JP2017500362A5 - - Google Patents
Download PDFInfo
- Publication number
- 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.)
- Pending
Links
- 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
- OBRPEOCSDIRWIZ-UHFFFAOYSA-N 4-(4-amino-2-fluorophenoxy)-N-pyridin-2-ylpyrazolo[1,5-a]pyridin-6-amine Chemical compound NC1=CC(=C(OC=2C=3N(C=C(C2)NC2=NC=CC=C2)N=CC3)C=C1)F OBRPEOCSDIRWIZ-UHFFFAOYSA-N 0.000 claims 1
- WDSLIKCXXPKXMT-UHFFFAOYSA-N 4-(4-amino-2-fluorophenoxy)-N-pyrimidin-2-ylpyrazolo[1,5-a]pyridin-6-amine Chemical compound NC1=CC(=C(OC=2C=3N(C=C(C2)NC2=NC=CC=N2)N=CC3)C=C1)F WDSLIKCXXPKXMT-UHFFFAOYSA-N 0.000 claims 1
- ZBGIXHJOGLAMTQ-UHFFFAOYSA-N 4-[2-fluoro-4-[[3-(4-fluorophenyl)-2,4-dioxo-1-propan-2-ylpyrimidine-5-carbonyl]amino]phenoxy]-N,N-dimethylpyrazolo[1,5-a]pyridine-6-carboxamide Chemical compound CN(C(=O)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)C(C)C)=O)C1=CC=C(C=C1)F)=O)F)C ZBGIXHJOGLAMTQ-UHFFFAOYSA-N 0.000 claims 1
- YRRBOQDGSYNRDF-UHFFFAOYSA-N 4-[4-[[1-ethyl-3-(4-fluorophenyl)-2,4-dioxopyrimidine-5-carbonyl]amino]-2-fluorophenoxy]pyrazolo[1,5-a]pyridine-6-carboxylic acid Chemical compound C(C)N1C(N(C(C(=C1)C(=O)NC1=CC(=C(OC=2C=3N(C=C(C=2)C(=O)O)N=CC=3)C=C1)F)=O)C1=CC=C(C=C1)F)=O YRRBOQDGSYNRDF-UHFFFAOYSA-N 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- DQSPVAFLMSGMCD-UHFFFAOYSA-N N-[3-fluoro-4-[6-(1,3-oxazol-2-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=NC=CO3)C=C2)C(=O)N(C1=O)C1=CC=C(F)C=C1 DQSPVAFLMSGMCD-UHFFFAOYSA-N 0.000 claims 1
- MJBDEYGSADKXOP-UHFFFAOYSA-N N-[3-fluoro-4-[6-(1-methylimidazol-4-yl)pyrazolo[1,5-a]pyridin-4-yl]oxyphenyl]-3-(4-fluorophenyl)-1-methyl-2,4-dioxopyrimidine-5-carboxamide Chemical compound CN1C=NC(=C1)C1=CN2N=CC=C2C(OC2=C(F)C=C(NC(=O)C3=CN(C)C(=O)N(C4=CC=C(F)C=C4)C3=O)C=C2)=C1 MJBDEYGSADKXOP-UHFFFAOYSA-N 0.000 claims 1
- DCPCFKJWZFOKBT-UHFFFAOYSA-N N-[3-fluoro-4-[6-(2-oxopyrrolidin-1-yl)pyrazolo[1,5-a]pyridin-4-yl]oxyphenyl]-3-(4-fluorophenyl)-2,4-dioxo-1-propan-2-ylpyrimidine-5-carboxamide Chemical compound FC=1C=C(C=CC=1OC=1C=2N(C=C(C=1)N1C(CCC1)=O)N=CC=2)NC(=O)C=1C(N(C(N(C=1)C(C)C)=O)C1=CC=C(C=C1)F)=O DCPCFKJWZFOKBT-UHFFFAOYSA-N 0.000 claims 1
- QZYORLHJKGVQKP-UHFFFAOYSA-N N-[4-(4-amino-2-fluorophenoxy)pyrazolo[1,5-a]pyridin-6-yl]acetamide Chemical compound NC1=CC(=C(OC=2C=3N(C=C(C2)NC(C)=O)N=CC3)C=C1)F QZYORLHJKGVQKP-UHFFFAOYSA-N 0.000 claims 1
- VYHJPVVMEWHESG-UHFFFAOYSA-N N-[4-(4-amino-2-fluorophenoxy)pyrazolo[1,5-a]pyridin-6-yl]methanesulfonamide Chemical compound NC1=CC(=C(OC=2C=3N(C=C(C2)NS(=O)(=O)C)N=CC3)C=C1)F VYHJPVVMEWHESG-UHFFFAOYSA-N 0.000 claims 1
