Title of Invention

ARYLALKYLCARBAMATE DERIVATIVES AND PROCESSES FOR PREPARATION THEREOF

Abstract The invention relates to a compound having general formula (I), wherein: n represents an integer of between 1 and 6; A is selected from one or more X, Y and/or Z groups; X represents an optionally-substituted C1-2-alkylene group; Y represents an optionally-substituted C2-alkenylene group or a -C<u>=</u>C- group; Z represents a C3-7-cycloalkyl group having formula (II) in which m represents an integer of between 1 and 5, and p and q represent integers and are defined such that p+q equals a number of between 1 and 5; R1 represents a hydrogen atom, a halogen atom or a hydroxyl, cyano, nitro, C1-3-alkyl, C1-3-alkoxy, C1-3-thioalkyl, C1-3-fluoroalkyl, C1-3-fluoroalkoxy, C1-3-fluorothioalkyl group; R2 represents a hydrogen atom, a halogen atom or a cyano, nitro, hydroxyl, C1-3-alkyl, C1-3-alkoxy, C1-3-thioalkyl, C1-3-fluoroalkyl, C1-3-fluoroalkoxy, C1-3-fluorothioalkyl group, or an optionally-substituted aromatic or heteroaromatic group; R3 represents either a 2,2,2-trifluoroethyl group or an optionally-substituted phenyl group; and R6 and R7 represent independently of each other a C1-3-alkyl group, a phenyl; said compound taking the form of a base, an acid addition salt, a hydrate or a solvate. The invention also relates to the use of the compound in therapeutics.
Full Text The invention relates to arylalkylcarbamate
derivatives, to the preparation thereof and to the use
thereof in therapeutics.
The compounds of the invention correspond to general
formula (I):

in which
n represents an integer between 1 and 6;
A is chosen from one or more groups X, Y and/or Z;
X represents a C1-2-alkylene group optionally
substituted with one or more C1-12-alkyl, C3-7-cycloalkyl
or C3-7-cycloalkyl-C1-6-alkylene groups;
Y represents a C2-alkenylene group optionally
substituted with one or more C1-12-alkyl, C3-7-cycloalkyl
or C3-7-cycloalkyl-C1-6-alkylene groups; or a group -C≡C-

Z represents a C3-7-cycloalkyl group of formula:

m represents an integer ranging from 1 to 5;
p and q represent integers and are defined such that
p+q is a number ranging from 1 to 5;
R1 represents a hydrogen atom, a halogen atom, or a
hydroxyl, cyano, nitro, C1-3-alkyl, C1-3-alkoxy, C1-3-
thioalkyl, C1-3-f luoroalkyl, C1-3-f luoroalkoxy or C1-3-

fluorothioalkyl group;
R2 represents
a hydrogen atom, a halogen atom,
or a cyano, nitro, hydroxyl, C1-3-alkyl, C1-3-alkoxy,
C1-3-thioalkyl, C1-3-fluoroalkyl, C1-3-f luoroalkoxy or
C1-3-fluorothioalkyl group;
or a group chosen from a phenyl, naphthalenyl,
biphenyl, phenylethylenyl, naphthylethylenyl,
pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl,
triazinyl, indanyl, indenyl, quinolinyl, isoquinolinyl,
quinazolinyl, quinoxalinyl, phthalazinyl, cinnolinyl,
thienyl, furyl, pyrrolyl, imidazolyl, pyrazolyl,
oxazolyl, thiazolyl, isoxazolyl, isothiazolyl,
thiadiazolyl, oxadiazolyl, triazolyl, benzothienyl,
benzofuryl, dibenzofuryl, benzimidazolyl, benzo-
triazolyl, indolyl, isoindolyl, indazolyl,
benzoxazolyl, benzisoxazolyl, benzothiazolyl, benziso-
thiazolyl, dihydroindolyl, pyrrolopyridinyl, furo-
pyridinyl, thienopyridinyl, imidazopyridinyl,
oxazolopyridinyl, thiazolopyridinyl, pyrazolopyridinyl,
isoxazolopyridinyl, isothiazolopyridinyl, tetrahydro-
quinolinyl, tetrahydroisoquinolinyl, phenyloxy,
phenylthio, phenylsulfonyl, benzoyl, phenylmethoxy,
phenylethoxy, phenylpropoxy, naphthalenyloxy,
naphthalenylmethoxy, naphthalenylethoxy, naphthalenyl-
propoxy, quinolinoxy and isoquinolinoxy, and optionally
substituted with one or more substituents chosen from a
halogen atom, and the following groups: hydroxyl,
cyano, nitro, C1-4-alkyl, C1-4-alkoxy, C1-4-thioalkyl,
C1-3-fluoroalkyl, C1-3-f luoroalkoxy, C1-3- fluorothioalkyl,
phenyloxy, benzyloxy, piperidyl, pyrrolidinyl,
morpholinyl, NH2, NHR6, NR6R7, NHCOR6, COR6, CO2RS, SO2R6,
-O- (C1-3-alkylene) -O-, 4-piperazinyl optionally
substituted with a C1-3-alkyl or with a benzyl;
R3 represents
either a 2,2,2-trifluoroethyl group,
or a phenyl group optionally substituted with one or
more halogen atoms or cyano, nitro, C1-3-alkyl, C1-3-
alkoxy, trifluoromethyl or trifluoromethoxy groups,

and
R6 and R7 represent, independently of one another, a
C1-3-alkyl group or a phenyl. .
In the context of the invention, the compounds of
general formula (I) can therefore comprise several
groups A which may be identical to or different from
one another.
The following compounds are not part of the invention:
- 2,2,2-trifluoroethyl benzylcarbamate;
- 2,2,2-trifluoroethyl 4-methoxybenzylcarbamate;
- 4-nitrophenyl 2-[4-(phenylmethoxy)phenyl]ethyl-
carbamate;
- 4-chloro-2-nitrophenyl 2-(4-(chlorophenyl)ethyl-
carbamate;
- 4-nitrophenyl 2- (3,4-dimethoxyphenyl)ethylcarbamate;
- phenyl 2-(3,4-dimethoxyphenyl)ethylcarbamate;
- 4-cyanophenyl 2-(4-methylphenyl)ethylcarbamate;
- 2,4,5-trichlorophenyl 2-(4-chlorophenyl)ethyl-
carbamate;
- phenyl 4-chlorobenzylcarbamate;
- phenyl 4-methoxybenzylcarbamate;
- 4-fluorophenyl 2-(4-methoxyphenyl)ethylcarbamate;
- phenyl 3-nitrobenzylcarbamate;
- 4-cyanophenyl 4-methoxybenzylcarbamate;
- phenyl 3-chlorobenzylcarbamate,•
- phenyl 3,4-dichlorobenzylcarbamate;
- 4-nitrophenyl 2-(4-hydroxyphenyl)ethylcarbamate;
- phenyl 2-[4-(2-ethyl-5,7-dimethyl-3H-imidazo-
[4,5-b]pyridin-3-yl)phenyl]ethylcarbamate;
- phenyl 2-[4-(3-thienyl)phenyl]propylcarbamate;
- phenyl 2-[4-(2-amino-4-thiazolyl)phenyl]ethyl-
carbamate;
- 2,3,4,5,6-pentafluorophenyl 4-bromobenzylcarbamate.
Among the compounds of general formula (I) , a first
subgroup of compounds consists of the compounds for
which:

n represents an integer between 1 and 6;
A is chosen from one or more groups X, Y and/or Z;
X represents a C1-2-alkylene group optionally-
substituted with one or more C1-12-alkyl, C3-7-cycloalkyl
or C3-7-cycloalkyl-C1-6-alkylene groups;
Y represents a C2-alkenylene group optionally
substituted with one or more C1-12-alkyl, C3-7-cycloalkyl
or C3-7-cycloalkyl-C1-6-alkylene groups; or a group
-C≡C-;
Z represents a C3-7-cycloalkyl group of formula:

m represents an integer ranging from 1 to 5;
p and q represent integers and are defined such that
p+q is a number ranging from 1 to 5;
R1 represents a hydrogen atom, a halogen atom, or a
hydroxyl, cyano, nitro, C1-3-alkyl, C1-3-alkoxy, C1-3-
thioalkyl, C1-3-f luoroalkyl, C1-3-f luoroalkoxy or C1-3-
fluorothioalkyl group;
R2 represents
a halogen atom, or a nitro, hydroxyl, C1-3-alkyl or C1-3-
alkoxy group; and
R3 represents
either a 2,2,2-trifluoroethyl group,
or a phenyl group optionally substituted with one or
more halogen atoms, or cyano, nitro, C1-3-alkyl, C1-3-
alkoxy, trifluoromethyl or trifluoromethoxy groups.
The following compounds are not part of the first
subgroup of compounds above:
- 2,2,2-trifluoroethyl 4-methoxybenzylcarbamate;
- 4-chloro-2-nitrophenyl 2-(4-chlorophenyl)ethyl-
carbamate;
- 4-nitrophenyl 2-(3,4-dimethoxyphenyl)ethylcarbamate;
- phenyl 2-(3,4-dimethoxyphenyl)ethylcarbamate;

- 4-cyanophenyl 2-(4-methylphenyl)ethylcarbamate;
- 2,4,5-trichlorophenyl 2-(4-chlorophenyl)ethyl-
carbamate;
- phenyl 4-chloropbenzylcarbamate;
- phenyl 4-methoxybenzylcarbamate;
- 4-fluorophenyl 2-(4-methoxyphenyl)ethylcarbamate;
- phenyl 3-nitrobenzylcarbamate;
- 4-cyanophenyl 4-methoxybenzylcarbamate;
- phenyl 3-chlorobenzylcarbamate;
- phenyl 3,4-dichlorobenzylcarbamate;
- 4-nitrophenyl 2-(4-hydroxyphenyl)ethylcarbamate;
- 2,3,4,5,6-pentafluorophenyl 4-bromobenzylcarbamate.
Among the compounds of the general formula (I) , a
second subgroup of compounds consists of the compounds
for which:
n represents an integer between 1 and 6;
A is chosen from one or more groups X, Y and/or Z;
X represents a C1-2-alkylene group optionally
substituted with one or more C1-12-alkyl, C3-7-cycloalkyl
or C3-7-cycloalkyl-C1-s-alkylene groups;
Y represents a C2-alkenylene group optionally
substituted with one or more C1-12-alkyl, C3-7-cycloalkyl
or C3-7-cycloalkyl-C1-6-alkylene groups; or a group
-C≡C-;
Z represents a C3-7-cycloalkyl group of formula:

m represents an integer ranging from 1 to 5;
p and q represent integers and are defined such that
p+q is a number ranging from 1 to 5;
R1 represents a hydrogen atom, a halogen atom, or a
hydroxyl, cyano, nitro, C1-3-alkyl, C1-3-alkoxy, C1-3-
thioalkyl, C1-3-f luoroalkyl, C1-3-f luoroalkoxy or C1-3-
fluorothioalkyl group;

