JP2010539188A5 - - Google Patents
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- Publication number
- JP2010539188A5 JP2010539188A5 JP2010525104A JP2010525104A JP2010539188A5 JP 2010539188 A5 JP2010539188 A5 JP 2010539188A5 JP 2010525104 A JP2010525104 A JP 2010525104A JP 2010525104 A JP2010525104 A JP 2010525104A JP 2010539188 A5 JP2010539188 A5 JP 2010539188A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- phenyl
- tert
- butyl
- dioxo
- 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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- 150000001875 compounds Chemical class 0.000 claims 79
- 150000003839 salts Chemical class 0.000 claims 79
- 125000001424 substituent group Chemical group 0.000 claims 77
- -1 hydroxy, methyl Chemical group 0.000 claims 63
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 55
- 229910052739 hydrogen Inorganic materials 0.000 claims 52
- 239000001257 hydrogen Substances 0.000 claims 52
- 239000013078 crystal Substances 0.000 claims 51
- 125000005843 halogen group Chemical group 0.000 claims 48
- 238000000634 powder X-ray diffraction Methods 0.000 claims 44
- 125000000217 alkyl group Chemical group 0.000 claims 42
- 125000000623 heterocyclic group Chemical group 0.000 claims 39
- 125000003342 alkenyl group Chemical group 0.000 claims 30
- 125000000304 alkynyl group Chemical group 0.000 claims 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 29
- 125000003545 alkoxy group Chemical group 0.000 claims 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 27
- 125000004452 carbocyclyl group Chemical group 0.000 claims 25
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 23
- 150000002431 hydrogen Chemical class 0.000 claims 21
- 125000004043 oxo group Chemical group O=* 0.000 claims 21
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 16
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 15
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 15
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 14
- 125000003302 alkenyloxy group Chemical group 0.000 claims 13
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 13
- 125000005133 alkynyloxy group Chemical group 0.000 claims 13
- XNKPMUBPFWXXAD-UHFFFAOYSA-N O.CS(N)(=O)=O Chemical compound O.CS(N)(=O)=O XNKPMUBPFWXXAD-UHFFFAOYSA-N 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 12
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 11
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 9
- 241000711549 Hepacivirus C Species 0.000 claims 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 8
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 7
- 239000003814 drug Substances 0.000 claims 7
- 125000000845 uracil-1-yl group Chemical group [*]N1C(=O)N([H])C(=O)C([H])=C1[H] 0.000 claims 7
- 125000005884 carbocyclylalkyl group Chemical group 0.000 claims 6
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 229920002477 rna polymer Polymers 0.000 claims 6
- 241000124008 Mammalia Species 0.000 claims 5
- 125000005193 alkenylcarbonyloxy group Chemical group 0.000 claims 5
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims 5
