IP Library Granted Patent US 6,897,231
Granted Patent B2
US 6,897,231 · App. 09/910,950 · Granted May 24, 2005

Indazole derivatives as JNK inhibitors and compositions and methods related thereto

Assignee: Signal Pharmaceuticals, Inc.
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Quick Facts
Patent No.
US 6,897,231
App. No.
09/910,950
Granted
May 24, 2005
Kind
B2
Abstract

Compounds having activity as selective inhibitors of JNK are disclosed. The compounds of this invention are indazole derivatives having the following structure: wherein R 1 , R 2 and A are as defined herein. Such compounds have utility in the treatment of a wide range of conditions that are responsive to JNK inhibition. Thus, methods of treating such conditions are also disclosed, as are pharmaceutical compositions containing one or more compounds of the above compounds.

Claims (449)

1. A compound having the structure:

or a pharmaceutically acceptable salt thereof, wherein:

A is —(CH 2 ) b C≡C(CH 2 ) c —;

R 1 is aryl, heteroaryl or heterocycle fused to phenyl, each being optionally substituted with one to four substituents independently selected from R 3 ;

R 2 is —R 3 , —R 4 , —(CH 2 ) b C(═O)R 5 , —(CH 2 ) b C(═O)OR 5 , —(CH 2 ) b C(═O)NR 5 R 6 , —(CH 2 ) b C(═O)NR 5 (CH 2 ) c C(═O)R 6 , —(CH 2 ) b NR 5 C(═O)R 6 , —(CH 2 ) b NR 5 C(═O)NR 6 R 7 , —(CH 2 ) b NR 5 R 6 , —(CH 2 ) b OR 5 , —(CH 2 ) b SO d R 5 or —(CH 2 ) b SO2NR 5 R 6 ;

b and c are the same or different and at each occurrence independently selected from 0, 1, 2, 3 or 4;

d is at each occurrence 0, 1 or 2;

R 3 is at each occurrence independently halogen, hydroxy, carboxy, alkyl, alkoxy, haloalkyl, acyloxy, thioalkyl, sulfinylalkyl, sulfonylalkyl, hydroxyalkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heterocycle, substituted heterocycle, heterocyclealkyl, substituted heterocyclealkyl, —C(═O)OR 8 , —C(O)R 8 , —C(O)NR 8 R 9 , —C(═O)NR 8 OR 9 , —SO 2 NR 8 R 9 , —NR 8 SO 2 R 9 , —CN, —NO 2 , —NR 8 R 9 , —NR 8 C(═O)R 9 , —NR 8 C(═O)(CH 2 ) b OR 9 , —NR 8 C(═O)(CH 2 ) b R 9 , —O(CH 2 ) b NR 8 R 9 , or heterocycle fused to phenyl;

R 4 is alkyl, aryl, arylalkyl, heterocycle or heterocyclealkyl, each being optionally substituted with one to four substituents independently selected from R 3 , or R 4 is halogen or hydroxy;

R 5 , R 6 and R 7 are the same or different and at each occurrence independently hydrogen, alkyl, aryl, arylalkyl, heterocycle or heterocyclealkyl, wherein each of R 5 , R 6 and R 7 are optionally substituted with one to four substituents independently selected from R 3 ; and

R 8 and R 9 are the same or different and at each occurrence independently hydrogen, alkyl, aryl, arylalkyl, heterocycle, or heterocyclealkyl, or R 8 and R 9 taken together with the atom or atoms to which they are bonded form a heterocycle, wherein each of R 8 , R 9 , and R 8 and R 9 taken together to form a heterocycle are optionally substituted with one to four substituents independently selected from R 3 .

2. A compound having the structure:

or a pharmaceutically acceptable salt thereof, wherein:

A is a direct bond, —(CH 2 ) a —, —(CH 2 ) b CH═CH(CH 2 ) c —, or —(CH 2 ) b C≡C(CH 2 ) c —;

R 1 is aryl, heteroaryl or heterocycle fused to phenyl, each being optionally substituted with one to four substituents independently selected from R 3 ;

R 2 is —(CH 2 ) b C(═O)R 5 ;

a is 1, 2, 3, 4, 5 or 6;

b and c are the same or different and at each occurrence independently selected from 0, 1, 2, 3 or 4;

R 3 is at each occurrence independently halogen, hydroxy, carboxy, alkyl, alkoxy, haloalkyl, acyloxy, thioalkyl, sulfinylalkyl, sulfonylalkyl, hydroxyalkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heterocycle, substituted heterocycle, heterocyclealkyl, substituted heterocyclealkyl, —C(═O)OR 8 , —C(═O)R 8 , —C(O)NR 8 R 9 , —C(═O)NR 8 OR 9 , —SO 2 NR 8 R 9 , —NR 8 SO 2 R 9 , —CN, —NO 2 , —NR 8 R 9 , —NR 8 C(═O)R 9 , —NR 8 C(═O)(CH 2 ) b OR 9 , —NR 8 C(═O)(CH 2 ) b R 9 , —O(CH 2 ) b NR 8 R 9 , or heterocycle fused to phenyl;

R 5, R 6 and R 7 are the same or different and at each occurrence independently alkyl, aryl, arylalkyl, heterocycle or heterocyclealkyl, wherein each of R 5, R 6 and R 7 are optionally substituted with one to four substituents independently selected from R 3 ; and

R 8 and R 9 are the same or different and at each occurrence independently hydrogen, alkyl, aryl, arylalkyl, heterocycle, or heterocyclealkyl, or R 8 and R 9 taken together with the atom or atoms to which they are bonded form a heterocycle, wherein each of R 8 , R 9 , and R 8 and R 9 taken together to form a heterocycle are optionally substituted with one to four substituents independently selected from R 3 .

3. A compound having the structure:

or a pharmaceutically acceptable salt thereof, wherein:

A is a direct bond, —(CH 2 ) a —, —(CH 2 ) b CH═CH(CH 2 ) c —, or —(CH 2 ) b C≡C(CH 2 ) c —;

R 1 is aryl, heteroaryl or heterocycle fused to phenyl, each being optionally substituted with one to four substituents independently selected from R 3 ;

R 2 is —(CH 2 ) b C(═O)NR 5 R 6 ;

a is 1, 2, 3, 4, 5 or 6;

b and c are the same or different and at each occurrence independently selected from 0, 1, 2, 3 or 4;

R 3 is at each occurrence independently halogen, hydroxy, carboxy, alkyl, alkoxy, haloalkyl, acyloxy, thioalkyl, sulfinylalkyl, sulfonylalkyl, hydroxyalkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heterocycle, substituted heterocycle, heterocyclealkyl, substituted heterocyclealkyl, —C(═O)OR 8 , —C(═O)R 8 , —C(O)NR 8 R 9 , —C(═O)NR 8 OR 9 , —SO 2 NR 8 R 9 , —NR 8 SO 2 R 9 , —CN, —NO 2 , —NR 8 R 9 , —NR 8 C(═O)R 9 , —NR 8 C(═O)(CH 2 ) b OR 9 , —NR 8 C(═O)(CH 2 ) b R 9 , —O(CH 2 ) b NR 8 R 9 , or heterocycle fused to phenyl;

R 5 , R 6 and R 7 are the same or different and at each occurrence independently hydrogen, alkyl, aryl, arylalkyl, heterocycle or heterocyclealkyl, wherein each of R 5 , R 6 and R 7 are optionally substituted with one to four substituents independently selected from R 3 ; and

R 8 and R 9 are the same or different and at each occurrence independently hydrogen, alkyl, aryl, arylalkyl, heterocycle, or heterocyclealkyl, or R 8 and R 9 taken together with the atom or atoms to which they are bonded form a heterocycle, wherein each of R 8 , R 9 , and R 8 and R 9 taken together to form a heterocycle are optionally substituted with one to four substituents independently selected from R 3 .

