IP Library Granted Patent US 7,105,544
Granted Patent B2
US 7,105,544 · App. 10/345,063 · Granted Sep 12, 2006

Substituted alkyl amido piperidines

Assignee: Synaptic Pharmaceutical Corporation
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Quick Facts
Patent No.
US 7,105,544
App. No.
10/345,063
Granted
Sep 12, 2006
Kind
B2
Abstract

This invention is directed to compounds which are selective antagonists for melanin concentrating hormone-1 (MCH1) receptors. The invention provides a pharmaceutical composition comprising a therapeutically effective amount of the compound of the invention and a pharmaceutically acceptable carrier. This invention provides a pharmaceutical composition made by combining a therapeutically effective amount of the compound of this invention and a pharmaceutically acceptable carrier. This invention further provides a process for making a pharmaceutical composition comprising combining a therapeutically effective amount of the compound of the invention and a pharmaceutically acceptable carrier. This invention also provides a method of reducing the body mass of a subject which comprises administering to the subject an amount of a compound of the invention effective to reduce the body mass of the subject. This invention further provides a method of treating a subject suffering from depression and/or anxiety which comprises administering to the subject an amount of a compound of the invention effective to treat the subject's depression and/or anxiety.

Claims (51)

1. A compound having the structure:

wherein each R 1 is independently hydrogen; —F; —Cl; —Br; —I; —CN; —NO 2 ; straight chained or branched C 1 –C 7 alkyl, monofluoroalkyl or polyfluoroalkyl; straight chained or branched C 2 –C 7 alkenyl; C 3 –C 7 cycloalkyl or C 5 –C 7 cycloalkenyl; aryl; heteroaryl; —N(R 5 ) 2 ; —(CH 2 ) m OR 5 ; —COR 5 ; —CO 2 R 5 ; —OCOR 5 ; —CON(R 5 ) 2 ; —N(R 5 )COR 5 ; —N(R 5 )CON(R 5 ) 2 ; —OCON(R 5 ) 2 or —N(R 5 )CO 2 R 5 ;

wherein R 2 and R 3 are independently hydrogen; —F; —Cl; —Br; —I; —CN; —(CH 2 ) m OR 5 ; —(CH 2 ) m SR 5 ; straight chained or branched C 1 –C 7 alkyl, monofluoroalkyl, polyfluoroalkyl; aryl or heteroaryl, wherein the aryl or heteroaryl may be substituted with one or more R 1 ; or

wherein R 2 and R 3 together can be —(CH 2 ) p —;

wherein R 4 is straight chained or branched C 1 –C 7 alkyl, monofluoroalkyl or polyfluoroalkyl, C 3 –C 6 cycloalkyl, —N(R 5 ) 2 or —(CH 2 ) m OR 5 ;

wherein each R 5 is independently hydrogen; aryl; heteroaryl or straight chained or branched C 1 –C 7 alkyl,

wherein the alkyl may be substituted with aryl or heteroaryl;

wherein each R 6 is independently hydrogen; straight chained or branched C 1 –C 7 alkyl;

wherein each R 7 is independently hydrogen; phenyl or straight chained or branched C 1 –C 7 alkyl, wherein the alkyl may be substituted with phenyl;

wherein each m is independently an integer from 0 to 5 inclusive;

wherein n is an integer from 1 to 5 inclusive;

wherein p is an integer from 2 to 7 inclusive;

wherein q is an integer from 0 to 2 inclusive;

wherein X is CH or N;

or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 , wherein each R 1 is independently hydrogen; straight chained or branched C 1 –C 7 alkyl; —F; —Cl; —Br; —I; —CN; —NO 2 ; straight chained or branched C 1 –C 4 alkyl or polyfluoroalkyl; —(CH 2 ) m OR 5 ; —COR 5 ; —CO 2 R 5 ; —OCOR 5 ; —CON(R 5 ) 2 ; —N(R 5 )COR 5 or —N(R 5 )CON(R 5 ) 2 ;

