Tyrosine kinase inhibitors
First Claim
Patent Images
1. A compound selected from4-(2-Phenyl-1H-imidazol-1-yl)-N-pyridin-4-ylpyrimidin-2-amine;
- 4-(2-Phenyl-1H-imidazol-1-yl)-N-pyrimidin-4-ylpyrimidin-2-amine;
4-(2-Phenyl-1H-imidazol-1-yl)-N-pyrimidin-2-ylpyrimidin-2-amine;
4-(2-Phenyl-1H-imidazol-1-yl)-N-pyrazin-2-ylpyrimidin-2-amine;
4-(2-Phenyl-1H-imidazol-1-yl)-N-(1,3,4-thiadiazol-2-yl)pyrimidin-2-amine;
N-(5-Methyl-1,3,4-thiadiazol-2-yl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-Isoxazol-3-yl-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(3-Methylisoxazol-5-yl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(4-Methyl-1,3-thiazol-2-yl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(2-Methylpyridin-4-yl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(2,6-Dimethylpyridin-4-yl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
4-(2-Phenyl-1H-imidazol-1-yl)-N-pyridin-3-ylpyrimidin-2-amine;
N-(1-Oxidopyndin-3-yl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-[3-Methoxy-5-(trifluoromethyl)phenyl]-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
(3-Methyl-5-{[4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-yl]amino}phenyl)methanol;
N-{3-[(4-Acetylpiperazin-1-yl)methyl]-5-methylphenyl}-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(3,5-Dimethylphenyl)-4-(2-pyridin-2-yl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(3,5-Dimethylphenyl)-4-(2-pyrimidin-5-yl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(3,5-Dimethylphenyl)-4-(2-pyridin-3-yl-1H-imidazol-1-yl)pyrimidin-2-amine;
4-(2-Cyclopropyl-1H-imidazol-1-yl)-N-(3,5-dimethylphenyl)pyrimidin-2-amine;
N-(3,5-Dimethylphenyl)-4-(4-methyl-2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
1-{2-[(3,5-Dimethylphenyl)amino]pyrimidin-4-yl}-1H-imidazole-2-carbonitrile;
N-(3,5-Dimethylphenyl)-4-(2-methyl-1H-imidazol-1-yl)pyrimidin-2-amine;
4-(2-Amino-1H-imidazol-1-yl)-N-(3,5-dimethylphenyl)pyrimidin-2-amine;
N-(2-methylphenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(2-methoxyphenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(2-fluorophenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(3-chlorophenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(3,5-dichlorophenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(3-fluorophenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(3-methoxyphenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(3-methylphenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(3,5-dimethoxyphenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(4-chlorophenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(4-fluorophenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(4-methoxyphenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(4-methylphenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-[3,5-bis(trifluoromethyl)phenyl]-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-[3-methyl-5-(trifluoromethyl)phenyl]-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(3,5-difluorophenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
4-(2-phenyl-1H-imidazol-1-yl)-N-[3-(trifluoromethyl)phenyl]pyrimidin-2-amine;
N-(3,5-dimethylphenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
4-(2-Phenyl-1H-imidazol-1-yl)-N-pyridin-2-ylpyrimidin-2-amine;
N-{3-[(4-acetylpiperazin-1-yl)methyl]phenyl}-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
4-(2-Chloro-1H-imidazol-1-yl)-N-(3,5-dimethylphenyl)pyrimidin-2-amine;
N-(3,5-Dimethylphenyl)-4-[2-(3-fluorophenyl)-1H-imidazol-1-yl]pyrimidin-2-amine;
or a pharmaceutically acceptable salts thereof.
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Abstract
The present invention relates to compounds which inhibit, regulate and/or modulate tyrosine kinase signal transduction, compositions which contain these compounds, and methods of using them to treat tyrosine kinase-dependent diseases and conditions, such as angiogenesis, cancer, tumor growth, atherosclerosis, age related macular degeneration, diabetic retinopathy, inflammatory diseases, and the like in mammals.
