Title of Invention | " A COMPOUND OF FORMULA I." |
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Abstract | PDE4 inhibition is achieved by novel compounds, e.g., N-substituted aniline and diphenylamine analogs. The compounds of the present invention are of Formula (I): wherein R1, R2, R3 and R4 are as defined herein. |
Full Text | DESCRIPTION (COMPLETE) OCR NOT PREPARE DUE TO PRINT PROBLEM WE CLAIM: 1. A compound relating to N-substituted aniline and diphenylamine analogs as phosphodiesterase 4-inhibitors of Formula I: (Formula Removed) wherein R1 is H or alkyl having 1 to 4 carbon atoms, which is branched or unbranched and which is unsubstituted or substituted one or more by halogen; R2 is alkyl having 1 to 12 carbon atoms, which is branched or unbranched and which is unsubstituted or substituted one or more times by halogen, hydroxy, cyano, C1-4-alkoxy, 0x0 or combinations thereof, and wherein optionally one or more -CH2CH2- groups is replaced in each case by -CH=CH- or -C≡C-, cycloalkyl having 3 to 10 carbon atoms, which is unsubstituted or substituted one or more times by halogen, hydroxy, 0x0, cyano, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, or combinations thereof, cycloalkylalkyl having 4 to 16 carbon atoms, which is unsubstituted or substituted in the cycloalkyl portion and/or the alkyl portion one or more times by halogen, 0x0, cyano, hydroxj', C1-4-alkyl, C1-4-alkoxy or combinations thereof, aryl having 6 to 14 carbon atoms, which is unsubstituted or substituted one or more times by halogen, CF3, OCF3, alkyl having 1 to 12 carbon atomi, hydroxy, alkoxy having 1 to 12 carbon atom, nitro, methylenedioxy, ethylenedioxy, cyano, or combinations thereof, arylalkyl in which the aryl portion has 6 to 14 carbon atoms and the alkyl portion, which is branched or unbranched, has 1 to 5 carbon atoms, which the arylalkyl radical is unsubstituted or is substituted in the aryl portion one or more times by halogen, CF3, OCF3, alkyl having 1 to 12 carbon atom, hydroxy, alkoxy having 1 to 12 carbon atom, nitro, cyano, methylenedioxy, ethylenedioxy, or combinations thereof, and wherein in the alkyl portion one or more -CH2CH2- groups are each optionally replaced by -CH=CH- or -C/C-, and one or more ~CH2- groups are each optionally replaced by -O- or -NH- and/or the alkyl portion is optionally substituted by halogen, 0x0, hydroxy, cyano, or combinations thereof, a partially unsaturated carbocyclic group having 5 to 14 carbon atoms, which is unsubstituted or substituted one or more times by halogen, alkyl having 1 to 12 carbon atom, alkoxy having 1 to 12 carbon atom, hydroxy, nitro, cyano, 0x0, or combinations thereof, a heterocyclic group, which is saturated, partially saturated or unsaturated, having 5 to 10 ring atoms in which at least 1 ring atom is a N, O or S atom, which is unsubstituted or substituted one or more times by halogen, hydroxy, aryl, alkyl having 1 to 12 carbon atom, alkoxy having 1 to 12 carbon atom, cyano, trifluoromethyl, nitro, 0x0, or combinations thereof, or a heterocycle-alkyl group, wherein the heterocyclic portion is saturated, partially saturated or unsaturated, and has 5 to 10 ring atoms in which at least 1 ring atom is a N, O or S atom, and the alkyl portion is branched or unbranched and has 1 to 5 carbon atoms, the heterocycle-alkyl group is unsubstituted or substituted one or more times in the heterocyclic portion by halogen, OCF3, hydroxy, aryl, alkyl having 1 to 12 carbon atom, alkoxy having 1 to 12 carbon atom, cyano, trifluoromethyl, nitro, 0x0, or combinations thereof, wherein in