JP2019521153A5 - - Google Patents
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- Publication number
- JP2019521153A5 JP2019521153A5 JP2019501720A JP2019501720A JP2019521153A5 JP 2019521153 A5 JP2019521153 A5 JP 2019521153A5 JP 2019501720 A JP2019501720 A JP 2019501720A JP 2019501720 A JP2019501720 A JP 2019501720A JP 2019521153 A5 JP2019521153 A5 JP 2019521153A5
- Authority
- JP
- Japan
- Prior art keywords
- methylquinoxalin
- difluoromethoxy
- thiazol
- alkyl
- thiazole
- 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
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- 125000000217 alkyl group Chemical group 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 208000035475 disorder Diseases 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 230000009424 thromboembolic effect Effects 0.000 claims 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 6
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 230000000747 cardiac effect Effects 0.000 claims 3
- -1 hydroxymethyl piperidinylmethyl Chemical group 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- QOZWJCBNEYYVPJ-UHFFFAOYSA-N 2,3-difluoro-5-[2-(2-methoxy-7-methylquinoxalin-5-yl)-1,3-thiazol-5-yl]phenol Chemical compound FC1=C(C=C(C=C1F)C1=CN=C(S1)C1=C2N=CC(=NC2=CC(=C1)C)OC)O QOZWJCBNEYYVPJ-UHFFFAOYSA-N 0.000 claims 2
- KMQLELIWGBYVTP-UHFFFAOYSA-N 2-(2-methoxy-7-methylquinoxalin-5-yl)-5-(5-methoxypyridin-2-yl)-1,3-thiazole Chemical compound COC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C1=NC=C(C=C1)OC)C KMQLELIWGBYVTP-UHFFFAOYSA-N 0.000 claims 2
- KLRYZTYAMPNRSC-UHFFFAOYSA-N 2-(difluoromethoxy)-7-methyl-5-(1-phenylpyrazol-4-yl)quinoxaline Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1C=NN(C=1)C1=CC=CC=C1)C)F KLRYZTYAMPNRSC-UHFFFAOYSA-N 0.000 claims 2
- GSWWWFNZWRLPBY-UHFFFAOYSA-N 2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-1,3-thiazole Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC=CN=1)C)F GSWWWFNZWRLPBY-UHFFFAOYSA-N 0.000 claims 2
- GUTFBFMPHVGVCH-UHFFFAOYSA-N 2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-4-ethenyl-1,3-thiazole Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC=C(N=1)C=C)C)F GUTFBFMPHVGVCH-UHFFFAOYSA-N 0.000 claims 2
- WXNNATVJGMDOEG-UHFFFAOYSA-N 2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-4-methyl-1,3-thiazole Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC=C(N=1)C)C)F WXNNATVJGMDOEG-UHFFFAOYSA-N 0.000 claims 2
- JRDLAWTVRYXZCD-UHFFFAOYSA-N 2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-4-methyl-5-(1H-pyrazol-5-yl)-1,3-thiazole Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=C(N=1)C)C1=CC=NN1)C)F JRDLAWTVRYXZCD-UHFFFAOYSA-N 0.000 claims 2
- QPBWHYFVCLNXCJ-UHFFFAOYSA-N 2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-5-(1H-indol-4-yl)-1,3-thiazole Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C1=C2C=CNC2=CC=C1)C)F QPBWHYFVCLNXCJ-UHFFFAOYSA-N 0.000 claims 2
- WTKCGISOQAZRGV-UHFFFAOYSA-N 2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-5-(1H-indol-6-yl)-1,3-thiazole Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C1=CC=C2C=CNC2=C1)C)F WTKCGISOQAZRGV-UHFFFAOYSA-N 0.000 claims 2
- BWIFAYWOWYSGTB-UHFFFAOYSA-N 2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-5-(1H-indol-7-yl)-1,3-thiazole Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C=1C=CC=C2C=CNC=12)C)F BWIFAYWOWYSGTB-UHFFFAOYSA-N 0.000 claims 2
