HRP20110632T1 - N-fenil-diokso-hidropirimidini korisni kao inhibitori virusa hepatitisa c (hcv) - Google Patents
N-fenil-diokso-hidropirimidini korisni kao inhibitori virusa hepatitisa c (hcv) Download PDFInfo
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- HRP20110632T1 HRP20110632T1 HR20110632T HRP20110632T HRP20110632T1 HR P20110632 T1 HRP20110632 T1 HR P20110632T1 HR 20110632 T HR20110632 T HR 20110632T HR P20110632 T HRP20110632 T HR P20110632T HR P20110632 T1 HRP20110632 T1 HR P20110632T1
- Authority
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- Croatia
- Prior art keywords
- phenyl
- group
- tert
- butyl
- dioxo
- Prior art date
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- 241000711549 Hepacivirus C Species 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 19
- 150000003839 salts Chemical class 0.000 claims abstract 19
- 239000003814 drug Substances 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims abstract 3
- 229940124597 therapeutic agent Drugs 0.000 claims abstract 3
- 208000005176 Hepatitis C Diseases 0.000 claims abstract 2
- 125000001424 substituent group Chemical group 0.000 claims 61
- 125000000217 alkyl group Chemical group 0.000 claims 37
- 125000000623 heterocyclic group Chemical group 0.000 claims 32
- 125000005843 halogen group Chemical group 0.000 claims 29
- 125000003342 alkenyl group Chemical group 0.000 claims 26
- 125000000304 alkynyl group Chemical group 0.000 claims 26
- -1 hydroxy, methyl Chemical group 0.000 claims 25
- 125000003545 alkoxy group Chemical group 0.000 claims 23
- 125000004452 carbocyclyl group Chemical group 0.000 claims 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 22
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 18
- 125000004043 oxo group Chemical group O=* 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- 239000001257 hydrogen Substances 0.000 claims 17
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 14
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 13
- 125000003302 alkenyloxy group Chemical group 0.000 claims 12
- 125000005133 alkynyloxy group Chemical group 0.000 claims 12
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 11
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 7
- 125000005884 carbocyclylalkyl group Chemical group 0.000 claims 6
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000005193 alkenylcarbonyloxy group Chemical group 0.000 claims 5
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims 5
- 125000005137 alkenylsulfonyl 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
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 229920002554 vinyl polymer Polymers 0.000 claims 4
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims 3
- 125000005087 alkynylcarbonyl group Chemical group 0.000 claims 3
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 claims 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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 group 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
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 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
- 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 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
- 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
- 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
- 239000005711 Benzoic acid Substances 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 241000124008 Mammalia 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 125000005091 alkenylcarbonylamino group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 1
- 125000005088 alkynylcarbonylamino group Chemical group 0.000 claims 1
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 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
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-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
- 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