the alkyl portion one or more -CH2CH2-groups are each optionally replaced by -CH=CH- or -C≡C-, and one or more -CH2- groups are each optionally replaced by -O- or -NH- and/or the alkyl portion is optionally substituted by halogen, oxo, hydroxy, cyano, or combinations thereof; R3 is, alkyl having 1 to 8 which is branched or unbranched and which is unsubstituted or substituted one or more times with halogen, cyano, C1-4-alkoxy, or combinations thereof, a partially unsaturated carbocycle-alkyl group wherein the carbocyclic portion has 5 to 14 carbon atoms and the alkyl portion which is branched or unbranched has 1 to 5 carbon atoms, and which is unsubstituted or substituted in the carbocyclic portion one or more times by halogen, alkyl having 1 to 12 carbon atom, alkoxy having 1 to 12 carbon atom, nitro, cyano, 0x0, or combinations thereof, and the alkyl portion is optionally substituted by halogen, C1-4-alkoxy, cyano or combinations thereof, aiylalkyl having 7 to 19 carbon atoms, wherein the aryl portion has 6 to 14 carbon atoms and the alkyl portion, which is branched or unbranched, has 1 to 5 carbon atoms, aiylalkyl radical is unsubstituted or substituted, in the aryl portion, one or more times by halogen, trifluoromethyl, CF3O, nitro, amino, alkyl having 1 to 12 carbon atom, alkoxy having 1 to 12 carbon atom, alkylamino wherein the alkyl group has 1 to 12 carbon atom, dialkylamino wherein each alkyl group has 1 to 12 carbon atom, and/or substituted in the alkyl portion by halogen, cyano, or methyl, or heteroarylalkyl group, wherein the heteroaryl portion is partially or fully saturated and has 5 to 10 ring atoms in which at least 1 ring atom is a N, O or S atom, the alkyl portion, which is branched or unbranched, has 1 to 5 carbon atoms, the heteroarylalkyl group is unsubstituted or substituted one or more times in the heteroaryl portion by halogen, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, cyano, trifluoromethyl, CF3O, nitro, 0x0, amino, alkylamino wherein the alkyl group has 1 to 12 carbon atom, dialkylamino wherein each alkyl group has 1 to 12 carbon atom, or combinations thereof and/or substituted in the alkyl portion by halogen, cyano, or methyl or combinations thereof; R4 is, aryl having 6 to 14 carbon atoms and which is unsubstituted or substituted one or more times by halogen, alkyl having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, alkynyl having 2 to 12 carbon atoms, hydroxy, alkoxy having 1 to 12 carbon atoms, alkoxyalkoxy wherein each alkoxy group has 1 to 12 carbon atoms, nitro, methylenedioxy, ethylenedioxy, trifluoromethyl, OCF3, amino, aminoalkyl wherein the alkyl group has 1 to 12 carbon atoms, aminoalkoxy wherein the alkyloxy group has 1 to 12 carbon atoms, dialkylamino wherein each alkyl group has 1 to 12 carbon atoms, hydroxyalkyl having 1 to 12 carbon atoms, hydroxamic acid, pyrrolyl, tetrazole-5-yl, 2(-heterocycle)tetrazole-5-yl, hydroxyalkoxy, carboxy, alkyl -O-CO- wherein the alkyl portion has 1 to 12 carbon atoms, cyano, alkanoyl having 1 to 13 carbon atoms, aroyl having 7 to 15 carbon atoms, alkylthio having 1 to 12 carbon atoms, alkylsulfinyl having 1 to 12 carbon atoms, alkylsulfonyl having 1 to 12 carbon atoms, phenoxy, trialkylsilyloxy wherein each alkyl group has 1 to 12 carbon atoms, R5-L-, or combinations thereof, or heteroaryl having 5 to 10 ring atoms in which at least 1 ring atom is a heteroatom, which is unsubstituted or substituted one or more times by halogen, alkyl having 1 to 12 carbon atoms, hydroxy, alkoxy having 1 to 12 carbon atoms, alkoxyalkoxy wherein each