acid (1-acetyl-piperidin-4-y))-amide; 4-(2-Cyclopropy)methoxy-4-{l,1-difluoro-methoxy)-5-fluoro-phenyl]-5H-pyrrolo[3,2-c(]pyrinnidine-7-carboxylic acid [1-(2-methoxy-ethanoyl)-piperidin-4-yl]-amide; 4-(2-Cyctopropylmethoxy-5-fluoro-4-hydroxy-phenyl)-5H-pyrro!o[3,2-d]pyrimidine-7-carboxylic acid [1-(2-hydroxy-acetyl)-piperidin-4-yl]-amide 4-(2-Cyclopropylnnethoxy-5-fluoro-4-hydroxy-phenyl)-5H-pyrro!o[3,2-d]pyrimidine-7-carboxylic acid 11-({S)-2-hydroxy-prQpionyl)-piperidin-4-yl]-amide; 4-[2-Cyclopropylmethoxy-4-(1,1-difluoro-fnethoxy)-5-fluoro-phenyl]-5H-pyrrolo[3,2-dlpyrlmidine-7-carboxylic acid [1-{2-hydroxy-acetyl)-piperidin-4-yll-annide; 4-l2-Cyclopropylnnetlnoxy-4-('l, 1 -difluoro-methoxy)-5-fluoro-phenyll-5H-pyrrolo[3,2-d]pyrimidine-7.carboxyllcacid (1-((S)-2-hydroxy-propionyl)-piperidin-4-yl]-annide; a salt thereof, or a stereoisomer of the compound or the salt thereof.
In a further preferred embodiment, the Invention relates to compounds of formula (1), selected from 4-(5-Cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1 -propionyl-piperidin-4-yl)-amid; 4-({1-[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-(flpyrimidin-7-yll-methanoyl}-amino)-piperidine-1-carboxylfc acid ethyl ester; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl}-5H-pyrrolo[3,2-cf]pyrimidine-7-carboxylic acid [1-(2-methoxy-acetyl)-piperidin-4-yl]-amide; trans-4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo(3,2-cf|pyrimidine-7-carboxylic acid (4-acetylamino-cyclohexyl)-amide; trans-4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4- [(1-cyclopropyl-methanoyl)-amino]-cyclohexyt}-amide; trans-[4-({1-[4-(5-Cyclopropylm&thoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d)pyrimidin-7-yl]-methanQyl}-amino)-cyclohexyl]-carbamic acid ethyl ester; cis-4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrro!o[3,2-d]pyrimidine-7-carboxyllc acid (4- acetylamino-cyclGhexyl)-amide; cis-4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-y))-5H-pyfrolo[3,2-o]pyrimid(ne-7-carboxylic acid (4- [(1-cyclopropyl-methanoyl)-aniirro]-cyclohexyl}-amide; cis-4-(5-Cyclopropylmethoxy-benzo(1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(2-methoxy-ethanoylamino)-cyclohexyl]-arTiide; cis-[4-({1-{4-{5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]-methanoyl}-amino)-cyclohexyl]-carbamic acid ethyl ester; 4-(5-Cyclopropylmethoxy-benzo[1,3ldioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {1-acetyl-piperidin-4-yl}-amide; 4-(5-Cyclopropylmethoxy-ben2o(1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(1-cyclopropyl-methanoyl)-piperidin-4-yl]-amide;4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1-(2-methoxy-acetyl}-pyrrolidin-3-yl]-amide; 4-(5-Cyclopropylmethoxy-

benzo[1,3]dioxoI-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {(R)-1-fornnyl-pyrrolidin-3-yi)-amide; 4-(5-Cyclopropylmethoxy-benzo[1.3]dioxol-4-yl>-5H-pyrrolo(3,2-d]pyrimidine-7-carboxyiic acid ({R)-1-acetyi-pyrrolidln-3-yl)-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl}-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyiic acid [(R)-1-{1-cyclopropyl-methanoyl)-pyrrolidin-3-yl]-amide; (R)-3-({1-[4-{5-cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrlmidin-7-yl]-methanoyl}-amino)-pyrrolidine-1-carboxylic acid ethyl ester; 4-(5-Cyclopropylmethoxy-benzo(1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {{S)-1-formyl-pyrrolidin-3-yl)-amide; 4-{5-Cyclopropylnnethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolof3,2-d]pyrirmidine-7-carboxylic acid {(S)-1-acetyl-pyrrolidin-3-yl)-amide; 4-(5-Cyc!opropylmethoxy-benzo[1,3]dioxoI-4-yl}-5H-pyfrolo[3,2-d]pyrimidine-7-carboxylic acid [(S)-1-(1-cyctopropyl-methanoyj)-pyrro[idin-3-yl]-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrirnidine-7-carboxyljc acid [(S)-1-(2-methoxy-ethanoyl}-pyrrolidin-3-yl)-amide; (S)-3-{{1-f4-(5'Cyc)opropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrro!o[3,2-d]pyrinnidin-7-yl]-methanoyl}-amino)-pyrrolidine-1-carboxylic acid ethyl ester; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidtne-7-carboxylic acid {1-formyl-piperidin-4-ylmethyl)-amide; 4-(5-cyclopropylmethoxy-benzo[1,3]dioxol-4-y()-5fy-pyrro[o[3,2-d]pyrinnidine-7-carboxylic acid (1-acety(-piperidin-4-ylmefhyl)-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yI)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(1-cyclopropyl-niethanoyI)-piperidin-4-ylmethyl]-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c(]pyrimldine-7-carboxylic acid [1-(2-melhoxy-ethanoyl)-piperidin-4-ylmethyl]-amide; 4-[({1-[4-{5-Cyclopropylmethoxy-benzo[1,3]dioxol~4-yl)-5H-pyrrolo[3,2-d]pyrirTiidin-7-yl]-methanoyl}-aiTino}-methyl]-piperidine-1-carboxylic acid ethyl ester; 4-(5~Cyclopropylm6thoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-(flpyrimidine-7-carboxylic acid (1-formyl-piperidin-3-ylmethyl)-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrroIo[3,2-d]pyrimidine-7-carboxylic acid (1 -propionyl-piperidirh3-ylmethyl)-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrroIo[3.2-of]pyrimidlne-7-carboxylic acid [1-{2-mGthoxy-acetyl)-piperidin-3-ylmethyl]-amide; 3-({[4-{5-Cyc lop ropy lmethoxy-benzo[ 1,3Id ioxol-4-y l)-5H-py rrolo [3,2-d]pyrinn id i ne-7-carbony l]-am i no}-methyl)-pip6ridine-1-carboxylic acid ethyl ester; 4-{5-Cyclopropylmethoxy-benzoI1,3]dioxol-4-yl>-5H-pyrrolo[3,2-d]pyrimidin6-7-carboxylic acid (1-formyl-pyrrolidir>-3-ylnnethyl)-arriide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrro!o[3,2-d]pyrimidine-7-carboxylic acid [1-(2-methoxy-acetyl)-pyrrolidin-3-ylmethyl]-amide; 3-({[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-cOpyrimidine-7-carbonyl]-amino}-methyl)-pyrrol]dine-1-cartKixylic add ethyl ester; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartx)xylic acid (4-formyl-morpholin-2-ylmethyl)-amide; 4-{5-Cyclopropylmethoxy-benzo[1,3]dtoxol-4-yl)-5H-pyrrolo[3,2-of|pyrimidine-7-carboxylic acid (4-propionyl-morpholin-2-ylniethyl}-amide; 4-{5-Cyclopropy(methoxy-benzo[1,3]droxol-4-y[)-5H-pyrro(o[3,2-olpyrimid(ne-7-carboxyl(cacid [4-(2-methoxy-acetyl)-morpholin-2-ylmethyl]-amide; 2-({[4-(5-Cyclopropylmethoxy-ben2o[1,3ldioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-methyl)-nnorpho!ine-4-carboxylic acid ethyl ester; 4-{5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-

acetyl-azetidin-3-yl)-arnide; 4-{5-cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrro!o[3,2-c^pyrimidine-7-carboxylic acid (1-propionyl-azetidin-3-yl)-amide; 4-(5-cyclopropylinethoxy-ben2o[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-nnethoxy-ethanoyl)-azetidin-3-yl]-amide; 3-({1-[4-(5-Cyclopropy(methoxy-benzof1,3Jdioxol-4-yl)-5H-pyrrolo(3,2-d]pyrimidin-7-yl]-tnethanoyl}-amino)-azetidine-1-carboxylic acid ethyl ester; 4-(5-Cyclopropylinethoxy-benzo[1,3]d!Oxol-4-y!)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-formyl-piperidin-4-yl)-amide; 4-(5-Cyc(opropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrro(o[3,2-a]pyrimidine-7-carboxylic acid ((S)-1-propionyl-piperidin-3-yl)-amide; 4-(5-Cyclopropy!methoxy-benzo[1,31dioxol-4-yl)-5H-pyrrolo(3,2-d]pyrimidine-7-carboxylic acid [(S)-1-(2-methoxy-ethanoyl)-piperidin-3-yl]-amide; 4-(5-cyclopropylmethioxy-benzo[1,3]dioxol-4-yl}-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ((S)-1 -acetyl-piperidin-3-yl)-anfiide; 4-{5-Cyclopropytmelhoxy-ben2o[1.3]dtoxol-4-yl)-5H-pyrrolo[3,2-c(lpyrimldine-7-carboxyiic acid ({R)-1-propionyl-prperidin-3-yl)-amide; 4-(5-CycIopropylmethoxy-benzo[1,3|dioxol--4-y!)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1-(2-methoxy-ethanoyl)-piperidin-3-yl]-amide; 4-(5-Cyclopropylm9!hoxy-benzo[1;3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine"7-carboxylic acid ((K)-1-acelyl-piperidin-3-yl)-amide; trans"4'(5-cyclopropylmethoxy-benzo[1.3]dioxol-4-yl)-5H'-pyrrolo(3,2-d]pyrimidine-7-carboxylic acid [4-(2-iiiethoxy-acetylamino}-cyclohexyl]-amide; trans-4-(2-Cyc!opropylmethoxy-1-methoxy-phenyl)-5H' pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-acetylainino-cyc!ohexyl)-amide; trans-4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-{cyclopropanecart»nyl-arnino}-cyclohexyl]-amide; trans-4-(2-Cycloprqpylnnethoxy-4-methoxy-phenyl)-5H-pyrroto[3,2-c^pyrim/dine-7-carboxylic acid [4-(2-methoxy-acetylamino}-cyclohexyl]-amide; trans-(4-{[4-(2-Cyclopropylnfiethoxy-4-methoxy-phenyl)-5H-pyrrola[3,2-d]pyrtnnidine-7-carbonyl]'amino}-cyclotiexyl)-carbamic acid ethyl ester; cis-4-{2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H'-pyrrofo[3,2-d]pyrimldlne-7-carboxyllc acid (4-acety(amino-cyclohexyl)-amide; cis-4-(2-CycloprQpylmethoxy-4-methoxy-phenyl)-5H-pyrrolo(3,2-dlpyrinnidine-7-carboxylic acid [4-(cyclopropanecarbonyl-amino)-cydohexyl]-amide; cis-4-(2-Cyclopropylmethoxy-4-methioxy-phenyl)-5H-pyrrolo[3,2-d]pyrimldine-7-carboxylic acid [4-(2-methoxy-acety(amino)-cyc(ohexyl]-amide; cis-(4-{[4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-cyclohexyl)-carbanitc acid ethyl ester; 4-(2-Cyclopropylnnethoxy-4-nnethoxy-phenyl)-5H-pyrro!o[3,2-d]pyrimidine-7-cartioxylic acid {1-acetyl-piperidin-4-yl)-amide; 4-{2-Cyclopropylm6thoxy-4-m6thoxy-phenyl)-5H-pyrrolo[3,2-djpyrimidine-7-carbioxylicacid [1-{1-cyclopropyl-methanoyl)-piperidin-4-yl]-amide; 4-(2-Cyclopropylnnethoxy-4-methoxy-phenyl}-5H-pyrrolot3,2-c(]pyrimidine-7-cartx>xylicacid [1-(2-methoxy-ethanoyl)-piperidin-4-yl]-amide; 4-({1-[4-(2-Cyclopropylmethoxy-4-niethoxy-phenyl)-5H-pyrrolo[3,2-d|pyrimidin-7-yl]-nnethanoyl}-amino)-piperidine-1-carboxyiic acid ethyl ester; trans-4-(2-Cyclopropylmethoxy-5-nnethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-acetylamino-cyclohexyl)-am ide; trans-4-(2-Cyclopropylmethoxy-S-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(cyclopropanecarbonyl-amino)-cyclohexyl]-amide; trans-4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyltcacid [4-{2-

methoxy-acetylamino)-cyclohexyl]-amide; trans-(4-{[4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrro!o[3,2-d]pyrimidine-7-carbonyl]-amino}-cyclohexyl)-carbamic acid ethyl ester; cis-4-(2-CycIopropylnnethoxy-5-methoxy-phenyl)-5H-pyrroto[3,2-d]pyrimidine-7-carboxylic acid (4-acetylamino-cyclohexyl)-annide; cis-4-(2-Cyclopropylmethoxy-5-methQxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(cyclopropanecarbonyl-amino)-cyclohexyl]-amide; cis-4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(2-methoxy-acetylamino)-cyclohexyl]-arTtide; cis-(4-{[4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl)-annino)-cyclohexyl)-carbamic acid ethyl ester; 4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d)pyrimidine-7-carboxylicacld (1-acetyl-piperidin-4-yl)-amide; 4-(2-Cyclopropylmethoxy-5-nnethoxy-phenyl)-5H-pyrroloI3,2-c/Jpyrimidine-7' cartxjxylic acid (1-cyclopropanecarbonyl-piperidin-4-yl)-amide; 4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-methoxy-acety!)-piper!d!n-4-yl]-amide; 4-{[4-(2-Cyclopropy!methoxy-5-rTiethoxy-phenyi)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-aminoj-piperidine-l-carboxylic acid ethyl ester, c'is-4-(2-Cyclopropy\melhoxy-4-Vuoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-acetylamino-cyclohexyl)-amide; cis-4-(2-Cyclopropylmethoxy-4-fluoro-ptienyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(2-melhoxy-acetylamino)-cyclohexyl]-amide; cis-{4-{[4-(2-Cyc!opropylmethoxy-4-fluoro-phenyl)-5H-pyrro!o[3,2-dlpyrimidine-7-carbonylI-amino}-cyc(ohexyl)-carbamic acid ethyl ester; trans-4-(2-Cyclopropylmethoxy.4-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartx)xylicacid (4-acetylannino-cyclohexyl)-arride; tran5-4-{2-Cyclopropy!methoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-dlpyrinnidine-7-carboxylic add [4-(2-methoxy-acetylarrino)-cyclohexyl]-amide; trans-(4-{[4-(2-Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartionyl]-amino}-cyclohexyl)-cart)arDic acid ethyl ester; 4-{2-Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-acetyl-piperidin-4-yl)-amideter;4-(2-Cyc!opropylmethoxy-4-fluoro-phenyl)-5H-pyrro!o[3,2-<: acid trans-4- pyrimidine-7-cartxjxylic trans->
acid ethyl ester; trans-4-{2-Cyclopropylnnethoxy-phenyl}-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(cyclopropanecarbonyl-annino)-cyclohexyl)-amide; 4-{2-Cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-cf]pyrimidine-7-carboxylic acid (1-acetyl-piperidin-4-yl)-amide; 4-{[4-(2-Cyclopropylmethoxy-phenyl)-5H-pyrroIo[3,2-d]pyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid ethyl ester; 4-(2-Cyclopropylmethioxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {1-cyclopropanecarbonyl-prperidin-4-yl)-arnide; 4-(2-Cyclopropylnnethioxy-4-fluoro-5-rnethoxy-ptienyl)-5H-pyrrolo[3,2-cf]pyrimidine-7-carboxylic acid (1 -propionyl-piperidin-4-yl)-amide; 4-(2-Cyclopropylmethoxy-4-fluoro-5-methioxy-ptienyl)-5H-pyrrolo[3,2-a']pyrimidine-7-carboxylic acid [1-(2-methoxy-ethianoyl)-piperidin-4-yl]-amide; 4-(2-Cyclopropylnfiethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrro)ot3,2-d]pyrimtdine-7-carboxy1ic acid (1-acety!-piperidtn-4-yl>amide; 4-(2-Cyclopropylmethoxy-4-fluoro-5-methoxy'phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {(R>-1-acetyl-ptperidin-3~yl)-annide;4-(2-Cyclopropylmethoxy-4-fli.ioro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ((R)-1-propionyl-piperidin-3-yi)-amide; 4-(2-Cyc!opropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrroloI3,2-d]pyrinnidine-7-carboxylic acid [{R)-1-(2-mettiaxy-acety|)-piperidin-3-yl]-amide; 4-(2-Cyc[opropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ((R)-1-acetyl-pyfrolidin-3-yl>-amide; 4-(2-Cyclopropylrrtethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyircacid ((R)-1-propiony(-pyrro[idin-3-yl)-amide; 4-(2-Cyclopropylmethoxy-4-fluQro-5-methoxy-pheny!)-5H-pyrrolo(3,2-af|pyrimidine-7-carboxylic acid [{R)-1-(2-methoxy-acetyl)-pyrrolidin-3~yll-amide; trans-4-(2-Cyclopropylnnettioxy-5-fluoro-4-methtoxy-phienyl)-5H-pyrrolo[3.2-d]pyrimidine-7-carboxylic acid (4-acetylamino-cyciotiexyl)-annide; trans-4-{2-Cyclopropylmethoxy-5-fluQro-4-methoxy-phenyl)-5H-pyrrolo[3,2-cy]pyrirnidine-7-carboxylic acid [4-(2-meltioxy-acetylamino)-cyclohexyl]-amide; 4-(2-Cyclopropylmettioxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-c/ipyrimidine-7-carboxylic acid (1-acetyl-piperidin-4-yl)-amide; 4-(2-Cyclopropylmethioxy-5-fiuoro-4-methoxy-phienyl)-5H-pyrrolo[3,2-c(|pyrimidine-7-carbDxylic acid [1-(2-methioxy-ethanoyl)-piperidin-4-yl]-amide; 4-(2-CycloprQpylmethoxv-5-fluoro-4-methoxy-phenyl)-5H-pyrrolot3,2-cOpyrimidine-7-carboxyficacid (1-propionyl-piperidin-4-yl)-amide; 4-(2-Cyclopropylmethoxy-5-nuoro-4-mettioxy-phenyl)-5H-pyrrolo[3,2-dlpyrirrii(jine-7-carboxylic acid ((R>-1-propionyl-piperidJn-3-yl>amide; 4-(2-Cyclopropylmethoxv-5-f)uoro-4-nnettioxy-phenyl)-5H-pyrroio[3,2-ci]pyrinnidine-7-carboxylic acid [(R)-1-(2-methoxy-ethanoyl)-piperidin-3-yl]-amide; 4-{2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ((R)-1-acetyl-piperidin-3-yl)-annide; 4-(2-Cyclopropy lmethoxy-5-fj uQro-4-m ethoxy-phe nyl)-5H-py rro lo[3,2-dlpy rim id I ne-7-carboxy I ic acid ((S)-1-propionyl-pJperidi^-3-yl).amide; 4-(2-Cyclopropylmethoxy-5-fJuoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-c(lpyrimi(3ine-7-carboxylic acid [(S)-1-(2-methoxy-ethanoyl)-piperidin-3-yl]-amide; 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylicacld ((S)-1 -acetyl-piperidIn-3-y|)-amide; 4-(2-cyclopropylmethoxy-5-fluoro-4-m ethoxy-phenyI)-5H-pyrrolo[3,2-dlpyrimic]ine-7-carboxylic acid ((R>-1-acety!-pyrrolidin-3-yl)-amide; 4-{2-Cyclopropy Imethoxy-5-fl uoro-4-m ethoxy-phe nyl)-5H-py rrolo[3,2-c(] py rim idi ne-7-ca rboxy lie acid ((R)-

1-propionyl-pyrrolidin-3-yl)-amide; 4-(2-Cyclopropylmethoxy-5-fluoro-4-nnethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid t(R)-1-(2-methoxy-acetyl)-pyrrolidin-3-yl]-amide; tran5-4-(2-Cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrrolo[3,2-d]pyrinnidine-7-carboxylic acid (4-acetylannino-cyclohexyl)-amide; trans-4-{2-Cyclopropylmefhoxy-5-methyl-phenyl)-5H-pyrrolo[3,2-c/]pyrimidine-7-carboxylic acid [4-(2-methoxy-acetylamino)-cyclohexyi]-amide; trans-{4-{[4-(2-Cyclopropylmethoxy-5-methyI-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-cyclohexyl)-carbamic acid ethyl ester; 4-{2-Cyctopropylmethoxy-5-methyl-phenyl)-5H-pyrrolo[3,2-a']pyr(mid(ne-7-carboxylic acid (1-acetyl-piperidin-4-yl)-amide; 4-(2-Cyclopropylmethoxy-5-fnethyl-phenyl)-5H-pyrro!o[3,2-d]pyrimidine-7-carboxylic acid [1-{2-methoxy-acetyl)-piperidin-4-yl]-amide; 4-{[4-{2-Cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrrolo[3,2-d)pyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid ethyl ester; trans-4-(5-Cyclobutylmethoxy-benzot1,3jdioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-acetylamino-cyclohexyl)-amide; trans-4-(5-Cyclobutylmettioxy-benzo[1,3]dioxoi-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(cyciopropanecarbonyl-amirto)-cyclohexylJ-amide; trans-4-(5-Cyclobufylmethoxy-benzo[1,3Jdfoxol-4-yl)-5/T'-pyrro!o[3,2-c/]pyrimidine-7-carboxylic acid [4-(2-methoxy-ethanoylamino)-cyclohexyl]-amide; 4-{5-Cyclobuty!mettioxy-benzo[1,3]dioxol-4-yt)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {1-acetyl-piperidin-*-yl)-amrde; 4-(5-Cyclobutylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrlmidine-7-carboxylic acid [1-(1-cycloprQpyi-methanoyl)-piperidin-4-yl]-amide; 4-{5-Cyclobutyimettioxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d)pyrimidine-7-carboxyiic acid [1-(2-methoxy-ethanoyi)-piperidin-4-yl]-amide; 4-({1-[4-(5-Cyclobutyimethoxy-benzo[1,3]dioxol-4-yi)-5H-pyrrolo[3,2-d]pyrim(d(n-7-yl]-rnethanoyl}-amino)-p(per(dine-1-carboxy/rc acid ethyl ester; 4-(5-Ethoxy-benzo[1,3]dioxoi-4-yl)-5H-pyrrolo[3,2-d]pyrinnidtne-7-carboxyiic acid (1-propionyl-piperidin-4-yl}-amide; 4-{[4-(5-Ethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid ethyl ester; 4--1-propionyi-pyrrolidin-3-yl)-amide; (R)-3-{[4-(5-Ethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrroIo[3,2-{:(]pyrimidine-7-carbonyl]-ai7i;no}-pyrrolidfne-1-carboxylic acid ethy} ester; 4-{5-Ethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1-(2-methoxy-acetyl)-pyrroiidin-amide; 4-(5-Propoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-propionyl-piperidin-4-yl}-amide; 4-{[4-(5-Propoxy-benzo[1,3]dk)xol-4-yi)-5H-pyrroio[3,2-d]pyrimidine-7-carbonyl]-annino}-pi peridine-1-carboxylic acid ethyl ester; 4-(5-Propoxy-benzo[1,3]dioxol-4-yl)-5H-pyrroio[3,2-d]pyrimidine-7-carboxylic acid ((R)-1-propionyl-pyrrolidin-3-yi}-amide; (R)-3-{[4-(5-Propoxy-benzo[1,3]dioxol-4-yi)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-annino}-pyrrolidine-1-carboxylic acid ethyl ester; 4-(5-Propoxy-benzof1,3]dioxo)-4-y))-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1-(2-methoxy-acetyi)-pyrrolidin-3-yl]-aniide; 4-(5-Butoxy-benzo[1,3IdioxaM-yl)-5H-pyrroto[3,2-d|pyrimidine-7-carboxylic acid (1-propionyl-piperidin-4-yl)-amide; 4-{[4-(5-Butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid ethyl ester; 4-(5-

Butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-formyl-piperidin-4-yl)-amide; 4-(5-Butoxy-benzon,3Jd(oxol-4-yl)-5H-pyrrolo[3,2-c(|pyrrmidine-7-carboxylic acid (1-propionyl-piperidin-3-yl)-amide; 3-{[4-(5-Butoxy-benzot1,3]dioxol-4-yl)-5H-pyrrolo(3,2-d]pyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid ethyl ester; 4-(5-Butoxy-benzo(1,3]dioxol-4-yl)-5H-pyrrolo[3,2-o]pyrimid(ne-7-carboxy(icacrd f1-(2-methoxy-acetyl)-p(peridrn-3-yl]-amrde;4-(5-Butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo(3,2-c(lpyrimidine-7-cartioxylic acid ({R)-1-propionyl-pyrrolidin-3-yl)-amide; {R)-3-{[4-(5-Butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbQnyl]-amino}-pyrro/tdine-1-carboxylic acid ethyl ester; cis-4-[4-Metfioxy-2-(2-methoxy-ethoxy)-pheny/]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid
trans-[4-{{1-[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxal-4-yl)-5H-pyrrolo[3..2-c/]pyrimidine-7-carboxylic acid [4-((S)-2-liydroxy-propanoylamino}-cyclohexyl]-amide; cis-[4-({1-[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl}-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-{2-hydroxy-ethanoylannino)-cyclohexyl]-amide; cis-[4-({1-[4-(5-CycIopropylnielhoxy-benzo[1,3]dioxol-4-yl )-5H-pyrrolo(3,2-c/| pyrimidine-7-carboxyIic acid [4-((S )-2-hydroxy-propanoylam ino)-cyclohexy!]-amide; 4-{5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyliG acid [1-((S)-2-hydroxy-propanoyl)-piperidin-4-yl]-amide; trans-4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-copyrinfiidine-7-carboxylic acid {4-[{1-lnydroxy-cyclopropanecarbonyl)-amino]-cydohexyl}-amide; cis-4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-y()-5H-pyrro(o[3,2-dlpyrimrdine-7-carboxylic acid {4-[(1-hydroxy-cyctopropanecarbonyl)-amino]-cyclohexyl}-annide; 4-{5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yt)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {1-[1-(1-hydroxy-cyclopropyl)-methancyl]-piperidin-4-yl}-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3Idioxol-4-yl)-5H-pyrrolo[3,2-djpyrimidine-7-carboxylic acid [(R)-1-(2-hydroxy-ethanoyl)-pyrrolidin-3-yl)-amide; 4-i5-Cyclopropylmethoxy-benzol 1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1-({S)-2-hydroxy-propanoyl)-pyrrolidin-3-yl]-amide; 4-(5-CyclopropyJmethoxy-benzo[1,3)dioxol-4-y!)-5H-pyrrolo[3,2--piperidin-4-ylmethyl]-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrro \o[3,2-d\ py rim id ine-7-carboxy I icacid{1-[1-{1 -inyd roxy-cyclopro py t)-m etiianoy l)-pi perid in-4-ylmethyl}-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dloxo!-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-hydrQxy-acetyl)-piperidin-3-ylmetliylI-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl}-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-((S)-2-hydroxy-propionyl)-piperidin-3-ylm6tliyl]-annide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxo!-4-yl)-5H-pyrrolo[3,2-d]pyrimidJne-7-carboxylic acid [1-(2-hydroxy-acetyl)-pyrrolidin-3-ylmethyl]-amide; 4-(5-Cyc!opropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-({S)-2-hydroxy-propionyl)-pyrroltdin-3-ylmethyl]-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(2-hydroxy-acetyl)-morpholin-2-ylmethyl]-amide; 4-(5-Cyc(opropy(methoxy-benzo[1,3]dioxo(-4-y(}-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic ac[d [4-((S)-2-hydroxy-propionyl)-morpliolin-2-ylmethyl]-amide; 4-{5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyiic acid [1-(2-hydroxy-ethanoyl)-azetidin-3-yl]-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-((S)-2-

hydroxy-propanoyl)-azetidin-3-yl]-amide; 4-(5-Cyclopropy!methoxy-benzo[1,3]dioxoi-4-y))-5H-pyrrolo[3,2-d]pyrimldine-7-carboxylic acid [(S)-1-((S)-2-hydroxy-propanoyl)-piperidin-3-yl]-annide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-dlpyrimidine-7-carboxylic acid [(R)-1-((S)-2-hydroxy-propanoyl)-piperidin-3-yl]-annide; trans-4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyJic acid [4-(2-hydroxy-acetylamino)-cyclohexyl]-amide; trans-4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrro!o[3,2-dtpyrinnidine-7-carboxylic acid [4-((S)-2-liydroxy-propionylamino)-cyclohexyl]-amide; trans-4-(2-Cyclopropylmethoxy-4-methoxy-plienyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4-[(1-liydroxy-cyclopropanecarbonyl)-amino]-cyclohexyl}-amide; cis-4-(2-Cyclopropylmetiioxy-4-nnethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(2-hydroxy-acetylainino)-cyclohexyl]-amide; cis-4-(2-Cyciopropylmethoxy-4-meHioxy-ph6nyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-((S)-2-hydroxy-propionylamino)-cyctohexyl]-annide; cis-4-(2-cyclopropylmethoxy-4-fnethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyl!cacid {4-[(1-hydroxy-cyclopropanecarbonyl)-amino]-cyclohexyl}-amide; 4-(2-cyclopropylmethoxy-4-methoxy-phenyl)-5Hpyrrolo[3-2-d]pyrimidine-7-carboxylic acid [1-(2-hydroxy-ethanoyl)-piperidin-4-yl]-aniide; 4-(2-Cyc!opropylmethoxy-4-mettioxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-({S}-2-hydroxy-propanoyl)-piperidin-4-yl]-atnide; 4-{2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {1-[1-{1-hydroxy-cyclopropyl)-methanoyl]-piperidin-4-yl}-amide; cis-4-{2-Cyciopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-c/lpyr(niidine-7-carboxylic acid [4-(2-hydrQxy-acetylamino)-cyclohexyl]-amide; cis-4-{2-Cyclopropylmethoxy-5-nnethoxy-piiehyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4-[(1-hydroxy-cyclopropanecarbonyl)-amino]-cyclohexyl}-amide; trans-4-(2-cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-c^pyrimic|ine-7-carboxylic acid {4-[{1-hydroxy-cyclopropanecarbonyl)-amino]-cyclohexyl}-amide; 4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-hydroxy-acetyl)-piperidin-4-yl]-amide; 4-(2-Cyclopropylmethoxy-5-methoxy-phenyi)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1 -({S)-2-hydroxy-propionyi)-piperidln-4-yl]-amide;4-(2-cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo(3,2-d]pyrim/d(ne-7-carboxylic acid [1 -(1 -hydroxy-cyclopropanecarbonyl)-pfperidin-4-ylJ-amide; cis-4-(2-Cyclopropylnnethoxy-4-fluoro-plienyl)-5H-pyrrolo[3,2-d]pyrinnidine-7-carboxylic acid [4-{2-hydroxy-acetylamino)-cyclohexyl]-amide; cis-4-{2-Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-((S)-2-hydroxy-propionylamino)-cyclohexyl]-amide; cis-4-(2-Cyclopropylmethoxy-4-fluofo-phenyl)-5H-pyrrolo[3,2-c/lpyrirTiidine-7-carboxylic acid {4-[(1 -hydroxy-cyclopropanecarbonyl)-amino)-cyclohexyi}-amide; transv4-(2-Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-c(]pyrimid!ne-7-carboxylic acid [4-(2-hydroxy-acetylamino)-cyciQhexyl]-amide; trans-4-(2-Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrroio[3,2-d]pyrimidine-7-carboxylic acid [4-{{ S)-2-hyd roxy-propiony I am i no)-cyclohexy l]-am ide; tra ns-4-(2-Cy clopropy I methoxy-4-flu oro-phenyl)-5H-pyrrolo[3,2-cf]pyrimidine-7-carboxylic acid {4-[{1-liydroxy-cyclopropanecarbonyl)-annino]-cyclohexyl}-amide; 4-{2-Cyclopropylniethoxy-5-fIuoro-ph6nyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-hydroxy-acetyl)-piperidin-4-yl]-amide; 4-(2-Cyclopropylmethioxy-5-fluoro-

phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid l1-{(S)-2-hydroxy-propionyl)-piperidin-4-yl]-amide; trans-4-(2-Cyclopropylmethoxy-5-ftuoro-phenyl)-5H-pyrrolo[3,2-clpyrimidine-7-carboxylic acid [4-(2-hydroxy-acetylamino}-cyclohexyl]-amide; trans-4-(2-Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-c^pyrimidme-7-carboxylic acid [4-((S)-2-hydrcixy-propionylamino)-cyclohexy\]-ami(ie; trans-4-(2'Cydopropylmethoxy-pheny\y5H'Pyrrolo[3,2-cflpyhmidine-7-c3rboxylic acid [4-(2-hydroxy-acetylamino)-cyclahexyl]-amide; trans-4-(2-Cyctopropylmethoxy-phenyl)-5H-pyrrolo(3,2-cf|pyrimidine-7-carboxylic acid [4-((S)-2-hydroxy-propionylamino)-cycIohexyl]-annide; trans-4-(2-Cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-c(ipyrimidine-7-carboxylic acid {4-[{1-hydroxy-cyclopropanecarbonyl)-amino]-cyclohexyl}-amide; 4-{2-Cyclopropylnnethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [ 1 -((S)-2-hydroxy-propionyi)-piperidin-4-yl]-amide; 4-(2-Cyclopropylmethoxy-4-fluoro-5-methoxy-plienyl)-5H-pyrrolc[3,2-d]pyrimidine-7-carboxylic acid [1-((S)-2-hydroxy-propionyl)-piperidin-4-yl]-amide; 4-(2-Cyc!opropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1-C2-hydroxy-acety!)-pJperidin-3-yl]-amicle; 4-(2-CyclopropylmeihDxy-4'fSuoro-5-meiboxy-phenyl)-5H-pyirolol3,2-cfjpynmi6ine-7-carboxylic acid [(R)-1-{(S)-2-hydroxy-propionyl)-piperidin-3-yl]-amide; 4-{2-Cyclopropylmethoxy-4-fluoro-5-nnethoxy-phenyt)-5H-pyrro[o[3,2-d]pyrimidine-7-carboxylic acid [{R)-1-(2-hydroxy-acetyl)-pyrrolid(n-3-yl]-amide; 4-(2-Cyclopropylmethoxy-4-fluoro-5-methDxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1-((S)-2-liydroxy-propionyl)-pyrrolidin-3-yl]-amide; trans-4-(2-Cy clopropy tmethoxy-5-f I uoro-4-nn ethoxy-pheny I )-5H-pyrrolo[3,2-d] pyrim idi ne-7-ca rboxy I ic acid [4-(2-hydroxy-acetylamino)-cyclohexyl]-amide; trans-4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrola[3,2-d]pyrimidirre-7-carboxylic acid [4-((S)-2-hydroxy-propionylamino)-cyclohexyt]-amide; trans-4-{2-CyclopropyJnfiethoxy-5-fluoro-4-m6thoxy-plienyl)-5H-pyrrolo[3,2-d)pyrimidine-7-carboxylic acid {4-[{1-hydroxy-cyc!opropanecarbonyl)-amino]-cyclohexyl}-amide; 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl}-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-liydroxy-ethanoyl)-piperidJn-4-yl]-amide; 4-(2-Cyclopropylmetlnoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrro!o[3,2-d]pyrimidine-7-carboxylic acid [1-{(S)-2-hydroxy-propanoyl)-piperidin-4-yl]-amide; 4-{2-Cyclopropylmethoxy-5-fIuoro-4-melhoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {1-[1-(1-hydroxy-cyclopropyl)-fnethanoyl]-pipBridin-4-yl}-aniide; 4-(2-cyclopropylmethoxy-5-fiuoro4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carlx>xylicacid [(S)-1-((S)-2-hydroxy-propanoyl>-piperidin-3-yl]-amide; 4-{2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo{3,2-c(]pyrinfiidine-7-carboxylic acid [(R)-1-({S)~2-hydroxy-propanoyl)-piperidin-3-y l]-am ide; 4-(2-Cyclopropy I methoxy-5-flu oro-4-met lioxy-pheny l)-5H-py rrolo(3,2-d\ pyrim id i ne-7-carboxylic acid [(R)-1-(2-hydroxy-acetyl)-pyrrolidin-3-yl]-amide; 4-(2-Cyclopropylmethoxy-5-flLioro-4-methoxy-phenyl)-5H-pyrrolo[3,2-c(lpyrinnidine-7-carboxylic acid [(R)-1-((S)-2-hydroxy-propionyl)-pyrrolidin-3-yl]-amide; trans-4-(2-Cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrrolo(3.2-c(]pyrimidine-7-carboxylic acid [4-(2-hydroxy-acety1amino)-cyclohexyl)-aniide; trans-4-(2-Cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-((S)-2-hydroxy-propionylamino)-cyclohexyl]-amide; trans-4-(2-Cyclopropylmethoxy-5-methyl-phenyl)-5H-

pyrroto[3,2-d]pyrimidine-7-carboxylic acid {4-[(1-hydroxy-cyclopropanecarbonyl)-amino]-cyclohexyl}-amide;4--benzo[1,3]dioxol-4-yl]-5H-pyrraio[3,2-<: acid cis-4- trans-4- tran5-4->
cyclopropylcafbamoyl-cycloti8xyl)-aniide; trans-4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimtdJne-7-carboxylic acid (4-cyclopropylcarbamoyl-cyclohexyl)-amide; trans-4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(2-methoxy-etlnylcarbamoyl)-cyclohexyl]-amide; trans-4-{2-Cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrlmldine-7-carboxylic acid (4-cyclopropylcarbamoyl-cyclohexyl)-annide; trans-4-(2-Cyclo propy Im ethoxy-5-flu oro-phe ny I )-5H- py rrolo[3,2-d]py rim id i ne-7-carboxy lie acid [4-{2-m et lioxy-ethylcarbamoyl)-cyclohexyl]-anfiide; trans-4-(5-Cyclobutylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-t/]pyrimidine-7-carboxylic acid (4-(2-methoxy-ethylcarbamoyl)-cyclohexyl]-annide: trans-4-(5-Cyclobutylmethoxy-benzo[1,3]dioxol-4-yl}-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-cyclopropylcarbamoyl-cydohexyl)-amtde; a salt thereof, or a stereoisomer of the compound or the salt thereof.
It is to be understood that the invention covers all combinations of substituent groups referred to hereinatiove. In particular, the invention covers all combinations of preferred groups described hereinabove.
Salts of the compounds according to the invention and the stereoisomers thereof include alf inorganic and organic acid addition salts and salts with bases, especially all pharmaceutically acceptable inorganic and organic acid addition sails and salts with bases, particularly al! pharmaceutically acceptable inorganic and organic acid addition salts and salts with bases customarily used in pharmacy.
Examples of acid addition salts include, but are not limited to, hydrochlorides, hydrobromides, phosphates, nitrates, sulfates, acetates, trifluoroacetates, citrates, gluconates including D-gluconates and L-gluconates, glucuronates including D-glucuronates and L-glucuronates, benzoates, 2-(4-hydroxyben2oyl)benzoates, butyrates, salicylates, sulfosalicylates, maleates, laurates, malates including L-malates and D-malates, lactates.including L-lactates and D-lactates, fumarates, succinates, oxalates, tartarates including L-tartarates, D-tartarates and meso-tartarates, stearates, benzenesuHbnates (besilates), toluenesulfonates (tosilates), methanesulfonates (mesilates), laurylsulfonates, 3-hydroxy-2-naphthoates, lactobionates (salts of 4-0-beta-D-galactopyranosyl-D-gluconic acid), galactarates, embonates and ascorbates.
Examples of salts with biases include, but are not limited to, lithium, sodium, potassium, calcium, aluminum, magnesium, titanium, ammonium, meglumine and guanidinium salts.
The salts include water-insoluble and, particularly, water-soluble salts.

The compounds according to the invention, the salts thereof, the N-oxides of the compounds and the salts thereof and the stereoisomers of the compounds, salts, N-oxides of the compounds and N-oxides of the salts thereof may contain, e.g. when isolated in crystalline form, varying amounts of solvents. Included within the scope of the invention are, therefore, all solvates of the compounds of formula (I), the salts thereof, the N-oxides of the compounds and the salts thereof and the stereoisomers of the compounds, salts, N-oxides of the compounds and N-oxides of the salts thereof. Hydrates are a preferred example of said solvates.
The compounds according to the invention and the salts thereof, the N-oxides of the compounds and the salts thereof include stereoisomers.

Examples of stereoisomers include, but are not limited to, compounds of formula (I) wherein R3 is a 3-6C-cycloalkyl group substituted by R6. Stereoisomers of one exemplified compound of formula ()) wherein R3 is a 3-6C-cyc}oalky} group substituted by R6 are shown below (cisJtrans stereoisomers):

R23
-R6 R6

Further examples of stereoisomers include, but are not limited to, compounds of formula (I) wherein R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4 and wherein said heterocydic ring contains a stereogenic center. Stereoisomers of an exemplified compound of formula (I) wherein R3 is a 4- to 7-membered saturated heterocydic ring containing one nitrogen atom and optionally one oxygen atom, said heterocydic ring being optionally substituted by R4 and said heterocyclic ring containing a stereogenic center are shown below:

N —R4
R1


r"- ^
^\^ N
H
-°^ f\ ^R21
R24 R23 R22

N—R4
(Ic)

R1


1 ^
^^'^ y
N. ^ H
-^Yl _^R21
R24^'^ '^R22
R23

(Id)

Stereoisomers of a further exemplified compound of formula (1) wherein R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4 and said heterocyclic ring containing a stereogenic center are shown below:




N—R4
rY^
\ N—R4
(le)

Stereoisomers of a further exemplified compound of formula (I) wherein R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4 and said heterocyclic ring containing a stereogenic center are shown below:


N —R4
R1



"^^^^ "N
H
/O^ r^ R21
824-"^^^ R22
R23

O

N —R4
Oh)

Further examples of stereoisomers include, but are not limited to, compounds of formula (I) wherein R4 is a group having a stereogenic center, such as a group -C(O)-CH(CH3)-0H. Further examples of stereoisomers include, but are not limited to, compounds of formula (I) wherein R6 is a group having a stereogenic center, such as a group -NH-C(O)-CH{CH3)-OCH3.
Each of said stereogenic centers may have the absolute configuration R or the absolute configuration S (according (o (he rufes of Cahn, Ingold and PrefogJ.
The invention relates to the pure stereoisomers and to mixtures of the stereoisomers independent of the ratio, including the racemates. Accordingly, the invention relates to the pure (cis)-isomers, the pure (trans)-isomers, and mixtures thereof, the pure (R)-jsomers, the pure (S)-isomers, and mixtures thereof.
Furthermore, the invention indudes the pure (trans,R)-isomers, (trans,S)-isomers, (cis,R)-isomers and (cis,S)-isomers, and mixtures of two or more thereof in any ratio. An example of said isomers is shown below:



■ OH



(trans,S)

(trans,R)


OH

(cis.R)
,.,.0H

Furthermore, the invention includes the pure {R,R)-lsomers, (R,S)-isomers, (S,R}-isomers and (S,S)-isomers, and mixtures of two or more thereof in any ratio. An example of said isomers is shown below:

H R
R1—O
R24
(R.SJ
R23 R22

R23 R22









OH
R1—O
R1 —O
R24
R2')
R23 R22

R23 R22

A = -CH2- or -O-i = 0, 1 or2
Furthermore, derivatives of the compounds according to the invention, the salts thereof, the N-oxides of the compounds or the salts thereof, the stereoisomers of the compounds, salts, N-oxides of the compounds or N-oxides of the salts thereof which are converted into compounds according to the invention, the salts thereof, an N-oxide of the compound or the salt thereof, the stereoisomers of the compounds, the salt, the N-oxide of the compound or the N-oxide of the salt thereof in a biological system (bioprecursors or pro-drugs) are covered by the invention. Said biological system is e.g. a mammalian organism, particularly a human subject. The bioprecursor is, for example, converted into the compounds according to the invention, the salts thereof, an N-oxide of the compound or the salt thereof, or a stereoisomers of the compounds, the salt, the N-oxide of the compound or the N-oxide of the salt thereof by metabolic processes.
The compounds according to the invention can be prepared as follows.


H^N
\^0
NOT"
o
(1-1)

r
o
(1-2)

(1-3)







(1-4)

m

Reaction scheme 1
The compound of fonriuia (1) can be obtained as shown in reaction scheme 1 according to the procedures described in US 2005/0124623A1,

HOv, R23 (11) .-0
R24 Y^R22 R23
(12) RaO ,ORb
R24'


R24"'y'^R22 R23
(2)
Reaction scheme 2
As shown in reaction scheme 2, synthesis of a troronic acid derivative of formula (2) may start from phenols of formula (11) wherein R21, R22, R23 and R24 have the above defined meanings. The phenols of formula (11) are commercially available or can be prepared by methods known to a person skilled in the art. in a first step R1, which has the atrave defined meaning, may be introduced by alkylation. The alkylation is for example carried out by suspending sodium hydride in an organic solvent, such as dimethylethane (DME) or dimethylsulfoxide (DMSO) or a mixture thereof, adding a solution of compound (11) in an organic solvent, such as DME, at a temperature in the range of from 0 to 40°C, then adding a compound Rl-halogen, preferably Rl-Br or R1-I, and reacting the mixture at a temperature of from 20 to 80°C for 1 to 48 h to give a compound of

formula (12). In a second step, directed orthometalation followed by reaction with a boron electrophile leads to the compounds of formula (2) wherein R1, R21, R22, R23 and R24 have the above defined meanings, and Ra and Rb represent 1-4C-alkyl or hydrogen, preferably Ra and Rb combine to form a straight-chain or branched alkylene group having 2 to 8 carbon atoms, for example without limitation -C(CH3)2-C(CH3)2-. In particular, a solution of compound (12) in an organic solvent, such as tetrahydrofuran (THF), can be reacted with n-butyl lithium (n-BuLi) in an organic solvent, such as hexane, at a temperature of from -78 to 0°C for 0.5 to 4 h. Subsequently, for example commercially available 2-iso-propoxy-4,4,5,5-tetramethyl-[1,3,2]dioxaborGlane is added and the reaction is performed at a temperature of from -7S to 0°C for 0.5 to 3 h to yield a compound of formula (2).

Br
H0^.,--^^R21 H0,J-;;^R21
R24''Y^^'^R22 ^ R24'Y^R22
R23 R23


Br
R1'^- A.R.1
R24 V"RZ2
R23

(11) (13) (14)

RaO. ,ORb
B
R1
^0^4,^ R21
R24'Y''^R22 R23
(2)

Reaction scheme 3
An alternative preparation of compounds of formula (2) is shown in reaction scheme 3. The preparation may start from phenols of formula (11), wherein R21, R22, R23 and R24 have the above defined meanings and which are commercially available or can be prepared by methods known to a person skilled in the art or as for example described in Yamamoto, Y.; Hattori, K.; Ishii, J.-l.; Nishiyama, H. Tetrahedron, 2006, 62, 4294. The phenols of formula (11) are for example reacted with bromine or N-bromosuccinimide in an organic solvent such as dichtoromethane (DCM) at a temperature of from -40 to 20°C for 0.5 to 4 h to give compounds of formula (13). In a second step R1, which has the above defined meaning, may be introduced by alkylation. The alkylation is for example carried out by suspending sodium hydride in an organic solvent, such as dimethylethane (DME) or dimethylsulfoxide (DMSO) or a mixture thereof, adding a solution of

compound (13) in an organic solvent, such as DME, at a temperature in the range of from 0 to 40°C, then adding a compound R1-halagen, preferably Rl-Br or R1-L and reacting the mixture at a temperature of from 20 to 80°C for 1 to 48 h leading to compounds of formula (14). In a third step, halogen-lithium exchange followed by reaction with a ttoron elecfrophile yields the compounds of formula (2), wherein R1, R21, R22, R23 and R24 have the above defined meanings, and Ra and Rb represent 1-4C-alkyl or hydrogen, preferably Ra and Rb combine to form a straight-chain or branched alkylene group having 2 to 8 carbon atoms, for example without limitation -C(CH3)2-C(CH3)2-. In particular, a solution of compound (14) in an organic solvent, such as tert-butylmethytether, can be reacted with n-BuLi (n-butyl lithium) in an organic solvertt, such as hexane, at a temperature of from -78 to 0°C for 0,5 to 3 h. Subsequently, for example commercially available 2-iso-propoxy-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane is added and the reaction is performed at a temperature of from -78 to 0°C for 0.5 to 3 h to yield a compound of formula (2).
Br
'^TTT'' Rr°YY^' '''TV''
R24"'Y'^'^R22 ^ R24''Y^'^R22 R24''y^'^R22
R23 R23 R23

(11)

(12) (14)



R1

RaO. ,ORb
B
,0.A^R21
R23 (2)

Reaction scheme 4
According to a further alternative preparation method shown in reaction scheme 4, synthesis of bioronic acid derivatives of formula (2) may start from phenols of formula (11) wherein R21, R22, R23 and R24 have the above defined meanings and which are commercially available or can be prepared by methods known to a person skilled in the art. In a first step R1, which has the above defined meaning, is introduced by alkylation. The alkytation is for example carried out by suspending sodium hydride in an organic solvent, such as dimethylethane (DME) or dimethylsulfoxide (DMSO) or a mixture thereof, adding a solution of compound (11) in an organic solvent, such as DME, at a temperature in the range of from 0 to 40°C, then adding a compound Rl-halogen, preferably Rl-Br or R1-I, and reacting the mixture at a temperature of from 20 to 80°C

for 1 to 48 h to give a compound of formula (12). In a second step, compound (14) may be prepared for example from compound (12) by reaction with N-bromosuccinimide in an organic solvent, such as dimethylformamide, at a temperature of from 0 to eCC for 0.5 to 5 h. In a third step, halogen-lithium exchange followed by reaction with a boron electrophile yields the compounds of formula (2), wherein R1, R21, R22, R23 and R24 have the above defined meanings, and Ra and Rb represent 1-4C-alkyl or hydrogen, preferably Ra and Rb combine to form a straight-chain or branched alkylene group having 2 to 8 carbon atoms, for example without limitation -C(CH3)2-C(CH3)2-. In particular, a solution of compound (14) in an organic solvent, such as tert-butylmethylether, can be reacted with n-BuLi (n-buty) lithium) in an organic solvent, such as hexane, at a temperature of from -78 to 0°C for 0.5 to 3 h. Subsequently, for example commercially available 2-iso-propoxy-4,4,5,5-tetrarinethyl-[1,3,2]dioxaboro!ane is added and the reaction is performed at a temperature of from -78 to 0°C for 0.5 to 3 h to yield a compound of formula (2). Alternatively, compounds of formula (2) may be synthesized from compounds of formula (14) and. an appropriate boron compound, such as bis(pinacolato)diboron, in the presence of a Pd catalyst, such as 1,1'-bis{diphenyl-phosphino)ferrocene palladium-{ll)-chloride, and a base, such as potassium acetate, in an organic solvent, such as dioxane, at a temperature of from 20 to lOO^C for 1 to 24 h. The Pd catalyzed preparation of boronic acid derivatives is. for example, described In Murata et al, J Org Chem 2000, 65, 6458 and J Org Chem 1997, 52, 164.


R24
(1)

RaO, ,ORb B
R24^'Y*'^R22 R23
(2)

R23

R22

(3)



R24
R23

R22

(4)

Reaction scheme 5
Reaction scheme 5 illustrates the synthesis of compounds of formula (4) in which R1, R21, R22, R23 and R24 have the above defined meanings. In a first step, compound (1) prepared according to reaction scheme 1 can be reacted with a compound of formula (2) prepared according to any of reaction scheme 2, 3 or 4, wherein R1, R21, R22, R23, R24, Ra and Rb have the above defined meanings, to otjtain a compound of formula (3). In particular, the compound of formula (1), a base, such as K2C03, CsjCOs or K3PO4, a solvent, such as dimethoxyethane, and a Pd catalyst, such as PdCl2(PCy3)5 (Cy = cyclohexyl), are preferably heated at a temperature in the range of from 60 to 160°C for 5 to 10 min, more preferably under microwave irradiation. After cooling to ambient temperature (e.g. 20 to 25°C), a compound of formula (2) can be added to the reaction mixture which is then preferably heated to a temperature in the range of from 60 to 160°C for 10 to 120 min, more preferably under microwave irradiation. The compound of formula (3) thus obtained can then be reacted with an alkali hydroxide, such as LiOH, in a solvent, preferably a mixture of an organic solvent, such as dioxane, and water, at a temperature in the range of from 20 to 100°C for 1 to 48 h to yield a compound of formula (4).

N'^^^RS—R4 H

R23

R22

(5)
H2N-Y-R3-R4

R23

R22



(4)

(1-1)

Reaction scheme 6
As shown in reaction scheme 6, starting from compounds of formula (4) prepared according to atMve reaction scheme 5, compounds of formula (1-1), wherein R1, R21, R22, R23, R24 and Y have the above defined meanings and R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and optionally one oxygen atom, said heterocyclic ring being substituted by R4 with R4 being -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the MC-alkyl group is optionally substituted by R43, with R41, R42 and R43 having the above defined meanings, can be prepared by reaction with compounds of formula (5), wherein Y has the above defined meaning and R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and optionally one oxygen atom, said heterocyclic ring being substituted by R4 with R4 being -C(O)-1-4C-alkyl. wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3~6C-cycloalkyl, wherein the 3-6C-cycloalkyl

group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, with R41, R42 and R43 having the above defined meanings, under standard amide lx)nd forming conditions. The compounds of formula (5) are commercially available or can be prepared by methods known to a person skilled in the art. An exemplified method for preparing compounds of formula (5) is shown in reaction scheme 15 below. In particular, a dehydrating agent, such as 1-(3-dimethylaminopropyl)-3'ethylcarbodiimide hydrochloride, a base, such as triethylamine, and a catalyst, such as l-hydroxybenzotriazole, can be added to a compound of formula (4) which is preferably dissolved or suspended in an organic solvent, e.g. dichloromethane. After stirring the mixture e.g. for 0.3 to 2 h, preferably at ambient temperature (e.g. 20 to 25°C), a compound of formula (5) can be added and the reaction is preferably performed at ambient temperature (e.g. 20 to 25°C) for 1 to 48 h to yield the compound of formula (1-1).

(6)
O!^ H2N-Y-R3-R6-R7

R23

R22
W

Y—R3 —R6-R7

(1.2)
Reaction scheme 7
As shown in reaction scheme 7, compounds of formula (1-2), wherein R1, R21, R22, R23, R24 and Y have the alxjve defined meanings and R3 is a 3-6C-cycloalkyl group substituted by R6, with R6 being -NH-C(O)R7 and R7 being 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, with R71, R72 and R73 having the alx)ve defined meanings, can be synthesized by reaction of compounds of formula (4) prepared according to above reaction scheme 5, with compounds of fomnula (6), wherein Y has the above defined meaning and R3 is a 3-6C-cyclQalkyl group substituted by R6, with R6 being -NH-C(O)-R7 and R7 being 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, which is optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, with R71, R72 and R73 having the above defined meanings. The compounds of formula (6) are commercially available or can be prepared by methods known to a person skilled in the art. In particular, a dehydrating agent, such as 1-(3-dimethylaminopropyl)-3-

ethylcarbodiimide hydrochloride, a base, such as triethylamine, and a catalyst, such as 1-hydroxybenzotriazole, can be added to a compound of formula (4) which is preferably dissolved or suspended in an organic solvent, such as dichloromethane. After stirring the mixture e.g. for 0.3 to 2 h preferably at ambient temperature (e.g. 20 to 25'C), a compound of formula (6) can be added and the reaction is preferably performed at ambient temperature (e.g. 20 to 25°C) for 1 to 48 h to yield the compound of formula (1-2).



Y—R3—R4
+ HCI

(1-3)

(M)

Reaction scheme 8
Compounds of fomnuia (1-3), wherein R1, R21, R22, R23, R24 and Y have the above defined meanings and R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and optionally one oxygen atom, said heterocyclic ring being substituted by R4 with R4 being -C(O)-O-C(CH3)3, prepared according to reaction scheme 6 can be converted into compounds of formula (1-4), wherein R1, R21, R22, R23, R24 and Y have the above defined meanings and R3 is a non-substituted 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and optionally one oxygen atom, as shown in reaction scheme 8. )n particular, HO preferably dissolved in an organic solvent, such as dioxane, can be added to the compound of formula (1-3) which is preferably dissolved in an organic solvent, such as an alcohol, e.g. 2-propanol. The reaction mixture is then preferably heated at 40 to 80°C for 1 to 4 h to yield the hydrochloride of the compound of formula (1-4). The compound of formula (1-4) can be prepared from said hydrochloride as known to a person skilled in the art, such as by treatment with a base, e.g. aqueous potassium cartwnate or aqueous ammonia.



O /Y—R3—R6-R7
N H
+ HCI

Y—R3—R6



(1-5)

(1-6)

Reaction scheme 9
Compounds of formula (1-5), wherein R1, R21, R22, R23, R24 and Y have the above defined meanings and R3 is a 3-6C-cycloalkyl group substituted by R6 with R6 being -NH-C(O)-R7 and R7 being -O-C(CH3)3, prepared according to reaction scheme 7 can be converted into compounds of formula (1-6), wherein R1, R21, R22, R23, R24 and Y have the above defined meanings and R3 is a 3-6C-cycloalkyl group substituted by R6 with R6 being -NH2 as shown in reaction scheme 9, In particular, HCI preferably dissolved in an organic solvent, such as dioxane, can be added to the compound of formula (1-5) which is preferably dissolved in an organic solvent, such as an alcohol, e.g. 2-propano). The reaction mixture is then preferably heated at 40 to 80°C for 1 to 4 h to yield the hydrochloride of the compound of formula (1-6). The compound of formula (1-6) can be prepared from said hydrochloride as known to a person skilled in the art, such as by treatment with a base, e.g. aqueous potassium carbonate or aqueous ammonia.



R4-CI

(1-4)

(1-1)

Reaction schieme 10
Alternatively, as shiown in reaction schieme 10, compounds of formula (1-1), wherein R1, R21, R22, R23, R24 and Y have the above defined meanings and R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and optionaily one oxygen atom, with R4 being -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionaliy substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1~4C-alkyi group is optionally substituted by R43, and R41, R42 and R43 are as defined above, may be prepared from compounds of formula (J-4), wherein R1, R21, R22, R23, R24 and Y have the above defined meanings and R3 is a non-substituted 4- to 7-memberGd saturated heterocyclic ring containing one nitrogen atom and optionally one oxygen atom prepared according to reaction scheme 8. In particular, a compound R4-CI can be added to the compound of formula (1-4) which is preferably dissolved in an organic solvent, such as dichloromethane, in the presence of a base, such as diazabicycloundecene (DBU). The compound of formula R4-CI is commercially available or can be prepared by methods known to a person skilled in the art. The addition is preferably carried out at a temperature of from 0 to 20*0. After complete addition, the reaction is preferably continued at ambient temperature (e.g. 20 to25°C)for 1 to 24 h. In case R41, R42 or R43 represent hydroxy, it is known to a person skilled in the art that the hydroxy group is preferably to be protected by a suitable protecting group, such as an acetate group or a silyl protective group, e.g. a tert-butyl-dimethylsilyl group or a tert-butyl-diphenylsilyl group. Said protective groups can be removed by methods known to a person skilled in the art with or without prior rsofation of the protected tntermedrate (r.e. the compound of formufa (1-1) in its protected form).


O ,Y—R3 —R6

Cr R7

Q ^Y—R3—R6-R7
N H



{(-6)

(1-2}

Reaction scheme 11
Alternatively, as shown in reaction scheme 11, compounds of formula (1-2), wherein R1, R21, R22, R23, R24 and Y have the above defined meanings and R3 is a 3-6C-cycloalkyl group substituted by R6, with R6 being -NH-C(O)-R7, with R7 being 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycloalkyI, which is optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, and R71, R72 and R73 are as defined above, may be prepared from compounds of formula (1-6), wherein R1, R21, R22, R23, R24 and Y have the above defined meanings and R3 is a 3-6C-cycloalkyl group substituted by Ro with R6 being NH2 prepared according to reaction scheme 9. In particular, a compound R7-C(O)-CI can be added to the compound of formula (1-6) which is preferably dissolved in an organic solvent, such as dichloromethane, in the presence of a base, such as diazabicycloundecene (DBU). The compound of formula R7-C(O)-CI is commercially available or can be prepared by methods known to a person skilled in the art. The addition is preferably carried out at a temperature of from 0 to 20°C. After complete addition, the reaction is preferably continued at ambient temperature (e.g. 20 to 25°C) for 1 to 24 h to yield the compound of formula (1-2). In case R71, R72 or R73 represent hydroxy, it is known to a person skilled in the art that the hydroxy group is preferably to be protected by a suitable protecting group, such as an acetate group or a silyl protective group, e.g. a tert-butyl-dtmethylsilyl group ortert-butyl-diphenylsilyl group. Said protective groups can be removed by methods known to a person skilled in the art with or without prior isolation of the protected intermediate (i.e. the compound of formula (1-2) in its protected form).



O
A
Y—R3
H,C OR4

Y—R3 —R4



(W)

(1-7)

Reaction scheme 12
As shown in reaction scheme 12, compounds of formula (1-7), wherein R1, R21, R22, R23, R24 and Y have the above defined meanings and R3 is a 4- to 7-mennbered saturated heterocyclic ring

containing one nitrogen atom and optionally one oxygen atom, said heterocyclic ring being substituted by R4, with R4 being -C(O)-H can be prepared from compounds of fonriula (1-4), wherein R1, R21, R22, R23, R24 and Y have the above defined meanings and R3 is a non-substituted 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and optionally one oxygen atom prepared according to reaction scheme 8. In particular, the compound R4-0-C(O)-CH3, which can be prepared by methods l


H3C, O
R7



'-R3'^^-R7



(1-6)

(l-B)

Reaction scheme 13
As shown in reaction scheme 13, compounds of fomnula (i-8), wherein R1, R21, R22, R23, R24 and Y have the above defined meanings and R3 is a 3-6C-cycloalkyl group substituted by R6 with R6 being -NH-C(O)-R7 with R7 being hydrogen can be prepared from compounds of formula (1-6), wherein R1, R21, R22, R23, R24 and Y have the above defined meanings and R3 is a 3-6C-cycloafkyl group substituted by R6 with R6 being -NH2, obtained according to reaction scheme 9. In particular, the compound R7-C(O)-O-C(O)-CH3 with R7 being hydrogen, which can be prepared by methods known to a person skilled in the art, can be added to the compound of formula (1-6) which is preferably dissolved in an organic solvent, such as dichloromethane, in the presence of a base, such as diazab'icydoundecens (DBU). The addition is preferably carried out at a temperature of from 0 to 20°C. After completion of addition, the reaction is preferably continued at ambient temperature (e.g. 20 to 25°C) for 1 to 24 h to yield a compound of formula (1-8).


(7)
OH H,N-Y-R3-R6
Ri^o \\ //
R24
R23
R22

(1-9)
Reaction scheme 14
As shown in reaction scheme 14, compounds of formula (1-9), w'herein R1, R21, R22, R23, R24 and Y have the above defined meanings and R3 is a 3-6C-cycloalkyl group substituted by R6, with R6 being -C(O)-NR8R9, with R^ and R9 having the above defined meanings, can be synthesized by reaction of compounds of formula (4) prepared according to above reaction scheme 5, with compounds of formula (7), wherein Y has the above defined meaning and R3 is a 3-6C-cycloalkyl qmu^ substituted by R6, with R6 being -C(O)-NR8R9, with R8 and R9 having the above defined meanings. The compounds of formula (7) are commercially availafa/e or can be prepared by methods known to a person skilled in the art. An exemplified method for preparing compounds of formula (7) is shown in reaction scheme 16 below. In particular, a dehydrating agent, such as 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, a base, such as triethylamine, and a catalyst, such as 1-hydroxybenzotriazole, can be added to a compound of formula (4) which is preferably dissolved or suspended in an organic solvent, such as dichloromethane. After stirring the mixture e.g. for 0.3 to 2 h preferably at ambient temperature (e.g. 20 to 25°C), a compound of fomnula (7) can be added and the reaction is preferably performed at ambient temperature (e.g. 20 to 25°C) for 1 to 48 h to yield the compound of formula (1-9).

H,N-Y-R3 + CI-R4

-*■ Hj,N-Y-R3-R4

(5)
Reaction scheme 15
A compound of formula (5) with Y having the above defined meaning and R3 being a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and optionally one oxygen

atom substituted by R4 with R4 being -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41, -C(O)-3-6C-cycloalky!, wherein the 3-6C'Cycloalkyl group is optionally substituted by R42, or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, with R41, R42 and R43 having the atxjve defined meanings, can be prepared by reacting a compound of formula NH2-Y-R3 with Y having the atxDve defined meaning and R3 being a non-substituted 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and optionally one oxygen atom, in which compound the -NH2 group is protected by a suitable protecting group, such as a tert-butoxycarbonyl group, with a compound of formula CI-R4 with R4 being -C(O)-1-4C-alkyl, wherein the 1-4C-alky/ group is optionally substituted by R41, -C(O)-3-6C-cydoalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42, or -C(O)-O-1'4C-alkyi, wherein the 1-4C-alkyl group is optionally substituted by R43, with R41, R42 and R43 having the above defined meanings, and subsequent removal of the protective group. In particular, a compound of the formula CI-R4 can be added to a solution of a compound of formula NH2-Y-RS in an organic solvent, such as dichloromethane, containing a base, such as Huenigs base at a temperature of from 0 to 25'C. The mixture is then stirred for 1 to 48 h at ambient temperature (e.g. 20 to 25°C). The protective group can be removed by methods known to a person skilled in the art, such as by treatment with hydrochloric acid in an organic solvent, such as dioxane or an alcohol, e.g. iso-propanol. The hydrochloride of the compound of formula (5) thus obtained can be converted into the compound of formula (5) by methods known to a person skilled in the art, such as treatment with a base, e.g. potassium carbonate or aqueous ammonia. In case R41, R42 or R43 represent hydroxy, it is known to a person skilled in the art to protect the hydroxy group by a suitable protecting group, such as an acetate group or a silyt protective group, e.g. a tert-butyf-dimethylsilyl group or tert-butyl-diphenylsilyl group. Said protective group can be removed by methods known to a person skilled in the art with or without prior isolation of the protected intermediate (i.e. the compound of formula (5) in its protected form).
R8
H2N-R3-COOH + H—N:^ ^ H,N-R3-R6
R9
(7)
Reaction scheme 16
As shown in reaction scheme 16, a compound of formula (7) with R3 being a 3-6C-cycloalkyl group substituted by R6 and R6 being 'C(O)-NR8R9 can be prepared by reacting a compound of formula NH2-R3-COOH, in which R3 is a 3-6C-cycloalkyl group and wherein the -NH2 group is protected by a suitable protecting group, such as a tert-butoxycarbonyl group, with a compound of formula NHR8R9, in which R8 and R9 have the above defined meanings, and subsequent removal of the protective group. In particufar, a dehydrating agent, such as 1-(3-dimethylaminopropyl)-3-

ethylcarbodiimide hydrochloride (EDCI) can be added to a mixture of a compound of formula NH;-R3-C00H, wherein the -NH2 group is protected by a suitable protecting group, and a compound of formula NHR8R9 in an organic solvent, such as dichloromethane. The reaction is preferably performed at ambient temperature {e.g. 20 to 25°C) for 1 to 48 hours, The protective group can be removed by methods known to a person skilled in the art, such as by treatment with hydrochloric acid in an organic solvent, such as dioxane or an alcohol, e.g. iso-propanol. The hydrochloride of the compound of formula (7) thus obtained can be converted into the compound of formula (7) by methods known to a person skilled in the art, such as by treatment with a base, e.g, potassium cartjonate or aqueous ammonia, in case R9 is substituted by R91 or R92 with R91 or R92 being hydroxy, it is known to a person skilled in the art to protect the hydroxy group by a suitable protecting group, such as an acetate group or a silyl protective group, e.g. a tert-butyl-dimethylsilyl group or tert-butyl-diphenylsilyt group. Said protective group can be removed by methods known to a person skilled in the art with or v/ithout prior isolation of the protected intermediate (i.e. the compound of formula (7) in its protected form).
It is known to the person skilled in the art that, if there are a number of reactive centers on a starting or intermediate compound, it may be necessary to block one or more reactive centers temporarily by protective groups in order to allow a reaction to proceed specifically at the desired reaction center.
The compounds according to the invention are isolated and purified in a manner known per se, e.g. by dist(/ling off the solvent in vacuo and recrystallizing the residue obtained from a suitable so!vent or subjecting them to one of the customary purification methods, such as column chromatography on a suitable support material.
Salts of the compounds of formula (I), the N-oxides thereof and the stereoisomers of the compounds and the N-oxides thereof can be obtained by dissolving the free compound in a suitable solvent (for example a ketone such as acetone, methylethylketone or methylisobutylketone, an ether such as diethyl ether, tetrahydrofurane or dioxane, a chlorinated hydrocarbon such as methylene chloride or chloroform, a low molecular weight aliphatic alcohol such as methanol, ethanol or isopropanol, a low molecular weight aliphatic ester such as ethyl acetate or isopropyl acetate, or water) which contains the desired acid or base, or to which the desired acid or base is then added. The add or base can be employed in salt preparation, depending on whether a mono- or polybasic acid or base is concerned and depending on which salt is desired, in an equimolar quantitative ratio or one differing therefrom. The salts are obtained by filtering, reprecipitating, precipitating with a non-solvent for the salt or by evaporating the solvent. Salts obtained can be converted into the free compounds which, in turn, can be converted into salts. In this manner, pharmaceuticalty unacceptable salts, which can be obtained, for

example, as process products in the manufacturing on an industrial scale, can be converted into pharmaceutically acceptable salts by processes known to the person skilled in the art.
The compounds of formula ((), the salts thereof and the stereoisomers of the compounds and the salts according to the invention can be converted into their N-oxides, for example, by reaction with peracids, such as m-chloroperbenzoic acid or peracetic acid. The person skilled in the art is familiar with the reaction conditions for carrying out the N-oxidation.
Pure diasfereomers and pure enantiomers of (he compounds of formula (I) and the sails thereof, the Nl-oxides of the compounds and the N-oxides of the salts can be obtained e.g. by asymmetric synthesis, by using chiral starting compounds in synthesis and/or by splitting up enantiomeric and diasteriomeric mixtures obtained in synthesis. Preferably, the pure diastereomeric and pure enantiomeric compounds of the invention are obtainable by using chiral starting compounds in synthesis and/or by splitting up enantiomeric and diasteriomeric mixtures obtained in synthesis.
Enantiomeric and diastereomeric mixtures can be split up into the pure enantiomers and pure diastereomers by methods known to a person skilled in the art. Preferably, diastereomeric mixtures are separated by crystallization, in particular fractional crystallization, or chromatography. Enartiomeric mixtures can be separated e.g. by forming diasfereomers with a chiral auxiliary agent, resolving the diastereomers obtained and removing the chiral auxiliary agent. As chiral auxiliary agents, for example, chiral acids can be used to separate enantiomeric bases and chiral bases can be used to separate enantiomeric acids via formation of diastereomeric salts. Furthermore, diastereomeric derivatives such as diastereomeric esters can be formed from enantiomeric mixtures of alcohols or enantiomeric mixtures of acids, respectively, using chiral acids or chiral alcohols, respectively, as chiral auxiliary agents. Additionally, diastereomeric complexes or diastereomeric dathrates may be used for separating enantiomeric mixtures. Alternatively, enantiomeric mixtures can be split up using chiral separating columns in chromatography. Another suitable method for the isolation of enantiomers is the enzymatic separation.
All patents, patent applications, publications, test methods and other materials cited herein are incorporated by reference in their entireties.
The following examples illustrate the invention in greater detail, without restricting it. Further compounds according to the invention, of which the preparation Is not explicitly described, can be prepared in an analogous way.
The compounds, salts and stereoisomers which are mentioned in the examples, and the salts of the compounds which are mentioned in the examples, and the stereoisomers of the compounds

mentioned in the examples, (he stereoisomers of the salts which are mentioned in the examples and the stereoisomers of the salts of the compounds which are mentioned in the examples represent preierred embodiments of the invention.
The compounds which are mentioned in the examples, the salts thereof, N-oxides of the compounds and the salts thereof and stereoisomers of the compounds, salts, N-oxides of the compounds and N-oxides of the salts thereof represent preferred embodiments of the invention.

Examples
the following abbreviations are used; min: minutes, h: hour(s), DCM: dichloromethane, DCE: dichloroethane, THF: tetrahiydrofuran, EA: ethyl acetate, sesamol: 3,4-methylenedioxyphenol, brine: saturated sodium chiloride solution, DBU: 1,8-diazabicyclo(5.4.0]undec-7-ene, Huenigs base: N-ethiyl-diisopropylamine, mp.: melting point, bp: boiling point, RT: room temperature (20 to 25°C), ambient temperature: 20 to 25°C, TLC: thiin layer ctiromatograptiy, HPLC: tiigh performance liquid chromatography, GC-MS (El): gas chromatography coupled to mass spectrometry with electron impact ionization, MS (ESI): mass spectrometry with electron spray ionization, 1H-NMR: 1H nuclear magnetic resonance spectroscopy (chemical shifts are reported as ppm against tetramethylsiiane as internal standard, coupling constants J are reported in Hz).
Example A1: 4-Fluoro-3-methoxymethoxy-phenol Under an atmosphere of argon a stirred solution of 4-bromo-1-fluoro-2-methoxymethoxy-benzene from example A25 (47.0 g: 0.200 mol) in dry terf-BuOMe (1000.0 mL) is cooled to -78'C before fert-BuLi (1.7 M solution in pentane; 247.0 mL; 0.420 mol) is added via syringe within 30 min. After complete addition stirring is continue at -78°C for one hour. 2-[sopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (91,6 mL; 0.440 mol) is slowly syringed into the reaction mixture. After complete addition the mixture is stin'ed at -78°C for 30 min. Stirring is continued without external cooling. At 0°C internal temperature the reaction mixture is quenched with 1 M citric acid (400.0 mL). The mixture is vigorously stirred for 30 min. The organic layer is separated. The aqueous layer is extracted with fert-BuOMe (2x100 mL). The combined organic layers are washed with saturated Na-HCO3 (250 mL) and concentrated to about 500 mL under reduced pressure. To the well stirred solution of the crude product HaO; (30% aqueous solution; 51.5 mL; 0.500 mol) is slowly added at 0°C and the reaction mixture is stirred at ambient temperature over night. The aqueous iayer Is separated. The organic layer is washed with water (2x100 mL), 1M aqueous Na2SO3 solution (several small portions) till free of peroxide and dried over MgSO*. After filtration the solvent is removed under reduced pressure. The residual oil is chromatographed on silica gel (cyc!Dhexane:AcOEt / 9:1) to give the title compound as colorless oil. Yield; 29.8 g. GC-MS (El): m/z = 172 (M'); 45 (100%).
'H-NMR (300 MHz. DMSO-de): 9.35 (s, 1H, -OH); 6.99 (dd, J, = 11.3, J2 = 8.9, 1H); 6.64 (dd, Ji = 7.1, J2 = 2.9, 1H); 6.36 (ddd, J, = 8.9, J2 = 3.4, J3 = 2.9, 1H); 5.15 (s, 2H); 3.40 {s, 3H).
The following compounds are obtained analogously to the procedure described in the above ax-ample A1.
Example A2: 3-(1,1-Difluoro-methoxy)-4-fIuoro-phenol

Starting from 4-bromo-2-(1,1-difluoro-methoxy)-1-fluoro-ben2ene (example A26) the title compound
is obtained as colorless oil.
GC-MS (El): m/z = 178 (M*); 128 (100%).
^H-NMR (300 MHz, DMSO-de): 9-72 (s, 1H, -OH); 7.18 (t, J = 74.0, 1H); 7.17 (dd, Ji = 10.8, J2 =
8.9, 1H); 6.70 (dd, J, = 6.8, J2 = 2.8, 1H); 6.63 (ddd, Ji = 8.9, Jj = 3.7, J3 = 2.8).
Example A3: 2-Bromo-5-fluoro-4-methoxy-phenol 3-Fluoro-4-mettioxy-phienol (21.32 g; 0.15 mol) prepared according to literature [Freedman, J.; Stewart, K.T.; J. Heterocycl. Ctiem. 1989, 26, 1547-1554] is dissolved in dry dichtoromethane (300 mL). The well stirred reaction mixture is cooled to -15°C (ice/salt). A solution of bromine (23.97 g; 0.15 mol) in dry dichloromettiane (75 nriL) is slowly dropped into the reaction mixture. After complete addition stirring is continued for one hour. Water (150 mL) containing sodium sulfite (3.0 g) is added to the reaction mixture. Stirring is continued at ambient temperature for 30 min. The organic layer is separated, washed with water (100 mL) and dried over MgSO4 in the presence of decolorizing charcoal. After filtration the solvent is completely removed under reduced pressure. The residue is crystallized from tert-butylmelhylether/hexane to give the title compound as a colorless solid. Yield: 30.74 g.
GC-MS (El): m/z = 222, 220 {M*) 207, 205 (M'-CHJ, 100%); 179, 177.
^H-NMR (300 MHz, DMSO-dg): 10.06 (s, 1H, -OH); 7.28 (d, J = 9.2, 1H); 6,81 (d, J = 12.6, 1H); 3.76 (s, 3H).
The following compound is obtained analogously to the procedure described in above example A3.
Example A4: 2-Bromo-4-fluoro-5-methoxy-phenol Starting from 4-fluoro-3-methoxy-phenol prepared according to literature [Belanger, P.C; Lau, C.K.; Williams, H.W.R.; Dufresne, C; Scheigetz, J. Can. J. Chem. 1988, 66, 1479-1482] the title compound is obtained as coloHess solid.
GC-MS (El): m/z = 222, 220 (M^ 100%); 207, 205 (M-CH3*); 179, 177.
'H-NMR (300 MHz, CDCIa): 7.16 (d, J = 10.2, 1H); 6.67 (d, J = 7.7, 1H); 5.29 (s, 1H, -OH); 3.85 (s, 3H)
Example AS: 2-Bromo-5-(1,1-difluoro-methoxy)-4-fluoro-phenol Starting from 3-(1,1-d(fluoro-methoxy)-4-f]uoro-phenol (example A2) the title compound is obtained as colorless oil.
GC-MS (Et): m/z = 256,258 (M*); 206, 208 (100%).
^H-NMR (300 MHz, DMSO-de): 10.55 (s, 1H, -OH); 7.65 (d, J = 10.0, 1H): 7.19 (t, J = 73.0, IN); 6.90 (d, J = 7.3, 1H).

Example A6: 1-(5-Bromo-4-cyclopropylmethoxy-2-methyl-phenyl)-ethanone A suspension of 1-{4-cyclopropylmethoxy-2-methyl-phenyl)-ethanone from example A24 (6.4 g, 31.3 mmol) and N-bromosuccinimide (6.20 g, 34.5 mmol) in dry dimethylformamide (50 mL) is heated for 3h at 50°C. After cooling to ambient temperature, water (200 mL) is added and the mixture is extracted with ethyl acetate (3 x 60 ml). The combined organic extracts are dried over sodium sulfate. The solvent is removed under reduced pressure. The crude is purified by column chromatography on silica gel using dichloromethane as eluent to give the title compound as a off-white solid. Yield: 4.80 g. MS (ESI): m/2 = 282 (MH*).
^H-NMR (300 MHz, DMSO-dg): 8.05 (s, 1H); 7.02 (m, 1H); 4.02 (d, J = 6.0, 2H); 2.50 (s, 3H); 2.45 (s, 3H); 1.30 (m, 1H); 0.62 (m, 2H); 0.40(m, 2H).
Example A7; 2-Bromo-4-flucro-5-methoxymeLhoxy-phenol 4-Fluoro-3-methoxymethoxy-phenol from example A1 (6.89 g; 40.0 mmol) is dissolved in dry di-chloromethane (160.0 mL). The stirred solution is cooled to '15°C. N-bromosuccinimide (7.12 g; 40.0 mmol) is added in small portions over one hour. After complete addition the reaction mixture is stirred for another 30 min at -15oC.
The reaction mixture is extracted with 2% aqueous sodium sulfite solution (25.0 mL). The organic layer is separated. The aqueous layer is extracted with dichloromethane (2x25.0 mL). The combined organic layers are dried over MGSO4. The crude material is chromatographed on silica gel (dichloromethane:MeOH / 99:01) to give the title compound as a colorless solid. Yield: 8.33 g. GC-MS (El): m/z = 250, 252 (M*); 45 (100%).
'H-NMR (300 MHz, DMSO-de): 10.14 (s, 1H, -OH); 7,41 (d, J = 10.8, 1H); 6.87 (d, J = 7.8, 1H); 5.17 (s, 2H); 3.41 (s, 3H).
Example A8: 5-Cyclopropylmethoxy-benzo[1,3]dioxole Sodium hydride (60 vrt% dispersion in mineral oil; 11.0 g; 275.0 mmol) is freed from oil by washing with hexane (2 x 50 mL) and suspended in dry DME (375 mL) and dry DMSO (37.5 mL). Under an atmosphere of nitrogen a solution of commercially available sesamol (3,4-methylenedioxy-phenol) (34.53 g; 250.0 mmol) in dry DME (250 mL) is dropped into the well-stirred suspension at a rate to keep the internal temperature below 40°C. After complete addition stirring is continued at ambient temperature for one hour.
Neat commercially available bromomethyl-cyclopropane (37.13 g; 275.0 mmol) is added in one fxsrtion and the reaction mixture is stirred at 80°C over night. Jce-cold water (125 mL) is drop wise added and the reaction mixture is stirred for 30 min at ambient temperature. After addition of brine (125 mL) the organic layer is separated and concentrated in vacuo. The aqueous layer is extracted with tert-butylmethylether (3 x 200 mL). All organic phases are combined, washed with brine (200 mL), dried over MgSO4 and filtered through a plug of neutral alumina containing 5 wt% of water.

