JP2017500362A5 - - Google Patents
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- JP2017500362A5 JP2017500362A5 JP2016542956A JP2016542956A JP2017500362A5 JP 2017500362 A5 JP2017500362 A5 JP 2017500362A5 JP 2016542956 A JP2016542956 A JP 2016542956A JP 2016542956 A JP2016542956 A JP 2016542956A JP 2017500362 A5 JP2017500362 A5 JP 2017500362A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- fluoro
- dioxo
- pyrazolo
- tetrahydro
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims 40
- -1 substituted Chemical class 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 21
- 125000001475 halogen functional group Chemical group 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 19
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 16
- GDDMXXIYSLJCRK-UHFFFAOYSA-N 3-(4-fluorophenyl)-2,4-dioxo-1-propan-2-ylpyrimidine-5-carboxylic acid Chemical compound O=C1N(C(C)C)C=C(C(O)=O)C(=O)N1C1=CC=C(F)C=C1 GDDMXXIYSLJCRK-UHFFFAOYSA-N 0.000 claims 10
- IGIJOGBLFJFFHO-UHFFFAOYSA-N 1-ethyl-3-(4-fluorophenyl)-2,4-dioxopyrimidine-5-carboxylic acid Chemical compound O=C1N(CC)C=C(C(O)=O)C(=O)N1C1=CC=C(F)C=C1 IGIJOGBLFJFFHO-UHFFFAOYSA-N 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- NSIBFUPUJYMBJZ-UHFFFAOYSA-N 3-fluoro-4-[6-(1-methylimidazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxyaniline Chemical compound FC=1C=C(C=CC1OC=1C=2N(C=C(C1)C=1N=CN(C1)C)N=CC2)N NSIBFUPUJYMBJZ-UHFFFAOYSA-N 0.000 claims 4
- LTNPQCGDRQDPKT-UHFFFAOYSA-N N-[3-fluoro-4-[6-(1-methylimidazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxyphenyl]-3-(4-fluorophenyl)-2,4-dioxo-1-propan-2-ylpyrimidine-5-carboxamide Chemical compound CC(C)N1C=C(C(=O)NC2=CC(F)=C(OC3=CC(=CN4N=CC=C34)C3=CN(C)C=N3)C=C2)C(=O)N(C1=O)C1=CC=C(F)C=C1 LTNPQCGDRQDPKT-UHFFFAOYSA-N 0.000 claims 4
- YVOOGZPMPPERIA-UHFFFAOYSA-N 1-ethyl-N-[3-fluoro-4-[6-(1-methylimidazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxyphenyl]-3-(4-fluorophenyl)-2,4-dioxopyrimidine-5-carboxamide Chemical compound FC=1C=C(C=CC=1OC=1C=2N(C=C(C=1)C=1N=CN(C=1)C)N=CC=2)NC(=O)C=1C(N(C(N(C=1)CC)=O)C1=CC=C(C=C1)F)=O YVOOGZPMPPERIA-UHFFFAOYSA-N 0.000 claims 3
- NYDHCFXFFOGARN-UHFFFAOYSA-N 3-(4-fluorophenyl)-N-[4-[6-(1-methylimidazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxy-3-(trifluoromethyl)phenyl]-2,4-dioxo-1-propan-2-ylpyrimidine-5-carboxamide Chemical compound CC(C)N1C=C(C(=O)NC2=CC(=C(OC3=CC(=CN4N=CC=C34)C3=CN(C)C=N3)C=C2)C(F)(F)F)C(=O)N(C1=O)C1=CC=C(F)C=C1 NYDHCFXFFOGARN-UHFFFAOYSA-N 0.000 claims 3
