JP2019524732A5 - - Google Patents
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- Publication number
- JP2019524732A5 JP2019524732A5 JP2019501630A JP2019501630A JP2019524732A5 JP 2019524732 A5 JP2019524732 A5 JP 2019524732A5 JP 2019501630 A JP2019501630 A JP 2019501630A JP 2019501630 A JP2019501630 A JP 2019501630A JP 2019524732 A5 JP2019524732 A5 JP 2019524732A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- thiazol
- methoxy
- methylquinoxalin
- carbamate
- 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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- -1 benzo[d]oxazolyl Chemical group 0.000 claims 127
- 125000005605 benzo group Chemical group 0.000 claims 63
- 125000000217 alkyl group Chemical group 0.000 claims 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 18
- 229910052731 fluorine Inorganic materials 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 9
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 208000035475 disorder Diseases 0.000 claims 7
- 230000009424 thromboembolic effect Effects 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000002757 morpholinyl group Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 3
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 claims 3
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000005873 benzo[d]thiazolyl group Chemical group 0.000 claims 3
- 125000005348 fluorocycloalkyl group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- BJZCVSWNTPRACJ-UHFFFAOYSA-N methyl n-pyridin-3-ylcarbamate Chemical compound COC(=O)NC1=CC=CN=C1 BJZCVSWNTPRACJ-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- CLUQDTCNSMWVAE-IBGZPJMESA-N (3-cyanophenyl)methyl N-[[(7S)-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2ccc3O[C@H](CNC(=O)OCc4cccc(c4)C#N)Cc3c2s1 CLUQDTCNSMWVAE-IBGZPJMESA-N 0.000 claims 2
- CGJDISUHKMOFCE-KRWDZBQOSA-N (4-methoxyphenyl) N-[[(7S)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]carbamate Chemical compound FC1=CC=2N=C(SC=2C=2C[C@H](OC=21)CNC(OC1=CC=C(C=C1)OC)=O)C1=C2N=CC(=NC2=CC(=C1)C)OC CGJDISUHKMOFCE-KRWDZBQOSA-N 0.000 claims 2
- BMCCUAHXQZRETB-HNNXBMFYSA-N (7S)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7-[(2-methylpyrimidin-5-yl)oxymethyl]-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazole Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2cc(F)c3O[C@@H](COc4cnc(C)nc4)COc3c2s1 BMCCUAHXQZRETB-HNNXBMFYSA-N 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- KUQQZWZEUIQCGW-UHFFFAOYSA-N 1-[7-(2-methoxy-7-methylquinoxalin-5-yl)-[1,3]dioxolo[4,5-g][1,3]benzothiazol-5-yl]-2,2-dimethylpropan-1-ol Chemical compound C1OC2=C3C(=C(C(C(C)(C)C)O)C=C2O1)N=C(S3)C1=CC(C)=CC2=NC(=CN=C12)OC KUQQZWZEUIQCGW-UHFFFAOYSA-N 0.000 claims 2
- RUOJLMWDYMDFTL-INIZCTEOSA-N 1-[[(7S)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]-3-phenylurea Chemical compound FC1=CC=2N=C(SC=2C=2C[C@H](OC=21)CNC(=O)NC1=CC=CC=C1)C1=C2N=CC(=NC2=CC(=C1)C)OC RUOJLMWDYMDFTL-INIZCTEOSA-N 0.000 claims 2
- BYWHPNJRQASNFX-ZDUSSCGKSA-N 1-cyclopropyl-3-[[(7S)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]urea Chemical compound C1(CC1)NC(=O)NC[C@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F BYWHPNJRQASNFX-ZDUSSCGKSA-N 0.000 claims 2
- ZPQKNQSQSNEYRR-SNVBAGLBSA-N 2,2,2-trifluoro-N-[[(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]acetamide Chemical compound FC(C(=O)NC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)(F)F ZPQKNQSQSNEYRR-SNVBAGLBSA-N 0.000 claims 2
- ZPQKNQSQSNEYRR-JTQLQIEISA-N 2,2,2-trifluoro-N-[[(7S)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]acetamide Chemical compound FC(C(=O)NC[C@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)(F)F ZPQKNQSQSNEYRR-JTQLQIEISA-N 0.000 claims 2
- RAFFBPODENQRNL-NSHDSACASA-N 2,2,2-trifluoroethyl N-[[(7S)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]carbamate Chemical compound FC1=CC=2N=C(SC=2C=2C[C@H](OC=21)CNC(OCC(F)(F)F)=O)C1=C2N=CC(=NC2=CC(=C1)C)OC RAFFBPODENQRNL-NSHDSACASA-N 0.000 claims 2
- GWTXHANAAMJDHR-UHFFFAOYSA-N 2-(2-methoxy-7-methylquinoxalin-5-yl)-7,7-dimethyl-8H-furo[2,3-g][1,3]benzothiazole Chemical compound COC1=NC2=CC(=CC(=C2N=C1)C=1SC2=C(N=1)C=CC1=C2CC(O1)(C)C)C GWTXHANAAMJDHR-UHFFFAOYSA-N 0.000 claims 2
- UHTOQUMQJHJBPC-LBPRGKRZSA-N 2-fluoroethyl N-[[(7S)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]carbamate Chemical compound FC1=CC=2N=C(SC=2C=2C[C@H](OC=21)CNC(OCCF)=O)C1=C2N=CC(=NC2=CC(=C1)C)OC UHTOQUMQJHJBPC-LBPRGKRZSA-N 0.000 claims 2
- ZKSNSVOTPCTKNL-ZDUSSCGKSA-N 2-methoxyethyl N-[[(7S)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]carbamate Chemical compound FC1=CC=2N=C(SC=2C=2C[C@H](OC=21)CNC(OCCOC)=O)C1=C2N=CC(=NC2=CC(=C1)C)OC ZKSNSVOTPCTKNL-ZDUSSCGKSA-N 0.000 claims 2
- UVOASFKGMCIGEE-HNNXBMFYSA-N 2-methylpropyl N-[[(7S)-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2ccc3O[C@H](CNC(=O)OCC(C)C)Cc3c2s1 UVOASFKGMCIGEE-HNNXBMFYSA-N 0.000 claims 2
- HRRZCIASTQFXRA-SANMLTNESA-N 2-methylpropyl N-[[(7S)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7-methyl-8H-furo[2,3-g][1,3]benzothiazol-7-yl]methyl]carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2cc(F)c3O[C@](C)(CNC(=O)OCC(C)C)Cc3c2s1 HRRZCIASTQFXRA-SANMLTNESA-N 0.000 claims 2
- KRIFIOHDMLYJPB-AUUYWEPGSA-N 2-methylpropyl N-[[(7S,8S)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-8-methyl-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2cc(F)c3O[C@H](CNC(=O)OCC(C)C)[C@@H](C)c3c2s1 KRIFIOHDMLYJPB-AUUYWEPGSA-N 0.000 claims 2
- UVOASFKGMCIGEE-UHFFFAOYSA-N 2-methylpropyl N-[[2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]carbamate Chemical compound COC1=NC2=CC(=CC(=C2N=C1)C=1SC2=C(N=1)C=CC1=C2CC(O1)CNC(OCC(C)C)=O)C UVOASFKGMCIGEE-UHFFFAOYSA-N 0.000 claims 2
- ZHVOCNVTYJHCGA-UHFFFAOYSA-N 5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,7-dimethyl-8H-furo[2,3-g][1,3]benzothiazole Chemical compound FC1=CC=2N=C(SC=2C=2CC(OC=21)(C)C)C1=C2N=CC(=NC2=CC(=C1)C)OC ZHVOCNVTYJHCGA-UHFFFAOYSA-N 0.000 claims 2
- FMYLAVXJLFJSMS-UHFFFAOYSA-N 6-[2-(methoxymethyl)-7-methylquinoxalin-5-yl]-[1,3]dioxolo[4,5-f][1,3]benzothiazole Chemical compound COCc1cnc2c(cc(C)cc2n1)-c1nc2cc3OCOc3cc2s1 FMYLAVXJLFJSMS-UHFFFAOYSA-N 0.000 claims 2
- APJYETRMZMJYLZ-RFAUZJTJSA-N 8-[(7S,8S)-5-fluoro-7-(hydroxymethyl)-8-methyl-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-2-yl]-3-methoxyquinoxaline-6-carbonitrile Chemical compound FC1=CC=2N=C(SC=2C=2[C@@H]([C@H](OC=21)CO)C)C=1C=C(C=C2N=C(C=NC=12)OC)C#N APJYETRMZMJYLZ-RFAUZJTJSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- NJIPQBHOGFBPBU-OAQYLSRUSA-N FC(C1=CC2=C(C3=C1N=C(S3)C1=C3N=CC(=NC3=CC(=C1)C)OC)OC[C@H](O2)OC(N(C=1C=NC(=CC=1)C)C)=O)F Chemical compound FC(C1=CC2=C(C3=C1N=C(S3)C1=C3N=CC(=NC3=CC(=C1)C)OC)OC[C@H](O2)OC(N(C=1C=NC(=CC=1)C)C)=O)F NJIPQBHOGFBPBU-OAQYLSRUSA-N 0.000 claims 2
- FFJATIYXODUOCE-OAQYLSRUSA-N FC(C1=CC2=C(C3=C1N=C(S3)C1=C3N=CC(=NC3=CC(=C1)C)OC)OC[C@H](O2)OC(N(C=1C=NC(=CC=1)OC)C)=O)F Chemical compound FC(C1=CC2=C(C3=C1N=C(S3)C1=C3N=CC(=NC3=CC(=C1)C)OC)OC[C@H](O2)OC(N(C=1C=NC(=CC=1)OC)C)=O)F FFJATIYXODUOCE-OAQYLSRUSA-N 0.000 claims 2
