JP2006502112A - 置換アントラニルアミド誘導体および使用方法 - Google Patents
置換アントラニルアミド誘導体および使用方法 Download PDFInfo
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- JP2006502112A JP2006502112A JP2004520114A JP2004520114A JP2006502112A JP 2006502112 A JP2006502112 A JP 2006502112A JP 2004520114 A JP2004520114 A JP 2004520114A JP 2004520114 A JP2004520114 A JP 2004520114A JP 2006502112 A JP2006502112 A JP 2006502112A
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- 238000000034 method Methods 0.000 title claims abstract description 98
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 title description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 310
- 150000003839 salts Chemical class 0.000 claims abstract description 47
- 238000011282 treatment Methods 0.000 claims abstract description 45
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 43
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 38
- 201000010099 disease Diseases 0.000 claims abstract description 25
- 230000033115 angiogenesis Effects 0.000 claims abstract description 21
- 201000011510 cancer Diseases 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 230000001404 mediated effect Effects 0.000 claims abstract description 6
- -1 amino, hydroxy Chemical group 0.000 claims description 521
- 238000002360 preparation method Methods 0.000 claims description 146
- 125000000623 heterocyclic group Chemical group 0.000 claims description 128
- 238000006243 chemical reaction Methods 0.000 claims description 94
- 125000000217 alkyl group Chemical group 0.000 claims description 66
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 61
- 125000001424 substituent group Chemical group 0.000 claims description 44
- 229920006395 saturated elastomer Polymers 0.000 claims description 41
- 125000005843 halogen group Chemical group 0.000 claims description 33
- 239000003814 drug Substances 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 229940079593 drug Drugs 0.000 claims description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 17
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 16
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 14
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 208000035475 disorder Diseases 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 101150065749 Churc1 gene Proteins 0.000 claims description 11
- 102100038239 Protein Churchill Human genes 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims description 10
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 9
- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims description 9
- 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 claims description 9
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 9
- 230000012010 growth Effects 0.000 claims description 9
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 9
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 8
- SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 8
- 108010050904 Interferons Proteins 0.000 claims description 7
- 102000014150 Interferons Human genes 0.000 claims description 7
- 108091008605 VEGF receptors Proteins 0.000 claims description 7
- 102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 7
- 229940079322 interferon Drugs 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 6
- 206010061218 Inflammation Diseases 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 230000004054 inflammatory process Effects 0.000 claims description 6
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 6
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 6
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 6
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 6
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 claims description 5
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 5