The product is completely eluted with several portions of tert-butylmethylether. The solvent is
removed under reduced pressure. The remaining crude product is purified by short path distillation
at 3 X 10'^ mbar (117°C) to give the title compound as colorless oil that solidifies at ambient
temperature. Yield: 47,28 g.
GC-MS (El): m/z = 192 (M). 138 (M'-C4H6, 100 %).
1H-NMR (200 MHz, DMSO-de): 6.77 (d, J = 8.5, 1H); 6.59 (d, J = 2.5, 1H); 6.32 (dd, Ji = 8.5, J2 =
2.5, 1H); 5.93 (s, 2H); 3.71 (d, J = 6.9, 2H); 1.15 (m, 1H); 0.53 (m, 2H); 0.27 (m, 2H).
The following compounds are obtained analogously to the procedure described in atfove example A8.
Example A9: 5-Cyclobutylmethoxy-benzo[1,3]dioxole Starting from commercially available bromomethyi-cyclobutane and sesamol the title compound is obtained as colorless solid. GC-MS (El): m/z = 206 (M+); 138 (100 %).
'H-NMR (300 MHz, DMSO-de): 6.78 (d, J = 8.4, 1H); 5.59 (d, J = 2.5, 1H); 6.34 (dd, J1 = 8.4, J2 = 2.5, IN); 5.94 (s, 2H); 3.85 (d, J ^ 6,7, 2H); 2.66 (m, 1H); 2,05 (m, 2H); 1.93-1,76 (m, 4H).
Example A10: 5-Ethoxy-benzolo[1,3]dioxole Starting from commercially available iodoethane and sesamol the title compound is obtained as colorless oil.
GC-MS (El): m/z = 166 (M*); 138 (M+-C2H4); 137 (M+-C2H5, 100%).
^H-NMR (300 MHz, DMSO-de): 6,78 (d, J = 8,4, IN); 6,59 (d, J = 2.5, 1H); 6:33 (dd, J, = 8.4, Jj = 2.5, 1H); 5.94 (s, 2H); 3.93 (qu, J = 7.0, 2H); 1,28 (t, J = 7.0. 3H),
Exannple A11: 5-Propoxy-benzo[1,3)dioxole Starting from commercially available iodopropane and sesamol the title compound is obtained as colorless oil.
GC-MS (El): m/z = 180 (M*); 138 (M'-C3H6. 100%); 137 (M+-C3H7).
'H-NMR (300 MHz, DMSO-de): 6,78 (d, J = 8.4, 1H); 6.59 (d, J = 2.5, 1H); 6.34 (dd, J, = 8.4, Jj = 2,5, 1H); 5.94 (s, 2H); 3.83 (t, J = 6.5, 2H); 1.68 (m, 2H); 0.95 (t, J = 7.4, 3H).
Example A12: 5-Butoxy-benzo[1,3]dioxole Starting from commercially available bromobutarte and sesamol the title compound is obtained as colorless oil.
GC-MS (El): m/z = 194 (M"); 138 (M'-C4H8, 100%); 137 (M+-C4H9).
'H-NMR (300 MHz, DMSO-d6): 6.78 (d, J = 8.4,1H); 6.59 (d, J = 2.5, 1H); 6.34 {dd, J, = 8.4, J2 = 2,5, IN); 5.94 (s, 2H); 3,87 (t, J = 6.5, 2H); 1,65 (m, 2H); 1.41 (m, 2H); 0.92 (t, J = 7.4, 3H).

Example A13: 5-(2-Methoxy-ethoxy)-benzo[1,3]dioxole Starting from commercially available 1-bromo-Z-methoxy-ethane and sesamol the title compound is obtained as coloriess oii.
GC-MS (El): m/z = 196 (M*); 138 (M'-C3H6O, 100%); 59.
'H-NMR (300 MHz, DMSO-de): 6-09 (d, J = 8.5, 1H); 6.53 (d, J = 2.5, 1H); 6.33 (dd, J, = 8.5, J2 = 2.5, IN); 5.90 (s, 2H); 4.04 (m, 2H); 3.71 (m, 2H); 3.44 (s, 3H).
Example A14: 1-Bromo-2-cycloprQpylmethoxy-4-methoxy-benzene Starting from commercially available 2-bromo-5-mettioxy-phienol and bromomethyl-cyclopropane the title compound is obtained as colorless solid. GC-MS (El); m/z = 258, 256 (M").
'H-NMR(200 MHZ, DMSO-do); 7.41 (d, J = 7.9. 1H); 6.48 (dd, J1 = 7.9, J2 = 2.2, 1H); 6,45 (d, J = 2.2, 1H); 3.87 (d, J - 5.6, 2H). 3.76 (s, 3H); 1.26 (m, 1H); 0.63 (m, 2H); 0,36 (m, 2H).
Example A15: 1-Bromo-4-methoxy-2-(2-methoxy-ethoxy)-benzene Starting from commercially available 2-bromo-5-methoxy-phenol and 1-bromo-2-methoxy-ethane the title compound is obtained as colorless solid. GC-MS (El); m/z = 260, 262 (M*); 202, 204 (M'-C3H6O, 100 %),
'H-NMR (200 MHz, DMSO-dg): 7.40 (d, J = 8.7,1H); 6.51 (d, J = 2.8, 1H); 6.41 (dd, J, = 8.7, Jj = 2.8. 1H); 4.15 (t, J ^ 4.8. 2H), 3.80 (t, J = 4.8, 2H); 3.78 (s, 3H); 3.48 (s, 3H).
Example A16; 1-Bromo-2-cyc!opropylmettioxy-5-methoxy-benzene Starting from commercially available 2-bromo-4-methoxy-pheno) and bromomethyl-cyclopropane the title compound is obtained as colorless oil. GC-MS (El): m/z = 256, 258 (M*); 202, 204 (100 %).
'H-NMR (200 MHz, CDCU): 7.11 (d, J = 2.8, 1H); 6.86 (d, J = 8.9, 1H); 6,78 (dd, J, = 8.9, J2 = 2.8, 1H); 3.82 (d, J = 6.8, 2H); 3.75 (s, 3H); 1,16 (m, 1H); 0.51 (m, 2H); 0.44 (m, 2H).
Example A17; 1-Bromo-2-cyclopropylmettioxy-4-fluoro-benzene Starting from commercially available 2-bromo-5-fluoro-phenol and bromomethyl-cyclopropane the title compound is prepared as colorless oil
GC-MS (El); m/z = 244, 246 (M*); 190, 192 (M*-C4H6); 55 (100%),
'H-NMR (300 MHz, DMSO-dg): 7,58 (dd, Ji = 8.7, J; = 6.4, 1H); 7.02 (dd, Ji = 11,2, Jj = 2.8, 1H); 6.75 (ddd, J, = J2 = 8.7, Js = 2.8, 1H); 3.93 (d, J = 6.8, 2H); 1.24 (m, 1H); 0.56 (m, 2H); 0.38 (m, 2H).
Example A18; 1-Bromo-2-cyclopropylmethoxy-5-fluoro-benzene

starting from commercially available 2-bramo-4-fluoro-phenol and bromomethyl-cyciopropane the
title compound is obtained as colorless oil.
GC-MS (El); m/z = 244, 246 (M*); 190, 192; (M'-C4H6); 55 (100%).
1H-NMR (400 MHz. DlVISO-dg): 7.52 (dd, J, = 8.2, J; = 3.1. 1H); 7.19 (ddd, J, = 9.1, J2 = 8.2, J3 =
3,1, 1H); 7.10(dd, J1 = 9.1, J2 =5.0,1H); 3,89 (d, J = 6.8, 2H); 1.22 (m, 2H); 0.57 (m, 2H); 0.35 (m,
2H).
Example A19: 1-Bromo-2-cyclopropylmethoxy~4-fluoro-5-methoxy-ben2ene Starting from 2-bromo-5-fluoro-4-methoxy-phenol (example A3) and bromomethyl-cyciopropane the title compound is obtained as colorless solid. GC-MS (El): m/z = 276, 274 (M*); 222, 220 (M'-C4H6, 100%); 206, 204.
1H-NMR (400 MHz, DMSO-de): 7.38 (d, J = 9.2, 1H); 7.13 (d, J = 13-1, 1H); 3.85 (d, J =6.9, 2H); 3.80 (s, 3H); 1.20 (m, IN); 0.57 (m, 2H); 0.33 (m, 2H).
Example A20: 1-Bromo-2-cyclopropylmethoxy-5-fluoro-4-methoxy-benzene Starting from commercially available 2-bromo-4-fluoro-5-methoxy-phenol (example A4) and bromomethyl-cyciopropane the title compound is obtained as colorless solid. GC-MS (El): m/z = 276, 274 (M*); 222, 219 (M+-C4H6. 100 %).
'H-NMR (400 MHz, DMSO-de): 7,48 (d, J = 10,8, 1H); 6.90 (d, J = 7.9, 1H); 3.93 (d, J =6.8, 2H); 3.85 (s, 3H); 1.24 (m, 1H); 0.58 (m, 2H); 0.36 (m, 2H),
Example A21: 1-Bromo-2-cyclopropylmethoxy-benzene Starting from commercially available 2-bromo-phenol and bromomethyl-cyciopropane the title compound is obtained as colorless oil.
GC-MS (El): m/z = 226, 228 (M*); 172, 174 (M'-C4H6), 55 (100%).
^H-NMR (400 MHz, DMSO-de): 7.56 (dd, J, = 7.9, J1 = 1.6, 1H); 7.31 (ddd, J, = 8.3, J2 = 7.3, J3 = 1.6, 1H); 7.08 (dd, J1 = 8.3, J2= 1.3, 1H); 6.87 (ddd, J1 = 7.9. J2= 7.3, Ja = 1.3, 1H);3.91 (d, J = 6.8, 2H); 1.24 (m, IN); 0.58(m, 2H); 0.35 (m, 2H).
Example A22: 2-Bromo-1-cyclopropylmethoxy-4-methyl-benzene Starting from commercially available 2-bromo-4-methyl-phenol and bromomethyl-cyciopropane the title compound is obtained as colorless oil, GC-MS (El): m/z = 240,242 (M'); 186,188 (M'-C4H6); 107.
'H-NMR (300 MHz, CDCI3):.7.34 (d, J = 2.1, 1H); 7,01 (dd, J1 = 8.2, J2 = 2,1, 1H); 6.78 (d. J = 8.2. 1H); 3.86 (d, J = 6.8, 2H); 2,28 (s, 3H); 1.30 (m, IN); 0.63 (m, 2H); 0.39 (m, 2H),
Example A23: 1-(3-Bromo-4-cyclopropylmethoxy-phenyl)-ethanone

Starting from 1-(3-bromo-4-hydroxy-phienyl)-ethanone prepared according to literature (Heravi etal, Tetrahedron Letters 2005, 46, 8959) and bromomethyl-cyclopropane the title compound is obtained as colorless solid.
'H-NMR (300 MHz, DMSO-de): 8.10 (d,J= 2.0,1H); 7.91 (dd, , J1 = 8.0, J2 = 2.0, 1H); 7.18 (d, J = 8.0, 1H); 4.03 (d, J = 6.0, 2H); 2.50 (s, 3H); 1.30 (m, 1H); 0.62 (m, 2H); 0.40 (m, 2H).
Example A24; 1-(4-Cyclopropylmethoxy-2-methyl-pherry/)-ethanone Starting from commercially available 1-(4-hydroxy-2-methyl-phenyl)-ethanoneand bromomethyl-cyclopropane the title compound is obtained as pale yellow oil.
'H-NMR (300 MHz, DMSO-dg): 7.78 (d, J = 2.0,1H), 6.80 (m, 2H), 3.88 (d, J = 6.0, 2H), 2.50 (s, 3H), 2.45 (s, 3H), 1.25 (m, IN), 0.55 (m, 2H), 0.32 (m, 2H).
Example A25: 4-Bromo-1-fluoro-2-methoxymethoxy-benzene Starling from commercially available 5-bromo-2-fluoro-phenol and 1-chloro-1-methoxy-methane prepared according to literature (Stadlw/ieser, J. Synthesis 1985. 490) the title compound is obtained as colorless oil,
GC-MS (El): m/2 = 234, 236 (M*); 45 (100%).
'H-NMR (300 MHz, DMSO-dg): 7.45 (dd, J, = 7.5, J2 = 2.2, 1H); 7,28-7.17 (m, 2H); 5,28 (s, 2H); 3.41 (s, 3H).
Example A26: 4-Bromo-2-(1,1-dtf(uoro-methoxy)-1-fluora-benzene A pressure reactor is charged with commercially available 5-bromo-2-fluoro-phenol (95.50 g; 0.50 mol), 6N NaOH (500 mL; 3.0 mol) amd dioxane (500 mL). The reactor is pressurized with 1-chloro-1,1-difluoro-methane to 6.0 bar and heated to 80°C for 72 hours.
The cooled reaction mixture is acidified to pH 2 by careful addition of 6N HCI and extracted with tert.-BuOMe (1000 mL + 2x 200mL). The combined organic layers are washed with brine (300 mL) and dried over MgSO4. Alfer filtration the solvent is removed under reduced pressure. The product is separated from remaining starting material by column chromatography orj silica geJ (cyclohex-ane) to give the title compound as colorless oil. Yield: 54.1 g. GC-MS (El): m/2 = 240, 242 (M'); 190, 192 (100 %).
^H-NMR (300 MHz, DMSO-dg): 7,64 (dd, J, = 7.1, Ja = 2.4, 1H); 7.52 (ddd, J, = 8.8, J2 = 4.2, J3 = 2.4, 1); 7.41 (dd, J1 = 10.4, J2 = 8.8, 1H); 7.3 (T. J = 73.0,1H).
Example A27: 1-Bromo-2-cyclopropylmethoxy-5-fluoro-4-methoxymethoxy-benzene Starting from 2-bromo-4-fluoro-5-methoxymethoxy-pheno) (example A7) and bromomethyJ-cyclopropane the title compound is obtained as colorless oil. GC-MS (El): m/z = 304, 306 (M*); 45 (100%).

1H-NMR (300 MHz, DMSO-d6): 7.54 (d, J = 10.4, 1H); 6.99 (d, J = 7.7, 1H); 5.26 (s, 2H); 3.88 (d, J = 6.9, 2H); 3.41 (s, 3H); 1.22 (m, 1H); 0.57 (m, 2H); 0.34 (m, 2H).
Example A28: 1 -Bromo-2-cyclopropylmethoxy-4-(1,1-difluoro-methoxy)-5-fluoro-benzene Starting from 2-bromo-5-{1,1-drfluorQ-methoxy)-4-fluoro-phenoI (example A5) and bromomethyl-cyclopropane the title compound is obtained as colorless oil. GC-MS (El): m/z = 310,312 (M'); 256,258; 206, 208; 177, 179; 55 (100%). 1H-NMR (300 MHz, DMSO-d6): 7,78 (d, J = 6.9, 1H); 7.25 (t, J = 74,0, 1H); 7.13 (d, J = 7.3, 1H); 3.92 (d, J = 6.9, 2H); 1.23 (m, 1H); 0.58 (m, 2H); 0.35 (m, 2H).
Example A29: 5-Cyclopropytmethoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzo[1,3]dioxole
The reaction is performed in flame-dried glassware under an atmosphere of argon. A stirred solution of 5-cyclopropyfmethoxy-benzo[1,3]dioxole from example A8 (38.44 g; 200.0 mmol) in dry THF (500 mL) is cooled to -40°C before n-butyl lithium (138.0 mL; 1.6 M solution in hexane; 220 mmol) is slowly added via syringe. After complete addition, stirring is continued at -40°C for two hours. At -78°C neat 2-:so-propoxy-4,4,5,5-tetramethyl-[1,3.2]dioxaborolane (40.95 g; 220.0 mmol) is added via syringe and stirring is continued at -78°C for two hours. At -15°C the reaction mixture is quenched with saturated NHiCI-solution (200 mL) and stirred at ambient temperature for 30 min. The organic layer is separated and concentrated under reduced pressure. The aqueous layer Is extracted with tert-butylmethylether (3 x 200 mL). All organic phases are combined, washed with saturated NaCI-solution (200 mL), dried over MgSO* and filtered through a plug of neutral alumina containing 5 wt% of water. The product is completely eluted with several small portions of tert-butylmethylether.
The solvent is removed under reduced pressure. The crude is treated with ice-cold methanol (50 mL) to deliver the title compound as colorless solid. Yield 54.32 g. GC-MS (El): m/z = 318 (M*); 264 (M'-C4H6); 207; 164 (100 %).
'H-NMR (200 MHz, DMSO-de): 6.78 (d, J = 8.4, 1H); 6.29 (d, J = 8.4; 1H); 5.92 (s. 2H); 3.71 (d, J = 6.3, 2H); 1.29 (s, 12H); 1.14 (m. 1H); 0.50 (m, 2H); 0.34 (m, 2H).
The following compounds are obtained analogously to the procedure described in above example A29.
Example A30: 5-Cyclobutylmethoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzo[1,3Idioxole
Starting from 5-cyclobutylmethoxy-benzo(1,3]dioxole (example A9) the title compound is prepared as colorless solid. GC-MS (El): m/z = 332 (M*); 164 (100 %);

'H-NMR (400 MHz, DMSO-d6): 6,81 (d, J = 8.4, 1H); 6,29 (d, J = 8,4; 1H); 5,92 (s, 2H); 3.76 (d, J =
6.0, 2H); 2.64 (m, 1H); 2.07-1,76 (m, 6H); 1.27 (s, 12H).
Example A31; 5-Ethoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-ben20(1,3]dioxole Starting from 5-ethoxy-benzo[1,3]dioxole (example AlO) the title compound is prepared as colorless solid,
GC-MS (El): m/z = 292 (M', 100%); 207; 164,
'H-NMR (300 MHz, DMSO-de): 6.80 (d, J = 8.4, 1H); 6,30 (d, J = 8.4; 1H); 5.92 (s, 2H); 3.86 (qu, J = 7,0, 2H); 1.27 (s, 12H); 1.25 (t, J = 7.0, 3H),
Example A32: 5-Propoxy-4-(4,4,5,5-tetramet]iyt-[1,3,2]dioxaborolan-2-yl)-benzo[1,3]dioxole
Starting from 5-propoxy-benzo[1,3]dioxole (example A11) the title compound is prepared as colorless solid.
GC-MS (El): m/z = 306 (M^); 207 (100 %); 164,
'H-NMR (300 MHz, DMSO-de): 6.80 (d, J = 8.4, 1H); 6.28 (d, J = 8.4; 1H); 5.92 (s, 2H); 3.77 (t, J = 6.2, 2H); 1.66 (m, 2H); 1.27 (s, 12H); 0.98 (t, J = 7,4, 3H),
Example A33; 5-Butoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzo[1,3]dioxole Starting from 5-butoxy-ben2o[1,3]dioxole (example A12) the title compound is prepared as colorless solid.
GC-MS (El): m/z = 320 (M*); 207 (100 %); 164. 1H-NMR (300 MHz, DMSO-dg): 6.80 (d, J = 8.5, 1H); 6.29 (d, J - 8,5; 1H); 5,92 (s, 2H); 3.81 (t, J =
6.1, 2H); 1.62 (m, 2H); 1,46 (m, 2H); 1.26 (s, 12H); 0.91 (t, J = 7.3, 3H).
Example A34; 5-(2-Methoxy-ethoxy)-4-(4,4,5.5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzo[1,3]dioxole
Starting from 5-(2-methoxy-ethoxy)-benzo[1,3]dioxole (example A13) the title compound is prepared as colorless solid. GC-MS (El): m/z = 322 (M*); 207 (100 %); 164.
'H-NMR (200 MHz, CDCI3): 6,81 (d, J = 8.5.1H); 6,31 (d, J = 8.5, IN); 5.93 (s, 2H); 3.93 (m, 2H); 3.59 (m, 2H); 3.30 (s, 3H); 1,27 (s, 12H).
Example A35:2-(2-Cydopropylmethoxy-4-fluoro-5-methoxy-phenyl)-4,4,5,5-tetramethyl-[1.3,2]d ioxa borolane
The reaction is performed in flame-dried glassware under an atmosptiere of argon. A stirred solution of 1-bromo-2-cyc!opropylmettioxy-4-fiuoro-5-mettioxy-benzenefrom example A19 (27.51 g; 0.10 mol) in dry tert-butylmethylether (500 mL) is cooled to -20°C before addition of n-

butyl lithium (1.6 M in hexane; 68.8 mL; 0.11 mol) via syringe. After complete addition stirring is continued for one hour. Neat 2-iso-propoxy-4,4,5,5-tetramethyl-[1,3,2]dioxabQrolane Is added via syringe into the reaction mixture at -40°C. After 30 min the reaction is quenched with 1M citric acid (200 mL) at 0°C and stirred for one hour al ambient temperature. The organic layer is separated. The aqueous layer is extracted with tert-butylmethylether (100 mL).The combined organic layers are washed with brine (200 mL) dried over MgSO4 and filtered through a plug of neutral alumina containing 5 wt% of water. The product is completely eluted with several small portions of tert-butylmethylether. The solvent is removed under reduced pressure. The crude is purified by short path distillation at 3x10"^ mbar (160°C) to give the title compound as a colorless oil that solidifies at ambient temperature. Yield: 22.65 g.
GC-MS (El): m/z = 322 (M'. 100%); 211, 168. Purity: >99.8%.
'H-NMR (300 MHz, DMSO-de): 7.14 (d, J = 10.5, IH); 6.91 (d, J = 13.6, 1H); 3.81 (d, J =6.0. 2H); 3.77 (s, 3H); 1.28 (s, 12H); 1.16 (m, IH); 0.48 (m, 2H); 0.38 (m, 2H).
The following compounds are obtained analogously to the procedure described in above example A35.
Example A36: 2-(2-Cyclopropylmethoxy-4-methoxy-ph6ny()-4,4,5,5-teframethyl-[1,3,2]dioxaborolane
Starting from 1-bromo-2-cyclopropylmethoxy-4-methoxy-benzene (example A14) the title compound is prepared as colorless solid after crystallization from hexane. GC-MS (El): m/z = 304 (M"); 276 ; 250; 193; 164 (100%); 150.
'H-NMR (200 MHz, DMSO-de): 7.41 (d, J = 7.9, IH); 6.48 (dd, J1 = 7.9, J; = 2.2, 1H); 6.45 (d. J = 2.2, 1H); 3.87 (d, J =5.6, 2H); 3.75 (s, 3H); 1.25 (s, 12H); 1.16 (m, 1H); 0.49 (m, 2H); 0.44 (m, 2H).
Example A37: 2-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxatx)rolane
Starting from 1-bromo-2-cyclopropylmethoxy-5-methoxy-benzene (example A16) the title compound is obtained as colorless oil after short path distillation at 3x10"^ mttar (leO'C). GC-MS (El): m/z = 304 (M'); 276; 250; 193 (100%); 150.
1H-NMR (200 MHz, CDCI3): 7.15 (d, J = 3.1, IH); 6.90 (dd, J1 = 9.0, J2 = 3.1, IH); 6.81 (d, J = 9.0, IH); 3.80 (d, J =6.3, 2H); 3.78 (s, 3H); 1.35 (s, 12H); 1.17 (m, IH); 0.55 (m, 2H); 0.38 (m, 2H).
Example A38: 2-(2-Cyclopropylmethoxy-4-fluoro-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
Starting from 1-bromo-2-cyclopropylmethoxy-4-fluoro-benzene (example A17) the title compound is obtained as colorless solid after short path distillation at 3x10"^ mbar (130°C). GC-MS (El): m/z = 292 (M'); 181, 55 (100%).

'H-NMR(300 MHz, DMSO-dg): 7.48 (dd, J1 =-J2 = 8.0, 1H); 6.80 (dd, J1 = 12.0, J2 = 2.2, 1H); 6.71 (ddd, J1 = 8.4, J2 = 8.0, J3 = 2.2, 1H); 3.89 (d, J = 5.8, 2H); 1.27 (s, 12H); 1.17 (m, 1H); 0.51 (m, 2H); 0.46 (m, 2H).
Example A39: 2-(2-Cyclopropylmethoxy-5-fluoro-phenyl)-4,4,5,5-tetramethyl-[1,3,2Idioxaborolane
Starting from 1-bromo-2-cyclopropylmethoxy-5-fluoro-benzene (example A18) the title compound is obtained as colorless solid after short patti distillation at 3x10'* mbar (10G°C). GC-MS (El): m/z = 292 (M+); 181 (100%); 55.
'H-NMR (300 MHz, DMSO-d6): 7.22-7 13 (m, 2H); 6.95 (dd, J1 = 8.9, J2 = 4.2, 1H); 3.85 (d, J =6.4, 2H); 1.28 (s, 12H); 1.17 (m, 1H); 0.52 (m, 2H): 0.46 (m, 2H).
Example A40: 2-(2-Cyclopropylnriethoxy-phenyl)-4,4,5,5-tetramethyi-[1,3,2]dioxaborolane Starting from 1-bromo-2-cyclopropylmethoxy-bertzene (example A21) the title compound is obtained as colorless viscous oil. GC-MS (El): m/z = 274 (M+); 163; 120; 83; 55 (100%).
'H-NMR (300 MHz, DMSO-d6): 7.45 (dd, J, = 7.4, Jj = 1.7, 1H); 7.37 (ddd, J, = 7.8, Js = 6.9, J3 = 1.7, 1H); 6.91 (d, J = 7.8. 1H); 6.89 (d, J = 6.9, 1H); 3.86 (d, J =5.8. 2H); 1.28 (s, 12H); 1.20 (m, 1H); 0.50 (m,2H); 0.44 (m,2H).
Example A41: 2-(2-Cyclopropylmethoxy-5-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
Starting from 1-bromo-2-cyclopropylmethoxy-5-methyl-benzene (example A22) the title compound is obtained as colorless solid.
'H-NMR 400 MHz, OMSO-d6): 7.26 (d. J = 2.1, 1H); 7.16 (dd, J, = 8.3, J2 - 2.1, 1H); 6.81 (d, J = 8.3, 1H);3.81 (d, J = 5.9, 2H); 2.21 (s, 3H); 1.27 (s, 12H); 1.15 (m, 1H);0.47(m, 2H); 0.40 (m, 2H).
Example A42: 2-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
Starting from 1-bromo-2-cyclopropylmethioxy-5-fluoro-4-methoxy-benzene (example A20) the title compound is obtained as colorless solid after crystallization from methanol. GC-MS (El): m/z = 322 (M'); 211; 182; 168 (100 %); 55.
'H-NMR (300 MHz, DMSO-de): 7.15 (d, J = 11.7, 1H); 6.73 (d, J = 7.0, 1H); 3.88 (d, J =6.0, 2H); 3.85 (s,3H); 1.26(s, 12H); 1.16 (m, 1H); 0.50 (m, 2H); 0.30 (m, 2H).
Example A43: 2-[4-Methioxy-2-(2-methoxy-ethoxy)-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Starting from 1-bromo-4-methioxy-2-(2-methoxy-ethoxy)-ben2ene (example A15) the title
compound Is obtained as colorless solid after crystallization from mettianol.
GC-MS (El): m/z = 308 {IV1+); 250 (M+-C3H6O); 164 (100 %).
'H-NMR (200 MHz, CDCI3): 7.61 (d, J = 8.2, 1H); 6.49 (dd, J, = 8.2, J2 = 2.2, 1H); 6.41 (d, J = 2.2
1H);4.10(t, J = 5.4, 2H);3.80(s. 3H);3.78(t, J = 5.4, 2H); 3-50 (s, 3H); 1.32 (s, 12H).
Example A44: 2-(2-Cyclopropylmethoxy-5-fluoro-4-mettioxymettioxy-plienyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
Starting from 1-bromo-2-cyclopropylmethoxy-5-fluoro-4-methoxymethQxy-benzene (example A27) the title compound is obtained as colorless oil thiat solidified on standing at ambient temperature after short path distillation at 3x10"^ mbar (150°C). GC-MS (El): m/z = 352 (M*): 45 (100%).
1H-NMR (300 MHz, DMSO-dfi): 7.19 (d, J = 11.3, 1H); 6.82 (d, J = 6.8, 1H); 5-28 (s, 2H); 3.83 (d, J = 6.0, 2H); 3,41 (s, 3H); 1.26 (s, 12H); 1.16 (m, 1H); 0.49 (m, 2H); 0.40 (m, 2H).
Example A45: 2-f2-Cyclopropyfmethoxy-4-( 1,1 -dif(uoro-methoxy)-5-fluoro-pheny(]-4,4,5,5-tetramethyl-[1,3,2]-dioxaboiane
Starting from 1-bromo-2-cyclopropylmethoxy-4-(1,1-difluoro-methoxy)-5-fluoro-benzene (example A28) the title compound is obtained as colorless oil after short path distillation at 2x10"^ mbar (130°C)
GC-MS (El): 358 (M+); 330, 247, 204, 154, 83, 55 (100%).
'H-NMR (300 MHz, DMSO-d6): 7.41 (d, J = 10.6, 1h); 6.69 (d, J = 6.0, 1H); 6.55 (t, J = 74.0, 1H); 3.83 (d, J = 6.0, 2H); 1.34 (s, 12H); 1.23 (m, IN); 0.57 (m, 2H); 0.42 (m, 2H).
Example A46: 1 -[4-Cyclopropylmethoxy-3-(4,4,5,5-tetramethyi-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethanone
A suspension of 1-(3-Bromo-4-cyclopropylmethoxy-phenyl)-ethanone from example A23 (3.00 g, 11.1 mmol), potassium acetate (3.30 g, 33.3 mmol), bis(pinacolato)diboron (5.70 g, 22.2 mmol) and 1,1'-bis(dipheny[-phosphino)ferrocene palladium-(ll)-chloride (0.90 g, 1.1 mmol) in 1,4-dioxane (50 mL) is heated under a nitrogen atmosphere for 4h at lOO'C. After cooling to ambient temperature the solvent is evaporated. The mixture is purified by column chromatography on silica gel (n-hexane / ethyl acetate (65:35 v/v) to give the title compound as a off white solid. Yield: 3.13 g.
MS (ESI): m/z = 317 (MH", 100%).
1H-NMR (300 MHz, DMSO-d6): 8.02 (m, 2H); 7.00 (m, 1H); 3.97 (d, J = 6.0, 2H); 2.50 (s, 3H); 1.30 (s, 12H); 1.23 (m. 1H); 0.50 (m, 4H).

The following compound is obtained analogously to the procedure described in above example A46.
Example A47: 1-[4-Cyclopropylmethoxy-2-methyl-5-(4,4,5,5-tetramethyl-[1,3:2]dioxabQrolan-2-yl)-phenyl]-ethanone
Starting from 1-(5-bromo-4-cyclopropylmethoxy-2-methyl-phenyl)-ethanone (example A6) the title compound is obtained as off-white solid after column chromatography on silica gel. MS (ESI): m/z = 331 (MH*, 100%).
'H-NMR (300 MHz, DMSO-de): 7.95 (s, 1H); 6.83 (s, 1H); 3.98 (d, J = 6.0, 2H); 2.50 (m, 6H); 1.35 (m, 1H); 1.30 (s. 12H); 0.60-0.30 (m, 4H).
Example A48: 4-(5-Cyclopropylmethoxy-1,3 benzodioxol-4-yl)-5H-pyrrolo(3,2-d]pyrimidine-7-carboxylic acid ethyl ester
A 25 ml pressure vial is charged with 4-chloro-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester (0.90 g; 4.0 mmol) prepared according to the procedure described in US 2005/124623A1, 2M aqueous CS2CO3 solution (6.0 mL), dimethoxyethane (10.0 mL) and PdCl2(PCy3)2 (236 mg, 0.32 mmol) (Cy = cyclohexyl). The mixture is heated to 150°C for 5 min under microwave irradiation. After cooling (o ambient temperature, 5-cyclopropylmethoxy-4-(4,4,5,5-teframethy(-[13,2]dioxaborolan-2-yl)-benzo[1,3]dioxole from example A29 (1.91 g; 5.0 mmol) is added to the reaction vial and the mixture is heated to 150°C for 30 min under microwave irradiation. After cooling to ambient temperature, water (10.0 mL) is added. The precipitated crude product is collected by suction filtration and washed with several small portions (10 to 25 mL) of DME / Wfater (1:2 v/v). Crude products from ten reactions are combined and dissolved in hot DME. The hot solution is filtered through a short column of neutral alumina containing 5 wt% of water. The column is washed with several portions of hot DME. The combined filtrates are evaporated to dryness. The crude is crystallized from DME / toluene to give the title compound as colorless solid. Yield 11.58 g MS (ESI): m/z = 404 (MNa"); 382 (MH*, 100 %)-
1H-NMR (200 MHz, DMSO-d6): 12.36 (s, 1H, -NH); 9.01 (s, 1H); 8.39 (s, IN); 7.00 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 5.99 (s, 2H); 4.31 (qu, J = 7.1, 2H); 3.75 (d, J = 6.7. 2H); 1.33 (t, J = 7.1, 3H); 0.87 (m, 1H); 0.29 (m, 2H); 0.08 (m, 2H).
The following compounds are obtained analogously to the procedure described in above example A48.
Example A49; 4-(5-Cyclobutylmethoxy-benzo(1,3]dioxo)-4-yl)-5H-pyrrolof3,2-c(lpynmfdine-7-carboxylic acid ethyl ester
Starting from 4-chloro-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester and 5-cyclobutylmethoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzo[1,3]dioxole (example A30) the title compound is obtained as colorless solid.

MS (ESI): m/z = 396 (MH*, 100%); 382 (MH+-CH2).
'H-NMR (400 MHz, DMSO-d6):. 12.42 (br.s, 1H, -NH); 9.00 (s, IN); 8.37 (d, J =3.0, IN); 7.01 (d, J = 8.6, 1H); 6.59 (d, J = 8.6, IN); 6.00 (s, 2H); 4.31 (qu, J = 7.1, 2H); 3.84 (d, J = 6.1, 2H); 2.36 (m, 1H); 1.65 (m, 3H); 1.50 (m, 3H); 1.33 (t, J = 7.1, 3H).
Example A50: 4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester:
Starting from 4-chloro-5H-pyrrolo[3.2-d]pyrimidine-7-carboxy]ic acid ethyl ester and 2-(2-cyc!opropylnnethoxy-4-methoxy-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (example A36) the title compound is obtained as colorless solid. MS (ESI): m/z = 390 (MNa*); 368 (MM*, 100%); 354 (MH'-CHa).
'H-NMR (200 MHz, DMSO-d6):. 12.03 (br.s, IN, -NH); 8.98 (s, 1H); 8.32 (s, IN); 7.59 (d, J = 8.2. 1H); 6.72 (dd,J1 = 8.2, J2 = 2.3, 1H); 6.69 (d, J = 2.3, 1H);4.31 (qu, J = 7.1, 2H); 3.91 (d, J = 6.9. 2H); 3.86 (s, 3H); 1.33 (t, J = 7.1, 3H); 0.96 (m, 1H); 0.35 (m, 2H): 0.23 (m, 2H).
Example A51: 4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartxjxytic acid ethyl ester:
Starting from 4-chloro-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester and 2-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (example A37) the title compound is obtained as colorless solid. MS (ESI): m/z = 390 (MNa'); 368 (MH\ 100%); 354 (MH^-CH2).
'H-NMR (200 MHz, DMSO-d6): 12.10 (br.s, 1H,-NH); 9.04 (s, 1H); 8.36 (d, J =3.2, 1H); 7.19 (t, J = 1.7, 1H);7.11 (t, J= 1.7, 2H); 6.69 (d, J = 2.3. 1H);4.31 (qu, J = 7.0, 2H); 3.81 (d, J = 6.8, 2H); 3.77 (s. 3H); 1.34 (I, J = 7.0, 3H): 0.91 (m, 1H); 0.32 (m, 2H); 0.15 (m, 2H).
Example A52: 4-(2-Cy clopropy I methoxy-4-f lu oro-pheny l)-5H-py rrolo[3,2-d] py rim id i ne-7-carboxylic acid ethyl ester:
Starting from 4-chloro-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester and 2-(2-cyciopropylmethoxy-4-fluoro-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (example A38)the title compound is obtained as colorless solid. MS (ESI): m/z = 378 (MNa*); 356 (MH*. 100 %).
'H-NMR (400 MHz, DMSO-d6): 12.18 (br.s, IN, -NH); 9.02 (s, 1H); 8.39 (s, 1H); 7.65 (dd. J, = 8.4, J2 = 2.3, 1H);7.08(dd,J1 = 11.5, J2 = 2.3, IN); 6.96 (ddd, J, = J2 = 8.4. J3 =2.3); 4.31 (qu,J = 7.1. 2H); 3.91 (d, J = 7.0. 2H); 1.33 (t, J = 7.1, 3H); 0.95 (m. 1H); 0.35 (m, 2H); 0.21 (m, 2H).
Example A53: 4-(2-cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartmxylic acid ethyl ester:

Starting from 4-ch\oro-5H-pyrro}ol3,2-d]pynmidine-7-carboxyl'ic add ethy} ester and 2-(2-
cyclopropylmethoxy-5-fluoro-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (example A39) the
title compound is obtained as colorless solid.
MS (ESI): m/2 = 378 (MNa*); 356 {MH+ 100%); 342 (MH'-CH;),
'H-NMR (200 MHz, DMSO-d6): 12.20 (br.s, 1H, -NH); 9.04 (s, 1H); 8.41 (s, 1H); 7.46-7.32 (m, 2H);
7.18 (dd, J1 = 8.9, Jj = 4.4,1H); 4.32 (qu, J = 7.1, 2H); 3.87 (d, J = 6.9, 2H); 1.34 (t, J = 7.1, 3H);
0.93 (m, IN); 0.33 (m, 2H); 0.17 (m, 2H).
Example A54: 4-(2-Cyclopropylmethoxy-ptienyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester:
Starting from 4-chloro-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethiyl ester and 2-(2-cycIopropylnnethoxy-phenyl)-4,4,5,5-tetrame[hyl-[1,3,2]dioxaborQlane (example A40) the title compound is obtained as colorless solid. MS (ESI): m/z = 360 (MNa*); 338 (MH*); 324 (MH'-CH2, 100%).
'H-NMR (400 MHz, DMSO-d6): 12.17 (br.s, 1H, -NH); 9.04 (s. 1H); 8.38 (d, J =3.4, 1H); 7.62 (dd, J, = 7.5 Jj = 1.2, 1H); 7.53 (ddd, J, = 8.6, J; = 7.5, Ja = 1.2, 1H); 7.17 (d, J = 8.6, 1H); 7.12 (d, J = 7.5, 1H); 4.32 (qu, J = 7.1, 2H); 3.90 (d, J = 6.9, 2H); 1,32 (t, J = 7.1, 3H); 0.95 (m, 1H); 0.34 (m, 2H); 0.22 (m, 2H).
Example A55; 4-(2-Cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester:
Starting from 4-chi!oro-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethiyl ester and 2-(2-cyclopropy1methoxy-4-fluoro-5-methoxy-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (example A35) the title compound is obtained as colorless solid. MS (ESI): m/2 = 389 {MH*, 100 %)
'H-NMR (300 MHz, DMSO-da): 12.11 (br.s, 1H, -NH); 9.03 (s, 1H); 8.38 (d, J = 3.2, 1H, -NH); 7.39 (d, J = 9.8, 1H); 7.18 (d, J = 13.4, 1H);4.31 (qu, J = 7.1, 2H); 3.84 (s, 3H & d, J = 5.1, 2H); 1.34 (t, J ^ 7.1, 3H); 0.92 (m, 1H); 0.33 (m, 2H); 0.15 (m, 2H).
Example A56: 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-ptienyl)-5H-pyrrolo[3.2-d]pyrimidine-7-carbioxylic acid ethyl ester:
Starting from 4-chloro-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester and 2-(2-cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (example A42) the title compound is obtained as pale yellow solid. MS (ESI): m/2 = 408 (MNa'); 386 (MH*, 100 %).
'H-NMR (400 MHz, DMSO-d6); 12.06 (br.s, 1H, -NH); 9.00 (s, 1H); 8.37 (d, J = 2.7, 1H); 7.48 (d, J = 11.9, 1H); 6.92 (d, J = 7.3, 1H); 4.32 (qu, J = 7.1, sH); 3.97 (s, 3H); 3,94 (d, J = 6.9, 2H); 1.34 (t, J = 7.1, 3H); 0.96 (m, 1H); 0.37 (m, 2H), 0.21 (m, 2H).

Example A57; 4-(5-Acetyl-2'Cyclopropytmethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester
Starting from 4-chlDro-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester and 1-[4-cyclopropylmethoxy-3-(4,4,5,5-(etramethy(-[1,3,2]dfoxaboralan-2-yl)-phenyl]-ethanone (example A46) the title compound is obtained as colorless solid. MS (ESI): m/z = 386 (MH*, 100 %).
'H-NMR (400 MHz, DMSO-d6): 12.30 (s, 1H,-NH); 9.08 (s, 1H), 8.42 (d, J = 3.5, 1H); 8.20 (d, J = 1.5 Hz, 1H); 8.12 (dd,J1 = 9.0, J2= 1.5, 1H); 7.25 (d, J = 9.0, 1H); 4.34 (q, J = 7,0, 2H); 4.05 (d, J = 7,0, 2H); 2.60 (s, 3H); 1,33 (t, J = 7.0, 3H); 1.00 (m, 1H); 0,35 (m, 2H); 0,24 (m, 2H).
Exannple A58: 4-(5-Acetyl-4-methyl-2-cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-cqpyrimldine-7-carboxylic acid ethyl ester
Starting from 4-chloro-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester and 1-[4-cydopropylmefhoxy-2-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yt)-phenyl]-ethanone (example A47) the title compound is obtained as colorless solid, MS (ESI): m/z = 394 (MH*, 100 %).
'H-NMR (400 MHz, OMSO-de): 12.20 (s, 1H, -NH); 9.05 (s, 1H); 8.40 (s, 1H), 8,12 (s, 1H); 7.10 (s, 1H); 4.34 (q, J = 7.0, 2H); 3.95 (d. J = 7.0, 2H); 2.60 (s, 3H); 2.55 (s, 3H); 1.33 (t, J = 7.0, 3H), 0.95 (m, 1H); 0.38 (m, 2H); 0.24 (m, 2H).
Example A59: 4-(2-Cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrroIo[3,2-d]pyrimidine-7-carlMxylic acid ethyl ester
Starting from 4-chlQro-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester and 2-(2-cyclopropylmethcxy-5-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (example A41) the title compound is obtained as colorless solid. MS (ESI): m/z = 352(MNH*, 100%); 338 (MH+-CH2).
1H-NMR (400 MHz, DMSO-d6): 12.09 (br.s, 1H, -NH); 9.02 (s, 1H); 8.35 (s, 1H); 7.43 (s, 1H); 7.33 (d, J = 8.5, 1H); 7.05 (d, J = 8.5, IN); 4.32 (qu, J = 7.1, 2H); 3.86 (d, J = 6.9, 2H); 2.33 (s, 3H); 1.34 (t, J = 7.1. 3H); 0.94 (m, IN); 0.34 (m, 2H); 0,18 (m, 2H).
Example A60: 4-(5-Ettioxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester
Starting from 4-chloro-5H-pyrrolo[3,2-aflpyrimidine-7-carboxylic acid ethyl ester and 5-ethoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzo[1,3]dioxole (example A31) the title compound is obtained as colorless solid. MS (ESI): m/z = 356 (MH', 100 %).

1H-NMR (400 MHz, DMSO-d6); 12.37 (s, 1H, -NH); 9.01 (s, 1H); 8,39 (s, 1H): 7,01 (d, J = 8.6, 1H); 6.58 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.32 (qu, J = 7.1, 2H); 3.95(qu, J = 6.9, 2H}; 1.33 (t, J = 7.1, 3H); 1.03(t, J = 6.9, 3H).
Example A61: 4-(5-Propoxy-benzo[1,3]diQxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester
Starting from 4-ctiloro-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester and 5-propoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzo[1,3]dJoxole (example A32) the title compound is obtained as colorless solid. MS (ESI): m/z = 370 (MH*, 100 %).
1H-NMR (400 MHz, DMSO-d6): 12.40 (s, 1H, ^NH); 9.01 (s, 1H); 8.38 (d, J = 3.5, 1H); 7.01 (d, J = 8.6, 1H);6.58(d, J = 8.6, 1H); 6.00 (s, 2H); 4.31 (qu, J = 7.1, 2H); 3.84 (t, J = 6.4, 2H): 1.42 (m, 2H); 1.33 (t, J = 7.1, 3H); 0.61 (t, J = 7.4, 3H).
Example A62: 4-(5-Butoxy-benzo[1,3]dioxo!-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7"carboxylic acid ethyl ester
Starting from 4-chloro-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester and 5-butoxy-4-{4,4,5,5-tetramethyl-(1,3,2]dioxaborolan-2-yl)-benzo[1,31dioxole (example A33) the title compound is obtained as colorless solid. MS (ESI): m/z = 384 (MH*, 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.40 (s, 1H, -NH); 9.00 (s, 1H); 8.38 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.59 (d, J = 8.6, IN); 6.00 (s, 2H); 4.31 (qu, J = 7.1, 2H); 3.88 (t, J = 6.3, 2H); 1.38 (m, 2H); 1.33 (t, J = 7.1, 3H); 1.05 (m, 2H); 0.68 (t, J = 7.4. 3H).
Example A63: 4-[5-(2-methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester
Starting from 4-chloro-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester and 5-(2-methoxy-ethoxy)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzo[1,3]dioxole (example A34) the title compound is obtained as colorless solid. MS (ESI): m/2 = 386 (MH+ 100%); 372 (MH+-CHz).
1H-NMR (200 MHz, DMSO-d6): 12.32 (br.s, IN, -NH); 9.01 (s, 1H); 8.39 (s, 1H); 7.02 (d, J = 8.5. IN); 6.61 (d, J = 8.5, 1H); 6.01 (s, 1H); 4.31 (qu, J = 7.1, 2H); 4.02 (t, J = 4.6, 2H); 3.38 (t, J ^ 4.6, 2H); 3.00 (s, 3H); 1.33 (t, J = 7.1, 3H).
Example A64: 4-[4-Methoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-dIpyrrmidine-7-cartxjxylic acid ethyl ester

Starting from 4-chloro-5H-pyrrolo[3,2-c']pyrimidine-7-carboxylic acid ethy) ester and 2-[4-methoxy-
2-(2-methoxy-ethoxy)-phenyl]-4,4,5,5-tetramethy!-[1,3,2]dioxaborolane (example A43) the title
compound is obtained as colorless solid.
MS (ESI): m/z = 372 (MH*. 100%); 358 (MH^-CH2).
1H-NMR (200 MHz, DMSO-D6): 11.87 (br.s, 1H,-NH); 8.98 (s, 1H); 8.33 (s, 1H); 7.65 (d, J = 8.1
1H); 6-77 (s, 1H); 6.75 (dd, J1 = 8.1, Jj = 2.2,1H); 4.31 (qu, J = 7.1, 2H); 4.21 (m, 2H); 3.87 (s, 3H);
3.52 (m, 2H); 3.10 (s, 3H); 1.33 (t, J = 7.1. 3H).
Example A65: 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxymethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyltc acid ethyl ester
Under an atmosphere of argon Pd(0Ac)2 (0.26 g; 1.14 mmol) and tricydohexylphosphine (0.64 g; 2.28 mmol) is added to oxygen free dioxane (117.0 mL). The mixture is stirred for 15 min at ambient temperature. 2M Cs2CO2 solution in oxygen free water (38.9 mL; 77.8 mmol) is added followed by 4-ch)oro-5H-pyrrok>l3,2-d\pyrimi6}n&-7-carboxyyic acid ethy] Bsier prepared according to the procedure described in US 2005/124623A1 (5.85 g; 25.95 mmol). The mixture is heated to 80°C before addition of 2-(2-Cyclopropylmethoxy-5-fluoro-4-methoxymethoxy-phenyl)-4,4,5,5-letramethyl-[1,3,2]dioxaborolane from example A44 (10.05 g; 28.53 mmol). Afterwards the stirred reaction mixture is heated at 100°C over night.
After addition of decolorizing charcoal (one spatula) the cooled reaction mixture is filtered through a plug of celite. The filtrate is concentrated under reduced pressure. The residue is distributed between water (100 mL) and dichloromethane (250 mL). The organic layer is separated the aqueous layer is extracted with dichloromethane (2x50 mL) and the combined organic layers are dried over MgSO4. The crud material is chromatographed on silica gel (dichloromethane; MeOH / 97:03) to give the title compound as colorless solid after triturating with tert-BuOMe. Yield: 7.30 g. MS (ESI): m/2 = 416 (MH*, 100%).
'H-NMR (300 MHz, DMSO-d6): 12,14 (br.s, 1H, -NH); 9.02 (s, 1H); 8.38 (d, J = 3.3, IN); 7.50 (d, J = 11.5, 1H); 7.03 (d, J - 6.9, 1H); 5.40 (s, 2H); 4.32 (qu J = 7.1, 2H); 3.88 (d, J = 6.9, 2H); 3.47 (s, 3H); 1.34 (t, J = 7.1, 3H); 0.95 (m, 1H); 0.35 (m, 2H); 0.20 (m, 2H).
The following compounds are obtained analogously to the procedure described in the above ax-ample A65.
Example A66: 4-[2-Cyclopropylmethoxy-4-(1,1 -difliioro-methoxy)-5-fluoro-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester
Starting from 4-chloro-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyllc acid ethyl ester prepared according to the procedure described in US 2005/124623A1 and 2-[2-cyclopropylmethoxy-4-(1,1-difluoro-nnethoxy)-5-f!uoro-phenyll-4,4,5,5-tetramethyl-[1,3,2]-dioxabolane (example A45) the title compund is obtained as colorless solid.

MS (ES)-): mlz = 420 (MH', 100%).
'H-NMR (300 MHz, DMSO-d6): 12.15 (br.s, IN, -NH); 9.04 (s, 1H); 8.44 (d, J = 3.5, 1H); 7.63 (d, J = 9.7, 1H); 7.40 (t, J = 73.0, 1H); 7.18 ( d, J = 6.6, IN); 4.32 (qu, J = 7.1, 2H); 3.90 (d, J = 6.9, 2H); 1.33 (t, J = 7.1, 3H); 0.94 (m, 1H); 0.35 (m, 2H); 0.20 (m, 2H).
Example A67: 4-(5-Cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-c9rboxylic acid
4-(6-CyclopropyJmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-cJ]pyrimJdine-7-carboxylic acid ethyl ester (9.53 g; 25,0 mmol)from example A48 is suspended in dioxane (170 mL)and water (100 mL). After addition of LiOH (2.99 g; 125.0 mmol) the reaction mixture is stirred at 100°C over night. The resulting solution is evaporated to dryness. The residue is dissolved in hot (60-90°C) water (250 mL) and pH is adjusted to 2-3 by addition of 2M citric acid while still hot. After cooling to ambient temperature the precipitated product is collected by suction filtration, washed with water, etbanoi and dried in high vacuo at 50°C to yieid S.22 g of the title compound as pate ye))ow solid. MS (ESI): miz = 354 (MM", 100 %)-
'H-NMR (300 MHz, DMSO-d6): 12.28 (br.s, 1H, -NH); 12.19 (br.s, 1H. -OH); 8.99 (s, 1H); 8.34 (d, J = 3.4, 1H); 7.00 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 3.76 (d, J = 6.7, 2H); 0.88 (m, 1H); 0.29 (m,2H); 0.09 (m,2H).
The following compounds are obtained analogously to the procedure described in above example A67.
Example A68: 4-(5-CycIobutylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolol3,2-d]pyrtmidine-7-carboxylic acid
4-(5-Cyclobutylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo(3,2-d]pyrinnidine-7-carboxylic acid ethyl ester (example A49) is used as starting material to give the title compound as pale yellow solid. MS (ESI): m/2 = 324 (MH^-CO2, 100 %); 256 (MH'-COs -C5H8).
'H-NMR (200 MHz, DMSO-d6): 12,32 (br.s, IN,-OH); 12,10 (br.s, 1H,-NH); 8,97 (s, 1H);8,31 (d, J = 3,2, 1H); 7.01 (d, J = 8.5, 1H); 6.5B (d, J = 8.5, IN); 6.00 (s, 2H); 3.83 (d, J = 6.1, 2H); 2.38 (m, 1H);1.67(m, 3H); 1.49 (m,3H).
Example A69: 4-(5-Ethoxy-benzo[1,3]dioxoM-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid
4-(5-Ethoxy-benzo[1,3]dioxol-4-yl>-5H-pyrroloI3,2-d]pyrimidine-7~carboxylic acid ethyl ester (example AGO) was used as starting material to give the title compound as pale yellow solid. MS (ESI): m/z = 356 (MH*, 100 %).

1H-NMR (400 MHz, DMSO-d6); 12.37 (s, 1H, -NH); 9.01 (s, 1H); 8.39 (s, 1H}; 7.01 (d, J = 8.6, IH); 6.58 (d, J = 8.6, IH); 6.00 {s, 2H); 4.32 (qu, J = 7.1, 2H); 3.95 (qu, J = 6.9, 2H); 1.33 (t, J = 7.1, 3H); 1.03(t, J = 6.9, 3H).
Example A70: 4-(5-Propoxy-ben2oI1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c(lpyrimidine-7-carboxylic acid
4-{5-PrQpoxy-benzo[1,3]dioxol-4-yl)"5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester (example A61) was used as starting material to give the title compound as pale yellow solid. MS (ESI): m/z = 342 (MH*, 100 %).
1H-NMR (400 MHz, DMSO-d6): 12.31 (s. 1H, -NH); 12.19{ br.s, IH, -OH); 8.98 (s, IN); 8.33 (d, J = 3.4, 1H);7.01 (d, J = 8.6, IH); 6.59 (d, J = 8.6, 1H); 6.00 (s, 2H); 3.84 (t, J = 6.4, 2H); 1.42 (m,2H); 0.61 {t, J= 7.4, 3H).
Example A71 -. 4-(5-Butoxy-benzoyl ,35dioxoi-4-vl)-5H-'pyrrolo[3,2--d]pyrimidine-7-carboxylic acid
4-(5-Butoxy-benzon,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester (example A62) was used as starting material to give the title compound as pale yellow solid. MS (ESI): m/z = 356 (MH*, 100 %).
'H-NMR (300 MHz, DMSO-d6): 12.31 (s, IH, -NH); 12.06 (br.s, IN, -OH); 8.99 (s, IH); 8.33 (d, J = 2.3, IH); 7.01 (d, J = 8.6, IH); 6.59 (d, J = 8.6, IH); 6.00 {s, 2H); 3,89 (t, J = 6.4. 2H); 1.48 (m, 2H); 1.03(m, 2H);0.68(t, J = 7.4. 3H).
Example A72: 4-[5-(2-MethQxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-c(tpyrimidine-7-carboxylic acid
4-[5-(2-MGthoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d)pyrimidine-7-carboxylic acid ethyl ester (example A63) was used as starting material to give the title compound as pale yellow solid. MS (ESI): m/z = 358 (MH*, 100%).
1H-NMR (200 MHz, DMSO-d6): 12.22 (br.s, 2H, -NH & -OH); 8.98 (s, 1H); 8.34 (s, IH); 7.02 (d, J = 8,6, 1H); 6.61 (d, J = 8.6, 1H); 6.01 (s, IH); 4.02 (t, J - 4.7, 2H); 3.39 (t, J = 4.7. 2H); 3.00 (s, 3H).
Example A73: 4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrro!of3,2-d)pyrimldine-7-carboxylic acid
4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester (example A50) is used as starting material to give the title compound as pale yellow solid. MS (ESI): m/z = 340 (MH*, 100 %).
1H-NMR (200 MHz, DMSO-d6): 11.95 (br.s, 2H. -NH, -OH); 8.96 (s, IH); 8.28 (d, J = 2.6, 1H); 7.59 (d, J = 8.3, IH); 6.72 (dd, J, = 8.3, Jz = 2.2, IH); 6.69 (d, J = 2.2, 1H}; 391 (d, J = 6.9, 2H); 3.86 (s, 3H); 0.97 (m, 1H); 0.35 (m, 2H); 0.23 (m, 2H).

Example A74:4-[4-Methoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyiic acid
4~[4-Methoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester {example A64) was used as starting material to give the title compound as pale yellow solid. MS (ESI): m/2 = 344 (MH', 100%).
'H-NMR (200 MHz, DMSO-d6): 12.11 (br.s, 1H, .OH); 11.80 (br.s, IN, -NH); 8.96 (s, 1H); 8.30 (d, J = 3.4, 1H); 7.66 (d, J = 8.1, 1H); 6,77 (s, 1H); 6.75 (dd, J, = 8.1, Js = 2.2, 1H); 4.22 (t, J = 4.6, 2H); 3,87 {s, 3H); 3.53 (t, J = 4,6, 2H); 3.10 (s, 3H).
Example A75: 4-(2-Cyclopropylrnethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrlmidine-7-carboxyiic acid
4-(2-Cyclopropylm6thoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester (example A,51) te used as starting material to give the title compound as pale yellow solid. MS(ESI):m/z=340{MH+ 100%).
'H-NIVIR (200 MHz, DMSO-d6): 12.06 (br.s, 2H, -NH, -OH); 9.01 (s, 1H); 8,31 (s, 1H); 7.17 (d, J = 1.8, 1H); 7,11 (t. J = 1.8, 2H); 3.82 (d, J = 6.8, 2H); 3.77 (s, 3H); 0.92 {m, 1H); 0.32 (m, 2H); 0.14 (m,2H).
Example A76: 4-(2-Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyiic acid
4-(2-Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester (example A52) is used as starting material to give the title compound as pale yellow solid. MS (ESI): m/z = 328 (MH' 100%).
'H-NMR (400 MHz, DMSO-d6); 12,10 (brs, 2H, -NH, -OH); 8,99 (s, 1H); 8.34 (s, 1H); 7.65 (dd, J, = 8.4, J2 = 7.0. 1H); 7.07 (dd, J, = 11.5, Jj = 2.3, 1H); 6.95 (ddd, J1 = J2 = 9-9, J3 = 2.3, 1H);3.92(d,J = 7.0, 2H); 0.96 (m, IN); 0.36 (m, 2H); 0.21 (m, 2H).
ExampleA77: 4-(2-Cyclopropylmethoxy-5-fluoro-phenyI)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid
4-(2-Cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester (example A53) is used as starting material to give the title compound as pale yellow solid. MS (ESI); m/z = 328 (MH\ 100 %).
1H-NMR (200 MHz, DMSO-d6): 12.15 (br.s, 2H, -NH, -OH); 9.02 (s, 1H); 8.36 (s, 1H); 7.45-7.31 (m, 2H); 7.18 (dd, J1 = 9.0, J2 = 5.4, IN); 3.87 (d, J = 6.1, 2H); 0.94 (m, 1H); 0.34 (m, 3H); 0.17 (m,3H).
Example A78: 4-(2-Cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-o(|pyrimidine-7-carboxylic acid

4-{2-Cyclopropylmethoxy-phenyi)-5H-pyrrolo[3,2-d]pyrimJdine-7-carboxylic acid ethyl ester
{example A54) is used as starting material to give the title compound as pale yellow solid.
MS (ESI): m/z = 310 (MH", 100 %); 266 (MH'-COj).
1H-NMR {400 MHz, DMSO-d6); 12.18 (br.s, 1H, -NH/-OH); 12.09 (br.s, 1H, -NH/-OH); 9.01 (s, 1H);
8.32 {s, 1H); 7.62 {dd, J1 = 7.5, J; = 1.5, 1H); 7.52 (ddd, J, = 8.4, J; = 7.5, J3 = 1.5, 1H); 7.17 (d, J =
8.4, 1H); 7.12 (d, J =7.5, 1H); 3.91 (d, J = 6.9, 2H); 0-95 (m, 1H); 0.35 (m, 2H); 0.21 (m, 2H).
Example A79:4-(2-Cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrinnidine-7-carboxylic acid
4-{2-Cyclopropytmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid
ethyl ester (example A55) is used as starting material to give the title compound as pale yellow
solid.
MS (ESI): m/z = 358 (MH*, 100%); 314 (MH* -CO2).
'H-NMR (300 MHz, DMSO-d6): 12.04 (br.s, 2H, -NH, -OH); 9.01 (s, IN); 8.34 (s, 1H); 7.39 (d, J =
9.8, 1H): 7.17 (d, J = 13.4, 1H); 4.84 (d, J = 6.8, 2H & s. 3H); 0.93 (m, IHj; 0.33 (m, 2H); 0.16 (m,
2H).
Example A80:4-(2-Cyc!opropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d)pyrimldfne-7-carboxyIic acid
4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-plienyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid
ethyl ester (example A56) is used as starting material to give the title compound as pale yellow
solid.
MS (ESI): m/z = 358.0 (MM", 100 %).
1H-NMR (200 MHz, DMSO-d6): 12.17 (br.s, 1H, -OH); 12.02 (br.s, 1H, -NH); 8.98 (s, 1H); 8.34 (s,
1H); 7.49 (d, J = 11.9, 1H); 6.92 (d, J = 7.3, IN); 3.97 (s, 3H); 3.95 (d, J = 7.0, 2H): 0.96 (m, IN);
0.36 {m,2H); 0.22 (m,2H).
Example A81: 4-{5-Acetyl-2-cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartxjxyllc acid
4-(5-Acelyl-2-cyclopropylmethoxy-phenyl)-5H-pyrrolot3,2-d)pyrimidine-7-carboxylic acid ethyl ester
(example A57) is used as starting material to give the title compound as pale yellows solid.
MS (ESI); m/2 = 352 (MH*, 100 %).
1H-NMR(400MHz, DMS0-d6): 12.40 (s, 1H,-NH); 9.10 (s, 1H); 8,48(d, J = 3.0, 1H); 8.19 (d, J =
2.0, 1H); 8.13 (dd, J, = 9.0, Jj = 3.0 1H); 7.27 (d, J = 9.0, 1H); 4.00 (d, J = 7.0, 2H); 2.60 (s, 3H);
0.95 (m); 0.37 (m, 2H); 0.23 (m, 2H).
Exam pie A82: 4-(5-Acetyl-4-methy l-2-cy clopropy Im ethoxy-pheny l)-5H-pyrrolo [3,2-a]pynmidine-7-carboxylic acid

4-(5-Ac6tyl-4-methyl-2-cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid
ethyl ester (example A58) is used as starting material to give thie title compound as pale yellow
solid.
MS (ESI): m/z = 366 (MH*, 100 %).
1H-NMR{400MHz, DMS0-d6): 12.10 (s, IN,-NH); 9.05(s, 1H); 8.36 (d, J = 3.0, 1H);8.10(s, 1H);
7.10 (s, 1H); 4.00 (d, J = 7.0 2H); 2.60 (s, 3H); 2.55 (s, 3H); 1.00 (m, 1H); 0,38 (m, 2H); 0,24 (m,
2H).
Example A83: 4-{2-Cyclopropylmethoxy-5-fnethyl-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid
4-(2-Cyclopropylniethoxy-5-methyl-ptienyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbDxy)icacid ethyl ester (example A59) is used as starling material to give the title compound as pale yellow solid. MS (ESI): m/z = 324 (MM' 100%).
'H-NMR (400 MHz, DMSO-d6): 12.10 (br.s, 2H, -NH, -OH); 8.99 (s, 1H); 8.30 (s, 1H); 7.43 (d, J = 1.8, 1H); 7.32(dd, J, =8.4 J2= 1.8, 1H); 7,06 (d, J = 8.4, 1H); 3,86(d, J = 6.9, 2H); 2.33 (s, 3H); 0.94 (m, 1H); 0.33 (m, 2H); 0.18 (m, 2H).
Example A&4: 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxymethoxy-phenyl)-5H-pyrro lo[3,2-d] py rim id i ne-7-ca rboxy He acid
Starting from 4-{2-cyclopropylmethoxy-5-'fluoro-4-methoxymethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ethyl ester (example A65) the title compound is obtained as colorless solid.
MS (ESI): m/z = 388 (MH", 100%).
'H-NMR (300 MHz, DMSO-d6): 12,06 (br.s, 2H, -NH, -OH); 8.98 (s, 1H); 8.33 (s, 1H); 7.49 (d, J = 11.5, 1H); 7.02 (d, J = 7.1, 1H); 5,39 (s, 2H); 3.87 (d, J = 6.9, 2H); 3.47 (s, 3H); 0.94 (m, 1H); 0.34 (m, 2H);0.20(m,2H),
Example A85: 4-[2-Gyclopropylmethoxy-4-(1,1 -difluoro-methoxy)-5-fluoro-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylicacid
Starting from 4-[2-cycloprDpylmethoxy-4-(1,1-difluoro-methoxy)-5-fluoro-phenyl]-5H-pyrrolo[3,2-c/]pyrlmidine-7-car[X)xylic acid ethyl ester (example A66) the title compound is obtained as colorless solid.
MS (ESI): 394 (MH*, 100%).
1H-NMR (300 MHz, DMSO-d6): 1H-NMR (300 MHz, DMSO-d6): 12.16 (br.s, 2H, -NH, -OH); 9.02 (s, 1H); 8.38 (s, 1H); 7.63 (d, J = 10.8, 1H); 7.40 (t, J = 73.2, 1H); 7.18 ( d, J = 6.9, 1H); 3.90 (d, J = 6.9, 2H); 0.95 (m, 1H); 0.35 (m, 2H); 0.20 (m, 2H).

Example A86: 4-({1-[4-(5-Cyclopropylm6tlioxy-1,3-ben2odioxol-4-yi)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]-methanoyi}-aniino)-piperidine-1-carboxy!ic acid tert-butyl ester To a suspension of 4-{5-cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (3.53 g; 10.0 mmol) from example A67 in dry dichloromethane (50 mL) is added 1-(3-dimethiylaminopropyl>-3-ethylcartxxJiimide hydrochiloride (12.0 mmol), triethylamine (15.0 mmol) and l-hydroxybenzotriazole (10.0 mmol). The suspension is stirred at ambient temperature for one hour. To the resulting solution, 4-amino-piperidlne-1-carboxylic acid tert-butyl ester (12.0 mmol) is added and stirring is continued overnight at ambient temperature. The reaction mixture is loaded onto a silica gel column and purified by flash chromatography using acetic acid ethyl ester / 2-propanol (98 : 2 v/v). The eluate containing the product fraction is collected and evaporated. The product is triturated with n-hexane and dried in high vacuo at 50°C to yield 3.85 g of the title compound as while solid.
MS (ESI): m/z = 558 (MNa'); 536 (MH", 100 %); 480 {MH"-C4H8).
'H-NMR (400 MHz, DMSO-d6): 12.28 (s, 1H, -NH); 9.03 (s, 1H); 8.44 (d, J = 7.7, 1H, -NH); 8.29 (d, J = 3.2, 1H); 7.01 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.07 (m, 1H); 3.87 (~ d, J ~ 13.5, 2H); 3.76 (d, J = 6.8, 2H); 1.94 (~ dd, J1 ~ 12.8, Jj ~ 3.4, 2H); 1.46 ( m, 2H); 1.42 (s 9H); 0.87 (m, 1H); 0.27 (m, 2H); 0.12 (m, 2H).
The following compounds are obtained analogously to the procedure described in above example A86.
Exannple A87: trans-(4-{[4-(5-Cyclopropylmethoxy-benzo(1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-cyclohexyl)-carbamic acid tert-butyl ester Starting from 4-(5-cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (example A67) and trans-{4-amino-cyclohexyl)-carbamic acid tert-butyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 550 (MH". 100%); 494 (MH*-C4H8).
1H-NMR (400 MHz, DMSO-d6): 12.26 (br.s, 1H, -NH); 9.02 (s, 1H); 8.29 (d, J = 8.1,1H, -NH); 8.27 (s, 1H); 7.00 (d, J = 8.6, 1H); 6.74 (d, J = 7.7, IN, -NH); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 3.76 (d, J = 6.7, 2H & m, 1H); 1.99 (m, 2H); 1.85 (m, 2H); 1.39 (s, 9H); 1.43-1.26 (m,4H); 0.85 (m, 1H); 0.29 (m, 2H);0.10(m,2H).
Example A68: cis-(4-{[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-cyclohexyl)-carbamic acid tert-butyl ester Starting from 4-(5-cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyr[midine-7-carboxylic acid (example A67) and cis-(4-amlno-cyclohexyl)-carbamic acid tert-butyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 550 (MH', 100%); 494 (MH+-C4H8); 450 (MH+-C5H6O2).

1H-NMR (400 MHz, DMSO-d6); 12.27 (br.s, 1H. -NH); 9.06 (s, 1H); 8.60 (d, J = 7.8, IN, -NH); 8.27 (s, 1H); 7.00 (d, J = 8.6, 1H); 6.94 (d, J = 6.7, 1H, -NH); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.02 (m, 1H); 3.77 (d, J = 6.7, 2H); 3.45 (m. 1H); 1.78 (m, 2H); 1.69-1.56{m, 6H); 1.39 (s, 9H); 0.86 (m, 1H); 0.30 (m,2H); 0.11 (m, 2H).
Example A89; (S)-3-{[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester Starting from 4-(5-cyclopropy(methoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-dJpyrimid(ne-7-carboxylic acid (example A67) and (S)-3-amino-pyrrolidine-1-carboxylic acid tert-butyl ester the title compound is obtained as colorless solid, MS (ESI): m/z = 522 (MH\ 100%); 466 (MH+-C2H6).
'H-NMR{300MHZ, DMSO-d6): 12.31 (br.s, 1H,-NH); 9.02 {s, 1H); 8.55 (d, J = 6.9, 1H, ~NH);8.31 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 6,01 (s, 2H); 4.50 (m, 1H); 3.76 (d, J = 6.7. 2H); 3.64 (m, 1H); 3.44 (m, 2H); 3.24 (m, 2H>; 2.21 (m, 1H); 1.96 (m, 1H); 1.42 (s, 9H); 0.87 (m, 1H); 0.29 (m,2H); 0.11 (m, 2H).
Example A90: (R)-3-{[4-(5-Cyc)opropylmethoxy-benzo[1,3]dioxol-4-yJ)-5H-pyrrofo[3,2-c/]pyrimidine-7-carbonyl]-amino}-pyrrolidine-1-carboxy!lc acid tert-butyl ester Starting from 4-(5-cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartxjxylic acid (exampie A67) and (R)-3-amino-pyrfolidin8-1-carboxylic acid tert-buty) ester the title compound Is obtained as colorless solid. MS (ESI): m/z = 522 (MH\ 100%); 466 (MH+-C4H8).
'H-NMR (300 MHz, DMSO-d6): 12.31 (br.s, 1H, -NH); 9.02 (s, 1H); 8.55 (d, J = 6.9, 1H, -NH); 8.31 (s, 1H);7.01 (d, J = 8.6, 1H); 6.56(d, J = 8.6, 1H); 6,01 (s, 2H); 4.50 (m, 1H); 3.76 (d, J = 6.7, 2H); 3.64 (m, 1H); 3.44 (m, 2H); 3.24 (m, 2H); 2.21 (m, 1H); 1.96 (m, 1H); 1.42 (s, 9H); 0.87 (m, 1H);' 0.29(m, 2H);0.11 (m, 2H).
Example A91: 4-({[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-methyl)~piperidine-1-carboxylrc acid tert-butyl ester Starting from 4-(5-cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrlmidine-7-carboxylic acid (example A67) and 4-aminomethyl-piperidine-1-carboxylic acid tert-butyl ester the title compound is obtained as colorless solid.
Example A92: 3-{{[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-methyl)-piperldine-1-carboxylic acid tert-butyl ester Starting from 4-(5-cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (example A67) and 3-aminomethyt-piperidine-1-cartioxylic acid tert-butyl ester the title compound is obtained as colorless solid.

Example A93: 3-({[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-methyl)-pyrrolidine-1-cartx)xylic acid tert-butyl ester Starting from 4-(5-cyclopropylnnettioxy-1,3-benzodioxol-4-yl)-5H-pyrroIo[3,2-d]pyrimidine-7-carboxylic acid (example A67) and 3-aminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester the title compound is obtained as colorless solid.
Example A94: 2-({(4-(5-Cyclopropylmethoxy-benzo[1,3jdloxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-methyl)-morptioline-4-carboxylic acid tert-butyl ester Starting from 4-(5-cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimtdine-7-carboxylic acid (example A67) and 2-amiriomethyl-morpholine-4-carboxylic acid tert-butyl ester the title compound is obtained as colorless solid.
Example A95: 2-({[4-(5-Cyclopropylmethoxy-benzo[1,3Jdioxol-4-yl)-5H-pyrrolo[3,2-dlpyrimidine-7-carbonyl]-amino}-methyl)-morpholine-4-carboxylic acid tert-butyl ester Starting from 4-(5-cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyljc add (example A67)and S-amino-azefidine-l-carboxylic acid tert-butyl ester the title compound is obtained as colorless solid.
Example A96: (S)-3-{[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidlne-7-carbonyl]-amino}-piperidine-1-cartK)xylic acid tert-butyl ester Starting from 4-(5-cyclopropylmethoxy-1,3-benzodloxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartoxylic acid (example A67) and (S)-3-amlno-piperidine-1-carboxylic acid tert-butyl ester the title compound is obtained as colorless solid.
Example A97: (R}-3-{[4-(5-Cyclopropylmetfioxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c^pyrimidine-7-carbonyl]-amino}-piperidine-1-carboxyljc acid tert-butyl ester Starting from 4-(5-cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H'pyrrolo[3,2-d]pyrimidine-7-cartXDxylic acid (example A67) and (R)-3-amino-piperjdine-1-carboxylic acid tert-butyl ester the title compound is obtained as colorless solid,
Example A98: 4-{[4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrlmidine-7-carbonyl]-amino}-piperidine-1-cartxjxylic acid tert-butyl ester
Starting from 4-(2-Cyclopropylmethoxy-4-methDxy-phenyl)-5H-pyrroloI3,2-d]pyr!midine-7-carboxylic acid (example A73) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 522 (MH*, 100 %); 466 (MH+-C4H8); 422 (MH'-C5H8Oj).

1H-NMR (200 MHz, DMSO-d6): 11.89 (br.s, 1H, -NH); 9.00 (s, 1H); 8.51 (d, J = 7.8, 1H, -NH); 8.22 (s, 1H); 7,62 (d, J = 8.3, IN); 6.72 ( dd, J, = 8.3, J2 = 2.2, 1H); 6.69 (d, J = 2.2, IN & br.s, 1H, -NH); 3.92 (d, J = 6.8, 2H); 3.86 (s, 3H & m, 2H); 3.03 (m, 2H}: 1.94 (m, 2H); 1.42 (m, 4H & s, 9H); 0.97 (m, 1H); 0.35 (m, 2H); 0.24 (m, 2H).
Example A99: cis-(4-{[4-(2-Cyclopropylmethoxy-4-fnettioxy-phenyl)-5H-pyrrolo[3,2-d]pyrinnid)ne-7-carbonyi]-amino}-cyclohexyl)-carbamic acid tert-butyl ester
Starting from 4-(2-cycloprapylnnethoxy-4'methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (example A73) and cis-(4-amino-cyclohexyi)-carbamic acid tert-butyl ester tlie title compound is obtained as colorless solid.
MS (ESI): m/z = 536 (MM', 100 %); 480 (MH+-C4H9); 436 (MH+-C5H8Oj).
1H-NMR {200 MHz, DMSO-d6); 11.88 (br.s, 1H, -NH); 9.03 (s, 1H); 8.68 (d. J = 7.7, 1H, -NH); 8.20 (s, 1H); 7.62 (d, J = 8.3, 1H); 6.92 (br.s, 1H, -NH); 6.72 (dd, J, = 8.3, Jj ^ 2.2, 1H); 6.69 (d, J = 2.2, 1H); 4.04 (m, 1H); 3.92 (d, J = 5.9, 2H); 3.86 (s, 3H); 3.45 (m, 1H); 1.90-1.48 (m, 8H); 1,40 (s, 9H); 0.98 (m, 1H); 0.35 {m, 2H); 0.24 (m, 2H).
Example A100: trans-(4-{[4-(2-Cyciopropylmethoxy-4-mellioxy-phenyl)-5H-pyrrolo[3,2-c(|pyrimidine-7-carbonyi]-amino)-cyclohexyl)carbamic acid tert-butyl ester
Starting from 4-(2-cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyIic acid (example A73) and trans-{4-amino-cyclohexyl)-carbamic acid tert-butyl ester the title compound is obtained as colorless solid. MS (ESI): m/2 = 536 (MH+, 100 %); 480 (MH'-C4H8).
1H^NMR (200 MHz, DMSO-d6): 1189 (br.s, 1H,-NH); 9.00 (s, 1H); 8.36 (d, J = 7.8, 1H,-NH);8.19 (s, 1H); 7.62 (d, J = 8.3, 1H); 6.92 (br.s, 1H, -NH); 6.72 (dd, J, = 8.3, J2 = 2.2, IH); 6.69 (d, J = 2.2, 1H); 3.91 (d. J = 6.9, 2H); 3.86 (s, 3H); 3,78 (m, 1H); 3.28 (m, IH); 2.00 (m, 2H); 1.86 (m, 2H); 1.34 (m, 4H & s, 9H); 0.97 (m, 1H); 0.34 (m, 2H); 0.24 (m, 2H).
Example A101: trans-(4-{[4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrraio[3,2- Starting from 4-(2-cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyiic acid (example A75) and trans-(4-amino-cydohexyl)-carbamic acid tert-butyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 536 (MH+, 100 %); 480 (MH+-C4H8).
'H-NMR (400 MHz, DMSO-d6): 12.00 (br.s, IH, -NH); 9.05 {s, 1H); 8.34 (d, J = 7,7, IH, -NH); 8.23 (s, 1H); 7,20 (t, J = 1.6, 1H); 7.12 (d, J = 1.6, 2H); 6,74 (d, J = 7.7, IH, -NH); 3.87 (d, J = 6.9, 2H); 3.77 (s, 3H &m, 1H); 3.31 (m, 1H); 2,00 (m, 2H); 1.85 (m, 2H); 1.43-1.22 (m, 4H); 1,39 (s, 9H); 0,84 (m, 1H); 0.32 (m, 2H); 0.15 (m, 2H).

Example A102; cis-(4-{[4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-cf]pyrimidine-7-carbonyl]-amino}-cyclohexyl)-carbamic acid tert-butyl ester
Starting from 4-(2-cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (example A75) and cis-(4-amino-cyclohexyl)-carbamic acid tert-butyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 536 (MH+, 100 %); 480 (MH+-C4H8).
1H-NMR (400 MHz, DMSO-d6): 11.99 (br.s, 1H, -NH); 9.08 (s. 1H); 8.65 (d, J = 7.7, 1H, -NH); 8.24 (d,J = 3.3, 1H);7.19(t, J= 1.6, 1H);7.11 (d, J = 1.6, 2H); 6.95 (d, J = 6.1, 1H,-NH); 4.04 (m, 1H); 3.83 (d, J = 6.8, 2H); 3.78 (s, 3H); 3.45 (m, 1H); 1.79 (m, 2H); 1.70-1.56 (m, 6H); 1.40 (s. 9H); 0.90 (m, 1H); 0.33 (m, 2H); 0.16 (m, 2H).
Example A103: 4-{[4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)'5H-pyrrDlo[3,2-cOpyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester Starting from 4-(2-cyclopropylmethoxy-5-nnethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyiic acid (example A75) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester the title compound is obtained as colorless solid.
MS (ESI): m/z = 522 (MH+. 100 %); 466 (MH+-C4H8).
'H-NMR (200 MHz, DMSO-d6): 12.00 (br.s, 1H, -NH); 9.05 (s, 1H); 8.50 (d, J = 7.8, 1H. -NH); 8.26 (s, 1H); 7.19 (t, J = 1.7, IN); 7.11 (d, J = 1.7, 2H); 4.09 (m, IN); 3.86 (m, 2H); 3.83 (d, J = 6.9, 2H); 3.77 (s, 3H): 3.04 (m, 2H); 1.94 (m, 2H); 1.47 (m, 2H); 1.43 (s, 9H); 0.93 (m, 1H); 0.32 (m. 2H); 0.15 (m,2H).
Example A104: trans-(4-{[4-(2-Cyclopropylmelhoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-cflpyrimidine-7-carbonyl]-amino}-cyclohexyi)-carbamic acid tert-butyl ester Starting from 4-(2-cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-of]pyrimidine-7-carboxylic acid (example A76) and trans-(4-amino-cyclohexyl)-carbamic acid tert-butyl ester the title compound is obtained as colorless solid.
MS (ESI): m/z = 524 (MH+. 100 %); 468 (MH+-C1Ha); 424 (MH+-C4H8Oj).
1H-NMR(300IVIHz, DMSO-d6): 12.05 (br.s. 1H,-NH); 9.06 (s, 1H); 8.34 (d, J = 7.9, 1H;-NH);8.26 (s, IN); 7.67 (dd, J1 = 8.4, J2 = 7.2, 1H); 7.08 (dd, J1 ^^ 11.6, Ja= 2.4, 1H); 6.96 (ddd, J1 = J2 = 8.5, J3 = 2.4, IN); 6.72 (d, J = 7.6, 1H, -NH); 3.92 (d, J = 7.0, 2H); 3.79 (m, 1H); 3.13 (m, 1H); 2.00 (m, 2H); 1.85 (m, 2H); 1.39 (s, 9H & m, 4H); 0.96 (m, 1H); 0.36 (m, 2H); 0.22 (m, 2H).
Example A105: cis-(4-{[4-(2-Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrim/d/ne-7-carbonylJ-amino}-cyclohexy))-carbamic acid tert-butyl ester Starting from 4-(2-cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrroto[3,2-d]pyrimidlne-7-carboxylic acid (example A76) and cls-(4-amino-cyclohexyl)-carbamic acid tert-butyl ester the title compound is obtained as colorless solid.

MS (ESI): m/z = 524 (MH+, 100 %): 468 (MH+-C2H8); 424 (MH+-C5H8O2).
1H-NMR {300 MHz, DMSO-d6): 12.05 (br.s, 1H, -NH); 9.06 (s, 1H); 8.65 (d, J = 7.7,1H; -NH); 8.26 {d, J = 2.0, 1H); 7.67 (dd, J1 = 8.5, Ja = 7.0, 1H); 7.08 (dd, J1 = 11.6, Ja = 2.4, 1H); 6.96 (ddd, J1 = J2 8.5, J3 = 2.4,1H); 6.91 (br.s, 1H, -NH); 4.05 (m, 1H); 3.92 (d, J = 7.0, 2H); 3.45 (m, 1H); 1.79 (m, 2H); 1.73-1.51 (m, 6H); 1.40 (s, 9H); 0.97 (m, 1H); 0.36 (m, 2H); 0.22 (m, 2H).
Example A106: 4-{l4~(2-Cyc}opropyimethoxy-4-iluoro-phenyiy5H-pyrroh[3,2'd]pynmidine-7-carbonyl]-amino}-piperrdine-1-carboxylic acid tert-butyl ester
Starting from 4-(2-cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (example A76) and 4-amino-plperidine-1-carboxylic acid tert-butyl ester the title compound is obtained as colorless solid.
MS (ESI): m/z = 510 (iVlH'); 454 (MH+-C4H8. 100 %); 410 (MH+-C5H8O2),
'H-NMR (300 MHz, DMSO-do): 12.07 (br.s, 1H, -NH); 9.03 (s, 1H); 8.49 (d, J = 7.8, 1H; -NH); 8.29 (d, J = 2.4, 1H); 7.67 (dd, J, = 8.5, Jz = 7.0, 1H); 7.08 (dd, J, = 11.6, Jj = 2.4, 1H); 6.96 (ddd, J, = Jj = 8.5, J3 = 2.4, 1H); 4.06 (m, 2H); 3.92 (d, J = 7.0, 2H); 3.87 (m, 1H); 3.03 (m, 2H); 1.94 (m, 2H); 1.44 (m,2H); 1.42 (s, 9H); 0.96 (m, 1H); 0.36 (m, 2H); 0.22 (m, 2H).
Example A107: trans-{4-{[4-(2-Cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2~ c/]pyrimidine-7-carbonyl]-amino}-cyclohexyl)-carbamic acid tert-butyl ester Starti ng f rom 4-(2-cyclopropy lmethoxy-5-fluoro-phe nyl )-5H-py rrolo[3,2-d]py rim id i ne-7-carboxy I ic acid (example A77) and trans-(4-amino-cyclohexyl)-carbamic acid tert-buty) ester the title compound is obtained as colorless solid. MS (ESI): m/z = 524 (MH+, 100 %); 468 (MH+-C4H8).
'H-NMR(300MHz, DMSO-d6): 12.08 (br.s, 1H,-NH); 9.06 (s, 1H); 8.33 (d, J = 7.9, 1H,-NH); 8.28 (d, J = 3.0, 1H); 7.45-7.34 (m, 2H); 7.18 (dd, J1 = 9.1, J2 = 4.5, 1H); 6.72 (d, J = 7.3, 1H, -NH); 3.88 (d, J = 6.9, 2H); 3.79 (m, 1H); 3.29 (m, 1H); 2.00 (m, 2H); 1.85 (m, 2H); 1.39 (s, 9H & m, 4H); 0.94 (m, 1H); 0.33 (m, 2H); 0.18 (m, 2H).
Example A108: 4-{[4-(2-Cyclopropylmethoxy-5-fluoro-ptienyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester
Sla rting from 4-{2-cyclopropy Im ethoxy-5-f I uoro-phe ny I )-5H-py rrolo[3,2-c(lpy rim id i n e-7-carboxy I ic acid (example A77) and 4-amino-piperidine-1-carboxylrc acid tert-butyl ester the title compound is obtained as colorless solid.
MS (ESI): m/z = 510 (MH+, 100 %); 454 (MH+-C4H8); 410 (MH'-C5H8O2).
'H-NMR (300 MHz, DMSO-d6): 12.11 (br.s, 1H, -NH); 9.06 (s, 1H); 8.37 (d, J = 3.4, 1H); 8.48 (d, J = 7.8, IN, -NH); 8.30 (s, 1H); 7.46-7.34 (m, 2H); 7.19 (dd, J, = 9.1, J2 = 4.4, IN); 4.09 (m, IN); 3.88 (d, J = 6.9, 2H & m, 2H); 3.03 (m, 2H); 1,94 (m, 2H); 1.46 (m, 2H); 1.42 (s, 9H); 0.94 (m, 1H); 0.34 (m, 2H);0.18(m, 2H).