alkoxy group has 1 to 12 carbon atoms, nitro, methylenedioxy, ethylenediox;y, trifluoromethyl, amino, aminoalkyl wherein the alkyl group has 1 to 12 carbon atoms, aminoalkoxy wherein the alkyloxy group has 1 to 12 carbon atoms, dialkylamino wherein each alkyl group has 1 to 12 carbon atoms, hydroxyalkyl, hydroxamic acid, tetrazole-5-yl, hydroxyalkoxy having 1 to 12 carbon atoms, carboxy, alkyl -O-CO- wherein the alkyl portion has 1 to 12 carbon atoms, cyano, alkanoyl having 1 to 13 carbon atoms, aroyl having 7 to 15 carbon atoms, alkylthio having 1 to 12 carbon atoms, alkylsulfinyl having 1 to 12 carbon atoms, alkylsulfonyl having 1 to 12 carbon atoms, phenoxy, trialkylsilyioxy wherein each alkyl group has 1 to 12 carbon atoms, R5-L-, or combinations thereof; R5 is H, alkyl having 1 to 8 carbon atoms, which is unsubstituted or substituted one or more times with halogen, C1-4-alkyl, C1-4-alkoxy, oxo, or combinations thereof, alkylamino or dialkylamino wherein each alkyl portion has independently 1 to 8 carbon atoms, a partially unsaturated carbocycle-alkyl group wherein the carbocyclic portion has 5 to 14 carbon atoms and the alkyl portion has 1 to 5 carbon atoms, which is unsubstituted or substituted, one or more times by halogen, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, nitro, cyano, oxo, or combinations thereof, cycloalkyl having 3 to 10 carbon atoms, which is unsubstituted or substituted one or more times by halogen, hydroxy, oxo, cyano, alkoxy having 1 to 12 carbon atoms, alkyl having 1 to 4 carbon atoms, or combinations thereof, cycloalkylalkyl having 4 to 16 carbon atoms, which is unsubstituted or substituted in the cycloalkyl portion and/or the alkyl portion one or more times by halogen, oxo, cyano, hydroxy, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, or combinations thereof, aryl having 6 to 14 carbon atoms and which is unsubstituted or substituted one or more times by halogen, alkyl, hydroxy, alkoxy, alkoxyalkoxy, nitro, methylenedioxy, ethylenedioxy, trifluoromethyl, amino, aminoalkyl having 1 to 12 carbon atoms, aminoalkoxy having 1 to 12 carbon atoms, dialkylamino wherein each alkyl group has 1 to 12 carbon atoms, hydroxyalkyl having 1 to 12 carbon atoms, hydroxamic acid, tetrazole-5-yl, hydroxyalkoxy having 1 to 12 carbon atoms, carboxy, alkyl -O-CO- wherein the alkyl portion has 1 to 12 carbon atoms, cyano, alkanoyl having 1 to 13 carbon atoms, aroyl having 7 to 15 carbon atoms, alkylthio having 1 to 12 carbon atoms, alkylsulfinyl having 1 to 12 carbon atoms, alkylsulfonyl having 1 to 12 carbon atoms, phenoxy, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 14 carbon atoms, heteroaiyl having one or two rings and a total number of 5 to 10 ring atoms wherein at least one of the ring atoms is a heteroatom, or combinations thereof, arylalkyl having 7 to 19 carbon atoms, wherein the aryl portion has 6 to 14 carbon atoms and the alkyl portion, which is branched or unbranched, has 1 to 5 carbon atoms, arylalkyl radical is unsubstituted or substituted, in the aryl portion, one or more times by halogen, trifluoromethyl, CF3O, nitro, amino, alkyl having 1 to 12 carbon atoms, alkoxy, amino having 1 to 12 carbon atoins, alkylamino having 1 to 12 carbon atoms, dialkylamino wherein each alkyl group has 1 to 12 carbon atoms, and/or substituted in the alkyl portion by halogen, cyano, or methyl, a heterocyclic group, which is saturated, partially saturated or unsaturated, having 5 to 10 ring atoms in which at least 1 ring atom is a N, O or S atom, which is unsubstituted or substituted one or more times