JP2011520908A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2011520908A5 JP2011520908A5 JP2011509721A JP2011509721A JP2011520908A5 JP 2011520908 A5 JP2011520908 A5 JP 2011520908A5 JP 2011509721 A JP2011509721 A JP 2011509721A JP 2011509721 A JP2011509721 A JP 2011509721A JP 2011520908 A5 JP2011520908 A5 JP 2011520908A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- oxo
- carboxamide
- dihydro
- methyl
- 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.)
- Granted
Links
- -1 bevacizumab Chemical compound 0.000 claims 42
- 125000000217 alkyl group Chemical group 0.000 claims 32
- 239000008194 pharmaceutical composition Substances 0.000 claims 19
- 125000000623 heterocyclic group Chemical group 0.000 claims 18
- 125000003118 aryl group Chemical group 0.000 claims 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims 9
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 9
- ORHWJCFXPIQGGV-UHFFFAOYSA-N 1-(2-hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound CC(O)(C)CN1C(C)=C(C(N)=O)C(=O)N1C1=CC=CC=C1 ORHWJCFXPIQGGV-UHFFFAOYSA-N 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 8
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 7
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 239000003112 inhibitor Substances 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 229940124674 VEGF-R inhibitor Drugs 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims 5
- 150000003857 carboxamides Chemical class 0.000 claims 5
- 125000001188 haloalkyl group Chemical class 0.000 claims 5
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 5
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- ZBWCOZDGHJCGSC-UHFFFAOYSA-N thieno[3,2-b]pyridine-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=N1 ZBWCOZDGHJCGSC-UHFFFAOYSA-N 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- HLYLVLPUVNOQHH-UHFFFAOYSA-N 1-(2-aminoethyl)-n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(CCN)N1C1=CC=CC=C1 HLYLVLPUVNOQHH-UHFFFAOYSA-N 0.000 claims 2
- ZTWMMBAANLTIFG-UHFFFAOYSA-N 1-cyclopentyl-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-6-oxo-5-(2-oxopyrrolidin-1-yl)pyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(=CN(C1=O)C2CCCC2)C=C1N1CCCC1=O ZTWMMBAANLTIFG-UHFFFAOYSA-N 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 206010038389 Renal cancer Diseases 0.000 claims 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 2
- 125000003418 alkyl amino alkoxy group Chemical group 0.000 claims 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 201000010536 head and neck cancer Diseases 0.000 claims 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims 2
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 201000010982 kidney cancer Diseases 0.000 claims 2
- 201000005202 lung cancer Diseases 0.000 claims 2
- 208000020816 lung neoplasm Diseases 0.000 claims 2
- 229950003968 motesanib Drugs 0.000 claims 2
- RAHBGWKEPAQNFF-UHFFFAOYSA-N motesanib Chemical compound C=1C=C2C(C)(C)CNC2=CC=1NC(=O)C1=CC=CN=C1NCC1=CC=NC=C1 RAHBGWKEPAQNFF-UHFFFAOYSA-N 0.000 claims 2
- AVOHPVUAPGVLAY-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-3-oxo-4-phenylmorpholine-2-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)OCCN1C1=CC=CC=C1 AVOHPVUAPGVLAY-UHFFFAOYSA-N 0.000 claims 2
- GODJFMYOWZKKJA-UHFFFAOYSA-N n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-1-methyl-3-oxo-2-phenyl-5-(pyrrolidin-1-ylmethyl)pyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C(N(C=1C=CC=CC=1)N1C)=O)=C1CN1CCCC1 GODJFMYOWZKKJA-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- OKEXWWXROOZIDZ-UHFFFAOYSA-N 1-(2,3-dihydroxy-2-methylpropyl)-n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(CC(C)(O)CO)N1C1=CC=CC=C1 OKEXWWXROOZIDZ-UHFFFAOYSA-N 0.000 claims 1
- PFNRBPBRWZUOHH-UHFFFAOYSA-N 1-(2,3-dihydroxy-2-methylpropyl)-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(CC(C)(O)CO)N1C1=CC=CC=C1 PFNRBPBRWZUOHH-UHFFFAOYSA-N 0.000 claims 1
- KLWBNEIPBOZAOQ-UHFFFAOYSA-N 1-(2-chlorophenyl)-n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-2,3-dimethyl-5-oxopyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(C)N1C1=CC=CC=C1Cl KLWBNEIPBOZAOQ-UHFFFAOYSA-N 0.000 claims 1
- RWTDTDOEQJHZMX-UHFFFAOYSA-N 1-(2-chlorophenyl)-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-2,3-dimethyl-5-oxopyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(C)N1C1=CC=CC=C1Cl RWTDTDOEQJHZMX-UHFFFAOYSA-N 0.000 claims 1
- JEBQCADLFAZBCB-UHFFFAOYSA-N 1-(2-chlorophenyl)-n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-2,3-dimethyl-5-oxopyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(C)N(C)N1C1=CC=CC=C1Cl JEBQCADLFAZBCB-UHFFFAOYSA-N 0.000 claims 1
- POEZAPIQLMNFDN-UHFFFAOYSA-N 1-(2-hydroxy-2-methylpropyl)-4-[7-(7-methoxyquinolin-4-yl)oxy-2,3-dihydro-1,4-benzoxazine-4-carbonyl]-5-methyl-2-phenylpyrazol-3-one Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=C1OCC2)=CC=C1N2C(=O)C(C1=O)=C(C)N(CC(C)(C)O)N1C1=CC=CC=C1 POEZAPIQLMNFDN-UHFFFAOYSA-N 0.000 claims 1
- IIZIRGJCJMFRDM-UHFFFAOYSA-N 1-(2-hydroxy-2-methylpropyl)-N-[5-(7-hydroxyquinolin-4-yl)oxypyridin-2-yl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound CC(O)(C)CN1C(C)=C(C(=O)NC=2N=CC(OC=3C4=CC=C(O)C=C4N=CC=3)=CC=2)C(=O)N1C1=CC=CC=C1 IIZIRGJCJMFRDM-UHFFFAOYSA-N 0.000 claims 1
- DSTCGXWRQMWOLU-UHFFFAOYSA-N 1-(2-hydroxy-2-methylpropyl)-n-[4-(7-methoxyquinolin-4-yl)sulfanylphenyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1SC(C=C1)=CC=C1NC(=O)C(C1=O)=C(C)N(CC(C)(C)O)N1C1=CC=CC=C1 DSTCGXWRQMWOLU-UHFFFAOYSA-N 0.000 claims 1
- KLCUYIJZSLYGPX-UHFFFAOYSA-N 1-(2-hydroxy-2-methylpropyl)-n-[4-[(7-methoxyquinolin-4-yl)amino]phenyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1NC(C=C1)=CC=C1NC(=O)C(C1=O)=C(C)N(CC(C)(C)O)N1C1=CC=CC=C1 KLCUYIJZSLYGPX-UHFFFAOYSA-N 0.000 claims 1
- GLBZSOQDAOLMGC-UHFFFAOYSA-N 1-(2-hydroxy-2-methylpropyl)-n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(C)N(CC(C)(C)O)N1C1=CC=CC=C1 GLBZSOQDAOLMGC-UHFFFAOYSA-N 0.000 claims 1
- GODQNRDRRFCJJI-UHFFFAOYSA-N 1-(2-hydroxy-3-methylbutyl)-n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(C)N(CC(O)C(C)C)N1C1=CC=CC=C1 GODQNRDRRFCJJI-UHFFFAOYSA-N 0.000 claims 1
- BSFOFLYNEZXJRV-UHFFFAOYSA-N 1-(2-hydroxyethyl)-n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(C)N(CCO)N1C1=CC=CC=C1 BSFOFLYNEZXJRV-UHFFFAOYSA-N 0.000 claims 1
- JQKLADMYWZPROY-UHFFFAOYSA-N 1-(2-hydroxypropyl)-n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(C)N(CC(C)O)N1C1=CC=CC=C1 JQKLADMYWZPROY-UHFFFAOYSA-N 0.000 claims 1
- YKCLPZQBFQBZAH-UHFFFAOYSA-N 1-(2-methoxyethyl)-n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound COCCN1C(C)=C(C(=O)NC=2N=CC(OC=3C4=CC=C(OC)C=C4N=CC=3)=CC=2)C(=O)N1C1=CC=CC=C1 YKCLPZQBFQBZAH-UHFFFAOYSA-N 0.000 claims 1
- NXVHOYBQFPQTBF-UHFFFAOYSA-N 1-(3-amino-2-hydroxypropyl)-n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(CC(O)CN)N1C1=CC=CC=C1 NXVHOYBQFPQTBF-UHFFFAOYSA-N 0.000 claims 1
- LSLNTRBLINLJPQ-UHFFFAOYSA-N 1-(3-chloro-2-hydroxypropyl)-n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(CC(O)CCl)N1C1=CC=CC=C1 LSLNTRBLINLJPQ-UHFFFAOYSA-N 0.000 claims 1
- GJQIRTVTEPSRFR-QGZVFWFLSA-N 1-(3-chlorophenyl)-2-[(2r)-2-hydroxypropyl]-n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-3-methyl-5-oxopyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(C)N(C[C@@H](C)O)N1C1=CC=CC(Cl)=C1 GJQIRTVTEPSRFR-QGZVFWFLSA-N 0.000 claims 1
- ZEBSTEYDIZZWEH-UHFFFAOYSA-N 1-(3-chlorophenyl)-n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-2,3-dimethyl-5-oxopyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(C)N1C1=CC=CC(Cl)=C1 ZEBSTEYDIZZWEH-UHFFFAOYSA-N 0.000 claims 1
- TUUULFZRCAPYRR-QGZVFWFLSA-N 1-(3-chlorophenyl)-n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-2-[(2r)-2-hydroxypropyl]-3-methyl-5-oxopyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(C[C@@H](C)O)N1C1=CC=CC(Cl)=C1 TUUULFZRCAPYRR-QGZVFWFLSA-N 0.000 claims 1
- QOQCJDLVGDYHPN-UHFFFAOYSA-N 1-(3-chlorophenyl)-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-2,3-dimethyl-5-oxopyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(C)N1C1=CC=CC(Cl)=C1 QOQCJDLVGDYHPN-UHFFFAOYSA-N 0.000 claims 1
- ZDYRMOXSICQXCU-UHFFFAOYSA-N 1-(3-chlorophenyl)-n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-2,3-dimethyl-5-oxopyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(C)N(C)N1C1=CC=CC(Cl)=C1 ZDYRMOXSICQXCU-UHFFFAOYSA-N 0.000 claims 1
- SXFOXKZSCPYKRZ-UHFFFAOYSA-N 1-(3-chlorophenyl)-n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-2,3-dimethyl-5-oxopyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(C)N(C)N1C1=CC=CC(Cl)=C1 SXFOXKZSCPYKRZ-UHFFFAOYSA-N 0.000 claims 1
- BGLJTUOUNXPWKK-GOSISDBHSA-N 1-[(2r)-2-fluoropropyl]-n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(C)N(C[C@@H](C)F)N1C1=CC=CC=C1 BGLJTUOUNXPWKK-GOSISDBHSA-N 0.000 claims 1
