RU2542099C2 - N-фенил-диоксо-гидропиримидины, используемые в качестве ингибитора вируса гепатита с (hcv) - Google Patents
N-фенил-диоксо-гидропиримидины, используемые в качестве ингибитора вируса гепатита с (hcv) Download PDFInfo
- Publication number
- RU2542099C2 RU2542099C2 RU2010114826/04A RU2010114826A RU2542099C2 RU 2542099 C2 RU2542099 C2 RU 2542099C2 RU 2010114826/04 A RU2010114826/04 A RU 2010114826/04A RU 2010114826 A RU2010114826 A RU 2010114826A RU 2542099 C2 RU2542099 C2 RU 2542099C2
- Authority
- RU
- Russia
- Prior art keywords
- tert
- butyl
- phenyl
- group
- methanesulfonamide
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title claims description 10
- 241000711549 Hepacivirus C Species 0.000 title description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 414
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 205
- 150000003839 salts Chemical class 0.000 claims abstract description 189
- 125000005843 halogen group Chemical group 0.000 claims abstract description 158
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 138
- 239000001257 hydrogen Substances 0.000 claims abstract description 138
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 74
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 69
- 238000000034 method Methods 0.000 claims abstract description 59
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 56
- 239000003814 drug Substances 0.000 claims abstract description 34
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 33
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 20
- 208000005176 Hepatitis C Diseases 0.000 claims abstract description 19
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 18
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 102000004163 DNA-directed RNA polymerases Human genes 0.000 claims abstract description 8
- 108090000626 DNA-directed RNA polymerases Proteins 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 7
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000005977 Ethylene Substances 0.000 claims abstract description 6
- 229940124683 HCV polymerase inhibitor Drugs 0.000 claims abstract description 4
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 350
- 125000001424 substituent group Chemical group 0.000 claims description 340
- 125000000623 heterocyclic group Chemical group 0.000 claims description 241
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 141
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 137
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 133
- 125000003545 alkoxy group Chemical group 0.000 claims description 117
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 77
- 238000002360 preparation method Methods 0.000 claims description 71
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 61
- 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 description 54
- 239000000843 powder Substances 0.000 claims description 44
- 238000011282 treatment Methods 0.000 claims description 44
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 27
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 23
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 22
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 20
- 239000000460 chlorine Substances 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 229940124597 therapeutic agent Drugs 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 17
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 17
- 102000014150 Interferons Human genes 0.000 claims description 15
- 108010050904 Interferons Proteins 0.000 claims description 15
- 150000001299 aldehydes Chemical class 0.000 claims description 15
- 229940079322 interferon Drugs 0.000 claims description 15
- 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 description 14
- 229960000329 ribavirin Drugs 0.000 claims description 14
- 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 description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 claims description 13
- 239000003446 ligand Substances 0.000 claims description 13
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 6
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- MXIWSDNQPPKKCQ-MLBSPLJJSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]phenyl]methanesulfonamide;potassium Chemical compound [K].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 MXIWSDNQPPKKCQ-MLBSPLJJSA-N 0.000 claims description 5
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 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 description 3
- 239000005725 8-Hydroxyquinoline Substances 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 230000005764 inhibitory process Effects 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 229960003540 oxyquinoline Drugs 0.000 claims description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 3
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- HEKAVWSAFBOGOD-UHFFFAOYSA-N n-[4-[2-[3-tert-butyl-5-(2,4-dioxo-1,3-diazinan-1-yl)-2-methoxyphenyl]cyclopropyl]phenyl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C2C(C2)C=2C=CC(NS(C)(=O)=O)=CC=2)C=C1N1CCC(=O)NC1=O HEKAVWSAFBOGOD-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 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 15
