US2011269774A1PendingUtilityA1
Pyrazolylaminopyridines as inhibitors of fak

Assignee: ADAMS JERRYPriority: Oct 27, 2008Filed: Apr 29, 2011Published: Nov 3, 2011
Est. expiryOct 27, 2028(~2.3 yrs left)· nominal 20-yr term from priority
Inventors:Jerry L. Adams Thomas H. Faitg Neil W. Johnson Jiri Kasparec Hong Lin Mark Mellinger Xin Peng Ren Xie
A61P 43/00A61P 35/00G01N 33/5752C07D 401/12C07D 401/14A61K 31/337A61K 31/4439A61K 31/47A61K 31/4375
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Claims
Abstract

The present invention relates to a compound of formula (I): or a pharmaceutically acceptable salt thereof, wherein R 1 , R 2 , R 3 , R 11 , R 12 , R 13 , Q, Z, and p are as described herein. Compounds of the present invention are useful for the treatment of cancers.
Claims

exact text as granted — not AI-modified
1 . A compound of formula (I): 
       
         
           
           
               
               
           
         
         or a salt thereof, wherein: 
         R 1  is halo, CF 3 , C 1 -C 6 -alkyl, isopropenyl, (C 2 -C 6 -alkylene) C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, or cyano; 
         in R 2 , when p is other than 0, each R 2  is independently F, Cl, CF 3 , methyl, methoxy, CH 2 CF 3 , —(X) q —C 1 -C 4 -alkylene-R 4 , -(X-C i -C 4 -alkylene) q —NR 5 —C(O)—R 6 , —(X—C 1 -C 4 -alkylene) q -(NR 5 ) q —SO x —R 7 , —(X—C 1 -C 4 -alkylene) q —Y—N(R 8 ) 2 , a 5- to 6-membered heterocycloalkyl-(R 9 ) q  group, or a 5- to 6-membered heteroaryl-(R 10 ) r  group; 
         each R 3  is independently H, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkyl, C 1 -C 6 alkoxy, C 1 -C 6 -alkylene-R 4 , —N(R 8 ) 2 , O—C 1 -C 6 -alkylene-R 4 , or, the R 3  groups, together with Z form a 5- to 6-membered cycloalkyl or cycloheteroalkyl where the hetero atom is N or O and ring is optionally substituted on a carbon or heteroatom by methyl, C 1 -C 4 -alkylene-R 4 , or C 3 -C 6 -cycloalkyl; 
         R 4  is H, -(Q) q -N(R 8 ) 2 , OH, SH, C 1 -C 6 -alkoxy, C 1 -C 6 -thioalkyl, or a 5- to 6-membered heterocycloalkyl-(R 9 ) q  group; 
         R 5  is H or C 1 -C 6 -alkyl; 
         R 6  is H, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, N(R 8 ) 2 , or a 5- to 6-membered heteroaryl-(R 10 ) r  group; 
         R 7  is C 1 -C 6 -alkyl, phenyl-(R 9 ) q , or 5- to 6-membered heteroaryl-(R 10 ) r    
         R 8  is independently H, C 1 -C 6 -alkyl, —O—C 1 -C 6 -alkyl or, together with the nitrogen atom to which they are attached, form a 5- or 6-membered heterocycloalkyl group; 
         R 9  is H, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, -(Q) q -N(R 8 ) 2 , -Q-C 1 -C 6 -alkyl,-C 1 -C 6 alkylR 4 , or 5- to 6-membered heterocycloalkyl; 
         R 10  is H, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, or -Q-C 2 -C 6 -alkyl; 
         R 11  is C 1 -C 6 -alkyl, CF 3 , —CH 2 CF 3 , -(Q) q -C 1 -C 4 -alkylene-R 4 , -Q-N(R 8 ) 2 , phenyl-(R 5 ) s , a 5- to 6-membered heterocycloalkyl-(R 9 ) q  group, or a 5- to 6-membered heteroaryl-(R 10 ) r  group; 
         R 12  is H, C 1 -C 6 -alkyl, F, Cl, CF 3 , OH, CN, nitro, COOH, —COO—C 1 -C 6 -alkyl, —C 1 -C 6 -alkylOH, —C 1 -C 6 -alkylN(R 8 ) 2 , —Y—N(R 8 ) 2 , C 3 -C 6 -cycloalkyl-R 14 , —(X) q —C 1 -C 6 -alkylene-R 4 , —(X—C 1 -C 6 -alkylene) q -NR 5 —C(O)—R 6 , —(X—C 1 -C 6 -alkylene) q -(NR 5 ) q —SO x —R 7 , —(X—C 1 -C 6 -alkylene) q -Y—N(R 8 ) 2 , heterocycloalkyl-(R 9 ) q , heteroaryl-(R 10 ) r , or phenyl-(R 15 ) s ; 
         R 13  is H, F, Cl, C 1 -C 6 -alkyl, or C 3 -C 6 -cycloalkyl; or R 12  and R 13 , together with the carbon atoms to which they are attached, form a fused 5-or 6-membered carbocycloalkyl or heterocycloralkyl group; 
         R 14  is independently H, C 1 -C 6 -alkyl. —NR 5 —SO 2 —R 7 , —Y—N(R 8 ) 2 , or —(X) q —C 1 -C 6 -alkylene-R 4 ; 
         each R 15  is independently F, Cl, CF 3 , C 1 -C 3 -alkyl, or C 1 -C 3 -alkoxy; 
         p is 0, 1, 2, or 3; 
         q is 0 or 1; 
         r is 0, 1, or 2; 
         s is 0, 1, 2, or 3; 
         x is 1 or 2; 
         Q is —C(O)—, —S(O)—, or —SO 2 —; 
         X is NR 5 , O, S, —S(O)—, or —SO 2 —; 
         Y is a bond, SO 2 , or C(O); and 
         Z is N or CR 5 . 
       