- RTPBRNZVUVGGAV-UHFFFAOYSA-N 3-methyl-4-[6-(1-methylimidazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxyaniline Chemical compound CC=1C=C(C=CC1OC=1C=2N(C=C(C1)C=1N=CN(C1)C)N=CC2)N RTPBRNZVUVGGAV-UHFFFAOYSA-N 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- KFDUMCRBSYJUHP-UHFFFAOYSA-N 1-ethyl-3-(4-fluorophenyl)-N-[4-[6-(1-methylimidazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxy-3-(trifluoromethyl)phenyl]-2,4-dioxopyrimidine-5-carboxamide Chemical compound CN1C=NC(=C1)C=1C=C(C=2N(C=1)N=CC=2)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(N(C=1)CC)=O)C1=CC=C(C=C1)F)=O)C(F)(F)F KFDUMCRBSYJUHP-UHFFFAOYSA-N 0.000 claims 2
- KIGCBVALXFPNSJ-UHFFFAOYSA-N 3-(4-fluorophenyl)-N-[3-hydroxy-4-[6-(1-methylimidazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxyphenyl]-2,4-dioxo-1-propan-2-ylpyrimidine-5-carboxamide Chemical compound CC(C)N1C=C(C(=O)NC2=CC(O)=C(OC3=CC(=CN4N=CC=C34)C3=CN(C)C=N3)C=C2)C(=O)N(C2=CC=C(F)C=C2)C1=O KIGCBVALXFPNSJ-UHFFFAOYSA-N 0.000 claims 2
- QFYBGEFISYHEDV-UHFFFAOYSA-N 3-(4-fluorophenyl)-N-[4-[6-(1-methylimidazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxy-3-phenylmethoxyphenyl]-2,4-dioxo-1-propan-2-ylpyrimidine-5-carboxamide Chemical compound C(C1=CC=CC=C1)OC=1C=C(C=CC1OC=1C=2N(C=C(C1)C=1N=CN(C1)C)N=CC2)NC(=O)C=2C(N(C(N(C2)C(C)C)=O)C2=CC=C(C=C2)F)=O QFYBGEFISYHEDV-UHFFFAOYSA-N 0.000 claims 2
- WWWRJWVQHULIEV-UHFFFAOYSA-N 3-(4-fluorophenyl)-N-[4-[6-(1-methylimidazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxyphenyl]-2,4-dioxo-1-propan-2-ylpyrimidine-5-carboxamide Chemical compound CC(C)N1C=C(C(=O)NC2=CC=C(OC3=CC(=CN4N=CC=C34)C3=CN(C)C=N3)C=C2)C(=O)N(C1=O)C1=CC=C(F)C=C1 WWWRJWVQHULIEV-UHFFFAOYSA-N 0.000 claims 2
- NAEPNESECOFESN-UHFFFAOYSA-N N-[3-fluoro-4-[6-(1-methylimidazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxyphenyl]-3-(4-fluorophenyl)-2,4-dioxo-1H-pyrimidine-5-carboxamide Chemical compound CN1C=NC(=C1)C1=CN2N=CC=C2C(OC2=C(F)C=C(NC(=O)C3=CNC(=O)N(C3=O)C3=CC=C(F)C=C3)C=C2)=C1 NAEPNESECOFESN-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- YBBLOADPFWKNGS-UHFFFAOYSA-N 1,1-dimethylurea Chemical compound CN(C)C(N)=O YBBLOADPFWKNGS-UHFFFAOYSA-N 0.000 claims 1
