IP Library Patent Application 12606390
Patent Application
App. No. 12/606,390

PYRAZOLYLAMINOPYRIDINES AS INHIBITORS OF FAK

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Patent No.
US None
App. No.
12/606,390
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 (152)

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 1 -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;

R 3 is H, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkyl, C 1 -C 6 alkoxy, C 1 -C 6 -alkylene-R 4 , O—C 1 -C 6 -alkylene-R 4 , or, the R 3 groups, together with Z, form a 5- to 6-membered cyclic ring optionally substituted with 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 alkyl R 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, —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 heterocycloalkyl 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 for 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 C 1 , 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 for 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:

2-[5-chloro-2-(2-methyl-5-phenyl-2H-pyrazol-3-ylamino)-pyridin-4-ylamino]-N-methyl-benzamide;

2-({5-chloro-2-[(1-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-methylbenzamide;

2-({5-chloro-2-[(1-ethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-methylbenzamide;

2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-methylbenzamide;

2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-methylbenzamide;

2-({5-chloro-2-[(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-methylbenzamide;

2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-5-fluoro-N-methylbenzamide;

2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-5-fluoro-N-methylbenzamide;

2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-3-fluoro-N-methylbenzamide;

2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-3-fluoro-N-methylbenzamide;

2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-4,5-difluoro-N-methylbenzamide;

2-({5-chloro-2-[(1-ethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-4,5-difluoro-N-methylbenzamide;

5-chloro-2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-methylbenzamide;

5-chloro-2-({5-chloro-2-[(1-ethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-methylbenzamide;

2-({5-chloro-2-[(1-ethyl-3-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-methylbenzamide;

2-[(5-chloro-2-{[3-(1,1-dimethylethyl)-1-methyl-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-methylbenzamide;

2-[(5-chloro-2-{[1-ethyl-3-(hydroxymethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-methylbenzamide;

2-[(5-chloro-2-{[1-(2-hydroxyethyl)-3-methyl-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-methylbenzamide; ethyl 5-{[5-chloro-4-({2-[(methylamino)carbonyl]phenyl}amino)-2-pyridinyl]amino }-1-ethyl-1H-pyrazole-3-carboxylate;

5-{[5-chloro-4-({2-[(methylamino)carbonyl]phenyl}amino)-2-pyridinyl]amino}-1-ethyl-1H-pyrazole-3-carboxylic acid;

5-{[5-chloro-4-({2-[(methylamino)carbonyl]phenyl}amino)-2-pyridinyl]amino}-1-ethyl-N-(methyloxy)-1H-pyrazole-3-carboxamide;

5-{[5-chloro-4-({2-[(methylamino)carbonyl]phenyl}amino)-2-pyridinyl]amino}-1-ethyl-N-methyl-1H-pyrazole-3-carboxamide;

2-[(5-chloro-2-{[3-methyl-1-(2,2,2-trifluoro ethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-methylbenzamide;

2-[(5-chloro-2-{[1-(1-methyl-4-piperidinyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-methylbenzamide;

2-{[5-chloro-2-({1-[2-(dimethylamino)ethyl]-3-methyl-1H-pyrazol-5-yl}amino)-4-pyridinyl]amino }-N-methylbenzamide;

5-{[5-chloro-4-({2-[(methylamino)carbonyl]phenyl}amino)-2-pyridinyl]amino }-N-[2-(dimethylamino)ethyl]-1-ethyl-1H-pyrazole-3-carboxamide;

5-{[5-chloro-4-({2-[(methylamino)carbonyl]phenyl}amino)-2-pyridinyl]amino }-N-[2-(dimethylamino)ethyl]-1-ethyl-N-methyl-1H-pyrazole-3-carboxamide;

2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-4-yl)amino]-4-pyridinyl}amino)-N-methylbenzamide;

2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-4-yl)amino]-4-pyridinyl}amino)-N-methylbenzamide;

2-{[2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-5-(trifluoromethyl)-4-pyridinyl]amino }-N-methylbenzamide;

2-{[2-[(1-ethyl-1H-pyrazol-5-yl)amino]-5-(trifluoromethyl)-4-pyridinyl]amino }-N-methylbenzamide;

