JP2021503458A5 - - Google Patents
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- JP2021503458A5 JP2021503458A5 JP2020526865A JP2020526865A JP2021503458A5 JP 2021503458 A5 JP2021503458 A5 JP 2021503458A5 JP 2020526865 A JP2020526865 A JP 2020526865A JP 2020526865 A JP2020526865 A JP 2020526865A JP 2021503458 A5 JP2021503458 A5 JP 2021503458A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyridine
- carboxamide
- dihydroisoxazolo
- trifluorophenyl
- 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.)
- Withdrawn
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- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 150000001875 compounds Chemical class 0.000 claims description 45
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims description 40
- 125000002947 alkylene group Chemical group 0.000 claims description 34
- -1 -NR 5 2 Chemical group 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- XKDDDACJDNQVRL-UHFFFAOYSA-N 3,4-dihydropyridine-5-carboxamide Chemical compound NC(=O)C1=CN=CCC1 XKDDDACJDNQVRL-UHFFFAOYSA-N 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 241000700721 Hepatitis B virus Species 0.000 claims description 4
- 102000014150 Interferons Human genes 0.000 claims description 4
- 108010050904 Interferons Proteins 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 229940079322 interferon Drugs 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 229940124597 therapeutic agent Drugs 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 3
- UVHBUEGWJHYBBN-QMMMGPOBSA-N (4S)-3-(2,5-dimethyl-1,3-oxazol-4-yl)-4-methyl-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound CC=1OC(=C(N=1)C=1ON=C2C=1[C@@H](N(CC2)C(=O)NC1=CC(=C(C(=C1)F)F)F)C)C UVHBUEGWJHYBBN-QMMMGPOBSA-N 0.000 claims description 2
- NZPMJWYBJSSFKB-VIFPVBQESA-N (4S)-3-(5-fluoropyridin-2-yl)-4-methyl-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound FC=1C=CC(=NC=1)C=1ON=C2C=1[C@@H](N(CC2)C(=O)NC1=CC(=C(C(=C1)F)F)F)C NZPMJWYBJSSFKB-VIFPVBQESA-N 0.000 claims description 2
- IJPFFWANXHQEAV-JTQLQIEISA-N (4S)-3-cyclopentyl-4-methyl-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound C1(CCCC1)C=1ON=C2C=1[C@@H](N(CC2)C(=O)NC1=CC(=C(C(=C1)F)F)F)C IJPFFWANXHQEAV-JTQLQIEISA-N 0.000 claims description 2
- YUSJPDCEFACERX-VIFPVBQESA-N (4S)-4-methyl-3-(1-methylpyrazol-3-yl)-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound C[C@@H]1N(CCC=2C1=C(ON=2)C1=NN(C=C1)C)C(=O)NC1=CC(=C(C(=C1)F)F)F YUSJPDCEFACERX-VIFPVBQESA-N 0.000 claims description 2
- WIOATQYDIZGLSD-VIFPVBQESA-N (4S)-4-methyl-3-(1-methylpyrazol-4-yl)-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound C[C@@H]1N(CCC=2C1=C(ON=2)C=1C=NN(C=1)C)C(=O)NC1=CC(=C(C(=C1)F)F)F WIOATQYDIZGLSD-VIFPVBQESA-N 0.000 claims description 2
