5-substituted indazoles as kinase inhibitors

1. A compound of formula (I)

or a pharmaceutically acceptable salt thereof,

wherein A is (ii)

R 1 is hydrogen or R a R b N;

R 2 is hydrogen, heterocyclecarbonyl, alkylcarbonyl, arylcarbonyl, or R e R f N-alkyl-C(O)—;

R 3 is alkyl, alkoxy, aryl, cyano, cycloalkyl, halogen, haloalkyl, heteroaryl, nitro, or R g R h N—;

R a and R b are each hydrogen;

R e and R f are each independently hydrogen or alkyl; R g and R h are each independently hydrogen, alkyl, or alkylcarbonyl;

R j and R k are each independently hydrogen, alkyl, aryl, arylalkyl, or heteroaryl;

R ii is alkoxyalkyl, alkoxycarbonyl, aryl, arylalkyl, aryl(hydroxy)alkyl, aryloxyalkyl, arylcarbonyl, arylthioalkyl, carboxy, cycloalkyl, cycloalkylalkyl, cycloalkylcarbonyl, halogen, heteroaryl, heteroarylalkyl, heterocycle, heterocyclealkyl, heterocyclecarbonyl, hydroxyalkyl, trialkylsilylalkyl, Z a Z b N—, Z a Z b Nalkyl- or Z c Z d NC(O)—;

Z a and Z b are each independently hydrogen, alkyl or H 2 NalkylC(O)—;

Z c and Z d are each independently hydrogen, alkyl, alkoxyalkyl, aryl, arylalkyl, cycloalkyl, cycloalkylalkyl, heteroarylalkyl, heterocyclealkyl, hydroxyalkyl or dialkylN-alkyl-;

m is 0; and

b is 1 or 2.

2. The compound according to claim 1 , wherein

R 2 is hydrogen, or R e R f N-alkyl-C(O)—;

R 4 is alkyl, alkoxyalkyl, aryl, cycloalkyl, R j R k N— or R j R k N-alkyl-;

R 5 is alkyl, aryl or heteroaryl;

R j and R k are each independently hydrogen, alkyl, or aryl;

R ii is alkoxyalkyl, aryl, arylalkyl, aryloxyalkyl, arylcarbonyl, arylthioalkyl, carboxy, cycloalkyl, cycloalkylalkyl, cycloalkylcarbonyl, halogen, heteroaryl, heteroarylalkyl, heterocyclealkyl, heterocyclecarbonyl, hydroxyalkyl, Z a Z b Nalkyl-, or Z c Z d NC(O)—;

Z a and Z b are each independently hydrogen or alkyl;

Z c and Z d are each independently hydrogen, alkyl, alkoxyalkyl, aryl, arylalkyl, cycloalkylalkyl or heterocyclealkyl;

m is 0; and

b is 1 or 2.

3. The compound according to claim 1 , wherein

R 2 is hydrogen;

R 4 is alkyl, alkoxyalkyl or aryl;

R 5 is alkyl or aryl;

R ii is aryl, arylalkyl, cycloalkyl, cycloalkylalkyl or halogen;

b is 1 or 2; and

m is 0.

4. The compound according to claim 1 , wherein

R 4 is alkoxyalkyl, alkyl, aryl, or R j R k N—;

R 5 is alkyl, aryl, or heteroaryl;

R j and R k are alkyl;

R ii is alkoxyalkyl, aryl, arylalkyl, aryl(hydroxy)alkyl, aryloxyalkyl, arylcarbonyl, arylthioalkyl, carboxy, cycloalkyl, cycloalkylalkyl, cycloalkylcarbonyl, halogen, heteroaryl, heteroarylalkyl, heterocyclealkyl, heterocyclecarbonyl, hydroxyalkyl, Z a Z b Nalkyl or Z c Z d NC(O)—;

Z a and Z b are each independently hydrogen or H 2 Nalkyl-C(O)—;

Z c and Z d are each independently hydrogen, alkoxyalkyl, alkyl, arylalkyl, cycloalkyl, cycloalkylalkyl, or heterocyclealkyl;

b is 1; and

m is 0.