- QEXQIXHJBRODJT-UHFFFAOYSA-N 1-(2-ethoxyethyl)-N-[3-fluoro-4-(6-morpholin-4-ylpyrazolo[1,5-a]pyridin-4-yl)oxyphenyl]-3-(4-fluorophenyl)-2,4-dioxopyrimidine-5-carboxamide Chemical compound FC=1C=C(C=CC=1OC=1C=2N(C=C(C=1)N1CCOCC1)N=CC=2)NC(=O)C=1C(N(C(N(C=1)CCOCC)=O)C1=CC=C(C=C1)F)=O QEXQIXHJBRODJT-UHFFFAOYSA-N 0.000 claims 1
- IIMIBKXPHHTFPJ-UHFFFAOYSA-N 1-(2-ethoxyethyl)-N-[3-fluoro-4-[6-(1-methylpyrazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxyphenyl]-3-(4-fluorophenyl)-2,4-dioxopyrimidine-5-carboxamide Chemical compound FC=1C=C(C=CC=1OC=1C=2N(C=C(C=1)C=1C=NN(C=1)C)N=CC=2)NC(=O)C=1C(N(C(N(C=1)CCOCC)=O)C1=CC=C(C=C1)F)=O IIMIBKXPHHTFPJ-UHFFFAOYSA-N 0.000 claims 1
- OPWIKWIRMOOCDF-UHFFFAOYSA-N 1-[4-(4-amino-2-fluorophenoxy)pyrazolo[1,5-a]pyridin-6-yl]pyrrolidin-2-one Chemical compound NC1=CC(=C(OC=2C=3N(C=C(C2)N2C(CCC2)=O)N=CC3)C=C1)F OPWIKWIRMOOCDF-UHFFFAOYSA-N 0.000 claims 1
- RXHIDKDEHIKDIJ-UHFFFAOYSA-N 1-ethyl-3-(4-fluorophenyl)-N-[3-fluoro-4-(6-pyrazin-2-ylpyrazolo[1,5-a]pyridin-4-yl)oxyphenyl]-2,4-dioxopyrimidine-5-carboxamide Chemical compound CCN1C=C(C(=O)NC2=CC(F)=C(OC3=CC(=CN4N=CC=C34)C3=CN=CC=N3)C=C2)C(=O)N(C1=O)C1=CC=C(F)C=C1 RXHIDKDEHIKDIJ-UHFFFAOYSA-N 0.000 claims 1
- CFZNDKYSBMPZRI-UHFFFAOYSA-N 1-ethyl-3-(4-fluorophenyl)-N-[3-fluoro-4-[6-(1,2-thiazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxyphenyl]-2,4-dioxopyrimidine-5-carboxamide Chemical compound CCN1C=C(C(=O)NC2=CC(F)=C(OC3=CC(=CN4N=CC=C34)C3=CSN=C3)C=C2)C(=O)N(C1=O)C1=CC=C(F)C=C1 CFZNDKYSBMPZRI-UHFFFAOYSA-N 0.000 claims 1
- JLLJQOHEHJAGJM-UHFFFAOYSA-N 1-ethyl-3-(4-fluorophenyl)-N-[3-fluoro-4-[6-(1,3-thiazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxyphenyl]-2,4-dioxopyrimidine-5-carboxamide Chemical compound CCN1C=C(C(=O)NC2=CC(F)=C(OC3=CC(=CN4N=CC=C34)C3=CSC=N3)C=C2)C(=O)N(C1=O)C1=CC=C(F)C=C1 JLLJQOHEHJAGJM-UHFFFAOYSA-N 0.000 claims 1
- JLPWQBJIMNSJND-UHFFFAOYSA-N 1-ethyl-3-(4-fluorophenyl)-N-[3-fluoro-4-[6-(pyridin-2-ylamino)pyrazolo[1,5-a]pyridin-4-yl]oxyphenyl]-2,4-dioxopyrimidine-5-carboxamide Chemical compound CCN1C=C(C(=O)NC2=CC(F)=C(OC3=CC(NC4=NC=CC=C4)=CN4N=CC=C34)C=C2)C(=O)N(C1=O)C1=CC=C(F)C=C1 JLPWQBJIMNSJND-UHFFFAOYSA-N 0.000 claims 1