- 125000005198 alkynylcarbonyloxy group Chemical group 0.000 claims 5
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims 5
- 125000005139 alkynylsulfonyl group Chemical group 0.000 claims 5
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 claims 5
- 229940124597 therapeutic agent Drugs 0.000 claims 5
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 5
- 208000005176 Hepatitis C Diseases 0.000 claims 4
- IEMLFQBMHICKAM-UHFFFAOYSA-N O.O.O.[K+].CS(=O)(=O)[NH-] Chemical compound O.O.O.[K+].CS(=O)(=O)[NH-] IEMLFQBMHICKAM-UHFFFAOYSA-N 0.000 claims 4
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims 4
- 125000005137 alkenylsulfonyl group Chemical group 0.000 claims 4
- 125000005087 alkynylcarbonyl group Chemical group 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 239000003112 inhibitor Substances 0.000 claims 4
- DYMRYCZRMAHYKE-UHFFFAOYSA-N n-diazonitramide Chemical compound [O-][N+](=O)N=[N+]=[N-] DYMRYCZRMAHYKE-UHFFFAOYSA-N 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 4
- IUIZXGRUCLCCJZ-UHFFFAOYSA-N O.O.O.O.C(C)NCC.CS(=O)(=O)N Chemical compound O.O.O.O.C(C)NCC.CS(=O)(=O)N IUIZXGRUCLCCJZ-UHFFFAOYSA-N 0.000 claims 3
- XYXZHGXFBKUGQB-UHFFFAOYSA-N O.O.[K+].CS(=O)(=O)[NH-] Chemical compound O.O.[K+].CS(=O)(=O)[NH-] XYXZHGXFBKUGQB-UHFFFAOYSA-N 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims 3
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 241001493065 dsRNA viruses Species 0.000 claims 3
- 239000003446 ligand Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- XMZSTQYSBYEENY-RMKNXTFCSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1 XMZSTQYSBYEENY-RMKNXTFCSA-N 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 2
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 2
- 102000014150 Interferons Human genes 0.000 claims 2
- 108010050904 Interferons Proteins 0.000 claims 2
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims 2
- 150000001299 aldehydes Chemical class 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 2
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims 2
- 125000005154 alkyl sulfonyl amino alkyl group Chemical group 0.000 claims 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 2
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000010949 copper Substances 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 229940079322 interferon Drugs 0.000 claims 2
- AKDZOVQEOINYEA-MLBSPLJJSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]phenyl]methanesulfonamide;hydrate Chemical compound O.C1=C(N2C(NC(=O)C=C2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1 AKDZOVQEOINYEA-MLBSPLJJSA-N 0.000 claims 2
- OQFYZQSEUGUAKQ-TWGQIWQCSA-N n-[4-[(z)-2-[3-tert-butyl-5-(2,4-dioxo-1,3-diazinan-1-yl)-2-methoxyphenyl]ethenyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)CC2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C/C1=CC=C(NS(C)(=O)=O)C=C1 OQFYZQSEUGUAKQ-TWGQIWQCSA-N 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 229960000329 ribavirin Drugs 0.000 claims 2
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims 2
- 159000000000 sodium salts Chemical class 0.000 claims 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