- 239000003242 anti bacterial agent Substances 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- HBLHQDSWCAZXOG-UHFFFAOYSA-N n-(4,4-dimethyl-2,3-dihydro-1h-quinolin-7-yl)-2-(quinazolin-6-ylamino)benzamide Chemical compound N1=CN=CC2=CC(NC3=CC=CC=C3C(=O)NC=3C=C4NCCC(C4=CC=3)(C)C)=CC=C21 HBLHQDSWCAZXOG-UHFFFAOYSA-N 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000004942 pyridazin-6-yl group Chemical group N1=NC=CC=C1* 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 230000000340 anti-metabolite Effects 0.000 claims description 4
- 229940100197 antimetabolite Drugs 0.000 claims description 4
- 239000002256 antimetabolite Substances 0.000 claims description 4
- 230000017531 blood circulation Effects 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- ZXOFVTMVRJWTAG-UHFFFAOYSA-N n-(1-acetyl-3,3-dimethyl-2h-indol-6-yl)-2-(pyridin-4-ylmethylamino)benzamide Chemical compound C1=C2N(C(=O)C)CC(C)(C)C2=CC=C1NC(=O)C1=CC=CC=C1NCC1=CC=NC=C1 ZXOFVTMVRJWTAG-UHFFFAOYSA-N 0.000 claims description 4
- COZSLNKBURQTJX-UHFFFAOYSA-N n-(1-acetyl-3,3-dimethyl-2h-indol-6-yl)-2-(quinolin-4-ylmethylamino)benzamide Chemical compound C1=CC=C2C(CNC3=CC=CC=C3C(=O)NC3=CC=C4C(C)(C)CN(C4=C3)C(=O)C)=CC=NC2=C1 COZSLNKBURQTJX-UHFFFAOYSA-N 0.000 claims description 4
- IKTFEBNTUYTPCK-UHFFFAOYSA-N n-(1-ethyl-3,3-dimethyl-2h-indol-6-yl)-2-(pyridin-4-ylmethylamino)benzamide Chemical compound C1=C2N(CC)CC(C)(C)C2=CC=C1NC(=O)C1=CC=CC=C1NCC1=CC=NC=C1 IKTFEBNTUYTPCK-UHFFFAOYSA-N 0.000 claims description 4
- JQVREGRYMBTPRO-UHFFFAOYSA-N n-(4,4-dimethyl-2,3-dihydro-1h-isoquinolin-7-yl)-2-[(2-methoxypyridin-4-yl)methylamino]benzamide Chemical compound C1=NC(OC)=CC(CNC=2C(=CC=CC=2)C(=O)NC=2C=C3C(C(CNC3)(C)C)=CC=2)=C1 JQVREGRYMBTPRO-UHFFFAOYSA-N 0.000 claims description 4
- GUIOOGNPPDHMRU-UHFFFAOYSA-N n-(4,4-dimethyl-2,3-dihydro-1h-isoquinolin-7-yl)-2-[1-[2-(methylamino)pyrimidin-4-yl]ethylamino]benzamide Chemical compound CNC1=NC=CC(C(C)NC=2C(=CC=CC=2)C(=O)NC=2C=C3C(C(CNC3)(C)C)=CC=2)=N1 GUIOOGNPPDHMRU-UHFFFAOYSA-N 0.000 claims description 4
- FNFSNNWULZMNNC-UHFFFAOYSA-N n-(4,4-dimethyl-2,3-dihydro-1h-isoquinolin-7-yl)-2-[[2-(methylamino)pyrimidin-4-yl]methylamino]benzamide Chemical compound CNC1=NC=CC(CNC=2C(=CC=CC=2)C(=O)NC=2C=C3C(C(CNC3)(C)C)=CC=2)=N1 FNFSNNWULZMNNC-UHFFFAOYSA-N 0.000 claims description 4
- MXMQURVEDWCCER-UHFFFAOYSA-N n-[4-[2-(1-methylpiperidin-4-yl)propan-2-yl]phenyl]-2-(pyridin-4-ylmethylamino)benzamide Chemical compound C1CN(C)CCC1C(C)(C)C(C=C1)=CC=C1NC(=O)C1=CC=CC=C1NCC1=CC=NC=C1 MXMQURVEDWCCER-UHFFFAOYSA-N 0.000 claims description 4
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 4
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 4
- 125000004547 quinazolin-6-yl group Chemical group N1=CN=CC2=CC(=CC=C12)* 0.000 claims description 4
- 125000005877 1,4-benzodioxanyl group Chemical group 0.000 claims description 3
- OIPPARMLEWQGSK-UHFFFAOYSA-N 2-[(4-fluorophenyl)methylamino]-n-[4-[2-(1-methylpiperidin-4-yl)propan-2-yl]phenyl]benzamide Chemical compound C1CN(C)CCC1C(C)(C)C(C=C1)=CC=C1NC(=O)C1=CC=CC=C1NCC1=CC=C(F)C=C1 OIPPARMLEWQGSK-UHFFFAOYSA-N 0.000 claims description 3
- IKDAWKWPRPYNJA-UHFFFAOYSA-N 2-[1-(2-aminopyrimidin-4-yl)ethylamino]-n-(4,4-dimethyl-2,3-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C=1C=CC=C(C(=O)NC=2C=C3C(C(CNC3)(C)C)=CC=2)C=1NC(C)C1=CC=NC(N)=N1 IKDAWKWPRPYNJA-UHFFFAOYSA-N 0.000 claims description 3
- 230000003115 biocidal effect Effects 0.000 claims description 3
- 208000035269 cancer or benign tumor Diseases 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims description 3
- BPPJLUFEJJNKCY-UHFFFAOYSA-N n-(3,3-dimethyl-1,2-dihydroindol-6-yl)-2-(pyridin-4-ylmethylamino)benzamide Chemical compound C=1C=C2C(C)(C)CNC2=CC=1NC(=O)C1=CC=CC=C1NCC1=CC=NC=C1 BPPJLUFEJJNKCY-UHFFFAOYSA-N 0.000 claims description 3
- QLFQMDKFOJZHBK-UHFFFAOYSA-N n-(4,4-dimethyl-2,3-dihydro-1h-isoquinolin-7-yl)-2-(pyridazin-4-ylmethylamino)benzamide Chemical compound C=1C=C2C(C)(C)CNCC2=CC=1NC(=O)C1=CC=CC=C1NCC1=CC=NN=C1 QLFQMDKFOJZHBK-UHFFFAOYSA-N 0.000 claims description 3
- FTNKCGULGWHQPV-UHFFFAOYSA-N n-(4,4-dimethyl-2,3-dihydro-1h-isoquinolin-7-yl)-2-[(4-fluorophenyl)methylamino]benzamide Chemical compound C=1C=C2C(C)(C)CNCC2=CC=1NC(=O)C1=CC=CC=C1NCC1=CC=C(F)C=C1 FTNKCGULGWHQPV-UHFFFAOYSA-N 0.000 claims description 3
