HRP20110809T1 - Protuupalni pirimidini i njihove uporabe - Google Patents
Protuupalni pirimidini i njihove uporabe Download PDFInfo
- Publication number
- HRP20110809T1 HRP20110809T1 HR20110809T HRP20110809T HRP20110809T1 HR P20110809 T1 HRP20110809 T1 HR P20110809T1 HR 20110809 T HR20110809 T HR 20110809T HR P20110809 T HRP20110809 T HR P20110809T HR P20110809 T1 HRP20110809 T1 HR P20110809T1
- Authority
- HR
- Croatia
- Prior art keywords
- group
- dioxo
- dihydropyrimidin
- tert
- butyl
- Prior art date
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- 230000002924 anti-infective effect Effects 0.000 title 1
- 150000003230 pyrimidines Chemical class 0.000 title 1
- 125000001424 substituent group Chemical group 0.000 claims abstract 71
- 125000000217 alkyl group Chemical group 0.000 claims abstract 46
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 41
- -1 hydroxy, methyl Chemical group 0.000 claims abstract 36
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 35
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 34
- 125000004452 carbocyclyl group Chemical group 0.000 claims abstract 34
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 27
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 23
- 150000001875 compounds Chemical class 0.000 claims abstract 22
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract 21
- 150000003839 salts Chemical class 0.000 claims abstract 19
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 15
- 125000005133 alkynyloxy group Chemical group 0.000 claims abstract 15
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 14
- 239000001257 hydrogen Substances 0.000 claims abstract 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 13
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract 9
- 125000005884 carbocyclylalkyl group Chemical group 0.000 claims abstract 8
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims abstract 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 7
- 150000002431 hydrogen Chemical class 0.000 claims abstract 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 5
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract 4
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims abstract 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract 2
- 125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 claims abstract 2
- 125000005843 halogen group Chemical group 0.000 claims 26
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 14
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 10
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 8
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 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
- NBRBXGKOEOGLOI-UHFFFAOYSA-N dasabuvir Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C=C1N1C=CC(=O)NC1=O NBRBXGKOEOGLOI-UHFFFAOYSA-N 0.000 claims 5
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims 4
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims 3
- 125000005087 alkynylcarbonyl group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- AQFWJMYYGAZRTL-UHFFFAOYSA-N 1-[3-(2-amino-1,3-benzothiazol-6-yl)-5-tert-butyl-4-methoxyphenyl]pyrimidine-2,4-dione Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3SC(N)=NC3=CC=2)C=C1N1C=CC(=O)NC1=O AQFWJMYYGAZRTL-UHFFFAOYSA-N 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
- 239000003814 drug Substances 0.000 claims 2
- VKHZYWVEBNIRLX-UHFFFAOYSA-N methanesulfonohydrazide Chemical compound CS(=O)(=O)NN VKHZYWVEBNIRLX-UHFFFAOYSA-N 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- YXRGAZPCDALZSP-UHFFFAOYSA-N 1-(3-tert-butyl-4-methoxy-5-naphthalen-2-ylphenyl)pyrimidine-2,4-dione Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3C=CC=CC3=CC=2)C=C1N1C=CC(=O)NC1=O YXRGAZPCDALZSP-UHFFFAOYSA-N 0.000 claims 1
- XZXYGRARNRNIPW-UHFFFAOYSA-N 1-[3-(1,3-benzothiazol-2-yl)-5-tert-butyl-4-methoxyphenyl]-1,3-diazinane-2,4-dione Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2SC3=CC=CC=C3N=2)C=C1N1CCC(=O)NC1=O XZXYGRARNRNIPW-UHFFFAOYSA-N 0.000 claims 1
