Indazole compounds

1. A compound of Formula (I)

wherein

R 1 is selected from the group consisting of H, benzyl substituted with OCH 3 , optionally substituted (C 1 -C 3 )alkyl, pyrimidine substituted with NH 2 and amino(C 1 -C 3 )alkyl;

R 3 is selected from the group consisting of H, halogen, NH 2 , OH, COOH, —C(O)—NH—CH 2 —C(O)—OCH 3 , —NH—CH 2 -phenyl, —C(O)-pyridinyl, —NH—C(O)-cyclobutyl and —NH—C(O)-phenyl wherein phenyl is optionally substituted with either N(CH 3 ) 2 or OCH 3 ; or

R 3 is selected from the optionally substituted group consisting of (C 1 -C 6 )alkyl, benzo[b]thienyl, 2,3-dihydrobenzofuranyl, indolyl, isoquinolinyl, morpholinyl, naphthyl, phenyl, piperazinyl, pyrazolyl, pyridinyl, pyrimidinyl, pyrrolyl, quinolinyl and thienyl;

wherein the substituent is selected from one or more CH 3 , NH 2 , Cl, F, dimethylamino, OH, CH 2 OH, —C(O)NH 2 , COOH, CF 3 , isopropyl, OCF 3 , OCH 3 , —O—CH 2 -phenyl, CN, OCH 2 CH 3 , —NH—C(O)-cyclobutyl, —NH—C(O)-phenyl, NH—C(O)—CH 3 , NHC(O)CH 3 , N(CH 3 ) 2 , S(O) 2 CH 3 and C(O)NH-phenyl; or

R 3 is —C(O)—NY 100 —(C(Y 100 ) 2 ) x —R a wherein

x is 0, 1, 2 or 3;

Y 100 is independently H or (C 1 -C 3 )alkyl; and

R a is —C(O)—CH 3 or is selected from the optionally substituted group (C 1 -C 3 )alkyl, amino, aminoalkyl, benzimidazolyl, benzo[b]thienyl, benzotriazolyl, biphenyl, 1,3-dihydrobenzimidazolyl, 1,3-dihydrobenzimidazolyl-2-one, imidazolyl, indolyl, naphthyl, phenyl, pyrazolyl, pyridinyl, pyrimidinyl, tetrahydropyranyl and thiazolyl; or

R 3 is A-B wherein A is connected to the indazole and

A is selected from the group consisting of —C≡C, —C≡C phenyl indazolyl, phenyl, pyridinyl and thienyl;

B is selected from the group consisting of benzyloxy, morpholinyl, phenyl, thienyl, t-butyl, —NH—C(O)-cyclobutyl and —NH—C(O)-phenyl;

R 4 is H or NH 2 ;

R 5 is selected from the optionally substituted group consisting of benzimidazolyl, 3,4-dihydrobenzo[1,4]thiazinyl, furo[3,2-c]pyridine, indazolyl, indolyl, isoquinolinyl, pyrazolo[3,4-d]pyrimidine, pyrrolo[2,3-b]pyridinyl, pyrrolo[2,3-c]pyridinyl, pyrrolo[2,3-d]pyridinyl, pyrrolo[3,2-d]pyridine, pyrrolo[2,3-d]pyrimidinyl, quinolinyl, quinazolinyl, thieno[2,3-c]pyridinyl, thieno[2,3-d]pyrimidine, thieno[3,2-c]pyridine, 7-azaindolinyl and 7-azaindolyl;

R 6 is H or R 6 is selected from the optionally substituted group consisting of (C 1 )alkoxy, (C 1 -C 3 )alkyl, benzo[b]thienyl, NH pyrimidinyl —NH—S(O) 2 -phenyl-NH-pyrimidinyl, —NH—C(O)-benzo[b]thienyl, pyrrolo[2,3-b]pyrimidinyl and pyridinyl; and

R 7 is selected from optionally substituted group consisting of benzofuranyl, benzothiazolyl, benzo[b]thienyl, indolyl, isoquinolinyl, quinolinyl, quinoxalinyl, and thieno[2,3-b]pyridinyl; or

R 7 is Y—Z wherein Y is attached to the indazole; and

Y is benzo[b]thienyl; and

Z is selected from the group consisting of phenyl, thienyl, CH 2 NHCH 2 CH 2 -morpholinyl and substituted piperazinyl.