- CMRCKCWAEWYWRN-UHFFFAOYSA-N [Na+].[Na+].CS(=O)(=O)[NH-].CS(=O)(=O)[NH-] Chemical compound [Na+].[Na+].CS(=O)(=O)[NH-].CS(=O)(=O)[NH-] CMRCKCWAEWYWRN-UHFFFAOYSA-N 0.000 claims 4
- 239000000945 filler Substances 0.000 claims 3
- ZLAGJEHVBCNXOA-SWSRPJROSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]phenyl]methanesulfonamide;sodium Chemical compound [Na].[Na].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 ZLAGJEHVBCNXOA-SWSRPJROSA-N 0.000 claims 3
- 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
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004845 (C1-C6) alkylsulfonylamino 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
- 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
- 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
- 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
- RZQLRSZSLPTHMQ-VOTSOKGWSA-N 2-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]-5-(methanesulfonamido)benzoic acid 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)=O RZQLRSZSLPTHMQ-VOTSOKGWSA-N 0.000 claims 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 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
- XNKPMUBPFWXXAD-UHFFFAOYSA-N O.CS(N)(=O)=O Chemical compound O.CS(N)(=O)=O XNKPMUBPFWXXAD-UHFFFAOYSA-N 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- YDSXAIMDAKZAHR-BQYQJAHWSA-N methyl 2-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]-5-(methanesulfonamido)benzoate Chemical compound COC(=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 YDSXAIMDAKZAHR-BQYQJAHWSA-N 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
- 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
- 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
- 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
- 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
- HMSDQYZFQDWDAH-VOTSOKGWSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]-3-(1,3-oxazol-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=CO1 HMSDQYZFQDWDAH-VOTSOKGWSA-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
- FYUJAZCPURPNIF-BQYQJAHWSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]-3-(methoxymethyl)phenyl]methanesulfonamide Chemical compound COCC1=CC(NS(C)(=O)=O)=CC=C1\C=C\C1=CC(N2C(NC(=O)C=C2)=O)=CC(C(C)(C)C)=C1OC FYUJAZCPURPNIF-BQYQJAHWSA-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
- 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
- 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
- WEDJJJMLEFPPNK-QPJJXVBHSA-N n-[4-[(e)-2-[5-(2,4-dioxopyrimidin-1-yl)-2-methoxy-3-methylsulfonylphenyl]ethenyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(S(C)(=O)=O)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1 WEDJJJMLEFPPNK-QPJJXVBHSA-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
- 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
- DLCHOHXVKAYPGB-UHFFFAOYSA-N n-[4-[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)=C1C=C(F)C1=CC=C(NS(C)(=O)=O)C=C1 DLCHOHXVKAYPGB-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
- AWRZGDBXGAFGGI-MDZDMXLPSA-N tert-butyl n-[2-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]-5-(methanesulfonamido)phenyl]carbamate 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=C1NC(=O)OC(C)(C)C AWRZGDBXGAFGGI-MDZDMXLPSA-N 0.000 claims 1
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
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- A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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| RU2543620C2 (ru) * | 2007-09-17 | 2015-03-10 | Эббви Бахамаз Лтд. | Производные урацила или тимина для лечения гепатита с |
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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). |
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| SG172778A1 (en) | 2008-12-22 | 2011-08-29 | Hoffmann La Roche | Heterocyclic antiviral compounds |
| TW201035083A (en) | 2009-03-06 | 2010-10-01 | Hoffmann La Roche | Heterocyclic antiviral compounds |
| 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 |
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| BR112012005616A2 (pt) | 2009-09-21 | 2016-06-21 | Hoffmann La Roche | compostos antivirais heterocíclicos |
| NZ598465A (en) | 2009-10-30 | 2013-10-25 | Boehringer Ingelheim Int | Dosage regimens for hcv combination therapy comprising bi201335, interferon alpha and ribavirin |
| EP2501679A1 (en) * | 2009-11-21 | 2012-09-26 | F. Hoffmann-La Roche AG | Heterocyclic antiviral compounds |
| CN102753173A (zh) * | 2009-12-18 | 2012-10-24 | 贝林格尔.英格海姆国际有限公司 | Hcv组合疗法 |
| US9216952B2 (en) | 2010-03-23 | 2015-12-22 | Abbvie Inc. | Process for preparing antiviral compound |
| JP5651239B2 (ja) * | 2010-07-07 | 2015-01-07 | エフ.ホフマン−ラ ロシュ アーゲーF. Hoffmann−La Roche Aktiengesellschaft | 複素環式抗ウイルス化合物 |
| US9255074B2 (en) | 2010-07-16 | 2016-02-09 | Abbvie Inc. | Process for preparing antiviral compounds |