- PVIVCOLZLYNGPB-UHFFFAOYSA-N 1-[3-(1,3-benzothiazol-6-yl)-5-tert-butyl-4-methoxyphenyl]pyrimidine-2,4-dione Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3SC=NC3=CC=2)C=C1N1C=CC(=O)NC1=O PVIVCOLZLYNGPB-UHFFFAOYSA-N 0.000 claims 1
- JAESXJLAMBRTBM-UHFFFAOYSA-N 1-[3-tert-butyl-4-methoxy-5-(1-methylsulfonyl-2,3-dihydroindol-5-yl)phenyl]pyrimidine-2,4-dione Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3CCN(C3=CC=2)S(C)(=O)=O)C=C1N1C=CC(=O)NC1=O JAESXJLAMBRTBM-UHFFFAOYSA-N 0.000 claims 1
- HHBKKXLZBBILEV-UHFFFAOYSA-N 1-[3-tert-butyl-4-methoxy-5-(1-oxo-2,3-dihydroinden-5-yl)phenyl]pyrimidine-2,4-dione Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3CCC(=O)C3=CC=2)C=C1N1C=CC(=O)NC1=O HHBKKXLZBBILEV-UHFFFAOYSA-N 0.000 claims 1
- RWPKQMZFXORKQF-UHFFFAOYSA-N 1-[3-tert-butyl-4-methoxy-5-(1-oxo-2,3-dihydroisoindol-5-yl)phenyl]pyrimidine-2,4-dione Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3CNC(=O)C3=CC=2)C=C1N1C=CC(=O)NC1=O RWPKQMZFXORKQF-UHFFFAOYSA-N 0.000 claims 1
- ZFRHKNRVKQELLK-UHFFFAOYSA-N 1-[3-tert-butyl-4-methoxy-5-(3-methyl-1-benzofuran-6-yl)phenyl]pyrimidine-2,4-dione Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3OC=C(C)C3=CC=2)C=C1N1C=CC(=O)NC1=O ZFRHKNRVKQELLK-UHFFFAOYSA-N 0.000 claims 1
- XNJMOOOQQDDAAE-UHFFFAOYSA-N 1-[3-tert-butyl-4-methoxy-5-(5-nitro-1,3-benzoxazol-2-yl)phenyl]-1,3-diazinane-2,4-dione Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2OC3=CC=C(C=C3N=2)[N+]([O-])=O)C=C1N1CCC(=O)NC1=O XNJMOOOQQDDAAE-UHFFFAOYSA-N 0.000 claims 1
- DHOPGXUASGTCKU-UHFFFAOYSA-N 1-[3-tert-butyl-4-methoxy-5-(6-methoxynaphthalen-2-yl)phenyl]pyrimidine-2,4-dione Chemical compound C1=CC2=CC(OC)=CC=C2C=C1C(C(=C(C=1)C(C)(C)C)OC)=CC=1N1C=CC(=O)NC1=O DHOPGXUASGTCKU-UHFFFAOYSA-N 0.000 claims 1
- SAGLGVMHVLWDRP-UHFFFAOYSA-N 1-[3-tert-butyl-4-methoxy-5-(6-nitro-1,3-benzoxazol-2-yl)phenyl]-1,3-diazinane-2,4-dione Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2OC3=CC(=CC=C3N=2)[N+]([O-])=O)C=C1N1CCC(=O)NC1=O SAGLGVMHVLWDRP-UHFFFAOYSA-N 0.000 claims 1
- NWHSVWGQIUBZQT-UHFFFAOYSA-N 1-[3-tert-butyl-4-methoxy-5-[2-(propylamino)-1,3-benzothiazol-6-yl]phenyl]pyrimidine-2,4-dione Chemical compound C1=C2SC(NCCC)=NC2=CC=C1C(C(=C(C=1)C(C)(C)C)OC)=CC=1N1C=CC(=O)NC1=O NWHSVWGQIUBZQT-UHFFFAOYSA-N 0.000 claims 1
- FBNXRQIJHASXJZ-UHFFFAOYSA-N 1-[3-tert-butyl-5-(1-hydroxy-2,3-dihydro-1h-inden-5-yl)-4-methoxyphenyl]pyrimidine-2,4-dione Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3CCC(O)C3=CC=2)C=C1N1C=CC(=O)NC1=O FBNXRQIJHASXJZ-UHFFFAOYSA-N 0.000 claims 1
- WWCQVRQPZOUFOP-UHFFFAOYSA-N 1-[3-tert-butyl-5-(2-chloro-1,3-benzothiazol-6-yl)-4-methoxyphenyl]pyrimidine-2,4-dione Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3SC(Cl)=NC3=CC=2)C=C1N1C=CC(=O)NC1=O WWCQVRQPZOUFOP-UHFFFAOYSA-N 0.000 claims 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 1
- MTNFZAKOJUMHNX-UHFFFAOYSA-N 2-[5-(2,4-dioxopyrimidin-1-yl)-3-[6-(methanesulfonamido)naphthalen-2-yl]-2-methoxyphenyl]-2-methylpropanoic acid Chemical compound C1=C(C(C)(C)C(O)=O)C(OC)=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C=C1N1C=CC(=O)NC1=O MTNFZAKOJUMHNX-UHFFFAOYSA-N 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- PCJMVHPWWFMSSS-UHFFFAOYSA-N 5-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-n-methylsulfonyl-2,3-dihydro-1h-indene-1-carboxamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3CCC(C3=CC=2)C(=O)NS(C)(=O)=O)C=C1N1C=CC(=O)NC1=O PCJMVHPWWFMSSS-UHFFFAOYSA-N 0.000 claims 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims 1
- 208000005176 Hepatitis C Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-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
- 125000005154 alkyl sulfonyl amino alkyl 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
- 125000005605 benzo group Chemical group 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
- 125000005508 decahydronaphthalenyl group Chemical group 0.000 claims 1
