CA2663577A1 - Kinase inhibitors useful for the treatment of proliferative diseases - Google Patents
Kinase inhibitors useful for the treatment of proliferative diseases Download PDFInfo
- Publication number
- CA2663577A1 CA2663577A1 CA002663577A CA2663577A CA2663577A1 CA 2663577 A1 CA2663577 A1 CA 2663577A1 CA 002663577 A CA002663577 A CA 002663577A CA 2663577 A CA2663577 A CA 2663577A CA 2663577 A1 CA2663577 A1 CA 2663577A1
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- Prior art keywords
- methyl
- oxo
- urea
- phenyl
- fluoro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 1
- NXNAPIZCMQILQT-UHFFFAOYSA-N 1-(1-cyclopentylpyrazol-4-yl)-3-[2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC(=C1)C=NN1C1CCCC1 NXNAPIZCMQILQT-UHFFFAOYSA-N 0.000 claims 1
- LCUBOMOGRVVEMF-UHFFFAOYSA-N 1-(1-cyclopentylpyrazol-4-yl)-3-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC(=C1)C=NN1C1CCCC1 LCUBOMOGRVVEMF-UHFFFAOYSA-N 0.000 claims 1
- WRJNZWLVJMFZQA-UHFFFAOYSA-N 1-(1-tert-butyl-2-methylpyrrol-3-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=CN(C(C)(C)C)C=1C WRJNZWLVJMFZQA-UHFFFAOYSA-N 0.000 claims 1
- QNSFVYOKDONZNW-UHFFFAOYSA-N 1-(1-tert-butyl-2-methylpyrrol-3-yl)-3-[4-chloro-2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)Cl)=CC=1NC(=O)NC=1C=CN(C(C)(C)C)C=1C QNSFVYOKDONZNW-UHFFFAOYSA-N 0.000 claims 1
- RJLCSKZDENWVON-UHFFFAOYSA-N 1-(1-tert-butyl-2-methylpyrrol-3-yl)-3-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC=1C=CN(C(C)(C)C)C=1C RJLCSKZDENWVON-UHFFFAOYSA-N 0.000 claims 1
- MGNZZPDEJOWXBA-UHFFFAOYSA-N 1-(1-tert-butyl-4-chloropyrrol-3-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CN(C(C)(C)C)C=C1Cl MGNZZPDEJOWXBA-UHFFFAOYSA-N 0.000 claims 1
- LTKYCTKVFFLXSE-UHFFFAOYSA-N 1-(1-tert-butyl-5-chloroimidazol-4-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1N=CN(C(C)(C)C)C=1Cl LTKYCTKVFFLXSE-UHFFFAOYSA-N 0.000 claims 1
- LLGJGSQSGIOLIT-UHFFFAOYSA-N 1-(1-tert-butyl-5-ethylpyrazol-4-yl)-3-[2,4-difluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C1=NN(C(C)(C)C)C(CC)=C1NC(=O)NC1=CC(C=2C(N(C)C3=CC(NC)=NC=C3C=2)=O)=C(F)C=C1F LLGJGSQSGIOLIT-UHFFFAOYSA-N 0.000 claims 1
- MXSWACJTOOSULO-UHFFFAOYSA-N 1-(1-tert-butyl-5-ethylpyrazol-4-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C1=NN(C(C)(C)C)C(CC)=C1NC(=O)NC1=CC(C=2C(N(C)C3=CC(NC)=NC=C3C=2)=O)=C(C)C=C1F MXSWACJTOOSULO-UHFFFAOYSA-N 0.000 claims 1
- JLBBRHWGMQBNPW-UHFFFAOYSA-N 1-(1-tert-butyl-5-ethylpyrazol-4-yl)-3-[4-chloro-2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C1=NN(C(C)(C)C)C(CC)=C1NC(=O)NC1=CC(C=2C(N(C)C3=CC(NC)=NC=C3C=2)=O)=C(Cl)C=C1F JLBBRHWGMQBNPW-UHFFFAOYSA-N 0.000 claims 1
- STJGNJAOWJEKCB-UHFFFAOYSA-N 1-(1-tert-butyl-5-fluoroimidazol-4-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1N=CN(C(C)(C)C)C=1F STJGNJAOWJEKCB-UHFFFAOYSA-N 0.000 claims 1
- JYNOOWLGBINTFP-UHFFFAOYSA-N 1-(1-tert-butyl-5-methylimidazol-4-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1N=CN(C(C)(C)C)C=1C JYNOOWLGBINTFP-UHFFFAOYSA-N 0.000 claims 1
- KFCSLFOKFCXGMZ-UHFFFAOYSA-N 1-(1-tert-butyl-5-methylimidazol-4-yl)-3-[2-fluoro-5-[1-(2-hydroxyethyl)-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(CCO)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC=1N=CN(C(C)(C)C)C=1C KFCSLFOKFCXGMZ-UHFFFAOYSA-N 0.000 claims 1
- GVMUHLYGVBRYFH-UHFFFAOYSA-N 1-(1-tert-butyl-5-methylimidazol-4-yl)-3-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluoro-4-methylphenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC=1N=CN(C(C)(C)C)C=1C GVMUHLYGVBRYFH-UHFFFAOYSA-N 0.000 claims 1
- ABFOPMJHZOURDR-UHFFFAOYSA-N 1-(1-tert-butyl-5-methylimidazol-4-yl)-3-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC=1N=CN(C(C)(C)C)C=1C ABFOPMJHZOURDR-UHFFFAOYSA-N 0.000 claims 1
- GJIIMJKHDBMKBG-UHFFFAOYSA-N 1-(1-tert-butyl-5-methylpyrazol-4-yl)-3-[2,4-difluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)F)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1C GJIIMJKHDBMKBG-UHFFFAOYSA-N 0.000 claims 1
- KPILQKCJWGUCBW-UHFFFAOYSA-N 1-(1-tert-butyl-5-methylpyrazol-4-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1C KPILQKCJWGUCBW-UHFFFAOYSA-N 0.000 claims 1
- YQKCNARAOFPIBA-UHFFFAOYSA-N 1-(1-tert-butyl-5-methylpyrazol-4-yl)-3-[2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC=1C=NN(C(C)(C)C)C=1C YQKCNARAOFPIBA-UHFFFAOYSA-N 0.000 claims 1
- SUSRIEOTADWQDW-UHFFFAOYSA-N 1-(1-tert-butyl-5-methylpyrazol-4-yl)-3-[2-fluoro-5-[7-(methylamino)-2-oxo-1-propan-2-yl-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C(C)C)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC=1C=NN(C(C)(C)C)C=1C SUSRIEOTADWQDW-UHFFFAOYSA-N 0.000 claims 1
- JJTIVARPAYHGPX-UHFFFAOYSA-N 1-(1-tert-butyl-5-methylpyrazol-4-yl)-3-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC=1C=NN(C(C)(C)C)C=1C JJTIVARPAYHGPX-UHFFFAOYSA-N 0.000 claims 1
- GMKSNZQXPKHPRH-UHFFFAOYSA-N 1-(1-tert-butyl-5-methylpyrazol-4-yl)-3-[4-chloro-2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)Cl)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1C GMKSNZQXPKHPRH-UHFFFAOYSA-N 0.000 claims 1
- ZZELQBZYQASTBF-UHFFFAOYSA-N 1-(1-tert-butyl-5-methylpyrazol-4-yl)-3-[4-chloro-2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)Cl)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1C ZZELQBZYQASTBF-UHFFFAOYSA-N 0.000 claims 1
- ZTGGDCZMKWHVAE-UHFFFAOYSA-N 1-(1-tert-butyl-5-methylpyrazol-4-yl)-3-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluoro-4-methylphenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1C ZTGGDCZMKWHVAE-UHFFFAOYSA-N 0.000 claims 1
- VQQQHKUJKARIGX-UHFFFAOYSA-N 1-(1-tert-butylindazol-3-yl)-3-[4-chloro-2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C1=CC=C2C(NC(=O)NC=3C=C(C(=CC=3F)Cl)C=3C(=O)N(C)C=4C=C(N=CC=4C=3)NC)=NN(C(C)(C)C)C2=C1 VQQQHKUJKARIGX-UHFFFAOYSA-N 0.000 claims 1
- WRVFKWVOGQKTBU-UHFFFAOYSA-N 1-(1-tert-butylpyrazol-4-yl)-3-[2,4-difluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)F)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1 WRVFKWVOGQKTBU-UHFFFAOYSA-N 0.000 claims 1
- MVBBKAJVEPKPDI-UHFFFAOYSA-N 1-(1-tert-butylpyrazol-4-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1 MVBBKAJVEPKPDI-UHFFFAOYSA-N 0.000 claims 1
- YOSYURJPUDLLPM-UHFFFAOYSA-N 1-(1-tert-butylpyrazol-4-yl)-3-[2-fluoro-4-methyl-5-[2-(methylamino)-7-oxo-8-propan-2-ylpyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C(C)C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1 YOSYURJPUDLLPM-UHFFFAOYSA-N 0.000 claims 1
- AZUVBHQPAQAAQP-UHFFFAOYSA-N 1-(1-tert-butylpyrazol-4-yl)-3-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1 AZUVBHQPAQAAQP-UHFFFAOYSA-N 0.000 claims 1
- BCVLLGZLRBFDOK-UHFFFAOYSA-N 1-(1-tert-butylpyrazol-4-yl)-3-[2-fluoro-4-methyl-5-[8-methyl-7-oxo-2-(propan-2-ylamino)pyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC(C)C)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1 BCVLLGZLRBFDOK-UHFFFAOYSA-N 0.000 claims 1
- NIJWKRSWGOLTSR-LJQANCHMSA-N 1-(1-tert-butylpyrazol-4-yl)-3-[2-fluoro-4-methyl-5-[8-methyl-7-oxo-2-[[(1r)-1-phenylethyl]amino]pyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound N([C@H](C)C=1C=CC=CC=1)C(N=C1N(C)C2=O)=NC=C1C=C2C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1 NIJWKRSWGOLTSR-LJQANCHMSA-N 0.000 claims 1
- NIJWKRSWGOLTSR-IBGZPJMESA-N 1-(1-tert-butylpyrazol-4-yl)-3-[2-fluoro-4-methyl-5-[8-methyl-7-oxo-2-[[(1s)-1-phenylethyl]amino]pyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=C1N(C)C2=O)=NC=C1C=C2C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1 NIJWKRSWGOLTSR-IBGZPJMESA-N 0.000 claims 1
- SHYKJAPIAVOPCK-UHFFFAOYSA-N 1-(1-tert-butylpyrazol-4-yl)-3-[2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC=1C=NN(C(C)(C)C)C=1 SHYKJAPIAVOPCK-UHFFFAOYSA-N 0.000 claims 1
- KUWDHHCZIRQRCR-UHFFFAOYSA-N 1-(1-tert-butylpyrazol-4-yl)-3-[2-fluoro-5-[2-(methylamino)-7-oxo-8-propan-2-ylpyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C(C)C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC=1C=NN(C(C)(C)C)C=1 KUWDHHCZIRQRCR-UHFFFAOYSA-N 0.000 claims 1
- MNSFABHZBDIRBS-OAHLLOKOSA-N 1-(1-tert-butylpyrazol-4-yl)-3-[2-fluoro-5-[2-[[(2r)-1-hydroxypropan-2-yl]amino]-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]-4-methylphenyl]urea Chemical compound O=C1N(C)C2=NC(N[C@@H](CO)C)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1 MNSFABHZBDIRBS-OAHLLOKOSA-N 0.000 claims 1
- MNSFABHZBDIRBS-HNNXBMFYSA-N 1-(1-tert-butylpyrazol-4-yl)-3-[2-fluoro-5-[2-[[(2s)-1-hydroxypropan-2-yl]amino]-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]-4-methylphenyl]urea Chemical compound O=C1N(C)C2=NC(N[C@H](CO)C)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1 MNSFABHZBDIRBS-HNNXBMFYSA-N 0.000 claims 1
- DYXVAZJONKPCGP-UHFFFAOYSA-N 1-(1-tert-butylpyrazol-4-yl)-3-[2-fluoro-5-[7-(methylamino)-2-oxo-1-phenyl-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound O=C1C(C=2C=C(NC(=O)NC3=CN(N=C3)C(C)(C)C)C(F)=CC=2)=CC=2C=NC(NC)=CC=2N1C1=CC=CC=C1 DYXVAZJONKPCGP-UHFFFAOYSA-N 0.000 claims 1
- DNIVNTRQMRKGDC-UHFFFAOYSA-N 1-(1-tert-butylpyrazol-4-yl)-3-[4-chloro-2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)Cl)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1 DNIVNTRQMRKGDC-UHFFFAOYSA-N 0.000 claims 1
- POWLMLSRWKIZTD-UHFFFAOYSA-N 1-(1-tert-butylpyrazol-4-yl)-3-[4-chloro-2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)Cl)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1 POWLMLSRWKIZTD-UHFFFAOYSA-N 0.000 claims 1
- PWFJZTVZXIECGU-UHFFFAOYSA-N 1-(1-tert-butylpyrazol-4-yl)-3-[4-methyl-3-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1)C)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1 PWFJZTVZXIECGU-UHFFFAOYSA-N 0.000 claims 1
- TVCBLQDNBUZOBW-UHFFFAOYSA-N 1-(1-tert-butylpyrazol-4-yl)-3-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluoro-4-methylphenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1 TVCBLQDNBUZOBW-UHFFFAOYSA-N 0.000 claims 1
- DUYZIRFOKFKQIV-UHFFFAOYSA-N 1-(1-tert-butylpyrazol-4-yl)-3-[5-[2-(2,3-dihydroxypropylamino)-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluoro-4-methylphenyl]urea Chemical compound C1=C(C=2C(N(C)C3=NC(NCC(O)CO)=NC=C3C=2)=O)C(C)=CC(F)=C1NC(=O)NC=1C=NN(C(C)(C)C)C=1 DUYZIRFOKFKQIV-UHFFFAOYSA-N 0.000 claims 1
- ZFSZERWOHCSEEC-UHFFFAOYSA-N 1-(1-tert-butylpyrazol-4-yl)-3-[5-[2-(2,3-dihydroxypropylamino)-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluorophenyl]urea Chemical compound O=C1N(C)C2=NC(NCC(O)CO)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC=1C=NN(C(C)(C)C)C=1 ZFSZERWOHCSEEC-UHFFFAOYSA-N 0.000 claims 1
- XQCAQFGRIKYCGZ-UHFFFAOYSA-N 1-(1-tert-butylpyrazol-4-yl)-3-[5-[2-[2-(dimethylamino)ethylamino]-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluoro-4-methylphenyl]urea Chemical compound O=C1N(C)C2=NC(NCCN(C)C)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1 XQCAQFGRIKYCGZ-UHFFFAOYSA-N 0.000 claims 1