R2 represents
a hydrogen atom, or a cyano, C1-3-thioalkyl, C1-3-
fluoroalkyl, C1-3-fluoroalkoxy or C1-3-f luorothioalkyl
group,
or a group chosen from a phenyl, naphthalenyl,
biphenyl, phenylethylenyl, naphthylethylenyl,
pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl,
triazinyl, indanyl, indenyl, guinolinyl, isoquinolinyl,
quinazolinyl, quinoxalinyl, phthalazinyl, cinnolinyl,
thienyl, furyl, pyrrolyl, imidazolyl, pyrazolyl,
oxazolyl, thiazolyl, isoxazolyl, isothiazolyl,
thiadiazolyl, oxadiazolyl, triazolyl, benzothienyl,
benzofuryl, dibenzofuryl, benzimidazolyl, benzo-
triazolyl, indolyl, isoindolyl, indazolyl,
benzoxazolyl, benzisoxazolyl, benzothiazolyl, benziso-
thiazolyl, dihydroindolyl, pyrrolopyridinyl, furo-
pyridinyl, thienopyridinyl, imidazopyridinyl,
oxazolopyridinyl, thiazolopyridinyl, pyrazolopyridinyl,
isoxazolopyridinyl, isothiazolopyridinyl, tetrahydro-
quinolinyl, tetrahydroisoquinolinyl, phenyloxy,
phenylthio, phenylsulfonyl, benzoyl, phenylmethoxy,
phenylethoxy, phenylpropoxy, naphthalenyloxy,
naphthalenylmethoxy, naphthalenylethoxy, naphthalenyl-
propoxy, quinolinoxy and isoquinolinoxy, and optionally
substituted with one or more substituents chosen from a
halogen atom, and the following groups: hydroxyl,
cyano, nitro, C1-4-alkyl, C1-4-alkoxy, C1-4-thioalkyl,
C1-3-fluoroalkyl, C1-3-f luoroalkoxy, C1-3-f luorothioalkyl,
phenyloxy, benzyloxy, piperidyl, pyrrolidinyl,
morpholinyl, NH2, NHRe, NR6R7, NHCOR6, COR5, C02R6, SO2R6,
-O-(C1-3-alkylene)-O-, 4-piperazinyl optionally
substituted with a C1-3-alkyl or with a benzyl;
R3 represents
either a 2,2,2-trifluoroethyl group,
or a phenyl group optionally substituted with one or
more halogen atoms or cyano, nitro, C1-3-alkyl, C1-3-
alkoxy, trifluoromethyl or trifluoromethoxy groups,
and
R6 and R7 represent, independently of one another, a

C1-3-alkyl group or a phenyl.
The following compounds are not part of the second
subgroup of compounds above:
- 2,2,2-trifluoroethyl benzylcarbamate;
- 4-nitrophenyl 2-[4-(phenylmethoxy)phenyl]ethyl-
carbamate;
- phenyl 2-[4-(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]-
pyridin-3-yl)phenyl]ethylcarbamate;
- phenyl 2-[4-(3-thienyl)phenyl]propylcarbamate;
- phenyl 2- [4-(2-amino-4-thiazolyl)phenyl]ethyl-
carbamate .
Among the compounds of general formula (I) , a first
family of compounds consists of the compounds for
which:
n represents an integer between 1 and 6;
A is chosen from one or more groups X, Y and/or Z;
X represents a C1-2-alkylene group optionally
substituted with one or more C1-12-alkyl, C3-7-cycloalkyl
or C3-7-cycloalkyl-C1-6-alkylene groups;
Y represents a C2-alkenylene group optionally
substituted with one or more C1-12-alkyl, C3-7-cycloalkyl
or C3-7-cycloalkyl-C1-6-alkylene groups; or a group
-C≡C-;
Z represents a C3-7-cycloalkyl group of formula:

m represents an integer ranging from 1 to 5;
p and q represent integers and are defined such that
p+q is a number ranging from 1 to 5;
R1 represents a hydrogen atom, a halogen atom, or a
hydroxyl, cyano, nitro, C1-3-alkyl, C1-3-alkoxy, C1-3-
thioalkyl, C1-3-fluoroalkyl, C1-3-fluoroalkoxy or C1-3-

fluorothioalkyl group;
R2 represents
a hydrogen atom, a halogen atom,
or a cyano, nitro, hydroxyl, C1-3-alkyl, C1-3-alkoxy,
C1-3-thioalkyl, C1-3-fluoroalkyl, C1-3-f luoroalkoxy or
C1-3-fluorothioalkyl group,
or a group chosen from a phenyl, naphthalenyl,
biphenyl, phenylethylenyl, naphthylethylenyl,
pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl,
triazinyl, indanyl, indenyl, quinolinyl, isoquinolinyl,
quinazolinyl, quinoxalinyl, phthalazinyl, cinnolinyl,
thienyl, furyl, pyrrolyl, imidazolyl, pyrazolyl,
oxazolyl, thiazolyl, isoxazolyl, isothiazolyl,
thiadiazolyl, oxadiazolyl, triazolyl, benzothienyl,
benzofuryl, dibenzofuryl, benzimidazolyl, benzo-
triazolyl, indolyl, isoindolyl, indazolyl,
benzoxazolyl, benzisoxazolyl, benzothiazolyl, benziso-
thiazolyl, dihydroindolyl, pyrrolopyridinyl, furo-
pyridinyl, thienopyridinyl, imidazopyridinyl,
oxazolopyridinyl, thiazolopyridinyl, pyrazolopyridinyl,
isoxazolopyridinyl, isothiazolopyridinyl, tetrahydro-
quinolinyl, tetrahydroisoquinolinyl, phenyloxy,
phenylthio, phenylsulfonyl, benzoyl, phenylmethoxy,
phenylethoxy, phenylpropoxy, naphthalenyloxy,
naphthalenylmethoxy, naphthalenylethoxy, naphthalenyl-
propoxy, quinolinoxy and isoquinolinoxy, and optionally
substituted with one or more substituents chosen from a
halogen atom, and the following groups: hydroxyl,
cyano, nitro, C1-4-alkyl, C1-4-alkoxy, C1-4-thioalkyl,
C1-3-fluoroalkyl, C1-3-f luoroalkoxy, C1-3-f luorothioalkyl,
phenyloxy, benzyloxy, piperidyl, pyrrolidinyl,
morpholinyl, NH2, NHR6, NR6R7, NHCOR6, COR6, CO2R6, SO2R6,
-O-(Ca-3-alkylene)-O-, 4-piperazinyl optionally
substituted with a C1-3-alkyl or with a benzyl;
R3 represents
either a 2,2,2-trifluoroethyl group,
or a phenyl group optionally substituted with one or
more halogen atoms or cyano, nitro, C1-3-alkyl, C1-3-
alkoxy, trifluoromethyl or trifluoromethoxy groups,

and
R6 and R7 represent, independently of one another, a
C1-3-alkyl group or a phenyl;
on the condition that
when R3 represents a phenyl group,
if A represents a propylene, then R2 does not represent
a thienyl.
The following compounds are not part of the first
family of compounds defined above:
- 2,2,2-trifluoroethyl benzylcarbamate;
- 2,2,2-trifluoroethyl 4-methoxybenzylcarbamate;
- 4-nitrophenyl 2-[4-(phenylmethoxy)phenyl]ethyl-
carbamate;
- 4-chloro-2-nitrophenyl 2- (4-(chlorophenyl)ethyl-
carbamate;
- 4-nitrophenyl 2-(3,4-dimethoxyphenyl)ethylcarbamate;
- phenyl 2-(3,4-dimethoxyphenyl)ethylcarbamate;
- 4-cyanophenyl 2-(4-methylphenyl)ethylcarbamate;
- 2,4,5-trichlorophenyl 2-(4-chlorophenyl)ethyl-
carbamate;
- phenyl 4-chlorobenzylcarbamate;
- phenyl 4-methoxybenzylcarbamate;
- 4-fluorophenyl 2-(4-methoxyphenyl)ethylcarbamate;
- phenyl 3-nitrobenzylcarbamate;
- 4-cyanophenyl 4-methoxybenzylcarbamate;
- phenyl 3-chlorobenzylcarbamate;
- phenyl 3,4-dichlorobenzylcarbamate;
- 4-nitrophenyl 2-(4-hydroxyphenyl)ethylcarbamate;
- phenyl 2- [4-(2-ethyl-5,7-dimethyl-3H-imidazo-
[4,5-b]pyridin-3-yl)phenyl]ethylcarbamate;
- phenyl 2-[4-(2-amino-4-thiazolyl)phenyl]ethyl-
carbamate;
- 2,3,4,5,6-pentafluorophenyl 4-bromobenzylcarbamate.
Among the compounds of general formula (I) , a second
family of compounds consists of the compounds for
which:
- when R3 represents a 2,2,2-trifluoroethyl group, then

n represents an integer between 1 and 6;
A is chosen from one or more groups X, Y and/or Z;
X represents a C1-2-alkylene group optionally
substituted with one or more C1-12-alkyl, C3-7-cycloalkyl
or C3-7-cycloalkyl-C1-6-alkylene groups;
Y represents a C2-alkenylene group optionally
substituted with one or more C1-12-alkyl, C3-7-cycloalkyl
or C3-7-cycloalkyl-C1-6-alkylene groups; or a group
-C≡C-;
Z represents a C3-7-cycloalkyl group of formula:

m represents an integer ranging from 1 to 5;
p and q represent integers and are defined such that
p+q is a number ranging from 1 to 5;
R1 represents a hydrogen atom, a halogen atom, or a
hydroxyl, cyano, nitro, C1-3-alkyl, C1-3-alkoxy, C1-3-
thioalkyl, C1-3-f luoroalkyl, C1-3-fluoroalkoxy or C1-3-
fluorothioalkyl group;
R2 represents
a hydrogen atom, a halogen atom,
or a cyano, nitro, hydroxyl, C1-3-alkyl, C1-3-alkoxy,
C1-3-thioalkyl, C1-3-f luoroalkyl, C1-3-f luoroalkoxy or
C1-3-fluorothioalkyl group,
or a group chosen from a phenyl, naphthalenyl,
biphenyl, phenylethylenyl, naphthylethylenyl,
pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl,
triazinyl, indanyl, indenyl, quinolinyl, isoquinolinyl,
quinazolinyl, quinoxalinyl, phthalazinyl, cinnolinyl,
thienyl, furyl, pyrrolyl, imidazolyl, pyrazolyl,
oxazolyl, thiazolyl, isoxazolyl, isothiazolyl,
thiadiazolyl, oxadiazolyl, triazolyl, benzothienyl,
benzofuryl, dibenzofuryl, benzimidazolyl, benzo-
triazolyl, indolyl, isoindolyl, indazolyl,