5. The compound according to claim 1 , wherein

R 2 is hydrogen, heterocyclecarbonyl, or arylcarbonyl;

R 4 is alkyl, alkoxyalkyl, aryl, R j R k N— or R j R k N-alkyl-;

R 5 is alkyl, or aryl;

R j and R k are each independently hydrogen, alkyl, aryl, or arylalkyl;

R ii is aryl, arylalkyl, arylcarbonyl, cycloalkyl, cycloalkylalkyl, halogen, heteroaryl, heterocyclealkyl, heterocyclecarbonyl, or Z c Z d NC(O)—;

Z c and Z d are each independently hydrogen, alkyl, alkoxyalkyl, aryl;

m is 0; and

b is 1 or 2.

6. The compound of claim 1 , that is selected from the group consisting of:

5-(1-benzyl-1H-1,2,3-triazol-4-yl)-1H-indazole;

5-[1-(2-methylbenzyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

5-[1-(3-methylbenzyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

5-[1-(4-methylbenzyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

5-[1-(3-methoxybenzyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

5-[1-(2-fluorobenzyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

5-[1-(3-fluorobenzyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

5-[1-(4-fluorobenzyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

5-[1-(2-chlorobenzyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

5-[1-(3-chlorobenzyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

5-[1-(4-chlorobenzyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

5-[1-(2-bromobenzyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

5-[1-(2-nitrobenzyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

5-[1-(3-nitrobenzyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

5-[1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

2-{[4-(1H-indazol-5-yl)-1H-1,2,3-triazol-1-yl]methyl}benzonitrile;

3-{[4-(1H-indazol-5-yl)-1H-1,2,3-triazol-1-yl]methyl}benzonitrile;

4-{[4-(1H-indazol-5-yl)-1H-1,2,3-triazol-1-yl]methyl}benzonitrile;

5-{1-[2-(trifluoromethyl)benzyl]-1H-1,2,3-triazol-4-yl}-1H-indazole;

5-{1-[3-(trifluoromethyl)benzyl]-1H-1,2,3-triazol-4-yl}-1H-indazole;

5-{1-[4-(trifluoromethyl)benzyl]-1H-1,2,3-triazol-4-yl}-1H-indazole;

5-{1-[3-(trifluoromethoxy)benzyl]-1H-1,2,3-triazol-4-yl}-1H-indazole;

5-{1-[4-(trifluoromethoxy)benzyl]-1H-1,2,3-triazol-4-yl}-1H-indazole;

5-[1-(4-tert-butylbenzyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

methyl 3-{[4-(1H-indazol-5-yl)-1H-1,2,3-triazol-1-yl]methyl}benzoate;

methyl 4-{[4-(1H-indazol-5-yl)-1H-1,2,3-triazol-1-yl]methyl}benzoate;

5-[1-(2,4-dimethylbenzyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

5-[1-(3,5-dimethylbenzyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

5-[1-(2,3-dichlorobenzyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

5-[1-(2,4-dichlorobenzyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

5-[1-(2,5-dichlorobenzyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

5-[1-(3,5-dichlorobenzyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

5-{1-[2,4-bis(trifluoromethyl)benzyl]-1H-1,2,3-triazol-4-yl}-1H-indazole;

5-(1-benzyl-1H-1,2,3-triazol-4-yl)-1H-indazol-3-amine;

5-(1-benzyl-1H-1,2,3-triazol-4-yl)-1-[(1-methylpiperidin-4-yl)carbonyl]-1H-indazol-3-amine;

5-(1-benzyl-5-cyclopropyl-1H-1,2,3-triazol-4-yl)-1H-indazole;

5-(1-benzyl-4-cyclopropyl-1H-1,2,3-triazol-5-yl)-1H-indazole;

5-[1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

5-(1-benzyl-5-phenyl-1H-1,2,3-triazol-4-yl)-1H-indazole;

5-(4-benzyl-1H-1,2,3-triazol-1-yl)-1H-indazole;

5-(1-benzyl-5-cyclopropyl-1H-1,2,3-triazol-4-yl)-1H-indazol-3-amine;

5-(1-benzyl-4-cyclopropyl-1H-1,2,3-triazol-5-yl)-1H-indazol-3-amine;

5-(1-benzyl-5-phenyl-1H-1,2,3-triazol-4-yl)-1H-indazol-3-amine;