- GBUIETYJWKMBJO-UHFFFAOYSA-N N-[4-(6-acetamidopyrazolo[1,5-a]pyridin-4-yl)oxy-3-fluorophenyl]-1-ethyl-3-(4-fluorophenyl)-2,4-dioxopyrimidine-5-carboxamide Chemical compound CCN1C=C(C(=O)NC2=CC(F)=C(OC3=CC(NC(C)=O)=CN4N=CC=C34)C=C2)C(=O)N(C1=O)C1=CC=C(F)C=C1 GBUIETYJWKMBJO-UHFFFAOYSA-N 0.000 claims 1
- BIHFARVNZDSLOR-UHFFFAOYSA-N N-[4-[6-(3,3-difluoropyrrolidin-1-yl)pyrazolo[1,5-a]pyridin-4-yl]oxy-3-fluorophenyl]-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)N3CCC(F)(F)C3)C=C2)C(=O)N(C1=O)C1=CC=C(F)C=C1 BIHFARVNZDSLOR-UHFFFAOYSA-N 0.000 claims 1
- IQPXOYXEBLLUIP-UHFFFAOYSA-N N-[4-[6-(4,4-difluoropiperidin-1-yl)pyrazolo[1,5-a]pyridin-4-yl]oxy-3-fluorophenyl]-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)N3CCC(F)(F)CC3)C=C2)C(=O)N(C1=O)C1=CC=C(F)C=C1 IQPXOYXEBLLUIP-UHFFFAOYSA-N 0.000 claims 1
- QAXXAQPEUNMZAK-UHFFFAOYSA-N N-[4-[6-(dimethylcarbamoylamino)pyrazolo[1,5-a]pyridin-4-yl]oxy-3-fluorophenyl]-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(NC(=O)N(C)C)=CN4N=CC=C34)C=C2)C(=O)N(C2=CC=C(F)C=C2)C1=O QAXXAQPEUNMZAK-UHFFFAOYSA-N 0.000 claims 1
- NBZVXQLJFLPHNC-UHFFFAOYSA-N N-[4-[6-[acetyl(methyl)amino]pyrazolo[1,5-a]pyridin-4-yl]oxy-3-fluorophenyl]-1-ethyl-3-(4-fluorophenyl)-2,4-dioxopyrimidine-5-carboxamide Chemical compound CCN1C=C(C(=O)NC2=CC(F)=C(OC3=CC(=CN4N=CC=C34)N(C)C(C)=O)C=C2)C(=O)N(C1=O)C1=CC=C(F)C=C1 NBZVXQLJFLPHNC-UHFFFAOYSA-N 0.000 claims 1
- MOTAGCYESGCWSG-UHFFFAOYSA-N N-[4-[6-[acetyl(methyl)amino]pyrazolo[1,5-a]pyridin-4-yl]oxy-3-fluorophenyl]-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)N(C)C(C)=O)C=C2)C(=O)N(C2=CC=C(F)C=C2)C1=O MOTAGCYESGCWSG-UHFFFAOYSA-N 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- KZGDBJYWJCTZGZ-UHFFFAOYSA-N methyl N-[4-[2-fluoro-4-[[3-(4-fluorophenyl)-2,4-dioxo-1-propan-2-ylpyrimidine-5-carbonyl]amino]phenoxy]pyrazolo[1,5-a]pyridin-6-yl]carbamate Chemical compound COC(NC=1C=C(C=2N(C=1)N=CC=2)OC1=C(C=C(C=C1)NC(=O)C=1C(N(C(N(C=1)C(C)C)=O)C1=CC=C(C=C1)F)=O)F)=O KZGDBJYWJCTZGZ-UHFFFAOYSA-N 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
- 125000004385 trihaloalkyl group Chemical group 0.000 claims 1
- 0 CC(C(C(N1c2ccccc2)=O)=*(*)N(*)C1=O)=O Chemical compound CC(C(C(N1c2ccccc2)=O)=*(*)N(*)C1=O)=O 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361920819P | 2013-12-26 | 2013-12-26 | |
| US61/920,819 | 2013-12-26 | ||
| PCT/US2014/071040 WO2015100117A1 (en) | 2013-12-26 | 2014-12-18 | Pyrazolo[1,5-a]pyridine derivatives and methods of their use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2017500362A JP2017500362A (ja) | 2017-01-05 |
| JP2017500362A5 true JP2017500362A5 (enExample) | 2018-02-01 |
Family
ID=52293273
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016542956A Pending JP2017500362A (ja) | 2013-12-26 | 2014-12-18 | ピラゾロ［１，５−ａ］ピリジン誘導体およびその使用方法 |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US9914731B2 (enExample) |