- VCPIFUVZLQPSIB-QMMMGPOBSA-N (4S)-4-methyl-3-(2-methyl-1,3-oxazol-4-yl)-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound C[C@@H]1N(CCC=2C1=C(ON=2)C=1N=C(OC=1)C)C(=O)NC1=CC(=C(C(=C1)F)F)F VCPIFUVZLQPSIB-QMMMGPOBSA-N 0.000 claims description 2
- HCHKJQDTHNTDGX-QMMMGPOBSA-N (4S)-4-methyl-3-(2-methyl-1,3-thiazol-4-yl)-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound C[C@@H]1N(CCC=2C1=C(ON=2)C=1N=C(SC=1)C)C(=O)NC1=CC(=C(C(=C1)F)F)F HCHKJQDTHNTDGX-QMMMGPOBSA-N 0.000 claims description 2
- VWQNYYJOLNMUOB-VIFPVBQESA-N (4S)-4-methyl-3-(5-methyl-1,2-oxazol-3-yl)-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound C[C@@H]1N(CCC=2C1=C(ON=2)C1=NOC(=C1)C)C(=O)NC1=CC(=C(C(=C1)F)F)F VWQNYYJOLNMUOB-VIFPVBQESA-N 0.000 claims description 2
- HSGVZSDPMVKESF-SECBINFHSA-N (6R)-3-(2,4-difluorophenyl)-6-methyl-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound FC1=C(C=CC(=C1)F)C=1ON=C2C=1CN([C@@H](C2)C)C(=O)NC1=CC(=C(C(=C1)F)F)F HSGVZSDPMVKESF-SECBINFHSA-N 0.000 claims description 2
- HSGVZSDPMVKESF-VIFPVBQESA-N (6S)-3-(2,4-difluorophenyl)-6-methyl-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound FC1=C(C=CC(=C1)F)C=1ON=C2C=1CN([C@H](C2)C)C(=O)NC1=CC(=C(C(=C1)F)F)F HSGVZSDPMVKESF-VIFPVBQESA-N 0.000 claims description 2
- UBWCVCIJBSRHPU-QMMMGPOBSA-N (6S)-3-(2,5-dimethyl-1,3-oxazol-4-yl)-6-methyl-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound CC=1OC(=C(N=1)C=1ON=C2C=1CN([C@H](C2)C)C(=O)NC1=CC(=C(C(=C1)F)F)F)C UBWCVCIJBSRHPU-QMMMGPOBSA-N 0.000 claims description 2
- XCVNUASPQHJLRG-QMMMGPOBSA-N (6S)-3-(2,5-dioxopyrrolidin-1-yl)-6-methyl-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound O=C1N(C(CC1)=O)C=1ON=C2C=1CN([C@H](C2)C)C(=O)NC1=CC(=C(C(=C1)F)F)F XCVNUASPQHJLRG-QMMMGPOBSA-N 0.000 claims description 2
- VWFZDYIVYXOSPI-JTQLQIEISA-N (6S)-3-(3,3-dimethyl-2-oxopyrrolidin-1-yl)-6-methyl-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound CC1(C(N(CC1)C=1ON=C2C=1CN([C@H](C2)C)C(=O)NC1=CC(=C(C(=C1)F)F)F)=O)C VWFZDYIVYXOSPI-JTQLQIEISA-N 0.000 claims description 2
- MFFVQTFEKWILKO-VIFPVBQESA-N (6S)-3-(5-fluoropyridin-2-yl)-6-methyl-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound FC=1C=CC(=NC=1)C=1ON=C2C=1CN([C@H](C2)C)C(=O)NC1=CC(=C(C(=C1)F)F)F MFFVQTFEKWILKO-VIFPVBQESA-N 0.000 claims description 2
- RFRAXIGRUQDTAG-GXSJLCMTSA-N (6S)-3-[(5R)-5-(methoxymethyl)-2-oxo-1,3-oxazolidin-3-yl]-6-methyl-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound COC[C@H]1CN(C(O1)=O)C=1ON=C2C=1CN([C@H](C2)C)C(=O)NC1=CC(=C(C(=C1)F)F)F RFRAXIGRUQDTAG-GXSJLCMTSA-N 0.000 claims description 2
- RFRAXIGRUQDTAG-ONGXEEELSA-N (6S)-3-[(5S)-5-(methoxymethyl)-2-oxo-1,3-oxazolidin-3-yl]-6-methyl-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound COC[C@@H]1CN(C(O1)=O)C=1ON=C2C=1CN([C@H](C2)C)C(=O)NC1=CC(=C(C(=C1)F)F)F RFRAXIGRUQDTAG-ONGXEEELSA-N 0.000 claims description 2
