# US 7,608,624 B2 · 1-[alkyl], 1-[(heteroaryl)alkyl] and 1-[(aryl)alkyl]-7-pyridinyl-imidazo[1,2-a]pyrimidin-5(1h)-one derivatives

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- Number: US 7,608,624 B2
- Document ID: US7608624B2
- Status: Granted
- Kind: B2
- Application number: 11/370,451
- Filed: 2006-03-08
- Published: 2006-07-06
- Granted: 2009-10-27
- Earliest claimed: 2000-09-01
- Assignees: Sanofi-Aventis; Mitsubishi Pharma Corporation Tokyo
- Inventors: Alistair Lochead; Severine Marguerie; Mourad Saady; Philippe Yaiche
- Web page: https://patentgrep.com/patent/US7608624B2

## CPC

- A61K 31/519: ortho- or peri-condensed with heterocyclic rings
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 17/14: for baldness or alopecia
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/02: for peripheral neuropathies
- A61P 25/16: Anti-Parkinson drugs
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A61P 25/24: Antidepressants
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 27/02: Ophthalmic agents
- A61P 27/06: Antiglaucoma agents or miotics
- A61P 35/00: Antineoplastic agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 487/04: Ortho-condensed systems
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The invention relates to a method of treatment of a variety of neurodegenerative diseases such as Alzheimer disease using a imidazo[1,2-a]pyrimidone derivative represented by formula (I) or a salt thereof: Wherein X, R1, R2, and n are as defined herein.

## Claims

### Claim 1

A method for the treatment of a disease selected from the group consisting of non-insulin dependent diabetes, and Alzheimer's disease, comprising administering to a patient in need of such treatment an effective amount of a compound represented by formula (I) or a salt thereof:
wherein:
X represents a bond, an ethenylene group, an ethynylene group, a methylene group optionally substituted by one or two groups selected from a C1-6 alkyl group, a hydroxy group and a C1-4 alkoxy group, a carbonyl group, an oxygen atom, a sulfur atom, a sulfonyl group, a sulfoxide group or a nitrogen atom being optionally substituted by a C1-6 alkyl group;
R1 represents a 2, 3 or 4-pyridyl group optionally substituted by a C1-4 alkyl group, C1-4 alkoxy group or a halogen atom;
R2 represents a C1-6 alkyl group, a C1-2 perhalogenated alkyl group, a C1-3 halogenated alkyl group, a benzyl group, a phenyl ring, a naphthyl ring, 5,6,7,8-tetrahydronaphthyl ring, a pyridyl ring, an indole ring, a pyrrole ring, a thiophene ring, a furan ring or an imidazole ring, the benzyl group and the rings being optionally substituted by 1 to 4 substituents selected from a C1-6 alkyl group, a phenyl ring, a halogen atom, a C1-2 perhalogenated alkyl group, a C1-3 halogenated alkyl group, a hydroxyl group, a C1-4 alkoxy group, a nitro, a cyano, an amino, a C1-6 monoalkylamino group or a C2-10 dialkylamino group;
and n represents 0 to 3.

### Claim 2 (depends on 1)

The method as set forth in claim 1 wherein the compound or a salt thereof is having R1 an unsubstituted 4-pyridyl group or 3-pyridyl group.

### Claim 3 (depends on 1)

The method as set forth in claim 1 wherein the compound or a salt thereof is having R2 a trifluoromethyl group, a 2,2,2-trifluoroethyl, a phenyl ring, a naphthyl ring, a 5,6,7,8-tetrahydronaphthyl ring or an indole ring, the rings being optionally substituted.

### Claim 4 (depends on 2)

The method as set forth in claim 2 wherein the compound or a salt thereof is having R2 a trifluoromethyl group, a 2,2,2-trifluoroethyl, a phenyl ring, a naphthyl ring, a 5,6,7,8-tetrahydronaphthyl ring or an indole ring, the rings being optionally substituted.

### Claim 5 (depends on 1)

The method as set forth in claim 1 wherein the compound is selected from the group consisting of:
1-[2-(phenyl)ethyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5(1H)-one,
1-[2-(1H-indol-3-yl)ethyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5(1H)-one,
1-[3-(phenyl)propyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5(1H)-one,
1-[3-(1H-indol-3-yl)propyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5(1H)-one,
1-[3-(4-methoxyphenyl)propyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5(1H)-one,
1-[2-(phenoxy)ethyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5(1H)-one,
1-[3-(2-methoxyphenyl)propyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5(1H)-one,
1-[3-(2-chlorophenyl)propyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5(1H)-one,
1-[3-(2-methylphenyl)propyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5(1H)-one,
1-[2-(phenylthio)ethyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5(1H)-one,
1-[3-(2,5-dimethoxyphenyl)propyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5(1H)-one,
1-[3-(4-methylphenyl)propyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5(1H)-one,
1-[3-(4-trifluoromethylphenyl)propyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5(1H)-one,
1-[4-(phenyl)butyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5 (1H)-one,
1-[3-(phenyl)propyl]-7-pyridin-3-ylimidazo[1,2-a]pyrimidin-5 (1H)-one,
1-(2-phenyl-2-oxo-ethyl)-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5 (1H)-one,
(S)-1-(4,4,4-trifluoro-3-hydroxybutyl)-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5(1H)-one,
1-(4,4,4-trifluorobut-2-enyl)-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5 (1H)-one,
(R)-1-(4,4,4-trifluoro-3-hydroxybutyl)-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5(1H)-one,
1-(4,4,4-trifluorobut-1-enyl)-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5 (1H)-one,
1-[2-(2,5-dimethoxyphenyl)ethyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5 (1H)-one,
1-[3-(2-fluorophenyl)propyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5 (1H)-one,
1-(3-phenyl-3-oxo-propyl)-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5 (1H)-one,
1-[3-(pyridin-3-yl)propyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5 (1H)-one,
(S)-1-(4,4,4-trifluoro-butyl)-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5 (1H)-one,
1-[2-(2-methoxyphenyl)ethyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5 (1H)-one,
1-[2-(5,5, 8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)-2-oxo-ethyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5(1H)-one,
1-[2-(4-phenyl-phenyl)-2-oxo-ethyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5(1H)-one,
1-[2-(3-methoxyphenyl)-2-oxo-ethyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5(1H)-one,
1-[2-(2-naphthyl)-2-oxo-ethyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5(1H)-one,
1-[2-(4-methylphenyl)-2-oxo-ethyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5(1H)-one,
1-[2-(4-fluorophenyl)-2-oxo-ethyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5 (1H)-one,
1-[2-(4-chlorophenyl)-2-oxo-ethyl]-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5(1H)-one,
1-(2-(4-fluorophenyl)-2-hydroxyethyl)-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5(1H)-one,
1-(2-naphthyl-2-hydroxyethyl)-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5 (1H)-one, and
1-(2-(1,1,4,4,-tetramethyl-1,2,3,4-tetrahydronaphth-6-yl)-2-hydroxyethyl)-7-pyridin-4-ylimidazo[1,2-a]pyrimidin-5 (1H)-one,
or a salt thereof.

### Claim 6 (depends on 1)

The method as set forth in claim 1 wherein the disease is Alzheimer's disease.

### Claim 7 (depends on 1)

The method as set forth in claim 1 wherein the disease is non-insulin dependent diabetes.