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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- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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| PT2203430E (pt) | 2007-09-17 | 2011-09-02 | Abbott Lab | N-fenildioxohidropirimidinas úteis como inibidores do vírus da hepatite c (vhc) |
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| CN102164909A (zh) | 2008-09-26 | 2011-08-24 | 弗·哈夫曼-拉罗切有限公司 | 用于治疗hcv的吡啶或吡嗪衍生物 |
| EP2361242B1 (en) | 2008-10-17 | 2018-08-01 | Oryzon Genomics, S.A. | Oxidase inhibitors and their use |
| US8993808B2 (en) | 2009-01-21 | 2015-03-31 | Oryzon Genomics, S.A. | Phenylcyclopropylamine derivatives and their medical use |
| CA2755023C (en) * | 2009-03-25 | 2016-12-13 | Abbott Laboratories | Antiviral compounds and uses thereof |
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| EP2486002B1 (en) | 2009-10-09 | 2019-03-27 | Oryzon Genomics, S.A. | Substituted heteroaryl- and aryl- cyclopropylamine acetamides and their use |
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| EA201200863A1 (ru) * | 2009-12-14 | 2013-01-30 | Мерк Патент Гмбх | Ингибиторы сфингозинкиназы |
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| 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 |
| CA2796726C (en) | 2010-04-19 | 2021-02-16 | Oryzon Genomics S.A. | Lysine specific demethylase-1 inhibitors and their use |
| US9255074B2 (en) | 2010-07-16 | 2016-02-09 | Abbvie Inc. | Process for preparing antiviral compounds |
| CN103097027B (zh) | 2010-07-16 | 2017-03-08 | 艾伯维巴哈马有限公司 | 用于催化反应的膦配体 |
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| EP3056486B1 (en) | 2010-07-16 | 2018-07-11 | AbbVie Ireland Unlimited Company | Process for preparing intermediates for antiviral compounds |
| SI2598482T1 (sl) | 2010-07-29 | 2018-09-28 | Oryzon Genomics, S.A. | Inhibitorji demetilaze lsd1 na osnovi arilciklopropilamina in njihova medicinska uporaba |
| WO2012013727A1 (en) | 2010-07-29 | 2012-02-02 | 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 |
| US9061966B2 (en) | 2010-10-08 | 2015-06-23 | 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 |
| EP2712315B1 (en) | 2011-02-08 | 2021-11-24 | 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 |
| MY187638A (en) | 2011-10-20 | 2021-10-06 | Oryzon Genomics Sa | (hetero)aryl cyclopropylamine compounds as lsd1 inhibitors |
| EP2768805B1 (en) | 2011-10-20 | 2020-03-25 | Oryzon Genomics, S.A. | (hetero)aryl cyclopropylamine compounds as lsd1 inhibitors |
| US8492386B2 (en) | 2011-10-21 | 2013-07-23 | Abbvie Inc. | Methods for treating HCV |
| US8466159B2 (en) | 2011-10-21 | 2013-06-18 | Abbvie Inc. | Methods for treating HCV |
| PT107924A (pt) * | 2011-10-21 | 2014-12-03 | Abbvie Inc | Tratamento de combinação de daa (eg. com abt-072 ou abt-333) para utilização no tratamento de hcv |
| CN104383541A (zh) | 2011-10-21 | 2015-03-04 | 艾伯维公司 | 用于治疗hcv的包含至少两种直接抗病毒剂和利巴韦林但无干扰素的方法 |
| MX360161B (es) | 2012-08-21 | 2018-10-09 | Abbvie Inc | Proceso para preparar compuestos antiviricos. |
| CN109260207A (zh) * | 2012-10-18 | 2019-01-25 | 艾伯维公司 | 嘧啶二酮衍生物化合物的制剂 |
| EP3089757A1 (en) | 2014-01-03 | 2016-11-09 | 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 |
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| WO2017202207A1 (zh) * | 2016-05-27 | 2017-11-30 | 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 |
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| DK2639226T3 (en) | 2007-09-17 | 2016-12-19 | Abbvie Bahamas Ltd | Anti-infective pyrimidines and uses thereof |
| AR070027A1 (es) * | 2007-09-17 | 2010-03-10 | Abbott Lab | Agentes anti-infecciosos contra el virus hcv |
| PT2203430E (pt) | 2007-09-17 | 2011-09-02 | Abbott Lab | N-fenildioxohidropirimidinas úteis como inibidores do vírus da hepatite c (vhc) |
| CA2730517A1 (en) | 2008-07-23 | 2010-01-28 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compounds |
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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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