4. A compound having the structure:

or a pharmaceutically acceptable salt thereof, wherein:

A is a direct bond, —(CH 2 ) a —, —(CH 2 ) b CH═CH(CH 2 ) c —, or —(CH 2 ) b C≡C(CH 2 ) c —;

R 1 is aryl, heteroaryl or heterocycle fused to phenyl, each being optionally substituted with one to four substituents independently selected from R 3 ;

R 2 is —(CH 2 ) b NR 5 C(═O)R 6 ;

a is 1, 2, 3, 4, 5 or 6;

b and c are the same or different and at each occurrence independently selected from 0, 1, 2, 3 or 4;

R 3 is at each occurrence independently halogen, hydroxy, carboxy, alkyl, alkoxy, haloalkyl, acyloxy, thioalkyl, sulfinylalkyl, sulfonylalkyl, hydroxyalkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heterocycle, substituted heterocycle, heterocyclealkyl, substituted heterocyclealkyl, —C(O)OR 8 , —C(═O)R 8 , —C(O)NR 8 R 9 , —C(═O)NR 8 OR 9 , —SO 2 NR 8 R 9 , —NR 8 SO 2 R 9 , —CN, —NO 2 , —NR 8 R 9 , —NR 8 C(═O)R 9 , —NR 8 C(═O)(CH 2 ) b OR 9 , —NR 8 C(═O)(CH 2 ) b R 9 , —O(CH 2 ) b NR 8 R 9 , or heterocycle fused to phenyl;

R 5 , R 6 and R 7 are the same or different and at each occurrence independently hydrogen, alkyl, aryl, arylalkyl, heterocycle or heterocyclealkyl, wherein each of R 5 , R 6 and R 7 are optionally substituted with one to four substituents independently selected from R 3 ; and

R 8 and R 9 are the same or different and at each occurrence independently hydrogen, alkyl, aryl, arylalkyl, heterocycle, or heterocyclealkyl, or R 8 and R 9 taken together with the atom or atoms to which they are bonded form a heterocycle, wherein each of R 8 , R 9 , and R 8 and R 9 taken together to form a heterocycle are optionally substituted with one to four substituents independently selected from R 3 .

5. A compound having the structure:

or a pharmaceutically acceptable salt thereof, wherein:

A is a direct bond, —(CH 2 ) a —, —(CH 2 ) b CH═CH(CH 2 ) c —, or —(CH 2 ) b C≡C(CH 2 ) c —;

R 1 is aryl, heteroaryl or heterocycle fused to phenyl, each being optionally substituted with one to four substituents independently selected from R 3 ;

R 2 is R 4 ;

a is 1, 2, 3, 4, 5 or 6;

b and c are the same or different and at each occurrence independently selected from 0, 1, 2, 3 or 4;

R 3 is at each occurrence independently halogen, hydroxy, carboxy, alkyl, alkoxy, haloalkyl, acyloxy, thioalkyl, sulfinylalkyl, sulfonylalkyl, hydroxyalkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heterocycle, substituted heterocycle, heterocyclealkyl, substituted heterocyclealkyl, —C(═O)OR 8 , —C(═O)R 8 , —C(O)NR 8 R 9 , —C(═O)NR 8 OR 9 , —SO 2 NR 8 R 9 , —NR 8 SO 2 R 9 , —CN, —NO 2 , —NR 8 R 9 , —NR 8 C(═O)R 9 , —NR 8 C(═O)(CH 2 ) b OR 9 , —NR 8 C(═O)(CH 2 ) b R 9 , —O(CH 2 ) b NR 8 R 9 , or heterocycle fused to phenyl;

R 4 is 3-triazolyl, optionally substituted at its 5-position with:

(a) a C 1 -C 4 straight or branched chain alkyl group optionally substituted with a hydroxyl, methylamino, dimethylamino or 1-pyrrolidinyl group; or (b) a 2-pyrrolidinyl group;

R 5 , R 6 and R 7 are the same or different and at each occurrence independently hydrogen, alkyl, aryl, arylalkyl, heterocycle or heterocyclealkyl, wherein each of R 5 , R 6 and R 7 are optionally substituted with one to four substituents independently selected from R 3 ; and

R 8 and R 9 are the same or different and at each occurrence independently hydrogen, alkyl, aryl, arylalkyl, heterocycle, or heterocyclealkyl, or R 8 and R 9 taken together with the atom or atoms to which they are bonded form a heterocycle, wherein each of R 8 , R 9 , and R 8 and R 9 taken together to form a heterocycle are optionally substituted with one to four substituents independently selected from R 3 .

6. A compound having the structure:

or a pharmaceutically acceptable salt thereof, wherein:

A is a direct bond, —(CH 2 ) a —, —(CH 2 ) b CH═CH(CH 2 ) c —, or —(CH 2 ) b C≡C(CH 2 ) c —;

R 1 is aryl, heteroaryl or heterocycle fused to phenyl, each being optionally substituted with one to four substituents independently selected from R 3 ;

R 2 is R 4 ;

a is 1, 2, 3, 4, 5 or 6;

b and c are the same or different and at each occurrence independently selected from 0, 1, 2, 3 or 4;

R 3 is at each occurrence independently halogen, hydroxy, carboxy, alkyl, alkoxy, haloalkyl, acyloxy, thioalkyl, sulfinylalkyl, sulfonylalkyl, hydroxyalkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heterocycle, substituted heterocycle, heterocyclealkyl, substituted heterocyclealkyl, —C(═O)OR 8 , —C(═O)R 8 , —C(O)NR 8 R 9 , —C(═O)NR 8 OR 9 , —SO 2 NR 8 R 9 , —NR 8 SO 2 R 9 , —CN, —NO 2 , —NR 8 R 9 , —NR 8 C(═O)R 9 , —NR 8 C(═O)(CH 2 ) b OR 9 , —NR 8 C(═O)(CH 2 ) b R 9 , —O(CH 2 ) b NR 8 R 9 , or heterocycle fused to phenyl;

R 4 is tetrazole;

R 5 , R 6 and R 7 are the same or different and at each occurrence independently hydrogen, alkyl, aryl, arylalkyl, heterocycle or heterocyclealkyl, wherein each of R 5 , R 6 and R 7 are optionally substituted with one to four substituents independently selected from R 3 ; and

R 8 and R 9 are the same or different and at each occurrence independently hydrogen, alkyl, aryl, arylalkyl, heterocycle, or heterocyclealkyl, or R 8 and R 9 taken together with the atom or atoms to which they are bonded form a heterocycle, wherein each of R 8 , R 9 , and R 8 and R 9 taken together to form a heterocycle are optionally substituted with one to four substituents independently selected from R 3 .