2. The compound of claim 1 wherein

R 1 is H or pyrimidinyl substituted with NH 2 ;

R 3 is selected from the group consisting of H, CH 3 , OH, Cl, benzo[b]thienyl, 2,3-dihydrobenzofuranyl, indolyl, naphthyl, phenyl, pyrazolyl, pyridinyl, pyrimidinyl, pyrrolyl, quinolinyl, thienyl, —NH—C(O)— cyclobutyl and —NH—C(O)-phenyl; wherein

the indolyl is optionally substituted with CH 3 ;

the naphthyl is optionally substituted with OCH 3 or OH; and

the phenyl optionally substituted with one or more substituents selected from the group consisting of CH 3 , NH 2 , Cl, F, N(CH 3 ) 2 , OH, CH 2 OH, C(O)NH 2 , COOH, CF 3 , OCF 3 , OCH 3 , CN, OCH 2 CH 3 , NHC(O)CH 3 , —S(O) 2 CH 3 and —C(O)—NH-pheny; or

R 3 is —C(O)—NY 100 —(C(Y 100 ) 2 ) x —R a wherein

x is 0 or 1;

Y 100 is H;

R a is selected from the optionally substituted group consisting of benzo[b]thienyl, benzimidazolyl, 1,3-dihydrobenzimidazolyl-2-one, benzotriazolyl, biphenyl, 1,3-dihydrobenzimidazolyl, indolyl, naphthyl and phenyl; wherein

the naphthyl is substituted with OH or OCH 3 ;

the phenyl is optionally substituted with one or more Cl, F, OH, CH 2 OH, CH 2 CH 2 OH, COOH, C(O)NH 2 , N(CH 3 ) 2 or methyl; or

R 3 is A-B wherein

A is selected from the group consisting of —C≡C, —C≡C-phenyl, phenyl and thienyl; and

B is selected from the group consisting of benzyloxy, phenyl, thienyl, —NH—C(O)-cyclobutyl and —NH—C(O)-phenyl;

R 4 is H;

R 5 is selected from the group consisting of

E is selected from the group consisting of H, OH, CH 3 , —CH 2 CH 2 NH 2 , CH 2 CH 2 CH 2 OH, CH 2 CH 2 OCH 3 , CH 2 CH 2 CH 2 NH 2 , CH 2 C(O)OH, CH 2 CH 2 C(O)OH, CH 2 CH 2 C(O)NH 2 , CH 2 CH 2 C(O)OCH 3 , CH 2 CH 2 CH 2 OCH 3 , NHCH 2 CH 2 CH 3 , CH 2 CH 2 C(O)NH(CH 3 ), CH 2 CH 2 C(O)N(CH 3 ) 2 , C(O)NHCH 2 CH 2 NH(CH 3 ), NHCH 2 CH 2 OCH 3 , NHCH 2 CH 2 OH, NHCH 2 CH 2 N(CH 3 ) 2 , isopropyl, CH 2 C(O)NH 2 , CH 2 CH(CH 3 )C(O)OH, CH 2 CH 2 CH 2 C(O)OH, CH 2 CH(CH 3 )C(O)OCH 3 , CH 2 CH 2 CH 2 CH 2 NH 2 , CH 2 CH 2 CH 2 C(O)NH 2 , N(CH 3 ) 2 , morpholinylethyl, piperidinylethyl,

 and 4-methylpiperazinylcyclohexyl;

R 6 is selected from the group consisting of H, pyrrolo[2,3-b]pyrimidinyl and

 and

R 7 is selected from the optionally substituted group consisting of benzofuranyl, benzo[b]thienyl, indolyl, pyrrolyl, quinolinyl, quinoxalinyl, and thieno[2,3-b]pyridinyl, wherein

the benzo[b]thienyl is optionally substituted with OH, CH 3 , OCH 3 , N(CH 3 ) 2 , OH, CH 2 ═CHNHCH 3 , CH 2 NH 2 , CH 2 CH 2 NH 2 or CH 2 NHCH 2 CH 2 N(CH 3 ) 2 ; and

the indolyl is substituted with C(O)N(CH(CH 3 ) 2 ) 2 , CH 2 OH, CH 2 C(O)NH 2 , COOH, C(O)NH 2 , N(CH 3 ) 2 or S(O) 2 CH 3 ;