- 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- UHMIQMCYZFEWKI-UHFFFAOYSA-N methyl 2-[5-(2,4-dioxopyrimidin-1-yl)-3-[6-(methanesulfonamido)naphthalen-2-yl]-2-methoxyphenyl]-2-methylpropanoate Chemical compound C=1C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)=C(OC)C(C(C)(C)C(=O)OC)=CC=1N1C=CC(=O)NC1=O UHMIQMCYZFEWKI-UHFFFAOYSA-N 0.000 claims 1
- JTRQHRROGPCQHE-UHFFFAOYSA-N methyl 5-(2,4-dioxopyrimidin-1-yl)-3-[6-(methanesulfonamido)naphthalen-2-yl]-2-methoxybenzoate Chemical compound C=1C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)=C(OC)C(C(=O)OC)=CC=1N1C=CC(=O)NC1=O JTRQHRROGPCQHE-UHFFFAOYSA-N 0.000 claims 1
- ASVOIZVEHMSFFT-UHFFFAOYSA-N methyl n-[[5-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-2,3-dihydroinden-1-ylidene]amino]carbamate Chemical compound C=1C=C2C(=NNC(=O)OC)CCC2=CC=1C(C(=C(C=1)C(C)(C)C)OC)=CC=1N1C=CC(=O)NC1=O ASVOIZVEHMSFFT-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- LWUPFIBYTKEWJQ-UHFFFAOYSA-N n'-[5-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-2,3-dihydro-1h-inden-1-yl]methanesulfonohydrazide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3CCC(C3=CC=2)NNS(C)(=O)=O)C=C1N1C=CC(=O)NC1=O LWUPFIBYTKEWJQ-UHFFFAOYSA-N 0.000 claims 1
- WTLGVHMLSDGNGC-SZXQPVLSSA-N n-[(e)-[6-[5-(2,4-dioxopyrimidin-1-yl)-2-methoxy-3-thiophen-2-ylphenyl]-2,3-dihydroinden-1-ylidene]amino]methanesulfonamide Chemical compound C1=C(C=2C=C3C(=N/NS(C)(=O)=O)/CCC3=CC=2)C(OC)=C(C=2SC=CC=2)C=C1N1C=CC(=O)NC1=O WTLGVHMLSDGNGC-SZXQPVLSSA-N 0.000 claims 1
- UZAAZICNWHJGFD-SZXQPVLSSA-N n-[(e)-[6-[5-(2,4-dioxopyrimidin-1-yl)-3-(furan-2-yl)-2-methoxyphenyl]-2,3-dihydroinden-1-ylidene]amino]methanesulfonamide Chemical compound C1=C(C=2C=C3C(=N/NS(C)(=O)=O)/CCC3=CC=2)C(OC)=C(C=2OC=CC=2)C=C1N1C=CC(=O)NC1=O UZAAZICNWHJGFD-SZXQPVLSSA-N 0.000 claims 1
- OIOOUZKXUXQCIF-JOCHJYFZSA-N n-[2-[(1r)-5-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-2,3-dihydro-1h-inden-1-yl]propan-2-yl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3CC[C@H](C3=CC=2)C(C)(C)NS(C)(=O)=O)C=C1N1C=CC(=O)NC1=O OIOOUZKXUXQCIF-JOCHJYFZSA-N 0.000 claims 1
- OIOOUZKXUXQCIF-QFIPXVFZSA-N n-[2-[(1s)-5-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-2,3-dihydro-1h-inden-1-yl]propan-2-yl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3CC[C@@H](C3=CC=2)C(C)(C)NS(C)(=O)=O)C=C1N1C=CC(=O)NC1=O OIOOUZKXUXQCIF-QFIPXVFZSA-N 0.000 claims 1
- FJGZPBUBGDMIEQ-UHFFFAOYSA-N n-[2-[3-tert-butyl-5-(2,4-dioxo-1,3-diazinan-1-yl)-2-methoxyphenyl]-1,3-benzothiazol-5-yl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2SC3=CC=C(NS(C)(=O)=O)C=C3N=2)C=C1N1CCC(=O)NC1=O FJGZPBUBGDMIEQ-UHFFFAOYSA-N 0.000 claims 1
- DOARMVDILKEQDJ-UHFFFAOYSA-N n-[2-[3-tert-butyl-5-(2,4-dioxo-1,3-diazinan-1-yl)-2-methoxyphenyl]-1,3-benzothiazol-6-yl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2SC3=CC(NS(C)(=O)=O)=CC=C3N=2)C=C1N1CCC(=O)NC1=O DOARMVDILKEQDJ-UHFFFAOYSA-N 0.000 claims 1
- GQSANLVBMNPJMC-UHFFFAOYSA-N n-[2-[3-tert-butyl-5-(2,4-dioxo-1,3-diazinan-1-yl)-2-methoxyphenyl]-1,3-benzoxazol-5-yl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2OC3=CC=C(NS(C)(=O)=O)C=C3N=2)C=C1N1CCC(=O)NC1=O GQSANLVBMNPJMC-UHFFFAOYSA-N 0.000 claims 1
- MEZSDRNJRNOHMP-UHFFFAOYSA-N n-[2-[3-tert-butyl-5-(2,4-dioxo-1,3-diazinan-1-yl)-2-methoxyphenyl]-1,3-benzoxazol-6-yl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2OC3=CC(NS(C)(=O)=O)=CC=C3N=2)C=C1N1CCC(=O)NC1=O MEZSDRNJRNOHMP-UHFFFAOYSA-N 0.000 claims 1
- IVIYULJLOWEVTN-UHFFFAOYSA-N n-[2-[3-tert-butyl-5-(2,4-dioxo-1,3-diazinan-1-yl)-2-methoxyphenyl]-3h-benzimidazol-5-yl]-n-methylsulfonylmethanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2NC3=CC=C(C=C3N=2)N(S(C)(=O)=O)S(C)(=O)=O)C=C1N1CCC(=O)NC1=O IVIYULJLOWEVTN-UHFFFAOYSA-N 0.000 claims 1
- KZJUZGIPMPKLQT-UHFFFAOYSA-N n-[2-[3-tert-butyl-5-(2,4-dioxo-1,3-diazinan-1-yl)-2-methoxyphenyl]-3h-benzimidazol-5-yl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2NC3=CC=C(NS(C)(=O)=O)C=C3N=2)C=C1N1CCC(=O)NC1=O KZJUZGIPMPKLQT-UHFFFAOYSA-N 0.000 claims 1