- KJYINAXOIHOZNB-JTQLQIEISA-N (6S)-3-[4-(difluoromethoxy)phenyl]-6-methyl-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound FC(OC1=CC=C(C=C1)C=1ON=C2C=1CN([C@H](C2)C)C(=O)NC1=CC(=C(C(=C1)F)F)F)F KJYINAXOIHOZNB-JTQLQIEISA-N 0.000 claims description 2
- ZDVZDGMQWGFYIV-VIFPVBQESA-N (6S)-6-methyl-3-(1-methylpyrazol-3-yl)-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound C[C@H]1CC=2C(CN1C(=O)NC1=CC(=C(C(=C1)F)F)F)=C(ON=2)C1=NN(C=C1)C ZDVZDGMQWGFYIV-VIFPVBQESA-N 0.000 claims description 2
- GMPGHCABNLUKQH-VIFPVBQESA-N (6S)-6-methyl-3-(1-methylpyrazol-4-yl)-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound C[C@H]1CC=2C(CN1C(=O)NC1=CC(=C(C(=C1)F)F)F)=C(ON=2)C=1C=NN(C=1)C GMPGHCABNLUKQH-VIFPVBQESA-N 0.000 claims description 2
- MKEGNZBFAXDDQQ-QMMMGPOBSA-N (6S)-6-methyl-3-(2-methyl-1,3-oxazol-4-yl)-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound C[C@H]1CC=2C(CN1C(=O)NC1=CC(=C(C(=C1)F)F)F)=C(ON=2)C=1N=C(OC=1)C MKEGNZBFAXDDQQ-QMMMGPOBSA-N 0.000 claims description 2
- JSZYIRAJUGCKIQ-QMMMGPOBSA-N (6S)-6-methyl-3-(2-methyl-1,3-thiazol-4-yl)-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound C[C@H]1CC=2C(CN1C(=O)NC1=CC(=C(C(=C1)F)F)F)=C(ON=2)C=1N=C(SC=1)C JSZYIRAJUGCKIQ-QMMMGPOBSA-N 0.000 claims description 2
- ICQVPMDDFGFVSX-QMMMGPOBSA-N (6S)-6-methyl-3-(2-oxo-1,3-oxazolidin-3-yl)-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound C[C@H]1CC=2C(CN1C(=O)NC1=CC(=C(C(=C1)F)F)F)=C(ON=2)N1C(OCC1)=O ICQVPMDDFGFVSX-QMMMGPOBSA-N 0.000 claims description 2
- VRUMABCEOCYRIQ-JTQLQIEISA-N (6S)-6-methyl-3-(2-oxopiperidin-1-yl)-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound C[C@H]1CC=2C(CN1C(=O)NC1=CC(=C(C(=C1)F)F)F)=C(ON=2)N1C(CCCC1)=O VRUMABCEOCYRIQ-JTQLQIEISA-N 0.000 claims description 2
- VDYQOGFMBFRUAY-ZDUSSCGKSA-N (6S)-6-methyl-3-(2-oxopiperidin-1-yl)-N-phenyl-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound C[C@H]1CC=2C(CN1C(=O)NC1=CC=CC=C1)=C(ON=2)N1C(CCCC1)=O VDYQOGFMBFRUAY-ZDUSSCGKSA-N 0.000 claims description 2
- NEDPNLXVPYPBTE-VIFPVBQESA-N (6S)-6-methyl-3-(2-oxopyrrolidin-1-yl)-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound C[C@H]1CC=2C(CN1C(=O)NC1=CC(=C(C(=C1)F)F)F)=C(ON=2)N1C(CCC1)=O NEDPNLXVPYPBTE-VIFPVBQESA-N 0.000 claims description 2
- ZIIBJWPMFGZYHC-AXDSSHIGSA-N (6S)-6-methyl-3-(3-methyl-2-oxopyrrolidin-1-yl)-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound C[C@H]1CC=2C(CN1C(=O)NC1=CC(=C(C(=C1)F)F)F)=C(ON=2)N1C(C(CC1)C)=O ZIIBJWPMFGZYHC-AXDSSHIGSA-N 0.000 claims description 2
- GUYFVZOBYJMYLB-JTQLQIEISA-N (6S)-6-methyl-3-[4-(trifluoromethoxy)phenyl]-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound C[C@H]1CC=2C(CN1C(=O)NC1=CC(=C(C(=C1)F)F)F)=C(ON=2)C1=CC=C(C=C1)OC(F)(F)F GUYFVZOBYJMYLB-JTQLQIEISA-N 0.000 claims description 2
- PIISANBTQLIGPW-JTQLQIEISA-N (6S)-6-methyl-3-morpholin-4-yl-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound C[C@H]1CC=2C(CN1C(=O)NC1=CC(=C(C(=C1)F)F)F)=C(ON=2)N1CCOCC1 PIISANBTQLIGPW-JTQLQIEISA-N 0.000 claims description 2
