AU2009246263B2 - Combinations VEGF(R) inhibitors and hepatocyte growth factor (c-Met) inhibitors for the treatment of cancer - Google Patents

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Publication number

AU2009246263B2

AU2009246263B2 AU2009246263A AU2009246263A AU2009246263B2 AU 2009246263 B2 AU2009246263 B2 AU 2009246263B2 AU 2009246263 A AU2009246263 A AU 2009246263A AU 2009246263 A AU2009246263 A AU 2009246263A AU 2009246263 B2 AU2009246263 B2 AU 2009246263B2

Authority

AU

Australia

Prior art keywords

phenyl

oxo

carboxamide

methyl

dihydro

Prior art date

2008-05-14

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.)

Expired - Fee Related

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• 239000003112 inhibitor Substances 0.000 title claims abstract description 94
• 206010028980 Neoplasm Diseases 0.000 title claims abstract description 67
• 201000011510 cancer Diseases 0.000 title claims abstract description 17
• 238000011282 treatment Methods 0.000 title claims description 42
• 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 title abstract description 25
• 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 title abstract 2
• 102000003745 Hepatocyte Growth Factor Human genes 0.000 title description 6
• 108090000100 Hepatocyte Growth Factor Proteins 0.000 title description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 53
• 238000000034 method Methods 0.000 claims abstract description 35
• -1 benzomorpholinyl Chemical group 0.000 claims description 92
• 125000000217 alkyl group Chemical group 0.000 claims description 76
• 125000000623 heterocyclic group Chemical group 0.000 claims description 59
• RAHBGWKEPAQNFF-UHFFFAOYSA-N motesanib Chemical group C=1C=C2C(C)(C)CNC2=CC=1NC(=O)C1=CC=CN=C1NCC1=CC=NC=C1 RAHBGWKEPAQNFF-UHFFFAOYSA-N 0.000 claims description 46
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 42
• 125000003118 aryl group Chemical group 0.000 claims description 40
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 29
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 27
• 229940124674 VEGF-R inhibitor Drugs 0.000 claims description 25
• 125000000304 alkynyl group Chemical group 0.000 claims description 23
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 23
• 125000001475 halogen functional group Chemical group 0.000 claims description 23
• 150000003839 salts Chemical class 0.000 claims description 22
• 125000001188 haloalkyl group Chemical class 0.000 claims description 20
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• 229950003968 motesanib Drugs 0.000 claims description 19
• 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 18
• 125000003342 alkenyl group Chemical group 0.000 claims description 17
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 16
• 239000011570 nicotinamide Substances 0.000 claims description 15
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 14
• 229960003966 nicotinamide Drugs 0.000 claims description 14
• 125000001072 heteroaryl group Chemical group 0.000 claims description 13
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 13
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 12
• 125000003282 alkyl amino group Chemical group 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 11
• NJQRAAHKQQPUIT-UHFFFAOYSA-N 1,2-dihydropyridine-3-carboxamide Chemical compound NC(=O)C1=CC=CNC1 NJQRAAHKQQPUIT-UHFFFAOYSA-N 0.000 claims description 10
• VTRPHKGMOTTZCK-UHFFFAOYSA-N 1-methyl-3-oxo-2-phenylpyrazole-4-carboxamide Chemical compound CN1C=C(C(N)=O)C(=O)N1C1=CC=CC=C1 VTRPHKGMOTTZCK-UHFFFAOYSA-N 0.000 claims description 10
• 208000005017 glioblastoma Diseases 0.000 claims description 10
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 9
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
• 229920006395 saturated elastomer Polymers 0.000 claims description 9
• 125000001424 substituent group Chemical group 0.000 claims description 9
• NDKGNYXCMKDBKK-UHFFFAOYSA-N 3-oxo-2-phenyl-1h-pyrazole-4-carboxamide Chemical compound O=C1C(C(=O)N)=CNN1C1=CC=CC=C1 NDKGNYXCMKDBKK-UHFFFAOYSA-N 0.000 claims description 8
• 206010009944 Colon cancer Diseases 0.000 claims description 7
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 7
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 7
• 208000006265 Renal cell carcinoma Diseases 0.000 claims description 6
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 6
• 125000003418 alkyl amino alkoxy group Chemical group 0.000 claims description 6
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 6
• 125000004104 aryloxy group Chemical group 0.000 claims description 6
• 150000003857 carboxamides Chemical class 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
• 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 6
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
• 235000005152 nicotinamide Nutrition 0.000 claims description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 5
• 125000005518 carboxamido group Chemical group 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 5
• 201000010536 head and neck cancer Diseases 0.000 claims description 5
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 5
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
• 201000005202 lung cancer Diseases 0.000 claims description 5
• 208000020816 lung neoplasm Diseases 0.000 claims description 5
• ZKWFSTHEYLJLEL-UHFFFAOYSA-N morpholine-4-carboxamide Chemical compound NC(=O)N1CCOCC1 ZKWFSTHEYLJLEL-UHFFFAOYSA-N 0.000 claims description 5