- LPOCEMVZJXJUTF-UHFFFAOYSA-N 1-(1-tert-butylpyrazol-4-yl)-3-[5-[2-[2-(dimethylamino)ethylamino]-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluorophenyl]urea Chemical compound O=C1N(C)C2=NC(NCCN(C)C)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC=1C=NN(C(C)(C)C)C=1 LPOCEMVZJXJUTF-UHFFFAOYSA-N 0.000 claims 1
- OIERBMZFLNFMLF-UHFFFAOYSA-N 1-(1-tert-butylpyrazol-4-yl)-3-[5-[7-[2-(dimethylamino)ethylamino]-1-methyl-2-oxo-1,6-naphthyridin-3-yl]-2-fluoro-4-methylphenyl]urea Chemical compound C=1C=2C=NC(NCCN(C)C)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1 OIERBMZFLNFMLF-UHFFFAOYSA-N 0.000 claims 1
- LFRAAPXYCJCDNH-UHFFFAOYSA-N 1-(1-tert-butylpyrazol-4-yl)-3-[5-[7-[3-(dimethylamino)propylamino]-1-methyl-2-oxo-1,6-naphthyridin-3-yl]-2-fluoro-4-methylphenyl]urea Chemical compound C=1C=2C=NC(NCCCN(C)C)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1 LFRAAPXYCJCDNH-UHFFFAOYSA-N 0.000 claims 1
- XRHUPZIUODKREL-UHFFFAOYSA-N 1-(1-tert-butylpyrazol-4-yl)-3-[5-[8-ethyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluoro-4-methylphenyl]urea Chemical compound O=C1N(CC)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1 XRHUPZIUODKREL-UHFFFAOYSA-N 0.000 claims 1
- AQZXNIBGOZRHHR-UHFFFAOYSA-N 1-(1-tert-butylpyrrol-3-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=CN(C(C)(C)C)C=1 AQZXNIBGOZRHHR-UHFFFAOYSA-N 0.000 claims 1
- QWRUXYXGSJZUTD-UHFFFAOYSA-N 1-(2,3-dichlorophenyl)-3-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC=CC(Cl)=C1Cl QWRUXYXGSJZUTD-UHFFFAOYSA-N 0.000 claims 1
- UCXOOYRWPVZMLD-UHFFFAOYSA-N 1-(2,3-difluorophenyl)-3-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC=CC(F)=C1F UCXOOYRWPVZMLD-UHFFFAOYSA-N 0.000 claims 1
- XWKIDGOLNVKQHD-UHFFFAOYSA-N 1-(2,3-difluorophenyl)-3-[2-fluoro-5-[2-(methylamino)-7-oxo-8-propan-2-ylpyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C(C)C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=CC(F)=C1F XWKIDGOLNVKQHD-UHFFFAOYSA-N 0.000 claims 1
- VAERHVYUGOMUNS-UHFFFAOYSA-N 1-(2-tert-butyl-1,3-oxazol-5-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CN=C(C(C)(C)C)O1 VAERHVYUGOMUNS-UHFFFAOYSA-N 0.000 claims 1
- RFQDYUZXDWTGCE-UHFFFAOYSA-N 1-(2-tert-butyl-1,3-oxazol-5-yl)-3-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CN=C(C(C)(C)C)O1 RFQDYUZXDWTGCE-UHFFFAOYSA-N 0.000 claims 1
- SSDJOMDUTNEOKQ-UHFFFAOYSA-N 1-(2-tert-butyl-1,3-oxazol-5-yl)-3-[2-fluoro-5-[1-(2-hydroxyethyl)-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-4-methylphenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(CCO)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CN=C(C(C)(C)C)O1 SSDJOMDUTNEOKQ-UHFFFAOYSA-N 0.000 claims 1
- ZDZINPZPXUQIAL-UHFFFAOYSA-N 1-(2-tert-butyl-1,3-oxazol-5-yl)-3-[4-chloro-2-fluoro-5-[1-(2-hydroxyethyl)-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(CCO)C(=O)C=1C(C(=CC=1F)Cl)=CC=1NC(=O)NC1=CN=C(C(C)(C)C)O1 ZDZINPZPXUQIAL-UHFFFAOYSA-N 0.000 claims 1
- LMJDTNZCFPHIPB-UHFFFAOYSA-N 1-(2-tert-butyl-1,3-oxazol-5-yl)-3-[4-chloro-2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)Cl)=CC=1NC(=O)NC1=CN=C(C(C)(C)C)O1 LMJDTNZCFPHIPB-UHFFFAOYSA-N 0.000 claims 1
- MDXRKTAYPWECHW-UHFFFAOYSA-N 1-(2-tert-butyl-1,3-oxazol-5-yl)-3-[4-chloro-2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)Cl)=CC=1NC(=O)NC1=CN=C(C(C)(C)C)O1 MDXRKTAYPWECHW-UHFFFAOYSA-N 0.000 claims 1
- SLIBHOOOEXBQBM-UHFFFAOYSA-N 1-(2-tert-butyl-1,3-oxazol-5-yl)-3-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CN=C(C(C)(C)C)O1 SLIBHOOOEXBQBM-UHFFFAOYSA-N 0.000 claims 1
- HQCLQLOKZMIYJF-UHFFFAOYSA-N 1-(2-tert-butyl-1,3-oxazol-5-yl)-3-[5-[8-ethyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluorophenyl]urea Chemical compound O=C1N(CC)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CN=C(C(C)(C)C)O1 HQCLQLOKZMIYJF-UHFFFAOYSA-N 0.000 claims 1
- BBPZBTTVYOYERR-UHFFFAOYSA-N 1-(2-tert-butyl-1,3-thiazol-5-yl)-3-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CN=C(C(C)(C)C)S1 BBPZBTTVYOYERR-UHFFFAOYSA-N 0.000 claims 1
- MDIBSOIRMMVELW-UHFFFAOYSA-N 1-(2-tert-butyl-4-morpholin-4-ylpyrimidin-5-yl)-3-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CN=C(C(C)(C)C)N=C1N1CCOCC1 MDIBSOIRMMVELW-UHFFFAOYSA-N 0.000 claims 1
- QYNZJFHATBTATG-UHFFFAOYSA-N 1-(2-tert-butyl-4-phenylpyrimidin-5-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CN=C(C(C)(C)C)N=C1C1=CC=CC=C1 QYNZJFHATBTATG-UHFFFAOYSA-N 0.000 claims 1
- FSKVLJQHYQRYML-UHFFFAOYSA-N 1-(2-tert-butyl-4-phenylpyrimidin-5-yl)-3-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CN=C(C(C)(C)C)N=C1C1=CC=CC=C1 FSKVLJQHYQRYML-UHFFFAOYSA-N 0.000 claims 1
- LBQYULJQRMMJCX-UHFFFAOYSA-N 1-(2-tert-butyl-4-phenylpyrimidin-5-yl)-3-[3-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=CC=1NC(=O)NC1=CN=C(C(C)(C)C)N=C1C1=CC=CC=C1 LBQYULJQRMMJCX-UHFFFAOYSA-N 0.000 claims 1
- QRJAFRHUTMHRSF-UHFFFAOYSA-N 1-(2-tert-butyl-4-piperazin-1-ylpyrimidin-5-yl)-3-[5-[8-ethyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluorophenyl]urea Chemical compound O=C1N(CC)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CN=C(C(C)(C)C)N=C1N1CCNCC1 QRJAFRHUTMHRSF-UHFFFAOYSA-N 0.000 claims 1
- JMTSNQKPPYZGIL-UHFFFAOYSA-N 1-(2-tert-butyl-4-pyridin-3-ylpyrimidin-5-yl)-3-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CN=C(C(C)(C)C)N=C1C1=CC=CN=C1 JMTSNQKPPYZGIL-UHFFFAOYSA-N 0.000 claims 1
- ZETLDDODEOGHSO-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-3-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(Cl)=CC(Cl)=C1 ZETLDDODEOGHSO-UHFFFAOYSA-N 0.000 claims 1
- ORBQMVXTHJTICG-UHFFFAOYSA-N 1-(3,5-dimethylphenyl)-3-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C)=CC(C)=C1 ORBQMVXTHJTICG-UHFFFAOYSA-N 0.000 claims 1
- AATVLBQXWLHXBT-UHFFFAOYSA-N 1-(3-bicyclo[2.2.1]heptanyl)-3-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound C=1C(NC(=O)NC2C3CCC(C3)C2)=C(F)C=C(C)C=1C1=CC2=CN=C(NC)N=C2N(C)C1=O AATVLBQXWLHXBT-UHFFFAOYSA-N 0.000 claims 1
- UBBXTTCWRYDPRT-UHFFFAOYSA-N 1-(3-bromo-2-methylphenyl)-3-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC=CC(Br)=C1C UBBXTTCWRYDPRT-UHFFFAOYSA-N 0.000 claims 1
- OFYJYKMXLMAXIH-UHFFFAOYSA-N 1-(3-bromophenyl)-3-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC=CC(Br)=C1 OFYJYKMXLMAXIH-UHFFFAOYSA-N 0.000 claims 1
- OZHQXJORGSJPMG-UHFFFAOYSA-N 1-(3-chloro-2-methylphenyl)-3-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC=CC(Cl)=C1C OZHQXJORGSJPMG-UHFFFAOYSA-N 0.000 claims 1
- YLCWWLUYKSOFES-UHFFFAOYSA-N 1-(3-chloro-2-methylphenyl)-3-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=CC(Cl)=C1C YLCWWLUYKSOFES-UHFFFAOYSA-N 0.000 claims 1
- VWUIYLHHLVFHED-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC=CC(Cl)=C1 VWUIYLHHLVFHED-UHFFFAOYSA-N 0.000 claims 1
- WZSJKIHXJIZEIC-UHFFFAOYSA-N 1-(3-cyanophenyl)-3-[2-fluoro-5-[2-(methylamino)-7-oxo-8-propan-2-ylpyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C(C)C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=CC(C#N)=C1 WZSJKIHXJIZEIC-UHFFFAOYSA-N 0.000 claims 1
- ZDARVGSILSOHRZ-UHFFFAOYSA-N 1-(3-cyclopentyl-1,2-oxazol-5-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC(ON=1)=CC=1C1CCCC1 ZDARVGSILSOHRZ-UHFFFAOYSA-N 0.000 claims 1
- ZMTWHRUQULGEHD-UHFFFAOYSA-N 1-(3-cyclopentyl-1,2-oxazol-5-yl)-3-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC(ON=1)=CC=1C1CCCC1 ZMTWHRUQULGEHD-UHFFFAOYSA-N 0.000 claims 1
- VDWNTJSNLRLMEC-UHFFFAOYSA-N 1-(3-cyclopentyl-1,2-oxazol-5-yl)-3-[2-fluoro-5-[1-(2-hydroxyethyl)-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-4-methylphenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(CCO)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC(ON=1)=CC=1C1CCCC1 VDWNTJSNLRLMEC-UHFFFAOYSA-N 0.000 claims 1
- LEWGQGRGXJKULF-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[2-fluoro-4-methyl-5-(1-methyl-2-oxo-7-phenyl-1,6-naphthyridin-3-yl)phenyl]urea Chemical compound C1=C(C=2C(N(C)C3=CC(=NC=C3C=2)C=2C=CC=CC=2)=O)C(C)=CC(F)=C1NC(=O)NC1=CC(C(C)(C)C)=NO1 LEWGQGRGXJKULF-UHFFFAOYSA-N 0.000 claims 1
- BQGUZDIBFFTJRX-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NO1 BQGUZDIBFFTJRX-UHFFFAOYSA-N 0.000 claims 1
- OINOFVJVXAZQJG-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[2-fluoro-4-methyl-5-[2-(methylamino)-7-oxo-8-propan-2-ylpyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C(C)C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NO1 OINOFVJVXAZQJG-UHFFFAOYSA-N 0.000 claims 1
- FKRGVOGXQQOYBE-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[2-fluoro-4-methyl-5-[7-(methylamino)-2-oxo-1-propan-2-yl-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C(C)C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NO1 FKRGVOGXQQOYBE-UHFFFAOYSA-N 0.000 claims 1
- MCFAUZUBUZSPLW-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NO1 MCFAUZUBUZSPLW-UHFFFAOYSA-N 0.000 claims 1
- ZAOSZBPDSRZXCQ-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[2-fluoro-5-(2-methoxy-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)-4-methylphenyl]urea Chemical compound O=C1N(C)C2=NC(OC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NO1 ZAOSZBPDSRZXCQ-UHFFFAOYSA-N 0.000 claims 1
- ZMBWZXAYGBJDHZ-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[2-fluoro-5-(2-oxo-1h-1,6-naphthyridin-3-yl)phenyl]urea Chemical compound O1N=C(C(C)(C)C)C=C1NC(=O)NC1=CC(C=2C(NC3=CC=NC=C3C=2)=O)=CC=C1F ZMBWZXAYGBJDHZ-UHFFFAOYSA-N 0.000 claims 1
- OFQRKBNGHGCRRC-QRWMCTBCSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[2-fluoro-5-[1-[(3r)-3-hydroxycyclopentyl]-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-4-methylphenyl]urea Chemical compound O=C1C(C=2C(=CC(F)=C(NC(=O)NC=3ON=C(C=3)C(C)(C)C)C=2)C)=CC=2C=NC(NC)=CC=2N1C1CC[C@@H](O)C1 OFQRKBNGHGCRRC-QRWMCTBCSA-N 0.000 claims 1
- YYUILDXNUBNILO-QRWMCTBCSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[2-fluoro-5-[1-[(3r)-3-hydroxycyclopentyl]-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound O=C1C(C=2C=C(NC(=O)NC=3ON=C(C=3)C(C)(C)C)C(F)=CC=2)=CC=2C=NC(NC)=CC=2N1C1CC[C@@H](O)C1 YYUILDXNUBNILO-QRWMCTBCSA-N 0.000 claims 1
- CGZIJYAIMZQBHZ-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NO1 CGZIJYAIMZQBHZ-UHFFFAOYSA-N 0.000 claims 1
- HPGHPSIAVZAOGD-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[2-fluoro-5-[2-(methylamino)-7-oxo-8-propan-2-ylpyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C(C)C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NO1 HPGHPSIAVZAOGD-UHFFFAOYSA-N 0.000 claims 1
- ISONFSPHJXOGHR-NRFANRHFSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[2-fluoro-5-[2-[[(2r)-1-hydroxy-3-methylbutan-2-yl]amino]-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]-4-methylphenyl]urea Chemical compound O=C1N(C)C2=NC(N[C@@H](CO)C(C)C)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NO1 ISONFSPHJXOGHR-NRFANRHFSA-N 0.000 claims 1