7. A compound having the structure:

or a pharmaceutically acceptable salt thereof, wherein:

A is a direct bond, —(OH 2 ) a —, —(CH 2 ) b CH═CH(CH 2 ) c —, or —(CH 2 ) b C≡C(CH 2 ) c —;

R 1 is aryl, heteroaryl or heterocycle fused to phenyl, each being optionally substituted with one to four substituents independently selected from R 3 ;

R 2 is R 4 ,

a is 1, 2, 3, 4, 5 or 6;

b and c are the same or different and at each occurrence independently selected from 0, 1, 2, 3 or 4;

R 3 is at each occurrence independently halogen, hydroxy, carboxy, alkyl, alkoxy, haloalkyl, acyloxy, thioalkyl, sulfinylalkyl, sulfonylalkyl, hydroxyalkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heterocycle, substituted heterocycle, heterocyclealkyl, substituted heterocyclealkyl, —C(═O)OR 8 , —O(═O)R 8 , —C(O)NR 8 R 9 , —C(═O)NR 8 OR 9 , —SO 2 NR 8 R 9 , —NR 8 SO 2 R 9 , —CN, —NO 2 , —NR 8 R 9 , —NR 8 C(═O)R 9 , —NR 8 C(═O)(CH 2 ) b OR 9 , —NR 8 C(═O)(CH 2 ) b R 9 , —O(CH 2 ) b NR 8 R 9 , or heterocycle fused to phenyl;

R 4 is imidazole;

R 5 , R 6 and R 7 are the same or different and at each occurrence independently hydrogen, alkyl, aryl, arylalkyl, heterocycle or heterocyclealkyl, wherein each of R 8 , R 6 and R 7 are optionally substituted with one to four substituents independently selected from R 3 ; and

R 8 and R 9 are the same or different and at each occurrence independently hydrogen, alkyl, aryl, arylalkyl, heterocycle, or heterocyclealkyl, or R 8 and R 9 taken together with the atom or atoms to which they are bonded form a heterocycle, wherein each of R 8 , R 9 , and R 8 and R 9 taken together to form a heterocycle are optionally substituted with one to four substituents independently selected from R 3 .

8. A compound having the structure:

or a pharmaceutically acceptable salt thereof, wherein:

—A—R 1 is phenyl, optionally substituted with one to four substituents independently selected from halogen, alkoxy, —NR 8 C(═O)R 9 , —C(═O)NR 8 R 9 , and —O(CH 2 ) b NR 8 R 9 ;

R 2 is 3-triazolyl or 5-tetrazolyl;

a is 1, 2, 3, 4, 5 or 6;

b is 2 or 3;

c is at each occurrence 0, 1, 2, 3 or 4;

R 3 is at each occurrence independently halogen, hydroxy, carboxy, alkyl, alkoxy, haloalkyl, acyloxy, thioalkyl, sulfinylalkyl, sulfonylalkyl, hydroxyalkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heterocycle, substituted heterocycle, heterocyclealkyl, substituted heterocyclealkyl, —C(═O)OR 8 , —C(═O)R 8 , —C(O)NR 8 R 9 , —C(═O)NR 8 OR 9 , —SO 2 NR 8 R 9 , —NR 8 SO 2 R 9 , —CN, —NO 2 , —NR 8 R 9 , —NR 8 C(═O)R 9 , —NR 8 C(═O)(CH 2 ) b OR 9 , —NR 8 C(═O)(CH 2 ) b R 9 , —O(CH 2 ) b NR 8 R 9 , or heterocycle fused to phenyl;

R 5 , R 6 and R 7 are the same or different and at each occurrence independently hydrogen, alkyl, aryl, arylalkyl, heterocycle or heterocyclealkyl, wherein each of R 5 , R 6 and R 7 are optionally substituted with one to four substituents independently selected from R 3 ; and

R 8 and R 9 are the same or different and at each occurrence independently hydrogen, alkyl, aryl, arylalkyl, heterocycle, or heterocyclealkyl, or R 8 and R 9 taken together with the atom or atoms to which they are bonded form a heterocycle, wherein each of R 8 , R 9 , and R 8 and R 9 taken together to form a heterocycle are optionally substituted with one to four substituents independently selected from R 3 .

9. A compound having the structure:

or a pharmaceutically acceptable salt thereof, wherein:

A is a direct bond, —(CH 2 ) a —, —(CH 2 ) b CH═CH(CH 2 ) c —, or —(CH 2 ) b C≡C(CH 2 ) c —;

R 1 is aryl, heteroaryl or heterocycle fused to phenyl, each being optionally substituted with one to four substituents independently selected from R 3 ;

R 2 is R 4 ;

a is 1, 2, 3, 4, 5 or 6;

b and c are the same or different and at each occurrence independently selected from 0, 1, 2, 3 or 4;

R 3 is at each occurrence independently halogen, hydroxy, carboxy, alkyl, alkoxy, haloalkyl, acyloxy, thioalkyl, sulfinylalkyl, sulfonylalkyl, hydroxyalkyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heterocycle, substituted heterocycle, heterocyclealkyl, substituted heterocyclealkyl, —C(═O)OR 8 , —C(═O)R 8 , —C(O)NR 8 R 9 , —C(═O)NR 8 OR 9 , —SO 2 NR 8 R 9 , —NR 8 SO 2 R 9 , —CN, —NO 2 , —NR 8 R 9 , —NR 8 C(═O)R 9 , —NR 8 C(═O)(CH 2 ) b OR 9 , —NR 8 C(═O)(CH 2 ) b R 9 , —O(CH 2 ) b NR 8 R 9 , or heterocycle fused to phenyl;

R 4 is 3-triazolyl, optionally substituted at its 5-position with:

(a) methyl, n-propyl, isopropyl, 1-hydroxyethyl, 3-hydroxypropyl, methylaminomethyl, dimethylaminomethyl, 1-(dimethylamino)ethyl, 1-pyrrolidinylmethyl or 2-pyrrolidinyl;

R 5 , R 6 and R 7 are the same or different and at each occurrence independently hydrogen, alkyl, aryl, arylalkyl, heterocycle or heterocyclealkyl, wherein each of R 5 , R 6 and R 7 are optionally substituted with one to four substituents independently selected from R 3 ; and

R 8 and R 9 are the same or different and at each occurrence independently hydrogen, alkyl, aryl, arylalkyl, heterocycle, or heterocyclealkyl, or R 8 and R 9 taken together with the atom or atoms to which they are bonded form a heterocycle, wherein each of R 8 , R 9 , and R 8 and R 9 taken together to form a heterocycle are optionally substituted with one to four substituents independently selected from R 3 .