- PCQHQLAEDXBIET-UHFFFAOYSA-N 1-ethyl-3-(4-fluorophenyl)-N-[3-methyl-4-[6-(1-methylimidazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxyphenyl]-2,4-dioxopyrimidine-5-carboxamide Chemical compound CCN1C=C(C(=O)NC2=CC(C)=C(OC3=CC(=CN4N=CC=C34)C3=CN(C)C=N3)C=C2)C(=O)N(C1=O)C1=CC=C(F)C=C1 PCQHQLAEDXBIET-UHFFFAOYSA-N 0.000 claims 1
- AIJPWDUPUIOLOJ-UHFFFAOYSA-N 1-ethyl-3-(4-fluorophenyl)-N-[4-[6-(1-methylimidazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxyphenyl]-2,4-dioxopyrimidine-5-carboxamide Chemical compound CN1C=NC(=C1)C=1C=C(C=2N(C=1)N=CC=2)OC1=CC=C(C=C1)NC(=O)C=1C(N(C(N(C=1)CC)=O)C1=CC=C(C=C1)F)=O AIJPWDUPUIOLOJ-UHFFFAOYSA-N 0.000 claims 1
- ZELZMDNEDICCAB-UHFFFAOYSA-N 1-ethyl-3-(4-fluorophenyl)-N-[6-[6-(1-methylimidazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxypyridin-3-yl]-2,4-dioxopyrimidine-5-carboxamide Chemical compound CCN1C=C(C(=O)NC2=CC=C(OC3=CC(=CN4N=CC=C34)C3=CN(C)C=N3)N=C2)C(=O)N(C1=O)C1=CC=C(F)C=C1 ZELZMDNEDICCAB-UHFFFAOYSA-N 0.000 claims 1
- XZZHFPGAUZWAJV-UHFFFAOYSA-N 1-ethyl-N-[3-fluoro-4-[6-(1,3-oxazol-5-yl)pyrazolo[1,5-a]pyridin-4-yl]oxyphenyl]-3-(4-fluorophenyl)-2,4-dioxopyrimidine-5-carboxamide Chemical compound CCN1C=C(C(=O)NC2=CC(F)=C(OC3=CC(=CN4N=CC=C34)C3=CN=CO3)C=C2)C(=O)N(C1=O)C1=CC=C(F)C=C1 XZZHFPGAUZWAJV-UHFFFAOYSA-N 0.000 claims 1
- YSLQKYCHNWYVDN-UHFFFAOYSA-N 1-ethyl-N-[3-fluoro-4-[6-(1-methylpyrazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxyphenyl]-3-(4-fluorophenyl)-2,4-dioxopyrimidine-5-carboxamide Chemical compound FC=1C=C(C=CC=1OC=1C=2N(C=C(C=1)C=1C=NN(C=1)C)N=CC=2)NC(=O)C=1C(N(C(N(C=1)CC)=O)C1=CC=C(C=C1)F)=O YSLQKYCHNWYVDN-UHFFFAOYSA-N 0.000 claims 1
- OIMFYTYTBICGEO-UHFFFAOYSA-N 1-ethyl-N-[3-fluoro-4-[6-(3-methylimidazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxyphenyl]-3-(4-fluorophenyl)-2,4-dioxopyrimidine-5-carboxamide Chemical compound CCN1C=C(C(=O)NC2=CC(F)=C(OC3=CC(=CN4N=CC=C34)C3=CN=CN3C)C=C2)C(=O)N(C1=O)C1=CC=C(F)C=C1 OIMFYTYTBICGEO-UHFFFAOYSA-N 0.000 claims 1
- UATJMCPQOQCKOA-UHFFFAOYSA-N 1-ethyl-N-[3-fluoro-4-[6-(6-methylpyridin-2-yl)pyrazolo[1,5-a]pyridin-4-yl]oxyphenyl]-3-(4-fluorophenyl)-2,4-dioxopyrimidine-5-carboxamide Chemical compound CCN1C=C(C(=O)NC2=CC(F)=C(OC3=CC(=CN4N=CC=C34)C3=NC(C)=CC=C3)C=C2)C(=O)N(C1=O)C1=CC=C(F)C=C1 UATJMCPQOQCKOA-UHFFFAOYSA-N 0.000 claims 1