| EP (2) | EP3087070B1 (enExample) |
| JP (1) | JP2017500362A (enExample) |
| KR (1) | KR20160110390A (enExample) |
| CN (1) | CN106029661B (enExample) |
| AU (1) | AU2014370186A1 (enExample) |
| BR (1) | BR112016015057A2 (enExample) |
| CA (1) | CA2934667A1 (enExample) |
| CL (1) | CL2016001604A1 (enExample) |
| DK (1) | DK3087070T3 (enExample) |
| EA (2) | EA201890061A3 (enExample) |
| ES (1) | ES2654931T3 (enExample) |
| HU (1) | HUE037579T2 (enExample) |
| IL (1) | IL246311A0 (enExample) |
| MX (1) | MX2016008445A (enExample) |
| NO (1) | NO3014707T3 (enExample) |
| PH (1) | PH12016501232A1 (enExample) |
| PL (1) | PL3087070T3 (enExample) |
| PT (1) | PT3087070T (enExample) |
| SG (1) | SG11201605207PA (enExample) |
| SI (1) | SI3087070T1 (enExample) |
| WO (1) | WO2015100117A1 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108349969B (zh) * | 2015-07-16 | 2022-05-10 | 阵列生物制药公司 | 作为RET激酶抑制剂的取代的吡唑并[1,5-a]吡啶化合物 |
| 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 |
| US10703757B2 (en) | 2016-12-23 | 2020-07-07 | Plexxikon Inc. | Compounds and methods for CDK8 modulation and indications therefor |
| ES2948194T3 (es) | 2017-01-18 | 2023-09-01 | Array Biopharma Inc | Compuestos de pirazolo[1,5-a]pirazina sustituida como inhibidores de la cinasa RET |
| JP7377798B2 (ja) * | 2017-11-24 | 2023-11-10 | 南京明徳新薬研発有限公司 | ｃ－ＭＥＴ／ＡＸＬ阻害剤としてのウラシル系化合物 |
| CN111971286B (zh) | 2018-01-18 | 2023-04-14 | 阿雷生物药品公司 | 作为RET激酶抑制剂的取代的吡咯并[2,3-d]嘧啶化合物 |
| US11472802B2 (en) | 2018-01-18 | 2022-10-18 | Array Biopharma Inc. | Substituted pyrazolyl[4,3-c]pyridine compounds as RET kinase inhibitors |
| CN111630054B (zh) | 2018-01-18 | 2023-05-09 | 奥瑞生物药品公司 | 作为RET激酶抑制剂的取代的吡唑并[3,4-d]嘧啶化合物 |
| SG11202101622VA (en) * | 2018-08-24 | 2021-03-30 | Nanjing Transthera Biosciences Co Ltd | Novel quinoline derivative inhibitor |
| 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 |
| WO2020055672A1 (en) | 2018-09-10 | 2020-03-19 | Array Biopharma Inc. | Fused heterocyclic compounds as ret kinase inhibitors |
| CN114364798A (zh) | 2019-03-21 | 2022-04-15 | 欧恩科斯欧公司 | 用于治疗癌症的Dbait分子与激酶抑制剂的组合 |
| 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 |
| CN112457295B (zh) * | 2019-09-06 | 2022-07-26 | 中国科学院上海药物研究所 | 具有Axl与c-Met激酶抑制活性的化合物及其制备和应用 |
| US20220401436A1 (en) | 2019-11-08 | 2022-12-22 | INSERM (Institute National de la Santé et de la Recherche Médicale) | 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 |
| CN115315422B (zh) | 2020-03-30 | 2023-11-07 | 和记黄埔医药（上海）有限公司 | 酰胺类化合物及其用途 |
| US20240317692A1 (en) * | 2021-07-13 | 2024-09-26 | Nippon Soda Co., Ltd. | Method for producing uracil compound |