2-[1-(1H-indazol-5-yl)-1H-1,2,3-triazol-4-yl]propan-2-ol;

5-[4-(methoxymethyl)-1H-1,2,3-triazol-1-yl]-1H-indazole;

1-[1-(1H-indazol-5-yl)-1H-1,2,3-triazol-4-yl]-1-phenylethanol;

1-[1-(1H-indazol-5-yl)-1H-1,2,3-triazol-4-yl]propan-2-ol;

3-[1-(1H-indazol-5-yl)-1H-1,2,3-triazol-4-yl]propan-1-ol;

1-{[1-(1H-indazol-5-yl)-1H-1,2,3-triazol-4-yl]methyl}-1H-1,2,3-benzotriazole;

5-{4-[(phenylthio)methyl]-1H-1,2,3-triazol-1-yl}-1H-indazole;

5-(4-cyclopropyl-1H-1,2,3-triazol-1-yl)-1H-indazole;

5-[4-(2-phenylethyl)-1H-1,2,3-triazol-1-yl]-1H-indazole;

5-[4-(cyclohexylmethyl)-1H-1,2,3-triazol-1-yl]-1H-indazole;

5-(4-cyclopentyl-1H-1,2,3-triazol-1-yl)-1H-indazole;

1-[1-(1H-indazol-5-yl)-1H-1,2,3-triazol-4-yl]cyclohexanol;

5-[4-(phenoxymethyl)-1H-1,2,3-triazol-1-yl]-1H-indazole;

5-{4-[(1,1-dioxidothiomorpholin-4-yl)methyl]-1H-1,2,3-triazol-1-yl}-1H-indazole;

5-[4-(3-phenylpropyl)-1H-1,2,3-triazol-1-yl]-1H-indazole;

[1-benzyl-4-(1H-indazol-5-yl)-1H-1,2,3-triazol-5-yl](phenyl)methanone;

N,N-diethyl-N-{[1-(1H-indazol-5-yl)-1H-1,2,3-triazol-4-yl]methyl}amine;

5-(1-benzyl-5-methyl-1H-1,2,3-triazol-4-yl)-1H-indazole;

5-(1-benzyl-5-methyl-1H-1,2,3-triazol-4-yl)-1H-indazol-3-amine;

5-(1-benzyl-5-iodo-1H-1,2,3-triazol-4-yl)-1H-indazol-3-amine;

N-{3-[4-(3-amino-1H-indazol-5-yl)-1-benzyl-1H-1,2,3-triazol-5-yl]phenyl}-N′-(3-methylphenyl)urea;

[1-benzyl-4-(1H-indazol-5-yl)-1H-1,2,3-triazol-5-yl](3-chlorophenyl)methanone;

[1-benzyl-4-(1H-indazol-5-yl)-1H-1,2,3-triazol-5-yl](cyclopropyl)methanone;

5-[5-cyclopropyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

N 1 -{[1-benzyl-4-(1H-indazol-5-yl)-1H-1,2,3-triazol-5-yl]methyl}glycinamide;

(4-fluorophenyl)[4-(1H-indazol-5-yl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-1,2,3-triazol-5-yl]methanone;

(4-chlorophenyl)[4-(1H-indazol-5-yl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-1,2,3-triazol-5-yl]methanone;

(3-chlorophenyl)[4-(1H-indazol-5-yl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-1,2,3-triazol-5-yl]methanone;

(2-chlorophenyl)[4-(1H-indazol-5-yl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-1,2,3-triazol-5-yl]methanone;

cyclopentyl[4-(1H-indazol-5-yl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-1,2,3-triazol-5-yl]methanone;

1-benzyl-4-(1H-indazol-5-yl)-1H-1,2,3-triazole-5-carboxylic acid;

5-{5-(4-fluorophenyl)-1-[4-(trifluoromethyl)benzyl]-1H-1,2,3-triazol-4-yl}-1H-indazol-3-amine;

5-[1-benzyl-5-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl]-1H-indazol-3-amine;

[4-(1H-indazol-5-yl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-1,2,3-triazol-5-yl](tetrahydro-2H-pyran-4-yl)methanone;

5-[1-benzyl-5-(2-methylphenyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

