IP Library Granted Patent US 8,148,364
Granted Patent B2
US 8,148,364 · App. 12/122,111 · Granted Apr 3, 2012

Substituted bicyclic pyrimidone derivatives

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Quick Facts
Patent No.
US 8,148,364
App. No.
12/122,111
Granted
Apr 3, 2012
Kind
B2
Abstract

A pyrimidone derivative represented by formula (I) or a salt thereof, or a solvate thereof or a hydrate thereof: Wherein Y, Z, R1, R2, R3, R4, R5, R6, R7, n, m, and o are as described herein. The invention relates also to a medicament comprising the said derivative or a salt thereof as an active ingredient which is used for preventive and/or therapeutic treatment of a neurodegenerative disease caused by abnormal activity of GSK3β, such as Alzheimer disease.

Claims (135)

1. A compound of formula (I) or a salt thereof:

wherein:

Y represents two hydrogen atoms, a sulfur atom, an oxygen atom or a C 1-2 alkyl group and a hydrogen atom;

Z represents a bond, an oxygen atom, a nitrogen atom substituted by a hydrogen atom or a C 1-3 alkyl group, a sulfur atom, a methylene group optionally substituted by one or two groups chosen from a C 1-6 alkyl group, a hydroxyl group, a C 1-6 alkoxy group, a C 1-2 perhalogenated alkyl group or an amino group;

R1 represents a 2, 3 or 4-pyridine ring or a 2, 4 or 5-pyrimidine ring, the ring being optionally substituted by a C 1-6 alkyl group, a C 1-6 alkoxy group or a halogen atom;

R2 represents a benzene ring or a naphthalene ring; the rings being optionally substituted by 1 to 4 substituents selected from a C 1-6 alkyl group, C 3-7 cycloalkyl group, a C 3-7 cycloalkyl-C 1-6 alkyl group, a halogen atom, a C 1-2 perhalogenated alkyl group, a C 1-3 halogenated alkyl group, a hydroxyl group, a C 1-6 alkoxy group optionally substituted by a C 3-5 cycloalkyl group, a C 1-2 perhalogenated alkoxy group, a C 1-6 alkylsulfonyl group, a nitro, a cyano, an amino, a C 1-6 monoalkylamino group, a C 2-12 dialkylamino group, an acetoxy group or an aminosulfonyl group;

R3 represents a hydrogen atom, a C 1-6 alkyl group or a halogen atom;

R4 represents a hydrogen atom or a C 1-6 alkyl group;

R5 represents a hydrogen atom, a C 1-6 alkyl group optionally substituted by 1 to 4 substituents selected from a halogen atom, a phenyl group, a hydroxyl group or a C 1-6 alkoxy group;

R6 represents a hydrogen atom, a C 1-6 alkyl group or a halogen atom;

R7 represents a hydrogen atom or a C 1-6 alkyl group; and

n represents 0 to 3; m represents 0 to 1; o represents 0 to 2.

2. The compound or a salt thereof according to claim 1 , wherein R1 represents an unsubstituted 4-pyridine ring or unsubstituted 4-pyrimidine ring.

3. The compound or a salt thereof according to claim 1 , wherein:

R1 represents a 3- or 4-pyridine ring or alternatively a 4- or 5-pyrimidine ring; the rings being optionally substituted by a C 1-2 alkyl group, a C 1-2 alkoxy group or a halogen atom;

R2 represents a benzene ring or a naphthalene ring; the rings being optionally substituted by 1 to 4 substituents selected from a C 1-3 alkyl group, C 3-5 cycloalkyl group, a C 3-5 cycloalkyl-C 1-4 alkyl group, a halogen atom, a C 1-3 halogenated alkyl group, a hydroxyl group, a C 1-3 alkoxy group optionally substituted by a C 3-5 cycloalkyl group, a C 1-2 perhalogenated alkoxy group, a C 1-6 alkylsulfonyl group, a nitro, a cyano, an amino, a C 1-3 monoalkylamino group or a C 2-6 dialkylamino group;

R3 represents a hydrogen atom, a C 1-3 alkyl group or a halogen atom;

R4 represents a hydrogen atom or a C 1-3 alkyl group;

R5 represents a hydrogen atom, a C 1-3 alkoxy carbonyl group or a C 1-3 alkyl group optionally substituted by 1 to 4 substituents selected from a halogen atom, a phenyl group, a hydroxyl group or a C 1-3 alkoxy group;

R6 represents a hydrogen atom, a C 1-3 alkyl group or a halogen atom;

R7 represents a hydrogen atom or a C 1-3 alkyl group;

Y represents two hydrogen atoms, an oxygen atom or a C 1-2 alkyl group and a hydrogen atom;

Z represents a bond, an oxygen atom, a nitrogen atom substituted by a hydrogen atom or a C 1-3 alkyl group, a methylene group optionally substituted by one or two groups chosen from a C 1-3 alkyl group, a hydroxyl group, a C 1-3 alkoxy group, a C 1-2 perhalogenated alkyl group or an amino group;

n represents 0 to 3; m represents 0 or 1 and o represents 1 to 2.