benzoxazolyl, benzisoxazolyl, benzothiazolyl, benziso-
thiazolyl, dihydroindolyl, pyrrolopyridinyl, furo-
pyridinyl, thienopyridinyl, imidazopyridinyl,
oxazolopyridinyl, thiazolopyridinyl, pyrazolopyridinyl,
isoxazolopyridinyl, isothiazolopyridinyl, tetrahydro-
quinolinyl, tetrahydroisoquinolinyl, phenyloxy,
phenylthio, phenylsulfonyl, benzoyl, phenylmethoxy,
phenylethoxy, phenylpropoxy, naphthalenyloxy,
naphthalenylmethoxy, naphthalenylethoxy, naphthalenyl-
propoxy, quinolinoxy and isoquinolinoxy, and optionally
substituted with one or more substituents chosen from a
halogen atom, and the following groups: hydroxyl,
cyano, nitro, C1-4-alkyl, C1-4-alkoxy, C1-4-thioalkyl,
C1-3-fluoroalkyl, C1-3-f luoroalkoxy, C1-3-f luorothioalkyl,
phenyloxy, benzyloxy, piperidyl, pyrrolidinyl,
morpholinyl, NH2, NHRS, NR6R7, NHCOR6, COR6l CO2R6, SO2R6,
-O-(C1-3-alkylene)-O-, 4-piperazinyl optionally
substituted with a C1-3-alkyl or with a benzyl; and
R6 and R7 represent, independently of one another, a
C1-3-alkyl group or a phenyl;
- when R3 represents a phenyl group optionally
substituted with one or more halogen atoms, or cyano,
nitro, C1-3-alkyl, C1-3-alkoxy, trifluoromethyl or
trifluoromethoxy groups, then
n represents an integer between 1 and 6;
A is chosen from one or more groups X, Y and/or Z;
X represents a C1-2-alkylene group optionally
substituted with one or more C1-12-alkyl, C3-7-cycloalkyl
or C3-7-cycloalkyl-C1-6-alkylene groups;
Y represents a C2-alkenylene group optionally
substituted with one or more C1-12-alkyl, C3-7-cycloalkyl
or C3-7-cycloalkyl-C1-6-alkylene groups; or a group
-C≡C-;
Z represents a C3-7-cycloalkyl group of formula:


m represents an integer ranging from 1 to 5;
p and g represent integers and are defined such that
p+q is a number ranging from 1 to 5;
R1 represents a hydrogen atom, a halogen atom, or a
hydroxyl, cyano, nitro, C1-3-alkyl, C1-3-alkoxy, C1-3-
thioalkyl, C1-3-f luoroalkyl, C1-3-fluoroalkoxy or C1-3-
fluorothioalkyl group;
R2 represents
a hydrogen atom, a halogen atom,
or a cyano, nitro, hydroxyl
, C1-3-alkyl, C1-3-alkoxy,
C1-3-thioalkyl, C1-3-f luoroalkyl, C1-3-f luoroalkoxy or
C1-3-fluorothioalkyl group,
or a group chosen from a phenyl, naphthalenyl,
biphenyl, phenylethylenyl, naphthylethylenyl,
pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl,
triazinyl, indanyl, indenyl, quinolinyl, isoquinolinyl,
quinazolinyl, quinoxalinyl, phthalazinyl, cinnolinyl,
furyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl,
thiazolyl, isoxazolyl, isothiazolyl, thiadiazolyl,
oxadiazolyl, triazolyl, benzothienyl, benzofuryl,
dibenzofuryl, benzimidazolyl, benzotriazolyl, indolyl,
isoindolyl, indazolyl, benzoxazolyl, benzisoxazolyl,
benzothiazolyl, benzisothiazolyl, dihydroindolyl,
pyrrolopyridinyl, furopyridinyl, thienopyridinyl,
imidazopyridinyl, oxazolopyridinyl, thiazolopyridinyl,
pyrazolopyridinyl, isoxazolopyridinyl,
isothiazolopyridinyl, tetrahydroquinolinyl,
tetrahydroisoquinolinyl, phenyloxy, phenylthio,
phenylsulfonyl, benzoyl, phenylmethoxy, phenylethoxy,
phenylpropoxy, naphthalenyloxy, naphthalenylmethoxy,
naphthalenylethoxy, naphthalenylpropoxy, quinolinoxy
and isoquinolinoxy, and optionally substituted with one
or more substituents chosen from a halogen atom, and

the following groups: hydroxyl, cyano, nitro, C1-4-
alkyl, C1-4-alkoxy, C1-4-thioalkyl, C1-3-f luoroalkyl, C1-3-
fluoroalkoxy, C1-3-fluorothioalkyl, phenyloxy,
benzyloxy, piperidyl, pyrrolidinyl, morpholinyl, NH2,
NHR6, NReR7, NHCOR6, COR6, CO2R6, S02Rs, -O-(C1-3-
alkylene)-O-, 4-piperazinyl optionally substituted with
a C1-3-alkyl or with a benzyl; and
R6 and R7 represent, independently of one another, a
C1-3-alkyl group or a phenyl.
The following compounds are not part of the second
family of compounds defined above:
- 2,2 ,2-trifluoroethyl benzylcarbamate;
- 2,2 , 2-trifluoroethyl 4-methoxybenzylcarbamate;
- 4-nitrophenyl 2- [4- (phenylmethoxy)phenyl]ethyl-
carbamate;
- 4-chloro-2-nitrophenyl 2-(4-(chlorophenyl)ethyl-
carbamate;
- 4-nitrophenyl 2-(3,4-dimethoxyphenyl)ethylcarbamate ;
- phenyl 2-(3,4-dimethoxyphenyl)ethylcarbamate;
- 4-cyanophenyl 2-(4-methylphenyl)ethylcarbamate;
- 2,4, 5-trichlorophenyl 2-(4-chlorophenyl)ethyl-
carbamate;
- phenyl 4-chlorobenzylcarbamate;
- phenyl 4-methoxybenzylcarbamate;
- 4-fluorophenyl 2-(4-methoxyphenyl)ethylcarbamate;
- phenyl 3-nitrobenzylcarbamate;
- 4-cyanophenyl 4-methoxybenzylcarbamate;
- phenyl 3-chlorobenzylcarbamate;
- phenyl 3,4-dichlorobenzylcarbamate;
- 4-nitrophenyl 2-(4-hydroxyphenyl)ethylcarbamate;
- phenyl 2-[4-(2-ethyl-5,7-dimethyl-3H-imidazo-
[4,5-b]pyridin-3-yl)phenyl]ethylcarbamate;
- phenyl 2-[4-(2-amino-4-thiazolyl)phenyl]ethyl-
carbamate;
- 2,3,4,5,6-pentafluorophenyl 4-bromobenzylcarbamate.
Among the compounds of general formula (I) , a third
family of compounds consists of the compounds for

which:
n represents an integer between 1 and 6;
A is chosen from one or more groups X, Y and/or Z;
X represents a C1-2-alkylene group optionally
substituted with one or more C1-12-alkyl, C3-7-cycloalkyl
or C3-7-cycloalkyl-C1-6-alkylene groups;
Y represents a C2-alkenylene group optionally
substituted with one or more C1-12-alkyl, C3-7-cycloalkyl
or C3-7-cycloalkyl-C1-6-alkylene groups; or a group
-C≡C-;
Z represents a C3-7-cycloalkyl group of formula:

m represents an integer ranging from 1 to 5;
p and q represent integers and are defined such that
p+q is a number ranging from 1 to 5;
R1 represents a hydrogen atom, a halogen atom, or a
hydroxyl, cyano, nitro, C1-3-alkyl, C1-3-alkoxy, C1-3-
thioalkyl, C1-3-f luoroalkyl, C1-3-f luoroalkoxy or C1-3-
fluorothioalkyl group;
R2 represents
a hydrogen atom, a halogen atom,
or a cyano, nitro, hydroxyl, C1-3-alkyl, C1-3-alkoxy,
C1-3-thioalkyl, C1-3-f luoroalkyl, C1-3-f luoroalkoxy or
C1-3-fluorothioalkyl group,
or a group chosen from a phenyl, naphthalenyl,
biphenyl, phenylethylenyl, naphthylethylenyl,
pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl,
triazinyl, indanyl, indenyl, quinolinyl, isoquinolinyl,
quinazolinyl, quinoxalinyl, phthalazinyl, cinnolinyl,
thienyl, furyl, pyrrolyl, imidazolyl, pyrazolyl,
oxazolyl, thiazolyl, isoxazolyl, isothiazolyl,
thiadiazolyl, oxadiazolyl, triazolyl, benzothienyl,
benzofuryl, dibenzofuryl, benzimidazolyl, benzo-

triazolyl, indolyl, isoindolyl, indazolyl,
benzoxazolyl, benzisoxazolyl, benzothiazolyl, benziso-
thiazolyl, dihydroindolyl, pyrrolopyridinyl, furo-
pyridinyl, thienopyridinyl, imidazopyridinyl,
oxazolopyridinyl, thiazolopyridinyl, pyrazolopyridinyl,
isoxazolopyridinyl, isothiazolopyridinyl, tetrahydro-
quinolinyl, tetrahydroisoquinolinyl, phenyloxy,
phenylthio, phenylsulfonyl, benzoyl, phenylmethoxy,
phenylethoxy, phenylpropoxy, naphthalenyloxy,
naphthalenylmethoxy, naphthalenylethoxy, naphthalenyl-
propoxy, quinolinoxy and isoquinolinoxy, and optionally
substituted with one or more substituents chosen from a
halogen atom, and the following groups: hydroxyl,
cyano, nitro, C1-4-alkyl, C1-4-alkoxy, C1-4-thioalkyl,
C1-3-f luoroalkyl, C1-3-f luoroalkoxy, C1-3-f luorothioalkyl,
phenyloxy, benzyloxy, piperidyl, pyrrolidinyl,
morpholinyl, NH2, NHR6, NR6R7, NHCOR6, COR6, CO2R6, SO2R6,
-O-(C1-3-alkylene)-O-, 4-piperazinyl optionally
substituted with a C1-3-alkyl or with a benzyl;
R3 represents
either a 2,2,2-trifluoroethyl group,
or a phenyl group optionally substituted with one or
more halogen atoms, or cyano, nitro, C1-3-alkyl, C1-3-
alkoxy, trifluoromethyl or trifluoromethoxy groups,
and
R6 and R7 represent, independently of one another, a
C1-3-alkyl group or a phenyl;
on the condition that
- when R3 represents a 2,2,2-trifluoroethyl group,
if A represents a methylene and if Ri represents a
hydrogen, then R2 is neither a hydrogen nor a methoxy;
if A represents a methylene and if R2 represents a
hydrogen, then R1 is neither a hydrogen nor a methoxy;
- when R3 represents a phenyl group,
if A represents a methylene, then neither R1 nor R2
represents a chlorine atom, a methoxy group or a nitro
group;
if A represents an ethylene, then
neither R1 nor R2 represents a methoxy;