Example A109: trans-(4-{[4-(2-Cyclopropylmethoxy-phenyl)-5H-pyrro!o[3,2-d]pyrinnidine-7-carbonyl]-amino}-cyclohexyl)-carbamic acid tert-butyl ester
Starting from 4-(2-cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (example A78) and trans-(4-amino-cyclohexy})-carbamic add tert-butyi ester the title compound is obtained as colorless solid.
MS (ESI): m/z = 506 {MH+ 100 %); 450 {MH+-C1Hg).
1H-NMR (3000 MHZ, DMSO-d6): 12.02 (s, 1H, -NH); 9.05 (s, 1H); 8.34 (d, J = 7.8, 1H, -NH); 8.26 (s, 1H);7.63(dd, J1 = 7.6,J2= 1.7, 1H); 7.53 (ddd, J1 = 8.0, J2= 7.6, J3= 1.7, 1H); 7.17 (dd, J1 = 8.0, Js = 0.9, 1H); 7.13 (ddd, J, = J2 = 7.6, J3 = 0.9, 1H); 6.73 (d, J = 7.5, 1H, -NH); 3.91 (d, J = 6.9, 2H);3.78(m, 1H); 3.41 (m, 1H); 2.00 (m, 2H); 1.86 (m, 2H); 1.40 (s, 9H); 1.34(m,4H); 0.97 (m, 1H): 0.34 (m,2H); 0.21 (m, 2H).
ExampJe A110: 4-{[4-(2-Cyc)opropylmethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrim)dine-7-carbonyl]-amino}-prperfdlne-1-carboxylic acid tert-butyl ester
Starting from 4-{2-cyc!opropyimethoxy-phenyl)-5H-pyrro!o[3,2-d]pyrimidine-7-carboxylrc acid (example A78) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester the title compound is obtained as colorless solid.
MS (ESI): m/z = 492 (MM*, 100 %); 436 (MH+-C4H6).
1H-NMR (300 MHz, DMSO-d6): 12.06 (s, 1H, -NH); 9.05 (s, 1H); 8.51 (d, J = 7.8, 1H, -NH); 8.26 (s, 1H); 7.63 (dd, J1 = 7.6, J2 = 1.7, 1H); 7.53 (ddd, J1 = 8.0, J2 = 7.6, J3 = 1.7, 1H); 7,17 (dd, J1 = 8.0, J2 = 0.9, 1H); 7,13 (ddd, J1 = J2 = 7.6, J3 = 0.9, 1H); 4,09 (m, 1H); 3.91 (d. J = 6,9, 2H); 3.88 (m, 2H); 3.04 (m, 1H); 1.93 (m, 2H); 1.47 (m, 2H); 1.42 (s, 9H); 0.96 (m, 1H); 0.34 (m, 2H); 0.21 (m, 2H).
Example A111: 4-{[4-(2-Cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-c(Ipyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester Starting from 4-(2-Cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbmxylic acid (example A79) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 540 (MH+ 100 %); 484 (MH+-C4H8).
1H-NMR (300 MHz, DMSO-d6): 12.02 (br.s, 1H, -NH); 9.05 (s, 1H); 8.49 (d, J = 7.8, 1H, -NH); 8.28 (s, 1H); 7.41 (d, J = 9.8, 1H); 7.18 (d, J = 13.3, 1H); 4.09 (m, 1H); 3.98 (m, 2H); 3.85 (s, 3H); 3.84 (d, J = 6.7, 2H); 3.03 (m, 1H); 1,96 (m, 2H); 1.46 (m, 2H); 1.42 (s, 9H); 0.93 (m, 1H); 0.34 (m, 2H); 0.17 (m,2H).
Example A112: (R)-3-{[4-(2-Cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimldine-7-carbonyl]-amino}-piperidlne-1-carboxylic acid tert-butyl ester

starting from 4-(2-cyclopropy)methoxy-4-fluoro-5-methoxy-pheny))-5H-pyrro)o[3,2-d)pyrimidine-7-
cartraxylic acid (example A79} and (R)-3-amino-piperidine-1-carboxylic acid tert-butyl ester the title
compound is obtained as colorless solid.
MS (ESI); m/2 = 540 (MH\ 100 %); 484 (MH'-C4H8); 440 (MH+-C5H8O2).
1H-NMR (300 MHz, DMSO-d6): 12.02 (br.s, IN, -NH); 9.02 (s, 1H); 8,58 (d, J = 7.9, 1H, -NH); 8,30
(s, 1H); 7.41 (d, J = 9.9, IN); 7.19 (d. J = 13.4, 1H); 3.99 (m, 1H); 3.88 (s. 3H & d, J = 6.8, 2H);
3.62 (m, 1H); 3.38 (m,3H); 1.92 (m, 1H); 1.72 (m,2H); 1.53 (m, 1H); 1.29 (br.s, 9H); 0.92 (m, IN);
0.32 (m, 2H);0.18(m, 2H).
Example A113: (R)-3-{[4-(2-Cyclopropylmethioxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-buty! ester Starting from 4-(2-cyclopropylmethoxy-4-ftuoro-5-methoxy-ptienyl)-5H-pyrrolo[3,2-d]pyrimidine"7-cartMxylic acid (exampte A79) and (R)-3-amino-pyrrolidine-1-carboxylic acid tert-butyl ester the title compound is obtained as colorless solid. MS (ESI): m/2 = 526 (MH+, 100 %); 470 (MH'-C4H8).
1H-NMR (300 MHz, DMSO-d6): 12.06 (br.s, 1H, -NH); 9.04 (s, 1H); 8.60 (d, J = 6.9, 1H, -NH); 8,31 (d, J = 2.2, 1H); 7.41 (d, J = 9.9,1H); 7.18 (d, J = 13.4,1H); 4.51 (m, 1H); 3,85 (s, 3H & d, J = 6.7, 2H); 3,62 (m, 1H); 3,44 {m, 2H); 3.26 (m, 1H); 2.22 {m, 1H); 1.99 (m, 2H); 1.42 (s, 9H); 0.93 (m, 1H); 0.34 (m,2H); 0.17 (m,2H).
Example A114: trans-(4-{f4-(2-Cyctopropylmethoxy-5-fluoro-4-methoxy-pheny;)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino]-cyclohiexy1)-carbamic acid tert-butyl ester Starting from 4-(2-Cyclopropy!methoxy-5-fluoro-4-methoxy-ptienyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (example A80) and frans-(4-amino-cyc(otiexyl)-carbamic acid tert-butyl ester the title compound is obtained as colortess solid. MS (ESI): m/2 = 554 (MH+. 100 %); 498 (MH+-C4H8).
1H-NMR (400 MHz, DMSO-d6): 11.96 (br.s, 1H, -NH); 9.01 (s,lH); 8.35 (d, J = 7.8, 1H, -NH); 8.24 (s, 1H); 7.49 (d, J = 11.8, 1H); 6.92 (d, J = 7.3, IN); 6.74 (d, J = 7,8, 1H, -NH); 397 (s, 1H); 3.94 (d, J = 7.0, 2H); 3.77 (m, 1H); 1.99 (m,2H); 1.85 (m,2H); 1.43-1.24 (m, 4H); 1.39 (s, 9H); 0.96 (m, 1H); 0.36 (m, 2H); 0.22 (m, 2H).
Example A115: 4-{[4-(2-Cyclopropy!methoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-piperidine-1-carb)Oxylic acid tert-butyl ester Starting from 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phienyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (example A80) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester the title compound is obtained as colorless solid. MS (ESI): m/2 = 540 (MH+ 100 %); 484 (MH+-C4H6).

1H-NMR (300 MHz, DMSO-d6); 11-97 (br.s, 1H, -NH); 9.01 (s,lH); 8.50 (d, J = 7.8, 1H, -NH); 8.26 (s, 1H);7.49(d, J = 11.8, 1H); 6.93 (d, J = 7.3, 1H);4.07(m, 1H);3.97(s. 1H); 3.95 (d, J = 7.3, 2H); 3.87 (m, 1H); 3.03 (m, 2H); 1.93(m, 2H); 1.46(m, 2H); 1.42 (s, 9H); 0,97 (m, 1H); 0.36 (m, 2H),0.21 (m, 2H).
Example A116: (R)-3-{[4-(2-Cyclopropylnnethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrroto[3,2-d]pyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester Starting from 4'(2-Cyclopropylmethoxy-5-fluoro4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (example A80) and (R)-3-amino-piperidine-1-carboxylic acid tert-butyl ester the title compound is obtained as colorless solid.
MS (ESI): m/z = 540 (MH+ 100 %); 484 (MH+'-C1Ha); 440 (MH+-C5H8O2).
1H-NMR (300 MHz, DMSO-d6,): 11.97 (br.s, 1H,-NH); 8.98 (s, IN); 8.59 (d, J = 7,8, 1H,-NH);8.2S (s, 1H); 7.50 (d, J = 11.9. 1H); 0.93 (d, J = 7.3, 1H); 3,97 (s, 3H & m, 1H): 3.95 (d, J = 7.0, 2H): 3.63 {m, 1H); 3.36 (m, ZH); 1.91 (m, 2H); 1.73 (m, 2H); 1,55 (m,1H); 0,98 (m, 1H); 0.36 (m, 2H); 0.22 (m,2H).
Example All7: (S)-3-{[4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbQnyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester Starting from 4-(2-cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyiic acid (example A80) and (S)-3-amino-piperidine-1-carboxylic acid tert-butyl ester the title compound is obtained as colorless so(;d.
MS (ESI): m/z = 540 (MH+, 100 %); 484 (MH+-C4H8); 440 (MH+-C5H8O2).
'1H-NMR (300 MHz, DMSO-ds,): 11.97 (br.s, 1H,-NH); 8.98 (s, 1H); 8.59 (d, J = 7.8, 1H,-NH);8.28 (s, 1H); 7.50(d, J = 11.9, 1H); 6.93 (d, J = 7.3, 1H); 3.97 (s, 3H & m, 1H); 3.95(d, J = 7.0, 2H); 3.63 (m, 1H};3.36(m, 3H); 1.91 (m, 2H); 1.73 (m,2H); 1.55(m,1H); 0.96 (m, 1H); 0.36 (m, 2H); 0.22 (m, 2H).
Example A118: (R)-3-{[4-(2~Cyclopropylmethoxy-5-fluoro-4-methoxy-ptienyl)-5H-pyrrolo[3,2-c^pyrim]dine-7-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester Starti ng from 4-(2-cyclopropylmethoxy-5-fluoro-4-nn ethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimid in&-7-carboxylic acid (example ABO) and (R)-3-amino-pyrroiidine-1-carbioxylic acid tert-butyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 548 (MNa'); 526 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.00 (br.s, 1H, -NH); 9.00 (s, 1H); 8.61 (d, J = 6.9, IN; -NH); 8.28 (s, 1H); 7.50 (d, J = 11.9, 1H); 6.93 (d, J = 7.3,1 H); 4.51 (m, 1H); 3.96 (s, 3H); 3.95 (d, J = 7.1, 2H); 3.61 (m, 1H); 3.43 (m, 2H); 3.24 (m, 1H); 2,21 (m, 1H); 1.96 (m, 1H); 1.42 (s, 9H); 0.97 (m, 1H); 0.36 (m, 2H), 0.21 (m, 2H).

Example A119: 4-{[4-(2-Cyctopropylmethoxy-5-methyl-phenyl)-5H-pyrro!o[3,2-d]pyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester Starting from 4-(2-cyclopropylmethoxy-5-methyl-ptienyl)-5H-pyrrolQ[3,2-d]pyrimidine-7-carboxylic acid (example A83) and 4-amino-pjperi6ine-1-carboxylic acid tert-butyl ester the title compound is obtained as colorless solid.
MS (ESI): m/2 = 506 (MH\ 100 %}; 450 (MH+-C4H8].
1H-NMR400MHZ, DMSO-d6): 11.98 (br.s, 1H,-NH); 9.03 (s, 1H); 8.50 (d, J = 7.7, 1H,-NH); 8.24 (s, 1H); 7.44 (d, J = 2.0, 1H); 7.33 (dd, J, = 8.4, J2 = 2.0, 1H); 7.06 (d, J = 8.4, 1H); 4.09 (m, 1H); 3.86 (d, J = 6.9, 2H & m, 2H); 3.04 (m, 2H); 2.33 (s, 3H); 1.94 (m,2H); 1.46 {m,2H); 1.43 (s,9H); 0.94 (m, 1H); 0.33 (m, 2H); 0.19 (m, 2H).
Example A120: trans-(4-{[4-(2-Cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-cyclotiexyl}-carbamic acid tert-butyl ester Starting from 4-(2-cyclopropylmethoxy-5-methy(-phenyl)-5H-pyfro(o[3,2-d]pyrimidine-7-carboxy(ic acid (example A83) and trans-(4-amino-cyclohexyl)-carbamic acid tert-butyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 520 (MH\ 100 %); 464 (MH'-C1He).
1H-NMR400IV1Hz, DMSO-da): 11.95 (br.s, 1H,-NH); 9.03 (s, 1H); 8.35(d, J = 7.8, 1H,-NH);8.21 (s, 1H); 7.44 (s, 1H); 7.33 (d, J = 8,4, 1H); 7.06 (d, J = 8.4, 1H); 6.72 (d, J = 7.3, 1H, -NH); 3.86 (d, J = 6.9, 2H); 3.77 (m, 1H);3.29(m, 1H);2.33(s, 3H); 2.00 (m, 2H); 1.85 (m,2H); 1.44-1.23 (m, 4H); 1.39 (s, 9H); 0.94 (m, 1H); 0.33 (m, 2H); 0.18 (m, 2H).
Example A121: trans-[4-({1-[4-(5-CyclobutyImethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrlmidin-7-yl]-mettianoyl}-amino)-cyclohexyl]-carbamic acid tert-butyl ester Starting from 4-(5-Cyclobutylmethoxy-benzo[1,3]dioxQl-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (example A68) and trans-(4-amino-cydohexyl)-carbamic acid tert-butyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 564 (MH+); 508 (MH+-C4H6).
1H-NMR (400 MHz, DMSO-d6):12.28 (br.s. 1H, -NH); 9.02 (s, 1H); 8.28 (d, J = 7.9, 1H. -NH); 8.24 (d, J = 3.2, 1H); 7.50 (s, 1H); 7.02 (d, J = 8.6, 1H); 6.56(d, J = 8.6, 1H); 6.00(s, 2H); 4.30 (m, 1H); 3.76 (d, J = 6.8, 2H); 3.50 (m, 1H); 3.30 (m, 1H); 2.30 (m, 2H); 2.00 (m, 2H); 0.95 (m, 1H); 0.30 (m, 2H);0.10(m,2H).
Example A122:4-({1-[4-(5-Cyclobutylmethoxy-ben2o[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c(/pyrimidin-7-yl]-methanoyl}-amino>-piperidine-1carboxylic acid tert-butyl ester Starting from 4-(5-cyclobutylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartxjxylic acid (example A68) and 4-amino-piperidin6-1-carboxylic acid tert-butyl ester the title compound is obtained as colorless solid,

MS (ESI): m/z = 550 (MH+); 494 (MH'-C4H8); 450 (IV1H'-CBHSOS).
1H-NMR (400 MHz, DMSO-d6): 12.32 (br.s, 1H, -NH); 9.02 (s, 1H); 8.42 (d, J = 7.7, 1H, -NH); 8.28 (d, J = 1.8, , 1H); 7.01 (d, J = 8.6,1H); 6.72 (d, J = 7.5, IN, -NH); 6.59 (d, J = 8.6, 1H); 6.01 (s, 2H); 3.85 (d, J = 6.2, 2H); 3.77 (m, 1H); 3.30 (m, 1H); 2.38(m, 1H); 2.00 (m, 2H); 1.85 (m, 2H); 1.67 (m, 3H); 1.50 (m, 3H); 1.40 (s, 9H); 1.34 (m, 4H).
Example A123: 4-{[4-(5-Ethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester
Starting from 4-(5-ethoxy-benzo(1,3]d/oxo)-4-y!)-5H-pyrrolo[3,2-c')pyrimidine-7-cartx)xylic acid (example A69) and commercially available 4-amino-piperidine-l-carboxylic acid tert-butyt ester the title compound was obtained as colorless solid. MS (ESI): m/z = 510 (MH+, 100 %); 454 (MH+-aHa).
1H-NMR (400 MHz, DIVlSO-de): 12.28 (s, 1H, -NH); 9.02 (s, 1H); 8.43 (d, J = 7.8, 1H, -NH); 8.29 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.59 (d, J = 8.6, 1H); 6.01 (s, 2H); 4.07 (m, 1H); 3.96 (qu, J = 7.0, 2H); 3.87 (m, 2H); 3.03 (m, 2H); 1.92 (m, 2H); 1.43 (m, 2H & s, 9H); 1.03 (t, J = 7.0, 3H).
Example A124: (R)-3-{[4-(5-Ettioxy-benzo[1,3]dloxol-4-yl)-5H-pyrrolo[3,2-d)pyrimidine-7-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester
Starting from 4-(5-ettioxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (example A69) and commercially available (R)-3-amino-pyrrolidine-1-carboxylic acid tert-butyl ester the title compound was obtained as colorless solid. MS (ES(): m/z = 496 (MH+ 100 %); 440 (MH+-C1H^).
1H-NMR (300 MHz, DMSO-d6): 12.32 (s, 1H, -NH); 9.02 (s, 1H); 8.56 (d, J = 6.9, 1H, -NH); 8.32 (s, 1H); 7.02 (d, J = 8.6, 1H); 6.59 (d, J = 8.6, 1H); 6.01 (s, 2H); 4.52 (m, 1H); 3.96 (qu, J = 6.9, 2H); 3.62 (m, 1H); 3.50-3.37 (m,2H); 3.25 (m, 1H);2.22(m. 1H); 1.98 (m, 2H); 1.42 (s,9H); 1.04 (t, J = 6.9, 3H),
Example A125: 4-{[4-(5-Propoxy-benzo[1,3]dioxol-4-yl)-5H-pyrro[o[3,2-d]pyrimidine-7-cartxpnyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester
Starting from 4-(5-propoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine^7-carboxylic acid (example A70) and commercially available 4-amino-piperidine-1-carboxylic acid tert-butyl ester the title compound was obtained as colorless solid. MS (ESI): m/z = 524 (MH+, 100 %); 468 (MH+-C1Hg).
1H-NMR (400 MHz, DMSO-d6): 12.31 (s, 1H, -NH); 9.02 (s, 1H); 8.43 (d, J = 7,8, 1H, -NH); 7.95 (s, 1H); 7.01 (d, J = 8.6, IN); 6.58 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.04 (m, 1H); 3.85 (t, J = 6.4, 2H & m, 2H); 3.03 (m, 2H); 1.97 (m, 2H); 1.52-1.37 (s, 9H & m, 4H); 0.61 (t, J = 7.4, 3H).

Example A126: (R)-3-{[4-(5-Propoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-cart)onyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester
Starting from 4-(5-propoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d)pyrimidine-7-carboxylic acid (example A70) and commercially available {R}-3-amino-pyrrolidin8-1-carboxylic acid tert-butyl ester thie title compound was obtained as colorless solid. IVtS (ESI): m/z = 510 (MH+, 100 %); 454 (MH'-C4H8].
1H-NMR (300 MHz, DMSO-d6): 12.34 (s, 1H, -NH); 9.01 (s, 1H); 8.55 (d, J = 6.9, 1H, -NH); 8.30 (s, 1H); 7.02 (d, J = 8.6. 1H); 6.58 (d, J = 8.6, 1H); 6.01 (s. 2H); 4.51 (m, 1H); 3.85 (t, J = 6.4, 2H); 3.62 (m, 1H);3.42(m, 2H); 3.24 (m, 1H); 2,21 (m, 1H); 1.98 (m, 1H); 1.42(s, 9H&m, 2H); 0.62 (t, J = 7.4, 3H).
Example A127; 4-{[4-(5-Butoxy-benzo[1,3]dioxol-4-yi)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester
Starting from 4-(5-butoxy-benzo[1,3]dioxol-4-yl>-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (example A71) and commercially available 4-amino-piperidine-1-carboxylic acid tert-butyl ester \he title compound was obtained as colorless solid. MS (ESI): m/z = 538 (MH+, 100 %); 482 (MH'-C4H8).
1H-NMR 300 MHz, DMSO-d6): 12.31 (br.s, 1H, -NH); 9.02 (s, 1H); 8.43 (d, J = 7.8, IN, -NH); 8.28 {s, 1H); 7.01 (d, J = 8.6,1H); 6.59 {d, J = 8.6, 1H); 6.01 {s, 2H); 4.07 (m, 1H); 3.88 (t, J = 6.4, 2H & m, 2H); 3.03 (m, 2H); 1.94 (m, 2H); 1,52-1.34 (m, 4H); 1.42 (s, 9H); 1.04 (m, 2H); 0.69 (t, J = 7.4, 3H).
Example A128; 3-{(4-(5-Butoxy-benzo[1,3]dioxol-4-yl)5H-pyrrolo[3,2-d]pyrimidine-7-cartranyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester
Starting from 4-(5-butoxy-benzo[1,3]dioxcl-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (example A70) and commercially available 3-amino-piperidine-1-carboxylic acid tert-butyl ester the title compound was obtained as colorless solid. MS (ESI): m/z = 538 (MH+. 100 %); 482 (MH+-C1HB).
1H-NMR 300 MHz, DMSO-d6): 12.31 (br.s, 1H, -NH); 9.00 (s, 1H); 8.54 (d, J = 7.8, 1H, -NH); 8.29 (s, 1H); 7.01 (d, J = a.6, 1H); 6.59 (d, J = 8.6, 1H); 6.01 (s, 2H); 3-99 (m, 1H); 3.88/t, J = 6.4, 2H); 3.61 (m, 2H); 3.38 (m, 2H); 1.92 (m, 1H); 1.72 (m, 2H); 1.56 (m, 2H); 1.38 (m, 2H); 1.28 (br.s, 9H); 1.04 (m, 2H); 0,69 (t, J = 7.4, 3H).
Example A129: {R)-3-{[4-(5-Butoxy-benzo[1,3Idioxo!-4-yl)-5H-pyn-olo[3,2-d]pyrimidine-7-cartx)nyll-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester
Starting from 4-{5-butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimldine-7-carboxylic acid (example A71) and commercially available (R)-3-amino-pyrrolidine-1-carboxylicacld tert-butyl ester the title compound was obtained as colorless solid.

MS (ES\}: miz = 524 (MH+, 100 %); 468 (MH'-C4H8).
1H-NMR 300 MHz, DMSO-d6): 12.33 (br.s, 1H,~NH):9.01 (s, 1H); 8.54 (d, J = 6.9, 1H,-NH);8.30 (s, 1H);7.01 (d, J = 8.6, 1H); 6.59 (d, J = 8-6, IN); 6.01 (s, 2H); 4.01 (m, IN); 3.89 (t, J = 6.4, 2H); 3.62 (m, 1H); 3.43 (m, 2H); 3.26 (m, 1H); 2.21 (m, 1H); 1.98 (m, 1H); 1.43 (s, 9H); 1.39 (m, 2H); • 1.05(m, 2H);0.69(t,J = 7.4, 3H).
Example A130: trans-[4-({4-[4-Methoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrofo[3.2-cOpyrimidine-7-carbonyl}-amino}-cyclohexyl]-carbamic acid tert-butyl ester
Starting from 4-[4-methoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (example A74) and commercially available trans-(4-amino-cyclohexyl)-carbamic acid tert-butyl ester the title compound was obtained as colorless solid. MS (ESI): m/z = 540 (MH+); 484 (MH'-C4H8}.
1H-NMR (400 MHz, DMSO-d6): 11.73 (br.s, 1H, -NH); 9.00 (s, 1H); 8.38 (d, J = 7.7, 1H, -NH); 8.22 (d, J =3.1, 1H);7.69(d, J = 8.2, 1H); 6.77 (s, 1H); 6.75 (dd, J1 = 8.2, J2 = 2.2, IN); 6.71 (d,J = 7.5, 1H, -NH); 4.23 (t, J = 4.6, 2H); 3.87 (s, 3H); 3.77 (m, 1H); 3.54 (t, J = 4.6, 2H); 3.31 (m, 1H); 3.13 (s, 3H); 1.99 (m, 2H); 1.85 (m, 2H); 1.39 (s, 9H); 1,33 (m, 4H).
Example A131: cis-(4-({4-[4-Methoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-c/]pyrimidine-7-carbonyl}-amino)-cyclohexyl]-carbamic acid tert-butyl ester Starting from 4-[4-methoxy-2-(2-methoxy-ettioxy)-ptienyl]-5H-pyrrolo[3,2-d]pyrimidine-7-cart)oxylic acid (example A74) and commercially available cts-(4-amino-cyclohexy()-carbamic acrd tert-butyl ester the title compound was obtained as colorless solid. MS (ESI): m/z = 540 (MH4); 484 (MH'-C1He); 440 (MH+-C5H8O2).
1H-NMR (400 MHz, DMSO-d6): 11.73 (br.s, 1H, -NH); 9.03 (s, 1H); 8.69 (d, J = 7.7, 1H, -NH); 8.22 (d, J = 3.3, 1H); 7.69 (d, J = 8.3, 1H); 6.93 (br.s, 1H, -NH); 6.77 (s, 1H); 6.76 (d, J = 8.3, IN); 4.24 (t, J = 4.6, 2H); 4.04 (br.s, 1H); 3.87 (s, 3H); 3.55 (t, J = 4.6, 2H); 3.44 (br.s, IN); 3.13 (s, 3H): 1.77 (m, 2H); 1.63 (m, 4H + 2H); 1.40 (s, 9H).
Example A132;4-({4-[4-Methoxy-2-(2-methoxy-ethoxy)-ptienyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl}-amino)-piperidine-1-carboxylic acid tert-butyl ester Starting from 4-[4-methioxy-2-(2-methoxy-ethoxy)-ptieny[]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (example A74) and commercially available 4-amino-piperidine-1-carlx)xylic acid tert-butyl ester the title compound was obtained as colorless solid. MS (ESI): m/z = 548 (MNa*); 526 (MM*); 470 (MH'-C1Hg).
1H-NMR (400 MHz, DMSO-d6): 11.76 (br.s, 1H, -NH); 9.00 (s, 1H): 8.53 (d, J = 7.8,1H, -NH); 8.24 (d, J = 3.3, 1H); 7.69 (d, J = 8.3,1H); 6.77 (s, 1H); 6.75 (dd, J, = 8.3, Jj = 2.2, 1H); 4.23 (t, J = 4.6, 2H); 4.06 (m, 1H); 3.87 (s, 3H + m, 2H); 3.54 (t, J = 4.6, 2H); 3,13 (s, 3H); 3.03 (m, 2H); 1.93 (m, 2H);1.42(s, 9H + m, 2H).

Example A133: trans-[4-{{4-[5-(2-Methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl}-amino)-cyclohexyl]-carbamic acid tert-butyl ester Starting from 4-[5-(2-methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (example A72) and commercially available trans-(4-amino-cyclohexyl)-carbamic acid tert-butyl ester the title compound was obtained as colorfess solid. MS (ESI): m/z = 554 (MH+, 100%); 498 (MH+-C4H8).
1H-NMR {200 MHz, DMSO-d6): 12.20 (br. s, 1H, -NH); 9.02 (s, 1H); 8.28 (d, J = 7.9, 1H, -NH); 8.27 (s, 1H); 7.02 (d, J = 8.6, 1H); 6.93 (d, J = 7.6, 1H, -NH); 6.62 (d, J = 8.6, 1H); 6.02 (s, 2H); 4.04 (t, J = 4.7, 2H &m. 1H);3.44(m, 1H); 3.40 (t, J = 4.7, 2H); 3.03 (s, 3H); 1.90-1.56 (m, 8H); 1.40 (s,9H).
Example A134: cis-[4-({4-[5-(2-methoxy-ethoxy)-benzo[1,3jdioxol-4-yl]-5H-pyrro!o[3,2-tf]pyrimidine-7-carbonyl}-aniino)-cycIohexyl]-Garbamic acid tert-butyl ester Starting from 4-[5-(2-mefhoxy-ethoxy)-benzo[1,3]dioxol-4-y(]-5H-pyrrolo[3,2-c(lpyrimidine-7-carboxylic acid (example A72) and commercially available cis-(4-amino-cyclohexyl)-carbamic acid tert-butyl ester the title compound was obtained as colorless solid. MS (ESI): m/z = 554 (MH+, 100%); 498 (MH+-C1Hg); 454 (MH+-C5H8O2).
1H-NMR (200 MHz, DMSO-d6): 12.21 (br. s, 1H, -NH); 9.05 (s, 1H); 8.60 (d, J = 7.8, 1H, -NH); 8.28 (d, J = 3.3, 1H);7.02(d,J = 8.6, 1H); 6.72 (d, J = 7.6, 1H,-NH):6.61 (d. J = 8.6, 1H); 6.01 (s, 2H); 4.03 (t, J = 4.7, 2H); 3.78 (m, 1H); 3.38 (t, J = 4.7, 2H); 3.30 (m, 1H); 3.02 (s, 3H); 2.00 (m, 2H); 1.85 (m, 2H); 1.50-1.28 (s, 9H & m, 4H).
Example A135: 4-({4-[5-(2-Methoxy-ettioxy)-benzo[1,3Idioxol-4-yl]-5H-pyrrolo[3,2-cfipyrimidine-7-carbonyl}-amino)-piperidine-1-carboxylic acid tert-butyl ester Starting from 4-[5-(2-methoxy-ettioxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d]pyrimidine-7-carlxixylic acid (example A72) and commercially available 4-amino-piperidine-1-carboxylic acid tert-butyl ester the title compound was obtained as colorless solid. MS (ESI): m/z = 540 (MH+, 100%); 484 (MH+-C4H8); 440 (MH+-C5H8O2).
1H-NMR (200 MHz, DMSO-d6): 12.23 (br.s, 1H, -NH); 9.02 (s, 1H); 8.43 (d, J = 7.8, 1H; -NH); 8.29 is, 1H); 7.02 (d, J = 8.6, 1H); 6.61 (d, J = 8.6, 1H); 6.01 (s, 2H); 4,08 (m, 1H); 4.03 {t. J = 4.7, 2H); 3.87 (m, 2H);3.39 (t, J = 4.7, 2H); 3.02 (s, 3H & m, 2H); 1.94 (m, 2H); 1.42 (s, 9H & m, 2H).
Example A136: 4-{[4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxymethoxy-phenyl)-5H-pyrrolo[3,2-c:(lpyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid fert-butyl ester Starting from 4-(2-cyclopropylm6thoxy-5-fluoro-4-methoxymethoxy-phenyl)-5H-pyrrolo[3,2-tf]pyrimidine-7-carboxylic acid (example A84) and commercially available 4-amino-piperidine-1-carlxixylic acid the title compound is obtained as colorless foam. IVIS (ESI): m/z = 570 (MH+ 100%).

1H-NMR (300 MHz, DMSO-d6): 12,04 (br.s, 1H, -NH); 9.02 (s, 1H); 8.49 (d, J = 7.9, 1H, -NH); 8.27 (s, 1H);7.51 (d, J = 11.5, 1H); 7.02 (d, J = 6.9, 1H);5.39(s, 2H); 4,07 (m, 1H); 3.88(d, J = 6.9, 2H); 3.87 (m, 2H); 3.47 (s, 3H); 3,03 (m, 2H); 1.93 (m, 2H); 1.46 (m, 2H); 1.42 (s, 9H); 0.95 (m, 1H); 0.35 (m,2H); 0.21 (m, 2H).
Example A137: 4-[2-cyclopropylmethoxy-4-(1,1-difluoro-methoxy)-5-fluoro-phenyl]-5H-pyrrolo[3,2-(;/]pyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid fert-bulyi ester Starting from 4-[2-cyclopropylnnethoxy-4-(1,1-difiuoro-methoxy)-5-fluoro-phenylJ-5H-pyrroloI3,2-d]pyrimidine-7-carboxylic acid (example A85) and commercially available 4-amino-piperidine-1-carboxylic acid the title compound is obtained as colorless foam. MS (ESt): m/2 = 576 (MH*); 520 (MH+-C1Ha); 476 (MH'-C5H8O2).
1H-NMR (300 MHz, DMSO-d6): 12.16 (br.s. 1H, -NH); 9.06 (s, lH); 8.47 (d, J - 7.7, 1H, -WH); 8.33 (s, 1H); 7.64 (d, J = 10.8, 1H); 7.40 (t, J = 73.1, 1H); 7.18 (d, J == 6.6, 1H); 4.07 (m, 1H); 3.91 (d. J = 6.9, 2H); 3.&7 (m, 2H); 3.03 (m, 2H); 1.93 (m, 2H); 1.46 (m, 2M); 1.42 (s, 9H); 0.95 (rn, 1H); 0.35 (m,2H);0.21 (m, 2H).
Example A138: 4-(5-Cyclopropylmethoxy-1,3-b6nzodioxol-4-yl)-5H-pyrrolo[3,2-c^pyrimidine-7-carboxylic acid piperidin-4-ylamide hydrochloride
4-({1-[4-(5-Gyclopropylmethoxy-1,3-benzodioxoI-4-yl)-5H-pyrro|o[3,2-d]pyrimidin-7-yl]-nnethanoyl}-amino)-prperidine-1-carboxylic acid tert-butyl ester from example A86 (4.02 g; 7.5 mmol) is dissolved in wami (40-70°C) 2-propanot (37.5 mL), After addition of 4M HCI in dioxane (7.5 mL) the stirred reaction mixture is heated to 80°C for two hours. Tert-butylmethylether (150 mL) is added to the reaction mixture while still warm (40-70°C). After cooling in an ice bath the precipitated product is collected, washed with tert-butylmethylether and dried in high vacuo at 50'C to yield 3.35 g of the title compound as bright yellow solid. MS (ESI): m/2 = 438 (MH+, 100%).
1H-NMR (400 MHz, DMSO-d6,): 12.56 (br.s. 1H, -NH); 9.10 (s, 1H}; 9.03 (br.s, 2H, -NH/); 8.44 (d, J = 7.3, 1H,-NH); 8-42(2, 1H); 7.03 (d, J = 8.6, IN); 6,58 (d, J = 8.6, 1H); 6.03 (s, 2H); 4.17 (m, 1H); 3.78 (d, J = 6.7, 2H); 3.32 (m, 2H): 3.07 (m. 2H); 2.13 (m. 2H); 1.83 (m, 2H); 0.88 (m, 1H); 0.30 (m,2H); 0.12 (m,2H).
Example A139: trans-4-(2-Cyclopropylmethoxy-5-fluoro-4-melhoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbioxylic acid (4-amino-cyclohexyl)-amide
Trans-[4-({1-[4-(2-cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrro!o[3,2-c(]pyrimidln-7-yl]-methanoyl}-amino)-cyctohexyl]-carbamtc acid tert-butyl ester from example A114 (3.05 g; 5.51 mmol) is dissolved in 2-propanol (27.5 ml). After addition of 4M HCI in dioxane (5.5 mL) the stirred reaction mixture is heated to 80°C for two hours, tert-bufyfmethytether (100 mL) is added (o the reaction mixture while still warm (40-70°C). After cooling in an ice bath the precipitated product is

collected, washed with tert-butylmethylether and dried in high vacuo at 50°C to yield the bright yellow hydrochloric acid salt of the title compound.
The salt is dissolved in hot (60-90°C) water (25 mL). The pH of the well stirred solution is adjusted to 9.0 by dropwise addition of 25 % NH4OH. After stirring for one hour in an ice bath the precipitated product IS collected, washed with ice-cold water and dried in high vacuo at 50°C to yield 2.18 g of the title compound as colorless solid. MS (ESI): m/z = 454 (MM", 100 %).
1H-NMR (400 MHz, DMSO-d6, MeOH-dn): 9.00 (s, 1H); 8.39 (d, J = 7.8, 1H, -NH); 8.24 (s, 1H); 7.50 (d, J =^ 11.8, 1H);6.92(d, J = 7.3, IN); 3.97 (s, 1H); 3.94 (d, J = 7.1, 2H); 3.80 (m, 1H); 2.74 (m, IN): 2.01 (m, 2H); 1.88 (m,2H); 1.40 (m,2H); 1.26 (m, 2H); 0.97 (m, 1H); 0.37 {m, 2H); 0.22 (m, 2H).
The following compounds are obtained analogously to the procedures described in above example A138orA139.
Example A140: tra ns-4-(5-Cy clop ropy lmethoxy-benzo[1,3]dioxol-4-yl)'5H-pyrrolo[3,2-G'lpyr(m(dir»e-7-carboxy/ic acid (4-ammo-cyctohexyl)-amtde
Starting from trans-{4-{[4-{5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartx)nyl]-amino}-cyclohexyl)-carbamic acid tert-butyl ester (example A87) the title compound is obtained as color/ess solid. MS (ESI): m/z = 450 (MH+, 100%).
1H-NMR (200 MHz, DMSO-dfi/MeOH-di): 9.02 (s, 1H); 8.29 (d, J = 8.8, 1H, -NH); 8.29 (s, 1H); 8.27 (s, 1H); 7.00 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 3.76 (d, J = 6.7, 2H & m, 1H}; 2.80 (m, 1H); 2.04 (m, 2H); 1.89 (m, 2H); 1.51-1.19 (m, 4H); 0.87 (m, 1H); 0.29 (m, 2H); 0.09 (m, 2H).
Exampte A141; ciE-4-(5-Cyc)opropylmetboxy-benzo[1,3]dioxol-4-y)-5H-pyrrolo[3,2-d]pyrilnidine-7-carboxylic acid (4-amino-cyclohexyl)-amide
Starting from cis-(4-{[4-(5-cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrroloI3,2-d]pyrimidine-7-carbonyl]-amino)-cyclohexyl)-carbamic acid tert-butyl ester (example A88) the title compound is obtained as colorless solid. MS (ESI): m/z = 450 (MH+, 100%).
1H-NMR (400 MHz, DMSO-d6): 12.33 (br.s, 1H, -NH); 9.06 (s, 1H); 8.62 (d, J = 7.2, 1H, -NH); 8.30 (s, 1H); 7.89 (br.s, 2H, -NH2); 7,02 (d, J = 8.6, 1H); 6.57 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.11 (m, 1H); 3.77 (d, J = 6.8, 2H); 3.23 (m, 1H); 1.87 (m, 4H); 1.73 (m, 4H); 0.88 (m, IN); 0.30 (m, 2H); 0.11 (m, 2H).
Example A142: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (R)-pyrrolidin-3-ylamide hydrochloride

starting from (R)-3-{[4-{5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolQ[3,2-a(]pyrimidine-7-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester (example A90) the title compound is obtained as bright yellow solid.
Example A143: 4-(5-Cyclopropylmethoxy-benzo[l ,3]dioxol-4-yl)-5H-pyrrolo[3,2-dlpyrimidfne-7-carboxylic acid (S}-pyrrolidin-3-ylam(de hydrochloride
Starting from (S)-3-{[4-{5-cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidlne-7-carbonyl]-amino}-pyrrolldlne-1-carboxylic acid tert-butyl ester (example A89) the title compound is obtained as bright yellow solid.
Example A144: 4-(5-CycloprQpylmethoxy-benzo[1,3]diDxol-4-yl)-5H-pyrrolo[3,2-c/jpyrimldine-7-carboxylic acid (piperidin-4'ylnriethyl)-amide
Starting from 4-({[4-(5-cyclopropylmethoxy-benzo[1,3]dioxo!-4-yl)-5/-y-pyrrolo[3,2-d]pyrimidine-7-carbonylI-amino}-methyl)-piperidtne-1-carboxylic acid tert-butyl ester (example A91) the title compound Is obtained as colorless solid.
Example A145; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5^/-pyrrolo[3,2-d]pyrimldine-7-carboxylic acid (piperidin-3-ylmethyl)-amide
Starting from 3-({[4-(5-cyc[opropylmethoxy-b6nzof1,3Id[oxol-4-y()-5H-pyrrolo[3,2-d]pyrimidine-7-cartjonyl]-amino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester (example A92) the title compound is obtained as colorless solid.
Example A146: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl}-5H-pyrrolo[3,2-c/]pyrimidine-7-carboxylic acid (pyrrolidin-3-ylmethyl)-amide
Starting from 3-({[4-(5-cyclopropylmethoxy-benzo[1,31dioxoi-4-yl)-5H-pyrrolo[3,2-cOpyrimidine-7-carbonyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (example A93) the title compound is obtained as colorless solid.
Example A147: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (morpholin-2-ylmethyl)-amide
Starting from 2-({[4-(5-cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pynro!o[3,2-d]pyrimidine-7-carbony(]-amino}-methyl)-morpho(frTe-4-carboxylic acid tert-butyl ester (example A94) the title compound is obtained as colorless solid.
Example A148: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolof3,2-d]pyrimidine-7-carboxylic acid {S)-piperidin-3-ylamide

Starting from (S)-3-{[4-(5-cyc)opropy)methoxy-benzo[1,3]dioxo)'4-yl)-5H-pyrrD)o[3,2-djpyrimidine-7-
carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester (example A96) the title compound Is
obtained as colorless solid.
MS (ESI): m/z = 436 (MH+, 100%).
1H-NMR (300 MHz, DMSO-d6/MeOH-d6): 9.03 (s, 1H); 8.51 (d, J = 8.1, 1H, -NH); 8.26 {s, 1H); 7.00
(d, J = 8.6, IN); 6.56 (d, J = 8.6, IN); 6.00 (s, 2H); 3,96 (m, IN); 3.76 (d, J = 6.7, 2H); 3.02 (m, 1H);
2.73 (m, 1H}; 2.63 (m, IN); 2.54 (m, 1H); 1.87 (m, IN); 1.66 (m. 1H); 1,50 (m, 1H);0.88(m, 1H);
0.29 (m,2H); 0.10 (m, 2H).
Example A149: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c/]pyrimidtne-7-carboxylic acid (R)-piperidin-3-ylamide
Sta rtlng f rem (R )-3-{ [4-(5-cyclopropy I methoxy-ben zo[1,3]d ioxol-4-y l}-5H-py rro ID [3,2-d]py rim id i ne-7-carbonyl]-amino}-piperidine-1-carboxyl!c acid tert-butyl ester (e) 1H-NMR (300 MHz, DMSO-d6): 12,85 (br.s, 1H, -NH); 9.38 (br,m, 2H, -NH?*); 9.13 (s, 1H); 8,60 (s, 1H); 8,51 (d, J = 7,6, 1H, -NH); 7.06 (d, J = 8,6, 1H); 6.58 (d, J *= 8.6, 1H); 6.05 (s, 2H); 4,31 (m, 1H); 3.79 (d, J = 6.7, 2H); 3,38 (m, 1H); 3.18 (m, 1H); 2.97 (m, 1H); 2,91 (m, 1H); 2.04 - 11.71 (m, 4H); 0,90 (m, 1H); 0.31 (m, 2H); 0.14 (m, 2H),
Example A150: trans-4-(2-Cyclopropy)methoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-c(lpyrimidine-7-cart»xylic acid (4-amino-cydohexyl)-amide
Starting from trans-(4-{[4~(2-cycloprQpylmethoxy-4-methioxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartx>nyl]-amino}-cyclohexyl)-carbafnrc acid tert-butyl ester (example A100) the title compound is obtained as colorless solid. MS (ESI): m/z = 436 (MH+, 100 %).
1H-NMR (400 MHz, DMSO-d6/MeOH-d4): 9.09 (s, 1H); 8.39 (d, J = 7.9, 1H, -NH); 8.21 (s, 1H); 7.61 (d, J = 8.5, 1H); 6,70 ( dd, J1 = 8,5, J2 = 2.2, 1H); 6,68 (d, J = 2,2, 1H); 3.92 (d, J = 6.9, 2H); 3.86 (s, 3H); 3.81 (m, 1H); 3,08 (m, 1H); 2.05 (m, 4H); 1.48 (m, 4H); 0.97 (m, 1H); 0.36 (m, 2H); 0.23 (m, 2H).
Example A151: cis-4-(2-CycloprQpylmethioxy-4-methoxy-plienyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide
Starting from cis-(4-{[4-(2-cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartx»nyl]-amino}-cyclohexyl)-carbamic acid tert-butyl ester (example A99) the title compound is obtained as colorless solid. MS (ESI): m/z = 436 (MH+ 100 %).

1H-NMR (400 MHz, DMSO-d6/MeOH-di): 9,01 (s, 1H); 8.74 (d, J = 7.7, IN, -NH); 8.19 {s, 1H); 7.63 (d, J = 8.5, -JH); 6.73 (dd, J, = 8.5, Jj = 2.2, 1H); 6.69 (d, J = 2.2. 1H); 4.04 (m, 1H); 3.93 (d, J -6.9, 2H); 3.86 (s, 3H); 2.79 {m, 1H); 1.80 (m, 2H); 1.66 (m, 4H); 1.47 (m, 2H); 0.99 (m, 1H); 0.37 (m, 2H); 0.24 (m, 2H).
Example A152;4-{2-Cyc!opropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4~ylamide
Starting from 4-{[4-(2-cyctopropylmethoxy-4-mefhoxy-phenyl)-5H-pyrroto[3,2-d]pyrimidine-7-
carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyi ester (example A98)the title compound is
obtained as colorless solid.
MS (ESI): m/z = 422 (MH+, 100 %).
1H-NMR {400 MHz, DMSO-d6/MeOH-d4): 9.02 (s. 1H); 8.57 {d, J = 7.5, 1H, -NH); 8.25 (s, 1H); 7.63
(d. J = 8.5,1H); 6.73 ( dd, J, = 8.5, J^ = 2.2, 1H); 6.69 {d, J = 2.2, 1H); 4.18 (m, 1H); 3.93 (d, J =
6.9, 2H]; 3.86 (s, 3H); 3.37 (m. 2H); 3.11 (m, 2H): 2.16 (m, 2H): 1.80 (m, ZH]; 0.98 (m, 1H); 0.37
(m, 2H); 0.24 (m, 2H).
Example A153; trans-4-(2-Cyc/opropy(methoxy-5-methoxy-phenyl)-5/i'-pyrrolo(3,2-c(|pyrimidine-7-carboxylic acid {4-amino-cyclohexyl)-amide
Starting from trans-C4-{[4-(2-cyclopropylmethoxy-5-niethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-
carbonyl]-am(no}-cydohexy()-carbamic acid tert-butyl ester (example A101) the title compound is
obtained as colorless solid.
MS (ESI): m/z = 436 (MH+, 100 %).
1H-NMR (400 MHz, DMSO-d6/MeOH-d^). 9.04 (s, 1H); 8.41 (d, J = 7.9, 1H, -NH); 8.25 (s, 1H); 7.20
(t, J = 1.6, 1H); 7.12 (d, J = 1.6, 2H); 3.83 (d, J = 6.9, 2H & m, 1H); 3.77 (s, 3H); 3.11 (m, 1H); 2.08
(m, 2H); 2.01 {m, 2H); 1.49 (m, 4H); 0.92 (m, 1H); 0.32 (m, 2H); 0.16 (m, 2H).
Example A154; cis-4-(2-Cyclopropylmethoxy-5-methoxy-ptienyl)-5H-pyrrolo(3,2-d]pyrimidine-7-carboxyllc acid (4-amino-cyclohexyl)-amide
Starting from cis-{4-{I4-(2-cyclopropylmethoxy-5-methoxy-pheny|)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-cyclotiexyl)-carbamic acid tert-bulyl ester (example A102) (tie tille compound is obtained as colorless solid. MS (ESI): m/z = 436 (MH+. 100 %).
1H-NMR (200 MHz, DMSO-d6/MeOH-d,): 9.06 (s, 1H); 8.65 (d, J = 7.8, 1H, -NH); 8.23 (s, 1H); 7.19 (t, J = 1.7, 1H); 7.11 (d, J = 1.7, 2H); 4.04 (m, 1H); 3.83 (d, J = 6.8, 2H); 3.77 (s, 3H); 2.82 (m, 1H); 1.88-1.54 (m, 6H); 1.54-1.32 (m, 2H); 0.93 (m, 1H); 0.33 (m, 2H); 0.11 (m, 2H).
Example A155:4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylrc acid piperidin-4-ylamide

Starting from 4-{[4-(2-cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-
carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl esler {example A103) the title compound is
obtained as colorless solid.
MS (ESI): m/z = 422 (MH\ 100 %).
1H-NMR (400 MHz, DMSO-d6/MeOH-di): 9,06 (s, 1H); 8.47 {d, J = 8.0, 1H. -NH); 8.24 (s, 1H); 7.19
(f, J = 1.6, 1H); 7.11 (ct, J = 1.6, 2H); 3.97 (m, 1H); 3.83 (d, J = 6.9, 2H); 3,77 (s, 3H); 3.11 (m, 1H);
2.97{nn, 2H); 2.59 (m, 2H); 1.90 (m,2H); 1.41 (m, 2H); 0.92 (m, 1H}; 0,32 (m, 2H); 0.16(nn,2H).
Example A156: cis-4-(2-Cyclopropylmethoxy-4-fluoro-ptnenyl)-5H-pyrrolo[3,2-d]pyrimidinG-7-carboxyiic acid (4-amino-cyclohexyl)-amide
Starting from cis-f4-{[4-(2-cycloprGpy!methoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-cyclohiexyl)-carbamic acid tert-butyl ester {example A105) the title compound is obtained as colorless solid. MS (ESI): m/z = 424 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6/MeOH-di): 9.05 (s, 1H); 8.66 (d, J = 7.8, 1H; -NH); 8.26 (s, 1H); 7.86 (d, J = 7.6, 1H, -NH); 7.65 (dd, J, = 8.5, J2 = 7.0, 1H); 7.08 (dd, J1 = 12.6, J^ = 2.3, 1H); 6.96 (ddd, J, = J2 = 8.5, J3 = 2.3, 1H); 4.04 (m, 1H); 3.93 (d, J = 7.0, 2H); 2.82 (m, 1H); 1.83 (s, 3H); 1.88-1.74 (m, 2H); 1.74-1.58 (m, 4H); 1.52-1.39 {m, 2H); 0.97 (m, 1H); 0.36 (m, 2H); 0.22 (m, 2H).
Example A157: trans-4-(2-Cyclopropylmethoxy-4-fluoro~phenyl)-5H-pyrrolo[3,2-c/lpyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide
Starting from {rans-(4-{[4-(2-cyclopropylmethoxy-4-ffuoro-phenyl)-5H-pyrrofo[3,2-d]pyrimfdine-7-carbionyl]-amino}-cyclohexyl)-carbamlc acid tert-butyl ester (example A104) the title compound is obtained as colorless solid. MS (ESI): m/z = 424 (MH\ 100 %).
1H-NMR (300 MHz, DMSO-d6/MeOH-d4): 9.01 (s,- IN); 8.33 (d, J = 7.9, 1H; -NH); 8.25 (s, 1H); 7.66 (dd, J1 = 8.5, J2 = 7.0,1H); 7.07 (dd, J, = 12.6, J2 = 2.3, 1H); 6.95 (ddd, J1 = Jz = 8.5, J3 = 2.3, 1H); 3.92(d,J = 6.9, 2H);3.79(m, 1H);2.63(m, 1H); 1.97 (m,2H); 1.82 {m,2H); 1.36 (m,2H); 1.18 {m, 2H); 0.95 (m, IN); 0.36 (m, 2H); 0.22 (m, 2H).
Example A158: 4-(2-Cyclopropylmethoxy-4-fluoro-ptienyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide
Starting from 4-{[4-(2-cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester (example A106) the title compound is obtained as colorless solid. MS (ESI): m/z = 410 (MH\ 100%).
1H-NMR (300 MHz, DMSO-d6): 12.45 (br.s, 1H, -NH); 9.11 (s, 1H); 9.10 (br.S, 2H, NH2+); 8.51 (d, J = 7.7, 1H;-NH); 8.48 (s, 1H); 7.70 (dd, J, = 8.5, J2 = 7.0, 1H);7.11 (dd, J, = 11.6, J2 = 2.4, 1H);

6.99 (ddd, J1 = Ja = 8.5, J3 = 2.4, 1H); 4.17 (m, 1H); 3.94 (d, J = 7.0, 2H); 3.32 (m, 2H); 3.08 (m, 2H); 2.12 (m, 2H); 1.83 (m, 2H); 0.97 (m, 1H); 0.36 (m, 2H); 0.24 (m, 2H),
Example A159: 4-(2-Cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimldine-7-carboxylic acid pIperidin-4-ylamide hydrochloride
Starting from 4-{(4-(2-cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-Garbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester (example A108)the title compound is obtained as bright yellow sofid. MS (ESI): m/z = 410 (MH', 100 %).
1H-NMR (300 MHz, DMSO-d6,); 12.28 (br.s, 1H, -NH); 9.08 {s, 1H); 8.37 (d, J = 3.4, 1H); 8.34 (s, 1H, -NH}; 8.09 (br.s, 3H, -NH:,"); 7.47-7,36 (m, 2H); 7.20 (dd, J1 = 9.1, J2 = 4.4, 1H); 3.90 (d, J = 6.9, 2H); 3.81 (m, 1H); 3.08 (m, 1H); 2.04 (m, 4H); 1,49 (m, 4H); 0,94 (m, 1H); 0.34 (m, 2H); 0,19 (m, 2H),
Example A160: trans-4-(2-CycloprQpylmethoxy-5-fluoro-phenyl)-5H~pyrrolo[3,2-dlpyrimidine-7-carbGxylic acid (4-amino-cyclohexyl)-amide hydrochloride Starting from trans-(4-{[4-(2-cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrroto[3,2-o]pyrim(d(ne-7-carbonyl]-amino}-cydohexyl>-carbamic acid tert-butyl ester (example A107) the title compound is obtained as bright yellow solid. MS (ESI); trt/z = 424 (MH+ 100 %).
1H-NMR (300 MHz, DMSO-d6,): 12.37 (br.s, 1H, -NH); 9.11 (s, 1H); 9.07 (br.s, 2H, -NH2*); 8.49 (d, J = 7,6, 1H, -NH); 8.44 (d, J = 3.3, 1H); 7.47-7.37 (m, 2H); 7.20 (dd, J, = 9,1, J2 = 4.4, 1H); 4.17 (m, 1H); 3.89 (d, J = 6.9, 2H); 3.31 (m, 2H); 3.08 (m, 2H); 2.12 (m, 2Hy, 1.82 (m, 2H); 0.94 (m, 1H); 0.33 (m, 2H); 0.19 (m, 2H).
Example A161: trans-4-(2-Cyclopropy)methoxy-pheny))-5H-pyrro)o[3,2-o5pyrimidine-7-cartxjxylic acid (4-amino-cyclohexyl)-amide
Starting from trans-(4-{[4-(2-cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-c/!pyrimidine-7-carbQnyi]-amino}-cyclohexyl)-carbamic acid tert-butyl ester (example A109) the title compound is obtained as colorless solid,
MS (ESI): m/z = 406 (MH+. 100 %).
1H-NMR (300 MHz, DMS0-d6, MeOH-d4): 9.02 (s, 1H); 8.34 (d, J = 8.0, IN, -NH); 8.22 (s, 1H); 7.63 (dd, J1 = 7.6, J2 = 1.7. 1H); 7.53 (ddd, J, = 8.0, 0; = 7.6, J3" 1.7, 1H); 7.17 (dd, J, = 8.0, J2 = 0.9, 1H); 7.13 (ddd, J, = J2 = 7.6, J3 = 0.9, 1H); 3.91 (d, J = 6.9, 2H); 3.80 (m. 1H); 2.62 (m, 1H); 1.98 (m,2H); 1.92 (m,2H); 1.36 {m,2H); 1.18 (m, 2H); 0.96 (m, 1H); 0.35 (m, 2H); 0,21 (m. 2H).
Example A162:4-(2-Cyclopropylmethoxy-phenyl)-5H-pyrrolo[3.2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide

starting from 4-{[4-(2-cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino)-
piperidine-1-carboxylic acid tert-butyl ester (example A110) the title compound is obtained as
colorless solid.
MS (ESI): m/z = 392 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6, MeOH-dj): 9.06 (s, 1H); 8.48 (d, J = 7.9, 1H, -NH); 8.23 (s, 1H);
7.63 (dd,J1= 7,6. J2= 1.7, 1H); 7.53 (ddd, J, = 8.0, J; = 7.6, J3= 1.7, 1H); 7.17 (dd, J, = 8.0, J2 =
0.9, IN); 7.13 (ddd, J1 = J; = 7.6, J3 = 0.9, 1H); 3.98 (m, 1H); 3.91 (d, J = 6.9, 2H); 2.98 (m, 2H);
2.60 (m, 2H); 1.89 (m, 2H); 1.42 (m, 2H); 0.97 (m, 1H); 0.34 (m, 2H); 0.21 (m, 2H).
Example A163: 4-(2-Cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-c(lpyrimidine-7-carboxy(ic acid pfperidin-4-ylamide hydrochloride
Starting from 4-{[4-(2-cyclopropylmethoxy-4-fluoro-5~methoxy-phenyl)-5H-pyrrolo[3,2-dlpyrinn!dine-7-carbonyl]-annino}-piperidine-1-carboxylic acid tert-butyl ester (example A111) the title compound is obtained as bright yellow solid. MS (ESI): m/z = 440 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6,): 12.44 (br.s, 1H, -NH); 9.13 (s, 1H & br.s, 2H, -NH2*); 8.51 (d, J = 5.6, 1H, -NH); 8.49 (s, 1H); 7.45 (d, J = 9.8, 1H); 7.22 (d, J = 13.4, 1H); 4.17 (m, 1H); 3.87 (d, J = 7.2. 2H & s, 3H); 3.32 (m, 2H); 3.07 {m, 2H); 2.13 (m, 2H); 1.83 (m, 2H); 0.93 (m, 1H); 0.34 (m, 2H);0.19(m, 2H).
Example A164: 4-(2-Cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (R)-piperidin-3-ylamide hydrochloride Start/rig from (R)-3-{(4-(2-cyclopropylmethoxy-4-fluoro-5-methoxy-pherjyl)-5/y-pyrrolo(3,2-(/|pyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester (example A112) the litle compound is obtained as bright yellow solid. MS (ESI): m/z = 440 (MH+ 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.46 (br.s, 1H, -NH); 9.29 (br.s, 1H, -NH); 9.19 (br.s, 1H. -NH); 9.11 (s, 1H); 8.55 (s, 1H); 8.53 (br.s, 1H, -NH); 7.45 (d, J = 9.8, 1H); 7.22 (d, J = 13.3, 1H); 4.28 (m, IN); 3.87 (d, J = 6.7, 2H); 3.86 s, 3H); 3.38 (m, 1H); 3.20 (m, 1H); 2.97 (m, 2H); 2.04-1.71 (m, 4H); 0.94 (m, 1H); 0.34 (m, 2H); 0.19 (m. 2H).
Example A165: 4-(2-Cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrroloI3,2-d]pyrimidine-7-carboxyIic acid (R)-pyrrolidin-3-ylamide hydrochloride Starting from (R)-3-{[4-(2-cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyi]-amino}-pyrrolidine-1-carboxyiic acid tert-butyl ester (example A113) the title compound is obtained as bright yellow solid. MS (ESI): m/z = 426 (MH\ 100 %).

1H-NMR (300 MHz, DMSO-d6): 12.41 (br.s, 1H, -NH); 9.39 (br.s, 1H, -NH2); 9.11 (s, 1H); 8.69 (d, J = 6.7, 1H, -NH); 8.51 (d, J = 3.3, 1H); 7.45 {d, J = 9.8, 1H); 7.21 (d, J = 13.3, 1H): 4.65 {m, 1H); 3.87 (d, J = 6.8, 2H); 3,86 s, 3H); 3.52-3.46 (m, 1H): 3,30-3.14 (m, 1H); 2.32 {m, 1H); 2.04 (m, 1H); 0.93 (m, 1H); 0.33 (m, 2H); 0,19 (m, 2H). solid.
Example A165: 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-<: acid pipertdin-4-ylamide hydrochloride> Starting from 4-{[4-(2-cyclopropylmethoxy-5-fluoro~4-methoxy-phenyl)-5H-pyrrolo[3,2-c/Ipyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid tert-buty! ester {example A115) the title compound is obtained as bright yellow solid. MS (ESI): m/z = 440 (MH\ 100 %).
1H-NMR (300 MHz. DMSO-d6,): 12.53 (br.s, 1H, -NH); 9.16 (br.s. 2H, -MHz'); 9.11 (s, 1H); 8,57 (d, J = 3.2, 1H);S.53(d, J = 7.6, 1H); 7.55 (d, J = 11.7, 1H); 6.96 (d. J = 7.3, 1H);4,17(m, 1H);4.00 (s, 3H); 3.99 (d, J = 5,2, 2H); 3.31 Example A167: 4-(2-Cyclopropylmethoxy-5-fiuoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-c/]pyrimidine-7-carboxylic acid (R)-piperidin-3-ylamide hydrochloride Starting from (R)-3-{[4-(2-cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-c')pyr(mid(ne-7-carbonyl]-amirTo)-piperid/ne-1-carboxy/ic acid tert-butyl ester (example A116) the title compound is obtained as bright yellow solid. MS (ESI): m/z = 440 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.48 (br.s, 1H, -NH); 9.28 (br.m, 2H, -NH2*); 9.08 (s, 1H); 8.59 (d, J = 6.8, 1H,-NH);8.57(s, 1H); 7.57 (d. J = 11.7, IN); 6.96 (d, J = 7.3, 1H);4.30(m, 1H);4.00(s, 3H); 3.99 (d, J = 5.2, 2H); 3.39 (m, IN); 3.20 (m, 1H); 2.99 (m, 1H); 2.97 (m, 1H); 1.98 (m, 2H); 1.76 (m, 2H); 0.98 (m, 1H); 0.38 (m, 2H); 0,25 (m, 2H).
Example A168: 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-c/]pyrimidine-7-carboxyllc acid (S)-piperidin-3-ylamide hydrochloride Starting from (S)-3-{[4-(2-cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrro!o[3,2-c/]pyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester (example A117) the title compound is obtained as bright yellow solid. MS (ESI); m/z = 440 (MH+ 100 %).
1H-NMR (300 MHz, DMSO-d6); 12.48 (br.s. 1H, -NH); 9.28 (br.m, 2H, -NH2*); 9.08 (s, 1H); 8.59 (d. J = 6.8, 1H,-NH);8.57(s, 1H); 7.57 (d, J = 11.7, 1H); 6.96 (d, J = 7,3. 1H);4.30(m, 1H);4.00{s, 3H); 3.99 (d, J = 5.2, 2H); 3.39 (m, 1H); 3.20 (m, 1H); 2.99 (m, 1H); 2.97 (m, 1H); 1.98 (m, 2H); 1.76 (m, 2H); 0.98 (m, 1H); 0.38 (m, 2H); 0.25 (m, 2H).

txampie A169: 4-(2-Cyclopropy[methoxy-5-fluoro-4-methoxy-pheny()-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (R)-pyrrolidin-3-ylamide hydrochloride Starting from (R)-3-{[4-(2-cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidirte-7-carbony(J-arriino}-pyrrotidine-1-carboxy((c acid fert-butyl ester (example A118) the title compound is obtained as bright yellow solid. MS (ESI): m/z = 426 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-ds): 12.39 (br.s, 1H, -NH); 9.37 (br.s, 2H, -NH2); 9.08 (s, 1H); 8.73 (d, J = 6.7, 1H;-NH);8.53(d, J = 3.2, 1H); 7.54 (d, J = 11.8, 1H); 6.95 (d, J = 7.2,1H); 4.65 (m, 1H); 3.98 (s, 3H); 3.96 (d, J = 6.2, 2H); 3.57-3.39 (m, 2H); 3.30-3.17 (m, 2H); 2.33 (m, 1H); 2.03 {m, 1H); 0.97 (m, 1H); 0.37 (m, 2H), 0.23 (m, 2H).
Example A170: trans-4-(2-Cyclopropylmethoxy-5-methyl-phenyl)-5f/-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4-annino-cyclohexyl)-amide
Starting from trans-{4-{[4-(2-cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-cyclohexyl)-carbamic acid lert-butyl ester (example A120) the title compound is obtained as colorless solid. MS (ESI): m/z = 420 (MH+, 100 %).
1H-NMR 400 MHz, DMSO-d6/MeOH-di): 9.01 (s, 1H); 8,38 (d, J = 7.9, IN, -NH); 8.21 (s, 1H); 7.45 (d, J = 1.9, 1H); 7.33 (dd, J1 = 8.4. J2 = 1.9, 1H); 7.06 (d, J = 8.4, 1H); 3.87 (d, J ^ 6.S, 2H).: 3.80 (m, 1H);2.63(m, 1H); 2.17 (s, 3H); 2.00 (m, 2H); 1.84 (m,2H); 1.38 (m,2H); 1.20 (m,2H); 0.95 (m, 1H); 0.34 (m,2H); 0.19 (m,2H).
Example A171: 4-(2-Cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide
Starting from 4-{[4-(2-cyclopropylmethoxy-5-methyl-pheny))-5H-pyrrolo(3,2-c(lpyfimidine-7-carbonyll-amino}-piperidine-1-carboxylic acid tert-butyl ester (example A119) the title compound is obtairied as colorless solid. MS (ESI): m/z = 406 (MH+, 100 %).
■1H-NMR 400 MHz, DMSO-d6/MeOH-d4): 9.04 (s, 1H); 8.53 (d, J = 7.7, 1H, -NH); 8.24 (s, 1H); 7.46 (d, J= 1.9,1H); 7.34 (dd,J1 = 8.4, J2= 1.9, 1H); 7.07 (d, J = 8.4, 1H);4.03(m, 1H)3.87 (d, J = 6.8, 2H); 3.13 (m, 2H); 2.80 (m, 2H); 2.34 (s, 3H); 2.01 (m, 2H); 1.57 (m, 2H); 0.95 (m, 1H); 0.34 (m, 2H);0.20(m,2H).
Example A172: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d] pyrim id ine-7-carboxylic acid azetidin-3-ylamide

Starting from 3-{[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol'4-yl)-5H-pyrrolo(3,2-d]pyrimidine-7-carbonylJ-amino}-azetidine-1-carboxylic acid tert-butyl ester (example A95) the title compound is obtained as colorless solid.
Example A173: tran&4-(5-Cyclobuty[methoxy-benzo[1,3]d[oxo[-4-yl)-5/-f-pyrrolo[3,2-cf]pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide hydrochloride
Starting from trans-[4-({1-[4-(5-cyclobutylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]-methanoy(}-amino)-cyc(ohexyl]-carbamic acid tert-butyl ester (Example A121) the title compound is obtained as bright yellow solid. MS (ESI): m/z = 464 (MH+, 100%).
1H-NMR (300 MHz, DMSO-d6): 12.88 (br.s, 1H, -NH); 9.12 (s, 1H); 8.52 (d, J = 3.1, 1H); 8.29 (d, J = 7.4, 1H, -NH & br.s, 3H, -NH3*); 7.07 (d, J = 8.6, IN); 6.62 (d, J = 8.6, 1H); 6.06 (s, 2H); 3.88 (d, J = 6.3, 2H); 3.82 (m, 2H); 3.07 (m, IN); 2.41 (m, 1H); 2.06 (m, 4H); 1.70 (m,3H); 1.63-1.40 (m, 7H}.
Example A174: 4-(5-Cyclobutylmethoxy-b8nzo[1,3]dloxol-4-yl)-5H-pyrrolo[3,2-o]pyrfmidine-7-cart)oxylic acid piperidfn-4-y!amide hydrochloride
Starting from 4-({1-[4-(5-cyclobutylmethoxy-benzo[1,3Idioxol-4-y|)-5H-pyrrolo[3,2-ci?pyrimidin-7-yl]-methanoyl}-amino)-piperidine-1carboxylic acid tert-butyl ester (example A122) the title compound is obtained as brfght yeltow solid. MS (ESI): m/z = 450 (MH+ 100%).
1H-NMR (300 MHz, DMSO-d6): 12.74 (br.s, 1H, -NH); 9.17 (br.s, 2H, -NH2"); 9.12 (s, 1H); 8.48 (d, J = 3.1, 1H); 8.43 (d, J = 7.5, 1H, -NH); 7.06 (d. J = 8.6, 1H); 6.61 (d, J = 8.6, 1H); 6.05 (s, 2H); 4.16 (m, 1H); 3.87 (d, J = 6.3, 2H); 3.31 (m, 2H); 3.07 (m, 2H); 2,40 (m, 1H); 2.12 (m. 2H); 1.83 (m, 2H); 1.70(m, 3H);1.52(m, 3H).
Example A175: 4-(5-Ethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxytic acid piperidin-4-ylamide
Starting from 4-{{4-(5-et hoxy-benzol 1,3]dioxol-4-y l)-5H-py rro loI3,2-0] py rim id i ne-7-carbonyJ]-a mino}-piperidine-1-carboxylic acid tert-butyl ester (example A123) the title compourid was obtained as colorless solid.
MS (ESI): m/z = 410 (MH+, 100 %).
1H-NMR (400 MHz, DMSO-d6/MeOH-d^): 9.04 (s, 1H); 8.47 (d, J = 7.8, 1H, -NH); 8.29 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.59 (d, J = 8.6, 1H); 6.01 (s, 2H); 4.03 (m, 1H); 3.96 (qu, J = 6.9, 2H); 3.09 (m, 1H); 2.93 (m, 1H); 2.76 (m, 1H); 2.21 (m. 1H); 1.98 (m, 2H); 1.57 (m, 2H); 1.03 (t, J = 6.9, 3H).
Example A176: 4-(5-Ethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartxDxylic acid (R)-pyrrolidin-3-ylamide

starting from {R)-3-{[4-(5-ethoxy-benzo[1,3Jdioxo)-4-yl)-5H-pyrrolo[3,2-d]pyrifnidine-7-carbonyl]-
amino}-pyrrolidine-1-carboxylic acid tert-butyl ester {example A124) the title compound was
obtained as colorless solid.
MS (ESI): m/z = 396 (MH+ 100 %).
1H-NMR (400 MHz, DMSO-d6/MeOH-dj): 9.04 (s. 1H); 8.49 (d, J = 7.3, 1H, -NH); 8.30 (s, 1H); 7.02
(d, J = 8.6, IN); 6.59 (d, J ^ 8.6, 1H); 6.01 (s, 2H); 4.45 (m, 1H): 3.96 (qu, J = 6.9, 2H); 3.17 (m,
1H); 3.02 (m, 1H); 2.89 (m, 1H); 2.75 (m, 1H); 2.13 (m, 1H); 1,70 (m, 1H); 1.03 (f, J = 6.9. 3H).
Example A177: 4-(5-Propoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-copyrimidine-7-carboxylic acid piperidin-4-ylamide
Starting from 4-{[4-(5-propoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3.2-copyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester (example A125) the title compound was obtained as colorless solid. MS (ESI): m/2 = 424 (MH+, 100 %).
1H-NMR (400 MHz, DMSO-d6/MeOH-d4): 9.03 (s, 1H); 8.49 (d, J = 8.0, 1H, -NH); 8.27 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.58 (d, J = 8.6, 1H); 6.01 (s, 2H); 4.03 (m, 1H); 3.86 (t, J = 6.4, 2H); 3.11 (m, IN); 2.87 (m, 1H); 2.69 (m, 2H); 1.92 (m. 1H); 1.72 (m, 1H); 1.57 (m, 2H); 1.40 (m, 2H); 0.62 (t, J = 7.4, 3H).
Example A178: 4-(5-Propoxy-benzo[1,3]dioxQl-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyYic add (R)-pyrrolidin-3-ylamide
Starting from (R)-3-{[4-(5-propoxy-benzo[1,3]dioxol-4-yl}-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester (example A126) the title compound was obtained as colorless solid. MS (ESI): m/z = 410 (MH+, 100 %).
1H-NMR (400 MHz, DMSO-d6/MeOH-da): 9.02 (s, 1H); 8.48(d, J = 7.3, 1H,-NH); 8.26 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.58 (d, J = 8.6, 1H); 6.01 (s, 2H); 4.43 (m, 1H); 3.86 (t, J = 6.4, 2H); 3.15 (m, 1H); 3.01 (m, 1H); 2.87 (m, 1H); 2.73 (m, IN); 2.12 (m, IN); 1.69 (m, 1H); 1.42 (m, 2H); 0.62 (t, J = 7.4, 3H).
Example A179: 4-(5-Butoxy-benzo[1,3]dioxol-4-yl>-5H-pyrroio[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide
Starting from 4-{[4-(5-butoxy-benzo[1,3]dloxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester (example A127) (tie title compound was obtained as colorless solid.
MS (ESI): m/z = 438 (MH\ 100 %).
1H-NMR 300 MHz, DMSO-d6/MeOH-d4): 9.03 (s. 1H); 8.50 (d, J = 8.0, 1H, -NH); 8.26 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.59 (d, J = 8.6, 1H); 6.01 (s, 2H); 4.00 (m. 1H); 3.89 (t, J = 6.4, 2H); 3.08 (m, 1H);

2.80 (nn, 1H); 2.70-2,55{m.2H); 1.90{m, 1H); 1.70 (m, 1H); 1,61-1.47 (m, 2H); 1.40 (m,2H); 1,04 (m, 2H);0.69{t, J = 7.4, 3H).
Exannple A180: 4-{5-Butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c(|pyrimidlne-7-carboxylic acid piperidin-3-ylamide
Starting from 3-{[4-(5-bufoxy-benzo[1,3]dioxo(-4-yl)-5H-pyrro(o[3,2-d]pyrimidine-7-carbony(]-aniino}-piperidine-1-carboxylic acid tert-butyl ester (example A128) the title compound was obtained as colorless solid.
MS (ESI); m/2 = 438 (MH\ 100 %).
1H-NMR (300 IV1Hz, DMSO-d6/MeOH-d4):9.03 (s, 1H); 8.46 (d, J = 7.8, 0-5H, -NH); 8.42 (d, J = 7.8, 0.5H, -NH); 8.27 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.59 (d, J = 8.6, IN); 6,01 (s, 2H); 4.09-3.91 (m, 1H); 3,89(t,J:^6.4, 2H);3.08(m, 1H);2.92(m. 1H); 2.73 (m, 2H); 2.22 (m, 1H); 1.97 (m,2H); 1.54 (m, 2H); 1.40 (m, 2H); 1.08 (m, 2H); 0.59 (t, J = 7.4, 3H).
Example A181: 4-(5-Butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (R)-pyrrolidin-3-ylamide
Starting from {R)-3-{[4-(5-butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrroio[3,2-d]pyrimidine-7-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester (example A129) the title compound was obtained as colorless solid. MS (ESI): m/z = 424 (MM", 100 %).
1H-NMR 300 MHz, DMSO-dB/MeOH-d4): 9.02 (s, 1H); 8.84 (d, J = 7.3, 1H, -NH); 8.26 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.59 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.43 (m, 1H); 3.89 (t, J = 6.4, 2H); 3.14 (m, 1H); 3.01 (m, 1H);2.89(m, 1H);2.74(m, 1H);2.12(m, 1H); 1.69 (m, 1H); 1.40 (m,2H); 1.07 (m,2H); 0.69 (t, J = 7.4, 3H).
Exannple A182: trans-4-[4-Methoxy-2-(2-methoxy-ethoxy)-ptienyl]-5H-pyrrolo[3,2-c/]pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide
Starting from trans-[4-({4-[4-methoxy-2-(2-methoxy-ettioxy)-phenyl)-5H-pyrrolo[3,2-rf]pyrimidine-7-carbonyl}-amino)-cyclotiexyl]-carbamic acid tert-butyl ester (example A130)the title compound was obtained as colorless solid. IViS (ESI): m/z = 440 (MH+, 100%).
1H-NMR {400 MHz, DMSO-d6/MeOH-d4): 8.99 (s, 1H); 8.45 (d, J= 7.9, 1H, -NH); 8.23 (s, 1H); 7.70 (d, J = 8.3, 1H); 6.77 (s, IN); 6.75 (dd, J1 = 8.3, Jz = 2.1, 1H); 4.25 (t, J = 4,6, 2H); 3.88 (s, 3H); 3.84 (m, IN); 3.55 (t, J = 4,6, 2H); 3.14 (s, 3H); 3.13 (m, 1H); 2.12-1.97 (m, 4H); 1.49 (m, 4H).
ExampleA183:cis-4-[4-Met hoxy-2-(2-methoxy-ethoxy )-phe nyl]-5H-py rro!o[3,2-dpyrimidine-7-carboxylic acid (4-amino-cyclohiexyl)-amide

starting from cis-[4-({4-[4-methoxy-2-{2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-
carbonyl}-amtno)-cyclohexyl]-carbarriic acid tert-butyl ester (example A131) the title compound was
obtained as colorless solid,
MS (ESI): m/z = 440 (MH+, 100%).
1H-NMR (400 MHz, DMSO-d6/MeOH-d,): 9.03 (s, 1H); 8.76 (d, J = 7.4, 1H, -NH); 8.23 (s, 1H); 7.71
(d, J = 8.3, 1H); 6.78 (s, 1H); 6.75 (dd, J, = 8.3, Jj = 2.1, 1H); 4,25 (t, J = 4,6, 2H); 3,88 (s, 3H);
3,56 (t, J = 4.6, 2H); 3.41 (m, 1H); 3.15 (s, 3H); 3.05 (m, 1H); 2.12-1.97 (m, 4H); 1.49 (m, 4H).
Example A184: 4-[4-Methoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4'ylamide
Starting from 4-{{4-[4-methoxy-2-(2-nnethoxy-ethioxy)-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl}-amino)-piperidine-1-carbdxy!ic acid tert-butyl ester (example A132) the title compound was obtained as colorless solid. MS (ES(): m/z = 426 (MH').
1H-NMR (400 MHz, DMSO-d6/MeOH-d4): 9.02 (s, 1H); 8.57 (d, J = 7.7, 1H, -NH); 8.24 (s, 1H); 7.72 (d, J = 8.2, 1H); 6.77 (s, IN); 6.75 (dd, J, = 8.2, J2 = 2.2,1H); 4.25 {t, J = 4.6, 2H); 4.06 (m, IN); 3.88 (s, 3H); 3.55 (t, J = 4.6, 2H); 3.15 (s, 3H & m, 2H); 1.92-1.87 (m, 4H); 1.73 (m, 2H); 1.61 (m, 2H).
Example A185; trans-4-[5-(2-Methoxy-ethoxy)-benzo(1,3Idioxol-4-yl]-5H-pyrrolo[3,2-o]pyrimidine-7-carbcixy(ic acid (4-amino-cyc(ohexyl)-amide
Starting from trans-[4-({4-[5-(2-methoxy-ethoxy)-benzo[1,3]dloxol-4-yl]-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl}-arDino)-cyclohexyl]-carbamic acid tert-butyl ester (example A133) the title compound was obtained as colorless solid. MS (ESI): m/z = 454 (MH\ 100%).
1H-NMR (200 MHz, DMSO-d6/MeOH-di): 9.00 (s, 1H); 8.31 (d, J = 7.9, 1H, -NH); 8.24 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.60 (d, J = 8.6, 1H); 6.01 (s, 2H); 4.02 (t, J = 4.7, 2H); 3.82 (m, 1H); 3.39 (t, J = 4.7, 2H); 3.03 (s, 3H); 2.81 (m, 1H); 1.92-1.38 (m, 8H).
Example A186: cis-4-[5-(2-Methoxy-ethoxy>-benzo[1,3]dioxol-4-yl]-5H-pyrralo[3,2-c/]pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide
Starting from cis-[4-({4-[5-(2-methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl}-amino)-cyctohexyl]-carbamic acid tert-butyl ester (example A134) the title compound was obtained as colorless solid. MS (ESI); m/z = 454 (MH+, 100%).
1H-NMR (200 MHz, DMSO-d6/MeOH-d^): 9.02 (s, 1H); 8.64 (d, J = 7.9, 1H, -NH); 8.27 (s, 1H); 7.01 (d, J = 8.6.1H); 6.62 (d, J = 8.6, 1H); 6.01 (s, 2H); 4.02 (t, J = 4.7, 2H & m, 1H); 3.40 (I, J = 4.7, 2H); 3.03 (s, 3H); 2,64 (m, 1H); 2.00 (m, 2H); 1.86 (m, 2H); 1.52-1.16 (m, 4H).