4. The compound or a salt thereof according to claim 1 , wherein:

R1 represents an unsubstituted 4-pyridine ring or 4-pyrimidine ring;

R2 represents a benzene ring or a naphthalene ring; the rings being optionally substituted by 1 to 4 substituents selected from a C 1-3 alkyl group, a C 1-2 perhalogenated alkyl group, a C 3-4 cycloalkyl group, a C 3-4 cycloalkyl-C 1-3 alkyl group, a halogen atom, a hydroxyl group, a nitro, a cyano, an amino, a C 1-3 alkoxy group optionally substituted by a C 3-4 cycloalkyl group, a C 1-2 perhalogenated alkoxy group or a C 1-3 alkylsulfonyl group;

R3 represents a hydrogen atom or a halogen atom;

R4 represents a hydrogen atom;

R5 represents a hydrogen atom;

R6 represents a hydrogen atom or a C 1-6 alkyl group;

R7 represents a hydrogen atom;

Y represents two hydrogen atoms, or an oxygen atom;

Z represents a bond, an oxygen atom, a nitrogen atom substituted by a hydrogen atom;

n represents 0 to 1;

m represents 0 to 1 and o represents 1 to 2.

5. The compound or a salt thereof according to claim 1 which is selected from the group consisting of:

(+/−) N-(4-Oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) 2-Methoxy-N-(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) N-(4-Oxo-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)-2-phenylacetamide;

(+/−) Phenyl(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)carbamate;

(+/−) N-(4-Fluorophenyl)-N′-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)urea;

(+/−) N-(4-Oxo-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)-N′-phenylurea;

(+/−) 9-[(2-Methoxybenzyl)amino]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin -4-one;

(+/−) 3-Fluoro-N-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) 4-Isopropoxy-N-(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) 2-Chloro-N-(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) 4-Fluoro-N-(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) 3-Cyano-N-(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) 2-Chloro-5-fluoro-N-(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin -9-yl)benzamide;

(+/−) 2-Methoxy-N-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) 4-Fluoro-N-(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)-2-(trifluoromethyl)benzamide;

(+/−) 4-Methoxy-N-(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)-3-(trifluoromethyl)benzamide;

(+/−) N-(4-Oxo-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)-2-(trifluoromethyl)benzamide;

(+/−) 2-Chloro-4-fluoro-5-nitro-N-(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) N-(4-Oxo-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)-2-naphthamide;

(+/−) 3-Chloro-N-(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) 2,6-Dimethoxy-N-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin -9-yl)benzamide;

(+/−) 3-Methoxy-N-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) 2-Fluoro-6-methoxy-N-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) 4-Fluoro-2-methoxy-N-(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) 4-Chloro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−)2-Ethoxy-N-(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) N-(3-Bromo-4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)-2-methoxybenzamide;

(+/−) 4-Amino-5-chloro-2-methoxy-N-(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) N-(4-Oxo-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)-2-(trifluoromethoxy)benzamide;

(+/−) 2-Isopropoxy-N-(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) 2-(Cyclopropylmethoxy)-N-(4-oxo-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) 4-Amino-5-chloro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H -pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) 4-Fluoro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) 2-(Cyclopropylmethoxy)-N-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) N-(4-Oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)-2-naphthamide;

(+/−) 3-Chloro-N-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) 5-Chloro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) 4-Amino-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) 2-Methoxy-N-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl) -4-trifluoromethyl-benzamide;

(+/−) 5-(Ethylsulfonyl)-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) 2,3-Dimethoxy-N-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin -9-yl)benzamide;

(−) 4-Chloro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+) 4-Chloro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) 5-Bromo-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) 2- {[(4-Oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)amino]carbonyl}phenyl acetate;

(+/−) 2-Hydroxy-N-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) 4-Chloro-2-methoxy-N-(9-methyl-4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H -pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+) 4-Chloro-2-methoxy-N-(9-methyl-4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(−) 4-Chloro-2-methoxy-N-(9-methyl-4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) 4-Chloro-2-methoxy-N-methyl-N-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H -pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+) 4-Fluoro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(−) 4-Fluoro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)benzamide;

(+/−) 5-Chloro-2-methoxy-N-(9-methyl-4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H -pyrido[1,2-a]pyrimidin-9-yl)-benzamide;

(+/−) 4-Fluoro-2-methoxy-N-(9-methyl-4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H -pyrido[1,2-a]pyrimidin-9-yl)-benzamide;

(+/−) 4-Amino-5-chloro-2-methoxy-N-(9-methyl-4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H -pyrido[1,2-a]pyrimidin-9-yl)-benzamide;

(+/−) 2-Methoxy-N-(9-methyl-4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)-4-trifluoromethyl-benzamide;

(+/−) 2-Fluoro-6-methoxy-N-(9-methyl-4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H -pyrido[1,2-a]pyrimidin-9-yl)-benzamide;

(+/−) 2-Methoxy-N-(9-methyl-4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)-benzamide;

(+/−) 5-Bromo-2-methoxy-N-(9-methyl-4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H -pyrido[1,2-a]pyrimidin-9-yl)-benzamide;