10. A composition comprising the compound of claim 1 and a pharmaceutically acceptable carrier.

11. A composition comprising the compound of claim 2 and a pharmaceutically acceptable carrier.

12. A composition comprising the compound of claim 3 and a pharmaceutically acceptable carrier.

13. A composition comprising the compound of claim 4 and a pharmaceutically acceptable carrier.

14. A composition comprising the compound of claim 5 and a pharmaceutically acceptable carrier.

15. A composition comprising the compound of claim 6 and a pharmaceutically acceptable carrier.

16. A composition comprising the compound of claim 7 and a pharmaceutically acceptable carrier.

17. A composition comprising the compound of claim 8 and a pharmaceutically acceptable carrier.

18. A composition comprising the compound of claim 9 and a pharmaceutically acceptable carrier.

19. A compound of claim 1 , wherein the compound is:

3-(2-phenylethynyl)-1H-indazole-5-carboxamide, or a pharmaceutically acceptable salt thereof.

20. A compound of claim 2 , wherein the compound is:

1-{(3-(4-fluorophenyl)-1H-indazol-5-yl)carbonyl}piperidine-4-carboxylic acid;

3-(4-fluorophenyl)(1H-indazol-5-yl)pyrrolidinyl ketone;

3-(4-fluorophenyl)(1H-indazol-5-yl)piperazinyl ketone;

1-(3-(4-fluorophenyl)-1H-indazol-5-yl)-2-phenylethan-1-one;

1-(3-(4-fluorophenyl)-1H-indazol-5-yl)ethan-1-one; or a pharmaceutically acceptable salt thereof.

21. A compound of claim 3 , wherein the compound is:

3-(4-fluorophenyl)-1H-indazole-5-carboxamide;

(3-(4-fluorophenyl)(1H-indazol-5-yl))-N-benzamide;

N-(2-(dimethylamino)ethyl)3-(4-fluorophenyl)(1H-indazol-5-yl))carboxamide;

methyl 4-{(3-(4-fluorophenyl)-1H-indazol-5-yl)carbonylamino}benzoate;

4-{3-(4-fluorophenyl)-1H-indazol-5-yl)carbonylamino}benzoic acid;

4-{(3-(4-fluorophenyl)-1H-indazole-5-yl)carbonylamino}benzamide;

(3-(4-fluorophenyl)(1H-indazol-5-yl))-N-(2-pyridyl)carboxamide;

(3-(4-fluorophenyl)(1H-indazol-5-yl))-N-(3-pyridyl)carboxamide;

(3-(4-fluorophenyl)(1H-indazol-5-yl))-N-(4-pyridyl)carboxamide;

tert-butyl 3-{(3-(4-fluorophenyl)-1H-indazol-5-yl)carbonylamino)propanoate;

(3-(4-fluorophenyl)(1H-indazol-5-yl))-N-(3-hydroxyphenyl)carboxamide;

3-{(3-(4-fluorophenyl)-1H-indazol-5-yl)carbonylamino)propanoic acid;

(3-(4-fluorophenyl)(1H-indazol-5-yl))-N-(3-nitrophenyl)carboxamide;

tert-butyl-2-{(3-(4-fluorophenyl)-1H-indazol-5-yl)carbonylamino}acetate;

4-{(3-(4-fluorophenyl)-1H-indazol-5-yl)carbonylamino}butanoic acid;

N-(3-aminophenyl)(3-(4-fluorophenyl)(1H-indazol-5-yl))carboxamide;

2-{(3-(4-fluorophenyl)-1H-indazol-5-yl)carbonylamino}acetic acid;

5-{(3-(4-fluorophenyl)-1H-indazol-5-yl)carbonylamino}pentanoic acid;

4-({(3-(4-fluorophenyl)-1H-indazol-5-yl)carbonylamino}methyl)benzoic acid;

(3-(4-fluorophenyl)(1H-indazol-5-yl))-N-(4-pyridylmethyl)carboxamide;

2-(4-{(3-(4-fluorophenyl)-1H-indazol-5-yl)carbonylamino}phenyl)acetic acid;

(3-(4-fluorophenyl)(1H-indazol-5-yl))-N,N-dimethylcarboxamide;

(3-(4-fluorophenyl)(1H-indazol-5-yl))-N-methylcarboxamide;

N-(3-aminoethyl)(3-(4-fluorophenyl)(1H-indazol-5-yl))carboxamide;

N-(3-aminopropyl)(3-(4-fluorophenyl)(1H-indazol-5-yl))carboxamide;

(3-(4-fluorophenyl)(1H-indazol-5-yl))-N-(2-hydroxypropyl)carboxamide;

N-(2H-1,2,3,4-tetrazol-5-yl)(3-(4-fluorophenyl)(1H-indazol-5-yl))carboxamide;

{3-(4-fluorophenyl)(1H-indazol-5-yl)}-N-(3-morpholin-4-ylpropyl)carboxamide;

(3-(4-fluorophenyl)(1H-indazol-5-yl)}-N-(3-pyridylmethyl)carboxamide;

N-(((2R)-2-hydroxycyclohexyl)methyl)(3-(4-fluorophenyl)(1H-indazole-5-yl)carboxamide

(3-(4-fluorophenyl)(1H-indazol-5-yl))-N-(2-(1-methylimidazol-5-yl)ethyl)carboxamide);

(3-(4-fluorophenyl)(1H-indazol-5-yl))-N-(2-pyridylmethyl)carboxamide

N-(2-carbamoylethyl)(3-(4-fluorophenyl)(1H-indazol-5-yl))carboxamide;

N-(3-carbamoylpropyl)(3-(4-fluorophenyl)(1H-indazol-5-yl))carboxamide;

3-(4-methoxyphenyl)-1H-indazole-5-carboxamide;

3-(4-hydroxyphenyl)-1H-indazole-5-carboxamide;

3-(2-naphthyl)-1H-indazole-5-carboxamide;

3-benzo(b)thiophen-2-yl-1H-indazole-5-carboxamide;

3-benzo(d)furan-2-yl-1H-indazole-5-caxboxamide;

3-(3-(methylethyl)phenyl)-1H-indazole-5-carboxamide;

3-(4-(dimethylamino)phenyl)-1H-indazole-5-carboxamide;

3-(3-furyl)-1H-indazole-5-carboxamide;

3-{4-(2-(dimethylamino)ethoxy)phenyl}-1H-indazole-5-carboxamide;

3-(3,4-dimethoxyphenyl)-1H-indazole-5-carboxamide;

3-(3-aminophenyl)-1H-indazole-5-carboxamide;

3-(2H-benzo(d)1,3-dioxolen-5-yl)-1H-indazole-5-carboxamide;

(3-benzo(d)furan-2-yl(1H-indazol-5-yl))-N-(methylethyl)carboxamide;

(3-benzo(d)furan-2-yl(1H-indazol-5-yl))-N-(2-methoxyethyl)carboxamide;

(3-benzo(d)furan-2-yl(1H-indazol-5-yl))-N-(2-(dimethylamino)ethyl)carboxamide;

(3-benzo(d)furan-2-yl(1H-indazol-5-yl))-N-(4-(dimethylamino)butyl)carboxamide;

