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US 2003/0191126 A1Published application
Serotonin reuptake inhibitor
AssigneeSumitomo Pharmaceuticals Company, Limited
InventorsToru Kodo, Shuji Masumoto, Koji Koyama, Naoya Kinomura
Life of this patent
Estimating the term…
Abstract
A serotonin reuptake inhibitor containing a cyclic amine represented by the following formula, a prodrug thereof, or a pharmaceutically acceptable salt of said cyclic amine or prodrug as an active ingredient: 1 wherein R0 is a hydrogen atom, a halogen atom, an alkyl group, a substituted alkyl group, a hydroxyl group, an alkoxy group or the like, R3 is a hydrogen atom or the like, Y is an alkylene group or the like, Z is a hydrogen atom, a cycloalkyl group, an aryl group or the like, n is 1, 2 or 3, and m is 2, 3, 4, 5 or 6.
Claims25
A serotonin reuptake inhibitor comprising a cyclic amine represented by the formula:
- 91
- wherein R0 is a hydrogen atom, a halogen atom, an alkyl group, a substituted alkyl group, a hydroxyl group, an alkoxy group, a substituted alkoxy group, an alkylthio group or a substituted alkylthio group, provided that when two or more R0s are present, they are independently selected from the above-mentioned groups or two of them may be taken together to form a ring;
- R3 is a hydrogen atom or a substituent;
- Y is a group represented by the formula:
- 92
- Z is a hydrogen atom, a cycloalkyl group, an aryl group, a substituted aryl group, an aromatic heterocyclic group, a substituted aromatic heterocyclic group, or an aliphatic heterocyclic group having an amide linkage (CO—N) or an imide linkage (CO—N—CO) in the ring;
- n is an integer of 1, 2 or 3;
- m is an integer of 2, 3, 4, 5 or 6;
- R5s are independently a hydrogen atom or a substituent;
- and
- R6s are independently a hydrogen atom or a substituent,
- a prodrug of said cyclic amine, or a pharmaceutically acceptable salt of said cyclic amine or prodrug, as an active ingredient.
9 more elements
Any compound selected from the group consisting of the following compounds (1) to (40), a pharmacologically acceptable salt thereof, or a solvate of said compound or salt:
- (1) N-benzyl-3-{2-[4-(2-bromo-5-methoxybenzyl)-1-piperidinyl]ethyl}benzamide,
- (2) 3-{2-[4-(2-bromo-5-methoxybenzyl)-1-piperidinyl]ethyl}benzamide,
- (3) 3-{2-[4-(2-bromo-5-ethoxybenzyl)-1-piperidinyl]ethyl}benzamide,
- (4) 3-{2-[4-(2-bromo-5-isopropoxybenzyl)-1-piperidinyl]ethyl}benzamide,
- (5) 3-{2-[4-(2-bromo-5-methoxybenzyl)-1-piperidinyl]ethyl}-N,N-dimethylbenzamide,
- (6) 3-{2-[4-(2-bromo-5-ethoxybenzyl)-1-piperidinyl]ethyl}-N,N-dimethylbenzamide,
- (7) 3-{2-[4-(2-bromo-5-isopropoxybenzyl)-1-piperidinyl]ethyl}-N,N-dimethylbenzamide,
- (8) 3-{2-[4-(2-bromo-5-chlorobenzyl)-1-piperidinyl]ethyl}-N,N-dimethylbenzamide,
- (9) 3-{2-[4-(2-bromo-5-fluorobenzyl)-1-piperidinyl]ethyl}-N,N-dimethylbenzamide,
- (10) 4-(2-bromo-5-methoxybenzyl)-1-[2-(2-chlorophenyl)ethyl]piperidine,
- (11) 4-(2-bromo-5-ethoxybenzyl)-1-[2-(2-chlorophenyl)ethyl]piperidine,
- (12) 4-(2-bromo-5-isopropoxybenzyl)-1-[2-(2-chlorophenyl)ethyl]piperidine,
- (13) 4-(2-bromo-5-methoxybenzyl)-1-[2-(2-methoxyphenyl)ethyl]piperidine,
- (14) 4-(2-bromo-5-methoxybenzyl)-1-[2-(2-ethoxyphenyl)ethyl]piperidine,
- (15) 4-(2-bromo-5-methoxybenzyl)-1-[2-(3-methoxyphenyl)ethyl]piperidine,
- (16) 4-(2-bromo-5-methoxybenzyl)-1-[2-(3-isopropoxyphenyl)ethyl]piperidine,
- (17) 4-(2-bromo-5-chlorobenzyl)-1-[2-(3-methoxyphenyl)ethyl]piperidine,
- (18) 4-(2-bromo-5-chlorobenzyl)-1-[2-(3-ethoxyphenyl)ethyl]piperidine,
- (19) 4-(2-bromo-5-chlorobenzyl)-1-[2-(3-isopropoxyphenyl)ethyl]piperidine,
- (20) 4-(2-bromo-5-fluorobenzyl)-1-[2-(3-methoxyphenyl)ethyl]piperidine,
- (21) 4-(2-bromo-5-fluorobenzyl)-1-[2-(3-ethoxyphenyl)ethyl]piperidine,
- (22) 4-(2-bromo-5-fluorobenzyl)-1-[2-(3-isopropoxyphenyl)ethyl]piperidine,