by halogen, alkyl having 1 to 12 carbon atoms, hydroxy, alkoxy having 1 to 12 carbon atoms, alkoxyalkoxy wherein each alkoxy group has 1 to 12 carbon atoms, nitro, methylenedioxy, ethylenedioxy, trifluoromethyl, amino, aminoalkyl having 1 to 12 carbon atoms, aminoalkoxy having 1 to 12 carbon atoms, dialkylamino wherein each alkyl group has 1 to 12 carbon atoms, hydroxyalkyl having 1 to 12 carbon atoms, hydroxamic acid, tetrazole-5-yl, hydroxyalkoxy having 1 to 12 carbon atoms, carboxy, alkyl -O-CO- wherein the alkyl portion has 1 to 12 carbon atoms, cyano, alkanoyl having 1 to 13 carbon atoms, aroyl having 7 to 15 carbon atoms, alkylthio having 1 to 12 carbon atoms, alkylsulfinyl having 1 to 12 carbon atoms, alkylsulfonyl having 1 to 12 carbon atoms, phenoxy, or combinations thereof, or a heterocycle-alkyl group, wherein the heterocyclic portion is saturated, partially saturated or unsaturated, and has 5 to 10 ring atoms in which at least 1 ring atom is a N, O or S atom, and the alkyl portion which is branched or unbranched and has 1 to 5 carbon atoms, the heterocycle-alkyl group is unsubstituted or substituted one or more times in the heterocyclic portion by halogen, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, cyano, trifluoromethyl, CF3O, nitro, 0x0, amino, alkylamino having 1 to 12 carbon atoms, dialkylamino wherein each alkyl group has 1 to 12 carbon atoms, or combinations thereof and/or substituted in the alkyl portion by halogen, cyano, or methyl or combinations thereof; L is a single bond or a divalent aliphatic radical having 1 to 8 carbon atoms wherein one or more -CH2- groups are each optionally replaced by -O-, -S-, -NR&-, -SO2NH-, -NHSO2-, -SO2NR6-, -NR6SO2 , -CO-, -NR6CO-, -CONR6-, -NHCONH-, -OCONH, -NHCOO-, -SCONH-, -SCSNH-, or -NHCSNH-; and R6' is H, alkyl having 1 to 8 carbon atoms, which is branched or unbranched and which is unsubstituted or substituted one or more times with halogen, C1-4-alkyl, C1-4-alkoxy, oxo, or combinations thereof; arylalkyl having 7 to 19 carbon atoms, wherein the aiyl portion has 6 to 14 carbon atoms and the alkyl portion, which is branched or unbranched, has 1 to 5 carbon atoms, the arylalkyl radical is unsubstituted or substituted, in the aryl portion, one or more times by halogen, trifluoromethyl, CF3O, nitro, amino, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkylamino having 1 to 12 carbon atoms, dialkylamino wherein each alkyl group has 1 to 12 carbon atoms, and/or substituted in the alkyl portion by halogen, cyano, or methyl; aiyl having 6 to 14 carbon atoms and which is unsubstituted or substituted one or more times by halogen, alkyl having 1 to 12 carbon atoms, hydroxy, alkoxy having 1 to 12 carbon atoms, alkoxyalkoxy wherein each alkoxy group has V to 12 carbon atoms, nitro, methylenedioxy, ethylenedioxy, trifluoromethyl, amino, aminoalkyl having 1 to 12 carbon atoms, aminoalkoxy having 1 to 12 carbon atoms, dialkylamino wherein each alkyl group has 1 to 12 carbon atoms, hydroxyalkyl having 1 to 12 carbon atoms, hydroxamic acid, tetrazole-5-yl, hydroxyalkoxy having 1 to 12 carbon atoms, carboxy, alkyl -O-CO- wherein the alkyl portion has 1 to 12 carbon atoms, cyano, alkanoyl having 1 to 13 carbon atoms, aroyl having 7 to 15 carbon atoms, alkylthio having 1 to 12 carbon atoms, alkylsulfinyl having 1 to 12 carbon atoms, or alkylsulfonyl having 1 to 12 carbon atoms; or a pharmaceutically acceptable salt thereof; with the provisos that: (a) R4 is at least monosubstituted by R5-L in which L is a divalent aliphatic radical having 1 to 8 carbon atoms wherein