- WXGACALVDQEAAO-UHFFFAOYSA-N n-[2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-1,3-benzoxazol-5-yl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2OC3=CC=C(NS(C)(=O)=O)C=C3N=2)C=C1N1C=CC(=O)NC1=O WXGACALVDQEAAO-UHFFFAOYSA-N 0.000 claims 1
- XBRUNJDSZNGABJ-UHFFFAOYSA-N n-[2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-1,3-dihydroisoindol-5-yl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(N2CC3=CC(NS(C)(=O)=O)=CC=C3C2)C=C1N1C=CC(=O)NC1=O XBRUNJDSZNGABJ-UHFFFAOYSA-N 0.000 claims 1
- YVFJERSHMIZROV-UHFFFAOYSA-N n-[2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-3,4-dihydro-1h-isoquinolin-6-yl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(N2CC3=CC=C(NS(C)(=O)=O)C=C3CC2)C=C1N1C=CC(=O)NC1=O YVFJERSHMIZROV-UHFFFAOYSA-N 0.000 claims 1
- XITJLAONOGOXPU-UHFFFAOYSA-N n-[2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]quinolin-6-yl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2N=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C=C1N1C=CC(=O)NC1=O XITJLAONOGOXPU-UHFFFAOYSA-N 0.000 claims 1
- OIOOUZKXUXQCIF-UHFFFAOYSA-N n-[2-[5-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-2,3-dihydro-1h-inden-1-yl]propan-2-yl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3CCC(C3=CC=2)C(C)(C)NS(C)(=O)=O)C=C1N1C=CC(=O)NC1=O OIOOUZKXUXQCIF-UHFFFAOYSA-N 0.000 claims 1
- QFNWRWSMBBUABM-UHFFFAOYSA-N n-[5-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-2,3-dihydro-1h-inden-1-yl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3CCC(C3=CC=2)NS(C)(=O)=O)C=C1N1C=CC(=O)NC1=O QFNWRWSMBBUABM-UHFFFAOYSA-N 0.000 claims 1
- ORZIFRIOPKCERB-UHFFFAOYSA-N n-[6-[3-(3-chlorophenyl)-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]naphthalen-2-yl]methanesulfonamide Chemical compound C1=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C(OC)=C(C=2C=C(Cl)C=CC=2)C=C1N1C=CC(=O)NC1=O ORZIFRIOPKCERB-UHFFFAOYSA-N 0.000 claims 1
- DONIOQPZCANINF-UHFFFAOYSA-N n-[6-[3-bromo-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]naphthalen-2-yl]methanesulfonamide Chemical compound C1=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C(OC)=C(Br)C=C1N1C=CC(=O)NC1=O DONIOQPZCANINF-UHFFFAOYSA-N 0.000 claims 1
- DHPZPQJFXMGFMT-UHFFFAOYSA-N n-[6-[3-tert-butyl-2-chloro-5-(2,4-dioxopyrimidin-1-yl)phenyl]naphthalen-2-yl]methanesulfonamide Chemical compound C=1C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)=C(Cl)C(C(C)(C)C)=CC=1N1C=CC(=O)NC1=O DHPZPQJFXMGFMT-UHFFFAOYSA-N 0.000 claims 1
- VTZYWEBKMIPMOK-UHFFFAOYSA-N n-[6-[3-tert-butyl-5-(2,4-dioxo-1,3-diazinan-1-yl)-2-methoxyphenyl]naphthalen-2-yl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C=C1N1CCC(=O)NC1=O VTZYWEBKMIPMOK-UHFFFAOYSA-N 0.000 claims 1
- YZNCUYVHKAAFNE-UHFFFAOYSA-N n-[6-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-ethoxyphenyl]naphthalen-2-yl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OCC)=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C=C1N1C=CC(=O)NC1=O YZNCUYVHKAAFNE-UHFFFAOYSA-N 0.000 claims 1
- BPDYNLZHRRLNKI-UHFFFAOYSA-N n-[6-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3SC(NC(C)=O)=NC3=CC=2)C=C1N1C=CC(=O)NC1=O BPDYNLZHRRLNKI-UHFFFAOYSA-N 0.000 claims 1
- VQTJHVDHKTWBNP-UHFFFAOYSA-N n-[6-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-1,3-benzothiazol-2-yl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3SC(NS(C)(=O)=O)=NC3=CC=2)C=C1N1C=CC(=O)NC1=O VQTJHVDHKTWBNP-UHFFFAOYSA-N 0.000 claims 1
- GQYTVPPMADGMEG-UHFFFAOYSA-N n-[6-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3CCN(CC3=CC=2)NS(C)(=O)=O)C=C1N1C=CC(=O)NC1=O GQYTVPPMADGMEG-UHFFFAOYSA-N 0.000 claims 1
- VHAQVZZQZQBPFL-UHFFFAOYSA-N n-[6-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]quinolin-2-yl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3C=CC(NS(C)(=O)=O)=NC3=CC=2)C=C1N1C=CC(=O)NC1=O VHAQVZZQZQBPFL-UHFFFAOYSA-N 0.000 claims 1
- JAQQZCHPFDGGCY-UHFFFAOYSA-N n-[6-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)phenyl]naphthalen-2-yl]methanesulfonamide Chemical compound C=1C(C(C)(C)C)=CC(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)=CC=1N1C=CC(=O)NC1=O JAQQZCHPFDGGCY-UHFFFAOYSA-N 0.000 claims 1