R2 represents neither a 2-ethyl-5,7-dimethyl-3H-
imidazo[4,5-b]pyridin-3-yl nor a 2-amino-4-thiazolyl;
if A represents a propylene, then R2 does not represent
a 3-thienyl;
- when R3 represents a phenyl group substituted with
one to five chlorine or fluorine atoms or nitro or
cyano groups,
if A represents a methylene, then neither R1 nor R2
represents a methoxy or a bromine atom;
if A represents an ethylene, then
neither R1 nor R2 represents a chlorine atom, or a
hydroxyl, methyl or methoxy group;
R2 does not represent a phenylmethoxy.
Among the compounds of general formula (I) , a fourth
family of compounds consists of the compounds for
which:
- when R3 represents a 2,2,2-trifluoroethyl group, then
n represents an integer between 1 and 6;
A is chosen from one or more groups X, Y and/or Z;
X represents a C1-2-alkylene group optionally
substituted with one or more C1-12-alkyl, C3-7-cycloalkyl
or C3-7-cycloalkyl-C1-6-alkylene groups;
Y represents a C2-alkenylene group optionally
substituted with one or more C1-12-alkyl, C3-7-cycloalkyl
or C3-7-cycloalkyl-C1-6-alkylene groups; or a group
-C≡C-;
Z represents a C3-7-cycloalkyl group of formula:

m represents an integer ranging from 1 to 5;
p and q represent integers and are defined such that
p+q is a number ranging from 1 to 5;
R1 represents a hydrogen atom, a halogen atom, or a

hydroxyl, cyano, nitro, C1-3-alkyl, C1-3-alkoxy, C1-3-
thioalkyl, C1-3-f luoroalkyl, C1-3-f luoroalkoxy or C1-3-
fluorothioalkyl group;
R2 represents
a halogen atom
or a cyano, nitro, hydroxyl, C1-3-alkyl, C2-3-alkoxy,
C1-3-thioalkyl, C1-3-f luoroalkyl, C1-3-f luoroalkoxy or
C1-3-fluorothioalkyl group,
or a group chosen from a phenyl, naphthalenyl,
biphenyl, phenylethylenyl, naphthylethylenyl,
pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl,
triazinyl, indanyl, indenyl, quinolinyl, isoquinolinyl,
quinazolinyl, quinoxalinyl, phthalazinyl, cinnolinyl,
thienyl, furyl, pyrrolyl, imidazolyl, pyrazolyl,
oxazolyl, thiazolyl, isoxazolyl, isothiazolyl,
thiadiazolyl, oxadiazolyl, triazolyl, benzothienyl,
benzofuryl, dibenzofuryl, benzimidazolyl, benzo-
triazolyl, indolyl, isoindolyl, indazolyl,
benzoxazolyl, benzisoxazolyl, benzothiazolyl, benziso-
thiazolyl, dihydroindolyl, pyrrolopyridinyl, furo-
pyridinyl, thienopyridinyl, imidazopyridinyl,
oxazolopyridinyl, thiazolopyridinyl, pyrazolopyridinyl,
isoxazolopyridinyl, isothiazolopyridinyl, tetrahydro-
quinolinyl, tetrahydroisoquinolinyl, phenyloxy,
phenylthio, phenylsulfonyl, benzoyl, phenylmethoxy,
phenylethoxy, phenylpropoxy, naphthalenyloxy,
naphthalenylmethoxy, naphthalenylethoxy, naphthalenyl-
propoxy, quinolinoxy and isoquinolinoxy, and optionally
substituted with one or more substituents chosen from a
halogen atom, and the following groups: hydroxyl,
cyano, nitro, C1-4-alkyl, C1-4-alkoxy, C1-4-thioalkyl,
C1-3-fluoroalkyl, C1-3-f luoroalkoxy, C1-3-f luorothioalkyl,
phenyloxy, benzyloxy, piperidyl, pyrrolidinyl,
morpholinyl, NH2, NHRS, NR6R7, NHCOR6, COR6, CO2R6, SO2R6,
-O-(C1-3-alkylene)-O-, 4-piperazinyl optionally
substituted with a C1-3-alkyl or with a benzyl;
and
R6 and R7 represent, independently of one another, a
C1-3-alkyl group or a phenyl;

- when R3 represents a phenyl group optionally
substituted with one or more halogen atoms, or cyano,
nitro, C1-3-alkyl, C1-3-alkoxy, trif luoromethyl or
trifluoromethoxy groups, then
n represents an integer between 1 and 6;
A is chosen from one or more groups X, Y and/or Z;
X represents a C1-2-alkylene group optionally
substituted with one or more C1-12-alkyl, C3-7-cycloalkyl
or C3-7-cycloalkyl-C1-6-alkylene groups;
Y represents a C2-alkenylene group optionally
substituted with one or more C1-12-alkyl, C3-7-cycloalkyl
or C3-7-cycloalkyl-C1-6-alkylene groups; or a group
-C≡C-;
Z represents a C3-7-cycloalkyl group of formula:

m represents an integer ranging from 1 to 5;
p and q represent integers and are defined such that
p+q is a number ranging from 1 to 5;
R1 represents a hydrogen atom, an iodine atom, or a
cyano, C2-3-alkyl, C2-3-alkoxy, C1-3-thioalkyl, C1-3-
fluoroalkyl, C1-3-fluoroalkoxy or C1-3-fluorothioalkyl
group;
R2 represents
a hydrogen atom, an iodine atom,
or a cyano, C2-3-alkyl, C2-3-alkoxy, C1-3-thioalkyl, C1-3-
fluoroalkyl, C1-3-f luoroalkoxy or C1-3f luorothioalkyl
group,
or a group chosen from a phenyl, naphthalenyl,
biphenyl, phenylethylenyl, naphthylethylenyl,
pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl,
triazinyl, indanyl, indenyl, quinolinyl, isoquinolinyl,
quinazolinyl, quinoxalinyl, phthalazinyl, cinnolinyl,
furyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl,

isoxazolyl, isothiazolyl, thiadiazolyl, oxadiazolyl,
triazolyl, benzothienyl, benzofuryl, dibenzofuryl,
benzimidazolyl, benzotriazolyl, indolyl, isoindolyl,
indazolyl, benzoxazolyl, benzisoxazolyl,
benzothiazolyl, benzisothiazolyl, dihydroindolyl,
pyrrolopyridinyl, furopyridinyl, thienopyridinyl,
oxazolopyridinyl, thiazolopyridinyl, pyrazolopyridinyl,
isoxazolopyridinyl, isothiazolopyridinyl, tetrahydro-
quinolinyl, tetrahydroisoquinolinyl, phenyloxy,
phenylthio, phenylsulfonyl, benzoyl, phenylethoxy,
phenylpropoxy, naphthalenyloxy, naphthalenylmethoxy,
naphthalenylethoxy, naphthalenylpropoxy, quinolinoxy
and isoquinolinoxy, and optionally substituted with one
or more substituents chosen from a halogen atom, and
the following groups: hydroxyl, cyano, nitro, Ci_4-
alkyl, C1-4-alkoxy, C1-4-thioalkyl, C1-3-f luoroalkyl, Ca-3-
f luoroalkoxy, C1-3-f luorothioalkyl, phenyloxy,
benzyloxy, piperidyl, pyrrolidinyl, morpholinyl, NH2,
NHR6, NR6R7, NHCOR6, COR6, CO2Rs, SO2R6, -O- (C1-3-
alkylene)-O-, 4-piperazinyl optionally substituted with
a Cx-3-alkyl or with a benzyl;
and
R6 and R7 represent, independently of one another, a
C1-3-alkyl group or a phenyl.
Among the compounds of general formula (I) , a fifth
family of compounds consists of the compounds for
which:
n represents an integer between 1 and 6;
A is chosen from one or more groups X, Y and/or Z;
X represents a C1-2-alkylene group optionally
substituted with one or more C1-12-alkyl, C3-7-cycloalkyl
or C3-7-cycolalkyl-1-6-alkylene groups;
Y represents a C2-alkenylene group optionally
substituted with one or more C1-12-alkyl, C3-7-cycloalkyl
or C3-7-cycloalkyl-C1-6-alkylene groups; or a group -C≡C-
7
Z represents a C3-7-cycloalkyl group of formula:


m represents an integer ranging from 1 to 5;
p and q represent integers and are defined such that
p+q is a number ranging from 1 to 5;
R1 represents a hydrogen atom, a halogen atom, or a
hydroxyl, cyano, nitro, C1-3-alkyl, C1-3-alkoxy, C1-3-
thioalkyl, C1-3-f luoroalkyl, C1-3-fluoroalkoxy or C1-3-
fluorothioalkyl group;
R2 represents
a hydrogen atom, or a phenyl or phenyloxy group, this
group being optionally substituted with one or more
substituents chosen from a halogen atom, and the
following groups: hydroxyl, cyano, nitro, C1-4-alkyl,
C1-4-alkoxy, C1-4-thioalkyl, C1-3-f luoroalkyl, C1-3-f luoro-
alkoxy, C1-3-f luorothioalkyl, phenyloxy, benzyl oxy,
piperidyl, pyrrolidinyl, morpholinyl, NH2, NHR6, NR6R7,
NHCOR6, COR6, CO2R6, SO2R6, -O-(C1-3-alkylene)-O-, 4-
piperazinyl optionally substituted with a C1-3-alkyl or
with a benzyl;
R3 represents
either a 2,2,2-trifluoroethyl group,
or a phenyl group optionally substituted with one or
more halogen atoms, or cyano, nitro, C1-3-alkyl, C1-3-
alkoxy, trifluoromethyl or trifluoromethoxy groups,
and
R6 and R7 represent, independently of one another, a
C1-3-alkyl group or a phenyl;
2,2,2-trifluoroethyl benzylcarbamate being excluded.
Among the compounds of general formula (I) , a sixth
family of compounds consists of the compounds for
which:
n represents an integer between 1 and 6;
A is a group X;