     
     
         2 . A compound according to  claim 1  which is represented by formula (IB): 
       
         
           
           
               
               
           
         
       
       or a salt thereof. 
     
     
         3 . A compound according to  claim 1  or a salt thereof wherein Q is C(O) and Z is N. 
     
     
         4 . The compound of  claim 1  or a salt thereof where one R 3  is methoxy and the other R 3  is H. 
     
     
         5 . The compound of  claim 1 or a salt thereof where one R 3  is methyl and the other R 3  is H. 
     
     
         6 . A compound according to  claim 1  or a salt thereof wherein R 1  is Cl, CF 3 , or CN. 
     
     
         7 . A compound according to  claim 1 or a salt thereof wherein p is 0 or 1 and R 2  is F. 
     
     
         8 . A compound according to  claim 1  or a salt thereof wherein R 11  is C 1 -C 3 -alkyl. 
     
     
         9 . The compound of  claim 1  or a salt thereof wherein R 12  is C 1 -C 4 -alkyl, hydroxymethyl, or cyclopropyl. 
     
     
         10 . A compound according to  claim 1  or a salt thereof wherein R 13  is H. 
     
     
         11 . A compound according to  claim 1  which is:
 1. 2-[5-chloro-2-(2-methyl-5-phenyl-2H-pyrazol-3-ylamino)-pyridin-4-ylamino]-N-methyl-benzamide; 
 2. 2-({5-chloro-2-[(1-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-methylbenzamide; 
 3. 2-({5-chloro-2-[(1-ethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-methylbenzamide; 
 4. 2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-methylbenzamide; 
 5. 2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-methylbenzamide; 
 6. 2-({5-chloro-2-[(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-methylbenzamide; 
 7. 2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-5-fluoro-N-methylbenzamide; 
 8. 2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-5-fluoro-N-methylbenzamide; 
 9. 2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-3-fluoro-N-methylbenzamide; 
 10. 2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-3-fluoro-N-methylbenzamide; 
 11. 2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-4,5-difluoro-N-methylbenzamide; 
 12. 2-({5-chloro-2-[(1-ethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-4,5-difluoro-N-methylbenzamide; 
 13. 5-chloro-2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-methylbenzamide; 
 14. 5-chloro-2-({5-chloro-2-[(1-ethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-methylbenzamide; 
 15. 2-({5-chloro-2-[(1-ethyl-3-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-methylbenzamide; 
 16. 2-[(5-chloro-2-{[3-(1,1-dimethylethyl)-1-methyl-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-methylbenzamide; 
 17. 2-[(5-chloro-2-{[1-ethyl-3-(hydroxymethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-methylbenzamide; 