- JXMWLBLQFGDONM-UHFFFAOYSA-N n-[6-[5-(2,4-dioxopyrimidin-1-yl)-2-methoxy-3-(1,1,2,2,2-pentafluoroethyl)phenyl]naphthalen-2-yl]methanesulfonamide Chemical compound C1=C(C(F)(F)C(F)(F)F)C(OC)=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C=C1N1C=CC(=O)NC1=O JXMWLBLQFGDONM-UHFFFAOYSA-N 0.000 claims 1
- RQFNDCIXKAIMTO-UHFFFAOYSA-N n-[6-[5-(2,4-dioxopyrimidin-1-yl)-2-methoxy-3-(1-methoxy-2-methylpropan-2-yl)phenyl]naphthalen-2-yl]methanesulfonamide Chemical compound C=1C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)=C(OC)C(C(C)(C)COC)=CC=1N1C=CC(=O)NC1=O RQFNDCIXKAIMTO-UHFFFAOYSA-N 0.000 claims 1
- SPMBLCQUTKXPRH-UHFFFAOYSA-N n-[6-[5-(2,4-dioxopyrimidin-1-yl)-2-methoxy-3-(2-methylbutan-2-yl)phenyl]naphthalen-2-yl]methanesulfonamide Chemical compound C=1C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)=C(OC)C(C(C)(C)CC)=CC=1N1C=CC(=O)NC1=O SPMBLCQUTKXPRH-UHFFFAOYSA-N 0.000 claims 1
- BFSOPAVRUAFZES-UHFFFAOYSA-N n-[6-[5-(2,4-dioxopyrimidin-1-yl)-2-methoxy-3-(2-trimethylsilylethynyl)phenyl]naphthalen-2-yl]methanesulfonamide Chemical compound C1=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C(OC)=C(C#C[Si](C)(C)C)C=C1N1C=CC(=O)NC1=O BFSOPAVRUAFZES-UHFFFAOYSA-N 0.000 claims 1
- OHJVMZMYTGBOFZ-UHFFFAOYSA-N n-[6-[5-(2,4-dioxopyrimidin-1-yl)-2-methoxy-3-(trifluoromethyl)phenyl]naphthalen-2-yl]methanesulfonamide Chemical compound C1=C(C(F)(F)F)C(OC)=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C=C1N1C=CC(=O)NC1=O OHJVMZMYTGBOFZ-UHFFFAOYSA-N 0.000 claims 1
- QIMHUFHWAWJIPS-UHFFFAOYSA-N n-[6-[5-(2,4-dioxopyrimidin-1-yl)-2-methoxy-3-methylsulfonylphenyl]naphthalen-2-yl]methanesulfonamide Chemical compound C1=C(S(C)(=O)=O)C(OC)=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C=C1N1C=CC(=O)NC1=O QIMHUFHWAWJIPS-UHFFFAOYSA-N 0.000 claims 1
- MOXQSCXVOXWDML-UHFFFAOYSA-N n-[6-[5-(2,4-dioxopyrimidin-1-yl)-2-methoxy-3-phenylphenyl]naphthalen-2-yl]methanesulfonamide Chemical compound C1=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C(OC)=C(C=2C=CC=CC=2)C=C1N1C=CC(=O)NC1=O MOXQSCXVOXWDML-UHFFFAOYSA-N 0.000 claims 1
- PZUHHFOWCAQSSK-UHFFFAOYSA-N n-[6-[5-(2,4-dioxopyrimidin-1-yl)-2-methoxy-3-thiophen-2-ylphenyl]naphthalen-2-yl]methanesulfonamide Chemical compound C1=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C(OC)=C(C=2SC=CC=2)C=C1N1C=CC(=O)NC1=O PZUHHFOWCAQSSK-UHFFFAOYSA-N 0.000 claims 1
- HSWQYCLLXRZTNO-UHFFFAOYSA-N n-[6-[5-(2,4-dioxopyrimidin-1-yl)-2-methoxy-3-thiophen-3-ylphenyl]naphthalen-2-yl]methanesulfonamide Chemical compound C1=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C(OC)=C(C2=CSC=C2)C=C1N1C=CC(=O)NC1=O HSWQYCLLXRZTNO-UHFFFAOYSA-N 0.000 claims 1
- MVWTZSAJNXJGAW-UHFFFAOYSA-N n-[6-[5-(2,4-dioxopyrimidin-1-yl)-3-(furan-2-yl)-2-methoxyphenyl]naphthalen-2-yl]methanesulfonamide Chemical compound C1=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C(OC)=C(C=2OC=CC=2)C=C1N1C=CC(=O)NC1=O MVWTZSAJNXJGAW-UHFFFAOYSA-N 0.000 claims 1
- IWCJOVAPXCYCKX-UHFFFAOYSA-N n-[6-[5-(2,4-dioxopyrimidin-1-yl)-3-(furan-3-yl)-2-methoxyphenyl]naphthalen-2-yl]methanesulfonamide Chemical compound C1=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C(OC)=C(C2=COC=C2)C=C1N1C=CC(=O)NC1=O IWCJOVAPXCYCKX-UHFFFAOYSA-N 0.000 claims 1
- WTXZYCQMXHDUAC-UHFFFAOYSA-N n-[6-[5-(2,4-dioxopyrimidin-1-yl)-3-(methanesulfonamido)-2-methoxyphenyl]naphthalen-2-yl]methanesulfonamide Chemical compound C1=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C(OC)=C(NS(C)(=O)=O)C=C1N1C=CC(=O)NC1=O WTXZYCQMXHDUAC-UHFFFAOYSA-N 0.000 claims 1
- DDQAGIWEIQNYDV-SANMLTNESA-N n-[[(1r)-5-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-1-fluoro-2,3-dihydroinden-1-yl]methyl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3C([C@@](CC3)(F)CNS(C)(=O)=O)=CC=2)C=C1N1C=CC(=O)NC1=O DDQAGIWEIQNYDV-SANMLTNESA-N 0.000 claims 1
- IYTYOXLXXMKIMX-SFHVURJKSA-N n-[[(1r)-5-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-2,3-dihydro-1h-inden-1-yl]methyl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3CC[C@@H](CNS(C)(=O)=O)C3=CC=2)C=C1N1C=CC(=O)NC1=O IYTYOXLXXMKIMX-SFHVURJKSA-N 0.000 claims 1