- GUIOOGNPPDHMRU-MRXNPFEDSA-N n-(4,4-dimethyl-2,3-dihydro-1h-isoquinolin-7-yl)-2-[[(1r)-1-[2-(methylamino)pyrimidin-4-yl]ethyl]amino]benzamide Chemical compound CNC1=NC=CC([C@@H](C)NC=2C(=CC=CC=2)C(=O)NC=2C=C3C(C(CNC3)(C)C)=CC=2)=N1 GUIOOGNPPDHMRU-MRXNPFEDSA-N 0.000 claims description 3
- SKHDQKQGFCSJDS-UHFFFAOYSA-N n-(4,4-dimethyl-2,3-dihydro-1h-isoquinolin-7-yl)-2-fluoro-6-[(2-methoxypyridin-4-yl)methylamino]benzamide Chemical compound C1=NC(OC)=CC(CNC=2C(=C(F)C=CC=2)C(=O)NC=2C=C3C(C(CNC3)(C)C)=CC=2)=C1 SKHDQKQGFCSJDS-UHFFFAOYSA-N 0.000 claims description 3
- SHNBMTHPUCMPQC-UHFFFAOYSA-N n-(4,4-dimethyl-2,3-dihydro-1h-isoquinolin-7-yl)-4-fluoro-2-[(2-methoxypyridin-4-yl)methylamino]benzamide Chemical compound C1=NC(OC)=CC(CNC=2C(=CC=C(F)C=2)C(=O)NC=2C=C3C(C(CNC3)(C)C)=CC=2)=C1 SHNBMTHPUCMPQC-UHFFFAOYSA-N 0.000 claims description 3
- FBSYURCCDOMSHX-UHFFFAOYSA-N n-(4,4-dimethyl-2,3-dihydro-1h-isoquinolin-7-yl)-5-fluoro-2-[(2-methoxypyridin-4-yl)methylamino]benzamide Chemical compound C1=NC(OC)=CC(CNC=2C(=CC(F)=CC=2)C(=O)NC=2C=C3C(C(CNC3)(C)C)=CC=2)=C1 FBSYURCCDOMSHX-UHFFFAOYSA-N 0.000 claims description 3
- YTITUUIWIKQKDQ-UHFFFAOYSA-N n-(4-tert-butylphenyl)-2-(isoquinolin-7-ylamino)benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1NC(=O)C1=CC=CC=C1NC1=CC=C(C=CN=C2)C2=C1 YTITUUIWIKQKDQ-UHFFFAOYSA-N 0.000 claims description 3
- HAZZWCMIYVZRGW-UHFFFAOYSA-N n-[4-[2-(1-methylpiperidin-4-yl)propan-2-yl]phenyl]-2-(quinolin-4-ylmethylamino)benzamide Chemical compound C1CN(C)CCC1C(C)(C)C(C=C1)=CC=C1NC(=O)C1=CC=CC=C1NCC1=CC=NC2=CC=CC=C12 HAZZWCMIYVZRGW-UHFFFAOYSA-N 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 2
- 229940125697 hormonal agent Drugs 0.000 claims description 2
- YYVHACOWHFZZJT-UHFFFAOYSA-N n-(3,3-dimethyl-1,2-dihydroindol-6-yl)-2-(quinolin-4-ylmethylamino)benzamide Chemical compound C1=CC=C2C(CNC3=CC=CC=C3C(=O)NC=3C=C4NCC(C4=CC=3)(C)C)=CC=NC2=C1 YYVHACOWHFZZJT-UHFFFAOYSA-N 0.000 claims description 2
- YAWXEPJVBFFVAI-UHFFFAOYSA-N n-(4,4-dimethyl-2,3-dihydro-1h-isoquinolin-7-yl)-3-fluoro-2-[(4-fluorophenyl)methylamino]benzamide Chemical compound C=1C=C2C(C)(C)CNCC2=CC=1NC(=O)C1=CC=CC(F)=C1NCC1=CC=C(F)C=C1 YAWXEPJVBFFVAI-UHFFFAOYSA-N 0.000 claims description 2
- JQUISUUSKKADNO-UHFFFAOYSA-N n-(4,4-dimethyl-2,3-dihydro-1h-isoquinolin-7-yl)-6-fluoro-6-[(4-fluorophenyl)methylamino]cyclohexa-2,4-diene-1-carboxamide Chemical compound C=1C=C2C(C)(C)CNCC2=CC=1NC(=O)C1C=CC=CC1(F)NCC1=CC=C(F)C=C1 JQUISUUSKKADNO-UHFFFAOYSA-N 0.000 claims description 2
- YHNUIHYDPTVZRY-UHFFFAOYSA-N n-(4,4-dimethyl-2,3-dihydro-1h-quinolin-7-yl)-2-(1h-pyrrolo[2,3-b]pyridin-3-ylmethylamino)benzamide Chemical compound C1=CC=C2C(CNC3=CC=CC=C3C(=O)NC=3C=C4NCCC(C4=CC=3)(C)C)=CNC2=N1 YHNUIHYDPTVZRY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- PYWPWPPRAYOLIB-UHFFFAOYSA-N 1-(3,3-dimethyl-2h-indol-1-yl)ethanone Chemical compound C1=CC=C2N(C(=O)C)CC(C)(C)C2=C1 PYWPWPPRAYOLIB-UHFFFAOYSA-N 0.000 claims 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- 239000000677 immunologic agent Substances 0.000 claims 1
- 229940124541 immunological agent Drugs 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 30
- 239000000543 intermediate Substances 0.000 abstract description 10
- 230000002265 prevention Effects 0.000 abstract description 4
- 239000000651 prodrug Substances 0.000 abstract 1
- 229940002612 prodrug Drugs 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 212
- 239000000203 mixture Substances 0.000 description 178
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 150
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 107
- 235000019439 ethyl acetate Nutrition 0.000 description 106
- 239000000460 chlorine Substances 0.000 description 104
- 230000002829 reductive effect Effects 0.000 description 98
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 80
- 238000001819 mass spectrum Methods 0.000 description 74
- 239000000243 solution Substances 0.000 description 73
- 239000007787 solid Substances 0.000 description 72
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 64
- 239000011734 sodium Substances 0.000 description 64
- 239000012267 brine Substances 0.000 description 54