- OERZGXZCWQGXSB-UHFFFAOYSA-N 1-ethyl-N-[3-fluoro-4-[6-(methanesulfonamido)pyrazolo[1,5-a]pyridin-4-yl]oxyphenyl]-3-(4-fluorophenyl)-2,4-dioxopyrimidine-5-carboxamide Chemical compound CCN1C=C(C(=O)NC2=CC(F)=C(OC3=CC(NS(C)(=O)=O)=CN4N=CC=C34)C=C2)C(=O)N(C1=O)C1=CC=C(F)C=C1 OERZGXZCWQGXSB-UHFFFAOYSA-N 0.000 claims 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims 1
- FDEAXGCAOSGCNC-UHFFFAOYSA-N 3-(4-fluorophenyl)-1-(2-hydroxyethyl)-2,4-dioxopyrimidine-5-carboxylic acid Chemical compound O=C1N(CCO)C=C(C(O)=O)C(=O)N1C1=CC=C(F)C=C1 FDEAXGCAOSGCNC-UHFFFAOYSA-N 0.000 claims 1
- AZIKNCZQDXXEIS-UHFFFAOYSA-N 3-(4-fluorophenyl)-1-methyl-2,4-dioxopyrimidine-5-carboxylic acid Chemical compound O=C1N(C)C=C(C(O)=O)C(=O)N1C1=CC=C(F)C=C1 AZIKNCZQDXXEIS-UHFFFAOYSA-N 0.000 claims 1
- JTZSVYCKAYMNCT-UHFFFAOYSA-N 3-(4-fluorophenyl)-2,4-dioxo-1h-pyrimidine-5-carboxylic acid Chemical compound O=C1C(C(=O)O)=CNC(=O)N1C1=CC=C(F)C=C1 JTZSVYCKAYMNCT-UHFFFAOYSA-N 0.000 claims 1
- LSDQPXYSLVYYIB-UHFFFAOYSA-N 3-(4-fluorophenyl)-N-(3-fluoro-4-pyrazolo[1,5-a]pyridin-4-yloxyphenyl)-2,4-dioxo-1H-pyrimidine-5-carboxamide Chemical compound FC=1C=C(C=CC=1OC=1C=2N(C=CC=1)N=CC=2)NC(=O)C=1C(N(C(NC=1)=O)C1=CC=C(C=C1)F)=O LSDQPXYSLVYYIB-UHFFFAOYSA-N 0.000 claims 1
- VAEZBGLPEMZOBD-UHFFFAOYSA-N 3-(4-fluorophenyl)-N-[3-fluoro-4-(6-pyridin-4-ylpyrazolo[1,5-a]pyridin-4-yl)oxyphenyl]-2,4-dioxo-1H-pyrimidine-5-carboxamide Chemical compound FC=1C=C(C=CC=1OC=1C=2N(C=C(C=1)C1=CC=NC=C1)N=CC=2)NC(=O)C=1C(N(C(NC=1)=O)C1=CC=C(C=C1)F)=O VAEZBGLPEMZOBD-UHFFFAOYSA-N 0.000 claims 1
- KVOQWZUWKAIRLV-UHFFFAOYSA-N 3-(4-fluorophenyl)-N-[3-fluoro-4-(6-pyrimidin-2-ylpyrazolo[1,5-a]pyridin-4-yl)oxyphenyl]-2,4-dioxo-1-propan-2-ylpyrimidine-5-carboxamide Chemical compound CC(C)N1C=C(C(=O)NC2=CC(F)=C(OC3=CC(=CN4N=CC=C34)C3=NC=CC=N3)C=C2)C(=O)N(C2=CC=C(F)C=C2)C1=O KVOQWZUWKAIRLV-UHFFFAOYSA-N 0.000 claims 1
- UTESHBALWOIEFS-UHFFFAOYSA-N 3-(4-fluorophenyl)-N-[3-fluoro-4-[6-(1,3-thiazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxyphenyl]-2,4-dioxo-1-propan-2-ylpyrimidine-5-carboxamide Chemical compound CC(C)N1C=C(C(=O)NC2=CC(F)=C(OC3=CC(=CN4N=CC=C34)C3=CSC=N3)C=C2)C(=O)N(C1=O)C1=CC=C(F)C=C1 UTESHBALWOIEFS-UHFFFAOYSA-N 0.000 claims 1
- MPIHOVWDSQXNJF-UHFFFAOYSA-N 3-(4-fluorophenyl)-N-[3-fluoro-4-[6-(1,3-thiazol-5-yl)pyrazolo[1,5-a]pyridin-4-yl]oxyphenyl]-2,4-dioxo-1-propan-2-ylpyrimidine-5-carboxamide Chemical compound CC(C)N1C=C(C(=O)NC2=CC(F)=C(OC3=CC(=CN4N=CC=C34)C3=CN=CS3)C=C2)C(=O)N(C1=O)C1=CC=C(F)C=C1 MPIHOVWDSQXNJF-UHFFFAOYSA-N 0.000 claims 1
