IP Library › Granted Patent US 8,846,935
Granted Patent B2
US 8,846,935 · App. 13/696,436 · Granted Sep 30, 2014

Indazoles

Inventors: Celine Duquenne (Collegeville, PA); Neil Johnson (Collegeville, PA); Steven D. Knight (Collegeville, PA); Louis Lafrance (Collegeville, PA); William H. Miller (Collegeville, PA); Kenneth Newlander (Collegeville, PA); Stuart Romeril (Collegeville, PA); Meagan B. Rouse (Collegeville, PA); Xinrong Tian (Collegeville, PA); Sharad Kumar Verma (Collegeville, PA)
Assignee: GlaxoSmithKline LLC
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Quick Facts
Patent No.
US 8,846,935
App. No.
13/696,436
Granted
Sep 30, 2014
Kind
B2
Abstract

Herein are disclosed indazoles of formula (I) where the various groups are defined herein, and which are useful for treating cancer.

Claims (90)

1. A compound of formula (I):

wherein

X and Z are selected independently from the group consisting of hydrogen, (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, unsubstituted or substituted (C 3 -C 8 )cycloalkyl, unsubstituted or substituted (C 3 -C 8 )cycloalkyl-(C 1 -C 8 )alkyl or —(C 2 -C 8 )alkenyl, unsubstituted or substituted (C 5 -C 8 )cycloalkenyl, unsubstituted or substituted (C 5 -C 8 )cycloalkenyl-(C 1 -C 8 )alkyl or —(C 2 -C 8 )alkenyl, (C 6 -C 10 )bicycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted aryl-(C 1 -C 8 )alkyl or —(C 2 -C 8 )alkenyl, halo, cyano, —COR a , —CO 2 R a , —CONR a R b , —CONR a NR a R b , —SR a , —SOR a , —SO 2 R a , —SO 2 NR a R b , nitro, —NR a R b , —NR a C(O)R b , —NR a C(O)NR a R b , —NR a C(O)OR a , —NR a SO 2 R b , —NR a SO 2 NR a R b , —NR a NR a R b , —NR a NR a C(O)R b , —NR a NR a C(O)NR a R b , —NR a NR a C(O)OR a , —OR a , —OC(O)R a , and —OC(O)NR a R b ;

Y is H or halo;

R 1 is (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, unsubstituted or substituted (C 3 -C 8 )cycloalkyl, unsubstituted or substituted (C 3 -C 8 )cycloalkyl-(C 1 -C 8 )alkyl or —(C 2 -C 8 )alkenyl, unsubstituted or substituted (C 5 -C 8 )cycloalkenyl, unsubstituted or substituted (C 5 -C 8 )cycloalkenyl-(C 1 -C 8 )alkyl or —(C 2 -C 8 )alkenyl, unsubstituted or substituted (C 6 -C 10 )bicycloalkyl, unsubstituted or substituted aryl, unsubstituted or substituted aryl-(C 1 -C 8 )alkyl or —(C 2 -C 8 )alkenyl, —COR a , —CO 2 R a , —CONR a R b , or —CONR a NR a R b ;

R 3 is hydrogen, (C 1 -C 8 )alkyl, cyano, trifluoromethyl, —NR a R b , or halo;

R 6 is pyridinyl which is optionally substituted by 1, 2, or 3 groups independently selected from the group consisting of—O(C 1 -C 6 )alkyl(R c ) 1-2 , —S(C 1 -C 6 )alkyl(R c ) 1-2 , —(C 1 -C 6 )alkyl(R c ) 1-2 , halo, (C 1 -C 6 )alkyl, (C 3 -C 8 )cycloalkyl, (C 5 -C 8 )cycloalkenyl, (C 1 -C 6 )haloalkyl, cyano, —COR a , —CO 2 R a , CONR a R b , —SR a , —SOR a , —SO 2 R a , —SO 2 NR a R b , nitro, —NR a R b , —NR a C(O)R b , —NR a C(O)NR a R b , —NR a C(O)OR a , —NR a SO 2 R b , —NR a SO 2 NR a R b , —OR a , —OC(O)R a , —OC(O)NR a R b , aryl, and aryl(C 1 -C 4 )alky;