- ISONFSPHJXOGHR-OAQYLSRUSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[2-fluoro-5-[2-[[(2s)-1-hydroxy-3-methylbutan-2-yl]amino]-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]-4-methylphenyl]urea Chemical compound O=C1N(C)C2=NC(N[C@H](CO)C(C)C)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NO1 ISONFSPHJXOGHR-OAQYLSRUSA-N 0.000 claims 1
- DGBBIVLMMQBCKO-INIZCTEOSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[2-fluoro-5-[2-[[(2s)-1-hydroxypropan-2-yl]amino]-7-oxo-8-propan-2-ylpyrido[2,3-d]pyrimidin-6-yl]-4-methylphenyl]urea Chemical compound O=C1N(C(C)C)C2=NC(N[C@H](CO)C)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NO1 DGBBIVLMMQBCKO-INIZCTEOSA-N 0.000 claims 1
- QEPYYDKSQNJCQB-ZDUSSCGKSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[2-fluoro-5-[2-[[(2s)-1-hydroxypropan-2-yl]amino]-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(N[C@H](CO)C)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NO1 QEPYYDKSQNJCQB-ZDUSSCGKSA-N 0.000 claims 1
- UKWRGQKQCOCMFE-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[2-fluoro-5-[7-(methylamino)-2-oxo-1-phenyl-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound O=C1C(C=2C=C(NC(=O)NC=3ON=C(C=3)C(C)(C)C)C(F)=CC=2)=CC=2C=NC(NC)=CC=2N1C1=CC=CC=C1 UKWRGQKQCOCMFE-UHFFFAOYSA-N 0.000 claims 1
- LYNHNAOMAYBHJG-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[2-fluoro-5-[7-(methylamino)-2-oxo-1-propan-2-yl-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C(C)C)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NO1 LYNHNAOMAYBHJG-UHFFFAOYSA-N 0.000 claims 1
- MQYLNQPBTDZWLQ-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NO1 MQYLNQPBTDZWLQ-UHFFFAOYSA-N 0.000 claims 1
- PBQDDSMCIYKEDD-QGZVFWFLSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[2-fluoro-5-[8-methyl-7-oxo-2-[[(1r)-1-phenylethyl]amino]pyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound N([C@H](C)C=1C=CC=CC=1)C(N=C1N(C)C2=O)=NC=C1C=C2C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NO1 PBQDDSMCIYKEDD-QGZVFWFLSA-N 0.000 claims 1
- PBQDDSMCIYKEDD-KRWDZBQOSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[2-fluoro-5-[8-methyl-7-oxo-2-[[(1s)-1-phenylethyl]amino]pyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=C1N(C)C2=O)=NC=C1C=C2C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NO1 PBQDDSMCIYKEDD-KRWDZBQOSA-N 0.000 claims 1
- SIEQYNFHFLXSEY-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[4-chloro-2-fluoro-5-[1-(2-hydroxyethyl)-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(CCO)C(=O)C=1C(C(=CC=1F)Cl)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NO1 SIEQYNFHFLXSEY-UHFFFAOYSA-N 0.000 claims 1
- VHRVVQJYCONUND-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[4-chloro-2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)Cl)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NO1 VHRVVQJYCONUND-UHFFFAOYSA-N 0.000 claims 1
- CPWBRPBXOQREAK-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[4-chloro-2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)Cl)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NO1 CPWBRPBXOQREAK-UHFFFAOYSA-N 0.000 claims 1
- YUOPLBXUVQGOPB-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[4-chloro-3-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C(=CC=1)Cl)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NO1 YUOPLBXUVQGOPB-UHFFFAOYSA-N 0.000 claims 1
- UZNVUEHZNGPPHR-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[4-chloro-3-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1)Cl)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NO1 UZNVUEHZNGPPHR-UHFFFAOYSA-N 0.000 claims 1
- OOIOLITWBYROII-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[4-chloro-5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C(=CC=1F)Cl)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NO1 OOIOLITWBYROII-UHFFFAOYSA-N 0.000 claims 1
- HWZFCZCIBMYZQZ-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[4-methyl-3-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1)C)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NO1 HWZFCZCIBMYZQZ-UHFFFAOYSA-N 0.000 claims 1
- ADKGNIUREJAARH-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[5-(1-ethyl-2-oxo-1,6-naphthyridin-3-yl)-2-fluorophenyl]urea Chemical compound O=C1N(CC)C2=CC=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NO1 ADKGNIUREJAARH-UHFFFAOYSA-N 0.000 claims 1
- KYRKYPZCHKJOTK-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[5-[1-cyclopentyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]urea Chemical compound O=C1C(C=2C=C(NC(=O)NC=3ON=C(C=3)C(C)(C)C)C(F)=CC=2)=CC=2C=NC(NC)=CC=2N1C1CCCC1 KYRKYPZCHKJOTK-UHFFFAOYSA-N 0.000 claims 1
- BWWSAKOFIQJSSK-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NO1 BWWSAKOFIQJSSK-UHFFFAOYSA-N 0.000 claims 1
- JEQWOWFWUPBCMY-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[5-[2-[2-(dimethylamino)ethylamino]-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluoro-4-methylphenyl]urea Chemical compound O=C1N(C)C2=NC(NCCN(C)C)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NO1 JEQWOWFWUPBCMY-UHFFFAOYSA-N 0.000 claims 1
- CNUYWFSQNXQDON-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[5-[2-[2-(dimethylamino)ethylamino]-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluorophenyl]urea Chemical compound O=C1N(C)C2=NC(NCCN(C)C)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NO1 CNUYWFSQNXQDON-UHFFFAOYSA-N 0.000 claims 1
- HFYUSVPACGHRDX-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[5-[2-[3-(dimethylamino)propylamino]-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluoro-4-methylphenyl]urea Chemical compound O=C1N(C)C2=NC(NCCCN(C)C)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NO1 HFYUSVPACGHRDX-UHFFFAOYSA-N 0.000 claims 1
- MMCLQBQOLLZJCF-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[5-[8-cyclopentyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluoro-4-methylphenyl]urea Chemical compound O=C1N(C2CCCC2)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NO1 MMCLQBQOLLZJCF-UHFFFAOYSA-N 0.000 claims 1
- GDTKBCJRGQGUIC-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[5-[8-cyclopentyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluorophenyl]urea Chemical compound O=C1N(C2CCCC2)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NO1 GDTKBCJRGQGUIC-UHFFFAOYSA-N 0.000 claims 1
- GSUAJSNEHOVCMA-UHFFFAOYSA-N 1-(3-tert-butyl-1,2-oxazol-5-yl)-3-[5-[8-ethyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluoro-4-methylphenyl]urea Chemical compound O=C1N(CC)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NO1 GSUAJSNEHOVCMA-UHFFFAOYSA-N 0.000 claims 1
- JWAWFIUNNAJBGE-UHFFFAOYSA-N 1-(3-tert-butyl-4-chloro-1,2-oxazol-5-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1ON=C(C(C)(C)C)C=1Cl JWAWFIUNNAJBGE-UHFFFAOYSA-N 0.000 claims 1
- UQSRLLXZPUOMTB-UHFFFAOYSA-N 1-(3-tert-butyl-4-fluoro-1,2-oxazol-5-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1ON=C(C(C)(C)C)C=1F UQSRLLXZPUOMTB-UHFFFAOYSA-N 0.000 claims 1
- LURPZPGYWODLEC-UHFFFAOYSA-N 1-(3-tert-butyl-4-fluoro-1,2-oxazol-5-yl)-3-[2-fluoro-5-[1-(2-hydroxyethyl)-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-4-methylphenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(CCO)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1ON=C(C(C)(C)C)C=1F LURPZPGYWODLEC-UHFFFAOYSA-N 0.000 claims 1
- XQLGUJZWZBIGHE-UHFFFAOYSA-N 1-(3-tert-butyl-4-methyl-1,2-oxazol-5-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1ON=C(C(C)(C)C)C=1C XQLGUJZWZBIGHE-UHFFFAOYSA-N 0.000 claims 1
- HSUFUVLJBJWOHL-UHFFFAOYSA-N 1-(3-tert-butyl-4-methyl-1,2-oxazol-5-yl)-3-[2-fluoro-5-[1-(2-hydroxyethyl)-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-4-methylphenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(CCO)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1ON=C(C(C)(C)C)C=1C HSUFUVLJBJWOHL-UHFFFAOYSA-N 0.000 claims 1
- RTFJXDOFKXBCRO-UHFFFAOYSA-N 1-(3-tert-butylphenyl)-3-[2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=CC(C(C)(C)C)=C1 RTFJXDOFKXBCRO-UHFFFAOYSA-N 0.000 claims 1
- IELFMFBQIQVSIP-UHFFFAOYSA-N 1-(3-tert-butylphenyl)-3-[5-[2-[2-(dimethylamino)ethylamino]-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluorophenyl]urea Chemical compound O=C1N(C)C2=NC(NCCN(C)C)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=CC(C(C)(C)C)=C1 IELFMFBQIQVSIP-UHFFFAOYSA-N 0.000 claims 1
- CEEONUSLWHFPGY-UHFFFAOYSA-N 1-(3-tert-butylphenyl)-3-[5-[8-ethyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluorophenyl]urea Chemical compound O=C1N(CC)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=CC(C(C)(C)C)=C1 CEEONUSLWHFPGY-UHFFFAOYSA-N 0.000 claims 1
- MHWUJGJZRCWUMM-UHFFFAOYSA-N 1-(4-tert-butyl-1-methylpyrrol-2-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)(C)C)=CN1C MHWUJGJZRCWUMM-UHFFFAOYSA-N 0.000 claims 1
- HXUPGUHKYKHIKA-UHFFFAOYSA-N 1-(4-tert-butyl-1-methylpyrrol-2-yl)-3-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=CN1C HXUPGUHKYKHIKA-UHFFFAOYSA-N 0.000 claims 1
- TXJPDLJUPOZJBU-UHFFFAOYSA-N 1-(4-tert-butyl-3-chloro-1-methylpyrrol-2-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=C(Cl)C(C(C)(C)C)=CN1C TXJPDLJUPOZJBU-UHFFFAOYSA-N 0.000 claims 1
- SBNKFZJJMUXBOL-UHFFFAOYSA-N 1-(4-tert-butyl-3-chlorofuran-2-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1OC=C(C(C)(C)C)C=1Cl SBNKFZJJMUXBOL-UHFFFAOYSA-N 0.000 claims 1
- LMXYEKAQKSPQFY-UHFFFAOYSA-N 1-(4-tert-butyl-3-chlorothiophen-2-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1SC=C(C(C)(C)C)C=1Cl LMXYEKAQKSPQFY-UHFFFAOYSA-N 0.000 claims 1
- CDRBCQCFVHSTFQ-UHFFFAOYSA-N 1-(4-tert-butyl-3-fluorofuran-2-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1OC=C(C(C)(C)C)C=1F CDRBCQCFVHSTFQ-UHFFFAOYSA-N 0.000 claims 1
- XCRSDZVFOCSUKC-UHFFFAOYSA-N 1-(4-tert-butyl-3-fluorothiophen-2-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1SC=C(C(C)(C)C)C=1F XCRSDZVFOCSUKC-UHFFFAOYSA-N 0.000 claims 1
- YQBSEFMMBBAFAM-UHFFFAOYSA-N 1-(4-tert-butyl-3-methylfuran-2-yl)-3-[2-fluoro-5-[1-(2-hydroxyethyl)-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-4-methylphenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(CCO)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1OC=C(C(C)(C)C)C=1C YQBSEFMMBBAFAM-UHFFFAOYSA-N 0.000 claims 1
- MSPKQEDIQWCKSP-UHFFFAOYSA-N 1-(4-tert-butyl-3-methylthiophen-2-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1SC=C(C(C)(C)C)C=1C MSPKQEDIQWCKSP-UHFFFAOYSA-N 0.000 claims 1
- RTBRCRUNLJHVHV-UHFFFAOYSA-N 1-(4-tert-butyl-3-methylthiophen-2-yl)-3-[2-fluoro-5-[1-(2-hydroxyethyl)-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-4-methylphenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(CCO)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1SC=C(C(C)(C)C)C=1C RTBRCRUNLJHVHV-UHFFFAOYSA-N 0.000 claims 1
- XTONXGMRNAEBLE-UHFFFAOYSA-N 1-(4-tert-butylfuran-2-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)(C)C)=CO1 XTONXGMRNAEBLE-UHFFFAOYSA-N 0.000 claims 1