Example A187: 4-[5-(2-Methoxy-ethoxy)-ben2o[1,3]dioxol-4-yl]-5H-pyrroio[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide
Starting from4-({4-[5-(2-methoxy-ethoxy)-benzo(1,3]dfoxo/-4-yl]-5H-pyrrola[3,2-c(lpyrJrrridine-7-carbonyl}-amino)-piperidine-1-carboxylic acid tert-butyl ester (example A135) the title compound was obtained as colorless solid. MS (ESI): m/z = 440 (MH+, 100%).
1H-NMR (200 MHz, DMSO-d6/MeOH-di): 9.02 (s, 1H); 8.40 (d, J = 8.0. 1H, -NH); 8.27 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.61 (d, J = 8.6, 1H); 6.01 (s, 2H); 4.03 (t, J = 4.7, 2H); 3.96 (m, 1H); 3.39 (t, J = 4.7, 2H); 3.02 (s, 3H); 2.98 (m, 2H); 2.60 (m, 2H); 1.90 (m, 2H); 1.41 (m, 2H),
Example A188: 4-(2-CyclQpropylmethoxy-5-fluoro-4-hydroxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide hydrochloride
Starling from 4-{[4-(2-cyclopropylmethoxy-5-fluoro-4-methoxymethoxy-phenyl)-5H-pyrrolD[3,2-d]pyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid 1H-NMR (300 MHz, DMSO-d6): 12.66 (br.s, 1H, -NH); 10.91 (br.s, 1H, -OH); 9.19 (br.s, 2H, -NH^'); 9.12(5, IN); 8.64 (d, J = 2.9, 1H); 8.53 (d, J = 7.5, 1H,-NH); 7.53 (d, J = 11.5, 1H); 6.85 (d, J = 7.3, 1H); 4.17 (m, 1H); 3.85 (d, J = 6.9, 2H); 3.32 (m, 2H); 3.06 (m, 2H); 2.11 (m, 2H); 1.85 (m, 2H); 0.99 (m, 1H); 0.36 (m, 2H); 0.26 (m, 2HI
Example A189: 4-[2-Cyclopropylmethoxy-4-(1,1-difluoro-methoxy)-5-fluoro-phenyl]-5H-pyrroto(3,2-Q]pyrimidine-7-carboxylic acid piperidin-4-yfam(de hydrochloride Starting from 4-{[4-(2-cyclopropylmethoxy-5-fluoro-4-methoxymethoxy-phenyl)-5H-pyrrolo[3,2-cf]pyrimidlne-7-carbony!]-amino}-piperidine-1-carboxyllc acid fert-butyl ester (example A136) the title compound is obtained as pale yellow solid. MS (ESI): m/z = 476 (MH+ 100%).
'H~NMR (300 MHz, DMSO-d6): 12.47 (br.s, 1H. -NH); 9.16 (br.s, 2H, -NH2'); 9.12 (s, 1H); 8.51 (d, J = 7.5, 1H, -NH); 8.50 (s, 1H); 7.67 (d, J = 10.9, 1H); 7.45 (t, J = 72.5, 1H); 7.21 (d, J = 6.0, 1H); 4.14 (m, 1H); 3,93 (d, J = 7.1, 2H); 3.31 (n, 2H); 3.07 (m, 2H); 2,13 (m, 2H}; 1.83 (m, 2H); 0.96 (m, 1H); 0,35 (m,2H); 0.23 (m,2H).
Example A190: (S)-1-(4-Amino-piperidin-1-yl)-2-hydroxy-propan-1-one hydrochloride To a solution of 4-amino-piperidine-4-carboxylic acid tert-butyl ester (2.50 g, 12.48 mmol) and Huenigs base (3.2 mL; 18.7 mmol) in dichloromethane (15 mL) is added (S)-2-acetoxypropionyl chloride (1.9 mL; 15.0 mmol) under ice-cooling. The mixture is stirred overnight at ambient temperature. The solvent is evaprarated and the obtained crude product is partitioned between ethyl

acetate and saturated sodium bicarbonate solution. Drying and evaporation of the solvent gave an orange oil (4.14 g) which is dissolved in methanol (30 mL). A4M HCI in 1,4-dioxane (30 mL) is added and the mixture is stirred for 20 min at ambient temperature. The voiatiles are evaporated and the obtained solid is triturated w\lh diethyl ether. Recrystalli2ation from methanol / 1,4-dioxane gave 1.63 g of the title compound as white solid. MS (ES)): m/z = 173 (MH', 100%).
1H-NMR (400 MHz, DMSO-d6): 8.20 (br.s, 3H, -NH3*); 4.85 (br.s, 1H, -OH); 4,30 (m, 2H); 4.00 (m. 1H); 3.10 (m, 2H); 2.30 (m, 1H); 2.00 (m, 2H}; 1.40 (m, 2H); 1.18 (d, 3H, J = 6.0),
Example A191: 1-(4-Amino-piperidin-1-yl)-ethanone To a solution of 4-amino-piperidine-4-carboxylic acid terf-lbutyl ester (2.50 9; 12.5 mmo/) and Huenigs base (3.2 mL) in dichloromethane (15 mL) is added acetyl chloride (l.lmL; 15.0 mmol) under ice-cooling, The mixture is stirred overnight at ambient temperature. The solvent is evaporated and the obtained crude is partitioned between ethyl acetate and 1M aqueous HCI. Drying and evaporation of the solvent gave an orange oil which is dissolved in dichloromethane (38 mL). Trifiuoroacetic acid (19 mL) Is added and the mixture is stirred for 20 min at ambient temperature. The vofatiles are completely evaporated at 35°C bath temperature and the obtained residue is dissolved in a mixture of dichloromethane / methanol (95 : 5 v/v). Solid sodium carbonate Is added and the suspension is stirred at ambient temperature overnight. Filtration and evaporation of the solvent gave 0.98 g of the title compound as slightly brown oil. MS (ESI): m/z = 142 (MH+, 100%).
1H-NMR (400 MHz, DMSO-d6): 4.12 (m, 1H); 3.65 (m, 1H); 3.35 (br.s, 2H, -NH); 3.00 (m, 1H); 2.74 (m. 1H); 2.57(m, 1H); 1.95 (s, 3H); 1.68 (m, 2H); 0.98 (m, 2H).
The following compound is obtained analogously to the procedure described in above example A191.
Example A192: 1-(4-AmmQ-piperidin-1-yl)-2-methQxy-ethanone Starting from 4-amino-piperidrne-4-carboxylic acid tert-butyl ester and methoxy-acetyl chloride the title compound Is obtained as slightly brown oil. MS (ESI): m/z = 173 (MH', 100 %).
Example A193: trans-(4-Cyclopropylcarbamoyl-cyclohexyl)-carbamic acid tert-butyl ester To a stirred mixture of trans-4-tert-butoxycarbonylamino-cyclohexanecarboxylic acid (6.1 g, 25.0 mmol) and cyclopropylamine (1.9 mL, 27.5 mmol) in dichloromethane (125 mL), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (5.3 g; 27.5 mmol) is added in one portion. The reaction is stirred at ambient temperature for 48 hours. The solvent is evaporated and the crude is stirred in ice-cold IN hydrochloric acid (100 mL) for 30 min. The solid product is isolated

by suction filtration, washed with small portions of water and recrystallized from ethanol/water to
deliver 5.2 g of the title compound as colorless solid.
MS (ESI): m/z = 305 (MNa*); 283 (MH'); 227 (MH+-C1Hs, 100 %).
1H-NIVIR (200 MHz, DMSO-da,): 7.70 (d, J =4.1, 1H,-NH); 6.64 (d, J = 7.6, 1H,-NH); 3.13 {m, 1H);
2.57 (m, 1H); 1.91 (m, 1H); 1.86-1.58 (m, 4H); 1.37 (m, 9H); 1.33 (m. 2H); 1.09 (m, 2H); 0.57 (m,
2H); 0.34 (m, 2H).
The foUowing compound is obtained analogously to the procedure described in above example A193.
Example A194: trans-[4-(2-Methoxy-ethylcarbamoyl)-cyclohexyl]-carbamic acid tert-butyl ester
Starting from trans-4-tert-butoxycarbonylamino-cyctohexanecarboxylic acid and 2-methoxy-ethylamine the title compound is obtained as colorless solid. MS (ESI): m/z = 323 (MNa*); 301 (MH\ 100 %); 245 (MH'-C4HB).
1H-NMR (200 MHz, DMSO-d6,): 7.72 (t, J = 5.4, IN, -NH); 6.65 (d, J = 7.7, IN, -NH); 3.30 (t, J = 5.3, 2H); 3.23 (s, 3H); 3.18 (m, 2H & m, 1H); 2.01 (m, 1H); 1.73 (m, 4H}; 1.37 (m. 9H); 134 (m, 2H); 1.11 (m, 2H).
Example A195: trans-4-Amino-cyclohexanecarboxylic acid cyclopropylamide hydrochloride Trans-(4-Cyclopropylcarbamoyl-cyclohexyl)-carbamic acid tert-butyl ester from example A193 (5.0 g; 17,7 mmol) is suspended in 1,4-dioxane (72 mL). 4N hydrochloric acid in 1,4-dioxane (18.0 mL) is added and the mixture is stirred at 80°C for six hours. The product is precipitated vi/ith tert-butylmethylether at ice bath temperature, isolated by suction filtration, washed with small portions of tert-butylmethylether and dried under reduced pressure to deliver 3.8 g of the title compound as colorless solid,
MS (ESI): m/z = 183 (MH+, 100 %); 166 MH+-NHs).
'1H-NMR (200 MHz. DMSO-d6,): 8.07 (br.s, 1H, -NH3'); 7.84 (d, J = 4.0,1H, -NH); 2.93 (m, 1H); 2.59 (m, 1H); 1.97 (m, 3H); 1.73 (m, 2H); 1.34 (m, 4H); 0.58 (m, 2H); 0.35 (m, 2H).
The following compound is obtained analogously to the procedure described in above example A195.
Example A196: trans-4-Amino-cyclohexanecarboxylic acid (2-methoxy-ethyl)-amide hydrochloride
Starting from trans-[4-(2-methoxy-ethylcarbamoyl)-cyclohexyl]-carbamic acid tert-butyl ester (example A194) the title compound is obtained as colorless solid, MS (ESI): m/z = 201 (MH+ 100 %); 183 MH'-NH2).

1H-NMR (200 MHz, DMSO-d6,): 8.19 {br.s, 1H, -NH3*); 7.87 (br.s. 1H, -NH); 3.31 (t, J = 5.4, 2H); 3.23 (s, 3H); 3.16 (t,j = 5.4, 2H); 2.91 (m, 1H); 2.08(m, 1H); 1.99 (m, 2H); 1.76 (m, 2H); 1.38 (m, 2H).

Example 1; 4-(5-Cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H'-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-propionyi-piperidln-4-yl)-amid
4-(5-Cyclopropylmethoxy-1,3-ben2odioxol-4-yl)-5H-pyrrol[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide hydrochloride from example A138 (472 mg; 1.0 mmol) and DBU (2.5 mmol) is dissolved in dry dichloromethane (5 mL). Propionyl chloride (1.1 mmol) is syringed into the reaction mixture at ice bath temperature. After complete addition stirring is continued at ambient temperature over night. Methanol {1 mL) is added and stirring is continued for two hours. The volatiles are evaporated. The residue is purified by reversed phase preparative HPLC. The collected product fraction is freeze-dried to yield 375 mg of the title compound as colorless solid. MS (ESI): m/2= 492.1 (MH').
1H-NMR (400 MHz, DMSO-d6): 12.28 (br.s, 1H. -NH); 9.02 (s, 1H); 8.45 (d, J = 7.8, 1H, -NH); 8.29 (s, 1H); 7.00 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.23 (m, 1H); 4.14 (m, 1H); 3,83 {m, 1H); 3.76 (d, J = 6.8, 2H); 3.24 The following compounds are obtained analogously to the procedure described in above example 1.
Example 2: 4-({1-[4-{5-Cyclopropylmethoxy-benzo[1,3]diaxol-4-yl)-5H-pyrrolo[3,2-c/|pyrimidin-7-yl]-methanoyl}-amino)-piperidine-1-carboxylic acid ethyl ester Starting from 4-(5-cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartxDxylic acid piperidin^-ylamide hydrochloride (example A138)and ethyl chloroformate the title compound is obtained as colorless solid. MS(ESI):m/z = 494(MH+).
1H-NMR (400 MHz, DMS0-d6): 12.27 (br.s, 1H, -NH); 9.03 (s, 1H); 8.44 (d, J = 7.8, 1H, -NH); 8.29 (s, IN); 7.01 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.08 (m, 1H & qu, J = 7.1, 2H); 3.91 (m, 2H); 3.76 (d, J = 6.8, 2H); 3.08 (m, 2H); 1.95 (m, 2H); 1.47 (m, 2H); 1.20 (t, J = 7.1, 3H); 0.87 (m, 1H); 0.29 (m, 2H); 0.10 (m, 2H).
Example 3: 4-(5-Cyclopropylmethoxy-benzo[1,3]dloxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-methoxy-acetyl)-piperidin-4-yl]-amide
Starting from 4-(5-cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide hydrochloride (example A138) and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/2 = 508 (MM*).
1H-NMR (400 MHz, DMSO-d6): 11,99 (br.s, 1H, -NH); 9.03 (s, 1H); 8.45 (d, J = 7.8,1H, -NH); 8.30 (s, 1H); 7.01 (d, J = 8.6,1H); 6.56 (d, J = 8.6, 1H); 6.00 {s, 2H); 4.15 (m, 2H); 4.12 (s, 2H); 3,76 (m, 1H&d,J = 6.8, 2H);3.31 (s, 3H); 3.21 (m, 1H); 2.94 (m, 1H); 1.97 (m, 2H); 1.55 (m. IN); 1.42 (m, 1H); 0.87 (m, 1H); 0.29 (m, 2H); 0.10 (m, 2H).

Example 4: trans-4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol4-yl)-5i4-pyrrolo[3,2-c']pyrimidine-7-carboxylic acid (4- acetylamino-cyclohexyl)-amide
Starting from tran&4-(5-cyclopropylmethoxy-benzo[1,3]dioxoM-ylJ-5H-pyrrolof3.2-o]pyrimidine-7-carboxylic acid (4-amlno-cyclohexyl)-amide (example A140) and acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 492 (MH').
1H-NMR (400 MHz, DMSO-d6): 11.42 (br. S, 1H, -NH); 9.03 (s, 1H); 8.30 (d, J = 7.9, 1H, -NH); 8.27 (s, 1H); 7.74 (d, J = 7.7, 1H, -NH); 7.00 (d. J - 8.5, 1H); 6,56 (d, J = 8.5, 1H); 6.00 (s, 2H); 3.82 (m, IN); 3.76 (d, J = 6.7, 2H); 3.58 (m, 1H); 2.01 (-d; J ~ 10.0, 2H); 1.86 (~d, J ~ 10.2, 2H); 1.63 (s, 3H); 1.42 (m, 2H); 1.31 (m, 2H). 0.87 (m, 1H); 0.29 (m, 2H); 0.11 (m, 2H).
Examples: trans-4-(5-Cyclopropylmelhoxy-benzo[1,3]dioxol-4-y])-5H-pyrrolo[3,2-d]gy{mKllfie-7-ca^baK^\\c add {4- [{1-cyclopropyl-methanoyl)-amino]-cyclohexyl}-amide Starting from trans-4-(5-cyclopropylmethoxy-benzo[1,3]dioxol-4-y|)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A140) and cyclopropanecarbonyl chloride the title compound is obtained as colorless solid, MS (ESI): m/z = 518 (MH+).
1H-NMR (400 MHz, DMSQ-de): 12.23 (br. S, 1H, -NH); 9.03 (s, 1H); 8.31 (d, J = 7.8, 1H, -NH); 8.27 (s, IN); 7.96 (d, J = 7.7, 1H, -NH); 7.00 (d, J = 8.5, 1H); 6.56 (d, J = 8.5, 1H); 6.00 (s, 2H); 3.82 (m, 1H); 3.76 (d, J = 6.8, 2H); 3.61 (m, 1H); 2.02 (~d; J ■- 10.0, 2H); 1.87 (~d, J ~ 10.2, 2H); 1.54 (m, 1H); 1.38 (m,4H); 0.87 (m, 1H); 0.64 (m, 4H); 0.31 (m, 2H);0.11 (m, 2H).
Examples: trans-f4-({1-(4-(5-Cyclopropylmethoxy-benzof1,3]dioxoJ-4-yt)-5H-pyrrolo[3,2-c(|pyrimidin-7-yl]-methanoyl}-ain1Ho)-cyclohexyl]-carbamic acid ethyl ester
Starting from trans-4-(5-cyclopropylmethoxy-benzo[1,3]dioxol-4-y|)-5H-pyrrolo[3,2-cr|pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A140) and ethyl chloroformate the title compound is obtained as colorless solid. MS (ESI): m/z = 522 (MM").
1H-NMR (400 MHz, DMSO-d6): 12.25 (br. s, 1H, -NH); 9.03 (s, 1H); 8.29 (d, J = 7.9, 1H, -NH); 8.27 (s, 1H); 7.02 (d, J = 9.2, 1H, -NH); 7.00 (d, J = 8.5, IN); 6.56 (d, j = 8.5,1H); 6.00 (s, 2H); 3.98 (qu, J = 7.0, 2H); 3.79 (m,1H); 3.76 (d, J = 6.7, 2H); 3.31 (m, 1H); 2.00 (~d, J ~ 10.3, 2H); 1.87 (~d, J ~ 11.4, 2H); 1.37 (m, 4H): 1.16 (t, J = 7.0, 3H); 0.86 (m, 1H); 0.29 (m, 2H); 0.10 (m, 2H).
Example 7: cis-4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c/]pyrjmidine-7-carboxylicacld (4- acetylamino-cyclohexyl)-amide

starting from cis-4-(5-cyclopropylmethoxy-benzo[1,3]dioxoi-4-yl}-5H-pyrrolo[3,2-d]pyrimldine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A141) and acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 492 (MM').
1H-NMR (400 MHz, DMSO-d6): 12.24 (br.s, IN, -NH); 9.06 (s, IN); 8,56 (d, J = 7.6,1H, -NH); 8.28 (s, 1H); 7.86 (d, J = 7.4, 1H, -NH); 7.01 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, IN); 6.01 (s, 2H); 4.03 (m, 1H); 3.77 (m, 1H &d, J = 6.7, 2H); 1.84 (s,3H); 1.73 (m,6H); 1.59 (m, 2H); 0.88 (m, 1H);0.30(m, 2H);0.11 (m,2H).
Example 8: cis-4-(5-Cyclopropylmethoxy-benzo[1,3jdioxol-4-yl)-5H-pyrro(o[3,2-d[pyrimidine-7-carboxytic acid {4- [(1-cyclopropyl-methanoyl)-amino]-cyclohexyl}-amide Starting from cis-4-(5-cyclopropylmethoxy-benzo[1,3]d!OXQl-4-y!)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)'amide (example A141) and cyclopropanecarbonyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 518 (MH+).
1H-NMR (400 MHz, DMSO-d6): 12.24 (br.s, IN, -NH); 9.07 (s, 1H); 8.58 (d, J = 7.5, 1H, -NH); 8.29 (s, 1H);8.07(d, J = 7.4, 1H,-NH);7.01 (d, J = 8.6, 1H); 6.56(d, J = 8.6, 1H); 6.01 (s, 2H); 4.03 (m, 1H); 3.77 (m, 1H & d, J = 6.7, 2H); 1.79 (m, 1H}; 1.67 (m, 8H); 0.87 (m, 1H); 0.65 (m, 4H); 0.31 (m, 2H);0.11 (m, 2H).
Example 9: cis-4-(5-Cyclopropylmethoxy-benzo[1,3]dioxDl-4-yl>-5H-pyrrolo[3,2-djpy rim id i ne-7-carboxy lie acid (4-(2-methoxy-ethanoylamino)-cyclohexyl]-amide Starting from cis-4-(5-cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic add (4-amino-cyclohexyl)-amide (example A141) and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/2 = 522 (MH+).
1H-NMR (400 MHz, DMSO-d6): 12.22 (br.s, IN, -NH); 9.06 (s, 1H); 8.59 (d, J = 7.4,1H, -NH); 8.28 (s, 1H); 7.70 (d, J = 7.7, 1H, -NH); 7.01 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 6.01 (s, 2H); 4.06 (m, 1H); 3.82 (s,2H); 3.77 (m, 1H & d, J = 6.8, 2H); 3.31 (s, 3H); 1.80 (m, 3H); 1.74 (m, 2H); 1.69 (m, 4H); 0.86 (m, 1H); 0.30 (m, 2H); 0.11 (m, 2H).
Example 10: cis-[4-({1-[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]-methanoyl}-amino)-cyclohexyl]-carbamic acid ethyl ester Starting from cis-4-(5-cyclopropylmethoxy-benzo[1,3]dioxol-4-yl>-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A141) and ethyl chloroformate the title compound is obtained as colorless solid. MS (ESI): m/2 = 522 (MH+).

1H-NMR (400 MHz, DMSO-d6): 12.26 (br.s, 1H, -NH); 9.05 (s, 1H); 8.60 (d, J = 7,7, 1H, -NH); 8.27 (s, 1H); 7.23 (d, J = 7.7, 1H, -NH); 7.01 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 6.01 (s, 2H); 3.99 (m, 1H&qu,J = 7.1,2H);3.50(rr, 1H); 1.80 {m,3H); 1.78 (m, 2H); 1.67 (m, 6H); 1.17 (t, J = 7.1, 3H); 0.88 (m, 1H); 0.30 (m, 2H); 0.11 (m, 2H),
Example 11: 4-(5-Cyclopropylmethoxy-benzo[1,31dioxoM-yl)-5H-pyrro[o[3,2-d]pyrimidine-7-carboxylic acid (1-acetyl-piperidin-4-yl}-amide
Starting from 4-(5-cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperldin-4-ylamide hydrochloride (example A138) and acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 478 (MH+).
1H-NMR (400 MHz, DMSO-d6): 11.91 (br.s, 1H, -NH); 9.03 (s, IN); 8.45 (d, J - 7.8, 1H, -NH); 8.30 (s, 1H); 7.01 (d, J = 8,6,1H); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.21 (m, 1H); 4.13 (m, 1H); 3,81 (m, 1H); 3.76 (d, J = 6.8, 2H); 3.24 (m, 1H); 2,91 (m. 1H); 2,04 (s, 3H); 1.97 (m, 2H); 1.56 (m, 1H); 1.40 (m, 1H); 0.87 (m, 1H); 0,29 (m, 2H); 0.10 (m, 2H).
Example 12: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidlne-7-carboxylic acid [1-(1-cyclopropyl-methanoyl)-piperidin-4-yl].amide Starting from 4-(5-cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide hydrochloride (example A138) and cyclopropanecarbonyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 504 (MH+).
1H-NMR (400 MHz, DMSO-d6): 12.16 (br.s, 1H, -NH); 9,03 (s, IN); 8.46 {d, J = 7,8, 1H, -NH); 8.30 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, IN); 6.00 (s, 2H); 4.18 (m, 3H); 3.76 (d, J - 6.8, 2H); 3.31 (m, 1H); 2.96 (m, 1H); 2.01 (m, 3H); 1.54 (m, IN); 1,42 (m, 1H); 0.87 (m, 1H); 0.72 (m, 4H); 0.29(m, 2H);0,13(m,2H),
Example 13: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxy1ic acid [(R)-1-(2-methoxy-acetyl)-pyrrolidin-3-yl]-amide
Starting from 4-{5-Cyclopropylmethoxy-ben20[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (R)-pyrrolidin-3-ylamide hydrochloride (example A142) and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 494 (MH+).
1H-NMR (300 MHz, DMSO-d6): 12,31 (br.s, 1H, -NH); 9.02 (s, 0.5H); 9.01 (s, 0.5H); 8.57 (d, J = 6.7, 0.5H, -NH);8.55 (d, J = 6.0, 0.5H, -NH); 8.31 (s, 1H); 7.00 (d, J = 8.6, 1H); 6.56 {d, J = 8,6, 1H); 6.00 (s, 2H); 4.61 (m, 0.5H); 4.51 (m, 0.5H); 4.06 (d, J = 4.0,1H); 4.01 (d, J = 1.5, 1H); 3.82 -3.67 (m. 1H); 3.76 (d, J = 6.7, 2H); 3.61 - 3.45 (m, 2H); 3.38 (m, IN); 3.32 (s, 1,5H); 3.30 (s, 1,5H); 2.31 - 2.17 (m, 1H); 2.06 (m, 0.5H); 1.93 (m, 0,5H); 0.87 (m, 1H); 0,29 (m, 2H); 0.10 (m, 2H).

Example 14; 4-{5-Cyclopropylmethoxy-benzo[1.3jdioxol-4-yl)-5H-pyrroio[3.2-d]pyrimidine-7-carboxylic acid ((R)-1-formyl-pyrrolidin-3-yl)-amide
Starting from 4-{5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-cGpyrimidine-7-cartKDxylic acid (R)-pyrrolidin-3-ylamide hydrochloride (example A142) and acetic formic anhydride the title compound is obtained as colorless solid. MS (ESI); m/z = 450 (MH+).
1H-NMR (300 MHz, DMSO-d6): 12.31 (br.s, 1H, -NH); 9.03 (s, 0.5H); 9.02 (s, 0.5H); 8.57 (d, J = 6,9, 0.5H, -NH); 8,53 (d, J = 6.9, 0,5H, -NH); 8.32 (s, 1H); 8.22 (s, 1H); 7.01 (d, J = 8,6, 1H); 6.56 (d, J = 8.6, 1H); 6,00 (s, 2H); 4,56 (m, 1H); 3.85 (m, 0.5H); 3.76 (d, J = 6.8, 2H); 3,66 (m, 1H & 0,5H); 3.47 (m, 1H & 0.5H); 3.27 (m, 0.5H); 2,26 (m, 1H); 2.01 (m, 1H); 0.87 (m, 1H); 0.29 (m, 2H); 0.10 (m,2H).
Example 15; 4-(5-Cyclopropyln"ie1Hoxy-benzo[1,3]dloxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ((R)-1-acetyl-pyrrolidin-3-yl)-amide
Starting from 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartxjxylic acid (R)-pyrrolidin-3-y!amide hydrochloride (example A142) and acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 464 (MH+).
1H-NMR (300 MHz, DMSO-d6): 12,31 (br.s, 1H, -NH); 9.03 (s, 1H); 8.58 (d, J = 6.9, 0.5H, -NH); 8.55 (d, J = 6,9, 0.5H, -NH); 8.31 (d, J = 1.6, 1H); 7.01 (d, J = 8.6, 1H); 6.56 (d, J = 8,6, 1H); 6.00 (s, 2H); 4.61 (m, 0.5H); 4.51 (m, 0.5H); 3.84 (m, 0.5H); 3,76 (d, J = 6,7, 2H); 3.64 (m, 1H & 0.5H); 3,46 (m, 1H&0,5H);3,31 (m, 0.5H); 2,25 (m, 1H); 2.06 (m, 0.5H); 1,98 (s, 1.5H); 1.96 (s, 1.5H); 1.95 (m, 0.5H); 0.87 (m, 1H); 0,29 (m, 2H); 0,10 (m, 2H),
Example 16; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [{R)-1-(1-cyclopropyl-methanoyl)-pyrrolidin-3-yl]-amide Starting from 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (R>-pyrnolidin-3-ylamide hydrochloride (example A142) and cyclopropanecarbonyl chloride the title compound Is obtained as colorless solid. MS (ESI): m/z = 490 (MH+).
1H-NMR (300 MHz, DMSO-d6): 12,31 (br.s, 1H, -NH); 9.03 (s, 1H); 8.61 (d, J = 6,9, 0.5H, -NH); 8.55 (d, J = 6.9, 0.5H, -NH); 8,32 (d, J = 2.6, IN); 7,01 (d, J = 8,6, 1H); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.65 (m, 0,5H); 4.54 (m, 0,5H); 4.02 (m, 0,5H); 3.82 (m, 1H); 3,76 (d, J = 6.7, 2H); 3.65 (m, 1H); 3.51 (m, 1H); 3,35 (m, 0.5H); 2,33 (m, 0.5H); 2,21 (m, 0,5H); 2.10 (m, 0.5H); 1.98 (m, 0.5H); 1.79 (m, 1H); 0.87 (m, 1H); 0.73 (m, 4H); 0.29 (m, 2H); 0.11 (m, 2H).

Example 17: (R)-3-({1-[4-(5-Cyclopropylmethoxy-ben20[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]-methanoyl}-amino)-pyrrolidine-1-carboxylic acid ethyl ester Starting from 4-(5-Cyclapropylmethoxy-benzo[1,3]dJoxol-4-yl)-5H-pyrroiot3,2-dtpyrimidine-7-carboxylic acid (R)-pyrrolidin-3-ylamide hydrochloride (example A142) and ethyl chloroformate the title compound is obtained as colorless solid. MS (ESI): m/z = 494.1 (MH+).
1H-NMR (300 MHz, DMSO-d6); 12.31 (br.s, 1H, -NH); 9.02 (s, 1H); 8.56 (d, J = 6.8, 1H, -NH); 8.31 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.56 (d, J = 8,6, 1H); 6.00 (s, 2H); 4,52 (m, 1H); 4,05 (qu, J = 7.0, 2H); 3.76 (d, J = 6.7, 2H); 3.65 (m, IN); 3.48 (m, 2H); 3.29 (m, 1H); 2.22 (m, 1H); 1.99 (m, 1H); 1.79 (m, 1H); 1.19 (t, J = 7.0, 3H); 0.87 (m, 1H); 0.29 (m, 2H); 0.10 (m, 2H).
Example 18: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyltc acid {(S)-1-formyl-pyrrolidin-3-yl)-amide
Starting from 4-(5-Cydopropy\metboxy-benzol 1,3]6k>xoi-4 -y\}-5H-pynotol3,2-d]pyrimidine-7-carboxylic acid (S)-pyrrolidin-3-ylamide hydrochloride (example A143) and acetic formic anhydride the title compound is obtained as colorless solid. MS (ESI): m/z = 450(MH+').
1H-NMR (300 MHz. DMSO-d6): 12,31 (br.s, 1H, -NH); 9.03 (s, 0.5H); 9.02 (s, 0.5H); 8.57 (d, J = 6.9, 0.5H, -NH); 8.53 (d, J = 6.9, 0.5H, -NH); 8.32 (s, IN); 8.22 (s, IN); 7,01 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, IN); 6.00 (s, 2H); 4.56 (m, IN); 3.85 (m, 0,5H); 3.76 (d. J = 6,8, 2H); 3.66 (m, 1H & 0.5H); 3.47 (m, 1H & 0,5H); 3.27 (m, 0.5H); 2.26 (m, IN); 2.01 (m, 1H); 0,87 (m, IN); 0.29 (m, 2H); 0,10 (m,2H).
Example 19: 4-(5^Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrro!o[3,2-d]pyrimidine-7-carboxylic acid ((S)-1-acetyl-pyrrolidin-3-yl)-amide
Starting from 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c(ipyrimidine-7-cartroxylic acid (S)-pyrrolidin-3-ylamide hydrochloride (example A143) and acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 464 (MM*).
1H-NMR (300 MHz, DMSO-d6): 12.31 (br.s, 1H. -NH); 9.03 (s, 1H); 8,58 (d, J = 6.9, 0,5H, -NH); 8,55 (d, J = 6.9, 0.5H, -NH); 8.31 (d, J = 1.6, 1H); 7.01 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.61 (m, 0.5H); 4.51 (m, 0.5H); 3.84 (m, 0.5H); 3.76 (d, J = 6.7, 2H); 3.64 (m, 1H & 0,5H); 3.46 (m, 1H & 0.5H); 3.31 (m, 0.5H); 2.25 (m. 1H); 2.06 (m, 0.5H); 1.98 (s, 1.5H); 1.96 (s, 1.5H); 1,95 (m, 0.5H); 0.87 (m, 1H); 0.29 (m, 2H); 0.10 (m, 2H),
Example 20: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [{S)-1-(1-cyclopropyl-methanoyl)-pyrrolidin-3-yl]-amide

starting from 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolD[3,2-d]pyrimidine-7-carboxylic acid (S)-pyrrolidin-3-ylamide hydrochloride {example A143) and cyclopropanecarbonyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 490 (MH+).
1H-NMR (300 MHz, DMSO-d6): 12.31 (br.s, 1H, -NH); 9.03 (s, 1H); 8.61 (d, J = 6,9, 0.5H, -NH); 8.55 (d, J = 6,9, 0.5H, -NH); 8,32 (d, J = 2.6, 1H); 7.01 (d, J = 8.6, 1H); 6.56 (d, J = 8,6, 1H); 6.00 (s, 2H): 4,65 {m, 0.5H); 4.54 (m, 0.5H); 4.02 {m, 0.5H); 3.82 (m, 1H); 3.76 (d, J = 6.7, 2H); 3.65 (m, 1H); 3.51 (m, 1H); 3.35 (m, 0.5H); 2.33 (m, 0,5H); 2.21 (m. 0.5H); 2.10 (m, 0.5H); 1,98 (m, 0.5H); 1.79 (m, 1H); 0.87 (m, 1H); 0.73 (m. 4H); 0.29 {m, 2H); 0.11 (m, 2H).
Example 21; 4-(5-cyclopropylmethoxy-ben2o[1,3]dioxol-4-yl)-5H-pyrrolo(3,2-d]pyrimidine-7-carboxylic acid [(S)-1-{2-methoxy-ethanoyl)-pyrrolidin-3-yl]-amide Starting from 4-{5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {S)-pyrrolidin-3-ylamide hydrochloride (example A143) and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI); m/z = 494 (MH+).
1H-NMR (300 MHz, DMSO-d6): 12.31 (br.s, 1H, -NH); 9.02 (s, 0.5H); 9,01 (s, 0.5H); 8.57 (d, J = 6.7, 0.5H, -NH);8.55 (d, J = 6.0, 0.5H, -NH); 8,31 (s, 1H); 7,00 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 4,61 (m, 0,5H); 4,51 (m, 0.5H); 4.06 (d, J = 4.0, 1H); 4.01 (d, J = 1.5, 1H); 3.82 -3.67 (m, 1H);3.76(d, J = 6.7, 2H);3.61 - 3.45 (m, 2H); 338 (m, 1H);3.32{s. 1.5H); 3.30 (s, 1.5H); 2.31 - 2.17 (m, 1H); 2.06 (m, 0.5H); 1.93 (m, 0.5H); 0.87 (m, 1H); 0.29 (m, 2H); 0,10 (m, 2H),
Example 22; {S)-3-({1-[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]-methanoyl}-amino)-pyrrolidine-1-carboxylic acid ethyl ester Starting from 4-{5-Cyclopropylmethoxy-benzo(1,3]dioxol-4-yl)-5H-pyrrolo[3,2-cf|pyrlmidine-7-carboxylic acid (S)-pyrrolidin-3-ylamide hydrochloride (example A143) and ethyl chloroformate the title compound is obtained as colorless solid, MS(ESI):m/2 = 494,1(MH+).
1H-NMR (300 MHz, DMSO-d6): 12.31 (br.s, 1H, -NH); 9.02 (s, 1H); 8.56 (d, J = 6.8, 1H, -NH); 8.31 (s. 1H); 7.01 (d, J = 8.6, 1H); 6.56 (d, J = 8,6, 1H); 6.00 (s, 2H); 4.52 (m, 1H); 4.05 (qu, J = 7.0, 2H); 3.76 (d, J = 6.7, 2H); 3.65 (m, 1H); 3.48 (m, 2H); 3.29 (m, 1H); 2.22 (m, 1H); 1.99 (m, 1H); 1.79 (m, 1H); 1.19 (t, J = 7.0, 3H); 0.87 (rr, 1H); 0.29 (m, 2H); 0.10 (m, 2H).
Example 23: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-fonnyl-piperidin-4-ylmethyl)-amide
Starting from 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (piperidin-4-ylmethyl)-amide (example A144) and acetic formic anhydride the title compound is obtained as colorless solid.

MS (ESI): m/z = 478 (MH+),
1H-NMR (400 MHz, DMSO-d6): 12.27 (br.s, 1H, -NH); 9.04 (s, 1H); 8.51 (t, J = 5.9, 1H, -NH); 8.28 (s, 1H); 7.97 (s, IN); 7.01 (d, J = 8.5, 1H); 6.57 (d, J = 8.5, 1H); 6.00 (s, 2H); 4.18 (m, 1H); 3.77 (d. J = 6.7, 2H); 3.69 (m, 1H); 3.35 (dd, J, = J2 = 6.2, 2H); 3.02 (m, 1H); 2.60 (m, 1H); 1.87 (m, 1H); 1.77 (m, 2H); 1.15 (m, 1H); 1.06 (m, 1H); 0.88 (m, 1H); 0.30 (m, 2H); 0.11 (m, 2H).
Example 24: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-acetyl-piperidin-4-ylmethyl)-am(de
Starting from 4-(5-CyclopropyJmethoxy-benzo(1,3]dioxol-4-yl)-5H-pyrralo[3,2-djpyhmidine-7-cartioxyllc acid (piperidin-4-ylmethyl}-amide (example A144) and acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 492 (MH+),
1H-NMR(400 MHz, DMSO-d6): 12.27 (br.s, 1H, -NH); 9.03 (s, 1H); 8.50 {t, J = 6,1, 1H, -NH); 8,27 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.57 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.38 (m, 1H); 3.82 (m, 1H); 3.77 (d, J = 6.8, 2H); 3.35 (dd, J1 = J2 = 6.0. 2H); 3.01 {m, 1H); 2.50 (m, 1H); 1.98 (s, 3H); 1.82 (m, 1H); 1.74(m,2H); 1.20 (m, 1H); 1.06 (m, 1H);0.88(m, IN); 0.30 (m, 2H); 0.11 (m, 2H).
Example 25: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxo^4-yl)-5H-pyrrolo[3,2-c^pyr^midine-7-carboxylic acid [1-(1-cyclopropyl-methanoyl)-piperidin-4-ylmethyl]-amide Starting from 4-(&-Cyclopropylmethoxy-benzo[1,3Jdioxol-4-yl)-5rt-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (piperidin-4-ylmethyl)-amide (example A144) and cyclopropanecarbonyl chloride the title compound is obtained as colorless solid. MS (ESI); m/z = 518 (MH+),
1H-NMR (400 MHz, DMSO-d6): 12.27 (br.s, 1H,-NH); 9.03 (s, 1H); 8.51 (t, J = 6.1, IN,-NH); 8.27 (d, J = 2.2, 1H); 7.01 (d, J = 8.6, IN); 6.57 (d, J = 8.6, 1H); 6.00 {s. 2H); 4.36 (m, 1H); 4.28 (m.1H); 3.77 (d, J = 6,7, 2H}; 3.35 (dd, J, = J2 = 6.2, 2H); 3.08 (m, 1H); 2.58 (m, 1H); 1.97 (m, 1H); 1.86 (m, 2H); 1.74 (m, IN); 1,20 (m, 1H); 1.09 (m, 1H); 0.88 (m, 1H); 0.68 (m, 4H); 0.30 (m, 2H); 0.10 (m, 2H).
Example 26: 4-(5-CyclQpropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-methoxy-ethanoyl)-piperidin-4-ylmethyl]-amide Starting from 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-o(|pyrimidine-7-cartioxylic acid (piperidin-4-ylmethyl>-amide (example A144) and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI); m/z = 522 (MM*).
1H-NMR (400 MHz, DMSO-d6): 12.26 (br.s, 1H. -NH); 9.03 (s, 1H); 8.50 (t, J = 6.1, IN, -NH); 8.27 (d, J = 2.3,1H); 7.01 (d, J = 8.6, 1H); 6.57 (d, J = 8.6, IN); 6.00 (s, 2H); 4.35 (m, IN); 4.09 (d, J = 13.6, IN); 4.02 (d, J = 13.6, 1H); 3.80 (m, 1H); 3.77 (d, J = 6.7, 2H}; 3.34 (dd, J1 = J2 = 6.2, 2H);

3,27 (s, 3H); 2.96 (m, 1H); 2.57 (m, 1H); 1.84 (m, 1H); 1.75 (m, 2H),- 1,20 (m, 1H); 1.09 (m, 1H); 0.87 (m, 1H); 0.30 (m, 2H); 0.10 Example 27: 4-[({1-[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c/jpyrimidin-7-yl]-methanoyl}-amino)-methyl]-piperidine-1-carboxylic acid ethyl ester Starting from 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yi)-5/^.pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (piperidfn-4-ylmethyl)amide (example A144) and ethyl chloroformate the title compound is obtained as colorless solid, MS (ESI); m/z = 522 (MH+).
1H-NMR (400 MHz, DMSO-d6): 12.27 (br.s, 1H, -NH); 9.03 (s, 1H); 8.50 (t, J = 6.0, 1H, -NH); 8.27 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.56 (d, J = 8,6. 1H); 6.00 (s, 2H); 4.03 (qu, J = 7.1, 2H); 3.98 (m, 2H); 3.77 (d, J = 6.7, 2H); 3,34 (dd, J1 = J^ = 6.2, 2H); 2.77 (m, 2H); 1.77 (m, 1H); 1.73 (m, 2H); 1.17 (t, J = 7.1, 3H); 1.10 (m, 2H); 0.88 (m. 1H); 0.30 (m, 2H); 0.10 (m, 2H).
Example 28: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol~4-yf)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-formyl-piperldin-3-ylmethyl)-amide
Starting from 4-{5-cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic add {piperidin-3-ylmethyl)-amide (example A145) and acetic formic anhydride the title compound is obtained as colorless solid. MS (ESI): m/2 = 478 (MM*).
1H-NMR (400 MHz, DMSO-d6): 12,28 (br.s, 1H, -NH); 9.05 (s, 0.5H); 9,04 (s, 0.5H); 8.52 (br.s, 1H, -NH); 8.29 (s. 0.5H); 8.28 (s, 0.5H); 7.98 (s, 0.5H); 7.97 (s, 0.5H); 7.00 (d, J = 8.6, 1H); 6.57 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.13 (m, 0.5H): 3.90 (m, 0.5H); 3.77 (d, J = 6.7, 2H); 3.64 (m, 0.5H); 3.56 (m, 0.5H); 3.36 (m, 2H); 3.02 (m, 0.5H); 2.92 (m, 0.5H); 2.78 (m, 0.5H); 2.54 (m, 0.5H); 1.87 (m, 1H); 1.71 (m, 2H); 1.33 (m, 2H); 0.89 (m, 1H); 0.30 (m, 2H); 0.11 (m, 2H).
Example 29: 4-(5-Cyclopropylmethoxy-benzof 1,3]dioxoJ-4-y)>-5H-pyrro)o[3,2-cDpyrimid!ne-7-carboxylic acid (1-propionyl-piperldin-3-ylmethyl)-amide
Starting from 4-(5-Cyclopropylmethoxy-benzoI1,3]dioxol-4-yl)-5H-pyrrolo[3,2-o]pyrimidine-7-carboxylic acid (piperidin-3-ylmethyl)-amide (example A145) and propionyl chloride the title compound is obtained as colorless solid. MS (ESI): m/2 := 506 (MH+).
1H-NMR (400 MHz, DMSO-d6): 12.28 (br.s, 1H, -NH); 9,03 (s, 1H); 8.51 (t, J = 6.9, 1H, -NH); 8.29 (s, 0.5H); 8,28 (s, 0.5H); 7,00 (d, J = 8.6, 1H); 6.57 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.34 (m, 0.5H); 4.13 (m, 0.5H); 3.84 (m, 0.5H); 3.77 (d, J = 6.6, 2H); 3.74 (m, 0.5H); 3.34 (m, 2H); 2.99 (m, 0,5H); 2.92 (m, 0.5H); 2.71 (m, 0.5H); 2.47 (m, 0.5H); 2.30 (qu, J = 7.3, 2H); 1.86 (m, 1H); 1.70 (m, 2H); 1.33 (m, 2H); 0.96 (I, J = 7.3, 3H); 0.89 (m, 1H); 0.29 (m, 2H); 010 (m, 2H).

Example 30; 4-(5-Cyclopropylmethoxy-benzo[13]dioxol-4-yl}-5H-pyrrolo[3,2-d]pyrimtdine-7-carboxylie acid [1-(2-methoxy-acetyl)-piperidin-3-ylmethylI-amide
Starting from 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-cOpyrimidine-7-carboxylic acid (piperidin-3-ylmethyl)-amide (example A145) and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 522 (MH+).
1H-NMR (400 MHz, DMSO-d6): 12.28 (br.s, 1H, -NH); 9,04 (s, 1H); 8.51 (br.s, 1H. -NH); 8.28 (s, 1H); 7.00 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.28 (m, 0.5H); 4.02 (m, 2H); 3,77 (d, J = 6.8, 2H); 3.65 (m. 0.5H); 3.34 (m, 3H); 3.27 (m, 1.5H); 3.17 (m, 1.5H); 2.97 (m, 0.5H); 2.87 (m, 0.5H); 2.74 (m,0.5H); 2.50 (m.0.5H); 1.83 (m, 1.5H); 1.68 (m, 1.5H); 1.33 (m, 2H); 0.89 (m, 1H); 0.29 (m,2H); 0.10 (m,2H).
Example 31: 3-({[4-(5-Cyclopropylinethoxy-benzoI1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-methyl)-piperidine-1-carboxylic acid ethyl ester Starting from 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (piperidin-3-ylmethyl)-amide (example A145) and ethyl chloroformate the title compound is obtained as colorless solid. MS (ESI): m/z = 522 (MH').
1H-NMR (400 MHz, DMSO-d6): 12.28 (br.s, 1H, -NH); 9,03 (s, 1H); 8.50 (t, J = 6.1, 1H, -NH); 8.28 (s, 1H); 7,00 (d, J = 8,6, 1H); 6.57 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.00 (qu, J = 7.1, 2H); 3.97 (m, 1H); 3.83 (m, 1H); 3.77 (d, J = 6.9, 2H); 2.86 (m, 1H); 2.68 (m, 1H); 1.81 (m, 1H); 1.67 (m, 2H); 1.30 (m,2H); 1.12 (br.s. 3H); 0.88 (m, 1H); 0.29 (m, 2H); 0.11 (m, 2H).
Example 32: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-formyl-pyrrolidin-3-ylmethyl)-amide
Starting from 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxoi-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (pyrrolidin-3-ylmethyl)-amide (example A146) and ethyl chloroformate the title compound is obtained as colorless solid, MS (ESI); m/z = 464 (MM*),
1H-NMR (400 MHz, DMSO-d6): 12.28 (br.s, 1H, -NH); 9.04 (s, 1H); 8.55 (br.s, 1H, -NH); 8.29 (s, 1H); 8.16 (s, 0.5H); 8.15 (s, 0.5H); 7.01 (d, J = 8,6, 1H); 6.57 (d, J = 8.6,1H); 6.00 (s, 2H); 3.77 (d, J = 6.7, 2H); 3.65 (m, 1H); 3.46 (m, 3H); 3.39 (m, 0.5H); 3.26 (m, IN); 3.07 (m, 0.5H); 2.51 (m, 1H); 2,00 (m, 1H); 1.70 (m, 1H): 0,88 (m, 1H); 0,30 (m, 2H); 0.10 (m, 2H).
Example 33; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylie acid [1 -(2-melhoxy-acetyI)-pyrrolidin-3-yImethyl]-amide

starting from 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl}-5H-pyrrolo[3,2-c/)pyrimidine-7-carboxylic acid {pyrrolldin-3-ylmethyl)-amide (example A146) and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI); m/z = 508 (MH+).
1H-NMR (400 MHz, DMSO-d6): 12.28 (br.s, 1H, -NH); 9.04 (s, 1H); 8.55 (m, 1H, -NH); 8.29 (s, 1H); 7.00 (d, J = 8.6, 1H); 6.57 (d, J = 8.6. 1H); 6.00 (s, 2H); 3.99 {s, 1H); 3.98 (s, 1H); 3.77 (d, J = 6.7, 2H); 3.50 (m, 4H); 3.37 (m, 0.5H); 3.29 (m, 0.5H); 3.28 (s, 1.5H); 3.27 (s, 1.5H); 3.21 (m, 0.5H); 3.13 (m, 0.5H); 2.56 (m, 0.5H); 2.44 (m, 0.5H); 2.05 (m, 0.5H); 1.95 (m, 0.5H); 1.75 (m, 0.5H); 1.65 (m, 0.5H); 0.88 (m, 1H); 0.30 (m, 2H); 0.10 (m, 2H).
Example 34: 3-({[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-(y|pyrimldine-7-carbonyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid ethyl ester Starting from 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {pyrro/id;n-3-y/mefhyl)-am(de (example A146) and ethyl chloroformate the title compound is obtained as colorless solid. MS (ESI); m/2 = 508 (MH+).
1H-NMR (400 MHz, DMSO-d6): 12.28 (br.s, 1H, -NH); 9.04 (s, 1H); 8.54 (t, J = 6.0, 1H, -NH); 8.29 (s, 1H); 7.00 (d, J = 8.6, 1H); 6.57 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.01 (qu, J = 7.1, 2H); 3.77 (d, J = 6.7, 2H); 3.46 (m, 4H); 3.29 (m, IN); 3.09 (s, IN); 2.50 (m, IN); 1.99 (m, 1H); 1.69 (m, 1H); 0.88 (m, 1H); 0.30 (m, 2H); 0.10 (m, 2H).
Example 35; 4-(5-Cydopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyllc acid (4-formyl-morpholin-2-ylmethyl)-amide
Starting from 4-{5-Cyclopropylmethoxy-benzo[1,3Idloxol-4-yl)-5H-pyrrolo[3,2-c(]pyrrmidine-7-carboxylic acid (morpholin-2-ylmethyl)-amide (example A147) and acetic formic anhydride the title compound Is obtained as colorless solid. MS (ESI): m/z = 480 (MM*).
1H-NMR (400 MHz, DMSO-d6): 12.30 (br.s, 1H, -NH); 9.04 (s, 0.5H); 9.03 (s, 0.5H); 8.59 (br.s, 1H, -NH); 8.30 (s, 1H); 8.05 (s, 0.5H); 8.04 (s, 0.5H); 7.01 (d, J = 8.6. 1H); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.13 (m, 0.5H); 3.98 (m, 0.5H); 3.94 (m, 1H); 3.77 (d, J = 6.7, 2H); 3.72 (m, 0.5H); 3.61 (m, 1.5H); 3.50 (m, 2H); 3.39 (m, 0.5H); 3.18 (m, 0.5H); 3.00 (m, 0.5H); 2.80 (m, 0.5H); 2.62 (m, 0.5H); 0.88 (m, 1H); 0.30 (m, 2H); 0.10 (m, 2H).
Example 36: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-propionyl-morpholin-2-ylmethyl)-amide
Starting from 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (morpho!ln-2-ylmethyl)-amide (example A147) and propionyl chloride the title compound is obtained as colorless solid.

MS (ESI): m/z = 508 (MH+).
1H-NMR (400 MHz, DMSO-d6): 12.29 (br.s, 1H, -NH); 9.04 (s, 1H); 8.58 (br.s, 1H, -NH); 8.30 (s, 1H); 7,01 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.32 (m, 0.5H); 4.16 (m, 0.5H); 3.89 (m, 1.5H); 3.76 (d, J = 6.7, 2H); 3.70 (m, 0.5H); 3.63 (m. 0.5H); 3.57 {m, 1H); 3.49 (m. 2H); 3.40 (m, 0.5H); 3,13 (m, 0.5H); 2.97 (m, 0.5H); 2.66 (m, 0.5H); 2.50 (m, 0.5H); 2.35 (m, 1H); 2.28 (m, 1H); 0,98 (t, J = 7.4, 3H); 0.88 (m, 1H); 0.29 (m, 2H); 0.10 (m, 2H).
Example 37: 4-(5-Cyclopropy!methoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7~carboxylic acid [4-(2-methoxy-acetyl)-morpholin-2-ylmethyl]-amide Starting from 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {morpholin-2-ylmethyl)-amide {example A147) and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 524 (MH+).
1H-NMR (400 MHz, DMSO-d6); 12.29 (br.s, 1H, -NH); 9.04 (s, 1H); 8.58 (t, J = 5.6, 1H, -NH); 8.30 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.56 (d, J ^ 8.6, 1H); 6.00 (s, 2H); 4.27 {m, 0.5H); 4.11 (m, 1.5H); 4.05 (m, 1H), 3.91 (m, 1H); 3.76 (d, J = 6.7, 2H & m, 1H); 3.61 (m, 2H); 3.48 (m, 2H); 3.27 (s, 1.5H); 3.25 (s, 1.5H); 3.12 (m, 0.5H); 2.97 (in, 0.5H); 2.76 (m, 0.5H); 2.56 (m, 0.5H); 0.88 (m, 1H); 0.29 (m, 2H);0.10(m,2H).
Example 38: 2-({[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-cflpyrimidine-7-carfaonyf]-amino}-methyl)-morpholine-4-carboxylic acid ethyl ester Starting from 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic add (morpholin-2-ylniiethyl)-amide (example A147) and ethyl chloroformate the title compound is obtained as colorless solid. MS (ESI): m/z = 524 (MH+).
1H-NMR (400 MHz, DMSO-d6): 12.30 (br.s, 1H, -NH); 9.04 (s. 1H); 8.57 (t, J = 6.1, 1H, -NH); 8.30 (s, 1H); 7.01 (d, J = 8.6, IN); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.05 (qu, J = 7.1, 2H); 3.90 (m, 2H); 3.76 (d, J = 6.7, 2H &m, 1H); 3,58 (m, 2H); 3.46 (m, 2H); 2.93 (m, 1H); 2.75 (m, 1H); 1.17 (t, J = 7.1, 3H); 0.88 (m, IN); 0.29 (m, 2H); 0.10 (m, 2H).
Example 39:4-(5-cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5/^-pyrrolo[3,2-d]pyrimidine-7-carboxyJ1c acid (1-acetyl-azetidin-3-yl)-amide
Starting from 4-(5-CyclopropylmethQXy-benzo[1,3]dioxQl-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartxixylic acid azetidin-3-ylamide (example A172) and acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 450 (MH+).
1H-NMR(400 MHz, DMSO-d6): 12.33 (br.s, 1H,-NH); 9,06(s, 1H); 8.84 (d, J = 7.2, 1H,-NH);8.32 (s, 1H); 7.01 (d, J = 8.6, IN); 6.57 (d, J = 8.6, 1H); 6.01 (s, 2H); 4.78 (m, 1H); 4.47 (m, 1H); 4.20

(m, 1H);4.16(m, 1H);3.85(m, 1H); 3.76 (d, J = 6.7, 2H); 1.80 (s, 3H); 0.86 (m, 1H); 0.29 (m, 2H); 0.09 (m,2H),
Example 40: 4-(5-Cyclopropylnnethoxy-benzo[1,3]dlaxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-propionyl-azetidin-3-yl)-amide
Starting from 4-{5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c/)pyrimidine-7-carboxylic acid azetidin-3-ylamide (example A172) and propionyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 463 (MH+).
1H-NMR (400 MHz, DMSO-d6): 12.32 (br.s, 1H, -NH); 9,06 (s, 1H); 8.84 (d, J = 7.2, 1H, -NH); 8,32 (s, 1H); 7.01 (d, J = 8,6, 1H); 6,57 (d, J = 8.6, IN); 6,01 (s, 2H); 4.79 (m, 1H); 4.46 (m, 1H); 4.21 (m, 1H); 4.14 (m, 1H); 3,86 (m, 1H); 3.76 (d, J = 6.8, 2H); 2.10 (qu, J = 7,5, 2H); 0.98 (t, J = 7.5, 3H); 0.86 (m, 1H); 0.29 (m, 2H); 0.09 (m, 2H).
Example 41: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo(3,2-rf]pyrimidine-7-carboxylic acid [1-(2-methoxy-ethanoyl)-azetidin-3-yl]-amide
Starting from 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrroio[3,2-d]pyrimidine-7-cartraxylic acid azetidin-3-y(amide (example A172) and methoxy-acetyl chloride the title compound is obtained as colorless solid, MS (ESI): m/z = 479 (MH+).
'1H-NMR (400 MHz, DMSO-d6): 12,33 (br.s, 1H, -NH); 9.06 (s, IN); 8.85 (d, J = 7.1, 1H, -NH); 8,32 (s, 1H); 7,01 (d, J = 8.6, 1H); 6.57 (d, J = 8,6, 1H); 6.01 (s, 2H); 4.82 (m, 1H); 4,52 (m, 1H); 4.27 (m, 1H); 4.20 (m, 1H); 3,94 (s, 2H); 3,92 (m, 1H); 3.76 (d, J = 6,8, 2H); 3.30 (s, 3H); 0,87 (m, 1H); 0,28 (m,2H); 0.09 (m,2H),
Example 42: 3-({1-[4-(5-Cyclopropylm8thoxy-benzo[1,3]dioxol-4-yl)-5H~pyrrolo[3,2-d]pyrimidin-7-yl]-methanoyl}-amino)-azetidine-1-carboxylic acid ethyl ester Starting from 4-(5-Cyclopropylmeltioxy-ben20[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimldine-7-carbioxylic acid a2etidin-3-ylamide (example A172) and ethyl chloroformate the title compound is obtained as colorless solid. MS (ESI): m/z = 479 (MM"),
'H-NIVIR (400 MHz, DMSO-d6): 12,32 (br.s, 1H, -NH); 9.06 (s, 1H); 8.84 (d, J = 7.1. 1H, -NH); 8.31 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.57 (d, J = 8.6, 1H); 6.01 (s, 2H); 4.79 (m, 1H); 4.26 (m, 2H); 4.04 (qu, J = 7.1, 2H), 3.96 (m, 2H); 3.76 (d, J = 6,8, 2H); 1.19 (t, J = 7.1, 3H); 0.87 (m, 1H); 0.28 (m, 2H);0.09(m,2H).
Example 43:4-(5-Cyclopropylmethoxy-ben2o[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-fonnyl-piperidin-4-yl)-amide

Starting from 4-(5-cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidlne-7-carboxylic acid piperidin-4-ylamide hydrochloride (example A138) and acetic formic anhydride the title compound is obtained as colorless solid. MS (ESI); m/z = 464 (MH+).
1H-NMR{400MHz, DMSO-d6): 12.29 (br.s, 1H,-NH); 9.03 (s, 1H); 8.46 (d, J = 7.8, 1H,-NH);8.30 (s. 1H); 8.03 (s, 1H); 7.00 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.17 (m, 1H); 4.06 (m, 1H);3.76(d, J=6.7, 2H):3,70(m, 1H);3.24(m, 1H);2.95(m, 1H);2.01 (m, 2H); 1.52 (m, 1H); 1.41 (m, 1H);0,B6{m, 1H); 0.30 (m,2H); 0.10 (m,2H).
Example 44: 4-(5-Cyclopropylmethoxy-benzo[1,3]dloxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-' 7-carboxylie acid ((S)-1-propionyl-piperidin-3-yl)-amide Starting from 4-(5-Cyclopropylmethoxy-benzo[1,3]dtoxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartMxytic acid (S)-piperidin-3-yiamide {example A148) and propionyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 492 (MH+, 100%}.
1H-NMR {300 MHz, DMSO-d6): 12.29 (br.s, 1H, -NH); 9.00 (s, 1H); 8.56 (d, J = 7.8, 0.5H, -NH); 8.51 (d, J = 7.8, 0.5H); 8.30 (s, 0.5H); 8.29 (s, 0.5H); 7.00 (d, J = 8.6,1H); 6.56 (d, J = 8.6,1H); 6.00 (s, 2H); 4.00 (m, 1H); 3.94 (m, 0,5H); 3.76 (d, J = 6.8, 2H & m, 0.5H); 3.57 (m, 1H); 3.40 (m, 1.5H); 3.26 (m, 0.5H); 2.38 (m, 1H); 2.31 (m, 1H); 1.97 (m, 1H); 1.74 (m, 2H); 1.53 (m, 1H); 1.01 (t, J = 7.3, 1.5H); 0.95 (I, J = 7.3, 1.5H); 0.87 (m, 1H); 0.29 (m, 2H); 0.10 (m, 2H).
Example 45; 4-(5-Cyclopropy)methoxy-benzo[1,3]dioxo)-4-yl)-5H-pyrrolo[3,2-c|]pyrimidine-7-carboxylic acid [(S)-1-{2-methoxy-ethanoyl)-pjperidin-3-yl]-amide
Starting from 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxoI-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (S)-piperidin-3-ylamide {example A148) and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/2 = 508.0 (MH+).
1H-NMR (300 MHz, DMSO-ds): 12.30 (br.s, IN, -NH); 9.00 (s, IN); 8.55 (m, 1H, -NH); 8.31 (s, 0.5H); 8.29 {s, 0.5H); 7.00 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.13-4.00 (m, 3H); 3.91 (m, 0.5H); 3.76 (d, J = 6.8, 2H); 3.68 (m, 0.5H); 3.50 (m, 1.5H); 3.35 {m, 1.5H); 3.29 (br.s, 0.5H); 3.17 (br.s,, 1,5H); 1.98 (m, IN); 1.75 (m, 2H); 1.58 (m, 1H); 0.87 {m, 1H); 0.29 (m, 2H); 0.10 (m, 2H).
Example 46: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c()pyrimidine-7-carboxylic acid {(S)-1-acetyl-piperidin-3-yl)-amide
Starting from 4-{5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (S)-piperidin-3-ylamide (example A14B) and acetyl chloride the title compound is obtained as colorless solid.

MS (ESI): m/z = 478.1 (MH+).
1H-NMR (300 MHz, DlVlSO-de): 12.26 (br.s, 1H, -NH); 9.01 (s, 0.5H); 9.00 (s, 0.5H); 8.58 (d, J = 7.8, 0.5H, -NH); 8.52 (d, J = 7.8, 0.5H); 8.31 (s, 0.5H); 8.28 (s, 0.5H); 7.01 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 6.01 (s, 2H): 3.99 (m, 1H); 3.95 (m, 0.5H); 3.76 (d, J = 6.8, 2H); 3.71 (m, 0.5H); 3.48 (m, 2H); 3.42 (m, 0.5H); 3.23 (m, 0.5H); 2.06 (s, 1.5H); 1.97 (s, 1.5H); 1.94 (m, 1H); 1.71 (m, 2H); 1.54 (m, 1H); 0.87 (m, 1H); 0.29 (m, 2H); 0.10 {m, 2H).
Example 47: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimtdine-7-carboxylic acid ((R)-1-prQpionyl-piperidin-3-yl)-amide
Starting from 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yi)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (R)-piperidin-3-ylamide hydrochloride (example A149) and propionyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 436 (MH+ 100%).
1H-NMR (300 MHz, DMSO-d6): 12.85 (br.s, 1H, -NH); 9.38 (br.m, 2H, -NH2"); 9.13 (s, 1H); 8.60 (s, 1H); 8.51 (d, J = 7.6, 1H, -NH); 7.06 (d, J = 8.6, 1H); 6.58 (d, J = 8.6, 1H); 6,05 (s, 2H); 4.31 (m, 1H);3.79(d,J = 6.7, 2H);3,38(m, 1H);3.18(rr, 1H);2,97(m, 1H);2,91(m, 1H); 2.04 - 11,71 (m, 4H); 0.90 (m, 1H); 0,31 (m, 2H); 0,14 (m, 2H).
Example 48: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1 -{2-methoxy-ethanoyl)-piperidin-3-yl]-am ide
Starting from 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (R)-piperidin-3-ylamide hydrochloride (example A149) and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 508.0 (MM*).
1H-NMR (300 MHz, DMSO-d6): 12.30 (br.s, 1H, -NH); 9.00 (s, 1H); 8.55 (m, 1H, -NH); 8.31 (s, 0.5H); 8,29 (s, 0.5H); 7.00 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.13 - 4.00 (m, 3H); 3.91 (m, 0.5H); 3,76 (d, J = 6.8, 2H); 3.68 (m, 0.5H); 3,50 (m, 1,5H); 3.35 (m, 1,5H); 3,29 (br,s, 0,5H); 3,17 (br.s,, 1.5H); 1.98 (m, 1H); 1.75 (m,2H); 1.58 (m, 1H);0.87(m, 1H); 0,29 (m, 2H); 0.10 (m, 2H),
Example 49: 4-(5-Cyclopropylmethoxy-benzo[1,3JdioxoM-yt)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ((R)-1-acetyl-piperidin-3-yl)-amide
Starting from 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (R)-piperidin-3-ylamide hydrochloride (example A149) and acetyl chloride the title compound is obtained as colorless solid, MS (ESI): m/z = 478,1 (MH'),
1H-NMR (300 MHz, DMSO-d6): 12,26 (br,s, 1H, -NH); 9,01 (s, 0.5H); 9,00 (s, 0.5H); 8.58 (d, J = 7.8, 0.5H, -NH); 8.52 (d, J = 7.8, 0,5H); 8.31 (s, 0,5H); 8.28 (s, 0.5H); 7.01 (d, J = 8.6, 1H); 6.56 (d,

J = 8.6, 1H); 6.01 (s, 2H); 3.99 (m, 1H); 3.95 (m, 0.5H); 3.76 {d, J = 6.8. 2H); 3.71 (m, 0.5H); 3.48 (m, 2H); 3.42 (m, 0.5H); 3.23 (m, 0.5H); 2.06 (s, 1,5H); 1.97 (s, 1.5H); 1,94 (m, 1H); 1.71 (m, 2H); 1.54 (m, 1H); 0,87 (m, 1H); 0.29 (m, 2H); 0.10 (m, 2H).
Example 50: trans~4-(5-Cyclopropylmethoxy-b8nzo[1,3)dioxo!-4-yl)-5H-pyrrolo[3,2-d] pyri midIne-7-carboxyIic acid [4-(2-methoxy-acetylamino)-cyclohexyl]-amide Starting from trans-4-(5-Cyclopropylmethoxy-benzo[1,3]dloxoi-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A140) and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 522 (MH+).
1H'NMR (400 MHz, DMS0-d6): 12.27 (br.s, 1H, -NH); 9.03 (s, 1H); 8.30 (d. J = 7,9, 1H, -NH); 8.27 (s, 1H); 7.58 (d, J = 8.2, 1H, -NH); 7.01 (d, J = 8.6, 1H): 6.56 (d, J = 8.&, 1H); 6,00 (s, 2H); 3.82 (m, 1H); 3,79 (s, 2H); 3.76 (d, J ^ 6,7, 2H); 3,70 (m, 1H); 3.31 (s, 3H); 2.00 (m, 2H); 1.81 (m, 2H); 1.44 (m, 4H)-, 0.6Q (m, 1H); 0.29 (m, 2H>, 0.10 (m, 2H).
Example 51: trans~4-(2-Cyclopropylmefhoxy-4-methoxy-phenyl)-5H-pyrrolo(3,2-c/]pyrimldine-7-carboxylic acid (4-acetylamino-cyclohexyl)-amide
Starting from trans-4-(2-cyclopropylmethoxy-4-methoxy-phenyl)'5H-pyrrolo[3,2-d]pyrlmidine-7-carboxylic acid (4-amtno-cyclohexyl)-amide (example A150) and acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 478 (MH+, 100 %).
1H-NMR (400 MHz, DMSO-d6): 11,90 (br.s, 1H, -NH); 9.00 (s, 1H); 8.38 (d, J = 7.8, 1H, -NH); 8.20 (s, 1H); 7.74 (d, J = 7,7, 1H); 7.61 (d, J = 8,5, 1H); 6.72 { dd, J1 = 8,5, J2 = 2.1, 1H); 6.69 (d, J = 2.1, 1H); 3.92 (d, J = 6.9, 2H); 3.86 (s, 3H); 3.80 (m, 1H); 3.59 (m, 1H); 2.01 (m, 2H); 1.87 (m, 2H); 1.80 (s, 3H); 1,42 (m, 2H); 1.31(m, 2H); 097 (m, 1H); 0.36 (m, 2H); 0.23 (m, 2H).
Example 52: trans-4-(2-Cyclopropy!methoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(cyclopropanecarbonyl-amino>-cyclohexyl]-amide Starting from trans-4-(2-cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrroio[3,2-d]pyrimidine-7-cartxjxyNc acid (4-amino-cydohexyl)-amide (example A150) and cyclopropanecarbonyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 504 (MH+, 100 %).
1H-NMR 400 MHz, DMSO-d6): 11.90 (br.s, 1H,-NH); 9.00 (s, 1H); 8.39 (d, J = 7.8, 1H,-NH);8.20 (s, 1H); 7.96 (d, J = 7.8, 1H); 7.62 (d, J = 8.5, 1H); 6.72 ( dd. J, = 8.5, Jj = 2,2, 1H); 6.69 (d, J = 2,2, 1H); 3.92 (d, J = 6.9, 2H); 3.86 (s, 3H); 3.81 (m, 1H); 3.61 (m, 1H); 2.01 (m. 2H); 1.88 (m, 2H); 1.53 (m, 1H); 1.38 (m. 4H): 0.97 (m, 1H); 0.62 (m, 4H); 0.36 (m, 2H); 0.23 (m, 2H).

Example 53: trans-4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(2-methoxy-acetylamino)-cyclohexyl]-amide Starting from trans-4-(2-cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4-amino-cyclohexyl)-amide (example A150) and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 508 (MH\ 100 %).
1H-NMR 400 MHz, DMSO-d6): 11.90(br.s. 1H,-NH); 9.00 (s, 1H); 8.38 (d, J - 7.6, 1H,-NH);8.21 (s, 1H); 7.61 (d, J = 8.5, 1H); 7.59 (d, J = 8.3, 1H, -NH); 6.72 ( dd, J1 = 8.5, J2 = 2.2, 1H); 6.69 (d, J = 2.2, 1H); 3.91 (d, J = 6.9, 2H); 3.85 (s, 3H & m, 1H); 3.78 (s. 2H); 3.68 (m, 1H); 3.31 (s, 3H); 2.01 (m, 2H); 1.81 (m, 2H); 1.44 (m, 4H); 0.97 (m, 1H); 0,36 {m, 2H); 0.23 (m, 2H).
Example 54: trans-(4-{[4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-cyclohexyl>carbamic acid ethyl ester
Starting from trans-4-(2-cyclopropylmethoxy-4-methoxy-phenyl)-5(S'-pyrrolo[3,2-olpynmidine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A150) and ethyl chloroformate the title compound is obtained as colorless solid. MS (ESI): m/z = 508 (MH+, 100 %).
1H-NMR400MHz, DMSO-d6): 11.90 (br.s, 1H,-NH); 9.00 (s, 1H); 8,38 (d, J = 7.9, 1H,-NH);8.21 (s, 1H);7.62(d,J = 8.5, 1H); 7.03 (d, J = 7.6, 1H,-NH); 6.73 ( dd, J, = 8.5, J2 = 2.1, 1H);6.69(d,J = 2.1. 1H); 3.98 (qu, J = 7.0. 2H); 3.92 (d. J = 6.9, 2H); 3.86 (s, 3H); 3.79 (m, 1H); 3.69 (m, 1H); 2.01 (m, 2H; 1.82 (m, 2H); 1.46 (m. 4H); 0.97 (m, 1H); 0.37 (m. 2H); 0.23 (m, 2H).
Example 55: cis-4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-t/)pyrimidine-7-carboxyIic acid (4-acetylamino-cyclohexyl)-amide
Starting from cis-4-(2-cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3.2-c/]pyrimidine-7-carboxyiic acid (4-amino-cyclohexyl)-amide (example A151) and acetyl chloride the title compound is obtained as colorless solid. MS (ESI); m/z = 478 (hAH\ 100 %).
1H-NMR400MHZ, DMSO-d6): 11,91 (br.s. 1H,-NH); 9.03 (s, 1H); 8.63 (d, J = 7.7, 1H,-NH);8.21 (s, 1H);7.87(d, J = 7.6, 1H,-NH);7.61 (d, J = 8.5, 1H); 6.72 (dd. J, = 8.5, Js = 2.1, 1H);6.69(d.J = 2.1, 1H);4.02(m, 1H); 3.91 (d, J = 6.9. 2H); 3.86 (s, 3H); 3.76 (m, 1H); 1.87-1.55 (m, 9H); 0.97 (m, 1H); 0.65 (m, 4H); 0.37 (m, 2H); 0.23 (m, 2H).
Example 56: ci&-4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-rflpyrimidlne-7-carboxylJc acid [4-(cyclopropanecarbonyl-amino)-cyclohexyl]-amide Starting from cis-4-(2-cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrroIo[3,2-d]pyrimidine-7-cartraxylic acid (4-amino-cyclohexyi)-amide (example A151) and cyclopropanecarbonyl chloride the title compound is obtained as colorless solid.

MS (ESI): m/z = 504 (MH+ 100 %).
1H-NMR 400 MHz, DMSO-d6): 11.91 {br.s. 1H, -NH); 9.03 (s, 1H); 8.68 (d, J = 7.6, IN, -NH); 8.21 (s, 1H); 8.08 (d, J = 7.6, 1H, -NH): 7.61 {d, J = 8.5, 1H); 6.72 ( dd, J, = 8.5, J2 = 2.1, 1H); 6.69 (d. J = 2.1,1H); 4.03 {m, 1H); 3.91 (d, J = 6.9, 2H); 3.86 (s, 3H); 3.79 (m, 1H); 1.83 (s, 1H): 1.82-1.55 (m, 8H); 0.97 (m, 1H); 0.37 (m, 2H); 0.23 (m, 2H).
Example 57; cJs-4-{2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4~(2-methoxy-acetylamino)-cyclohexyl]-amide
Starting from cis-4-(2-cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartxjxylic acid (4-amino-cyclohexyl)-amide {example A151) and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 508 (MH+, 100 %).
■1H-NMR 400 MHz, DMSO-d6): 11.90 (br.s, 1H, -NH); 9.03 (s, 1H); 8.68 (d, J = 7.5, 1H, -NH); 8.20 (s, 1H);7.70(d. J = 7.7, 1H,-NH);7.61 (d, J = 8.5. 1H); 6.72 ( dd, J-, = 8.5, J2= 2.1, 1H);6.69(d, J = 2.1, 1H);4.06{m, 1H);3.91 (d, J = 7.0, 2H); 3.86 {s, 3H); 3.81 (s, 2H & m, 1H);3.31 (s, 3H); 1.86-1.59 {m, 8H); 0.97 (m, 1H); 0.37 (m, 2H); 0.23 (m, 2H).
Example 5B; cis-(4-{(4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-cyclohexyl)-carbamic acid ethyl ester Starting from cis-4-(2-cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cyclohexy(}-ami'de (example A151) and ethyl chloroformate the title compound is obtained as colorless solid. MS (ESI): m/z = 508 (MH\ 100 %).
1H-NMR 400 MHz, DMSO-d6): 11.90 (br.s, 1H, -NH); 9.03 (s, 1H); 8.67 (d, J = 7.7, 1H, -NH); 8.20 (d, J = 3.3, IN); 7.61 (d, J = 8.5, 1H); 7.22 (d, J = 6.5, 1H, -NH); 6.72 ( dd, J, = 8.5, J2 = 2.1, 1H); 6.69 (d, J = 2.1, IN); 4.00 (qu, J = 7.1, 2H & m, 1H); 3.91 (d, J = 6.9, 2H); 3.86 (s, 3H); 3.50 (m, 1H); 1.87-1.56 (m, 8H); 1.18 {t, J = 7.1, 3H); 0.97 (m, 1H); 0.37 (m, 2H); 0.23 (m, 2H).
Example 59: 4-(2-cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d!pyrimidine-7-carboxylic acid (1-acety(-piperidin-4-y()-amide
Starting from 4-(2-cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ytamide (example A152) and acetyl chloride the title compound is obtained as colorless solid.
MS (ESI): m/2 = 464 (MH+, 100 %).
1H-NMR400 MHz, DMSO-d6): 11.92 (br.s, 1H,-NH); 9.00 (s, 1H); 8.54 (d, J = 7.7, 1H, -NH); 8.23 (d, J = 3.2, 1H);7.61 (d, J = 8.5, 1H); 6.72 (dd, J1 =8.5, J2 = 2.1, 1H); 6,69 (d, J = 2.1, 1H);4.20 (m, 1H); 4.12 (m, 1H); 3.91 (d, J = 7.0, 2H); 3.86 (s, 3H); 3.79 (m, 1H); 3.27 (m, 1H); 2.92 (m, 1H); 1.96 (m, 2H); 1.55 (m, 1H); 1.39 (m 1H); 0.98 (m, 1H); 0.37 (m, 2H); 0.23 (m, 2H).

Example 60: 4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-(/|pyrimidine-7-carboxylic acid [1-(1-cyclopropyl-methanoyl)-piperidin-4-yl]-amide
Starting from 4-(2-cyc!opropylmethoxy-4-methoxy-plieny!)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide (example A152) and cyclopropanecarbonyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 490 {MH\ 100 %).
1H-NMR 400 MHz, DMSO-d6): 11.93 {br.s, 1H, -NH); 9.00 (s, 1H); 8.56 (d, J = 7.8, 1H, -NH); 8.23 (d,J = 2.2, 1H);7.61 (d, J = 8.5,1H); 6.72 ( dd, J, = 8.5, J; = 2.1, 1H); 6.69 (d, J = 2.1, 1H);4.15 (m, 2H); 4.12 (d, J = 4.4, 2H); 3.92 (d, J = 7.0, 2H); 3.86 (s, 3H); 3.75 (m, 1H); 3.31 (s, 3H); 3.21 (m, 1H):2.96(m, 1H); 1.97 (m,2H); 1.54 (m, 1H); 1.41 (m 1H); 0.98 (m, 1H); 0.37 (m, 2H); 0.23 (m, 2H).
Example57: 4-(2-Cyctopropyimfe\boxv-A-me1HDxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7 -carboxylic acid [1-(2-methoxy-etlianoyl)-piperidin-4-yl]-amide
Starting from 4-(2-cyclopropylmefhoxy-4-methoxy-phenyl)-5H-pyrro(o[3,2'0]pyrrmrdtne-7-carboxy(ic acid piperidin-4-ylamide (example A152) and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 494 (MH+, 100 %).
1H-NMR 400 MHz, DMSO-d6): 11.92 (br.s, 1H, -NH); 9.00 {s, 1H); 8.53 (d, J = 7.8, IN, -NH); 8.23 (d, J = 3.0, 1H); 7.61 (d, J = 8.5,1H); 6.72 ( dd, J, = 8.5, J2 = 2.1, 1H); 6.69 (d, J = 2.1, 1H); 4.30-4.10 (m, 3H); 3.92 (d, J = 7.0, 2H); 3.86 (s, 3H); 3.39 (m, 1H); 2.97 (m, IN); 2.10-1.89 (m. 2H); 1.53 (m, 1H); 1.41 (m, IN); 0.98 (m, IN); 0.74 (m, 4H); 0.38 (m, 2H); 0.23 (m, 2H).
Example 62: 4-({1-[4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo(3,2-c(|pyrimidin-7-yl]-methanoyl}-amino)-piperidine-1-carboxylic acid ethyl ester Starting from 4-(2-cyclopropy Jmethoxy-4-methoxy-phenyI )-5H-pyrrolo[3,2-d] pyrimidine-7-carboxylic acid piperidin-4-ylamide (example A152) and ethyl chloroformate the title compound is obtained as colorless solid.
MS (ESI): m/z = 494 (MH+, 100 %).
1H-NMR 400 MHz, DMSO-d6): 11.91 (br.s, 1H, -NH); 9.00 (s, 1H); 8.57 (d, J = 7.6, IN, -NH); 8.21 (s, 1H); 7.62 (d, J = 8.4, 1H); 6.73 (dd, J, = 8.4, J2 = 2.1,1H); 6.69 (d, J = 2.1, IN); 4,07 (qu, J = 7.1. 2H & m, 1H); 3.92 (d, J = 7.1, 2H & m. 2H); 3,86 (s, 3H); 3.10 {m, 2H); 1.96 (m, 2H); 1.49 (m, 2H); 1.20 (t, J = 7.1, IN); 0.98 (m, 1H); 0.37 (m, 2H); 0.24 (m, 2H).
Exam pi e 63: tra ns-4-(2-Cyclop ropy lmethoxy-5-methoxy-pheny l)-5H-pyrrolo[3,2-c/]pyrimid!ne-7-carboxylic acid (4-acetylamino-cyclohexyl)-amide

Starting from trans-4-(2-cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-
carboxylic acid (4-amino-cyclohexyl)-amide (example A153) and acetyl chloride the title compound
is obtained as colorless solid.
MS (ESI): m/z = 478 {MH\ 100 %).
1H-NMR 200 MHz, DMSO-d6); 11,98 (br.s, 1H,-NH); 9,05 (s, IN); 8.36 (d, J = 7.8, IN,-NH); 8.23
(s, 1H);7.73(d, J = 7.7, 1H,-NH); 7,19 (I, J = 1.7, 1H):7.11 (d, J = 1.7, 2H); 3.82 (d, J = 6.9, 2H &
m, 1H); 3,77 (s, 3H): 3.57 (m, 1H); 2.02 (m, 2H); 1.87 (m, 2H); 1.79 (s, 3H); 1.53-1.20 (m, 4H); 0.92
(m, IN); 0,32 (m, 2H); 0.15 (m, 2H}.
Example 64: trans-4-{2-Cyclopropy!methoxy-5-methoxy-phenyl)-5H-pyrro!o[3,2-c/lpyrimidine-Z-carboxylic acid [4-(cyclopropanecarbonyl-amino)cyclohexyl]-amide Starting from trans-4-(2-cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartjoxylic acid (4-amino-cyclohexyl)-amide (example A153) and cyclopropanecarbonyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 504 (MH\ 100 %).
1H-NMR200MHZ, DMSO-d6): 11.98 (br.s, 1H,-NH); 9.05(s, 1H); 8.36 (d, J = 7.8, 1H,-NH);8.23 (s, 1H); 7.94 (d, J = 7.7, 1H,-NH); 7.18 (t, J = 1.7. 1H);7.11 (d, J = 1.7, 2H); 3.82 (d, J = 6.9, 2H & m, IN); 3.77 (s, 3H); 3.60 (m, 1H); 2.02 (m, 2H); 1.87 (m, 2H); 1.53 (m, 1H); 1.52-1.20 (m, 4H); 0.92 (m, 1H); 0.63 (m, 4H); 0.32 (m, 2H); 0.15 (m, 2H).
Exam pie 65: trans-4-(2-CyclopropyIm ethoxy-5-methoxy-pheny I )-5H-pyrrolo [3,2-c(]pyrimidine-7-carboxylic acid [4-(2-methoxy-acetylamino)-cyclohexyl]-amide Starting from trans-4-(2-cyclopropylmethoxy-5-nietho>cy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A153) and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 508 (MH\ 100 %).
1H-NMR 200 MHz, DMSO-d6): 11.98 (br.s, IN, -NH); 9.05 (s, 1H); 8.35 (d, J = 7,8, 1H, -NH); 8.23 (s. 1H);7,57(d,J = 8.2, 1H,-NH); 7,19 (t, J = 1.7, 1H);7.11 (d, J = 1.7, 2H); 3.82 (d, J = 6.9, 2H & m, 1H&s, 2H); 3.77 (s,3H); 3,66 (m, 1H);3.31 (s, 3H); 2.04 (m, 2H); 1.81 (m, 2H}; 1,58-1.32 (m, 4H); 0.92 (m. 1H); 0.32 (m, 2H); 0.15 (m, 2H).
Example 66: trans-(4-{[4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-dlpyrimidine-7-carbonyl]-amino}-cyclohexyl)-carbamic acid ethyl ester Starting from trans-4-(2-cycloprapy(methoxy-5-methoxy-phenyl)-5H-pyrroto[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A153) and ethyl chloroformate the title compound is obtained as colorless solid. MS (ESI): m/z = 508 (MH+, 100 %).

