# US 7,608,717 B2 · Sulfonyldihydroimidazopyridinone compounds as 5-hydroxytryptamine-6 ligands

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- Number: US 7,608,717 B2
- Document ID: US7608717B2
- Status: Granted
- Kind: B2
- Application number: 11/901,892
- Filed: 2007-09-19
- Published: 2008-03-20
- Granted: 2009-10-27
- Earliest claimed: 2003-07-23
- Assignees: Wyeth
- Inventors: Derek Cecil Cole; Ronald Charles Bernotas
- Web page: https://patentgrep.com/patent/US7608717B2

## CPC

- C07D 471/04: Ortho-condensed systems
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A61P 25/22: Anxiolytics
- 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 25/30: for treating abuse or dependence
- A61P 25/32: Alcohol-abuse
- A61P 25/34: Tobacco-abuse
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention provides a compound of formula I and the use thereof in the therapeutic treatment of a central nervous system disorder related to or affected by the 5-HT6 receptor.

## Claims

### Claim 1

A pharmaceutical composition which comprises a pharmaceutically acceptable carrier and an effective amount of a compound of formula I
wherein
Q is —(CR2R3)n—NR4R5,
W is N;
X is CR7;
Y is CR8;
Z is CR9;
R is an optionally substituted aryl or heteroaryl group or an optionally substituted 8-membered bicyclic ring system having a N atom at the bridgehead and containing 2 additional heteroatoms selected from N or S wherein said ring system is an imidazothiazole ring;
R7, R8 and R9 are each independently H;
R2 and R3 are each independently H or an optionally substituted C1-C6alkyl group;
n is an integer of 2, 3, 4 or 5;
p is 0 or an integer of 1 or 2
R4 and R5 are each independently H or a C1-C6alkyl group;
R6 is H or an optionally substituted C1-C6alkyl group; and
represents a single bond or a double bond; or
a stereoisomer thereof or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The composition according to claim 1 having a formula I compound wherein R is an optionally substituted phenyl, naphthyl, thienyl or imidazo[2,1-b][1,3]-thiazolyl group.

### Claim 3 (depends on 2)

The composition according to claim 2 having a formula I compound wherein Q is —CH2CH2—NR4R5; 4-piperidinyl or 4-(1,2,3,6-tetrahydropyridinyl).

### Claim 4 (depends on 2)

The composition according to claim 2 having a formula I compound wherein R2 and R3 are each H.

### Claim 5 (depends on 1)

The composition according to claim 1 having a formula I compound selected from the group consisting of:
3-[2-(dimethylamino)ethyl]-1-[(3-fluorophenyl)sulfonyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one;
1-[(2-chloroimidazo[2,1-b]pyridin-3-yl)sulfonyl]-3-[2(dimethylamino)ethyl]1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one;
1-[(2,6-dichloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl]-3-[2(dimethylamino)ethyl]1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one
1-[(3-bromophenyl)sulfonyl]3-[2(dimethylamino)ethyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one;
3-[2-(dimethylamino)ethyl]1-(thien-2-ylsulfonyl)-1,3-dihydro-2H-imidazo[4,5b]pyridin-2-one;
3-(2-aminoethyl)-1-(phenylsulfonyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one;
3-(2-aminoethyl)-1-[(3-chlorophenyl)sulfonyl]-1,3-dihydro-2H-imidazo[4,5b]pyridin-2-one;
3-(2-aminoethyl)-1-[(5-chlorothien-2-yl)sulfonyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one;
3-(2-aminoethyl)-1-[(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one;
3-(2-aminoethyl)-1-(2-naphthylsulfonyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one;
3-(2-aminoethyl)-1-[(3-methoxyphenyl)sulfonyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one;
3-(2-aminoethyl)-1-[(2-fluorophenyl)sulfonyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one
3-(2-aminoethyl)-1-[(3-fluorophenyl)sulfonyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one;
3-(2-aminoethyl)-1-[(2-chlorophenyl)sulfonyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one;
3-(2-aminoethyl)-1-[(4-chlorophenyl)sulfonyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one;
3-(2-aminoethyl)-1-[(2,3-dichlorophenyl)sulfonyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one
3-(2-aminoethyl)-1-[3-bromophenyl)sulfonyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one
3-(2-aminoethyl)-1-[(5-bromothien-2-yl)sulfonyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one;
3-(2-aminoethyl)-1-[(2,5-dichlorothien-3-yl)sulfonyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one;
1-(2-aminoethyl)-3-phenylsulfonyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one
1-(2-aminoethyl)-3-[(naphth-1-yl)sulfonyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one;
1-[2-(dimethylamino)ethyl]-3-phenylsulfonyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one;
3-phenylsulfonyl-1-(pyrrolidin-3-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one;
a stereoisomer thereof; and
a pharmaceutically acceptable salt thereof.

### Claim 6 (depends on 1)

The composition according to claim 1 having a formula I compound wherein Q is —(CR2R3)n—NR4R5.

### Claim 7 (depends on 6)

The composition according to claim 6 having a formula I compound wherein R2 and R3 are each H; and n is an integer of 1.

### Claim 8 (depends on 1)

The composition according to claim 1 having a formula I compound wherein Q is

### Claim 9 (depends on 8)

The composition according to claim 8 having a formula I compound wherein R6 is H; and p is an integer of 1.