wherein any aryl moiety of said aryl or aryl(C 1 -C 4 )alkyl is optionally substituted by 1, 2, or 3 groups independently selected from the group consisting of halo, (C 1 -C 6 )alkyl, (C 3 -C 8 )cycloalkyl, (C 5 -C 8 )cycloalkenyl, (C 1 -C 6 )haloalkyl, cyano, —COR a , —CO 2 R a , —CONR a R b , —SR a , —SOR a , —SO 2 R a , —SO 2 NR a R b , nitro, —NR a R b , —NR a C(O)R b , —NR a C(O)NR a R b , —NR a C(O)OR a , —NR a SO 2 R b , —NR a SO 2 NR a R b , —OR a , —OC(O)R a , and —OC(O)NR a R b ;

R a and R b are each independently hydrogen, (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, (C 3 -C 8 )cycloalkyl, (C 5 -C 8 )cycloalkenyl, (C 6 -C 10 )bicycloalkyl, or aryl, wherein said (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, cycloalkyl, cycloalkenyl, bicycloalkyl, or aryl group is optionally substituted by 1, 2, or 3 groups independently selected from halo, hydroxyl, (C 1 -C 4 )alkoxy, amino, (C 1 -C 4 )alkylamino, ((C 1 -C 4 )alkyl)((C 1 -C 4 )alkyl)amino, —CO 2 H, —CO 2 (C 1 -C 4 )alkyl, —CONH 2 , —CONH(C 1 -C 4 )alkyl, —CON((C 1 -C 4 )alkyl)((C 1 -C 4 )alkyl), —SO 2 (C 1 -C 4 )alkyl, —SO 2 NH 2 , —SO 2 NH(C 1 -C 4 )alkyl, and —SO 2 N((C 1 -C 4 )alkyl)((C 1 -C 4 )alkyl);

or R a and R b taken together with the nitrogen to which they are attached represent a 5-8 membered saturated or unsaturated ring, optionally containing an additional heteroatom selected from oxygen, nitrogen, and sulfur, wherein said ring is optionally substituted by 1, 2, or 3 groups independently selected from (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, amino, (C 1 -C 4 )alkylamino, ((C 1 -C 4 )alkyl)((C 1 -C 4 )alkyl)amino, hydroxyl, oxo, (C 1 -C 4 )alkoxy, and (C 1 -C 4 )alkoxy(C 1 -C 4 )alkyl, wherein said ring is optionally fused to a (C 3 -C 8 )cycloalkyl or aryl ring;

or R a and R b taken together with the nitrogen to which they are attached represent a 6- to 10-membered bridged bicyclic ring system optionally fused to a (C 3 -C 8 )cycloalkyl, or aryl ring; and

each R c is independently —NR a SO 2 R b , —SOR a , —SO 2 R a , —NR a C(O)OR a , —NR a R b , or —CO 2 R a ;

or a pharmaceutically acceptable salt thereof.

2. The compound according to claim 1 wherein:

X and Z are selected independently from the group consisting of (C 1 -C 8 )alkyl, (C 3 -C 8 )cycloalkyl, aryl, —NR a R b , and —OR a ;

Y is H;

R 1 is (C 1 -C 8 )alkyl or (C 3 -C 8 )cycloalkyl;

R 3 is hydrogen, (C 1 -C 8 )alkyl, or halo;

R 6 is pyridinyl which is optionally substituted by 1, 2, or 3 groups independently selected from halo, (C 1 -C 6 )alkyl, (C 3 -C 8 )cycloalkyl, (C 5 -C 8 )cycloalkenyl, (C 1 -C 6 )haloalkyl, cyano, —COR a , —CO 2 R a , —CONR a R b , —SR a , —SOR a , —SO 2 R a , —SO 2 NR a R b , nitro, —NR a R b , —NR a C(O)R b , —NR a C(O)NR a R b , —NR a C(O)OR a , —NR a SO 2 R b , —NR a SO 2 NR a R b , —OR a , —OC(O)R a , —OC(O)NR a R b , aryl, and aryl(C 1 -C 4 )alkyl; and