the groups A being identical to or different from one
another when n is an integer between 2 and 6;
X represents a C1-2-alkylene group optionally-
substituted with one or more C1-12-alkyl, C3-7-cycloalkyl
or C3-7-cycloalkyl-C1-6-alkylene groups;
R1 represents a hydrogen atom, a halogen atom, or a
hydroxyl, cyano, nitro, C1-3-alkyl, C1-3-alkoxy, C1-3-
thioalkyl, C1-3-f luoroalkyl, C1-3 luoroalkoxy or C1-3-
fluorothioalkyl group;
R2 represents
a hydrogen atom, a halogen atom,
or a cyano, nitro, hydroxyl, C1-3-alkyl, C1-3-alkoxy,
C1-3-thioalkyl, C1-3-f luoroalkyl, C1-3-f luoroalkoxy, C1-3-
fluorothioalkyl group,
or a group chosen from a phenyl, naphthalenyl,
biphenyl, phenylethylenyl, naphthylethylenyl,
pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl,
triazinyl, indanyl, indenyl, quinolinyl, isoquinolinyl,
quinazolinyl, quinoxalinyl, phthalazinyl, cinnolinyl,
thienyl, furyl, pyrrolyl, imidazolyl, pyrazolyl,
oxazolyl, thiazolyl, isoxazolyl, isothiazolyl,
thiadiazolyl, oxadiazolyl, triazolyl, benzothienyl,
benzofuryl, dibenzofuryl, benzimidazolyl, benzo-
triazolyl, indolyl, isoindolyl, indazolyl,
benzoxazolyl, benzisoxazolyl, benzothiazolyl, benziso-
thiazolyl, dihydroindolyl, pyrrolopyridinyl, furo-
pyridinyl, thienopyridinyl, imidazopyridinyl,
oxazolopyridinyl, thiazolopyridinyl, pyrazolopyridinyl,
isoxazolopyridinyl, isothiazolopyridinyl, tetrahydro-
quinolinyl, tetrahydroisoquinolinyl, phenyloxy,
phenylthio, phenylsulfonyl, benzoyl, phenylmethoxy,
phenylethoxy, phenylpropoxy, naphthalenyloxy,
naphthalenylmethoxy, naphthalenylethoxy, naphthalenyl-
propoxy, quinolinoxy and isoquinolinoxy, and optionally
substituted with one or more substituents chosen from a
halogen atom, and the following groups: hydroxyl,
cyano, nitro, C1-4-alkyl, C1-4-alkoxy, C1-4-thioalkyl,
C1-3-f luoroalkyl, C1-3-f luoroalkoxy, C1-3-f luorothioalkyl,
phenyloxy, benzyloxy, piperidyl, pyrrolidinyl,

morpholinyl, NH2, NHR6, NR6R7, NHCOR6, COR6, CO2R6, SO2R6,
-O- (C1-3-alkylene) -O-, 4-piperazinyl optionally
substituted with a C1-3-alkyl or with a benzyl;
R3 represents
either a 2,2,2-trifluoroethyl group,
or a phenyl group optionally substituted with one or
more halogen atoms, or cyano, nitro, C1-3-alkyl, C1-3-
alkoxy, trifluoromethyl or trifluoromethoxy groups,
and
R6 and R7 represent, independently of one another, a
C1-3-alkyl group or a phenyl;
on the condition that:
- when R3 represents a 2,2,2-trifluoroethyl group and
the group - [A] n- represents a -CH2- group,
then R1 is other than a hydrogen atom or than a methoxy
group;
- when R3 represents an optionally substituted phenyl
group and the group - [A]n- represents a -CH2-, -CH2CH2-,
-CH(CH3)- or -CH(CH3)-CH2- group;
then R1 is other than a hydrogen or chlorine atom or
than a methyl or methoxy group, and R2 is other than a
hydrogen atom.
The compounds of general formula (I) can comprise one
or more asymmetrical carbons. They can exist in the
form of enantiomers or of diastereoisomers. These
enantiomers and diastereoisomers, and also mixtures
thereof, including racemic mixtures, are part of the
invention.
The compounds of formula (I) can exist in the form of
bases or of addition salts with acids. Such addition
salts are part of the invention.
These salts are advantageously prepared with
pharmaceutically acceptable acids, but the salts of
other acids useful, for example, for the purification
or the isolation of the compounds of formula (I) are
also part of the invention. The compounds of general

formula (I) can be in the form of hydrates or of
solvates, i.e. in the form of associations or of
combinations with one or more molecules of water or
with a solvent. Such hydrates and solvates are also
part of the invention.
In the context of the invention:
the expression "Ct-Z where t and z can have the
values from 1 to 12" is intended to mean a carbon-
based chain that can have from t to z carbon
atoms; for example, "C1-3" is intended to mean a
carbon-based chain which can have from 1 to 3
carbon atoms;
the term "alkyl" is intended to mean a linear or
branched, saturated aliphatic group; for example,
a C1-3-alkyl group represents a linear or branched
carbon-based chain of 1 to 3 carbon atoms, more
particularly a methyl, ethyl, propyl or 1-methyl-
ethyl;
the term "alkylene" is intended to mean a linear
or branched, saturated divalent alkyl group; for
example, a C1-3-alkylene group represents a linear
or branched divalent carbon-based chain of 1 to 3
carbon atoms, more particularly a methylene,
ethylene, 1-methylethylene or propylene;
the term "cycloalkyl" is intended to mean a cyclic
alkyl group; for example, a C3-5-cycloalkyl group
represents a cyclic carbon-based group of 3 to 5
carbon atoms, more particularly a cyclopropyl,
cyclobutyl or cyclopentyl;
the term "alkenylene" is intended to mean a
divalent unsaturated aliphatic group, more
particularly an ethylene;
the term "alkoxy" is intended to mean an -O-alkyl
group comprising a linear or branched, saturated
aliphatic chain;
the term "thioalkyl" is intended to mean an -S-
alkyl group comprising a linear or branched,
saturated aliphatic chain;

the term "fluoroalkyl" is intended to mean an
alkyl group in which one or more hydrogen atoms
have been substituted with a fluorine atom;
the term "fluoroalkoxy" in intended to mean an
alkoxy group in which one or more hydrogen atoms
have been substituted with a fluorine atom;
the term "fluorothioalkyl" is intended to mean a
thioalkyl group in which one or more hydrogen
atoms have been substituted with a fluorine atom;
the term "halogen atom" is intended to mean a
fluorine, a chlorine, a bromine or an iodine.
The compounds of the invention can be prepared
according to various methods, illustrated by the
schemes which follow.
Thus, a first method (scheme 1) for preparing the
compounds of general formula (I) consists in reacting
an amine of general formula (II), in which R1, R2, n and
A are as defined above, with a carbonate of general
formula (III), in which U represents a hydrogen atom or
a nitro group and R3 is as defined above, in a solvent
such as toluene or dichloroethane, at a temperature of
between 0 and 80°C.

According to a second method, the compounds of general
formula (I) for which R3 represents more particularly
an optionally substituted phenyl can be prepared by
reacting an amine of general formula (II), as defined

above, with an aryl chlorof ormate of general formula
(IIIa)

where R3 represents a phenyl group optionally
substituted with one or more halogen atoms, or cyano,
nitro, C1-3-alkyl, C1-3-alkoxy, trif luoromethyl or
trifluoromethoxy groups,
in a solvent such as dichloromethane or dichloroethane
in the presence of a base such as triethylamine or
diisopropylethylamine, at a temperature of between 0°C
and the reflux temperature of the solvent.
The carbonates of general formula (III) can be prepared
according to any method described in the literature,
for example by reaction of an alcohol of general
formula HOR3 with phenyl chloroformate or para-
nitrophenyl chloroformate, in the presence of a base
such as triethylamine or diisopropylethylamine.
The compounds of general formulae (II) and (IIIa) are
commercially available or described in the literature,
or else can be prepared according to methods which are
described therein or which are known to those skilled
in the art.
When R2 represents a group of aryl or heteroaryl type
in a compound of formula (I) or (II), the introduction
of R2 onto the phenyl ring can be carried out by
reacting a derivative of a compound of general formula
(I) or (II) in which the phenyl ring bears a chlorine,
bromine or iodine atom or a trif late group, in the
position where it is desired to introduce R2, with an
aryl- or heteroaryl boronic acid derivative in

accordance with the Suzuki reaction conditions (Chem.
Rev. (1995), 95, 2457-2483; Angew. Chem. Int., Ed.
(1999), 38, 3387-3388), or with an aryl- or heteroaryl
trialkyltin derivative in accordance with the Stille
reaction conditions (Angew. Chem. Int. Ed. Engl.
(1986), 25, 508-524).
The following examples illustrate the preparation of
some compounds of the invention. They are not limiting
and merely illustrate the invention. The NMR spectra
and/or the LC-MS (Liquid Chromatography coupled to Mass
Spectroscopy) confirm the structures and the purities
of the compounds obtained.
Mp (°C) represents the melting point in degrees
Celsius.
The numbers indicated between parentheses in the titles
of the examples correspond to those of the 1st column
of the table hereinafter.
The IUPAC nomenclature (International Union of Pure and
Applied Chemistry) was used to name the compounds in
the following examples. For example, for the biphenyl
group, the following numbering was observed:

Example 1 (Compound No. 1)
2,2,2-Trifluoroethyl 1,1'-biphenyl-4-ylmethylcarbamate
0.119 ml (1.64 mmol) of 2,2,2-trifluoroethanol and
0.306 ml (1.49 mmol) of N,N-diisopropylethylamine are
added, dropwise and at ambient temperature, to a
solution of 0.3 g (1.49 mmol) of para-nitrophenyl
chloroformate in 15 ml of methylene chloride. The

mixture is stirred at ambient temperature for 2 h, and
then 0.275 g (1.5 mmol) of 4-phenylbenzylamine is
added. N,N-Diisopropyleth.ylamine is subsequently added,
dropwise and at ambient temperature, until the
precipitate which has formed disappears. The
transparent solution thus obtained is stirred at
ambient temperature for 1 h. The reaction medium is
diluted with a further 10 ml of methylene chloride and
washing is carried out with a saturated aqueous
ammonium chloride solution and with a saturated aqueous
sodium chloride solution. The phases are separated and
the organic phase is dried over sodium sulfate. The
product is filtered, the filtrate is concentrated under
reduced pressure and the residue is purified by silica
gel chromatography with methylene chloride.
0.215 g of white solid is obtained.
LC-MS: 310
Mp(°C): 123-125°C
1H NMR (DMSO-d6) δ(ppm) : 8.25 (t, 1H) ; 7.75-7.30 (m,
9H); 4.65 (q, 2H); 4.25 (d, 2H).
Example 2 (Compound No. 19)
2,2,2-Trifluoroethyl 2 -(1,1'-biphenyl-4-yl)ethyl-
carbamate
The procedure is carried out in a manner similar to
Example 1, replacing the 4-phenylbenzylamine with 2- (4-
biphenyl)ethylamine.
0.311 g of white solid is obtained.
LC-MS: 324
Mp(°C): 79-81°C
1H NMR (DMSO-dg) δ (ppm) : 7.80-7.20 (m, 10H) ; 4.65 (q,
2H); 3.3 0 (m, 2H) ; 2.75 (t, 2H).