- 229920002554 vinyl polymer Polymers 0.000 claims 2
- 230000029812 viral genome replication Effects 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- DRFUIFXSXHKDAJ-VMPITWQZSA-N 1-[3-[(e)-2-(4-aminophenyl)ethenyl]-5-tert-butyl-4-methoxyphenyl]-1,3-diazinane-2,4-dione Chemical compound C1=C(N2C(NC(=O)CC2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(N)C=C1 DRFUIFXSXHKDAJ-VMPITWQZSA-N 0.000 claims 1
- ZKBISQZXGWNNJF-RMKNXTFCSA-N 1-[3-tert-butyl-4-methoxy-5-[(e)-2-(4-methoxyphenyl)ethenyl]phenyl]-1,3-diazinane-2,4-dione Chemical compound C1=CC(OC)=CC=C1\C=C\C1=CC(N2C(NC(=O)CC2)=O)=CC(C(C)(C)C)=C1OC ZKBISQZXGWNNJF-RMKNXTFCSA-N 0.000 claims 1
- ZZDZUFNWIQXKMK-VMPITWQZSA-N 1-[3-tert-butyl-4-methoxy-5-[(e)-2-(4-nitrophenyl)ethenyl]phenyl]-1,3-diazinane-2,4-dione Chemical compound C1=C(N2C(NC(=O)CC2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C([N+]([O-])=O)C=C1 ZZDZUFNWIQXKMK-VMPITWQZSA-N 0.000 claims 1
- WOCXMPVSZIXTTL-NTCAYCPXSA-N 1-[3-tert-butyl-4-methoxy-5-[(e)-2-(4-nitrophenyl)prop-1-enyl]phenyl]-1,3-diazinane-2,4-dione Chemical compound C1=C(N2C(NC(=O)CC2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C(/C)C1=CC=C([N+]([O-])=O)C=C1 WOCXMPVSZIXTTL-NTCAYCPXSA-N 0.000 claims 1
- CECKEKPWSKBXKR-ZHACJKMWSA-N 1-[3-tert-butyl-4-methoxy-5-[(e)-2-phenylethenyl]phenyl]-1,3-diazinane-2,4-dione Chemical compound C1=C(N2C(NC(=O)CC2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=CC=C1 CECKEKPWSKBXKR-ZHACJKMWSA-N 0.000 claims 1
- PCHJCRRNWRTOPH-VMPITWQZSA-N 1-[3-tert-butyl-5-[(e)-2-(4-fluorophenyl)ethenyl]-4-methoxyphenyl]-1,3-diazinane-2,4-dione Chemical compound C1=C(N2C(NC(=O)CC2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(F)C=C1 PCHJCRRNWRTOPH-VMPITWQZSA-N 0.000 claims 1
- UXVJNJXNFTVINO-SNAWJCMRSA-N 1-[3-tert-butyl-5-[(e)-2-(4-nitrophenyl)ethenyl]phenyl]-1,3-diazinane-2,4-dione Chemical compound C=1C(N2C(NC(=O)CC2)=O)=CC(C(C)(C)C)=CC=1\C=C\C1=CC=C([N+]([O-])=O)C=C1 UXVJNJXNFTVINO-SNAWJCMRSA-N 0.000 claims 1
- VEILLWAJWLVBMO-UNOMPAQXSA-N 1-[3-tert-butyl-5-[(z)-2-chloro-2-(4-nitrophenyl)ethenyl]-4-methoxyphenyl]-1,3-diazinane-2,4-dione Chemical compound C1=C(N2C(NC(=O)CC2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C(/Cl)C1=CC=C([N+]([O-])=O)C=C1 VEILLWAJWLVBMO-UNOMPAQXSA-N 0.000 claims 1
- WINYGBXNPMHJAH-CMDGGOBGSA-N 2-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]-5-(methanesulfonamido)-n,n-dimethylbenzamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1C(=O)N(C)C WINYGBXNPMHJAH-CMDGGOBGSA-N 0.000 claims 1
- NWYGQDJZLJQVAW-CMDGGOBGSA-N 2-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]-5-(methanesulfonamido)-n-(2-methoxyethyl)-n-methylbenzamide Chemical compound COCCN(C)C(=O)C1=CC(NS(C)(=O)=O)=CC=C1\C=C\C1=CC(N2C(NC(=O)C=C2)=O)=CC(C(C)(C)C)=C1OC NWYGQDJZLJQVAW-CMDGGOBGSA-N 0.000 claims 1
- NOKWDXQYOYSYCU-BQYQJAHWSA-N 2-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]-5-(methanesulfonamido)-n-(2-methoxyethyl)benzamide Chemical compound COCCNC(=O)C1=CC(NS(C)(=O)=O)=CC=C1\C=C\C1=CC(N2C(NC(=O)C=C2)=O)=CC(C(C)(C)C)=C1OC NOKWDXQYOYSYCU-BQYQJAHWSA-N 0.000 claims 1