N-methyl-2-{[2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-5-(trifluoromethyl)-4-pyridinyl]amino}benzamide;

2-{[2-({1-[2-(dimethylamino)ethyl]-3-methyl-1H-pyrazol-5-yl]amino)-5-(trifluoromethyl)-4-pyridinyl}amino }-N-methylbenzamide;

2-{[2-[(1-ethyl-3-methyl-1H-pyrazol-5-yl)amino]-5-(trifluoromethyl)-4-pyridinyl]amino}-N-methylbenzamide;

N-methyl-2-{[2-[(3-methyl-1-phenyl-1H-pyrazol-5-yl)amino]-5-(trifluoromethyl)-4-pyridinyl]amino}benzamide;

2-{[2-{[1-(2-hydroxyethyl)-3-methyl-1H-pyrazol-5-yl]amino }-5-(trifluoromethyl)-4-pyridinyl]amino }-N-methylbenzamide;

2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)benzoic acid;

2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-(methyloxy)benzamide;

2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-methyl-N-(methyloxy)benzamide;

2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-{[2-(dimethylamino)ethyl]oxy}benzamide;

2-({5-chloro-2-[(1-ethyl-3-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-(methyloxy)benzamide;

2-({5-chloro-2-[(1-ethyl-3-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-(methyloxy)benzamide;

2-({5-chloro-2-[(1-ethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-(methyloxy)benzamide;

2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-(methyloxy)benzamide;

2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-(methyloxy)benzamide HCl;

2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-(methyloxy)benzamide formate;

2-({5-chloro-2-[(1-ethyl-3-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-ethylbenzamide;

2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-ethylbenzamide;

2-({5-chloro-2-[(1-ethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-ethylbenzamide;

2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-ethylbenzamide;

2-{[5-chloro-2-({1-ethyl-3-[2-(1-pyrrolidinyl)ethyl]-1H-pyrazol-5-yl}amino)-4-pyridinyl]amino }-N-methylbenzamide;

2-({5-chloro-2-[(1,5-dimethyl-1H-pyrazol-4-yl)amino]-4-pyridinyl}amino)-N-(methyloxy)benzamide;

2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-4-yl)amino]-4-pyridinyl}amino)-N-(methyloxy)benzamide;

2-[(5-chloro-2-{[4-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-(methyloxy)benzamide;

2-({5-chloro-2-[(1-ethyl-4-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-(methyloxy)benzamide;

2-[(5-chloro-2-{[4-methyl-1-(2-methylpropyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-(methyloxy)benzamide;

2-[(5-chloro-2-{[3-(hydroxymethyl)-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-(methyloxy)benzamide;

2-[5-cyclopropyl-2-(2,5-dimethyl-2H-pyrazol-3-ylamino)-pyridin-4-ylamino]-N-methyl-benzamide;

2-[5-cyclopropyl-2-(2-ethyl-5-methyl-2H-pyrazol-3-ylamino)-pyridin-4-ylamino]-N-methylbenzamide;

2-[5-cyclopropyl-2-(2,5-dimethyl-2H-pyrazol-3-ylamino)-pyridin-4-ylamino]-N-methoxy-benzamide;

2-[5-cyclopropyl-2-(2-ethyl-5-methyl-2H-pyrazol-3-ylamino)-pyridin-4-ylamino]-N-methoxy-benzamide;

2-[2-(2,5-dimethyl-2H-pyrazol-3-ylamino)-5-isopropenyl-pyridin-4-ylamino]-N-methyl-benzamide;

2-[2-2,5-dimethyl-2H-pyrazol-3-ylamino)-5-isopropyl-pyridin-4-ylamino]-N-methyl-benzamide;

2-({5-chloro-2-[(1,5-dimethyl-1H-pyrazol-4-yl)amino]-4-pyridinyl}amino)-N-methylbenzamide;

2-{[5-chloro-2-({1-ethyl-3-[(methyloxy)methyl]-1H-pyrazol-5-yl}amino)-4-pyridinyl]amino }-N-methylbenzamide;

2-{[5-chloro-2-({1-ethyl-3-[(methyloxy)methyl]-1H-pyrazol-5-yl}amino)-4-pyridinyl]amino }-N-methylbenzamide;