- IWKRSDRQNDVIHJ-QGZVFWFLSA-N N-[[(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]-2-phenylacetamide Chemical compound FC1=CC=2N=C(SC=2C=2C[C@@H](OC=21)CNC(CC1=CC=CC=C1)=O)C1=C2N=CC(=NC2=CC(=C1)C)OC IWKRSDRQNDVIHJ-QGZVFWFLSA-N 0.000 claims 2
- RPLZWPRURWHSQI-GFCCVEGCSA-N N-[[(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]acetamide Chemical compound FC1=CC=2N=C(SC=2C=2C[C@@H](OC=21)CNC(C)=O)C1=C2N=CC(=NC2=CC(=C1)C)OC RPLZWPRURWHSQI-GFCCVEGCSA-N 0.000 claims 2
- XUKKJIZDCNQDSE-LBPRGKRZSA-N N-[[(7S)-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]methanesulfonamide Chemical compound CS(=O)(=O)NC[C@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2 XUKKJIZDCNQDSE-LBPRGKRZSA-N 0.000 claims 2
- RPLZWPRURWHSQI-LBPRGKRZSA-N N-[[(7S)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]acetamide Chemical compound FC1=CC=2N=C(SC=2C=2C[C@H](OC=21)CNC(C)=O)C1=C2N=CC(=NC2=CC(=C1)C)OC RPLZWPRURWHSQI-LBPRGKRZSA-N 0.000 claims 2
- HTHMMHFOYQYNMM-AWEZNQCLSA-N N-[[(7S)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]morpholine-4-carboxamide Chemical compound N1(CCOCC1)C(=O)NC[C@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F HTHMMHFOYQYNMM-AWEZNQCLSA-N 0.000 claims 2
- PKKBGWLLLMUVLB-JOCHJYFZSA-N OCC1=CC(=C2N=CC(=NC2=C1)OC)C=1SC2=C(N=1)C(=CC1=C2OC[C@H](O1)OC(N(C1=CC(=NC=C1)C)C)=O)C Chemical compound OCC1=CC(=C2N=CC(=NC2=C1)OC)C=1SC2=C(N=1)C(=CC1=C2OC[C@H](O1)OC(N(C1=CC(=NC=C1)C)C)=O)C PKKBGWLLLMUVLB-JOCHJYFZSA-N 0.000 claims 2
- WXOGPQOZSOZMRS-JOCHJYFZSA-N OCC1=CC(=C2N=CC(=NC2=C1)OC)C=1SC2=C(N=1)C(=CC1=C2OC[C@H](O1)OC(N(C=1C=NC(=CC=1)C)C)=O)C Chemical compound OCC1=CC(=C2N=CC(=NC2=C1)OC)C=1SC2=C(N=1)C(=CC1=C2OC[C@H](O1)OC(N(C=1C=NC(=CC=1)C)C)=O)C WXOGPQOZSOZMRS-JOCHJYFZSA-N 0.000 claims 2
- XOIVZDGZBVDSTN-JOCHJYFZSA-N OCC1=CC(=C2N=CC(=NC2=C1)OC)C=1SC2=C(N=1)C(=CC1=C2OC[C@H](O1)OC(N(C=1C=NC(=CC=1)OC)C)=O)C Chemical compound OCC1=CC(=C2N=CC(=NC2=C1)OC)C=1SC2=C(N=1)C(=CC1=C2OC[C@H](O1)OC(N(C=1C=NC(=CC=1)OC)C)=O)C XOIVZDGZBVDSTN-JOCHJYFZSA-N 0.000 claims 2
- 208000007536 Thrombosis Diseases 0.000 claims 2
- 206010047249 Venous thrombosis Diseases 0.000 claims 2
- IPFUNVYETGNHBA-GOSISDBHSA-N [(3R)-8-(2-methoxy-7-methylquinoxalin-5-yl)-2,3-dihydrofuro[2,3-h][1,4]benzodioxin-3-yl]methyl N-(2-methylpyridin-4-yl)carbamate Chemical compound COC1=NC2=CC(C)=CC(C3=CC4=C5OC[C@H](COC(=O)NC6=CC(C)=NC=C6)OC5=CC=C4O3)=C2N=C1 IPFUNVYETGNHBA-GOSISDBHSA-N 0.000 claims 2
- OOLGDPWOGVJHRM-QGZVFWFLSA-N [(3R)-8-(2-methoxy-7-methylquinoxalin-5-yl)-2,3-dihydrofuro[2,3-h][1,4]benzodioxin-3-yl]methyl N-(6-methoxypyridin-3-yl)carbamate Chemical compound COC1=CC=C(NC(=O)OC[C@H]2COC3=C4C=C(OC4=CC=C3O2)C2=C3N=CC(OC)=NC3=CC(C)=C2)C=N1 OOLGDPWOGVJHRM-QGZVFWFLSA-N 0.000 claims 2
- UATAIEGDSXSHHS-GOSISDBHSA-N [(3R)-8-(2-methoxy-7-methylquinoxalin-5-yl)-2,3-dihydrofuro[2,3-h][1,4]benzodioxin-3-yl]methyl N-(6-methylpyridin-3-yl)carbamate Chemical compound COC1=NC2=CC(C)=CC(C3=CC4=C5OC[C@H](COC(=O)NC6=CC=C(C)N=C6)OC5=CC=C4O3)=C2N=C1 UATAIEGDSXSHHS-GOSISDBHSA-N 0.000 claims 2
- RDCNMUARNUFIFP-GJZGRUSLSA-N [(3S)-oxolan-3-yl] N-[[(7S)-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]carbamate Chemical compound COC1=NC2=CC(=CC(=C2N=C1)C=1SC2=C(N=1)C=CC1=C2C[C@H](O1)CNC(O[C@@H]1COCC1)=O)C RDCNMUARNUFIFP-GJZGRUSLSA-N 0.000 claims 2
- BYBDGSXTWBDRIF-MRXNPFEDSA-N [(7R)-2-(2-ethoxy-7-methylquinoxalin-5-yl)-5-fluoro-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-methylpyrimidin-5-yl)carbamate Chemical compound CCOc1cnc2c(cc(C)cc2n1)-c1nc2cc(F)c3O[C@@H](COC(=O)Nc4cnc(C)nc4)Cc3c2s1 BYBDGSXTWBDRIF-MRXNPFEDSA-N 0.000 claims 2
- AINCGZSTBVVTEJ-QGZVFWFLSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(1,3-benzothiazol-5-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(C)cc3O[C@@H](COC(=O)Nc4ccc5scnc5c4)COc3c2s1 AINCGZSTBVVTEJ-QGZVFWFLSA-N 0.000 claims 2
- AYTMSKMIIMXIJC-QGZVFWFLSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(1,3-benzothiazol-6-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(C)cc3O[C@@H](COC(=O)Nc4ccc5ncsc5c4)COc3c2s1 AYTMSKMIIMXIJC-QGZVFWFLSA-N 0.000 claims 2
- BRBJYBGHAMJMFD-OAHLLOKOSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-chloropyrimidin-5-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(C)cc3O[C@@H](COC(=O)Nc4cnc(Cl)nc4)COc3c2s1 BRBJYBGHAMJMFD-OAHLLOKOSA-N 0.000 claims 2
- PYCJFTRYFSPCIG-QGZVFWFLSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-methoxypyridin-4-yl)carbamate Chemical compound COc1cc(NC(=O)OC[C@H]2COc3c(O2)cc(C)c2nc(sc32)-c2cc(C)cc3nc(OC)cnc23)ccn1 PYCJFTRYFSPCIG-QGZVFWFLSA-N 0.000 claims 2
- FIBWLQBDRLNSGC-GOSISDBHSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-methylpyridin-4-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(C)cc3O[C@@H](COC(=O)Nc4ccnc(C)c4)COc3c2s1 FIBWLQBDRLNSGC-GOSISDBHSA-N 0.000 claims 2
- KOAAASVHBYDFDL-LJQANCHMSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(3-cyanophenyl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(C)cc3O[C@@H](COC(=O)Nc4cccc(c4)C#N)COc3c2s1 KOAAASVHBYDFDL-LJQANCHMSA-N 0.000 claims 2
- VTRVNZOQTAGRTG-QGZVFWFLSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(3-methylimidazo[4,5-b]pyridin-6-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(C)cc3O[C@@H](COC(=O)Nc4cnc5n(C)cnc5c4)COc3c2s1 VTRVNZOQTAGRTG-QGZVFWFLSA-N 0.000 claims 2
- LGRYOKOUNHCGBJ-GOSISDBHSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(5-cyanopyridin-3-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(C)cc3O[C@@H](COC(=O)Nc4cncc(c4)C#N)COc3c2s1 LGRYOKOUNHCGBJ-GOSISDBHSA-N 0.000 claims 2
- LTRNEAALPWSWDG-QGZVFWFLSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(5-fluoropyridin-3-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(C)cc3O[C@@H](COC(=O)Nc4cncc(F)c4)COc3c2s1 LTRNEAALPWSWDG-QGZVFWFLSA-N 0.000 claims 2
- GEVDKHROJMQUMK-GOSISDBHSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(5-methoxypyridin-3-yl)carbamate Chemical compound COc1cncc(NC(=O)OC[C@H]2COc3c(O2)cc(C)c2nc(sc32)-c2cc(C)cc3nc(OC)cnc23)c1 GEVDKHROJMQUMK-GOSISDBHSA-N 0.000 claims 2
- NZBCUCKLYHUATO-GOSISDBHSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(5-methylpyridin-3-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(C)cc3O[C@@H](COC(=O)Nc4cncc(C)c4)COc3c2s1 NZBCUCKLYHUATO-GOSISDBHSA-N 0.000 claims 2
- QOKSSEPYWBJTCQ-MRXNPFEDSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-chloropyridin-3-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(C)cc3O[C@@H](COC(=O)Nc4ccc(Cl)nc4)COc3c2s1 QOKSSEPYWBJTCQ-MRXNPFEDSA-N 0.000 claims 2
- BRSKKDILFRCVIB-GOSISDBHSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-cyanopyridin-3-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(C)cc3O[C@@H](COC(=O)Nc4ccc(nc4)C#N)COc3c2s1 BRSKKDILFRCVIB-GOSISDBHSA-N 0.000 claims 2
- NVFOJQUYEJICMU-QGZVFWFLSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-fluoro-5-methylpyridin-3-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(C)cc3O[C@@H](COC(=O)Nc4cnc(F)c(C)c4)COc3c2s1 NVFOJQUYEJICMU-QGZVFWFLSA-N 0.000 claims 2
- AFCUWGUYIBLKLB-MRXNPFEDSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-fluoropyridin-3-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(C)cc3O[C@@H](COC(=O)Nc4ccc(F)nc4)COc3c2s1 AFCUWGUYIBLKLB-MRXNPFEDSA-N 0.000 claims 2