Example 3 (Compound No. 10)
2,2,2-Trifluoroethyl 4-phenyloxybenzylcarbamate
The procedure is carried out in a manner similar to
Example 1, replacing the 4-phenylbenzylamine with
4-phenyloxybenzylamine.
0.252 g of white solid is obtained.
LC-MS: 326
Mp(°C): 145-148°C
1HNMR(DMSO-d6) δ(ppm): 8.15 (t, 1H) ; 7.40-6.90 (m, 9H) ;
4.65 (q, 2H); 4.20 (d, 2H).
Example 4 (Compound No. 3)
4-Fluorophenyl 1,1'-biphenyl-4-ylmethylcarbamate
0.069 ml (0.522 mmol) of 4-fluorophenyl chloroformate
and 0.149 ml (0.82 mmol) of N,N-diisopropylethylamine
are added, dropwise and at ambient temperature, to a
solution of 0.107 g (0.58 mmol) of 4-phenylbenzylamine
in 4 ml of methylene chloride. The mixture is stirred
at ambient temperature for 1 h. The reaction medium is
diluted with a further 2 ml of methylene chloride and
washed with a saturated aqueous ammonium chloride
solution and with a saturated aqueous sodium chloride
solution. The phases are separated and the organic
phase is filtered through a hydrophobic sintered glass
funnel. The filtrate is concentrated under reduced
pressure and the solid residue is washed with 5 ml of
diisopropyl ether.
0.136 g of white solid is obtained.
LC-MS: 322
Mp(°C): 155-157°C
1H NMR(DMS0-d6) δ(ppm) : 8.30 (t, 1H) ; 7.70-7.10 (m,
13H); 4.30 (d, 2H).

Example 5 (Compound No. 26)
4-Methylphenyl 2-(1,1'-biphenyl-4-yl)ethylcarbamate
The procedure is carried out in a manner similar to
Example 4, replacing the 4-phenylbenzylamine with 2-(4-
biphenyl)ethylamine and the 4-fluorophenyl chloro-
formate with 4-methylphenyl chloroformate.
0.126 g of white solid is obtained.
LC-MS: 332
Mp(°C): 172-174°C
1H NMR(DMSO-d6) δ(ppm) : 7.75 (t, 1H) ; 7.70-7.30 (m, 9H) ;
7.10 (d, 2H); 6.90 (d, 2H); 3.30 (m, 2H); 2.80 (t, 2H);
2.25 (s, 3H).
Example 6 (Compound No. 16)
4-Methoxyphenyl 4-phenyloxybenzylcarbamate
The procedure is carried out in a manner similar to
Example 4, replacing the 4-phenylbenzylamine with
4-phenyloxybenzylamine and the 4-fluorophenyl
chloroformate with 4-methoxyphenyl chloroformate.
0.137 g of white solid is obtained.
LC-MS: 350
Mp(°C): 89-91°C
1H NMR(DMS0-d6) δ(ppm) : 8.20 (t, 1H) ; 7.45-7.25 (m, 4H) ;
7.20-6.80 (m, 9H) ; 4.25 (d, 2H) ; 3.75 (s, 3H) .
The following table illustrates the chemical structures
and the physical properties of some compounds according
to the invention. In this table, "n.d." signifies that
the melting point could not be determined (product in
the form of a gum, for example).


The compounds of the invention were subjected to
pharmacological assays to determine their inhibitory
effect on the FAAH enzyme (fatty acid amido hydrolase) .
The inhibitory activity was demonstrated in a
radioenzymatic assay based on measuring the product of
hydrolysis (ethanolamine [1-3H] ) of anandamide
[ethanolamine 1-3H] by FAAH (Life Sciences (1995), 56,
1999-2005) and (Journal of Pharmacology and
Experimented Therapeutics (1997), 283, 729-734). Thus,
mouse brains (minus the cerebellum) are removed and
conserved at -80°C. Membrane homogenates are prepared
extemporaneously by homogenization of the tissues with
a Polytron in a 10mM Tris-HCl buffer (pH 8.0)
containing 150 mM NaCl and 1 mM EDTA. The enzymatic
reaction is subsequently carried out in 70 µl of buffer
containing fatty acid-free bovine serum albumin
(1 mg/ml) . The compounds tested, at various
concentrations, anandamide [ethanolamine 1-3H]
(specific activity of 15-20 Ci/mmol) diluted to 10 /xM
with cold anandamide, and the membrane preparation
(400 µg of frozen tissue per assay) are added
successively. After 15 minutes at 25°C, the enzymatic
reaction is stopped by adding 14 0 µl of
chloroform/methanol (2:1). The mixture is stirred for
10 minutes and then centrifuged for 15 minutes at
3500 g. An aliquot (30 µl) of the aqueous phase
containing the ethanolamine [1-3H] is counted by liquid
scintillation.
Under these conditions, the most active compounds of
the invention exhibit IC50 values (concentration that

inhibits 50% of the control enzymatic activity of FAAH)
between 0.001 and 1 µM.
It therefore appears that the compounds according to
the invention have an inhibitory activity on the FAAH
enzyme.
The FAAH enzyme (Chemistry and Physics of Lipids,
(2000), 108, 107-121) catalyses the hydrolysis of
endogenous derivatives of amides and of esters of
various fatty acids such as N-arachidonoylethanolamine
(anandamide) , N-palmitoylethanolamine, N-oleylethanol-
amine, oleamide or 2-arachidonoylglycerol. These
derivatives exert various pharmacological activities by
interacting, inter alia, with cannabinoid and vanilloid
receptors.
The compounds of the invention block this degradation
pathway and increase the tissue content of these
endogenous substances. They can be used in this respect
in the prevention and treatment of pathologies in which
endogenous cannabinoids and/or any other substrates
metabolized by the FAAH enzyme are involved.
Mention may, for example, be made of the following
diseases and conditions:
pain, in particular acute or chronic pain of neurogenic
type: migraine, neuropathic pain including the forms
associated with the herpesvirus and with diabetes;
acute or chronic pain associated with inflammatory
diseases: arthritis, rheumatoid arthritis,
osteoarthritis, spondylitis, gout, vasculitis, Crohn's
disease, irritable bowel syndrome;
acute or chronic peripheral pain:
dizziness, vomiting, nausea, in particular those
subsequent to chemotherapy;
eating disorders, in particular anorexia and cachexia
of various natures;
neurological and psychiatric pathologies: shaking,

dyskinesia, dystonia, spasticity, obsessive compulsive
disorders, Tourette's syndrome, all forms of depression
and anxiety of any nature and origin, mood disorders,
psychoses;
acute and chronic neurodegenerative diseases:
Parkinson's disease, Alzheimer's disease, senile
dementia, Huntington's chorea, lesions related to
cerebral ischemia and to cranial and medullary traumas;
epilepsy;
sleeping disorders, including sleep apnoea;
cardiovascular diseases, in particular hypertension,
cardiac arrhythmias, arteriosclerosis, heart attack,
cardiac ischemias;
renal ischemia;
cancers: benign skin tumors, papillomas and brain
tumors, prostate tumors, brain tumors (glioblastomas,
medulloepitheliomas, medulloblastomas, neuroblastomas,
tumors of embryonic origin, astrocytomas,
astroblastomas, ependyomas, oligodendrogliomas, plexus
tumors, neuroepitheliomas, epiphyseal tumors,
ependymoblastomas, malignant meningiomas, sarcomatoses,
malignant melanomas, schwannomas);
immune system disorders, in particular autoimmune
diseases: psoriasis, lupus erythematosus, connective
tissue diseases or connectivitis, Sjogren's syndrome,
ankylosing spondylarthritis, undifferentiated
spondylarthritis, Behcet's disease, hemolytic auto-
immune anemia, multiple sclerosis, amyotrophic lateral
sclerosis, amyloses, transplant rejection, diseases
affecting the plasmocyte line;
allergic diseases: immediate or delayed hyper-
sensitivity, allergic rhinitis or conjunctivitis,
contact dermatitis;
parasitic, viral or bacterial infectious diseases:
AIDS, meningitis;
inflammatory diseases, in particular articular
diseases: arthritis, rheumatoid arthritis, osteo
arthritis, spondylitis, gout, vasculitis, Crohn's
disease, irritable bowel syndrome;

osteoporosis ,-
ocular conditions: ocular hypertension, glaucoma;
pulmonary conditions: respiratory tract diseases,
bronchospasms, coughs, asthma, chronic bronchitis,
chronic respiratory tract obstruction, emphysema;
gastrointestinal diseases: irritable bowel syndrome,
intestinal inflammatory disorders, ulcers, diarrhea;
urinary incontinence and bladder inflammation.
The use of the compounds according to the invention for
preparing a medicinal product for use in the treatment
of the pathologies mentioned above is an integral part
of the invention.
The use of the following compounds for preparing a
medicinal product for use in the treatment of the
pathologies mentioned above is also an integral part of
the invention:
- 2,2,2-trifluoroethyl benzylcarbamate;
- 2,2,2-trifluoroethyl 4-methoxybenzylcarbamate;
- 4-nitrophenyl 2 -[4-phenylmethoxy)phenyl]ethyl-
carbamate,
- 4-chloro-2-nitrophenyl 2-(4-chlorophenyl)ethyl-
carbamate;
- 4-nitrophenyl 2-(3,4-dimethoxyphenyl)ethylcarbamate;
- phenyl 2-(3,4-dimethoxyphenyl)ethylcarbamate;
- 4-cyanopheny1 2-(4-methylphenyl)ethylcarbamate;
- 2,4,5-trichlorophenyl 2-(4-chlorophenyl)ethyl-
carbamate;
- phenyl 4-chlorobenzylcarbamate;
- phenyl 4-methoxybenzylcarbamate;
- 4-fluorophenyl 2-(4-methoxyphenyl)ethylcarbamate;
- phenyl 3-nitrobenzylcarbamate;
- 4-cyanophenyl 4-methoxybenzylcarbamate;
- phenyl 3-chlorobenzylcarbamate;
- phenyl 3,4-dichlorobenzylcarbamate;
- 4-nitrophenyl 2-(4-hydroxyphenyl)ethylcarbamate,
- phenyl 2-[4-(2-ethyl-5,7-diimethyl-3H-imidazo-
[4,5-b]pyridin-3-yl)phenyl]ethylcarbamate;