- GODQNRDRRFCJJI-SANMLTNESA-N 1-[(2r)-2-hydroxy-3-methylbutyl]-n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(C)N(C[C@H](O)C(C)C)N1C1=CC=CC=C1 GODQNRDRRFCJJI-SANMLTNESA-N 0.000 claims 1
- KDEGIEOWBSKWFB-GOSISDBHSA-N 1-[(2r)-2-hydroxypropyl]-n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-2-methyl-3-oxo-5-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C(N(C)N1C[C@@H](C)O)=O)=C1C1=CC=CC=C1 KDEGIEOWBSKWFB-GOSISDBHSA-N 0.000 claims 1
- CQWDSBGPARDPDD-UYAOXDASSA-N 1-[(2r,3r)-3-hydroxybutan-2-yl]-n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(C)N([C@H](C)[C@@H](C)O)N1C1=CC=CC=C1 CQWDSBGPARDPDD-UYAOXDASSA-N 0.000 claims 1
- PUVFWTQKDQUFCP-FQEVSTJZSA-N 1-[(2s)-2-(dimethylamino)propyl]-n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(C[C@H](C)N(C)C)N1C1=CC=CC=C1 PUVFWTQKDQUFCP-FQEVSTJZSA-N 0.000 claims 1
- GNPMSGXAUSJKSF-SFHVURJKSA-N 1-[(2s)-2-aminopropyl]-n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(C[C@H](C)N)N1C1=CC=CC=C1 GNPMSGXAUSJKSF-SFHVURJKSA-N 0.000 claims 1
- UDCKDKQRKKIFNW-SFHVURJKSA-N 1-[(2s)-2-azidopropyl]-n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(C[C@H](C)N=[N+]=[N-])N1C1=CC=CC=C1 UDCKDKQRKKIFNW-SFHVURJKSA-N 0.000 claims 1
- BGLJTUOUNXPWKK-SFHVURJKSA-N 1-[(2s)-2-fluoropropyl]-n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(C)N(C[C@H](C)F)N1C1=CC=CC=C1 BGLJTUOUNXPWKK-SFHVURJKSA-N 0.000 claims 1
- GODQNRDRRFCJJI-AREMUKBSSA-N 1-[(2s)-2-hydroxy-3-methylbutyl]-n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(C)N(C[C@@H](O)C(C)C)N1C1=CC=CC=C1 GODQNRDRRFCJJI-AREMUKBSSA-N 0.000 claims 1
- OABFOLORAWZNJA-UHFFFAOYSA-N 1-[2-(1,3-dioxoisoindol-2-yl)ethyl]-n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(CCN2C(C3=CC=CC=C3C2=O)=O)N1C1=CC=CC=C1 OABFOLORAWZNJA-UHFFFAOYSA-N 0.000 claims 1
- XSSFHNSBYMMVCU-UHFFFAOYSA-N 1-[3-(dimethylamino)-2-hydroxypropyl]-n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(CC(O)CN(C)C)N1C1=CC=CC=C1 XSSFHNSBYMMVCU-UHFFFAOYSA-N 0.000 claims 1
- XUJAABYTWJFTEW-UHFFFAOYSA-N 1-benzyl-5-bromo-n-[2-chloro-4-(6,7-dimethoxyquinolin-4-yl)oxyphenyl]-2-oxopyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1Cl)=CC=C1NC(=O)C(C1=O)=CC(Br)=CN1CC1=CC=CC=C1 XUJAABYTWJFTEW-UHFFFAOYSA-N 0.000 claims 1
- INDIBSRESKHAFT-UHFFFAOYSA-N 1-benzyl-n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-2-methyl-5-oxo-3-pyridin-4-ylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C(N(CC=1C=CC=CC=1)N1C)=O)=C1C1=CC=NC=C1 INDIBSRESKHAFT-UHFFFAOYSA-N 0.000 claims 1
- QYXHMYYFMRXTPC-UHFFFAOYSA-N 1-benzyl-n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C(N1C=2C=CC=CC=2)=O)=C(C)N1CC1=CC=CC=C1 QYXHMYYFMRXTPC-UHFFFAOYSA-N 0.000 claims 1
- NDMASZSOUPWTIW-UHFFFAOYSA-N 1-benzyl-n-[3-fluoro-4-[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinolin-4-yl]oxyphenyl]-2-oxo-5-phenylpyridine-3-carboxamide Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC(C=2C=CC=CC=2)=CN1CC1=CC=CC=C1 NDMASZSOUPWTIW-UHFFFAOYSA-N 0.000 claims 1
- SXMPGEUQDPFYEA-UHFFFAOYSA-N 1-benzyl-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-2,3-dimethyl-5-oxopyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(C)N1CC1=CC=CC=C1 SXMPGEUQDPFYEA-UHFFFAOYSA-N 0.000 claims 1
- DQOIOXHXYBCWOD-UHFFFAOYSA-N 1-benzyl-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-2-oxo-5-pyrimidin-2-ylpyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC(C=2N=CC=CN=2)=CN1CC1=CC=CC=C1 DQOIOXHXYBCWOD-UHFFFAOYSA-N 0.000 claims 1
- VOYMQBVUKYZKRM-UHFFFAOYSA-N 1-benzyl-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C(N1C=2C=CC=CC=2)=O)=C(C)N1CC1=CC=CC=C1 VOYMQBVUKYZKRM-UHFFFAOYSA-N 0.000 claims 1
- BJPUMWQUGHZEOZ-UHFFFAOYSA-N 1-benzyl-n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-2,3-dimethyl-5-oxopyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(C)N(C)N1CC1=CC=CC=C1 BJPUMWQUGHZEOZ-UHFFFAOYSA-N 0.000 claims 1
- RZTXWZJWBLFFBD-UHFFFAOYSA-N 1-benzyl-n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-2-oxo-4-(pyridin-4-ylamino)pyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C(N(CC=1C=CC=CC=1)C=C1)=O)=C1NC1=CC=NC=C1 RZTXWZJWBLFFBD-UHFFFAOYSA-N 0.000 claims 1
- SYRGGVAJBRMNTA-UHFFFAOYSA-N 1-benzyl-n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-2-oxo-4-[4-(trifluoromethyl)anilino]pyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C(N(CC=1C=CC=CC=1)C=C1)=O)=C1NC1=CC=C(C(F)(F)F)C=C1 SYRGGVAJBRMNTA-UHFFFAOYSA-N 0.000 claims 1
- BOBZMFUSDFFCLS-UHFFFAOYSA-N 1-benzyl-n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-2-oxo-5-(1,2,3,6-tetrahydropyridin-4-yl)pyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=CC(C=2CCNCC=2)=CN1CC1=CC=CC=C1 BOBZMFUSDFFCLS-UHFFFAOYSA-N 0.000 claims 1
- NLQPFOFVGIQSAL-UHFFFAOYSA-N 1-benzyl-n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-2-oxo-5-pyrazin-2-ylpyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=CC(C=2N=CC=NC=2)=CN1CC1=CC=CC=C1 NLQPFOFVGIQSAL-UHFFFAOYSA-N 0.000 claims 1
- GGMLJZRRHXTGSJ-UHFFFAOYSA-N 1-benzyl-n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-2-oxo-5-pyridin-3-ylpyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=CC(C=2C=NC=CC=2)=CN1CC1=CC=CC=C1 GGMLJZRRHXTGSJ-UHFFFAOYSA-N 0.000 claims 1
- HPFRJPDLSIHOSC-UHFFFAOYSA-N 1-benzyl-n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-2-oxo-5-thiophen-2-ylpyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=CC(C=2SC=CC=2)=CN1CC1=CC=CC=C1 HPFRJPDLSIHOSC-UHFFFAOYSA-N 0.000 claims 1
- BSFMLWRRSOWTEQ-UHFFFAOYSA-N 1-benzyl-n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-4-(2-methoxyethylamino)-2-oxopyridine-3-carboxamide Chemical compound O=C1C(C(=O)NC=2N=CC(OC=3C4=CC(OC)=C(OC)C=C4N=CC=3)=CC=2)=C(NCCOC)C=CN1CC1=CC=CC=C1 BSFMLWRRSOWTEQ-UHFFFAOYSA-N 0.000 claims 1
- ZVMBBZJEGOQZHF-UHFFFAOYSA-N 1-benzyl-n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-4-(4-methylpiperazin-1-yl)-2-oxopyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(N2CCN(C)CC2)C=CN1CC1=CC=CC=C1 ZVMBBZJEGOQZHF-UHFFFAOYSA-N 0.000 claims 1
- ZLYIWZZKBFXXBS-UHFFFAOYSA-N 1-benzyl-n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-4-(dimethylamino)-2-oxopyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(N(C)C)C=CN1CC1=CC=CC=C1 ZLYIWZZKBFXXBS-UHFFFAOYSA-N 0.000 claims 1
- HMPBJXGQRFGDCD-UHFFFAOYSA-N 1-benzyl-n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-4-(methylamino)-2-oxopyridine-3-carboxamide Chemical compound O=C1C(C(=O)NC=2N=CC(OC=3C4=CC(OC)=C(OC)C=C4N=CC=3)=CC=2)=C(NC)C=CN1CC1=CC=CC=C1 HMPBJXGQRFGDCD-UHFFFAOYSA-N 0.000 claims 1
- QMSSRMSGVQTIJN-UHFFFAOYSA-N 1-benzyl-n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-4-(oxan-4-ylamino)-2-oxopyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C(N(CC=1C=CC=CC=1)C=C1)=O)=C1NC1CCOCC1 QMSSRMSGVQTIJN-UHFFFAOYSA-N 0.000 claims 1
- DQPLHSQRODNPOZ-UHFFFAOYSA-N 1-benzyl-n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-5-methyl-2-oxopyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=CC(C)=CN1CC1=CC=CC=C1 DQPLHSQRODNPOZ-UHFFFAOYSA-N 0.000 claims 1
- CLZOZOSHJCABEL-UHFFFAOYSA-N 1-benzyl-n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-2-methyl-5-oxo-3-pyridin-4-ylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C(N(CC=1C=CC=CC=1)N1C)=O)=C1C1=CC=NC=C1 CLZOZOSHJCABEL-UHFFFAOYSA-N 0.000 claims 1
- WOMSVOUVSINKRP-UHFFFAOYSA-N 1-benzyl-n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-2-oxopyrazolo[1,5-a]pyridine-3-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C2C=CC=CN2N1CC1=CC=CC=C1 WOMSVOUVSINKRP-UHFFFAOYSA-N 0.000 claims 1
- OSCBXCDDUKCMTK-UHFFFAOYSA-N 2-benzyl-n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-6-methyl-3-oxopyridazine-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=CC(C)=NN1CC1=CC=CC=C1 OSCBXCDDUKCMTK-UHFFFAOYSA-N 0.000 claims 1
- XSUNRMDPAMACKN-UHFFFAOYSA-N 2-phenyl-1,5-dihydropyrazole-4-carboxamide Chemical compound C1(=CC=CC=C1)N1NCC(=C1)C(=O)N XSUNRMDPAMACKN-UHFFFAOYSA-N 0.000 claims 1
- AHGCTVPKMZGQPH-UHFFFAOYSA-N 3-(dimethylamino)pyrrolidine-1-carboxamide Chemical compound CN(C)C1CCN(C(N)=O)C1 AHGCTVPKMZGQPH-UHFFFAOYSA-N 0.000 claims 1
- ONWIGSJBMCHKOV-UHFFFAOYSA-N 3-benzyl-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-2-oxoimidazolidine-1-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)N(C1=O)CCN1CC1=CC=CC=C1 ONWIGSJBMCHKOV-UHFFFAOYSA-N 0.000 claims 1
- AKLARZWWYXICKZ-UHFFFAOYSA-N 4-(2-methoxyethylamino)-n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-2-oxo-1-phenylpyridine-3-carboxamide Chemical compound O=C1C(C(=O)NC=2N=CC(OC=3C4=CC=C(OC)C=C4N=CC=3)=CC=2)=C(NCCOC)C=CN1C1=CC=CC=C1 AKLARZWWYXICKZ-UHFFFAOYSA-N 0.000 claims 1
- KMFUHVPATMACJR-UHFFFAOYSA-N 4-(6,7-dimethoxyquinolin-4-yl)oxy-n-[(1,2-dimethyl-3-oxo-5-phenylpyrazol-4-yl)methyl]-3-fluorobenzamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1C(=O)NCC(C(N(C)N1C)=O)=C1C1=CC=CC=C1 KMFUHVPATMACJR-UHFFFAOYSA-N 0.000 claims 1