 18. 2-[(5-chloro-2-{[1-(2-hydroxyethyl)-3-methyl-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-methylbenzamide; 
 19. ethyl 5-{[5-chloro-4-({2-[(methylamino)carbonyl]phenyl}amino)-2-pyridinyl]amino}-1-ethyl-1H-pyrazole-3-carboxylate; 
 20. 5-{[5-chloro-4-({2-[(methylamino)carbonyl]phenyl}amino)-2-pyridinyl]amino}-1-ethyl-1H-pyrazole-3-carboxylic acid; 
 21. 5-{[5-chloro-4-({2-[(methylamino)carbonyl]phenyl}amino)-2-pyridinyl]amino}-1-ethyl-N-(methyloxy)-1H-pyrazole-3-carboxamide; 
 22. 5-{[5-chloro-4-({2-[(methylamino)carbonyl]phenyl}amino)-2-pyridinyl]amino}-1-ethyl-N-methyl-1H-pyrazole-3-carboxamide; 
 23. 2-[(5-chloro-2-{[3-methyl-1-(2,2,2-trifluoroethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-methylbenzamide; 
 24. 2-[(5-chloro-2-{[1-(1-methyl-4-piperidinyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-methylbenzamide; 
 25. 2-{[5-chloro-2-({1-[2-(dimethylamino)ethyl]-3-methyl-1H-pyrazol-5-yl}amino)-4-pyridinyl]amino}-N-methylbenzamide; 
 26. 5-{[5-chloro-4-({2-[(methylamino)carbonyl]phenyl}amino)-2-pyridinyl]amino}-N-[2-(dimethylamino)ethyl]-1-ethyl-1H-pyrazole-3-carboxamide; 
 27. 5-{[5-chloro-4-({2-[(methylamino)carbonyl]phenyl}amino)-2-pyridinyl]amino}-N-[2-(dimethylamino)ethyl]-1-ethyl-N-methyl-1H-pyrazole-3-carboxamide; 
 28. 2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-4-yl)amino]-4-pyridinyl}amino)-N-methylbenzamide; 
 29. 2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-4-yl)amino]-4-pyridinyl}amino)-N-methylbenzamide; 
 30. 2-{[2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-5-(trifluoromethyl)-4-pyridinyl]amino}-N-methylbenzamide; 
 31. 2-{[2-[(1-ethyl-1H-pyrazol-5-yl)amino]-5-(trifluoromethyl)-4-pyridinyl]amino}-N-methylbenzamide; 
 32. N-methyl-2-{[2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-5-(trifluoromethyl)-4-pyridinyl]amino}benzamide; 
 33. 2-{[2-({1-[2-(dimethylamino)ethyl]-3-methyl-1H-pyrazol-5-yl}amino)-5-(trifluoromethyl)-4-pyridinyl]amino}-N-methylbenzamide; 
 34. 2-{[2-[(1-ethyl-3-methyl-1H-pyrazol-5-yl)amino]-5-(trifluoromethyl)-4-pyridinyl]amino}-N-methylbenzamide; 
 35. N-methyl-2-{[2-[(3-methyl-1-phenyl-1H-pyrazol-5-yl)amino]-5-(trifluoromethyl)-4-pyridinyl]amino}benzamide; 
 36. 2-{[2-{[1-(2-hydroxyethyl)-3-methyl-1H-pyrazol-5-yl]amino}-5-(trifluoromethyl)-4-pyridinyl]amino}-N-methylbenzamide; 
 37. 2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)benzoic acid; 
 38. 2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-(methyloxy)benzamide; 
 39. 2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-methyl-N-(methyloxy)benzamide; 
 40. 2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-{[2-(dimethylamino)ethyl]oxy}benzamide; 
 41. 2-({5-chloro-2-[(1-ethyl-3-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-(methyloxy)benzamide; 
 42. 2-({5-chloro-2-[(1-ethyl-3-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-(methyloxy)benzamide; 