- CKAUPHBNBDEVND-BQYQJAHWSA-N 2-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]-5-(methanesulfonamido)-n-methylbenzamide Chemical compound CNC(=O)C1=CC(NS(C)(=O)=O)=CC=C1\C=C\C1=CC(N2C(NC(=O)C=C2)=O)=CC(C(C)(C)C)=C1OC CKAUPHBNBDEVND-BQYQJAHWSA-N 0.000 claims 1
- LOXYJRGWZOQFKX-VOTSOKGWSA-N 2-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]-5-(methanesulfonamido)benzamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1C(N)=O LOXYJRGWZOQFKX-VOTSOKGWSA-N 0.000 claims 1
- YNFBMDWHEHETJW-UHFFFAOYSA-N 2-pyridin-2-yl-1h-benzimidazole Chemical compound N1=CC=CC=C1C1=NC2=CC=CC=C2N1 YNFBMDWHEHETJW-UHFFFAOYSA-N 0.000 claims 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- ZXZFBQUBGNMVNG-SJCDEPGCSA-N N-[4-[2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]-3-[(E)-methoxyiminomethyl]phenyl]methanesulfonamide Chemical compound CO\N=C\C1=CC(NS(C)(=O)=O)=CC=C1C=CC1=CC(N2C(NC(=O)C=C2)=O)=CC(C(C)(C)C)=C1OC ZXZFBQUBGNMVNG-SJCDEPGCSA-N 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 241000700605 Viruses Species 0.000 claims 1
- 125000005091 alkenylcarbonylamino group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000005088 alkynylcarbonylamino group Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims 1
- YZDBZOOCRDOXFK-UHFFFAOYSA-N cyano-(diazidoamino)carbamic acid Chemical compound C(=O)(O)N(N(N=[N+]=[N-])N=[N+]=[N-])C#N YZDBZOOCRDOXFK-UHFFFAOYSA-N 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- WQODBAJDFZPKSG-UHFFFAOYSA-N ethyl 3-(methanesulfonamido)benzoate Chemical compound CCOC(=O)C1=CC=CC(NS(C)(=O)=O)=C1 WQODBAJDFZPKSG-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- YXJKGYFXOITURZ-UHFFFAOYSA-N methyl 2-[2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethyl]-5-(methanesulfonamido)benzoate Chemical compound COC(=O)C1=CC(NS(C)(=O)=O)=CC=C1CCC1=CC(N2C(NC(=O)C=C2)=O)=CC(C(C)(C)C)=C1OC YXJKGYFXOITURZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- CMOBXBANKIGTSJ-UHFFFAOYSA-N n-(2-cyanophenyl)pyridine-2-carboxamide Chemical compound C=1C=CC=NC=1C(=O)NC1=CC=CC=C1C#N CMOBXBANKIGTSJ-UHFFFAOYSA-N 0.000 claims 1
- WUYINQBOZASLCM-UHFFFAOYSA-N n-(4-cyanophenyl)pyridine-2-carboxamide Chemical compound C=1C=CC=NC=1C(=O)NC1=CC=C(C#N)C=C1 WUYINQBOZASLCM-UHFFFAOYSA-N 0.000 claims 1
- JOQBTUICIQOKES-BQYQJAHWSA-N n-[3-(azetidine-1-carbonyl)-4-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1C(=O)N1CCC1 JOQBTUICIQOKES-BQYQJAHWSA-N 0.000 claims 1
- PWNCIGITAJRSBB-VOTSOKGWSA-N n-[3-amino-4-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1N PWNCIGITAJRSBB-VOTSOKGWSA-N 0.000 claims 1
- QVNCCANKCIORFZ-DTQAZKPQSA-N n-[4-[(e)-1-[3-tert-butyl-5-(2,4-dioxo-1,3-diazinan-1-yl)-2-methoxyphenyl]prop-1-en-2-yl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)CC2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C(/C)C1=CC=C(NS(C)(=O)=O)C=C1 QVNCCANKCIORFZ-DTQAZKPQSA-N 0.000 claims 1
- IAUYTNDVCVBDFZ-ZZXKWVIFSA-N n-[4-[(e)-2-[3-bromo-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]phenyl]methanesulfonamide Chemical compound COC1=C(Br)C=C(N2C(NC(=O)C=C2)=O)C=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1 IAUYTNDVCVBDFZ-ZZXKWVIFSA-N 0.000 claims 1