- XXJWYDDUDKYVKI-UHFFFAOYSA-N 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-[3-(1-pyrrolidinyl)propoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C(=C4C=C(C)NC4=CC=3)F)N=CN=C2C=C1OCCCN1CCCC1 XXJWYDDUDKYVKI-UHFFFAOYSA-N 0.000 claims 1
- RMGQMRSYLWLCJR-UHFFFAOYSA-N 4-[[[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]amino]methyl]-1,5-dimethyl-2-phenylpyrazol-3-one Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NCC(C1=O)=C(C)N(C)N1C1=CC=CC=C1 RMGQMRSYLWLCJR-UHFFFAOYSA-N 0.000 claims 1
- MCYOHLCVBAFURV-UHFFFAOYSA-N 4-anilino-1-benzyl-n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-2-oxopyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C(N(CC=1C=CC=CC=1)C=C1)=O)=C1NC1=CC=CC=C1 MCYOHLCVBAFURV-UHFFFAOYSA-N 0.000 claims 1
- WEEMSRUOVNMUPV-UHFFFAOYSA-N 4-anilino-n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-2-oxo-1-phenylpyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C(N(C=1C=CC=CC=1)C=C1)=O)=C1NC1=CC=CC=C1 WEEMSRUOVNMUPV-UHFFFAOYSA-N 0.000 claims 1
- RYQBKVFFHMNFTM-UHFFFAOYSA-N 5-(aminomethyl)-n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(CN)N(C)N1C1=CC=CC=C1 RYQBKVFFHMNFTM-UHFFFAOYSA-N 0.000 claims 1
- FWXODUHNWANOFN-UHFFFAOYSA-N 5-[[ethyl(methyl)amino]methyl]-n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound CN1C(CN(C)CC)=C(C(=O)NC=2C=C(F)C(OC=3C4=CC=C(OC)C=C4N=CC=3)=CC=2)C(=O)N1C1=CC=CC=C1 FWXODUHNWANOFN-UHFFFAOYSA-N 0.000 claims 1
- SEJFSSIRSRIMHC-UHFFFAOYSA-N 5-benzyl-n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-2-oxo-1-phenylpyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C(N(C=1C=CC=CC=1)C=1)=O)=CC=1CC1=CC=CC=C1 SEJFSSIRSRIMHC-UHFFFAOYSA-N 0.000 claims 1
- GGEHWHTYDAHDRG-UHFFFAOYSA-N 5-bromo-n-[2-chloro-4-(6,7-dimethoxyquinolin-4-yl)oxyphenyl]-2-oxo-1-phenylpyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1Cl)=CC=C1NC(=O)C(C1=O)=CC(Br)=CN1C1=CC=CC=C1 GGEHWHTYDAHDRG-UHFFFAOYSA-N 0.000 claims 1
- XHAJFXSLJHVISJ-UHFFFAOYSA-N 5-bromo-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-1-(3-methylphenyl)-2-oxopyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC(Br)=CN1C1=CC=CC(C)=C1 XHAJFXSLJHVISJ-UHFFFAOYSA-N 0.000 claims 1
- FGMKYZHFCFZOFF-UHFFFAOYSA-N 6-(diethylaminomethyl)-n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-3-oxo-2-phenylpyridazine-4-carboxamide Chemical compound N1=C(CN(CC)CC)C=C(C(=O)NC=2C=C(F)C(OC=3C4=CC(OC)=C(OC)C=C4N=CC=3)=CC=2)C(=O)N1C1=CC=CC=C1 FGMKYZHFCFZOFF-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- MLDQJTXFUGDVEO-UHFFFAOYSA-N BAY-43-9006 Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 MLDQJTXFUGDVEO-UHFFFAOYSA-N 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 1
- AZIBPFHNLVDQOV-DKXQDJALSA-N CCCN1C(C)=C(C(=O)N[C@@H]2CC[C@@H](CC2)OC=2C3=CC=C(OC)C=C3N=CC=2)C(=O)N1C1=CC=CC=C1 Chemical compound CCCN1C(C)=C(C(=O)N[C@@H]2CC[C@@H](CC2)OC=2C3=CC=C(OC)C=C3N=CC=2)C(=O)N1C1=CC=CC=C1 AZIBPFHNLVDQOV-DKXQDJALSA-N 0.000 claims 1
- AZIBPFHNLVDQOV-AFARHQOCSA-N CCCN1C(C)=C(C(=O)N[C@@H]2CC[C@H](CC2)OC=2C3=CC=C(OC)C=C3N=CC=2)C(=O)N1C1=CC=CC=C1 Chemical compound CCCN1C(C)=C(C(=O)N[C@@H]2CC[C@H](CC2)OC=2C3=CC=C(OC)C=C3N=CC=2)C(=O)N1C1=CC=CC=C1 AZIBPFHNLVDQOV-AFARHQOCSA-N 0.000 claims 1
- KZEVZMPRNWJITB-UHFFFAOYSA-N COC1=CC2=NC=CC(=C2C=C1)OC3=C(C=C(C=C3)C4=C(C(=O)N(N=C4)C5=CC=CC=C5)C(=O)N)F Chemical compound COC1=CC2=NC=CC(=C2C=C1)OC3=C(C=C(C=C3)C4=C(C(=O)N(N=C4)C5=CC=CC=C5)C(=O)N)F KZEVZMPRNWJITB-UHFFFAOYSA-N 0.000 claims 1
- ONJQMAAALBEIGV-UHFFFAOYSA-N COC1=CC2=NC=CC(=C2C=C1)OC3=CN=C(C=C3)N4C=C(C(=O)N4C5=CC=CC=C5)C(=O)N Chemical compound COC1=CC2=NC=CC(=C2C=C1)OC3=CN=C(C=C3)N4C=C(C(=O)N4C5=CC=CC=C5)C(=O)N ONJQMAAALBEIGV-UHFFFAOYSA-N 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 201000010915 Glioblastoma multiforme Diseases 0.000 claims 1
- UQRCJCNVNUFYDX-UHFFFAOYSA-N Golvatinib Chemical compound C1CN(C)CCN1C1CCN(C(=O)NC=2N=CC=C(OC=3C=C(F)C(NC(=O)C4(CC4)C(=O)NC=4C=CC(F)=CC=4)=CC=3)C=2)CC1 UQRCJCNVNUFYDX-UHFFFAOYSA-N 0.000 claims 1
- 239000002147 L01XE04 - Sunitinib Substances 0.000 claims 1
- 239000005511 L01XE05 - Sorafenib Substances 0.000 claims 1
- 239000002176 L01XE26 - Cabozantinib Substances 0.000 claims 1
- UCEQXRCJXIVODC-PMACEKPBSA-N LSM-1131 Chemical compound C1CCC2=CC=CC3=C2N1C=C3[C@@H]1C(=O)NC(=O)[C@H]1C1=CNC2=CC=CC=C12 UCEQXRCJXIVODC-PMACEKPBSA-N 0.000 claims 1
- LQXMERNISNQUEX-AFARHQOCSA-N N([C@H]1CC[C@@H](CC1)OC=1C2=CC=C(C=C2N=CC=1)OC)C(=O)C(C1=O)=C(C)N(CC(C)(C)O)N1C1=CC=CC=C1 Chemical compound N([C@H]1CC[C@@H](CC1)OC=1C2=CC=C(C=C2N=CC=1)OC)C(=O)C(C1=O)=C(C)N(CC(C)(C)O)N1C1=CC=CC=C1 LQXMERNISNQUEX-AFARHQOCSA-N 0.000 claims 1
- XWQFRGPCPMQYEV-UHFFFAOYSA-N N-[3-fluoro-4-(7-hydroxyquinolin-4-yl)oxyphenyl]-1-(2-hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound CC(O)(C)CN1C(C)=C(C(=O)NC=2C=C(F)C(OC=3C4=CC=C(O)C=C4N=CC=3)=CC=2)C(=O)N1C1=CC=CC=C1 XWQFRGPCPMQYEV-UHFFFAOYSA-N 0.000 claims 1
- UYMSIPINLJNNOU-UHFFFAOYSA-N N-[3-fluoro-4-[(7-methoxy-4-quinolinyl)oxy]phenyl]-1-(2-hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenyl-4-pyrazolecarboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(CC(C)(C)O)N1C1=CC=CC=C1 UYMSIPINLJNNOU-UHFFFAOYSA-N 0.000 claims 1
- VNBRGSXVFBYQNN-UHFFFAOYSA-N N-[4-[(2-amino-3-chloro-4-pyridinyl)oxy]-3-fluorophenyl]-4-ethoxy-1-(4-fluorophenyl)-2-oxo-3-pyridinecarboxamide Chemical compound O=C1C(C(=O)NC=2C=C(F)C(OC=3C(=C(N)N=CC=3)Cl)=CC=2)=C(OCC)C=CN1C1=CC=C(F)C=C1 VNBRGSXVFBYQNN-UHFFFAOYSA-N 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- CXQHYVUVSFXTMY-UHFFFAOYSA-N N1'-[3-fluoro-4-[[6-methoxy-7-[3-(4-morpholinyl)propoxy]-4-quinolinyl]oxy]phenyl]-N1-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide Chemical compound C1=CN=C2C=C(OCCCN3CCOCC3)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NC(=O)C1(C(=O)NC=2C=CC(F)=CC=2)CC1 CXQHYVUVSFXTMY-UHFFFAOYSA-N 0.000 claims 1
- 208000006265 Renal cell carcinoma Diseases 0.000 claims 1
- 125000004946 alkenylalkyl group Chemical group 0.000 claims 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 1
- 229960003005 axitinib Drugs 0.000 claims 1
- RITAVMQDGBJQJZ-FMIVXFBMSA-N axitinib Chemical compound CNC(=O)C1=CC=CC=C1SC1=CC=C(C(\C=C\C=2N=CC=CC=2)=NN2)C2=C1 RITAVMQDGBJQJZ-FMIVXFBMSA-N 0.000 claims 1
- 125000005335 azido alkyl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 229960000397 bevacizumab Drugs 0.000 claims 1
- HFCFMRYTXDINDK-WNQIDUERSA-N cabozantinib malate Chemical compound OC(=O)[C@@H](O)CC(O)=O.C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1)=CC=C1NC(=O)C1(C(=O)NC=2C=CC(F)=CC=2)CC1 HFCFMRYTXDINDK-WNQIDUERSA-N 0.000 claims 1
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 229960002412 cediranib Drugs 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 229940125782 compound 2 Drugs 0.000 claims 1
- 229940126214 compound 3 Drugs 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 229950007540 glesatinib Drugs 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000001145 hydrido group Chemical group *[H] 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- UMWXVGCBUMYAFH-UHFFFAOYSA-N n-[2-chloro-4-(6,7-dimethoxyquinolin-4-yl)oxyphenyl]-1,5-dimethyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1Cl)=CC=C1NC(=O)C(C1=O)=C(C)N(C)N1C1=CC=CC=C1 UMWXVGCBUMYAFH-UHFFFAOYSA-N 0.000 claims 1
- QTSXUAWJQYJGBT-UHFFFAOYSA-N n-[2-chloro-4-(6,7-dimethoxyquinolin-4-yl)oxyphenyl]-6-methyl-3-oxo-2-phenylpyridazine-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=C1Cl)=CC=C1NC(=O)C(C1=O)=CC(C)=NN1C1=CC=CC=C1 QTSXUAWJQYJGBT-UHFFFAOYSA-N 0.000 claims 1
- HNGRVFLMDJYCQR-UHFFFAOYSA-N n-[3-fluoro-4-(1h-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]-1-(2-hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound CC(O)(C)CN1C(C)=C(C(=O)NC=2C=C(F)C(OC=3C=4C=CNC=4N=CC=3)=CC=2)C(=O)N1C1=CC=CC=C1 HNGRVFLMDJYCQR-UHFFFAOYSA-N 0.000 claims 1
- BIPCVEKMUOMGHB-SFHVURJKSA-N n-[3-fluoro-4-(6-methoxyquinolin-4-yl)oxyphenyl]-1-[(2s)-2-hydroxypropyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C12=CC(OC)=CC=C2N=CC=C1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(C[C@H](C)O)N1C1=CC=CC=C1 BIPCVEKMUOMGHB-SFHVURJKSA-N 0.000 claims 1
- ZXDCZKKTUPQTEM-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1,2-dimethyl-3-oxo-5-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C(N(C)N1C)=O)=C1C1=CC=CC=C1 ZXDCZKKTUPQTEM-UHFFFAOYSA-N 0.000 claims 1
- MINABFBKQMEGEQ-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1,5-dimethyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(C)N1C1=CC=CC=C1 MINABFBKQMEGEQ-UHFFFAOYSA-N 0.000 claims 1
- UKIOLJVLQRIDFS-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-(2-hydroxy-2-methylbutyl)-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound CCC(C)(O)CN1C(C)=C(C(=O)NC=2C=C(F)C(OC=3C4=CC=C(OC)C=C4N=CC=3)=CC=2)C(=O)N1C1=CC=CC=C1 UKIOLJVLQRIDFS-UHFFFAOYSA-N 0.000 claims 1