- SPVMOCBHTHZQPR-QGZVFWFLSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-methoxypyridin-3-yl)carbamate Chemical compound COc1ccc(NC(=O)OC[C@H]2COc3c(O2)cc(C)c2nc(sc32)-c2cc(C)cc3nc(OC)cnc23)cn1 SPVMOCBHTHZQPR-QGZVFWFLSA-N 0.000 claims 2
- HCCFXSKOWROQLF-GOSISDBHSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-methylpyridin-3-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(C)cc3O[C@@H](COC(=O)Nc4ccc(C)nc4)COc3c2s1 HCCFXSKOWROQLF-GOSISDBHSA-N 0.000 claims 2
- CFRQSFNCMXNWFD-LJQANCHMSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-thiophen-2-ylpyridin-3-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(C)cc3O[C@@H](COC(=O)Nc4ccc(nc4)-c4cccs4)COc3c2s1 CFRQSFNCMXNWFD-LJQANCHMSA-N 0.000 claims 2
- SAUJPUNXEPYGJC-LJQANCHMSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-[6-(3-methyl-1,2,4-triazol-1-yl)pyridin-3-yl]carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(C)cc3O[C@@H](COC(=O)Nc4ccc(nc4)-n4cnc(C)n4)COc3c2s1 SAUJPUNXEPYGJC-LJQANCHMSA-N 0.000 claims 2
- GRMKJWSBCRCQNK-QGZVFWFLSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-pyridin-3-ylcarbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(C)cc3O[C@@H](COC(=O)Nc4cccnc4)COc3c2s1 GRMKJWSBCRCQNK-QGZVFWFLSA-N 0.000 claims 2
- HTSFBDCOOXQCLT-QGZVFWFLSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-pyridin-4-ylcarbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(C)cc3O[C@@H](COC(=O)Nc4ccncc4)COc3c2s1 HTSFBDCOOXQCLT-QGZVFWFLSA-N 0.000 claims 2
- JANLPHZWGSKYQR-OAQYLSRUSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-7-methyl-8H-furo[2,3-g][1,3]benzothiazol-7-yl]methanol Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2ccc3O[C@@](C)(CO)Cc3c2s1 JANLPHZWGSKYQR-OAQYLSRUSA-N 0.000 claims 2
- OGHZGBGBDGNCCF-HHHXNRCGSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-7-methyl-8H-furo[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-methylpyrimidin-5-yl)carbamate Chemical compound CC1=NC=C(C=N1)NC(OC[C@@]1(OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2)C)=O OGHZGBGBDGNCCF-HHHXNRCGSA-N 0.000 claims 2
- RMVYWUWDNUFXJO-GDLZYMKVSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-7-methyl-8H-furo[2,3-g][1,3]benzothiazol-7-yl]methyl N-(3-cyanophenyl)carbamate Chemical compound C(#N)C=1C=C(C=CC=1)NC(OC[C@@]1(OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2)C)=O RMVYWUWDNUFXJO-GDLZYMKVSA-N 0.000 claims 2
- RPCABWULNIEIRA-HHHXNRCGSA-N [(7R)-2-(2-methoxy-7-methylquinoxalin-5-yl)-7-methyl-8H-furo[2,3-g][1,3]benzothiazol-7-yl]methyl N-pyridin-3-ylcarbamate Chemical compound N1=CC(=CC=C1)NC(OC[C@@]1(OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2)C)=O RPCABWULNIEIRA-HHHXNRCGSA-N 0.000 claims 2
- ASXFSDSYVLHWNQ-GOSISDBHSA-N [(7R)-2-(6-chloro-3-ethoxyquinolin-8-yl)-5-fluoro-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-methylpyrimidin-5-yl)carbamate Chemical compound CC1=NC=C(C=N1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C=1C=C(C=C3C=C(C=NC=13)OCC)Cl)C=C2F)=O ASXFSDSYVLHWNQ-GOSISDBHSA-N 0.000 claims 2
- HDDXOSWIDIGFDE-GFCCVEGCSA-N [(7R)-2-(6-chloro-3-methoxyquinolin-8-yl)-5-fluoro-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methanol Chemical compound ClC=1C=C2C=C(C=NC2=C(C=1)C=1SC2=C(N=1)C=C(C1=C2C[C@@H](O1)CO)F)OC HDDXOSWIDIGFDE-GFCCVEGCSA-N 0.000 claims 2
- NLAQZBHRPVKYSP-QGZVFWFLSA-N [(7R)-2-(6-chloro-3-methoxyquinolin-8-yl)-5-fluoro-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-methylpyrimidin-5-yl)carbamate Chemical compound COc1cnc2c(cc(Cl)cc2c1)-c1nc2cc(F)c3O[C@@H](COC(=O)Nc4cnc(C)nc4)Cc3c2s1 NLAQZBHRPVKYSP-QGZVFWFLSA-N 0.000 claims 2
- AGJWWLGCRZWEJJ-GOSISDBHSA-N [(7R)-2-(6-chloro-3-methoxyquinolin-8-yl)-5-fluoro-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(3-carbamoylphenyl)carbamate Chemical compound C(N)(=O)C=1C=C(C=CC=1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C=1C=C(C=C3C=C(C=NC=13)OC)Cl)C=C2F)=O AGJWWLGCRZWEJJ-GOSISDBHSA-N 0.000 claims 2
- KYMSHRSHZYVECF-QGZVFWFLSA-N [(7R)-2-(6-chloro-3-methoxyquinolin-8-yl)-5-fluoro-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-pyridin-3-ylcarbamate Chemical compound N1=CC(=CC=C1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C=1C=C(C=C3C=C(C=NC=13)OC)Cl)C=C2F)=O KYMSHRSHZYVECF-QGZVFWFLSA-N 0.000 claims 2
- NTPJTLYPZFSDQJ-GOSISDBHSA-N [(7R)-2-(7-cyano-2-methoxyquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-methylpyridin-4-yl)carbamate Chemical compound COc1cnc2c(cc(cc2n1)C#N)-c1nc2c(C)cc3O[C@@H](COC(=O)Nc4ccnc(C)c4)COc3c2s1 NTPJTLYPZFSDQJ-GOSISDBHSA-N 0.000 claims 2
- QJZROYPBDWPCHE-QGZVFWFLSA-N [(7R)-2-(7-cyano-2-methoxyquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-methoxypyridin-3-yl)carbamate Chemical compound COc1ccc(NC(=O)OC[C@H]2COc3c(O2)cc(C)c2nc(sc32)-c2cc(cc3nc(OC)cnc23)C#N)cn1 QJZROYPBDWPCHE-QGZVFWFLSA-N 0.000 claims 2
- ZPOHBEMDXUWTLZ-GOSISDBHSA-N [(7R)-2-(7-cyano-2-methoxyquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-methylpyridin-3-yl)carbamate Chemical compound COc1cnc2c(cc(cc2n1)C#N)-c1nc2c(C)cc3O[C@@H](COC(=O)Nc4ccc(C)nc4)COc3c2s1 ZPOHBEMDXUWTLZ-GOSISDBHSA-N 0.000 claims 2
- WOTFBWNTSRTGSH-QGZVFWFLSA-N [(7R)-2-(7-cyano-2-methoxyquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-pyridin-3-ylcarbamate Chemical compound COc1cnc2c(cc(cc2n1)C#N)-c1nc2c(C)cc3O[C@@H](COC(=O)Nc4cccnc4)COc3c2s1 WOTFBWNTSRTGSH-QGZVFWFLSA-N 0.000 claims 2
- VHUVSWASPTVKRF-GOSISDBHSA-N [(7R)-2-[6-(difluoromethyl)-3-methoxyquinolin-8-yl]-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-methylpyrimidin-5-yl)carbamate Chemical compound COc1cnc2c(cc(cc2c1)C(F)F)-c1nc2ccc3O[C@@H](COC(=O)Nc4cnc(C)nc4)COc3c2s1 VHUVSWASPTVKRF-GOSISDBHSA-N 0.000 claims 2
- NMNLGFGYAUNRKO-LJQANCHMSA-N [(7R)-2-[6-(fluoromethyl)-3-methoxyquinolin-8-yl]-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-methylpyrimidin-5-yl)carbamate Chemical compound COc1cnc2c(cc(CF)cc2c1)-c1nc2ccc3O[C@@H](COC(=O)Nc4cnc(C)nc4)COc3c2s1 NMNLGFGYAUNRKO-LJQANCHMSA-N 0.000 claims 2
- HTDPATIVTDPMTR-MRXNPFEDSA-N [(7R)-2-[6-chloro-3-(difluoromethoxy)quinolin-8-yl]-5-fluoro-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-methylpyrimidin-5-yl)carbamate Chemical compound CC1=NC=C(C=N1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C=1C=C(C=C3C=C(C=NC=13)OC(F)F)Cl)C=C2F)=O HTDPATIVTDPMTR-MRXNPFEDSA-N 0.000 claims 2
- DFNBDYGGHGWGIB-QGZVFWFLSA-N [(7R)-2-[6-chloro-3-(difluoromethoxy)quinolin-8-yl]-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-methylpyrimidin-5-yl)carbamate Chemical compound Cc1ncc(NC(=O)OC[C@H]2COc3c(O2)ccc2nc(sc32)-c2cc(Cl)cc3cc(OC(F)F)cnc23)cn1 DFNBDYGGHGWGIB-QGZVFWFLSA-N 0.000 claims 2
- QTUVZJWUYJSNKM-OAQYLSRUSA-N [(7R)-2-[7-(difluoromethyl)-2-methoxyquinoxalin-5-yl]-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl] N-methyl-N-(2-methylpyridin-4-yl)carbamate Chemical compound FC(C1=CC(=C2N=CC(=NC2=C1)OC)C=1SC2=C(N=1)C(=CC1=C2OC[C@H](O1)OC(N(C1=CC(=NC=C1)C)C)=O)C)F QTUVZJWUYJSNKM-OAQYLSRUSA-N 0.000 claims 2