- QJDQNIZHIUOCHA-UHFFFAOYSA-N 2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-5-(1H-pyrazol-5-yl)-1,3-thiazole Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C1=CC=NN1)C)F QJDQNIZHIUOCHA-UHFFFAOYSA-N 0.000 claims 2
- OQWZSPQLGJQOOG-UHFFFAOYSA-N 2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-5-[2-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C1=C(C=CC=C1)C(F)(F)F)C)F OQWZSPQLGJQOOG-UHFFFAOYSA-N 0.000 claims 2
- PUGGNWYCUNTNTQ-UHFFFAOYSA-N 2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-5-methyl-1,3-thiazole Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C)C)F PUGGNWYCUNTNTQ-UHFFFAOYSA-N 0.000 claims 2
- VLOVPGDPMNSXDU-UHFFFAOYSA-N 2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-5-phenyl-1,3,4-thiadiazole Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=NN=1)C1=CC=CC=C1)C)F VLOVPGDPMNSXDU-UHFFFAOYSA-N 0.000 claims 2
- YOAAQWMMPXYFPH-UHFFFAOYSA-N 2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-5-phenyl-1,3-thiazole Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C1=CC=CC=C1)C)F YOAAQWMMPXYFPH-UHFFFAOYSA-N 0.000 claims 2
- CFKDJJWLPLMMJF-UHFFFAOYSA-N 2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-5-piperidin-1-yl-1,3-thiazole Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)N1CCCCC1)C)F CFKDJJWLPLMMJF-UHFFFAOYSA-N 0.000 claims 2
- SVFNEKRBCIMEPP-UHFFFAOYSA-N 2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-5-pyridin-2-yl-1,3-thiazole Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C1=NC=CC=C1)C)F SVFNEKRBCIMEPP-UHFFFAOYSA-N 0.000 claims 2
- VNNWJZDZGJZSDO-UHFFFAOYSA-N 2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-5-pyridin-3-yl-1,3-thiazole Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C=1C=NC=CC=1)C)F VNNWJZDZGJZSDO-UHFFFAOYSA-N 0.000 claims 2
- FCECAADEPLEMGD-UHFFFAOYSA-N 2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-5-pyridin-4-yl-1,3-thiazole Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C1=CC=NC=C1)C)F FCECAADEPLEMGD-UHFFFAOYSA-N 0.000 claims 2
- BCUXLBVQPQKOSL-UHFFFAOYSA-N 2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-N-(4-methoxyphenyl)-1,3-thiazole-4-carboxamide Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC=C(N=1)C(=O)NC1=CC=C(C=C1)OC)C)F BCUXLBVQPQKOSL-UHFFFAOYSA-N 0.000 claims 2
- ZWBMYZLDNQTFAT-UHFFFAOYSA-N 2-[2-(methoxymethyl)-7-methylquinoxalin-5-yl]-5-(1H-pyrazol-5-yl)-1,3-thiazole Chemical compound COCC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C1=CC=NN1)C ZWBMYZLDNQTFAT-UHFFFAOYSA-N 0.000 claims 2
- BVZVTIBTGGMYHW-UHFFFAOYSA-N 2-[2-(methoxymethyl)-7-methylquinoxalin-5-yl]-5-(5-methoxypyridin-2-yl)-1,3-thiazole Chemical compound COCC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C1=NC=C(C=C1)OC)C BVZVTIBTGGMYHW-UHFFFAOYSA-N 0.000 claims 2
- NRCOAUXFFVLOMG-UHFFFAOYSA-N 2-[2-(methoxymethyl)-7-methylquinoxalin-5-yl]-5-phenyl-1,3-thiazole Chemical compound COCC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C1=CC=CC=C1)C NRCOAUXFFVLOMG-UHFFFAOYSA-N 0.000 claims 2
- KUDWAJKSHBBXSZ-UHFFFAOYSA-N 2-[2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-4-methyl-1,3-thiazol-5-yl]-3-fluorophenol Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=C(N=1)C)C1=C(C=CC=C1F)O)C)F KUDWAJKSHBBXSZ-UHFFFAOYSA-N 0.000 claims 2