 43. 2-({5-chloro-2-[(1-ethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-(methyloxy)benzamide; 
 44. 2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-(methyloxy)benzamide; 
 45. 2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-(methyloxy)benzamide HCl; 
 46. 2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-(methyloxy)benzamide formate; 
 47. 2-({5-chloro-2-[(1-ethyl-3-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-ethylbenzamide; 
 48. 2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-ethylbenzamide; 
 49. 2-({5-chloro-2-[(1-ethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-ethylbenzamide; 
 50. 2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-ethylbenzamide; 
 51. 2-{[5-chloro-2-({1-ethyl-3-[2-(1-pyrrolidinyl)ethyl]-1H-pyrazol-5-yl}amino)-4-pyridinyl]amino}-N-methylbenzamide; 
 52. 2-({5-chloro-2-[(1,5-dimethyl-1H-pyrazol-4-yl)amino]-4-pyridinyl}amino)-N-(methyloxy)benzamide; 
 53. 2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-4-yl)amino]-4-pyridinyl}amino)-N-(methyloxy)benzamide; 
 54. 2-[(5-chloro-2-{[4-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-(methyloxy)benzamide; 
 55. 2-({5-chloro-2-[(1-ethyl-4-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-(methyloxy)benzamide; 
 56. 2-[(5-chloro-2-{[4-methyl-1-(2-methylpropyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-(methyloxy)benzamide; 
 57. 2-[(5-chloro-2-{[3-(hydroxymethyl)-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-(methyloxy)benzamide; 
 58. 2-[5-cyclopropyl-2-(2,5-dimethyl-2H-pyrazol-3-ylamino)-pyridin-4-ylamino]-N-methyl-benzamide; 
 59. 2-[5-cyclopropyl-2-(2-ethyl-5-methyl-2H-pyrazol-3-ylamino)-pyridin-4-ylamino]-N-methylbenzamide; 
 60. 2-[5-cyclopropyl-2-(2,5-dimethyl-2H-pyrazol-3-ylamino)-pyridin-4-ylamino]-N-methoxy-benzamide; 
 61. 2-[5-cyclopropyl-2-(2-ethyl-5-methyl-2H-pyrazol-3-ylamino)-pyridin-4-ylamino]-N-methoxy-benzamide; 
 62. 2-[2-(2,5-dimethyl-2H-pyrazol-3-ylamino)-5-isopropenyl-pyridin-4-ylamino]-N-methyl-benzamide; 
 63. 2-[2-(2,5-dimethyl-2H-pyrazol-3-ylamino)-5-isopropyl-pyridin-4-ylamino]-N-methyl-benzamide; 
 64. 2-({5-chloro-2-[(1,5-dimethyl-1H-pyrazol-4-yl)amino]-4-pyridinyl}amino)-N-methylbenzamide; 
 65. 2-{[5-chloro-2-({1-ethyl-3-[(methyloxy)methyl]-1H-pyrazol-5-yl}amino)-4-pyridinyl]amino}-N-methylbenzamide; 
 66. 2-{[5-chloro-2-({1-ethyl-3-[(methyloxy)methyl]-1H-pyrazol-5-yl}amino)-4-pyridinyl]amino}-N-methylbenzamide; 
 67. 2-[(5-chloro-2-{[3-[(ethyloxy)methyl]-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-methylbenzamide; 
 68. 2-[(5-chloro-2-{[3-[(ethyloxy)methyl]-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-methylbenzamide; 
 69. 2-{[5-chloro-2-({1-ethyl-3-[(ethyloxy)methyl]-1H-pyrazol-5-yl}amino)-4-pyridinyl]amino}-N-methylbenzamide; 