- RYYHOLOJVZACQD-QGZVFWFLSA-N [(7R)-2-[7-(hydroxymethyl)-2-methoxyquinoxalin-5-yl]-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-pyridin-3-ylcarbamate Chemical compound COc1cnc2c(cc(CO)cc2n1)-c1nc2c(C)cc3O[C@@H](COC(=O)Nc4cccnc4)COc3c2s1 RYYHOLOJVZACQD-QGZVFWFLSA-N 0.000 claims 2
- MEHGUAXDUJQBJU-OAHLLOKOSA-N [(7R)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(1,3-benzothiazol-5-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(Cl)cc3O[C@@H](COC(=O)Nc4ccc5scnc5c4)COc3c2s1 MEHGUAXDUJQBJU-OAHLLOKOSA-N 0.000 claims 2
- RRIWOSUWAMIANB-OAHLLOKOSA-N [(7R)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(1,3-benzothiazol-6-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(Cl)cc3O[C@@H](COC(=O)Nc4ccc5ncsc5c4)COc3c2s1 RRIWOSUWAMIANB-OAHLLOKOSA-N 0.000 claims 2
- NFEIRPUJSSKYRJ-CYBMUJFWSA-N [(7R)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-chloropyrimidin-5-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(Cl)cc3O[C@@H](COC(=O)Nc4cnc(Cl)nc4)COc3c2s1 NFEIRPUJSSKYRJ-CYBMUJFWSA-N 0.000 claims 2
- LVBHQJQJQMYNQF-OAHLLOKOSA-N [(7R)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-methoxypyridin-4-yl)carbamate Chemical compound COc1cc(NC(=O)OC[C@H]2COc3c(O2)cc(Cl)c2nc(sc32)-c2cc(C)cc3nc(OC)cnc23)ccn1 LVBHQJQJQMYNQF-OAHLLOKOSA-N 0.000 claims 2
- JVJOVIBBHMCILO-MRXNPFEDSA-N [(7R)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-methylpyridin-4-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(Cl)cc3O[C@@H](COC(=O)Nc4ccnc(C)c4)COc3c2s1 JVJOVIBBHMCILO-MRXNPFEDSA-N 0.000 claims 2
- GCDVOTKFAXKRCZ-CQSZACIVSA-N [(7R)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-oxo-3H-1,3-benzoxazol-6-yl)carbamate Chemical compound O=C(NC1=CC=2OC(=O)NC=2C=C1)OC[C@H]1COC2=C(O1)C=C(Cl)C=1N=C(SC2=1)C1=CC(C)=CC2=NC(=CN=C12)OC GCDVOTKFAXKRCZ-CQSZACIVSA-N 0.000 claims 2
- ONYKCKZGXFRLTA-QGZVFWFLSA-N [(7R)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(3-cyanophenyl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(Cl)cc3O[C@@H](COC(=O)Nc4cccc(c4)C#N)COc3c2s1 ONYKCKZGXFRLTA-QGZVFWFLSA-N 0.000 claims 2
- BWRWOWSSVKYXIY-OAHLLOKOSA-N [(7R)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(3-methylimidazo[4,5-b]pyridin-6-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(Cl)cc3O[C@@H](COC(=O)Nc4cnc5n(C)cnc5c4)COc3c2s1 BWRWOWSSVKYXIY-OAHLLOKOSA-N 0.000 claims 2
- XZJRZNRDDHASGE-QGZVFWFLSA-N [(7R)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(5,6-dimethylpyridin-3-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(Cl)cc3O[C@@H](COC(=O)Nc4cnc(C)c(C)c4)COc3c2s1 XZJRZNRDDHASGE-QGZVFWFLSA-N 0.000 claims 2
- SDELRTAVQOBQID-OAHLLOKOSA-N [(7R)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(5-chloropyridin-3-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(Cl)cc3O[C@@H](COC(=O)Nc4cncc(Cl)c4)COc3c2s1 SDELRTAVQOBQID-OAHLLOKOSA-N 0.000 claims 2
- OROPJKKVSPQJMN-MRXNPFEDSA-N [(7R)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(5-cyanopyridin-3-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(Cl)cc3O[C@@H](COC(=O)Nc4cncc(c4)C#N)COc3c2s1 OROPJKKVSPQJMN-MRXNPFEDSA-N 0.000 claims 2
- KAYRZLRMPVENMZ-OAHLLOKOSA-N [(7R)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(5-fluoropyridin-3-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(Cl)cc3O[C@@H](COC(=O)Nc4cncc(F)c4)COc3c2s1 KAYRZLRMPVENMZ-OAHLLOKOSA-N 0.000 claims 2
- BQXWIFYGYBTDOM-CQSZACIVSA-N [(7R)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-chloropyridin-3-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(Cl)cc3O[C@@H](COC(=O)Nc4ccc(Cl)nc4)COc3c2s1 BQXWIFYGYBTDOM-CQSZACIVSA-N 0.000 claims 2
- GORLSLKPSIDIOR-MRXNPFEDSA-N [(7R)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-cyanopyridin-3-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(Cl)cc3O[C@@H](COC(=O)Nc4ccc(nc4)C#N)COc3c2s1 GORLSLKPSIDIOR-MRXNPFEDSA-N 0.000 claims 2
- BCUNBNNICRCGFC-OAHLLOKOSA-N [(7R)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-fluoro-5-methylpyridin-3-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(Cl)cc3O[C@@H](COC(=O)Nc4cnc(F)c(C)c4)COc3c2s1 BCUNBNNICRCGFC-OAHLLOKOSA-N 0.000 claims 2
- LNKZFVATLOPJQY-CQSZACIVSA-N [(7R)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-fluoropyridin-3-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(Cl)cc3O[C@@H](COC(=O)Nc4ccc(F)nc4)COc3c2s1 LNKZFVATLOPJQY-CQSZACIVSA-N 0.000 claims 2
- GZRBIJYGDCLWCQ-OAHLLOKOSA-N [(7R)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-methoxypyridin-3-yl)carbamate Chemical compound COc1ccc(NC(=O)OC[C@H]2COc3c(O2)cc(Cl)c2nc(sc32)-c2cc(C)cc3nc(OC)cnc23)cn1 GZRBIJYGDCLWCQ-OAHLLOKOSA-N 0.000 claims 2
- YWPACMIBVJMQND-QGZVFWFLSA-N [(7R)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-[6-(3-methyl-1,2,4-triazol-1-yl)pyridin-3-yl]carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(Cl)cc3O[C@@H](COC(=O)Nc4ccc(nc4)-n4cnc(C)n4)COc3c2s1 YWPACMIBVJMQND-QGZVFWFLSA-N 0.000 claims 2
- BXAGZCPMDHWMDO-MRXNPFEDSA-N [(7R)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-[6-(dimethylamino)pyridin-3-yl]carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(Cl)cc3O[C@@H](COC(=O)Nc4ccc(nc4)N(C)C)COc3c2s1 BXAGZCPMDHWMDO-MRXNPFEDSA-N 0.000 claims 2
- JVPHYOSQSJXJMN-MRXNPFEDSA-N [(7R)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-phenylcarbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(Cl)cc3O[C@@H](COC(=O)Nc4ccccc4)COc3c2s1 JVPHYOSQSJXJMN-MRXNPFEDSA-N 0.000 claims 2
- KIOKUHVJGDKORR-CQSZACIVSA-N [(7R)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-pyridazin-4-ylcarbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(Cl)cc3O[C@@H](COC(=O)Nc4ccnnc4)COc3c2s1 KIOKUHVJGDKORR-CQSZACIVSA-N 0.000 claims 2
- PICVDJPHPDLTLS-OAHLLOKOSA-N [(7R)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-pyridin-3-ylcarbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(Cl)cc3O[C@@H](COC(=O)Nc4cccnc4)COc3c2s1 PICVDJPHPDLTLS-OAHLLOKOSA-N 0.000 claims 2
- OFCNBJNXIQFSDB-OAHLLOKOSA-N [(7R)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-pyridin-4-ylcarbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(Cl)cc3O[C@@H](COC(=O)Nc4ccncc4)COc3c2s1 OFCNBJNXIQFSDB-OAHLLOKOSA-N 0.000 claims 2
- VCCZAJMRFSASIZ-MRXNPFEDSA-N [(7R)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-methylpyridin-3-yl)carbamate Chemical compound CC1=CC=C(C=N1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C(=C2)Cl)=O VCCZAJMRFSASIZ-MRXNPFEDSA-N 0.000 claims 2
- IWTSMRZVOPRBGR-MRXNPFEDSA-N [(7R)-4-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-methylpyridin-4-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(F)cc3O[C@@H](COC(=O)Nc4ccnc(C)c4)COc3c2s1 IWTSMRZVOPRBGR-MRXNPFEDSA-N 0.000 claims 2
- AKVNTVOQWANEMB-QGZVFWFLSA-N [(7R)-4-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(3-cyanophenyl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(F)cc3O[C@@H](COC(=O)Nc4cccc(c4)C#N)COc3c2s1 AKVNTVOQWANEMB-QGZVFWFLSA-N 0.000 claims 2
- AZEZRYICOXXESL-CQSZACIVSA-N [(7R)-4-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-fluoropyridin-3-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(F)cc3O[C@@H](COC(=O)Nc4ccc(F)nc4)COc3c2s1 AZEZRYICOXXESL-CQSZACIVSA-N 0.000 claims 2