1H-NMR 200 MHz, DMSO-d6): 11.97 (br.s, 1H, -NH): 9.05 (s, 1H): 8.35 (d, J - 7.9, 1H, -NH); 8.23 (s, IN); 7.18 (t, J = 1.7, 1H); 7.11 (d, J = 1.7, 2H); 7.01 (d, J = 7.8, IN, -NH); 3.98 (qu. J = 7.1, 2H); 3.82 (d, J = 6.B, 2H & m, 1H); 3.77 (s, 3H); 3.38 (m, 1H); 2.02 (m, 2H); 1.89 (m, 2H); 1,52-1.23 (m, 4H); 1.16 (t, J = 7.1, 3H); 0.92 (m, 1H); 0.32 (m, 2H); 0.16 (m, 2H).
Example 67: cis-4-{2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-acetylamino-cyclohexyl>-amide
Starting from cis-4-(2-cyciopropylmethoxy-5-niethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-
carboxylic acid (4-amino-cyclohexyl)-amide (example A154) and acetyf cti/oride the title compound
is obtained as colorless solid.
MS (ESI): m/z = 478 (MH+, 100 %).
1H-NMR 200 MHz, DMSO-d6): 12.00 {br.s, 1H,-NH); 9.08 (s, 1H); 8.61 (d, J = 7.6, 1H,-NH); 8.25
(s, 1H); 7.86 (d, J = 7,6, 1H, -NH); 7.19 (t, J = 1.7, 1H); 7,12 (d, J = 1.7, 2H); 4.02 (m, 1H); 3,83 (d,
J=6.e. ZH);3.77(s, 3H&m, 1H); 1.84 (s. 3H): 1.81-1.53(m. 8Hy,0.92(m, 1H);0.33(m. 2H);0.17
(m, 2H),
Example 68; cis-4-(2-Cyclopropylmethoxy-5-methoxy-pheny!)-5H-pyrrolo[3,2-d]pyrimJdine-7-carboxylic acid [4-(cyclopropanecarbonyl-amino)-cyclohexyl]-amide Starting from cis-4-{2-cyclopropy/methoxy-5-mett?oxy-phenyl)-5A/-pyrro(o[3,2-£^pyrimid(ne-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A154) and cyclopropanecarbonyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 504 (MH+, 100 %).
1H-NMR 200 MHz, DMSO-d6): 12.01 (br.s, 1H, -NH); 9.09 (s, 1H); 8.63 (d, J = 7.5, 1H, -NH); 8.25 (s, 1H); 8.07 (d, J = 7.5, 1H, -NH); 7.20 (t, J = 1.7, 1H}; 7.12 (d, J = 1.7, 2H); 4.04 (m, 1H); 3.83 (d, J = 6.8, 2H); 3.78 (s, 3H & m. IN); 1.84 (s, 3H); 1.91-1.50 (m, 9H); 0.93 (m, IN); 0.65 (m, 4H); 0.33 (m,2H);0.17(m, 2H).
Example 69: cis-4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid f4-(2-methoxy-acetylamlno)-cyclohexyl]-amide
Starting from cis-4-(2-cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrtmJdine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A154) and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 508 (MH+, 100 %).
1H-NMR 200 MHz. DMSO-d6): 12.00 (br.s, 1H, -NH); 9,08 (s, 1H); 8.64 (d, J = 7.5, 1H, -NH); 8.24 (s, 1H); 7.69 (d, J = 7.6, 1H, -NH); 7.19 (t, J = 1.7, 1H); 7.12 (d, J = 1.7, 2H); 4.06 (w, 1H); 3.83 (d, J - 6.8, 2H & s, 2H); 3,78 (s, 3H & m, 1H); 3.31 (s, 3H); 1.90-1.58 (m, 8H); 0.92 (m, 1H); 0.31 (m, 2H);0.17(m, 2H),

Example 70; cis-(4-{[4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo(3,2-c(]pyrinnidine-7-carbonyl]-amino}-cyclohexyl}-carbamic acid ethyl ester Starting from cis-4-(2-cyctopropylnr1ethoxy-5-^net^^oxy-phenyl)-5^/-pyrrolo(3,2-d]pyrimidine~7-carboxylic acid (4-amino-cyclohexyl)-amide (example A154) and ethyl chloroformate the title compound is obtained as colorless solid. MS (ESI): m/2 = 508 (MH+, 100 %).
1H-NMR 200 MHz, OIVISO-dB); 12.00 (br.s, 1H. -NH); 9.08 (s, 1H); 8.64 (d, J = 7.8, 1H, -NH); 8.24 (s, 1H); 7.19 (t, J = 1.7, 1H & br.s, 1H,-NH); 7.12 (d, J = 1.7, 2H); 4.00 (qu, J = 7.1, 2H & m, 1H); 3.83(d, J = 6.8, 2H);3.78(s. 3H);3.51 (m, 1H); 1,88-1.58 (m, 8H); 1.18 (t, J = 7.1. 3H); 0.93 (m, 1H); 0.33 (m,2H); 0.17 (m,2H).
Example 71: 4-(2-Cyclopropylmethoxy-5-methioxy-ptienyl)-5H-pyrrolo[3,2-dIpy! imidine-7-carboxylic acid (1-acetyl-piperidin-4-yi)-amide
Stei'tJi'Tg l,'om 4-{2-cyck!f!fcpy!fnetf}Oxy-5-meilTOxy-phsfty>}'5h'-pyrroh{3,2-^pyr/m/d/ne- 7-cafboxy}'ic acid piperidin-4-ylamide (example A155) and acetyl diloride the title compound is obtained as colorless solid.
MS (ESI); m/2 = 464 (MH+, 100 %).
1H-NMR 400 MHz, DMSO-d6): 12.03 (br.s, 1H, -NH); 9.05 (s, 1H); 8.51 (d, J = 7.8. 1H, -NH); 8.27 (s, 1H); 7.19 (t, J = 1.6, 1H); 7.11 (d, J = 1.6, 2H); 4.21 (m, 1H); 4.14 (m, 1H); 3.83 (d, J = 6.8, 2H & m, 1H); 3.77 (s, 3H); 3.27 (m, 1H); 2.92 (m, 1H); 2.04 (s, 3H); 1.97 (m, 2H); 1.56 (m, 1H); 1.40 (m, 1H); 0.92 (m, 1H); 0.32 (m, 2H); 0.16 (m, 2H).
Example 72: 4-(2-Cyclopropylmethoxy-5-methoxy-pheny|)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-cyclopropanecarbonyl-piperidin-4-yl)-amide
Starting from 4-(2-cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide (example A155) and cyclopropanecarbonyl chloride the title compound is obtained as colorless solid. MS (ESI): m/2 = 490 (MH\ 100 %).
1H-NMR 400 MHz, DMSO-d6): 12.03 (br.s, 1H, -NH); 9.05 (s, 1H); 8.51 (d, J = 7.8, 1H, -NH); 8.27 (s, 1H); 7.19 (t, J = 1.6, 1H); 7.11 (d, J = 1,6, 2H); 4.20 (m, 3H); 3.83 (d, J-= 6.8, 2H); 3.77 (s. 3H); 3.39 (m, 1H); 2.98 (m. IN); 2.01 (m, 1H); 1.99 {m,2H); 1.56 (m,1H); 1.42 (m, 1H);0.92(m, 1H); 0.73 (m, 4H); 0.32 (m, 2H); 0.16 (m, 2H).
Example 73: 4-(2-Cyclopropylmethoxy-5-methoxy-phenvi)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-methoxy-acetyl)-piperidin-4-yl]-amide
Starting from 4-(2-cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide (example A155) and methoxy-acetyl chloride the title compound is obtained as colorless solid.

MS (ESI): m/2 = 494 (MH+, 100 %).
1H-NMR 400 MHz, DMSO-d6): 12.03 (br.s, 1H, -NH); 9.05 (s, 1H); 8.51 (d, J = 7.8, 1H, -NH); 8.27 (s, 1H);7.19(t,J= 1.6, 1H};7.11 (d, J = 1.6, 2H); 4.17 (m, 2H); 4.11 (d, J = 4.7, 2H); 3.83 (d, J = 6.9, 2H); 3.77 (s. 3H & m, 1H); 3.31 (s, 3H); 3,21 (m, 1H); 2.94 (m, 1H); 1.97 (m, 2H); 1.56 (m, 1H); 1.41 (m, 1H);0.91(m, 1H); 0.32 (m, 2H); 0.17 (m, 2H).
Example 74: 4-{[4-(2-Cyclopropylmethoxy-5-methoxy-phenyl}-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid ethyl ester
Starting from 4-(2'C;yclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide (example A155) and ethyl chloroformate the title compound is obtained as colorless solid,
MS (ESI): m/z= 494 (MH+, 100 %).
1H-NMR 400 MHz, DMSO-d6): 12.03 (br.s, 1H, -NH); 9.05 (s, IN); 8,51 (d, J = 7.8, 1H, -NH); 8,27 (s, 1H);7.19(t,J=1.6, 1H);7.11 (d, J ^ 1.6, 2H);4.08 (qu, J= 7.1, 2H & m, 1H);3.91 (m, 2H),-3,83 (d, J = 6.8, 2H); 3.78 (s, 3H); 3,09 (m, 2H); 1.97 (m, 2H): 1.48 (m, 2H); 0.92 (m, 1H); 0.32 (m, 2H);0.17(m, 2H),
Example 75: cis-4-(2-Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimrdine-7-carboxylic acid (4-acetylamino-cyclohexyl)-amide
Starting from cis-4-(2-Cyclopropylmethoxy-4-fluoro-phenyl)-5f/-pyrrolo[3,2-c(lpyrimldine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A156) and acetyl chloride the title compound is obtained as colorless solid, MS (ESI); m/z = 466 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.06 (br,s, IN, -NH); 9,07 (s, 1H); 8.62 (d, J = 7,6, 1H; -NH); 8,28 (s, 1H); 7.86 (d, J = 7.6, 1H, -NH); 7.68 (dd, J, = 8.5, J2 = 7.0, 1H); 7.08 (dd, J1 = 11.6, J2 = 2,3, 1H);6.96(ddd, J1 = Jj = 8.5, J3 = 2.3, IN); 4.03 (m, 1H); 3.92 (d, J = 6.9, 2H); 3.78 (m, 1H); 1.83 (s, 3H); 1.81-1.50 (m, 8H); 0.98 (m, IN); 0,36 (m, 2H); 0.22 (m, 2H),
Exam pi e 76: c(s-4-(2-Cyclop ropy lmethoxy-4-fluoro-pheny I )-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(2-methoxy-acetylamir>o)-cyclohexyl]-amide
Starting from cis-4-{2-Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-c(Ipyrimidine-7-cartxjxyiic acid (4-amino-cyclohexyl)-amide (example A156) and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESl): m/z = 496 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.06 (br.s, 1H, -NH); 9.07 (s, 1H); 8.65 (d, J = 7.4, IN; -NH); 8.28 (s, 1H); 7.68 (dd, J-, = 8.5, J2 = 7.0, 1H & br.s, 1H, -NH); 7.08 (dd, J1 = 12.6, J2 = 2.3, IN); 6.96 (ddd, J1 = J2 = 8.5, J3 = 2.3, 1H); 4.05 (m, 1H); 3.92 (d, J = 7.0, 2H); 3.82 (m, IN & s, 2H); 3.31 (s, 3H); 1.89-1.58 (m, 8H); 0.98 (m, 1H); 0.36 (m, 2H); 0.22 (m, 2H).

Example 77: cis-(4-{[4-{2-Cyclopropylmethoxy-4-fluoro~phenyl)-5H-pyrrolo[3,2-dlpyrimidine-7-carbonyl)-amino}-cyclohexyl)-carbamic acid ethyl ester Starting from cis-4-{2-Cyc(opropylmethoxy-4-fluoro-phenyl)-5H'-pyrrolo[3,2-d]pyrimidine-7-carboxyllc acid {4-amino-cyclohexyl)-amide (example A156) and ethyl chloroformate the title compound is obtained as colorless solid. MS (ESI): m/z = 496 {MH+, 100 %).
1H-NMR(300 MHz, DMSO-d6): 12.05 (br.s, 1H,-NH); 9.06 {s, 1H): 8.65 (d, J = 7.8, 1H;-NH);8.27 (s, 1H); 7.68 (dd, J, = 8.5, J2 = 7.0, 1H); 7.20 (br.s, 1H, -NH); 7.08 (dd, J1 = 12.6, J2 = 2.3, 1H); 6.96 {ddd, J1 = J2 = 8.5, J3 = 2.3, 1H); 4 03 (m, 1H); 4.00 (qu, J = 7.1, 2H); 3.92 (d, J = 7.0, 2H); 3.50 (m, 1H); 1.88-1.53 (m,8H); 1.17 (t, J = 7.1, 3H); 0.98 (m, 1H); 0.36 (m, 2H); 0,22 (m, 2H).
Example 78: trans-4-(2-Cyciopropylmethoxy-4-fiuoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbaxylic acid (4-acetylaminocyclohexyl)-amide
Starting from trans-4-(2-Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A157) and acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 466 (MH+, 100 %).
1H-NMR (400 MHz, DMSO-d6): 12.05 (br.s, 1H, -NH), 9.03 (s. 1H); 8.35 (d, J = 7.9, 1H, -NH); 8.26 (s, 1H); 7.72 (d, J = 7.6, 1H. -NH); 7.67 (dd, J, = 8.4. J2 = 7.1, 1H); 7.08 (dd, J1 = 11.5, Jz = 2.2, 1H); 6.96 (ddd, J, ^ J^ = 8.4, J3 = 2.2, 1H); 3.92 (d, J = 7.0, 2H); 3.82 (m, 1H); 3.58 (m, 1H); 2.01 (m, 2H); 1.87 (m, 2H); 1.79 (s, 3H); 1.42 (m, 2H); 1.31 (m, 2H); 0.96 (m, 1H); 0.36 (m, 2H); 0.22 (m, 2H).
Example 79: trans-4-(2-Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2- Starting from trans-4-(2-Cyclopropylmethoxy-4-fluoro-phenyl)-5Ay-pyrrolo[3,2-d]pyrimidine-7-carboxytic acid (4-amino-cyclohexyl)-amide (example A157) and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI):'m/z = 496 (MH+. 100 %).
1H-NMR (400 MHz, DMSO-d6): 12.05 (br.s, 1H, -NH); 9.04 (s, 1H); 8.35 (d, J = 7.8,1H; -NH); 8.27 (s, 1H); 7.67 (dd, J, = 8.4, J2 = 7.1, 1H); 7.56 (d, J = 8.2, 1H, -NH); 7.08 (dd, J, = 11.5, J2 = 2.2, 1H); 6.96 (ddd, J1 = J2 = 8.4, J3 = 2.2, 1H); 3.92 (d, J = 6.9, 2H); 3.79 (m, 1H & s, 2H); 3.70 (m, 1H); 3.31 (s, 3H); 2,01 (m, 2H); 1.87 (m, 2H); 1.43 (m, 4H); 0.96 (m, 1H); 0.36 (m, 2H); 0.22 (m. 2H).
Example 80: trans-(4-{[4-(2-Cyclopropylmethoxy-4-fluoro-phenyi)-5H-pyrrolo[3,2-cqpyrimidine-7-carbonyl]-amino}-cyclohexyl]-carbamic acid ethyl ester

starting from trans-4-(2-Cyclopropylmethoxy-4-f!uoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cyclotnexyl)-amide {example A157) and ethyl chloroform ate the title compound is obtained as colorless solid. MS (ESI): m/z = 496 (MH\ 100 %).
1H-NMR {400 MHz, DMSO-d6): 12.04 (br.s, 1H, -NH); 9.03 (s, 1H); 8.34 (d, J = 7.8, 1H; -NH); 8.26 (s. IN); 7.67 (dd, J, = 8.4, J2 = 7.2.1H); 7.07 (dd, J1 - 11.5, J2= 2.2, 1H); 7.01 {d, J = 7.2, 1H, -NH); 6.96 (ddd, J1 = J2 = 8.5, J3 = 2.2, 1H); 3.98 (qu, J = 7.0, 2H); 3.92 (d, J = 7.0, 2H); 3.79 (m, 1H); 3.35 (m, 1H); 2.04 (m, 2H); 1.88 (m, 2H); 1.37 (m, 4H); 1.16 (t, J - 7.0, 3H); 0.96 (m, 1H); 0.36 (m, 2H); 0.22 (m, 2H).
Example 81: 4-(2-Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyljc acid (1-acetyl-piperidin-4-yl)-amide
Starting from 4-(2-Cyc]opropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic
ac/d ff:'pef/dt,T-4-y,'amide ,'rja'.'Cfc/7itor,Gte {example A153} and aceiy/ chloride the iltle compound is
obtained as colorless solid.
MS (ESI): m/z = 452 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 11.98 (br.s, 1H, -NH); 9.03 (s, 1H); 8.50 (d, J = 7.8, 1H; -NH); 8.29
(s, 1H); 7.67 (dd, J-, = 8.5, J^ = 7.0,1H); 7.08 (dd, J, = 11.6, J2 ^ 2.3, 1H); 6.96 (ddd, J, = J2 = 8.5,
J3 = 2.3, 1H); 4.27-4.06 (m, 2H); 3.92 (d, J = 6.9, 2H); 3.79 (m, 1H); 3.28 (m, 1H); 2.91 (m, 1H);
2.04 (s, 3H); 1.97 (m, 2H); 1.57 (m, 1H); 1.40 (m, 1H); 0,96 (m, 1H); 0.36 (m, 2H); 0.22 (m, 2H),
Example 82: 4-(2-Cyclopropylmethoxy-4-fluoro-phenyl)s5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-proplonyl-piperidin-4-yl)-amide
Starting from 4-(2-CyclopropylmethDxy-4-fluoro-phenyl)-5H-pyrrDlof3,2-d]pyrimidine-7-carboxylic
acid piperidin-4-ylamide hydrochloride (example A158) and propionyl chloride the title compound is
obtained as colorless solid.
MS (ESI): m/2 = 466 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.07 (br.s, 1H, -NH); 9.02 (s, 1H); 8.50 (d, J = 7,8,1H; -NH); 8,29
(s, IN); 7.67 (dd, J1 = 8.5, Jj = 7.0, 1H); 7.08 (dd, J, = 11.6, J2 = 2.3, 1H); 6.96 (ddd, J, = J2 = 8.5,
J3 = 2.3. 1H); 4.23 (m, IN); 4.14 (m, 1H); 3.92 (d, J = 7,0, 2H); 3.82 (m, 1H); 3.25 (m, 1H); 2.93 (m,
1H); 2,36 (qu, J = 7.4, 2H); 1.97 (m, 2H); 1.52 (m, 1H); 1.40 (m, 1H); 1.01 (t, J = 7.4, 3H); 0.96 (m,
1H); 0.37 (m,2H); 0.22 (m,2H).
Example 83: 4-(2-Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-dlpyrimldine-7-carboxylic acid (1-(2-methoxy-acetyl)-pipertdin-4-yl]-amide
Starting from 4-(2-Cyclopropylmethoxy-4-fiuoro-phenyl)-5H-pyrrQ|o[3,2-d]pyrimidine-7-carboxylic acid piperldin-4-ylamide hydrochloride (example A158) and methoxy-acetyl chloride the title compound is obtained as colorless solid.

MS (ESI): m/z = 482 (MH+. 100 %).
1H-NMR (300 MHz. DMSO-d6): 11.99 (br.s, 1H, -NH); 9.01 (s, 1H); 8.50 (d, J = 7.8, 1H; -NH); 8,29 (s, 1H); 7.67 (dd, J, = 8.5, J2 = 7.0, 1H); 7.08 (dd, J1 = 11.6, Jz = 2.4, 1H); 6.96 (ddd, J1 = J2 = 8.5, J3 = 2.4, 1H); 4,17 (m, 1H); 4.12 (d, J = 2.3, 2H); 3.92 (d, J = 7.0, 2H); 3.76 (m, 1H); 3.29 (s, 3H); 3.22 (m, 1H); 2.95 (m, 1H); 1.98 (m, 2H); 1.59 (m, 1H); 1.41 (m, 1H); 0.96 (m, 1H); 0.37 (m. 2H); 0.22 (m, 2H).
Example 84: 4-(2-Cyc)opropy!methoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyllc acid (1-acetyl-piperidin-4-yl)-amide
Starting from 4-(2-cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic
acid piperidin-4-ylamide hydrochloride (example A159) and acetyl chloride the title compound is
obtained as colorless solid.
MS (ESI): m/z = 452 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6.y. 12.11 (br.s. 1H, -NH); 9.05 (s. 1H); 8.49 (d, J = 7.8, 1H, -NH); 8.31
(s, 1H); 7.44 (dd. J, = 9.0, J2 =3.2, 1H); 7.38 (ddd, J1 = J2 = 9.1. J3 = 3.2, 1H); 7.19 (dd, J1 = 9.1, J2
= 4.4, 1H); 4.28-4.07 (m, 2H); 3.88 (d, J = 6.9, 2H); 3.80 (m, IN); 3.27 (m, 1H); 2.92 (m. 1H); 2.04
(s, 3H}; 1.97 (m, 2H): 1,56 (m, IN); 1.42 (m, 1H); 0.94 (m, 1H); 0.34 (m, 2H); 0.19 (m, 2H).
Example 85: 4-(2-Cyclopropylmethoxy-5-fluoro-phenyl>-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-propionyl-piperidin-4-yl)-amide
Starting from 4-(2-Cyclopropylmethoxy-5-fiuoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic
acid piperidin-4-ylamide hydrochloride (example A159) and propionyl chloride the title compound is
obtained as colorless solid.
MS (ESI); m/z = 466 (MH+. 100 %).
1H-NMR (300 MHz, DMSO-d6,): 12,11 (br.s, 1H. -NH); 9.05 (s, 1H); 8.49 (d, J = 7.9, 1H, -NH); 8.31
(s, 1H); 7,44 (dd, J1 = 8.9. J2 =3.2, 1H); 7,38 (ddd, J, = J2 = 9.1, J3 = 3.2, 1H); 7.19 (dd, J^ = 9.1, Ja
= 4.4, 1H); 4.23 (m. 1H); 4.14 (m, 1H); 3.88 (d. J = 6.9, 2H); 3.82 (m, 1H); 3.25 (m, 1H); 2.92 (m,
1H); 2.36 (qu, J = 7,3, 2H); 1.97 (m, 2H); 1.54 (m, 1H); 1.40 (m, 1H); 1.01 (t, J = 7.3, 3H); 0.94 (m,
1H); 0.34 (m,2H); 0.19 (m,2H).
Example 86: 4-(2-Cyclopropylmethoxy-5-ftuoro-phenyl>5H-pyrrolo[3,2-£/|pyrimidine-7-carboxylic acid [1-(2-methoxy-acetyl)-piperidin-4-yl]-amide
Starting from 4-{2-Cydopropylmethoxy-5-fluoro-phenyl>-5/y-pyrrolo[3,2-d]pyrimidine-7-carboxy(ic acid piperidin-4-ylamide hydrochloride (example A159) and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 482 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6,): 12.11 (br.s, 1H. -NH); 9.05 (s, 1H); 8.49 (d, J = 7.7, 1H. -NH); 8.31 (s. 1H); 7.44 (dd, J, = 9.0, J2 =3.2. 1H); 7.38 (ddd. J1 = J2 = 9.1, J3 - 3.2, 1H); 7.19 (dd, J1 = 9,1, J;

= 4.4, 1H); 4.16 (m, 2H); 4.12 (d, J = 2.6, 2H); 3.88 (d, J ^ 6.9, 2H); 3.76 {m, 1H); 3.31 (s, 3H); 3.21 (m, 1H);2.95(m, 1H): 1.98 (m, 2H); 1.56 (m, 1H); 1.42 (m, 1H); 0.94 (m, 1H); 0.34 (m, 2H); 0.19 {m, 2H).
Example 87: trans-4-(2-Cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2-i:/lpyrimidJne-7-carboxylic acid (4-acetylannino-cyclohexy!)-amide
Starting from trans~4-(2-Cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrroto[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide hydrochloride (example A160) and acetyl chloride the title compound is obtained as colorless solid, MS (ESI): m/z = 466 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6,): 12.08 {br.s, 1H, -NH); 9.06 {s, 1H); 8.34 (d, J = 7.7, 1H,-NH), 8.28 (s, 1H); 7.73 {d, J = 7.7, 1H. -NH); 7.44 (dd, J, = 8.9, J2 = 3.2, 1H); 7.38 (ddd, J1 = J2 = 9.1. J3 -3.2, 1H); 7.19 (dd, J, = 9.1, Jj = 4.4, 1H); 3.88 (d, J =^ 6.9, 2H); 3.82 (m, 1H); 3.57 (m, 1H); 2.02 (m. 2H); 1.86 (m, 2H); 1.79 (s, 3H); 1.37 (m, 4Hy, 0.94 (m, 1H); 0.34 (m, 2H); 0.18 (m, 2H).
Example 88: trans-4-(2-Cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrroIo[3,2-d]pyrimidine-7-carboxytic acid (4-propionylamino-cyclohexy))-amide
Starting from trans-4-(2-Cyclopropylmethoxy-5-1luoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amirjo-cydohexyl>amide hydrochtorrde (example A160)and propionyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 480 (MH+. 100 %).
1H-NMR (300 MHz, DMSO-d6,): 12.08 (br.s, 1H, -NH); 9.06 (s, 1H); 8.34 (d, J = 7.8, 1H,-NH), 8.28 (s, 1H); 7.63 (d, J = 7.8, 1H, -NH); 7.44 (dd, J, - 8.9, J2 = 3.2,1H); 7.38 (ddd, J1 = J2 = 9.2, J3 = 3.2, 1H); 7.19 (dd, J, = 9.2, J2 = 4.4, 1H); 3.88 (d, J = 6.9, 2H); 3.82 (m, 1H); 3.58 (m, 1H); 2.06 (qu, J = 7.5, 2H); 2.02 (m, 2H); 1.86 (m, 2H); 1.37 (m, 4H); 0.94 (m, IN); 0.34 (m, 2H); 0.18 (m, 2H).
Example 89: trans-4-(2-Cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimtdine-7-carboxy)lc acid I4-(2-methoxy-acetylamino)-cyclohexyl]-amide
Starting from trans-4-(2-Cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartKJxylic acid {4-amino-cyclohexyl)-amide hydrochloride (example A160)and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/2 = 496 (MH+, 100 %).
1H-NMR(300MHZ, DMSO-d6,): 12.08 (br.s, 1H.-NH); 9.06 (s, 1H); 8.33 (d, J = 7.9, 1H,-NH), 8.28 (s, 1H); 7.56 (d, J - 8.2, 1H, -NH); 7.43 (dd, J1, = 9.0, J2= 3.3, 1H); 7.38 (ddd, J1, = J2 = 9.1, J3 = 3.3, 1H); 7.19 (dd, J1 = 9.1, J2 = 4.4, 1H); 3.88 (d, J = 6.9, 2H); 3,82 (m, 1H & s, 2H); 3.71 (m, 1H); 3.31 (s, 3H); 2.02 (m, 2H); 1.82 (m, 2H); 1.45 (m, 4H); 0,94 (m, IN); 0.34 (m, 2H); 0.18 (m, 2H).

Example 90: trans-4-(2-cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carlDoxylic acid {4-acetylamino-cyclohexyl)-amide
Starting from trans-4-{2-cydopropylmethoxy-phenyI)-5H-pyrrolo[3,2-cy|pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A161) and acetyl chloride the title compound is obtained as colorless solid.
MS (ESI): m/z = 448 (IV1H', 100 %).
1H-NMR (300 MHz, DMSO-d6): 1202 (s, 1H, -NH); 9.05 (s, 1H); 8.37 (d, J = 7.9. 1H, -NH); 8.24 (s, 1H); 7.73 (d, J - 7.7, 1H, -NH); 7.64 (dd, J1 = 7.6, J2 = 1.7, 1H); 7.53 (ddd, J, = 8.0, J; = 7.6, J3 = 1.7. 1H); 7,17 (dd, J, = 8.0, J2 = 0.9, 1H); 7.13 (ddd. J1 - J2 = 7,6, J3 = 0.9, 1H); 3.91 (d, J - 6.9, 2H); 3.82 (m, 1H); 3.69 (m, 1H); 2.01 (m, 2H); 1.83 (m, 2H); 1.80 (s, 3H): 1.48-1.24 (m, 4H); 0.96 (m, 1H); 0.36 (m, 2H); 0.22 (m, 2H).
Example 91: trans-4-(2-Cyclopropylmethoxy-phenyl)-5fy.pyrrolo[3,2-d]pyrimidine-7-carboxylic add {4-{2-methoxy-aceylamino)-cyclohexyl-amide
Starting from trans-4-(2-Cyclopropylmethoxy-ptienyl)-5H-pyrrolQ[3,2-d]pyrimidine-7-carboxy!ic acid (4-amino-cyclohiexyl)-amide (example A161)and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 478 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.03 (s, 1H, -NH); 9.05 (s, 1H); 8.36 (d, J = 7.3. 1H, -NH); 8.24 (s, 1H); 7.64 (dd, J, = 7,6, J; = 1.7, 1H); 7.57 (, J - 8.3, 1H, -NH); 7.53 {ddd, J, = 8.0, Jj = 7.6, J3 -1.7. 1H); 7.17 (dd, J, = 8.0, J2 = 0.9, 1H); 7.13 (ddd. J, = J2 = 7.6, J3 = 0:9, 1H); 6.20 (s, 1H, -OH); 3.91 (d. J = 6.9, 2H); 3.80 (s, 2H & m, 1H); 3.71 (m, 1H); 3.30 (s, 3H); 2.03 (m. 2H); 1.82 (m, 2H); 1.47 (m, 4H); 0.96 (m, 1H); 0.36 (m, 2H); 0.22 (m, 2H).
Example 92: trans-(4-{[4-(2-Cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-cOpyrimidine-7-carbonyl]-amino}-cyclohexyl)-carbamic acid ethyl ester
Starting from trans-4-(2-Cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid
(4-amino-cyclohexyl)-amide (example A161) and ethyl chloroformate the title compound is obtained
as colorless solid.
MS (ESI): m/z = 478 (MH+ 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.02 (s, 1H, -NH); 9.05 (s, 1H); 8.36 (d, J = 7.8, 1H, -NH); 8.24 (s,
1H); 7.64 (dd, J1 = 7.6, Jj = 1.7, 1H); 7.53 (ddd, J, = 8.0, J2 = 7.6, j, = 1.7, 1H); 7.17 (dd, J, = 8.0,
Jj = 0.9, 1H); 7.13 (ddd, J, = J2 = 7.6, J3 = 0.9, 1H); 7.02 (d, J = 7.4, 1H, -NH); 3.98 (qu, J = 7.0,
2H); 3.91 (d, J = 6.8, 2H); 3.80 (m, 1H); 3.34 (m, 1H); 2.01 (m, 2H); 1.89 (m, 2H); 1.80 (s, 3H); 1.48
(m, 4H); 1.18 (t, J = 7.0, 3H); 0.96 (m, 1H); 0.36 (m, 2H); 0.22 (m. 2H).
Example 93: trans-4-(2-Cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(cyclopropanecarbonyl-amino)-cyclohexyl]-amide

starting from trans-4-(2-cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid
(4-amino-cyclohexyl)-amide (example A161) and cyclopropanecarbonyl chloride the title compound
is obtained as colorless solid.
MS (ESI): m/z = 474 (MH\ 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.03 (s, 1H, -NH); 9.05 (s, 1H); 8.37 (d. J = 7.8, 1H, -NH); 8.24 (s,
1H); 7.95 (d, J = 7.8, 1H, -NH); 7.64 (dd, J1 = 7.6, J2 = 1.7, 1H); 7.53 (ddd, J, = 8.0, Jj = 7.6, J3 =
1.7, 1H); 7.17 (dd, J, = 8.0, 4 = 0.9, 1H); 7.13 (ddd, J1 = J2 = 7.6, J3 = 0.9, 1H); 3.91 (d, J = 6.8,
2H); 3.84 (m, 1H); 3.61 (m, 1H); 2.01 (m, 2H)i 1,89 (m, 2H); 1.05 (m, 1H); 1.39 {m, 4H); 0.96 (m,
1H); 0.67 (m, 4H); 0.36 (m, 2H); 0.22 (m, 2H).
Example 94: 4-(2-Cyclopropylmethoxy-phenyl)-5H-pyrrolol3,2-c(|pyrimidine-7-carboxylic acid (1-acetyl-piperidin-4-yl)-amide
Starting from 4-(2-cyclopropylmethoxy-phenyi)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamidB (example A152) and acetyl chloride the title compound is obtained as colorless solid.
MS (ESI): m/z = 434 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.06 (s, 1H, -NH); 9.05 (s, 1H): 8.52 (d, J = 7.8, 1H, -NH); 8.26 (s, 1H); 7.64 (dd, J, = 7.6, J2 = 1.7, 1H); 7.53 (ddd, J1 = 8.0, J2 = 7.6, J3 = 1.7, 1H); 7.17 (dd, J, = 8.0, J1 = 0.9, 1H); 7.13 (ddd, J, = J2 = 7.6, J3 = 0.9, 1H); 4.21 (m, 1H); 4.17 (m, 1H); 3,91 (d, J = 6.8, 2H); 3.80 (m, 1H); 3.28 (m, 1H); 2.92 (m, 1H); 2.04 (s, 3H); 1.98 (m, 2H); 1.57 (m, 1H); 1.40 (m, 1H); 0.96 (m, 1H); 0.36 (m, 2H); 0.22 (m, 2H).
Example 95: 4-([4-(2-Cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-c(ipyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid ethyl ester
Starting from 4-(2-cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyllc acid piperidin-4-ylamide (example A162) and ethyl chloroformate the title compound is obtained as colorless solid.
MS (ESI): m/z = 464 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.05 (s, 1H. -NH); 9.05 (s, 1H); 8.51 (d, J = 7.8, 1H, -NH); 8.27 (s. 1H); 7.64 (dd,J1 = 7.6, J2== 1.7,1H); 7.53 (ddd, J, = 8.0, Jz = 7.6, J3= 1-7, 1H); 7.17 (dd, J1 = 80, J3 = 0.9, IN); 7.13 (ddd, J1 = J? = 7.6, J3= 0.9, 1H); 4.13 (m, 1H); 4.08 (qu, J = 7.1, 1H); 3.91 (d, J = 6.8, 2H & m, 2H); 3.10 (m, 2H); 1.97 (m, 2H); 1.50 (rr, 2H); 1.21 (t, J = 7.1. 3H); 0.97 (m, 1H); 0,36 (m, 2H); 0.22 (m, 2H).
Example 96: 4-(2-Cyclopropylmethoxy-phenyl)-5/^-pyrrolo{3,2-c(]pyrimidine-7-carboxylic acid (1-cyclopropanecarbonyl-piperidin-4-yl)-amide

starting from 4-(2-cyclopropylmethoxy-ptienyl)-5H-pyrrola[3,2-d]pyrimidine-7-carboxylic acid
piperidin-4-y!amide (example A162) and cyclopropanecarbonyl chloride the title compound is
obtained as colorless solid.
MS (ESI): m/z = 460 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.05 (s, IN, -NH); 9.05 (s, 1H); 8.54 (d, J = 7.8, IN, -IMH); 8.27 (s,
1H); 7.64 (dd, J1 = 7.6, J2 = 1.7, 1H); 7.53 (ddd, J1 = 8.0, J2 = 7.6, J3 = 1.7,1H); 7.17 (dd, J, = 8.0,
J2 = 0.9, 1H); 7.13 (ddd, J, = J2 = 7.6, J3 = 0.9, 1H); 4.27-4.10 (m, 3H); 3.91 (d, J = 6.8, 2H); 3.40
(m, IN); 2.98 (m, IN); 2.10-1.90 (m, 3H); 1.69-1.34 {m, 2H); 0.96 (m, 1H); 0.72 (m, 4H); 0.35 (m,
2H);0.22(m, 2H).
Example 97: 4-(2-Cyclopropylmethoxy-4-fluoro-5-melhoxy-phenyl)-5H-pyrrolo[3,2-dIpyrlmidine-7-carboxylic acid {1-propronyl-piperidin-4-yl)-amide
Starting from 4-(2-cyclopropylmethoxy-4-fluoro-5-fnethoxy-phenyl)-5H-pyrrolo|3,2-dlpyrimidine-7-carboxylic acid piperidin-4-y/am(de hydrochloride (example A163) and propionyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 496 (MH', 100 %).
1H-NMR(300 MHz, DMSO-d6): 12.03 (br.s, 1H,-NH); 9.05(s, IN); 8.50 (d, J = 7,8, 1H;-NH);8.29 (s, 1H); 7.41 (d, J = 9.8, 1H); 7.18 (d, J = 13.4,1H); 4.23 (m, 1H); 4.14 (m, 1H)); 3.85 (s, 3H & d, J = 6.8, 2H); 3.84 (m, 1H); 3.24 (m, 1H); 2.93 (m, 1H); 2.36 (qu, J = 7.4, 2H); 1.97 (m, 2H); 1.53 (m, 1H); 1.40 (m, 1H); 1.01 (t, J = 7.4, 3H); 0.93 (m, IN); 0.34 (m, 2H), 0.18 (m, 2H).
Example 98: 4-(2-Cyclopropylnnethoxy-4-fluoro-5-melhoxy-phenyl>-5H-pyrrolo[3,2-dlpyrimidlne-7-carboxylic acid [1-(2-methoxy-ethanoyi)-piperidin-4-yl]-amide Starting from 4-(2-cyclopropylrrethoxy-4-fluoro-5-methoxy-phenyl}-5H-pyrro!o[3,2-d]pyrimldine-7-carboxylic acid piperidin-4-ylannide hydrochloride (example A163) and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 512 (MH+, 100 %).
1H-NMR {300 MHz, DMSO-d6): 12.03 (br.s, 1H, -NH); 9,05 (s, 1H); 8.50 (d, J = 7.8. 1H; -NH), 8.29 (s, 1H); 7.41 (d, J = 9.8, 1H); 7.18 (d, J = 13.4,1H); 4.16 (m, 1H); 4.12 (d, J = 2.7, 2H)); 3.85 (s, 3H & d, J = 6.8, 2H); 3.77 (m, 1H);3.31 (s, 3H); 3.22 (m, 1H);2.95(m, 1H); 1,98{m, 2H); 1.54 (m, 1H); 1.44 (m, 1H); 0.92 (m. 1H); 0.34 (m, 2H), 0.17 (m, 2H).
Example 99: 4-(2-Cyclopropylmethoxy-4-fluoro-5-nrielhoxy-phenyl)-5H-pyrrolo[3,2-c/]pyrimidine-7-carboxylic acid (1-acetyl-piperidin-4-yl)-amide
Starting from 4-(2-cyclopropylmethoxy-4-fluoro-5-methoxy-pheny))-5H-pyrrolo[3,2-d]pyrimidine-7-cartxjxylic acid piperidin-4-ylamide hydrochloride (example A163) and acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 482 (MH+, 100 %).

1H-NMR(300MHz, DMSO-d6): 12.03 (br.s, 1H.-NH); 9.05 (s, 1H); 8.50 (d, J = 7.8, 1H:-NH);8.29 (s, 1H); 7.41 {d, J = 9.8, 1H); 7.18 (d, J = 13.4,1H); 4.18 (m, 1H): 4.13 (m, 1H)}; 3.85 (s, 3H & d, J = 6.8. 2H); 3.81 (m, 1H}; 3.27 (m, 1H); 2.92 (m, 1H); 2.04 (s, 3H); 1.97 (m, 2H); 1.56 {m, 1H); 1.40 {m, 1H); 0.93 (m, 1H); 0.34 (m, 2H), 0.17 (m, 2H).
Example 100: 4-(2-Cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-cOpyrimidine-7-carboxylic acid ((R)-1-acetyl-piperidin-3-yl]-amide
Starting from 4-{2-cyclopropylmethoxy-4-fIuoro-5-methoxy-phenyi)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (R>-piperidin-3-ylamide hydrochloride (example A164) and acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 482 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 11.89 (br.s, 1H. -NH); 9.03 (s, 0.5H); 9.02 (s, 0.5H); 8.63 (d, J = 7.2, 0.5H, -NH); 8.57 (d, J = 8.3. 0.5H, -NH); 8.30 (s, 0.5H); 8.28 (s, 0.5H); 7.41 (d, J = 9.9, 1H): 7.16 (d, J = 13.4, 1H), 4.08-3.30 (m, 1.5H), 3.67 (a, 3H &d, J = 6.8, 1H); 3.72(m, 0.5H), 3.60-3.19 (m, 3H); 2.06 (s, 1.5H); 1.97 (s. 1.5H & m. 1H); 1.86-1.45 (m, 3H); 0.94 (m, 1H); 0.33 (m, 2H); 0.17 (m, 2H).
Example 101: 4-(2-Cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-c/|pyrimidine-7-carboxylic acid ({R)-1-propionyl-piperidin-3-yl)-amide
Starting from 4-(2-Cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {R)-piperidin-3-ylaniide hydrochloride (example A164) and propionyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 496 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.31 (br.s, 1H, -NH); 9.01 (s, 1H); 8.61 (d, J = 7.5, 0.5H, -NH); 8.57 (d, J = 7.5, 0.5H, -NH); 8.30 (s, 0.5H); 8.29 (s, 0.5H); 7.41 (d, J = 9.9, 1H); 7.18 (d, J = 13.4, 1H); 4.08-3.91 (m, 1.5H); 3.85 (s. 3H & d, J = 6.7. 2H); 3,76 (m, 0.5H); 3.57 (m, IN); 3.48-3.21 (m, 2H); 2.45-2.23 (m, 2H); 1.98 (m, 1H); 1.75 (m, 2H); 1.53 (m, 1H); 1.05-0.89 (m, 4H); 0.32 (m, 2H); 0.18 (m,2H).
Example 102: 4-(2-Cyc!opropy)methoxy-4-f)uoro-5-methoxy-pheny)}-5H-pyrrolo[3,2-d]pyrimidlne-7-carboxylic acid [(R)-1-(2-methoxy-acetyl)-piperidin-3-yl]-amide Starting from 4-(2-Cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (R>-piperidin-3-ylamide hydrochloride (example A164) and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 512 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 11.90 (br.s, 1H, -NH); 9,02 (s, 1H); 8.60 (br.m, 1H. -NH); 8.31 (m, 1H); 7.41 (d, J = 9.8,1H); 7.18 (d. J = 13.3, 1H); 4.16-3.95 (m, 3H); 3.92 (m, 0.5H); 3.84 (s, 3H & d,

J = 6.8, 2H); 3,69 (m.0.5H); 3.55-3.21 (m, 3H): 3.30 {s, 1H); 3.17 (s, 1H); 1.98 (m, 1H); 1.75 (m, 2H); 1.57 (m, 1H); 0.93 (m, 1H); 0.33 (m, 2H); 0.17 (m, 2H).
Example 103: 4-{2-Cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-£:/]pyrim!dine-7-carboxylic acid ((R}-1-acetyl-pyrrolidin-3-yl)-amide
Starting from 4-(2-Cyctopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (R)-pyrrolidin-3-ylamide hydrochloride (example A165) and acetyl chloride the title compound is obtained as colorless MS (ESI): m/z = 426 (MH+, 100 %),
■1H-NMR (300 MHz. DMSO-d6): 12.41 (br.s, 1H. -NH); 9.39 (br.s, 1H, -NH2); 9.11 (s, 1H); 8.69 (d, J = 6.7, 1H, -NH); 8.51 (d, J = 3.3, 1H); 745 (d, J = 9.8, 1H); 7.21 (d, J = 13.3, 1H); 4.65 (m, 1H); 3.S7 (d, J = 6.8, 2H); 3.86 s, 3H); 3.52-3.46 (m, IN); 3.30-3.14 (m, 1H); 2.32 (m, 1H); 2,04 (m, IN); 0.93 (m, 1H); 0.33 (m, 2H); 0.19 (m, 2H).solid.
Example 104: 4-(2-Cyclopropylmethoxy-4-flLioro-5-m8thoxy-phenyl)-5H-pyrrolo[3,2-c^pyrimidine-7-carboxylic acid {(R)-1-propionyl-pyrrolidin-3-yl)-amide
Starting from 4-(2-CycIopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (R)-pyrrolidin-3-ylamide hydrochloride (example A165) and propionyl chtoride the title compound is obtained as colorless solid. MS (ESI): m/z = 482 (MH+. 100 %),
1H-NMR (400 MHz, DMSO-d6): 11.98 (br.s, 1H,-NH); 9.04 (s, 1H); 8.62 (d, J = 7.0, IN,-NH); 8.59 (d, J = 7.0, 0.5H, -NH); 8.31 (d, J = 1,8, 1H); 7.41 (d, J = 9.6, 1H); 7.18 (d, J = 13.3, 1H); 4.59 (m, 0.5H); 4.51 (m, 0,5H); 3.84 (s, 3H & d, J = 4.4, 2H & m, 0.5H); 3.70-3.58 (m, 1.5H); 3.56-3.38 (m, 1.5H); 3.30 (m, 0.5H); 2.33-2,18 (m, 1H & m, 2H); 2.06 (m, 0.5H); 1.94 (m, 0.5H); 1,00 (m, 3H); 0.92 (m, 1H); 0.33 (m, 2H); 0,17 (m, 2H).
Example 105: 4-(2-Cyclopropylmethoxy-4-fluoro-5-m8thoxy-phenyl)-5H-pyrrolo[3,2-(/|pyrimidine-7-carboxylic acid [(R)-1-(2-methoxy-acetyl)-pyrrolidin-3-yl]-amide Starting from 4-(2-Cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartxDxylic acid (R)-pyrrolidin-3-ylamide hydrochloride (example A165) and methoxy-acetyl chloride the title compound is obtained as colorless solid, MS (ESI): m/z = 498 (MH\ 100 %).
1H-NMR (400 MHz, DMSO-d6): 11,95 (br.s, 1H, -NH); 9.04 (s, IN); 8.61 (d, J = 7,2,1H, -NH); 8.59 (d, J = 7.2, 0.5H, -NH); 8,31 (s. IN); 7.41 (d, J = 9.7, 1H); 7,18 (d, J = 13.2, 1H); 4.59 (m, 0.5H); 4.51 (m, 0,5H); 4.10-3.97 (m, 2H); 3,84 (s, 3H & d, J = 4.4, 2H); 3.79 (m, 0.5H); 3.70 (m, 0.5H); 3.57 (m, 1H); 3.48 (m, 0.5H); 3.41-3,30 (m, 1.5H); 3.31 (s, 1,5H); 3.29 (s, 1.5H); 2.33-2.17 (m. 1H); 2,10 (m, 0.5H); 1.93 (m, 0.5H); 0.92 (m. 1H); 0.33 (m, 2H); 0.17 (m, 2H).

Example 106: trans-4-(2-Cyclopropy!methoxy-5-'fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-c^pyrimidine-7-carboxyllc acid (4-acetylannino-cyclohexyl)-annide Starting from trans-4-(2-cyclopropylmethoxy-5-fluoro-4-methaxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4-amino-cyclohexyl}-amide (example A139) and acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 496 (MH+. 100 %).
1H-NMR (300 MHz, DMSO-d6): 11.95 (br.s, 1H, -NH); 9,01 (s, 1H); 8,36 (d, J = 7.8, 1H: -NH); 8.24 (s, 1H); 7.73 (d, J = 7.7, 1H, -NH); 7.49 (d, J = 11,8, 1H); 6,93 {d, J = 7.3,1H); 3.97 (s, 3H); 3,95 (d, J = 7.1,2H);3,81 (m, IN); 3.58 (m, 1H);2.01 (m, 2H): 1,86(m,2H); 1.79(s,3H); 1.36 (m,4H): 0,97 (m, 1H); 0,36 {m, 2H); 0,21 (m, 2H),
Example 107: lrans-4-(2-Cyc[oprQpylmethoxy-5-fluoro-4-methoxy-phenyI)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(2-methoxy-acetylamino)-cyclohexyl]-amide Starting from trans-4-(2-cyclopropylmethoxy-5-f!uoro-4-methoxy-phenyl)-5H-pyrroio[3,2-c/]pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A139) and methoxy-acetyl chloride the title compound is obtained as colorless solid, MS (ESI): m/z = 526 {MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 11,94 (br.s, IN,-NH); 9.01 (s, IN); 8.35 (d, J = 7.8, 1H;-NH);8,24 (s, 1H); 7.57 (d, J = 8.2, 1H, -NH); 7,49 (d, J = 11.9, 1H); 6,93 (d, J = 7,3,1 H); 3.97 (s, 3H); 3.95 (d, J = 7.0, 2H);3,79(m, IN & s, 2H); 3.54 (m, 1H); 3,31 (s, 3H); 2.03 (m, 2H); 1,80 (m,2H); 1.45(m, 4H); 0,96 (m, 1H); 0.36 (m, 2H); 0,21 (m, 2H).
Example 108: 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-c/]pyrinnidine-7-carboxylic acid (1-acetyl-piperidin-4-yl)-amide
Starting from 4-(2-cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide hydrochloride (example A166) and acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 482 (MM', 100 %),
1H-NMR (300 MHz, DMSO-d6): 11.98 (br.s, 1H,-NH); 9.01 (s, 1H);8.51 (d, J = 7.8, 1H;-NH);8.27 (s, 1H); 7.50 (d, J = 119, 1H); 6.93 (d, J ^ 7.3,1H); 4,20 (m, 1H); 4.13 (m. 1H); 3.97 (s, 3H); 3.95 (d, J = 7.1,2H);3.79(m, 1H): 3.27 (m, 1H);2.92(m, 1H); 2.04 (s, 3H); 1.97 (m,2H); 1.56 (m, 1H); 1.40 (m, 1H); 0.95 (m, 1H); 0.36 (m, 2H), 0.22 (m, 2H).
Example 109: 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d| pyrimidine-7-carboxyiic acid [1 -(2-methoxy-ethanoyl )-piperidin-4-yl]-amide Starting from 4-(2-cyclopropylmethoxy-5-fluoro-4-melhoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide hydrochloride (example A166) and methoxy-acetyl chloride the title compound is obtained as colorless solid.

MS (ESI): m/z = 512 (MH+, 100 %)
1H-NMR (300 MHz, DMSO-d6): 11.98 (br.s, 1H. -NH); 9.01 (s, 1H); 8.51 (d, J = 7.8, 1H; -NH); 8.27 (s, 1H); 7.50 (d, J = 11.9, 1H); 6.93 (d, J = 7.3,1H); 4.16 (m, 1H); 4.12 (d, J = 2.5, 2H); 3.97 (s, 3H); 3,95(d, J = 7.1,2H);3.76(m, 1H);3.31 (s, 3H); 3.22 (m, 1H); 2,95 (m, 1H); 1.98 (m,2H); 1.55 (m, 1H); 1.40 (m, 1H); 0.96 (m, 1H); 0.36 (m, 2H), 0.22 (m, 2H).
Example 110: 4-(2-Cyclopropytmethoxy-5'fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-<:lpyrimidine-7-carboxylic acid> Starting from 4-(2-cyclopropylmethoxy-5-fluoro-4-methoxy-pheny|)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide hydrochloride (example A166) and propionyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 496 (MH+, 100 %),
1H-NMR (300 MHz, DMSO-d6): 11.97 (br.s, 1H, -NH); 9.00 (s, 1H); 8.51 (d, J = 7.8, 1H; -NH); 8.27 /s, 1H); 7,49 (d, J = 118, W); 6.93 (d, J = 7.3, W); 4.23 (m, 1H); 4.13 (m, W); 3.97(s, 3H): 3.95 (d, J = 7.1, 2H); 3.83 (m, 1H); 3.24 (m, IN); 2.93 (m, 1H); 2.36 (qu, J = 7.4. 3H); 1.96 (m, 2H); 1.53 (m, IN); 1.40 (m. 1H); 1.01 (t, J = 7.4, 3H); 0.97 (m, 1H); 0.36 (m, 2H), 0.22 (m, 2H).
Example 111: 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-cflpyrimidine-7-carboxylic acid ((R)-1-propronyI-piperidin-3-yl)-amide
Starting from 4-(2-cyciopropylmethoxy-5-fluoro-4-melhoxy-phenyi)-5H-pyrrolo[3,2-d)pyrimidine-7-carboxylic acid (R)-piperidin-3-ylamide hydrochloride (example Al67) and propionyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 496 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 11.98 (br.s, 1H, -NH); 8.97 (s, 1H); 8.61 (d, J = 7.3, 0.5H; -NH); 8.56 (d, J = 7.3, 0.5H, -NH); 8.28 (s, 0.5H); 8.27 (s, 0.5H); 7.50 (d, J = 11.9, 1H); 6.93 (d, J = 7.3,1H); 4.16 (m, 1H); 4.12 (d, J = 2.5, 2H); 3.97 (s, 3H & m, 1.5H); 3.95 (d, J = 7.1, 2H); 3.77 (m, 0.5H); 3.57 (m, 1H);3.40(m, 1.5H); 3.27 (m, 0.5H); 2.38 (m, 1H);2.32(m, IN); 1.96 (m, 1H); 1.74 (m, 2H); 1.53 (m, 1H); 0.99 (m, 3H & m, 1H); 0.36 (m, 2H), 0.21 (m, 2H).
Example 112: 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-cf] py rim id i ne-7-carboxylic acid [(R)-1-(2-methoxy-ethanoyl)-piperidin-3-yl]-am id e Starting from 4-(2-cyclopropylmethoxy-5-fluoro-4-methoxy-pheny|)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (R)-piperidin-3-ylamide hydrochloride (example A167) and methoxy-acetyl chloride the title compound is obtained as colorless solid.
Example 113: 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-c(lpyrim!dine-7-carboxylic acid ((R)-1-acetyl-plperidin-3-yl)-amide

starting from 4-(2-cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl}-5H-pyrroio[3,2-d]pyrinnidine-7-carboxylic acid (R)-piperidin-3-ylamide hydrochloride (example A167) and acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 482 (MH', 100 %).
1H-NMR (300 MHz, DMSO-d6): 11.98 (br.s, 1H, -NH); 8.99 (s, 0.5H); 8.98 (s, 0.5H); 8.64 (d, J = 7.3, 0.5H; -NH); 8.56 (d. J = 7.3, 0.5H, -NH); 8.28 (s, 0.5H); 8.26 (s, 0.5H); 7.50 (d, J = 11.8, IN); 6.93 (d, J = 7.3,1H); 3.97 (s, 3H & m, 1.5H): 3.94 (d, J = 7.3, 2H); 3.73 (m, 0.5H); 3.49 (m. 2H); 3.41 (m, 0.5H); 3.22 (m, 0.5H); 2.05 (s, 1.5H); 1.98 (s, 1.5H&m, 1H); 1.71 (m, 2H); 1.54 (m, 1H); 0.97 (m, IN); 0.36 (m, 2H), 0.22 (m. 2H).
Example 114; 4-(2-Cyclopropylmethoxy-5-'tluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-c(|pyrimidine-7-carboxylic acid ((S)-1 -proptonyl-piperidin-3-yl)-amide
Starting from 4-(2-cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylie acid (S)-piperJdin-3-yfamide hydrochloride (example A168) and propionyl chloride the title compound is obtained as colorless solid. I^S (ESI): m/z = 496 (MH+, 100 %).
1H-NIVIR (300 MHz. DMSO-do): 11.98 (br.s, 1H,-NH); 8.97 (s, 1H); 8.61 (d, J = 7.3, 0.5H;-NH); 8.56(d, J = 7.3, 0.5H,-NH);8.28(s, 0.5H); 8.27 (s, 0.5H); 7.50 (d, J = 11.9, 1H); 6.93 (d, J = 7.3,1H); 4.16 (m, 1H); 4.12 (d, J = 2.5, 2H); 3.97 (s, 3H & m, 1.5H); 3.95 (d, J = 7.1, 2H); 3.77 (m, 0.5H); 3.57 (m, 1H); 3.40 (m, 1.5H); 3.27 (m, 0.5H); 2.38 (m, 1H); 2.32 (m, 1H); 1.96 (m, 2H); 1.74 (m, 2H); 1.53 (m, 1H); 0.99 (m, 3H & m, 1H); 0.36 (m, 1H), 0.21 (m, 2H).
Example 115: 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(S)-1-(2-methoxy-ethanoyl)-piperidin-3-yl]-amide Starting from 4-(2-cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-ty]pyrimidine-7-cartxixylic acid (S)-piperidin-3-ylamide hydrochloride (example A168) and methoxy-acetyl chloride the title compound is obtained as colorless solid.
Example 116: 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-c(]pyrtmidine-7-carboxylic acid ((S)-1-acetyl-piperidin-3-yl)-amide
Starting from 4-(2-cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (S)-piperidin-3-ylamide hydrochloride (example A168) and acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 482 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 1198 (br.s, 1H, -NH); 8.99 (s, 0.5H); 8.98 (s, 0.5H); 8.64 (d, J = 7.3, 0.5H; -NH); 8.56 (d, J = 7.3, 0.5H, -NH); 8.28 (s, 0.5H); 8.26 (s, 0.5H); 7.50 (d, J = 11.8, 1H); 6.93 (d, J = 7.3,IN); 3.97 (s, 3H & m, 1.5H); 3.94 (d, J = 7.3, 2H); 3.73 (m, 0.5H); 3.49 (m, 2H);

3.41 (m, 0.5H); 3.22 (m,0.5H); 2.05 (s,1.5H); 1,98 (s, 1.5H & m, 1H); 1.71 (m, 2H): 1.54 (m, 1H); 0.97 (m, 1H); 0.36 (m, 2H), 0.22 {m, 2H).
Example 117; 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-c(]pyrimidine-7-carboxylic acid ((R)-1-acetyl'pyrrolidin-3-yl)-amide
Starting from 4-{2-cyciopropylmethoxy-5-f!uoro-4-nnethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (R)pyrrolidin-3-ylamide hydrochloride (example A169) and acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 468.1 (MH\ 100 %).
1H-NMR (300 MHz, DMSO-d6): 11.93 (br.s, 1H,-NH);9.01 (s, 1H); 8.64 (d, J = 7.1, 0.5H;-NH); 8,61 (d, J = 8.6, 0.5H, -NH); 8.29 (d, J = 2.3. 1H); 7.50 (dd, J1 - 11.8, J2 = 1.3, 1H); 6,93 (d, J = 7.2. IN); 4.61 (m, 0.5H); 4.51 (m, 0.5H); 3.97 (s, 3H); 3.95 (d. J = 7.0, 2H); 3.85 (m, 0.5H); 3.67-3.56 (m, 1.5H); 3.54-3.30 (m, 1,5H); 3,32 (m, 0,5H); 2.30 (m, 0,5H); 2.22 (m, 0.5H); 2.10 (m, 0.5H); 1.93 (m, 1.5H),- 1.96 (m, 1.5H);1.95 (m. 0,5H); 0.96 (m, 1H); 0.36 (m, 2H), 0.22 (m, 2H>.
Example 118: 4-(2-Cyclopropylmethoxy-5-fIuoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-c/lpyrimidine-7-carboxylic acid ((R)-1'propionyl-pyrrolidin-3-yl)-amide
Starting from 4-(2-cyclopropy(methoxy-5-fluoro-4-nnethoxy-pheny()-5H-pyTolof3,2-o]pyrimidine-7-carboxylic acid (R>pyrrotidin-3-ylamide hydrochloride (example A169) and propionyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 482 (MH+, 100 %),
1H-NMR (300 MHz, DMSO d6): 11,97 (br.s, 1H, -NH); 9.00 (s, 0,5H); 8.99 (s, 0.5H); 8.64 (d, J = 7.1, 0.5H; -NH); 8.61 (d, J = 8.6, 0.5H, -NH); 8.29 (d, J = 1.8, 1H); 7.50 (dd, J, = 11.9, J2 = 1.1, 1H); 6.93 (d, J - 7.3, 1H); 4.61 (m. 0.5H); 4.51 (m, 0.5H); 3,97 (s, 3H); 3.95 (d, J = 6.9, 2H); 3.82 (m, 0.5H); 3.65 (m, 0.5H); 3,51 (m, 0.5H); 3.42 (m, 1H); 3.33 (m, 0,5H); 2.33-2.17 (m, 3H); 2.05 (m, 0,5H); 1.93 (m, 0.5H); 0.98 (m, 1H); 0.36 (m, 2H), 0,23 (m, 2H).
Example 119: 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phGnyl>-5H-pyrrolo[3,2-dlpyrimidine-7-carbDxylic acid [(R)-1-(2-methoxy-acetyl)-pyrrolidin-3-yl]-amide Starting from 4-(2-cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-c/Ipyrimidine-7-carboxylic acid (R)-pyrrolidin-3-ylamide hydrochloride (example A169)and methoxy-acetyl chloride \he title compound is obtained as colorless solid. MS (ESI): m/z = 498 (MH\ 100 %).
1H-NMR (300 MHz, DMSO-d6): 11.21 (br.s, 1H, -NH); 9.00 (s, 0,5H); 8.99 (s, 0.5H); 8.63 (d, J = 7.3, 0.5H; -NH); 8.61 (d, J = 7.3, 0.5H, -NH); 8.29 (s, 1H); 7.50 (dd, J1 = 11.8, J2 = 1.0, 1H); 6.93 (d, J = 7.3, 1H); 4.61 (m, 0.5H); 4.51 (m, 0.5H); 4.07-4.01 (m, 2H); 3.97 (s, 3H); 3.95 (d, J = 7.0, 2H); 3.79 (m, 0.5H); 3,69 (m, 0,5H); 3.58 (m, 1H); 3.47 (m, 0.5H); 3.41-3.30 (m, 1,5H); 3.32 (m, 1.5H);

3.30 {m. 1.5H); 2.29 (m, 0.5H); 2.20 (m, 0.5H); 2.06 (m, 0.5H); 1,93 (m, 0,5H); 0.95 (m, 1H); 0.33 {m, 2H), 0.21 (m, 2H).
Example 120: trans-4-{2-Cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrrolo[3,2-a]pyrimidine-7-carboxylic acid {4-acetylamino-cyclohexyl)-amide
Starting from trans-4-(2-cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrrolo[3,2-d]pyrlmidine-7-carboxylic acid (4-amlno-cyclohexyl)-amide (example A170) and acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 462 (MH+, 100 %).
1H-NMR 400 MHz, DMSO-d6): 11.96 (br.s, 1H, -NH); 9.03 (s, 1H); 8.36 (d, J = 7.8, 1H, -NH); 8.22 (s, 1H); 7.73{d, J = 7.7, 1H,-NH); 7.44 (d, J = 1.9, 1H); 7.33 (dd, J, = 8.4, Jj^ 1.9, 1H); 7.06 (d, J = 8.4, 1H); 3.86 (d, J = 6.8, 2H); 3.82 (m, 1H); 3.59 (m, 1H); 2.33 (s, 3H); 2.02 (m, 2H); 1.87 (m, 2H); 1.63 (s, 3H); 1.46-1.27 (m, 4H); 0,93 (m, 1H); 0.34 (m, 2H); 0.19 (m, 2H).
Example 121: trans-4-(2-Cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrrolo[3,2-d|pyrimidine-7-carboxylic acid [4-{2-methoxy-acetylamino)-cyclohexyl]-amide Starting from trans-4-(2-cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A170) and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 492 (MH\ 100 %).
1H-NMR 400 MHz, DMSO-d6): 11.96 (br.s, 1H,-NH); 9.03 (s, 1H); 8.36{d. J = 7.8, 1H,-NH); 8.22 (s, 1H); 7.56 (d, J = 8.2, 1H, -NH); 7.44 (d, J = 1.9, 1H); 7.33 (dd, J1 = 8.4, J2 = 1.9, 1H); 7.06 (d, J = 8.4, 1H); 3.86 (d, J = 6.8, 2H); 3.78 (s, 2H & m, 1H); 3.71 (m, 1H); 3.31 (s, 3H); 2.33 (s, 3H); 2.02 (m,2H); 1.87 (m,2H); 1.32 (m, 4H); 0.93 (m, 1H); 0.34 (m. 2H); 0.19 (m, 2H).
Example 122: trans-(4-{[4-(2-Cyclopropylmethoxy-5-methyl-pheny!)-5H-pyrrolo[3,2-cOpyrimidine-7-carbo^yl]-amino}-cyclohexyl)-carbamic acid ethyl ester Starting from trans-4-(2-cyclopropylmethoxy-5-methyl-phenyl)-5^/-pyrrolo[3,2-dIpyrimtdine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A170) and ethyl chloroformate the title compound is obtained as colorless solid. MS (ESI): m/z = 492 (MH\ 100 %).
1H-NMR 400 MHz, OMSO-de): 11.96 (br.s, 1H,-NH); 9.03 (s, 1H); 8.36 (d, J = 7.8, 1H,-NH); 8.22 (s, 1H);7.44(d, J=1.9, 1H); 7.33 (dd, J, = 8.4, J2= 1.9, 1H); 7.06 (d, J = 8.4,1H); 7.01 (d, J = 7.1, 1H, -NH); 3.98 (qu, J = 7.0, 1H); 3.86 (d, J = 6.8, 2H); 3.79 (m, 1H); 3.34 (m, 1H); 2.33 (s, 3H); 2.01 (m, 2H);1.88(m, 2H); 1.46-1.26 (m, 4H); 1.16{t, J = 7.0, 3H); 0.93 (m, 1H); 0.34 (m, 2H); 0.19 (m, 2H).

Example 123: 4-(2-Cyclopropy(methoxy-5-methyl-phenyl)-5H-pyrrolo[3,2-0]pyrimidine-7-carboxylic acid (1-acetyl-piperidin-4-yi)-amide
Starting from 4-(2-cyclopropylmethoxy-5-methy!-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide (example A172) and acetyl chloride the title compound is obtained as colorless solid.
MS (ESI); m/z = 448 (MH+, 100 %).
1H-NMR 300 MHz, DMSO-d6): 11.99 (br.s, 1H, -NH); 9.03 (s, 1H); 8.52 (d, J = 7.8, 1H, -NH); 8.25 (s, 1H);7.44(d, J = 2.0, 1H); 7.33 (dd, J1 = 8.5, J2 = 2.0, 1H); 7.06 (d, J = 8.5, 1H); 4.23-4.10 (m, 2H); 3.87 (d, J = 6.8, 2H); 3.80 (m, 1H); 3.27 (m, 1H); 2.92 (m, 1H); 2.33 (s, 3H); 2.04 (s, 3H); 1.97 (m, 2H); 1.56 (m, 1H); 1.39 (m, 1H); 0.93 (m, 1H); 0.34 (m, 2H); 0.19 (m, 2H).
Example 124: 4-(2-Cyclopropylniethoxy-5-methyl-phenyl)-5H-pyrroloI3,2-c(]pyrimidine-7-carboxylic acid [1-(2-methQxy-acstyl)-piperJdin-4-yl]-amide
StacUag from 4-(2-cvclopropylmethQy.y-5-methvl-pheavlV5H-pvff°'°t3,2-dlpv"f^viine-7-Garboxylic acid piperidin-4-ylamide (example A172) and methoxy-acetyl chloride the title compound is obtained as colorless solid, MS (ESI): m/z = 478 (MH+, 100 %).
1H-NMR 300 MHz, DMSO-d6): 11.99 (br.s, 1H, -NH); 9.03 (s, 1H); 8.51 (d, J = 7.9, 1H, -NH); 8.25 (s, IN); 7.44 (d, J = 1.9, 1H); 7.33 (dd, J, = 8.5, J2= 1.9, 1H); 7.06 (d, J = 8.5, IN); 4.16 (m, 2H); 4.12 (d, J = 2.7, 2H); 3.87 (d, J = 6.9, 2H); 3.76 (m, 1H); 3.31 (s, 3H); 3.22 (m, 1H); 2.96 (m, 1H); 2.33 (s, 3H); 1.97 (m. 2H); 1.56 (m, 1H); 1.41 (m, 1H); 0.93 (m, IN); 0.34 (m, 2H); 0.19 (m, 2H).
Example 125: 4-{[4-(2-Cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid ethyl ester
Starting from 4-(2-cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ytamide (example A172) and ethyl chloroformate the title compound is obtained as colorless solid.
MS (ESI): m/z = 478 (MH+, 100 %).
1H-NMR 400 MHz, DMSO-d6): 11.98 (br.s, 1H, -NH); 9.03 (s, 1H); 8.51 (d, J = 7.8, 1H, -NH); 8.24 (s, IN); 7.44 (d, J = 2.1, IN); 7.33 (dd, J, = 8.5, J2= 2.1,1H); 7.06 (d, J = 8.5, 1H); 4.15^.03 (m, 2H); 4.06 (qu, J = 7.1, 2H); 3.89 (m, 2H); 3.87 (d, J = 6.9, 2H); 2.67 (m, IN); 2.33 (s, 3H); 1.96 (m, 2H); 1.48 (m, 2H); 1.20 (t, J = 7.1, 3H); 0.93 (m, 1H); 0.34 (m, 2H); 0,19 (m, 2H).
Example 126: trans-4-{5-Cyclobutylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d|pyrimidine-7-carboxylic acid (4-acetylamjno-cyclohexyl)-amide
Starting from trans-4-(5-cyclobutylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-af]pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide hydrochloride (example A173) and acetyl chloride the title compound is obtained as colorless solid.

MS (ESI); m/z = 506 (MH+).
1H-NMR (400 MHz, DMSO-d6): 12.29 (br.s, 1H, -NH); 9.02 (s, 1H); 8.29 (d, J = 7.8, 1H, -NH); 8.24 (s, 1H); 7.73 (d, J = 7.7, 1H, -NH); 7.01 (d, J = 8.6, 1H); 6.59 (d, J = 8.6, 1H); 6.01 (s, 2H); 3.84 (d, J ^ 6.3, 2H); 3.80 (m, 1H);3.58(m, 1H);2.38(m, 1H);2.01 (m, 2H); 1.86 (m, 2H); 1.79{s,3H); 1.68 (m, 3H); 1.53 (m, 3H); 1.36 (m, 4H).
Example 127: trans-4-(5-Cyclobutylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxy!ic acid [4-(cyclopropanecarbonyl-amino)-cyclohexyl]-amide Starting from trans-4-{5-cyclobutylmethoxy-benzo[1,3]dioxol-4-y!)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4-amino-cyclohexyl)-amide hydrochloride (example A173) and cyclopropanecarbonyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z =532 (MM').
1H-NMR (400 MHz, DMSO-d6): 12,29 (br.s, 1H. -NH); 9.02 (s, 1H); 8.29 (d, J = 7.8, 1H, -NH); 8.24 (s, 1H); 7.94 (d, J = 7.7, 1H. -NH); 7.01 (d. J = 8.6. 1H); 6.59 (d. J = 3.6, 1H}: 6.91 (s, 2H}; 3.84 (d. J = 6.2, 2H); 3.80 {m, 1H); 3.60 {m, 1H); 2.39 (m, 1H); 2.02 (m, 2H); 1.88 (m, 2H); 1.69 (m, 3H); 1.51 (m, 4H); 1.39 (nn, 4H); 0.63 {m, 4H).
Example 128: trans-4-(5-Cyclobutylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c(]pyrimidine-7-carboxylic acid [4-(2-m6thoxy-ethanoylamino)-cyclohexyl]-amide Starting frorr trans-4-{5-cyclobutylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-cOpyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide hydrochloride (example A173) and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 536 (MH+).
1H-NMR (400 MHz, DMSO-d6): 12.28 (br.s, 1H, -NH); 9.01 (s, 1H); 8.28 (d, J = 7.8, 1H, -NH); 8.24 {s, 1H); 7.56 (d, J = 8.2, 1H, -NH); 7.01 (d, J = 8.6, 1H); 6.59 (d, J = 8.6, 1H); 6.00 (s, 2H); 3.84 (d, J = 6.2, 2H); 3.78 (s, 2H & m, 1H); 3.70 (m, 1H); 3.31 (s, 3H); 2.38 (m, 1H); 2.01 (m, 2H); 1.82 (m, 2H); 1.68 (m, 3H); 1-50 (m, 3H); 1.44 (m, 4H).
Example 129: 4-{5-Cyclobutylmethaxy-benzo[1,3]dioxo-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-acetyl-piperidin-4-yl)-amide
Starting from 4-(5-cyclobutytmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrJmidlne-7-carboxylic acid piperidin-4-ylamide hydrochloride (example A174) and acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 492 (MH').
1H-NMR (400 MHz, DMSO-d6): 12.31 (br.s, 1H, -NH); 9,01 (s, 1H); 8.43 (d, J = 7.7, 1H, -NH); 8.27 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.59 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.20 (m, 1H); 4.12 (m, 1H); 3.85 (d, J = 6.2,2H);3.79(m, 1H);3.28(m, 1H);2.90(m, 1H);2.37(m, 1H); 2,03 (s, 3H); 1.96 (m,2H); 1.68 (m,3H); 1.59-1.34 (m, 5H).

Example 130: 4-(5-Cyclobutylmelhoxy-benzo[1,3]dioxo|-4-y|).5H-pyrrolo[3,2-cGpyrinntdine-7-carboxylic acid [1-{1-cyclopropyl-nnethanoyl)-piperidin-4-yl]-amide Starting from 4-(5-cyclobutylmethoxy-benzo[1,3]dioxo-4-yl)-5H-pyrrolQ[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide hydrochloride (example A174) and cyclopropanecarbonyl chloride the title compound is obtained as colorless solid. MS(ESI):m/z = 518(MH+).
'H>NMR{40Q MHZ, DMSO-d6): 12.31 (br.s, 1H, -NH); 9.01 (s, 1H); 8.45 {d, J = 7.8, 1H, -NH); 8.27 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.59 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.27-4.10 (m, 3H); 3.85 (d, J = 6.3, 2H);3.38(m, 1H); 2.95 (m, 1H); 2.37 (m, 1H); 2.09-1.90 (m, 3H); 1.69 (m,3H); 1,59-1.36 (m, 5H); 0.72 (m, 4H).
Example 131; 4-(5-Cyclobutylmethoxy-benzG[1.3jdioxoi-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic CID [1-(2-methoxy-ethanoyl)-piperidine-4-yl]-amide
Starting from 4-(5-cyclobutylmethoxy-benzo[1,3]dioxol-4-yl}-5H-pyrrolo[3,2-cOpyrimidine-7~ carboxylic acid piperidin-4-ylamide hydrochloride (example A174) and methoxy-acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 522 (MH+).
1H-NMR (400 MHz, DMSO-d6): 12.31 (br.s, IN, -NH); 9.01 (s, IN); 8.43 (d, J = 7.8, 1H, -NH); 8.27 (S, 1H); 7.01 (d, J = 8.6, 1H); 6.59 (d, J = 8.6, 1H); 6.00 (s, 2H); 4,24-4.08 (m, 2H); 4.11 (d, J ^^ 4.5, 2H);3.85(d,J = 6.2,2H);3.76(m, IN); 3.31 (s, 3H); 3.21 (m, 1H);2.93(m, 1H);2.37(m, IN); 1.98 (m, 1H); 1.68 (m,3H); 1.58-1.37 (m, 5H).
Example 132; 4-{{1-[4-(5-Cyclobutylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c(]pyrimidin-7-yl]-methanoyl}-amino)-piperidine-1-carboxylic acid ethyl ester Starting from 4-(5-cyclobutylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid p)peridin-4-ylamide hydrochloride (example A174)and ethyl chloroformate the title compound is obtained as colorless solid. MS (ESI): m/z = 522 (MH+).
1H-NMR (400 MHz, DMSO-d6): 12.31 (br.s, 1H, -NH); 9.01 (s, 1H); 8.42 (d, J = 7.8,1H, -NH); 8.26 (s, 1H); 7.01 (d, J = 8.6,1H); 6.59 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.06 (qu, J = 7.1, 2H & m, 1H); 3.90 (m, 2H); 3.83 (d, J = 6.2, 2H); 3.09 (m, 2H); 2.38 (m, 1H); 1.95 (m, 2H); 1.69 (m, 3H); 1.58-1.43 (m,5H); 1.21 (t, J = 7.1, 3H).
Example 133: 4-(5-Ethoxy-benzo[1,3]dioxol-4-yl)-5H-pyi'ro!o[3,2-d]pyrimidine-7-carboxylic acid (1-propionyl-piperidin-4-yl)-amide

starting from 4-{5-ethaxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-cr]pyrimidlne-7-carboxylic acid
plperidin-4-ylamide (example A175) and propionyl chloride the title compound was obtained as
colorless solid.
MS (ESI): m/z = 466 (MH+, 100 %).
1H-NMR (400 MHz, DMSO-d6): 12.25 (s, 1H, -NH); 9.02 (s. 1H); 8.44 (d, J = 7.8, 1H, -NH); 8.29 (s,
1H); 7.02 (d, J = 8.6, 1H); 6.58 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.23 (m, 1H); 4.12 (m, 1H); 3.95 (qu, J
= 7.0, 2H); 3.72 (m, 1H); 3.23 (m, 1H); 2.92 (m, 1H); 2.36 (qu, J = 7.3, 2H); 1.95 (m, 2H); 1.60-1.31
(m, 2H); 1.03 (t, J = 7.0, 3H); 1.01 (t, J = 7.3, m. 3H).
Example 134: 4-{[4-(5-Ethoxy-benzo(1,3]dioxol-4-yl)-5/T'-pyrrolo[3,2-cqpyrimidine-7-carbonyl]-amino}-piperidine-1-carboxylic acid ethyl ester
Starting from 4-(5-ethoxy-benzo[1,3]dioxoM-yl)-5H-pyrrolof3.2-c(lpyrJmidine-7-carboxylic acid piperidin-4-ylamide (example A175) and ethyl chloroformate the title compound was obtained as colorless solid.
MS (ESI): m/z = 482 (MH\ 100 %).
1H-NMR (400 MHz, DMSO-d^): 12.28 (s, 1H, -NH); 9.02 (s, 1H); 8.44 (d, J = 7.8, 1H, -WH); 8.29 (s, 1H); 7.02 (d, J = 8.6, 1H); 6.58 (d, J = 8.6. 1H); 6.00 (s, 2H); 4.06 (qu, J = 7.1, 2H & m, 1H); 3.95 (qu, J = 6.9, 2H & m, 2H); 3.09 (m, 2H); 1,95 (m, 2H); 1.48 (m, 2H}; 1.20 (t, J = 7.1, 3H); 1.03 (t, J = 6.9, 3H).
Example 135: 4-{5-EthQxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-methoxy-acetyl)-piperidin-4-yl]-amide
Starting from 4-(5-ethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide (example A175) and methoxy-acetyl chloride the title compound was obtained as colorless solid. MS (ESI): m/z = 482 (MH\ 100 %).
1H-NMR (400 MHz, DMSO-d6): 11.99 (s, 1H, -NH); 9.02 (s, 1H); 8.45 (d. J = 7.8, 1H, -NH); 8.30 (s, IN); 7.02 (d, J = 8.6, 1H); 6.58 (d, J - 8.6, 1H); 6.00 (s, 2H); 4.17 (m, 2H); 4.12 (d, J = 2.6, 2H); 3.95 (qu, J = 6.9, 2H); 3.76 (m, 1H); 3.31 (s, 3H); 3,22 (m, 1H); 2.95 (m, 1H); 1.98 (m, 2H); 1.63-1.37 (m,2H); 1.03 (t, J = 6.9, 3H).
Example 136: 4-(5-Ethoxy-benzoI1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid((R)-1-propionyl-pyrroljdin-3-yl)-amide
Starting from 4-(5-ethoxy-benzo[1,3]dioxo-4-yl)-5H-pyrrolo(3,2-d]pyrimidine-7-carboxylic acid (R)-pyrrolidin-3-yl)amide (example A176) af7d propionyl chloride the title compound was obtained as colorless solid. MS (ESI): m/z = 452 (MH+, 100 %).

1H-NMR (300 MHz, DMSO-d6): 12.19 (s, 1H, -NH); 9.02 (s, 1H); 8.58 (d, J = 7.2. 0.5H, -NH); 8.55 (d, J =6.9, 0.5H, -NH); 8.32 {s, 1H); 7.02 (d, J = 8.6, 1H); 6.58 (d, J = 8.6, 1H); 6.01 (s, 2H); 4.61 (m, 0.5H); 4.51 (m, 0.5H); 3.96 (qu, J = 6.9, 2H); 3.82 (m, 0.5H); 3.71-3.32 (m, 3.5H); 2.36-2.16 (m, 3H); 2.07 (m, 0.5H); 1.94 (m, 0.5H); 1.03 (m, 6H).
Example 137: (R)-3-{l4-(5-Ethoxy-benzo[1,31dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-pyrrolidme-1-carboxylic acid ethyl ester
Starting from 4-(5-ethioxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3.2-d]pyrimidine-7-carlxDxylic acid (R)-pyrrolidin-3-ylamide (example A176) and ethyl chloroformate the title compound was obtained as colorless solid.
MS (ESI); m/z = 468 (MH', 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.26 (s. 1H, -NH); 9.02 (s, 1H); 8.56 (d, J = 7.0, 1H, -NH); 8.31 (s, 1H); 7.02 (d, J = 8.6, IN); 6.58 (d, J = 8.6, 1H); 6.01 (s, 2H); 4.53 (m, IN); 4.05 (qu, J = 7.0, 2H); 3.95 (qu, J = 6.9,2H); 3.67 (m, W); 3.46 {m. 2Hy, 3.31 (ni, 1H); 2.23 [m, \H); 1.9& (m, 1H); 1.19 (t, J = 7.0, 3H); 1.03(t,J = 6.9, 3H).
Example 138: 4-(5-Ethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3.2-c(|pyrlmidine-7-carboxylic acid [(R)-1-(2-methoxy-acstyl)-pyrrolidin-amide
Starting from 4-(5-ettiQxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (R)-pyrrolidin-3-ylamide (example A176) and methoxy-acetyl chloride the title compound was obtained as colorless solid. MS (ESI): m/z = 468 (MH', 100 %).
'1H-NMR (300 MHz, DMSO-d6): 11.89 (s, 1H, -NH); 9.02 (s, 1H); 8.57 (d, J = 6.7, 0.5H, -NH); 8.54 (d, J =6.3, 0.5H); 8.31 (s, 1H); 7.02 (d, J = 8.6, IN); 6.58 (d, J = 8.6, IN); 6.00 (s, 2H); 4.61 (m, 0.5H); 4.51 (m, 0,5H); 4.08 (d, J = 3.8, IN); 4.01 (d, J = 1.4, 2H); 3.97 (qu, J = 6.9, 2H); 3.80 (m, 0.5H); 3.70 (m, 0.5H); 3.62-3.33 (m, 3H); 3.32 (s, 1.5H); 3.30 (s, 1.5H); 2.32-2.14 (m, 1H); 2.07 (m, 0.5H}; 1.92 (m, 0.5H); 1.03 (t, J = 6,9, 3H).
Example 139: 4-(5-Propoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-propionyl-piperidin-4-yl)-amide
Starting from 4-(5-propoxy-benzoI1,3]dioxol-4-yl)-5H-pyrrolo(3,2-c/]pyrimtdine-7-carboxylic acid piperidin-4-ylamide (example A177) and propionyl chloride the title compound was obtained as colorless solid.
MS (ESI): m/z = 480 (MH+, 100 %),
1H-NMR (300 MHz, DMSO-d6): 12.28 (s, 1H, -NH); 9.02 (s, 1H); 8,44 (d, J = 7,7, 1H, -NH); 8.28 (s. 1H); 7.01 (d, J = 8.6, 1H); 6.58 (d, J = 8.6, 1H); 6,00 (s, 2H); 4.24 (m, 1H); 4.14 (m, 1H); 3.85 (t, J = 6.3, 2H&m, 1H);3.24(m, 1H); 2.92 (m, 1H); 2.36(qu, J = 7.4, 2H); 1.97 (m,2H); 1.53 (m, 1H); 1.42 (m, 2H & m, 1H); 1.01 (t, J = 7.4, 3H); 0.63 (t, J = 7.4, 3H).