- phenyl 2-[4-(2-amino-4-thiazolyl)phenyl]ethyl-
carbamate;
- 2,3,4,5,6-pentafluorophenyl 4-bromobenzylcarbamate.
A subject of the invention is also medicinal products
which comprise a compound of formula (I), or a salt, or
else a hydrate or a solvate, that is pharmaceutically
acceptable, of the compound of formula (I). These
medicinal products find their use in therapeutics, in
particular in the treatment of the pathologies
mentioned above.
A subject of the invention is also medicinal products
which comprise a compound chosen from the list of
compounds below, or a salt, or else a hydrate or a
solvate, that is pharmaceutically acceptable, of this
compound:
- 2,2,2-trifluoroethyl benzylcarbamate;
- 2,2,2-trifluoroethyl 4-methoxybenzylcarbamate;
- 4-nitrophenyl 2-[4-phenylmethoxy)phenyl]ethyl-
carbamate,
- 4-chloro-2-nitrophenyl 2-(4-chlorophenyl)ethyl-
carbamate;
- 4-nitrophenyl 2-(3,4-dimethoxyphenyl)ethylcarbamate;
- phenyl 2-(3,4-dimethoxyphenyl)ethylcarbamate;
- 4-cyanophenyl 2-(4-methylphenyl)ethylcarbamate;
- 2,4,5-trichlorophenyl 2-(4-chlorophenyl)ethyl-
carbamate;
- phenyl 4-chlorobenzylcarbamate;
- phenyl 4-methoxybenzylcarbamate;
- 4-fluorophenyl 2-(4-methoxyphenyl)ethylcarbamate;
- phenyl 3-nitrobenzylcarbamate;
- 4-cyanophenyl 4-methoxybenzylcarbamate;
- phenyl 3-chlorobenzylcarbamate;
- phenyl 3,4-dichlorobenzylcarbamate;
- 4-nitrophenyl 2-(4-hydroxyphenyl)ethylcarbamate;
- phenyl 2-[4-(2-ethyl-5,7-diimethyl-3H-imidazo-
[4,5-b]pyridin-3-yl)phenyl]ethylcarbamate;
- phenyl 2-[4-(2-amino-4-thiazolyl)phenyl]ethyl-

carbamate;
- 2,3,4,5,6-pentafluorophenyl 4-bromobenzylcarbamate.
These medicinal products find their use in thera-
peutics, in particular in the treatment of the
pathologies mentioned above.
According to another of its aspects, the present
invention relates to pharmaceutical compositions
containing, as active ingredient, at least one compound
according to the invention. These pharmaceutical
compositions contain an effective dose of a compound
according to the invention, or a salt, or a hydrate, or
a solvate, that is pharmaceutically acceptable, of said
compound, and, optionally, one or more excipients that
are pharmaceutically acceptable.
According to another of its aspects, the present
invention relates to pharmaceutical compositions
containing, as active ingredient, at least one compound
chosen from the list of compounds below. These
pharmaceutical compositions contain an effective dose
of a compound chosen from the list of compounds below,
or a salt, or a hydrate, or a solvate, that is
pharmaceutically acceptable, of said compound, and,
optionally, one or more excipients that are pharma-
ceutically acceptable:
- 2,2,2-trifluoroethyl benzylcarbamate;
- 2,2,2-trifluoroethyl 4-methoxybenzylcarbamate;
- 4-nitrophenyl 2-[4-phenylmethoxy)phenyl]ethyl-
carbamate,
- 4-chloro-2-nitrophenyl 2-(4-chlorophenyl)ethyl-
carbamate;
- 4-nitrophenyl 2-(3,4-dimethoxyphenyl)ethylcarbamate;
- phenyl 2- (3 ,4-dimethoxyphenyl) ethylcarbamate,-
- 4-cyanophenyl 2-(4-methy1phenyl)ethylcarbamate;r
- 2,4,5-trichlorophenyl 2-(4-chlorophenyl)ethyl-
carbamate ;
- phenyl 4-chlorobenzylcarbamate;

- phenyl 4-methoxybenzylcarbamate;
- 4-fluorophenyl 2-(4-methoxyphenyl)ethylcarbamate;
- phenyl 3-nitrobenzylcarbamate;
- 4-cyanophenyl 4-methoxybenzylcarbamate;
- phenyl 3-chlorobenzylcarbamate;
- phenyl 3,4-dichlorobenzylcarbamate;
- 4-nitrophenyl 2-(4-hydroxyphenyl)ethylcarbamate;
- phenyl 2-[4-(2-ethyl-5,7-dimethyl-3H-imidazo-
[4,5-b]pyridin-3-yl)phenyl]ethylcarbamate;
- phenyl 2-[4-(2-amino-4-thiazolyl)phenyl]ethyl-
carbamate ;
- 2,3,4,5,6-pentafluorophenyl 4-bromobenzylcarbamate.
Said excipients are chosen, according to the pharma-
ceutical form and the method of administration desired,
from the usual excipients that are known to those
skilled in the art.
In the pharmaceutical compositions of the present
invention for oral, sublingual, subcutaneous, intra-
muscular, intravenous, topical, local, intrathecal,
intranasal, transdermal, pulmonary, ocular or rectal
administration, the active ingredient of formula (I)
above or one of the compounds below:
- 2,2,2-trifluoroethyl benzylcarbamate;
- 2,2,2-trifluoroethyl 4-methoxybenzylcarbamate;
- 4-nitrophenyl 2-[4-phenylmethoxy)phenyl]ethyl-
carbamate,
- 4-chloro-2-nitrophenyl 2-(4-chlorophenyl)ethyl-
carbamate;
- 4-nitrophenyl 2-(3,4-dimethoxyphenyl)ethylcarbamate;
- phenyl 2-(3,4-dimethoxyphenyl)ethylcarbamate;
- 4-cyanophenyl 2-(4-methylphenyl)ethylcarbamate;
- 2,4,5-trichlorophenyl 2-(4-chlorophenyl)ethyl-
carbamate;
- phenyl 4-chlorobenzylcarbamate;
- phenyl 4-methoxybenzylcarbamate;
- 4-fluorophenyl 2-(4-methoxyphenyl)ethylcarbamate;
- phenyl 3-nitrobenzylcarbamate;

- 4-cyanophenyl 4-methoxybenzylcarbamate;
- phenyl 3-chlorobenzylcarbamate;
- phenyl 3,4-dichlorobenzylcarbamate;
- 4-nitrophenyl 2-(4-hydroxyphenyl)ethylcarbamate;
- phenyl 2-[4-(2-ethyl-5,7-dimethyl-3H-imidazo-
[4, 5-b]pyridin-3-yl)phenyl]ethylcarbamate;
- phenyl 2-[4-(2-amino-4-thiazolyl)phenyl]ethyl-
carbamate;
- 2,3,4,5,6-pentafluorophenyl 4-bromobenzylcarbamate;
or its possible salt, solvate or hydrate, can be
administered in unit administration form as a mixture
with conventional pharmaceutical excipients, to animals
and to human beings for the prophylaxis or the
treatment of the disorders or of the diseases above.
Suitable unit administration forms comprise oral
administration forms such as tablets, soft or hard
gelatin capsules, powders, granules, chewing gums and
oral solutions or suspensions, sublingual, buccal,
intratracheal, intraocular and intranasal admini-
stration forms, forms for administration by inhalation,
subcutaneous, intramuscular or intravenous
administration forms, and rectal or vaginal admini-
stration forms. For topical application, the compounds
according to the invention can be used in creams,
ointments or lotions.
By way of example, a unit administration form of a
compound according to the invention in tablet form can
comprise the following components:
Compound according to the invention 50.0 mg
Mannitol 223.75 mg
Sodium croscarmellose 6.0 mg
Corn starch 15.0 mg
Hydroxypropylmethylcellulose 2.25 mg
Magnesium stearate 3.0 mg
Said unit forms contain doses so as to allow a daily
administration of 0.01 to 20 mg of active ingredient

per kg of bodyweight, according to the pharmaceutical
form.
There may be specific cases where higher or lower doses
are appropriate, such doses are also part of the
invention. According to the usual practice, the dosage
suitable for each patient is determined by the
physician according to the method of administration,
and the weight and response to said patient.
According to another of its aspects, the invention also
relates to a method of treatment of the pathologies
indicated above, which comprises the administration of
an effective dose of a compound according to the
invention, of one of its salts that are
pharmaceutically acceptable, or of a solvate or a
hydrate of said compound.