- OZVUURZFQAHRJQ-OAHLLOKOSA-N [(7R)-4-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-methoxypyridin-3-yl)carbamate Chemical compound COc1ccc(NC(=O)OC[C@H]2COc3c(O2)cc(F)c2nc(sc32)-c2cc(C)cc3nc(OC)cnc23)cn1 OZVUURZFQAHRJQ-OAHLLOKOSA-N 0.000 claims 2
- OUJXBWYJGMPZGQ-MRXNPFEDSA-N [(7R)-4-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-methylpyridin-3-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(F)cc3O[C@@H](COC(=O)Nc4ccc(C)nc4)COc3c2s1 OUJXBWYJGMPZGQ-MRXNPFEDSA-N 0.000 claims 2
- HWIGERRBYXEYGC-OAHLLOKOSA-N [(7R)-4-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-pyridin-3-ylcarbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(F)cc3O[C@@H](COC(=O)Nc4cccnc4)COc3c2s1 HWIGERRBYXEYGC-OAHLLOKOSA-N 0.000 claims 2
- RGVOJEAFKLKKEW-OAHLLOKOSA-N [(7R)-4-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-pyridin-4-ylcarbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(F)cc3O[C@@H](COC(=O)Nc4ccncc4)COc3c2s1 RGVOJEAFKLKKEW-OAHLLOKOSA-N 0.000 claims 2
- OOPCASMPEYIIKF-OAQYLSRUSA-N [(7R)-4-fluoro-2-[7-(hydroxymethyl)-2-methoxyquinoxalin-5-yl]-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl] N-methyl-N-(2-methylpyridin-4-yl)carbamate Chemical compound CN(C(O[C@H]1OC2=C(C3=C(N=C(S3)C3=C4N=CC(=NC4=CC(=C3)CO)OC)C(=C2)F)OC1)=O)C1=CC(=NC=C1)C OOPCASMPEYIIKF-OAQYLSRUSA-N 0.000 claims 2
- FPGSQYQZIXMNAZ-OAHLLOKOSA-N [(7R)-4-fluoro-2-[7-(hydroxymethyl)-2-methoxyquinoxalin-5-yl]-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-pyridin-3-ylcarbamate Chemical compound COc1cnc2c(cc(CO)cc2n1)-c1nc2c(F)cc3O[C@@H](COC(=O)Nc4cccnc4)COc3c2s1 FPGSQYQZIXMNAZ-OAHLLOKOSA-N 0.000 claims 2
- AFFJFLNEVBUGCJ-OAHLLOKOSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-methoxypyridin-4-yl)carbamate Chemical compound COC1=NC=CC(=C1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O AFFJFLNEVBUGCJ-OAHLLOKOSA-N 0.000 claims 2
- XPIGUUHLWDLQGM-CQSZACIVSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-methoxypyrimidin-5-yl)carbamate Chemical compound COC1=NC=C(C=N1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O XPIGUUHLWDLQGM-CQSZACIVSA-N 0.000 claims 2
- RFWNTLWQYACJBA-MRXNPFEDSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-methylpyridin-4-yl)carbamate Chemical compound CC1=NC=CC(=C1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O RFWNTLWQYACJBA-MRXNPFEDSA-N 0.000 claims 2
- SGYYQMJPGDIKMA-OAHLLOKOSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-methylpyrimidin-5-yl)carbamate Chemical compound CC1=NC=C(C=N1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O SGYYQMJPGDIKMA-OAHLLOKOSA-N 0.000 claims 2
- RITBMZBJUAKFLP-MRXNPFEDSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(3-carbamoylphenyl)carbamate Chemical compound C(N)(=O)C=1C=C(C=CC=1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O RITBMZBJUAKFLP-MRXNPFEDSA-N 0.000 claims 2
- BBJXVZHAWXDYDL-QGZVFWFLSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(3-cyano-5-fluorophenyl)carbamate Chemical compound C(#N)C=1C=C(C=C(C=1)F)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O BBJXVZHAWXDYDL-QGZVFWFLSA-N 0.000 claims 2
- PUYRXVLZHWMDRQ-QGZVFWFLSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(3-cyanophenyl)carbamate Chemical compound C(#N)C=1C=C(C=CC=1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O PUYRXVLZHWMDRQ-QGZVFWFLSA-N 0.000 claims 2
- TVVHUJCSLFDADQ-MRXNPFEDSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(3-oxo-1,2-dihydroisoindol-5-yl)carbamate Chemical compound O=C1NCC2=CC=C(C=C12)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O TVVHUJCSLFDADQ-MRXNPFEDSA-N 0.000 claims 2
- HVJRYHVLIDLJSG-OAHLLOKOSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(5-carbamoylpyridin-3-yl)carbamate Chemical compound C(N)(=O)C=1C=C(C=NC=1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O HVJRYHVLIDLJSG-OAHLLOKOSA-N 0.000 claims 2
- WFUWMYDPVQFJDM-MRXNPFEDSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(5-cyanopyridin-3-yl)carbamate Chemical compound C(#N)C=1C=C(C=NC=1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O WFUWMYDPVQFJDM-MRXNPFEDSA-N 0.000 claims 2
- AUJYPKGSWUJSDN-OAHLLOKOSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(5-fluoropyridin-3-yl)carbamate Chemical compound FC=1C=C(C=NC=1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O AUJYPKGSWUJSDN-OAHLLOKOSA-N 0.000 claims 2
- FMWAKDDCCAYRFB-MRXNPFEDSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(5-methoxypyridin-3-yl)carbamate Chemical compound COC=1C=C(C=NC=1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O FMWAKDDCCAYRFB-MRXNPFEDSA-N 0.000 claims 2
- SEZXJSFICJIHFO-CQSZACIVSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-fluoropyridin-3-yl)carbamate Chemical compound FC1=CC=C(C=N1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O SEZXJSFICJIHFO-CQSZACIVSA-N 0.000 claims 2
- VYFGNNJEVVAVEI-OAHLLOKOSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-methoxypyridin-3-yl)carbamate Chemical compound COC1=CC=C(C=N1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O VYFGNNJEVVAVEI-OAHLLOKOSA-N 0.000 claims 2
- ZJCXUCCIMZSZQH-MRXNPFEDSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-methylpyridin-3-yl)carbamate Chemical compound CC1=CC=C(C=N1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O ZJCXUCCIMZSZQH-MRXNPFEDSA-N 0.000 claims 2
- VCXHLRUSWRAFLK-OAHLLOKOSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-[2-(2-hydroxyethoxy)pyrimidin-5-yl]carbamate Chemical compound OCCOC1=NC=C(C=N1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O VCXHLRUSWRAFLK-OAHLLOKOSA-N 0.000 claims 2
- BOPWXRBZHMPZKJ-OAHLLOKOSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-[2-(2-hydroxyethyl)pyrimidin-5-yl]carbamate Chemical compound OCCC1=NC=C(C=N1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O BOPWXRBZHMPZKJ-OAHLLOKOSA-N 0.000 claims 2
- UZSDQNAAHBHOSD-GOSISDBHSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-[3-(dimethylcarbamoyl)phenyl]carbamate Chemical compound CN(C(=O)C=1C=C(C=CC=1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O)C UZSDQNAAHBHOSD-GOSISDBHSA-N 0.000 claims 2
- LGNIKFCRHAXESW-GOSISDBHSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-[4-(1,3-oxazol-2-yl)phenyl]carbamate Chemical compound O1C(=NC=C1)C1=CC=C(C=C1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O LGNIKFCRHAXESW-GOSISDBHSA-N 0.000 claims 2
- HMKHZCNTJJJBJE-GOSISDBHSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-[4-(dimethylcarbamoyl)phenyl]carbamate Chemical compound CN(C(=O)C1=CC=C(C=C1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O)C HMKHZCNTJJJBJE-GOSISDBHSA-N 0.000 claims 2
- MWAMZVUVLFCMDW-QGZVFWFLSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-[4-(methylcarbamoyl)phenyl]carbamate Chemical compound CNC(=O)C1=CC=C(C=C1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O MWAMZVUVLFCMDW-QGZVFWFLSA-N 0.000 claims 2
- KNPSQCUTYFTKRG-HXUWFJFHSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-[4-(morpholine-4-carbonyl)phenyl]carbamate Chemical compound N1(CCOCC1)C(=O)C1=CC=C(C=C1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O KNPSQCUTYFTKRG-HXUWFJFHSA-N 0.000 claims 2
