IP Library › Granted Patent US 7,557,098
Granted Patent B2
US 7,557,098 · App. 11/841,686 · Granted Jul 7, 2009

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

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Quick Facts
Patent No.
US 7,557,098
App. No.
11/841,686
Granted
Jul 7, 2009
Kind
B2
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 (51)

1. A compound of formula I

wherein

A is N;

X is N;

Y is CH;

R 1 is H or C 1 -C 4 alkyl substituted with 0-3 of halogen, hydroxyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy or combinations thereof;

R 2 , R 3 , R 4 , R 5 and R 6 are each independently H, halogen, OH or a C 1 -C 6 alkyl group;

R 8 is phenyl or naphthyl each substituted with 0-3 of halogen, hydroxyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy or combinations thereof;

R 9 is H;

m is an integer of 3;

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

---- represents a single bond; or

a pharmaceutically acceptable salt thereof.

2. A compound of the following formula:

wherein

R 1 is H or C 1 -C 4 alkyl substituted with 0-3 of halogen, hydroxyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy or combinations thereof;

R 8 is phenyl or naphthyl each substituted with 0-3 of halogen, hydroxyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy or combinations thereof; or

a pharmaceutically acceptable salt thereof.

3. The compound according to claim 2 , wherein R 1 is H or C 1 -C 4 alkyl.

4. The compound according to claim 3 , wherein R 1 is H.

5. The compound according to claim 2 , wherein R 8 is phenyl substituted with 0-3 of halogen, hydroxyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy or combinations thereof.

6. The compound according to claim 2 , wherein the compound is selected from:

4-(homopiperazin-1yl)-1-(phenylsulfonyl)-benzimidazole or a pharmaceutically acceptable salt thereof.

7. A method for the treatment of a disorder of the central nervous system related to or affected by the 5-HT6 receptor selected from anxiety disorder, schizophrenia, depression, or attention deficit disorder in a patient in need thereof which comprises administering to said patient a therapeutically effective amount of a compound of the following formula:

wherein

R 1 is H or C 1 -C 4 alkyl substituted with 0-3 of halogen, hydroxyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy or combinations thereof;

R 8 is phenyl or naphthyl each substituted with 0-3 of halogen, hydroxyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy or combinations thereof; or

a pharmaceutically acceptable salt thereof.

8. The method according to claim 7 , wherein said disorder is a anxiety disorder.

9. The method according to claim 7 , wherein said disorder is schizophrenia.

10. The method according to claim 7 , wherein said disorder is an attention deficit disorder.

11. The method according to claim 7 , wherein said disorder is depression.

12. A pharmaceutical composition which comprises a pharmaceutically acceptable carrier and an effective amount of a compound of the following formula:

wherein

R 1 is H or C 1 -C 4 alkyl substituted with 0-3 of halogen, hydroxyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy or combinations thereof;

R 8 is phenyl or naphthyl each substituted with 0-3 of halogen, hydroxyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy or combinations thereof; or

a pharmaceutically acceptable salt thereof.

13. The composition according to claim 12 , wherein R 1 is H or C 1 -C 4 alkyl.

14. The composition according to claim 13 , wherein R 1 is H.

15. The composition according to claim 12 , wherein R 8 is phenyl substituted with 0-3 of halogen, hydroxyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy or combinations thereof.

16. The composition according to claim 12 , wherein the compound is selected from:

4-(homopiperazin-1yl)-1-(phenylsulfonyl)-benzimidazole or a pharmaceutically acceptable salt thereof.

17. A method for the preparation of a compound of the following formula:

wherein

R 1 is H or C 1 -C 4 alkyl substituted with 0-3 of halogen, hydroxyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy or combinations thereof;

R 8 is phenyl or naphthyl each substituted with 0-3 of halogen, hydroxyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy or combinations thereof; or a pharmaceutically acceptable salt thereof;

said method which comprises reacting a compound of the following formula:

with a compound R 1 -Hal, wherein R 1 and R 8 are as defined hereinabove and Hal is Cl, Br or I.

18. The method according to claim 7 , wherein R 1 is H or C 1 -C 4 alkyl.

19. The method according to claim 7 , wherein R 1 is H.

20. The method according to claim 7 , wherein R 8 is phenyl substituted with 0-3 of halogen, hydroxyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy or combinations thereof.