JP2010539188A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US97288707P | 2007-09-17 | 2007-09-17 | |
| US60/972,887 | 2007-09-17 | ||
| US9679408P | 2008-09-13 | 2008-09-13 | |
| US61/096,794 | 2008-09-13 | ||
| PCT/US2008/076594 WO2009039135A1 (en) | 2007-09-17 | 2008-09-17 | N-phenyl-dioxo-hydropyrimidines useful as hepatitis c virus (hcv) inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010539188A JP2010539188A (ja) | 2010-12-16 |
| JP2010539188A5 true JP2010539188A5 (enExample) | 2012-11-15 |
| JP5726527B2 JP5726527B2 (ja) | 2015-06-03 |
Family
ID=40091991
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010525104A Active JP5726527B2 (ja) | 2007-09-17 | 2008-09-17 | Ｃ型肝炎ウイルス（ｈｃｖ）阻害薬として有用なｎ−フェニル−ジオキソ−ヒドロピリミジン |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US8178548B2 (enExample) |
| EP (3) | EP2548873A1 (enExample) |
| JP (1) | JP5726527B2 (enExample) |
| CN (3) | CN101918369B (enExample) |
| AT (1) | ATE512954T1 (enExample) |
| CA (1) | CA2699989C (enExample) |
| DK (1) | DK2203430T3 (enExample) |
| HR (1) | HRP20110632T1 (enExample) |
| MX (1) | MX2010002904A (enExample) |
| PL (1) | PL2203430T3 (enExample) |
| PT (1) | PT2203430E (enExample) |
| RU (1) | RU2542099C2 (enExample) |
| WO (1) | WO2009039135A1 (enExample) |
| ZA (1) | ZA201002690B (enExample) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI534137B (zh) | 2007-09-17 | 2016-05-21 | 艾伯維巴哈馬有限公司 | 抗感染劑及其用途 |
| PT2203431E (pt) | 2007-09-17 | 2011-10-12 | Abbott Lab | Pirimidinas anti-infecciosas e seus usos |
| CN101918369B (zh) | 2007-09-17 | 2016-02-24 | 艾伯维巴哈马有限公司 | 治疗丙型肝炎的尿嘧啶或胸腺嘧啶衍生物 |
| BRPI0916233A2 (pt) | 2008-07-23 | 2018-03-13 | F.Hoffman-La Roche Ag | compostos heterocíclicos antivirais |
| KR20110061640A (ko) | 2008-09-26 | 2011-06-09 | 에프. 호프만-라 로슈 아게 | Ｈｃｖ 치료용 피린 또는 피라진 유도체 |
| MX2011004133A (es) | 2008-10-30 | 2011-05-24 | Hoffmann La Roche | Derivados de arilpiridona antiviral heterociclica. |
| EP2379534A1 (en) | 2008-12-22 | 2011-10-26 | F. Hoffmann-La Roche AG | Heterocyclic antiviral compounds |
| SG174252A1 (en) | 2009-03-06 | 2011-10-28 | Hoffmann La Roche | Heterocyclic antiviral compounds |
| CN102361858B (zh) * | 2009-03-24 | 2014-07-23 | 艾伯维巴哈马有限公司 | 制备抗病毒化合物的方法 |
| CA2758838A1 (en) * | 2009-04-25 | 2010-10-28 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compounds |
| AR077004A1 (es) | 2009-06-09 | 2011-07-27 | Hoffmann La Roche | Compuestos heterociclicos antivirales |
| SG176976A1 (en) * | 2009-06-24 | 2012-02-28 | Hoffmann La Roche | Heterocyclic antiviral compound |
| AU2010297290A1 (en) | 2009-09-21 | 2012-03-15 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compounds |
| NZ598465A (en) | 2009-10-30 | 2013-10-25 | Boehringer Ingelheim Int | Dosage regimens for hcv combination therapy comprising bi201335, interferon alpha and ribavirin |
| KR20120085918A (ko) * | 2009-11-21 | 2012-08-01 | 에프. 호프만-라 로슈 아게 | 헤테로환형 항바이러스성 화합물 |
| KR20120116404A (ko) * | 2009-12-18 | 2012-10-22 | 베링거 인겔하임 인터내셔날 게엠베하 | Ｈｃｖ 병용 요법 |
| US9216952B2 (en) | 2010-03-23 | 2015-12-22 | Abbvie Inc. | Process for preparing antiviral compound |
| MX2012014235A (es) * | 2010-07-07 | 2013-01-28 | Hoffmann La Roche | Compuestos hetericiclicos antiviricos. |
| EA028082B1 (ru) | 2010-07-16 | 2017-10-31 | ЭббВи Айэленд Анлимитед Компани | Способ получения сульфонамидного противовирусного соединения |