- NQMWGEWHYNMNKP-VMPITWQZSA-N n-[4-[(e)-2-[3-tert-butyl-2-chloro-5-(2,4-dioxopyrimidin-1-yl)phenyl]ethenyl]phenyl]methanesulfonamide Chemical compound ClC=1C(C(C)(C)C)=CC(N2C(NC(=O)C=C2)=O)=CC=1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1 NQMWGEWHYNMNKP-VMPITWQZSA-N 0.000 claims 1
- DLCHOHXVKAYPGB-DEDYPNTBSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxo-1,3-diazinan-1-yl)-2-methoxyphenyl]-1-fluoroethenyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)CC2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C(\F)C1=CC=C(NS(C)(=O)=O)C=C1 DLCHOHXVKAYPGB-DEDYPNTBSA-N 0.000 claims 1
- HOAKSCSACRUZKT-SOFGYWHQSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxo-1,3-diazinan-1-yl)-2-methoxyphenyl]ethenyl]-2-fluorophenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)CC2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C(F)=C1 HOAKSCSACRUZKT-SOFGYWHQSA-N 0.000 claims 1
- WZVUIUYGBVDNJW-BQYQJAHWSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxo-1,3-diazinan-1-yl)-2-methoxyphenyl]ethenyl]-3-methoxyphenyl]methanesulfonamide Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1\C=C\C1=CC(N2C(NC(=O)CC2)=O)=CC(C(C)(C)C)=C1OC WZVUIUYGBVDNJW-BQYQJAHWSA-N 0.000 claims 1
- OQFYZQSEUGUAKQ-RMKNXTFCSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxo-1,3-diazinan-1-yl)-2-methoxyphenyl]ethenyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)CC2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1 OQFYZQSEUGUAKQ-RMKNXTFCSA-N 0.000 claims 1
- GXHLZLVGAAGVHA-AATRIKPKSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxo-1,3-diazinan-1-yl)phenyl]ethenyl]phenyl]methanesulfonamide Chemical compound C=1C(N2C(NC(=O)CC2)=O)=CC(C(C)(C)C)=CC=1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1 GXHLZLVGAAGVHA-AATRIKPKSA-N 0.000 claims 1
- OGDQRPNBONVZTO-JXMROGBWSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-ethoxyphenyl]ethenyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C(C)(C)C)C(OCC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1 OGDQRPNBONVZTO-JXMROGBWSA-N 0.000 claims 1
- WZXHXAMWFDIQQO-BQYQJAHWSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]-2-fluoro-5-methylphenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC(F)=C(NS(C)(=O)=O)C=C1C WZXHXAMWFDIQQO-BQYQJAHWSA-N 0.000 claims 1
- IPQZQHWJLZZJQG-SOFGYWHQSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]-2-fluorophenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C(F)=C1 IPQZQHWJLZZJQG-SOFGYWHQSA-N 0.000 claims 1
- KQZZQJKOIGYKGZ-VOTSOKGWSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]-3-(1h-imidazol-2-yl)phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1C1=NC=CN1 KQZZQJKOIGYKGZ-VOTSOKGWSA-N 0.000 claims 1
- HETHBDSMTRIUDF-JDRVRGJNSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]-3-(hydroxyiminomethyl)phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1C=NO HETHBDSMTRIUDF-JDRVRGJNSA-N 0.000 claims 1
- GYIVSZXIRSYQAR-VOTSOKGWSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]-3-(hydroxymethyl)phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1CO GYIVSZXIRSYQAR-VOTSOKGWSA-N 0.000 claims 1
- UIRJEJXGDNPWCF-VOTSOKGWSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]-3-(morpholine-4-carbonyl)phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1C(=O)N1CCOCC1 UIRJEJXGDNPWCF-VOTSOKGWSA-N 0.000 claims 1