- YMFWEIKNDBLHIR-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-(2-hydroxy-3-methylbutyl)-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(CC(O)C(C)C)N1C1=CC=CC=C1 YMFWEIKNDBLHIR-UHFFFAOYSA-N 0.000 claims 1
- IJPGNMKSMUVFIK-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-(2-hydroxy-3-morpholin-4-ylpropyl)-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C(N1C=2C=CC=CC=2)=O)=C(C)N1CC(O)CN1CCOCC1 IJPGNMKSMUVFIK-UHFFFAOYSA-N 0.000 claims 1
- VCMSULGORSGFSP-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-(2-hydroxyethyl)-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(CCO)N1C1=CC=CC=C1 VCMSULGORSGFSP-UHFFFAOYSA-N 0.000 claims 1
- OHLUERTUZNIQEE-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-(2-hydroxypropyl)-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(CC(C)O)N1C1=CC=CC=C1 OHLUERTUZNIQEE-UHFFFAOYSA-N 0.000 claims 1
- JGIANKPNCUQJIC-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-(2-methoxyethyl)-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound COCCN1C(C)=C(C(=O)NC=2C=C(F)C(OC=3C4=CC=C(OC)C=C4N=CC=3)=CC=2)C(=O)N1C1=CC=CC=C1 JGIANKPNCUQJIC-UHFFFAOYSA-N 0.000 claims 1
- ZGJSJVTYUHGLAA-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-(4-fluorophenyl)-2,3-dimethyl-5-oxopyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(C)N1C1=CC=C(F)C=C1 ZGJSJVTYUHGLAA-UHFFFAOYSA-N 0.000 claims 1
- GGYBIRJRKABRRC-QGZVFWFLSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-(4-fluorophenyl)-2-[(2r)-2-hydroxypropyl]-3-methyl-5-oxopyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(C[C@@H](C)O)N1C1=CC=C(F)C=C1 GGYBIRJRKABRRC-QGZVFWFLSA-N 0.000 claims 1
- YMFWEIKNDBLHIR-MHZLTWQESA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-[(2r)-2-hydroxy-3-methylbutyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(C[C@H](O)C(C)C)N1C1=CC=CC=C1 YMFWEIKNDBLHIR-MHZLTWQESA-N 0.000 claims 1
- GYCPBMYHPVDKFK-JOCHJYFZSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-[(2r)-2-hydroxybutyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound CC[C@@H](O)CN1C(C)=C(C(=O)NC=2C=C(F)C(OC=3C4=CC=C(OC)C=C4N=CC=3)=CC=2)C(=O)N1C1=CC=CC=C1 GYCPBMYHPVDKFK-JOCHJYFZSA-N 0.000 claims 1
- QPOOABIQRIACQT-GOSISDBHSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-[(2r)-2-hydroxypropyl]-2-methyl-3-oxo-5-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C(N(C)N1C[C@@H](C)O)=O)=C1C1=CC=CC=C1 QPOOABIQRIACQT-GOSISDBHSA-N 0.000 claims 1
- OHLUERTUZNIQEE-GOSISDBHSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-[(2r)-2-hydroxypropyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(C[C@@H](C)O)N1C1=CC=CC=C1 OHLUERTUZNIQEE-GOSISDBHSA-N 0.000 claims 1
- GTUZGJWSECDOOP-UYAOXDASSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-[(2r,3r)-3-hydroxybutan-2-yl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N([C@H](C)[C@@H](C)O)N1C1=CC=CC=C1 GTUZGJWSECDOOP-UYAOXDASSA-N 0.000 claims 1
- ZSCKVSNJUQIJRK-SFHVURJKSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-[(2s)-2-fluoropropyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(C[C@H](C)F)N1C1=CC=CC=C1 ZSCKVSNJUQIJRK-SFHVURJKSA-N 0.000 claims 1
- YMFWEIKNDBLHIR-HHHXNRCGSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-[(2s)-2-hydroxy-3-methylbutyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(C[C@@H](O)C(C)C)N1C1=CC=CC=C1 YMFWEIKNDBLHIR-HHHXNRCGSA-N 0.000 claims 1
- GYCPBMYHPVDKFK-QFIPXVFZSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-[(2s)-2-hydroxybutyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound CC[C@H](O)CN1C(C)=C(C(=O)NC=2C=C(F)C(OC=3C4=CC=C(OC)C=C4N=CC=3)=CC=2)C(=O)N1C1=CC=CC=C1 GYCPBMYHPVDKFK-QFIPXVFZSA-N 0.000 claims 1
- PTDDHBPPQNYQQA-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-[2-hydroxy-3-(methylamino)propyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound CNCC(O)CN1C(C)=C(C(=O)NC=2C=C(F)C(OC=3C4=CC=C(OC)C=C4N=CC=3)=CC=2)C(=O)N1C1=CC=CC=C1 PTDDHBPPQNYQQA-UHFFFAOYSA-N 0.000 claims 1
- VQYLPAYBNMFHIP-NRFANRHFSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-methyl-3-oxo-2-[(1s)-1-phenylethyl]-5-pyridin-4-ylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C(N([C@@H](C)C=1C=CC=CC=1)N1C)=O)=C1C1=CC=NC=C1 VQYLPAYBNMFHIP-NRFANRHFSA-N 0.000 claims 1
- YRCSFWQLJFRPEI-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-methyl-3-oxo-2-phenyl-5-(pyrrolidin-1-ylmethyl)pyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C(N(C=1C=CC=CC=1)N1C)=O)=C1CN1CCCC1 YRCSFWQLJFRPEI-UHFFFAOYSA-N 0.000 claims 1
- JGNJPNUXMMZIHN-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-methyl-3-oxo-2-phenyl-5-pyrazin-2-ylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C(N(C=1C=CC=CC=1)N1C)=O)=C1C1=CN=CC=N1 JGNJPNUXMMZIHN-UHFFFAOYSA-N 0.000 claims 1
- JGLMIFHYFCEGCU-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-methyl-3-oxo-2-phenyl-5-pyridin-2-ylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C(N(C=1C=CC=CC=1)N1C)=O)=C1C1=CC=CC=N1 JGLMIFHYFCEGCU-UHFFFAOYSA-N 0.000 claims 1
- MGTZNLRHGWNOTR-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-methyl-3-oxo-2-phenyl-5-pyridin-4-ylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C(N(C=1C=CC=CC=1)N1C)=O)=C1C1=CC=NC=C1 MGTZNLRHGWNOTR-UHFFFAOYSA-N 0.000 claims 1
- ZEHGCUVZJRBDQM-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-methyl-5-(2-methyl-1,3-thiazol-4-yl)-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C(N(C=1C=CC=CC=1)N1C)=O)=C1C1=CSC(C)=N1 ZEHGCUVZJRBDQM-UHFFFAOYSA-N 0.000 claims 1
- PMKVHCSAPYJDMR-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-methyl-5-(5-methyl-1,2-oxazol-3-yl)-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C(N(C=1C=CC=CC=1)N1C)=O)=C1C=1C=C(C)ON=1 PMKVHCSAPYJDMR-UHFFFAOYSA-N 0.000 claims 1
- LDRHWDNTNFXKEE-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-1-methyl-5-(oxan-4-yl)-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C(N(C=1C=CC=CC=1)N1C)=O)=C1C1CCOCC1 LDRHWDNTNFXKEE-UHFFFAOYSA-N 0.000 claims 1
- PQEMVZSWNHFWMZ-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-3-methyl-5-oxo-1-phenyl-2-(2-pyrrolidin-1-ylethyl)pyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C(N1C=2C=CC=CC=2)=O)=C(C)N1CCN1CCCC1 PQEMVZSWNHFWMZ-UHFFFAOYSA-N 0.000 claims 1
- QQANYCOFSUVVIT-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-3-methyl-5-oxo-1-phenyl-2-propylpyrazole-4-carboxamide Chemical compound CCCN1C(C)=C(C(=O)NC=2C=C(F)C(OC=3C4=CC=C(OC)C=C4N=CC=3)=CC=2)C(=O)N1C1=CC=CC=C1 QQANYCOFSUVVIT-UHFFFAOYSA-N 0.000 claims 1
- NVPAHLWVYDAHJO-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-3-oxo-2-phenylpyridazine-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC=NN1C1=CC=CC=C1 NVPAHLWVYDAHJO-UHFFFAOYSA-N 0.000 claims 1
- KLRVDEZKNVCVEM-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-4-(2-methoxyethylamino)-2-oxo-1-phenylpyridine-3-carboxamide Chemical compound O=C1C(C(=O)NC=2C=C(F)C(OC=3C4=CC=C(OC)C=C4N=CC=3)=CC=2)=C(NCCOC)C=CN1C1=CC=CC=C1 KLRVDEZKNVCVEM-UHFFFAOYSA-N 0.000 claims 1
- KQVYGGAQCPUYTL-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-5-methyl-1-(1,3-oxazolidin-5-ylmethyl)-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C(N1C=2C=CC=CC=2)=O)=C(C)N1CC1CNCO1 KQVYGGAQCPUYTL-UHFFFAOYSA-N 0.000 claims 1
- ZOQOSBOUUBEFAD-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-5-methyl-1-(3-methyl-2-oxobutyl)-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(CC(=O)C(C)C)N1C1=CC=CC=C1 ZOQOSBOUUBEFAD-UHFFFAOYSA-N 0.000 claims 1
- DUXQIGFYYKLFIE-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-5-methyl-1-[(3-methyl-2-oxo-1,3-oxazolidin-5-yl)methyl]-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C(N1C=2C=CC=CC=2)=O)=C(C)N1CC1CN(C)C(=O)O1 DUXQIGFYYKLFIE-UHFFFAOYSA-N 0.000 claims 1
- KJKMLGDIPXBBOS-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-5-methyl-3-oxo-1-(2-oxobutyl)-2-phenylpyrazole-4-carboxamide Chemical compound CCC(=O)CN1C(C)=C(C(=O)NC=2C=C(F)C(OC=3C4=CC=C(OC)C=C4N=CC=3)=CC=2)C(=O)N1C1=CC=CC=C1 KJKMLGDIPXBBOS-UHFFFAOYSA-N 0.000 claims 1
- GZMFYPWWSXGVTC-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-5-methyl-3-oxo-1-(2-oxopropyl)-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(CC(C)=O)N1C1=CC=CC=C1 GZMFYPWWSXGVTC-UHFFFAOYSA-N 0.000 claims 1
- WYIOGRCUILYATA-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-5-methyl-3-oxo-1-(oxolan-2-ylmethyl)-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C(N1C=2C=CC=CC=2)=O)=C(C)N1CC1CCCO1 WYIOGRCUILYATA-UHFFFAOYSA-N 0.000 claims 1
- UZSHRNLVCGJSAA-UHFFFAOYSA-N n-[3-fluoro-4-(7-methoxyquinolin-4-yl)oxyphenyl]-6-methyl-3-oxo-2-phenylpyridazine-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC(C)=NN1C1=CC=CC=C1 UZSHRNLVCGJSAA-UHFFFAOYSA-N 0.000 claims 1
- JZOLSIWVEDHXFB-UHFFFAOYSA-N n-[3-fluoro-4-(7h-pyrrolo[2,3-d]pyrimidin-4-yloxy)phenyl]-1-(2-hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound CC(O)(C)CN1C(C)=C(C(=O)NC=2C=C(F)C(OC=3C=4C=CNC=4N=CN=3)=CC=2)C(=O)N1C1=CC=CC=C1 JZOLSIWVEDHXFB-UHFFFAOYSA-N 0.000 claims 1