5-{1-benzyl-5-[(4-methylpiperazin-1-yl)carbonyl]-1H-1,2,3-triazol-4-yl}-1H-indazole;

1-{[1-benzyl-4-(1H-indazol-5-yl)-1H-1,2,3-triazol-5-yl]carbonyl}piperidin-4-ol;

1-acetyl-5-[5-(4-fluorophenyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

1-benzyl-4-(1H-indazol-5-yl)-N,N-dimethyl-1H-1,2,3-triazole-5-carboxamide;

N,1-dibenzyl-4-(1H-indazol-5-yl)-1H-1,2,3-triazole-5-carboxamide;

5-[1-benzyl-5-(2-methylphenyl)-1H-1,2,3-triazol-4-yl]-1H-indazol-3-amine;

2-{2-[1-(1H-indazol-5-yl)-1H-1,2,3-triazol-4-yl]ethyl}-1H-isoindole-1,3(2H)-dione;

5-{4-[(2,4-dichlorophenoxy)methyl]-1H-1,2,3-triazol-1-yl}-1H-indazole;

5-{4-[(2,6-dichlorophenoxy)methyl]-1H-1,2,3-triazol-1-yl}-1H-indazole;

5-[5-(4-fluorophenyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

1-{[1-(1H-indazol-5-yl)-1H-1,2,3-triazol-4-yl]methyl}-1H-indazole;

5-[1-benzyl-5-(piperidin-1-ylcarbonyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

5-[5-(2-methylphenyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

5-[5-(2-methylphenyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-1,2,3-triazol-4-yl]-1H-indazol-3-amine;

5-[1-benzyl-5-(morpholin-4-ylcarbonyl)-1H-1,2,3-triazol-4-yl]-1H-indazole;

5-[1-benzyl-5-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl]-1H-indazol-3-amine;

5-{1-benzyl-5-[3-(dimethylamino)phenyl]-1H-1,2,3-triazol-4-yl}-1H-indazol-3-amine;

5-{1-benzyl-5-[4-(dimethylamino)phenyl]-1H-1,2,3-triazol-4-yl}-1H-indazol-3-amine;

N-{3-[4-(3-amino-1H-indazol-5-yl)-1-benzyl-1H-1,2,3-triazol-5-yl]phenyl}acetamide;

N-{4-[4-(3-amino-1H-indazol-5-yl)-1-benzyl-1H-1,2,3-triazol-5-yl]phenyl}acetamide;

5-{1-benzyl-5-[3-(1H-pyrazol-1-yl)phenyl]-1H-1,2,3-triazol-4-yl}-1H-indazol-3-amine;

5-[1-benzyl-5-(1-methyl-1H-pyrazol-4-yl)-1H-1,2,3-triazol-4-yl]-1H-indazol-3-amine;

3-[4-(3-amino-1H-indazol-5-yl)-1-benzyl-1H-1,2,3-triazol-5-yl]-N-phenylbenzamide;

3-[4-(3-amino-1H-indazol-5-yl)-1-benzyl-1H-1,2,3-triazol-5-yl]-N-benzylbenzamide;

5-[1-benzyl-5-(1-methyl-1H-indol-5-yl)-1H-1,2,3-triazol-4-yl]-1H-indazol-3-amine;

5-[1-benzyl-5-(3-methoxyphenyl)-1H-1,2,3-triazol-4-yl]-1H-indazol-3-amine;

5-[1-benzyl-5-(3-morpholin-4-ylphenyl)-1H-1,2,3-triazol-4-yl]-1H-indazol-3-amine;

1-{[1-benzyl-4-(1H-indazol-5-yl)-1H-1,2,3-triazol-5-yl]carbonyl}piperidin-4-amine;

3-[4-(3-amino-1H-indazol-5-yl)-1-benzyl-1H-1,2,3-triazol-5-yl]phenol;

3-[4-(3-amino-1H-indazol-5-yl)-1-benzyl-1H-1,2,3-triazol-5-yl]benzamide;

5-{1-benzyl-5-[4-(methylsulfonyl)phenyl]-1H-1,2,3-triazol-4-yl}-1H-indazol-3-amine;

1-benzyl-4-(1H-indazol-5-yl)-N-[(2S)-tetrahydrofuran-2-ylmethyl]-1H-1,2,3-triazole-5-carboxamide;