- BVOIMQZYOZNAGN-UHFFFAOYSA-N 3-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-1,2-thiazole Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C1=NSC=C1)C)F BVOIMQZYOZNAGN-UHFFFAOYSA-N 0.000 claims 2
- DDOBKAYUABHCJH-UHFFFAOYSA-N 3-[2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-1,3-thiazol-5-yl]-4-(trifluoromethoxy)phenol Chemical compound Cc1cc(-c2ncc(s2)-c2cc(O)ccc2OC(F)(F)F)c2ncc(OC(F)F)nc2c1 DDOBKAYUABHCJH-UHFFFAOYSA-N 0.000 claims 2
- CULBBOWPCSQHGH-UHFFFAOYSA-N 3-[2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-1,3-thiazol-5-yl]-4-fluorophenol Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C=1C=C(C=CC=1F)O)C)F CULBBOWPCSQHGH-UHFFFAOYSA-N 0.000 claims 2
- XBEAYGDOKCPXOA-UHFFFAOYSA-N 3-[2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-1,3-thiazol-5-yl]-5-fluorophenol Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C=1C=C(C=C(C=1)F)O)C)F XBEAYGDOKCPXOA-UHFFFAOYSA-N 0.000 claims 2
- MZKVNVCFYUDHPG-UHFFFAOYSA-N 3-[2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-1,3-thiazol-5-yl]phenol Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C=1C=C(C=CC=1)O)C)F MZKVNVCFYUDHPG-UHFFFAOYSA-N 0.000 claims 2
- FXEGBEVHBCPYOU-UHFFFAOYSA-N 3-[2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-4-methyl-1,3-thiazol-5-yl]phenol Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=C(N=1)C)C=1C=C(C=CC=1)O)C)F FXEGBEVHBCPYOU-UHFFFAOYSA-N 0.000 claims 2
- FAGGJNLCKCDAEH-UHFFFAOYSA-N 4-cyclopropyl-2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-1,3-thiazole Chemical compound C1(CC1)C=1N=C(SC=1)C1=C2N=CC(=NC2=CC(=C1)C)OC(F)F FAGGJNLCKCDAEH-UHFFFAOYSA-N 0.000 claims 2
- SOSAJXSWMYGAFJ-UHFFFAOYSA-N 4-tert-butyl-2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-1,3-thiazole Chemical compound C(C)(C)(C)C=1N=C(SC=1)C1=C2N=CC(=NC2=CC(=C1)C)OC(F)F SOSAJXSWMYGAFJ-UHFFFAOYSA-N 0.000 claims 2
- XSVQNMQAIASBQG-UHFFFAOYSA-N 5-(2-methoxy-7-methylquinoxalin-5-yl)-3-phenyl-1,2-oxazole Chemical compound COC1=NC2=CC(=CC(=C2N=C1)C1=CC(=NO1)C1=CC=CC=C1)C XSVQNMQAIASBQG-UHFFFAOYSA-N 0.000 claims 2
- HWENIHCSOOMUDU-UHFFFAOYSA-N 5-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-2-phenyl-1,3-thiazole Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C1=CN=C(S1)C1=CC=CC=C1)C)F HWENIHCSOOMUDU-UHFFFAOYSA-N 0.000 claims 2
- WHAQPMUTBYPVOD-UHFFFAOYSA-N 5-[2-(difluoromethyl)phenyl]-2-(2-methoxy-7-methylquinoxalin-5-yl)-1,3-thiazole Chemical compound FC(C1=C(C=CC=C1)C1=CN=C(S1)C1=C2N=CC(=NC2=CC(=C1)C)OC)F WHAQPMUTBYPVOD-UHFFFAOYSA-N 0.000 claims 2
- RIKXXIBNHADDBN-UHFFFAOYSA-N 5-[2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-1,3-thiazol-5-yl]pyridin-3-ol Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C=1C=C(C=NC=1)O)C)F RIKXXIBNHADDBN-UHFFFAOYSA-N 0.000 claims 2
- UCGOODZKGTWZLQ-UHFFFAOYSA-N 5-benzyl-2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-1,3-thiazole Chemical compound C(C1=CC=CC=C1)C1=CN=C(S1)C1=C2N=CC(=NC2=CC(=C1)C)OC(F)F UCGOODZKGTWZLQ-UHFFFAOYSA-N 0.000 claims 2
- GCGWCTZFJFFJGW-UHFFFAOYSA-N 5-cyclohexyl-2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-1,3-thiazole Chemical compound C1(CCCCC1)C1=CN=C(S1)C1=C2N=CC(=NC2=CC(=C1)C)OC(F)F GCGWCTZFJFFJGW-UHFFFAOYSA-N 0.000 claims 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 2