- MADGSPBVPKIRMM-CMDGGOBGSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]-3-(propan-2-yloxymethyl)phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1COC(C)C MADGSPBVPKIRMM-CMDGGOBGSA-N 0.000 claims 1
- LPXDFJCZJYVNQV-CMDGGOBGSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]-3-(pyrrolidin-1-ylmethyl)phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1CN1CCCC1 LPXDFJCZJYVNQV-CMDGGOBGSA-N 0.000 claims 1
- RCLXXTQSDOATIA-CMDGGOBGSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]-3-(pyrrolidine-1-carbonyl)phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1C(=O)N1CCCC1 RCLXXTQSDOATIA-CMDGGOBGSA-N 0.000 claims 1
- YSVDGCAABXJPLN-VOTSOKGWSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]-3-[(3-hydroxyazetidin-1-yl)methyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1CN1CC(O)C1 YSVDGCAABXJPLN-VOTSOKGWSA-N 0.000 claims 1
- JRSUAVVNBNGFPJ-CMDGGOBGSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]-3-[(3-methylbutylamino)methyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1CNCCC(C)C JRSUAVVNBNGFPJ-CMDGGOBGSA-N 0.000 claims 1
- USKJJFVDENKFPG-VOTSOKGWSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]-3-formylphenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1C=O USKJJFVDENKFPG-VOTSOKGWSA-N 0.000 claims 1
- UETWUMCNWIJTIC-RMKNXTFCSA-N n-[4-[(e)-2-[3-tert-butyl-5-(5-chloro-2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C(Cl)=C2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1 UETWUMCNWIJTIC-RMKNXTFCSA-N 0.000 claims 1
- ZRYYUSRSKNQPOS-RMKNXTFCSA-N n-[4-[(e)-2-[3-tert-butyl-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C(F)=C2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1 ZRYYUSRSKNQPOS-RMKNXTFCSA-N 0.000 claims 1
- IJTCBUGBHGTSCF-VMPITWQZSA-N n-[4-[(e)-2-[5-(2,4-dioxopyrimidin-1-yl)-2-methoxy-3-pyridin-3-ylphenyl]ethenyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C=2C=NC=CC=2)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1 IJTCBUGBHGTSCF-VMPITWQZSA-N 0.000 claims 1
- RMOODACIVICURL-ZZXKWVIFSA-N n-[4-[(e)-2-[5-(2,4-dioxopyrimidin-1-yl)-2-methoxy-3-pyridin-4-ylphenyl]ethenyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C=2C=CN=CC=2)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1 RMOODACIVICURL-ZZXKWVIFSA-N 0.000 claims 1
- MEAXCWNKDXGYRD-VMPITWQZSA-N n-[4-[(e)-2-[5-(2,4-dioxopyrimidin-1-yl)-2-methoxy-3-thiophen-2-ylphenyl]ethenyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C=2SC=CC=2)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1 MEAXCWNKDXGYRD-VMPITWQZSA-N 0.000 claims 1
- HWTXCVILTQZFAO-ZZXKWVIFSA-N n-[4-[(e)-2-[5-(2,4-dioxopyrimidin-1-yl)-2-methoxy-3-thiophen-3-ylphenyl]ethenyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C2=CSC=C2)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1 HWTXCVILTQZFAO-ZZXKWVIFSA-N 0.000 claims 1
- QXGFUWDHDLOEMF-VMPITWQZSA-N n-[4-[(e)-2-[5-(2,4-dioxopyrimidin-1-yl)-3-(1-hydroxy-2-methylpropan-2-yl)-2-methoxyphenyl]ethenyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C(C)(C)CO)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1 QXGFUWDHDLOEMF-VMPITWQZSA-N 0.000 claims 1