- 125000004432 carbon atom Chemical group C* 0.000 description 54
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 54
- 239000012044 organic layer Substances 0.000 description 53
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 41
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 40
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- 229960000523 zalcitabine Drugs 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Indole Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
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| US39514402P | 2002-07-09 | 2002-07-09 | |
| US10/615,809 US7307088B2 (en) | 2002-07-09 | 2003-07-08 | Substituted anthranilic amide derivatives and methods of use |
| PCT/US2003/021601 WO2004005279A2 (en) | 2002-07-09 | 2003-07-09 | Substituted anthranilic amide derivatives and methods of use |
Publications (2)
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| JP2004520114A Pending JP2006502112A (ja) | 2002-07-09 | 2003-07-09 | 置換アントラニルアミド誘導体および使用方法 |
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| EP (1) | EP1519921A2 (enExample) |
| JP (1) | JP2006502112A (enExample) |
| AU (1) | AU2003256481B2 (enExample) |
| CA (1) | CA2489166A1 (enExample) |
| MX (1) | MXPA05000120A (enExample) |
| PL (1) | PL375586A1 (enExample) |
| WO (1) | WO2004005279A2 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012512905A (ja) * | 2008-12-19 | 2012-06-07 | アムジエン・インコーポレーテツド | 1−アセチル−6−アミノ−3,3−ジメチル−2,3−ジヒドロインドールを調製するための改良された方法 |
| JP2012521995A (ja) * | 2009-03-25 | 2012-09-20 | アボット・ラボラトリーズ | 抗ウィルス性化合物およびこの使用 |
Families Citing this family (101)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10023484A1 (de) * | 2000-05-09 | 2001-11-22 | Schering Ag | Anthranylamide und deren Verwendung als Arzneimittel |
| US7615565B2 (en) * | 2002-07-31 | 2009-11-10 | Bayer Schering Pharma Aktiengesellschaft | VEGFR-2 and VEGFR-3 inhibitory anthranilamide pyridines |
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| KR101254371B1 (ko) | 2003-07-18 | 2013-05-02 | 암젠 프레몬트 인코포레이티드 | 간세포 성장인자에 결합하는 분리된 항체 |
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| US12441736B2 (en) | 2018-12-20 | 2025-10-14 | Amgen Inc. | KIF18A inhibitors |
| CA3123042A1 (en) | 2018-12-20 | 2020-06-25 | Amgen Inc. | Kif18a inhibitors |
| JP2022513967A (ja) | 2018-12-20 | 2022-02-09 | アムジエン・インコーポレーテツド | Kif18a阻害剤として有用なヘテロアリールアミド |
| US20230148450A9 (en) | 2019-03-01 | 2023-05-11 | Revolution Medicines, Inc. | Bicyclic heteroaryl compounds and uses thereof |
| AU2020232616A1 (en) | 2019-03-01 | 2021-09-09 | Revolution Medicines, Inc. | Bicyclic heterocyclyl compounds and uses thereof |
| EP3738593A1 (en) | 2019-05-14 | 2020-11-18 | Amgen, Inc | Dosing of kras inhibitor for treatment of cancers |
| NZ782284A (en) | 2019-05-21 | 2024-11-29 | Amgen Inc | Solid state forms |
| JP7699100B2 (ja) | 2019-08-02 | 2025-06-26 | アムジエン・インコーポレーテツド | Kif18a阻害剤 |
| CN114269731A (zh) | 2019-08-02 | 2022-04-01 | 美国安进公司 | Kif18a抑制剂 |
| WO2021026098A1 (en) | 2019-08-02 | 2021-02-11 | Amgen Inc. | Kif18a inhibitors |
| JP7756070B2 (ja) | 2019-08-02 | 2025-10-17 | アムジエン・インコーポレーテツド | Kif18a阻害剤としてのピリジン誘導体 |
| MX2022004656A (es) | 2019-10-24 | 2022-05-25 | Amgen Inc | Derivados de piridopirimidina utiles como inhibidores de kras g12c y kras g12d en el tratamiento del cancer. |
| CA3159561A1 (en) | 2019-11-04 | 2021-05-14 | Revolution Medicines, Inc. | Ras inhibitors |
| KR20220109406A (ko) | 2019-11-04 | 2022-08-04 | 레볼루션 메디슨즈, 인크. | Ras 억제제 |
| EP4055028A1 (en) | 2019-11-04 | 2022-09-14 | Revolution Medicines, Inc. | Ras inhibitors |
| EP4620531A3 (en) | 2019-11-08 | 2025-11-26 | Revolution Medicines, Inc. | Bicyclic heteroaryl compounds and uses thereof |
| JP2023501522A (ja) | 2019-11-14 | 2023-01-18 | アムジエン・インコーポレーテツド | Kras g12c阻害剤化合物の改良合成法 |
| AR120457A1 (es) | 2019-11-14 | 2022-02-16 | Amgen Inc | Síntesis mejorada del compuesto inhibidor de g12c de kras |
| WO2021108683A1 (en) | 2019-11-27 | 2021-06-03 | Revolution Medicines, Inc. | Covalent ras inhibitors and uses thereof |