R 7 is Y—Z wherein

Y is benzo[b]thienyl; and

Z is selected from the optionally substituted group consisting of CH═CHNHCH 3 , NHCH 3 , CH 2 NH 2 , CH 2 CH 2 NH 2 , CH 2 NHCH 3 , CH 2 NHCH 2 CH 2 N(CH 3 ) 2 , N(CH 3 ) 2 , CH 2 NHCH 2 CH 2 -morpholinyl, benzo[b]thienyl, morpholinylmethyl, piperazinylmethylphenyl and thienyl.

3. The compound of claim 2 wherein

R 1 is H or pyrimidinyl substituted with NH 2 ;

R 3 is selected from the group consisting of H, CH 3 , OH, Cl, benzo[b]thienyl, 2,3-dihydrobenzofuranyl, indolyl, naphthyl, phenyl, pyrazolyl, pyridinyl, pyrimidinyl, pyrrolyl, quinolinyl, thienyl, —NH—C(O)—cyclobutyl and —NH—C(O)-phenyl; wherein

the indolyl is optionally substituted with CH 3 ;

the naphthyl is optionally substituted with OH; and

the phenyl optionally substituted with one or more substituents selected from the group consisting of OH, F, CH 3 , CF 3 , CN, —C(O)NH 2 , NH 2 , NHC(O)CH 3 , OCH 3 , OCF 3 , OCH 2 CH 3 , N(CH 3 ) 2 , —C(O)—NH-phenyl and —S(O) 2 CH 3 ; or

R 3 is —C(O)—NY 100 —(C(Y 100 ) 2 ) x —R a wherein

Y 100 is H;

x is 0;

R a is selected from the optionally substituted group consisting of benzimidazolyl, 1,3-dihydrobenzimidazolyl-2-one, benzotriazolyl, biphenyl, indolyl, naphthyl and phenyl; wherein

the naphthyl is substituted with OH or OCH 3 ;

the phenyl is optionally substituted with one or more Cl, F, OH, CH 2 OH, CH 2 CH 2 OH, C(O)NH 2 , N(CH 3 ) 2 or methyl; or

R 3 is A-B wherein

A is selected from the group consisting of phenyl and thienyl; and

B is selected from the group consisting of benzyloxy, phenyl, thienyl, —NH—C(O)-cyclobutyl and —NH—C(O)-phenyl;

R 5 is selected from the group consisting of

 wherein

E is selected from the group consisting of H, CH 3 , CH 2 C(O)OH, CH 2 CH 2 CH 2 OH, CH 2 CH 2 CH 2 NH 2 , CH 2 CH 2 C(O)OH, CH 2 CH 2 C(O)NH 2 , CH 2 CH 2 C(O)OCH 3 , CH 2 CH 2 CH 2 OCH 3 , NHCH 2 CH 2 CH 3 , CH 2 CH 2 C(O)NH(CH 3 ), NHCH 2 CH 2 OCH 3 , NHCH 2 CH 2 OH, isopropyl, CH 2 C(O)NH 2 , CH 2 CH(CH 3 )C(O)OH, morpholinylethyl, piperidinylethyl, CH 2 CH 2 CH 2 C(O)OH, CH 2 CH(CH 3 )C(O)OCH 3 , CH 2 CH 2 NH 2 , CH 2 CH 2 CH 2 CH 2 NH 2 , CH 2 CH 2 CH 2 C(O)NH 2 , CH 2 CH 2 C(O)N(CH 3 ) 2 , and N(CH 3 ) 2 ;

R 6 is H or

 and

R 7 is selected from the optionally substituted group consisting of benzofuranyl, benzo[b]thienyl, indolyl, quinolinyl, quinoxalinyl, and thieno[2,3-b]pyridinyl, wherein

the benzo[b]thienyl is optionally substituted with OH, CH 3 , OCH 3 , N(CH 3 ) 2 , CH 2 ═CHNHCH 3 , CH 2 NH 2 , CH 2 CH 2 NH 2 or CH 2 NHCH 2 CH 2 N(CH 3 ) 2 ; and

the indolyl is substituted with methyl, CN, C(O)H, CH 2 CH 2 CH 2 NH 2 , CH 2 NHCH 2 CH═CH 2 , C(O)CH 3 , C(O)OCH 3 , OCH 3 , C(O)N(CH(CH 3 ) 2 ) 2 , CH 2 OH, CH 2 C(O)NH 2 , C(O)NH 2 , CH 2 NHCH 2 CH 2 N(CH 3 ) 2 or piperidinylmethyl; or