- OTZPURVNXZIJMY-UHFFFAOYSA-N 1-(4-tert-butylthiophen-2-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)(C)C)=CS1 OTZPURVNXZIJMY-UHFFFAOYSA-N 0.000 claims 1
- UCRZOWQXAJVQFK-UHFFFAOYSA-N 1-(5-bicyclo[2.2.1]hept-2-enyl)-3-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound C=1C(NC(=O)NC2C3CC(C=C3)C2)=C(F)C=C(C)C=1C1=CC2=CN=C(NC)N=C2N(C)C1=O UCRZOWQXAJVQFK-UHFFFAOYSA-N 0.000 claims 1
- FDNWDRASCMQDED-UHFFFAOYSA-N 1-(5-cyclopentyl-2-methylpyrazol-3-yl)-3-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC(N(N=1)C)=CC=1C1CCCC1 FDNWDRASCMQDED-UHFFFAOYSA-N 0.000 claims 1
- VURZUHOFBKDXNZ-UHFFFAOYSA-N 1-(5-cyclopentyl-2-methylpyrazol-3-yl)-3-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC(N(N=1)C)=CC=1C1CCCC1 VURZUHOFBKDXNZ-UHFFFAOYSA-N 0.000 claims 1
- PVOJRXVONLVAOZ-UHFFFAOYSA-N 1-(5-cyclopentyl-2-methylpyrazol-3-yl)-3-[5-[2-[2-(dimethylamino)ethylamino]-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluoro-4-methylphenyl]urea Chemical compound O=C1N(C)C2=NC(NCCN(C)C)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC(N(N=1)C)=CC=1C1CCCC1 PVOJRXVONLVAOZ-UHFFFAOYSA-N 0.000 claims 1
- AKOKBOQWYYAOTG-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[2,4-difluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)F)=CC=1NC(=O)NC=1C=C(C(C)(C)C)ON=1 AKOKBOQWYYAOTG-UHFFFAOYSA-N 0.000 claims 1
- BIOHTYDCSGXRIC-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=C(C(C)(C)C)ON=1 BIOHTYDCSGXRIC-UHFFFAOYSA-N 0.000 claims 1
- OJQQILOSHZAZFX-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[2-fluoro-5-[1-(2-hydroxyethyl)-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-4-methylphenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(CCO)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=C(C(C)(C)C)ON=1 OJQQILOSHZAZFX-UHFFFAOYSA-N 0.000 claims 1
- KGUQGHHYXOWJRA-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC=1C=C(C(C)(C)C)ON=1 KGUQGHHYXOWJRA-UHFFFAOYSA-N 0.000 claims 1
- GKGVDGLHNWWFKT-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-chloro-2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)Cl)=CC=1NC(=O)NC=1C=C(C(C)(C)C)ON=1 GKGVDGLHNWWFKT-UHFFFAOYSA-N 0.000 claims 1
- WGFXGQXFFZXDNX-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-chloro-2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)Cl)=CC=1NC(=O)NC=1C=C(C(C)(C)C)ON=1 WGFXGQXFFZXDNX-UHFFFAOYSA-N 0.000 claims 1
- MIRDGCPMEYQDAY-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-chloro-5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C(=CC=1F)Cl)=CC=1NC(=O)NC=1C=C(C(C)(C)C)ON=1 MIRDGCPMEYQDAY-UHFFFAOYSA-N 0.000 claims 1
- PVHRQQKXBQHCDD-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-cyano-2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C#N)=CC=1NC(=O)NC=1C=C(C(C)(C)C)ON=1 PVHRQQKXBQHCDD-UHFFFAOYSA-N 0.000 claims 1
- PWEGZMBZHNTYRJ-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-ethynyl-2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C#C)=CC=1NC(=O)NC=1C=C(C(C)(C)C)ON=1 PWEGZMBZHNTYRJ-UHFFFAOYSA-N 0.000 claims 1
- IIVDLWWOMBXOAH-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[4-methyl-3-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1)C)=CC=1NC(=O)NC=1C=C(C(C)(C)C)ON=1 IIVDLWWOMBXOAH-UHFFFAOYSA-N 0.000 claims 1
- PNUNCIPMUKNDMD-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluoro-4-methylphenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=C(C(C)(C)C)ON=1 PNUNCIPMUKNDMD-UHFFFAOYSA-N 0.000 claims 1
- KEPQIKKOUOULMH-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[5-[2-[2-(dimethylamino)ethylamino]-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluoro-4-methylphenyl]urea Chemical compound O=C1N(C)C2=NC(NCCN(C)C)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=C(C(C)(C)C)ON=1 KEPQIKKOUOULMH-UHFFFAOYSA-N 0.000 claims 1
- FCNCEFOPFHNDLN-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[5-[2-[2-(dimethylamino)ethylamino]-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluorophenyl]urea Chemical compound O=C1N(C)C2=NC(NCCN(C)C)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC=1C=C(C(C)(C)C)ON=1 FCNCEFOPFHNDLN-UHFFFAOYSA-N 0.000 claims 1
- HMKJSXCPFGYVAB-UHFFFAOYSA-N 1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[5-[8-ethyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluoro-4-methylphenyl]urea Chemical compound O=C1N(CC)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=C(C(C)(C)C)ON=1 HMKJSXCPFGYVAB-UHFFFAOYSA-N 0.000 claims 1
- RCFNOPLNWCVEJN-UHFFFAOYSA-N 1-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-3-[2,4-difluoro-5-[1-(2-hydroxyethyl)-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(CCO)C(=O)C=1C(C(=CC=1F)F)=CC=1NC(=O)NC1=NN=C(C(C)(C)C)S1 RCFNOPLNWCVEJN-UHFFFAOYSA-N 0.000 claims 1
- ARKXLIFFQZQIQX-UHFFFAOYSA-N 1-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-3-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=NN=C(C(C)(C)C)S1 ARKXLIFFQZQIQX-UHFFFAOYSA-N 0.000 claims 1
- QUYBUNNIHBKSBC-UHFFFAOYSA-N 1-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-3-[2-fluoro-5-[1-(2-hydroxyethyl)-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-4-methylphenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(CCO)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=NN=C(C(C)(C)C)S1 QUYBUNNIHBKSBC-UHFFFAOYSA-N 0.000 claims 1
- VBVYEMMAUIQOKD-UHFFFAOYSA-N 1-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-3-[2-fluoro-5-[1-(2-hydroxyethyl)-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(CCO)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC1=NN=C(C(C)(C)C)S1 VBVYEMMAUIQOKD-UHFFFAOYSA-N 0.000 claims 1
- DJMVMSCOQJOQTQ-UHFFFAOYSA-N 1-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-3-[2-fluoro-5-[2-(methylamino)-7-oxo-8-propan-2-ylpyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C(C)C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=NN=C(C(C)(C)C)S1 DJMVMSCOQJOQTQ-UHFFFAOYSA-N 0.000 claims 1
- CFYZNKHRSZCRKZ-UHFFFAOYSA-N 1-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-3-[4-chloro-2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)Cl)=CC=1NC(=O)NC1=NN=C(C(C)(C)C)S1 CFYZNKHRSZCRKZ-UHFFFAOYSA-N 0.000 claims 1
- LUJYXFLNBQBRDP-UHFFFAOYSA-N 1-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-3-[4-chloro-2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)Cl)=CC=1NC(=O)NC1=NN=C(C(C)(C)C)S1 LUJYXFLNBQBRDP-UHFFFAOYSA-N 0.000 claims 1
- ROKDVHBJZSOKGV-UHFFFAOYSA-N 1-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-3-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluoro-4-methylphenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=NN=C(C(C)(C)C)S1 ROKDVHBJZSOKGV-UHFFFAOYSA-N 0.000 claims 1
- ZPWYOPBWJCIDLT-UHFFFAOYSA-N 1-(5-tert-butyl-2-ethylpyrazol-3-yl)-3-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound CCN1N=C(C(C)(C)C)C=C1NC(=O)NC1=CC(C=2C(N(C)C3=NC(NC)=NC=C3C=2)=O)=CC=C1F ZPWYOPBWJCIDLT-UHFFFAOYSA-N 0.000 claims 1
- OZHKZUOYTPQPBZ-UHFFFAOYSA-N 1-(5-tert-butyl-2-ethylpyrazol-3-yl)-3-[5-[8-ethyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluorophenyl]urea Chemical compound CCN1N=C(C(C)(C)C)C=C1NC(=O)NC1=CC(C=2C(N(CC)C3=NC(NC)=NC=C3C=2)=O)=CC=C1F OZHKZUOYTPQPBZ-UHFFFAOYSA-N 0.000 claims 1
- ZXHDJABKWXWDII-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NN1C ZXHDJABKWXWDII-UHFFFAOYSA-N 0.000 claims 1
- AJLFNGNEOGAEMN-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-[2-fluoro-4-methyl-5-[2-(methylamino)-7-oxo-8-propan-2-ylpyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C(C)C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NN1C AJLFNGNEOGAEMN-UHFFFAOYSA-N 0.000 claims 1
- SZUBVKQPJBWQET-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NN1C SZUBVKQPJBWQET-UHFFFAOYSA-N 0.000 claims 1
- FVPIUIGAPHUIND-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-[2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NN1C FVPIUIGAPHUIND-UHFFFAOYSA-N 0.000 claims 1
- ZUMNZMSYXCYPLG-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-[2-fluoro-5-[2-(methylamino)-7-oxo-8-propan-2-ylpyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C(C)C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NN1C ZUMNZMSYXCYPLG-UHFFFAOYSA-N 0.000 claims 1
- DDQXENLLNRIPIU-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-[2-fluoro-5-[7-(methylamino)-2-oxo-1-propan-2-yl-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C(C)C)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NN1C DDQXENLLNRIPIU-UHFFFAOYSA-N 0.000 claims 1
- BJYUUECNPBMAEC-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NN1C BJYUUECNPBMAEC-UHFFFAOYSA-N 0.000 claims 1
- JYLUNVGWSVQOBL-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-[4-chloro-2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)Cl)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NN1C JYLUNVGWSVQOBL-UHFFFAOYSA-N 0.000 claims 1
- VRZSDEJGEOLBGM-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-[4-chloro-2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)Cl)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NN1C VRZSDEJGEOLBGM-UHFFFAOYSA-N 0.000 claims 1
- ALHKWUHXTAEKEW-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-[4-methyl-3-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1)C)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NN1C ALHKWUHXTAEKEW-UHFFFAOYSA-N 0.000 claims 1
- JPQRTNIYTQSYPE-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluoro-4-methylphenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NN1C JPQRTNIYTQSYPE-UHFFFAOYSA-N 0.000 claims 1
- KPVNZZMFEXBTJT-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NN1C KPVNZZMFEXBTJT-UHFFFAOYSA-N 0.000 claims 1
- DBYAWSSNKHEXLB-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-[5-[2-[2-(dimethylamino)ethylamino]-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluoro-4-methylphenyl]urea Chemical compound O=C1N(C)C2=NC(NCCN(C)C)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NN1C DBYAWSSNKHEXLB-UHFFFAOYSA-N 0.000 claims 1
- AHKPIOKDSSOTBL-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-[5-[2-[2-(dimethylamino)ethylamino]-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluorophenyl]urea Chemical compound O=C1N(C)C2=NC(NCCN(C)C)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NN1C AHKPIOKDSSOTBL-UHFFFAOYSA-N 0.000 claims 1
- GEBCTIJUEWGEJG-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-[5-[8-cyclopentyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluoro-4-methylphenyl]urea Chemical compound O=C1N(C2CCCC2)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NN1C GEBCTIJUEWGEJG-UHFFFAOYSA-N 0.000 claims 1
- JWAUVVYWOUZWRE-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-[5-[8-cyclopentyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluorophenyl]urea Chemical compound O=C1N(C2CCCC2)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NN1C JWAUVVYWOUZWRE-UHFFFAOYSA-N 0.000 claims 1