| TW202140011A (zh) | 2020-01-07 | 2021-11-01 | 美商銳新醫藥公司 | Shp2抑制劑給藥和治療癌症的方法 |
| AU2021293228A1 (en) | 2020-06-18 | 2023-02-09 | Revolution Medicines, Inc. | Methods for delaying, preventing, and treating acquired resistance to RAS inhibitors |
| US20250195521A1 (en) | 2020-09-03 | 2025-06-19 | Revolution Medicines, Inc. | Use of sos1 inhibitors to treat malignancies with shp2 mutations |
| IL301298A (en) | 2020-09-15 | 2023-05-01 | Revolution Medicines Inc | Indole derivatives as RAS inhibitors in cancer therapy |
| CN116134017B (zh) * | 2020-09-24 | 2025-03-04 | 贝达药业股份有限公司 | 双环化合物及其应用 |
| JP2024501280A (ja) | 2020-12-22 | 2024-01-11 | キル・レガー・セラピューティクス・インコーポレーテッド | Sos1阻害剤およびその使用 |
| TW202309052A (zh) | 2021-05-05 | 2023-03-01 | 美商銳新醫藥公司 | Ras抑制劑 |
| WO2022235870A1 (en) | 2021-05-05 | 2022-11-10 | Revolution Medicines, Inc. | Ras inhibitors for the treatment of cancer |
| EP4334324A1 (en) | 2021-05-05 | 2024-03-13 | Revolution Medicines, Inc. | Covalent ras inhibitors and uses thereof |
| AR127308A1 (es) | 2021-10-08 | 2024-01-10 | Revolution Medicines Inc | Inhibidores ras |
| TW202340214A (zh) | 2021-12-17 | 2023-10-16 | 美商健臻公司 | 做為shp2抑制劑之吡唑并吡𠯤化合物 |
| EP4227307A1 (en) | 2022-02-11 | 2023-08-16 | Genzyme Corporation | Pyrazolopyrazine compounds as shp2 inhibitors |
| JP2025509217A (ja) | 2022-03-07 | 2025-04-11 | アムジエン・インコーポレーテツド | 4-メチル-2-プロパン-2-イル-ピリジン-3-カルボニトリルを調製するための方法 |
| WO2023172940A1 (en) | 2022-03-08 | 2023-09-14 | Revolution Medicines, Inc. | Methods for treating immune refractory lung cancer |
| KR20250022133A (ko) | 2022-06-10 | 2025-02-14 | 레볼루션 메디슨즈, 인크. | 거대고리 ras 억제제 |
| AU2023358792A1 (en) | 2022-10-14 | 2025-04-17 | Black Diamond Therapeutics, Inc. | Methods of treating cancers using isoquinoline or 6-aza-quinoline derivatives |
| KR20250164828A (ko) | 2023-03-30 | 2025-11-25 | 레볼루션 메디슨즈, 인크. | Ras gtp 가수분해 유도를 위한 조성물 및 이의 용도 |
| AU2024243852A1 (en) | 2023-04-07 | 2025-11-06 | Revolution Medicines, Inc. | Macrocyclic ras inhibitors |
| WO2024211663A1 (en) | 2023-04-07 | 2024-10-10 | Revolution Medicines, Inc. | Condensed macrocyclic compounds as ras inhibitors |
| KR20250172857A (ko) | 2023-04-14 | 2025-12-09 | 레볼루션 메디슨즈, 인크. | Ras 억제제의 결정형 |
| KR20250169290A (ko) | 2023-04-14 | 2025-12-02 | 레볼루션 메디슨즈, 인크. | Ras 억제제의 결정형, 이를 함유하는 조성물 및 이의 사용 방법 |
| AU2024265078A1 (en) | 2023-05-04 | 2025-12-11 | Revolution Medicines, Inc. | Combination therapy for a ras related disease or disorder |
| WO2025034702A1 (en) | 2023-08-07 | 2025-02-13 | Revolution Medicines, Inc. | Rmc-6291 for use in the treatment of ras protein-related disease or disorder |
| WO2025080946A2 (en) | 2023-10-12 | 2025-04-17 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2025137507A1 (en) | 2023-12-22 | 2025-06-26 | Regor Pharmaceuticals, Inc. | Sos1 inhibitors and uses thereof |
| WO2025171296A1 (en) | 2024-02-09 | 2025-08-14 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2025240847A1 (en) | 2024-05-17 | 2025-11-20 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2025255438A1 (en) | 2024-06-07 | 2025-12-11 | Revolution Medicines, Inc. | Methods of treating a ras protein-related disease or disorder |
Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4880574A (enExample) * | 1972-01-21 | 1973-10-29 | ||
| GB1474296A (en) * | 1975-01-23 | 1977-05-18 | Wyeth John & Brother Ltd | 4-aminoquinoline derivatives |
| US4357333A (en) * | 1977-09-14 | 1982-11-02 | John Wyeth & Brother Limited | N-Substituted 2-(8-halo and trifluoromethyl 4-quinolylamino)benzamides and analgesic use thereof |
| WO2000027820A1 (en) * | 1998-11-10 | 2000-05-18 | Novartis Ag | N-aryl(thio)anthranilic acid amide derivatives, their preparation and their use as vegf receptor tyrosine kinase inhibitors |
| WO2000027819A2 (de) * | 1998-11-10 | 2000-05-18 | Schering Aktiengesellschaft | Anthranilsäureamide und deren verwendung als arzneimittel |
| WO2001085671A2 (de) * | 2000-05-09 | 2001-11-15 | Schering Aktiengesellschaft | Anthranylamide und deren verwendung als arzneimittel |
| WO2001085719A1 (de) * | 2000-05-09 | 2001-11-15 | Schering Aktiengesellschaft | Ortho substituierte anthranilsäureamide und deren verwendung als arzneimittel |
