IP Library › Granted Patent US 7,034,029

Granted Patent B2

US 7,034,029 · App. 10/759,595 · Granted Apr 25, 2006

1-aryl- or 1-alkylsulfonyl-heterocyclylbenzazoles as 5-hydroxytryptamine-6 ligands

View Patent ↗

Loading inventors, assignments & file history…

Monitor This Case

Get email alerts when status or documents change.

Order Certified Copies

Most orders are placed with the USPTO same day — all within 24 business hours.

Order via The Patent Place →

Pre-filled with this patent's details

Quick Facts

Patent No.: US 7,034,029
App. No.: 10/759,595
Granted: Apr 25, 2006
Kind: B2

External Links

USPTO Patent Center↗ Full Patent PDF↗

Abstract

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

Claims (126)

1. A compound of formula I

wherein

A is N;

X is CR 11 or N;

Y is CR 7 or N with the proviso that when X is N, then Y must be CR 7 ;

R 1 is H, C 1 –C 6 alkylcarbonyl, C 1 –C 6 alkylcarbonyloxy or an C 1 –C 6 alkyl, C 2 –C 6 alkenyl, C 2 –C 6 alkynl or cycloheteroalkyl group each optionally substituted;

R 2 , R 3 , R 4 , R 5 and R 6 are each independently H, halogen, OH or an optionally substituted C 1 –C 6 alkyl group;

R 7 and R 11 are each independently H, halogen or an C 1 –C 6 alkyl, aryl, heteroaryl or C 1 –C 6 alkoxy group each optionally substituted;

R 8 is an C 1 –C 6 alkyl, aryl or heteroaryl group each optionally substituted;

R 9 is H, halogen or an C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 alkenyl, aryl or heteroaryl group each optionally substituted;

R 10 is H, OH or an optionally substituted C 1 –C 6 alkoxy group;

m is an integer of 2;

n is 0 or an integer of 1, 2 or 3; and

represents a single bond or a double bond; or

a pharmaceutically acceptable salt thereof.

2. The compound according to claim 1 wherein X is CR 11 and Y is N.

3. The compound according to claim 1 wherein X is CR 11 and Y is CR 7 .

4. The compound according to claim 1 wherein R 8 is an optionally substituted phenyl group.

5. The compound according to claim 1 wherein R 2 , R 3 , R 4 , R 5 and R 6 are H.

6. The compound according to claim 1 wherein R 1 is H or a C 1 –C 6 alkyl or cycloheteroalkyl group each optionally substituted.

7. The compound according to claim 1 selected from the group consisting of:

1-(phenylsulfonyl)-4-piperazin-1-yl-1H-indole;

1-[(2-bromophenyl)sulfonyl]-4-piperazin-1-yl-1H-indole;

1-[(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl]-4-piperazin-1-yl-1H-indole;

1-[(3,4-dimethoxyphenyl)sulfonyl]-4-piperazin-1-yl-1H-indole;

1-[(5-chloro-3-methyl-1-benzothien-2-yl)sulfonyl]-4-piperazin-1-yl-1H-indole;

1-[(4-bromophenyl)sulfonyl]-4-piperazin-1-yl-1H-indole;

1-[(5-bromothien-2-yl)sulfonyl]-4-piperazin-1-yl-1H-indole;

1-[(4,5-dichlorothien-2-yl)sulfonyl]-4-piperazin-1-yl-1H-indole;

methyl 4-[(4-piperazin-1-yl-1H-indol-1-yl)sulfonyl]phenyl ether;

4-piperazin-1-yl-1-{[4-(trifluoromethoxy)phenyl]sulfonyl}-1H-indole;

4-(4-benzylpiperazin-1-yl)-1-(phenylsulfonyl)-1H-indole;

4-(4-benzylpiperazin-1-yl)-1-[(2-bromophenyl)sulfonyl]-1H-indole;

4-(4-benzylpiperazin-1-yl)-1-[(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl]-1H-indole;

4-(4-benzylpiperazin-1-yl)-1-[(3,4-dimethoxyphenyl)sulfonyl]-1H-indole;

4-[4-(3-methoxybenzyl)piperazin-1-yl]-1-(phenylsulfonyl)-1H-indole;

1-(phenylsulfonyl)-4-[4-(pyridin-4-ylmethyl)piperazin-1-yl]-1H-indole;

1-(phenylsulfonyl)-4-[4-(pyridin-3-ylmethyl)piperazin-1-yl]-1H-indole;

1-[(2-bromophenyl)sulfonyl]-4-[4-(3-methoxybenzyl)piperazin-1-yl]-1H-indole;

1-[(2-bromophenyl)sulfonyl]-4-[4-(pyridin-4-ylmethyl)piperazin-1-yl]-1H-indole;

1-[(2-bromophenyl)sulfonyl]-4-[4-(pyridin-3-ylmethyl)piperazin-1-yl]-1H-indole;

1-(phenylsulfonyl)-5-piperazin-1-yl-1H-indazole;

1-(phenylsulfonyl)-6-piperazin-1-yl-1H-indazole;

1-[(2-bromophenyl)sulfonyl]-6-piperazin-1-yl-1H-indazole;

1-[(4-bromophenyl)sulfonyl]-5-piperazin-1-yl-1H-indazole;

1-[(4-bromophenyl)sulfonyl]-6-piperazin-1-yl-1H-indazole;

1-[(5-bromothien-2-yl)sulfonyl]-5-piperazin-1-yl-1H-indazole;

1-[(5-bromothien-2-yl)sulfonyl]-6-piperazin-1-yl-1H-indazole;

1-[(4-fluorophenyl)sulfonyl]-5-piperazin-1-yl-1H-indazole;

1-[(4-fluorophenyl)sulfonyl]-6-piperazin-1-yl-1H-indazole;

methyl 4-[(5-piperazin-1-yl-1H-indazol-1-yl)sulfonyl]phenyl ether;

1-phenylsulfonyl-4-(4-propylpiperazin-1-yl)-1H-indazole;

1-phenylsulfonyl-4-piperazin-1-yl-1H-indazole;

1-phenylsulfonyl-4-(4-phenethylpiperazin-1-yl)-1H-indazole;

1-phenylsulfonyl-4-[4-(3-phenylpropyl)-piperazin-1-yl]-1H-indazole; and

the pharmaceutically acceptable salts thereof.

8. A pharmaceutical composition which comprises a pharmaceutically acceptable carrier and an effective amount of a compound of formula I