(3-benzo(d)furan-2-yl(1H-indazol-5-yl))-N-(3-(dimethylamino)propyl)carboxamide;

(3-benzo(d)furan-2-yl(1H-indazol-5-yl))-N-(2-methylpropyl)carboxamide;

(3-benzo(d)furan-2-yl(1H-indazol-5-yl))-N-methylcarboxamide;

3-(3-(3-pyridylcarbonylamino)phenyl)-1H-indazole-5-carboxamide;

3-(3-(2-methoxyacetylamino)phenyl)-1H-indazole-5-carboxamide;

3-(3-(4-pipendylcarboxyamino)phenyl)-1H-indazole-5-carboxamide;

(1S)-1-{N-(3-(5-carbamoyl(1H-indazol-3-yl))phenyl)carbamoyl}ethyl acetate;

3-{3-(2-methoxyethyl)amino)phenyl}-1H-indazole-5-carboxamide;

3-(3-(3-piperidylpropanoylamino)phenyl)-1H-indazole-5-carboxamide;

3-(3-(2-furylcarbonylamino)phenyl)-1H-indazole-5-carboxamide;

3-{3-(2-(dimethylamino)acetylamino)phenyl}-1H-indazole-5-carboxamide;

3-(3-(2-phenylacetylamino)phenyl)-1H-indazole-5-carboxamide;

3-{3-(2-(4-methoxyphenyl)acetylamino)phenyl}-1H-indazole-5-carboxamide;

3-{3-(2-(2-methyl-1,3-thiazol-5-yl)acetylamino)phenyl}-1H-indazole-5-carboxamide;

3-(3-(oxolan-3yl-carbonylamino)phenyl)-1H-indazole-5-carboxamide;

3-(3-(2-(3-thienyl)acetylamino)phenyl)-1H-indazole-5-carboxamide;

3-(3-(2-thienylcarbonylamino)phenyl)-1H-indazole-5-carboxamide;

3-(3-(2-(4-pyridyl)acetylamino)phenyl)-1H-indazole-5-carboxamide;

3-(3-(2-(2-pyridyl)acetylamino)phenyl)-1H-indazole-5-carboxamide;

3-{3-(2-(4-fluorophenyl)acetylamino)phenyl}-1H-indazole-5-carboxamide;

3-(3-(cyclopropylcarbonylamino)phenyl-1H-indazole-5-carboxamide;

3-{3-((3-hydroxyphenyl)carbonylamino)phenyl}-1H-indazole-5-carboxamide;

3-{3-(2-(2,4-dichlorophenyl)acetylamino)phenyl}-1H-indazole-5-carboxamide;

3-(3-{2-(4-(trifluoromethyl)phenyl)acetylamino}phenyl)-1H-indazole-5-carboxamide;

3-(3-{2-(4-(dimethylamino)phenyl)acetylamino}phenyl)-1H-indazole-5-carboxamide;

3-{3-(2-(2-chloro-4-fluorophenyl)acetylamino)phenyl}-1H-indazole-5-carboxamide;

3-{3-(2-(4-chlorophenyl)acetylamino)phenyl}-1H-indazole-5-carboxamide;

3-(3-(3-phenylpropanoylamino)phenyl)-1H-indazole-5-carboxamide;

3-{3-(3-(4-fluorophenyl)propanoylamino)phenyl}-1H-indazole-5-carboxamide;

3-{3-(2-(3,4-difluorophenyl)acetylamino)phenyl}-1H-indazole-5-carboxamide;

3-{3-(2-(2-fluorophenyl)acetylamino)phenyl}-1H-indazole-5-carboxamide;

3-(3-(2-phenylpropanoylamino)phenyl}-1H-indazole-5-carboxamide;

3-(3-(2-piperidylethoxy)phenyl}-1H-indazole-5-carboxamide;

N-ethyl-3-{(3-(4-fluorophenyl)(1H-indazol-5-yl))carbonylamino}propanamide;

(3-(4-fluorophenyl)(1H-indazol-5-yl))-N-(3-methoxypropyl)carboxamide;

3-{3-(N-(2-piperidylethyl)carbamoyl)phenyl}-1H-indazole-5-carboxamide;

(3-(4-fluorophenyl)(1H-indazol-5-yl))-N-(2-hydroxyethyl)carboxamide;

(3-(4-fluorophenyl)(1H-indazol-5-yl))-N-(3-hydroxypropyl)carboxamide;

(3-(4-fluorophenyl)(1H-indazol-5-yl))-N-(2-metoxyethyl)carboxamide;

(3-(4-fluorophenyl)(1H-indazol-5-yl))-N-(oxolan-2-ylmethyl)carboxamide;

3-(2H, 3H-benzo(e)1,4-dioxin-6-yl)-1H-indazole-5-carboxamide;

3-(3-quinolyl)-1H-indazole-5-carboxamide;

3-(6-methoxy-2-naphthyl)-1H-indazole-5-carboxamide;

3-(2,3-dihyddrobenzo(b)furan-5-yl)-1H-indazole-5-carboxamide;

(3-(4-fluorophenyl)(1H-indazol-5-yl))-N-(3-oxo-3-pyrrolidinylpropyl)carboxamide;

3-{(3-(4-fluorophenyl)(1H-indazol-5-yl))carbonylamino}-N-methyl propanamide;

3-{(3-(4-fluorophenyl)(1H-indazol-5-yl))carbonylamino}-N,N-dimethyl propanamide;

3-{(3-(4-fluorophenyl)(1H-indazol-5-yl))carbonylamino}-N-(2-methoxyethyl)propanamide; or a pharmaceutically acceptable salt thereof.

22. A compound of claim 4 , wherein the compound is:

phenyl-N-(3-phenyl(1H-indazol-5-yl))carboxamide;

N-(3-phenyl(1H-indazol-5-yl))-2-pyridylcarboxamide;

methyl 4-(N-(3-phenyl-1H-indazol-5-yl)carbamoyl)benzoate,

4-(N-(3-phenyl-1H-indazol-5-yl)carbamoyl)benzoic acid;

(2-hydroxyphenyl)-N-(3-phenyl(1H-indazol-5-yl)carboxamide,

N-(3-phenyl-1H-indazole-5-yl))acetamide;

(4-aminophenyl)-N-(3-phenyl(1H-indazol-5-yl))carboxamide;

(3-aminophenyl)-N-(3-phenyl(1H-indazol-5-yl))carboxamide;

N-(3-(4-fluorophenyl)(1H-indazol-5-yl))(2-methylphenyl)carboxamide;

N-(3-(4-fluorophenyl)(1H-indazol-5-yl))(2-methoxyphenyl)carboxamide;

N-(3-(4-fluorophenyl)(1H-indazol-5-yl))(4-phenylphenyl)carboxamide;

benzo(b)thiophen-2-yl-N-(3-(4-fluorophenyl)(1H-indazol-5-yl))carboxamide;

methyl 4-{N-(3-(4-fluorophenyl)-1H-indazol-5-yl)carbamoyl}benzoate;

N-(3-(4-fluorophenyl)(1H-indazol-5-yl))-2-pyridylcarboxamide;