R 7 is Y—Z wherein

Y is benzo[b]thienyl; and

Z is selected from the optionally substituted group consisting of CH═CHNHCH 3 , NHCH 3 , CH 2 NH 2 , CH 2 CH 2 NH 2 , CH 2 NHCH 3 , CH 2 NHCH 2 CH 2 N(CH 3 ) 2 , N(CH 3 ) 2 , CH 2 NHCH 2 CH 2 -morpholinyl, benzo[b]thienyl, morpholinylmethyl and piperazinylmethyl; wherein

the piperazinyl is optionally substituted with methyl.

4. The compound of claim 3 wherein

R 1 and R 4 are H;

R 3 is selected from the optionally substituted group consisting of H, OH, 2,3-dihydrobenzofuranyl, naphthyl, pyrazolyl and pyrrolyl; wherein

R 3 is —C(O)—NY 100 —(C(Y 100 ) 2 ) x —R a wherein

Y 100 is H;

x is 0;

R a is selected from the optionally substituted group consisting of naphthyl and phenyl; wherein

the naphthyl is optionally substituted with OH;

the phenyl is optionally substituted with OH; or

R 3 is selected from the group consisting of —NH—C(O)-cyclobutyl and —NH—C(O)-phenyl;

R 3 is A-B wherein

A is selected from the group consisting of phenyl and thienyl; and

B is selected from the group consisting of benzyloxy, phenyl and thienyl;

R 5 is

 wherein

E is selected from the group consisting of H, CH 2 C(O)NH 2 , CH 2 CH(CH 3 )C(O)OCH 3 , CH 2 CH 2 CH 2 OH, CH 2 CH 2 C(O)OCH 3 , CH 2 CH 2 CH 2 OCH 3 , CH 2 CH 2 NH 2 , CH 2 CH 2 CH 2 NH 2 , CH 2 CH 2 C(O)OH, CH 2 CH 2 C(O)NH 2 , CH 2 CH 2 CH 2 CH 2 NH 2 , CH 2 CH 2 CH 2 OCH 3 , CH 2 CH 2 CH 2 C(O)OH, CH 2 CH 2 CH 2 C(O)NH 2 , CH 2 CH(CH 3 )C(O)OH, CH 2 CH 2 C(O)NH(CH 3 ), CH 2 CH 2 C(O)N(CH 3 ) 2 , N(CH 3 ) 2 , isopropyl, morpholinylethyl and piperidinylethyl;

R 6 is H or

 and

R 7 is selected from the optionally substituted group consisting of benzofuranyl, benzo[b]thienyl, indolyl, and quinolinyl, wherein

the benzo[b]thienyl is optionally substituted with OH, CH 3 , OCH 3 , N(CH 3 ) 2 , CH 2 ═CH 2 NHCH 3 , CH 2 NH 2 , CH 2 CH 2 NH 2 , CH 2 NHCH 2 CH 2 N(CH 3 ) 2 , piperidinylmethyl or CH 2 NHCH 2 N(CH 3 ) 2 ; and

the indolyl is optionally substituted with methyl, CN, C(O)H, CH 2 CH 2 CH 2 NH 2 , CH 2 NHCH 2 CH═CH 2 , C(O)CH 3 , C(O)OCH 3 , or OCH 3 ; methyl, CN, C(O)H, CH 2 CH 2 CH 2 NH 2 , CH 2 NHCH 2 CH═CH 2 , C(O)CH 3 , C(O)OCH 3 , or OCH 3 ;

or

R 7 is Y—Z wherein

Y is benzo[b]thienyl; and

Z is selected from the group consisting of CH═CHNHCH 3 , NHCH 3 , CH 2 NH 2 , CH 2 CH 2 NH 2 , CH 2 NHCH 3 , CH 2 NHCH 2 CH 2 N(CH 3 ) 2 , N(CH 3 ) 2 , CH 2 NHCH 2 CH 2 -morpholinyl, benzo[b]thienyl, morpholinylmethyl and piperazinylmethyl;

wherein the piperazinyl is optionally substituted with methyl.