1-benzyl-4-(1H-indazol-5-yl)-N-(2-isopropoxyethyl)-1H-1,2,3-triazole-5-carboxamide;

1-benzyl-4-(1H-indazol-5-yl)-N-[(2R)-tetrahydrofuran-2-ylmethyl]-1H-1,2,3-triazole-5-carboxamide;

1-benzyl-4-(1H-indazol-5-yl)-N-(tetrahydrofuran-3-ylmethyl)-1H-1,2,3-triazole-5-carboxamide;

1-benzyl-N-cyclopentyl-4-(1H-indazol-5-yl)-1H-1,2,3-triazole-5-carboxamide;

1-benzyl-N-(cyclopentylmethyl)-4-(1H-indazol-5-yl)-1H-1,2,3-triazole-5-carboxamide;

1-benzyl-N-ethyl-4-(1H-indazol-5-yl)-N-methyl-1H-1,2,3-triazole-5-carboxamide;

1-benzyl-4-(1H-indazol-5-yl)-N-isopropyl-N-methyl-1H-1,2,3-triazole-5-carboxamide;

1-benzyl-4-(1H-indazol-5-yl)-N-(2-methoxyethyl)-N-methyl-1H-1,2,3-triazole-5-carboxamide;

1-benzyl-4-(1H-indazol-5-yl)-N-phenyl-1H-1,2,3-triazole-5-carboxamide;

1-benzyl-N-(4-chlorophenyl)-4-(1H-indazol-5-yl)-1H-1,2,3-triazole-5-carboxamide;

1-benzyl-4-(1H-indazol-5-yl)-N-(2-morpholin-4-ylethyl)-1H-1,2,3-triazole-5-carboxamide;

1-benzyl-N-[2-(dimethylamino)ethyl]-4-(1H-indazol-5-yl)-N-methyl-1H-1,2,3-triazole-5-carboxamide;

1-benzyl-N-(2-hydroxyethyl)-4-(1H-indazol-5-yl)-N-propyl-1H-1,2,3-triazole-5-carboxamide;

1-benzyl-N-[3-(dimethylamino)propyl]-4-(1H-indazol-5-yl)-N-methyl-1H-1,2,3-triazole-5-carboxamide;

1-benzyl-N-[2-(diethylamino)ethyl]-4-(1H-indazol-5-yl)-N-methyl-1H-1,2,3-triazole-5-carboxamide;

N,1-dibenzyl-N-ethyl-4-(1H-indazol-5-yl)-1H-1,2,3-triazole-5-carboxamide;

N,1-dibenzyl-N-(2-hydroxyethyl)-4-(1H-indazol-5-yl)-1H-1,2,3-triazole-5-carboxamide;

(3R)-1-{[1-benzyl-4-(1H-indazol-5-yl)-1H-1,2,3-triazol-5-yl]carbonyl}piperidin-3-ol;

1-{[1-benzyl-4-(1H-indazol-5-yl)-1H-1,2,3-triazol-5-yl]carbonyl}piperidine-4-carboxamide;

5-{1-benzyl-5-[(2,6-dimethylmorpholin-4-yl)carbonyl]-1H-1,2,3-triazol-4-yl}-1H-indazole;

5-{5-[(4-acetylpiperazin-1-yl)carbonyl]-1-benzyl-1H-1,2,3-triazol-4-yl}-1H-indazole;

5-{1-benzyl-5-[(4-phenylpiperazin-1-yl)carbonyl]-1H-1,2,3-triazol-4-yl}-1H-indazole;

1-benzyl-N-[(1R)-1-(hydroxymethyl)-2-methylpropyl]-4-(1H-indazol-5-yl)-1H-1,2,3-triazole-5-carboxamide;

1-benzyl-N-[(1S)-1-(hydroxymethyl)-2-methylpropyl]-4-(1H-indazol-5-yl)-1H-1,2,3-triazole-5-carboxamide; and

1-benzyl-N-[3-(1H-imidazol-1-yl)propyl]-4-(1H-indazol-5-yl)-1H-1,2,3-triazole-5-carboxamide.

7. A pharmaceutical composition comprising a therapeutically effective amount of a compound of formula (I) according to claim 1 , in combination with a pharmaceutically suitable carrier.