- BPVPERPKKHJHNY-UHFFFAOYSA-N n-[3-fluoro-4-[(7-methoxyquinolin-4-yl)amino]phenyl]-1-(2-hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1NC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(CC(C)(C)O)N1C1=CC=CC=C1 BPVPERPKKHJHNY-UHFFFAOYSA-N 0.000 claims 1
- KTHBTMQUMOBCSP-UHFFFAOYSA-N n-[3-fluoro-4-[2-(3-methyl-1,2,4-oxadiazol-5-yl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-(2-hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound CC1=NOC(C=2SC3=C(OC=4C(=CC(NC(=O)C=5C(N(C=6C=CC=CC=6)N(CC(C)(C)O)C=5C)=O)=CC=4)F)C=CN=C3C=2)=N1 KTHBTMQUMOBCSP-UHFFFAOYSA-N 0.000 claims 1
- UENKHXBWOAXYLM-UHFFFAOYSA-N n-[3-fluoro-4-[2-(3-methylimidazol-4-yl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-(2-hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound O=C1N(C=2C=CC=CC=2)N(CC(C)(C)O)C(C)=C1C(=O)NC(C=C1F)=CC=C1OC(C=1S2)=CC=NC=1C=C2C1=CN=CN1C UENKHXBWOAXYLM-UHFFFAOYSA-N 0.000 claims 1
- FPFUZEPSNTYFGN-GOSISDBHSA-N n-[3-fluoro-4-[2-(3-methylimidazol-4-yl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-[(2r)-2-hydroxypropyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound O=C1N(C=2C=CC=CC=2)N(C[C@H](O)C)C(C)=C1C(=O)NC(C=C1F)=CC=C1OC(C=1S2)=CC=NC=1C=C2C1=CN=CN1C FPFUZEPSNTYFGN-GOSISDBHSA-N 0.000 claims 1
- FHECOQJNQDTJEQ-UHFFFAOYSA-N n-[3-fluoro-4-[2-(4-methylpiperazine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxyphenyl]-1-(2-hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C1CN(C)CCN1C(=O)C1=CC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC=CC=5)N(CC(C)(C)O)C=4C)=O)=CC=3)F)=C2S1 FHECOQJNQDTJEQ-UHFFFAOYSA-N 0.000 claims 1
- JKWZQYHWZKVBQQ-UHFFFAOYSA-N n-[3-fluoro-4-[2-(pyrrolidine-1-carbonylamino)pyridin-4-yl]oxyphenyl]-1,5-dimethyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound O=C1N(C=2C=CC=CC=2)N(C)C(C)=C1C(=O)NC(C=C1F)=CC=C1OC(C=1)=CC=NC=1NC(=O)N1CCCC1 JKWZQYHWZKVBQQ-UHFFFAOYSA-N 0.000 claims 1
- KXSARLBLNVFWIU-UHFFFAOYSA-N n-[3-fluoro-4-[2-(pyrrolidine-1-carbonylamino)pyridin-4-yl]oxyphenyl]-1-(2-hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound O=C1N(C=2C=CC=CC=2)N(CC(C)(C)O)C(C)=C1C(=O)NC(C=C1F)=CC=C1OC(C=1)=CC=NC=1NC(=O)N1CCCC1 KXSARLBLNVFWIU-UHFFFAOYSA-N 0.000 claims 1
- UVOHFDHMAHMCPV-UHFFFAOYSA-N n-[3-fluoro-4-[2-(pyrrolidine-1-carbonylamino)pyridin-4-yl]oxyphenyl]-3-methyl-5-oxo-1-phenyl-2-propylpyrazole-4-carboxamide Chemical compound O=C1N(C=2C=CC=CC=2)N(CCC)C(C)=C1C(=O)NC(C=C1F)=CC=C1OC(C=1)=CC=NC=1NC(=O)N1CCCC1 UVOHFDHMAHMCPV-UHFFFAOYSA-N 0.000 claims 1
- CLNGMKGWQLPUPG-UHFFFAOYSA-N n-[3-fluoro-4-[2-(pyrrolidine-1-carbonylamino)pyridin-4-yl]oxyphenyl]-3-oxo-2-phenylpyridazine-4-carboxamide Chemical compound C=1C=C(OC=2C=C(NC(=O)N3CCCC3)N=CC=2)C(F)=CC=1NC(=O)C(C1=O)=CC=NN1C1=CC=CC=C1 CLNGMKGWQLPUPG-UHFFFAOYSA-N 0.000 claims 1
- MIHCWLIBCJAHNQ-UHFFFAOYSA-N n-[3-fluoro-4-[6-(pyrrolidine-1-carbonylamino)pyrimidin-4-yl]oxyphenyl]-1-(2-hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound O=C1N(C=2C=CC=CC=2)N(CC(C)(C)O)C(C)=C1C(=O)NC(C=C1F)=CC=C1OC(N=CN=1)=CC=1NC(=O)N1CCCC1 MIHCWLIBCJAHNQ-UHFFFAOYSA-N 0.000 claims 1
- KPELLIUDYWGXRD-UHFFFAOYSA-N n-[3-fluoro-4-[6-(pyrrolidine-1-carbonylamino)pyrimidin-4-yl]oxyphenyl]-3-methyl-5-oxo-1-phenyl-2-propylpyrazole-4-carboxamide Chemical compound O=C1N(C=2C=CC=CC=2)N(CCC)C(C)=C1C(=O)NC(C=C1F)=CC=C1OC(N=CN=1)=CC=1NC(=O)N1CCCC1 KPELLIUDYWGXRD-UHFFFAOYSA-N 0.000 claims 1
- UNPIVOKFBCHYCD-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-1,2-dimethyl-3-oxo-5-phenylpyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C(N(C)N1C)=O)=C1C1=CC=CC=C1 UNPIVOKFBCHYCD-UHFFFAOYSA-N 0.000 claims 1
- WQBDJRYMGUATFA-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-1,5-dimethyl-2-(4-methylphenyl)-3-oxopyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(C)N1C1=CC=C(C)C=C1 WQBDJRYMGUATFA-UHFFFAOYSA-N 0.000 claims 1
- NAKMEZJNUJCUEH-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-1-(2-hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(CC(C)(C)O)N1C1=CC=CC=C1 NAKMEZJNUJCUEH-UHFFFAOYSA-N 0.000 claims 1
- DJGDSWWUWDWPSL-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-1-(4-fluorophenyl)-2,3-dimethyl-5-oxopyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(C)N1C1=CC=C(F)C=C1 DJGDSWWUWDWPSL-UHFFFAOYSA-N 0.000 claims 1
- VNJQWCBSSDYYRS-GOSISDBHSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-1-[(2r)-2-hydroxypropyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(C[C@@H](C)O)N1C1=CC=CC=C1 VNJQWCBSSDYYRS-GOSISDBHSA-N 0.000 claims 1
- QOIIHDGSHWSVIC-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-1-methyl-3-oxo-2-phenyl-5-pyridin-4-ylpyrazole-4-carboxamide Chemical group C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C(N(C=1C=CC=CC=1)N1C)=O)=C1C1=CC=NC=C1 QOIIHDGSHWSVIC-UHFFFAOYSA-N 0.000 claims 1
- JDPDBPPUGDILQQ-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-2-oxo-1,5-diphenylpyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC(C=2C=CC=CC=2)=CN1C1=CC=CC=C1 JDPDBPPUGDILQQ-UHFFFAOYSA-N 0.000 claims 1
- MUTNFXVIYFRXNC-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-2-oxo-1-phenyl-5-(1h-pyrazol-4-yl)pyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC(C2=CNN=C2)=CN1C1=CC=CC=C1 MUTNFXVIYFRXNC-UHFFFAOYSA-N 0.000 claims 1
- KNPGGOCAKBFOPN-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-5-(1-methylpyrazol-4-yl)-2-oxo-1-phenylpyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=CC(C2=CN(C)N=C2)=CN1C1=CC=CC=C1 KNPGGOCAKBFOPN-UHFFFAOYSA-N 0.000 claims 1
- FPJDJIFCTZAITG-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-5-[(dimethylamino)methyl]-1-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(CN(C)C)N(C)N1C1=CC=CC=C1 FPJDJIFCTZAITG-UHFFFAOYSA-N 0.000 claims 1
- DFTHAFRGPKNQPB-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-5-[(dimethylamino)methyl]-2-oxo-3-phenyl-1,3-diazinane-1-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)N(C1=O)CC(CN(C)C)CN1C1=CC=CC=C1 DFTHAFRGPKNQPB-UHFFFAOYSA-N 0.000 claims 1
- PTYAHNMUDNBBGM-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-5-[[ethyl(methyl)amino]methyl]-1-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound CN1C(CN(C)CC)=C(C(=O)NC=2C=C(F)C(OC=3C4=CC(OC)=C(OC)C=C4N=CC=3)=CC=2)C(=O)N1C1=CC=CC=C1 PTYAHNMUDNBBGM-UHFFFAOYSA-N 0.000 claims 1
- LBNUJYYTRRKYID-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-5-methyl-1-(2-methylprop-2-enyl)-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(CC(C)=C)N1C1=CC=CC=C1 LBNUJYYTRRKYID-UHFFFAOYSA-N 0.000 claims 1
- TUOUDQPJUIAYBY-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-5-methyl-3-oxo-1-(2-oxopropyl)-2-phenylpyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(CC(C)=O)N1C1=CC=CC=C1 TUOUDQPJUIAYBY-UHFFFAOYSA-N 0.000 claims 1
- GZAGUSLONPQDBT-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-5-methyl-3-oxo-2-phenyl-1h-pyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)NN1C1=CC=CC=C1 GZAGUSLONPQDBT-UHFFFAOYSA-N 0.000 claims 1
- GKYSYTSYXWQUQM-RUZDIDTESA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-6-[[(3r)-3-(dimethylamino)pyrrolidin-1-yl]methyl]-3-oxo-2-phenylpyridazine-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1NC(=O)C(C(N(C=1C=CC=CC=1)N=1)=O)=CC=1CN1CC[C@@H](N(C)C)C1 GKYSYTSYXWQUQM-RUZDIDTESA-N 0.000 claims 1
- MVCODGCQFJXMTG-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-n,1,5-trimethyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C(=C1)F)=CC=C1N(C)C(=O)C(C1=O)=C(C)N(C)N1C1=CC=CC=C1 MVCODGCQFJXMTG-UHFFFAOYSA-N 0.000 claims 1
- VBFKCCNMXFXRBF-CQSZACIVSA-N n-[4-(6-aminopyrimidin-4-yl)oxy-3-fluorophenyl]-1-[(2r)-2-hydroxypropyl]-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound O=C1N(C=2C=CC=CC=2)N(C[C@H](O)C)C(C)=C1C(=O)NC(C=C1F)=CC=C1OC1=CC(N)=NC=N1 VBFKCCNMXFXRBF-CQSZACIVSA-N 0.000 claims 1
- DPDFZTKJHYCDSX-UHFFFAOYSA-N n-[4-(6-ethyl-7-methoxyquinolin-4-yl)oxy-3-fluorophenyl]-1,5-dimethyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C1=CN=C2C=C(OC)C(CC)=CC2=C1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(C)N1C1=CC=CC=C1 DPDFZTKJHYCDSX-UHFFFAOYSA-N 0.000 claims 1
- CIQCAEOYTAZOFC-UHFFFAOYSA-N n-[4-[2-(azetidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-3-fluorophenyl]-1-(2-hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound O=C1N(C=2C=CC=CC=2)N(CC(C)(C)O)C(C)=C1C(=O)NC(C=C1F)=CC=C1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC1 CIQCAEOYTAZOFC-UHFFFAOYSA-N 0.000 claims 1
- MSIVJSNJVSVGCG-UHFFFAOYSA-N n-[4-[2-(azetidine-1-carbonyl)thieno[3,2-b]pyridin-7-yl]oxy-3-fluorophenyl]-3-methyl-5-oxo-1-phenyl-2-propylpyrazole-4-carboxamide Chemical compound O=C1N(C=2C=CC=CC=2)N(CCC)C(C)=C1C(=O)NC(C=C1F)=CC=C1OC(C=1S2)=CC=NC=1C=C2C(=O)N1CCC1 MSIVJSNJVSVGCG-UHFFFAOYSA-N 0.000 claims 1
- FPTHWHHGUONGJR-UHFFFAOYSA-N n-[4-[2-[3-(dimethylamino)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridin-7-yl]oxy-3-fluorophenyl]-1-(2-hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C1C(N(C)C)CCN1C(=O)C1=CC2=NC=CC(OC=3C(=CC(NC(=O)C=4C(N(C=5C=CC=CC=5)N(CC(C)(C)O)C=4C)=O)=CC=3)F)=C2S1 FPTHWHHGUONGJR-UHFFFAOYSA-N 0.000 claims 1