| 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 |
| WO2025034912A2 (en) | 2023-08-07 | 2025-02-13 | 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 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20020506A1 (es) * | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
| US20050288290A1 (en) * | 2004-06-28 | 2005-12-29 | Borzilleri Robert M | Fused heterocyclic kinase inhibitors |
| US7547782B2 (en) * | 2005-09-30 | 2009-06-16 | Bristol-Myers Squibb Company | Met kinase inhibitors |
| JP2009529047A (ja) * | 2006-03-07 | 2009-08-13 | アレイ バイオファーマ、インコーポレイテッド | ヘテロ二環系ピラゾール化合物およびその使用 |
| WO2008072634A1 (ja) * | 2006-12-12 | 2008-06-19 | Takeda Pharmaceutical Company Limited | 縮合複素環化合物 |
| EP1972628A1 (en) | 2007-03-21 | 2008-09-24 | Schwarz Pharma Ag | Indolizines and aza-analog derivatives thereof as CNS active compounds |
| US8455477B2 (en) | 2008-08-05 | 2013-06-04 | Merck Sharp & Dohme Corp. | Therapeutic compounds |
| SI3511330T1 (sl) * | 2009-12-31 | 2021-01-29 | Hutchison Medipharma Limited | Sintetična umetna spojina uporabna v pripravi triazolopiridinskih zaviralcev c-Met |
| EA201391230A1 (ru) * | 2011-02-25 | 2014-01-30 | АйАрЭм ЭлЭлСи | Соединения и композиции в качестве ингибиторов 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 |
| JP6001072B2 (ja) * | 2011-08-10 | 2016-10-05 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | ピリド−ピリミジン誘導体 |
| BR112014006419A2 (pt) * | 2011-09-19 | 2018-08-07 | Genentech Inc | métodos para tratar um paciente com câncer, kit e artigo |
| JP6051434B2 (ja) * | 2011-11-14 | 2016-12-27 | イグニタ、インク． | ＡＸＬおよびｃ−ＭＥＴキナーゼ阻害剤としてのウラシル誘導体 |
| WO2013180949A1 (en) * | 2012-05-27 | 2013-12-05 | Ning Xi | Substituted quinoline compounds and methods of use |
-
2014
- 2014-12-18 EA EA201890061A patent/EA201890061A3/ru unknown
- 2014-12-18 PL PL14824711T patent/PL3087070T3/pl unknown
- 2014-12-18 AU AU2014370186A patent/AU2014370186A1/en not_active Abandoned
- 2014-12-18 EA EA201691164A patent/EA029757B1/ru not_active IP Right Cessation
- 2014-12-18 SI SI201430533T patent/SI3087070T1/en unknown
- 2014-12-18 WO PCT/US2014/071040 patent/WO2015100117A1/en not_active Ceased
- 2014-12-18 MX MX2016008445A patent/MX2016008445A/es unknown
- 2014-12-18 EP EP14824711.7A patent/EP3087070B1/en not_active Not-in-force
- 2014-12-18 ES ES14824711.7T patent/ES2654931T3/es active Active
- 2014-12-18 SG SG11201605207PA patent/SG11201605207PA/en unknown
- 2014-12-18 KR KR1020167019605A patent/KR20160110390A/ko not_active Withdrawn
- 2014-12-18 JP JP2016542956A patent/JP2017500362A/ja active Pending
- 2014-12-18 US US15/108,400 patent/US9914731B2/en not_active Expired - Fee Related