- GEZJPGSEQPDBRG-UHFFFAOYSA-N 3-(4-fluorophenyl)-N-[3-fluoro-4-[6-(pyrimidin-2-ylamino)pyrazolo[1,5-a]pyridin-4-yl]oxyphenyl]-2,4-dioxo-1-propan-2-ylpyrimidine-5-carboxamide Chemical compound CC(C)N1C=C(C(=O)NC2=CC(F)=C(OC3=CC(NC4=NC=CC=N4)=CN4N=CC=C34)C=C2)C(=O)N(C2=CC=C(F)C=C2)C1=O GEZJPGSEQPDBRG-UHFFFAOYSA-N 0.000 claims 1
- XCRNALAPOFFGOT-UHFFFAOYSA-N 3-(4-fluorophenyl)-N-[3-methyl-4-[6-(1-methylimidazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxyphenyl]-2,4-dioxo-1-propan-2-ylpyrimidine-5-carboxamide Chemical compound CC(C)N1C=C(C(=O)NC2=CC(C)=C(OC3=CC(=CN4N=CC=C34)C3=CN(C)C=N3)C=C2)C(=O)N(C1=O)C1=CC=C(F)C=C1 XCRNALAPOFFGOT-UHFFFAOYSA-N 0.000 claims 1
- XKLXXMGZSAVQGD-UHFFFAOYSA-N 3-(4-fluorophenyl)-N-[4-[6-(1-methylimidazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxy-2-(trifluoromethyl)phenyl]-2,4-dioxo-1-propan-2-ylpyrimidine-5-carboxamide Chemical compound CC(C)N1C=C(C(=O)NC2=C(C=C(OC3=CC(=CN4N=CC=C34)C3=CN(C)C=N3)C=C2)C(F)(F)F)C(=O)N(C1=O)C1=CC=C(F)C=C1 XKLXXMGZSAVQGD-UHFFFAOYSA-N 0.000 claims 1
- HJLFIISRAJGKMR-UHFFFAOYSA-N 3-(4-fluorophenyl)-N-[6-[6-(1-methylimidazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxypyridin-3-yl]-2,4-dioxo-1-propan-2-ylpyrimidine-5-carboxamide Chemical compound CC(C)N1C=C(C(=O)NC2=CC=C(OC3=CC(=CN4N=CC=C34)C3=CN(C)C=N3)N=C2)C(=O)N(C2=CC=C(F)C=C2)C1=O HJLFIISRAJGKMR-UHFFFAOYSA-N 0.000 claims 1
- KDSGRFDWQSNHMH-UHFFFAOYSA-N 3-fluoro-4-(6-morpholin-4-ylpyrazolo[1,5-a]pyridin-4-yl)oxyaniline Chemical compound FC=1C=C(C=CC1OC=1C=2N(C=C(C1)N1CCOCC1)N=CC2)N KDSGRFDWQSNHMH-UHFFFAOYSA-N 0.000 claims 1
- KSTSPGCWFAVOJH-UHFFFAOYSA-N 3-fluoro-4-(6-pyrimidin-2-ylpyrazolo[1,5-a]pyridin-4-yl)oxyaniline Chemical compound FC=1C=C(C=CC1OC=1C=2N(C=C(C1)C1=NC=CC=N1)N=CC2)N KSTSPGCWFAVOJH-UHFFFAOYSA-N 0.000 claims 1
- MFILJCOKHXQDIA-UHFFFAOYSA-N 3-fluoro-4-[6-(1,2-thiazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxyaniline Chemical compound FC=1C=C(C=CC=1OC=1C=2N(C=C(C=1)C=1C=NSC=1)N=CC=2)N MFILJCOKHXQDIA-UHFFFAOYSA-N 0.000 claims 1
- QQVPWYSNFKXQPS-UHFFFAOYSA-N 3-methoxy-4-[6-(1-methylimidazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxyaniline Chemical compound COC=1C=C(C=CC1OC=1C=2N(C=C(C1)C=1N=CN(C1)C)N=CC2)N QQVPWYSNFKXQPS-UHFFFAOYSA-N 0.000 claims 1
