IP Library Granted Patent US 7,566,720
Granted Patent B2
US 7,566,720 · App. 11/841,285 · Granted Jul 28, 2009

2-pyridinyl-6,7,8,9-tetrahydropyrimido[1,2-a] pyrimidin-4-one and 7-pyridinyl-2,3-dihydroimidazo[1,2-a] pyrimidin-5(1

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Quick Facts
Patent No.
US 7,566,720
App. No.
11/841,285
Granted
Jul 28, 2009
Kind
B2
Abstract

The invention relates to therapeutic uses of a pyrimidone derivative represented by formula (I) or a salt thereof: Wherein X, Y, R1, R2, m and n are as defined herein. Specifically, a medicament comprising the said derivative or a salt thereof as an active ingredient is used for preventive and/or therapeutic treatment of a neurodegenerative diseases caused by abnormal activity of GSK3β such as Alzheimer's disease.

Claims (144)

1. A method of inhibiting the activity of glycogen synthase kinase 3-beta (GSK3-β), which comprises administering to a patient in need of said inhibition a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt thereof:

wherein:

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

Y represents a bond, an ethenylene group, an ethynylene group, a 1,2-cyclopropylene, an oxygen atom, a sulfur atom, a sulfonyl group, a sulfinyl group, a carbonyl group, an NH group being optionally substituted by a C 1-6 alkyl group, a phenyl or a benzyl group; or a methylene group optionally substituted by one or two groups chosen from a C 1-6 alkyl group, a phenyl group, a hydroxyl group and a C 1-4 alkoxy group;

R1 represents a 2, 3 or 4-pyridyl group optionally substituted by a C 3-6 cycloalkyl group, a C 1-4 alkyl group, a C 1-4 alkoxy group, a benzyl group or a halogen atom;

when Y represents a bond, a 1,2-cyclopropylene, a methylene group optionally substituted or a carbonyl group then R2 represents a C 1-6 alkyl group, a C 3-6 cycloalkyl group, a C 1-4 alkylthio group, a C 1-4 alkoxy group, a perhalogenated alkyl group, a C 1-3 halogenated alkyl group, a 5,6,7,8-tetrahydronaphthyl ring, a naphthyl ring, a phenylthio group, a benzyl group, a phenyl ring, a pyridyl ring, an indole ring, a pyrrole ring, a thiophene ring, a furan ring or an imidazole ring; the benzyl group or the rings being optionally substituted by 1 to 4 substituents selected from a C 1-6 alkyl group, a methylenedioxy group, a halogen atom, a C 1-2 perhalogenated alkyl group, a C 1-3 halogenated alkyl group, a hydroxyl group, a C 1-4 alkoxy group, a nitro, a cyano, an amino, a C 1-5 monoalkylamino group, a C 2-10 dialkyl-amino group, a C 1-6 alkylcarbonylamino group, a C 6,10 arylcarbonylamino group, a C 1-4 alkyl-sulfonyl group, C 1-4 alkylsulfonyloxy group and a phenyl group;

when Y represents an ethenylene group, an ethynylene group, an oxygen atom, a sulfur atom, a sulfonyl group, a sulfinyl group or an NH group being optionally substituted then R2 represents a C 1-6 alkyl group, a C 3-6 cycloalkyl group, a C 1-2 perhalogenated alkyl group, a C 1-3 halogenated alkyl group, a naphthyl ring, a 5,6,7,8-tetrahydronaphthyl ring, a benzyl group, a phenyl ring, a pyridyl ring, an indole ring, a pyrrole ring, a thiophene ring, a furan ring or an imidazole ring; the benzyl group or the rings being optionally substituted by 1 to 4 substituents selected from a C 1-6 alkyl group, a methylenedioxy group, a halogen atom, a C 1-2 perhalogenated alkyl group, a C 1-3 halogenated alkyl group, a hydroxyl group, a C 1-4 alkoxy group, a nitro, a cyano, an amino, a C 1-5 monoalkylamino group, a C 2-10 dialkylamino group, a C 1-6 alkylcarbonylamino group, a C 6,10 arylcarbonylamino group, a C 1-4 alkylsulfonyl group, a C 1-4 alkylsulfonyloxy group and a phenyl group;

m represents 1 or 2;

and n represents 0 to 3.