2-[(5-chloro-2-{[3-[(ethyloxy)methyl]-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-methylbenzamide;

2-[(5-chloro-2-{[3-[(ethyloxy)methyl]-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-methylbenzamide;

2-{[5-chloro-2-({1-ethyl-3-[(ethyloxy)methyl]-1H-pyrazol-5-yl}amino)-4-pyridinyl]amino }-N-methylbenzamide;

2-{[5-chloro-2-({1-ethyl-3-[(ethyloxy)methyl]-1H-pyrazol-5-yl}amino)-4-pyridinyl]amino }-N-methylbenzamide;

2-({5-chloro-2-[(1-ethyl-3-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-hydroxy-N-methylbenzamide;

2-({5-chloro-2-[(1-ethyl-3-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-hydroxy-N-methylbenzamide;

2-({5-chloro-2-[(1-ethyl-3-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-(ethyloxy)benzamide;

2-({5-cyano-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-N-methylbenzamide;

2-({5-chloro-2-[(1-ethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-5-[4-(2-hydroxyethyl)-1-piperazinyl]-N-methylbenzamide;

2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-5-[4-(2-hydroxyethyl)-1-piperazinyl]-N-methylbenzamide;

4-chloro-2-[(5-chloro-2-{[3-methyl-1-(1-methyl ethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-(methyloxy)benzamide;

4-chloro-2-[(5-chloro-2-{[3-methyl-1-(1-methyl ethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-(methyloxy)benzamide;

2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-5-fluoro-N-(methyloxy)benzamide;

2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-3-fluoro-N-(methyloxy)benzamide;

2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-4-fluoro-N-(methyloxy)benzamide;

2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-3-fluoro-N-methylbenzamide;

2-({5-chloro-2-[(1-ethyl-3-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-3-fluoro-N-methylbenzamide;

2-({5-chloro-2-[(1,5-dimethyl-1H-pyrazol-4-yl)amino]-4-pyridinyl}amino)-3-fluoro-N-methylbenzamide;

2-{[2-[(1-ethyl-3-methyl-1H-pyrazol-5-yl)amino]-5-(trifluoromethyl)-4-pyridinyl]amino}-3-fluoro-N-methylbenzamide;

2-{[2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-5-(trifluoromethyl)-4-pyridinyl]amino }-3-fluoro-N-methylbenzamide;

2-{[2-{[1-ethyl-3-(hydroxymethyl)-1H-pyrazol-5-yl]amino }-5-chloro-4-pyridinyl]amino}-3-fluoro-N-methylbenzamide;

3-fluoro-2-{[2-{[3-(hydroxymethyl)-1-methyl-1H-pyrazol-5-yl]amino }-5-chloro-4-pyridinyl]amino }-N-methylbenzamide;

2-{[2-{[1-ethyl-3-(2-hydroxyethyl)-1H-pyrazol-5-yl]amino }-5-chloro-4-pyridinyl]amino }-3-fluoro-N-methylbenzamide;

3-fluoro-2-{[2-{[3-(2-hydroxyethyl)-1-methyl-1H-pyrazol-5-yl]amino }-5-chloro-4-pyridinyl]amino }-N-methylbenzamide;

2-{[2-({3-[(dimethylamino)methyl]-1-methyl-1H-pyrazol-5-yl}amino)-5 chloro-4-pyridinyl]amino }-3-fluoro-N-methylbenzamide;

2-{[2-({3-[(dimethylamino)methyl]-1-ethyl-1H-pyrazol-5-yl}amino)-5 chloro-4-pyridinyl]amino }-3-fluoro-N-methylbenzamide;

2-({5-chloro-2-[(3-{[ethyl(methyl)amino]methyl}-1-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-3-fluoro-N-methylbenzamide;

2-{[5-chloro-2-({3-[(diethylamino)methyl]-1-methyl-1H-pyrazol-5-yl}amino)-4-pyridinyl]amino }-3-fluoro-N-methylbenzamide;