- VAPLAAHRJUSDQJ-UHFFFAOYSA-N n-[4-[4-[(1,5-dimethyl-3-oxo-2-phenylpyrazole-4-carbonyl)amino]-2-fluorophenoxy]pyridin-2-yl]morpholine-4-carboxamide Chemical compound O=C1N(C=2C=CC=CC=2)N(C)C(C)=C1C(=O)NC(C=C1F)=CC=C1OC(C=1)=CC=NC=1NC(=O)N1CCOCC1 VAPLAAHRJUSDQJ-UHFFFAOYSA-N 0.000 claims 1
- OTVVVPAVJMOGCU-UHFFFAOYSA-N n-[4-[4-[(1,5-dimethyl-3-oxo-2-phenylpyrazole-4-carbonyl)amino]-2-fluorophenoxy]pyridin-2-yl]piperidine-1-carboxamide Chemical compound O=C1N(C=2C=CC=CC=2)N(C)C(C)=C1C(=O)NC(C=C1F)=CC=C1OC(C=1)=CC=NC=1NC(=O)N1CCCCC1 OTVVVPAVJMOGCU-UHFFFAOYSA-N 0.000 claims 1
- UVBUNGUGIALSIJ-HSZRJFAPSA-N n-[4-[6-[[(3r)-3-(dimethylamino)pyrrolidine-1-carbonyl]amino]pyrimidin-4-yl]oxy-3-fluorophenyl]-3-methyl-5-oxo-1-phenyl-2-propylpyrazole-4-carboxamide Chemical compound O=C1N(C=2C=CC=CC=2)N(CCC)C(C)=C1C(=O)NC(C=C1F)=CC=C1OC(N=CN=1)=CC=1NC(=O)N1CC[C@@H](N(C)C)C1 UVBUNGUGIALSIJ-HSZRJFAPSA-N 0.000 claims 1
- BGUNZRILROPVEM-UHFFFAOYSA-N n-[4-[hydroxy-(7-methoxyquinolin-4-yl)methyl]phenyl]-3-methyl-5-oxo-1-phenyl-2-propylpyrazole-4-carboxamide Chemical compound CCCN1C(C)=C(C(=O)NC=2C=CC(=CC=2)C(O)C=2C3=CC=C(OC)C=C3N=CC=2)C(=O)N1C1=CC=CC=C1 BGUNZRILROPVEM-UHFFFAOYSA-N 0.000 claims 1
- DZPJELBGNNEVCC-UHFFFAOYSA-N n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-1,5-dimethyl-2-(4-methylphenyl)-3-oxopyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(C)N(C)N1C1=CC=C(C)C=C1 DZPJELBGNNEVCC-UHFFFAOYSA-N 0.000 claims 1
- WOXHVVUMSWSAPY-UHFFFAOYSA-N n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-1-(2-hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(C)N(CC(C)(C)O)N1C1=CC=CC=C1 WOXHVVUMSWSAPY-UHFFFAOYSA-N 0.000 claims 1
- DQULTZGTZLATBW-UHFFFAOYSA-N n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-1-(4-fluorophenyl)-2,3-dimethyl-5-oxopyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(C)N(C)N1C1=CC=C(F)C=C1 DQULTZGTZLATBW-UHFFFAOYSA-N 0.000 claims 1
- KGUYNHFFDBOFLD-UHFFFAOYSA-N n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-1-methyl-3-oxo-2-phenyl-5-pyrazin-2-ylpyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C(N(C=1C=CC=CC=1)N1C)=O)=C1C1=CN=CC=N1 KGUYNHFFDBOFLD-UHFFFAOYSA-N 0.000 claims 1
- JZUVVTPSJAHDMJ-UHFFFAOYSA-N n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-1-methyl-3-oxo-2-phenyl-5-pyridin-4-ylpyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C(N(C=1C=CC=CC=1)N1C)=O)=C1C1=CC=NC=C1 JZUVVTPSJAHDMJ-UHFFFAOYSA-N 0.000 claims 1
- OSFRXXXXHQZGKZ-UHFFFAOYSA-N n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-1-methyl-5-(2-methyl-1,3-thiazol-4-yl)-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C(N(C=1C=CC=CC=1)N1C)=O)=C1C1=CSC(C)=N1 OSFRXXXXHQZGKZ-UHFFFAOYSA-N 0.000 claims 1
- NGXGOGZBCNTXTJ-UHFFFAOYSA-N n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-1-methyl-5-(5-methyl-1,2-oxazol-3-yl)-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C(N(C=1C=CC=CC=1)N1C)=O)=C1C=1C=C(C)ON=1 NGXGOGZBCNTXTJ-UHFFFAOYSA-N 0.000 claims 1
- HGTRCNFAHXJADA-UHFFFAOYSA-N n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-2-oxo-1-phenyl-5-pyrazin-2-ylpyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=CC(C=2N=CC=NC=2)=CN1C1=CC=CC=C1 HGTRCNFAHXJADA-UHFFFAOYSA-N 0.000 claims 1
- DKVMKJCVCCLKAD-UHFFFAOYSA-N n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-2-oxo-1-phenyl-5-pyridin-3-ylpyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=CC(C=2C=NC=CC=2)=CN1C1=CC=CC=C1 DKVMKJCVCCLKAD-UHFFFAOYSA-N 0.000 claims 1
- WZTFASVDMINVIL-UHFFFAOYSA-N n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-2-oxo-1-phenyl-5-thiophen-2-ylpyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=CC(C=2SC=CC=2)=CN1C1=CC=CC=C1 WZTFASVDMINVIL-UHFFFAOYSA-N 0.000 claims 1
- AIYKRNWHVLHHRQ-UHFFFAOYSA-N n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-3-methyl-5-oxo-1-phenyl-2-prop-2-enylpyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(C)N(CC=C)N1C1=CC=CC=C1 AIYKRNWHVLHHRQ-UHFFFAOYSA-N 0.000 claims 1
- KVPRSEQEHWCFIY-UHFFFAOYSA-N n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-3-methyl-5-oxo-1-phenyl-2-propylpyrazole-4-carboxamide Chemical compound CCCN1C(C)=C(C(=O)NC=2N=CC(OC=3C4=CC(OC)=C(OC)C=C4N=CC=3)=CC=2)C(=O)N1C1=CC=CC=C1 KVPRSEQEHWCFIY-UHFFFAOYSA-N 0.000 claims 1
- FLNBFIBKDFIVSN-UHFFFAOYSA-N n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-4-(2-methoxyethylamino)-2-oxo-1-phenylpyridine-3-carboxamide Chemical compound O=C1C(C(=O)NC=2N=CC(OC=3C4=CC(OC)=C(OC)C=C4N=CC=3)=CC=2)=C(NCCOC)C=CN1C1=CC=CC=C1 FLNBFIBKDFIVSN-UHFFFAOYSA-N 0.000 claims 1
- KKIIRQGJRIUEDS-UHFFFAOYSA-N n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-4-(4-methylpiperazin-1-yl)-2-oxo-1-phenylpyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(N2CCN(C)CC2)C=CN1C1=CC=CC=C1 KKIIRQGJRIUEDS-UHFFFAOYSA-N 0.000 claims 1
- WULRGSKYDLRNLL-UHFFFAOYSA-N n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-4-(dimethylamino)-2-oxo-1-phenylpyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(N(C)C)C=CN1C1=CC=CC=C1 WULRGSKYDLRNLL-UHFFFAOYSA-N 0.000 claims 1
- DSTDNBAORRODRL-UHFFFAOYSA-N n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-4-(methylamino)-2-oxo-1-phenylpyridine-3-carboxamide Chemical compound O=C1C(C(=O)NC=2N=CC(OC=3C4=CC(OC)=C(OC)C=C4N=CC=3)=CC=2)=C(NC)C=CN1C1=CC=CC=C1 DSTDNBAORRODRL-UHFFFAOYSA-N 0.000 claims 1
- QFBIGXSOTHTHGD-UHFFFAOYSA-N n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-4-(oxan-4-ylamino)-2-oxo-1-phenylpyridine-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C(N(C=1C=CC=CC=1)C=C1)=O)=C1NC1CCOCC1 QFBIGXSOTHTHGD-UHFFFAOYSA-N 0.000 claims 1
- RDNKBFQPLVQQDJ-UHFFFAOYSA-N n-[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]-6-methyl-3-oxo-2-phenylpyridazine-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=CC(C)=NN1C1=CC=CC=C1 RDNKBFQPLVQQDJ-UHFFFAOYSA-N 0.000 claims 1
- RQBXZJYRCJXDDL-UHFFFAOYSA-N n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-1,2-dimethyl-3-oxo-5-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C(N(C)N1C)=O)=C1C1=CC=CC=C1 RQBXZJYRCJXDDL-UHFFFAOYSA-N 0.000 claims 1
- JKAJGMJZIYLQBG-UHFFFAOYSA-N n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-1,5-dimethyl-2-(4-methylphenyl)-3-oxopyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(C)N(C)N1C1=CC=C(C)C=C1 JKAJGMJZIYLQBG-UHFFFAOYSA-N 0.000 claims 1
- NJPZYQYDYUEVPF-UHFFFAOYSA-N n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-1,5-dimethyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(C)N(C)N1C1=CC=CC=C1 NJPZYQYDYUEVPF-UHFFFAOYSA-N 0.000 claims 1
- HFVGCWCGBAZRCP-NRFANRHFSA-N n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-1-methyl-3-oxo-2-[(1s)-1-phenylethyl]-5-pyridin-4-ylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C(N([C@@H](C)C=1C=CC=CC=1)N1C)=O)=C1C1=CC=NC=C1 HFVGCWCGBAZRCP-NRFANRHFSA-N 0.000 claims 1
- DMUUMPYJFUHKCR-UHFFFAOYSA-N n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-1-methyl-3-oxo-2-phenyl-5-pyrazin-2-ylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C(N(C=1C=CC=CC=1)N1C)=O)=C1C1=CN=CC=N1 DMUUMPYJFUHKCR-UHFFFAOYSA-N 0.000 claims 1
- QPKFJNSFZBUDOA-UHFFFAOYSA-N n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-1-methyl-3-oxo-2-phenyl-5-pyridin-2-ylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C(N(C=1C=CC=CC=1)N1C)=O)=C1C1=CC=CC=N1 QPKFJNSFZBUDOA-UHFFFAOYSA-N 0.000 claims 1
- HKGJCZLDFIJHIO-UHFFFAOYSA-N n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-1-methyl-3-oxo-2-phenyl-5-pyridin-4-ylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C(N(C=1C=CC=CC=1)N1C)=O)=C1C1=CC=NC=C1 HKGJCZLDFIJHIO-UHFFFAOYSA-N 0.000 claims 1
- ISRQETGPAFAXMC-UHFFFAOYSA-N n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-1-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=CN(C)N1C1=CC=CC=C1 ISRQETGPAFAXMC-UHFFFAOYSA-N 0.000 claims 1
- OSHPEWCCDRPGGK-UHFFFAOYSA-N n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-1-methyl-5-(2-methyl-1,3-thiazol-4-yl)-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C(N(C=1C=CC=CC=1)N1C)=O)=C1C1=CSC(C)=N1 OSHPEWCCDRPGGK-UHFFFAOYSA-N 0.000 claims 1
- QAXSZRIWQDFFMT-UHFFFAOYSA-N n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-1-methyl-5-(oxan-4-yl)-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C(N(C=1C=CC=CC=1)N1C)=O)=C1C1CCOCC1 QAXSZRIWQDFFMT-UHFFFAOYSA-N 0.000 claims 1
- KFDHIQVUEANUNN-UHFFFAOYSA-N n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-2-oxo-1-phenyl-5-pyrazin-2-ylpyridine-3-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=CC(C=2N=CC=NC=2)=CN1C1=CC=CC=C1 KFDHIQVUEANUNN-UHFFFAOYSA-N 0.000 claims 1
- PPAKRHMKGUVRPM-UHFFFAOYSA-N n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-2-oxo-1-phenyl-5-pyridin-3-ylpyridine-3-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=CC(C=2C=NC=CC=2)=CN1C1=CC=CC=C1 PPAKRHMKGUVRPM-UHFFFAOYSA-N 0.000 claims 1