Example 140: 4-{[4-(5-Propoxy-benzo[1,3]dioxoi-4-yl)-5H-pyrrolo[3,2-d]py^imidine-7-carlx)nyi]-amino}-piperidi^e-1-carboxylic acid ethyl ester
Starting from 4-{5-propoxy-benzo[1,3]dioxol-4-yl}-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide (example A177) and ethyl chloroformate the title compound was obtained as colorless solid.
MS (ESI): m/z = 496 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.31 (s, 1H, -NH); 9.02 (s, 1H); 8.43 (d, J = 7.8, 1H, -NH); 8.27 (s. 1H); 7.02 (d, J = 8.6, 1H); 6.58 (d, J = 8.6, 1H); 6.00 (s, 2H): 4.47 (m, 1H); 4.06 (qu, J = 7.0, 2H & m, 1H}; 3.91 (m, 2H); 3.85 (t, J = 6.4, 2H); 3.09 (m, 2H); 1.95 {m, 2H); 1.49 (m, 2H); 1.42 (m, 2H); 1.20 (t, J = 7.0, 3H); 0.63 (t, J = 7.4, 3H}.
Example 141: 4-(5-Propoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2'C(]pyrimidine-7-carboxylic acid ((R)-1 -propionyl-pyrrolidin-3-yl)-amide
Starting from 4-(5-propoxy-benzo[1,3]dioxol-4-y!)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (R)-pyrrolidin-3-ylamide (example A178) and propionyl chloride the title compound was obtained as colorless solid.
MS (ESI): m/z = 466 (MH', 100 %),
1H-NMR (300 MHz, DMSO-d6): 12.25 (s, 1H. -NH); 9.02 (s, 1H); 8.57 (d, J = 7.2, 0.5H, -NH); 8.54 (d, J = 6.9, 0.5H, -NH); 8.30 (s, IN); 7,02 (d, J = 8,6, 1H); 6.58 (d, J = 8.6, 1H); 6.01 (s, 2H); 4.61 (m, 0.5H); 4.51 (m, 0.5H); 3.86 (t, J = 6.4, 2H); 3.71-3.32 (m, 4H); 2.37-2.15 (m, 3H); 2.07 (m, 0.5H); 1.94 (m, 0.5H); 1.41 (m, 2H); 1.00 (m, 3H); 0.62 (t, J = 7.4, 3H).
Example 142: (R>-3-{(4-(5-Propoxy-benzo[1,3]dioxot-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-pyrrolidine-1-carboxylic acid ethyl ester
Starting from 4-(5-propoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (R)-pyrrolidin-3-ylamide (example A178) and ethyl chloroformate the title compound was obtained as colorless solid.
MS (ESI): m/z = 482 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.32 (s, 1H, -NH); 9.02 (s, 1H); 8.55 (d, J ^ 7.8. IN, -NH); 8.30 (s, 1H); 7.02 (d, J = 8.6, IN); 6.58 (d, J = 8.6,1H); 6.01 (s, 2H); 4.52 (m, 1H); 4.05 (qu, J = 7.0, 2H); 3.84(t, J = 6.4, 2H);3.67(m, 1H);3.47(m, 2H); 3.30 (m, IN); 2.23 (m, IN); 2.00 (m, 1H); 1.41 (m, 2H); 1.19 (t, J = 7.0, 3H); 0.62 (t, J = 7.4, 3H).
Example 143; 4-(5-Propoxy-benzo[1,3]dioxol-4-yl)-5/V-pyrralo[3,2-cOpyrimidJne-7-carboxylic acid [(R)-1-(2-methoxy-acetyl)-pyrrolidin-3-yl]-amide

starting from 4-(5-propoxy-benzo[1,3]dioxoi-4-yl)-5H-pyrrolo[3,2-c(Ipyrimidine-7-carboxylic acid (R)-
pyrrolidin-3-ylamide (example A178) and methoxy-acetyl chloride the title compound was obtained
as colorless solid.
MS (ESI): m/z = 482 {MH\ 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.15 (s, 1H, -NH); 9,02 (s, 0.5H); 9.01 (s, 0.5H); 8.57 (d, J = 6.8,
0.5H, -NH); 8.54 (d, J = 6.3, 0.5H, -NH); 8.30 (s, 1H); 7.02 (d, J = 8.6, 1H); 6.58 (d, J = 8.6, 1H);
6.00 (s, 2H); 4.61 (m, 0.5H); 4.52 (m, 0.5H); 4.07 (d. J = 4.0, 1H); 4.01 (d, J = 1.5. 1H); 3.85 (t, J =
6.4, 2H); 3.80 (m, 0.5H); 3.70 (m, 0.5H); 3.62-3.34 (m, 3H); 3.32 (s, 1.5H); 3.30 (s, 1.5H); 2.34-2.15
(m, 1H); 2.07 (m, 0.5H); 1.92 (nn, 0.5H); 1.41 (m, 2H); 0.62 (t, J = 7.4, 3H)-
Example 144: 4-(5-Butoxy-benzo[1,3]dioxol-4-yl)-5f/-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-propionyl-piperidin-4-yi)-amide
Starting from 4-(5-butoxy-benzo[l,3]dioxol-4-yl)-5H-pyrroio[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-yJamide (example A179) and propionyl chloride the title compound was obtained as colorless solid.
MS (ESI); m/z = 494 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.29 (s, IN, -NH); 9.01 (s, 1H); 8.43 (d, J = 7.8, IN, -NH); 8.28 (s, 1H); 7.01 (d, J = 8.S, 1H); 6.58 (d, J - 8.6, 1H); 6.00 (s, 2H); 4.24 (m, 1H); 4.14 (m, 1H); 3.88 (t, J = 6.4, 2H); 3.86 (m, 1H); 3.24 (m, 1H); 2.92 (m, 1H); 2,36 (qu, J = 7.4, 2H); 1.97 (m, 2H); 1.53 (m, IN); 1.42 (m, 2H & m, 1H); 1.07 (m, 2H); 1.01 (t, J = 7.4, 3H); 0.69 (t, J = 7.4, 3H).
Example 145: 4-{[4-(5-Butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-piperidine-1-cartx3xylic acid ethyl ester
Starting from 4-(5-butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide (example A179) and ethyl chloroformate the title compound was obtained as colorless solid.
MS (ESI): m/z = 510 (MH', 100 %).
1H-NMR (300 MHz, DMSO-d6): 12,31 (s, 1H, -NH); 9.02 (s, 1H); 8.43 (d, J = 7.7, 1H, -NH); 8.28 (s, 1H): 7.02 (d, J = 8.6, 1H); 6.58 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.06 (qu, J = 7.0, 2H & m, 1H); 3.90 (t, J = 6.4, 2H & m, 2H); 3.09 (m, 2H); 1.95 (m, 2H); 1.48 (m. 1H); 1.36 (m, 2H); 1.20 (t, J = 7.0, 3H); 1.05(m, 2H);0.69(t, J = 7.4, 3H).
Example 146; 4-{5-Butoxy-ben20[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyllc acid (1-fonnyl-piperidin-4-yl)-amide
Starting from 4-(5-butoxy-benzo[1,3]dioxol-4-yl)-5/V-pyrrolol3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide (example A179) and acetic formic anhydride the title compound was obtained as colorless solid. MS (ESI): m/z = 466 (MH+, 100 %).

1H-NMR (300 MHz, DMSO-d6): 12.25 (s, 1H, -NH); 9.02 (s. 1H); 8.44 (d. J = 7.8, 1H): 8.29 (s, 1H); 8.03 (s, 1H); 7.01 (d. J- 8.6, 1H); 6.58 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.17 (m, 1H); 4.10 (m, 1H); 3.88 (t, J - 6.4, 2H); 3.53 (m, 1H); 3.26 (m, 1H); 2,95 (m, 1H); 2.00 (m, 1H); 1.52 (m, 1H); 1.39 (m, 2H & m, 1H); 1.05 (m, 2H); 0,69 (t, J = 7.4, 3H).
Example 147: 4-(5-Bu[oxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-tyipyrimidine-7-carboxylic acid (1-propionyl-piperidin-3-yl)-amide
Starting from 4-(5-butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c/lpyrinnidine-7-carboxylic acid piperldin-3-ylannide (example A180) and propionyl chloride the title compound was obtained as colorless solid.
MS(ESI):m/z=494(MH+, 100%),
1H-NMR (300 MHz, DMSO-dj): 12,31 (s, 1H, -NH); 8,98 (s, 1H); 8.56 (d, J = 7.3, 0.5H, -NH); 8.51 (d, J = 7.9, 0.5H, -NH); 8.29 (s, 0,5H); 8.28 (s. 0.5H); 7.01 (d, J = 8.6, 1H); 6,59 (d, J = 8.6, 1H); 6.01 (s, 2H); 4,08-3.93 (m, 1,5H); 3.88 (t, J = 6,4, 2H); 3.75 (m. 0,5H); 3.54 (m, 1H); 3.50-3,35 (m, 1.5H); 3,30 (m, 0,5H); 2.37 (m, 1H); 2.30 (m, 1H); 1.97 (m, 1H); 1.74 (m, 2H); 1.56 (m, 1H); 1.39 (m, 2H): 0.99 (m, 2H S m, 3H); 0.68 (t, J = 7.4. 3H).
Example 148: 3-{[4-(5-Butoxy-benzo[1,3]dioxol-4-yl)-5f/-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-piperidin&-1-carboxylic acid ethyl ester
Starting from 4-(5-butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid pipertdin-3-ylamide (example A180) and ethyl chloroformate the title compound was obtained as colorless solid.
MS (ESI): m/z = 510 (MH+, 100 %),
1H-NMR (300 MHz, DMSO-d6): 12.31 (s, 1H, -NH); 8.99 (s, 1H); 8.53 (d, J = 7.9, 1H, -NH); 8.28 (s, IN); 7.01 (d, J = 8.6, 1H); 6,59 (d, J = 8.6, IN); 6.01 (s, 2H); 4.01-3.92 (m, 3H); 3.88 (t, J = 6.4, 2H); 3.75 (m, 1H); 3,48 (m, 1H); 3,32 (m, 2H); 1.94 (m, 1H); 1.73 (m, 2H); 1.56 (m, 1H); 1.39 (m, 2H); 1.05 (m, 2H & m, 3H); 0.69 (t, J = 7.4, 3H).
Example 149: 4-(5-Butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1 -(2-methoxy-acetyl)-piperidin-3-yl]-amide
Starting from 4-(5-butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-dlpyrimldine-7-carboxylic acid piperidin-3-ylamide (example A180) and methoxy-acetyl chloride the title compound was obtained as colorless solid. MS (ESI): m/z = 510 (MH\ 100 %).
1H-NMR (300 MHz, DMSO-d6); 12.28 (s, 1H, -NH); 8.98 (s, 1H); 8.55 (br.s, 1H, -NH); 8.29 (s, 0.5H); 8.27 (s, 0.5H); 7.01 (d, J = 8.6, 1H); 6.59 (d, J = 8,6, 1H); 6.01 (s, 2H); 4.12-3.97 (m, 3H); 3.88 (t, J = 6.4, 2H & m, 0.5H); 3.68 (m, 0.5H); 3,49 (m, 1H); 3.31 (m, 2H); 3,28 (s, 1.5H); 3.16 (s, 1.5H); 1.97 (m, 1H); 1.76 (m, 2H); 1,57 (m, 1H); 1.39 (m, 2H); 1.05 (m. 2H); 0.69 (t, J = 7,4, 3H).

Example 150: 4-(5-Butoxy-benzo[l ,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carixJxylic acid ((R)-1-propionyl-pyrrolidin-3-yl)-amide
Starting from 4-(5-butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2- MS (ESI): m/z = 480 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 12,29 (br,5,1H, -NH); 9,01 (s, 1H); 8.57 (d, J = 7,1, 1H, -NH); 8.54 (d, J = 7.1, 0.5H, -NH): 8,30 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.59 (d, J = 8.6, 1H); 6.00 (s, 2H): 4.61 (m. 0.5H); 4.50 (m, 0.5H): 3.89 (t, J = 6.4, 2H); 3.82 (m, 0.5H); 3.66 (m, 0.5H); 3,63-3.31 (m, 3H); 2.35-2.17 (m, 3H); 2.07 {m, 0.5H); 1.94 (m, 0.5H); 1.40 (m, 2H); 1.10-0,98 (m, 4H); 0.69 (t, J = 7.4, 3H).
Example 151; (R)-3-{[4-(5-Buloxv-benzol1,3]dioxol-4-yl)-5H-pyrro!o[3,2-d]pyrimidine-7-carbonyl]-amino}-pyrrolldine-1-carboxylic acid ethyl ester
Starting from 4-(5-butoxy-benzo[1,3]dioxo|.4-yl)-5J4-pyrrolo[3,2-d]pyrimldine-7-carboxylic acid (R)-pyrro(idln-3-ylamide (example A181) and ethyl chloroformate the title compound was obtained as colorless solid,
MS (ESI): m/z = 496 (MH', 100 %),
1H-NMR 300 MHz, DMSO-d6): 12.32 (br.s, 1H, -NH); 9.02 (s, 1H); 8,56 (d, J = 6.7, 1H, -NH); 8.30 (s, 1H); 7.02 (d, J = 8.6. 1H); 6,59 (d, J = 8.6, 1H); 6.01 (s, 2H); 4.53 (m, IN); 4.05 (qu, j = 7.0, 2H); 3,88 (t, J = 6.4. 2H); 3.67 (m, 1H); 3.48 (m, 2H); 3.30 (m, 1H); 2,22 (m, 1H); 1.99 (m, 1H); 139 (m. 2H); 1,19 (t, J = 7,0, 2H); 1.05 (m, 2H); 0.69 (t, J = 7.4, 3H).
Example 152: cis-4-[4-Methoxy-2^(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimldine-7-carboxylic acid (4-acetylamino-cyclohexy|)-amide
Starting from cis-4-[4-methoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-c(]pyrimldine-7-
carboxylic acid (4-amino-cyclohexyl)-amide (example A183) and acetyl chloride the title compound
was obtained as colorless solid.
MS (ESI): m/z = 482 (MH+).
1H-NMR (400 MHz, DMSO-d6): 11.75 (br.s, m, -NH): 903 (s, 1H); 8.65 (d, J = 7,6, 1H -NH); 8.23 (d, J = 3.2, IN); 7.86 (d, J - 7,6, IN, -NH); 7.70 (d, J = 8.3, 1H); 6,77 (s, 1H); 6.76 (dd, j, = 8.3, Jj = 2.2, 1H); 4,24 (t, J = 4.6, 2H); 4.03 (m, 1H); 3.88 (s, 3H); 3,76 (m, 1H); 3.55 (t, J = 4,6, 2H); 3.13 (s, 3H); 1.83 (s. 3H); 1.80-1.63 (m, 6H); 1.60 (s, 2H).
Example 153: cis-4-[4-Methoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyJ1c acid [4-(cyclopropanecarbony|-amino)-cycIohexyl]-amide

Starting from cls-4-(4-m6thoxy-2-{2-methoxy-ethoxy>phenyl]-5N-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A183) and cyclopropanecarbonyl chloride the title compound was obtained as colorless solid. MS (ESI): m/z = 508 (MH+).
1H-NMR (400 MHz, DMSO-d6): 11.75 (br.s, 1H, -NH); 9.04 (s, 1H): 8.67 (d, J = 7.6, 1H, -NH); 8.23 (s, 1H); 8,07 (d, J = 7.6, 1H, -NH); 7.70 (d, J = 8.3, 1H); 6.77 (s, 1H); 6.76 (dd, J, = 8.3, Jj = 2.2, 1H): 4,24 (t, J = 4.6, 2H); 4.04 (m, 1H); 3.88 {s, 3H): 3.78 (m, 1H); 3.55 (I, J = 4.6, 2H); 3.13 (s, 3H); 1.86-1.54 (m,9H); 0.65 (m,4H).
Example 154: cis-4-[4-Methoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-c/)pyrimidine-7-carboxylic acid [4-(2-methoxy-acetylamino)-cyclohexyl]-amide
Starting from cis-4-[4-methoxy-2-(2-methoxy-Gthoxy)-phanyl]-5H-pyrrolo[3,2~cy]pyrimidine-7-carboxylic acid {4-amino-cyclohexyi)-amide (example A183) and methoxy-acetyt chloride the title compound was obtained as colorless solid. MS (ESI): m/z = 512 (MH+).
1H-NMR (400 MHz, DMSO-d6): 11.74 (br.s, 1H, -NH); 9.03 (s, 1H); 8.61 (d, J = 7.3, 1H, -NH); 8.22 (s, 1H); 7.69 (d, J = 8.2, 1H & d, J = 5.4, 1H, -NH); 6.77 (s, 1H); 6.76 (dd, J, = 8.2, J; = 2.2, 1H); 4.24 (t, J = 4.6, 2H); 4,05 (m, 1H); 3.88 (s, 3H); 3.82 (s, 2H & m, 1H); 3.55 (t, J = 4,6. 2H); 3.29 (s, 3H); 3.13 (s, 3H); 1.79 (m, 2H); 1.77-1.60 (m, 6H).
Example 155: trans-4-[4-Methoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-acetylamino-cyclohexyl)-amide
Starting from trans-4-[4-methoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-tf]pyrimidine-7-carboxylic acid (4-amino-cyclQhexyl)-amide (example A182) and acetyl chloride the title compound was obtained as colorless solid. MS (ESI): m/z = 482 (MH+).
1H-NMR (400 MHz, DMSO-d6): 11.73 (br.s, 1H, -NH); 9.00 (s, 1H); 8.39 (d, J = 7.8, 1H, -NH); 8.22 (d, J = 3.4, 1H); 7.74 (d, J = 7.6, 1H, -NH); 7.69 (d, J - 8.2, 1H); 6.77 (s, IN); 6.76 (dd, J, = 8.2, J2 = 2.2, 1H); 4.24 (t, J = 4.6, 2H); 3.87 (s, 3H); 3.82 (m, 1H); 3.58 (m, 1H); 3.54 (t, J = 4.6, 2H); 3.13 (s, 3H); 2.01 (m, 2H); 1.88 (m, 2H); 1.63 (s, 3H); 1.42 (m, 2H); 1.31 (m, 2H).
Example 156: trans-4-[4-Methoxy-2-(2-methoxy-ethoxy)-phenylj-5H-pyrrolo[3,2-d]pyrimidfne-7-carboxylic acidf4-{cyclopropanecarbonylnam(no)-cyclohexyl]-amide Starting from trans-4-[4-methoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cydohexyl)-amide (example A182) and cyclopropanecarbonyl chloride the title compound was obtained as colorless solid. MS (ESI): m/z = 508 (MH+).

1H-NMR (400 MH2, DMSO-d6): 11.73 (br.s, IN, -NH); 9.00 (s, 1H); 8.40 (d, J = 7.8, 1H, -NH); 8.22 (s, 1H); 7.95 (d, J ^ 7.7, 1H, -NH); 7.69 (d, J = 8.3. 1H); 6.77 (s, 1H); 6.76 {dd, J1 = 8.3, J2 = 2,2, 1H); 4.24 (t, J = 4.6, 2H); 3,87 (s, 3H); 3.82 (m, 1H}; 3.61 (m, 1H); 3.54 (t, J = 4.6, 2H); 3,13 (s, 3H);2.01 (m, 2H); 1,88 (m, 2H): 1.52 (m, 1H); 1.48 (m, 4H); 0.65 (m, 4H),
Example 157; trans-4-[4-Melhoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d] py rim Id i ne-7-carboxy lie acid [4- (2-methoxy-acetylamino)-cyclohexyI] -am id e Starting from lrans4-[4-methoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-dlpyrimidtne'7-carboxylic acid (4-amino-cycloliexyi)-afnide (example A182) and methoxy-acetyl chloride the title compound was obtained as colorless solid, MS(ESI):m/z = 5l2(MH+),
1H-NMR (400 MHz, DMSO-d6): 11.73 (br,s, 1H, -NH); 9.00 (s, IN); 8.39 (d, J = 7.8, 1H, -NH); 8.22 (s, 1H); 7.69 (d, J ^ 8,3, 1H); 7.58 (d, J = 3.2, 1H, -NH); 6.77 (s, 1H); 6.76 (dd, J, = 8.3, Jz - 2.2, 1H); 4.24 (t, J = 4.6. 2H): 3.87 (s, 3H); 3.79 (s, 2H & m, 1H); 3.70 (m, 1H); 3.54 (t, J = 4.6, 2H); 3.31 (s, 3H); 3.13 (s, 3H); 2.01 (m, 2H); 1.81 (m, 2H); 1,44 (m, 4H).
Example 158: 4-[4-IVlethoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-6icetyl-pjperidin-4-yl)-amide
Starting from 4-[4-nnethoxy-2-(2-m8thoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide (example A184) and acetyl chloride the title compound was obtained as colorless solid, MS (ESI); m/z = 468 (MH+).
1H-NMR (400 MHz, DMSO-d6): 11.76 (br.s, 1H, -NH); 9.00 (s, 1H); 8.56 (d, J = 7.8,1H, -NH); 8.25 (s, 1H); 7.69 (d, J = 8,3, 1H); 6.77 (s, 1H); 6.76 (dd, J1 = 8.3, J2 = 2.2,1H); 4.24 (t, J = 4,6, 2H); 4.20-4.09 (m, 3H); 3.87 (s, 3H); 3.79 (m, 1H); 3.54 (t, J = 4.6, 2H); 3.27 (m, 1H); 3,13 (s, 3H); 2.91 (m, 1H); 1.97 (m, 2M); 1.56 (m. 1H); 1.40 (m, 1H).
Example 159: 4-[4.|viethoxy-2-(2-melhoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-G'lpyrlmidme-7-carboxylic acid (1-cyclopropanecarbQnyl-piperidin-4-yl)-amide
Starting from 4-[4-nriethoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylahiide (example A184) and cyclopropanecarbonyl chloride the title compound was obtained as colorless solid. MS (ESI): m/z = 494 (MH').
1H-NMR (400 MHz, DMSO-d6): 11.76 (br.s, 1H, -NH); 9.00 (s, 1H); 8,57 (d, J = 7.7, 1H, -NH); 8.25 (d, J = 3.4, 1H); 7.69 (d, J = 8,2, 1H); 6.77 (s, 1H); 6.76 (dd, J1 = 8.2, J2 = 2.3,1H); 4,24 (t, J = 4.6, 2H); 4.24-4.10 (m, 3H); 3.87 (s. 3H); 3,54 (t, J = 4.6, 2H); 3,39 (m, 1H); 3,13 (s, 3H); 2.97 (m, 1H); 2.09-1.90 (m, 3H); I.53 (m, 1H); 1.42 (m, 1H); 0.73 (m, 4H).

Example 160; 4-[4-Methoxy-?-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo(3,2-c(fpyrimidine-7-carboxylic acid [1-(2-methoxy-acelyl)-piperidin-4-yl]-amide
Starting from 4-[4-methoxy-2-{2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid pipe rid in-4-ylamide (example A184) and methoxy-acetyl chloride the title compound was obtained as colorless solid, MS(ESI):m/z = 498(MH+).
1H-NMR (400 MHz, DMSO-d6): 11-76 (br.s, 1H, -NH); 8.99 (s, 1H); 8.55 (d, J = 7.8, 1H, -NH); 8.25 (s, 1H);7.69{d,J = 8.2, 1H); 6.77 (s, 1H); 6.75 (dd, J, = 8.2, Jj ^ 2.2, 1H); 4.22 (t, J - 4.6, 2H & m, 1H): 4.15 (m, 1H); 4.12 (d, J = 4.3, 2H); 3.87 (s, 3H); 3.75 (m, IN); 3.54 (t, J = 4.6, 2H); 3.31 (s, 3H);3.21 (m, 1H); 3.12 (s, 3H); 2.95 (m, 1H); 1.98 (m,2H); 1 57 (m, 1H); 1.42 (m, 1H).
Example 161: trans-4-[5-(2-Methoxy-ethoxy)-benzo[1,31dioxal-4-yl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-acetylamino-cyclohexyl)-amide
Starting from trans-4-[5-[2-methoxy-ethoxy)-benzo[1,3]dioxol-4-y}]-5H-pyrro)o[3.2-d]pyrimidme-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A185) and acetyl chloride the title compound was obtained as colorless solid. MS (ESI): m/z=496(MH+).
1H-NMR (200 MHz. DMSO-d6): 12.13 (br. s, 1H, -NH); 9.02 (s, 1H); 8.34 (d, J = 7.9, 1H, -NH); 8.26 (s, IN); 7.73 (d, J = 7.7, -NH); 7.02 (d, J = 8.5. 1H); 6.61 (d, J = 8.5, 1H); 6.01 (s, 2H); 4.03 (t, J = 4.7, 2H); 3.83 (m, 1H); 3.56 (m,1H); 3.39 (t, J = 4.7, 2H); 3.02 (s. 3H): 2.04 (m, 2H); 1.83 (m, 2H); 1.77 (s,3H); 1.36 (m,4H).
Example 162: trans-4-[5-(2-M6thoxy-ethoxy>benzo[1,31dioxol-4-yl]-5H-pyrrolo(3,2-c/lpyrimidine-7-carboxylic acid (4-acetylamino-cyclohexyl)-amide
Starting from trans-4-[5-(2-methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A185) and cyclopropanecarbonyl chloride the title compound was obtained as colorless solid. MS(ESI):m/2=522(MH').
1H-NMR (200 MHz, DMSO-d6): 12.20 (br. s, 1H, -NH); 9.02 (s, 1H); 8.34 (d, J = 7,8, IN, -NH); 8.27 (s, 1H); 7.90 (d, J = 7.6, -NH); 7.02 (d. J = 8.6, 1H); 6.61 (d, J = 8.6, 1H); 6.01 (s, 2H); 4.03 (t, J = 4.7, 2H); 3.84 (m, 1H); 3.59 (m,1H); 3.39 (t, J = 4.7, 2H); 3.02 (s, 3H); 2.04 (m, 2H); 1.83 (m, 2H); 1.53 (m, 1H); 1.38 (m, 4H); 0.64 (m, 4H).
Example 163: trans-4-[5-(2-Methoxy-ethoxy)-benzoI1.3]dioxol-4-yl]-5H-pyrrolo[3,2-c(]pyrimidine-7-ca^boxylicacid [4-(2-methoxy-acetylamino)-cyclohexyl]-amide Starting from trans-4-[5-(2-methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyllc acid (4-amino-cyclohexyl)-amide (example A185) and methoxy-acetyl chloride the title compound was obtained as colorless solid.

MS (ESI): m/z = 526 (MHl.
1H-NMR (200 MHz, DMSOOe): 12.15 (br. s, 1H, -NH); 9.02 (s, 1H); 8.33 Example 164: cis-4-[5-(2-Methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3.2-c/lpyrimidine-7-carboxylic acid (4-acetylafnino-cyclohexyl)-amide
Starting from cis-4-[5-{2-methoxy-eHioxy)-benzo[1,3]dioxol-4-yl].5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amlno-cyclohiexyl)-amide (example A186) and acetyl chloride the title compound was obtained as colorless solid. MS (ESI): m/z = 496 (MH+).
1H-NMR (200 MHz. DMSO-d6): 12.10 (br.s, IN, -NH); 9.05 (s, 1H); 8.55 (d, J - 7.6, 1H; -NH); 8.28 (s, W); 7.B5 (d, J = 7.6, 1H, -NH); 7.03 (d, J = 8.6, 1H); 6.62 (d, J=&.6, 1H); 6.02 (s. 2H): 4.04 (t. J = 4.7, 2H); 3.76 (m, 1H); 3.39 (t, J = 4.7, 2H & m, 1H); 3.02 (s, 3H); 1.83 (s, 3H); 1.73 (m. 4H), 1.66 (m,4H).
Example 165: cis-4-[5-(2-Methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-aGetylamino-cyclohexyl)-amide
Starting from cis-4-[5-(2-methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A186) and cyclopropanecarbonyl chloride the title compound was obtained as colorless solid. MS (ESI): m/z = 522 (MH+).
1H-NMR (200 MHz, DMSO-d6): 12.18 (br.s, 1H, -NH); 9.06 (s, 1H); 8.57 (d, J = 7.6, 1H; -NH); 8.29 (s, IN); 8.06 (d, J - 7.6, 1H, -NH); 7.03 (d, J = 8.6, IN); 6.62 (d, J = 8.6, IN); 602 (s, 2H); 4.04 (t, J = 4.7, 2H); 3.76 (m. 1H); 3.79 (m, 1H); 340 (t, J = 4.7, 2H); 3.03 (s, 3H); 1.75 (m. 4H), 1.66 (m, 5H);0.65(m,4H).
Example 166: cis-4-[5-(2-Methoxy-ethoxy)-benzo[1,3]dioxot-4-yl]-5/-iLpyrrolo[3,2-c(]pyrimidine-7-carboxylic acid [4-(2-methoxy-acetylamino)-cyclohexyl]-amide Starting from ci&4-[5-(2-methoxy-ethoxy>-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d]pyrimldine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A186) and methoxy-acetyl chloride the title compound was obtained as colorless solid. MS (ESI): m/z = 526 (MH').
1H-NMR (200 MHz, DMSO-d6): 12.13 (br.s, 1H, -NH); 9.05 (s, IN); 8.58 (d, J = 7.4, 1H; -NH); 8.28 (s, 1H); 7.69 (d, J = 7.6, 1H, -NH); 7.03 (d, J = 8.6, 1H); 6.62 (d. J = 8.6. 1H); 6.02 (s, 2H); 4.04 (t. J = 4.7, 2H & m, 1H); 3.82 (s, 2H & m, 1H); 3.39 (t, J = 4.7, 2H); 3.31 (s, 3H); 3.03 (s, 3H); 1.73 (m. 8H).

Example 167: cis-[4-({4-[5-(2-Methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2- Starting from cis-4'[5-(2-methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo(3,2-c/]pyrimidine-7-carboxylic acid (4-amirtG-cyctohexyl)-amide (example A186) and ethyl chloroformate the title compound was obtained as colorless solid. MS (ESi): m/z = 526 (MH+).
1H-NMR (200 MHz, DMSO-d6): 12.20 (br.s, 1H, -NH); 9.05 (s, 1H); 8.59 (d, J = 7.8, IN; -NH); 8.27 (s, 1H); 7.19 (d, J = 7.6, 1H, -NH); 7.03 (d, J = 8.6, 1H); 6.62 (d, J = 8.6, 1H); 6.02 (s, 2H); 4.04 (t, J = 4.7, 2H&m, 1H);3.99(qu,J = 7.1, 2H); 3.50 (m, 1H); 3.39 (t, J =4.7, 2H); 3,03 (s, 3H); 1.67 (m. 8H); 1.17(t, J = 7.1,3H).
Example 168; 4-[5-(2-Methoxy-e;hoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-cflpyr!midine-7-cart)Oxylic acid (l-acetyl-pipefttiin-4-yl)-amide
Starting from 4-[5-(2-methoxy-ethoxy)-ben2o[1,3jdioxol-4-yl]-5H-pyrrolo[3,2-cf|pyrimidine-7-carboxytic acid piperidin-4-ylamide (example A187) and acetyl chloride the title compound was obtained as colorless sofid. MS (ESI); m/z = 482 (MH+).
1H-NMR (200 MHz, DMSO-d6): 12.17 (br.s, 1H, -NH); 9.02 (s, IN); 8.45 (d, J = 7.8,1H; -NH); 8.30 (s, 1H); 7.02 (d, J = 8.6. IN); 6.61 (d, J = 8.6, 1H); 6.01 (s, 2H); 4.17 (m, 2H); 4.03 (t, J = 4.7, 2H); 3.80 (m, 1H);3.39 (t, J = 4.7, 2H); 3.27 (m, 1H); 3.03 (s, 3H); 2.93 (m, 1H); 2.05 (s, 3H); 1.97 (m, 2H);1.47(m, 2H).
Example 169: 4-[5-(2-Methoxy-ethoxy)-benzol1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-cyclopropanecarbonyl-piperidin-4-yl)-amide
Starting from 4-[5-(2-methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide (example A187) and cyclopropanecarbonyl chloride the title compound was obtained as colorless solid. MS (ESI); m/z = 508 (MH+).
1H-NMR (200 MHz, DMS0-d6): 12.16 (br.s, 1H, -NH); 9.02 (s, 1H); 8.46 (d, J = 7.8, IN; -NH); 8.30 (s, 1H); 7.02 (d. J = 8.6, 1H); 6.61 (d, J = 8,6, 1H); 601 (s, 2H); 4.20(m, 3H); 4.03 (t, J = 4.7, 2H); 3.39 (t, J = 4.7, 2H & m, 1H); 3.02 (s, 3H & m, 2H); 2.00 (m, 3H); 1.49 (m, 2H); 0.73 (m, 4H).
Example 170: 4-[5-(2-Methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolD[3,2-d]pyfimJdine-7-carboxylic acid [1-(2-methoxy-acetyl)-piperidin-4-yl)-amide
Starting from 4-[5-(2-methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2'af]pyrimidine-7-carboxylic add piperidin-4-ylamide (example A187) and methoxy-acetyl chloride the title compound was obtained as colorless solid.

IVlS(ESI):m/z=512{MH+),
1H-NMR (200 MHz, DMSO-d6): 12,18 (br.s, 1H, -NH); 9.02 {s, 1H); 8,44 (d, J = 7.8, 1H; -NH); 8.30 (s, 1H);7.02{d, J = 8.6, 1H); 6.61 (d, J = 8.6, 1H);6.01 (s, 2H); 4.12 (m, 2H &s, 2H); 4.03 {t, J = 4.7, 2H); 3.73 (m, 1H); 3.38 (t. J = 4.7, 2H); 3.31 (s, 1H); 3.28 (m, 1H); 3.02 (s, 3H); 2.95 {m, 1H); 1.98 (m, 2H); 1.52 (m,2H).
Example 171: 4-(5-Gyclopropylmethoxy-benzo[1,3]dioxol-4-yl>5H-pyrrolo[3,2-d]pyrirnldine-7-carboxylic acid (1-(2'hydrQxy-ethanoyl)-piperldin-4-yl]-amide
4-(5-Cyclopropylmethoxy-1,3-benzodioxol-4-y!)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyllcacid piperidin-4-ylamide hydrochloride from example A138 (472 mg; 1.0 mmol) is dissolved in dry dichloromethane (5 mL) and DBU (2.5 mmol). Acetic acid chlorocarbonylmethyl ester (1,1 mmol) is dropped into (he reaction mixture at ice bath temperature. After complete addition stirring is continued at ambient temperature overnight. Methanol (1 mL) is added and stirring is continued for two hours. The volatiles are evaporated.
The residue is dissolved in methanol (5 mL), treated with 5M KOH (1.5 mmol) and stirred overnight at ambient temperature. The pH of the reaction mixture is adjusted to 6-7 by addition of 2M citric acid. The volatiles are evaporated. The residue is purified by reversed phase preparative HPLC. The coiiected product fraction is freeze-dried to yield 364 mg of the title compound as colorless solid.
MS (ESI): m/z = 494 (MH+, 100%).
1H-NMR (400 MHz, DMSOnde): 9.02 (s. 1H); 8.45 (d, J = 7.8, 1H, -NH); 8.30 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, IN); 6,01 (s, 2H); 4.52 (br.s, 1H, -OH); 4,16 (m, 2H & d, J = 7.9, 2H); 3.76 (d, J = 6.8, 2H); 3.69 (m, IN); 3.19 (m, 1H);2.98(m, 1H); 1.98 (m,2H); 1.56 (m, 1H); 1.43 (m, 1H); 0.87 (m, IN); 0.29 (m, 2H); 0,10 (m, 2H).
The following compounds are obtained analogously to the procedure described in above example 171.
Example 172: trans-[4-({1-[4-(5-Cyclopropylmethoxy-benzo[1,3Jdioxol-4-yi)-5H-pyrrolo[3,2-c/] py rim id i ne-7-carboxyIic acid [4-{2-hydroxy-ethanoylamino)-cyclohexyl]-amide Starting from trans-4-(5-cyclopropylmethoxy-benzo(1,3Jdioxol-4-yl)-5H-pyrrolo[3,2-d)pyrJmidine-7-cartxjxylic acid (4-amino-cyclohexyi)-amide (example A140)and acetic acid chlorocarbonyl-methyl ester the tilie compound is obtained as colorless solid. MS (ESI): m/z = 508 (MH+ 100%)
1H-NMR (400 MHz, DMSO-d6). 12.27 (br.s, 1H, -NH); 9.03 (s, 1H); 8.30 (d, J = 7,9, 1H, -NH); 8,27 (s, 1H); 7.49 (d, J = 8.3, 1H, -NH); 7.01 (d. J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 5.42 (t, J = 5.5, 1H, -OH); 3.79 (m, 1H &d, J = 5.5, 2H); 3.76 (d, J = 6.8, 2H); 3.69 (m, 1H); 2.02 (~d, J ~ 8.9, 2H); 1.82 (~d,J~ 8.8, 2H); 1.46 (m, 4H); 0.86 (m, 1H); 0.29 (m, 2H); 0,11 (m, 2H).

Example 173: trans-[4-({1-[4-{5-Cyclopropytmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-a^pyrimidine-7-carboxylic acid [4-((S)-2-hydroxy-propanoylamino}-cyclohexyl]-amide Starting from trans-4-(5-cyclopropylmethoxy-benzo(1,3]dioxo!-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A140) and acetic acid (S)-1-chlorocarbonyl-ethyl ester the title compound is obtained as colorless solid. MS(ESI);m/z=522(MH').
1H-NMR (400 MHz, DMSO-d6): 9.03 (s, IN); 8.30 (d, J = 7.9, 1H, -NH); 8.27 (s, 1H); 7.44 (d, J = 8.3, 1H, -NH); 7.00 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, '1H); 6.00 (s, 2H); 5.45 (brs, 1H, -OH); 3.94 (qu, J = 6.7, 1H); 3.81 (m, 1H); 3.76 (d, J = 6.7, 2H); 3.63 (m, 1H); 2.02 (m, 2H); 1.81 (m, 2H); 1.44 (m, 4H); 1.22 (d. J = 6.7, 3H); 0.87 (m, 1H); 0.29 (m, 2H); 0,10 (m, 2H).
Example 174: cis-[4-({1-[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yi)-5H'pyrrolo[3,2-dlpyrimidine-7-carboxylic acid l4-(2-hydroxy-ethanoyiamino)-cyclohexyl]-amide Starting from cis-4-(5-cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cyclohiexyl)-amide (example A141) and acetic acid chlorocarbonyl-methyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 508 (MM*, 100%).
1H-NMR (400 MHz, DMSO-d6): 9.06 (s, 1H); 8.59 (d, J = 7.4, 1H, -NH); 8.28 (s, 1H); 7.57 (d. J = 7.7, 1H,-NH);7.01 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 6.01 (s, 2H); 5.34 (br.s, 1H,-OH); 4.06 (m, 1H); 3.82 (s, 2H & m, 1H); 3.77 (d, J = 6.7, 2H); 1.76 (m, 4H); 1.67 (m, 4H); 0.88 (m, 1H); 0.30 (m,2H);0,11 (m, 2H).
Example 175: cis-[4-({1 -[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4.((S)-2-hydroxy-propanoylamino>-cyclohexyl]-amide Starting from cis-4-(5-cyclopropylmethoxy-benzo[1,3]diGXOl-4-yl)-5H-pyrrolo[3,2-(flpyrimldine-7-cartxjxylic acid (4-amino-cyclohexyl)-amide (example A141) and acetic acid (3)-1-chlorocartxtnyl-ethyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 522 (MH+, 100%).
1H-NMR (400 MHz, DMSO-d6): 12.16 (br.s, 1H, -NH); 9.06 (s, 1H); 8.58 (d, J = 7.4, 1H, -NH); 8.28 (s, 1H); 7.52 (d, J = 7.8,1H, -NH); 7.01 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 6.01 (s, 2H); 5.37 (d, J = 5.3, 1H, -OH); 4.05 (m, 1H); 3.99(m, 1H); 3.77 (m, 1H & d, J = 6.7, 2H); 1.75 (m, 4H); 1.66 (m, 4H); 1.22 (d, J = 6.7, 3H); 0.87 (m, 1H); 0.30 (m, 2H); 0,11 (m, 2H).
Example 176: 4-{5-Cyclopropylmethoxy-benzo[1,3Jdioxol-4-yl)-5H-pyrrolo[3,2-d)pyrimidine-7-carboxylic acid [1-((S)-2-hydroxy-propanoyI)-piperidin-4-yl]-amide

starting from 4-(5-cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolQ[3;2-d]pyrimldine-7-carboxylic acid piperidin-4-ylannide hydrochloride (example A138) and acetic acid (S)-1-chlorocarbonyl-ethyl ester the title compound is obtained as colorless solid. MS (ESI); m/z = 508 (MH+, 100%).
1H-NMR (400 MHz, DMSO-d6): 11.91 (br.s, 1H, -NH); 9.03 (s, 1H); 8.45 (d, J = 7.7, 1H, -NH); 8.30 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.88 (br.s, 1H, -OH); 4.46 (m. IN); 4.25 (m, 1H); 4.16 (m, IN); 3.84 (m, 1H);3.76(d,J = 6.8, 2H); 3.16 (m, 1H);2.96(m, 1H); 1.99 (m, 2H); 1.56 {m, 1H); 1.42 (m, 1H); 1,21 (dd. J, = 6.9, J2 =^ 6.6, 3H); 0.87 (m, 1H); 0.29 (m, 2H); 0,11 (m, 2H).
Example 177; trans-4-(5-CycIopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c(lpyrimidine-7-carboxylic acid {4-[{1-hydroxy-cydopropanecarbonyl)-amino]-cyclohexyl)-am(de Starting from transr4-(5-cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4-amino-cyclohexyl)-amide (example A140)and acetic acid 1-chlorocarbonyi-cyclopropyl ester the title compound is obtained as colorless solid.
Example 178; cis-4-(5-Cyclopropylmethoxy-ben2o[1,3Jdioxol-4-yl)-5H-pyrroio[3,2-d]pyrimidine-7-carboxylic acid {4-[(1-hydroxy-cyclopropanecarbonyl)-amino]-cyclohexyl}-amide Starting from cis-4-{5-cyclopropy!methoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimtdtne-7-carboxyiic acid (4-amino-cyclohexyl}-amide {example A141)and acetic acid 1-chlorocarbonyl-cyclopropyl ester the title compound is obtained as colorless solid.
Example 179; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c/ipyrimidine-7-carboxylic acid {1-[1-(1-hydroxy-cyclopropyl)-methanoyl]-piperidin-4-yl}-amide Starting from 4-(5-cyclopropylmethoxy-benzo[1,3]dioxo(-4-yl)-5H-pyrrolo[3,2-(/]pyrimidine-7-cartwxylic acid piperidin-4-ylamide hydrochloride (example A138) and acetic acid 1-chlorocarbonyl-cyclopropyl ester the title compound is obtained as colorless solid.
Example 180: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1-(2-hydroxy-ethanoyl)-pyrrolidin-3~yl]-amide Starting from 4-(5-cyclopropy)methoxy-ben2of 1,3]dioxol-4-yl)-5H-py^rolo[3,2-d]pyrimidine-7-carboxylic acid (R)-pyrrolidin-3-ylamide hydrochloride (example A142) and acetic acid chlorocarbonyl-methyl ester the title compound is obtained as colorless solid. MS (ESI); m/z = 480.0 (MH+).
1H-NMR (300 MHz, DMSO-d6): 12.31 (br.s, 1H, -NH); 9.03 (s, 1H); 8.57 (d, J = 7.1, 0.5H, -NH); 8.54(d,J = 7.1,0.5H,-NH);8.31 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.56(d, J = 8.6, IN); 6.00 (s, 2H); 4.62 (m, 0.5H); 4.56 (t, J = 5.6, 1H, -OH & m, 0.5H); 4.06 (d, J = 5.6, 1H); 4.01 (d, J = 5.6, 1H);

3,76 (m, 1H); 3.53 (m, 2H); 3.37 (m, 1H); 2.32 • 2.18 (m, 1H); 2.07 (m, 0.5H); 1.94 (m, 0.5H); 0,87 (m, 1H); 0.29 (m, 2H); 0.10 {m, 2H).
Example 181: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1-{(S)-2-hydroxy-propanoyl)-pyrrolidin-3-yl]-amide Starting from 4-(5-cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (R}-pyrrolidin-3-ylamide J1ydrochloride (example A142) and acetic acid (S)-1-chlorocarbonyl-ethyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 494 (MH+).
1H-NMR (300 IV1Hz, DMSO-d6): 12.31 (br.s, 1H, -NH); 9.02 (s, 0.5H); 9.00 (s, 0.5H); 8.58 (d, J = 7.1. 1H, -NH); 8.31 (s. 1H); 7.01 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.92 (d, J = 6.7, 0.5H. -OH); 4.86 (d, J = 6.7, 0.5H, -OH); 4.61 (m, 0.5H); 4.53 (m, 0.5H); 4.33 (m, 0.5H); 4.26 (m, 0.5H); 3.84 (m, 0.5H); 3.76 (d, J = 6.7, 2H); 3.75 - 3.45 (m, 3H); 3.37 (m, 0.5H); 2.24 (m, 1H); 2.07 (m, 0.5H); 1.96(m, 0.5H); 1.23 (d, J = 6.6, 1.5H); 1.20 (d, J = 5,6, 1.5H); 0.87 (m, 1H); 0.29 (m, 2H);0.10(m, 2H).
Example 182: 4-(5-Cyc:opropylmethoxy-benzo[1,31dioxol-4-yi)-5H-pyrro(o[3,2-o]pyrimid!ne-7-carboxylic acid {{R)-1-[1-(1-hydroxy-cyclopropyl)-methanoyl]-pyrrolidin-3-yl}-amide Starting from 4-(5-cyclopropylmethoxy-benzo[1,31dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (R)-pyrralcdtn-3-y(amtde hydrochtoride (example A142} and acetic acid U chlorocarbonyl-cyclopropyl ester the title compound is obtained as colorless solid.
Example 183; 4-(5-Cyclopropy(methoxy-benzo{1,3]dioxol-4-yl)-5H-pyrrolo(3,2-d]pyrimidine-7-carboxylic acid [(S)-1-(2-tiydroxy-ethanoyl)-pyrrolidin-3-yl]-amide Starting from 4-(5-cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3.2-d]pyrimidine-7-carboxylic acid (S)-pyrrolidin-3-ylamide hydrochloride (example A143) and acetic acid chlorocarbonyl-methyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 480.0 (MH+).
1H-NMR (3DD MHz, DMSO-d6): 12.31 (br.s, 1H, -NH); 9.03 (s, 1H); 8.57 (d, J = 7.1, 0.5H, -NH); 8.54 (d, J = 7.1, 0.5H, -NH); 8.31 (s. 1H); 7.01 (d, J = 8.6. 1H); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.62 (m, 0.5H); 4.56 (t, J = 5.6, 1H, -OH & m, 0.5H); 4.06 (d, J = 5.6, 1H); 4.01 (d, J = 5.6, 1H); 3.76 (m, 1H); 3.53 (m, 2H); 3.37 (m, 1H); 2.32 - 2.18 (m, 1H); 2.07 (m, 0.5H); 1.94 (m, 0.5H); 0.87 (m, 1H); 0.29 (m, 2H); 0.10 (m, 2H).
Example 184: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d)pyrimidine-7-carboxylic acid [(S)-1-((S)-2-hydroxy-propanoyl)-pyrrolidin-3-yl]-amide

starting from 4~(5-cycloprapylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (S)-pyrrolidin-3-ylamide hydrochloride (example A143) and acetic acid (S)-1-chlorocarbonyl-ethyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 494 (MH*).
1H-NMR (300 IV1Hz, DMSG-de): 12.31 (br.s, 1H, -NH); 9.03 (s, 0.5H); 9.01 {s, 0.5H); 8.57 (d, J = 7.0, 0.5H, -NH); 8.56 (d, J = 6.7, 0.5H, -NH); 8.31 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.87 (d, J = 6.8, 0.5H, -OH); 4.86 (d, J = 6.8, 0.5H, -OH); 4.57 (m, 1H); 4.29 (m, 1H); 3.96 {m, 0.5H); 3.84 - 3.44 (m, 3H); 3.76 (d, J = 6.8, 2H); 3.38 (m, 0.5H); 2.33 - 2.18 (m, 1H); 2.07 (m, a.5H); 1.96 (m, 0.5H); 1.23 (d, J = 5.5, 1.5H); 1.19 {d, J = 6.5, 1.5H); 0.87 (m, 1H); 0.30 (m, 2H);0.10(m, 2H).
Example 185: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrroio[3,2-d]pyrimidine-7-carboxylic acid {(S)-1-(1-(1 -hydroxy-cyclopropyl)-methanoyl]-pyrrolidin-3-yi}-amide Starting from 4-(5-cyc/apropylmethQxy-benzo[1,3]dtoxol-4-yf)-5/T'-pyrrolo[3,2-c'Ipyrim(dfne-7-carboxylic acid {S)-pyrrolidin-3-ylamide hydrochloride (example A143) and acetic acid 1-chlorocarbonyl-cyclopropyl ester the title compound is obtained as colorless solid.
Example 186; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c'|pyrimidine-7-carboxylic acid [1-(2-hydroxy-ethanoyl)-piperidin-4-ylmethyl]-amide Starting from 4-(5-cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {piperidin-4-ylmethyl)-amide (example A144) and acetic acid chlorocarbonyl-methyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 508 (MH+).
1H-NMR (400 MHz, DMSO-d6): 12.27 (br.s, 1H. -NH); 9.03 (s, 1H); 8,51 (t, J = 6.0, 1H, -NH); 8.27 (s, 1H); 7.01 (d, J = 8.6, 1H); 656 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.41 (t, J = 5.3, 1H, -OH); 4.35 (m, 1H); 4,07 (m, 2H); 3.77 (d, J = 6.8, 2H); 3.69 (m. 1H); 3.34 (dd, J1 = J2 = 5.8, 2H); 2.94 (m, 1H); 2.63 (m, 1H); 1.84 (m,1H); 1.76 (m,2H); 1.19 (m, 1H); 1.12 (m,1H); 0.87 (m, 1H); 0.30 (m, 2H); 0.10 (m,2H).
Example 187; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimldine-7-carboxylic acid [1 -((S)-2-hydroxy-propanoyl)-piperidin-4-ylmethyl]-amide Starting -from 4-(5-cyclopropy I methoxy-benzo[1,3]d ioxol-4-yl )-5H-pyrrolo[3,2-d] pyrimidine-7-carboxylic add (piperidin-4-yImethyl)-amide (example A144) and acetic acid (S)-1-chlorocarl3onyl-ethyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 522 (MH+).
1H-NMR (400 MHz, DMSO-d6): 12.27 (br.s, 1H, -NH); 9.03 (s, IN); 8.51 (t, J = 6.0, IN, -NH); 8.27 (s, 1H); 7.01 (d, J = 8.5, 1H); 6.57 (d, J = 8.5, 1H); 6.00 (s, 2H); 4,74 (br.s, 1H, -OH); 4,41 (m, 1H & 1H); 4.35 (m. 1H); 3,99 (m, 1H); 3.77 (d, J = 6.7. 2H); 3.35 (dd, J1 = J2 = 6.1, 2H); 2.98 (m, 1H);

2.60 (m, 1H); 1.86 (m, 1H); 1.76 (m,2H); 1.19 (m, 1H); 1.17 (m, 3H); 1.12 (m.1H); 0.88 (m, 1H); 0.30(m, 2H);0,10{m, 2H).
Example 188: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid{1-[1-(1-hydroxy-cyctopropyl>-methanoyl]-piperidin-4-ylmethyl}-amide Starting from 4-(5-cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {piperidin-4-ylmethyl)-amide (example A144) and acetic acid 1-chlorocarbonyl-cyclopropyl ester the title compound is obtained as colorless solid. MS (ESI): m/2 = 534 (MH+).
1H-NMR (400 MHz, DMSO-d6): 12.27 (br.s, 1H, -NH); 9,04 (s, 1H); 8.51 (t, J = 6.0, 1H, -NH); 8.27 (s, 1H); 7.01 (d, J - 8.6, 1H); 6.57 (d, J - 8.6, 1H); 6.23 (s, 1H, -OH); 6.00 (s, 2H); 4.42 (m, 2H); 3.77 (d, J = 6.8, 2H); 3.35 (dd, J, = Jj = 6.3, 2H); 2.818 (m, 2H); 1.86 (m, 1H); 1.76 (m, 2H); 1.20 (m, 2H); 0.88 (m, 1H & 2H); 0.74 (m, 2H); 0.30 (m, 2H); 0.11 (m, 2H).
Example 189: 4-(5-Cycloprapylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-hydroxy-acetyl>-piperidln-3-ylmethyl]-amide
Starting from 4-(5-cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic add (piperidin-3-ylmetliyl)-amide (example A145) and acetic add clilorocarbonyl-methyl ester the title compound is obtained as colorless solid. MS (ESI): w/z = 508 (MH+).
1H-NMR (400 MHz, DMSO-d6): 12.28 (br.s, 1H, -NH); 9.04 (s, 1H); 8.52 (br.s, 1H, -NH); 8.28 (s, 1H); 7.01 (d, J = 8.6, IN); 6.57 (d, J = 8.6, 1H); 6.00 (s. 2H); 4.40 (br.s, 1H, -OH); 4.29 (m, 0.5H); 4.07 (m, 2.5H); 3.77 (d, J = 6.7, 2H); 3.66 (m, 0.5H); 3.56 (m, 0.5H): 3.35 (m. 2H); 2.95 (m, 0.5H); 2.82 (m, 1H);2.58(m, 0.5H); 1.84 (m, 1.5H); 1.68 (m, 1.5H); 1.35 (m, 2H); 0.89 (m, 1H); 0.30 (m, 2H);0.11 (m,2H).
Example 190; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5y4^pyrrolo[3,2-Q]pyrimidine-7-carboxylic add [1 -((S)-2-hydroxy-propionyl)-prperldin-3-ylniethyl]-amide Starting from 4-(5-cyclopropylmethoxy-benzo[1,31droxol-4-yl)-5H-pyrrolo[3,2-d]pyrimldine-7-carboxylic add (piperidin-3-ylmethyl)-amide (example A145) and acetic acid (S)-1-chlorocarbonyl-ethyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 522 (MH+).
1H-NMR (400 MHz, DMSO-d6): 12.28 (br.s, 1H, -NH); 9.04 (s, 1H); 8.52 (br.s, 1H, -NH); 8.28 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.57 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.73 (m, 1H, -OH); 4.41 (m, 1H); 4.31 (m, 0.5H); 4.19 (m, 0.5H); 3.97 (m, 0.5H); 3.83 (m, 0.5H); 3.77 (d, J = 6.7, 2H); 3.35 (m, 2H); 3.01 (m, 0.5H); 2.89 (m, 0.5H); 2.66 (m, 0.5H); 2.56 (m, 0.5H); 1.87 (m, 1H); 1.69 (m, 2H); 1.35 (m, 2H); 1.16 (m, 3H); 0.89 (m, 1H); 0.30 (tn, 2H); 0.11 (m, 2H).

Example 191: 4-(5-Cyclopropy[methoxy-ben2o[13]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-{2-hydroxy-acetyl)-pyrrolidln-3-y!methyl]-amide
Starting from 4-(5-cyclopropylmethoxy-benzo[1,3Jd!oxol-4-yl)-5H'pyrrolo[3,2-d)pyrimidine-7-cartxDxyllc acid {pyrrolidin-3-ylmeltiyl)-amide (example A146) and acetic acid chlorocarbonyl-methyl ester the title compound is obtained as colorless solid. MS(ESI):m/z = 494(MH+).
'H-NIVIR (400 MHz, DMSO-d6): 12.28 (br.s, 1H,-NH); 9.04 (s, 1H); 8.55 (m, 1H.-NH); 8.29 (s, 1H); 7.00 (d, J = 8.6, 1H); 6.57 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.44 (t, J = 5.4, 1H, -OH); 3.99 (m, 2H); 3.77 (d, J = 6.7, 2H); 3.48 (m, 4H); 3.33 (m, 1H); 3.16 (m, 1HJ; 2.57 (m, 1H); 2.47 (m. 1H); 2.06 (, 0.5H); 1.97(m, 0.5H); 1.76 (m, 0.5H); 1.66 (m, 0.5H); 0.88 (m, 1H); 0.29 (m, 2H); 0.10 {m, 2H).
Example 192: 4-{5-Cyclopropylmethoxy-ben2o[1,3]dioxol-4-yl)-5^/-pyrrolo(3,2-d]pyrimidine-7-carboxylic acid [1-((S)-2-hydroxy-propionyl)-pyrroliciin-3-yimethyl]-ajnide Starting from 4-(5-cyc(opropy(methoxy-benzo[1,3Jdroxo/-4-yl}-5/T'-pyrro(o[3,2-c(Ipyrim(drne-7-cartwxylic acid (pyrrolidin-3-ylmethyl)-amide (example A146) and acetic acid {S)-1-chlorocarbonyl-ettiyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 508 (MH+).
1H-NMR (400 MHz, DMSO-d6): 12.28 (br.s, 1H, -NH); 9.05 (s, 0.5H); 9.04 (s, 0.5H); 8.54 (m, 1H, -NH); 8.29 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.57 (d, J = 8.6, 1H); 6.00 (s, 2H); 4,77 (m, 1H, -OH); 4.24 (m, 1H); 3.77 (d, J = 6.8, 2H); 3.75 (m, 0.5H); 3.64 - 3.38 (m, 4.5H); 3.29 (m, 0.5H); 3.13 (m, 0.5H); 2.55 (m, 0.5H); 2.47 {m, 0.5H); 2.05 (m, 0.5H); 1.97 (m, 0.5H); 1.77 (m, 0.5H); 1.66 (m, 0.5H); 1.16 (m, 3H); 0.88 (m, 1H); 0.30 (m, 2H): 0.10 (m, 2H).
Example 193: 4-(5-Cyclopropylmethoxy-ben2o[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(2-hydroxy-acetyl)-morpholin-2-ylmethyl]-amide Starting from 4-(5-cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (morpholin-2-ylmethyl)-amide (example A147) and acetic acid chlorocarbonyl-methyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 510 (MH+").
1H-NMR(400 MHz, DMSO-d6): 12.29 (br.s, 1H, -NH); 9,04 (s, IN); 8.58 (t, J = 5.7, 1H, -NH); 8.30 (s, 1H); 7.01 (d, J = 8.6, IN); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.59 (br.s, 1H, -OH); 4.28 (m, 0.5H); 4.14 (m, 1.5H); 4.05 (m, 1H); 3.91 (m, 1H); 3.76 (d. J = 6.7, 2H & m. 0.5H); 3.59 (m, 2.5H); 3.23 (m, 2H); 3.11 (m, 0.5H); 2.95 (m, 0.5H); 2.80 (m, 0.5H); 2.60 (m, 0.5H); 0.88 (m, 1H); 0.29 (m, 2H):0.10(m, 2H).
Example 194: 4-(5-Cyclopropylmethoxy-ben2o[1,3]dioxot-4-yl)-5H-pyrroio[3,2-d]pyrimidine-7-carboxylic acid [4-((S)-2-hydroxy-propionyl)-morphQlin-2-ylmethyl]-amide

Starting from 4-(5-cydopmpylmethaxy-benzo[1,3]dloxal-4-y\)-5N-pyrrolol3,2-d]pyrimidine-7-carboxylic acid (nnorpholin-2-ylmethyl)-amide {example A147) and acetic acid (S)-l-chlorocarbonyl-ethyl ester the title compound is obtained as colorless solid. MS (ESI): m/2 = 524 (MH+).
1H-NMR (400 MHz, DMSO-d6): 12.29 (br.s, 1H, -NH); 9.04 {s, 1H); 8.59 (t, J = 5.6, 1H, -NH); 8.30 (s, 1H);7.01 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.92 (br.s, 1H,-OH); 4.42 (m, 1H); 4.30 (m, 0.5H); 4.16 (m, 0.5H); 4.05 (m, 0.5H); 3.91 (m, 1.5H); 3.77 {d, J = 67. 2H): 3.59 (m, 2H); 3.49 (m, 2H); 3.15 (m, 0.5H); 2.99 (m. 0.5H); 2.77 (m, 0,5H); 2.58 (m, 0.5H); 1,18 (br.s, 3H); 0.88 (m, 1H): 0.29 (M, 2H); 0.10 (m. 2H).
Example 195: 4-(5-Cyclapropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-tiydroxy-ethanoyl}-azetidin-3-yl]-amide
Starting from 4-(5-cyciopropylmethoxy-benzo[1,31dioxo!-4-yl)-5H-pyr;ola[3,2-d]pyrimidine-7-carboxyiic acid azetidin-3-yiamkie (example A172)and acetic acid chlorocarbonyl-methyl ester the title compound is obtained as colorless solid. MS (ESI): m/2 = 466 (MH+).
1H-NMR{400 MHz, DMSO-d6): 12.32 (br.s, 1H, -NH); 9.06 (s, 1H); 8.86 (d, J = 7.2, 1H, -NH); 8.32 (s, 1H); 7.01 (d, J = 8.6, 1H); 6.57 (d, J = 8.6, 1H); 6.01 (s, 2H); 4.90 (t, J = 5.4, IN, -OH); 4.82 (m, IN); 4.54 (m, 1H); 4.28 (m, 1H); 4.21 (m, 1H); 3.94 (d, J = 5.4, 2H); 3.90 (m, 1H); 3.76 (d, J = 6.7, 2H); 0.87 {m, IN); 0.29 (M, 2H); 0.09 (m, 2H).
Example 196: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxo|-4-y|)-5H-pyrrolo[3,2-d]pyrimidrne-7-carboxylic acid [1-((S)-2-hydroxy-prGpanoyl)-azetidin-3-yl]-amide
Starting from 4-(5-cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c(Ipyrimidine-7-carboxylic acid azetidin-3-ylamide (example A172) and acetic acid {S)-1-chlorocarbonyl-ethyl ester the title compound is obtained as colorless solid. MS (ESI); m/z = 480 (MH+).
1H-NMR (400 MHz, DMSO-d6): 12,33 (br.s, IN, -NH); 9.07 (s, 1H); 8.85 (d, J = 7,2, 1H, -NH); 8.32 {s, 1H); 7.01 (d, J = 8.6, IN); 6.57 {d, J = 8.6, 1H); 6.01 (s, 2H); S.06 (m, 1H, -OH); 4.80 (m, 1H); 4.63 (m, IN); 4.26 {m,1H); 4.15 (m, 1H); 3.89 (d. J = 5.4, 2H); 3.76 (d, J = 6.7, 2H); 1.21 (d, J = 6.7, 3H); 0.87 (m, 1H); 0.29 (M, 2H); 0.10 (m, 2H).
Example 197: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxo|-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(S)-1 -((S)-2-hydroxy-propanoyl)-piperid in-3-yl]-am ide Starting from 4-(5-cyclopropylmethoxy-ben2o[1,3]dioxol-4-yl)-5H^pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (S)-piperidin-3-ylannide (example A148) and acetic acid (S)-1-chlorocarbonyl-ethyl ester the title compound is obtained as colorless solid. MS (ESI): m/z= 508.1 (MH+).

1H-NMR (400 MHz, DMSO-d6): 11,86 (br.s, 1H, -NH); 9.01 (s, 0.5H); 8,98 (s, 0.5H); 8.52 (d, J = 7.7, 1H, -NH); 8.30 (br.s, 1H); 7.01 (d, J = 8.6, 1H); 6.56 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.76 (-d, 0.5H, -OH); 4.62 (-d, 0.5H, ~0H); 4.46 (m. 1H); 4.06 (m, 0.5H); 3.92 (m, 2H); 3.76 (d, J = 6,7, 2H); 3,59 (m, 0,5H); 3.38 (m, 1H); 3.20 (m, 1H); 2.96 (m, 1H); 1.99 (m, 1H); 1.76 (m, 2H); 1.52 (m, 1H); 1.24 (br.s, 3H); 0.87 (m, 1H); 0.29 (m, 2H); 0.10 (m, 2H),
Example 198: 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1 -((S )-2-hydroxy-propanoy I )-piperidm-3-yl)-amide Starting from 4-(5-cyclopropylmethoxy-benzo(1.3]dioxol-4-yl)-5H-pyrrolo[3,2~d]pyrifnidine-7-carboxylic acid (R)-piperidin-3-ylamide (example A149) and acetic acid (S)-1-chlorocarbonyl-etliyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 508.1 (MH+).
1H-NMR (400 MHz, DMSO-d6): 11.86 (br.s, 1H, -NH); 9.01 (s, 0.5H); 8.98 (s, 0.5H); 8.52 {d. J = 7.7, 1H, -NH); 8.30 (br.s, 1H); 7.01 (d, J = 8.6, 1H); 6.56 (d, J = 8.6. 1H); 6.00 (s, 2H); 4.76 (~d, 0.5H, -OH); 4,62 {~d, 0,5H, -OH); 4.46 (m, 1H); 4.06 (m, 0.5H); 3,92 (m, 2H); 3.76 (d, J = 6.7, 2H); 3.59 (m, 0.5H); 3,38 (m, 1H); 3.20 (m, 1H); 2,96 (m, 1H); 1,99 (m, 1H); 1.76 (m, 2H); 1.52 (m, 1H); 1.24 (brs. 3H); 0.87 (m, 1H); 0.29 (m, 2H); 0,10 (m, 2H).
Example 199:trans-4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-(:/Jpyrimidine-7-carboxylicacid[4-(2-hydroxy-acety(amino)-cyclohexyl)-amide Starting from trans-4-(2-cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxytic acid (4-amino-cyclohexyl)-amide (example A150) and acetic acid chlorocarbonyl-methyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 494 (MH+. 100 %).
1H-NMR (400 MHz. DMSO-d6): 11.90 (br.s, 1H, -NH); 9.01 (s, 1H); 8.39 (d, J = 7.9, 1H, -NH); 8.21 (s, 1H); 7,62 (d, J = 8,5, 1H); 7.49 (d, J = 8.3, 1H. -NH); 6.73 (dd, J, = 8.5, Js = 2.1, 1H); 6.69 (d, J = 2,1, 1H); 5,42 (t. J = 5.8, 1H. -OH); 3.92 (d, J - 6.9, 2H); 3.86 (s, 3H & m, 1H); 3.80 (d, J = 5.8, 1H); 3.33 (m, 1H); 2.01 (m, 2H; 1.82 (m, 2H); 1.38 (m, 4H); 1.17 (t. J = 7.0, 3H); 0.97 (m, 1H); 0.37 (m, 2H); 0.23 (m, 2H>.
Example 200: trans-4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid[4-((S)-2-hydroxy-proptonylamino)-cyclohexyl]-amide Starting from trans-4-(2-cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxytic acid (4-amino-cyclohexyl)-amide (example A150) and acetic acid (S)-1-chlorocarbonyl-ethyl ester the title compound is obtained as colorless solid. MS (ESI); m/z = 508 (MH', 100 %).
1H-NMR (400 MHz, DMSO-d6): 11.90 (br.s. 1H, -NH); 9.01 (s, 1H); 8.39 (d, J = 7.9, 1H, -NH); 8.21 (s, 1H); 7.62 (d, J = 8.5. 1H); 7.43 (d. J = 8.3, 1H, -NH); 6.73 ( dd, J, = 8.5, J2 = 2,1, 1H); 6,69 (d, J

= 2.1, 1H); 5.43 (d, J = 5.2, 1H,-0H}; 3.96 (m, 1H); 3.92 (d, J = 6.9, 2H); 3.86 {s, 3H); 3.B0 (m, 1H); 3,64 (m, IN); 2.00 (m, 2H; 1.82 (m, 2H); 1.43 (m, 4H); 1.21 {d. J = 6.7, 3H); 0.97 (m, 1H); 0.37 (m, 2H); 0.23 (m, 2H).
Example 201: trans-4-{2-Cyclopropylmethoxy-4-methoxy-phenyi)-5H-pyrrolo[3,2-c/]pyrimidine'7-carboxylic acid {4-[(1-hydroxy-cyclopropanecartionyl)-amino]-cyclohexyl}-amide Starting from trans-4-(2-cyctopropylmethoxy-4-methoxy-pheny)}'5H-pyrroiof3,2-c']pynmidme-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A150) and acetic acid 1-chlorocarbonyl-cyclopropyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 520 (MH+, 100 %).
'H-NIVIR 300 MHz, DMSO-d6): 11.89 (br.s, 1H,-NH); 9.00 (s, 1H); 8.37 (d, J = 7.9, IN,-NH); 8.20 (d, J = 3.2, 1H);7.61 (d, J = 8.4, 1H); 7.56 (d, J = 8.5, 1H,-NH); 6.72 { dd, J, = 8.4, J1 = 2.2, IN); 6.69 (d, J = 2.2, 1H); 6.20 (s, 1H, -OH); 3.91 (d. J = 6.9, 2H); 3.86 (s, 3H); 3.81 (m, 1H); 3.70 (m, 1H); 2.01 (m, 2H); 1.82 (m, 2H): 1.47 (m, 4H); 1.02 (m, 2H); 0.97 (m, IN); 0.83 (m, 2H); 0.34 (m, 2H); 0.24 (m, 2H).
Example 202: cis-4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-dlpyrimidine-7-carboxylic acid [4-(2-hydroxy-acetylamino)-cyclohexyl)-amide Starting from cis-4-(2-cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbwxylic acid (4-amino-cyclohexy))-amide (example A151) and acetic acid chlorocarbonyl-methyl ester the title compound is obtained as colorless solid. MS(ESI):m/z = (MH+, 100%).
1H-NMR (400 MHz, DMSO-d6): 11.91 (br.s, 1H, -NH); 9.03 (s, 1H); 8.68 (d, J = 7.5, 1H, -NH); 8.21 (d, J = 3.3, 1H); 7.62 (d, J = 8.5, 1H); 7.56 (d, J = 7.8, 1H, -NH); 6.72 ( dd, J, = 8.5, J2 = 2.2, 1H); 6.69 (d, J = 2.2, 1H); 5.34 (t, J = 5.9, 1H, -OH); 4.07 (m, 1H); 3.92 (d, J = 6.9, 2H); 3.85 (s. 3H); 3.82 (d, J = 5.9, 2H & m, 1H); 1.82-1.58 (m, 8H); 1.22 (d, J = 6.7, 1H); 0.97 (m, 1H); 0.37 (m, 2H); 0.23 (m,2H).
Example 203: cis-4-{2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrob[3,2-d]pyrimidine-7-carboxyf(c acid [4-((S)-2-hydroxy-propionylamino)-cyclohexyl]-amide Starting from cis-4-(2-cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbwxylic acid (4-amino-cydohexyl)-amide (example A151) and acetic acid (S)-1-chlorocarbonyl-ethyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 508 (MH+, 100 %).
1H-NMR (400 MHz. DMSO-d6): 11.90 (br.s, 1H, -NH); 9,03 (s, 1H); 8.67 (d, J = 7.5, 1H. -NH); 8.21 (s, 1H); 7.62 (d, J = 8.4, 1H); 7.51 (d, J = 7.7, 1H, -NH); 6.72 ( dd, J1 = 8.4, J2 = 2.2, 1H); 6.69 (d, J = 2.2, 1H); 5.37 (d, J = 5.4,1H, -OH); 4.07 (m, 1H); 3.99 (m, 1H); 3.92 (d, J = 7.0, 2H); 3.87 (s, 3H); 3.76 (m, 1H); 1.82-1.58 (m, 8H); 1.22 (d, J = 6.7, 1H); 0.97 (m, 1H); 0.37 (m, 2H); 0.23 (m, 2H).

Example 204: cis-4-{2-Cyclopropylmethoxy-4'methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylie acid {4-[(1-hydroxy-cyclopropanecarbonyl)-amino]-cyclohexyl}-amide Starting from cfs-4-(2-cyclopropyltnethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-dJpyrimi'dfne-7-carboxylic acid (4-amino-cyclotiexyl)-amide (example A151) and acetic acid 1-chlorocarbonyl-cyclopropyl ester (he title compound is obtained as colorless solid. MS (ESI): m/z = 520 (MH\ 100 %).
1H-NMR 400 MHz, DMSO-de): 11.90(br.s, 1H,-NH); 9.04 (s, 1H); 8.37 (d, J = 7.9, 1H,-NH); 8.20 (d, J = 3,2, 1H); 7.61 (d, J = 8,4, 1H); 7.56 (d, J = 8.5, 1H, -NH); 6,72 (dd, J1 = 8.4, J2 = 2.2, 1H); 6.69 (d, J = 2.2, IN); 6.26 (s, IN, -OH); 4.09 (m, 1H); 3.92 (d, J = 7.0, 2H); 3.86 (s, 3H); 3.78 (m, 1H); 1,87-1.66 (m, 8H); 1.02 (m, 2H); 0.98 (m, 1H); 0.83 (m, 2H); 0.34 (m, 2H); 0.24 (m, 2H).
Example 205: 4-(2-Cyc!opropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carfjoxyfic acid f1-(2-hydroxy-ethanoyl)-p(peridfn-4-ylJ-am(de
Starting from 4-(2-cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide (example A152) and acetic acid chlorocarbonyl-methyl ester tine title compound is obtained as colorless solid. MS (ESI): m/2 = 480 {MH\ 100 %).
1H-NMR 400 MHz, DMSO-d6); 11.92 (br.s, 1H, -NH); 9.00 (s, 1H); 8.53 (d, J = 7.8, 1H, -NH); 8.22 (s, 1H); 7.62 (d, J ^^ 8.5, 1H); 6.73 (dd, J, = 8.5, J2 = 2.1, 1H); 6.69 (d, J = 2.1, 1H); 4.51 (t. J = 5.4, IN, -OH); 4,27-4.05 (m, 4H); 3,92 (d, J = 6.9, 2H); 3.86 (s, 3H); 3.69 (m, 1H); 3.19 (m, 1H); 2.99 (m, 1H);2,00(m, 2H); 1.56 (m, 1H); 1.42 (m, 1H); 1,21 (m, 3H); 0.98 (m, 1H); 0.36 (m, 2H); 0.23 (m, 2H).
Example 206: 4~(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-((S>-2-tiydroxy-propanoyl)-piperidin-4-yl]-amide
Starting from 4-(2-cyclopropylmethQxy-4-methoxy-pheny!)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide (example A152) and acetic acid (S)-l-chlorocarbonyl-ethyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 494 (MM', 100 %).
1H-NMR (400 MHz, DMSO-d6): 11,94 (br.s, 1H, -NH); 9,00 (s, 1H); 8.53 (d, J = 7.7, 1H, -NH); 8.23 (s, 1H); 7,62 (d, J = 8.5, 1H); 6.73 ( dd, J1 = 8.5, J2 = 2.1, 1H): 6.69 (d, J = 2.1,1H); 4.88 (d, J = 6.9,1H, -OH): 4.46 (m, 1H); 4.26 (m, 1H); 4,18 (m, 1H); 3.98 (m, 1H); 3.93 (d, J = 6.9, 2H); 3.87 (s. 3H);3.31 (m, 1H);2.98(m, 1H); 1.98 (m,2H): 1,56 (m, 1H); 1.42 (m 1H);0.97(m, 1H); 0.36 (m, 2H); 0,23 (m. 2H),
Example 207: 4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {1-[1-(1-hydroxy-cyclopropyl)-methanoyl]-piperidin-4-yl}-amide

starting from 4-(2-cyclopropylmethoxy-4-nnethoxy-phenyl)-5H-pyrrolo[3,2-cy|pyrimidine-7-carboxylic acid pjperidin-4-ylamide (example A152) and acetic acid 1-chlorocarbonyl-cyclopropyl ester the title compound is obtained as colorless solid, MS (ESI): m/z = 506 (MH+, 100 %).
1H-NMR 400 IV1Hz, DIVISO-de): 11.92 (br.s, 1H, -NH); 9.00 (s, 1H); 8.54 (d, J = 7.9, 1H, -NH); 8.23 (s. 1H); 7.62 (d, J = 8.5, 1H); 6.72 ( dd, J1 = 8.5, J2= 2.2, 1H); 6.69 (d, J = 2.2. 1H); 6.31 (s, 1H, -OH); 4.28 (m, 1H); 4.17 (m, 2H); 3.91 (d, j = 6.9, 2H); 3.86 (s, 3H); 3,16 (m, 2H); 1.99 (m, 2H); 1.51 (m, 2H); 0.97 (m, 1H); 0.94 (m, 2H): 0.77 (m, 2H); 0.36 fm, 2H); 0.23 fm, 2H).
Example 208: cis-4-(2-cyclopropylmethoxy-5-metiioxy-phenyl)-5H-pyrrolo[3,2~ c/]pyrimidine-7-carboxylic acid [4-(2-hydroxy-acetylamino)-cyclohexyl]-amide Starting from cis^-(2-cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo [3.2-o]pyrimidine-7-carboxylic acid (4-aminQ-cyciohexyl)-amide (example AI54) and acetic acid chlorocarbonyl-methyl ester the title compound is obtained as coforiess solid. MS (ESI): m/z = 494 (MH+, 100 %).
1H-NMR 200 MHz, DMSO-d6): 12.00 (br.s, 1H, -NH); 9.08 (s, 1H); 8.65 (d, J = 7.8, 1H, -NH); 8.25 (s, 1H); 7.56 (d, J = 7,7, 1H, -NH); 7.19 (t, J = 1.7, 1H); 7.12 (d, J = 1 J, 2H); 5.33 (t. J - 5.9, 1H, -OH); 4.07 (m, 1H); 3.83 (d, J = 6.8, 2H & d, J = 5.9, 2H); 3.78 (s, 3H & m. 1H); 1.89-1.61 (m, 8H); 0.93 (m, 1H); 0.33 (m, 2H); 0.17 (m, 2H).
Example 209: cis-4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-cf]pyrimidine-7-carboxylic acid{4-[(1-hydroxy-cyclopropanecarbonyl)-amino]-cyclohexyl}-amide Starting from cis-4-(2-cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amincKcyclohexyl)-amide (example A154) and acetic acid 1-chlorocarbonyl-cyclopropyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 520 (MH\ 100 %).
1H-NMR 200 MHz, DMSO-d6): 12.00 (br.s, 1H, -NH); 9.09 (s, 1H); 8.67 (d, J = 7.4, 1H, -NH); 8.24 (s, 1H); 7.56 (d, J = 7.8, 1H, -NH); 7.18 (t, J = 1.6, 1H); 7,11 (d, J = 1.6, 2H); 6.27 (s, 1H, -OH); 4.10 (m, 1H); 3.82 (d, J - 6.8, 2H); 3.77 (s, 3H & m, 1H); 1.85-1.68 (m, 8H); 1.07 (m, 2H); 0.91 (m, 1H); 0.83 (m, 2H); 0.32 (m, 2H); 0.17 (m, 2H),
Example 210: trans-4-(2-cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-
'H-NIVtR 200 MHz, DMSO-d6); 11.98 (br.s, 1H, -NH); 9.05 (s, 1H); 8.35 (d, J = 7.8, 1H, -NH); 8.24 (s, 1H);7.56(d, J = 8.4, 1H,-NH); 7.18 (t, J = 1.6, 1H);7.11 (d, J = 1.6, 2H); 6.15 (s, 1H,-OH); 3.82 (d, J = 6.8, 2H & m, 1H); 3.77 {s, 3H); 3.68 (m, 1H); 2.03 (m, 2H); 1.83 (m, 2H); 1.57-1.39 (m, 4H); 1.02 {m,2H); 0.91 (m, 1H); 0.82 (m, 2H); 0.32 {m. 2H); 0.15 {m, 2H).
Example 211: 4-{2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrroIo[3,2-rf]pyrimidine-7-carboxylic acid I1-(2-tiydroxy-acetyl)-piperidin-4-yl]-amide
Starting from 4-(2-cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimldine-7-carboxyiic acid piperidin-4-y!amide (example A155) and acetic acid chlorocarbonyl-methyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 480 (MH+ 100 %).
1H-NMR 400 MHz, DMSO-d6); 12.03 (br.s, 1H,-NH); 9.05 (s, 1H); 8.51 (d, J = 7.8, IN,-NH); 8.27 (s, 1H); 7.19 (t, J = 1.6, 1H); 7.11 (d, J = 1.6, 2H); 4.52 (t, J = 5.4, 1H, -OH); 4.27-4.08 (m, 4H); 3.82 (d, J = 6,8, 2H); 3.77 (s, 3H); 3.69 (m, 1H); 3.20 (m, 1H); 3.00 (m, 1H); 1.99 (m, 2H); 1.58 (m, 1H); 1,43 (m, 1H); 0.91 (m, 1H); 0.32 (m, 2H); 0.17 (m, 2H).
Example 212: 4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimldine-7-carboxylic acid[1-({S)-2-tiydrDxy-propJony))-pjperidin-4-y)J-amide
Starting from 4-(2-cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-G'lpyrimidine-7-carboxylic acid ptperidin-4-ylamide (example A155) and acetic acid (S)-l-chlorocarbonyl-ethyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 494 (MH+, 100 %).
1H-NMR 400 MHz, DMSO-d6): 12.03 (br.s, 1H, -NH); 9.05 (s, 1H); 8.51 (d, J = 7.8, 1H. -NH); 8.27 (s, 1H);7.19(t, J= 1.6. 1H);7.11 (d, J = 1.6, 2H); 488(d, J = 6.9, 1H,-OH); 447 (m, 1H); 4.30-4.20 (m, 2H); 3.97 (m, 1H); 3.82 (d, J = 6.9, 2H); 3.78 (s, 3H); 3.28 (m, 1H);2.96(m, IN); 1.99 (m,2H); 1.57 (m, 1H); 1.42 (m, 1H); 1.21 (m, 3H); 0.91 (m, 1H); 0.32 (m, 2H); 0.17 (m, 2H).
Example 213: 4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo(3,2-c(]pyrimidine-7-carboxylic acid [1-(1-tiydroxy-cycJopropanecarbonyl>-piperidin-4-yI]-amide
Starting from 4-(2-cyclopropylmethoxy-5-methoxy-ptienyl)-5/4-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide (example A155) and acetic acid 1-chlorocarbonyl-cyclopropy1 ester the title compound is obtained as colorless solid. MS (ESI): m/z = 506 (MH', 100 %).
1H-NMR 400 MHz, DMSO-d6): 12.01 (br.s, 1H, -NH); 9.06 (s, 1H); 8.52 (d, J = 7.8, 1H, -NH); 8.27 (s, 1H); 7.19 (t, J = 1.6, 1H); 7.11 (d, J = 1.6, 2H); 6.31 (s, 1H, -OH); 4.29 (m, ZH); 4.18 (m, 1H); 3.83 (d, J = 6.9, 2H); 3.77 (s, 3H); 3.17 (m, 2H); 2.00 (m, 2H); 1.51 (m, 2H); 0.92 (m, 3H); 0.78 (m, 2H); 0.32 (m,2H); 0.17 (m,2H).