| JP2004528379A (ja) * | 2001-05-08 | 2004-09-16 | シエーリング アクチエンゲゼルシャフト | Vegfr−2およびvegfr−3インヒビターとしての選択的アントラニルアミドピリジンアミド |
| JP2004528378A (ja) * | 2001-05-08 | 2004-09-16 | シエーリング アクチエンゲゼルシャフト | N−オキシドアントラニルアミド誘導体と医薬製剤としての利用 |
| JP2004532281A (ja) * | 2001-05-08 | 2004-10-21 | シエーリング アクチエンゲゼルシャフト | シアノアントラニルアミド誘導体およびそれらの薬剤としての使用 |
| JP2005508382A (ja) * | 2001-11-08 | 2005-03-31 | ノバルティス アクチエンゲゼルシャフト | アントラニル酸アミド類およびその医薬的使用 |
| JP2005511602A (ja) * | 2001-11-08 | 2005-04-28 | ノバルティス アクチエンゲゼルシャフト | アントラニル酸アミドおよびvegf受容体チロシンキナーゼ阻害剤としてのその使用 |
Family Cites Families (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH438343A (de) * | 1962-11-08 | 1967-06-30 | Thomae Gmbh Dr K | Verfahren zur Herstellung von 5,6-Dihydro-6-oxo-11H-pyrido (2,3-b) (1,4)-benzodiazepinen |
| US3226394A (en) * | 1964-06-16 | 1965-12-28 | Shulton Inc | Pyridylethylated anthranilamides and derivatives thereof |
| US3822277A (en) * | 1967-11-13 | 1974-07-02 | C Dufour | Certain pyridyl cyclopropylamides |
| US3452019A (en) * | 1967-11-16 | 1969-06-24 | Wallace & Tiernan Inc | 1-phenylalkyl-tetrahydro-halo-sulfamyl-quinazolinone |
| US3557111A (en) * | 1968-03-29 | 1971-01-19 | Bola Vithal Shetty | N and n,n-alkyl,acyl and arylsulfamyl-tetrahydroquinazolinones |
| US3567746A (en) * | 1968-07-10 | 1971-03-02 | Pennwalt Corp | N-aryl benzamides |
| DE2934543A1 (de) * | 1979-08-27 | 1981-04-02 | Basf Ag, 6700 Ludwigshafen | Substituierte n-benzoylanthranilsaeurederivate und deren anydroverbindungen, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| JPH0233030B2 (ja) | 1982-01-18 | 1990-07-25 | Mitsui Toatsu Chemicals | Surufuamoiruansokukosanjudotaioyobisoreojukoseibuntoshitefukumuchiryoyososeibutsu |
| FR2540870A1 (fr) * | 1983-02-15 | 1984-08-17 | Provesan Sa | Nouveaux derives de betaines n-iminopyridinium, leur preparation et leur application en tant que medicaments |
| SU1156362A1 (ru) | 1983-02-17 | 1991-07-30 | Пермский государственный фармацевтический институт | Ариламиды П-(2 @ ,4 @ )- или (3 @ ,4 @ )-диметоксибензилантраниловых кислот как промежуточные вещества дл синтеза биологически активных перхлоратов 1-[(2 @ ,4 @ ) или (3 @ ,4 @ )-диметоксибензил]-2-метил-3-арил-4-(3Н)-хиназолинони |
| DE3305755A1 (de) * | 1983-02-19 | 1984-08-23 | Gödecke AG, 1000 Berlin | N-phenyl-benzamid-derivate, verfahren zu deren herstellung und deren verwendung bei der bekaempfung von erkranungen des immunsystems |
| DE69002079T2 (de) | 1989-04-20 | 1993-11-18 | Boehringer Ingelheim Pharma | 5,11-Dihydro-6H-dipyrido [3,2-b:2',3'-e]diazepin-6-one und deren Verwendung in der Vorbeugung und Behandlung von AIDS. |
| DK0410148T3 (da) | 1989-06-28 | 1994-08-08 | Boehringer Ingelheim Pharma | Hidtil ukendte 5,11-dihydro-6H-dipyrido(3,2-b:2,3-e)-(1,4)diazepin-6-oner og -thioner og deres anvendelse til forebyggelse eller behandling af AIDS |
| CA2030056C (en) | 1989-11-17 | 1995-10-17 | Karl D. Hargrave | 5,11-dihydro-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepines and their use in the prevention or treatment of hiv infection |
| US5571912A (en) * | 1990-10-19 | 1996-11-05 | Boehringer Ingelheim Pharmaceuticals, Inc. | Method for the preparation of 5,11-dihydro-6h-dipyrido [3,2-b:2',3'-e][1,4]diazepines |
| EP1195372A1 (en) | 1994-04-18 | 2002-04-10 | Mitsubishi Pharma Corporation | N-heterocyclic substituted benzamide derivatives with antihypertensive activity |
| US5559135A (en) * | 1994-09-14 | 1996-09-24 | Merck & Co., Inc. | Endothelin antagonists bearing pyridyl amides |
| US5532358A (en) * | 1994-10-12 | 1996-07-02 | Boehringer Ingelheim Pharmaceuticals, Inc. | Method for preparing alkyl-5,11-dihydro-6h-dipyrido[3,2-B:2',3'-E] [1,4] diazepin-6-ones |
| GB9511694D0 (en) | 1995-06-09 | 1995-08-02 | Fujisawa Pharmaceutical Co | Benzamide derivatives |
| US5770613A (en) * | 1995-09-29 | 1998-06-23 | Geron Corporation | Telomerase inhibitors |
| US5663357A (en) * | 1995-11-22 | 1997-09-02 | Allergan | Substituted heteroarylamides having retinoid-like biological activity |