- HQISKAXBFMODOZ-UHFFFAOYSA-N 3-methyl-4-(6-morpholin-4-ylpyrazolo[1,5-a]pyridin-4-yl)oxyaniline Chemical compound CC=1C=C(C=CC1OC=1C=2N(C=C(C1)N1CCOCC1)N=CC2)N HQISKAXBFMODOZ-UHFFFAOYSA-N 0.000 claims 1
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| BR112018000808A2 (pt) * | 2015-07-16 | 2018-09-04 | Array Biopharma Inc | compostos de pirazolo[1,5-a]piridina substituída como inibidores de ret cinase |
| CN106467541B (zh) | 2015-08-18 | 2019-04-05 | 暨南大学 | 取代喹诺酮类衍生物或其药学上可接受的盐或立体异构体及其药用组合物和应用 |
| CN106543145B (zh) * | 2016-10-28 | 2019-07-19 | 山西医科大学 | c-Met激酶抑剂3-(4-氟苯基)嘧啶酮-5-甲酸酰胺衍生物、制备方法与应用 |
| EP3558991A2 (en) * | 2016-12-23 | 2019-10-30 | Plexxikon Inc. | Compounds and methods for cdk8 modulation and indications therefor |
| WO2018136661A1 (en) | 2017-01-18 | 2018-07-26 | Andrews Steven W | SUBSTITUTED PYRAZOLO[1,5-a]PYRAZINE COMPOUNDS AS RET KINASE INHIBITORS |
| US11623923B2 (en) * | 2017-11-24 | 2023-04-11 | Medshine Discovery, Inc. | Uracil compound as c-MET/AXL inhibitor |
| US11472802B2 (en) | 2018-01-18 | 2022-10-18 | Array Biopharma Inc. | Substituted pyrazolyl[4,3-c]pyridine compounds as RET kinase inhibitors |
| JP7060694B2 (ja) | 2018-01-18 | 2022-04-26 | アレイ バイオファーマ インコーポレイテッド | Ｒｅｔキナーゼ阻害剤としての置換ピロロ［２，３－ｄ］ピリミジン化合物 |
| EP3740490A1 (en) | 2018-01-18 | 2020-11-25 | Array Biopharma, Inc. | Substituted pyrazolo[3,4-d]pyrimidine compounds as ret kinase inhibitors |
| ES2985569T3 (es) * | 2018-08-24 | 2024-11-06 | Transthera Sciences Nanjing Inc | Nuevo inhibidor de derivado de quinolina |
| UY38349A (es) * | 2018-08-30 | 2020-03-31 | Array Biopharma Inc | Compuestos de pirazolo[3,4-b]piridina como inhibidores de cinasas tam y met |
| CN112996794A (zh) | 2018-09-10 | 2021-06-18 | 阿雷生物药品公司 | 作为ret激酶抑制剂的稠合杂环化合物 |
| EA202192575A1 (ru) | 2019-03-21 | 2022-01-14 | Онксео | Соединения dbait в сочетании с ингибиторами киназ для лечения рака |
| CN110467616B (zh) * | 2019-07-01 | 2021-12-21 | 江西科技师范大学 | 含杂芳基取代哒嗪酮结构的三唑并吡嗪类化合物的制备及应用 |
| CN110330479A (zh) * | 2019-07-19 | 2019-10-15 | 南京华威医药科技集团有限公司 | 一种用作axl抑制剂的抗肿瘤化合物及其用途 |
| JP7542613B2 (ja) * | 2019-09-06 | 2024-08-30 | 上海 インスティテュート オブ マテリア メディカ、チャイニーズ アカデミー オブ サイエンシーズ | Ａｘｌとｃ－Ｍｅｔキナーゼ阻害活性を有する化合物およびその製造と使用 |