Example 214: cis-4-(2-Cyclopropylmethoxy-4-fluorQ-ptienyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-{2-hydroxy-acetylaminc)-cyclohexyl]-amide
Starting from cis-4-(2-cyclopropylmethoxy-4-fiuorophenyl)-5H-pyrrolo[3,2-c/jpyrimidine-7-carboxylic acid (4-amino-cyctoliexyl)-amide (example A156) and acetic acid chlorocarbonyl-methyl ester tine title compound is obtained as colorless solid. IVIS (ESI): m/z = 482 (MH+. 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.04 (br.s, 1H, -NH); 9.07 {s, 1H); 8.65 (d, J = 7.5. 1H; -NH); 8.28 (s, 1H); 7.68 (dd,J1 = 8.6, J2 = 7.0, 1H); 7.55 (d, J = 7.7, 1H,-NH); 7.09 (dd, J, = 11.6, J2 = 2.4, 1H); 6.97 (ddd, J1 = Ja = 8.5, J3 = 2.4, 1H); 5.33 (t, J = 5.9. 1H, -OH); 4.07 (m, 1H); 3.93 (d, J = 7.0, 2H);3.82(d.J = 5.9, 2H&m, IN); 1.88-1.53 (m. 8H); 0.97 (m, 1H);0.36(m, 2H); 0.22 (m, 2H).
Example 215: cis-4-(2-Cyclopropylmethoxy-4-flLioro-plienyl)-5H-pyrrolo[3,2-c'}pyrimidine-7-carboxylic acid [4-((S)-2-hydroxy'prGpionylamino)-cyclohexyl]-amide
Starting from cis-4-(2-cyclopropylmet lioxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyIic acid (4-amino-cyclohexyl)-amide (example A156) and acetic acid (S}-1-cfilorocarbonyl-etiiyl ester the title compound is obtained as colorless solid. MS (ESJ): m/2 = 496 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-de): 11.95 (br.s, 1H, -NH); 9.08 (s. 1H); 8.64 (d, J = 7.4, 1H; -NH); 8.28 (s, 1H); 7.68 (dd, J1 = 8.4, J1 = 7.1,1H); 7.50 (d, J = 7.7, 1H, -NH); 7.09 (dd, J, = 11.5, J2 = 2.2, 1H); 6.97 (ddd, J, = J2 = 8.5, J3 = 2.2, 1H); 5.37 (d, J = 5.4, 1H, -OH); 4.07 (m, 1H); 3.99 (m, 1H); 3.93 (d, J = 6.9, 2H); 3.76 (m, 1H); 1.82-1.59 (m, 8H); 0.97 (m, 1H); 0.37 (m, 2H); 0.22 (m, 2H).
Example 216: cis-4-(2-Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartxDxylie acid {4-[(1-hydroxy-cyclopropanecarbonyl)-amino]-cyclohexyl}-amide Starting from cis-4-(2-cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A156) and acetic acid 1-chlorocarbonyl-cyclopropyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 508 (MH+. 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.03 (br.s, IN, -NH); 9.09 (s, IN); 8.67 (d, J = 7.4, 1H; -NH); 8.28 (s. 1H);7.68(dd, J1 = 8.4, J2 = 7.0,1H);7.55(d,J = 7.8, 1H,-NH); 7.09 (dd, J1 = 11.5, J; = 2.2, 1H); 6.97 (ddd, J1 = J2 = 8.5, J3 = 2.2, 1H); 6.25 (s, 1H, -OH); 4.09 (m, 1H); 3.93 (d, J ^ 7.0, 2H); 3.78 (m. 1H); 1.85-1.64 (m, 8H); 1.03 (m, 2H); 0.97 (m, 1H); 0.83 (m, 2H); 0.37 (m, 2H); 0,22 (m, 2H).
Example 217: trans-4-(2-Cyclopropylmethoxy-4-fluQro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyllc acid [4-(2-hydroxy-acetylamino)-cyclohexyl]-amide

starting from trans-4-{2-cyclopropylmethoxy-4-fluoro-phenyt}-5H-pyrrolo[3.2-c(lpyrimidine-7-carboxylic acid {4-amino-cyclohexyi)-amide (example A157) acetic acid chlorocarbonyl-methyl ester the title compound is obtained as colorless solid.
MS (ESI); m/z = 482 (MM*, 100 %).
1H-NMR (400 MHz, DMSO-d6): 12.05 (br.s, IN, -NH); 9.04 (s, 'IN); 8.35 (d, J = 7.9, 1H; -NH); 8.27 (d, J = 3.3, 1H); 7.67 (dd, J1 = 8.4. J2 = 7.2, 1H); 7.47 (d, J = 8.2, 1H, -NH); 7.07 (dd, J, = 11.5, J2 = 2.2, 1H); 6.96 (ddd, J, = J2 = 8.5, J3 = 2.2, 1H); 5.41 (t, J = 5.7, 1H, -OH); 3.92 (d, J = 7.0, 2H); 3.79 (d, J = 5.7, 2H & m, 1H); 2.02 (m, 2H); 1.83 (m, 2H); 1.46 (m, 4H); 0.96- (m, 1H); 0.36 (m, 2H); 0.22 (m, 2H).
Example 218; trans-4-(2-Cyc)opropyfmelhoxy-4-fluoro-plienyl)-5H-pyrrolo[3,2-d]pyrimldine-7-carbDxylicacld[4-((S)-2-hydroxy-propionylamino)-cyclohexyl]'amide Starting from trans-4-(2-cyclopropylmethoxy-4-fluorG-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cydohexyl)-amide (example A157) and acetic acid (S)-1-chtorocarbonyi-ethyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 496 (MH\ 100 %).
1H-NMR (400 MHz, DMSO-d6): 12.05 (br.s, 1H, -NH); 9.04 (s, 1H); 8.35 (d, J = 7,8, 1H; -NH); 8.27 (d, J = 3.3, 1H); 7.67 (dd, J, = 8.4, J2 = 7.2, 1H); 7.41 (d, J = 8.2, 1H, -NH); 7.07 (dd, J, = 11,5, Js = 2.2, 1H); 6.96 (ddd, J, = Jj = 8.5, J3 = 2.2, IN); 5.41 (d. J = 5.2, 1H, -OH); 3.92 (d, J = 7.0, 2H & m, 1H); 3.781 (m. 1H); 3.64 (m, 1H); 2.03 (m, 2H); 1.81 (m, 2H); 1.44 (m, 4H); 1.21 (d, J = 6.7, 3H); 0.96 (m, 1H); 0.36 (m, 2H); 0.22 (m, 2H).
Example 219: trans-4-(2-Cyclopropylmethoxy-4-fluoro-ptienyl)-5H-pyrrolo[3,2-rf]pyrimidine-7-carboxylic acid(4-[(1-hydroxy-cyclopropanecarbonyl)-amino]-cyclohexyl}-amide Starting from trans-4-(2-cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolot3,2-d)pyrimidine-7-carboxylic acid (4-amino-cyclohexy()-amide (example A157) and acetic acid l-chlorocarbonyl-cyclopropyl ester the title compound is obtained as colorless solid. MS (ESI); m/z = 508 (MH+, 100 %).
1H-NMR (400 MHz, DMSO-d6); 12.05 (br.s, 1H, -NH); 9.04 (s, 1H); 8.35 (d, J = 7.9, 1H; -NH); 8.27 (s, 1H); 7.67 (dd, J, = 8.4, J1 = 7.2, 1H); 7.56 (d, J = 8.4,1H, -NH); 7.07 (dd. J1 = 11.5, J2 = 2.2, 1H); 6.96 (ddd, J, = J2 = 8.5, J3 = 2.2, 1H); 6.20 (s, 1H, -OH); 3.92 (d, J = 7.0, 2H); 3.83 (m, 1H); 3.68 (m, 1H); 2.03 (m, 2H); 1.81 (m, 2H); 1.44 (m, 4H); 1.02 (m, 2H); 0.96 (m, 1H); 0.82 (m, 2H); 0.36 (m,2H); 0.22 (m,2H).
Example 220; 4-(2-Cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2-o(lpyrimidine-7-carboxylic acid [1-(2-hydroxy-acetyl)-piperidin-4-ylJ-amide

Starting from 4-(2-cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide hydrochloride {example A159} and acetic acid chlorocarbonyl-methyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 468 (MH\ 100 %).
1H-NMR (300 MHz, DMSOKle,): 12.11 (br.s, 1H, -NH); 9.05 (s, 1H); 8.49 (d, J = 7.7, 1H, -NH); 8.31 {s, 1H); 7.44 (dd, J1 = 8.9, J2 =3.2, 1H); 7.38 (ddd, J1 =J2 = 9.1, J3= 3.2, 1H); 7.19 (dd, J1 =9.1, J2 = 4.4, 1H); 4.51 (t, J = 5.4, 1H, -OH); 4.18 (m, 2H); 4.13 (d. J = 5.4, 2H); 3.88 (d, J = 6.9, 2H); 3.69 (m, 1H); 3.19 (m, 1H); 2.99 (m, 1H); 1.98 (m, 2H); 1.57 (m, 1H); 1.42 (m. 1H); 0.94 (m, 1H); 0.34 (m.2H);0.19{m, 2H).
Example 221: 4-(2-Cyclopropy!methoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2-(yipyrimidine-7-carboxylic acid [1-((S)-2-hydroxy-propionyl)-piperidin-4-yl]-amide
Starting from 4-(2-cyclopropylmethoxy-5-fluoro-phenyi)~5H-pyrrolo[3.2-cf]pyrimidine-7-carboxylic acid piperidin-4-ylamide hydrochloride (example A159) and acetic acid (S)-1-chlorocarbonyl-ethyi ester the title compound is obtained as colorless solid. MS (ESI): m/z = 482 (MM*, 100 %).
1H-NMR (300 MHz, DMSO-d6,): 12.11 (br.s, 1H,-NH); 9.05 (s, 1H); 8.49 (d, J = 7.7, 1H,-NH);8.31 (s, 1H); 7.44 (dd, J1 = 8.9, J2 =3.2, IN); 7.38 (ddd, J1 = J2 = 9.1, J3 = 3.2, 1H); 7.19 (dd, J1 = 9.1, J2 = 4.4, IN); 4.86 (d, J = 7.0, IN,-OH); 4.47(m, 1H); 4.31-4.10 (m, 2H); 3.97 (m, 1H); 3.88 (d, J = 6.9, 2H); 3.28 (m, 1H); 2.97 (m, 1H); 1.99 (m, 2H); 1.55 (m, 1H); 1.44 (m, 1H); 1.20 (br.s, 3H); 0.94 (m, 1H); 0.34 (m, 2H); 0.19 (m, 2H).
Example 222: trans-4-(2-Cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2-c(]pyrimtdine-7-carboxylic acid [4-(2-hydroxy-acetylamino)-cyclohexyl-amide
Starting from trans-4-(2-cyclopropylm ethoxy-5-ftuoro-pheny I )-5H-pyrrolo[3,2-d]pyrimidIne-7-cartraxylic acid (4-amino-cyclohexyl)-amide (example A160) acetic acid chlorocarbonyl-methyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 482 (MH\ 100 %).
1H-NMR (300 MHz, DMSO-d6,): 12.08 (br.s, 1H, -NH); 9.06 {s, 1H); 8.34 (d, J = 7.9, 1H,-NH), B.29 (d, J = 3.3, 1H); 7.4? (d. J = 8.9, 1H, -NH); 7.44 (dd, J1 = 8.9. J2 = 3.3, 1H); 7.38 (ddd, J, = J^ = 9.2, J3 = 3.3, 1H); 7.19 {dd, J1 = 9.2, J2 = 4.4, 1H); 5.39 (br.s, 1H, -OH); 3.88 (d, J = 6.9, 2H); 3.79 (m, 1H & s, 2H); 3.70 (m, 1H); 2.02 (m, 2H); 1.83 (m, 2H); 1.45 (m, 4H); 0.94 (m, 1H); 0.34 (m, 2H); 0.18 (m,2H).
Example 223: trans-4-(2-Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimldine-7-carboxyllc acid [4-({S)-2-hydroxy-propionylamino)-cyclohexyl]-amide

starting from trans-4-(2-cyclapropylmelhoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2-c(|pyrinnidine-7-carboxylic acid (4-amino-cyclohexyl}-amide (example A160) and acetic acid (S)-1-chilorocarbonyl-ethiyl ester tine title compound is obtained as colorless solid. MS (ESI): m/z = 496 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6,): 12.08 (br.s, 1H, -NH); 9.06 (s, 1H); 8.34 (d, J = 7.8, 1H,-NH), 8.28 (s, 1H); 7.46-7.34 (m, 3H): 7.19 (dd, J1 =9.2, J2 = 4.4, 1H); 5.41 (d, J = 5.1 1H,-0H); 3.95 (m, 1H); 3.88 (d, J = 6.9, 2H); 3.86 (m, 1H); 3.64 (m, 1H); 2.01 (m, 2H): 1.83 (m, 2H); 1.44 (m, 4H); 1.21 (d, J = 6.8, 3H); 0.94 (m, 1H); 0.34 (m, 2H); 0.18 (m, 2H).
Example 224: frans-4-(2-Cyclopropy(methoxy-phenyl)-5H-pyrrolo[3,2-c3]pyrimidine-7-carboxylic acid (4-(2-hydroxy-acetylamino)-cyclohexylJ-amide
Starting from trans-4-(2-cyclQpropylmethQxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyllc acid (4-amino-cyclohexyl)-amide (example A161) acetic acid chlorocarbonyl-methyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 464 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.03 (s, 1H, -NH); 9.05 (s, IN); 8.36 (d, J =^ 7.8, 1H, -NH); 8.24 (s, 1H);7.64(dd, J, = 7.6, J2= 1.8, 1H); 7.53 (ddd, J1 = 7.9. J2 = 7.6, J2 = 1.8, 1H); 7.48 (d, J = 8.3, 1H, -NH); 7.17 (dd, J, = 7.9, J2 = 0.9, 1H); 7.13 (ddd, J, = J2 = 7.6, J3 = 0.9, 1H); 5.41 (t, J = 5.7, 1H, -OH); 3.91 (d, J = 6.9, 2H); 3.80 (d, J = 5.7, 2H & m, 1H); 3.70 (m, 1H); 2.02 (m, 2H); 1.82 (m, 2H); 1.48 (m, 4H); 0.96 (m, 1H); 0.35 (m, 2H); 0.22 (m, 2H).
Example 225: trans-4-(2-Cyclopropylmeltioxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-{(S)-2-hydroxy-propionylamino)-cyclohexyl]-amide
Starting from trans-4-(2-cycloprDpylmethoxy-phenyl)-5H-pyrrolo(3,2-c/]pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A161) and acetic acid (S)-1-chlorocarbonyl-ethyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 478 (MH+. 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.02 (s. IN,-NH); 9.05 (s, 1H); 8.36 (d, J = 7.9, 1H,-NH); 8.24 (s, 1H); 7.64 (dd, J1 = 7.6, J2 = 18, 1H); 7.53 (ddd. J1 = 7.9, J? = 7.6, J3 = 18, IN); 7.24 (d, J = 8.3, 1H, -NH); 7.17 (dd, J1 = 7.9, J2 = 0.9, 1H); 7.13 (ddd, J1 = J2 = 7.6, J3 = 0.9,1H); 5.42 (d, J = 5.2, 1H, -OH); 3.95 (m, 1H); 3.91 (d, J = 6.9, 2H); 3.82 (m, 1H); 3.64 (m, 1H); 2.02 (m, 2H); 182 (m, 2H); 1.43 (m,4H); 1.21 (d, J = 6.8, 3H); 0.96 (m, 1H); 0.35 (m, 2H); 0.22 (m, 2H).
Example 226: trans-4-(2-Cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4-[(1-hydroxy-cydopropanecarbony()-aminoI-cyc[ohexy(}-amide Starting from trans-4-(2-cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cydohexyl)-amide (example A161) and acetic acid l-chlorocartronyl-cyclopropyl ester the title compound is obtained as colorless solid.

MS (ESI): m/z = 490 (MH\ 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.02 (s, 1H, -NH); 9.05 (s, 1H); 8.36 (d, J = 7.8, 1H, -NH); 8.24 (s, 1H); 7.63 (dd, J, = 7.6, J2 = 1.8, 1H); 7.57 (, J = 8.8, 1H, -NH); 7,53 (ddd, J, = 7.9, J2 = 7,6, J3 = 1.8. 1H); 7.17 {dd,J1= 7.9, J2 = 0.9, 1H); 7,13 (ddd, J, = Js = 7.6, Js^ 0,9, 1H); 6.20 (s, 1H,-OH); 3.91 (d, J = 6.9, 2H);3.82(m, 1H); 3,70 (m, 1H); 2.02 (m, 2H); 1.83 (m, 2H); 1.48 {m, 4H); 1.02 (m, 2H); 0.95 (m, 1H); 0.82 (m, 2H); 0.35 (m, 2H}; 0,22 (m, 2H),
Example 227: 4-(2-Cyclopropylmethoxy-ptienyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxy!ic acid [1-((S)-2-hydroxy-proptonyl)-piperidin-4-yl]-amide
Starting from 4-(2-cyclopropylnnethoxy-plnenyl)-5/-f-pyrrolo[3,2-d]pyrimidin8-7-carboxy[ic acid piperidin-4-ylamide (example A162) and acetic acid (S)-1-chlorocarbonyi-etliyl ester the title compound is obtained as colorless solid. MS (ESI); m/z = 464 (MH\ 100 %).
1H-NMR (300 MHz, DMSO-d6): 12,05 (s, 1H, -NH); 9,05 (s, 1H); 8,52 (d, J = 7.8, 1H, -NH): 8.26 (s, 1H); 7,64 (dd, J, = 7.6, J2 = 1.7, 1H); 7,53 (ddd, J, = 8.0, J2 = 7.6, J3 = 1.7. 1H); 7.17 (dd, J, = 8.0, Jj = 0.9, IN); 7.13 (ddd, J, = J2 = 7,6, J3 = 0.9, 1H); 4.87 (d, J = 6,9, 1H, -OH); 4.47 (m, 1H); 4.21 (m, 1H); 4.17 (m, 1H): 3.98 (m, 1H); 3,91 (d, J = 6,8, 2H); 3.28 (m, 1H); 2.98 (m, IN); 1.99 (m, 2H); 1.53 (m, 1H); 1.44 (m, 1H); 1.21 (br.s, 3H); 0.96 (m, 1H); 0.36 (m, 2H); 0.22 (m, 2H),
Example 228: 4-(2-Cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrola[3,2-c(]pyrimidine-7-carboxylic acid [1-((S)-2-hydroxy-propionyl)-piperidin-4-yl]-amide Starting from 4-(2-cyclopropylnnethoxy-4-fluoro-5-methoxy-ptienyl)-5H-pyrroloI3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide (example A163) and acetic acid (S)-l-chlorocarbonyl-ethyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 512 (MM*, 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.03 (br.s, 1H, -NH); 9.05 (s, 1H); 8.50 (d, J = 7.8, 1H, -NH); 8,29 (s, 1H); 7.41 (d, J = 9.8, 1H); 7,18 (d, J = 13.4, 1H); 4,86 (d, J = 7.0, IN, -OH); 4,47 (m, 1H); 4,20 (m, 2H);3,97(m, 1H); 3,85 (s, 3H &d, J = 6,8, 2H); 3,30 (m, 1H); 2.97 (m, 1H); 1.99 (m,2H); 1.53 (m, 1H); 1.44 (m, 1H); 1,21 (br.s, 3H); 0.92 (m, 1H); 0.34 (m, 2H); 0.17 (m, 2H).
Example 229: 4- 1H-NMR (300 MHz, DMSO-d6): 11.87 (br.s, 1H, -NH); 9.02 (s, 1H); 8,61 (br.m, 1H, -NH); 8.30 (s, 1H); 7,41 (d, J = 9.9, 1H); 7.18 (d, J = 13.3, 1H); 4.46 (br.m, 1H, -OH); 4,15 (br.s, 1H); 4.08 (br.s,

1H); 4.02 (m, 1H); 3.85 (s, 3H & d, J = 6.8, 2H); 3.69-3.40 (m, 2H); 3.40-3.19 (m, 2H); 1.98 {m, 1H); 1.76 (m, 2H); 1.58 (m, 1H); 0.93 (m, 1H); 0.33 (m, 2H); 0.18 (m, 2H).
Example 230: 4-(2-Cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1-((S)-2-hydroxy-propionyl)-piperidin-3-yl]-amide Starting from 4-(2-cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-c(]pyrimldine-7-carboxyfic acid (R)-prperrdin-3-ylamfde hydrochloride (example A164) and acetic acid (S}-1-chlorocarbonyl-ethyl ester the title compound is obtained as colorless solid. MS(ESI):m/z=512(MH\ 100%).
1H-NMR (300 MHz, DMSO-d6): 11.91 {br.s, 1H, -NH); 8.04(s, 0.5H); 9,00 {s, 0,5H); 8.57 (d, J = 7.7, 1H, -NH); 8.30 (br.s, 1H); 7.41 {d, J = 9.8, IN); 7.18 (d, J = 13.3, 1H); 4.76 (~d, 0,5H, -OH); 4.62 (~d, 0.5H, -OH); 4.46 {m, 1H); 4.12-3.84 (m, 2.5H); 3,85 (s, 3H & d, J = 6.8. 2H); 3.59 (m, 0.5H); 3.38(m, 1H); 3.20 (m, 1H); 1,99 (m, 1H); 1.76 (m, 2H); 1.52 (m, 1H); 1.24 (br.s, 3H); 0.93 (m, 1H); 0.363 (m, 2H); 0.18 (m,2H).
Example 231: 4-(2-Cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-c/]pyrimidine-7-carboxylic acid [(R)-1-(2-hydroxy-acetyl)-pyrrolidin-3-yl]-amide Starting from 4-(2-cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartwDxylic acid (R>-pyrrolidin-3-ylanride hydrochloride (example A165) and acetic acid chlorocarbonyl-methyl ester the title compound is obtained as colorless solid. MS (ES(): m/z = 464 (MH+, 100 %).
1H-NMR(400MHz, DMSO-d6): 11,35 (br.s, 1H,-NH); 9.05 (s, 1H);8.61 (d, J = 7.0,1H,-NH); 8.59 (d, J = 7.0, 0.5H, -NH); 8.31 (s, 1H); 7.41 (d, J = 9.8, 1H); 7.18 (d, J = 13.4, 1H); 4.63 (m, 0.5H); 4.51 (m, 0.5H & br.s, IN, -OH); 4.06 (s, IN); 3.86 (s, 1H); 3.84 (s, 3H & d, J 0 4.4, 2H); 3.80-3.70 (m, 1H); 3.62-3,44 (m, 1.5H); 3.41-3.29 (m, 1.5H); 2.33-2.17 (m, IN); 2.07 (m, 0.5H); 1.93 (m, 0.5H); 0.92 (m, 1H); 0.33 (m, 2H); 0.17 (m, 2H).
Example 232: 4-(2-Cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrok>[3,2-dlpyrimidine-7-carboxylic acid [(R)-1-({S)-2-hydroxy-propionyl)-pyrrolidin-3-yl]-amide Starting from 4-(2-cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (R}-pyrTolldin-3-ylamide hydrochloride (example A165) and acetic acid (S)-1-chlorocarbonyl-ethyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 498 (MH+. 100 %).
1H-NMR (400 MHz, DMSO-d6): 11.61 (br.s, 1H, -NH); 9.04 (s, 0.5H}; 9.01 (s, 0.5H); 8.61 (d, J = 6.9, 1H, -NH); 8.59 (d, J = 7.0, 0,5H, -NH); 8.31 (s, 1H); 7.41 (d, J = 9.8, 1H); 7.18 (d, J = 13.4, IN); 4.91 (d, J = 6.8, 0.5H, -OH); 4,86 (d, J = 6,8, 0.5H, -OH); 4.60 (m, 0.5H); 4.53 (m, 0.5H); 4.26 (m, 0.5H); 4.02 (m, 0.5H); 3.84 (s, 3H & d, J 0 4.4, 2H); 3.82-3.72 (m, 1H); 3.71-3,52 (m, 2.5H);

3.47 (m, 0.5H); 3.40-3-30 (m, 1H); 2.33-2.17 (m, 1H); 2.07 (m. 0.5H); 1.93 (m, 0.5H); 1.23 (d, J = 6.6, 1.5H); 1.20 (d, J = 6.6, 1.5H); 0-92 (m, 1H); 0.33 {m, 2H); 0.17 (m, 2H).
Example 233: trans-4-(2-Cyc!opropyimethoxy-5-fluoro-4-methoxy-phenyl)-5j4-pyrro(o[3,2-d]pyrimidine-7-carboxylic acid [4-(2-hydroxy-acetylamino)-cyclohexyl]-amide Starting from trans-4-(2-cyclopropylmethoxy-5-fluoro-4-methoxy-pheny!)-5H-pyrrolo[3,2-cf]pyrimidine-7-carboxylic acid {4-amino-cyclohexyl)-amide {example A139) and acetic acid chlorocarbonyl-methyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 512.1 (MH+, 100%)
1H-NMR (300 MHz. DMSO-d6): 11.95 (br.s, 1H, -NH); 9.01 (s, 1H); 8.36 (d, J = 7.8, 1H, -NH); 8.24 (d,J = 2.6, 1H); 7.50 (d, J =11.8, 1H); 7.47 (d, J = 8.3,1H,-NH); 6.93 (d, J = 7.3, 1H):5.41 (t, J = 5.8, 1H, -OH): 3.97 (s, 3H); 3.95 (d, J = 7.1, 2H}; 3.79 {m, 1H & d, J = 5.8, 2H); 3.69 {m, 1H); 2.03 (m, 2H); 1.82 (m, 2H); 1.46 (m, 4H): 0.96 (m, 1H): 0.35 (m, 2H); 0.21 (m, 2H).
Example 234: trans-4-(2-Cyclopropylmethoxy-5-fluorc-4-methoxy-ptienyl)-5H-pyrrolo[3,2-d]pyrimidtne-7-carboxyllc add [4-((S)-2-hydroxy-proplonylamino)-cyclohexyl]-amide Starting from trans-4-(2-cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-cflpyrJmJdine-7-carboxylic add (4-amino-cyclohexyl)-amide [example A139) and acetic acid (S)-1-chlorocarbonyl-ethyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 526 (MH+, 100%).
■H-NMR (300 MHz, DMSO-d6): 11.95 (br.s, 1H, -NH); 9.01 (s, 1H); 6.36 (d, J = 7.9, 1H, -NH); 8.25 (s IN); 7.50 (d, J = 11.8, IN); 7.42 (d, J = 8.3, 1H, -NH); 693 (d, J = 7.3, 1H); 5.41 (d, J = 5.2, 1H, -OH); 3.97 (s, 3H); 3.94 (d, J = 7.1, 2H & m, IN); 3.81 (m, 1H); 3.64 (m, 1H): 2.03 (m, 2H); 1.81 (m, 2H); 1.44 (m, 4H); 1.21 (d, 3H); 0.97 (m, 1H); 0.36 (m, 2H); 0.21 (m, 2H).
Example 235: tran5-4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrroio[3,2-d]pyrlmidlne-7-carboxylic acid {4-[{1-hydroxy-cyclopropanecarbonyl)-amino]-cyclohexyl}-amide Starting from trans-4-(2-cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-c(]pyrlmidlne-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A139) and acetic acid 1-chlorocarbonyl-cydopropyl ester the title compound Is obtained as colorless solid. MS (ESI): m/2 = 538 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 11.95 (br.s, 1H,-NH); 9.01 (s, IN); 8.36 (d, J = 7.9, 1H,-NH);8.25 (s, 1H); 7.57 (d, J = 8.4, 1H, -NH); 7-49 (d, J = 11.8, 1H); 6,93 (d, J = 7.3, 1H); 6.20 (s, 1H, -OH); 3.97(s, 3H);3.95(d, J = 7.1,2H);3.81 (m, 1H); 3.69 (m, 1H); 2.02 (m. 2H); 1.83 (m,2H); 1.48 (m, 4H); 1.02 (m, 2H); 0.97 (m, 1H); 0.82 (m, 2H); 0.36 (m, 2H); 0.21 (m, 2H).
Example 236: 4-(2-Cyclopropylmethoxy-5-fluoro-4~methoxy-phenyl)-5H-pyrrolo[3,2-djpy rim id i ne-7-carboxy lie add [1 -(2-hydroxy-ethanoy l)-piperidin-4-y l]-amide

starting from 4-(2-cyciopropylmethoxy-5-fiuoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrlmidine-7-carboxylic acid piperidin-4-ylamide hydrochloride (example A166) and acetic acid chlorocarboryl-methyl ester the title compound is obtained as colorless solid. MS (ESI): m/2 = 496 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 11-97 (br.s, 1H, -NH); 9.01 (s, 1H); 8.52 (d, J = 7.8, 1H, -NH); 8.27 (d,J = 3.3. 1H);7.48(d, J= 11.9, 1H); 6.93 (d, J = 7.3, 1H);4.51 (t, J = 5.2, 1H,-0H); 4,18 (m, 2H); 4.13(dd, J1 = J2 = 5.2, 2H); 3.97 (m, 3H); 3.95 (d, J = 7.2, 2H); 3.69 (m, 1H); 3.19 (m, 1H); 2.99 (m, 1H); 1.98 (m, 2H); 1.56 (m, 1H); 1.45 (m, 1H); 0.97 (m, 1H); 0.36 (m, 2H); 0.22 (m, 2H).
Example 237: 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-dlpyrimidine-7-carboxylic acid [1-{(S)-2-hydroxy-propanoyl)-piperidin-4-yl]-amide Starting from 4-(2-cyclopropylmethoxy'5-fluoro-4-methoxy-phenyl)-5H-pyrroloI3,2-c(]pyrimidine-7-carboxylic acid piperidin-4-ylamide hydrochloride (example A166) and acetic acid (S)-1-chlorocarbonyl-ethyl ester the title compound is obtained as colorless solid. MS(ESI):m/z=512 1H-NMR (300 MHz, DMSO-d6): 11.98 (br.s, 1H, -NH); 9.01(s, 1H); 8.52 (d, J = 7.8, 1H, -NH); 8.27 (s, 1H); 7.50 (d, J = 11.9, 1H); 6.93 [d, J = 7.3, IN); 4.86 (d, J = 6.9, 1H,-OH); 4.47 (m, 1H);4.20 (m, 2H); 3.97 (s, 3H & m, IN); 3.95 (d, J = 7.1, 2H): 3.29 (m, 1H); 2.97 (m, 1H); 1.98 (m, 2H); 1.53 (m, IN); 1.43 (m, 1H); 1.21 (br.s, 3H); 0.97 (m, 1H); 0.36 (m, 2H); 0.22 (m, 2H).
Example 238: 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyl(c acid {1-[1-{1-hydroxy-cyclopropyl-methanoyl]-piperidin-4-yl}-am(de Starting from 4-(2-cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid pipe rid in-4-ylamide hydrochloride (example A166) and acetic acid 1-chlorocarbonyl-cyclopropyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 524 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 11,98 (br.s, 1H, -NH); 9.02 (s, 1H); 8.53 (d, J = 7.8, 1H, -NH); 8.27 (s, 1H); 7.50 (d, J = 11.8, 1H); 6.93 (d, J = 7.3, 1H); 6.31 (s, 1H,-OH); 4.28 (m. 1H); 4.18 (m, 2H); 3.97 (s, 3H); 3.95 (d, J = 7.2, 2H); 3.16 (m, 2H); 1.99 (m, 2H); 1.52 (m, 2H); 0.95 (m, 1H & m, 2H); 0.77 (m, 2H); 0.37 (m, 2H); 0.22 (m, 2H).
Example 239: 4-(2-cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl}-5H-pyrrolo[3,2-c(]pyrimidine-7-cartioxylic acid [(S)-1-((S>2-hydroxy-propanoyl)-piperidin-3-yl]-amide Starting from 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartxjxylic acid (S)-p)per]din-3-ylamide hydrochloride (example A168) and acetic acid (S)-1-chlorocarfaonyl-ethyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 512 (MH+; 100 %).

1H-NMR (300 MHz, DMSO-d6): 11.99 (br.s, 1H, -NH); 8.99(s, IN); 8.58 (d, J = 7.7, 1H, -NH); 8.27 {br.s, 1H); 7.50 (d, J = 11.9, IN); 6.93 (d, J = 7.3, 1H); 4.87 {-d, 0.5H,-OH); 4.81 {-d, 0.5H,-OH); 4.46 (m, 1H); 4.05 (m, 0.5H); 3.97 (s, 3H); 3.94 (d, J = 7.2, 2H & m, 2H); 3.70 (m, 1H); 3.34(m, 1H); 3.14 (m, 0.5H); 1.99 (m. 1H); 1.76 (m,2H); 1.56 (m, 1H); 1,21 (-d, 1,5H); 1.13 (~d, 1,5H); 0.97 (m, 1H); 0.36 (m,2H); 0.21 (m, 2H).
Example 240: 4-(2-CyclopropylrDethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-cflpyrimidine-7-carboxylic acid KR)-1 -((S)-2-hydroxy-propanoyl)-piperidin-3-yl]-amide Starting from 4-(2-cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-cdpyrimidine-7-carboxylic acid (R)-piperidin-3-ylamide hydrochloride (example A167) and acetic acid (S}-1-chlorocarbonyl-ethyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 512 (MH+; 100 %),
1H-NMR (300 MHz, DMSO-d6): 11.98 (br.s, 1H, -NH); 8.99(s, 0.5H); 8.96 (s, 0.5H); 8.57 (d, J = 7.7, IN, -NH); 8.27 (br.s, 1H); 7.50 (d, J = 11.9, 1H); 6,93 (d, J = 7,3, 1H); 4.76 (-d, 0.5H, -OH); 4.62 (~d, 0.5H, -OH); 4.46 (m, 1H); 4.06 (m, 0,5H); 3.97 (s, 3H); 3.94 (d, J = 7.2, 2H & m, 2H); 3.59 (m, 0,5H); 3,38(m, 1H); 3,20 (m, 1H); 1.98 (m, 1H); 1.76 (m, 2H); 1.52 (m, 1H); 1.24 (br.s, 3H); 0,97 (m, 1H); 0.36 (m,2H); 0.22 (m,2H),
Example 241: 4-(2-Cyc(opropylmethoxy-5-f]uoro-4-methoxy-phienyl)-5H-pyrrolo[3,2-cf\pyrimidine-7-carboxylic acid [(R)-1 -(2-hydroxy-acetyl)-pyrrolidin-3-yl]-amide Starting from 4-(2-cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo(3,2-cf]pyrimidine-7-carboxylic acid (R)-pyrroiidin-3-ylamide hydrochloride (example A169) and acetic acid chlorocarbonyl-methyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 484 (MH+, 100 %),
1H-NMR (300 MHz, DMSO-d6/MeOH-di): 9.01 (s, 1H); 8,63 (d, J = 7.3, 0.5H; -NH); 8.61 (d, J = 7.3, 0.5H,-NH); 8.29 (s, 1H); 7.49 (d, J = 11.8, 1H); 6.92 (d, J = 7.3, 1H); 4.62 (m, 0.5H); 4.52 (m, 0.5H); 4.06 (s, 1H); 4,01 (s, 1H); 3,97 (s, 3H); 3,95 (d. J = 7,0, 2H); 3.77 (m, 1H); 3.53 (m, 1.5H); 3.36 (m, 1.5H); 2.33-2.17 (m, 1H); 2,07 (m, 0.5H); 1.93 (m, 0.5H); 0.96 (m, 1H); 0.36 (m, 2H); 0.21 (m,2H).
Example 242: 4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-ptienyl)-5H-pyrrolo[3,2-c/lpyrimidine-Z-carboxylic acid [(R)-1-((S)-2-hydroxy-propronyl)-pyrrolidin-3-yl)-amide Starting from 4-(2-cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (R)-pyrrolidin-3-ylamide hydrochloride (example A169) and acetic acid (S)-1-chlorocartonyl-ethyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 498 (MH+, 100 %).
1H-NMR (300 MHz. DMSO-d6): 11.86 (br.s, 1H, -NH); 9,00 (s, 0,5H); 8.97 (s. 0,5H); 8.64 (d, J = 7.0, 1H;-NH);8.28(s, 1H); 7.50 (d, J = 11.8); 6.92 (d, J = 7.2, 1H);4.91 (d, J = 6.8, 0.5H,-OH);

4.85 {d, J = 6.8, 0.5H, -OH); 4.60 (m, 0.5H); 4.55 {m, 0,5H); 4.41 (m, 0.5H): 4.26 {m, 0.5H); 3.97 (s, 3H); 3.95 (d, J - 7,0, 2H); 3.83 (m, 0.5H); 3.78 (m, 0.5H); 3.71-3.53 (m, 1.5H); 3.34 (m, IN); 2.29 (m, 0.5H); 2.19 (m, 0.5H); 2.07 (m, O.SH); 1.95 (m, 0.5H); 1.23 {d, J = 6.5, 1.5H); 1.19 (d, J = 6,5, 1.5H); 0.96 (m, 1H); 0.36 (m, 2H), 0.22 (m, 2H).
Example 243: trans-4-(2-Cyclopropylmethoxy-5-nnethyl-phenyl)-5H-pyrrolo(3,2-cr|pyrimrdine-7-carboxylic acidf4-(2-hydroxy-acetyiani(no)-cyclohexyl)-amide Starting from trans-4-(2-cyclopropylmethoxy-5-methyl-pheny!)-5H-pyrrolo[3,2-c/lpyrJmidine-7-carboxylic acid (4-amino-cydohexyl)-amide (example A170) and acetic acid chlorocarbonyl-methyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 478 (MH+, 100 %).
1H-NMR400MHZ, DMSO-d6): 11.96 (br.s, 1H,-NH); 9,03 (s, 1H); 8.36 (d, J = 7,8, 1H,-NH);8.22 (s, 1H); 7.47 (d, J = 8.2, 1H. -NH); 7.44 (s, 1H); 7.33 {d, J = 8,4, 1H); 7.06 (d, J = 8.4, 1H); 5.41 (t, J = 5.6, 1H, -OH); 3.66 (d, J = 6,8, 2H); 3.79 (d, J = 5.6, 2H & m, 1H); 3.69 (m, 1H); 2.33 (s, 3H); 2,02 (m, 2H); 1.83 (m, 2H); 1.47 (m, 4H); 0.93 (m, 1H); 0.34 (m, 2H); 0.19 (m, 2H).
Example244: trans-4-{2-Cyclopropy)methoxy-5-methyl-phenyl)-5H-pyrrolQ[3,2-c^py^imidine-7-carboxylic acid [4-{(S)-2-hydroxy-propionyiamino)-cyclohexyl]-amide Starting from trans-4-(2-cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A170) and acetic acid (S)-l-chlorocarbonyl-ethyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 492 (MM*, 100 %).
1H-NMR 300 MHz, DMSO-d6): 11.96 (br.s, 1H, -NH); 9.03 (s. 1H); 8.36 (d, J = 7.9. 1H, -NH); 8.22 (s, 1H); 7.44 (d, J = 2.0, 1H); 7.42 (d, J = 10.0, 1H, -NH); 7.33 (dd, J, = 8.4, J^ = 2.0, 1H); 7.06 (d, J =8.4, 1H);5.41 (d, J = 6.1, 1H,-OH); 3.96 (m, 1H); 3.86(d, J = 6.8, 2H & m, 1H);3.64(m, 1H); 2.32 (s, 3H); 2.03 (m, 2H); 1.81 (m, 2H); 1.44 (m, 4H); 1.21 (d, J = 6.8, 3H); 0.93 (m, 1H); 034 (m, 2H);0.19(m,2H).
Example 245: trans-4-(2-CyclopropylmethDxy-5-methyl-phenyl)-5H-pyrrolo[3,2-d] pyrimidine-7-carboxylic acid {4-[( 1 -hydroxy-cyclopropanecarbonyl)-amino]-cyclohexyl}-am id e Starting from trans-4-(2-cyclopropylmethoxy-5-methyl-ptienyl)-5fy-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cydohexyl)-amide (example A170) and acetic acid 1-chlorocarbonyI-cyclopropyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 504 (MH+, 100 %).
1H-NMR 300 MHz, DMSO-d6): 11.95 (br.s, 1H,-NH); 9.03 (s, 1H); 8.36(d, J = 7.9, 1H,-NH);8.22 (d, J = 3.4, 1H); 7.57 (d, J = 8.4, 1H, -NH); 7.44 (d, J = 2.1, IN); 7.33 (dd, J1 = 8.4, Jj = 2.1, 1H); 7.06 (d, J = 8.4, 1H); 6.20 (s, 1H, -OH); 3.86 (d, J = 6.9, 2H & m, 1H); 3.70 (m. 1H); 2.32 {s, 3H);

2.03 (m, 2H); 1.82 (m, 2H); 1.59-1.38 (m, 4H); 1.03 (m, 2H); 0.93 (m, 1H); 0.83 (m, 2H); 0.34 (m. 2H);0.19(m, 2H),
Example 246: 4-(2-Cyclopropyfmethoxy-5-methyl-pheny()-5H-pyrro(o[3,2-d]pyrimidine-7-carboxylic acid [1-(2-tiydroxy-acetyl)-piperidin-4-yl]-amide
Starting from 4-(2-cyclopropylmethoxy-5-metliyl-ptienyl)-5H-pyrrolo[3,2-d]pyrimtdine-7-carboxylic acid piperidin-4-ylamide (example A171) and acetic acid chlorocarbonyl-methyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 464 (MH', 100 %).
1H-NMR 400 MHz, DMSO-d6): 11.99 (br.s, 1H, -NH); 9.03 (s, 1H); 8.52 (d, J = 7.8, 1H, -NH); 8.25 (s, IN); 7.44 (d, J = 1.9, 1H); 7.33 (dd, J, = 8.5, J2= 1.9.1H); 7.06 {d, J = 8.5, 1H);4.51 (t, J = 5.4, 1H, -OH); 4.23-4.11 (m, 2H); 4.14 (d, J = 5.4, 2H); 3.87 (d, J = 6.9, 2H}; 3.69 (m, 1H); 3.20 {m, 1H); 3.00 {m, 1H);2.33(s, 3H); 1.99 (m,2H); 1.56 (m, IN); 1.44 (m, 1H);0.94(m, IN); 0.34 (m, 2H}; 0.19 (m,2H).
Example 247: 4-{2-Cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrrolo[3,2-c(!pyrimidine-7-carboxylie acid [1-((S)-2-hydroxy-propiony!)-piperidin-4-yl]-amide
Starting from 4-(2-cyc)opropylmethoxy-5-methyl-pheny))-5H-pyrro)o[3,2-c']pyrJmidine-7-carboxylic acid piperidin-4-ylamide (example A171) and acetic acid (S)-l-chlorocarbonyl-ettiyl ester the title compound is obtained as colorless solid. MS (ESI); m/z = 478 (MH+, 100 %).
1H-NMR400MHZ, DMSO-d6): 11.99 (br.s, 1H,-NH); 9.03 (s, 1H); 8.52 (d. J = 7.8, 1H,-NH);8.25 (s, 1H);7.44(d,J= 1.9, 1H); 7.33 (dd, J, =8.5, Jj^ 1.9, 1H); 7.06 (d, J = 8.5, 1H); 4.86 (d, J = 6.9, IN, -OH); 4.47 (m, 1H); 4.29-4.10 (m, 2H); 3.97 (m, 1H); 3.86 (d, J = 6.8, 2H); 3.29 (m, 1H); 3.97 (m, 1H);2.33(s, 3H); 1,99 (m, 2H); 1.57 (m,1H); 1.43 (m, 1H); 1.21 (br.s, 3H); 0.94 (m, IN); 0.34 (m,2H); 0.19 (m,2H).
Example 248: 4-(2-Cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylie acid [1-(1-hydroxy-cyclopropanecartxjnyl)-piperidin-4-yl]-amide Starting from 4-(2-cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrrolo[3,2-cqpyrimidine-7-carboxylic acid piperidin-4-ylamide (example A171) and acetic acid 1-chlorocarbonyl-cyclopropyl ester the title compound is obtained as colorless solid. MS (ESI): m/z = 490 (MH+, 100 %).
1H-NMR 400 MHz, DMSO-d6): 11.99 (br.s, IN, -NH); 9.03 (s, 1H); 8.53 (d, J = 7.9, 1H, -NH); 8.25 (s, 1H); 7.44 (d, J = 1.9, 1H); 7.33 (dd, J1 = 8.5, J2 = 1.9, 1H); 7.06 (d, J = 8.5, 1H); 6.31 (s, 1H, -OH); 4.28 (m, IN); 4.24-4.10 (m, 2H); 3.87 (d, J = 6.9, 2H); 3.17 (m, 2H); 2.33 (s, 3H); 1.99 (m, 2H); 1.53 (m, 1H); 0.94 (m, 3H); 0.77 (m, 2H); 0.34 (m, 2H); 0.19 (m, 2H).

Example 249: 4-{5-Ethoxy-ben2o[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-((S)-2-hydroxy-propionyl)-piperidin-4-yl]-amide
Starting from 4-{2-cyclopropylmethoxy'5-methyi-phenyl)-5h'-pyrrolo[3,2-d]pyrlmidine-7-carboxylic acid piperidin-4-ylamide (example A175) and acetic acid {S)-1-chlorocarbonyl-ethyl ester the title compound was obtained as colorless solid. MS (ESI): m/z = 482 (IV1H^ 100 %).
1H-NMR (400 MHz, DMSO-d6): 12.15 (s, 1H, -IMH); 9.02 {s, 1H); 8.45 (d, J = 7.7, 1H, -NH); 8.29 (s, 1H); 7.02 (d, J = 8.6, 1H); 6.58 (d, J = 8.6, 1H); 6,00 (s, 2H); 4.86 (d, J = 6.7, 1H, -OH); 4,47 (m, 1H); 4,31-4.10 (m, 2H); 3.96 (qu, J = 6.9, 2H & m, 1H); 3.27 (m, 1H); 2,97 (m, 1H); 1.99 (m, 2H); 1.62^1.31 (m, 2H); 1.20 (br.s, 3H); 1.03 (t, J = 6.9, 3H).
Example 250: 4-(5-Ethoxy-benzo[1,3jdioxol-4-yi)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1-((S)-2-hydroxy-propionyl)-pyrrolidin-3-yl]-amide
Starting from 4-(5-ethoxy-benzo[1,3Idioxai-4-yl)-5H'pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (R)-pyrrolidin-3-ylamide (example A176) and acetic acid (S)-l-chlorocarbonyl-ethyl ester the title compound was obtained as colorless solid. MS (ESI): m/z = 468 (MH', 100 %}.
1H-NMR (300 MHz, DMSO-d6): 11.72 (s, IN, -NH); 9.01 (s, 0.5H); 8,99 (s, 0.5H); 8.57 (d, J = 7.0, IN, ~NH); 8.31 (s, 1H); 7.02 {d, J - 8.6, 1H); 6.58 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.90 (br,s, 1H, -OH); 4,60 (m, O.SH); 4,53 (m, 0.5H); 4.33 (m, 0.5H); 4.27 (m, 0.5H); 3,95 (qu, J = 6.9, 2H); 3.88-3.32 (m, 4H); 2.34-2.13 (m, 1H); 2.08 (m, 0.5H); 1.94 (m, 0.5H); 1.20 (m, 3H); 1,03 (t, J = 6.9, 3H).
Example 251: 4-(5-Propoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-a]pyrfmidine-7-carboxylic acid [1-((S)-2-hydroxy-propionyl)-piperidin-4-yl]-amide
Starting from 4-(5-propoxy-benzo[1,3]dioxol-4-yl)-5H-pyrralo[3,2-d]pyrimidine-7-carboxylic acid p(peridin-4-ylamide (example A177) and acetic acid (S)-1-ch!orocarbony(-ethyl ester the title compound was obtained as colorless solid. MS (ESI): m/z = 496 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.14 (s. 1H, -NH); 9.02 (s, 1H); 8.44 (d, J = 7.8, 1H, -NH); 8.28 (s, 1H); 7.02 (d, J = 8.6, IN); 6.58 (d, J = 8.6.1H); 6.00 (s, 2H); 4.86 (d, J = 6.3.1H, -OH); 4.47 (m, IN); 4.23 (m, 1H);4.16{m, 1H);3.97(m, 1H); 3.85(t, J = 6.4, 2H); 3.27 (m, 1H);2.96(m, 1H); 1.99 (m, 2H); 1,54 (m, 1H); 1.42(m, 2H&m, IN); 1.21 (br.s, 3H); 0,63 (t, J = 7.4, 3H).
Example 252: 4-(5-Propoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid I(R)-1 -((S>2-hydroxy-propionyl)-pyrrolidin-3-yl]-amide
Starting from 4-(5-propoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrQ!o[3,2-cl]pyrimidine-7-carboxylic acid (R)-pyn-olidin-3-ylamide (example A178) and acetic acid (S)-1-chlorocarbonyl-ethyl ester the title compound was obtained as colorless solid.

MS (ESI): m/z - 482 (MH+, 100 %).
1H-NMR (300 MHz, DMSO-d6): 11.99 (s, IN, -NH); 9.01 (s. 0.5H); 8.99 (s, 0.5H); 8.57 (d, J = 6.9, 1H,-NH);8.30(s, 1H): 7.03 (d, J = 8.6, IN); 6.58 (d, J = 8.6, 1H); 6.00 (s, 2H); 4.90 (br.s, 1H,-OH); 4.60 (m, 0.5H); 4.52 (m, 0.5H); 4.32 (m, 0.5H); 4.27 (m, 0.5H); 3.86 (t, J = 6.4, 2H); 3.80-3.34 (m,4H); 2.33-2.14 (m. 1H); 2.08 (m, 0.5H); 1.97 (m, 0.5H); 1.42 {m.2H); 1.23 (d, J = 6.5, 1.5H); 1.20 (d, J = 6.5, 1.5H); 0.62 (t, J = 7.4, 3H).
Example 253: 4-(5-Butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-((S)-2-hydroxy-propionyl)-piperidin-4-yl]-amide
Starting from 4-(5-butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide (example A179) and acetic acid (S)-1-chlorocarbonyl-ethyl ester the title compound was obtained as colorless solid. MS (ESI): m/z =510 (MH\ 100 %).
1H-NMR (300 MHz, DMSO-d6): 12.24 (s, 1H, -NH); 9.02 (s, 1H); 8.44 (d, J = 7.7, 1H, -NH); 8.28 (s, IN); 7.02 (d, J = 8.6. IN); 6.59 (d, J = 8.6, IN); 6.00 (s, 2H); 4.86 (d, J = 6.9, 1H, -OH); 4.47 (m, 1H); 4.23 (m,1H); 4.16 (m, 1H);3.97{m, 1H); 3.88 (t, J = 6.4, 2H); 3.27 (m, 1H); 2.96 (m, IN); 1.99 (m, 2H); 1.54 (m. IN); 1.42 (m, 2H & m, 1H); 1.21 (br.s, 3H); 0.99 (m, 2H); 0.69 (t, J = 7.4, 3H).
Example 254: 4-(5-Butoxy-benzo[1.3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimldine-7-carboxylic acid [(R)-1-((S)-2-hydroxy-propionyl)-pyrrolidln-3-yr|-amide
Starting from 4-(5-butoxy-benzo[1,3IdfoxoW-yl)-5/V-pyrrolo[3,2-alpyrimidine-7-carboxyl(c acid (R)-pyrrolidin-3-ylamide (example A181) and acetic acid (S)-1-chlorocarbonyl-ethyl ester the title compound was obtained as colorless solid. MS (ESI): m/z = 496 (MH+, 100 %).
1H-NMR 300 MHz, DMSO-d6): 12.17 (br.s, IN, -NH); 9.01 (s, 0-5H); 8.99 (s, 0.5H); 8.57 (d, J = 7.0, IN, -NH); 8.30 (s, 1H); 7.02 (d, J = 8 6. 1H); 6.59 (d, J = 8.6, 1H); 6 01 (s, 2H); 4.99-4.81 (m, 1H, -OH); 4.60 (m, 0.5H); 4.52 (m, 0.5H); 3.88 (t. J = 6.4, 2H); 3.84-3.33 (m, 4H); 2.33-2.12 (m. 1H); 2.06 (m, 0.5H}; 1.96 (m, 0.5H); 1.39 (m, 2H); 1.23 (d, J = 6.5, 1.5H), 1.20 (d, J = 6.5, 1.5H); 1.05 (m, 2H); 0.69 (t, J = 7.4, 3H).
Example 255: trans-4-[4-Methoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-c/lpyrimidine-7-carboxylie acid [4-(2-hydroxy-acetylamino)-cyclohexyl]-amide Starting from trans-4-[4-methoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyllc acid (4-amino-cyclohexyl)-amide (example A182) and acetic acid chlorocarbonyl-m ethyl ester the title compound was obtained as colorless solid. MS (ESI): m/z = 498 (MH').
1H-NMR (400 MHz, DMSO-d6): 11.73 (br.s, 1H, -NH); 9.00 (s, 1H); 8.39 (d, J = 7.8, 1H, -NH); 8.22 (d, J = 3.3, 1H); 7.69 (d, J = 8.3, 1H); 7.48 (d, J = 8.3, 1H, -NH); 6.77 (s, 1H); 6.76 (dd, J, = 8.3, J2

= 2.2,1H); 5.42 (t, J = 5.7, 1H. -OH); 4.23 (t, J = 4.6, 2H); 3.88 (s, 3H); 3.78 (d, J = 5.7, 2H & m, 1H); 3.68 (m, 1H); 3.54 (t, J = 4.6, 2H); 3.13 (s, 3H); 2.01 (m, 2H); 1.82 (m, 2H); 1.44 (m, 4H).
Example 256: trans-4-[4-Methoxy-2-(2-met:hoxy-ethoxy)-phenyl]-5H-pyr^olo[3,2-(:/Ipyrimidine-7-carboxyfic acid (4-((S)-2-hydroxy-propiony(am[no)-cyclohexy(]-amide Starting from trans-4-[4-methoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cydohexyl)-amide (example A182) and acetic acid (S)-l-chlorocarbonyl-ethyl ester the title compound was obtained as colorless solid. MS (ESI): m/z = 512(MH+).
'1H-NMR (400 MHz, DMSO-do): 11.73 (br.s, 1H,-NH); 9.00 (s, 1H); 8.39 (d, J = 7.8, 1H, ~NH);8.22 (s, 1H); 7.69 (d, J = 8.3, 1H); 7.43 (d, J = 8.3, 1H, -NH); 6.77 (s, 1H); 6.76 (dd, J1 = 6-3, J^ = 2.2, 1H); 5.43 (d, J = 5.1, 1H, -OH); 4.23 (t, J = 4.6, 2H); 3.93 (m, 1H); 3.88 (s, 3H); 3.82 (m, 1H): 3.63 (m, 1H); 3.53 (t, J =4.6, 2H); 3.13 {s,3H); 2.01 (m, 2H); 1.80{m,2H); 1.43(m,4H); 1.20(d, J = 6.7, 3H).
Example 257: trans-4-[4-Methoxy-2-(2-methoxy-ethoxy)-ptienyl]-5H-pyrrolo[3,2- 1H-NMR(400 MHz, DMSO-d6): 11-72 (br.s, 1H, -NH); 9.00 (s, 1H); 8.39 (d, J = 7.8, 1H, ~NH); 8.22 (s, 1H); 7-69 (d, J - 8.5, 1H); 7.57 (d, J = 8.5, 1H, -NH); 6-77 (s, 1H); 6-76 (dd, J, = 8-5, J2 = 2.2, 1H); 6.20 (s, 1H, -OH); 4.23 (t, J = 4.6, 2H); 3.87 (s, 3H); 3.84 (m, 1H); 3-68 (m, 1H); 3.54 (t, J = 4.6, 2H); 3.13 (s,3H); 2-01 (m, 2H); 1.82 (m, 2H); 1.48 (m, 4H); 1.01 (m, 2H); 0.81 (m, 2H).
Example 258: cis-4-[4-Methoxy-2-(2-methioxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimldine-7-carboxylic acid {4-[(1 -hydroxy-cyclopropanecarbonyl)-amino]-cyclohexyl}-amide Starting from cis-4-[4-metfioxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolof3,2-d)pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A183) and acetic acid 1-chlorocarbonyl-cyclopropyl ester the title compound was obtained as colorless solid. MS (ESI): m/z = 524 (MH+).
1H-NMR (400 MHz, DMSO-d6): 11.73 (br.s, 1H, -NH); 9.04 (s, 1H); 8.71 (d, J = 7.8, 1H, -NH); 8.23 (s, 1H); 7.70 (d, J = 8.3, 1H); 7.56 (d, J = 7.8, 1H, -NH); 6.77 (s. 1H); 6,76 (dd, J1 = 8.3, J2 = 2-2, 1H); 6.25 (s, 1H, -OH); 4.24 (t, J = 4.6, 2H); 4-08 (m, 1H); 3.88 (s, 3H); 3.78 (m, 1H); 3.55 (t, J = 4.6, 2H); 3-14 (s, 3H); 1.85-1-67 (m, 8H); 1.82 (m, 2H); 1.03 (m, 2H); 0.83 (m, 2H).

Example 259: 4-[4-Melhoxy-2-(2-nnettioxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylie acid [l-(1-fiydroxy-cyclopropanecarbonyi)-piperidin-4-yl]-anmide
Starting from 4-[4-methoxy-2-(2-methoxy-ettioxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide (example A184) and acetic acid 1-chlorocarbonyl-cyclopropyl ester the title compound was obtained as colorless solid. MS(ESI):m/z=510{MH').
1H-NMR (400 MHz, DMSO-d6): 11.74 (br.s, 1H. -NH); 9.00 (s, 1H); 8.56 (d, J = 7.8, 1H, ~NH); 8.24 (s, 1H); 7.70 (d, J = 8.3, 1H); 6.77 (s, 1H); 6.76 (dd, J, = 8.3, Jz = 2.1, 1H); 6.30 (s, 1H, -OH); 4.30 (m, 1H); 4.24 (t, J = 4,6, 2H); 4.18 (m, 2H); 3.87 (s, 3H); 3.54 {t, J = 4.6, 2H); 3.13 (s, 3H & m, 2H); 2.00 (m, 2H); 1.51 (m, 2H); 0.94 (m, 2H); 0.77 (m, 2H).
Example 260: trans-4-[5-(2-Methoxy-ethoxy)-ben20[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-tf]pyrimidine-7-carboxylic acid [4-(2-hydroxy-acetylamino)-cyclohexyl]-amide Starting from trans-4-[5-{2-methoxy-ethoxy)-ben2o[1,3]diGxol-4-yl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amino-cyclohexyl)-amide (example A185) and acetic acid chlorocarbonyl-methyl ester the title compound was obtained as colorless solid. MS (ESI): m/z = 512 (MH+).
1H-NMR (200 MHz, DIVISO-de): 12.12 {br.s, 1H,-NH); 9.02 (s, 1H); 8.33 (d, J ^ 7.8, 1H,-NH);8.23 (s, IN); 7.47 (d, J = 8,2, -NH); 7.02 (d, J = 8.6, 1H); 6.61 (d, J = 8.6,1H); 6.01 (s, 2H); 5.42 (br.s, 1H, OH)- 4.03 (f, J = 4.7, 2H); 3.79 (s, 2H & m, 2H); 3.39 (t, J = 4.7, 2H); 3.02 (s, 3H); 2.04 (m, 2H); 1.81 (m,2H); 1.45 (m,4H).
Example 261: c/s-4-[5-(2-Methoxy-ethoxy)-benzo[1,3]dioxol-4-y(]-5/V-pyrroto[3,2-cd py rim id i ne-7-carboxyIic acid [4-(2- hydroxy-acetylamino)-cyclohexyl]-am id e Starting from cis-4-[5-(2-methQxy-ethoxy)-benzo(1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-amJno-cycJohexyl)-amide (example A186) and acetic acid chlorocarbonyl-methy) ester the title compound was obtained as colorless solid. MS (ESI): m/z = 512 (MH+).
1H-NMR (200 MHz, DMSO-d6): 11-20 (br.s, 1H, -NH); 9.05 (s, IN); 8.59 (d, J = 7.5, 1H; -NH); 8.28 (s, 1H); 7.56 (d, J = 7.7, 1H, -NH); 7.03 {d, J = 8.6, 1H); 6.62 (d, J = 8.6, 1H); 6,02 (s, 2H); 5,40 (br.s, 1H, -OH); 4.04 (t, J = 4,7, 2H & m, 1H); 3.82 (s, 2H & m, 1H); 3,39 (t, J = 4.7, 2H); 3.03 (s, 3H); 1.72 (m.8H).
Example 262: cis-4-[5-(2-Methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-c(|pyrimidine-7-carboxylic acid [4-((S)-2-hydroxy-propionylamino)-cyclohexyl]-amide Starting from cis-4-[5-(2-methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d]pyrimidine-7-cartoxylic acid (4-am!no-cyclohexyl)-amide (example A186) and acetic acid (S)-1-chlorocarbonyl-ethyl ester the title compound was obtained as colorless solid,

MS (ESI); m/z = 526 (MH+).
1H-NMR (200 MHz, DMSO-d6): 11-82 (br.s, 1H, -NH); 9.05 (s, 1H); 8.57 (d, J = 7.4, 1H; ~NH); 8.28 (s, 1H); 7.50 (d, J = 11.. 1H, -NH); 7.03 (d, J = 8.6, 1H); 6.62 (d, J = 8.6, 1H); 6.02 (s, 2H); 5.37 (br.s, 1H, -OH); 4,04 (t, J = 4.7, 2H & m, 1H); 3.99 (m. 1H); 3.76 (rr, 1H); 3.39 (t, J = 4.7, 2H); 3.03 (s, 3H); 1,74 (m. 8H); 1.22 (d, J =6.7, 3H),
Example 263: 4-[5-(2-Melhoxy-elhoxy)-ben2o[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d]pyrim^dine-7-ca^boxylic acid [1-((S)-2-hydroxy-propionyl)-piperidin-4-ylJ-amide
Starting from 4-[5-{2-methoxy-ettioxy)-benzo[1,3]dioxol-4-yi]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide (example A187) and acetic acid (S)-1-chlorocarbonyl-ethyl ester the tide compound was obtained as colorless solid. MS (ESI): m/z = 512 (MH+).
1H-NMR (200 MHz, DMSO-d6): 12.19 (br.s, 1H,-NH); 9.02 (s, IN); 8.45 (d, J = 7.7, 1H;-NH);8.30 (s, 1H); 7.02 (d, J = 8.6, 1H); 6.61 (d, J = 8.6, 1H); 6.01 (s, 2H); 4.87 (d, J = 6.9, 1H, -OH); 4.47 (m, 1H); 4.18 (m, 2H); 4.03 (t, J = 4.7, 2H); 3.92 (m, 1H); 3.39 (t, J = 4.7, 2H); 3.30 (s, 1H); 3.02 (s, 3H); 2.94 (m, 1H); 1.99 (m, 2H); 1.51 (m, 2H); 1.21 (d, J = 6.3, 3H).
Example 264: 4-(5-Acetyl-2-cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-((S)-2-hydroxy-propanoyl)-piperidin-4-yl]-amide
To a solution of 4-(5-acety/-2-cyctopropylrnethoxy-pheny()-5H-pyrrolo[3,2-G(lpyrrmidine-7-carboxylic acid from example A81 (43 mg; 0.12 mmol) in dichloromethane (2mL) Is added 1-(3-dim6thylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.16 mmol), triethylamine (0.24 mmol) and 1-hydroxybenzotrrazole (0.12 mmol). The suspension is stirred for 20 min at ambient temperature and then (S)-1-(4-amino-piperidin-1-yl)-2-hydroxy-propan-1-on6 hydrochloride from example A190 (0.16 mmol) is added. The reaction mixture is stirred overnight at ambient temperature. The volatiles are evaporated and the crude is distributed between ethyl acetate and aqueous phosphate buffer (1M, pH=7). The organic phase is separated, washed with aqueous phosphate buffer and evaporated to dryness. The obtained crude product is purified by preparative HPLC yielding 3B mg of the titJe compound as white solid. MS (ESI): m/z = 506 (MH+. 100%).
1H-NMR (400 r/1Hz, DMSO-d6): 12.15 (s, 1H,-NH), 9.10 (s, 1H), 8.52(d, 1H, J= 7Hz, NH), 8.30 (s, 1H), 8.21 (d, 1H, J=1.5Hz), 8.12(dd, 1H,J=9, 1.5 Hz), 7.28 (d, 1H, J= 9 Hz), 4.45 (m, 1H), 4.18 (m, 2H), 4.02 (d, 2H, J= 7Hz), 3.28 (m, 1H). 2.98(m, 1H), 2.60 (s, 3H), 1.98 (m,2H), 1.50 (m,2H),' 1.20 (m, 3H), 1.00 (m, 1H), 0.35 (m, 2H), 0.24 (m. 2H),
The following compounds are obtained analogously to the procedure described in above example 264.

Example 265: 4-(5-Acety}~2-cycloropylmethoxy-phenyl)-5H-pyrrolol3,2-cflpynrnidine-7-carboxytic acid [1-(2-methoxy-acetyl)'piperidin-4-yI]-amide
Starting from 4-(5-acetyl-2-cyclopropylmethoxy-phenyl}-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (example A81) and 1-(4-amlno-piperidin-1-yl)-2-methoxy-ethanone (A192) the title compound is obtained as colorless solid. MS (ESI): m/z = 506 (MH+, 100%).
1H-NMR (400 MHz, DMSO-d6) 12.15 (s, 1H, -NH); 9.10 (s, 1H); 8.50 (d, J = 7.0, 1H, -NH); 8.32 (s, 1H);8.20(d, J =1.5, 1H); 8.12 (dd. J, = 9.0, J2 = 1.5, 1H): 7.25 (d, J = 9.0, 1H); 4.22 (m, 2H); 4.03 (m, 2H); 4.02 (d, J ^ 7.0, 2H); 3.75 (m, 1H); 3.20 (m, 1H); 2.93 (m, 1H); 2.60 (s, 3H); 1.95 (m, 2H); 1.75 (m, 2H); 1.00 (m, 1H); 0,35 (m, 2H); 0.24 (m, 2H).
Example 266: 4-(5-Acetyl-2-cyc!opropylmethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-acetyl-piperidin-4-yl)-amide
Starting from 4-(5-acefyl'2-cychpropy}methoxy-phenyl)-5H-pyrrolo[3.2-dJpyriividifie'7-carboxylic acid (example A81) and 1-(4-Amino-piperidin-1-yl)-ethanone (A191) the title compound is obtained as colorless solid.
MS (ESI): m/2 = 476,0 (MH+, 100%).
1H-NMR (400 MHz, DMS0-d6) 12.15 (s, 1H, -NH); 9.10 (s, IN); 8.52 (d, J = 7.0, 1H); 8.32 (s, 1H); 8.20 (d, J = 1.5, 1H); 8.12 {dd,J1 = 9.0, J2= 1.5, 1H); 7.25 (d, J = 9.0, 1H); 4.18 (m, 2H); 4.02 (d, J = 7.0, 2H); 3.80 (m. 1H); 3.30 (m, IN); 2.93 (m, 1H); 2.60 (s, 3H); 2.05 (s, 3H); 1.96 (m, 2H); 1.45 (m, 2H); 1.00 (m, 1H); 0.35 (m, 2H); 0.24 (m, 2H).
Example 267: 4-(5-Acetyl-2-cyclopropylmethoxy-4-methy|-ptienyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1 -((S)-2-hydroxy-propionyl)-piper(din-4-yl]-amide Starting from 4-(5-acetyl-2-cyclopropylmethoxy-4-methyl-phenyl>-5H-pyrrolo[3,2-c(]pyrlmidine-7-carboxylic acid (example A82) and (S)-1-(4-amino-piperidin-1-yl)-2-hydroxy-propan-1-one; hydrochloride (A 190) the title compound is obtained as colorless solid. MS (ESI): m/2 = 520 (MH+, 100%).
1H-NMR (400 MHz, DMSO-d6): 12.10 (s, 1H, -NH); 9.08 (s, 1H); 8.52 (d, 1H, J = 8.0, -NH); 8.30 (s, 1H); 8.13 (s, 1H); 7.10 (m, IN); 4.87 (d, 1H. J = 7.0, -OH); 4.45 (m, IN); 4.20 {m, 2H); 4.02 (d, 2H, J = 7.0); 3.98 (m, 1H); 3.30 (m, 1H); 3.00 (m, 1H); 2.60 (s, 3H); 2.55 (s, 3H); 1.98 (m, 2H); 1.40 (m, 2H); 1.23 (m, 3H): 1.00 (m, IN); 0.35 (m, 2H); 0.24 (m, 2H).
Example 268: 4-(5-Acetyl-2-cyclopropylmethoxy-4-methy|-phenyl)-5H-pyrrolo[3,2-c/]pyrimidine-7-carboxylic acid (1-acetyl-piperidin-4-yl)-amide
Starting from 4-(5-acetyl-2-cyclopnopylmethoxy-4-methyl-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (example A82) and 1-(4-amino-piperidin-1-yl)-ethanone (A191) the title compound is obtained as colorless solid.

MS (ES)); m/2 = 490 (MH+, 100%).
1H^NMR(400MHz, DMSO-d6): 12.10 (s, 1H,-NH);9.05 (s, 1H);8.36(d, J = 3.0, 1H);8.10(s, 1H);
7.10 (s, 1H); 4.00 {d, J = 7.0, 2H); 2.60 (s, 3H); 2.55 (s, 3H); 1.00 (m, 1H); 0.37 (m, 2H); 0.24 (m,
2H).
Example 269: trans-4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-(/Ipyrimidine-7-carbioxylic acid [4-(2-metho.xy-ethylcarbamoyl)-cyclohexyl]-amide Starting from 4-(5-cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (example A67) and trans-4-amino-cyclohexanecarboxylic acid (2-methoxy-etiiyl)-amide hydrochloride (A196) the title compound is obtained as colorless solid. IV1S (ESI): m/z = 536 (MH+).
1H~NMR (400 MHz, DMSO-d6): 12.25 (br.s, 1H, -NH); 9,03 (s, 1H); 8,29 (d, J = 7,8, 1H, -NH); 8.26 (s, 1H); 7.99 (t, J = 5.6, 1H, -NH); 7.01 (d, J = 8.6, 1H); 6.56 (d, J = 8,6, 1H); 6.00 (s, 2H); 3.80 (m, 1H); 3.76 (d, J = 6.8, 2H); 3.34 (m, 2H); 3.25 (s, 3H); 3.20 (m, 2H); 2.18 (m, 1H); 2.05 (m, 2H); 1.80 (m, 2H); 1.50 (m, 2H); 1.34 (m, 2H)); 0.87 (m, 1H); 0.29 (m, 2H); 0.10 (m, 2H).
Example 270: trans-4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yi)-5H-pyrrolo[3,2-c(jpyrimJdine-7-carboxylJc acid (4-cyclopropylcarbamoyJ-cydohexyl)-amide Starting from 4-(5-cyclopropylmethoxy-benzo[1.3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (example A67) and trans-(4-cyclopropylcarbamoyl-cyclohexyl)-carbamic acid tert-butyl ester (A195) the title compound is obtained as colorless solid. MS (ESI): m/z = 518 (MH+).
1H-NMR (400 MHz, DMSO-d6): 12.25 (br.s, 1H,-NH); 9.02 (s, 1H); 8.28 (d, J = 7.9, 1H,-NH);8.26 (s, 1H); 711 (d, J = 4,3, 1H, -NH); 7.01 (d, J = 8.6, 1H); 6,56 (d, J = 8.6, 1H); 6,00 (s, 2H); 3.79 (m, 1H);3.76(d, J = 6.7, 2H);2.62(m, 1H); 2.11-2.04 (m, 3H); 1.78 (m,2H); 1.49 (m,2H); 1.32 (m, 2H)); 0.87 (m, IN); 0.59 (m, 2H); 0.38 (m, 2H); 0.29 (m, 2H); 0.10 (m, 2H).
Example 271: trans-4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-c(]pyrimldine-7-carboxylic acid (4-cyclopropylcarbamoyl-cyclotiexyl)-amide
Starting from 4-(2-cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimldine-7-carboxylic acid (example A73) and trans-(4-cyclopropylcarbamoyl-cyclohiexyl)-carbamic acid tert-butyl ester (A195) the title compound is obtained as colorless solid. MS (ESI): m/z = 504 (MH+, 100 %).
'H~NMR (400 MHz, DMSO-d6): 1188 (br.s, 1H, -NH); 8.99 (s, 1H); 8.36 (d, J = 7.9, 1H, -NH); 8.19 (s, 1H);7.77(d,J = 4.3, 1H,-NH);7,61 (d, J = 8.5, 1H); 6.72( dd, J, = 8.5, J2 = 2.2, 1H);6.69(d,J = 2.2, 1H); 3.91 (d, J = 6.9, 2H); 3.86(s, 3H); 3.79 (m, 1H);2.62(m, 1H); 2.11-2.03 (m, 3H); 1.78 (m, 2H); 1.49 (m, 2H); 1.32 (m, 2H); 0.97 (m, 1H); 0.37 (m, 2H); 0.23 (m, 2H).

Example 272.- kanS'4-(2-Cyctopropyimethoxy-4-methoxy-pbenyl}-5H-pyno\o[3,2-c^pyrimidine-7-carboxylic acid [4-(2-methoxy-ethylcarbamoyl)-cyclohexyl]-amide Starting from 4-(2-cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-cf|pyrinnidine-7-carboxy!ic acid (example A73) and frans-4-amrno-cyclohexanecarboxylic acid (2~methoxy-ethyl)-amide hydrochloride (A196) the title compound is obtained as colorless solid, MS (ESI): m/z = 522 (MH+, 100 %).
1H-NMR (400 MHz, DMSO-d6): 11.89 (br.s, 1H, -NH); 9.00 (s, 1H); 8.37 (d, J = 7.9, 1H, -NH); 8.19 (s, 1H); 7.78 (t, J = 5.6, 1H, -NH); 7.61 {d, J = 8.5, 1H); 6.72 { dd, J1 = 8.5, J2 = 2.3, 1H); 6.69 (d, J = 2.3, 1H); 3.92 (d, J = 7.0, 2H); 3.86 (s, 3H); 3.80 (m, 1H); 3.34 (m, 2H); 3.25 (s, 3H); 3.20 (m, 2H); 2.18 (m, 1H); 2.05 {m, 2H); 1,80 (m, 2H); 1.50 (m, 2H); 1.33 (m, 2H); 0.97 (m, 1H); 0.36 (m, 2H); 0.23 (m, 2H).
Example 273: trans-4-(2-Cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-cyclopropylcarbamoyl-cyclohexyl)-amide
Starting from 4-(2-cyclopropylmethoxy-5-fiuoro-phenyt)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (example A77) and trans-(4-cyclopropylcarbamoyl-Gyclohexyl}-carbamic acid tert-butyl ester (A195) the title compound is obtained as colorless solid. MS (ESI); m/z = 492 (MH+, 100 %).
1H-NMR(400MHz, DMSO-d6); 12.08 {br.s, 1H,-NH); 9.05 (s, 1H); 8.32 (d, J = 7.9, 1H,-NH);8.28 (s, 1H); 7.77 (d, J = 4.3, 1H, -NH); 7.43 (dd, J1 = 8.9, J2 =3,3, 1H); 7.38 (ddd, J1 = J2 = 9.2, J3 = 3.3, 1H);7.19(dd, J1 =9.2, J2= 4.4, 1H); 3.88 (d, J :^ 6.9, 2H); 3.80 (m, 1H);2.61 (m, 1H); 2.11-2.04 (m, 3H); 1.79 (m,2H); 1.50 {m, 2H); 1.32 (m, 2H); 0.94 (m, 1H); 0.59 (m, 2H); 0.38 (m, 2H); 0.33 (m, 2H);0.19{m, 2H).
Example 274: trans-4-(2-CycIopropyimethoxy-5-fluoro-phenyt)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(2-methoxy-ethylcarbamoyl)-cyclohexyl]-amide
Starting from 4-(2-cyc!opropyImethoxy-5-fIuoro-phenyI)-5H-pyrroio[3,2-d]pyrimidine-7-carboxylie acid (example A77) and trans-4-amino-cyclohexanecartioxylic acid (2-methoxy-ethyl)-amide hydrochloride (A196) the title compound is obtained as colorless solid, MS (ESI): m/z = 510 (MH', 100 %).
1H-NMR (400 MHz, DMSO-d6): 12.08 (br.s, 1H, -NH); 9.06 (s, 1H); 8,33 (d, J = 7.9, 1H, -NH); 8.28 (s, 1H); 7.79 (d, J = 5.5, 1H, -NH); 7.43 (dd, J1 = 9.0, J2 =3.3, 1H); 7.38 (ddd, J1 = J2 = 9.1, J3 = 3.3, IN); 7.19 (dd, J1 = 9.1, J1 = 4.4, 1H); 3.88 (d, J = 6.9, 2H); 3,79 (m, 1H); 3.34 (m, 2H); 3.25 (s, 3H); 3.20 (m, 2H); 2.17 (m, 1H); 2.06 (m, 2H); 1.80 (m,2H); 1.50 (m, 2H); 1.33 (m, 2H); 0.94 (m, 1H); 0.34 (m,2H); 0.18 (m,2H).
Example 275: trans^-(5-Cyclobutylmethoxy-ben2o[1,3]dioxGl-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(2-methoxy-ethylcarbamoyl)-cyclohexyl]-amide

Starting 4-(5-cyclobutylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbaxylic acid (example A68) and trans-4-amino-cyclohexanecarboxylic acid (2-mGthoxy-ethyl)-amide hydrochloride (A196) the title compound is obtained as colorless solid. MS (ESI): m/z = 550 (MM*, 100 %).).
1H-NMR (400 MHz, DMSO-d6): 12-28 (br.s, 1H, -NH); 9.01 (s, 1H); 8.28 (d, J = 7.8, 1H, -NH); 8.24 (s, 1H); 7.78 (t, J = 5.6, 1H, ~NH); 7.01 (d, J = 8.6, IN); 6.59 (d, J = 8,6, 1H}; 6.00 (s, 2H): 3-84 (d, J = 6-2, 1H); 3.79 (m, IN); 3.33 (m, 2H); 3.25 (s, 3H): 3-20 (m, 2H); 2.36 {m, 1H); 2.17 (m, 2H); 2.05 (m, 2H); 1-80 (m, 2H); 1.68 (m, 3H); 1.57-1.44 (m, 5H); 1,33 (m, 2H)-
Example 276: trans-4-(5-Cyclobutylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3.2-c(]pyrimidlne-7-cartlOxylic acid (4-cyclopropylcarbamoyl-cyclohexy()-amide Starting from 4-(5-cyclobutylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-clpyrimidine-7-carboxylic acid (example A68) and trans-(4-cyclopropylcarbamoyl-cyclohexyl)-carbamic acid tert-butyl ester (A195) the title compound is obtained as colorless solid-MS (ESI): m/z = 532 (MH+, 100 %).
1H-NMR (400 MHz, DMSO-d6): 12.28 (br.s, 1H, -NH); 9.01 (s, 1H); 8.27 (d, J = 7.8, 1H, -NH); 8.24 (s, 1H); 7.77 (d, J = 4.3, 1H, -NH); 7.01 (d. J = 8.6, 1H); 6,59 (d, J = 8-6, 1H); 6-00 (s, 2H); 3.84 (d, J = 6.2, 1H);3.79(m, 1H); 3.25 (s, 3H); 2.61 (m, 1H); 2-36 (m, 1H); 2-10-2,02 (m, 2H); 1-79(m, 2H); 1.68 (m, 3H); 1.57-1.44 (m, 5H); 1.32 (m, 2H); 0.59 (m, 2H); 0-39 (m, 2H),
The following compounds are obtained analogously to the procedure described in above example 1.
Example 277: 4-(2-Cyclopropy[methoxy-5-fluoro-4-hydroxy-phenyl)-5H-pyrralo[3,2-d]pyrimidine-7-carboxylic acid {1-acetyl-piperidin-4-yl)-amide
Starting from4-(2-cyctopropylmet^Ioxy-5-fluoro-hydroxy-phenyl)5H-pyrroto[3,2-o5pyrim(d;ne-7-carboxylic acid piperidin-4-ylamide hydrochloride (example A188) and acetyl chloride the title compound is obtained as colorless solid MS (ESI); m/z = 468 (MH+, 100%)-
1H-NMR (300 MHz, DMSO-ds): 11.90 (br.d, J = 3-5, 1H,-NH); 10-43 (s, 1H,-OH); 8-99 (s, 1H); 8.52 (d, J = 7-9, 1H, -NH); 8.29 (d, J = 3-5, 1H); 7.45 (d, J = 11.5, 1H); 6.70 (d, J = 7-5,1H); 4-27-4-06 (m, 2H); 3.81 (d, J = 6-9, 2H); 3.80 {m, 1H); 3-27 (m, 1H); 2-92 (m, 1H); 2.04 (s, 3H); 1-96 (m, 2H); 1-55 (m,1H); 1-39 (m, 1H); 0,96 (m, 1H); 0.35 (m, 2H); 0.22 (m, 2H)-
Example 278: 4-(2-Cyclopropylmethoxy-5-fluoro-4-hydroxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-propionyl-piperidin-4-yl)-amide

starting from 4-(2-cyclopropylmethoxy-5-fluoro-4-hydroxy-phenyi)-5H-pyrrolo[3,2-d]pyrimidJne-7-cartioxylic acid piperidin-4-ylamide hydrochloride (example A188) and propionyl chloride the title compound is obtained as colorless solid MS (ESI): m/z = 482 (MH\ 100%).
1H^NMR (300 MHz, DMSO-d6): 11.90 (br.d, J = 3.1, 1H, -NH}; 10.43 (br.s, 1H,-0H); 8.99 (s, IN); 8.52 (d, J = 7.8, 1H,-NH);8,25{d, J = 3.1, 1H); 7.44 (d, J = 11,5, 1H); 6.70 (d, J = 7.3, 1H);4.23 (m, 1H); 4.13 (m, 1H); 3.83 (m, 1H); 3.81 (d, J ~ 6.8, 2H); 3.24 (m, 1H); 2.93 (m, IN); 2.36 (qu, J = 7.3, 2H); 1.96 (m,2H); 1.53 (m,1H); 1.39 (m, 1H); 1.01 (t, J = 7.3, 3H); 0.96 (m, 1H); 0.35 (m, 2H); 0.22 (m, 2H).
Example 279: 4-[2-Cyclopropylmethoxy-4-(1,1-drfluoro-methoxy)-5-fluoro-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-acetyi-pipertdin-4-yi)-amide Starting from 4-[2-cyclopropylmethoxy-4-(1,1-difluoro-methoxy)-5-fiuoro-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide hydrochloride (example A189) and acetyl chloride the title compound is obtained as colorless solid. MS (ESI): m/z = 518 (MM*, 100%).
1H-NMR (300 MHz, DMSO-d6): 12.16 (br.s. 1H, -NH); 9.05 (s, 1H); 8.48 (d, J = 7.9, IN, -NH); 8.35 (s, 1H); 7.64 (d, J = 10.8, 1H); 7.40 (t, J = 73.2, 1H); 7.18 (d, J = 6.8, 1H); 4.21 (m, 1H); 4.14 (m, 1H); 3.91 (d, J = 6.9, 2H); 3.80 (m, 1H); 3.27 (m, 1H); 2.92 (m, IN); 2.04 (s, 3H); 1.96 {m, 2H); 1.56 (m,1H); 1.40 (m, 1H);0.95(m, 1H); 0.35 (m, 2H); 0.21 (m, 2H).
Example 280: 4-[2-Cyclopropy!methoxy-4-(1,1-d!fiuoro-methoxy)-5-fluoro-phenyl]-5H-pyrroIo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-methoxy-ethanoyl)-piperidin-4-yl]-amide Starting firom 4-[2-cyc(opropy(me{hoxy-4-(1,1-difluoro-methoxy)-5-fruoro-pheny(J-5H-pyrrolo[3,2-c/|pyrimidine-7-carboxylic acid piperidin-4-ylamide hydrochloride (example A189) and methoxy-acetyl chloride the title compound is obtained as colorless solid MS (ESI): m/z = 548 (MH\ 100%).
1H-NMR (300 MHz, DMSO-d6): 12.01 (br.s, 1H, -NH); 9.05 (s, IN); 8.48 (d, J = 7.9, 1H, -NH); 8.34 (s, 1H); 7.64 (d, J = 10.9, 1H); 7.41 (t, J = 77.6,1H); 7.18 (d, J = 6.6, 1H); 4.16 (m, 2H); 4.12 (d J = 2.6, 1H); 3.91 (d, J = 7.1, 2H); 3.76 (m, 1H); 3.31 (s, 3H); 3.22 (m, 1H); 2.95 (m, 1H); 1.98 (m, 2H); 1.56 {m,1H); 1.43 (m, 1H); 0.95 (m, 1H); 0.36 (m, 2H); 0.21 (m, 2H),
The following compounds are obtained analogously to the procedure described in above example 171.
Example 281: 4-(2-Cyclopropylmethoxy-5-fluoro-4-hydroxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-hydroxy-acetyl)-piperidin-4-yl]-amide

Starting from 4-(2-cyc)opropylmethoxy-5-fluoro-4-hydroxy-phenyJ)-5>V-pyrrotof3,2-c']pyrimidine-7-carboxylic acid piperidin-4-ylamide hydrochloride (example A188) and acetic acid chlorocarbonyl-methyl ester the title compound is obtained as colorless solid MS (ES/); m/z = 484 (MH+, 100%).
1H-NMR(300 MHz, DMSO-d6): 11.91 (br.d, J = 3.3, 1H,-NH); 10.43 (br.s, 1H,-0H); 8.99 (s, 1H); 8.52 (d, J = 7.7, 1H,-NH);8.25(d,J = 3.3, 1H); 7.44 (d, J = 11.5, 1H); 6.70 (d, J = 7.3, 1H);4.51 (t, J = 5.3, 1H, -OH); 4.28 (m, 2H); 4.13 (m, 2H); 3.81 (d, J = 6.8, 2H); 3.69 (m, 1H); 3.19 (m, 1H); 3.00 (m, 1H); 1.97 (m, 2H); 1.56{nn,1H); 1.42 (m, 1H); 0.96 (m, 1H); 0.35 (m, 2H); 0.22 (m, 2H).
Example 282: 4-(2-Cyclopropylmethoxy-5-fluoro-4-hydroxy-phenyl)-5H-pyrrolo[3,2-d]pyrinnidine-7-carboxylic acid [1-((S)-2-hydroxy-propionyl)-piperidin-4-yl]-amide Starting from 4-(2-cyclopropylmethoxy-5-fluoro-4-hydroxy-phenyl)-5H-pyrrolo[3,2-t/lpyrimidine-7-carboxylic acid piperidin-4-ylamide hydrochloride (example A188) and acetic acid (S)-1-chlorocarbonyl-ethy) ester the title compound is obtained as colorless solid MS (ESI): m/z = 498 (MH+, 100%).
1H-NMR(300MHZ, DMSO-d6):11-99(br.d,J = 3.5, 1H,-NH); 10.48 (br.s, 1H,-OH); 9.01 (s, 1H); 8.51 (d, J=7.7, 1H,-NH);8.29(d, J = 3.5, IN); 7.54 (d, J = 11.5, 1H);6.71 (d, J = 7.5. 1H);4.46 (m, 1H); 4.32-3.87 (m. 4H); 3.82 {d, J = 6.9, 2H); 3.27 (m, 1H); 2.97 (m, 1H); 1.98 (m, 2H); 1.55 (m,1H); 1.42 (m, 1H); 1.21 (br.s, 3H); 0.96 (m, 1H); 0.35 (m, 2H); 0.22 (m, 2H).
Example 283: 4-[2-Cyclopropylmethoxy-4-(1,1-dfflooro-methoxy)-5-fluorophenyi]-5/^-pyrrolo[3,2-d]pyrimid!ne-7-carboxylic acid [1-(2-hydroxy-acetyl)-piperidin-4-yl]-amide Starting from 4-(2-cyclopropylfnethoxy-5-fluoro-4-hydroxy-phenyI)-5H-pyrrolo[3,2-d]pyrimidlne-7-carboxylic acid pipe rid in-4-ylamide hydrochloride (example A188)and acetic acid chlorocarbonyl-methyl ester the title compound is obtained as colorless solid MS (ESI): m/z = 534 (MH+, 100%).
1H-NMR (300 MHz, DMSO-d6): 12.16 (br.s, 1H, -NH); 9.05 (s, 1H); 8.48 (d, J = 7.9, 1H, -NH); 8.34 (d, J = 3.5, 1H); 7.64 (d, J = 10.9, 1H); 7.40 (t, J = 73.2, 1H); 7.18 (d, J = 6.6, 1H); 4.51 (br.s, 1H. -OH); 4.18 (m, 1H);4.13(m, 1H &d, J = 4.6, 2H); 3.91 (d, J = 7.1, 2H); 3.70 (m, 1H);3.20(m, 1H); 2.99 (m, 1H); 1.98 (m. 2H); 1.56 (m,1 H); 1.43 (m, 1H); 0.95 (m, 1H); 0.35 (m, 2H); 0.21 (m, 2H).
Example 284: 4-{2-Cyclopropylmethoxy-4-(1,1-difluoro-methoxy)-5-fluoro-phenyl]-5H-pyrrolo(3,2-d]pyrimidine-7-carboxylic acid (1-((S)-2-hydroxy-propionyl)-piperidin-4-yl]-amide Starting from 4-(2-cyclopropylmethoxy-5-fluoro-4-hydroxy-phenyl)-5H-pyrrolo[3,2-d]pyrimldine-7-carboxylic acid pipendin-4-ylamide hydrochloride (example A188) and acetic acid (S)-1-chlorocarbonyl-ethyl ester the title compound is obtained as colorless solid MS (ESI): m/z = 548 (MH+. 100%).