- SQSKAVYPMFFZTE-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-[5-[8-ethyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluorophenyl]urea Chemical compound O=C1N(CC)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NN1C SQSKAVYPMFFZTE-UHFFFAOYSA-N 0.000 claims 1
- RHVQYOQTJBWZSJ-UHFFFAOYSA-N 1-(5-tert-butyl-2-phenylpyrazol-3-yl)-3-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=CC=C1 RHVQYOQTJBWZSJ-UHFFFAOYSA-N 0.000 claims 1
- QXXKQWZTPZXTOP-UHFFFAOYSA-N 1-(5-tert-butyl-2-phenylpyrazol-3-yl)-3-[2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=CC=C1 QXXKQWZTPZXTOP-UHFFFAOYSA-N 0.000 claims 1
- GSJKAUXMCOXQDE-UHFFFAOYSA-N 1-(5-tert-butyl-2-phenylpyrazol-3-yl)-3-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=CC=C1 GSJKAUXMCOXQDE-UHFFFAOYSA-N 0.000 claims 1
- KAIYLDWVUZAZBW-UHFFFAOYSA-N 1-(5-tert-butyl-2-propan-2-ylpyrazol-3-yl)-3-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NN1C(C)C KAIYLDWVUZAZBW-UHFFFAOYSA-N 0.000 claims 1
- KKDOFBALBZLPEW-UHFFFAOYSA-N 1-(5-tert-butyl-4-methyl-1,2-oxazol-3-yl)-3-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluoro-4-methylphenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=NOC(C(C)(C)C)=C1C KKDOFBALBZLPEW-UHFFFAOYSA-N 0.000 claims 1
- WOLNRNBOONZZAJ-UHFFFAOYSA-N 1-(5-tert-butyl-4-methyl-1,2-oxazol-3-yl)-3-[5-[8-ethyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluoro-4-methylphenyl]urea Chemical compound O=C1N(CC)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=NOC(C(C)(C)C)=C1C WOLNRNBOONZZAJ-UHFFFAOYSA-N 0.000 claims 1
- UMIIXUOCQUMIHJ-UHFFFAOYSA-N 1-(5-tert-butylthiophen-3-yl)-3-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CSC(C(C)(C)C)=C1 UMIIXUOCQUMIHJ-UHFFFAOYSA-N 0.000 claims 1
- XPMWDAHZMOCUFJ-OAQYLSRUSA-N 1-[(1r)-2,3-dihydro-1h-inden-1-yl]-3-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1CC2=CC=CC=C2[C@@H]1NC(=O)NC1=C(F)C=C(C)C(C2=CC3=CN=C(N=C3N(C)C2=O)NC)=C1 XPMWDAHZMOCUFJ-OAQYLSRUSA-N 0.000 claims 1
- XPMWDAHZMOCUFJ-NRFANRHFSA-N 1-[(1s)-2,3-dihydro-1h-inden-1-yl]-3-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1CC2=CC=CC=C2[C@H]1NC(=O)NC1=C(F)C=C(C)C(C2=CC3=CN=C(N=C3N(C)C2=O)NC)=C1 XPMWDAHZMOCUFJ-NRFANRHFSA-N 0.000 claims 1
- VNKRAHNKGZKCKI-UHFFFAOYSA-N 1-[1-[2-(dimethylamino)ethyl]-5-propan-2-ylpyrazol-3-yl]-3-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=C(C(C)C)N(CCN(C)C)N=1 VNKRAHNKGZKCKI-UHFFFAOYSA-N 0.000 claims 1
- MKOYFFAMZSCDAN-UHFFFAOYSA-N 1-[1-tert-butyl-5-(1-hydroxyethyl)pyrazol-4-yl]-3-[2,4-difluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)F)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1C(C)O MKOYFFAMZSCDAN-UHFFFAOYSA-N 0.000 claims 1
- HQSRDBZHBDTLPV-UHFFFAOYSA-N 1-[1-tert-butyl-5-(1-hydroxyethyl)pyrazol-4-yl]-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1C(C)O HQSRDBZHBDTLPV-UHFFFAOYSA-N 0.000 claims 1
- PMORCZIWMGAJGZ-UHFFFAOYSA-N 1-[1-tert-butyl-5-(1-hydroxyethyl)pyrazol-4-yl]-3-[4-chloro-2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)Cl)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1C(C)O PMORCZIWMGAJGZ-UHFFFAOYSA-N 0.000 claims 1
- PSGKUVWKAVNVHB-UHFFFAOYSA-N 1-[1-tert-butyl-5-(hydroxymethyl)pyrazol-4-yl]-3-[2,4-difluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)F)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1CO PSGKUVWKAVNVHB-UHFFFAOYSA-N 0.000 claims 1
- LQECOGMHIIZVQS-UHFFFAOYSA-N 1-[1-tert-butyl-5-(hydroxymethyl)pyrazol-4-yl]-3-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1CO LQECOGMHIIZVQS-UHFFFAOYSA-N 0.000 claims 1
- VWOJFXKTLBKVRO-UHFFFAOYSA-N 1-[1-tert-butyl-5-(hydroxymethyl)pyrazol-4-yl]-3-[4-chloro-2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)Cl)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1CO VWOJFXKTLBKVRO-UHFFFAOYSA-N 0.000 claims 1
- KHDGCQVEHCXKAM-UHFFFAOYSA-N 1-[1-tert-butyl-5-(trifluoromethyl)pyrazol-4-yl]-3-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1C(F)(F)F KHDGCQVEHCXKAM-UHFFFAOYSA-N 0.000 claims 1
- JZCNGDOCIPGJSQ-UHFFFAOYSA-N 1-[1-tert-butyl-5-(trifluoromethyl)pyrazol-4-yl]-3-[2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC=1C=NN(C(C)(C)C)C=1C(F)(F)F JZCNGDOCIPGJSQ-UHFFFAOYSA-N 0.000 claims 1
- QCEYNALQJFIDNP-UHFFFAOYSA-N 1-[1-tert-butyl-5-(trifluoromethyl)pyrazol-4-yl]-3-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC=1C=NN(C(C)(C)C)C=1C(F)(F)F QCEYNALQJFIDNP-UHFFFAOYSA-N 0.000 claims 1
- HKADULHDOIBTBO-UHFFFAOYSA-N 1-[1-tert-butyl-5-(trifluoromethyl)pyrazol-4-yl]-3-[4-chloro-2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)Cl)=CC=1NC(=O)NC=1C=NN(C(C)(C)C)C=1C(F)(F)F HKADULHDOIBTBO-UHFFFAOYSA-N 0.000 claims 1
- ADAZZRHBYOVNDP-UHFFFAOYSA-N 1-[2,4-difluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[5-(trifluoromethyl)pyridin-3-yl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)F)=CC=1NC(=O)NC1=CN=CC(C(F)(F)F)=C1 ADAZZRHBYOVNDP-UHFFFAOYSA-N 0.000 claims 1
- PCWATPUXNAFKDL-UHFFFAOYSA-N 1-[2,4-difluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-[3-(trifluoromethyl)-1,2-oxazol-5-yl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)F)=CC=1NC(=O)NC1=CC(C(F)(F)F)=NO1 PCWATPUXNAFKDL-UHFFFAOYSA-N 0.000 claims 1
- IJLFPWGYNGLAMY-UHFFFAOYSA-N 1-[2-chloro-5-(trifluoromethyl)phenyl]-3-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(F)(F)F)=CC=C1Cl IJLFPWGYNGLAMY-UHFFFAOYSA-N 0.000 claims 1
- WJFNUMHOIBXOMK-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-(1-pyridin-3-ylethyl)urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC(C)C1=CC=CN=C1 WJFNUMHOIBXOMK-UHFFFAOYSA-N 0.000 claims 1
- XFKGNAWBANTIHZ-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-(2-phenyl-5-propan-2-ylpyrazol-3-yl)urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)C)=NN1C1=CC=CC=C1 XFKGNAWBANTIHZ-UHFFFAOYSA-N 0.000 claims 1
- FOXFRRGYKQNDPI-MRXNPFEDSA-N 1-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[(1r)-1-phenylethyl]urea Chemical compound C1([C@@H](C)NC(=O)NC=2C=C(C(=CC=2F)C)C=2C(=O)N(C)C=3C=C(N=CC=3C=2)NC)=CC=CC=C1 FOXFRRGYKQNDPI-MRXNPFEDSA-N 0.000 claims 1
- HKKSSFBCDUEAKI-JLTOFOAXSA-N 1-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[(1r,2r)-2-methylcyclohexyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)N[C@@H]1CCCC[C@H]1C HKKSSFBCDUEAKI-JLTOFOAXSA-N 0.000 claims 1
- HKKSSFBCDUEAKI-XOBRGWDASA-N 1-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[(1s,2s)-2-methylcyclohexyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)N[C@H]1CCCC[C@@H]1C HKKSSFBCDUEAKI-XOBRGWDASA-N 0.000 claims 1
- UYZSTDZANFAJHR-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F UYZSTDZANFAJHR-UHFFFAOYSA-N 0.000 claims 1
- PBKXCNNSARFVAT-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[3-(trifluoromethyl)-1,2-oxazol-5-yl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(F)(F)F)=NO1 PBKXCNNSARFVAT-UHFFFAOYSA-N 0.000 claims 1
- GHVWBSJTPTZREA-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 GHVWBSJTPTZREA-UHFFFAOYSA-N 0.000 claims 1
- WSLFYEUFMNOSRR-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[4-fluoro-5-(trifluoromethyl)pyridin-3-yl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CN=CC(C(F)(F)F)=C1F WSLFYEUFMNOSRR-UHFFFAOYSA-N 0.000 claims 1
- XXRCQUWJSONCRT-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[4-methyl-5-(trifluoromethyl)pyridin-3-yl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CN=CC(C(F)(F)F)=C1C XXRCQUWJSONCRT-UHFFFAOYSA-N 0.000 claims 1
- FPSIDFFYENCSKT-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[5-(trifluoromethyl)pyridin-3-yl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CN=CC(C(F)(F)F)=C1 FPSIDFFYENCSKT-UHFFFAOYSA-N 0.000 claims 1
- LBNJTGASTPOIBY-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-propan-2-ylurea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C1=CC(NC(=O)NC(C)C)=C(F)C=C1C LBNJTGASTPOIBY-UHFFFAOYSA-N 0.000 claims 1
- BTDSENMGXDQDAA-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-(1,2,3,4-tetrahydronaphthalen-1-yl)urea Chemical compound C1CCC2=CC=CC=C2C1NC(=O)NC1=C(F)C=C(C)C(C2=CC3=CN=C(N=C3N(C)C2=O)NC)=C1 BTDSENMGXDQDAA-UHFFFAOYSA-N 0.000 claims 1
- XFEHTZCUCIUCGD-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-(1-methylpiperidin-4-yl)urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1CCN(C)CC1 XFEHTZCUCIUCGD-UHFFFAOYSA-N 0.000 claims 1
- HKISGYNOBLLIFR-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-(1-pyridin-3-ylethyl)urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC(C)C1=CC=CN=C1 HKISGYNOBLLIFR-UHFFFAOYSA-N 0.000 claims 1
- SRPOHYLKKGDBGR-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-(2-phenyl-5-propan-2-ylpyrazol-3-yl)urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)C)=NN1C1=CC=CC=C1 SRPOHYLKKGDBGR-UHFFFAOYSA-N 0.000 claims 1
- HZIITFKDMSKIEI-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-(3-fluorophenyl)urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC=CC(F)=C1 HZIITFKDMSKIEI-UHFFFAOYSA-N 0.000 claims 1
- XTYXZPLRAZGPDN-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-(3-methylphenyl)urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC=CC(C)=C1 XTYXZPLRAZGPDN-UHFFFAOYSA-N 0.000 claims 1
- KEHHPCKJWVYWIE-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-(3-propan-2-yl-1,2-oxazol-5-yl)urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)C)=NO1 KEHHPCKJWVYWIE-UHFFFAOYSA-N 0.000 claims 1
- OTCWTJXJKPZCFD-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-(5-propan-2-yl-1,2-oxazol-3-yl)urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=C(C(C)C)ON=1 OTCWTJXJKPZCFD-UHFFFAOYSA-N 0.000 claims 1
- IQADBXPPROEXGA-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-(oxan-4-yl)urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1CCOCC1 IQADBXPPROEXGA-UHFFFAOYSA-N 0.000 claims 1
- PGZQYERBEXBRRK-OAHLLOKOSA-N 1-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-[(1r)-1-phenylethyl]urea Chemical compound C1([C@@H](C)NC(=O)NC=2C=C(C(=CC=2F)C)C2=CC3=CN=C(N=C3N(C)C2=O)NC)=CC=CC=C1 PGZQYERBEXBRRK-OAHLLOKOSA-N 0.000 claims 1
- VISLVYSZEXMFPU-BFUOFWGJSA-N 1-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-[(1r,2r)-2-methylcyclohexyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)N[C@@H]1CCCC[C@H]1C VISLVYSZEXMFPU-BFUOFWGJSA-N 0.000 claims 1
- NQPVWEIOXDHVHH-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F NQPVWEIOXDHVHH-UHFFFAOYSA-N 0.000 claims 1
- BNIARTULZKHTKE-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-[2-methyl-5-(trifluoromethyl)phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(F)(F)F)=CC=C1C BNIARTULZKHTKE-UHFFFAOYSA-N 0.000 claims 1
- IZFRVWXSQBWGDZ-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-[2-phenyl-5-(trifluoromethyl)pyrazol-3-yl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(F)(F)F)=NN1C1=CC=CC=C1 IZFRVWXSQBWGDZ-UHFFFAOYSA-N 0.000 claims 1