at least one -CH2- group isreplaced by -SO2NR6- or -NR6SO2- in which R6 is aryl or aiylalkyl which in each case is substituted or unsubstituted, or (b) R4 is at least mono substituted by R5-L in which L is -SO-, -SO2-, -CONR6SO2-, -SO2NR6CO-, or -SO2NR6-, wherein if L is -SO2NR6-, then R6 is other than H. 2. A compound as claimed in claim 1, wherein R4 is cycloalkyl having 3 to 10 carbon atoms, which is unsubstituted or substituted one or more times by halogen, hydroxy, 0x0, cyano, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, or combinations thereof. 3. A compound according claim 1, wherein R4 is at least monosubstituted by R5-L in which L is a divalent aliphatic radical having 1 to 8 carbon atoms wherein at least one -CH2- group is replaced by -SO2NR6- or -NR6SO2- in which R6 is aryl or arylalkyl which in each case is substituted or unsubstituted. 4. A compound as claimed in claim 1, wherein R4 is at least monosubstituted by R5-L in which L is -SO-, -SO2-, -CONR6SO2-, -SO2NR6CO-, or -SO2NR6-, with the further proviso that when R4 is at least monosubstituted by R5-L in which L is -SO2NR6-, then R6 is other than H. 5. A compound as claimed in claim 1, wherein said compound is selected from: 3-Cyclopentyloxy-4-methoxy-N-(4-(N,N-bis(2,4-dimethoxy)benzyl)-aminosulfonylphenyl)-N-(3-pyridylmethyl)aniline, N-(4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4-methanesulfonylaniline, N-(4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4-(4- piperidinyl) sulfonylaniline, N-(3-Cyclopentyloxy-4-methoxyphenyl)-N-{3-pyridylinethyl)-3-methylsulfonyl- aminocarbonylaniline, N-(3-Cyclopentyloxy-4-methoxyphenyl)-N-(3-pyridylmethyl)-3-(2-methylphenyl)- sulfonylaminocarbonylaniline, N-(3-Cyclopentyloxy-4-methoxyphenyl)-N-(3-pyridylmethyl)-3-phenylsulfonyl- aminocarbonylaniline, N-(3-Cyclopentyloxy-4-methoxyphenyl)-N-(3-pyridylmethyl)-4-phenylsulfonyl- aminocarbonylaniline, N-(3-Cyclopentyloxy-4-inethoxyphenyl)-N-(3-pyridylmethyl)-4-methylsulfonyl- aminocarbonylaniline, N-(4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4-(4- fluorophenyi) sulfonylaminocarbonylaniline, N-(4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(4-(3,5- dichloropyridylmethyl)-4-phenylsulfonylaminocarbonylaniline, N-(4-Methoxy-3-(3R)-tetrahydrofuranylojQrphenyl)-N-(4-(3,5- dichloropyridylmethyl)-4-methylsulfonylaminocarbonylaniline, N-(4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4- ethylsulfonylaminocarbonylaniline, N-(4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4-(2- fluoro phenyl) sulfonylaminocarbonylaniline, N-(4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4-(4- metho>yphenyl) sulfonylaminocarbonylaniline, N-(4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4-(3- chlorophenyl) sulfonylaminocarbonylaniline, N-(4-Difluoromethoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4- methylsulfonylaminocarbonylaniline, N-(4-Difluoromethoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4- phenylsulfonylaminocarbonylaniline, N-(4-Methoxy-3-(3R)-tetraJiydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4- phenylsulfonylaminocarbonylaniline,N-(3-Cyclopentyloxy-4-inethoxyphenyl)-N-(5-fluoro-3-pyridylmethyl)-3-(4- fluorophenyl)sulfonylaminocarbonylaniline, N-|4-Difluoromethoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-3- methylsulfonylaminocarbonylaniline, N - (4 - Difluoromethoxy-3 - (3 R) - te trahydrofuranyloxyphenyl) - N-(3-pyridylmethy 1) - 3- phenylsulfonylaminocarbonylaniline, N-(4-Difluoromethoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-{3-pyridylinethyl)-4- (3 - chlorophenyl) sulfonylaminocarbonylaniline, N-(4-Difluoromethoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4- (2-fluorophenyl) sulfonylaminocarbonylaniline, N-(4-Difluoroniethoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4- (2,4-difluorophenyl)sulfonylaminocarbonylaniline, N-(4-Difluoromethoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylniethyl)-4- (3,4-difluorophenyl)sulfonylaininocarbonylaniline, N-(4-Difluoroniethoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylniethyl)-4- (1,1 -dime thylethyl) sulfonylaminocarbonylaniline, N-(4-Difluoromethoxyy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4- (5-chloro-2-thienyl)sulfonylaminocarbonylaniline, N-(4-Difluoromethoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4- (3 - thieny 1) sulfonylaminocarbonylaniline, N-(3,4-Bisdifluoromethoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3- pyridylmethyl)-4-(4-fluorophenyl)sulfonylaminocarbonylaniline, N-{3,4-Bisdifluoromethoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3- pyridylmethyl)-4-(3-fluorophenyl)sulfonylaminocarbonylaniline, N-(3,4-Bisdifluoromethoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3- pyridylmethyl)-4 - (3-chlorophenyl) sulfonylaminocarbonylaniline, N-(4-Difluoromethoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-{3-pyridylmethyl)-4- (3 - c:y anophenyl) sulfonylaminocarbonylaniline, N-(4-Difluoromethoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4- (4-fluorophenyl) sulfonylaminocarbonylaniline, N-(4-Difluoromethoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4- (2-thienyl)sulfonylaminocarbonylaniline,N-(4-Difluoromethoxy-3-(3R)-tetrahydrofuranyloxy^phenyl)-N-(3-pyridylmethyl)-4- (3--fluorophenyl)sulfonylaminocarbonylaniline, N-(4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-f3-pyridylmethyl)-4-(3- cyanophenyljsulfonylaminocarbonylaniline, N-(4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(2,6-difluoroben2yl)-4-(4- fluorophenyl)sulfonylaminocarbonylaniline, N-(4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4-(3- fluorophenyl)sulfonylaininocarbonylaniline, N-(4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4-(2,4- difluorophenyl) sulfonylaminocarbonylaniline, N-(4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4-(3,4- difluoropheny 1) sulfonylaminocarbonylaniline, N-(3-Cyclopropylniethoxy-4-methoxyphenyl)-N-(3-pyridylniethyl)-4-(3- chlorophenyl) sulfonylaminocarbonylaniline, N-(4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-fluorobenzyl)-4-(4- fluorophenyl) sulfonylaminocarbonylaniline, N-(3-Cyclopropylmethoxy-4-methoxyphenyl)-N-(3-pyridylmethyl)-4-(4- fluorophenyl) sulfonylaminocarbonylaniline, N-(3-Cyclopropylmethoxy-4-methoxyphenyl)-N-(3-pyridylmethyl)-4-(3- fluorophenyl)sulfonylaminocarbonylaniline, N-(4-Difluoromethoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4- ethylsulfonylaminocarbonylaniline, N-(3-Cyclopentyloxy-4-difluoromethoxyphenyl)-N-(3-pyridylmethyl)-4-(3- cyanophenyl) sulfonylaminocarbonylaniline, N-(3-Cyclopentyloxy-4-difluoromethoxyphenyl)-N-(3-pyridylmethyl)-4-(4- fluorophenyl)sulfonylaminocarbonylaniline, N-(3-Cyclopentyloxy-4-difluoromethoxyphenyl)-N-(3~pyridylmethyl)-4-(3- fluorophenyl)sulfonylaminocarbonylaniline, N-(3-Cyclopentyloxy-4-difluoromethoxyphenyl)-N-(3-pyridylmethyl)-4-(3- chiorophenyl)sulfonylaminocarbonylaniline, N-(3-Ethoxy-4-methoxyphenyl)-N-(3-pyridylmethyl)-4-{2,4- difluorophenyl)sulfonylaminocarbonylaniline, N-(3,4-Bisdifluoromethoxy-3-{3R)-tetrahydrofuranyloxyphenyl)-N-(3- pyridylmethyl)-4-methylsulfonylaminocarbonylaniline, N-(3-Cyclopropylmethoxy-4-methoxyphenyl)-N-(3-pyridylinethyl)-4- ethyl