- DDQAGIWEIQNYDV-AREMUKBSSA-N n-[[(1s)-5-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-1-fluoro-2,3-dihydroinden-1-yl]methyl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3C([C@](CC3)(F)CNS(C)(=O)=O)=CC=2)C=C1N1C=CC(=O)NC1=O DDQAGIWEIQNYDV-AREMUKBSSA-N 0.000 claims 1
- IYTYOXLXXMKIMX-GOSISDBHSA-N n-[[(1s)-5-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-2,3-dihydro-1h-inden-1-yl]methyl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3CC[C@H](CNS(C)(=O)=O)C3=CC=2)C=C1N1C=CC(=O)NC1=O IYTYOXLXXMKIMX-GOSISDBHSA-N 0.000 claims 1
- DDQAGIWEIQNYDV-UHFFFAOYSA-N n-[[5-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-1-fluoro-2,3-dihydroinden-1-yl]methyl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3C(C(CC3)(F)CNS(C)(=O)=O)=CC=2)C=C1N1C=CC(=O)NC1=O DDQAGIWEIQNYDV-UHFFFAOYSA-N 0.000 claims 1
- SNZYDZSZLNFANX-UHFFFAOYSA-N n-[[5-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-1-methyl-2,3-dihydroinden-1-yl]methyl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3C(C(CC3)(C)CNS(C)(=O)=O)=CC=2)C=C1N1C=CC(=O)NC1=O SNZYDZSZLNFANX-UHFFFAOYSA-N 0.000 claims 1
- IYTYOXLXXMKIMX-UHFFFAOYSA-N n-[[5-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-2,3-dihydro-1h-inden-1-yl]methyl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3CCC(CNS(C)(=O)=O)C3=CC=2)C=C1N1C=CC(=O)NC1=O IYTYOXLXXMKIMX-UHFFFAOYSA-N 0.000 claims 1
- MNFQFJFIUOVKFY-UHFFFAOYSA-N n-[[5-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-3h-inden-1-yl]methyl]-n-methylmethanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3CC=C(CN(C)S(C)(=O)=O)C3=CC=2)C=C1N1C=CC(=O)NC1=O MNFQFJFIUOVKFY-UHFFFAOYSA-N 0.000 claims 1
- QEQINMWJWJSCMD-UHFFFAOYSA-N n-[[5-[5-(2,4-dioxopyrimidin-1-yl)-2-methoxy-3-thiophen-2-ylphenyl]-3h-inden-1-yl]methyl]methanesulfonamide Chemical compound C1=C(C=2C=C3CC=C(CNS(C)(=O)=O)C3=CC=2)C(OC)=C(C=2SC=CC=2)C=C1N1C=CC(=O)NC1=O QEQINMWJWJSCMD-UHFFFAOYSA-N 0.000 claims 1
- DLRBINTUAXJWPN-UHFFFAOYSA-N n-[[5-[5-(2,4-dioxopyrimidin-1-yl)-2-methoxy-3-thiophen-3-ylphenyl]-3h-inden-1-yl]methyl]methanesulfonamide Chemical compound C1=C(C=2C=C3CC=C(CNS(C)(=O)=O)C3=CC=2)C(OC)=C(C2=CSC=C2)C=C1N1C=CC(=O)NC1=O DLRBINTUAXJWPN-UHFFFAOYSA-N 0.000 claims 1
- JKMROEKFKNRCQC-UHFFFAOYSA-N n-[[5-[5-(2,4-dioxopyrimidin-1-yl)-3-(furan-2-yl)-2-methoxyphenyl]-3h-inden-1-yl]methyl]methanesulfonamide Chemical compound C1=C(C=2C=C3CC=C(CNS(C)(=O)=O)C3=CC=2)C(OC)=C(C=2OC=CC=2)C=C1N1C=CC(=O)NC1=O JKMROEKFKNRCQC-UHFFFAOYSA-N 0.000 claims 1
- KSLSIEFZPSLNIF-UHFFFAOYSA-N n-[[5-[5-(2,4-dioxopyrimidin-1-yl)-3-(furan-3-yl)-2-methoxyphenyl]-3h-inden-1-yl]methyl]methanesulfonamide Chemical compound C1=C(C=2C=C3CC=C(CNS(C)(=O)=O)C3=CC=2)C(OC)=C(C2=COC=C2)C=C1N1C=CC(=O)NC1=O KSLSIEFZPSLNIF-UHFFFAOYSA-N 0.000 claims 1
- OHYYUFSMPNNOPR-UHFFFAOYSA-N n-[[6-[3-tert-butyl-2-chloro-5-(2,4-dioxopyrimidin-1-yl)phenyl]-1-benzothiophen-3-yl]methyl]methanesulfonamide Chemical compound C=1C(C=2C=C3SC=C(CNS(C)(=O)=O)C3=CC=2)=C(Cl)C(C(C)(C)C)=CC=1N1C=CC(=O)NC1=O OHYYUFSMPNNOPR-UHFFFAOYSA-N 0.000 claims 1
- AGGBXQKHIOJSOM-UHFFFAOYSA-N n-[[6-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-1,2-benzoxazol-3-yl]methyl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3ON=C(CNS(C)(=O)=O)C3=CC=2)C=C1N1C=CC(=O)NC1=O AGGBXQKHIOJSOM-UHFFFAOYSA-N 0.000 claims 1
- DSBZMFBIBUTQAU-UHFFFAOYSA-N n-[[6-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-1-benzofuran-3-yl]methyl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3OC=C(CNS(C)(=O)=O)C3=CC=2)C=C1N1C=CC(=O)NC1=O DSBZMFBIBUTQAU-UHFFFAOYSA-N 0.000 claims 1
- NWDQPWDUNFAXND-UHFFFAOYSA-N n-[[6-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-1-benzothiophen-2-yl]methyl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3SC(CNS(C)(=O)=O)=CC3=CC=2)C=C1N1C=CC(=O)NC1=O NWDQPWDUNFAXND-UHFFFAOYSA-N 0.000 claims 1
