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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| PT3322706T (pt) * | 2015-07-16 | 2021-03-08 | Array Biopharma Inc | Compostos de pirazolo[1,5-a]piridina substituídos como inibidores da quinase do ret |
| 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 |
| WO2018136202A2 (en) * | 2016-12-23 | 2018-07-26 | Plexxikon Inc. | Compounds and methods for cdk8 modulation and indications therefor |
| JP6888101B2 (ja) | 2017-01-18 | 2021-06-16 | 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ラゾロ［１，５−ａ］ピラジン化合物 |
| CN111372925B (zh) * | 2017-11-24 | 2022-09-02 | 南京明德新药研发有限公司 | 作为c-MET/AXL抑制剂的尿嘧啶类化合物 |
| WO2019143977A1 (en) | 2018-01-18 | 2019-07-25 | Array Biopharma Inc. | Substituted pyrrolo[2,3-d]pyrimidines compounds as ret kinase inhibitors |
| JP6997876B2 (ja) | 2018-01-18 | 2022-02-04 | 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ラゾリル［４，３－ｃ］ピリジン化合物 |
| WO2019143991A1 (en) | 2018-01-18 | 2019-07-25 | Array Biopharma Inc. | SUBSTITUTED PYRAZOLO[3,4-d]PYRIMIDINE COMPOUNDS AS RET KINASE INHIBITORS |
| CN110857293B (zh) * | 2018-08-24 | 2023-01-10 | 药捷安康(南京)科技股份有限公司 | 一种新型的喹啉衍生物抑制剂 |
| 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 |
| CA3111984A1 (en) | 2018-09-10 | 2020-03-19 | Array Biopharma Inc. | Fused heterocyclic compounds as ret kinase inhibitors |
| BR112021018168B1 (pt) | 2019-03-21 | 2023-11-28 | Onxeo | Composição farmacêutica, combinação e kit compreendendo uma molécula dbait e um inibidor de quinase para o tratamento de câncer |
| 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 |
| AU2020342108B2 (en) | 2019-09-06 | 2024-03-07 | Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences | Compound having Axl and c-Met kinase inhibitory activity, preparation thereof and application thereof |
| CA3159348A1 (en) | 2019-11-08 | 2021-05-14 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Methods for the treatment of cancers that have acquired resistance to kinase inhibitors |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| WO2021197276A1 (en) | 2020-03-30 | 2021-10-07 | Hutchison Medipharma Limited | Amide compounds and uses thereof |
| 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 |
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| 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 |
| CA2645137A1 (en) * | 2006-03-07 | 2007-09-13 | James F. Blake | Heterobicyclic pyrazole compounds and methods of use |
| RU2009126576A (ru) * | 2006-12-12 | 2011-01-20 | Такеда Фармасьютикал Компани Лимитед (Jp) | Конденсированное гетероциклическое соединение |
| EP1972628A1 (en) | 2007-03-21 | 2008-09-24 | Schwarz Pharma Ag | Indolizines and aza-analog derivatives thereof as CNS active compounds |
| WO2010017047A1 (en) | 2008-08-05 | 2010-02-11 | Merck & Co., Inc. | Therapeutic compounds |
| HUE025504T2 (en) * | 2009-12-31 | 2016-02-29 | Hutchison Medipharma Ltd | Certain triazolopyrazines, compositions thereof and methods of use therefor |
| KR20140014184A (ko) * | 2011-02-25 | 2014-02-05 | 아이알엠 엘엘씨 | Trk 억제제로서의 화합물 및 조성물 |
| 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 |
| CA2844588A1 (en) * | 2011-08-10 | 2013-02-14 | Merck Patent Gmbh | Pyrido-pyrimidine derivatives |
| US20130078252A1 (en) * | 2011-09-19 | 2013-03-28 | Genentech, Inc. | Combination treatments comprising c-met antagonists and b-raf antagonists |
| AU2012339640B2 (en) * | 2011-11-14 | 2017-01-05 | Ignyta, 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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