| US6008234A (en) * | 1996-09-12 | 1999-12-28 | Berlex Laboratories, Inc. | Benzamidine derivatives substituted by cyclic amino acid and cyclic hydroxy acid derivatives and their use as anti-coagulants |
| AUPO395396A0 (en) | 1996-12-02 | 1997-01-02 | Fujisawa Pharmaceutical Co., Ltd. | Benzamide derivatives |
| TW523506B (en) * | 1996-12-18 | 2003-03-11 | Ono Pharmaceutical Co | Sulfonamide or carbamide derivatives and drugs containing the same as active ingredients |
| EA003528B1 (ru) | 1997-04-04 | 2003-06-26 | Пфайзер Продактс Инк. | Производные никотинамида, их применение, фармацевтическая композиция, способ лечения и способ ингибирования изоферментов фдэ4 d |
| US5919970A (en) * | 1997-04-24 | 1999-07-06 | Allergan Sales, Inc. | Substituted diaryl or diheteroaryl methanes, ethers and amines having retinoid agonist, antagonist or inverse agonist type biological activity |
| EP1014962A4 (en) * | 1997-06-26 | 2007-06-27 | Lilly Co Eli | ANTITHROMBOTIC AGENTS |
| AU8270298A (en) * | 1997-06-26 | 1999-01-19 | Eli Lilly And Company | Antithrombotic agents |
| US6417200B1 (en) * | 1997-06-26 | 2002-07-09 | Eli Lilly And Company | Antithrombotic agents |
| ATE306261T1 (de) * | 1997-06-26 | 2005-10-15 | Lilly Co Eli | Antithrombosemittel |
| US6140351A (en) * | 1997-12-19 | 2000-10-31 | Berlex Laboratories, Inc. | Ortho-anthranilamide derivatives as anti-coagulants |
| IL135536A0 (en) | 1997-12-19 | 2001-05-20 | Schering Ag | Ortho-anthranilamide derivatives and pharmaceutical compositions containing the same |
| US6271237B1 (en) * | 1997-12-22 | 2001-08-07 | Dupont Pharmaceuticals Company | Nitrogen containing heteromatics with ortho-substituted P1s as factor Xa inhabitors |
| CA2332957A1 (en) | 1998-06-05 | 1999-12-09 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substituted 1-(4-aminophenyl)pyrazoles and their use as anti-inflammatory agents |
| CZ302691B6 (cs) | 1998-07-08 | 2011-09-07 | Sanofi - Aventis Deutschland GmbH | N-Arylamidová sloucenina, zpusob její prípravy, farmaceutický prostredek tuto slouceninu obsahující, tato sloucenina pro použití jako aktivátor a pro použití k terapii nebo profylaxi |
| US6331640B1 (en) * | 1998-10-13 | 2001-12-18 | Hoffmann-La Roche Inc. | Diaminopropionic acid derivatives |
| WO2000039117A1 (en) | 1998-12-23 | 2000-07-06 | Eli Lilly And Company | HETEROROAROMATIC AMIDES AS INHIBITOR OF FACTOR Xa |
| EP1140903B1 (en) | 1998-12-23 | 2004-08-04 | Eli Lilly And Company | Aromatic amides |
| JP2004522689A (ja) * | 1998-12-23 | 2004-07-29 | イーライ・リリー・アンド・カンパニー | 抗血栓アミド類 |
| JP2000256358A (ja) | 1999-03-10 | 2000-09-19 | Yamanouchi Pharmaceut Co Ltd | ピラゾール誘導体 |
| DE19941540C2 (de) | 1999-09-01 | 2002-08-29 | Aventis Pharma Gmbh | Sulfonylcarboxamide zur Herstellung von Medikamenten zur Prophylaxe oder Behandlung von Hyperlipidämie |
| GB9924862D0 (en) | 1999-10-20 | 1999-12-22 | Celltech Therapeutics Ltd | Chemical compounds |
| AUPQ365299A0 (en) | 1999-10-25 | 1999-11-18 | Fujisawa Pharmaceutical Co., Ltd. | Anthranilic acid derivatives |
| JP2003520854A (ja) * | 2000-01-27 | 2003-07-08 | サイトビア インコーポレイテッド | カスパーゼのアクチベーターおよびアポトーシスのインデューサーとしての置換ニコチンアミドおよび類似物およびそれらの使用 |
| GB0001930D0 (en) | 2000-01-27 | 2000-03-22 | Novartis Ag | Organic compounds |
| WO2001064642A2 (en) | 2000-02-29 | 2001-09-07 | Cor Therapeutics, Inc. | Benzamides and related inhibitors of factor xa |
| DE10021246A1 (de) | 2000-04-25 | 2001-10-31 | Schering Ag | Substituierte Benzoesäureamide und deren Verwendung als Arzneimittel |
| DE10023485A1 (de) | 2000-05-09 | 2001-11-22 | Schering Ag | Anthranylalkyl- und -cycloalkylamide und deren Verwendung als Arzneimittel |
| DE10023492A1 (de) | 2000-05-09 | 2001-11-22 | Schering Ag | Aza- und Polyazanthranylamide und deren Verwendung als Arzneimittel |
| US6934248B1 (en) | 2000-07-20 | 2005-08-23 | Nortel Networks Limited | Apparatus and method for optical communication protection |
| DE10060809A1 (de) | 2000-12-07 | 2002-06-20 | Aventis Pharma Gmbh | Substituierte Anthranilsäuren, ihre Verwendung als Medikament oder Diagnostikum, sowie sie enthaltendes Medikament, sowie ein pharmazeutisches Kombinationspräparat mit einem Natrium/Wasserstoff-Austausch (NHE)-Blocker |
