PYRROLOTRIAZINE DERIVATIVES USEFUL FOR TREATING CANCER THROUGH INHIBITION OF AURORA KINASE
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Abstract
This invention relates to novel compounds and processes for their preparation, methods of treating diseases, particularly Cancer, comprising administering said compounds, and methods of making pharmaceutical compositions for the treatment or prevention of disorders, particularly Cancer.
21 Citations
22 Claims
- 1. A compound of formula (I)
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10. A compound having the formula:
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4-amino-5-[4-(1H-benzimidazol-2-ylamino)phenyl]-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5-cyano-1H-benzimidazol-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(7-hydroxy-1H-benzimidazol-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(6-chloro-1H-benzimidazol-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-N-(2,2,2-trifluoroethyl)-5-(4-{[6-(trifluoromethyl)-1H-benzimidazol-2-yl]amino}phenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(6-fluoro-1H-benzimidazol-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(6-methoxy-1H-benzimidazol-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(6-bromo-1H-benzimidazol-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(6-tert-butyl-1H-benzimidazol-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(6-benzoyl-1H-benzimidazol-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5,6-dichloro-1H-benzimidazol-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(6-chloro-5-fluoro-1H-benzimidazol-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5,6-difluoro-1H-benzimidazol-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(6,7-dimethyl-1H-benzimidazol-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-[4-(1H-thieno[3,4-d]imidazol-2-ylamino)phenyl]-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(2,2-difluoro-5H-[1,3]dioxolo[4,5-f]benzimidazol-6-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-[4-(3H-imidazo[4,5-b]pyridin-2-ylamino)phenyl]-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-(4-{[6-(4-methoxyphenyl)-1H-benzimidazol-2-yl]amino}phenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5-pyrrolidin-1-yl-3H-imidazo[4,5-b]pyridin-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-[4-(9H-purin-8-ylamino)phenyl]-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(7-methyl-1H-benzimidazol-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(6-nitro-1H-benzimidazol-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(6-iodo-3H-imidazo[4,5-b]pyridin-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5-chloro-3H-imidazo[4,5-b]pyridin-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(6-phenoxy-1H-benzimidazol-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5-methyl-3H-imidazo[4,5-b]pyridin-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-(4-{[6-(4-fluorophenoxy)-1H-benzimidazol-2-yl]amino}phenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(6-methyl-3H-imidazo[4,5-b]pyridin-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-N-(2,2,2-trifluoroethyl)-5-(4-{[6-(trifluoromethoxy)-1H-benzimidazol-2-yl]amino}phenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(7-fluoro-6-phenoxy-1H-benzimidazol-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5-ethoxy-1H-benzimidazol-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-(4-{[7-fluoro-6-(4-methylphenoxy)-1H-benzimidazol-2-yl]amino}phenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-(4-{[7-fluoro-6-(4-fluorophenoxy)-1H-benzimidazol-2-yl]amino}phenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(1-methyl-1H-benzimidazol-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(7-fluoro-6-pyrrolidin-1-yl-1H-benzimidazol-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5-phenoxy-3H-imidazo[4,5-b]pyridin-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-(4-{[7-fluoro-6-(2-fluorophenoxy)-1H-benzimidazol-2-yl]amino}phenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-(4-{[7-fluoro-6-(3-fluorophenoxy)-1H-benzimidazol-2-yl]amino}phenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-(4-{[7-fluoro-6-(2-methylphenoxy)-1H-benzimidazol-2-yl]amino}phenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-(4-{[7-fluoro-6-(3-methylphenoxy)-1H-benzimidazol-2-yl]amino}phenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-(4-{[7-fluoro-6-(isopropylamino)-1H-benzimidazol-2-yl]amino}phenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide trifluoroacetate; 5-{4-[(6-acetyl-1-methyl-1H-benzimidazol-2-yl)amino]phenyl}-4-amino-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(6-methyl-9H-purin-8-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5-morpholin-4-yl-3H-imidazo[4,5-b]pyridin-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-(4-{[5-(cyclobutylamino)-3H-imidazo[4,5-b]pyridin-2-yl]amino}phenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-(4-{[5-(cyclohexylamino)-3H-imidazo[4,5-b]pyridin-2-yl]amino}phenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-(4-{[5-(3,4-dimethylphenoxy)-3H-imidazo[4,5-b]pyridin-2-yl]amino}phenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-[4-({5-[(3-fluorophenyl)thio]-3H-imidazo[4,5-b]pyridin-2-yl}amino)phenyl]-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-[4-({5-[(cyclohexylmethyl)amino]-3H-imidazo[4,5-b]pyridin-2-yl}amino)phenyl]-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-(4-{[5-(isobutylamino)-3H-imidazo[4,5-b]pyridin-2-yl]amino}phenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-[4-({5-[(2-methoxyethyl)amino]-3H-imidazo[4,5-b]pyridin-2-yl}amino)phenyl]-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-(4-{[5-(tert-butylamino)-3H-imidazo[4,5-b]pyridin-2-yl]amino}phenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-(4-{[5-(propylamino)-3H-imidazo[4,5-b]pyridin-2-yl]amino}phenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-[4-({5-[(2-methoxyethyl)(methyl)amino]-3H-imidazo[4,5-b]pyridin-2-yl}amino)phenyl]-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-(4-{[5-(cyclopropylamino)-3H-imidazo[4,5-b]pyridin-2-yl]amino}phenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-(4-{[5-(3,3-difluoropyrrolidin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl]amino}phenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]-3-fluorophenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(2,2-difluoro-5H-[1,3]dioxolo[4,5-f]benzimidazol-6-yl)amino]-3-fluorophenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(6-chloro-1H-benzimidazol-2-yl)amino]-3-fluorophenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{3-fluoro-4-[(5-methyl-3H-imidazo[4,5-b]pyridin-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{3-fluoro-4-[(5-morpholin-4-yl-3H-imidazo[4,5-b]pyridin-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{3-fluoro-4-[(5-pyrrolidin-1-yl-3H-imidazo[4,5-b]pyridin-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-[3-fluoro-4-(3H-imidazo[4,5-b]pyridin-2-ylamino)phenyl]-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5-chloro-6-fluoro-1H-benzimidazol-2-yl)amino]-3-fluorophenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-[3-fluoro-4-(1H-thieno[3,4-d]imidazol-2-ylamino)phenyl]-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5-benzoyl-1H-benzimidazol-2-yl)amino]-3-fluorophenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-[3-fluoro-4-(1H-imidazo[4,5-c]pyridin-2-ylamino)phenyl]-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{3-fluoro-4-[(7-methyl-1H-benzimidazol-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid; 4-amino-N-(tert-butyl)-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}-N-ethylpyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}-N,N-dimethylpyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}-N-(2-methoxyethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}-6-(morpholin-4-ylcarbonyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine; 4-amino-N-cyclobutyl-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-N-cyclohexyl-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}-N-(3-methylbutyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-N-(cyclopropylmethyl)-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 1-[(4-amino-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}pyrrolo[2,1-f][1,2,4]triazin-6-yl)carbonyl]piperidine-4-carboxamide; 4-amino-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}-N-(3-pyrrolidin-1-ylpropyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}-N-(3-morpholin-4-ylpropyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}-N-[2-(dimethylamino)ethyl]pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-N-cyclopentyl-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}-N-(2-ethoxyethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}-N-(2-hydroxycyclohexyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}-N-(tetrahydro-2H-pyran-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}-N-ethyl-N-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}-N-ethyl-N-isopropylpyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}-6-{[2-(methoxymethyl)pyrrolidin-1-yl]carbonyl}pyrrolo[2,1-f][1,2,4]triazin-4-amine; 