WE. CLAIM:
1. A compound of the formula (I);

in which
n represents an integer between 1 and 6;
A is a group X;
X represents a C1-2-alkylene group optionally
substituted with one or more C1-12-alkyl, C3-7-cycloalkyl
or C3-7-cycloalkyl-C1-6-alkylene groups;
R1 represents a hydrogen atom, a halogen atom, or a
hydroxyl, cyano, nitro, C1-3-alkyl, C1-3-alkoxy, C1-3-
thioalkyl, C1-3-fluoroalkyl, C1-3-f luoroalkoxy or C1-3-
fluorothioalkyl group;
R2 represents a hydrogen atom, a halogen atom, or a
cyano, nitro, hydroxyl, C1-3-alkyl, C1-3-alkoxy, C1-3-
thioalkyl, C1-3-fluoroalkyl, C1-3-fluoroalkoxy or C1-3-
fluorothioalkyl group;
or a group chosen from a phenyl, naphthalenyl biphenyl,
phenylethylenyl, naphthylethylenyl, phenyloxy,
phenylthxo, phehylsulfonyl, benzoyl phenylmethoxy,
phenylethoxy, phenylpropoxy, naphthalenyloxy,
naphthalenylmethoxy, naphthalenylethoxy, and
naphthalenylpropoxy, and optionally substituted with
one or more substituents chosen from a halogen atom,
and the following groups: hydroxyl, cyano, nitro, C1-4-
alkyl, C1-4-alkoxy, C1-4-thioalkyl, C1-3-fluoroalkyl, C1-3-
fluoroalkoxy, C1-3-fluorothioalkyl, phenyloxy,
benzyloxy, piperidyl, pyrrolidinyl, morpholinyl, NH2,

NHR6, NR6R7; NHCOR6, COR6, CO2R6, SO2R6, -O-(C1-3-
alkylene)-O-, 4-piperazinyl optionally substituted with
a C1-3-alkyl or with a benzyl,
R3 represents either a 2,2,2-trifluoroethyl group,
or a phenyl group optionally substituted with one or
more halogen atoms or cyano, nitro, C1-3-alkyl, C1-3-
alkoxy, trifluoromethyl or. trifluoromethoxy groups,
and
R6 and R7 represent, independently of one another, a
C1-3-alkyl group or a phenyl;
with the proviso that:
when R3 represents 2,2,2-trifluoroethyl group and the
group - [A]n- represents a -CH2- group, then R1 is other
thana hydrogen atom or a methoxy group; and
when R3 represents an optionally substituted phenyl
group and the group - [A]n- represents a -CH2-, -CH2CH2-,
-CH(CH3)- or -CH(CH3)-CH2- group, then R1 is other than
a hydrogen or chlorine atom or a methyl or methoxy
group and R2 is other than a hydrogen atom; and
wherein said compound is in the form of a base, or an
addition salt with an acid.
2. A process for preparing a compound of formula (I)

in which R1, R2, R3, A and n are as defined according to
claim 1,
comprising the step of:
reacting an amine of formula (II)


in which R1, R2, n and A are as defined in formula (I) ,
with a carbonate of formula (III)

in which U represents a hydrogen atom or a nitro group
and R3 is as defined in formula (I).
3. A process for preparing a compound of formula (I)

in which
R1, R2, A and n are aa defined according to claim 1, and
R3 represents a phenyl group optionally substituted
with one or more halogen atoms, or cyano, nitro, C1-3-
alkyl, C1-3-alkoxy, trifluoromethyl or trifluoromethoxy
groups, comprising the step of
reacting an amine of general formula (II)


in which R1, R2, n and A are as defined in general
formula (I) , with an aryl chloroformate of general
formula (IIIa)

in which R3 represents a phenyl group optionally
substituted with one or more halogen atoms, or cyano,
nitro, C1-3-alkyl, C1-3-alkoxy, trifluoromethyl or
trifluoromethoxy groups.
4. A pharmaceutical composition comprising at least
one compound of formula (I) as claimed in claim 1, in
the form of a base, or a pharmaceutically acceptable
salt, in combination with one or more pharmaceutically
acceptable excipients.
5. The pharmaceutical composition as claimed in claim
4, wherein compound of formula (I) is selected from the
group consisting of:

- 2, 2, 2-trifluoroethyl benzylcarbamate;
- 2,2,2-trifluorbethyl 4-methoxybenzylcarbamate;
- 4-nitrophenyl 2- [4-(phenylmethoxy) phenyl] ethyl-
carbamate ;
- 4-chloro-2-nitrophenyl 2-(4-(chlorophenyl)ethyl-
carbamate;
- phenyl 2 - (3,4 -dimethoxyphenyl) ethylcarbamate ;
- 2,4,5-trichlorophenyl 2-(4-chlorophenyl)ethyl-
carbamate ;
- phenyl 4-chlorobenzylcarbamate;
- phenyl 4-methoxybenzylcarbamate;

- 4 -fluorophenyl 2 -(4-methoxyphenyl)ethylcarbamate;
- phenyl 3-nitrobenzylcarbamate;
- 4-cyanophenyl 4-methoxybenzylcarbamate;
- phenyl 3-chlorobenzylcarbamate;
- phenyl 3,4-dichlorobenzylcarbamate;
- 4-nitrophenyl 2-(4-hydroxyphenyl)ethylcarbamate;
- phenyl 2-[4-(2-amino-4-thiazolyl) phenyl]ethyl-
carbamate; and
- 2,3,4,5,6-pentafluorophenyl 4 -bromobenzylcarbamate;
in the form of a base, or a pharmaceutically acceptable
salt, hydrate or a solvate thereof.
6. The compound of formula (I) as claimed in claim 1,
in the form of a base, or a pharmaceutically acceptable
salt thereof.
7. The compound of formula (I) as claimed in claim 1,
which is chosen from the following compounds:
- 2,2,2-trifluoroethyl benzylcarbamate;
- 2,2,2-trifluoroethyl 4-methoxybenzylcarbamate;
- 4 -nitrophenyl 2-[4 - (pheriylmethoxy) phenyl] ethyl -
carbamate;
- 4-chloro-2-nitrophenyl 2-(4-(chlorophenyl)ethyl-
carbamate ;
- phenyl 2 - (3,4-dimethoxyphenyl)ethylcarbamate;
- 2,4,5-trichlorophenyl 2-(4-chlorophenyl)ethyl-
carbamate;
- phenyl 4-chlorobenzylcarbamate;
- phenyl 4-methoxybenzylcarbamate;
- 4-fluorophenyl 2-(4-methoxyphenyl) ethylcarbamate;
- phenyl 3-nitrobenzylcarbamate;

- 4-cyanophenyl 4-methoxybenzylcarbamate;
- phenyl 3 -chlorobenzylcarbamate;
- phenyl 3,4-dichlorobenzylcarbamate;
- 4-nitrophenyl 2-(4-hydroxyphenyl)ethylcarbamate;
- phenyl 2-[4-(2-amino-4-thiazolyl)phenyl]ethyl-
carbamate;
- 2,3, 4,5,6-pentafluorophenyl 4-bromobenzylcarbamate;
in the form of a base, or a pharmaceutically acceptable
salt thereof.


ARYLALKYLCARBAMATE DERIVATIVES AND PROCESSES FOR
PREPARATION THEREOF



(57) Abstract: The invention relates to a compound
having general formula (I), wherein: n represents
an integer of between 1 and 6; A is selected from
one or more X, Y and/or Z groups; X represents an
optionally-substituted C1-2-alkylene group; Y represents
an optionally-substituted C2-alkenylene group or a
-C=C- group; Z represents a C3-7-cycloalkyl
group having formula (II) in which m represents an
integer of between 1 and 5, and p and q represent integers
and are defined such that p+q equals a number of between
1 and 5; R1 represents a hydrogen atom, a halogen atom
or a hydroxyl, cyano, nitro, C1-3-alkyl, C1-3-alkoxy,
C1-3-thioalkyl, C1-3-fluoroalkyl, C1-3-fluoroalkoxy,
C1-3-fluorothioalkyl group; R2 represents a hydrogen
atom, a halogen atom or a cyano, nitro, hydroxyl,
C1-3-alkyl, C1-3-alkoxy, C1-3-thioalkyl, C1-3-fluoroalkyl,
C1-3-fluoroalkoxy, C1-3-fluorothioalkyl group, or an
optionally-substituted aromatic or heteroaromatic group;
R3 represents either a 2,2,2-trifluoroethyl group or an
optionally-substituted phenyl group; and R6 and R7
represent independently of each other a C1-3-alkyl group,
a phenyl; said compound taking the form of a base, an
acid addition salt, a hydrate or a solvate. The invention
also relates to the use of the compound in therapeutics.

Documents:

00779-kolnp-2006-abstract.pdf

00779-kolnp-2006-claims.pdf

00779-kolnp-2006-description complete.pdf

00779-kolnp-2006-form 1.pdf

00779-kolnp-2006-form 3.pdf

00779-kolnp-2006-form 5.pdf

00779-kolnp-2006-gpa.pdf

00779-kolnp-2006-international exm report.pdf

00779-kolnp-2006-international publication.pdf

00779-kolnp-2006-priority document.pdf

779-KOLNP-2006-ABSTRACT.pdf

779-KOLNP-2006-AMANDED CLAIMS.pdf

779-KOLNP-2006-ASSIGNMENT.pdf

779-KOLNP-2006-CORRESPONDENCE.pdf

779-KOLNP-2006-DESCRIPTION (COMPLETE).pdf

779-KOLNP-2006-EXAMINATION REPORT REPLY RECIEVED.pdf

779-KOLNP-2006-EXAMINATION REPORT.pdf

779-KOLNP-2006-FORM 1.pdf

779-KOLNP-2006-FORM 13-1.1.pdf

779-KOLNP-2006-FORM 13-1.2.pdf

779-KOLNP-2006-FORM 18.pdf

779-KOLNP-2006-FORM 2.pdf

779-KOLNP-2006-FORM 3-1.1.pdf

779-KOLNP-2006-FORM 3.pdf

779-KOLNP-2006-FORM 5.pdf

779-kolnp-2006-form13.PDF

779-KOLNP-2006-GPA.pdf

779-KOLNP-2006-GRANTED-ABSTRACT.pdf

779-KOLNP-2006-GRANTED-CLAIMS.pdf

779-KOLNP-2006-GRANTED-DESCRIPTION (COMPLETE).pdf

779-KOLNP-2006-GRANTED-FORM 1.pdf

779-KOLNP-2006-GRANTED-FORM 2.pdf

779-KOLNP-2006-GRANTED-SPECIFICATION.pdf

779-KOLNP-2006-OTHERS-1.1.pdf

779-KOLNP-2006-OTHERS.pdf

779-KOLNP-2006-PETITION UNDER RULE 137.pdf

779-KOLNP-2006-REPLY TO EXAMINATION REPORT.pdf

abstract-00779-kolnp-2006.jpg


Patent Number 264782
Indian Patent Application Number 779/KOLNP/2006
PG Journal Number 04/2015
Publication Date 23-Jan-2015
Grant Date 21-Jan-2015
Date of Filing 30-Mar-2006
Name of Patentee SANOFI AVENTIS
Applicant Address 174, AVENUE DE FRANCE, PARIS, 75013, FRANCE.
Inventors:
# Inventor's Name Inventor's Address
1 ABOUABDELLAH, AHMED 2 RUE DES EGLANTIERS, F-94320, THIAIS, FRANCE.
2 ALMARIO GARCIA, ANTONIO 26 AVENUE ROGER SALENGRO, F-92290, CHATENAY, MALABRY, FRANCE.
PCT International Classification Number C07C 271/48
PCT International Application Number PCT/FR2004/002486
PCT International Filing date 2004-10-01
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 0311615 2003-10-03 France