 70. 2-{[5-chloro-2-({1-ethyl-3-[(ethyloxy)methyl]-1H-pyrazol-5-yl}amino)-4-pyridinyl]amino}-N-methylbenzamide; 
 71. 2-({5-chloro-2-[(1-ethyl-3-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-hydroxy-N-methylbenzamide; 
 72. 2-({5-chloro-2-[(1-ethyl-3-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-hydroxy-N-methylbenzamide; 
 73. 2-({5-chloro-2-[(1-ethyl-3-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-(ethyloxy)benzamide; 
 74. 2-({5-cyano-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-methylbenzamide; 
 75. 2-({5-chloro-2-[(1-ethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-5-[4-(2-hydroxyethyl)-1-piperazinyl]-N-methylbenzamide; 
 76. 2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-5-[4-(2-hydroxyethyl)-1-piperazinyl]-N-methylbenzamide; 
 77. 4-chloro-2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-(methyloxy)benzamide; 
 78. 4-chloro-2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-(methyloxy)benzamide; 
 79. 2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-5-fluoro-N-(methyloxy)benzamide; 
 80. 2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-3-fluoro-N-(methyloxy)benzamide; 
 81. 2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-4-fluoro-N-(methyloxy)benzamide; 
 82. 2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-3-fluoro-N-methylbenzamide; 
 83. 2-({5-chloro-2-[(1-ethyl-3-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-3-fluoro-N-methylbenzamide; 
 84. 2-({5-chloro-2-[(1,5-dimethyl-1H-pyrazol-4-yl)amino]-4-pyridinyl}amino)-3-fluoro-N-methylbenzamide; 
 85. 2-{[2-[(1-ethyl-3-methyl-1H-pyrazol-5-yl)amino]-5-(trifluoromethyl)-4-pyridinyl]amino}-3-fluoro-N-methylbenzamide; 
 86. 2-{[2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-5-(trifluoromethyl)-4-pyridinyl]amino}-3-fluoro-N-methylbenzamide; 
 87. 2-{[2-{[1-ethyl-3-(hydroxymethyl)-1H-pyrazol-5-yl]amino}-5-chloro-4-pyridinyl]amino}-3-fluoro-N-methylbenzamide; 
 88. 3-fluoro-2-{[2-{[3-(hydroxymethyl)-1-methyl-1H-pyrazol-5-yl]amino}-5-chloro-4-pyridinyl]amino}-N-methylbenzamide; 
 89. 2-{[2-{[1-ethyl-3-(2-hydroxyethyl)-1H-pyrazol-5-yl]amino}-5-chloro-4-pyridinyl]amino}-3-fluoro-N-methylbenzamide; 
 90. 3-fluoro-2-{[2-{[3-(2-hydroxyethyl)-1-methyl-1H-pyrazol-5-yl]amino}-5-chloro-4-pyridinyl]amino}-N-methylbenzamide; 
 91. 2-{[2-({3-[(dimethylamino)methyl]-1-methyl-1H-pyrazol-5-yl}amino)-5chloro-4-pyridinyl]amino}-3-fluoro-N-methylbenzamide; 
 92. 2-{[2-({3-[(dimethylamino)methyl]-1-ethyl-1H-pyrazol-5-yl}amino)-5chloro-4-pyridinyl]amino}-3-fluoro-N-methylbenzamide; 
 93. 2-({5-chloro-2-[(3-{[ethyl(methyl)amino]methyl}-1-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-3-fluoro-N-methylbenzamide; 
 94. 2-{[5-chloro-2-({3-[(diethylamino)methyl]-1-methyl-1H-pyrazol-5-yl}amino)-4-pyridinyl]amino}-3-fluoro-N-methylbenzamide; 