• 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 description 5
• UBPZDKDOVRZZBT-UHFFFAOYSA-N 2-phenyl-1,3-dihydropyrazole-4-carboxamide Chemical compound C1C(C(=O)N)=CNN1C1=CC=CC=C1 UBPZDKDOVRZZBT-UHFFFAOYSA-N 0.000 claims description 4
• IOKCOVMKPFXPBM-UHFFFAOYSA-N 5-methyl-3-oxo-2-phenyl-1h-pyrazole-4-carboxamide Chemical compound O=C1C(C(N)=O)=C(C)NN1C1=CC=CC=C1 IOKCOVMKPFXPBM-UHFFFAOYSA-N 0.000 claims description 4
• 206010006187 Breast cancer Diseases 0.000 claims description 4
• 208000026310 Breast neoplasm Diseases 0.000 claims description 4
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 4
• 150000001204 N-oxides Chemical class 0.000 claims description 4
• 206010038389 Renal cancer Diseases 0.000 claims description 4
• 229910052799 carbon Inorganic materials 0.000 claims description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
• 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 4
• 201000010982 kidney cancer Diseases 0.000 claims description 4
• 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 description 4
• 239000012453 solvate Substances 0.000 claims description 4
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
• QFXAYLJEIJWKJR-UHFFFAOYSA-N 2-oxo-1-phenylpyridine-3-carboxamide Chemical compound O=C1C(C(=O)N)=CC=CN1C1=CC=CC=C1 QFXAYLJEIJWKJR-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 3
• 201000010915 Glioblastoma multiforme Diseases 0.000 claims description 3
• 125000004946 alkenylalkyl group Chemical group 0.000 claims description 3
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 3
• 125000005335 azido alkyl group Chemical group 0.000 claims description 3
• 125000004432 carbon atom Chemical group C* 0.000 claims description 3
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 3
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
• 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 description 3
• VNJQWCBSSDYYRS-SFHVURJKSA-N n-[4-(6,7-dimethoxyquinolin-4-yl)oxy-3-fluorophenyl]-1-[(2s)-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-SFHVURJKSA-N 0.000 claims description 3
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 3
• IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 3
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 3
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• SHCQHOOTJJNVAZ-IBGZPJMESA-N 1-[(2s)-2-acetamidopropyl]-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)NC(C)=O)N1C1=CC=CC=C1 SHCQHOOTJJNVAZ-IBGZPJMESA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• PBDCPKUBHSMIMC-UHFFFAOYSA-N 2-pyridin-4-yl-1,5-dihydropyrazole-4-carboxamide Chemical compound N1CC(C(=O)N)=CN1C1=CC=NC=C1 PBDCPKUBHSMIMC-UHFFFAOYSA-N 0.000 claims description 2
• KRNXUXJJPNCQNB-UHFFFAOYSA-N 3-oxo-1,2-dihydropyrazole-4-carboxamide Chemical compound NC(=O)C1=CNNC1=O KRNXUXJJPNCQNB-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• LFXLYXBXSOBBCY-UHFFFAOYSA-N 5-(1,2,3,6-tetrahydropyridin-4-yl)-1,2-dihydropyridine-3-carboxamide Chemical compound NC(=O)C1=CC(=CNC1)C1=CCNCC1 LFXLYXBXSOBBCY-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• LGFPQHVZHQSCLS-UHFFFAOYSA-N 6-[(dimethylamino)methyl]-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(CN(C)C)=NN1C1=CC=CC=C1 LGFPQHVZHQSCLS-UHFFFAOYSA-N 0.000 claims description 2
• YWNYGVOVVRSQSS-UHFFFAOYSA-N 7-[2-fluoro-4-[[1-(2-hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenylpyrazole-4-carbonyl]amino]phenoxy]thieno[3,2-b]pyridine-2-carboxamide Chemical compound CC(O)(C)CN1C(C)=C(C(=O)NC=2C=C(F)C(OC=3C=4SC(=CC=4N=CC=3)C(N)=O)=CC=2)C(=O)N1C1=CC=CC=C1 YWNYGVOVVRSQSS-UHFFFAOYSA-N 0.000 claims description 2
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 2
• 208000029742 colonic neoplasm Diseases 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• GBDSEEYQRPYJFZ-UHFFFAOYSA-N n-[4-(6,7-dimethoxy-1-oxidoquinolin-1-ium-4-yl)oxy-3-fluorophenyl]-3-methyl-5-oxo-1-phenyl-2-prop-2-enylpyrazole-4-carboxamide Chemical compound C1=C[N+]([O-])=C2C=C(OC)C(OC)=CC2=C1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(CC=C)N1C1=CC=CC=C1 GBDSEEYQRPYJFZ-UHFFFAOYSA-N 0.000 claims description 2
• CMFUWQFMLWEMFY-UHFFFAOYSA-N n-[4-(6,7-dimethoxyquinazolin-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=NC=1OC(C(=C1)F)=CC=C1NC(=O)C(C1=O)=C(C)N(CC(C)(C)O)N1C1=CC=CC=C1 CMFUWQFMLWEMFY-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• ABZOIGXCNVWVPX-UHFFFAOYSA-N n-[4-(7-methoxyquinolin-4-yl)sulfinylphenyl]-3-methyl-5-oxo-1-phenyl-2-propylpyrazole-4-carboxamide Chemical compound CCCN1C(C)=C(C(=O)NC=2C=CC(=CC=2)S(=O)C=2C3=CC=C(OC)C=C3N=CC=2)C(=O)N1C1=CC=CC=C1 ABZOIGXCNVWVPX-UHFFFAOYSA-N 0.000 claims description 2
• QPKPHMWUZAYEGT-UHFFFAOYSA-N n-[4-[(7-methoxyquinolin-4-yl)amino]phenyl]-3-methyl-5-oxo-1-phenyl-2-propylpyrazole-4-carboxamide Chemical compound CCCN1C(C)=C(C(=O)NC=2C=CC(NC=3C4=CC=C(OC)C=C4N=CC=3)=CC=2)C(=O)N1C1=CC=CC=C1 QPKPHMWUZAYEGT-UHFFFAOYSA-N 0.000 claims description 2
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• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
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• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
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• 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
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• 230000000052 comparative effect Effects 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
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