- XRMNFZOZCSZGFR-JXMROGBWSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxo-1,3-diazinan-1-yl)-2-methoxyphenyl]ethenyl]phenyl]-n-methylsulfonylacetamide 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(C)=O)S(C)(=O)=O)C=C1 XRMNFZOZCSZGFR-JXMROGBWSA-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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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 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
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D413/10—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 linked by a carbon chain containing aromatic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Gastroenterology & Hepatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US97288707P | 2007-09-17 | 2007-09-17 | |
| US9679408P | 2008-09-13 | 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 |
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| EP (3) | EP2203430B1 (de) |
| JP (1) | JP5726527B2 (de) |
| CN (3) | CN105294569A (de) |
| AT (1) | ATE512954T1 (de) |
| CA (1) | CA2699989C (de) |
| DK (1) | DK2203430T3 (de) |
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| PL (1) | PL2203430T3 (de) |
| PT (1) | PT2203430E (de) |
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| ZA (1) | ZA201002690B (de) |
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| CN104628654A (zh) | 2007-09-17 | 2015-05-20 | 艾伯维巴哈马有限公司 | 抗感染嘧啶及其用途 |
| MX2010002904A (es) | 2007-09-17 | 2010-06-02 | Abbott Lab | N-fenil-dioxo-hidropirimidinas utiles como inhibidores de virus de hepatitis c (hcv). |
| WO2009039127A1 (en) * | 2007-09-17 | 2009-03-26 | Abbott Laboratories | Uracil or thymine derivative for treating hepatitis c |
| ES2383273T3 (es) | 2008-07-23 | 2012-06-19 | F. Hoffmann-La Roche Ag | Compuestos heterocíclicos antivíricos |
| WO2010034671A1 (en) | 2008-09-26 | 2010-04-01 | F. Hoffmann-La Roche Ag | Pyrine or pyrazine derivatives for treating hcv |
| MX2011004133A (es) | 2008-10-30 | 2011-05-24 | Hoffmann La Roche | Derivados de arilpiridona antiviral heterociclica. |
| KR20110094352A (ko) | 2008-12-22 | 2011-08-23 | 에프. 호프만-라 로슈 아게 | 헤테로사이클릭 항바이러스 화합물 |
| WO2010100178A1 (en) | 2009-03-06 | 2010-09-10 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compounds |
| ES2488821T3 (es) * | 2009-03-24 | 2014-08-29 | Abbvie Bahamas Ltd. | Proceso de preparación de un compuesto antiviral |
| MX2011011112A (es) * | 2009-04-25 | 2011-11-18 | Hoffmann La Roche | Compuestos antivirales heterociclicos. |
| TWI428332B (zh) | 2009-06-09 | 2014-03-01 | Hoffmann La Roche | 雜環抗病毒化合物 |
| CA2762675A1 (en) * | 2009-06-24 | 2010-12-29 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compound |
| JP2013505218A (ja) | 2009-09-21 | 2013-02-14 | エフ．ホフマン−ラ ロシュ アーゲー | 複素環式抗ウイルス化合物 |
| EA201200650A1 (ru) | 2009-10-30 | 2012-12-28 | Бёрингер Ингельхайм Интернациональ Гмбх | Курсы комбинированного лечения вируса гепатита с, включающие bi201335, интерферон-альфа и рибавирин |
| BR112012012085A2 (pt) * | 2009-11-21 | 2016-05-17 | Hoffmann La Roche | compostos antivirais heterocíclicos |
| CA2784646A1 (en) * | 2009-12-18 | 2011-06-23 | Boehringer Ingelheim International Gmbh | Hcv combination therapy |
| US9216952B2 (en) | 2010-03-23 | 2015-12-22 | Abbvie Inc. | Process for preparing antiviral compound |
| CA2801670A1 (en) * | 2010-07-07 | 2012-01-12 | Leanna Renee Staben | Heterocyclic antiviral compounds |
| US9255074B2 (en) | 2010-07-16 | 2016-02-09 | Abbvie Inc. | Process for preparing antiviral compounds |
| EP2593226B1 (de) | 2010-07-16 | 2018-11-14 | AbbVie Ireland Unlimited Company | Phosphinliganden für katalytische reaktionen |
| CR20180412A (es) | 2010-07-16 | 2018-11-01 | Abbvie Ireland Unlimited Co | Proceso para preparar compuestos antivirales |
| US8975443B2 (en) | 2010-07-16 | 2015-03-10 | Abbvie Inc. | Phosphine ligands for catalytic reactions |
| CA2829768A1 (en) * | 2011-03-18 | 2012-09-27 | Abbvie Inc. | Formulations of phenyl uracil compounds |