- SHJSOMIZBZBZSR-UHFFFAOYSA-N FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=C(N=1)C)C1=C(C=CC(=C1)F)O)C)F Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=C(N=1)C)C1=C(C=CC(=C1)F)O)C)F SHJSOMIZBZBZSR-UHFFFAOYSA-N 0.000 claims 2
- WRZOOBRURVNSOA-UHFFFAOYSA-N FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C1=C(C(=CC=C1)Cl)O)C)F Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C1=C(C(=CC=C1)Cl)O)C)F WRZOOBRURVNSOA-UHFFFAOYSA-N 0.000 claims 2
- LBICURXYXNRMTK-UHFFFAOYSA-N FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C1=C(C=CC(=C1)C)O)C)F Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C1=C(C=CC(=C1)C)O)C)F LBICURXYXNRMTK-UHFFFAOYSA-N 0.000 claims 2
- DSEDINXQOPTGSB-UHFFFAOYSA-N FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C1=C(C=CC(=C1)Cl)O)C)F Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C1=C(C=CC(=C1)Cl)O)C)F DSEDINXQOPTGSB-UHFFFAOYSA-N 0.000 claims 2
- TUAWZKJUMZTYAA-UHFFFAOYSA-N FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C1=C(C=CC(=C1)F)O)C)F Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C1=C(C=CC(=C1)F)O)C)F TUAWZKJUMZTYAA-UHFFFAOYSA-N 0.000 claims 2
- UTGHDPLSHHVLOJ-UHFFFAOYSA-N FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C1=C(C=CC=C1F)O)C)F Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)C1=C(C=CC=C1F)O)C)F UTGHDPLSHHVLOJ-UHFFFAOYSA-N 0.000 claims 2
- SUUZZXXTYDCFDK-UHFFFAOYSA-N FC1=CC(=C(C=C1)O)C1=CN=C(S1)C1=C2N=CC(=NC2=CC(=C1)C)COC Chemical compound FC1=CC(=C(C=C1)O)C1=CN=C(S1)C1=C2N=CC(=NC2=CC(=C1)C)COC SUUZZXXTYDCFDK-UHFFFAOYSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- PTJYLPJJSRBOJJ-UHFFFAOYSA-N N-ethyl-2-(2-methoxy-7-methylquinoxalin-5-yl)-1,3-thiazole-5-carboxamide Chemical compound C(C)NC(=O)C1=CN=C(S1)C1=C2N=CC(=NC2=CC(=C1)C)OC PTJYLPJJSRBOJJ-UHFFFAOYSA-N 0.000 claims 2
- 208000007536 Thrombosis Diseases 0.000 claims 2
- 206010047249 Venous thrombosis Diseases 0.000 claims 2
- PXIAJXMOKPRXML-UHFFFAOYSA-N [2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-1,3-thiazol-4-yl]-[4-(hydroxymethyl)piperidin-1-yl]methanone Chemical compound Cc1cc(-c2nc(cs2)C(=O)N2CCC(CO)CC2)c2ncc(OC(F)F)nc2c1 PXIAJXMOKPRXML-UHFFFAOYSA-N 0.000 claims 2
- HJBLUNKXPNKGLH-UHFFFAOYSA-N [2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-1,3-thiazol-5-yl]methanol Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC(=CN=1)CO)C)F HJBLUNKXPNKGLH-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 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 2
- HMNDGNKXHCKSLS-UHFFFAOYSA-N cyclohexyl-[2-(2-methoxy-7-methylquinoxalin-5-yl)-4-(trifluoromethyl)-1,3-thiazol-5-yl]methanone Chemical compound C1(CCCCC1)C(=O)C1=C(N=C(S1)C1=C2N=CC(=NC2=CC(=C1)C)OC)C(F)(F)F HMNDGNKXHCKSLS-UHFFFAOYSA-N 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 2
- 239000000178 monomer Substances 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims 1
- 206010002388 Angina unstable Diseases 0.000 claims 1
- 206010003178 Arterial thrombosis Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010003658 Atrial Fibrillation Diseases 0.000 claims 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 206010008088 Cerebral artery embolism Diseases 0.000 claims 1
- 206010008092 Cerebral artery thrombosis Diseases 0.000 claims 1
- 206010051055 Deep vein thrombosis Diseases 0.000 claims 1
- 208000005189 Embolism Diseases 0.000 claims 1
- 206010014513 Embolism arterial Diseases 0.000 claims 1