2-{[2-{[1-ethyl-3-(hydroxymethyl)-1H-pyrazol-5-yl]amino }-5-(trifluoromethyl)-4-pyridinyl]amino }-3-fluoro-N-methylbenzamide;

3-fluoro-2-{[2-{[3-(hydroxymethyl)-1-methyl-1H-pyrazol-5-yl]amino }-5-(trifluoromethyl)-4-pyridinyl]amino }-N-methylbenzamide;

2-{[2-{[1-ethyl-3-(2-hydroxyethyl)-1H-pyrazol-5-yl]amino }-5-(trifluoromethyl)-4-pyridinyl]amino }-3-fluoro-N-methylbenzamide;

3-fluoro-2-{[2-{[3-(2-hydroxyethyl)-1-methyl-1H-pyrazol-5-yl]amino}-5-(trifluoromethyl)-4-pyridinyl]amino }-N-methylbenzamide;

2-{[2-({3-[(dimethylamino)methyl]-1-methyl-1H-pyrazol-5-yl}amino)-5-(trifluoromethyl)-4-pyridinyl]amino }-3-fluoro-N-methylbenzamide;

2-({5-chloro-2-[(1-ethyl-3-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-3-fluoro-N-(methyloxy)benzamide;

2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-3-fluoro-N-(methyloxy)benzamide;

2-[(5-chloro-2-{[1-ethyl-3-(hydroxymethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-3-fluoro-N-(methyloxy)benzamide;

2-[(5-chloro-2-{[3-(hydroxymethyl)-1-methyl-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-3-fluoro-N-(methyloxy)benzamide;

2-{[5-chloro-2-({3-[(dimethylamino)methyl]-1-ethyl-1H-pyrazol-5-yl}amino)-4-pyridinyl]amino }-3-fluoro-N-(methyloxy)benzamide;

2-({5-chloro-2-[(1,5-dimethyl-1H-pyrazol-4-yl)amino]-4-pyridinyl}amino)-3-fluoro-N-(methyloxy)benzamide;

2-{[5-chloro-2-({3-[(dimethylamino)methyl]-1-ethyl-1H-pyrazol-5-yl}amino)-4-pyridinyl]amino }-N-(methyloxy)benzamide;

2-({5-chloro-2-[(1-ethyl-3-methyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-4-fluoro-N-(methyloxy)benzamide;

2-({5-chloro-2-[(1,3-dimethyl-1H-pyrazol-5-yl)amino]-4-pyridinyl}amino)-4-fluoro-N-(methyloxy)benzamide;

2-[(5-chloro-2-{[1-ethyl-3-(hydroxymethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-4-fluoro-N-(methyloxy)benzamide;

2-[(5-chloro-2-{[1-ethyl-3-(2-hydroxyethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-4-fluoro-N-(methyloxy)benzamide;

2-[(5-chloro-2-{[3-(hydroxymethyl)-1-methyl-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-4-fluoro-N-(methyloxy)benzamide;

2-{[5-chloro-2-({3-[(dimethylamino)methyl]-1-ethyl-1H-pyrazol-5-yl}amino)-4-pyridinyl]amino}-4-fluoro-N-(methyloxy)benzamide;

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 for a pharmaceutically acceptable salt thereof.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 3, 2011
From: ADAMS, JERRY LEROY; FAITG, THOMAS H; JOHNSON, NEIL W; KASPAREC, JIRI; LIN, HONG; MELLINGER, MARK; PENG, XIN; XIE, REN
To: GLAXOSMITHKLINE LLC
Reel/Frame 026257/0460 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 27, 2010
From: ADAMS, JERRY LEROY; FAITG, THOMAS F.; JOHNSON, NEIL W.; LIN, HONG
To: SMITHKLINE BEECHAM CORPORATION
Reel/Frame 023855/0510 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 4, 2010
From: ADAMS, JERRY LEROY; FAITG, THOMAS F.; JOHNSON, NEIL W.; LIN, HONG
To: SMITHKLINE BEECHAM CORPORATION
Reel/Frame 023727/0194 →
CHANGE OF NAME Recorded Jan 4, 2010
From: SMITHKLINE BEECHAM CORPORATION
To: GLAXOSMITHKLINE LLC
Reel/Frame 023727/0497 →