- WFDAWIPJPPHQTK-UHFFFAOYSA-N n-[[6-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-1-benzothiophen-3-yl]methyl]-n-methylmethanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3SC=C(CN(C)S(C)(=O)=O)C3=CC=2)C=C1N1C=CC(=O)NC1=O WFDAWIPJPPHQTK-UHFFFAOYSA-N 0.000 claims 1
- CNFBZBKPLGSFTC-UHFFFAOYSA-N n-[[6-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-1-benzothiophen-3-yl]methyl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3SC=C(CNS(C)(=O)=O)C3=CC=2)C=C1N1C=CC(=O)NC1=O CNFBZBKPLGSFTC-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 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
- 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 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
- 125000001475 halogen functional group Chemical group 0.000 abstract 7
- 150000001345 alkine derivatives Chemical group 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
- C07D239/24—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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
-
- 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
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- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
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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 |
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| JP5571167B2 (ja) * | 2009-03-25 | 2014-08-13 | アッヴィ・インコーポレイテッド | 抗ウイルス組成物およびこの使用 |
| 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 |
| US8859555B2 (en) | 2009-09-25 | 2014-10-14 | Oryzon Genomics S.A. | Lysine Specific Demethylase-1 inhibitors and their use |
| US8946296B2 (en) | 2009-10-09 | 2015-02-03 | Oryzon Genomics S.A. | Substituted heteroaryl- and aryl-cyclopropylamine acetamides and their use |
| BR112012012085A2 (pt) * | 2009-11-21 | 2016-05-17 | Hoffmann La Roche | compostos antivirais heterocíclicos |
| RU2012129657A (ru) * | 2009-12-14 | 2014-01-27 | Ф.Хоффманн-Ля Рош Аг | Гетероциклические противовирусные соединения |
| EP2513057B1 (de) * | 2009-12-14 | 2013-09-04 | Merck Patent GmbH | Inhibitoren der sphingosinkinase |
| WO2011106574A2 (en) | 2010-02-24 | 2011-09-01 | Oryzon Genomics, S.A. | Inhibitors for antiviral use |
| WO2011106106A2 (en) | 2010-02-24 | 2011-09-01 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for diseases and disorders associated with hepadnaviridae |
| US9216952B2 (en) | 2010-03-23 | 2015-12-22 | Abbvie Inc. | Process for preparing antiviral compound |
| RS55348B1 (sr) | 2010-04-19 | 2017-03-31 | Oryzon Gnomics S A | Inhibitori lizin specifične demetilaze-1 i njihova upotreba |
| 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 |
| EP2593226B1 (en) | 2010-07-16 | 2018-11-14 | AbbVie Ireland Unlimited Company | Phosphine ligands for catalytic reactions |
| CR20180412A (es) | 2010-07-16 | 2018-11-01 | Abbvie Ireland Unlimited Co | Proceso para preparar compuestos antivirales |
| EP2598482B1 (en) | 2010-07-29 | 2018-04-04 | Oryzon Genomics, S.A. | Arylcyclopropylamine based demethylase inhibitors of lsd1 and their medical use |
| EP2598480B1 (en) | 2010-07-29 | 2019-04-24 | Oryzon Genomics, S.A. | Cyclopropylamine derivatives useful as lsd1 inhibitors |
| WO2012020725A1 (ja) * | 2010-08-10 | 2012-02-16 | 塩野義製薬株式会社 | Ｎｐｙ ｙ５受容体拮抗作用を有するヘテロ環誘導体 |
| WO2012045883A1 (en) | 2010-10-08 | 2012-04-12 | Oryzon Genomics S.A. | Cyclopropylamine inhibitors of oxidases |
| WO2012072713A2 (en) * | 2010-11-30 | 2012-06-07 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for diseases and disorders associated with flaviviridae |
| WO2012107498A1 (en) | 2011-02-08 | 2012-08-16 | Oryzon Genomics S.A. | Lysine demethylase inhibitors for myeloproliferative disorders |
| CN102675092B (zh) * | 2011-03-14 | 2014-11-05 | 江苏中丹药物研究有限公司 | 一种制备2-芳基-2,2-二甲基乙酸甲酯的方法 |
| US10201584B1 (en) | 2011-05-17 | 2019-02-12 | Abbvie Inc. | Compositions and methods for treating HCV |
| MX356344B (es) | 2011-10-20 | 2018-05-23 | Oryzon Genomics Sa | Compuestos de (hetero)arilciclopropilamina como inhibidores de lsd1. |
| IN2014CN03337A (ru) | 2011-10-20 | 2015-07-03 | Oryzon Genomics Sa | |