4-{N-(3-(4-fluorophenyl)-1H-indazol-5-yl)carbamoyl}benzoic acid;

cyclopropyl-N-(3-(4-fluorophenyl)(1H-indazol-5-yl))carboxamide;

methyl 4-{N-(3-(4-fluorophenyl)(1H-indazol-5-yl))-N-methylcarbamoyl}benzoate;

4-{N-(3-fluorophenyl)(1H-indazol-5-yl))-N-methylcarbamoyl}benzoic acid;

methyl 3-{N-((4-fluorophenyl)-1H-indazol-5-yl) carbamoyl}benzoate;

3-{N-(3-(4-fluorophenyl)-1H-indazol-5-yl)carbamoyl}benzoic acid;

N-(3-(4-fluorophenyl)-(1H-indazol-5-yl))(4-(N-methylcarbamoyl)phenyl)carboxamide;

4-{N-(3-(4-fluorophenyl)-1H-indazol-5-yl)carbamoyl}benzamide;

1-4-{N-(3-(4-methoxyphenyl)-1H-indazol-5-yl)carbamoyl}benzoic acid;

4-(N-(3-(4-pyridyl)-1H-indazol-5-yl)carbamoyl)benzoic acid;

N-(3-(4-fluorophenyl)(1H-indazol-5-yl)benzamide;

(3,4-bis(trifluoromethyl)phenyl)-N-(3-(4-fluorophenyl)(1H-indazol-5-yl))carboxamide;

N-(3-(4-fluorophenyl)(1H-indazol-5-yl))-2-furylcarboxamide;

N-(3-(4-fluorophenyl)(1H-indazol-5-yl))(3,4-dichlorophenyl)carboxamide;

N-(3-(4-fluorophenyl)(1H-indazol-5-yl))(2-hydroxyphenyl)carboxamide;

N-(3-(4-fluorophenyl)(1H-indazol-5-yl))-4-pyridylcarboxamide;

N-(3-(4-fluorophenyl)(1H-indazol-5-yl))-3-pyridylcarboxamide;

N-(3-(4-fluorophenyl)(1H-indazol-5-yl))-2-thienylcarboxamide;

N-(3-(4-fluorophenyl)(1H-indazol-5-yl))morpholin-4-yl-carboxamide;

[N-(((2R)-2-hydroxycyclohexyl)methyl)(3-(4-fluorophenyl)(1H-indazol-5-yl))carboxamide;] or a pharmaceutically acceptable salt thereof.

23. A compound of claim 5 , wherein the compound is:

3-(3-(4-fluorophenyl)-1H-indazol-5-yl)-1H-1,2,4-triazole;

5-(3-(4-fluorophenyl)(1H-indazole-5-yl))-3-methyl-4H-1,2,4-triazole;

5-{3-(4-fluorophenyl)(1H-indazole-5-yl)]-3-(methylethyl)-4H-1,2,4-triazole;

1-{5-(3-(4-fluorophenyl)-1H-indazole-5-yl)4H-1,2,4-triazol-3-yl}propan-2-ol;

5-(3-(4-fluorophenyl)(1H-indazol-5-yl))-3-propyl-4H-1,2,4-triazole;

5-{3-(3-(methylethyl)phenyl)-1H-indazol-5-yl}-1H-1,2,4-triazole;

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

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

{2-(4-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))phenoxy)ethyl}dimethylamine;

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

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

5-(3-naphthyl-1H-indazol-5-yl)-1H-1,2,4-triazole;

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

5-(3-(2-naphthyl)-1H-indazol-5-yl)-1H-1,2,4-triazole;

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

3-(3-(3,4-dichlorophenyl)-1H-indazol-5-yl)-1H-1,2,4-triazole;

3-(5-(1H-1,2,4-triazol-5-yl)-1H-indazol-3-yl)benzo(b)thiophene;

3-(3-(4-methylphenyl)-1H-indazol-5-yl)-1H-1,2,4-triazole;

N-(3-(5-(1H-1,2,4-triazol-3-yl)-1H-indazol-3-yl)phenyl)acetamide;

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

2-(5-(1H-1,2,4-triazol-5-yl)-1H-indazol-3-yl)benzo(b)furan;

1-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))-4-(methylsulfonyl)benzene;

1-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))-4-(methylsulfinyl)benzene;

5-(5-(1H-1,2,4-triazol-5-yl)-1H-indazol-3-yl)-2H-benzo(d)1,3-dioxolene;

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

5-{3-(4-(trifluoromethyl)phenyl)-1H-indazol-5-yl}-1H-1,2,4-triazole;

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

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)-2-methoxyacetamide;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)-2-phenylacetamide;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)-2-furylcarboxamide;

5-(3-(2-phenylethynyl)-1H-indazol-5-yl)-1H-1,2,4-triazole;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)-3-pyridylcarboxamide;

1-{5-{3-(4-fluorophenyl)1H-indazol-5-yl}-4H-1,2,4-Triazol-3-yl}ethan-1-ol;

1-{5-(3-(4-fluorophenyl)-1H-indazol-5-yl}-4H-1,2,4-triazol-3-yl}propan-2-ol;

{3-(3-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))phenoxy)propyl}dimethylamine;

{2-(3-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))phenoxy)ethyl}dimethylamine;

1-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))-3-(2-morpholin-4-yl-ethoxy)benzene;

1-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))-3-(2-pyrrolidinylethoxy)benzene;

1-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))-3-(2-piperidylethoxy)benzene;

1-{2-(3-(5-(1H-1,2,4-triazol-5-yl)-1H-indazol-3-yl)phenoxy)ethyl}pyrrolidin-2-one;

1-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))-3-(2-piperazinylethoxy)benzene;

1-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))-3-(3-piperdylpropoxy)benzene;

4-{2-(3-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))phenoxy)ethyl}-1-acetylpiperazine;

2-(3-(5-(1H-1,2,4-triazol-5-yl)-1H-indazol-3-yl)phenoxy)ethylamine;

1-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))-3-(2-cyclohexylethoxy)benzene;

1-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))-3-(2-azaperhyroepinylethoxy)benzene;

N-(4-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))phenyl)-2-furyl caroxamide;

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

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

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

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

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

(3-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))phenyl)-4-methyl piperazinyl ketone;

(3-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))phenyl)-N-((4-fluorophenyl)methyl)carboxamide;

(3-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))phenyl)-N-indan-2-ylcarboxamide;

(3-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))phenyl)-N-((1R)indanyl)carboxamide;

(3-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))phenyl)-N-((1S)indanyl)carboxamide;

(3-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))phenyl)-N-((1S,2R)-2-hydroxyindanyl)carboxamide;

(3-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))phenyl)-N-((2S,1R)-2-hydroxyindanyl)carboxamide;

(3-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))phenyl)-N-(1-methyl-1-phenylethyl)carboxamide;

(3-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))phenyl)-N-(tert-butyl)carboxamide;

(3-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))phenyl)-N-((1R)-1-phenylethyl)carboxamide;

1-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))-3-(2-piperidylethoxy)benzene;