- PPQJTCAMXPUBSU-NSHDSACASA-N (6S)-6-methyl-3-phenyl-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound C[C@H]1CC=2C(CN1C(=O)NC1=CC(=C(C(=C1)F)F)F)=C(ON=2)C1=CC=CC=C1 PPQJTCAMXPUBSU-NSHDSACASA-N 0.000 claims description 2
- HYKKDULXSMSBBK-NSHDSACASA-N (6S)-N-(3-cyano-4-fluorophenyl)-6-methyl-3-(2-oxopyrrolidin-1-yl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound C(#N)C=1C=C(C=CC=1F)NC(=O)N1CC=2C(C[C@@H]1C)=NOC=2N1C(CCC1)=O HYKKDULXSMSBBK-NSHDSACASA-N 0.000 claims description 2
- MGZBOXJGQBWBJN-LBPRGKRZSA-N (6S)-N-(4-cyano-3-fluorophenyl)-6-methyl-3-(2-oxopiperidin-1-yl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound C(#N)C1=C(C=C(C=C1)NC(=O)N1CC=2C(C[C@@H]1C)=NOC=2N1C(CCCC1)=O)F MGZBOXJGQBWBJN-LBPRGKRZSA-N 0.000 claims description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
- TXWTXQMIYAKTNX-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-4-methyl-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound FC1=C(C=CC(=C1)F)C=1ON=C2C=1C(N(CC2)C(=O)NC1=CC(=C(C(=C1)F)F)F)C TXWTXQMIYAKTNX-UHFFFAOYSA-N 0.000 claims description 2
- HSGVZSDPMVKESF-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-6-methyl-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound FC1=C(C=CC(=C1)F)C=1ON=C2C=1CN(C(C2)C)C(=O)NC1=CC(=C(C(=C1)F)F)F HSGVZSDPMVKESF-UHFFFAOYSA-N 0.000 claims description 2
- PCEXGHZIDJLECJ-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-N-(3,4,5-trifluorophenyl)-4,5,6,7-tetrahydro-2,1-benzoxazole-5-carboxamide Chemical compound FC1=C(C=CC(=C1)F)C1=C2C(=NO1)CCC(C2)C(=O)NC1=CC(=C(C(=C1)F)F)F PCEXGHZIDJLECJ-UHFFFAOYSA-N 0.000 claims description 2
- WIAIAMDEYRNDGC-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound FC1=C(C=CC(=C1)F)C=1ON=C2C=1CN(CC2)C(=O)NC1=CC(=C(C(=C1)F)F)F WIAIAMDEYRNDGC-UHFFFAOYSA-N 0.000 claims description 2
- UVLPLEKFXBKBKK-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,5-c]pyridine-5-carboxamide Chemical compound FC1=C(C=CC(=C1)F)C1=NOC2=C1CN(CC2)C(=O)NC1=CC(=C(C(=C1)F)F)F UVLPLEKFXBKBKK-UHFFFAOYSA-N 0.000 claims description 2
- TULMYEKSAZXSTA-UHFFFAOYSA-N 3-(2-oxo-1,3-oxazolidin-3-yl)-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound O=C1OCCN1C=1ON=C2C=1CN(CC2)C(=O)NC1=CC(=C(C(=C1)F)F)F TULMYEKSAZXSTA-UHFFFAOYSA-N 0.000 claims description 2
- VHDQWAUACHPBMC-UHFFFAOYSA-N 3-(2-oxopyrrolidin-1-yl)-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound O=C1N(CCC1)C=1ON=C2C=1CN(CC2)C(=O)NC1=CC(=C(C(=C1)F)F)F VHDQWAUACHPBMC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- LSEYORLPHQWFIC-UHFFFAOYSA-N 3-cyclohexyl-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound C1(CCCCC1)C=1ON=C2C=1CN(CC2)C(=O)NC1=CC(=C(C(=C1)F)F)F LSEYORLPHQWFIC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- HQUFQKYHNODMHF-UHFFFAOYSA-N 3-pyrrolidin-1-yl-N-(3,4,5-trifluorophenyl)-6,7-dihydro-4H-[1,2]oxazolo[4,3-c]pyridine-5-carboxamide Chemical compound N1(CCCC1)C=1ON=C2C=1CN(CC2)C(=O)NC1=CC(=C(C(=C1)F)F)F HQUFQKYHNODMHF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 208000035143 Bacterial infection Diseases 0.000 claims description 2