- AJRQLAJAVMXLBM-MRXNPFEDSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-[6-(2,2-difluoro-3-hydroxypropoxy)pyridin-3-yl]carbamate Chemical compound FC(COC1=CC=C(C=N1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O)(CO)F AJRQLAJAVMXLBM-MRXNPFEDSA-N 0.000 claims 2
- KYRIIAUUCKLWOW-MRXNPFEDSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-[6-(2-hydroxyethoxy)pyridin-3-yl]carbamate Chemical compound OCCOC1=CC=C(C=N1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O KYRIIAUUCKLWOW-MRXNPFEDSA-N 0.000 claims 2
- GDKWZDCFVMSWQE-CQSZACIVSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-pyridazin-4-ylcarbamate Chemical compound N1=NC=C(C=C1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O GDKWZDCFVMSWQE-CQSZACIVSA-N 0.000 claims 2
- ZJXWVVFRUIQQEL-OAHLLOKOSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-pyridin-3-ylcarbamate Chemical compound N1=CC(=CC=C1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O ZJXWVVFRUIQQEL-OAHLLOKOSA-N 0.000 claims 2
- HUMCMRSVVDOGFO-CQSZACIVSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-pyrimidin-5-ylcarbamate Chemical compound N1=CN=CC(=C1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2F)=O HUMCMRSVVDOGFO-CQSZACIVSA-N 0.000 claims 2
- GBGYEPMGCVEGTH-OAQYLSRUSA-N [(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7-methyl-8H-furo[2,3-g][1,3]benzothiazol-7-yl]methanol Chemical compound FC1=CC=2N=C(SC=2C=2C[C@](OC=21)(C)CO)C1=C2N=CC(=NC2=CC(=C1)C)OC GBGYEPMGCVEGTH-OAQYLSRUSA-N 0.000 claims 2
- UPDAZVIXZJJWAX-GOSISDBHSA-N [(7R)-5-fluoro-2-(3-methoxy-6-methylquinolin-8-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-methylpyrimidin-5-yl)carbamate Chemical compound CC1=NC=C(C=N1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C=1C=C(C=C3C=C(C=NC=13)OC)C)C=C2F)=O UPDAZVIXZJJWAX-GOSISDBHSA-N 0.000 claims 2
- HCUNRFPGGVOTIO-QGZVFWFLSA-N [(7R)-5-fluoro-2-(6-fluoro-3-methoxyquinolin-8-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-methylpyrimidin-5-yl)carbamate Chemical compound CC1=NC=C(C=N1)NC(OC[C@@H]1OC2=C(C1)C1=C(N=C(S1)C=1C=C(C=C3C=C(C=NC=13)OC)F)C=C2F)=O HCUNRFPGGVOTIO-QGZVFWFLSA-N 0.000 claims 2
- VOYIQZJXBICUOX-NSHDSACASA-N [(7S)-2-(2-ethoxy-7-methylquinoxalin-5-yl)-5-fluoro-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methanol Chemical compound C(C)OC1=NC2=CC(=CC(=C2N=C1)C=1SC2=C(N=1)C=C(C1=C2C[C@H](O1)CO)F)C VOYIQZJXBICUOX-NSHDSACASA-N 0.000 claims 2
- YYIYJSQEJAIUQL-NSHDSACASA-N [(7S)-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methanol Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2ccc3O[C@H](CO)Cc3c2s1 YYIYJSQEJAIUQL-NSHDSACASA-N 0.000 claims 2
- JANLPHZWGSKYQR-NRFANRHFSA-N [(7S)-2-(2-methoxy-7-methylquinoxalin-5-yl)-7-methyl-8H-furo[2,3-g][1,3]benzothiazol-7-yl]methanol Chemical compound COC1=NC2=CC(=CC(=C2N=C1)C=1SC2=C(N=1)C=CC1=C2C[C@@](O1)(C)CO)C JANLPHZWGSKYQR-NRFANRHFSA-N 0.000 claims 2
- GWBRYYMKCDDDCA-NRFANRHFSA-N [(7S)-2-(6-chloro-3-methoxyquinolin-8-yl)-5-fluoro-7-methyl-8H-furo[2,3-g][1,3]benzothiazol-7-yl]methanol Chemical compound ClC=1C=C2C=C(C=NC2=C(C=1)C=1SC2=C(N=1)C=C(C1=C2C[C@@](O1)(C)CO)F)OC GWBRYYMKCDDDCA-NRFANRHFSA-N 0.000 claims 2
- GZRBIJYGDCLWCQ-HNNXBMFYSA-N [(7S)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-methoxypyridin-3-yl)carbamate Chemical compound COc1ccc(NC(=O)OC[C@@H]2COc3c(O2)cc(Cl)c2nc(sc32)-c2cc(C)cc3nc(OC)cnc23)cn1 GZRBIJYGDCLWCQ-HNNXBMFYSA-N 0.000 claims 2
- VCCZAJMRFSASIZ-INIZCTEOSA-N [(7S)-4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-methylpyridin-3-yl)carbamate Chemical compound CC1=CC=C(C=N1)NC(OC[C@H]1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C(=C2)Cl)=O VCCZAJMRFSASIZ-INIZCTEOSA-N 0.000 claims 2
- SHKFWXHGFUFEJB-JTQLQIEISA-N [(7S)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methanol Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2cc(F)c3O[C@@H](CO)COc3c2s1 SHKFWXHGFUFEJB-JTQLQIEISA-N 0.000 claims 2
- CEJYKZJDMKBMQW-JTQLQIEISA-N [(7S)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methanol Chemical compound FC1=CC=2N=C(SC=2C=2C[C@H](OC=21)CO)C1=C2N=CC(=NC2=CC(=C1)C)OC CEJYKZJDMKBMQW-JTQLQIEISA-N 0.000 claims 2
- SGYYQMJPGDIKMA-HNNXBMFYSA-N [(7S)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-methylpyrimidin-5-yl)carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2cc(F)c3O[C@H](COC(=O)Nc4cnc(C)nc4)Cc3c2s1 SGYYQMJPGDIKMA-HNNXBMFYSA-N 0.000 claims 2
- GBGYEPMGCVEGTH-NRFANRHFSA-N [(7S)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7-methyl-8H-furo[2,3-g][1,3]benzothiazol-7-yl]methanol Chemical compound FC1=CC=2N=C(SC=2C=2C[C@@](OC=21)(C)CO)C1=C2N=CC(=NC2=CC(=C1)C)OC GBGYEPMGCVEGTH-NRFANRHFSA-N 0.000 claims 2
- JANLPHZWGSKYQR-UHFFFAOYSA-N [2-(2-methoxy-7-methylquinoxalin-5-yl)-7-methyl-8H-furo[2,3-g][1,3]benzothiazol-7-yl]methanol Chemical compound COC1=NC2=CC(=CC(=C2N=C1)C=1SC2=C(N=1)C=CC1=C2CC(O1)(C)CO)C JANLPHZWGSKYQR-UHFFFAOYSA-N 0.000 claims 2
- INLUMHLYFJRCGX-UHFFFAOYSA-N [2-(2-methoxy-7-methylquinoxalin-5-yl)-8-methyl-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methanol Chemical compound COC1=NC2=CC(=CC(=C2N=C1)C=1SC2=C(N=1)C=CC1=C2C(C(O1)CO)C)C INLUMHLYFJRCGX-UHFFFAOYSA-N 0.000 claims 2
- YVTYOJPYNLAXHP-UHFFFAOYSA-N [2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-4-fluoro-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-8-yl]methanol Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C=1SC2=C(N=1)C(=CC1=C2OC(CO1)CO)F)C)F YVTYOJPYNLAXHP-UHFFFAOYSA-N 0.000 claims 2
- PFUZHMAMGRGSAR-UHFFFAOYSA-N [2-[7-(1-hydroxyethyl)-2-methoxyquinoxalin-5-yl]-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-methoxypyridin-3-yl)carbamate Chemical compound COc1ccc(NC(=O)OCC2COc3c(O2)cc(C)c2nc(sc32)-c2cc(cc3nc(OC)cnc23)C(C)O)cn1 PFUZHMAMGRGSAR-UHFFFAOYSA-N 0.000 claims 2
- WVJXBYJGDBVDLF-UHFFFAOYSA-N [2-[7-(hydroxymethyl)-2-methoxyquinoxalin-5-yl]-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-methoxypyridin-3-yl)carbamate Chemical compound COc1ccc(NC(=O)OCC2COc3c(O2)cc(C)c2nc(sc32)-c2cc(CO)cc3nc(OC)cnc23)cn1 WVJXBYJGDBVDLF-UHFFFAOYSA-N 0.000 claims 2
- RYYHOLOJVZACQD-UHFFFAOYSA-N [2-[7-(hydroxymethyl)-2-methoxyquinoxalin-5-yl]-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-pyridin-3-ylcarbamate Chemical compound COc1cnc2c(cc(CO)cc2n1)-c1nc2c(C)cc3OC(COC(=O)Nc4cccnc4)COc3c2s1 RYYHOLOJVZACQD-UHFFFAOYSA-N 0.000 claims 2
- ARTILVZUFLLVCL-UHFFFAOYSA-N [4-(difluoromethyl)-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl N-(2-methylpyridin-4-yl)carbamate Chemical compound CC1=NC=CC(=C1)NC(OCC1OC2=C(C3=C(N=C(S3)C3=C4N=CC(=NC4=CC(=C3)C)OC)C(=C2)C(F)F)OC1)=O ARTILVZUFLLVCL-UHFFFAOYSA-N 0.000 claims 2
- FIOVFVCLWRDYPX-UHFFFAOYSA-N [4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-pyridin-3-ylcarbamate Chemical compound ClC1=CC2=C(CC(O2)COC(NC=2C=NC=CC=2)=O)C2=C1N=C(S2)C1=C2N=CC(=NC2=CC(=C1)C)OC FIOVFVCLWRDYPX-UHFFFAOYSA-N 0.000 claims 2
- WPTMKZUOMVJQBU-UHFFFAOYSA-N [4-chloro-2-[7-(hydroxymethyl)-2-methoxyquinoxalin-5-yl]-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl N-(6-methylpyridin-3-yl)carbamate Chemical compound COc1cnc2c(cc(CO)cc2n1)-c1nc2c(Cl)cc3OC(COC(=O)Nc4ccc(C)nc4)Cc3c2s1 WPTMKZUOMVJQBU-UHFFFAOYSA-N 0.000 claims 2
