JP2010539187A5 - - Google Patents
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- Publication number
- JP2010539187A5 JP2010539187A5 JP2010525103A JP2010525103A JP2010539187A5 JP 2010539187 A5 JP2010539187 A5 JP 2010539187A5 JP 2010525103 A JP2010525103 A JP 2010525103A JP 2010525103 A JP2010525103 A JP 2010525103A JP 2010539187 A5 JP2010539187 A5 JP 2010539187A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- dioxo
- dihydropyrimidin
- tert
- butyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000001424 substituent group Chemical group 0.000 claims 47
- 150000001875 compounds Chemical class 0.000 claims 45
- -1 hydroxy, methyl Chemical group 0.000 claims 39
- 150000003839 salts Chemical class 0.000 claims 39
- 125000000217 alkyl group Chemical group 0.000 claims 32
- 239000003814 drug Substances 0.000 claims 32
- 125000003342 alkenyl group Chemical group 0.000 claims 30
- 125000000304 alkynyl group Chemical group 0.000 claims 27
- 125000005843 halogen group Chemical group 0.000 claims 23
- 241000711549 Hepacivirus C Species 0.000 claims 22
- 229940124597 therapeutic agent Drugs 0.000 claims 22
- 125000000623 heterocyclic group Chemical group 0.000 claims 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 20
- 125000003545 alkoxy group Chemical group 0.000 claims 19
- 125000004452 carbocyclyl group Chemical group 0.000 claims 18
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- 239000003112 inhibitor Substances 0.000 claims 13
- 125000004043 oxo group Chemical group O=* 0.000 claims 13
- 125000003302 alkenyloxy group Chemical group 0.000 claims 12
- 125000005133 alkynyloxy group Chemical group 0.000 claims 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 11
- 229910052757 nitrogen Inorganic materials 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims 9
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 9
- 239000002259 anti human immunodeficiency virus agent Substances 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- 229960000329 ribavirin Drugs 0.000 claims 9
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims 9
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 8
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 102000014150 Interferons Human genes 0.000 claims 6
- 108010050904 Interferons Proteins 0.000 claims 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 6
- 229940079593 drug Drugs 0.000 claims 6
- 229940079322 interferon Drugs 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 229920002477 rna polymer Polymers 0.000 claims 6
- 241000124008 Mammalia Species 0.000 claims 5
- 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
- 229940124411 anti-hiv antiviral agent Drugs 0.000 claims 5
- 125000005884 carbocyclylalkyl 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
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- DYMRYCZRMAHYKE-UHFFFAOYSA-N n-diazonitramide Chemical compound [O-][N+](=O)N=[N+]=[N-] DYMRYCZRMAHYKE-UHFFFAOYSA-N 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 208000005176 Hepatitis C Diseases 0.000 claims 4
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims 4
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 4
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 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 3
- 125000005087 alkynylcarbonyl group Chemical group 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims 3
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 claims 3
- 241001493065 dsRNA viruses Species 0.000 claims 3
- 230000002401 inhibitory effect Effects 0.000 claims 3
- 239000003446 ligand Substances 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims 3
- 229910052717 sulfur Inorganic materials 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
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- 125000006650 (C2-C4) alkynyl 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
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 2
- 125000005193 alkenylcarbonyloxy group Chemical group 0.000 claims 2
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 2
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 239000010949 copper Substances 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 230000010076 replication Effects 0.000 claims 2
- 159000000000 sodium salts Chemical class 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000000845 uracil-1-yl group Chemical group [*]N1C(=O)N([H])C(=O)C([H])=C1[H] 0.000 claims 2
- 230000029812 viral genome replication Effects 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 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
- DGTXGWLRWHJWAO-UHFFFAOYSA-N 1-[3-tert-butyl-5-[2-(2,5-dimethylpyrrol-1-yl)-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(=NC3=CC=2)N2C(=CC=C2C)C)C=C1N1C=CC(=O)NC1=O DGTXGWLRWHJWAO-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
- YNFBMDWHEHETJW-UHFFFAOYSA-N 2-pyridin-2-yl-1h-benzimidazole Chemical compound N1=CC=CC=C1C1=NC2=CC=CC=C2N1 YNFBMDWHEHETJW-UHFFFAOYSA-N 0.000 claims 1
- 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
- 239000005725 8-Hydroxyquinoline Substances 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims 1
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims 1
- 241000700605 Viruses Species 0.000 claims 1
- 125000005091 alkenylcarbonylamino group Chemical group 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000004466 alkoxycarbonylamino 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