- 208000032382 Ischaemic stroke Diseases 0.000 claims 1
- 208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims 1
- 208000010378 Pulmonary Embolism Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000007814 Unstable Angina Diseases 0.000 claims 1
- 210000001367 artery Anatomy 0.000 claims 1
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 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
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005348 fluorocycloalkyl group Chemical group 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 239000007943 implant Substances 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims 1
- 201000010849 intracranial embolism Diseases 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 230000003836 peripheral circulation Effects 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 230000009862 primary prevention Effects 0.000 claims 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 201000005060 thrombophlebitis Diseases 0.000 claims 1
- 230000001052 transient effect Effects 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 210000003462 vein Anatomy 0.000 claims 1
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| PCT/US2017/041873 WO2018013772A1 (en) | 2016-07-14 | 2017-07-13 | Monocyclic heteroaryl substituted compounds |
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| ES2823127T3 (es) | 2016-07-14 | 2021-05-06 | Bristol Myers Squibb Co | Compuestos tricíclicos de quinolina y azaquinolina sustituidos con heteroarilo como inhibidores de PAR4 |
| CN109689649B (zh) | 2016-07-14 | 2022-07-19 | 百时美施贵宝公司 | 经二环杂芳基取代的化合物 |
| JP7058256B2 (ja) | 2016-07-14 | 2022-04-21 | ブリストル－マイヤーズ スクイブ カンパニー | 二環式ヘテロアリール置換化合物 |
| EP4070733A4 (en) | 2019-12-04 | 2022-11-30 | NEC Corporation | SYSTEM, METHOD AND COMPUTER PROGRAM FOR DETERMINING ABNORMAL PHYSICAL CONDITIONS |
| CN111440146B (zh) * | 2020-05-15 | 2022-10-21 | 中国药科大学 | 一种具有par4拮抗活性的苯并三嗪类化合物及其应用 |
| CN116041341B (zh) * | 2022-11-24 | 2025-02-28 | 中国药科大学 | 一种喹唑啉类par4拮抗剂及其医药应用 |
| KR20250110929A (ko) | 2022-12-02 | 2025-07-21 | 뉴모라 테라퓨틱스, 인코포레이티드 | 신경학적 장애를 치료하는 방법 |
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| US4567269A (en) * | 1982-11-12 | 1986-01-28 | Riker Laboratories, Inc. | Intermediates for the preparation of 6,7-dihydro-8-(imidazol-1-yl)-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acids |
| US4472406A (en) * | 1982-11-12 | 1984-09-18 | Riker Laboratories, Inc. | Antimicrobial 6,7-dihydro-8-(imidazol-1-yl)-5-methyl-1-oxo-1H,5H-benzo [ij]quinolizine-2-carboxylic acids and derivatives |
| US4567186A (en) * | 1985-01-14 | 1986-01-28 | Sterling Drug Inc. | 5-Heteryl-1,6-naphthyridin-2(1H)-ones, cardiotonic use thereof and intermediates therefor |
| DE3541722A1 (de) * | 1985-11-26 | 1987-05-27 | Basf Ag | Chinolinderivate und ihre verwendung zur bekaempfung von unerwuenschtem pflanzenwachstum |
| EP0224823A3 (de) * | 1985-11-26 | 1988-02-10 | BASF Aktiengesellschaft | Chinolinderivate und ihre Verwendung zur Bekämpfung von unerwümschtem Pflanzenwachstum |
| KR900004213A (ko) * | 1988-08-12 | 1990-03-27 | 최근선 | 쌍 방향 송수신의 원격 제어 시스템 |
| US5110347A (en) | 1990-11-26 | 1992-05-05 | E. I Du Pont De Nemours And Company | Substituted fused heterocyclic herbicides |
| JP2928079B2 (ja) | 1994-02-14 | 1999-07-28 | 永信薬品工業股▲ふん▼有限公司 | １−（置換ベンジル）−３−（置換アリール）縮合ピラゾール類、その製造法及びその用途 |