- LUAWSFFQLRPDPM-UHFFFAOYSA-N n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-3-methyl-5-oxo-1-phenyl-2-propylpyrazole-4-carboxamide Chemical compound CCCN1C(C)=C(C(=O)NC=2N=CC(OC=3C4=CC=C(OC)C=C4N=CC=3)=CC=2)C(=O)N1C1=CC=CC=C1 LUAWSFFQLRPDPM-UHFFFAOYSA-N 0.000 claims 1
- GHKSBYMPPJLVOA-UHFFFAOYSA-N n-[5-(7-methoxyquinolin-4-yl)oxypyridin-2-yl]-5-methyl-1-(2-methylpropyl)-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=C(C)N(CC(C)C)N1C1=CC=CC=C1 GHKSBYMPPJLVOA-UHFFFAOYSA-N 0.000 claims 1
- JEDCUDZEGIOLNY-UHFFFAOYSA-N n-[5-(7-methoxyquinolin-4-yl)oxypyrimidin-2-yl]-1,5-dimethyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1OC(C=N1)=CN=C1NC(=O)C(C1=O)=C(C)N(C)N1C1=CC=CC=C1 JEDCUDZEGIOLNY-UHFFFAOYSA-N 0.000 claims 1
- SLOJHNSCGMOADR-UHFFFAOYSA-N n-[5-(7-methoxyquinolin-4-yl)oxypyrimidin-2-yl]-3-methyl-5-oxo-1-phenyl-2-propylpyrazole-4-carboxamide Chemical compound CCCN1C(C)=C(C(=O)NC=2N=CC(OC=3C4=CC=C(OC)C=C4N=CC=3)=CN=2)C(=O)N1C1=CC=CC=C1 SLOJHNSCGMOADR-UHFFFAOYSA-N 0.000 claims 1
- PYCPSKNKICEHNC-UHFFFAOYSA-N n-[6-(6,7-dimethoxyquinolin-4-yl)oxypyridin-3-yl]-1,5-dimethyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(N=C1)=CC=C1NC(=O)C(C1=O)=C(C)N(C)N1C1=CC=CC=C1 PYCPSKNKICEHNC-UHFFFAOYSA-N 0.000 claims 1
- FNZXNVKKMPFSSC-UHFFFAOYSA-N n-[6-[2-fluoro-4-[(3-methyl-5-oxo-1-phenyl-2-propylpyrazole-4-carbonyl)amino]phenoxy]pyrimidin-4-yl]-4-methylpiperazine-1-carboxamide Chemical compound O=C1N(C=2C=CC=CC=2)N(CCC)C(C)=C1C(=O)NC(C=C1F)=CC=C1OC(N=CN=1)=CC=1NC(=O)N1CCN(C)CC1 FNZXNVKKMPFSSC-UHFFFAOYSA-N 0.000 claims 1
- KNECMKOMLLHKGO-UHFFFAOYSA-N n-[6-[2-fluoro-4-[(3-methyl-5-oxo-1-phenyl-2-propylpyrazole-4-carbonyl)amino]phenoxy]pyrimidin-4-yl]morpholine-4-carboxamide Chemical compound O=C1N(C=2C=CC=CC=2)N(CCC)C(C)=C1C(=O)NC(C=C1F)=CC=C1OC(N=CN=1)=CC=1NC(=O)N1CCOCC1 KNECMKOMLLHKGO-UHFFFAOYSA-N 0.000 claims 1
- RSVBIUVWFKMUOU-UHFFFAOYSA-N n-[6-[2-fluoro-4-[(3-methyl-5-oxo-1-phenyl-2-propylpyrazole-4-carbonyl)amino]phenoxy]pyrimidin-4-yl]piperidine-1-carboxamide Chemical compound O=C1N(C=2C=CC=CC=2)N(CCC)C(C)=C1C(=O)NC(C=C1F)=CC=C1OC(N=CN=1)=CC=1NC(=O)N1CCCCC1 RSVBIUVWFKMUOU-UHFFFAOYSA-N 0.000 claims 1
- SETROZIVWIONQM-UHFFFAOYSA-N n-[6-[4-[(1,5-dimethyl-3-oxo-2-phenylpyrazole-4-carbonyl)amino]-2-fluorophenoxy]pyrimidin-4-yl]morpholine-4-carboxamide Chemical compound O=C1N(C=2C=CC=CC=2)N(C)C(C)=C1C(=O)NC(C=C1F)=CC=C1OC(N=CN=1)=CC=1NC(=O)N1CCOCC1 SETROZIVWIONQM-UHFFFAOYSA-N 0.000 claims 1
- YRCHYHRCBXNYNU-UHFFFAOYSA-N n-[[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]carbamothioyl]-2-(4-fluorophenyl)acetamide Chemical compound N1=CC(CNCCOC)=CC=C1C1=CC2=NC=CC(OC=3C(=CC(NC(=S)NC(=O)CC=4C=CC(F)=CC=4)=CC=3)F)=C2S1 YRCHYHRCBXNYNU-UHFFFAOYSA-N 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 1
- JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 229960003787 sorafenib Drugs 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- WINHZLLDWRZWRT-ATVHPVEESA-N sunitinib Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C WINHZLLDWRZWRT-ATVHPVEESA-N 0.000 claims 1
- 229960001796 sunitinib Drugs 0.000 claims 1
- MBEWZJPHVIBZJD-UHFFFAOYSA-N tert-butyl 4-[5-[[5-(6,7-dimethoxyquinolin-4-yl)oxypyridin-2-yl]carbamoyl]-6-oxo-1-phenylpyridin-3-yl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C=12C=C(OC)C(OC)=CC2=NC=CC=1OC(C=N1)=CC=C1NC(=O)C(C1=O)=CC(C=2CCN(CC=2)C(=O)OC(C)(C)C)=CN1C1=CC=CC=C1 MBEWZJPHVIBZJD-UHFFFAOYSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 229950005976 tivantinib Drugs 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
- 239000002525 vasculotropin inhibitor Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12775308P | 2008-05-14 | 2008-05-14 | |
| US61/127,753 | 2008-05-14 | ||
| PCT/US2009/044034 WO2009140549A1 (en) | 2008-05-14 | 2009-05-14 | Combinations vegf(r) inhibitors and hepatocyte growth factor (c-met) inhibitors for the treatment of cancer |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011520908A JP2011520908A (ja) | 2011-07-21 |
| JP2011520908A5 true JP2011520908A5 (https=) | 2012-06-14 |
| JP5699075B2 JP5699075B2 (ja) | 2015-04-08 |
Family
ID=40908799
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011509721A Expired - Fee Related JP5699075B2 (ja) | 2008-05-14 | 2009-05-14 | 癌の治療のためのｖｅｇｆ（ｒ）阻害剤および肝細胞増殖因子（ｃ−ｍｅｔ）阻害剤との組合せ |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US20110104161A1 (https=) |
| EP (1) | EP2288383A1 (https=) |
| JP (1) | JP5699075B2 (https=) |
| AU (1) | AU2009246263B2 (https=) |
| CA (1) | CA2723617A1 (https=) |
| MX (1) | MX2010012290A (https=) |
| WO (1) | WO2009140549A1 (https=) |
Families Citing this family (77)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU9598601A (en) | 2000-10-20 | 2002-04-29 | Eisai Co Ltd | Nitrogenous aromatic ring compounds |
| ATE428421T1 (de) | 2004-09-17 | 2009-05-15 | Eisai R&D Man Co Ltd | Medizinische zusammensetzung mit verbesserter stabilität und reduzierten gelierungseigenschaften |
| JP4989476B2 (ja) | 2005-08-02 | 2012-08-01 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 血管新生阻害物質の効果を検定する方法 |
| AU2006309551B2 (en) | 2005-11-07 | 2012-04-19 | Eisai R & D Management Co., Ltd. | Use of combination of anti-angiogenic substance and c-kit kinase inhibitor |
| CN104706637A (zh) | 2006-05-18 | 2015-06-17 | 卫材R&D管理有限公司 | 针对甲状腺癌的抗肿瘤剂 |
| WO2008026748A1 (en) | 2006-08-28 | 2008-03-06 | Eisai R & D Management Co., Ltd. | Antitumor agent for undifferentiated gastric cancer |
| CA2676796C (en) | 2007-01-29 | 2016-02-23 | Eisai R & D Management Co., Ltd. | Composition for treatment of undifferentiated gastric cancer |
| US8952035B2 (en) | 2007-11-09 | 2015-02-10 | Eisai R&D Management Co., Ltd. | Combination of anti-angiogenic substance and anti-tumor platinum complex |
| EP2265270A1 (en) | 2008-02-04 | 2010-12-29 | OSI Pharmaceuticals, Inc. | 2-aminopyridine kinase inhibitors |
| AR070317A1 (es) | 2008-02-06 | 2010-03-31 | Osi Pharm Inc | Furo (3,2-c) piridina y tieno (3,2-c) piridinas |
| TW201019961A (en) * | 2008-10-17 | 2010-06-01 | Genentech Inc | Combination therapy |
| US8592448B2 (en) | 2008-11-20 | 2013-11-26 | OSI Pharmaceuticals, LLC | Substituted pyrrolo[2,3-b]-pyridines and -pyrazines |
| MY162940A (en) | 2009-08-19 | 2017-07-31 | Eisai R&D Man Co Ltd | Quinoline derivative-containing pharmaceutical composition |
| US8293925B2 (en) | 2009-09-21 | 2012-10-23 | Chemocentryx, Inc. | Pyrrolidinone carboxamide derivatives |
| CA2800998A1 (en) | 2010-04-29 | 2011-11-10 | Deciphera Pharmaceuticals, Llc | Pyridone amides and analogs exhibiting anti-cancer and anti-proliferative activities |
| EP2569315A1 (en) | 2010-05-14 | 2013-03-20 | OSI Pharmaceuticals, LLC | Fused bicyclic kinase inhibitors |
| AR081039A1 (es) | 2010-05-14 | 2012-05-30 | Osi Pharmaceuticals Llc | Inhibidores biciclicos fusionados de quinasa |
| CN102958523B (zh) | 2010-06-25 | 2014-11-19 | 卫材R&D管理有限公司 | 使用具有激酶抑制作用的组合的抗肿瘤剂 |
| US20130315895A1 (en) * | 2010-07-01 | 2013-11-28 | Takeda Pharmaceutical Company Limited | COMBINATION OF A cMET INHIBITOR AND AN ANTIBODY TO HGF AND/OR cMET |
| JP2013540759A (ja) * | 2010-09-27 | 2013-11-07 | エクセリクシス， インク． | 去勢抵抗性前立腺癌および造骨性転移の治療のためのｍｅｔおよびｖｅｇｆの二元阻害薬 |
| US20140057908A1 (en) * | 2010-09-27 | 2014-02-27 | Exelixis, Inc. | Method of Treating Cancer |
| MX352926B (es) * | 2010-09-27 | 2017-12-14 | Exelixis Inc | Inhibidores dobles de met y factor de crecimiento endotelial vascular (vegf) para el tratamiento de cancer de prostata resistente a la castracion y metastasis osteoblasticas en los huesos. |
| WO2012042421A1 (en) * | 2010-09-29 | 2012-04-05 | Pfizer Inc. | Method of treating abnormal cell growth |
| RU2568258C2 (ru) * | 2011-02-28 | 2015-11-20 | Саншайн Лейк Фарма Ко., Лтд | Замещенные соединения хинолина и способы их использования |
| KR20120100027A (ko) * | 2011-03-02 | 2012-09-12 | 한국생명공학연구원 | 엔도사이토시스 모티프 및 단백질 도입 도메인을 포함하는 암 예방 또는 치료용 약학적 조성물 |
| JPWO2012133416A1 (ja) | 2011-03-29 | 2014-07-28 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | フェノキシピリジン誘導体の製造方法（３） |
| CN103402519B (zh) | 2011-04-18 | 2015-11-25 | 卫材R&D管理有限公司 | 肿瘤治疗剂 |
| JP2014513724A (ja) | 2011-05-16 | 2014-06-05 | オーエスアイ・ファーマシューティカルズ，エルエルシー | 融合二環キナーゼ阻害剤 |
| JP6038128B2 (ja) | 2011-06-03 | 2016-12-07 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | レンバチニブ化合物に対する甲状腺癌対象及び腎臓癌対象の反応性を予測及び評価するためのバイオマーカー |
| WO2013003606A1 (en) * | 2011-06-29 | 2013-01-03 | Amgen Inc. | Predictive biomarker of survival in the treatment of renal cell carcinoma |
| SG11201400724SA (en) * | 2011-09-19 | 2014-04-28 | Genentech Inc | Combination treatments comprising c-met antagonists and b-raf antagonists |
| TWI594986B (zh) * | 2011-12-28 | 2017-08-11 | Taiho Pharmaceutical Co Ltd | Antineoplastic agent effect enhancer |