(3-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))phenyl-isoindolin-2-yl ketone;

(3-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))phenyl)-N-(2-(dimethylamino)ethyl)carboxamide;

1-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))-3-(2-piperidylethoxy)benzene;

(3-(5-(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))phenyl)-N-(1R)indanyl benzene;

{5-(3-(4-fluorophenyl)-1H-indazol-5-yl)-4H-(1,2,4)-triazol-3-ylmethyl}-dimethyl-amine;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)-3-piperidylpropanamide;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)-2-hydroxypropanamide;

N-(3-(5-(1H-1,2,4-triazol-3yl-)(1H-indazol-3-yl))phenyl)-2-(dimethylamino)acetamide;

N-(3-(5-(1H-1,2,4-triazol-3-yl)-1H-indazol-3-yl)phenyl)butanamide;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)-2-phenoxypropanamide;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)-3,3-dimethylbutanamide;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)cyclopropylcarboxamide;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)(6-chloro(3-pyridyl))carboxamide;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)cyclopentylcarboxamide;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)benzo(b)thiophen-2-carboxamide;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)-2-pyridylcarboxamide;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)-3-furylcarboxamide;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)-2-hydroxy-2-phenylacetamide;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)isoxazol-5-ylcarboxamide;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)pentanamide;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)-4-pyridylcarboxamide;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)-2-cyclohexylacetamide;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)-3-propanamide;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)-2-(4-fluorophenyl)acetic acid;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)(2R)-2-hydroxy-2-phenylacetamide;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)(2S)-2-hydroxy-2-phenylacetamide;

(2-{3-(3-(4-fluorophenyl)(1H-indazol-5-yl))(1H-1,2,4-triazol-5-yl)}ethyl)dimethylamine;

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

({3-(3-(4-fluorophenyl)(1H-indazol-5-yl))(1H-1,2,4-triazol-5-yl)}methyl)methylamine;

({3-(3-(4-fluorophenyl)(1H-indazol-5-yl))(1H-1,2,4-triazol-5-yl)}ethyl)dimethylamine;

(2R)-N-(3-(5-{5-((dimethylamino)methyl)(1H-1,2,4-triazol-3-yl)}(1H-indazol-3-yl))phenyl)-2-hydroxy-2-phenylacetamide;

N-(3-(5-{5-((dimethylamino)methyl)(1H-1,2,4-triazol-3-yl)}(1H-indazol-3-yl))phenyl)-3,3-dimethylbutanamide;

N-(3-(5-{5-((dimethylamino)methyl)(1H-1,2,4-triazol-3-yl)}(1H-indazol-3-yl))phenyl)-3-methylbutanamide;

N-(3-(5-{5-((dimethylamino)methyl)(1H-1,2,4-triazol-3-yl)}(1H-indazol-3-yl))phenyl)-3-pyridylcarboxamide;

(3-(5-{5-((dimethylamino)methyl)(1H-1,2,4-triazol-3-yl)}(1H-indazol-3-yl))phenyl)-N-((4-fluorophenyl)methyl)carboxamide;

(3-(5-{5-((dimethylamino)methyl)(1H-1,2,4-triazol-3yl)}(1H-indazol-3-yl))phenyl)-N-(tert-butyl)methyl)carboxamide;

((1R)indanyl)(3-(5-{5-((dimethylamino)methyl)(1H-1,2,4-triazol-3-yl)}(1H-indazol-3-yl))phenyl)carboxamide;

({3-(3-(4-methoxyphenyl)(1H-indazol-5-yl))(1H-1,2,4-triazol-5-yl)}methyl)dimethylamine;

{(3-(3-(2H-benzo(d)1,3-dioxolen-5-yl))(1H-indazol-5-yl))(1H-1,2,4-triazol-5-yl)}methyl}dimethylamine;

(3-(5-(3-((dimethylamino)methyl)(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))phenyl)-N-(2-piperidylethyl)carboxamide;

((5-(3-benzo(D)furan-2-yl(1H-indazol-5-yl))(1H-1,2,4-triazol-3-yl))methyl)dimethylamine;

(3-(5-(3-((dimethylamino)methyl)(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))phenyl)-N-benzamide;

(3-(5-(3-((dimethylamino)methyl)(1H-1,2,4-triazol-5-yl))(1H-indazol-3-yl))phenyl)-N-(4-fluorophenyl)carboxamide-2HCl;

(3-(5-(3-((dimethylamino)methyl)(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))phenyl)-N-indan-2-yl-carboxamide;

(3-(5-(3-((dimethylamino)methyl)(1H-1,2,4-triazol-5-yl)(1H-indazol-3-yl))phenyl)-N-cyclopropylcarboxamide;

(3-(5-(3-((dimethylamino)methyl)(1H-1,2,4-triazol-5-yl))(1H-indazol-3-yl))phenyl)-N-cyclobutylcarboxamide-2HCl;

1-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl)-3-(2-methoxyethoxy)benzene;

1-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl)-3-(3-pyridylmethoxy)benzene;

3-(5-(1H-1,2,4-triazol-3-y)-1H-indazol-3-yl)benzoic acid;

3-(5-(1H-1,2,4-triazol-3-yl)-1H-indazol-3-yl)benzoic acid N-(4-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)-2-(3-pyridyl)acetamide;

N-(4-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)-2-phenylacetamide;

N-(4-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)-2-methoxyacetamide;

N-(4-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)-2-(dimethylamino)acetamide;

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

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

(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)-N-benzamide;

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

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

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

(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl-N-cyclohexylcarboxamide;

(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl-N-cyclopentylcarboxamide;

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

(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl-N-((1R,2R)-2-phenylcyclopropyl)carboxamide;

(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl-N-cyclopropylcarboxamide;

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

(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl-N-(5,6,7,8-tetrahydronaphthyl)carboxamide;

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

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

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

(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl-N-cyclobutylcarboxamide;

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

6-(5-(1H-1,2,4-triazol-3-yl)-1H-indazol-3-yl)-2H,3h-benzo(e)1,4-dioxin;

6-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))-2-methoxynaphthalene;

3-(3-(3-quinoyl)-1H-indazol-5-yl)-1H-1,2,4-triazole;

5-(5-(1H-1,2,4-triazol-3-yl)-1H-indazol-3-yl)-2,3-dihydrobenzo(b)furan;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)benzamide;

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

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

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

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

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)-2-methylpropanamide;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)-3-methylbutanamide;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)-2-morpholin-4-yl-acetamide;

N-(3-(5-(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl))phenyl)-2-(4-methylpiperazinyl)acetamide;

2-methoxy-6-{5-(5-(pyrrolidinylmethyl)(1H-1,2,4-triazol-3-yl)(1H-indazol-3-yl)}naphthalene;

N-phenyl(3-{5-(5-(pyrrolidinylmethyl)(1H-1,2,4-triazol-3-yl))(1H-indazol-3-yl)}phenyl)carboxamide;

6-{5-(5-(pyrrolidinylmethyl)-1H-1,2,4-triazol-3-yl)-1H-indazol-3-yl}-2H,3H-benzo(e)1,4-dioxin; or a pharmaceutically acceptable salt thereof.