| US5633218A (en) * | 1995-05-24 | 1997-05-27 | E. I. Du Pont De Nemours And Company | Herbicidal benzodioxoles and benzodioxanes |
| US6245760B1 (en) * | 1997-05-28 | 2001-06-12 | Aventis Pharmaceuticals Products, Inc | Quinoline and quinoxaline compounds which inhibit platelet-derived growth factor and/or p56lck tyrosine kinases |
| US6387942B2 (en) | 2000-06-19 | 2002-05-14 | Yung Shin Pharmaceutical Ind. Co. Ltd | Method of treating disorders related to protease-activated receptors-induced cell activation |
| CA2505873A1 (en) * | 2002-11-12 | 2004-05-27 | Pfizer Products Inc. | Quinoline derivatives |
| US6894062B1 (en) * | 2002-11-12 | 2005-05-17 | Pfizer Inc. | Quinoline derivatives |
| US20080015193A1 (en) | 2006-06-20 | 2008-01-17 | Mendoza Jose S | Certain azoles exhibiting ATP-utilizing enzyme inhibitory activity, compositions, and uses thereof |
| US7592342B2 (en) | 2007-05-10 | 2009-09-22 | Smithkline Beecham Corporation | Quinoxaline derivatives as PI3 kinase inhibitors |
| US20120101032A1 (en) | 2010-10-22 | 2012-04-26 | Intermune, Inc. | Novel macrocyclic inhibitors of hepatitis c virus replication |
| CN102827073A (zh) * | 2011-06-17 | 2012-12-19 | 安吉奥斯医药品有限公司 | 治疗活性组合物和它们的使用方法 |
| CN103814020B (zh) * | 2011-06-17 | 2017-07-14 | 安吉奥斯医药品有限公司 | 治疗活性组合物和它们的使用方法 |
| US9394297B2 (en) * | 2012-02-28 | 2016-07-19 | Amgen Inc. | Amides as pim inhibitors |
| EP2847200B1 (en) | 2012-04-26 | 2017-03-29 | Bristol-Myers Squibb Company | Imidazothiadiazole derivatives as protease activated receptor 4 (par4) inhibitors for treating platelet aggregation |
| EP2855489B1 (en) | 2012-04-26 | 2017-01-04 | Bristol-Myers Squibb Company | Imidazothiadiazole and imidazopyridazine derivatives as protease activated receptor 4 (par4) inhibitors for treating platelet aggregation |
| JP6073464B2 (ja) | 2012-04-26 | 2017-02-01 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | 血小板凝集を治療するためのプロテアーゼ活性化受容体４（ｐａｒ４）阻害剤としてのイミダゾチアジアゾールおよびイミダゾピラジン誘導体 |
| US9873670B2 (en) | 2013-11-22 | 2018-01-23 | University Of Kentucky Research Foundation | Arylquinoline and analog compounds and use thereof to treat cancer |
| ES2929208T3 (es) | 2015-02-26 | 2022-11-25 | Univ Montreal | Compuestos de imidazotiadiazol como inhibidores de PAR4 |
| WO2017019828A1 (en) | 2015-07-30 | 2017-02-02 | Bristol-Myers Squibb Company | Aryl substituted bicyclic heteroaryl compounds |
| ES2823127T3 (es) * | 2016-07-14 | 2021-05-06 | Bristol Myers Squibb Co | Compuestos tricíclicos de quinolina y azaquinolina sustituidos con heteroarilo como inhibidores de PAR4 |
| JP7058256B2 (ja) | 2016-07-14 | 2022-04-21 | ブリストル－マイヤーズ スクイブ カンパニー | 二環式ヘテロアリール置換化合物 |
| CN109689649B (zh) * | 2016-07-14 | 2022-07-19 | 百时美施贵宝公司 | 经二环杂芳基取代的化合物 |
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2017
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- 2017-07-13 EP EP17742924.8A patent/EP3484874B1/en active Active
- 2017-07-13 WO PCT/US2017/041873 patent/WO2018013772A1/en not_active Ceased
- 2017-07-13 JP JP2019501720A patent/JP7102388B2/ja active Active
- 2017-07-13 US US16/317,232 patent/US10815224B2/en active Active
- 2017-07-13 KR KR1020197004281A patent/KR102492715B1/ko active Active
- 2017-07-13 ES ES17742924T patent/ES2805030T3/es active Active
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