IP Library › Patent Application 10541991
Patent Application
App. No. 10/541,991

Substituted alkyl amido piperidines

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Patent No.
US None
App. No.
10/541,991
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 (61)

1 - 38 . (canceled)

39 . A method of treating a subject suffering from depression comprising administering to the subject a therapeutically effective amount of 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 is hydrogen; —F; —Cl; —Br; —I; —CN; —(CH 2 ) m OR 5 ; —(CH 2 ) m SR 5 ; —NH 2 ; 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

wherein R 3 is 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, 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; aryl; heteroaryl or straight chained or branched C 1 -C 7 alkyl, wherein the alkyl may be substituted with an 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 a 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; and

wherein each X is independently CR 1 or N, provided that if one X is N then the remaining X are CR 1 ;

or a pharmaceutically acceptable salt thereof.

40 . The method of claim 39 , wherein the compound has the structure:

41 . The method of claim 40 , wherein the compound has the structure:

wherein R 2 and R 3 are each 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 ; and X is CH or N.

42 . The method of claim 41 , wherein X is CH.

43 . The method of claim 41 , wherein X is N.

44 . A method of treating a subject suffering from anxiety comprising administering to the subject a therapeutically effective amount of 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 is hydrogen; —F; —Cl; —Br; —I; —CN; —(CH 2 ) m OR 5 ; —(CH 2 ) m SR 5 ; —NH 2 ; 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

wherein R 3 is 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, 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; aryl; heteroaryl or straight chained or branched C 1 -C 7 alkyl, wherein the alkyl may be substituted with an 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 a 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; and

wherein each X is independently CR 1 or N, provided that if one X is N then the remaining X are CR 1 ;

or a pharmaceutically acceptable salt thereof.

45 . The method of claim 44 , wherein the compound has the structure:

46 . The method of claim 45 , wherein the compound has the structure:

wherein R 2 and R 3 are each 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 ; and X is CH or N.

47 . The method of claim 46 , wherein X is CH.

48 . The method of claim 46 , wherein X is N.

49 . A method of treating a subject suffering from obesity comprising administering to the subject a therapeutically effective amount of 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 is hydrogen; —F; —Cl; —Br; —I; —CN; —(CH 2 ) m OR 5 ; —(CH 2 ) m SR 5 ; —NH 2 ; 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

wherein R 3 is 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, 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; aryl; heteroaryl or straight chained or branched C 1 -C 7 alkyl, wherein the alkyl may be substituted with an 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 a 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; and

wherein each X is independently CR 1 or N, provided that if one X is N then the remaining X are CR 1 ;

or a pharmaceutically acceptable salt thereof.

50 . The method of claim 49 , where the compound has the structure:

51 . The method of claim 50 , wherein the compound has the structure:

wherein R 2 and R 3 are each 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 ; and X is CH or N.

52 . The method of claim 51 , wherein X is CH.

53 . The method of claim 51 , wherein X is N.