4-amino-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}-N-isopropyl-N-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}-N-methyl-N-propylpyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}-N-[2-(dimethylamino)ethyl]-N-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}-6-{[(3R)-3-(dimethylamino)pyrrolidin-1-yl]carbonyl}pyrrolo[2,1-f][1,2,4]triazin-4-amine; 5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}-6-(pyrrolidin-1-ylcarbonyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine; 4-amino-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}-N-ethyl-N-propylpyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}-6-[(4-methylpiperazin-1-yl)carbonyl]pyrrolo[2,1-f][1,2,4]triazin-4-amine; 4-[(4-amino-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}pyrrolo[2,1-f][1,2,4]triazin-6-yl)carbonyl]piperazin-2-one; 4-amino-5-{4-[(5,7-difluoro-1H-benzimidazol-2-yl)amino]phenyl}-N-methyl-N-(tetrahydro-2H-pyran-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(7-fluoro-6-phenoxy-1H-benzimidazol-2-yl)amino]phenyl}pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid; 4-amino-5-{4-[(7-fluoro-6-phenoxy-1H-benzimidazol-2-yl)amino]phenyl}-N-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(7-fluoro-6-phenoxy-1H-benzimidazol-2-yl)amino]phenyl}-N-propylpyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(7-fluoro-6-phenoxy-1H-benzimidazol-2-yl)amino]phenyl}-N-isopropylpyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-N-cyclopropyl-5-{4-[(7-fluoro-6-phenoxy-1H-benzimidazol-2-yl)amino]phenyl}pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-N-ethyl-5-{4-[(7-fluoro-6-phenoxy-1H-benzimidazol-2-yl)amino]phenyl}-N-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 5-{4-[(7-fluoro-6-phenoxy-1H-benzimidazol-2-yl)amino]phenyl}-6-(piperidin-1-ylcarbonyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine; 5-{4-[(7-fluoro-6-phenoxy-1H-benzimidazol-2-yl)amino]phenyl}-6-(morpholin-4-ylcarbonyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine; 4-amino-N-ethyl-5-{4-[(5-pyrrolidin-1-yl-3H-imidazo[4,5-b]pyridin-2-yl)amino]phenyl}pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(7-fluoro-6-phenoxy-1H-benzimidazol-2-yl)amino]phenyl}-N-(2-methoxyethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-{4-[(7-fluoro-6-phenoxy-1H-benzimidazol-2-yl)amino]phenyl}-N-isobutylpyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-N-cyclopentyl-5-{4-[(7-fluoro-6-phenoxy-1H-benzimidazol-2-yl)amino]phenyl}pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 5-{4-[(7-fluoro-6-phenoxy-1H-benzimidazol-2-yl)amino]phenyl}-6-(pyrrolidin-1-ylcarbonyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine; 4-amino-N-(cyclopropylmethyl)-5-{4-[(7-fluoro-6-phenoxy-1H-benzimidazol-2-yl)amino]phenyl}pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-(4-{[5-(4-methylphenyl)-3H-imidazo[4,5-b]pyridin-2-yl]amino}phenyl)-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-[4-({5-[3-(methoxymethyl)phenyl]-3H-imidazo[4,5-b]pyridin-2-yl}amino)phenyl]-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-N-(tert-butyl)-5-{4-[(6-chloro-3H-imidazo[4,5-b]pyridin-2-yl)amino]-3-fluorophenyl}pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-N-(tert-butyl)-5-{4-[(2,2-difluoro-5H-[1,3]dioxolo[4,5-f]benzimidazol-6-yl)amino]-3-fluorophenyl}pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; 4-amino-5-(4-{[5-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl]amino}phenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid; 4-amino-N-(2,2,2-trifluoroethyl)-5-(4-{[5-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl]amino}phenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide; ethyl 4-amino-5-[4-(1H-benzimidazol-2-ylamino)phenyl]pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate; ethyl 4-amino-5-{4-[(5-methoxy-1H-benzimidazol-2-yl)amino]phenyl}pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate; or a pharmaceutically acceptable salt thereof.
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- 14. (canceled)
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16. (canceled)
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17. (canceled)
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18. (canceled)
Specification