24. A compound of claim 6 , wherein the compound is:

5-(3-(4-fluorophenyl)-1H-indazol-5-yl)-2H-1,2,3,4-tetrazole;

1-(5-(2H-1,2,3,4-tetrazol-5-yl)(1H-indazol-3-yl))-2-methoxybenzene;

5-(3-(3-pyridyl)-1H-indazol-5-yl)-2H-1,2,3,4-tetrazole;

2-(5-(2H-1,2,3,4-tetrazol-5-yl)-1H-indazol-3-yl)thiophene;

5-{3-(4-(methylethyl)phenyl)-1H-indazol-5-yl}-2H-1,2,3,4-tetrazole;

2-(5-(2H-1,2,3,4-tetrazol-5-yl)-1H-indazol-3-yl)furan;

3-(5-(2H-1,2,3,4-tetrazol-5-yl)-1H-indazol-3-yl)phenylamine;

5-(5-(1H-1,2,3,4-tetraazol-5-yl)-1H-indazol-3-yl)-2H-benzo(d)1,3-dioxolene;

3-(5-(2H-1,2,3,4-tetrazol-5-yl)-1H-indazol-3-yl)thiophene;

5-(3-(2-naphthyl)-1H-indazol-5-yl)-1H-1,2,3,4-tetrazole;

1-(5-(1H-1,2,3,4-tetraazol-5-yl)(1H-indazol-3-yl))-4-methoxybenzene;

1-(5-(1H-1,2,3,4-tetraazol-5-yl)(1H-indazol-3-yl))-4-(2-methylpropoxy)benzene;

5-(3-(4-chlorophenyl)-1H-indazol-5-yl)-2H-1,2,3,4-tetrazole;

1-(5-(2H-1,2,3,4-tetrazol-5-yl)(1H-indazol-3-yl))-3-methoxybenzene;

5-(3-(4-pyridyl)-1H-indazol-5-yl)-2H-1,2,3,4-tetrazole;

2-(5-(2H-1,2,3,4-tetraazol-5-yl)-1H-indazol-3-yl)benzo(b)furan;

2-(5-(2H-1,2,3,4-tetrazol-5-yl)-1H-indazol-3-yl)phenol;

3-(5-(2H-1,2,3,4-tetrazol-5-yl)-1H-indazol-3-yl)phenol;

5-(3-(2-phenylethynyl)-1H-indazol-5-yl)-1H-1,2,3,4-tetrazole;

5-(3-(2-phenylethyl)-1H-indazol-5-yl)-2H-1,2,3,4-tetrazole;

N-(3-(5-(2H-1,2,3,4-tetrazol-5-yl)(1H-indazol-3-yl))phenyl)-2-methoxyacetamide;

2-(5-(1H-1,2,3,4-tetraazol-5-yl)-1H-indazol-3-yl)benzo(b)thiophene;

1-(5-(1H-1,2,3,4-tetraazol-5-yl)(1H-indazol-3-yl))-4-(2-morpholin-4-ylethoxy)benzene;

N-(3-(5-2H-1,2,3,4-tetrazol-5-yl)(1H-indazol-3-yl))phenyl)2-phenoxypropanamide;

N-(3-(5-(2H-1,2,3,4-tetrazol-5-yl)(1H-indazol-3-yl))phenyl)-3-piperidylpropanamide;

N-(3-(5-(2H-1,2,3,4-tetrazol-5-yl)(1H-indazol-3-yl))phenyl)-2-furylcarboxamide;

1-(5-(1H-1,2,3,4-tetraazol-5-yl)(1H-indazol-3-yl))-3-(2-morpholin-4-ylethoxy)benzene;

4-(5-(2H-1,2,3,4-tetraazol-5-yl)(1H-indazol-3-yl))-1,2-dimethoxybenzene;

N-(3-(5-(2H-1,2,3,4-tetrazol-5-yl)(1H-indazol-3-yl))phenyl)-3-methoxypropanamide;

N-(3-(5-(2H-1,2,3,4-tetrazol-5-yl)(1H-indazol-3-yl))phenyl)-3-pyridylcarboxamide;

{3-(4-(5-(1H-1,2,3,4-tetrazo-5-yl)(1H-indazol-3-yl))phenoxy)propyl}dimethylamine;

{3-(3-(5-(1H-1,2,3,4-tetrazol-5-yl)(1H-indazol-3-yl))phenoxy)propyl}dimethylamine;

{2-(3-(5-(1H-1,2,3,4-tetrazol-5-yl)(1H-indazol-3-yl))phenoxy)ethyl}dimethylamine;

N-(3-(5-(2H-1,2,3,4-tetrazol-5-yl)(1H-indazol-3-yl))phenyl)(2S)-2-hydroxypropanamide;

N-(4-(5-(2H-1,2,3,4-tetrazol-5-yl)(1H-indazol-3-yl))phenyl)-3-pyridylcarboxamide;

or a pharmaceutically acceptable salt thereof.

25. A compound of claim 7 , wherein the compound is:

3-(4-fluorophenyl)-5-imidazol-2-yl-1H-indazole, or a pharmaceutically acceptable salt thereof.

26. A compound, wherein the compound is:

3-phenyl-5-(phenylmethoxy)-1H-indazole;

(3-(4-fluorophenyl)(1H-indazol-5-yl)(phenylsulfonyl)amine;

3-(4-fluorophenyl)-1H-indazole-5-carboxylate;

(3-(4-fluorophenyl)(1H-indazol-5-yl))-N-(phenylmethoxy)carboxamide;

3-(4-fluorophenyl)-1H-indazole-5-carbohydroxamic acid;

N-((tert-butoxy)carbonylamino)(3-(4-fluorophenyl)(1H-indazol-5-yl))carboxamide;

N-amino(3-(4-fluorophenyl)(1H-indazol-5-yl))carboxamide;

methyl-3-benzo(B)thiophen-2-yl-1H-indazole-5-carboxylate;

3-benzo(B)thiophen-2-yl-1H-indazole-5-carboxylic acid;

or a pharmaceutically acceptable salt thereof.

Assignments (3)
CONVERSION FROM INC. TO LLC Recorded Jan 14, 2005
From: SIGNAL PHARMACEUTICALS, INC.
To: SIGNAL PHARMACEUTICALS, LLC
Reel/Frame 016152/0692 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 18, 2002
From: BHAGWAT, SHRIPAD S.; SATOH, YOSHITAKA; SAKATA, STEVEN T.; ALBERS, RONALD; SAPIENZA, JOHN; PLANTEVIN, VERONIQUE; CHAO, QI; SAHASRABUDHE, KIRAN; FERRI, RACHEL
To: SIGNAL PHARMACEUTICALS, INC.
Reel/Frame 012692/0030 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 15, 2002
From: BUHR, CHRIS A.
To: SIGNAL PHARMACEUTICALS, INC.
Reel/Frame 012680/0489 →
Continuity (2)
Provisional Application 6022179900 · Jul 31, 2000
Related Publication 20020103229A1 · Aug 1, 2002