| US9255074B2 (en) | 2010-07-16 | 2016-02-09 | Abbvie Inc. | Process for preparing antiviral compounds |
| WO2012009698A1 (en) | 2010-07-16 | 2012-01-19 | Abbott Laboratories | Phosphine ligands for catalytic reactions |
| US8975443B2 (en) | 2010-07-16 | 2015-03-10 | Abbvie Inc. | Phosphine ligands for catalytic reactions |
| EP2685964A1 (en) * | 2011-03-18 | 2014-01-22 | AbbVie Inc. | Formulations of phenyl uracil compounds |
| US8989328B2 (en) * | 2013-03-14 | 2015-03-24 | Qualcomm Incorporated | Systems and methods for serial communication |
| EP3043803B1 (en) | 2013-09-11 | 2022-04-27 | Emory University | Nucleotide and nucleoside compositions and their uses |
| CN106065009B (zh) * | 2014-06-28 | 2019-03-01 | 广东东阳光药业有限公司 | 作为丙型肝炎抑制剂的化合物及其在药物中的应用 |
| WO2017189978A1 (en) | 2016-04-28 | 2017-11-02 | Emory University | Alkyne containing nucleotide and nucleoside therapeutic compositions and uses related thereto |
| US11026958B2 (en) | 2016-11-01 | 2021-06-08 | Merck Sharp & Dohme Corp. | Substituted 6-membered aryl or heteroaryl allosteric modulators of nicotinic acetylcholine receptors |
| CN111936498B (zh) | 2018-03-26 | 2024-04-16 | 诺华股份有限公司 | N-(3-(7H-吡咯并[2,3-d]嘧啶-4-基)苯基)苯甲酰胺衍生物 |
| CN110483496B (zh) * | 2019-07-17 | 2021-05-04 | 杭州市西溪医院 | 一类具有尿嘧啶-苯并噻唑结构衍生物、其制备方法及抗hcv药物的应用 |
| JP7785663B2 (ja) * | 2019-09-16 | 2025-12-15 | ノバルティス アーゲー | 二機能性分解誘導薬及びそれらの使用方法 |
| US12260392B2 (en) | 2019-09-16 | 2025-03-25 | Visa International Service Association | System, method, and computer program product for verifying a card image |
| EP3819006A1 (en) | 2019-11-05 | 2021-05-12 | Technische Universität Dresden | Compounds with thymine skeleton for use in medicine |
| CN111018910A (zh) * | 2019-12-05 | 2020-04-17 | 上海应用技术大学 | 一种铜催化合成含芳环α-羟基膦酸酯的方法 |
| CN111518036A (zh) * | 2020-04-29 | 2020-08-11 | 杭州勇诚睿生物科技有限公司 | 一种达沙布韦关键中间体的制备方法 |
| US12274700B1 (en) | 2020-10-30 | 2025-04-15 | Accencio LLC | Methods of treating symptoms of coronavirus infection with RNA polymerase inhibitors |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4239888A (en) * | 1974-11-04 | 1980-12-16 | Pfizer Inc. | 1-Phenyluracils |
| JPS60243017A (ja) * | 1984-05-16 | 1985-12-03 | Kyowa Hakko Kogyo Co Ltd | 抗けいれん組成物 |
| AU627906B2 (en) * | 1989-07-14 | 1992-09-03 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
| US5084084A (en) * | 1989-07-14 | 1992-01-28 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
| US5162326A (en) * | 1990-02-15 | 1992-11-10 | Takeda Chemical Industries, Ltd. | Pyrimidinedione derivatives, their production and use |
| NL9001075A (enExample) * | 1990-05-04 | 1991-12-02 | Duphar Int Res | |
| EP0489480A1 (en) * | 1990-12-05 | 1992-06-10 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
| JPH05213755A (ja) | 1992-02-07 | 1993-08-24 | Nikko Kyodo Co Ltd | 肝臓障害治療薬 |
| DE19528305A1 (de) | 1995-08-02 | 1997-02-06 | Bayer Ag | Substituierte Phenyluracile |
| SI1237878T1 (sl) | 1999-12-06 | 2007-08-31 | Hoffmann La Roche | 4-pirimidinil-n-acil-l-fenilanin |
| US6380387B1 (en) * | 1999-12-06 | 2002-04-30 | Hoffmann-La Roche Inc. | 4-Pyrimidinyl-n-acyl-l phenylalanines |
| IL141034A0 (en) * | 2000-02-04 | 2002-02-10 | Sumitomo Chemical Co | Uracil compounds and use thereof |
| RU2264395C2 (ru) * | 2000-02-04 | 2005-11-20 | Сумитомо Кемикал Компани, Лимитед | Производные урацила, гербицидная композиция, способ борьбы с сорняками и промежуточные продукты (варианты) |