(+/−)-4-Dimethylamino-2-methoxy-N-(9-methyl-4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H -pyrido[1,2-a]pyrimidin-9-yl)-benzamide;

(+/−)-2,4-Dimethoxy-N-(9-methyl-4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-9-yl)-benzamide;

(+/−) 4-Chloro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-8-yl)-benzamide;

(+/−) 4-Fluoro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-8-yl)-benzamide;

(+/−) 4-Amino-5-chloro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-8-yl)-benzamide;

(+/−) 5-Chloro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-8-yl)-benzamide;

(+/−) 4-Chloro-2-methoxy-N-(4-oxo-2-pyridin-4-yl-4,6,7,8-tetrahydro-pyrrolo [1,2-a]pyrimidin -8-yl)-benzamide;

(+/−) 4-Fluoro-2-methoxy-N-(4-oxo-2-pyridin-4-yl-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidin-8-y1)-benzamide;

(+/−) 4-Chloro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-10-yl)benzamide;

(+/−) 4-Fluoro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-10-yl)benzamide;

(+/−) 5-Chloro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydropyrimido[1,2-a] azepin- 10-yl)benzamide;

(+/−) 4-Amino-5-chloro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-10-yl)benzamide;

(+/−) 4-Amino-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-10-yl)benzamide;

(+/−) 2-Methoxy-N-(4-oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-10-yl)benzamide;

(+/−) 5-(Aminosulfonyl)-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-10-yl)benzamide;

(+/−) 2-Hydroxy-N-(4-oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-10-yl)benzamide;

(+/−) 5-Bromo-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-10-yl)benzamide;

(+/−) 2,4-Dimethoxy-N-(4-oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydropyrimido [1,2-a]azepin -10-yl)benzamide;

(+/−) 2-{[(4-Oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-10-yl)amino]carbonyl}phenyl acetate;

(+/−) 2,3-Dimethoxy-N-(4-oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydropyrimido [1,2-a]azepin -10-yl)benzamide;

(+/−) 2-Methoxy-N-(4-oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-10-yl)-5-(trifluoromethoxy)benzamide;

(+/−) 2,5-Dimethoxy-N-(4-oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydropyrimido [1,2-a]azepin -10-yl)benzamide;

(+) 4-Fluoro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-10-yl)benzamide;

(−) 4-Fluoro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-10-yl)benzamide;

(+/−) 4-Chloro-2-methoxy-N-(4-oxo-2-pyridin-4-yl-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-10-yl)benzamide;

(+/−) 5-Bromo-2-methoxy-N-(4-oxo-2-pyridin-4-yl-4,6,7,8,9,1 0-hexahydropyrimido [1,2-a]azepin-10-yl)benzamide;

(+/−) 4-Fluoro-2-methoxy-N-(4-oxo-2-pyridin-4-yl-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-10-yl)benzamide;

(+/−) 2-Methoxy-N-(4-oxo-2-pyridin-4-yl-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-10-yl)benzamide;

(+/−) 5-Chloro-2-methoxy-N-(4-oxo-2-pyridin-4-yl-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-10-yl)benzamide;

(+/−) 4-Amino-2-methoxy-N-(4-oxo-2-pyridin-4-yl-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-10-yl)benzamide;

(+/−) 2- {[(4-Oxo-2-pyridin-4-yl-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-10-yl)amino]carbonyl}phenyl acetate;

(+/−) 2,4-Dimethoxy-N-(4-oxo-2-pyridin-4-yl-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-10-yl)benzamide;

(+) 4-chloro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-10-yl)benzamide; and

(−) 4-chloro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-10-yl)benzamide.

6. A pharmaceutical composition comprising a compound of formula (I) or a pharmaceutically acceptable salt thereof according to claim 1 in combination with at least one pharmaceutically acceptable excipient.

7. A pharmaceutical composition comprising a compound of formula (I) or a pharmaceutically acceptable salt thereof according to claim 2 in combination with at least one pharmaceutically acceptable excipient.

8. A pharmaceutical composition comprising a compound of formula (I) or a pharmaceutically acceptable salt thereof according to claim 3 in combination with at least one pharmaceutically acceptable excipient.

9. A pharmaceutical composition comprising a compound of formula (I) or a pharmaceutically acceptable salt thereof according to claim 4 in combination with at least one pharmaceutically acceptable excipient.

10. A pharmaceutical composition comprising a compound of formula (I) or a pharmaceutically acceptable salt thereof according to claim 5 in combination with at least one pharmaceutically acceptable excipient.

Assignments (2)
CHANGE OF NAME Recorded Jun 20, 2012
From: SANOFI-AVENTIS
To: SANOFI
Reel/Frame 028413/0927 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 25, 2008
From: CHEREZE, NATHALIE; LOCHEAD, ALISTAIR; SAADY, MOURAD; SLOWINSKI, FRANCK; YAICHE, PHILIPPE
To: SANOFI-AVENTIS; MITSUBISHI TANABE PHARMA CORPORATION
Reel/Frame 021585/0247 →