 95. 2-{[2-{[1-ethyl-3-(hydroxymethyl)-1H-pyrazol-5-yl]amino}-5-(trifluoromethyl)-4-pyridinyl]amino}-3-fluoro-N-methylbenzamide; 
 96. 3-fluoro-2-{[2-{[3-(hydroxymethyl)-1-methyl-1H-pyrazol-5-yl]amino}-5-(trifluoromethyl)-4-pyridinyl]amino}-N-methylbenzamide; 
 97. 2-{[2-{[1-ethyl-3-(2-hydroxyethyl)-1H-pyrazol-5-yl]amino}-5-(trifluoromethyl)-4-pyridinyl]amino}-3-fluoro-N-methylbenzamide; 
 98. 3-fluoro-2-{[2-{[3-(2-hydroxyethyl)-1-methyl-1H-pyrazol-5-yl]amino}-(trifluoromethyl)-4-pyridinyl]amino}-N-methylbenzamide; 
 99. 2-{[2-({3-[(dimethylamino)methyl]-1-methyl-1H-pyrazol-5-yl}amino)-5-(trifluoromethyl)-4-pyridinyl]amino}-3-fluoro-N-methylbenzamide; 
 100. 2-({5-chloro-2-[(1-ethyl-3-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-3-fluoro-N-(methyloxy)benzamide; 
 101. 2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-3-fluoro-N-(methyloxy)benzamide; 
 102. 2-[(5-chloro-2-{[1-ethyl-3-(hydroxymethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-3-fluoro-N-(methyloxy)benzamide; 
 103. 2-[(5-chloro-2-{[3-(hydroxymethyl)-1-methyl-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-3-fluoro-N-(methyloxy)benzamide; 
 104. 2-{[5-chloro-2-({3-[(dimethylamino)methyl]-1-ethyl-1H-pyrazol-5-yl}amino)-4-pyridinyl]amino}-3-fluoro-N-(methyloxy)benzamide; 
 105. 2-({5-chloro-2-[(1,5-dimethyl-1H-pyrazol-4-yl)amino]-4-pyridinyl}amino)-3-fluoro-N-(methyloxy)benzamide; 
 106. 2-{[5-chloro-2-({3-[(dimethylamino)methyl]-1-ethyl-1H-pyrazol-5-yl}amino)-4-pyridinyl]amino}-N-(methyloxy)benzamide; 
 107. 2-({5-chloro-2-[(1-ethyl-3-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-4-fluoro-N-(methyloxy)benzamide; 
 108. 2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-4-fluoro-N-(methyloxy)benzamide; 
 109. 2-[(5-chloro-2-{[1-ethyl-3-(hydroxymethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-4-fluoro-N-(methyloxy)benzamide; 
 110. 2-[(5-chloro-2-{[1-ethyl-3-(2-hydroxyethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-4-fluoro-N-(methyloxy)benzamide; 
 111. 2-[(5-chloro-2-{[3-(hydroxymethyl)-1-methyl-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-4-fluoro-N-(methyloxy)benzamide; 
 112. 2-{[5-chloro-2-({3-[(dimethylamino)methyl]-1-ethyl-1H-pyrazol-5-yl}amino)-4-pyridinyl]amino}-4-fluoro-N-(methyloxy)benzamide; 
 113. 2-({5-chloro-2-[(1,5-dimethyl-1H-pyrazol-4-yl)amino]-4-pyridinyl}amino)-4-fluoro-N-(methyloxy)benzamide; or 
 
       a salt or a thereof. 
     
     
         12 . A pharmaceutically acceptable composition comprising a compound of formula (I) according  claim 1  or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable excipient. 
     
     
         13 . A method of treating cancer comprising administering to a patient in need thereof a pharmaceutically effective amount of a compound according to  claim 1  or a pharmaceutically acceptable salt thereof.
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