2. The method according to claim 1 , wherein in said compound of formula I, R1 represents an unsubstituted 4-pyridyl group.

3. The method according to claim 2 , wherein in said compound according to formula I, R2 represents a C 1-4 alkyl group, C 1-2 alkylthio group, C 1-2 alkoxy group, a trifluoromethyl group, a C 5-6 cycloalkyl group, a naphthyl ring, a 5,6,7,8-tetrahydronaphthyl ring, a phenyl ring, a pyridyl ring, an indole ring, a thiophene ring; the rings being optionally substituted by 1 to 4 substituents.

4. The method according to claim 1 , wherein said compound of formula I is selected from the group consisting of:

9-[2-(1H-indol-3-yl)ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-(3-phenylpropyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-(2-phenylethyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3-(1H-indol-3-yl)propyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-(2-phenoxyethyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3-(3,4-methylenedioxyphenyl)propyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(2-methoxyphenyl)ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(4-fluorophenoxyethyl)]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3-(2-chlorophenyl)propyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3-(4-methylphenyl)propyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3-(4-trifluoromethylphenyl)propyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-(4-phenylbutyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3-(2-methylphenyl)propyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(2,5-dimethoxyphenyl)ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(2-methoxyphenoxy)ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3-(2-methoxyphenyl)propyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(4-chlorophenoxy)ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3-(3-methoxyphenyl)propyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-(2-methoxyphenylmethyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-phenylthioethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3-(3,4-dimethoxyphenyl)propyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3-(3,4,5-trimethoxyphenyl)propyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(phenylsulfonyl)ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3-(3,4-fluorophenyl)propyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3-phenylpropanoyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3-(4-fluorophenyl)propyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3-(2,5-dimethoxyphenyl)propyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3-(2,4-dichlorophenyl)propyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3-(3-fluorophenyl)propyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3-(4-chlorophenyl)propyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-(3,3-dimethylbutyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-(2-cyclohexylethyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3-(pyridin-3-yl)propyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(4-methylsulfonyloxyphenyl)ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-(3-methylbutyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-(3,3-diphenylpropyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[4-(4-methoxyphenyl)butyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[4-(4-nitrophenyl)butyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3-(2-fluorophenyl)propyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-(3-phenylprop-2-ynyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-(3-phenylbutyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(2-chloro-4-fluorophenyl)ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-(2-phenyl-2-oxo-ethyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-(3-benzyloxypropyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-(3-methylthiobutyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(1-naphthyl)ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(thiophen-2-yl)ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(3-trifluoromethylphenyl)ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[(2-(thiophen-3-yl)ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(2-bromophenyl)ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-(4-cyclohexylbutyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(3-bromophenyl)ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(4-ter-butylphenyl)ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(2,4,6-trimethylphenyl)ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(4-ethoxyphenyl)ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(2-chloro-6-fluorophenyl)ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(3-chlorophenyl)ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(3-methylphenyl)ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-(3-methoxybutyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-(3-cyclohexylpropyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3-[di(phenylmethyl)amino]propyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-(2-phenyl-cyclopropylmethyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-(3-phenylprop-2-enyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-(2-phenyl-2-hydroxypropyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3-(4-fluorophenyl)-3-oxo-propyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-(4,4,4-trifluorobutyl)-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3-phenyl-3-oxo-propyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3-phenyl-3-hydroxypropyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3,3,3-trifluoro-2-hydroxypropyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

(R)-9-[2-phenyl-2-hydroxyethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