15 Citations
12 Claims
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1. A compound selected from
4-(2-Phenyl-1H-imidazol-1-yl)-N-pyridin-4-ylpyrimidin-2-amine; -
4-(2-Phenyl-1H-imidazol-1-yl)-N-pyrimidin-4-ylpyrimidin-2-amine;
4-(2-Phenyl-1H-imidazol-1-yl)-N-pyrimidin-2-ylpyrimidin-2-amine;
4-(2-Phenyl-1H-imidazol-1-yl)-N-pyrazin-2-ylpyrimidin-2-amine;
4-(2-Phenyl-1H-imidazol-1-yl)-N-(1,3,4-thiadiazol-2-yl)pyrimidin-2-amine;
N-(5-Methyl-1,3,4-thiadiazol-2-yl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-Isoxazol-3-yl-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(3-Methylisoxazol-5-yl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(4-Methyl-1,3-thiazol-2-yl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(2-Methylpyridin-4-yl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(2,6-Dimethylpyridin-4-yl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
4-(2-Phenyl-1H-imidazol-1-yl)-N-pyridin-3-ylpyrimidin-2-amine;
N-(1-Oxidopyndin-3-yl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-[3-Methoxy-5-(trifluoromethyl)phenyl]-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
(3-Methyl-5-{[4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-yl]amino}phenyl)methanol;
N-{3-[(4-Acetylpiperazin-1-yl)methyl]-5-methylphenyl}-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(3,5-Dimethylphenyl)-4-(2-pyridin-2-yl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(3,5-Dimethylphenyl)-4-(2-pyrimidin-5-yl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(3,5-Dimethylphenyl)-4-(2-pyridin-3-yl-1H-imidazol-1-yl)pyrimidin-2-amine;
4-(2-Cyclopropyl-1H-imidazol-1-yl)-N-(3,5-dimethylphenyl)pyrimidin-2-amine;
N-(3,5-Dimethylphenyl)-4-(4-methyl-2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
1-{2-[(3,5-Dimethylphenyl)amino]pyrimidin-4-yl}-1H-imidazole-2-carbonitrile;
N-(3,5-Dimethylphenyl)-4-(2-methyl-1H-imidazol-1-yl)pyrimidin-2-amine;
4-(2-Amino-1H-imidazol-1-yl)-N-(3,5-dimethylphenyl)pyrimidin-2-amine;
N-(2-methylphenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(2-methoxyphenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(2-fluorophenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(3-chlorophenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(3,5-dichlorophenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(3-fluorophenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(3-methoxyphenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(3-methylphenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(3,5-dimethoxyphenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(4-chlorophenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(4-fluorophenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(4-methoxyphenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(4-methylphenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-[3,5-bis(trifluoromethyl)phenyl]-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-[3-methyl-5-(trifluoromethyl)phenyl]-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
N-(3,5-difluorophenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
4-(2-phenyl-1H-imidazol-1-yl)-N-[3-(trifluoromethyl)phenyl]pyrimidin-2-amine;
N-(3,5-dimethylphenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
4-(2-Phenyl-1H-imidazol-1-yl)-N-pyridin-2-ylpyrimidin-2-amine;
N-{3-[(4-acetylpiperazin-1-yl)methyl]phenyl}-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine;
4-(2-Chloro-1H-imidazol-1-yl)-N-(3,5-dimethylphenyl)pyrimidin-2-amine;
N-(3,5-Dimethylphenyl)-4-[2-(3-fluorophenyl)-1H-imidazol-1-yl]pyrimidin-2-amine;
or a pharmaceutically acceptable salts thereof. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9)
or a pharmaceutically acceptable salt thereof.
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3. The compound according to claim 1 which is
N-(3,5-dimethylphenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine; -
or a pharmaceutically acceptable salts thereof.
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4. The compound according to claim 1 which is
N-(3-chlorophenyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine; -
or a pharmaceutically acceptable salt thereof.
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5. The compound according to claim 1 which is
N-(3,5-dimethoxyphenyl)-2-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-amine; -
or a pharmaceutically acceptable salts thereof.
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6. The compound according to claim 1 which is
4-(2-phenyl-1H-imidazol-1-yl)-N-[3-(trifluoromethyl)phenyl]pyrimidin-2-amine; -
or a pharmaceutically acceptable salt thereof.
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7. The compound according to claim 1 which is
(3-methyl-5-{[4-(2-phenyl-1H-imidazol-1-yl)pyrimidin-2-yl]amino}phenyl)methanol; -
or a pharmaceutically acceptable salt thereof.
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8. A pharmaceutical composition which is comprised of a compound in accordance with claim 1 and a pharmaceutically acceptable carrier.
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9. A method of treating breast cancer in a mammal in need of such treatment which is comprised of administering to said mammal a therapeutically effective amount of a compound of claim 1.
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10. The composition of clain 8 further comprising a second compound selected from:
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1) an estrogen receptor modulator, 2) an androgen receptor modulator, 3) retinoid receptor modulator, 4) a cytotoxic agent, 5) an antiproliferative agent, 6) a prenyl-protein transferase inhibitor, 7) an HMG-CoA reductase inhibitor, 8) an HIV protease inhibitor, 9) a reverse transcriptase inhibitor, and 10) another angiogenesis inhibitor. - View Dependent Claims (11, 12)
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Specification