sulfonylaminocarbonylaniline, N-(3-Ethoxy-4-methoxyphenyl)-N-(3-p5n-idylmethyl)-4-(4- fluorophenyl) sulfonylaminocarbonylaniline, N-(3-Ethoxy-4-met±ioxyphenyl)-N-(3-pyridylmethyl)-4-(3- chlorophenyl)sulfonylaminocarbonylaniline, N~(3-Ethoxy-4-methoxyphenyl)-N-(3-pyridylmethyl)-4-(3,4- difluorophenyl)sulfonylaminocarbonylaniline, N-(3-Ethoxy-4-methoxyphenyl)-N-(3-pyridylmethyl)-4-(2- thienyl)sulfonylaininocarbonylaniline, N-(4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyTidylmethyl)-4- cyclopentylmethylcarbonylaminosulfonylaniline, N-(4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4-{4- fluorophenyljcarbonylaminosulfonylaniline, N~(4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmet±iyl)-4-( 1-ethyl- 5-methylpyrazol-4-yl)carbonylaminosulfonylaniline, N-(3-Cyclopentyloxy-4-inethoxyphenyl)-N-(3-pyridylmethyl)-3-(4-methylpiperazin- 1 - yl)sulfonylaniline, N-(3-Cyclopentyloxy-4-niethoxyphenyl)-N-(3-pyridylmethyl)-3-(4- morpholinyl) sulfonylaniline, N-(3-Cyclopentyloxy-4-methoxyphenyl)-N-(3-pyridylmethyl)-4-(4-niethylpiperazin- 1 - yl) sulfonylaniline, N-(3-Cyclopentyloxy-4-niethoxyphenyl)-N-(3-pyridylmethyl)-4-(4- morpholinyl) sulfonylaniline, N-(4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-3-(4- me;thylpiperazin-1 -yl) sulfonylaniline, N-(4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4-(4- methylpiperazin-1 -yl) sulfonylaniline, N-(4-Methoxyr-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4-(4- morpholinyl) sulfonylaniline,N-(4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-3-(4-morpholinyl) sulfonylaniline, N-(4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4-(4-ethylpiperazin-1 -yl) sulfonylaniline, N-(4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4-(4-cyclohexylpiperazin-1 -yl) sulfonylaniline, N (4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4-(3,5-dimethylpiperazin-1 -yl) sulfonylaniline, N-(4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4-(4-(2-pyridyl)piperazin-1 -yl) sulfonylaniline, N-(4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4-(4-(4-fluorophenyl)piperazin-l-yl)sulfonylaniline, N (4-Methoxy-3-(3R)-tetrahydrofuranyloxyphenyl)-N-(3-pyridylmethyl)-4-(2,5-dimethylpyrrol- 1 -yl) sulfonylaniline, and pharmaceutically acceptable salts thereof, wherein compounds that are optically active can be in the form of their separate enantiomers or mixtures thereof, including racemic mixtures. 6. A compound as claimed in any one of claims 1 to 5, wherein R1 is methyl or difluoromethyl. 7. A compound as claimed in any one of claims 1 to 6, wherein R2 is cyc;loalkyl. 8. A compound as claimed in claim 7, wherein R2 is cyclopentyl. 9. A compound as claimed in any one of claims 1 to 6, wherein R2 is phenyl, methylphenyl, methoxyphenyl, chlorophenyl, phenethyl, phenpropyl, phenbutyl, phenylethenyl, phenoxyethyl, phenoxypropyl, phenoxybutyl, chlorophenylethyl, methoxyphenyl ethyl, chlorophenylethenyl. chlorophenoxyethyl, chlorophenypropyl, methoxyphenpropyl, methoxyphenbutyl, chlorophenbulyl, nitrophenbutyl, or chlorophenylaminoethyl. 10. A compound as claimed in any one of claims 1 to 6, wherein R2 is cyclohexenyl, cyclohexadienyl, or indan-2-yl which in each case is unsubstituted or svibstituted, particularly. 11. A compound as claimed in any one of claims 1 to 6, wherein R2 is an alkyl group having 1 to 4 carbon atoms, which is substituted or unsubstituted. 12. A compound as claimed in any one of claims 1 to 6, wherein R2 is methyl, diiluoromethyl, trifluoromethyl, or methoxyethyl. 