(S)-9-[2-phenyl-2-hydroxyethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[3-(4-fluorophenyl)-3-hydroxypropyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[1-methyl-2-oxo-2-phenyl-ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[1-methyl-2-hydroxy-2-phenyl-ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(4-methylphenyl)-2-oxo-ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(4-chlorophenyl)-2-oxo-ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(4-fluorophenyl)-2-oxo-ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(4-phenylphenyl)-2-oxo-ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(3-methoxyphenyl)-2-oxo-ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(2-naphthyl)-2-oxo-ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronapht-2-yl)-2-oxo-ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(3-methoxy-4,5-methylendioxyphenyl)-2-oxo-1-methylethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(4-methylphenyl)-2-hydroxy-ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(1,1,4,4,-tetramethyl-1,2,3,4-tetrahydronapht-6-yl)-2-hydroxy-ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(phenylamino)-2-oxo-ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(3-chlorophenyl)-2-oxo-ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(3-chlorophenyl)-2-hydroxy-ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

9-[2-(3-fluorophenyl)-2-oxo-ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one; and

9-[2-(3-fluorophenyl)-2-hydroxy-ethyl]-2-pyridin-4-yl-6,7,8,9-tetrahydro-4H-pyrimido[1,2-a]pyrimidin-4-one;

or a pharmaceutically acceptable salt thereof.

5. The method according to claim 1 , wherein said compound of formula I is selected from the group consisting of:

1-[2-(1H-Indol-3-yl)ethyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[3-(phenyl)propyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5 (1H)-one,

1-[3-(1H-indol-3-yl)propyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[2-(phenyl)ethyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5 (1H)-one,

1-[3-(2-methylphenyl)propyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[3-(2-methoxyphenyl)propyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-(4-phenylbutyl)-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5 (1H)-one,

1-[3-(2-chlorophenyl)propyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[3-(2,5-dimethoxyphenyl)propyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[3-(4-methylphenyl)propyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[3-(3-methoxyphenyl)propyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[3-(3,4,5-trimethoxyphenyl)propyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[2-(4-fluorophenoxy)ethyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[2-(4-chlorophenoxy)ethyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[3-(2,4-dichlorophenyl)propyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[2-(phenylthio)ethyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-(3-phenylpropanoyl)-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[3-(4-fluorophenyl)propyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[3-(3,4-difluorophenyl)propyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-(2-cyclohexylethyl)-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5 (1H)-one,

1-(3,3-dimethylbutyl)-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5 (1H)-one,

1-(2-phenyl-2-oxo-ethyl)-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

(S)-1-(4,4,4-trifluoro-3-hydroxybutyl)-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-(4,4,4-trifluoro-but-2-en-1-yl)-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[3-(4-trifluoromethylphenyl)propyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

(R)-1-(4,4,4-trifluoro-3-hydroxybutyl)-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[3-(2-fluorophenyl)propyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[2-(2,5-dimethoxy-phenyl)ethyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[2-(phenylsulfonyl)ethyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-(4,4,4-trifluorobutyl)-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[3-(pyridin-3-yl)propyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[2-(2-methoxy)ethyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[2-(4-chloro-phenyl)-2-oxo-ethyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[2-(napht-2-yl)-2-oxo-ethyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[2-(3-methoxy-4,5-methylendioxy-phenyl)-2-oxo-1-methyl-ethyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5 (1H)-one,

1-[2-(4-phenyl-phenyl)-2-oxo-ethyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[2-(4-methylphenyl)-2-oxo-ethyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronapht-2-yl)-2-oxo-ethyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one,

1-[2-(4-fluorophenyl)-2-oxo-ethyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one, and

1-[2-(3-methoxyphenyl)-2-oxo-ethyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one;

or a pharmaceutically acceptable salt thereof.

Assignments (3)
CHANGE OF NAME Recorded Jun 20, 2012
From: SANOFI-AVENTIS
To: SANOFI
Reel/Frame 028413/0927 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 15, 2009
From: GARCIA, ANTONIO ALMARIO; GALLET, THIERRY; LI, ADRIEN TAK; LOCHEAD, ALISTAIR; MARGUERIE, SEVERINE; NEDELEC, ALAIN; SAADY, MOURAD; YAICHE, PHILIPPE
To: SANOFI-SYNTHELABO; MITSUBISHI PHARMA CORPORATION
Reel/Frame 022825/0347 →
CHANGE OF NAME Recorded Jun 15, 2009
From: SANOFI-SYNTHELABO
To: SANOFI-AVENTIS
Reel/Frame 022828/0049 →