- 2014-12-18 CA CA2934667A patent/CA2934667A1/en not_active Abandoned
- 2014-12-18 BR BR112016015057A patent/BR112016015057A2/pt not_active IP Right Cessation
- 2014-12-18 EP EP17196014.9A patent/EP3309160A1/en not_active Withdrawn
- 2014-12-18 DK DK14824711.7T patent/DK3087070T3/en active
- 2014-12-18 CN CN201480075903.4A patent/CN106029661B/zh not_active Expired - Fee Related
- 2014-12-18 PT PT148247117T patent/PT3087070T/pt unknown
- 2014-12-18 HU HUE14824711A patent/HUE037579T2/hu unknown
-
2015
- 2015-06-23 NO NO15745380A patent/NO3014707T3/no unknown
-
2016
- 2016-06-19 IL IL246311A patent/IL246311A0/en unknown
- 2016-06-21 CL CL2016001604A patent/CL2016001604A1/es unknown
- 2016-06-22 PH PH12016501232A patent/PH12016501232A1/en unknown
-
2018
- 2018-01-24 US US15/879,175 patent/US20180148447A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2017500362A5 (enExample) | ||
| SI3087070T1 (en) | Pyrazolo (1,5-a) pyridine derivatives and processes for their use | |
| US10669269B2 (en) | Substituted N-(1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide compounds as type III receptor tyrosine kinase inhibitors | |
| US12133841B2 (en) | Heterocyclic compounds as kinase inhibitors, compositions comprising the heterocyclic compound, and methods of use thereof | |
| US9796719B2 (en) | Compounds and pharmaceutical compositions thereof for the treatment of inflammatory disorders | |
| ES2642586T3 (es) | Compuestos heterocíclicos condensados como moduladores de canales iónicos | |
| CN102105471B (zh) | 用于治疗变性和炎性疾病的化合物 | |
| US9862707B2 (en) | TrkA kinase inhibitors, compositions and methods thereof | |
| US8614226B2 (en) | Hetaryl-[1,8]naphthyridine derivatives | |
| US9809573B2 (en) | Substituted pyridine derivatives useful as GSK-3 inhibitors | |
| HRP20200962T1 (hr) | Novi spojevi | |
| JP2016523911A5 (enExample) | ||
| US20220402911A1 (en) | Novel compounds and pharmaceutical compositions thereof for the treatment of diseases | |
| JP2017530960A5 (enExample) | ||
| US10807988B2 (en) | 3-((hetero-)aryl)-8-amino-2-oxo-1,3-diaza-spiro-[4.5]-decane derivatives | |
| ME02416B (me) | Trpv4 antagonisтi | |
| JP2014518214A5 (enExample) | ||
| US20140142097A1 (en) | Pyridine-and pyrazine derivatives | |
| JP2017512794A (ja) | ＴｒｋＡキナーゼ阻害薬、その組成物および方法 | |
| US20130237519A1 (en) | Bicyclic heterocycle derivatives for the treatment of pulmonary arterial hypertension | |
| US20130217664A1 (en) | Novel compounds useful for the treatment of degenerative and inflammatory diseases | |
| US20140323468A1 (en) | Aldosterone synthase inhibitors | |
| US20170158698A1 (en) | TrKA Kinase Inhibitors, Compositions and Methods Thereof | |
| US11814384B2 (en) | Inhibtors of Raf kinases |