wherein R 2 and R 3 are independently hydrogen; —F; —Cl; —Br; —I; —CN; —(CH 2 ) m SR 5 ; straight chained or branched C 1 –C 7 alkyl; aryl or heteroaryl, wherein the aryl or heteroaryl may be substituted with one or more R 1 ; or

wherein R 2 and R 3 together can be —(CH 2 ) p —;

wherein R 4 is straight chained or branched C 1 –C 7 alkyl; C 3 –C 6 cycloalkyl; —N(R 5 ) 2 or —(CH 2 ) m OR 5 ;

wherein each R 5 is independently hydrogen or straight chained or branched C 1 –C 3 alkyl, wherein the alkyl may be substituted with phenyl;

wherein m is 0 to 3;

wherein n is 1 to 3;

wherein p is an integer from 2 to 5 inclusive;

wherein q is 0; and

wherein X is CH.

3. The compound of claim 2 , wherein the compound has the following structure:

4. The compound of claim 3 , wherein the compound has the following structure:

5. The compound of claim 4 , wherein R 1 is hydrogen; —F; —Cl; —Br; —I or straight chained or branched C 1 –C 7 alkyl; and

wherein R 2 is hydrogen or straight chained or branched C 1 –C 7 alkyl.

6. The compound of claim 5 , wherein R 4 is straight chained or branched C 1 –C 7 alkyl.

7. The compound of claim 6 , wherein the compound has the structure:

8. The compound of claim 7 , wherein the compound is selected from the group consisting of:

9. The compound of claim 7 , wherein the compound is selected from the group consisting of:

10. The compound of claim 7 , wherein the compound is selected from the group consisting of:

11. The compound of claim 4 , wherein R 4 is C 3 –C 6 cycloalkyl.

12. The compound of claim 11 , wherein the compound is selected from the group consisting of:

13. The compound of claim 2 , wherein R 2 and R 3 are independently hydrogen; —F; —Br or straight chained or branched C 1 –C 7 alkyl.

14. The compound of claim 13 , wherein R 2 and R 3 are independently hydrogen or straight chained or branched C 1 –C 7 alkyl.

15. The compound of claim 14 , wherein the compound has the structure:

16. The compound of claim 13 , wherein R 2 and R 3 are independently hydrogen; —F or —Br.

17. The compound of claim 16 , wherein the compound has the structure:

18. The compound of claim 1 , wherein the compound is enantiomerically pure.

19. The compound of claim 1 , wherein the compound is diastereomerically pure.

20. A pharmaceutical composition that comprises a therapeutically effective amount of the compound of claim 1 and a pharmaceutically acceptable carrier.

21. A pharmaceutical composition made by admixing a therapeutically effective amount of a compound of claim 1 and a pharmaceutically acceptable carrier.

22. A process for making a pharmaceutical composition comprising admixing a therapeutically effective amount of a compound of claim 1 and a pharmaceutically acceptable carrier.

23. A method of treating a subject suffering from a disorder selected from the group consisting of depression, anxiety, urge incontinence or obesity, comprising administering to the subject a therapeutically effective amount of the compound of claim 1 .

24. The method of claim 23 , wherein the therapeutically effective amount is between about 0.03 and about 300 mg.

25. The method of claim 23 , wherein the disorder is depression.

26. The method of claim 23 , wherein the disorder is anxiety.

27. The method of claim 23 , wherein the disorder is obesity.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 13, 2004
From: SYNAPTIC PHARMACEUTICAL CORPORATION
To: H. LUNDBECK A/S
Reel/Frame 015156/0196 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 27, 2003
From: MARZABADI, MOHAMMAD R.; WETZEL, JOHN M.; CHEN, CHIEN-AN; JIANG, YU; LU, KAI
To: SYNAPTIC PHARMACEUTICAL CORPORATION
Reel/Frame 014626/0496 →
Continuity (5)
Continuation In Part 1018843400 · Jul 3, 2002
Provisional Application 6034699700 · Jan 9, 2002
Provisional Application 6030309100 · Jul 5, 2001
Related Publication 20040073036A1 · Apr 15, 2004
Related Publication 20060041139A9 · Feb 23, 2006