1H-NMR (300 MHz, DMSO-d6): 12.16 (br.s, 1H, -NH); 9.06 {s. 1H); 8.49 (d, J = 7.9, 1H, -NH); 8.34 (d, J = 3.1, 1H); 7.65 (d, J = 10.8, 1H); 7.41 (t, J = 73.2, 1H); 7.18 (d, J = 6.6, 1H); 4,87 (d, J = 6.9, 1H, -OH); 4,47 {m, IN); 4.23 (m, 1H); 4.17 (m, 1H) 3.95 (m, 1H); 3.91 (d, J = 6.9, 2H); 3.26 (m, IN); 2.97 (m, 1H); 1.99 (m. 2H); 1.56 (m,1H); 1.44 (m, IN); 1.22 (br.s, 3H): 0.94 (m, IN); 0.35 (m, 2H); 0.21 (m, 2H).

Commercial utility
The compounds of formula (I), the salts thereof, N-oxides of the compounds and the salts thereof, and the stereoisomers of the compounds, the salts, the N-oxides of the compounds and the N-oxides of the salts thereof are hereinafter referred to as the compounds of the invention. In particular, the compounds of the invention are pharmaceutically acceptable.
The compounds of the invention have valuable pharmaceutical properties which make them commercially utilizable. In particular, as type 5 phosphodiesterase (PDE5) inhibitors, they are able to influence the physiological and pathophysiological function of various cells, e.g., but not limited to, smooth muscle cells, fibroblasts, myofibroblasts and platelets, which are involved in a great variety of physiological and pathophysiological mechanisms. In particular, the PDE5 inhibiting compounds of the invention can effect relaxation of the vasculature, thus increasing blood flow, improve the spatial balance between blood perfusion and ventilation within the lung ("re-matching" effect} thereby reducing the amount of so-called low V/Q-areas [areas within the lung with high perfusion (Q) but no or reduced ventilation (V)] and high V/Q-areas (areas within the lung with low perfusion but high ventilation), induce neurogenesis, inhibit platelet function, such as aggregation, adhesion and mediator release and, thus, have an anti-inflammatory effect. The compounds of the invention are distinguished by valuable and desirable properties, such as, for example, high efficacy, high selectivity, low toxicity, superior bioavailability in general (e.g. good enteral absorption), superior therapeutic window, superior pharmacokinetics (e.g. half-life), absence of significant side effects, and further beneficial effects related with their therapeutic and pharmaceutical suitability.
Accordingly, the invention further relates to the compounds of the invention for the treatment or prophylaxis of diseases, especially diseases alleviated by inhibition of the type 5 phosphodiesterase. In particular, the invention relates to the compounds of the invention for the treatment or prophylaxis of the following diseases:
male and female sexual dysfunction, such as, but not limited to, male erectile dysfunction, premature ejaculation,.Peyronie's disease;
acute and chronic ain/vay diseases, such as, but not limited to, COPD (chronic obstructive pulmonary disease), bronchitis, emphysema, pulmonary vascular remodeling, pulmonary hypertension, lung fibrosis, asthma, cystic fibrosis, bronchiectasis, bronchiolitis obliterans, connective tissue diseases, sarcoidosis, kyphoscoliosis, pneumoconiosis, amyotrophic lateral sclerosis, thoracoplasty, extrinsic allergic alveolitis;
inflammatory diseases, such as, but not limited to, vasculature inflammation, acute respiratory distress syndrome, mesangial glomerulonephritis, chronic inflammatory bowel disease, disseminated intravascular inflammation, allergic vasculitis, dermatoses (e.g., but not limited to,

psoriasis, toxic and allergic contact eczema, atopic eczema, seborrhoeic eczema, Lichen simplex,
sunburn, pruritus in the anogenital area, alopecia areata, hypertrophic scars, discoid lupus
erythematosus, follicular and widespread pyodermias, endogenous and exogenous acne, acne
rosacea), disorders of the arthritis type (e.g., but not limited to, rheumatoid arthritis, rheumatoid
spondylitis, osteoarthritis), disorders of the immune system [e.g., but not limited to, AIDS (acquired
immunodeficiency syndrome), multiple sclerosis], graft versus host reaction, allograft rejections,
shocic [e.g., but not (imited to, septic shocit, endotoxin shock, gram-negative sepsis shock, toxic
shock syndrome and ARDS (adult respiratory distress syndrome)], gastrointestinal inflammations
(e.g., but not limited to, Crohn's disease and ulcerative colitis); disorders which are based on
allergic and/or chronic, immunological false reactions (e.g., but not limited to, allergic rhinitis,
allergic sinusitis, chronic rhinitis, chronic sinusitis, allergic conjunctivitis, nasal polyps);
pain, such as, but not limited to, inflammatory pain;
right-heart failure, right heart hypertrophy (cor pulmonale), hypertension, hypercholesterolemia,
hypertrigiyceridemia;
ischaemic diseases, such as, but not limited to, diabetes mellitus, stroke, coronary artery disease,
angina (including, but not limited to, vasospastic angina), myocardial infarction, peripheral artery
disease, cerebrovascular obstruction, sleep apnea, macular ischaemia, arterial and venous
occlusion, congestive heart failure;
diabetic gastroparesis and diseases with symptoms of gastroparesis;
diseases or conditions in which it is desirable to suppress platelet function, for example, but not
limited to, after stent implantations (e.g., but not limited to, coronary sfenting), after bypass
operations, in pulmonary hypertension, thrombotic diseases, post-angioplasty stenosis, coronary
artery disease, infarction (e.g., but not limited to, myocardial infarction), instable angina pectoris,
stroke, and arterial and venous occlusion diseases (e.g., but not limited to, claudicatio intermittens);
diseases or conditions with an impairment or dysfunction of cerebral vascular reactivity and/or
neurovascular coupling, such as, but not limited to, arteriosclerotic dementia, multi-infarct
dementia, cerebral senility;
diseases which are based on neuronal damage or degradation, such as but not limited to, stroke,
spinal cord injury, brain injury, morbus parkinson, amyotrophic lateral sclerosis, morbus alzheimer,
amyloidosis, prion diseases and neuropathy;
peripheral arterial diseases, chronic renal failure, chronic heart failure, sepsis, senile dementia
(Alzheimer's disease), Creutzfeld-Jacob disease, septic encephalopathy, arteriosclerotic
encephalopathy, diabetes associated encephalopathy, toxic encephalopathy, vascular and
neuronal dementia, Huntington's disease, Parkinson's disease, multiple sclerosis and
preeclampsia;
portal hypertension, liver cirrhosis, toxic liver damage (e.g., but not limited to, alcohol-induced liver
damage), hepatitis, thrombosis of the portal vein, Budd-Chiari syndrome, malformation of liver
veins, compression of liver veins (e.g., but without limitation, due to tumors), arteriovenous fistula.

diseases associated with an enlarged spleen, schistosomiasis (bilharziosis), sarcoidosis and other granulomatous diseases, primary biliary cirrhosis, myeloproliferative disorders (e.g., but not limited to, chronic myeloid leukemia, osteomyeiofibrosis), lymphatic systemic diseases, collagenosis (e.g., but not limited to, systemic lupus erythematodes, sclerodermia), morbus Osier (congenital arteriovenous malformations, inter alia in the liver), nodular regenerative hyperplasia, tricuspid insufficiency, pericarditis constridiva, veno-occlusive disease (VOD), non-alcoholic steatohepatitis (NASH), liver fibrosis; benign prostatic hyperplasia;
insufficient uteroplacental blood flow in pregnancies with fetal growth restriction; insufficient brain sl^ills, such as but not limited to, verbal attainment, attention, concentration, deductive thinking, central auditory processing, cognition, learning, vigilance, apprehension and reagibility; Overactive Bladder; LUTS - lower urinary tract symptoms; Raynauds syndrome/phenomenon.
In this respect, the term "pulmonary hypertension" in particular embraces
pulmonary arterial hypertension including primary pulmonary hypertension (e.g. sporadic or familial) and pulmonary arterial hypertension related, for example, but without limitation, to collagen vascular disease, congenital systemic-to-pulmonary shunts, portal hypertension, human immunodeficiency virus infection, drugs or toxins {e.g., but not limited to, anorexigens), persistent pulmonary hypertension of the newborn;
pulmonary venous hypertension due to, for example, but without limitation, left-sided atrial or ventricufar heart disease, (eft-sided valvular heart disease, extrinsic compression of central pulmonary veins (e.g. fibrosing mediastinitis, adenopathy in relation to tumors), pulmonary veno-occlusive disease;
pulmonary hypertension associated with disorders of the respiratory system or hypoxemia including, for example, but without limitation, chronic obstructive pulmonary disease (COPD), interstitial lung disease, sleep-disordered breathing, alveolar hypoventilation disorders, chronic exposure to high altitude, neonatal lung disease, alveolar-capillary dysplasia;
pulmonary hypertension caused by chronic thrombotic or embolic diseases including thromboembolic obstruction of proximal pulmonary arteries and obstruction of distal pulmonary arteries, such as pulmonary embolism (due to thrombus, tumor, ova, parasites, or foreign material), in situ thrombosis and sickle-cell disease, in particular chronic thromboembolic pulmonary hypertension (CTEPH);
pulmonary hypertension caused by disorders directly affecting the pulmonary vasculature including inflammatory disorders (e.g., but not limited to, schistosomiasis, sarcoidosis) and pulmonary capillary hemangiomatosis.

Preferably, the invention further relates to the compounds of the invention for the treatment or prophylaxis of the following diseases: acute and chronic airway diseases, such as pulmonary hypertension, in particular chronic thromboembolic pulmonary hypertension, lung fibrosis, asthma, bronchitis, emphysema and chronic obstructive pulmonary disease.
The invention also relates to the use of a compound of the invention in the manufacture of a pharmaceutical composition inhibiting the type 5 phosphodiesterase, in particular a pharmaceutical composition for the treatment or prophylaxis of diseases alleviated by inhibition of the type 5 phosphodiesterase, preferably, a pharmaceutical composition for the treatment or prophylaxis of the diseases exemplified above.
Preferably, the invention relates to the use of a compound of the invention in the manufacture of a pharmaceutical composition for the treatment or prophylaxis of an acute or chronic air^vay disease, such as, but not limited to, pulmonary hypertension, lung fibrosis, asthma, bronchitis, emphysema and chronic obstructive pulmonary disease.
In a particularly preferred embodiment of the invention, the invention relates to the use of a compound of the above examples in the manufacture of a pharmaceutical composition for the treatment or prophylaxis of an acute or chronic airway disease, such as, but not limited to, pulmonary hypertension, lung fibrosis, asthma, bronchitis, emphysema and chronic obstructive pulmonary disease.
The invention further relates to a method of treating or preventing a disease comprising administering to a patient in need thereof a therapeutically effective amount of at least one of the compounds of the invention.
in particular, the invention relates to a method of treating or preventing one of the atiove mentioned diseases comprising administering lo a patient in need thereof a therapeutically effective amount of at least one of the compounds of the invention.
Especially, the invention relates to a method of treating or preventing a disease which is alleviated by inhibition of the type 5 phosphodiesterase comprising administering to a patient in need thereof a therapeutically effective amount of at least one of the compounds of the invention.
Preferably, the invention relates to a method of treating or preventing an acute or chronic ainA/ay disease, for example, but not limited to, pulmonary hypertension, lung fibrosis, asthma, bronchitis, emphysema and chronic obstructive pulmonary disease, comprising administering to a patient in need thereof a therapeutically effective amount of at least one of the compounds of the invention,

In the.above methods, the patient is preferably a mammal, more preferably a human. Furthermore. in the above methods, at least one of the compounds of the invention can be used. Preferably, one or two of the compounds of the invention are used, more preferably, one of the compounds of the invention is used.
In a particularly preferred embodiment of the invention, the atmve methods of treating or preventing one of the above mentioned diseases comprise administering to a patient in need thereof a therapeutically effective amount of one compound of the examples according to the present
invention. ,
The invention furthermore relates to a pharmaceutical composition which comprises at least one of the compounds of the invention together with at least one pharmaceutically acceptable auxiliary.
The invention additionally relates to a pharmaceutical composition for the treatment or prophylaxis of an acute or chronic airway disease, in particular for the treatment or prophylaxis of pulmonary hypertension, lung fibrosis, asthma, bronchitis, emphysema and chronic obstructive pulmonary disease.
Preferably, the pharmaceutical composition comprises one or two of the compounds of the invention. More preferably, the pharmaceutical composition comprises one of the compounds of the invention.
In a particularly preferred embodiment of the invention, the pharmaceutical composition comprises a compound of the examples according to the present invention together with at least one pharmaceutically acceptable auxiliary.
The invention additionally relates to a pharmaceutical composition comprising at least one of the compounds of the invention, at least one pharmaceutically acceptable auxiliary and at least one therapeutic agent selected from the group consisting of corticosteroids, anticholinergics, beta-mimetics, lung surfactants, endothelin antagonists, prostacyclins, calcium channel blockers, beta-blockers, type 4 phosphodiesterase inhibitors, antidepressants, antibiottcs, anticoagulants, diuretics and digitalis glycosides.
In this respect, the therapeutic agent includes the corticosteroids, anticholinergics, beta-mimetics, lung surfactants, endothelin antagonists, prostacyclins, calcium channel blockers, beta-blockers, type 4 phosphodiesterase Inhibitors, antidepressants, antibiotics, anticoagulants, diuretics and digitalis glycosides in form of the free compounds, the pharmaceutically acceptable salts thereof,

the pharmaceutically acceptable derivatives thereof (e.g., but not limited to, ester derivatives), the solvates thereof and the stereoisomers of the compounds, salts, derivatives and solvates.
Examples of corticosteroids include without limitation budesonide, fluticasone such as fluticasone propionate, beclometasane such as beclometasone dipropionate, triamcinolone sifch as triamcinolone acetonide, and ciclesonide. Examples of anticholinergics include without limitation indacaterol, tiotropium such as tiotropium bromide, and ipratropium such as ipratropium bromide. Examples of treta-mimetics include without limitation formotero! such as formoterol fumarate, and salmeterol such as salmeterol xinafoate. Examples of lung surfactants include without limitation lusupultide, poractant alfa, sinapultide, beractant, bovactant, colfosceril auch as colfosceril palmitate, surfactant-TA, and calfactant. Examples of endothelin antagonists include without limitation bosentan, ambrisentan and sitaxsentan such as sitaxsentan sodium. Examples of prostacyclins include without limitation iloprost such as iloprost tromethamine, epoprostenol such as epoprostenol sodium and treprostinil such as treprostinit sodium. Examples of calcium channel blockers include without limitation amiodipine such as amiodipjne besylate and amlodjpine maleale, nifedipine, diltiazem such as diltiazem hydrochloride, verapamil such as verapamil hydrochloride, and felodipine. Examples of beta-blockers include without limitation bisoprolol such as bisoprotol fumarate, nebivolol, metoprolol such as metoprolol succinate and metoprolol tartrate, carvedilol, atenolol and nadolol. Examples of type 4 phosphodiesterase inhibitors include without limitation roflumilast, roflumilast N-oxide, cilomilast, tetomilast and oglemilast. Examples of antidepressants include without limitation bupropion such as bupropion hydrochloride. Examples of antibiotics include without limitation amoxicillin, ampicillin, levofloxacin, clarithromycin, ciprofloxacin such as ciprofloxacin hydrochloride, telithromycin and azithromycin. Examples of anticoagulants include without limitation clopidogrel, enoxaparin, cilostazol, nadroparin, warfarin and abciximab. Examples of diuretics include without limitation furosemide, bumetanlde and torsemide. Examples of digitalis glycosides include without limitation digoxin and digitoxin.
In a preferred embodiment, the pharmaceutical composition comprises a compound of the
invention in combination with a corticosteroid. In a particularly preferred embodiment, the
pharmaceutical composition comprises:
a compound of the invention and budesonide,
a compound of the invention and fluticasone,
a compound of the invention and beclometasone,
a compound of the invention and triamcinolone, or
a compound of the invention and ciclesonide.
In a further preferred embodiment, the pharmaceutical composition comprises a compound of the
invention in combination with an anticholinergic. In a particularly preferred emtwdiment, the
pharmaceutical composition comprises:

a compound of the invention and indacateroL
a compound of the invention and tiotropium, or
a compound of the invention and ipratropium.
In a further preferred embodiment, the pharmaceutical composition comprises a compound of the
invention in combination with a beta-mimetic. In a particularly preferred embodiment, the
pharmaceutical composition comprises:
a compound of the invention and formoterol, or
a compound of the invention and salmeterol.
In a further preferred emtxKiiment, the pharmaceutical composition comprises a compound of the
invention In combination with a lung surfactant. In a particularly preferred embodiment, the
pharmaceutical composition comprises:
a compound of the invention and lusupultide,
a compound of the invention and poractant alfa,
a compound of the invention and sinapuKide,
a compound of the invention and beractant,
a compound of the invention and ttovactant,
a compound of the invention and colfosceril,
a compound of the invention and surfactant-TA, or
a compound of the Invention and calfactant.
In a further preferred embodiment, the pharmaceutical composition comprises a compound of the
invention in combination with an endothelin antagonist. In a particularly preferred embodiment, the
pharmaceutical composition comprises:
a compound of the invention and tMsentan,
a compound of the invention and ambrlsentan, or
a compound of the Invention and sitaxsentan.
In a further preferred embodiment, the pharmaceutical composition comprises a compound of the
invention in combination with a prostacyclin. In a particularly preferred embodiment, the
pharmaceutical composition comprises:
a compound of the invention and iloprost,
a compound of the invention and epoprostenol,
a compound of the Invention and triprostinil.
In a further preferred emtxxJiment, the pharmaceutical composition comprises a compound of the
invention in combination with a calcium channel blocker. In a particularly preferred embodiment,
the pharmaceutical composition comprises:
a compound of the invention and amiodipine,
a compound of the invention and nifedipine,
a compound of the Invention and diltiazem,
a compound of the invention and verapamil, or

a compound of the invention and felodipine.
In a further preferred embodiment, the pharmaceutical composition comprises a compound of the
invention in combination wWh a beta-blocl pharmaceutical composition comprises:
a compound of the invention and bisoprolol,
a compound of the invention and nebivolol,
a compound of the invention and metoprolol,
a compound of the invention and carvediiol,
a compound of the invention and atenotot, or
a compound of the invention and nadolol.
In a further preferred embodiment, the pharmaceutical composition comprises a compound of the
invention in combination with a type 4 phosphodiesterase inhibitor, in a particularly preferred
embodiment, the pharmaceutical composition comprises;
a compound of the invention and rofiumifast,
a compound of the invention and roflumilast N-oxide,
a compound of the invention and cilomilast,
a compound of the invention and tetomiiast, or
a compound of the invention and oglemilast.
In a further preferred embodiment, the pharmaceutical composition comprises a compound of the
invention m combination with an antidepressant. In a particulariy preferred embodiment, the
pharmaceutical composition comprises:
a compound of the invention and bupropion.
In a further preferred embodiment, the pharmaceutical composition comprises a compound of the
invention in combination with an antibiotic. In a particularly preferred embodiment, the
pharmaceutical composition comprises:
a compound of the invention and amoxjciflin,
a compound of the invention and ampicillin,
a compound of the invention and levofloxacin,
a compound of the invention and clarithromycin,
a compound of the invention and ciprofloxacin,
a compound of the invention and telithromycin, or
a compound of the invention and azithromycin.
In a further preferred embiodiment, the pharmaceutical composition comprises a compound of the
invention in combination with an anticoagulant. In a particularly preferred embodiment, the
pharmaceutical comf)osttton comprises:
a compound of the invention and clopidogrel,
a compound of the invention and enoxaparin,
a compound of the invention and cilostazol,

a compound of the invention and nadroparin,
a compound of the invention and warfarin, or
a compound of the invention and abciximab.
In a further preferred embodiment, the pharmaceutical composition comprises a compound of the
invention in combination with a diuretic. In a particularly preferred embodiment, the pharmaceutical
composition comprises:
a compound of the invention and furosemide,
a compound of the invention and bumetanide, or
a compound of the invention and torsemide.
In a further preferred embodiment, the phamiaceutical composition comprises a compound of the
invention in combination with a digitalis glycoside. In a particularly preferred embodiment, the
pharmaceutical composition comprises:
a compound of the invention and digoxin, or
a compound of the invention and digiioxin.
In a further preferred embodiment, the pharmaceutical composition comprises a compound of the
invention in combination with a corticosteroid and a beta-mimetic. In a particularly preferred
embodiment, the pharmaceutical composition comprises:
a compound of the invention, budesonide and indacaterol,
a compound of the invention, budesonide and formoteroi,
a compound of the invention, budesonide and salmeterol,
a compound of the invention, fluticasone and indacaterol,
a compound of the invention, fluticasone and formoteroi,
a compound of the invention, fluticasone and salmeterol,
a compound of the invention, bedometasone and indacaterot,
a compound of the invention, bedometasone and formoteroi,
a compound of the invention, bedometasone and salmeterol,
a compound of the invention, triamcinolone and indacaterol,
a compound of the invention, triamcinolone and formoteroi,
a compound of the invention, triamcinolone and salmeterol,
a compound of the invention, ciclesonide and indacaterol,
a compound of the invention, ciclesonide and formoteroi, or
a compound of the invention, ciclesonide and salmeterol.
In a further preferred embodiment, the phaimaceutical composition comprises a compound of the
invention in combination with a corticosteroid and an anticholinergic. In a particularly preferred
emtxxliment, the pharmaceutical composition comprises:
a compound of the invention, budesonide and tiotropium,
a compound of the invention, budesonide and ipratropium,
a compound of the invention, fluticasone and tiotropium,

a compound of the invent/on, fluticasone and ipratropium, a compound of the invention, beclometasone and tiotropium, a compound of the invention, beclometasone and ipratropium, a compound of the invention, triamcinolone and tiotropium, a compound of the invention, triamcinolone and ipratropium, a compound of the invention, ciclesonide and tiotropium, or a compound of the invention, ciclesonide and ipratropium,
The above mentioned compound of the invention is preferably a compound according to the examples.
The invention furthermore relates to pharmaceutical compositions according to the invention, as defined above, inhibiting the type 5 phosphodiesterase, especially for the treatment or prophylaxis of diseases alleviated by inhibition of type 5 phosphodiesterase, in particular for the treatment or prophylaxis of the diseases exemplified above.
The invention also encompasses pharmaceutical compositions according to the invention, as defined above, for the treatment or prophylaxis of the following diseases; acute and chronic airway diseases, such as pulmonary hypertension, lung fibrosis, asthma, bronchitis, emphysema and chronic obstructive pulmonary disease.
The pharmaceutical compositions according to the invention preferably contain the compound or compounds of the invention in a total amount of from 0.1 to 99.9 wt%, more preferably 5 to 95 vkft%, in particular 20 to 80 wt%. In case at least one therapeutic agent selected from the group consisting of corticosteroids, anticholinergics, beta-mimetics, lung surfactants, endothelin antagonists, prostacyclins, calcium channel blockers, tieta-bloclters, type 4 phosphodiesterase inhibitors, antidepressants, antibiotics, anticoagulants, diuretics and digitalis glycosides is present in the pharmaceutical compositions of the invention, the total amount of said therapeutic agent or therapeutic agents in the pharmaceutical compositions is preferably in the range of from 0.1 to 99.9 wt%, more preferably 5 to 95 wt%, in particular 20 to 80 vA.%, under the provision that the total amount of the compound or compounds of the invention and the therapeutic agent or therapeutic agents is less than 100 wt%. Preferably, the at least one compound of the invention and the at least one therapeutic agent are present in the pharmaceutical composition in a weight ratio of from 1000 : 1 to 1: 1000, more preferably 500 : 1 to 1: 500,
As pharmaceutically acceptable auxiliaries, any auxiliaries l
antioxidants, preservatives, stabilizers, carriers, fillers, binders, thickeners, complexing agents, disintegrating agents, buffers, permeation promoters, polymers, lubricants, coating agents, propellents, tonicity adjusting agents, surfactants, colorants, flavorings, sweeteners and dyes. In particular, auxilfaries of a type appropriate to the desired formulation and the desired mode of administration are used.
The pharmaceutical compositions can be formulated, for example, info tablets, coated tabfets (dragees), pills, cachets, capsules (caplets), granules, powders, suppositories, solutions (e.g., but not limited to, sterile solutions), emulsions, suspensions, ointments, creams, lotions, pastes, oils, gels, sprays and patches (e.g., but not limited to, transdermal therapeutic systems). Additionally, the pharmaceutical compositions can be prepared as e.g. liposome delivery systems, systems in which the compound of the invention is coupled to monoclonal antibodies and systems in which the compound of the invention is coupled to polymers (e.g., but not limited to, soluble or biodegradable polymers).
In case of pharmaceutical compositions comprising at least one of the compounds of the invention and at least one therapeutic agent selected from the group consisting of corticosteroids, anticholinergics, beta-mimetics, lung surfactants, endothetin antagonists, prostacyclins, calcium channel blockers, beta-blockers, type 4 phosphodiesterase inhibitors, antidepressants, antibiotics, anticoagulants, diuretics and digitalis glycosides, the compound of the invention and the therapeutic agent may be formulated together into the same dosage form (e.g., but not limited to, tablets), separately into the same dosage form (e.g., but not limited to, tablets), or into different dosage forms (without limitation e.g. the compound of the invention may be formulated as tablet and (he therapeutic agent may be formulated as powder, solution or suspension).
The pharmaceutical compositions can be manufactured in a manner known to a person skilled in the art, e.g. by dissolving, mixing, granulating, dragee-making, levigating, emulsifying, encapsulating, entrapping or lyophilizing processes.
The selected formulation depends inter alia on the route of administering the pharmaceutical composition. The pharmaceutical compositions of the invention can be administered by any suitable route, for example, by the oral, sublingual, buccal, intravenous, intraarterial, intramuscular, subcutaneous, intracutaneous, topical, transdermal, intranasal, intraocular, intraperitoneal, intrasternal, intracoronary, transurethral, rectal or vaginal route, by inhalation or by insufflation. Oral administration is preferred.
In case of pharmaceutical compositions comprising at least one of the compounds of the invention and at least one therapeutic agent selected from the group consisting of corticosteroids,

anticholinergics, beta-mimetics, lung surfactants, endothetin antagonists, prostacyclins, calcium channel blockers, beta-blockers, type 4 phosphodiesterase inhibitors, antidepressants, antibiotics, anticoagulants, diuretics and digitalis glycosides, the compound of the invention and the therapeutic agent may be administered by the same route, e.g., without limitation, orally, or by different routes, e.g., without limitation, the compound of the invention can be administered orally and the therapeutic agent can be administered by inhalation or instillation.
Tablets, coated tablets (dragees), pills, cachets, capsules (caplets), granules, solutions, emulsions and suspensions are e.g. suitable for oral administration. In particular, said formulations can be adapted so as to represent, for example, an enteric form, an immediate release form, a delayed release form, a repeated dose release form, a prolonged release form or a sustained release form. Said forms can be obtained, for example, by coating tablets, by dividing tablets into several compartments separated by layers disintegrating under different conditions (e.g. pH conditions) or by coupling the compound of the invention to a biodegradable polymer.
Administration by inhalation or instillation is preferably made by using an aerosol. The aerosol is a liquid-gaseous dispersion, a solid-gaseous dispersion or a mixed liquid/solid-gaseous dispersion,
The aerosol may be generated by means of aerosol-producing devices such as dry powder inhalers (DPIs), pressurized metered dose inhalers (PMDIs) and nebulizers. Depending on the kind of the compound of the invention, and optionally the therapeutic agent, to be administered, the aerosol-producing device can contain the compound and, optionally, the therapeutic agent in form of a powder, a solution or a dispersion. The powder may contain, for example, one or more of the following auxiliaries: carriers, stabilizers and fillers. The solution may contain in addition to the solvent, for example, one or more of the following auxiliaries: propellants, solubilizers (co-solvents), surfactants, stabilizers, buffers, tonicity adjusting agents, preservatives and flavorings. The dispersion may contain in addition to the dispersant, for example, one or more of the following auxiliaries: propellants, surfactants, stabilizers, buffers, preservatives and flavorings. Examples of carriers include, but are not limited to, saccharides, e.g. lactose and glucose. Examples of propellants include, but are not limited to, fluorohydrocarbons, e.g. 1,1,1,2-tetrafluoroethane and 1,1,1,2,3,3,3-heptafluoropropane.
The particle size of the aerosol particles (solid, liquid or solid/liquid particles) is preferably less than 100 pm, more preferably it is in the range of from 0.5 to 10 [jm, in particular in the range of from 2 to 6 pm (D50 value, measured by laser diffraction).
Specific aerosol-producing devices which may be used for inhaled administration include, but are not limited to, Cyclohaler®, Diskhaler®, Roladisk®, Turbohaler®, Autohaler®, Turbohaler®,

Novolizer®, Easyhaler®, Aerolizer®, Jethaier®, Diskus®, Ultrahaler® and Mystic® inhalers. The aerosol-producing devices may be combined with spacers or expanders, e.g. Aerochamber®, Nebulator®, Volumatic® and Rondo®, for improving inhalation efficiency.
In case of topical administration, suitable pharmaceutical formulations are, for example, ointments, creams, lotions, pastes, gels, powders, solutions, emulsions, suspensions, oils, sprays and patches (e.g., but not limited to, transdermal therapeutic systems).
For parenteral modes of administration such as, for example, intravenous, intraarterial, intramuscular, subcutaneous, intracutaneous, intraperitoneal and intrasternal administration, preferably solutions (e.g., but not limited to, sterile solutions, isotonic solutions) are used. They are preferably administered by injection or infusion techniques.
in case of intranasal administration, for example, sprays and solutions to be applied in drop form are preferred formulations.
For intraocular administration, solutions to be applied in drop form, gels and ointments are exemplified fbrmulations.
Generally, the pharmaceutical compositions according ta the invention can be administered such that the dose of the compound of the invention is in the range customary for type 5 phosphodiesterase inhibitors. In particular, a dose in the range of from 0.01 to 4000 mg of the compound of the inventron per day is preferred. In this respect, it is to be noted that the dose is dependent, for example, on the specific compound used, the species treated, age, body weight, general health, sex and diet of the subject treated, mode and time of administration, rate of excretion, severity of the disease to be treated and drug combination. In case the pharmaceutical composition of the invention comprises at least one of the compounds of the invention and at least one therapeutic agent selected from the group consisting of corticosteroids, anticholinergics, beta-mimetics, lung surfactants, endothelin antagonists, prostacyclins, calcium channel blockers, beta-btockers, type 4 phosphodiesterase inhibitors, antidepressants, antibiotics, anticoagulants, diuretics and digitalis glycosides, the same dose ranges apply to the therapeutic agent.
The pharmaceutical compositions according to the invention can be administered in a single dose per day or in multiple subdoses, for example. 2 to 4 doses per day. A single dose unit of the pharmaceutical composition can contain e.g. from 0.01 mg to 4000 mg, preferably 0.1 mg to 2000 mg, more preferably 0.5 to 1000 mg, most preferably 1 to 500 mg, of the compound of the invention. In case the pharmaceutical composition of the invention comprises at least one of the compounds of the invention and at least one therapeutic agent selected from the group consisting

of corticosteroids, anticholinergics, beta-mimetics, lung surfactants, endothelin antagonists, prostacyclins, calcium channel blockers, beta-blockers, type 4 phosphodiesterase inhibitors, antidepressants, antibiotics, anticoagulants, diuretics and digitalis glycosides, a single dose unit of the pharmaceutical composition can contain e.g. from 0.01 mg to 4000 mg, preferably 0.1 mg to 2000 mg, more preferably 0.5 to 1000 mg, most preferably 1 to 500 mg, of the therapeutic agent. Furthermore, the pharmaceutical composition can be adapted to weekly, monthly or even more infrequent administration, for example by using an implant, e.g. a subcutaneous or intramuscular implant, by using the compound of the invention In form of a sparingly soluble salt or by using the compound of the invention coupled to a polymer. Administration of the pharmaceulica) composition in a single dose per day is preferred.
In case the pharmaceutical composition of the invention comprises at least one of the compounds of the invention and at least one therapeutic agent selected from the group consisting of corticosteroids, anticholinergics, beta-mimetics, lung surfactants, endothelin antagonists, prostacyclins, calcium channel blockers, beta-blockers, type 4 phosphodiesterase inhibitors, antidepressants, antibiotics, anticoagulants, diuretics and digitalis glycosides, administration of the compound of the invention and administration of the therapeutic agent can be made simultaneously or sequentially. In case of sequential administration, the compound of the invention can be administered before or after administration of the therapeutic agent.

Biological investigations
Method for measuring inhibition of the type 5 phosphodiesterase (PDE5) activity:
As a source for human PDE5, platelets are used. For that purpose, 150 ml fresh blood from human donors anticoagulated with citrate [final concentration 0.3% (w/v)] is centrifuged at 200 g for 10 min to obtain the so-called platelet-rich-plasma (PRP) as a supernatant. 1/10 volume of ACD solution (85 mM Na3-citrate, 111 mM D-glucose, 71 mM citric acid, pH 4.4) is added to 9/10 volume of PRP. After centrifugation (1,400 g, 10 min) the cell peUet is resuspended in 3 mi homogenizalion buffer (NaCi 140 mM, KCI 3.8 mM, EGTA (ethylene glycol tetraacetic acid) ImM, MgCb ImM, Tris-HCl 20 mM, beta-mercaptoethanol 1mM, pH 8.2) plus protease-inhibitor mix giving rise to the final concentrations of 0.5 mM Pefablock (Roche), 10 |jM Leupeptin, 5 |jM Trypstninhibitor, 2 mM Benzamidin and 10 |jM Pepstatin A. The suspension is sonified and thereafter centrifuged for 15 min at 10,000 g. The resulting supernatant (platelet lysale) is used for enzymatic testings.
PDE5A1 activity is inhibited by the compounds of the invention in a modified SPA (scintillation proximity assay) test, supplied by Amersham Biosciences (see procedural instructions "phosphodiesterase [3H]cAMP SPA enzyme assay, code TRKQ 7090"), carried out in 96-well microtitre plates (MTP's). The test volume is 100 ^.1 and contains 20 mM Tris buffer (pH 7.4), 0.1 mg of BSA (travine serum albumin)/ml, 5 mM Mg^*, 1 pM motapizone, 10 nM PDE2 inhibitor 2-(3,4-dimethoxybenzyt)-7-[(1R,2R)-2-hydroxy-1-(2-phenylethyl)propyl]-5-methylimidazo(5,1-/][1,2.4]triazin-4(3H)-one, 0.5 ^M cGMP (cyclic guanosine monophosphate) (incladmg about 50,000 cpm of (3H]cGMP as a tracer), 1 jil of the respective compound dilution in dimethylsulfoxide (DMSO) and sufficient PDE5-containing platelet lysat (10,000xg supernatant, see above) to ensure that 10-20 vrt% of the cGMP is converted under the said experimental conditions. The final concentration of DMSO in the assay (1 % v/v) does not substantially affect the activity of the PDE investigated. After a preincubation of 5 min at 37°C, the reaction is started by adding the substrate (cGMP) and the assay is incubated for a further 15 min; after that, it is stopped by adding SPA beads (50 nl). In accordance with the manufacturer's instructions, the SPA beads had previously been resuspended in water, but are then diluted 1:3 (v/v) in water; the diluted solution also contains 3 mM 8-methoxymethyl-3-isobutyl-1-methylxanthine (IBMX) to ensure a complete PDE activity stop. After the beads have been sedi-mented {> 30 min), the MTP's are analyzed in commercially available luminescence detection devices. The corresponding iCw values of the compounds for the inhibition of PDE activity are determined from the concentration-effect curves by means of non-linear regression.
Representative inhibitory values determined for the compounds of the invention are given in the
following table:

Example -log lC50(mol/l)
1 10.11
2 10.01
3 9.40
4 9.79
5 9.91
6 10.07
7 9.67
8 9.65
9 8.94
10 9.70
11 9.84
12 10.16
13 9.11
14 8.86
15 9.00
16 9.41
17 9.47
18 6.74
19 8.61
20 9.27
21 8.74
22 9.31
23 9.35
24 9.52
25 9.62
26 9.34

27 9.43
28 9.16
29 9.56
30 9.32
31 9.65
32 8.96
33 8.82
34 9.46
35 9-15
36 9.31
37 9.04
38 9.40
39 9.11
40 9.37
41 9.05
42 9.72
43 9.55
44 9.10
45 8.81
46 8.86
47 9.64
48 9.37
49 9.47
50 9.85
51 9.31
52 9.52
53 9.43
54 9.38

55 9.43
56 9-55
57 9.33
58 9.47
59 9.13
60 9.58
61 9.28
62 9.51
63 9.04
64 9,22
1 65 8.94
66 9.20
67 8.86
68 9.04
69 8.75
70 8.97
71 8.87
72 9.36
73 8.73
74 9.26
75 8.80
76 8.62
77 8.67
78 8.64
79 8.81
80 8.85
81 8.83
82 8.96

83 8.29
84 8.53
85 8.80
86 8.40
87 8.95
88 8.78
89 8.89
90 8.25
91 8.20
92 8.47
93 8.60
94 8.06
95 8.48
96 8.67
97 9.93
98 9.66
99 9.75
100 9.90
101 9.79
102 9.94
103 9.33
104 9.63
105 9.43
106 9.05
107 9.27
108 9.18
109 9.16
110 9.67

111 9.98
112 9.86
113 9.70
114 8.65
115 8.42
116 8.51
117 8.96
118 9.30
119 8.92
120 8.92
121 8.75
122 8.86
123 8.74
124 8.66
125 8.93
126 9.33
128 9.68
129 9.41
130 9.90
131 9.31
132 9.53
133 9.20
134 9.46
135 8.70
136 8.43
137 8.65
138 8.22
139 9.69

140 9.83
141 9.03
142 9.21
143 8.82
144 9.94
145 10.00
146 9.64
147 9.62
148 9.39
149 9.53
150 9.41
151 9.53
152 7.84
153 8.21
154 7.77
155 8.02
156 8.18
157 7.81
158 7.62
159 8.22
160 7.63
161 8.28
162 7.96 •
164 8.11
165 8.23
166 7.99
167 8.28
168 8.10

169 8.76
170 7.86
171 9.52
172 9.95
173 9.73
174 9.41
175 9.61
176 9.61
177 9.91
178 9.64
179 9.74
180 8.92
181 9.23
182 9.32
183 8.73
184 8.50
185 8.69
186 9.26
187 9.34
188 9.29
189 9.41
190 9.60
191 8.99
192 9.08
193 8.97
194 9.08
195 8.88
196 9.12

197 9.07
198 9.21
199 9.23
200 9.32
201 9.39
202 9.13
203 9.41
204 9.59
205 9.06
206 9.18
207 9.61
208 8.73
209 9.16
210 9.19
211 8.63
212 8.97
213 9.26
214 8.58
215 8.59
216 8.82
217 8.65
218 8.60
219 8.70
220 8.13
221 8.19
222 8.72
223 8.46
224 8.16

225 8.15
226 8.47
227 7.85
228 9.79
229 9.70
230 9.62
231 9.16
232 9.45
233 9.12
234 9.01
235 9.34
236 8.78
237 9.21
238 9.50
239 8.60
240 9.30
241 8.87
242 9.01
243 8.64
244 8.71
245 8.94
246 8.44
247 8.63
248 8.96
249 8.67
250 8.32
251 9.44
252 8.92

253 9.77
254 9.23
255 7.87
256 7.92
257 8.03
258 8.20
259 8.07
260 8.32
261 7.96
262 8.03
263 8.00
264 9.66
265 9.54
266 10.10
267 9.49
268 9.10
269 9.24
270 9.72
271 9.26
272 9.15
273 8.66
274 8.28
275 9.46
276 9.78
277 7.03
278 7.24
279 8.63
280 8.76

281 6.07
282 6.60
283 8.29
284 8.54

Animal pharmacological testing
Nitric oxide regulates smooth muscle tone by elevation of cGMP via activation of guanylate cyclase and subsequent activation of cyclic GMP-dependent protein kinase. The amplitude and duration of the cGMP signal in smooth muscle is largely regulated by cGIVIP-specific cyclic nucleotide phosphodiesterase 5 (PDE5). Therefore, inhibition of PDE5 or activation of guanylate cyclase causes altered arterial blood pressure response, which is more pronounced under conditions of acute arterial hypertension, which can be easily induced by continuous intravenous (i.v.) phenylephrine(PE)-infusion. The aim of the study was to evaluate the effects of the selective PDE5 inhibitors described in this invention on phenylephrine-induced acute arterial hypertension and sodium-nitroprusside (SNP) induced blood pressure response in anaesthetised male Spraque Dawley rats.
Method
The test compound (suspended in a 4% w/v aqueous methylcellulose solution either 3 or 10 mg/kg) or placebo {i.e. 4% aqueous methylcellulose solution) is administered orally to conscious Spraque Dawley rats 90 min prior to SNP administration. 40 min later, rats are anaesthetised by intramuscular administration of 80 mg/kg ketamine-HCI + 4 mg^g xylazin-HCI and ventilated with -1.5% isoflurane in a mixture of ambient air and 40% oxygen. Catheters for i.v. PE- and SNP- administration and recording of mean arterial blood pressure (MAP) are inserted. One hour after compound or placebo administration, a continuous i.v. (V. femoralis) PE-infusion (3 pg/kg/min at an infusion rate of 0.06 ml/min) is started and maintained till the end of the experiment. 30 min after start of the PE-infusfon, an i.v.-bolus of the NO-donor sodium nifroprusside (SNP, 30 pg/kg at a volume of 1.0 ml/kg) is administered. To assess the effect of test compounds (PDE5 inhibitory activity) in comparison to placebo, MAP response is analysed, MAP prior to SNP-administration and area under the curve of MAP within 180 s following SNP-administration, corrected for initial MAP (corr. AUCMAPO-I8OS) is used, to describe altered arterial vascular response and thus in vivo PDE5-inhibitory activity. The efficacy (% change vs. control) achievable in this model is approximately between -13% and ^5% effectforthe examples 2, 3, 4, 6, 7, 8. 10, 11, 15, 16, 23, 24, 26, 50, 98, 99, 112, 113, 132, 171, 172, 173, 176, 177, 178, 179,181, 182, 187, 228, 237, 269 and 272.

WE CLAIM
1. Compound of formula (I)



wherein
R1 is –CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally susstituted by R11,
R11 is 1-4C-alkoxy or hydroxyl,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or-C(O)-1-4C-
alkyl,
or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, hatogen, 1-4C-alkyl, 1-4C-a/koxy, hydroxy or 1-4C-fluoroalkoxy,
or R22 and R23 combine to form a group -O-CH2-O-.
R24 is hydrogen,
Y is -(CH2),-
n is0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6,
R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-CCO)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyi, wherein the 1-4C-alkyi group is optionaiiy substituted by R43,
R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-aikoxy or hydroxy,
R43 is 1-4C-aikoxy or hydroxy,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,

R7 is hydrogen, 1-4C-alkyt, which is optionally substituted by R71, 3-6C-cycloalkyl, which is optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73,
R71 is 1-4C-alkoxy or hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl, which Is optionally substituted by R92,
R91 is 1-4C-alkoxy or hydroxy,
R92 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof or a stereoisomer of the compound,
the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
2. Compound according to claim t, wherein
R1 is -CH2-3-4C-cycloalkyl or 2-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fiuoroalkoxy or -C{0}-1-4C-
alkyl,
or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyf, 1-4C-alkoxy, hydroxy or 1-4C-fluaroalkoxy,
R24 is hydrogen,
Y is -(CH;),-,
n is 0 or 1,
R3 is a 4- to 6-membered saturated1Heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4,
R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cydoalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R43, R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-aikoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof or a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
3. Compound according to claim 1, wherein
R1 is -CH2-3-4C-cycloalkyl or 2-4C-alkyl which is optionally substituted by R11, R11 is 1-4C-alkoxy or hydroxy,

R21 is hydrogen,
R22 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy, 1-4C-fluoroalkoxy or -C(O)-1-4C-
alkyl,
or R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-alkoxy, hydroxy or 1-4C-fluoroalkoxy,
R24 is hydrogen,
Y is -{CH2),-,
n is 0 or 1,
R3 is a cyclohexyl group substituted by R6,
R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C-alkyl, which is optionally substituted by R71, 3-6C-cycfoalkyl, which is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy or hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1 -4C-aIkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof or a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
4. Compound according to claim 1, wherein
R1 is -CH2-3-6C-cycloalkyl or 1-4C-alkyl which is optionally substituted by R11,
R11 is 1-4C-alkoxy or hydroxy,
R21 and R22 combine to form a group -O-CH2-O-,
R23 is hydrogen, halogen, 1-4C-alkyl, 1-4C-a!koxy, hydroxy or 1-4C-fluoroatkoxy,
R24 Is hydrogen,
Y is -(CH2)n-,
n is 0 or 1,
R3 is a 4- to 7-membered saturated heterocyclic ring containing one nitrogen atom and
optionally one oxygen atom, said heterocyclic ring being optionally substituted by R4, or a
3-6C-cycloalkyl group substituted by R6,
R4 is -C(O)-H, -C(O)-1-4C-alkyl, wherein the 1-4C-alkyl group is optionally substituted by R41,
-C(O)-3-6C-cycloalkyl, wherein the 3-6C-cycloalkyl group is optionally substituted by R42,
or -C(O)-O-1-4C-alkyl, wherein the 1-4C-alkyl group is optronally substituted by R43, R41 is 1-4C-alkoxy or hydroxy,
R42 is 1-4C-alkoxy or hydroxy,
R43 is 1-4C-alkoxy or hydroxy,

R6 is -NH-C(O)-R7, -C(O)-NR8R9 or NH2,
R7 is hydrogen, 1-4C'alkyl, which is optionally substituted by R71, 3-6C-cycloalkyl, whiich is
optionally substituted by R72, or 1-4C-alkoxy, which is optionally substituted by R73, R71 is 1-4C-alkoxy Of hydroxy,
R72 is 1-4C-alkoxy or hydroxy,
R73 is 1-4C-alkoxy or hydroxy,
R8 is hydrogen,
R9 is 1-4C-alkyl, which is optionally substituted by R91, or 3-6C-cycloalkyl,
R91 is 1-4C-alkoxy or hydroxy,
a salt thereof, an N-oxide of the compound or the salt thereof or a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof,
5. Compound according to claim 1 selected from 4-(5-Cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolot3,2-d]pyrimidine-7-carboxyIic acid (1-propionyl-piperidin-4-yl)-amid; 4-({1-[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]-methanoyl}-amino)-prperidine-1-carboxylic acid ethyl ester; 4-(5-Cyclopropylmethoxy-benzofl ,3]dioxol-4-yi)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-m6thoxy-acetyl)-piperidin-4-yl]-amide; trans-4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4- acetylamino-cyclohexyl)-amide; trans-4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4- [(1-cyclopropyl-methanoyl}-amino]-cyclohexyl)-amide; trans-[4-({1-[4-(5-Cyclopropy/methoxy-benzo(1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]-methanoyl}-amino}-cyclohexyl]-carbamic acid ethyl ester; cis-4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl}-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4- acetylamino-cyclohexyl)-amide; cis-4-(5-Cycfopropyfmethoxy-benzo[1,3]clioxol-4-yl)-5H-pyrrolo[3,2-o]pyrimidine-7-carboxylic acid {4- [(1-cyclopropyl-methanoyl}-amino]-cyclohexyl}-amide; cis-4-(5-CyclQpropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(2-methoxy-ethanoylamino)-cyclohexyl]-amide; cis-[4-({1-[4-{5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]-methanoyl}-amino)-cyclohexyl]-carbamic acid ethyl ester; 4-{5-Cyclopropylmethoxy-benzo[1,3]dioxoi-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-acetyl-piperidin-4-yl)-amide; 4-{5-Cyclopropy[methoxy-benzo[1,3jdioxQl-4-yi)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(1-cyclopropyl-methanoyl)-piperidin-4-yI]-amide; 4-(5-Cyclopropylmethoxy-benzot1,3]dtoxol-4-yl)-5H-pyrrolo(3,2-d]pyrimidine-7-carboxylic acid [(R)-1-{2-methoxy-acetyl)-pyrrolidin-3-yl]-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ((R)-1-formyl-pyrrolidin-3-yl)-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrroto[3,2-d]pyrimidine-7-carboxylic acid ((R)-1-acetyl-pyrrolidin-3-yl)-amide; 4--azetidin-3-yl]-amide; 3-{{1-[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c/]pyrimidin-7-yl]-methanoyl}-amino)-azetidine-1-carboxylic acid ethyl ester; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxoi-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-formyl-piperidin-4-yl)-amide; 4-(5-Cyclopropylmethoxy-benzo[1-1-(2-methoxy-ethanoyl)-prperidin-3-yl]-amide; 4-(2-Cyclopropylmethoxy-5-fluoro-4-fnethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimldine-7-carboxylicactd {{S)-1-acetyl-piperldln-3-yl)-amide;4-(2-Cyclopropylmethoxy-5-tluoro-4-fnethoxy-plienyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ((R)-1-acelyl-pyrrolidin-3-yl)-amide; 4-(2-Cyclopropy Imethoxy-5-fIuoro-4-methoxy-plnenyl)-5H-pyrrolo[3,2-d] pyrimidine-7-carboxyIic acid ({R)-1-propionyl-pyrrolidin-3-yl)-amide; 4-(2-Cyclopropylmethoxy-5-fluorcH4-methoxy-phenyt)-5H-pyrrolo[3,2-d]pyrimldine-7-carboxylic acid [(R)-1-{2-nnethoxy-acetyl)-pyrrolid!n-3-ylI-amide; trans-4-(2-Cyclopropylnnethoxy-5-methyl-plienyl)-5H-pyrrolo[3,2-d]pyrinfiidine-7-carboxylic acid (4-acetylamino-cyclohexyl)-amide; lrans-4-(2-Cyclopropylmelhoxy-5-methyl-phenyl)-5H-pyrrolo[3,2-d)pyrimidine-7-carboxylic acid [4-(2-methoxy-acelylaminocydohexyl]-amide; trans-(4-{[4-(2-Cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrro!o(3,2-d]pyrimidine-7-carbonyl]-amino}-cyclohexyl>-carbamic acid ethyl ester; 4-(2-Cyclopropy(methoxy-5-methy!-phenyi)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-acetyl-piperidin-4-yl)-amide; 4-(2-cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrrolol3,2-o(]pyrimidine-7-carboxylic acid i1-(2-nnettioxy-acetyi)-piperidin-4-yl]-amide; 4-{[4-(2-cyclopropylmethoxy-5-methyl-phenyl)-5H-pyrroIo[3,2-d]pyrimidine-7-carbonyi]-amino}-piperidine-1-carboxylie acid ethyl ester; trans-4-(5-Cyclobutylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-dlpyrimldirie-7-carboxylic acid (4-acetylamino-cyclohexyl)-amide; trans-4-(5-Cyclobutylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7'carboxyiic acid [4-(cyclopropanecarbonyl-amino)-cyclohexyl]-amide; trans-4-(5-Cycfobutylmethoxy-benzoll, 3]dioxol-4-yl)-5H-pyrrolo[3,2-c/]pyrimidine-7-carboxylic acid [4-{2-niethoxy-etlnanoylamino)-cyclohexyl]-amide; 4-{5-Cyclobutylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-cartxDxylic acid (1-acetyl-piperidin-4-yl)-amide;'4-{5-Cyclobuty!methoxy-benzo[1,3]dioxol-4-yi)-5H-pyrrolo[3,2-d]pyritnidine-7-carboxylic acid l1-(1-cycloprapyl-nnethanoyl)-piperidin-4-yl]-amide; 4-(5-Cyclobutylmethoxy-benzo[1,3]dioxo!-4-yl)-5H-pyrrolo[3,2-d]pyrimldine-7-carboxylic acid [1-(2-methioxy-ethanoyl)-piperidin-4-yl]-amide; 4-({1-[4-(5-Cyclobutylmethoxy-benzo[1,3ldioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]-methanoyl}-amino)-piperidine-1-carboxylic acid ethyl ester; 4-{5-Ettioxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyllcacid (1-propionyl-piperldin-4-yl)-amide; 4-{[4-(5-Ethoxy-ben2o[1,3]dioxol-4-yl>-5H-pyrrolo[3,2-<: acid ethyl ester>3]dioxol-4-yl>5H-pyrroto{3,2-d]pyrimidine-7-cafboxy/ic acid {(R)- 1-propionyl-pyrro(id(n-3-yj)-amide; (R)-3-{[4-(5-Ethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-pyrrolidine-1-carboxylic acid ethyl ester; 4-(5-Ethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-dlpyrimidine-7-carboxylic acid [(R)-1-{2-methoxy-acetyl)-pyrrolidin-amide; 4-(5-Propoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo(3,2-d]pyrinnidine-7-carboxylic acid (1-propionyl-piperidin-4-yl)-amide; 4-{[4-{5-Propoxy-benzo[1,3]dioxol-4-yl)-5H-pyrro(o[3,2-d]pyrimidine-7-carbonylI-amino}-piperidine-1-carboxylic acid ethyl ester; 4-{5-Propoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ((R)-1-propionyl-pyrrolidin-3-yl)-amide; (R)-3-{I4-(5-Propoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrirridine-7-carbonyl]-amino}-pyrrolidine-1-carboxylic acid ethyl ester; 4-(5-Prcpoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d)pyrimidine-7-carboxyiicacid [(R)-1-(2-methoxy-acetyl)-pyrrolidin-3-yl]-amide; 4-{5-Butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolol3,2-d]pyrimidine-7-carboxylic acid {1-propionyl-piperidin-4-yl)-amide; 4-{[4-(5-Butoxy-benzo[1,3]dioxol-4-y))-5H-pyrrolo[3,2-d]pyrimidine-7-carbonylJ-amino}-piperidine-1-carboxylic acid ethyl ester; 4-(5-Butoxy-benzo|1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyiic acid {1-formyl-piperidin-4-yl)-amide; 4-(5-Butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-o(|pyrimidine-7-carboxylic acid (1-propior)yl-piperidin-3-yl)-amide; 3-{[4-(5-Butoxy-benzo[1,3]dioxoI-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl]-amino}-piperidine-1-cartioxylic acid ethyl ester; 4-(5-Butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-rf|pyr(midine-7-carboxyi(c acid [1-(2-fnethoxy-acetyl)-piper(din-3-ylJ-afn(de; 4-(5-Butoxy-
benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid ({R)-1-propionyl-pyrrolidin-3-yl}-amide; {R)-3-{[4-(5-Butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c(|pyrirnidine-7-carbonyl]-amino}-pyrrotdine-1-carboxy)Jcacid etliy) ester, cis-4-(4-Methoxy-2-(2-methoxy-ethoxy)-pheny)]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-acetylamino-cyciohexyl)-annide; cis-4-[4-IVfethoxy-2-(2-methoxy-ethoxy)-plienyl]-5H-pyrrolo[3,2-d]pyrinriidine-7-carboxylic acid [4-(cyclopropanecarbony(-amino}-cyclohexyl]-amide; cis-4-[4-Methoxy-2-(2-methoxy-ethoxy)-plienyl)-5H-pyrroio[3,2-d]pyrimidine-7-carboxylic acid [4-(2-methoxy-acetyIamino)-cyclohexyl]-amide; trans-4-[4-Methoxy-2-(2-meHioxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-acetylamino-cyclohexyl)-amide; trans-4-[4-Methoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(cyclopropanecarbonyl-amino)-cyciohexyi]-amide; trans-4-[4-M ethoxy-2-f 2-m eth oxy-ethoxy)-pheny)]-5H-pyrroio(3,2-d]py rim id in e-7-carboxylic acid [4-(2-methoxy-acetyiannino)-cyclohexyl]-amide; 4-[4-Methoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrrolo[3,2'C(|pyrinnidine-7-carboxylic acid {1-acelyl-piperidin-4-yl)-amide; 4-[4-Melhoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrroio[3,2-d]pyrimidine-7-carboxylic acid {1-cyclopropanecarbonyl-piperidin-4-yl}-amide; 4-[4-Methoxy-2-(2-methoxy-ethoxy)-phenyl]-5H-pyrroio[3,2-cf|pyrimidine-7-carboxylic acid [1-(2-methoxy-acetyl)-piperidin-4-yi]-amide; lrans-4-[5-(2-Methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrroiQ[3,2-d]pyrimidine-7-carboxylic acid (4-acetylamino-cyclohexyl)-amide; lrans-4-[5-(2-Methoxy-ethoxy)-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-acetylamino-cyclohexyl)-amide; trans-4-[5-(2-IVIethoxy-ethoxy)-ben2o[1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-{2-methoxy-acetylamino)-cyclohexyl]-amide; cts-4-[5-{2-l\1ethoxy-ethoxy)-ben2o(1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-acetytamino-cycfohexyl)-amtde; cis-4-[5-(2-IWefhoxy-ethoxy)-benzo[1,3]dioxo(-4-yl]-5H-pyrrofo[3,2-cf|pyrimidine-7-carboxylic acid (4~acetylamino-cyclohexyl)-amide; cis-4-[5-(2-Methoxy-ethoxy)-ben2o[1,3]djoxol-4-yl)-5H-pyrrolo[3,2-c(]pyrinfiidine-7-carboxy!ic acid [4-{2-methoxy-acetyiamino)-cyclohexylj-amide; cl&-[4-({4-[5-(2-Methoxy-ethoxy)-benzo[1,3]dioxoi-4-yl]-5H-pyrroio[3,2-cf|pyrimidin6-7-carbonyl}-amino)-cyclohexyl]-carbamic acid ethyl ester; 4-[5-{2-Methoxy-eHioxy)-benzo[1,3]dioxol-4-yl]-5H-pyrroio[3,2-d]pyrimidine-7-carboxylic acid (1-acetyl-piperidin-4-yl)-amide; 4-[5-(2-Methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrro!o[3,2-d]pyrimldine-7-carboxylic acid (1-cyclopropanecarbonyl-piperidin-4-yl)-amide; 4-[5-(2-Methoxy-ethoxy)-benzo[1,3]dioxol-4-y!]-5H-pyrralo[3,2-d]pyrimidine-7-carboxy(rc acid [1-(2-methoxy-acetyl)-piperidin-4-ylJ-amide; 4-{5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyltcac!d [1-(2-hydroxy-ethanoyl)-piperidin-4-yl]-amide; trans-[4-{{1-[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol~4-yl)-5H-pyrrolo[3,2-copyrimidine-7~carboxylic acid [4-(2-hydroxy-ethanoylamino)-cyclohexyl]-amide; t ra ns-[4-({1 -[4-(5-Cyclopropy I methoxy-be nzo[1,3]d ioxol-4-y I )-5H- py rrolo[3,2-c(l pyri mid I ne-7-carboxylic acid [4-((S)-2-hydroxy-propanoyIamino)-cyclohexyl]-amide; cis-[4-({1-[4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yI)-5H-pyrrola[3,2-d]pyrimidine-7-carboxyiic acid [4-(2-hydroxy-elhanoylamino)-cyclohexyl]-amide; cis-[4-({ 1 -[4-(5-Cyclopropylmethoxy-benzo[ 1,3]dioxol-4-yl)-5H-pyrrolo[3.2-c5pyrJmidine-7-carboxylic acid [4-((S)-2-hydroxy-propanoylamino)-cyclohexyl]-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxo)-4-yl}-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-((S)-2-hydroxy-propanoyl)-piperidin-4-yl]-annide; trans-4-(5-Cyclopropylmetlnoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4-[(1-hydrQxy-cyclopropanecarbonyl)-amino]-cyclohexyl}-amide; cis-4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-(/|pyrimidine-7-carboxylic acid {4-[(1-hydroxy-cyclopropanecarbonyl)-amino]-cyclohexyl}-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {1-[1-(1-hydroxy-cyclopropyl)'methanoyl]-piperJdJn-4-yl}-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d)pyrinnidine-7-carboxylicactd [(R)-1-(2-hydroxy-ethanoyl)-pyrrolidin-3-yl]-ainide; 4-(5-Cyc[opropylmethoxy-benzof1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1-((S)-2-hydroxy-propanoyl)-pyrrolidin-3-yl]-amide; 4-(5-Cyclopropy!methoxy-benzo[1,3Idioxol-4-yl)-5AV-pyrrolo[3,2-cOpyrimidine-7-carboxylic acid {(R)-1-[1-(1-hydroxy-cyclopropyl)-niethanoyl]-pyrrolidin-3-yl}-amide; 4-{5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [{S)-'l-(2-hydroxy-ethanoyl)-pyrrolidin-3-yl)-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c(]pyrimJdine-7-carboxylic acid [(S)-1-((S)-2-hydroxy-propanoyl)-pyrrolidln-3-yl]-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidlne'7-carboxylic acid {(S)-1-I1-(1-hydroxy-cyclopropyl)-nnetlianoyl]-pyrrolidin-3-yt}-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-hydroxy-ethanoyl)-piperidin-4-ylmethyl]-amide; 4-{5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl>-5H-pyrrolot3,2-d]pyrimidine-7-carboxylic acid [1-((S}-2-hydroxy-propanoyl}-piperidin-4-ylmethyl]-amide; 4-{5-Cyciopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-cOpyrimidine-7-carboxyhcacid (1-[1-(1-hydroxy-cyc(opropyl)-methanoylI-piperidin-4-ylmethyl}-amide; 4-(5-Cyclopropylnriethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-hydroxy-acetyl)-piperidin-3-ylmetliyl)-aTnide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d!pyrimidine-7-carboxylic acid [1-((S)-2-hydroxy-propionyl)-piperidin-3-ylmethyl]-amJde; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid J1-(2-hydroxy-acetyl>pyrrolidln-3-ylmethyl]-amide; 4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrrmid[ne-7-carboxylic acid [1-((S)-2-hydroxy-propionyl)-pyrrolidin-3-yimethyl]-amide;4-(5-CyclQpropylmethoxy-ben2o[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c(jpyrimidine-7-carboxylic acid [4-(2-hydroxy-acetyl)-morpholin-2-ylmetliyi]'annide; 4-(5-Cyclopropylmethoxy-benzof 1,3]dio);ol-4-yl)-5H-pyrroto[3,2-c(]pyrim;d(ne-7-carboxylic acid [4-((S)-2-hydroxy-propionyl)-morpholin-2-ylmethyl]-amide; 4-(5-Cyc(opropylmethoxy-benzo[1,3]dioxol-4-yi)-5H-pyrrolo[3.2-d|pyrimidine-7-carboxylic acid [1-(2-hydroxy-ethanoyl)-azetidin-3-yi]-amide; 4-{5-Cyclopropylmelhoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-G(]pyrimidine-7-carboxylJc acid [1-({S)-2-hydroxy-propanoyl>-azetidin-3-yl]-amide; 4-(5-Cyc(opropylmethoxy-benzo(1,3]dioxol-4-y!)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(S)-1-({S)-2-hydroxy-propanoyl)-piperidin-3-yl]-amide; 4-(5-cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrroio[3,2-d]pyrtmidine-7-carboxylic acid [(R)-1-((S)-2-hydroxy-propanoyl)-piperidrn-3-yl]-amide; trans-4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo{3,2-c(]pyrimidine-7-carboxylic acid [4-(2-hydroxy-acetylamino)-cyclohexyl]-

amide; trans-4-(2-Cyc)opropylmethoxy-4-metboxy-phenyJ)-5H-pyrro)o[3,2-d]pyrimidine-7-carboxylJc acid [4-({S)-2-hydroxy-propionylamino)-cyclohexyl]-amide; trans-4-{2-Cyclopropylmethoxy-4-methoxy-plnenyl)-5H-pyrrolo[3,2-cf)pyrimidine-7-carboxylicgcid {4-[(1-hydroxy-cycfopropanecarbanyl)-amlno]-cyclohexy(}-am(de; cis-4-(2-Cyclopropyfmethoxy-4-methoxy-phe nyl)-5H-pyrro!o[3,2-d]pyrimidine-7-carboxylic acid [4-{2-hydroxy-acetylamino)-cyclohexyl]-amide; cis-4-{2-Cyc!opropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-{(S)-2-hydroxy-propiony[amlno)-cyclohexyl]-amide; cls-4-{2-Cyc!opropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4-[{1-hydroxy-cyclopropanecarbonyl)-amino]-cyclohexyl}-amide; 4-(2-Cyclopropylmethoxy-4-methoxy-pheny!)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-hydroxy-ethanoyl)-piperidin-4-yl]-amide; 4-(2-Cyclopropylmethoxy-4-nnethoxy-pheny!)-5H-pyrrolo[3,2-d]pyrrmidine-7-carboxylic acid [1-((3)-2-hydroxy-propanoyl)-piperidin-4-yI]-amide; 4-(2-Cyclopropylmethoxy-4-methoxy-phenyl)-5f/-pyrrolo[3,2-d]pyrimldine-7-carboxylic acid {1-[1-(1-hydroxy-cyclopropyl)-methanQyl]-piperldin-4-yl}-annide; cis-4-(2-Cyclopropylmethoxy-5-methoxy-pheriyl)-5H-pyrrolol3,2-d)pyrimidine-7-carboxylic acid 14-(2-hydroxy-acetylamino)-cyclohexyl)-anfiide; cis-4-(2-Cyclopropylmethoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4-[(1-hydroxy-cyclopropanecarbonyi)-amino]-cyclohexyl}-amide; trans-4-(2-Cyclopropylmethoxy-5-melhoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyiicacid {4-[(1-hydroxy-cycloprDpanecarbonyl)-amino]-cyclohexyl}-amide; 4-(2'Cyc)opropy)methoxy-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-(2-hydroxy-acetyf)-piperidin-4-ylj-amide; 4-(2-Cyclopropylmethoxy-5-methoxy-pheny!)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-((S)-2-hydroxy-propionyl>-p(per(din-4-yl]-amide,"4-(2-Cyctopropylmethoxy-5-methoxy-phenyl)-5H-py rrolo[3,2-c(l py rim id i ne-7-ca rboxy lie acid[1-(1-hyd roxy-cy clopropaneca rbony l)-piperid in-4-y I] -amide; cls-4-{2-Cy clopropy Im ethoxy^-f!u oro-phe ny I )-5H-py rro lo[3,2-dl py rim id i ne-7-ca rboxyl ic acid (4-(2-hydroxy-acety(amino}-cyciohexyf]-amide; cis-4-(2-Cyciopropyfm6thoxy'4-fluoro-phenyl)-5H-pyrroio[3,2-d]pyrimidine-7-carboxylic acid [4-((S)-2-hydroxy-propiony!amino)-cyclohexyl]-amide; cis-4-{2-Cyclopropylmethoxy-4-fiuoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4-[(1-hydroxy-cyclopropanecarbonyl)-amino]-cyc)ohexyl}-amide; trans-4-(2-Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-(2~hydroxy-acetylamino)-cyclohexyl]-amide; trans-4-(2-Cyclopropylmethoxy-4-f1uoro-phenyl)-5H-pyrroto[3,2-d]pyrimidine-7-carboxylic acid t4-((S}-2-hydroxy-propionylamino)-cyclohexyl]-amide; trans-4-(2-Cyclopropylmethoxy-4-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4-[(1-hydroxy-cyclopropanecarbonyl)-amino]-cyclohexyl}-amide; 4-(2-Cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2-o(]py"n^idine-7-carboxylic acid [1-{2-hydroxy-acetyl)-piperidrn-4-yl]-amide; 4-(2-Cyclopropylmethoxy-5-fiuoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-((S)-2-hydroxy-propionyl)-piperidin-4-yl]-amide; lrans-4-(2-Cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-{2-hydroxy-acetylamino)-cydohexyl]-amide; trans-4-{2-Cyclopropylmelhoxy-4-fluoro-phenyl}-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-({S)-2-hydroxy-propionylamino)-cycloh exy l]-a mide; trans-4-(2-Cyclopropylm ethoxy-phe ny l)-5H-py rrolo[3,2-c(]py rim id ine-7-carboxylic acid [4-{2-hydroxy-acetylamino)-cyclohexyl]-amide; trans-4-(2-Cyc)opropylmethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyiicacid [4-({S)-2-hydroxy-propionylamino)-cyclohexyl]-amide; trans-4-(2-Cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrinidine-7-carboxylie acid {4-[{ 1 -hydroxy-cydopropanecarbony/)-amino]-cyclohexyl}-amide; 4-(2-Cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-((S)-2-hydroxy-propionyl)-piperidin-4-yi]-amide; 4-(2-Cyclopropylmethoxy-4-fluoro-5-nnethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [1-((S)-2-hydroxy-propionyl)-piperidin-4-yl]-amide; 4-(2-Cyctopropylnfiethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1-(2-hydroxy-acetyl)-piperidin-3-yl]-amide; 4-{2-Cyclopropylmethoxy-4-fiuoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidlne-7-carboxylic acid [(R)-1-((S)-2-hydroxy-propionyl)-piperidin-3-yl]-amide; 4-(2-Cyclopropylmethoxy-4-f!uoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1-(2-hydroxy-acetyl)-pyrrolidin-3-yl]-amide; 4-(2-cyclopropylmethoxy-4-fluoro-5-methoxy-phenyl)-5H-pyrrolo[3,2-c/]pyrimidine-7-carboxyi]c acid [(R)-1-((S)-2-hydroxy-propionyl)-pyrrolidin-3-yl]-amide; trans-4-(2-Cyclopropylmethoxy-5-fluoro-4-methoxy-phenyl)-5H-pyrrolol3,2-d]pyrimidine-7-carboxylic acid [4-(2-hyd roxy-acetylam i no)-cycloli exyl]~a m ide; tra ns-4-{2-Cyc!opropyIm ethoxy-5-flu Qro-4-m ethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4-((S)-2-hydroxy-propionylamino)-cyclohexyl]-amide; trans-4-{2-cyclopropylmethoxy-5-fiuoro-4-methoxy-phenyl)-5H--pyrro(o[3,2-cflpyrimidine-7-carboxylic acid {4-[(1~hydroj-piperidin-4-y!]-amide; 4-{5-Butoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [(R)-1 -((S)-2-hydroxy-propionyl}-pyrrolidin-3-yl]-amide; trans-4-[4-Methoxy-2-(2-methoxy-ethoxy)-pheny)]-5H-pyrrolof3,2-cOpyrtmidine-7-carboxylic acid [4-(2-hydroxy-acetylamino)-cyclohexyl]-amide; trans-4-[4-Methoxy-2-(2-meHioxy-eHioxy)-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid [4'((S)-2-hydroxy-propionylamino)-cyclohexyl]-amide; trans-4-[4-Methoxy-2-{2-methoxy-ethoxy)-ptienyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid {4-[(1-hydroxy-cydapropan9carbQnyl)-amino]-cyclohexyl)-am'ide; cis-4-[4-MethQxy-2-(2-methoxy-ethoxy)-phenyl)-5H-pyrrolo[3,2-d]pyrimldine-7-carboxylic acid {4-[(1 -hydroxy-cyclopropanecarbonyl)-am i no]-cyclohexy l}-amide; 4-[4-Methoxy-2-(2-methoxy-ethoxy )-phenyl]-5H-pyrrolo [3,2-d] pyrimidine-7-carboxylic acid [1-(1-hydroxy-cyclopropanecarbonyl)-piperidiri-4-yl]-amide; trans-4-{5-(2-Methoxy-ethoxy)-benzo(1,3]dioxol-4-y)]-5H-pyrrolo[3,2-d)pyrimidine-7-carboxylic acid [4-(2-hydroxy-acetylamino)-cyclohexyl]-amide; cts-4-[5-(2-Methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrfolo[3,2-d]pyrimidine-7-carboxylic acid [4-(2-tiydroxy-acetylamino)-cyclohexylJ-amide; cis-4-[5-(2-Methoxy-ethoxy)-benzo[1,3]dioxol-4-yl]-5H-pyrroto[3,2-d]pyrimidine-7-carboxylic acid [4-((S)-2-hydroxy-propionylamino)-cyciohexyl]-amide; 4-[5-(2-Methoxy-ethoxy)-benzo{1,3]dioxol-4-yl]-5H-pyrrolo[3,2-d}pyrimidine-7-carboxylic acid [1-((S)-2-hydroxy-propionyl)-piperidin-4-yt]-amid6; 4-(5-Acety[-2-cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyiicacid [1-((S)-2-hydroxy-propanoyl)-pip6ridin-4-yl)-annidG; 4-(5-Acetyl-2-cydopropylmethoxy-plienyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-(2-methoxy-acelyl)-piperidin-4-yl]-amide; 4-(5-Acety!-2-cyclopropylmethoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-acetyl-piperidin-4-yl)-amide; 4-(5-Acetyl-2-cydopropylmefhoxy-4-methy(-phenyl)-5H-pyrro(o[3,2-0]pyrimidine-7-carboxylic acid [1-((S)-2-hydroxy-propionyi)-piperidin-4-yl]-amide; 4-(5-Acetyl-2-cyclopropytmethoxy-4-nnethyi-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-acetyl-piperidin-4-yl)-amtde; trans-4-(5-Cyc!opropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-c(]pyrimidine-7-carboxylic acid [4-(2-methoxy-ethylcarbamoyl)-cyclohexyl]-amide; trans-4-(5-Cyclopropylmethoxy-benzo[1,3ldioxol-4-yiy5H-pyrrolo[3,2-dlpynmidine-7-carboxylic acid (4-cyciopropylcarbamoyl-cyclohexyl)-amide; trans-4-(2-Cyclopropyfmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-cyclopropylcarbamoyl-cyclohexyl)-amide; trans-4-{2-Cyclopropylmethoxy-4-methoxy-phenyl)-5H-pyrrolo[3,2-d]pyrimrdine-7-carboxylic acid [4-(2-methoxy-ethylcarbamoyl}-cyclohexyll-amide; tran5-4-(2-Cyciopropylmethoxy-5-fluoro-phenyl)-5H-pyrroJo[3,2-0]pyrimidine-7-carboxy)ic acid {4-cyclopropy)carbamoyl-cydohexyl)-amide; trans-4-(2-Cyclopropylmethoxy-5-fluoro-phenyl)-5H-pyrrolo[3,2-c(jpyrimidine-7-carboxylic acid [4-(2-methoxy-ethylcarbamoyl}-cyclohexyl)-amide; trans-4-(5-Cyclobutylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrinnidine-7-carboxytic acid [4-(2-methoxy-ethylcarbamoyl}-cyclohexyl]-amide; trans-4-(5-Cyclopropylmethoxy-benzo[1,3]dioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (4-cyctopropylcarbamoyl-cyclohexyi)-amide; 4-(2-Cyclopropylmethoxy-5-fluoro-4-hydroxy-phenyJ)-5H-pyrrolo[3,2-d]pyrtmidine-7-carboxylic acid (1-acetyl-piperidln-4-yl)-amide; 4-(2-Cyctopropylnnethoxy-5-fluoro-4-hydroxy-phenyi)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-propionyl-piperidin-4-yl)-amide; 4-[2-Cyclopropylmethoxy-4-(1,1-difluoro-methoxy)-5-fluoro-phenyl]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid (1-acetyl-prperidin-4-yl)-amide: 4-[2-cyclopropylnnethoxy-4-{1,1-dit]uoro-methoxy)-5~f)uoro-phenyl]-5H-pyrrolo{3,2-dlpyrimidine-7-carboxylic acid [1 -(2-metJioxy-ethanoyi)-piperidfn-4-yl]-amide; 4-(2-cyclopropylmethoxy-5-fluoro-4-hydroxy-phenyl}-5H-pyrrolo(3,2-d]pyrimidine-7-carboxylic acid [1-(2-hydroxy-acetyl)-piperidin-4-yi]-aniide 4-(2-cyclopropylmethoxy-5-fIuoro-4-hydroxy-phenyl)-5H-pyrrolo[3,2-d]pyrJmidine-7-carboxyiicacld l1-{{S)-2-hydroxy-propionyl)-piperidin-4-yl]-amide; 4-l2-Cyclopropylmethoxy-4-(1,1-difluoro-methoxy>5-fiuoro-phenyl]-5H-pyrroloI3,2-d]pyrimidine-7-carboxylic acid fl -{2-hydroxy-acetyl)-plperidin-4-yl]-annide; 4-[2-Cyciopropylmethoxy-4-(1,1-difluoro-methoxy)-5-fluoro-phenyi]-5H-pyrrolo[3,2-d]pyrimidine-7-carboxyiic acid [1-((S)-2-hydroxy-propionyl)-piperidin-4-y)]-amide; a salt thereof, an N-oxide of the compound or the sait thereof or a stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof.
6. Compound, pharmaceuticaliy acceptable salt thereof, N-oxide of the compound or the salt thereof or stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt or the pharmaceuticaliy acceptable salt thereof according to any of claims 1 to 5 for the treatment or prophylaxis of diseases.
7. Compound, pharmaceuticaliy acceptable salt thereof, N-oxide of the compound or the salt thereof or stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt or the pharmaceuticaliy acceptable salt thereof according to any of claims 1 to 5 for the treatment or prophylaxis of an acute or chronic airway disease.
8. Pharmaceutical composition comprising at least one of the compounds, pharmaceuticaliy acceptable salts thereof, N-oxides of the compounds and the salts thereof and stereoisomers of the compounds, salts, N-oxides of the compounds or N-oxides of the salts thereof or the pharmaceuticaliy acceptable salts thereof according to any of claims 1 to 5 together with at least one pharmaceuticaliy acceptable auxiliary.
9. Pharmaceutical composition according to claim 8 further comprising at least one therapeutic
agent selected from the group consisting of corticosteroids, anticholinergics, beta-mimetics, tung surfactants, endothelin antagonists, prostacyclins, calcium channel blockers, beta-blockers, type 4 phosphodiesterase inhibitors, antidepressants and antibiotics.
10. Use of a compound, pharmaceutically acceptable salt thereof, N-oxide of the compound or
the salt thereof or stereoisomer of the compound, tfie salt, the N-oxide of the compound or the
N-oxide of the salt thereof or the pharmaceutically acceptable salt thereof according to any of
claims 1 to 5 in the manufacture of a pharmaceutical composition inhibiting (he type 5
phosphod i esterase.
11. Use of a compound, pharmaceutically acceptable salt thereof, N-oxide of the compound or the salt thereof or stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof or the pharmaceutically acceptable salt thereof according to any of claims 1 to 5 in the manufacture of a pharmaceutical composition for the treatment or prophylaxis of an acute or chronic airway disease.
12. Use according to claim 11, wherein the acute or chronic airway disease is selected from pulmonary hypertension, lung fibrosis, asthma, bronchitis, emphysema and chronic obstructive pulmonary disease.
13. Use of a compound, phamnaceutically acceptable salt thereof, N-oxide of the compound or (he salt thereof or stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof or the pharmaceutically acceptable salt thereof according to any of claims
1 to 5 in the manufacture of a pharmaceutical composition for the treatment or prophylaxis of portal hypertension, liver cirrhosis, toxic liver damage, hepatitis, non-alcoholic steatohepatitis or liver fibrosis.
14. Method for treating or preventing an acute or chronic airway disease comprising adminis
tering to a patient in need thereof a therapeutically effective amount of a compound, pharmaceuti
cally acceptable salt thereof, N-oxide of the compound or the salt thereof
or stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof or the pharmaceutically acceptable salt thereof according to any of claims 1 to 5.
15. tylethod fortreating or preventing an acute or chronic airway disease according to claim 14,
in which the acute or chronic ainway disease is selected from the group consisting of pulmonary
hypertension, lung fibrosis, asthma, bronchitis, emphysema and chronic obstructive pulmonary
disease.

16. Method of treating or preventing portal hypertension, liver cirrhosis, toxic liver damage, hepatitis, non-alcoholic steatohepatitis or liver fibrosis comprising administering to a patient in need thereof a therapeutically effective amount of a compound, pharmaceutically acceptable salt thereof, N-oxide of the compound or the salt thereof or stereoisomer of the compound, the salt, the N-oxide of the compound or the N-oxide of the salt thereof or the pharmaceutically acceptable salt thereof according to any of claims 1 to 5.

Documents:

http://ipindiaonline.gov.in/patentsearch/GrantedSearch/viewdoc.aspx?id=2rrWuMXWIg9cQoQ9udABLQ==&amp;loc=vsnutRQWHdTHa1EUofPtPQ==


Patent Number 271899
Indian Patent Application Number 1980/MUMNP/2010
PG Journal Number 11/2016
Publication Date 11-Mar-2016
Grant Date 09-Mar-2016
Date of Filing 20-Sep-2010
Name of Patentee TAKEDA GMBH
Applicant Address BYK-GULDEN-STR. 2, 78467 KONSTANZ, GERMANY
Inventors:
# Inventor's Name Inventor's Address
1 JOSEF STADLWIESER IM APFELGARTEN 3, 78465 KONSTANZ, GERMANY
2 BEATE SCHMIDT ALLENSBACHER STR. 5, 78476 ALLENSBACH, GERMANY
3 HEIKO BERNSMANN SCHUBERTSTR. 21, 60325 FRANKFURT, GERMANY
4 ALEXANDER SUDAU BRUCHERWEG 5A, 42799 LEICHLINGEN, GERMANY
5 TORSTEN DUNKERN KASTANIENWEG 24, 78269 VOLKERTSHAUSEN, GERMANY
6 DEGENHARD MARX OBERE REUTE 15, 78345 MOOS, GERMANY
7 JORG DIEFENBACH AM HOPFENBUHL 17, 78333 STOCKACH- WINTERSPUREN, GERMANY
PCT International Classification Number C07D487/04,A61K31/519,A61P11/00
PCT International Application Number PCT/EP2009/052198
PCT International Filing date 2009-02-25
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 08102052.1 2008-02-27 EUROPEAN UNION