| US8989328B2 (en) * | 2013-03-14 | 2015-03-24 | Qualcomm Incorporated | Systems and methods for serial communication |
| HRP20220911T1 (hr) | 2013-09-11 | 2022-10-28 | Emory University | Sastav nukleotida i nukleozida i njihova uporaba |
| 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 |
| WO2018085170A1 (en) | 2016-11-01 | 2018-05-11 | Merck Sharp & Dohme Corp. | Substituted 6-membered aryl or heteroaryl allosteric modulators of nicotinic acetylcholine receptors |
| 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 |
| EP3819006A1 (de) * | 2019-11-05 | 2021-05-12 | Technische Universität Dresden | Verbindungen mit thymin-gerüst zur verwendung in der medizin |
| 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 |
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| 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 |
| EP0442473B1 (de) * | 1990-02-15 | 1998-08-19 | Takeda Chemical Industries, Ltd. | Pyrimidindionderivate, deren Herstellung und Verwendung |
| NL9001075A (de) * | 1990-05-04 | 1991-12-02 | Duphar Int Res | |
| EP0489480A1 (de) * | 1990-12-05 | 1992-06-10 | Nissan Chemical Industries Ltd. | Urazil-Derivate und diese als aktiven Bestandteil enthaltende Herbizide |
| 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 |
| PT1237878E (pt) | 1999-12-06 | 2007-06-18 | Hoffmann La Roche | 4-pirimidinil-n-acil-fenilalaninas |
| US6380387B1 (en) * | 1999-12-06 | 2002-04-30 | Hoffmann-La Roche Inc. | 4-Pyrimidinyl-n-acyl-l phenylalanines |
| IL167955A (en) * | 2000-02-04 | 2007-10-31 | Sumitomo Chemical Co | Inilines are converted by troiril |
| 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 |
| CN104628654A (zh) | 2007-09-17 | 2015-05-20 | 艾伯维巴哈马有限公司 | 抗感染嘧啶及其用途 |
| MX2010002904A (es) | 2007-09-17 | 2010-06-02 | Abbott Lab | N-fenil-dioxo-hidropirimidinas utiles como inhibidores de virus de hepatitis c (hcv). |
| WO2009039127A1 (en) * | 2007-09-17 | 2009-03-26 | Abbott Laboratories | Uracil or thymine derivative for treating hepatitis c |
| ES2383273T3 (es) | 2008-07-23 | 2012-06-19 | F. Hoffmann-La Roche Ag | Compuestos heterocíclicos antivíricos |
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2008
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- 2008-09-17 DK DK08831558.5T patent/DK2203430T3/da active
- 2008-09-17 RU RU2010114826/04A patent/RU2542099C2/ru active
- 2008-09-17 EP EP08831558A patent/EP2203430B1/de not_active Not-in-force
- 2008-09-17 CN CN201510508424.3A patent/CN105294569A/zh active Pending
- 2008-09-17 EP EP12185550A patent/EP2548873A1/de not_active Withdrawn
- 2008-09-17 US US12/212,315 patent/US8178548B2/en active Active
- 2008-09-17 WO PCT/US2008/076594 patent/WO2009039135A1/en active Application Filing
- 2008-09-17 CN CN201610091594.0A patent/CN105693626A/zh active Pending
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- 2008-09-17 PL PL08831558T patent/PL2203430T3/pl unknown
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- 2008-09-17 CA CA2699989A patent/CA2699989C/en not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| JP2010539188A (ja) | 2010-12-16 |
| US8178548B2 (en) | 2012-05-15 |
| EP2377854A1 (de) | 2011-10-19 |
| ZA201002690B (en) | 2015-12-23 |
| US8986740B2 (en) | 2015-03-24 |
| PT2203430E (pt) | 2011-09-02 |
| EP2203430A1 (de) | 2010-07-07 |
| US20090176784A1 (en) | 2009-07-09 |
| CN101918369A (zh) | 2010-12-15 |
| CN101918369B (zh) | 2016-02-24 |
| EP2203430B1 (de) | 2011-06-15 |
| EP2548873A1 (de) | 2013-01-23 |
| RU2010114826A (ru) | 2011-10-27 |
| CN105693626A (zh) | 2016-06-22 |
| PL2203430T3 (pl) | 2011-12-30 |
| ATE512954T1 (de) | 2011-07-15 |
| JP5726527B2 (ja) | 2015-06-03 |
| CA2699989C (en) | 2014-03-25 |
| RU2542099C2 (ru) | 2015-02-20 |
| WO2009039135A1 (en) | 2009-03-26 |
| MX2010002904A (es) | 2010-06-02 |
| HK1145839A1 (en) | 2011-05-06 |
| DK2203430T3 (da) | 2011-09-26 |
| CN105294569A (zh) | 2016-02-03 |
| CA2699989A1 (en) | 2009-03-26 |
| US20120189580A1 (en) | 2012-07-26 |
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