| CN114761006A (zh) | 2019-11-08 | 2022-07-15 | Inserm(法国国家健康医学研究院) | 对激酶抑制剂产生耐药性的癌症的治疗方法 |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| BR112022019517A2 (pt) | 2020-03-30 | 2022-12-06 | Hutchison Medipharma Ltd | Compostos de amida e usos dos mesmos |
| JP7802077B2 (ja) * | 2021-07-13 | 2026-01-19 | 日本曹達株式会社 | ウラシル化合物の製造方法 |
| IT202100022682A1 (it) * | 2021-09-01 | 2023-03-01 | Luigi Frati | Derivati pirimidinici e loro uso nel trattamento di tumori |
| CN116655626B (zh) * | 2023-05-24 | 2025-03-11 | 遵义医科大学 | 一种含咪唑并[l，2-a]吡啶骨架的环丙二酰胺化合物及其制备方法和用途 |
| AU2024319770A1 (en) | 2023-08-07 | 2026-02-19 | Cogent Biosciences, Inc. | Compounds for fgfr inhibition |
| WO2025111224A1 (en) * | 2023-11-21 | 2025-05-30 | Fmc Corporation | Linked bicyclic compounds for controlling and combating invertebrate pests |
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| US7173031B2 (en) * | 2004-06-28 | 2007-02-06 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| US7547782B2 (en) * | 2005-09-30 | 2009-06-16 | Bristol-Myers Squibb Company | Met kinase inhibitors |
| WO2007103308A2 (en) * | 2006-03-07 | 2007-09-13 | Array Biopharma Inc. | Heterobicyclic pyrazole compounds and methods of use |
| US20100004238A1 (en) * | 2006-12-12 | 2010-01-07 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compound |
| EP1972628A1 (en) | 2007-03-21 | 2008-09-24 | Schwarz Pharma Ag | Indolizines and aza-analog derivatives thereof as CNS active compounds |
| JP2011530511A (ja) | 2008-08-05 | 2011-12-22 | メルク・シャープ・エンド・ドーム・コーポレイション | 治療用化合物 |
| EA030141B1 (ru) * | 2009-12-31 | 2018-06-29 | Хатчисон Медифарма Лимитед | Определенные триазолопиридины и триазолопиразины, их композиции и способы их применения |
| MA34969B1 (fr) * | 2011-02-25 | 2014-03-01 | Irm Llc | Composes et compositions en tant qu inibiteurs de trk |
| CN102827186A (zh) * | 2011-06-16 | 2012-12-19 | 中国科学院上海药物研究所 | 一类吡啶并五元杂环衍生物及其制备方法和用途 |
| WO2013022519A1 (en) * | 2011-08-10 | 2013-02-14 | Merck Patent Gmbh | Pyrido-pyrimidine derivatives |
| SG11201400724SA (en) * | 2011-09-19 | 2014-04-28 | Genentech Inc | Combination treatments comprising c-met antagonists and b-raf antagonists |
| SG11201402004YA (en) * | 2011-11-14 | 2014-05-29 | Cephalon Inc | Uracil derivatives as axl and c-met kinase inhibitors |
| WO2013180949A1 (en) * | 2012-05-27 | 2013-12-05 | Ning Xi | Substituted quinoline compounds and methods of use |
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