| MY164523A (en) * | 2000-05-23 | 2017-12-29 | Univ Degli Studi Cagliari | Methods and compositions for treating hepatitis c virus |
| TW200505872A (en) * | 2003-06-13 | 2005-02-16 | Lg Life Science Ltd | Hepatitis C virus inhibitors |
| US7163937B2 (en) | 2003-08-21 | 2007-01-16 | Bristol-Myers Squibb Company | Cyclic derivatives as modulators of chemokine receptor activity |
| CN101918369B (zh) | 2007-09-17 | 2016-02-24 | 艾伯维巴哈马有限公司 | 治疗丙型肝炎的尿嘧啶或胸腺嘧啶衍生物 |
| TWI534137B (zh) * | 2007-09-17 | 2016-05-21 | 艾伯維巴哈馬有限公司 | 抗感染劑及其用途 |
| PT2203431E (pt) | 2007-09-17 | 2011-10-12 | Abbott Lab | Pirimidinas anti-infecciosas e seus usos |
| BRPI0916233A2 (pt) | 2008-07-23 | 2018-03-13 | F.Hoffman-La Roche Ag | compostos heterocíclicos antivirais |
-
2008
- 2008-09-17 CN CN200880116208.2A patent/CN101918369B/zh not_active Expired - Fee Related
- 2008-09-17 DK DK08831558.5T patent/DK2203430T3/da active
- 2008-09-17 RU RU2010114826/04A patent/RU2542099C2/ru active
- 2008-09-17 CN CN201610091594.0A patent/CN105693626A/zh active Pending
- 2008-09-17 PL PL08831558T patent/PL2203430T3/pl unknown
- 2008-09-17 MX MX2010002904A patent/MX2010002904A/es active IP Right Grant
- 2008-09-17 US US12/212,315 patent/US8178548B2/en active Active
- 2008-09-17 AT AT08831558T patent/ATE512954T1/de active
- 2008-09-17 CA CA2699989A patent/CA2699989C/en not_active Expired - Fee Related
- 2008-09-17 HR HR20110632T patent/HRP20110632T1/hr unknown
- 2008-09-17 JP JP2010525104A patent/JP5726527B2/ja active Active
- 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 PT PT08831558T patent/PT2203430E/pt unknown
- 2008-09-17 CN CN201510508424.3A patent/CN105294569A/zh active Pending
- 2008-09-17 EP EP11163527A patent/EP2377854A1/en not_active Withdrawn
- 2008-09-17 EP EP08831558A patent/EP2203430B1/en not_active Not-in-force
-
2010
- 2010-04-16 ZA ZA2010/02690A patent/ZA201002690B/en unknown
-
2012
- 2012-04-06 US US13/441,528 patent/US8986740B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010539188A5 (enExample) | ||
| JP2010539187A5 (enExample) | ||
| JP2010539186A5 (enExample) | ||
| HRP20110632T1 (hr) | N-fenil-diokso-hidropirimidini korisni kao inhibitori virusa hepatitisa c (hcv) | |
| RU2013104270A (ru) | Производные урацила или тимина для лечения гепатита с | |
| RU2014147354A (ru) | Пиримидины, которые могут быть использованы в качестве противоинфекционных средств, и их применения | |
| RU2015144653A (ru) | Противовирусные соединения и их применения | |
| JP2010510242A5 (enExample) | ||
| JP2015526441A5 (enExample) | ||
| JP2010534654A5 (enExample) | ||
| JP2017511794A5 (enExample) | ||
| JP2013530240A5 (enExample) | ||
| JP2009046489A (ja) | Ｃ−グリコシド誘導体又はその塩 | |
| JP2004532227A5 (enExample) | ||
| CA2570942A1 (en) | Substituted tetrahydro-2h-isoquinolin-1-one derivatives, method for the production thereof, and use of the same as medicament | |
| JP2013505949A5 (enExample) | ||
| JP2005514432A5 (enExample) | ||
| JP2013537913A5 (enExample) | ||
| JP2020500192A5 (enExample) | ||
| WO2007002637B1 (en) | N-linked heterocyclic antagonists of p2y1 receptor useful in the treatment of thrombotic conditions | |
| JP2007532654A5 (enExample) | ||
| JP2014500252A5 (enExample) | ||
| HK1182090A (en) | N-phenyl-dioxo-hydropyrimidines useful as hepatitis c virus (hcv) inhibitors | |
| HK1145839B (en) | N-phenyl-dioxo-hydropyrimidines useful as hepatitis c virus (hcv) inhibitors |