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
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| KR102494647B1 (ko) | 2016-07-14 | 2023-01-31 | 브리스톨-마이어스 스큅 컴퍼니 | 비시클릭 헤테로아릴 치환된 화합물 |
| JP7298711B2 (ja) | 2019-12-04 | 2023-06-27 | 日本電気株式会社 | 体調異常判定システム、体調異常判定システムの作動方法、及びコンピュータプログラム |
| 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 |
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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 |
| 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 |
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| KR900004213A (ko) * | 1988-08-12 | 1990-03-27 | 최근선 | 쌍 방향 송수신의 원격 제어 시스템 |
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| KR102494647B1 (ko) * | 2016-07-14 | 2023-01-31 | 브리스톨-마이어스 스큅 컴퍼니 | 비시클릭 헤테로아릴 치환된 화합물 |
| EP3484878B1 (en) * | 2016-07-14 | 2020-08-19 | Bristol-Myers Squibb Company | Bicyclic heteroaryl substituted compounds |
| CN109689664B (zh) | 2016-07-14 | 2022-04-15 | 百时美施贵宝公司 | 作为par4抑制剂的三环杂芳基取代的喹啉和氮杂喹啉化合物 |
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