- SOWGPHBQMBRKDJ-VMPITWQZSA-N n-[4-[(e)-2-[5-(2,4-dioxopyrimidin-1-yl)-3-(furan-2-yl)-2-methoxyphenyl]ethenyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C=2OC=CC=2)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1 SOWGPHBQMBRKDJ-VMPITWQZSA-N 0.000 claims 1
- GZPGLYCWHREZSK-ZZXKWVIFSA-N n-[4-[(e)-2-[5-(2,4-dioxopyrimidin-1-yl)-3-(furan-3-yl)-2-methoxyphenyl]ethenyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C2=COC=C2)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1 GZPGLYCWHREZSK-ZZXKWVIFSA-N 0.000 claims 1
- LTRUMANBSIKPFC-ZZXKWVIFSA-N n-[4-[(e)-2-[5-(2,4-dioxopyrimidin-1-yl)-3-iodo-2-methoxyphenyl]ethenyl]phenyl]methanesulfonamide Chemical compound COC1=C(I)C=C(N2C(NC(=O)C=C2)=O)C=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1 LTRUMANBSIKPFC-ZZXKWVIFSA-N 0.000 claims 1
- MRZJFMIOPBWFEC-MOSHPQCFSA-N n-[4-[(z)-2-[3-tert-butyl-5-(2,4-dioxo-1,3-diazinan-1-yl)-2-methoxyphenyl]-1-chloroethenyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)CC2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C(/Cl)C1=CC=C(NS(C)(=O)=O)C=C1 MRZJFMIOPBWFEC-MOSHPQCFSA-N 0.000 claims 1
- DLCHOHXVKAYPGB-MOSHPQCFSA-N n-[4-[(z)-2-[3-tert-butyl-5-(2,4-dioxo-1,3-diazinan-1-yl)-2-methoxyphenyl]-1-fluoroethenyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)CC2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C(/F)C1=CC=C(NS(C)(=O)=O)C=C1 DLCHOHXVKAYPGB-MOSHPQCFSA-N 0.000 claims 1
- HSXLICOMYMMQRM-STZFKDTASA-N n-[4-[(z)-2-[3-tert-butyl-5-(2,4-dioxo-1,3-diazinan-1-yl)-2-methoxyphenyl]-1-methoxyethenyl]phenyl]methanesulfonamide Chemical compound C=1C=C(NS(C)(=O)=O)C=CC=1C(/OC)=C/C(C(=C(C=1)C(C)(C)C)OC)=CC=1N1CCC(=O)NC1=O HSXLICOMYMMQRM-STZFKDTASA-N 0.000 claims 1
- XMZSTQYSBYEENY-TWGQIWQCSA-N n-[4-[(z)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C/C1=CC=C(NS(C)(=O)=O)C=C1 XMZSTQYSBYEENY-TWGQIWQCSA-N 0.000 claims 1
- FNCXOQVFRIJGCX-UHFFFAOYSA-N n-[4-[2-[3-tert-butyl-5-(2,4-dioxo-1,3-diazinan-1-yl)-2-methoxyphenyl]ethyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)CC2)=O)C=C(C(C)(C)C)C(OC)=C1CCC1=CC=C(NS(C)(=O)=O)C=C1 FNCXOQVFRIJGCX-UHFFFAOYSA-N 0.000 claims 1
- VUBMBVKDVRKAGN-UHFFFAOYSA-N n-[4-[2-[3-tert-butyl-5-(2,4-dioxo-1,3-diazinan-1-yl)phenyl]ethyl]phenyl]methanesulfonamide Chemical compound C=1C(N2C(NC(=O)CC2)=O)=CC(C(C)(C)C)=CC=1CCC1=CC=C(NS(C)(=O)=O)C=C1 VUBMBVKDVRKAGN-UHFFFAOYSA-N 0.000 claims 1
- WBFRMRWRFQYBOF-UHFFFAOYSA-N n-[4-[2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C(C)(C)C)C(OC)=C1CCC1=CC=C(NS(C)(=O)=O)C=C1 WBFRMRWRFQYBOF-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229960003540 oxyquinoline Drugs 0.000 claims 1
- 159000000001 potassium salts Chemical class 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims 1
- 230000010076 replication Effects 0.000 claims 1
- 125000005504 styryl group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
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| PCT/US2008/076594 WO2009039135A1 (en) | 2007-09-17 | 2008-09-17 | N-phenyl-dioxo-hydropyrimidines useful as hepatitis c virus (hcv) inhibitors |