R a and R b are each independently hydrogen, (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, (C 3 -C 8 )cycloalkyl, (C 5 -C 8 )cycloalkenyl, (C 6 -C 10 )bicycloalkyl, or aryl, wherein said (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, cycloalkyl, cycloalkenyl, bicycloalkyl, or aryl group is optionally substituted by 1, 2, or 3 groups independently selected from halo, hydroxyl, (C 1 -C 4 )alkoxy, amino, (C 1 -C 4 )alkylamino, ((C 1 -C 4 )alkyl)((C 1 -C 4 )alkyl)amino, —CO 2 H, —CO 2 (C 1 -C 4 )alkyl, —CONH 2 , —CONH(C 1 -C 4 )alkyl, —CON((C 1 -C 4 )alkyl)((C 1 -C 4 )alkyl), —SO 2 (C 1 -C 4 )alkyl, —SO 2 NH 2 , —SO 2 NH(C 1 -C 4 )alkyl, and —SO 2 N((C 1 -C 4 )alkyl)((C 1 -C 4 )alkyl);

or R a and R b taken together with the nitrogen to which they are attached represent a 5-8 membered saturated or unsaturated ring, optionally containing an additional heteroatom selected from oxygen, nitrogen, and sulfur, wherein said ring is optionally substituted by 1, 2, or 3 groups independently selected from (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, amino, (C 1 -C 4 )alkylamino, ((C 1 -C 4 )alkyl)((C 1 -C 4 )alkyl)amino, hydroxyl, oxo, (C 1 -C 4 )alkoxy, and (C 1 -C 4 )alkoxy(C 1 -C 4 )alkyl, wherein said ring is optionally fused to a (C 3 -C 8 )cycloalkyl, or aryl ring;

or R a and R b taken together with the nitrogen to which they are attached represent a 6- to 10-membered bridged bicyclic ring system optionally fused to a (C 3 -C 8 )cycloalkyl or aryl ring;

wherein any aryl is selected from the group consisting of phenyl and naphthyridine;

or a pharmaceutically acceptable salt thereof.

3. The compound according to claim 1 wherein:

X is methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, trifluoromethyl, tetrahydropyran, hydroxymethyl, methoxymethyl, or benzyl;

Y is H;

Z is methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, or benzyl;

R 1 is isopropyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl or benzyl;

R 3 is H, methyl, or Br; and

R 6 is 3 pyridinyl, 4-pyridinyl, 2-(4-morpholinyl)-4-pyridinyl, 2-amino-4-pyridinyl, 5-(methyloxy)-3-pyridinyl, 5-(methylsulfonyl)-3-pyridinyl, 5-[(cyclopropylsulfonyl)amino]-6-(methyloxy)-3-pyridinyl, 5-[(phenylsulfonyl)amino]-3-pyridinyl, 6-(4-methyl-1-piperazinyl)-3-pyridinyl, 6-(4-morpholinyl)-3-pyridinyl, 6-(acetylamino)-3-pyridinyl, 6-(dimethylamino)-3-pyridinyl, 6-(methyloxy)-3-pyridinyl, 6-[(methylamino)carbonyl]-3-pyridinyl, 6-[(methylamino)sulfonyl]-3-pyridinyl, or 6-methyl-3-pyridinyl;

or a pharmaceutically acceptable salt thereof.

4. The compound according to claim 1 wherein:

X is (C 1 -C 8 )alkyl or (C 3 -C 8 )cycloalkyl;

Y is H;

Z is (C 1 -C 3 )alkyl;

R 1 is (C 3 -C 8 )alkyl or (C 3 -C 8 )cycloalkyl;

R 3 is hydrogen, (C 1 -C 3 )alkyl, or halo;