- (23) 4-(2-bromo-5-methoxybenzyl)-1-[2-(2-chloro-6-fluorophenyl)ethyl]piperidine,
- (24) 1-[2-(1,3-benzodioxol-5-yl)ethyl]-4-(2-bromo-5-methoxybenzyl)piperidine,
- (25) 1-[2-(1,3-benzodioxol-5-yl)ethyl]-4-(2-bromo-5-ethoxybenzyl)piperidine,
- (26) 1-[2-(1,3-benzodioxol-5-yl)ethyl]-4-(2-bromo-5-isopropoxybenzyl)piperidine,
- (27) 1-[2-(1,3-benzodioxol-5-yl)ethyl]-4-(2-bromo-5-fluorobenzyl)piperidine,
- (28) 1-[2-(1,3-benzodioxol-5-yl)ethyl]-4-(2-bromo-5-chlorobenzyl)piperidine,
- (29) 4-(2-bromo-5-methoxybenzyl)-1-[2-(6-chloro-1,3-benzodioxol-5-yl)ethyl]piperidine,
- (30) 4-(2-bromo-5-ethoxybenzyl)-1-[2-(6-chloro-1,3-benzodioxol-5-yl)ethyl]piperidine,
- (31) 4-(2-bromo-5-isopropoxybenzyl)-1-[2-(6-chloro-1,3-benzodioxol-5-yl)ethyl]piperidine,
- (32) 4-(2-bromo-5-chlorobenzyl)-1-[2-(6-chloro-1,3-benzodioxol-5-yl)ethyl]piperidine,
- (33) 4-(2-bromo-5-fluorobenzyl)-1-[2-(6-chloro-1,3-benzodioxol-5-yl)ethyl]piperidine,
- (34) 4-(2-bromo-5-methoxybenzyl)-1-[2-(2-chloro-3-methoxyphenyl)ethyl]piperidine,
- (35) 4-(2-bromo-5-fluorobenzyl)-1-[2-(2-chloro-4-methoxyphenyl)ethyl]piperidine,
- (36) 4-(2-bromo-5-methoxybenzyl)-1-[2-(2-naphthyl)ethyl]piperidine,
- (37) 4-(2-bromo-5-methoxybenzyl)-1-[2-(4-fluorophenyl)ethyl]piperidine,
- (38) 4-benzyl-2-{4-[4-(5-methoxy-2-methylbenzyl)-1-piperidinyl]butyl}-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one,
- (39) 4-benzyl-2-{4-[4-(2-bromo-5-methoxybenzyl)-1-piperidinyl]butyl}-1,2,4-triazine-3,5(2H,4H)-dione, and
- (40) 2-{3-[4-(2-bromo-5-methoxybenzyl)-1-piperidinyl]propyl}-1H-isoindole-1,3(2H)-dione.
- (41) 4-(2-bromo-5-methoxyethoxybenzyl)-1-[2-(7-chloro-1,4-benzodioxan-6-yl)ethyl]piperidine,
- (42) 4-(2-chloro-5-methoxyethoxybenzyl)-1-[2-(7-chloro-1,4-benzodioxan-6-yl)ethyl]piperidine.
39 more elements
A cyclic amine represented by the formula:
- 96
- wherein R1 is a bromine atom, a chlorine atom or a lower alkyl group;
- R2 is a hydroxyl group, a lower alkoxy group, a substituted lower alkoxy group or a halogen atom;
- R3 is a hydrogen atom or a lower alkyl group;
- R4 is a hydrogen atom, a halogen atom or an alkoxy group, or R4 may be taken together with R2 to form a ring;
- and
- n is an integer of 1 or 2, or a salt of said cyclic amine.
4 more elements
A cyclic amine represented by the formula:
- 97
- wherein R1 is a bromine atom, a chlorine atom or a lower alkyl group;
- R2 is a hydroxyl group, a lower alkoxy group, a substituted lower alkoxy group or a halogen atom, provided that R1 and R2 are not chlorine atoms at the same time;
- R3 is a hydrogen atom or a lower alkyl group;
- R4 is a hydrogen atom, a halogen atom or an alkoxy group, or R4 may be taken together with R2 to form a ring;
- and
- n is an integer of 1 or 2, or
- a salt of said cyclic amine.
5 more elements
Any compound selected from the group consisting of the following compounds (1) to (16), a salt thereof, or a solvate of said compound or salt:
- (1) 4-(2-bromo-5-methoxybenzyl)piperidine,
- (2) 4-(2-bromo-5-hydroxybenzyl)piperidine,
- (3) 4-(2-bromo-5-ethoxybenzyl)piperidine,
- (4) 4-(2-bromo-5-isopropoxybenzyl)piperidine,
- (5) 4-[2-bromo-5-(difluoromethoxy)benzyl]-piperidine,
- (6) 4-(2-bromo-5-fluorobenzyl)piperidine,
- (7) 4-(2-bromo-5-chlorobenzyl)piperidine,
- (8) 4-[(6-bromo-1,3-benzodioxol-5-yl)methyl]-piperidine,
- (9) 4-(2-chloro-5-methoxybenzyl)piperidine,
- (10) 4-(2-chloro-5-hydroxybenzyl)piperidine,
- (11) 4-(2-chloro-5-ethoxybenzyl)piperidine,
- (12) 4-(2-chloro-5-isopropoxybenzyl)piperidine,
- (13) 4-[2-chloro-5-(difluoromethoxy)benzyl]-piperidine,
- (14) 4-(2-chloro-5-fluorobenzyl)piperidine,
- (15) 4-(2-chloro-5-chlorobenzyl)piperidine, and
- (16) 4-[(6-chloro-1,3-benzodioxol-5-yl)methyl]-piperidine.
- (17) 4-(2-bromo-5-methoxyethoxybenzyl)piperidine
- (18) 4-(2-chloro-5-methoxyethoxybenzyl)piperidine
15 more elements
Dependencies are inferred from the claim text.