- UJMPSGZNIGDLGL-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-[3-(1-methylcyclopentyl)-1,2-oxazol-5-yl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC(ON=1)=CC=1C1(C)CCCC1 UJMPSGZNIGDLGL-UHFFFAOYSA-N 0.000 claims 1
- MPMLWFDSFMJLJJ-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-[3-(trifluoromethyl)-1,2-oxazol-5-yl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(F)(F)F)=NO1 MPMLWFDSFMJLJJ-UHFFFAOYSA-N 0.000 claims 1
- DKRDEICSKOQKQU-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 DKRDEICSKOQKQU-UHFFFAOYSA-N 0.000 claims 1
- SKZLYFATZTXWMH-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-naphthalen-1-ylurea Chemical compound C1=CC=C2C(NC(=O)NC=3C=C(C(=CC=3F)C)C3=CC4=CN=C(N=C4N(C)C3=O)NC)=CC=CC2=C1 SKZLYFATZTXWMH-UHFFFAOYSA-N 0.000 claims 1
- XKEPHYRVVQKEKZ-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-piperidin-4-ylurea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1CCNCC1 XKEPHYRVVQKEKZ-UHFFFAOYSA-N 0.000 claims 1
- VPZJHOSFAFJLEQ-UHFFFAOYSA-N 1-[2-fluoro-4-methyl-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-propan-2-ylurea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C1=CC(NC(=O)NC(C)C)=C(F)C=C1C VPZJHOSFAFJLEQ-UHFFFAOYSA-N 0.000 claims 1
- WOQLAKZUENGIAO-UHFFFAOYSA-N 1-[2-fluoro-5-(2-oxo-1h-1,6-naphthyridin-3-yl)phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound FC1=CC=C(C=2C(NC3=CC=NC=C3C=2)=O)C=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 WOQLAKZUENGIAO-UHFFFAOYSA-N 0.000 claims 1
- ZCJJZFFUFWBWTP-UHFFFAOYSA-N 1-[2-fluoro-5-[1-(2-hydroxyethyl)-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-4-methylphenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(CCO)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F ZCJJZFFUFWBWTP-UHFFFAOYSA-N 0.000 claims 1
- DYBSNMAHLKBQEX-UHFFFAOYSA-N 1-[2-fluoro-5-[1-(2-hydroxyethyl)-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-4-methylphenyl]-3-propan-2-ylurea Chemical compound C=1C=2C=NC(NC)=CC=2N(CCO)C(=O)C=1C1=CC(NC(=O)NC(C)C)=C(F)C=C1C DYBSNMAHLKBQEX-UHFFFAOYSA-N 0.000 claims 1
- LFDNHEXKKGCFMQ-UHFFFAOYSA-N 1-[2-fluoro-5-[1-(2-hydroxyethyl)-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(CCO)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F LFDNHEXKKGCFMQ-UHFFFAOYSA-N 0.000 claims 1
- OCKFMFYKJANIAE-UHFFFAOYSA-N 1-[2-fluoro-5-[1-(2-hydroxyethyl)-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[5-(trifluoromethyl)pyridin-3-yl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(CCO)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC1=CN=CC(C(F)(F)F)=C1 OCKFMFYKJANIAE-UHFFFAOYSA-N 0.000 claims 1
- LXYAVQFZACXPKS-ZYMOGRSISA-N 1-[2-fluoro-5-[1-[(3r)-3-hydroxycyclopentyl]-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-4-methylphenyl]-3-propan-2-ylurea Chemical compound O=C1C(C=2C(=CC(F)=C(NC(=O)NC(C)C)C=2)C)=CC=2C=NC(NC)=CC=2N1C1CC[C@@H](O)C1 LXYAVQFZACXPKS-ZYMOGRSISA-N 0.000 claims 1
- XIHNSUYXHFQDBV-UHFFFAOYSA-N 1-[2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-(2-phenyl-5-propan-2-ylpyrazol-3-yl)urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)C)=NN1C1=CC=CC=C1 XIHNSUYXHFQDBV-UHFFFAOYSA-N 0.000 claims 1
- ILDVZFQXRJTILD-UHFFFAOYSA-N 1-[2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[2-phenyl-5-(trifluoromethyl)pyrazol-3-yl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(F)(F)F)=NN1C1=CC=CC=C1 ILDVZFQXRJTILD-UHFFFAOYSA-N 0.000 claims 1
- AFBKZYCXZGLULN-UHFFFAOYSA-N 1-[2-fluoro-5-[1-methyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 AFBKZYCXZGLULN-UHFFFAOYSA-N 0.000 claims 1
- UQBLYBDGAPFUMF-UHFFFAOYSA-N 1-[2-fluoro-5-[2-(1-hydroxypropan-2-ylamino)-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound O=C1N(C)C2=NC(NC(CO)C)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 UQBLYBDGAPFUMF-UHFFFAOYSA-N 0.000 claims 1
- LALPCYMIZBJPFI-UHFFFAOYSA-N 1-[2-fluoro-5-[2-(methylamino)-7-oxo-8-propan-2-ylpyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound O=C1N(C(C)C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F LALPCYMIZBJPFI-UHFFFAOYSA-N 0.000 claims 1
- PSWQICCRMPFGKL-UHFFFAOYSA-N 1-[2-fluoro-5-[2-(methylamino)-7-oxo-8-propan-2-ylpyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound O=C1N(C(C)C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 PSWQICCRMPFGKL-UHFFFAOYSA-N 0.000 claims 1
- SSXGTLWKNFWTJT-UHFFFAOYSA-N 1-[2-fluoro-5-[2-(methylamino)-7-oxo-8-propan-2-ylpyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-naphthalen-1-ylurea Chemical compound C1=CC=C2C(NC(=O)NC=3C(F)=CC=C(C=3)C3=CC4=CN=C(N=C4N(C(C)C)C3=O)NC)=CC=CC2=C1 SSXGTLWKNFWTJT-UHFFFAOYSA-N 0.000 claims 1
- KMLHXZXRCXYESU-UHFFFAOYSA-N 1-[2-fluoro-5-[2-(methylamino)-7-oxo-8-propan-2-ylpyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-phenylurea Chemical compound O=C1N(C(C)C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=CC=C1 KMLHXZXRCXYESU-UHFFFAOYSA-N 0.000 claims 1
- QNCIMMKFUYYGFP-UHFFFAOYSA-N 1-[2-fluoro-5-[2-(methylamino)-7-oxo-8-propan-2-ylpyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-pyridin-3-ylurea Chemical compound O=C1N(C(C)C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=CN=C1 QNCIMMKFUYYGFP-UHFFFAOYSA-N 0.000 claims 1
- ZRBSZQIVEMOCEQ-ZDUSSCGKSA-N 1-[2-fluoro-5-[2-[[(2s)-1-hydroxypropan-2-yl]amino]-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-(3-propan-2-yl-1,2-oxazol-5-yl)urea Chemical compound O=C1N(C)C2=NC(N[C@H](CO)C)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)C)=NO1 ZRBSZQIVEMOCEQ-ZDUSSCGKSA-N 0.000 claims 1
- AKSVOXUHYLZBPP-UHFFFAOYSA-N 1-[2-fluoro-5-[7-(methylamino)-2-oxo-1-phenyl-1,6-naphthyridin-3-yl]phenyl]-3-(3-propan-2-yl-1,2-oxazol-5-yl)urea Chemical compound O=C1C(C=2C=C(NC(=O)NC=3ON=C(C=3)C(C)C)C(F)=CC=2)=CC=2C=NC(NC)=CC=2N1C1=CC=CC=C1 AKSVOXUHYLZBPP-UHFFFAOYSA-N 0.000 claims 1
- PMZHKRHHUMHWRN-UHFFFAOYSA-N 1-[2-fluoro-5-[7-(methylamino)-2-oxo-1-propan-2-yl-1,6-naphthyridin-3-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C(C)C)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F PMZHKRHHUMHWRN-UHFFFAOYSA-N 0.000 claims 1
- JFONXTNNTJGCQE-UHFFFAOYSA-N 1-[2-fluoro-5-[7-(methylamino)-2-oxo-1-propan-2-yl-1,6-naphthyridin-3-yl]phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C=1C=2C=NC(NC)=CC=2N(C(C)C)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 JFONXTNNTJGCQE-UHFFFAOYSA-N 0.000 claims 1
- CYPYNLLRJUXMAJ-UHFFFAOYSA-N 1-[2-fluoro-5-[7-(methylamino)-2-oxo-1-propan-2-yl-1,6-naphthyridin-3-yl]phenyl]-3-phenylurea Chemical compound C=1C=2C=NC(NC)=CC=2N(C(C)C)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=CC=C1 CYPYNLLRJUXMAJ-UHFFFAOYSA-N 0.000 claims 1
- LBBBRYWOPDUUMK-UHFFFAOYSA-N 1-[2-fluoro-5-[8-(2-hydroxyethyl)-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound O=C1N(CCO)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F LBBBRYWOPDUUMK-UHFFFAOYSA-N 0.000 claims 1
- WGVQKGMSXGTNLB-UHFFFAOYSA-N 1-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-(1-propan-2-ylpyrazol-4-yl)urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC=1C=NN(C(C)C)C=1 WGVQKGMSXGTNLB-UHFFFAOYSA-N 0.000 claims 1
- MQCVSPUIUTWKBD-UHFFFAOYSA-N 1-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-(2-methylpyrazol-3-yl)urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=NN1C MQCVSPUIUTWKBD-UHFFFAOYSA-N 0.000 claims 1
- UGOFJXRRZUKQDS-UHFFFAOYSA-N 1-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-(2-phenyl-5-propan-2-ylpyrazol-3-yl)urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)C)=NN1C1=CC=CC=C1 UGOFJXRRZUKQDS-UHFFFAOYSA-N 0.000 claims 1
- APFUBMSXXYIOMT-UHFFFAOYSA-N 1-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-(3-propan-2-yl-1,2-oxazol-5-yl)urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)C)=NO1 APFUBMSXXYIOMT-UHFFFAOYSA-N 0.000 claims 1
- PKVOASZLGYEBRL-UHFFFAOYSA-N 1-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-(4-methylpyrimidin-5-yl)urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CN=CN=C1C PKVOASZLGYEBRL-UHFFFAOYSA-N 0.000 claims 1
- QISBYECEZZNMES-UHFFFAOYSA-N 1-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-(6-phenylpyrimidin-4-yl)urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC(N=CN=1)=CC=1C1=CC=CC=C1 QISBYECEZZNMES-UHFFFAOYSA-N 0.000 claims 1
- GOWUQMRDZJYUPZ-UHFFFAOYSA-N 1-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F GOWUQMRDZJYUPZ-UHFFFAOYSA-N 0.000 claims 1
- VMSTXRHETJVGGD-UHFFFAOYSA-N 1-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-[2-phenyl-5-(trifluoromethyl)pyrazol-3-yl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(F)(F)F)=NN1C1=CC=CC=C1 VMSTXRHETJVGGD-UHFFFAOYSA-N 0.000 claims 1
- OPFCEVOEWZZZSX-UHFFFAOYSA-N 1-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-[3-(trifluoromethyl)-1,2-oxazol-5-yl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(F)(F)F)=NO1 OPFCEVOEWZZZSX-UHFFFAOYSA-N 0.000 claims 1
- KCXYKIJHNPETIV-UHFFFAOYSA-N 1-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 KCXYKIJHNPETIV-UHFFFAOYSA-N 0.000 claims 1
- GGOZYUTWOASRCZ-UHFFFAOYSA-N 1-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-[5-(1-hydroxy-2-methylpropan-2-yl)-2-methylpyrazol-3-yl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)CO)=NN1C GGOZYUTWOASRCZ-UHFFFAOYSA-N 0.000 claims 1
- NRVDIHGVOLMRKP-UHFFFAOYSA-N 1-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-[5-(1-hydroxy-2-methylpropan-2-yl)-2-phenylpyrazol-3-yl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)CO)=NN1C1=CC=CC=C1 NRVDIHGVOLMRKP-UHFFFAOYSA-N 0.000 claims 1
- UVXPRHGHFOPBDK-UHFFFAOYSA-N 1-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-[5-(2-fluorophenyl)-2-methylpyrazol-3-yl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC(N(N=1)C)=CC=1C1=CC=CC=C1F UVXPRHGHFOPBDK-UHFFFAOYSA-N 0.000 claims 1
- PEMWQMOWLSWIAM-UHFFFAOYSA-N 1-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]-3-[5-(trifluoromethyl)pyridin-3-yl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CN=CC(C(F)(F)F)=C1 PEMWQMOWLSWIAM-UHFFFAOYSA-N 0.000 claims 1
- QGCZZALGBFWUQS-UHFFFAOYSA-N 1-[2-tert-butyl-4-(1-methylindol-5-yl)pyrimidin-5-yl]-3-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=C2N(C)C=CC2=CC(C2=NC(=NC=C2NC(=O)NC=2C(F)=CC=C(C=2)C2=CC3=CN=C(N=C3N(C)C2=O)NC)C(C)(C)C)=C1 QGCZZALGBFWUQS-UHFFFAOYSA-N 0.000 claims 1
- IGABSTITMNBLBZ-UHFFFAOYSA-N 1-[2-tert-butyl-4-(3-fluorophenyl)pyrimidin-5-yl]-3-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CN=C(C(C)(C)C)N=C1C1=CC=CC(F)=C1 IGABSTITMNBLBZ-UHFFFAOYSA-N 0.000 claims 1
- JGFIPXWYUQVVAK-UHFFFAOYSA-N 1-[2-tert-butyl-4-(4-methylpiperazin-1-yl)pyrimidin-5-yl]-3-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CN=C(C(C)(C)C)N=C1N1CCN(C)CC1 JGFIPXWYUQVVAK-UHFFFAOYSA-N 0.000 claims 1
- KZRLEXWUGVVXTP-UHFFFAOYSA-N 1-[2-tert-butyl-4-(trifluoromethyl)pyrimidin-5-yl]-3-[2-fluoro-5-[8-methyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound O=C1N(C)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CN=C(C(C)(C)C)N=C1C(F)(F)F KZRLEXWUGVVXTP-UHFFFAOYSA-N 0.000 claims 1