13. A compound as claimed in any one of claims 1 to 6, wherein R2 is a heterocyclic or heterocycle-alkyl group, in which the heterocyclic group has 5 to 6 ring atoms and 1 to 2 hetero-ring atoms selected from N, O and S. 14. A compound as claimed in any one of claims 1 to 6, wherein R2 is tetrahydrofuranyl, pyrrolidinyl, pyrrolyl, pyridylmethyl, pyridylethyl, pyridylpropyl, piperazinylmethyl, piperazinylethyl, or methylpiperazinylethyl. 15. A compound as claimed in any one of claims 1 to 6, wherein R2 is cyclopentyi, tetrahydrofuranyl, CHF2, methoxyethyl, cyclopropylmethyl, phenethyl, phenpropyl, phenylethenyl, phenoxyethyl, phenoxybutyl, phenylaminoethyl, indan-2-yI, pyridylethyl, or pyridylpropyl. 16. A compound as claimed in any one of claims 1 to 15, wherein R3 is alkyl having 1 to 4 carbon atoms, arylalkyl or a heteroarylalkyl group, which in each case is substituted or unsubstituted. 17. A compound as claimed in claim 16, wherein R3 is methyl, ethyl, n-propyl, n-but, substituted or unsubstitituted benayl, substituted or unsubstitituted phenethyl, substituted or unsubstitituted phenpropyl, substituted or unsubstituted pyridylmethyl, substituted or unsubstitituted furanylmethyl, substituted or unsubstitituted thienylmethyl, substituted or unsubstitituted pyrrolylmethyl, substituted or unsubstitituted oxazolylmethyl, substituted or unsubstitituted isoxazolylmethyl, substituted or unsubstitituted pyrimidinylmethyl, substituted or unsubstitituted thiazolylmethyl, substituted or unsubstitituted isoquinolinylmethyl, substituted or unsubstitituted qumolinylmethyl. 18. A compound as claimed in claim 16, wherein R3 is arylalkyl or a heteroarylalkyl group, which in each case is unsubstituted or substituted in the aiyi or heteroaiyl portion by F, Cl, CH3, C2H5, OCH3, or CN. 19. A compound as claimed in anyone of claims 3 to 4, wherein R4 is phenyl which is at least mono substituted by R5-L. 20. A compound as claimed in anyone of claims 3 to 4, wherein R4 is phenyl, naphthyl, biphenyl, furanyl, pyrazinyl, pyrimidinyl, pyridyl, quinolinyl, or isoquinolinyl which is at least monosubstituted by R5-L. 21. A pharmaceutical composition comprising 0.1-50 mg of a compound as claimed in any one of claims 1 to 20 and a pharmaceutical acceptable amount as a pharmaceutically acceptable carrier. |
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91-delnp-2005-complete specification (as files).pdf
91-delnp-2005-complete specification (granted).pdf
91-delnp-2005-correspondence-others.pdf
91-delnp-2005-correspondence-po.pdf
91-delnp-2005-description (complete).pdf
91-delnp-2005-petition -138.pdf
Patent Number | 243900 | |||||||||||||||||||||||||||
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Indian Patent Application Number | 91/DELNP/2005 | |||||||||||||||||||||||||||
PG Journal Number | 46/2010 | |||||||||||||||||||||||||||
Publication Date | 12-Nov-2010 | |||||||||||||||||||||||||||
Grant Date | 10-Nov-2010 | |||||||||||||||||||||||||||
Date of Filing | 10-Jan-2005 | |||||||||||||||||||||||||||
Name of Patentee | MEMORY PHARMACEUTICALS CORPORATIONS | |||||||||||||||||||||||||||
Applicant Address | 100 PHILIPS PARKWAY, MONTVALE, NEW JERSEY 07645, UNITED STATE OF AMERICA. | |||||||||||||||||||||||||||
Inventors:
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PCT International Classification Number | C07D 213/38 | |||||||||||||||||||||||||||
PCT International Application Number | PCT/US2003/022543 | |||||||||||||||||||||||||||
PCT International Filing date | 2003-07-21 | |||||||||||||||||||||||||||
PCT Conventions:
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