- GBGYEPMGCVEGTH-UHFFFAOYSA-N [5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7-methyl-8H-furo[2,3-g][1,3]benzothiazol-7-yl]methanol Chemical compound FC1=CC=2N=C(SC=2C=2CC(OC=21)(C)CO)C1=C2N=CC(=NC2=CC(=C1)C)OC GBGYEPMGCVEGTH-UHFFFAOYSA-N 0.000 claims 2
- OMXQUQIMZUZZLA-SFHVURJKSA-N benzyl N-[[(7S)-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]carbamate Chemical compound COC1=NC2=CC(=CC(=C2N=C1)C=1SC2=C(N=1)C=CC1=C2C[C@H](O1)CNC(OCC1=CC=CC=C1)=O)C OMXQUQIMZUZZLA-SFHVURJKSA-N 0.000 claims 2
- OMXQUQIMZUZZLA-UHFFFAOYSA-N benzyl N-[[2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]carbamate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2ccc3OC(CNC(=O)OCc4ccccc4)Cc3c2s1 OMXQUQIMZUZZLA-UHFFFAOYSA-N 0.000 claims 2
- 230000000747 cardiac effect Effects 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- VJZGBYRPIGXGRO-UHFFFAOYSA-N ethyl N-[[2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]carbamate Chemical compound C(C)OC(NCC1OC2=C(C1)C1=C(N=C(S1)C1=C3N=CC(=NC3=CC(=C1)C)OC)C=C2)=O VJZGBYRPIGXGRO-UHFFFAOYSA-N 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 2
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- APOQRLNLXUYJCH-INIZCTEOSA-N methyl (7S)-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazole-7-carboxylate Chemical compound COC(=O)[C@@H]1Cc2c(O1)ccc1nc(sc21)-c1cc(C)cc2nc(OC)cnc12 APOQRLNLXUYJCH-INIZCTEOSA-N 0.000 claims 2
- GIQSVLWUOUIWBD-UHFFFAOYSA-N methyl 4-[[2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methoxycarbonylamino]pyridine-2-carboxylate Chemical compound COC(=O)c1cc(NC(=O)OCC2COc3c(O2)cc(C)c2nc(sc32)-c2cc(C)cc3nc(OC)cnc23)ccn1 GIQSVLWUOUIWBD-UHFFFAOYSA-N 0.000 claims 2
- LHNJYHXTVXUUPX-LBPRGKRZSA-N methyl N-[[(7S)-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]carbamate Chemical compound COC(=O)NC[C@@H]1Cc2c(O1)ccc1nc(sc21)-c1cc(C)cc2nc(OC)cnc12 LHNJYHXTVXUUPX-LBPRGKRZSA-N 0.000 claims 2
- LHNJYHXTVXUUPX-UHFFFAOYSA-N methyl N-[[2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]carbamate Chemical compound COC1=NC2=CC(=CC(=C2N=C1)C=1SC2=C(N=1)C=CC1=C2CC(O1)CNC(OC)=O)C LHNJYHXTVXUUPX-UHFFFAOYSA-N 0.000 claims 2
- 239000000178 monomer Substances 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- QVJIWCBNCVRCNH-DJNXLDHESA-N oxan-2-ylmethyl N-[[(7S)-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]carbamate Chemical compound COC1=NC2=CC(=CC(=C2N=C1)C=1SC2=C(N=1)C=CC1=C2C[C@H](O1)CNC(OCC1OCCCC1)=O)C QVJIWCBNCVRCNH-DJNXLDHESA-N 0.000 claims 2
- HSNVHGKSOKSIOZ-LYKKTTPLSA-N oxan-3-yl N-[[(7S)-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]carbamate Chemical compound COC1=NC2=CC(=CC(=C2N=C1)C=1SC2=C(N=1)C=CC1=C2C[C@H](O1)CNC(OC1COCCC1)=O)C HSNVHGKSOKSIOZ-LYKKTTPLSA-N 0.000 claims 2
- QBLZCMYFAWHQQU-INIZCTEOSA-N oxan-4-yl N-[[(7S)-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]carbamate Chemical compound COC1=NC2=CC(=CC(=C2N=C1)C=1SC2=C(N=1)C=CC1=C2C[C@H](O1)CNC(OC1CCOCC1)=O)C QBLZCMYFAWHQQU-INIZCTEOSA-N 0.000 claims 2
- KXVFGJYJNPTXKZ-HNNXBMFYSA-N oxan-4-yl N-[[(7S)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]carbamate Chemical compound FC1=CC=2N=C(SC=2C=2C[C@H](OC=21)CNC(OC1CCOCC1)=O)C1=C2N=CC(=NC2=CC(=C1)C)OC KXVFGJYJNPTXKZ-HNNXBMFYSA-N 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- JWJZIXHFFSITPX-UHFFFAOYSA-N phenyl N-[[2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]carbamate Chemical compound COC1=NC2=CC(=CC(=C2N=C1)C=1SC2=C(N=1)C=CC1=C2CC(O1)CNC(OC1=CC=CC=C1)=O)C JWJZIXHFFSITPX-UHFFFAOYSA-N 0.000 claims 2
- LSWGNKBPTDQDBV-UHFFFAOYSA-N tert-butyl 3-[[2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methoxycarbonylamino]-7,8-dihydro-5H-1,6-naphthyridine-6-carboxylate Chemical compound COc1cnc2c(cc(C)cc2n1)-c1nc2c(C)cc3OC(COC(=O)Nc4cnc5CCN(Cc5c4)C(=O)OC(C)(C)C)COc3c2s1 LSWGNKBPTDQDBV-UHFFFAOYSA-N 0.000 claims 2
- LGAWIAJROQKYOM-UHFFFAOYSA-N tert-butyl 4-[5-[[2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methoxycarbonylamino]pyridin-2-yl]piperazine-1-carboxylate Chemical compound COC1=NC2=CC(C)=CC(C3=NC4=C(S3)C3=C(OC(COC(=O)NC5=CN=C(C=C5)N5CCN(CC5)C(=O)OC(C)(C)C)CO3)C=C4C)=C2N=C1 LGAWIAJROQKYOM-UHFFFAOYSA-N 0.000 claims 2
- DDDQMDXTLHMKTQ-CYBMUJFWSA-N tert-butyl N-[[(7R)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]carbamate Chemical compound FC1=CC=2N=C(SC=2C=2C[C@@H](OC=21)CNC(OC(C)(C)C)=O)C1=C2N=CC(=NC2=CC(=C1)C)OC DDDQMDXTLHMKTQ-CYBMUJFWSA-N 0.000 claims 2
- CSEGWHMYVIMXKS-SANMLTNESA-N tert-butyl N-[[(7S)-5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7-methyl-8H-furo[2,3-g][1,3]benzothiazol-7-yl]methyl]carbamate Chemical compound FC1=CC=2N=C(SC=2C=2C[C@@](OC=21)(C)CNC(OC(C)(C)C)=O)C1=C2N=CC(=NC2=CC(=C1)C)OC CSEGWHMYVIMXKS-SANMLTNESA-N 0.000 claims 2
- YSWDGQMWTIFTEE-UHFFFAOYSA-N tert-butyl N-[[2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-4-fluoro-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-7-yl]methyl]carbamate Chemical compound Cc1cc(-c2nc3c(F)cc4OC(CNC(=O)OC(C)(C)C)COc4c3s2)c2ncc(OC(F)F)nc2c1 YSWDGQMWTIFTEE-UHFFFAOYSA-N 0.000 claims 2
- XMMQTLKKGFZFTE-UHFFFAOYSA-N tert-butyl N-[[2-[2-(difluoromethoxy)-7-methylquinoxalin-5-yl]-4-fluoro-7,8-dihydro-[1,4]dioxino[2,3-g][1,3]benzothiazol-8-yl]methyl]carbamate Chemical compound C(C)(C)(C)OC(NCC1COC2=C(C3=C(N=C(S3)C3=C4N=CC(=NC4=CC(=C3)C)OC(F)F)C(=C2)F)O1)=O XMMQTLKKGFZFTE-UHFFFAOYSA-N 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- UUBPRIUBEQJUQL-UHFFFAOYSA-N (1-methylcyclohexyl)methanol Chemical compound OCC1(C)CCCCC1 UUBPRIUBEQJUQL-UHFFFAOYSA-N 0.000 claims 1
- OMFLONXSOVRUGA-DIFFPNOSSA-N (1R)-1-[(7S)-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]ethanol Chemical compound COC1=NC2=CC(=CC(=C2N=C1)C=1SC2=C(N=1)C=CC1=C2C[C@H](O1)[C@@H](C)O)C OMFLONXSOVRUGA-DIFFPNOSSA-N 0.000 claims 1
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 1
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims 1
- 206010002388 Angina unstable Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010003658 Atrial Fibrillation Diseases 0.000 claims 1
- 125000002853 C1-C4 hydroxyalkyl 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
- 206010011091 Coronary artery thrombosis Diseases 0.000 claims 1
- 206010051055 Deep vein thrombosis Diseases 0.000 claims 1
- 206010014513 Embolism arterial Diseases 0.000 claims 1
- 208000032382 Ischaemic stroke Diseases 0.000 claims 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims 1
- 208000010378 Pulmonary Embolism Diseases 0.000 claims 1
- 206010063544 Renal embolism Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000007814 Unstable Angina Diseases 0.000 claims 1
- UQSIEHVSHVIAPB-UHFFFAOYSA-N [1-(trifluoromethyl)cyclobutyl]methanol Chemical compound OCC1(C(F)(F)F)CCC1 UQSIEHVSHVIAPB-UHFFFAOYSA-N 0.000 claims 1
- YYWSKSKIJXVNTH-UHFFFAOYSA-N [1-(trifluoromethyl)cyclopropyl]methanol Chemical compound OCC1(C(F)(F)F)CC1 YYWSKSKIJXVNTH-UHFFFAOYSA-N 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 210000001367 artery Anatomy 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 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