R 6 is pyridinyl which is optionally substituted by 1, 2, or 3 groups independently selected from —O(C 1 -C 6 )alkyl(R c ) 1-2 , —S(C 1 -C 6 )alkyl(R c ) 1-2 , —(C 1 -C 6 )alkyl(R c ) 1-2 , halo, (C 1 -C 6 )alkyl, (C 3 -C 8 )cycloalkyl, (C 5 -C 8 )cycloalkenyl, (C 1 -C 6 )haloalkyl, cyano, —COR a , —CO 2 R a , —CONR a R b , —SR a , —SOR a , —SO 2 R a , —SO 2 NR a R b , nitro, —NR a R b , —NR a C(O)R b , —NR a C(O)NR a R b , —NR a C(O)OR a , —NR a SO 2 R b , —NR a SO 2 NR a R b , —OR a , —OC(O)R a , —OC(O)NR a R b , aryl, and aryl(C 1 -C 4 )alkyl;

R a and R b are each independently hydrogen, (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, (C 3 -C 8 )cycloalkyl, (C 5 -C 8 )cycloalkenyl, (C 6 -C 10 )bicycloalkyl, or aryl, wherein said (C 1 -C 8 )alkyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, cycloalkyl, cycloalkenyl, bicycloalkyl, or aryl group is optionally substituted by 1, 2, or 3 groups independently selected from halo, hydroxyl, (C 1 -C 4 )alkoxy, amino, (C 1 -C 4 )alkylamino, ((C 1 -C 4 )alkyl)((C 1 -C 4 )alkyl)amino, —CO 2 H, —CO 2 (C 1 -C 4 )alkyl, —CONH 2 , —CONH(C 1 -C 4 )alkyl, —CON((C 1 -C 4 )alkyl)((C 1 -C 4 )alkyl), —SO 2 (C 1 -C 4 )alkyl, —SO 2 NH 2 , —SO 2 NH(C 1 -C 4 )alkyl, and —SO 2 N((C 1 -C 4 )alkyl)((C 1 -C 4 )alkyl);

or R a and R b taken together with the nitrogen to which they are attached represent a 5-8 membered saturated or unsaturated ring, optionally containing an additional heteroatom selected from oxygen, nitrogen, and sulfur, wherein said ring is optionally substituted by 1, 2, or 3 groups independently selected from (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, amino, (C 1 -C 4 )alkylamino, ((C 1 -C 4 )alkyl)((C 1 -C 4 )alkyl)amino, hydroxyl, oxo, (C 1 -C 4 )alkoxy, and (C 1 -C 4 )alkoxy(C 1 -C 4 )alkyl; and

each R c is independently —NR a SO 2 R b , —SOR a , —SO 2 R a , —NR a C(O)OR a , —NR a R b , or —CO 2 R a ;

or a pharmaceutically acceptable salt thereof.

5. The compound according to claim 1 which is:

N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-[6-(1-piperazinyl)-3-pyridinyl]-1H-indazole-4-carboxamide;

1-isopropyl-N-((4-isopropyl-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(6-(piperazin-1-yl)pyridin-3-yl)-1H-indazole-4-carboxamide;

1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-6-[6-(1-piperazinyl)-3-pyridinyl]-1H-indazole-4-carboxamide;

N-((4-ethyl-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-6-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-indazole-4-carboxamide;

6-[6-(dimethylamino)-3-pyridinyl]-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide;

1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-6-[6-(4-morpholinyl)-3-pyridinyl]-1H-indazole-4-carboxamide;

6-(6-amino-3-pyridinyl)-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide;

1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-6-[6-(methyloxy)-3-pyridinyl]-1H-indazole-4-carboxamide;

1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-6-[6-(4-methyl-1-piperazinyl)-3-pyridinyl]-1H-indazole-4-carboxamide;

1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-6-(2-methyl-3-pyridinyl)-1H-indazole-4-carboxamide;

1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-6-(6-methyl-3-pyridinyl)-1H-indazole-4-carboxamide;

6-[6-(dimethylamino)-3-pyridinyl]-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-indazole-4-carboxamide;

N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-[6-(trifluoromethyl)-3-pyridinyl]-1H-indazole-4-carboxamide;

1-cyclopentyl-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(6-methoxypyridin-3-yl)-1H-indazole-4-carboxamide;

1-cyclopentyl-N-((6-methyl-2-oxo-4-propyl-1,2-dihydropyridin-3-yl)methyl)-6-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-indazole-4-carboxamide;