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| MX2010002904A (es) * | 2007-09-17 | 2010-06-02 | Abbott Lab | N-fenil-dioxo-hidropirimidinas utiles como inhibidores de virus de hepatitis c (hcv). |
| KR101552474B1 (ko) * | 2007-09-17 | 2015-09-11 | 애브비 바하마스 리미티드 | Ｃ형 간염 치료용 우라실 또는 티민 유도체 |
| EP2639226B1 (en) | 2007-09-17 | 2016-08-31 | AbbVie Bahamas Ltd. | Anti-infective pyrimidines and uses thereof |
| CN102099335A (zh) | 2008-07-23 | 2011-06-15 | 弗·哈夫曼-拉罗切有限公司 | 杂环抗病毒化合物 |
| JP2012503620A (ja) | 2008-09-26 | 2012-02-09 | エフ．ホフマン−ラ ロシュ アーゲー | Ｈｃｖを処置するためのピリンまたはピラジン誘導体 |
| AU2009309813A1 (en) | 2008-10-30 | 2010-05-06 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral arylpyridone derivatives |
| BRPI0924121A2 (pt) | 2008-12-22 | 2019-09-24 | Hoffmann La Roche | compostos antivirais heterocíclicos |
| BRPI1016266A2 (pt) | 2009-03-06 | 2019-09-24 | Hoffmann La Roche | compostos antivirais heterocíclicos |
| JP5744003B2 (ja) * | 2009-03-24 | 2015-07-01 | アッヴィ・バハマズ・リミテッド | 抗ウイルス化合物を調製する方法 |
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| TWI428332B (zh) | 2009-06-09 | 2014-03-01 | Hoffmann La Roche | 雜環抗病毒化合物 |
| AU2010264802A1 (en) * | 2009-06-24 | 2012-01-19 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compound |
| BR112012005616A2 (pt) | 2009-09-21 | 2016-06-21 | Hoffmann La Roche | compostos antivirais heterocíclicos |
| US8822496B2 (en) | 2009-10-30 | 2014-09-02 | Boehringer Ingelheim International Gmbh | Dosage regimens for HCV combination therapy |
| CN102639504A (zh) * | 2009-11-21 | 2012-08-15 | 弗·哈夫曼-拉罗切有限公司 | 杂环抗病毒化合物 |
| PH12012501216A1 (en) * | 2009-12-18 | 2012-11-05 | Boehringer Ingelheim Int | Hcv combination therapy |
| US9216952B2 (en) | 2010-03-23 | 2015-12-22 | Abbvie Inc. | Process for preparing antiviral compound |
| BR112013000245A2 (pt) * | 2010-07-07 | 2016-05-24 | Hoffmann La Roche | compostos antivirais heterocíclicos |
| US9255074B2 (en) | 2010-07-16 | 2016-02-09 | Abbvie Inc. | Process for preparing antiviral compounds |
| US8841487B2 (en) | 2010-07-16 | 2014-09-23 | Abbvie Inc. | Phosphine ligands for catalytic reactions |
| US8975443B2 (en) | 2010-07-16 | 2015-03-10 | Abbvie Inc. | Phosphine ligands for catalytic reactions |
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2008
- 2008-09-17 MX MX2010002904A patent/MX2010002904A/es active IP Right Grant
- 2008-09-17 HR HR20110632T patent/HRP20110632T1/hr unknown
- 2008-09-17 PT PT08831558T patent/PT2203430E/pt unknown
- 2008-09-17 EP EP11163527A patent/EP2377854A1/en not_active Withdrawn
- 2008-09-17 CN CN201510508424.3A patent/CN105294569A/zh active Pending
- 2008-09-17 CA CA2699989A patent/CA2699989C/en not_active Expired - Fee Related
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- 2008-09-17 CN CN201610091594.0A patent/CN105693626A/zh active Pending
- 2008-09-17 AT AT08831558T patent/ATE512954T1/de active
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- 2008-09-17 EP EP12185550A patent/EP2548873A1/en not_active Withdrawn
- 2008-09-17 WO PCT/US2008/076594 patent/WO2009039135A1/en not_active Ceased
- 2008-09-17 JP JP2010525104A patent/JP5726527B2/ja active Active
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