- SXTBPNGDXBZODQ-UHFFFAOYSA-N 1-[3-(2-amino-8-ethyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)phenyl]-3-(5-propan-2-yl-2-quinolin-6-ylpyrazol-3-yl)urea Chemical compound N1=CC=CC2=CC(N3N=C(C=C3NC(=O)NC=3C=CC=C(C=3)C3=CC4=CN=C(N)N=C4N(C3=O)CC)C(C)C)=CC=C21 SXTBPNGDXBZODQ-UHFFFAOYSA-N 0.000 claims 1
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- VVENLCYOXXMQGH-UHFFFAOYSA-N 1-[5-(2-amino-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)-2-fluoro-4-methylphenyl]-3-[2-phenyl-5-(trifluoromethyl)pyrazol-3-yl]urea Chemical compound C1=C(C=2C(N(C)C3=NC(N)=NC=C3C=2)=O)C(C)=CC(F)=C1NC(=O)NC1=CC(C(F)(F)F)=NN1C1=CC=CC=C1 VVENLCYOXXMQGH-UHFFFAOYSA-N 0.000 claims 1
- QEQZRNNMRLHWLG-UHFFFAOYSA-N 1-[5-(2-amino-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl]-3-(2-fluoro-5-methylphenyl)urea Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C(=CC=C(C=2)C=2C(N(C)C3=NC(N)=NC=C3C=2)=O)F)=C1 QEQZRNNMRLHWLG-UHFFFAOYSA-N 0.000 claims 1
- KRHBTRQYMHUWBE-UHFFFAOYSA-N 1-[5-(2-amino-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl]-3-(2-phenyl-5-propan-2-ylpyrazol-3-yl)urea Chemical compound N1=C(C(C)C)C=C(NC(=O)NC=2C(=CC=C(C=2)C=2C(N(C)C3=NC(N)=NC=C3C=2)=O)F)N1C1=CC=CC=C1 KRHBTRQYMHUWBE-UHFFFAOYSA-N 0.000 claims 1
- BWOBTWFOJNYTOS-UHFFFAOYSA-N 1-[5-(2-amino-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl]-3-(2-phenyl-5-thiophen-2-ylpyrazol-3-yl)urea Chemical compound O=C1N(C)C2=NC(N)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C=2SC=CC=2)=NN1C1=CC=CC=C1 BWOBTWFOJNYTOS-UHFFFAOYSA-N 0.000 claims 1
- WZWDTNVUCOBTLL-UHFFFAOYSA-N 1-[5-(2-amino-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl]-3-(2-propan-2-yl-5-thiophen-2-ylpyrazol-3-yl)urea Chemical compound C1=C(NC(=O)NC=2C(=CC=C(C=2)C=2C(N(C)C3=NC(N)=NC=C3C=2)=O)F)N(C(C)C)N=C1C1=CC=CS1 WZWDTNVUCOBTLL-UHFFFAOYSA-N 0.000 claims 1
- ONZKJDYGKHCASO-UHFFFAOYSA-N 1-[5-(2-amino-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl]-3-(3-methylphenyl)urea Chemical compound CC1=CC=CC(NC(=O)NC=2C(=CC=C(C=2)C=2C(N(C)C3=NC(N)=NC=C3C=2)=O)F)=C1 ONZKJDYGKHCASO-UHFFFAOYSA-N 0.000 claims 1
- RIULDCMAEAWYSI-UHFFFAOYSA-N 1-[5-(2-amino-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl]-3-(3-tert-butyl-1,2-oxazol-5-yl)urea Chemical compound O=C1N(C)C2=NC(N)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NO1 RIULDCMAEAWYSI-UHFFFAOYSA-N 0.000 claims 1
- SKSHGSZCXAYQCU-UHFFFAOYSA-N 1-[5-(2-amino-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl]-3-(5-tert-butyl-2-methylpyrazol-3-yl)urea Chemical compound CN1N=C(C(C)(C)C)C=C1NC(=O)NC1=CC(C=2C(N(C)C3=NC(N)=NC=C3C=2)=O)=CC=C1F SKSHGSZCXAYQCU-UHFFFAOYSA-N 0.000 claims 1
- QFIJWFDKLFZOLH-UHFFFAOYSA-N 1-[5-(2-amino-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl]-3-(5-tert-butyl-2-phenylpyrazol-3-yl)urea Chemical compound O=C1N(C)C2=NC(N)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=CC=C1 QFIJWFDKLFZOLH-UHFFFAOYSA-N 0.000 claims 1
- ZTARDGLRHCCIAP-UHFFFAOYSA-N 1-[5-(2-amino-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl]-3-[2-(6-methylpyridin-3-yl)-5-(trifluoromethyl)pyrazol-3-yl]urea Chemical compound C1=NC(C)=CC=C1N1C(NC(=O)NC=2C(=CC=C(C=2)C=2C(N(C)C3=NC(N)=NC=C3C=2)=O)F)=CC(C(F)(F)F)=N1 ZTARDGLRHCCIAP-UHFFFAOYSA-N 0.000 claims 1
- AJRUTCOMQLITSB-UHFFFAOYSA-N 1-[5-(2-amino-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl]-3-[2-phenyl-5-(trifluoromethyl)pyrazol-3-yl]urea Chemical compound O=C1N(C)C2=NC(N)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(F)(F)F)=NN1C1=CC=CC=C1 AJRUTCOMQLITSB-UHFFFAOYSA-N 0.000 claims 1
- XKSUGTQTSSSUBC-UHFFFAOYSA-N 1-[5-(2-amino-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound O=C1N(C)C2=NC(N)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 XKSUGTQTSSSUBC-UHFFFAOYSA-N 0.000 claims 1
- ZYWDYTFJXCLTPA-UHFFFAOYSA-N 1-[5-(2-amino-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl]-3-[4-chloro-3-(trifluoromethyl)phenyl]urea Chemical compound O=C1N(C)C2=NC(N)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 ZYWDYTFJXCLTPA-UHFFFAOYSA-N 0.000 claims 1
- ZRVLORCKVQQLOC-UHFFFAOYSA-N 1-[5-(2-amino-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl]-3-[5-(2-fluorophenyl)-2-methylpyrazol-3-yl]urea Chemical compound C1=C(NC(=O)NC=2C(=CC=C(C=2)C=2C(N(C)C3=NC(N)=NC=C3C=2)=O)F)N(C)N=C1C1=CC=CC=C1F ZRVLORCKVQQLOC-UHFFFAOYSA-N 0.000 claims 1
- OMMLQJIMIZVWJQ-UHFFFAOYSA-N 1-[5-(2-amino-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl]-3-[5-tert-butyl-2-(2-methylquinolin-6-yl)pyrazol-3-yl]urea Chemical compound N1=C(N)N=C2N(C)C(=O)C(C=3C=C(C(=CC=3)F)NC(=O)NC3=CC(=NN3C3=CC4=CC=C(N=C4C=C3)C)C(C)(C)C)=CC2=C1 OMMLQJIMIZVWJQ-UHFFFAOYSA-N 0.000 claims 1
- FDVNMJDCMFSVOI-UHFFFAOYSA-N 1-[5-(2-amino-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl]-3-[5-tert-butyl-2-(2-morpholin-4-ylethyl)pyrazol-3-yl]urea Chemical compound O=C1N(C)C2=NC(N)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NN1CCN1CCOCC1 FDVNMJDCMFSVOI-UHFFFAOYSA-N 0.000 claims 1
- UJTGSIMAKBBSOQ-UHFFFAOYSA-N 1-[5-(2-amino-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl]-3-[5-tert-butyl-2-(3-fluorophenyl)pyrazol-3-yl]urea Chemical compound O=C1N(C)C2=NC(N)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NN1C1=CC=CC(F)=C1 UJTGSIMAKBBSOQ-UHFFFAOYSA-N 0.000 claims 1
- FLPXASQOSZVFTK-UHFFFAOYSA-N 1-[5-(2-amino-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl]-3-[5-tert-butyl-2-[2-(dimethylamino)ethyl]pyrazol-3-yl]urea Chemical compound CN(C)CCN1N=C(C(C)(C)C)C=C1NC(=O)NC1=CC(C=2C(N(C)C3=NC(N)=NC=C3C=2)=O)=CC=C1F FLPXASQOSZVFTK-UHFFFAOYSA-N 0.000 claims 1
- ANOVFOOZKALOBA-UHFFFAOYSA-N 1-[5-(2-amino-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl]-3-[5-tert-butyl-2-[4-(1,3,4-oxadiazol-2-yl)phenyl]pyrazol-3-yl]urea Chemical compound O=C1N(C)C2=NC(N)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NN1C(C=C1)=CC=C1C1=NN=CO1 ANOVFOOZKALOBA-UHFFFAOYSA-N 0.000 claims 1
- CTUKHIYYZYDNGS-UHFFFAOYSA-N 1-[5-(2-amino-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl]-3-naphthalen-1-ylurea Chemical compound C1=CC=C2C(NC(=O)NC=3C(F)=CC=C(C=3)C3=CC4=CN=C(N)N=C4N(C3=O)C)=CC=CC2=C1 CTUKHIYYZYDNGS-UHFFFAOYSA-N 0.000 claims 1
- JFGXVBLHONHYOY-UHFFFAOYSA-N 1-[5-(2-amino-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)-2-fluorophenyl]-3-quinolin-8-ylurea Chemical compound C1=CN=C2C(NC(=O)NC=3C(F)=CC=C(C=3)C3=CC4=CN=C(N)N=C4N(C3=O)C)=CC=CC2=C1 JFGXVBLHONHYOY-UHFFFAOYSA-N 0.000 claims 1
- JLTDCNBYPAHOMA-UHFFFAOYSA-N 1-[5-(7-amino-1-ethyl-2-oxo-1,6-naphthyridin-3-yl)-2-fluoro-4-methylphenyl]-3-(5-tert-butyl-1,2-oxazol-3-yl)urea Chemical compound O=C1N(CC)C2=CC(N)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC=1C=C(C(C)(C)C)ON=1 JLTDCNBYPAHOMA-UHFFFAOYSA-N 0.000 claims 1
- WGHGGBMGCQSNCD-UHFFFAOYSA-N 1-[5-(7-amino-1-ethyl-2-oxo-1,6-naphthyridin-3-yl)-2-fluorophenyl]-3-(3-tert-butyl-1,2-oxazol-5-yl)urea Chemical compound O=C1N(CC)C2=CC(N)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)(C)C)=NO1 WGHGGBMGCQSNCD-UHFFFAOYSA-N 0.000 claims 1
- SZAZTNLBSWEIGX-UHFFFAOYSA-N 1-[5-(7-amino-1-methyl-2-oxo-1,6-naphthyridin-3-yl)-2-fluoro-4-methylphenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C=2C(N(C)C3=CC(N)=NC=C3C=2)=O)C(C)=CC(F)=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 SZAZTNLBSWEIGX-UHFFFAOYSA-N 0.000 claims 1
- MABLMEFRPBGWTG-UHFFFAOYSA-N 1-[5-(7-anilino-1-methyl-2-oxo-1,6-naphthyridin-3-yl)-2-fluoro-4-methylphenyl]-3-(3-tert-butyl-1,2-oxazol-5-yl)urea Chemical compound C1=C(C=2C(N(C)C3=CC(NC=4C=CC=CC=4)=NC=C3C=2)=O)C(C)=CC(F)=C1NC(=O)NC1=CC(C(C)(C)C)=NO1 MABLMEFRPBGWTG-UHFFFAOYSA-N 0.000 claims 1
- WLDAXJSYCJAVRI-UHFFFAOYSA-N 1-[5-[1-cyclopentyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluoro-4-methylphenyl]-3-propan-2-ylurea Chemical compound O=C1C(C=2C(=CC(F)=C(NC(=O)NC(C)C)C=2)C)=CC=2C=NC(NC)=CC=2N1C1CCCC1 WLDAXJSYCJAVRI-UHFFFAOYSA-N 0.000 claims 1
- JEUKAQWMYXQVKI-UHFFFAOYSA-N 1-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluoro-4-methylphenyl]-3-(2-phenyl-5-propan-2-ylpyrazol-3-yl)urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)C)=NN1C1=CC=CC=C1 JEUKAQWMYXQVKI-UHFFFAOYSA-N 0.000 claims 1
- UBEVGCSHFAFHDC-UHFFFAOYSA-N 1-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluoro-4-methylphenyl]-3-[3-(trifluoromethyl)-1,2-oxazol-5-yl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(F)(F)F)=NO1 UBEVGCSHFAFHDC-UHFFFAOYSA-N 0.000 claims 1
- GHFPWSHLGZJOGE-UHFFFAOYSA-N 1-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluoro-4-methylphenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 GHFPWSHLGZJOGE-UHFFFAOYSA-N 0.000 claims 1
- KRKFQJUZHAFOAZ-UHFFFAOYSA-N 1-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(F)(F)F)=CC=C1F KRKFQJUZHAFOAZ-UHFFFAOYSA-N 0.000 claims 1
- MBICPGBJQCUQNW-UHFFFAOYSA-N 1-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 MBICPGBJQCUQNW-UHFFFAOYSA-N 0.000 claims 1
- GDENILKFMBNOQR-UHFFFAOYSA-N 1-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]-3-[5-(trifluoromethyl)pyridin-3-yl]urea Chemical compound O=C1N(CC)C2=CC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CN=CC(C(F)(F)F)=C1 GDENILKFMBNOQR-UHFFFAOYSA-N 0.000 claims 1
- POCMKRLYZZZJKE-UHFFFAOYSA-N 1-[5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]-3-naphthalen-1-ylurea Chemical compound C1=CC=C2C(NC(=O)NC=3C(F)=CC=C(C=3)C3=CC4=CN=C(NC)C=C4N(C3=O)CC)=CC=CC2=C1 POCMKRLYZZZJKE-UHFFFAOYSA-N 0.000 claims 1
- NBUSJSSHKQHULF-UHFFFAOYSA-N 1-[5-[2-[2-(dimethylamino)ethylamino]-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluoro-4-methylphenyl]-3-[3-(trifluoromethyl)-1,2-oxazol-5-yl]urea Chemical compound O=C1N(C)C2=NC(NCCN(C)C)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(F)(F)F)=NO1 NBUSJSSHKQHULF-UHFFFAOYSA-N 0.000 claims 1
- MMDVGRYTSBHTMZ-UHFFFAOYSA-N 1-[5-[2-[2-(dimethylamino)ethylamino]-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluoro-4-methylphenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound O=C1N(C)C2=NC(NCCN(C)C)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 MMDVGRYTSBHTMZ-UHFFFAOYSA-N 0.000 claims 1
- WRVXHUHDSNTPIP-UHFFFAOYSA-N 1-[5-[2-[2-(dimethylamino)ethylamino]-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluorophenyl]-3-(3-propan-2-yl-1,2-oxazol-5-yl)urea Chemical compound O1N=C(C(C)C)C=C1NC(=O)NC1=CC(C=2C(N(C)C3=NC(NCCN(C)C)=NC=C3C=2)=O)=CC=C1F WRVXHUHDSNTPIP-UHFFFAOYSA-N 0.000 claims 1
- KLFRDCVQEJRTDB-UHFFFAOYSA-N 1-[5-[2-[2-(dimethylamino)ethylamino]-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluorophenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound O=C1N(C)C2=NC(NCCN(C)C)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 KLFRDCVQEJRTDB-UHFFFAOYSA-N 0.000 claims 1