1-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-[6-(1-piperazinyl)-3-pyridinyl]-1H-indazole-4-carboxamide;

1-isopropyl-3-methyl-N-((6-methyl-2-oxo-4-propyl-1,2-dihydropyridin-3-yl)methyl)-6-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-1H-indazole-4-carboxamide;

3-methyl-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-6-[6(1-piperazinyl)-3-pyridinyl]-1H-indazole-4-carboxamide;

6-(6-(dimethylamino)pyridin-3-yl)-N-((1,2-dihydro-4,6-dimethyl-2-oxopyridin-3-yl)methyl)-1-isopropyl-3-methyl-1H-indazole-4-carboxamide;

N-((1,2-dihydro-4,6-dimethyl-2-oxopyridin-3-yl)methyl)-1-isopropyl-3-methyl-6-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-indazole-4-carboxamide;

N-((1,2-dihydro-4,6-dimethyl-2-oxopyridin-3-yl)methyl)-1-isopropyl-3-methyl-6-(6-(piperazin-1-yl)pyridin-3-yl)-1H-indazole-4-carboxamide;

N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-3-methyl-6-(6-(4-methylpiperazin-1-yl)pyridin-2-yl)-1H-indazole-4-carboxamide;

N-((1,2-dihydro-4,6-dimethyl-2-oxopyridin-3-yl)methyl)-1-isopropyl-3-methyl-6-(pyridin-3-yl)-1H-indazole-4-carboxamide;

N-((1,2-dihydro-4,6-dimethyl-2-oxopyridin-3-yl)methyl)-1-isopropyl-3-methyl-6-(pyridin-3-yl)-1H-indazole-4-carboxamide;

N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-1-(1-methylethyl)-6-(6-methyl-3-pyridinyl)-1H-indazole-4-carboxamide;

6-[6-(dimethylamino)-3-pyridinyl]-3-methyl-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide;

3-methyl-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-6-(3-pyridinyl)-1H-indazole-4-carboxamide; or

3-methyl-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-6-[6-(4-methyl-1-piperazinyl)-3-pyridinyl]-1H-indazole-4-carboxamide;

or a pharmaceutically acceptable salt thereof.

6. The compound according to claim 1 which is:

N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(4-pyridinyl)-1H-indazole-4-carboxamide;

N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-[6-(4-methyl-1-piperazinyl)-3-pyridinyl]-1H-indazole-4-carboxamide;

6-[6-(acetylamino)-3-pyridinyl]-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-indazole-4-carboxamide;

N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(3-pyridinyl)-1H-indazole-4-carboxamide;

N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-[6-(4-morpholinyl)-3-pyridinyl]-1H-indazole-4-carboxamide;

N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-[6-(methyloxy)-3-pyridinyl]-1H-indazole-4-carboxamide;

1-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-[2-(4-methyl-1-piperazinyl)-4-pyridinyl]-1H-indazole-4-carboxamide;

1-(1-methylethyl)-N-{[6-methyl-4-(1-methylethyl)-2-oxo-1,2-dihydro-3-pyridinyl]methyl}6-[2-(4-methyl-1-piperazinyl)-4-pyridinyl]-1H-indazole-4-carboxamide;

1-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-(6-methyl-3-pyridinyl)-1H-indazole-4-carboxamide;

1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-6-[2-(4-methyl-1-piperazinyl)-4-pyridinyl]-1H-indazole-4-carboxamide;

1-cyclopentyl-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-6-(6-methyl-3-pyridinyl)-1H-indazole-4-carboxamide;

1-cyclopentyl-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-6-(3-pyridinyl)-1H-indazole-4-carboxamide;

1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-6-(3-pyridinyl)-1H-indazole-4-carboxamide; or

1-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-[6-(4-morpholinyl)-3-pyridinyl]-1H-indazole-4-carboxamide;

or a pharmaceutically acceptable salt thereof.

7. A pharmaceutical composition comprising the compound or pharmaceutically acceptable salt thereof according to claim 1 and a pharmaceutically acceptable excipient.

Continuity (2)
Provisional Application 61332312 · May 7, 2010
Related Publication 20130053383A1 · Feb 28, 2013