| AR088463A1 (es) | 2011-10-21 | 2014-06-11 | Abbvie Inc | Metodos para el tratamiento de hcv |
| US8466159B2 (en) | 2011-10-21 | 2013-06-18 | Abbvie Inc. | Methods for treating HCV |
| ES2527544T1 (es) * | 2011-10-21 | 2015-01-26 | Abbvie Inc. | Tratamiento mono (PSI-7977) o de combinación con AAD para su uso en el tratamiento del VHC |
| US8492386B2 (en) | 2011-10-21 | 2013-07-23 | Abbvie Inc. | Methods for treating HCV |
| MX360161B (es) | 2012-08-21 | 2018-10-09 | Abbvie Inc | Proceso para preparar compuestos antiviricos. |
| EA028481B1 (ru) * | 2012-10-18 | 2017-11-30 | Эббви Инк. | Препараты производных пиримидиндиона |
| WO2015103490A1 (en) | 2014-01-03 | 2015-07-09 | Abbvie, Inc. | Solid antiviral dosage forms |
| 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 |
| WO2016105547A1 (en) | 2014-12-24 | 2016-06-30 | Concert Pharmaceuticals, Inc. | Deuterated dasabuvir |
| JP7021100B2 (ja) * | 2016-03-17 | 2022-02-16 | エフ エム シー コーポレーション | Ｓ－エナンチオマーのラセミ体への変換方法 |
| WO2017189978A1 (en) | 2016-04-28 | 2017-11-02 | Emory University | Alkyne containing nucleotide and nucleoside therapeutic compositions and uses related thereto |
| CN108290844B (zh) * | 2016-05-27 | 2021-04-30 | 深圳市塔吉瑞生物医药有限公司 | 一种取代的萘环化合物及药物组合物及其应用 |
| 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 |
| 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 |
Family Cites Families (24)
| 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 |
| US5084084A (en) | 1989-07-14 | 1992-01-28 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
| AU627906B2 (en) | 1989-07-14 | 1992-09-03 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
| EP0442473B1 (en) | 1990-02-15 | 1998-08-19 | Takeda Chemical Industries, Ltd. | Pyrimidinedione derivatives, their production and use |
| NL9001075A (ru) * | 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 |
| 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 |
| MY164523A (en) | 2000-05-23 | 2017-12-29 | Univ Degli Studi Cagliari | Methods and compositions for treating hepatitis c virus |
| KR20040094692A (ko) * | 2002-02-14 | 2004-11-10 | 파마셋, 리미티드 | 변형된 불소화 뉴클레오사이드 유사체 |
| EA200500721A1 (ru) * | 2002-11-28 | 2005-12-29 | Шеринг Акциенгезельшафт | Пиримидины, ингибирующие chk, pdk и акт, их получение и применение в качестве лекарственных средств |
| TW200505872A (en) * | 2003-06-13 | 2005-02-16 | Lg Life Science Ltd | Hepatitis C virus inhibitors |
| AU2004261667A1 (en) * | 2003-08-01 | 2005-02-10 | Genelabs Technologies, Inc. | Bicyclic imidazol derivatives against Flaviviridae |
| US7163937B2 (en) | 2003-08-21 | 2007-01-16 | Bristol-Myers Squibb Company | Cyclic derivatives as modulators of chemokine receptor activity |
| KR20070083484A (ko) * | 2004-07-14 | 2007-08-24 | 피티씨 테라퓨틱스, 인크. | Ｃ형 간염 치료 방법 |
| AR057986A1 (es) * | 2005-11-21 | 2008-01-09 | Japan Tobacco Inc | Compuesto heterociclico y su uso farmaceutico |
| MX2010002904A (es) | 2007-09-17 | 2010-06-02 | Abbott Lab | N-fenil-dioxo-hidropirimidinas utiles como inhibidores de virus de hepatitis c (hcv). |
| 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 |
| 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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2013
- 2013-03-15 US US13/838,223 patent/US9139536B2/en active Active
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2014
- 2014-11-12 CY CY20141100943T patent/CY1115893T1/el unknown
- 2014-11-12 HR HRP20141102 patent/HRP20141102T1/hr unknown
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2015
- 2015-02-25 LU LU92666C patent/LU92666I2/xx unknown
- 2015-03-04 LT LTPA2015013C patent/LTC2203431I2/lt unknown
- 2015-03-17 HU HUS1500013C patent/HUS1500013I1/hu unknown
- 2015-03-26 CY CY2015013C patent/CY2015013I1/el unknown
- 2015-04-08 NL NL300729C patent/NL300729I1/nl unknown
- 2015-04-14 JP JP2015082240A patent/JP2015187106A/ja active Pending
- 2015-04-22 NO NO2015011C patent/NO2015011I1/no not_active IP Right Cessation
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