| WO2002076959A1 (en) * | 2001-03-23 | 2002-10-03 | Takeda Chemical Industries, Ltd. | Five-membered heterocyclic alkanoic acid derivative |
| US7312235B2 (en) * | 2001-03-30 | 2007-12-25 | Millennium Pharmaceuticals, Inc. | Benzamide inhibitors of factor Xa |
| DE10125295A1 (de) | 2001-05-15 | 2002-11-21 | Schering Ag | Cyanoanthranylamid-Derivate und deren Verwendung als Arzneimittel (II) |
| GB0203193D0 (en) | 2002-02-11 | 2002-03-27 | Pfizer Ltd | Nicotinamide derivatives useful as pde4 inhibitors |
| MXPA04007737A (es) | 2002-02-11 | 2004-10-15 | Pfizer | Derivados de nicotinamida utiles como inhibidores de fosfodesterasas 4. |
| US20030195192A1 (en) | 2002-04-05 | 2003-10-16 | Fortuna Haviv | Nicotinamides having antiangiogenic activity |
| US7517894B2 (en) * | 2002-07-31 | 2009-04-14 | Bayer Schering Pharma Ag | VEGFR-2 and VEGFR-3 inhibitory anthranilamide pyridines |
-
2003
- 2003-07-08 US US10/615,809 patent/US7307088B2/en not_active Expired - Lifetime
- 2003-07-09 JP JP2004520114A patent/JP2006502112A/ja active Pending
- 2003-07-09 CA CA002489166A patent/CA2489166A1/en not_active Abandoned
- 2003-07-09 MX MXPA05000120A patent/MXPA05000120A/es not_active Application Discontinuation
- 2003-07-09 EP EP03763451A patent/EP1519921A2/en not_active Withdrawn
- 2003-07-09 WO PCT/US2003/021601 patent/WO2004005279A2/en not_active Ceased
- 2003-07-09 PL PL03375586A patent/PL375586A1/xx unknown
- 2003-07-09 AU AU2003256481A patent/AU2003256481B2/en not_active Ceased
Patent Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4880574A (enExample) * | 1972-01-21 | 1973-10-29 | ||
| GB1474296A (en) * | 1975-01-23 | 1977-05-18 | Wyeth John & Brother Ltd | 4-aminoquinoline derivatives |
| US4357333A (en) * | 1977-09-14 | 1982-11-02 | John Wyeth & Brother Limited | N-Substituted 2-(8-halo and trifluoromethyl 4-quinolylamino)benzamides and analgesic use thereof |
| WO2000027820A1 (en) * | 1998-11-10 | 2000-05-18 | Novartis Ag | N-aryl(thio)anthranilic acid amide derivatives, their preparation and their use as vegf receptor tyrosine kinase inhibitors |
| WO2000027819A2 (de) * | 1998-11-10 | 2000-05-18 | Schering Aktiengesellschaft | Anthranilsäureamide und deren verwendung als arzneimittel |
| WO2001085671A2 (de) * | 2000-05-09 | 2001-11-15 | Schering Aktiengesellschaft | Anthranylamide und deren verwendung als arzneimittel |
| WO2001085719A1 (de) * | 2000-05-09 | 2001-11-15 | Schering Aktiengesellschaft | Ortho substituierte anthranilsäureamide und deren verwendung als arzneimittel |
| JP2004528379A (ja) * | 2001-05-08 | 2004-09-16 | シエーリング アクチエンゲゼルシャフト | Vegfr−2およびvegfr−3インヒビターとしての選択的アントラニルアミドピリジンアミド |
| JP2004528378A (ja) * | 2001-05-08 | 2004-09-16 | シエーリング アクチエンゲゼルシャフト | N−オキシドアントラニルアミド誘導体と医薬製剤としての利用 |
| JP2004532281A (ja) * | 2001-05-08 | 2004-10-21 | シエーリング アクチエンゲゼルシャフト | シアノアントラニルアミド誘導体およびそれらの薬剤としての使用 |
| JP2005508382A (ja) * | 2001-11-08 | 2005-03-31 | ノバルティス アクチエンゲゼルシャフト | アントラニル酸アミド類およびその医薬的使用 |
| JP2005511602A (ja) * | 2001-11-08 | 2005-04-28 | ノバルティス アクチエンゲゼルシャフト | アントラニル酸アミドおよびvegf受容体チロシンキナーゼ阻害剤としてのその使用 |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012512905A (ja) * | 2008-12-19 | 2012-06-07 | アムジエン・インコーポレーテツド | 1−アセチル−6−アミノ−3,3−ジメチル−2,3−ジヒドロインドールを調製するための改良された方法 |
| JP2012521995A (ja) * | 2009-03-25 | 2012-09-20 | アボット・ラボラトリーズ | 抗ウィルス性化合物およびこの使用 |
| US9353091B2 (en) | 2009-03-25 | 2016-05-31 | Abbvie Inc. | Antiviral compounds and uses thereof |
| US9637478B2 (en) | 2009-03-25 | 2017-05-02 | Abbvie Inc. | Antiviral compounds and uses thereof |
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| CA2489166A1 (en) | 2004-01-15 |
| PL375586A1 (en) | 2005-11-28 |
| MXPA05000120A (es) | 2005-04-08 |
| AU2003256481B2 (en) | 2007-08-09 |
| AU2003256481A1 (en) | 2004-01-23 |
| WO2004005279A3 (en) | 2004-03-11 |
| WO2004005279A2 (en) | 2004-01-15 |
| US7307088B2 (en) | 2007-12-11 |
| EP1519921A2 (en) | 2005-04-06 |
| US20040087568A1 (en) | 2004-05-06 |
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