5. The compound of claim 4 wherein

R 1 and R 4 are H;

R 3 is selected from the group consisting of H, OH, 2,3-dihydrobenzofuranyl, pyrrolyl and optionally substituted napthyl; or

R 3 is —C(O)—NY 100 —(C(Y 100 ) 2 ) x —R a wherein

Y 100 is H;

x is 0; and

R a is phenyl substituted with OH;

R 5 is

 wherein

E is selected from the group consisting of H, CH 2 C(O)NH 2 , CH 2 CH 2 NH 2 , CH 2 CH 2 CH 2 NH 2 , CH 2 CH 2 CH 2 CH 2 NH 2 , CH 2 CH 2 CH 2 OCH 3 , CH 2 CH 2 CH 2 OH, CH 2 CH 2 C(O)OH, CH 2 CH 2 CH 2 C(O)OH, CH 2 CH 2 C(O)NH 2 , CH 2 CH 2 CH 2 C(O)NH 2 , CH 2 CH(CH 3 )C(O)OCH 3 CH 2 CH(CH 3 )C(O)OH, CH 2 CH 2 C(O)OCH 3 , CH 2 CH 2 C(O)NH(CH 3 ), CH 2 CH 2 C(O)N(CH 3 ) 2 , N(CH 3 ) 2 , isopropyl, morpholinylethyl and piperidinylethyl;

R 6 is H or

 and

R 7 is selected from the optionally substituted group consisting of benzofuranyl, benzo[b]thienyl, indolyl, and quinolinyl;

wherein

the benzo[b]thienyl optionally substituted with OH, CH 3 , OCH 3 , CH 2 ═CH 3 —NHCH 3 , CH 2 NH 2 , CH 2 CH 2 NH 2 , CH 2 NHCH 2 CH 2 N(CH 3 ) 2 , N(CH 3 ) 2 or piperidinylmethyl; and

the indolyl is optionally substituted with methyl, CN, C(O)H, CH 2 CH 2 CH 2 NH 2 , CH 2 NHCH 2 CH═CH 2 , C(O)CH 3 , C(O)OCH 3 , or OCH 3 ;

or

R 7 is Y—Z wherein

Y is benzo[b]thienyl; and

Z is selected from the group consisting of CH 2 NHCH 2 CH 2 -morpholinyl, morpholinylmethyl and piperazinylmethyl wherein the piperazinyl is optionally substituted with methyl.

6. The compound of claim 5 wherein

R 1 , R 3 , R 4 and R 6 are H;

R 5 is

 wherein

E is selected from the group consisting of H, —CH 2 CH 2 NH 2 , CH 2 CH 2 CH 2 NH 2 , CH 2 CH 2 CH 2 OH, CH 2 CH 2 C(O)OH and CH 2 CH 2 C(O)NH 2 ; and

R 7 is selected from the group consisting of benzo[b]thienyl, and indolyl, wherein

the benzo[b]theinyl is optionally substituted by piperidinylmethyl; and

the indolyl is optionally substituted by CN, methyl or C(O)H.

7. The compound of claim 6 wherein

R 1 , R 3 , R 4 and R 6 are H;

R 5 is

 wherein

E is selected from the group consisting of H, —CH 2 CH 2 NH 2 , CH 2 CH 2 CH 2 NH 2 , CH 2 CH 2 CH 2 OH, CH 2 CH 2 C(O)OH and CH 2 CH 2 C(O)NH 2 ; and

R 7 is benzo[b]thienyl or indolyl wherein

the benzo[b]theinyl is optionally substituted by piperidinylmethyl;

the indolyl is optionally substituted by CN, methyl or C(O)H.

8. The compound of claim 7 wherein R 1 , R 3 , R 4 and R 6 are H;

R 5 is

 wherein

E is selected from the group consisting of —CH 2 CH 2 NH 2 , CH 2 CH 2 CH 2 NH 2 , CH 2 CH 2 CH 2 OH, CH 2 CH 2 C(O)OH and CH 2 CH 2 C(O)NH 2 ; and

R 7 is benzo[b]thienyl.