- CRMYHHQZNQZHNI-UHFFFAOYSA-N 1-[5-[2-[2-(dimethylamino)ethylamino]-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluorophenyl]-3-naphthalen-1-ylurea Chemical compound C1=CC=C2C(NC(=O)NC=3C(F)=CC=C(C=3)C3=CC4=CN=C(N=C4N(C)C3=O)NCCN(C)C)=CC=CC2=C1 CRMYHHQZNQZHNI-UHFFFAOYSA-N 0.000 claims 1
- MICNQBWZFBQXPL-UHFFFAOYSA-N 1-[5-[7-[2-(dimethylamino)ethylamino]-1-methyl-2-oxo-1,6-naphthyridin-3-yl]-2-fluoro-4-methylphenyl]-3-[3-(trifluoromethyl)-1,2-oxazol-5-yl]urea Chemical compound C=1C=2C=NC(NCCN(C)C)=CC=2N(C)C(=O)C=1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(F)(F)F)=NO1 MICNQBWZFBQXPL-UHFFFAOYSA-N 0.000 claims 1
- UXKHWWQXNHZEAD-UHFFFAOYSA-N 1-[5-[7-[2-(dimethylamino)ethylamino]-1-methyl-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]-3-(2-phenylphenyl)urea Chemical compound C=1C=2C=NC(NCCN(C)C)=CC=2N(C)C(=O)C=1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC=CC=C1C1=CC=CC=C1 UXKHWWQXNHZEAD-UHFFFAOYSA-N 0.000 claims 1
- CQGLJFRHEAVBJW-UHFFFAOYSA-N 1-[5-[8-ethyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluoro-4-methylphenyl]-3-(2-phenyl-5-propan-2-ylpyrazol-3-yl)urea Chemical compound O=C1N(CC)C2=NC(NC)=NC=C2C=C1C(C(=CC=1F)C)=CC=1NC(=O)NC1=CC(C(C)C)=NN1C1=CC=CC=C1 CQGLJFRHEAVBJW-UHFFFAOYSA-N 0.000 claims 1
- FDRZBUDXBZJZAW-UHFFFAOYSA-N 1-[5-[8-ethyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluorophenyl]-3-(2-methyl-5-propan-2-ylpyrazol-3-yl)urea Chemical compound O=C1N(CC)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)C)=NN1C FDRZBUDXBZJZAW-UHFFFAOYSA-N 0.000 claims 1
- SVPITFFSBXFLLC-UHFFFAOYSA-N 1-[5-[8-ethyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluorophenyl]-3-(2-phenyl-5-propan-2-ylpyrazol-3-yl)urea Chemical compound O=C1N(CC)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(C)C)=NN1C1=CC=CC=C1 SVPITFFSBXFLLC-UHFFFAOYSA-N 0.000 claims 1
- JCLOMOOEFWCODU-UHFFFAOYSA-N 1-[5-[8-ethyl-2-(methylamino)-7-oxopyrido[2,3-d]pyrimidin-6-yl]-2-fluorophenyl]-3-[2-methyl-5-(trifluoromethyl)pyrazol-3-yl]urea Chemical compound O=C1N(CC)C2=NC(NC)=NC=C2C=C1C(C=1)=CC=C(F)C=1NC(=O)NC1=CC(C(F)(F)F)=NN1C JCLOMOOEFWCODU-UHFFFAOYSA-N 0.000 claims 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
- IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
Landscapes
- Health & Medical Sciences (AREA)
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- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
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- Communicable Diseases (AREA)
- Transplantation (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84455206P | 2006-09-14 | 2006-09-14 | |
| US60/844,552 | 2006-09-14 | ||
| US11/854,354 | 2007-09-12 | ||
| US11/854,354 US8188113B2 (en) | 2006-09-14 | 2007-09-12 | Dihydropyridopyrimidinyl, dihydronaphthyidinyl and related compounds useful as kinase inhibitors for the treatment of proliferative diseases |
| PCT/US2007/078408 WO2008034008A2 (en) | 2006-09-14 | 2007-09-13 | Kinase inhibitors useful for the treatment of proliferative diseases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2663577A1 true CA2663577A1 (en) | 2008-03-20 |
Family
ID=39184593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002663577A Abandoned CA2663577A1 (en) | 2006-09-14 | 2007-09-13 | Kinase inhibitors useful for the treatment of proliferative diseases |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US8188113B2 (https=) |
| EP (1) | EP2063897A4 (https=) |
| JP (1) | JP5265550B2 (https=) |
| KR (1) | KR101110530B1 (https=) |
| AU (1) | AU2007296450C1 (https=) |
| BR (2) | BR122012012032B8 (https=) |
| CA (1) | CA2663577A1 (https=) |
| EA (2) | EA026730B1 (https=) |
| MX (1) | MX2009002814A (https=) |
| WO (1) | WO2008034008A2 (https=) |
Families Citing this family (85)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7897762B2 (en) * | 2006-09-14 | 2011-03-01 | Deciphera Pharmaceuticals, Llc | Kinase inhibitors useful for the treatment of proliferative diseases |
| WO2008051757A1 (en) * | 2006-10-20 | 2008-05-02 | Irm Llc | Compositions and methods for modulating c-kit and pdgfr receptors |
| EA018551B1 (ru) | 2008-02-22 | 2013-08-30 | Айрм Ллк | ГЕТЕРОЦИКЛИЧЕСКИЕ СОЕДИНЕНИЯ И СОДЕРЖАЩИЕ ИХ КОМПОЗИЦИИ В КАЧЕСТВЕ ИНГИБИТОРОВ КИНАЗ c-KIT И PDGFR |
| JP2011513331A (ja) * | 2008-02-29 | 2011-04-28 | アレイ バイオファーマ、インコーポレイテッド | ピラゾール［３，４−ｂ］ピリジンＲＡＦ阻害剤 |
| CA2716947A1 (en) * | 2008-02-29 | 2009-09-11 | Array Biopharma Inc. | Imidazo [4,5-b] pyridine derivatives used as raf inhibitors |
| KR20100122505A (ko) * | 2008-02-29 | 2010-11-22 | 어레이 바이오파마 인크. | Ｒａｆ 저해물질 화합물 및 이들의 이용 방법 |
| JP2011513332A (ja) * | 2008-02-29 | 2011-04-28 | アレイ バイオファーマ、インコーポレイテッド | 癌の治療のためのｒａｆ阻害剤としてのｎ−（６−アミノピリジン−３−イル）−３−（スルホンアミド）ベンズアミド誘導体 |
| EP2112150B1 (en) * | 2008-04-22 | 2013-10-16 | Forma Therapeutics, Inc. | Improved raf inhibitors |
| US8232283B2 (en) | 2008-04-22 | 2012-07-31 | Forma Therapeutics, Inc. | Raf inhibitors |
| US9315449B2 (en) | 2008-05-15 | 2016-04-19 | Duke University | Substituted pyrazoles as heat shock transcription factor activators |
| JP5693452B2 (ja) | 2008-08-04 | 2015-04-01 | シーエイチディーアイ ファウンデーション，インコーポレーテッド | 特定のキヌレニン−３−モノオキシゲナーゼインヒビター、医薬組成物およびそれらの使用方法 |
| WO2010071846A2 (en) | 2008-12-19 | 2010-06-24 | Afraxis, Inc. | Compounds for treating neuropsychiatric conditions |
| TWI423962B (zh) * | 2009-10-07 | 2014-01-21 | Lg Life Sciences Ltd | 有效作為黃嘌呤氧化酶抑制劑之新穎化合物、其製備方法及含該化合物之醫藥組成物 |
| US8372970B2 (en) | 2009-10-09 | 2013-02-12 | Afraxis, Inc. | 8-ethyl-6-(aryl)pyrido[2,3-D]pyrimidin-7(8H)-ones for the treatment of CNS disorders |
| CA2787365A1 (en) | 2010-01-25 | 2011-07-28 | Chdi Foundation, Inc. | Certain kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| DK2595995T3 (en) | 2010-07-22 | 2016-02-29 | Basf Se | Herbicidal isoxazolo [5,4-b] pyridines |
| JP5605104B2 (ja) * | 2010-09-10 | 2014-10-15 | セントラル硝子株式会社 | ピラゾール化合物の製造方法 |
| US9139534B2 (en) | 2011-04-22 | 2015-09-22 | Signal Pharmaceuticals, Llc | Substituted diaminocarboxamide and diaminocarbonitrile pyrimidines, compositions thereof, and methods of treatment therewith |
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| KR20140072037A (ko) | 2011-08-30 | 2014-06-12 | 씨에이치디아이 파운데이션, 인코포레이티드 | 키뉴레닌-3-모노옥시게나제 억제제, 약학적 조성물 및 이의 사용 방법 |
| SI2750677T1 (sl) | 2011-08-30 | 2017-10-30 | Chdi Foundation, Inc. | Inhibitorji kinurenin-3-monooksigenaze, farmacevtski sestavki in postopki njihove uporabe |
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| US9408885B2 (en) | 2011-12-01 | 2016-08-09 | Vib Vzw | Combinations of therapeutic agents for treating melanoma |
| MY167216A (en) | 2011-12-09 | 2018-08-14 | Chiesi Farm Spa | Kinase inhibitors |
| UA115320C2 (uk) | 2011-12-09 | 2017-10-25 | К'Єзі Фармачеутічі С.П.А. | Інгібітори кінази |
| EP2802212B1 (en) | 2012-01-12 | 2015-12-30 | Basf Se | Herbicidal isoxazolo[5,4-b]pyridines |
| WO2013134298A1 (en) * | 2012-03-07 | 2013-09-12 | Deciphera Pharmaceuticals, Llc | Raf inhibitor compounds |
| AR090151A1 (es) * | 2012-03-07 | 2014-10-22 | Lilly Co Eli | Compuestos inhibidores de raf |
| US8461179B1 (en) | 2012-06-07 | 2013-06-11 | Deciphera Pharmaceuticals, Llc | Dihydronaphthyridines and related compounds useful as kinase inhibitors for the treatment of proliferative diseases |
| SI3366293T1 (sl) * | 2012-06-07 | 2020-08-31 | Deciphera Pharmaceuticals, Llc | Dihidronafthiridini in sorodne spojine uporabne kot kinazni inhibitorji za zdravljenje proliferativnih bolezni |
| DE102012016908A1 (de) | 2012-08-17 | 2014-02-20 | Aicuris Gmbh & Co. Kg | Tris-(Hetero)Aryl-Pyrazole und ihre Verwendung |
| WO2014078372A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | Pyrrolidinyl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| WO2014078325A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | N-(monocyclic aryl),n'-pyrazolyl-urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| WO2014078417A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | Pyrazolyl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| US9822118B2 (en) | 2012-11-13 | 2017-11-21 | Array Biopharma Inc. | Bicyclic heteroaryl urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors |
| RS55593B1 (sr) | 2012-11-13 | 2017-06-30 | Array Biopharma Inc | Jedinjenja biciklične uree, tiouree, guanidina i cijanoguanidina korisna za lečenje bola |
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| MX374242B (es) | 2012-11-13 | 2025-03-05 | Array Biopharma Inc | Compuestos de n-pirrolidinil, n' -pirazolil-urea, tiourea, guanidina y cianoguanidina como inhibidores de trka cinasa. |
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| WO2014078328A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | N-bicyclic aryl,n'-pyrazolyl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| US9981959B2 (en) | 2012-11-13 | 2018-05-29 | Array Biopharma Inc. | Thiazolyl and oxazolyl urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors |
| RU2015151886A (ru) | 2013-06-06 | 2017-06-08 | КЬЕЗИ ФАРМАЧЕУТИЧИ С.п.А. | Ингибиторы киназ |
| GB201320729D0 (en) * | 2013-11-25 | 2014-01-08 | Cancer Rec Tech Ltd | Therapeutic compounds and their use |
| KR102736869B1 (ko) | 2014-03-07 | 2024-12-02 | 바이오크리스트파마슈티컬즈,인코포레이티드 | 인간 혈장 칼리크레인 저해제 |
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| AU2015289492B2 (en) | 2014-07-17 | 2020-02-20 | Chdi Foundation, Inc. | Methods and compositions for treating HIV-related disorders |
| AU2015369712B2 (en) | 2014-12-22 | 2020-05-07 | The United States Of America As Represented By The Secretary, Department Of Health And Human Services | Mutant IDH1 inhibitors useful for treating cancer |
| KR102155125B1 (ko) | 2015-07-17 | 2020-09-11 | 경희대학교 산학협력단 | 악성 중피종 예방 또는 치료용 조성물 |
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| WO2018146253A1 (en) | 2017-02-10 | 2018-08-16 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment of cancers associated with activation of the mapk pathway |
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| BRPI0716981A2 (pt) | 2013-10-15 |
| AU2007296450C1 (en) | 2013-05-02 |
| JP2010503702A (ja) | 2010-02-04 |
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| EA201101341A1 (ru) | 2012-04-30 |
| BR122012012032B8 (pt) | 2021-05-25 |
| KR20090069296A (ko) | 2009-06-30 |
| EP2063897A4 (en) | 2010-09-29 |
| BRPI0716981B8 (pt) | 2021-05-25 |
| BR122012012032A2 (pt) | 2015-07-14 |
| US8188113B2 (en) | 2012-05-29 |
| AU2007296450B2 (en) | 2012-08-30 |
| BRPI0716981B1 (pt) | 2021-02-02 |
| AU2007296450A1 (en) | 2008-03-20 |
| KR101110530B1 (ko) | 2012-04-24 |
| BR122012012032B1 (pt) | 2021-02-23 |
| EA026730B1 (ru) | 2017-05-31 |
| WO2008034008A2 (en) | 2008-03-20 |
| EA016055B1 (ru) | 2012-01-30 |
| MX2009002814A (es) | 2009-07-24 |
| US20120289540A1 (en) | 2012-11-15 |
| EP2063897A2 (en) | 2009-06-03 |
| EA200970280A1 (ru) | 2009-10-30 |
| US20080114006A1 (en) | 2008-05-15 |
| JP5265550B2 (ja) | 2013-08-14 |
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