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 210000005242 cardiac chamber Anatomy 0.000 claims 1
- 208000002528 coronary thrombosis Diseases 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 239000007943 implant Substances 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
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims 1
- CTNQBQFJYWXHNM-UHFFFAOYSA-N methyl n-(1-oxo-3,4-dihydro-2h-isoquinolin-7-yl)carbamate Chemical compound C1CNC(=O)C2=CC(NC(=O)OC)=CC=C21 CTNQBQFJYWXHNM-UHFFFAOYSA-N 0.000 claims 1
- FJRMETKXKAGNEA-UHFFFAOYSA-N methyl n-[6-(trifluoromethyl)pyridin-3-yl]carbamate Chemical compound COC(=O)NC1=CC=C(C(F)(F)F)N=C1 FJRMETKXKAGNEA-UHFFFAOYSA-N 0.000 claims 1
- IAGUPODHENSJEZ-UHFFFAOYSA-N methyl n-phenylcarbamate Chemical compound COC(=O)NC1=CC=CC=C1 IAGUPODHENSJEZ-UHFFFAOYSA-N 0.000 claims 1
- LDDQKRQOYOCEPD-UHFFFAOYSA-N methyl pyridin-3-yl carbonate Chemical compound COC(=O)OC1=CC=CN=C1 LDDQKRQOYOCEPD-UHFFFAOYSA-N 0.000 claims 1
- 125000006393 methylpyrimidinyl group Chemical group 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 230000003836 peripheral circulation Effects 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- FIAJDPJBWYGPMS-AWEZNQCLSA-N tert-butyl N-[[(7S)-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrofuro[2,3-g][1,3]benzothiazol-7-yl]methyl]carbamate Chemical compound COC1=NC2=CC(=CC(=C2N=C1)C=1SC2=C(N=1)C=CC1=C2C[C@H](O1)CNC(OC(C)(C)C)=O)C FIAJDPJBWYGPMS-AWEZNQCLSA-N 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 201000005060 thrombophlebitis Diseases 0.000 claims 1
- 230000001052 transient effect Effects 0.000 claims 1
- 210000003462 vein Anatomy 0.000 claims 1
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| PCT/US2017/041880 WO2018013776A1 (en) | 2016-07-14 | 2017-07-13 | Tricyclic heteroaryl-substituted quinoline and azaquinoline compounds as par4 inhibitors |
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| WO2018013772A1 (en) * | 2016-07-14 | 2018-01-18 | Bristol-Myers Squibb Company | Monocyclic heteroaryl substituted compounds |
| KR102494647B1 (ko) | 2016-07-14 | 2023-01-31 | 브리스톨-마이어스 스큅 컴퍼니 | 비시클릭 헤테로아릴 치환된 화합물 |
| 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 |
| 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 |
| CN117285527A (zh) * | 2023-09-25 | 2023-12-26 | 中国药科大学 | 一种噌啉类par4拮抗剂及其医药应用 |
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| CA1164459A (en) * | 1980-11-11 | 1984-03-27 | Yung-Hsiung Yang | Process for preparing (imidazo¬1,2-a|pyridine- 2-yl)-carbostyril or -3,4-dihydrocarbostyryl derivatives |
| TW279162B (cg-RX-API-DMAC7.html) * | 1991-09-26 | 1996-06-21 | Mitsubishi Chem Corp | |
| 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 |
| US6166041A (en) | 1995-10-11 | 2000-12-26 | Euro-Celtique, S.A. | 2-heteroaryl and 2-heterocyclic benzoxazoles as PDE IV inhibitors for the treatment of asthma |
| 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 |
| EP1348701A1 (en) | 2002-03-28 | 2003-10-01 | Warner-Lambert Company LLC | (2,4-disubstituted-thiazol-5-yl) amine compounds as PDE7 inhibitors |
| JP2007501189A (ja) | 2003-08-01 | 2007-01-25 | ジェネラブス テクノロジーズ，インコーポレイテッド | フラビウイルス科に対する二環式イミダゾール誘導体 |
| US20050272784A1 (en) | 2004-05-07 | 2005-12-08 | Xiaobing Li | Inhibitors of bacterial Type III protein secretion systems |
| AU2005267798A1 (en) | 2004-07-28 | 2006-02-09 | Irm Llc | Compounds and compositions as modulators of steroid hormone nuclear receptors |
| KR20070098914A (ko) | 2005-01-14 | 2007-10-05 | 제네랩스 테크놀로지스, 인코포레이티드 | 바이러스 감염을 치료하기 위한 인돌 유도체 |
| WO2007149395A2 (en) | 2006-06-20 | 2007-12-27 | Amphora Discovery Corporation | 2,5-substituted oxazole derivatives as protein kinase inhibitors for the treatment of cancer |
| CN101479249B (zh) | 2006-06-29 | 2012-10-10 | 霍夫曼-拉罗奇有限公司 | 苯并咪唑衍生物、其制备方法、它们作为fxr激动剂的用途及含有它们的药物制剂 |
| WO2008073451A2 (en) | 2006-12-11 | 2008-06-19 | Sirtris Pharmaceuticals, Inc. | Benzoimidazole derivatives as sirtuin (sir) modulating compounds |
| AU2008331480A1 (en) | 2007-11-30 | 2009-06-11 | Glaxosmithkline Llc | Prolyl hydroxylase inhibitors |
| ES2586459T3 (es) | 2008-05-01 | 2016-10-14 | Glaxosmithkline Llc | Quinolinas y análogos relacionados como moduladores de sirtuina |
| EA021421B1 (ru) | 2008-05-23 | 2015-06-30 | Новартис Аг | Производные хинолинов и хиноксалинов в качестве ингибиторов протеинтирозинкиназы, способ их получения, содержащая их фармацевтическая композиция и способ лечения заболеваний с применением таких соединений |
| JP5631310B2 (ja) | 2008-07-23 | 2014-11-26 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | 三環式ピラゾロピリジンキナーゼ阻害剤 |
| US20130072473A1 (en) | 2011-05-09 | 2013-03-21 | Proteostasis Therapeutics, Inc. | Compounds for treating protein folding disorders |
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| RS59882B1 (sr) | 2012-04-26 | 2020-03-31 | Bristol Myers Squibb Co | Derivati imidazotiadiazola i imidazopirazina kao inhibitori proteazom aktiviranog receptora 4 (par4) za lečenje agregacije trombocita |
| WO2013163244A1 (en) * | 2012-04-26 | 2013-10-31 | Bristol-Myers Squibb Company | Imidazothiadiazole derivatives as protease activated receptor 4 (par4) inhibitors for treating platelet aggregation |
| AU2013251680A1 (en) * | 2012-04-26 | 2014-11-13 | Bristol-Myers Squibb Company | Imidazothiadiazole and imidazopyridazine derivatives as protease activated receptor 4 (par4) inhibitors for treating platelet aggregation |
| CA2922542A1 (en) * | 2013-11-22 | 2015-05-28 | University Of Kentucky Research Foundation | Arylquinoline and analog compounds and use thereof to treat cancer |
| US9598419B1 (en) | 2014-06-24 | 2017-03-21 | Universite De Montreal | Imidazotriazine and imidazodiazine compounds |
| US9617279B1 (en) | 2014-06-24 | 2017-04-11 | Bristol-Myers Squibb Company | Imidazooxadiazole compounds |
| WO2016138199A1 (en) | 2015-02-26 | 2016-09-01 | Bristol-Myers Squibb Company | Benzothiazole and benzothiophne compounds |
| 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 |
| WO2018013772A1 (en) | 2016-07-14 | 2018-01-18 | Bristol-Myers Squibb Company | Monocyclic heteroaryl substituted compounds |
| KR102494647B1 (ko) | 2016-07-14 | 2023-01-31 | 브리스톨-마이어스 스큅 컴퍼니 | 비시클릭 헤테로아릴 치환된 화합물 |
| 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 |
-
2017
- 2017-07-13 JP JP2019501630A patent/JP6903732B2/ja active Active
- 2017-07-13 EP EP17742926.3A patent/EP3484894B1/en active Active
- 2017-07-13 KR KR1020197004282A patent/KR102468661B1/ko active Active
- 2017-07-13 US US16/317,258 patent/US20190315774A1/en not_active Abandoned
- 2017-07-13 CN CN201780056459.5A patent/CN109689664B/zh active Active
- 2017-07-13 ES ES17742926T patent/ES2823127T3/es active Active
- 2017-07-13 WO PCT/US2017/041880 patent/WO2018013776A1/en not_active Ceased
-
2021
- 2021-01-06 US US17/142,288 patent/US11932658B2/en active Active
-
2023
- 2023-12-06 US US18/530,405 patent/US20240309019A1/en active Pending
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