| US8975443B2 (en) | 2010-07-16 | 2015-03-10 | Abbvie Inc. | Phosphine ligands for catalytic reactions |
| AU2011278927B2 (en) | 2010-07-16 | 2015-05-21 | Abbvie Ireland Unlimited Company | Process for preparing antiviral compounds |
| BR112013001138A2 (pt) | 2010-07-16 | 2016-07-05 | Abbvie Inc | ligantes de fosfina para reações catalíticas |
| TWI558400B (zh) * | 2011-03-18 | 2016-11-21 | 艾伯維有限公司 | 苯基尿嘧啶化合物之調配物 |
| US8989328B2 (en) * | 2013-03-14 | 2015-03-24 | Qualcomm Incorporated | Systems and methods for serial communication |
| PL3043803T3 (pl) | 2013-09-11 | 2022-11-07 | Emory University | Kompozycje nukleotydowe i nukleozydowe oraz ich zastosowanie |
| 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 |
| US11192914B2 (en) | 2016-04-28 | 2021-12-07 | Emory University | Alkyne containing nucleotide and nucleoside therapeutic compositions and uses related thereto |
| JP7041140B2 (ja) * | 2016-11-01 | 2022-03-23 | メルク・シャープ・アンド・ドーム・コーポレーション | 置換された6員アリール又はヘテロアリール系ニコチン性アセチルコリン受容体アロステリック調節剤 |
| EP3774804A1 (en) | 2018-03-26 | 2021-02-17 | Novartis AG | N-(3-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)phenyl)benzamide derivatives |
| 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 |
| EP4031247A1 (en) * | 2019-09-16 | 2022-07-27 | Novartis AG | Bifunctional degraders and their methods of use |
| EP4032006A4 (en) | 2019-09-16 | 2022-11-23 | Visa International Service Association | SYSTEM, METHOD AND COMPUTER PROGRAM PRODUCT FOR VERIFYING A MAP 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 |
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| DE19528305A1 (de) | 1995-08-02 | 1997-02-06 | Bayer Ag | Substituierte Phenyluracile |
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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). |
| PL2203431T3 (pl) | 2007-09-17 | 2012-01-31 | Abbvie Bahamas Ltd | Pirymidyny o działaniu przeciw zakaźnym oraz ich zastosowania |
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2008
- 2008-09-17 MX MX2010002904A patent/MX2010002904A/es active IP Right Grant
- 2008-09-17 CN CN200880116208.2A patent/CN101918369B/zh not_active Expired - Fee Related
- 2008-09-17 WO PCT/US2008/076594 patent/WO2009039135A1/en not_active Ceased
- 2008-09-17 DK DK08831558.5T patent/DK2203430T3/da active
- 2008-09-17 EP EP12185550A patent/EP2548873A1/en not_active Withdrawn
- 2008-09-17 PL PL08831558T patent/PL2203430T3/pl unknown
- 2008-09-17 CA CA2699989A patent/CA2699989C/en not_active Expired - Fee Related
- 2008-09-17 US US12/212,315 patent/US8178548B2/en active Active
- 2008-09-17 JP JP2010525104A patent/JP5726527B2/ja active Active
- 2008-09-17 HR HR20110632T patent/HRP20110632T1/hr unknown
- 2008-09-17 CN CN201510508424.3A patent/CN105294569A/zh active Pending
- 2008-09-17 RU RU2010114826/04A patent/RU2542099C2/ru active
- 2008-09-17 EP EP08831558A patent/EP2203430B1/en not_active Not-in-force
- 2008-09-17 EP EP11163527A patent/EP2377854A1/en not_active Withdrawn
- 2008-09-17 PT PT08831558T patent/PT2203430E/pt unknown
- 2008-09-17 AT AT08831558T patent/ATE512954T1/de active
- 2008-09-17 CN CN201610091594.0A patent/CN105693626A/zh active Pending
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| RU2040523C1 (ru) * | 1990-12-05 | 1995-07-25 | Ниссан Кемикал Индастриз, Лтд. | Производное урацила |
| RU2264395C2 (ru) * | 2000-02-04 | 2005-11-20 | Сумитомо Кемикал Компани, Лимитед | Производные урацила, гербицидная композиция, способ борьбы с сорняками и промежуточные продукты (варианты) |
| EA007178B1 (ru) * | 2000-05-23 | 2006-08-25 | Айденикс (Кайман) Лимитед | Производные beta-d-нуклеозида в качестве лекарственного средства для лечения инфекции вируса гепатита c у хозяина |
| US20060116390A1 (en) * | 2003-06-13 | 2006-06-01 | Jae-Hong Lim | Hepatitis c virus inhibitors |
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| R.D. FRANCESCO ET AL., Approaching a new era for hepatitis C virus therapy: inhibitors of the NS3-4A serine protease and the NS5B RNA-dependent RNA polymerase, Antiviral Research, 58, 2003, pp.1-16 * |
Also Published As
| Publication number | Publication date |
|---|---|
| US8986740B2 (en) | 2015-03-24 |
| JP2010539188A (ja) | 2010-12-16 |
| CA2699989C (en) | 2014-03-25 |
| CN105294569A (zh) | 2016-02-03 |
| MX2010002904A (es) | 2010-06-02 |
| PL2203430T3 (pl) | 2011-12-30 |
| HRP20110632T1 (hr) | 2011-10-31 |
| US20120189580A1 (en) | 2012-07-26 |
| CA2699989A1 (en) | 2009-03-26 |
| EP2377854A1 (en) | 2011-10-19 |
| PT2203430E (pt) | 2011-09-02 |
| JP5726527B2 (ja) | 2015-06-03 |
| DK2203430T3 (da) | 2011-09-26 |
| RU2010114826A (ru) | 2011-10-27 |
| EP2203430A1 (en) | 2010-07-07 |
| EP2548873A1 (en) | 2013-01-23 |
| ZA201002690B (en) | 2015-12-23 |
| ATE512954T1 (de) | 2011-07-15 |
| US8178548B2 (en) | 2012-05-15 |
| HK1145839A1 (en) | 2011-05-06 |
| CN105693626A (zh) | 2016-06-22 |
| EP2203430B1 (en) | 2011-06-15 |
| CN101918369B (zh) | 2016-02-24 |
| CN101918369A (zh) | 2010-12-15 |
| US20090176784A1 (en) | 2009-07-09 |
| WO2009039135A1 (en) | 2009-03-26 |
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