- 108700024845 Hepatitis B virus P Proteins 0.000 claims description 2
- 229940123066 Polymerase inhibitor Drugs 0.000 claims description 2
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| US10738035B2 (en) | 2015-05-13 | 2020-08-11 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
| JP6904970B2 (ja) | 2016-03-07 | 2021-07-21 | エナンタ ファーマシューティカルズ インコーポレイテッド | Ｂ型肝炎抗ウイルス剤 |
| US10952978B2 (en) | 2017-08-28 | 2021-03-23 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
| CN111247131B (zh) * | 2017-11-16 | 2022-02-18 | 正大天晴药业集团股份有限公司 | 抗HBV的四氢异噁唑并[4,3-c]吡啶类化合物 |
| CA3083797A1 (en) * | 2017-12-21 | 2019-06-27 | Janssen Sciences Ireland Unlimited Company | Isoxazole compounds for the treatment of diseases associated with hbv infections |
| US11058678B2 (en) | 2018-01-22 | 2021-07-13 | Enanta Pharmaceuticals, Inc. | Substituted heterocycles as antiviral agents |
| WO2019191166A1 (en) | 2018-03-29 | 2019-10-03 | Enanta Pharmaceuticals, Inc. | Hepatitis b antiviral agents |
| UY38383A (es) | 2018-09-21 | 2020-04-30 | Enanta Pharm Inc | Heterociclos funcionalizados como agentes antivirales |
| US11198693B2 (en) | 2018-11-21 | 2021-12-14 | Enanta Pharmaceuticals, Inc. | Functionalized heterocycles as antiviral agents |
| WO2020247444A1 (en) | 2019-06-03 | 2020-12-10 | Enanta Pharmaceuticals, Inc, | Hepatitis b antiviral agents |
| WO2020247575A1 (en) | 2019-06-04 | 2020-12-10 | Enanta Pharmaceuticals, Inc. | Hepatitis b antiviral agents |
| WO2020247561A1 (en) | 2019-06-04 | 2020-12-10 | Enanta Pharmaceuticals, Inc, | Hepatitis b antiviral agents |
| US11738019B2 (en) | 2019-07-11 | 2023-08-29 | Enanta Pharmaceuticals, Inc. | Substituted heterocycles as antiviral agents |
| US11236108B2 (en) | 2019-09-17 | 2022-02-01 | Enanta Pharmaceuticals, Inc. | Functionalized heterocycles as antiviral agents |
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| JP7755319B2 (ja) * | 2020-06-05 | 2025-10-16 | パシオス セラピューティクス リミテッド | Ｇｐｒ６５のモジュレーターとしてのｎ－（フェニルアミノカルボニル）テトラヒドロ－イソキノリン及び関連する化合物 |
| CN114539148A (zh) * | 2022-01-25 | 2022-05-27 | 北京英飞智药科技有限公司 | 一种环状n-羟基酰亚胺类化合物及其用途 |
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-
2018
- 2018-11-16 EP EP18812295.6A patent/EP3710455A1/en not_active Withdrawn
- 2018-11-16 CN CN201880072633.XA patent/CN111315749A/zh active Pending
- 2018-11-16 US US16/764,525 patent/US20210079015A1/en not_active Abandoned
- 2018-11-16 WO PCT/IB2018/059059 patent/WO2019097479A1/en not_active Ceased
- 2018-11-16 JP JP2020526865A patent/JP2021503458A/ja not_active Withdrawn
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