| JP2015512447A (ja) * | 2012-04-03 | 2015-04-27 | ノバルティス アーゲー | チロシンキナーゼ阻害薬の組合せおよびその使用 |
| WO2013166296A1 (en) | 2012-05-02 | 2013-11-07 | Exelixis, Inc. | A dual met - vegf modulator for treating osteolytic bone metastases |
| HUE032306T2 (en) | 2012-06-26 | 2017-09-28 | Bayer Pharma AG | N- [4- (quinolin-4-yloxy) cyclohexyl (methyl)] (hetero) arylcarboxamides as androgen receptor antagonists, their production and use as pharmaceutical products |
| JP6342392B2 (ja) * | 2012-07-28 | 2018-06-13 | カリター・サイエンシーズ・エルエルシー | 置換型ピラゾロン化合物及び使用方法 |
| EP2708556B1 (en) | 2012-09-12 | 2018-11-07 | Samsung Electronics Co., Ltd | Pharmaceutical composition for the use in a combination therapy for prevention or treatment of c-met or angiogenesis factor induced diseases |
| KR20150098605A (ko) | 2012-12-21 | 2015-08-28 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 퀴놀린 유도체의 비정질 형태 및 그의 제조방법 |
| EP2956138B1 (en) | 2013-02-15 | 2022-06-22 | Kala Pharmaceuticals, Inc. | Therapeutic compounds and uses thereof |
| MX368903B (es) | 2013-02-20 | 2019-10-21 | Kala Pharmaceuticals Inc | Compuestos terapéuticos y sus usos en el tratamiento de enfermedades proliferativas. |
| US9688688B2 (en) | 2013-02-20 | 2017-06-27 | Kala Pharmaceuticals, Inc. | Crystalline forms of 4-((4-((4-fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazolin-7-yl)oxy)-1-(2-oxa-7-azaspiro[3.5]nonan-7-yl)butan-1-one and uses thereof |
| KR102049990B1 (ko) | 2013-03-28 | 2019-12-03 | 삼성전자주식회사 | c-Met 항체 및 VEGF 결합 단편이 연결된 융합 단백질 |
| NZ714049A (en) | 2013-05-14 | 2020-05-29 | Eisai R&D Man Co Ltd | Biomarkers for predicting and assessing responsiveness of endometrial cancer subjects to lenvatinib compounds |
| TWI649308B (zh) | 2013-07-24 | 2019-02-01 | 小野藥品工業股份有限公司 | 喹啉衍生物 |
| US9458169B2 (en) | 2013-11-01 | 2016-10-04 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
| US9890173B2 (en) | 2013-11-01 | 2018-02-13 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
| TW201622744A (zh) * | 2014-03-04 | 2016-07-01 | 美國禮來大藥廠 | 癌症之組合療法 |
| US20150299219A1 (en) * | 2014-04-22 | 2015-10-22 | Calitor Sciences, Llc | Bicyclic pyrazolone compounds and methods of use |
| PT3524595T (pt) | 2014-08-28 | 2022-09-19 | Eisai R&D Man Co Ltd | Derivado de quinolina altamente puro e método para produção do mesmo |
| JP6267619B2 (ja) * | 2014-09-30 | 2018-01-24 | 学校法人近畿大学 | 慢性骨髄性白血病の治療用組成物 |
| ES2749726T3 (es) * | 2014-12-25 | 2020-03-23 | Ono Pharmaceutical Co | Derivado de quinolina |
| LT3263106T (lt) | 2015-02-25 | 2024-01-10 | Eisai R&D Management Co., Ltd. | Chinolino darinių kartumo sumažinimo būdas |
| KR102662228B1 (ko) | 2015-03-04 | 2024-05-02 | 머크 샤프 앤드 돔 코포레이션 | 암을 치료하기 위한 pd-1 길항제 및 vegfr/fgfr/ret 티로신 키나제 억제제의 조합 |
| MX373231B (es) | 2015-06-16 | 2020-05-08 | Eisai R&D Man Co Ltd | Agente anticancerigeno. |
| US12220398B2 (en) | 2015-08-20 | 2025-02-11 | Eisai R&D Management Co., Ltd. | Tumor therapeutic agent |
| EP3373932B1 (en) * | 2015-11-14 | 2022-03-30 | Sunshine Lake Pharma Co., Ltd. | Crystalline form of a substituted quinoline compound and pharmaceutical compositions thereof |
| IL287136B2 (en) | 2016-02-05 | 2023-09-01 | Denali Therapeutics Inc | Receptor inhibitors - interacting with protein kinase 1 |
| AU2017324713B2 (en) | 2016-09-08 | 2020-08-13 | KALA BIO, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
| US10336767B2 (en) | 2016-09-08 | 2019-07-02 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
| EP3509423A4 (en) | 2016-09-08 | 2020-05-13 | Kala Pharmaceuticals, Inc. | CRYSTALLINE FORMS OF THERAPEUTIC COMPOUNDS AND USES THEREOF |
| TWI782930B (zh) | 2016-11-16 | 2022-11-11 | 美商再生元醫藥公司 | 抗ｍｅｔ抗體，結合ｍｅｔ之雙特異性抗原結合分子及其使用方法 |
| JP7208137B2 (ja) | 2016-12-09 | 2023-01-18 | デナリ セラピューティクス インコーポレイテッド | 化合物、組成物および方法 |
| TWI779007B (zh) | 2017-01-26 | 2022-10-01 | 日商小野藥品工業股份有限公司 | 喹啉衍生物的乙磺酸鹽 |
| US12303505B2 (en) | 2017-02-08 | 2025-05-20 | Eisai R&D Management Co., Ltd. | Tumor-treating pharmaceutical composition |
| WO2018151177A1 (ja) | 2017-02-15 | 2018-08-23 | 大鵬薬品工業株式会社 | 医薬組成物 |
| JP7128204B2 (ja) | 2017-04-27 | 2022-08-30 | アストラゼネカ・アクチエボラーグ | Ｃ５－アニリノキナゾリン化合物及び癌の処置におけるそれらの使用 |
| RU2019134940A (ru) | 2017-05-16 | 2021-06-16 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Лечение гепатоцеллюлярной карциномы |
| JP7074760B2 (ja) | 2017-09-08 | 2022-05-24 | 大鵬薬品工業株式会社 | 抗腫瘍剤及び抗腫瘍効果増強剤 |
| US11826363B2 (en) | 2017-10-13 | 2023-11-28 | Ono Pharmaceutical Co., Ltd. | Therapeutic agent for solid cancers, which comprises Axl inhibitor as active ingredient |
| CN111303024B (zh) | 2018-12-12 | 2023-03-28 | 安徽中科拓苒药物科学研究有限公司 | 一种喹啉结构的pan-KIT激酶抑制剂及其用途 |
| AU2020349462A1 (en) | 2019-09-16 | 2022-03-03 | Regeneron Pharmaceuticals, Inc. | Radiolabeled MET binding proteins for immuno-PET imaging |
| CN112778217B (zh) * | 2019-11-08 | 2024-01-26 | 沈阳化工研究院有限公司 | 一种喹唑啉类化合物及其应用 |
| BR112022019517A2 (pt) * | 2020-03-30 | 2022-12-06 | Hutchison Medipharma Ltd | Compostos de amida e usos dos mesmos |
| US20230301972A1 (en) * | 2020-05-20 | 2023-09-28 | Fred Hutchinson Cancer Center | Anti-fibrotic composition and related methods |
| TW202309022A (zh) | 2021-04-13 | 2023-03-01 | 美商努法倫特公司 | 用於治療具egfr突變之癌症之胺基取代雜環 |
| TW202334164A (zh) | 2022-01-12 | 2023-09-01 | 美商戴納立製藥公司 | （Ｓ）－５－苄基－Ｎ－（５－甲基－４－側氧基－２，３，４，５－四氫吡啶並［３，２－ｂ］［１，４］氧氮呯－３－基）－４Ｈ－１，２，４－三唑－３－甲醯胺的晶型 |
| CN117126142B (zh) * | 2023-08-30 | 2026-02-10 | 遵义医科大学珠海校区 | 杂环类egfr突变抑制剂及其应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040208876A1 (en) * | 2003-04-18 | 2004-10-21 | Kim Kyung Jin | Monoclonal antibodies to hepatocyte growth factor |
| DE102004035655A1 (de) * | 2004-07-22 | 2006-02-16 | Henkel Kgaa | Verfahren zur Herstellung von Mehrphasen-Sticks für die WC-Reinigung |
| CA2575402A1 (en) * | 2004-08-05 | 2006-02-09 | Genentech, Inc. | Humanized anti-cmet antagonists |
| JO2787B1 (en) * | 2005-04-27 | 2014-03-15 | امجين إنك, | Alternative amide derivatives and methods of use |
| US20080108664A1 (en) * | 2005-12-23 | 2008-05-08 | Liu Belle B | Solid-state form of AMG 706 and pharmaceutical compositions thereof |
| JP2009526050A (ja) * | 2006-02-10 | 2009-07-16 | アムジエン・インコーポレーテツド | Ａｍｇ７０６の水和物形態 |
| US8101727B2 (en) * | 2006-03-30 | 2012-01-24 | Novartis Ag | Compositions and methods of use for antibodies of c-Met |
| AR059922A1 (es) * | 2006-04-01 | 2008-05-07 | Galaxy Biotech Llc | Anticuerpos monoclonales humanizados para el factor de crecimiento de hepatocitos |
-
2009
- 2009-05-14 AU AU2009246263A patent/AU2009246263B2/en not_active Expired - Fee Related
- 2009-05-14 EP EP09747630A patent/EP2288383A1/en not_active Withdrawn
- 2009-05-14 CA CA2723617A patent/CA2723617A1/en not_active Abandoned
- 2009-05-14 JP JP2011509721A patent/JP5699075B2/ja not_active Expired - Fee Related
- 2009-05-14 US US12/992,359 patent/US20110104161A1/en not_active Abandoned
- 2009-05-14 MX MX2010012290A patent/MX2010012290A/es not_active Application Discontinuation
- 2009-05-14 WO PCT/US2009/044034 patent/WO2009140549A1/en not_active Ceased
-
2014
- 2014-02-28 US US14/194,431 patent/US20140243339A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2011520908A5 (https=) | ||
| CA2605680A1 (en) | Substituted amide derivatives as protein kinase inhibitors | |
| HRP20231310T1 (hr) | Heteroarilaminopirimidin amidni inhibitori autofagije i postupci njihove primjene | |
| HRP20251479T1 (hr) | Pesticidno aktivni kondenzirani biciklički heteroaromatski spojevi | |
| JP2008521900A5 (https=) | ||
| JP2022531801A5 (https=) | ||
| JP2023501253A5 (https=) | ||
| JP2022531932A5 (https=) | ||
| HRP20231730T1 (hr) | Fenilaminopirimidin amidni inhibitori autofagije i postupci njihove primjene | |
| CA2587642A1 (en) | Substituted heterocycles and methods of use | |
| RU2016124176A (ru) | Композиции тетрагидрохинолинов в качестве ингибиторов бромодомена вет | |
| JP2019504821A5 (https=) | ||
| HRP20140265T1 (hr) | Derivat aminopirazina i odgovarajuä†i lijek | |
| MX2010012290A (es) | Combinaciones de inhibidores del receptor del factor de crecimiento endotelial vascular e inhibidores del factor de crecimiento de hepatocito para el tratamiento de cancer. | |
| RU2014110172A (ru) | Гетероциклическое производное и фармацевтическое средство | |
| CA2671744A1 (en) | Compounds and compositions as protein kinase inhibitors | |
| JP2014062093A5 (https=) | ||
| JP2015500332A5 (https=) | ||
| HRP20201337T1 (hr) | Inhibitori lizin-specifične demetilaze-1 | |
| SI3074386T1 (en) | New aminopyrimidine derivatives | |
| SI3177619T1 (en) | 2- (morpholin-4-yl) -1,7-naphthyridines | |
| JP2017530185A5 (https=) | ||
| IL295076A (en) | Piperidinone derivatives as mdm2 inhibitors for cancer therapy | |
| RU2018131766A (ru) | 6-гетероциклил-4-морфолин-4-илпиридин-2-оны, пригодные для лечения рака и диабета | |
| RU2014131378A (ru) | Ингибиторы бромдомена |