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims 1
- YZDBZOOCRDOXFK-UHFFFAOYSA-N cyano-(diazidoamino)carbamic acid Chemical compound C(=O)(O)N(N(N=[N+]=[N-])N=[N+]=[N-])C#N YZDBZOOCRDOXFK-UHFFFAOYSA-N 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 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
- 125000002485 formyl group Chemical class [H]C(*)=O 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
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000002346 iodo group Chemical group I* 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
- 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
- CMOBXBANKIGTSJ-UHFFFAOYSA-N n-(2-cyanophenyl)pyridine-2-carboxamide Chemical compound C=1C=CC=NC=1C(=O)NC1=CC=CC=C1C#N CMOBXBANKIGTSJ-UHFFFAOYSA-N 0.000 claims 1
- WUYINQBOZASLCM-UHFFFAOYSA-N n-(4-cyanophenyl)pyridine-2-carboxamide Chemical compound C=1C=CC=NC=1C(=O)NC1=CC=C(C#N)C=C1 WUYINQBOZASLCM-UHFFFAOYSA-N 0.000 claims 1
- BSGREXYSTRLYNX-SZXQPVLSSA-N n-[(e)-[5-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-2,3-dihydroinden-1-ylidene]amino]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3CCC(/C3=CC=2)=N\NS(C)(=O)=O)C=C1N1C=CC(=O)NC1=O BSGREXYSTRLYNX-SZXQPVLSSA-N 0.000 claims 1
- WZXVXZFFDOBSBD-YYADALCUSA-N n-[(e)-[5-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)phenyl]-2,3-dihydroinden-1-ylidene]amino]methanesulfonamide Chemical compound C=1C(C(C)(C)C)=CC(C=2C=C3CCC(/C3=CC=2)=N\NS(C)(=O)=O)=CC=1N1C=CC(=O)NC1=O WZXVXZFFDOBSBD-YYADALCUSA-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
- 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
- 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
- SZESPTRIDHGUMG-UHFFFAOYSA-N n-[2-[5-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]-3h-inden-1-yl]propan-2-yl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3CC=C(C3=CC=2)C(C)(C)NS(C)(=O)=O)C=C1N1C=CC(=O)NC1=O SZESPTRIDHGUMG-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
- 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
- QIPZQFYINUXBFX-UHFFFAOYSA-N n-[6-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]quinoxalin-2-yl]methanesulfonamide Chemical compound C1=C(C(C)(C)C)C(OC)=C(C=2C=C3N=CC(NS(C)(=O)=O)=NC3=CC=2)C=C1N1C=CC(=O)NC1=O QIPZQFYINUXBFX-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
- 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
- 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
- JUEYZKZXMUYVJK-UHFFFAOYSA-N n-[6-[5-(2,4-dioxopyrimidin-1-yl)-2-methoxy-3-(5-methylfuran-2-yl)phenyl]naphthalen-2-yl]methanesulfonamide Chemical compound C1=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C(OC)=C(C=2OC(C)=CC=2)C=C1N1C=CC(=O)NC1=O JUEYZKZXMUYVJK-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
- 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
- QNBYHXKNWCQTLS-UHFFFAOYSA-N n-[6-[5-(2,4-dioxopyrimidin-1-yl)-3-(1-hydroxy-2-methylpropan-2-yl)-2-methoxyphenyl]naphthalen-2-yl]methanesulfonamide Chemical compound C1=C(C(C)(C)CO)C(OC)=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C=C1N1C=CC(=O)NC1=O QNBYHXKNWCQTLS-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
- IWENBQYSPNHRJN-UHFFFAOYSA-N n-[6-[5-(2,4-dioxopyrimidin-1-yl)-3-iodo-2-methoxyphenyl]naphthalen-2-yl]methanesulfonamide Chemical compound C1=C(C=2C=C3C=CC(NS(C)(=O)=O)=CC3=CC=2)C(OC)=C(I)C=C1N1C=CC(=O)NC1=O IWENBQYSPNHRJN-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
- OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 claims 1
- ICTGBOFCIDHVPA-UHFFFAOYSA-N n-methylsulfonylmethanesulfonamide Chemical compound CS(=O)(=O)NS(C)(=O)=O ICTGBOFCIDHVPA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 229960003540 oxyquinoline Drugs 0.000 claims 1
- 239000000825 pharmaceutical preparation 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
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 1
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Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2725015A1 (en) | 2007-09-17 | 2014-04-30 | AbbVie Bahamas Ltd. | Uracil or thymine derivative for treating hepatitis c |
| US8178548B2 (en) | 2007-09-17 | 2012-05-15 | Abbott Laboratories | Anti-infective agents and uses thereof |
| ES2368879T3 (es) * | 2007-09-17 | 2011-11-23 | Abbott Laboratories | Pirimidinas antiinfecciosas y usos de las mismas. |
| JP2011528686A (ja) * | 2008-07-23 | 2011-11-24 | エフ．ホフマン−ラ ロシュ アーゲー | ヘテロ環式抗ウイルス性化合物 |
| KR20110061640A (ko) | 2008-09-26 | 2011-06-09 | 에프. 호프만-라 로슈 아게 | Ｈｃｖ 치료용 피린 또는 피라진 유도체 |
| EP2361242B1 (en) | 2008-10-17 | 2018-08-01 | Oryzon Genomics, S.A. | Oxidase inhibitors and their use |
| WO2010084160A1 (en) | 2009-01-21 | 2010-07-29 | Oryzon Genomics S.A. | Phenylcyclopropylamine derivatives and their medical use |
| RU2552533C2 (ru) * | 2009-03-25 | 2015-06-10 | Эббви Инк. | Противовирусные соединения и их применения |
| CN102448936A (zh) | 2009-04-25 | 2012-05-09 | 弗·哈夫曼-拉罗切有限公司 | 杂环抗病毒化合物 |
| TWI428332B (zh) | 2009-06-09 | 2014-03-01 | Hoffmann La Roche | 雜環抗病毒化合物 |
| CN102803212A (zh) | 2009-06-24 | 2012-11-28 | 弗·哈夫曼-拉罗切有限公司 | 抗病毒的杂环化合物 |
| BR112012005616A2 (pt) | 2009-09-21 | 2016-06-21 | Hoffmann La Roche | compostos antivirais heterocíclicos |
| KR101736218B1 (ko) | 2009-09-25 | 2017-05-16 | 오리존 지노믹스 에스.에이. | 라이신 특이적 디메틸라아제-1 억제제 및 이의 용도 |
| EP2486002B1 (en) | 2009-10-09 | 2019-03-27 | Oryzon Genomics, S.A. | Substituted heteroaryl- and aryl- cyclopropylamine acetamides and their use |
| KR20120085918A (ko) * | 2009-11-21 | 2012-08-01 | 에프. 호프만-라 로슈 아게 | 헤테로환형 항바이러스성 화합물 |
| EP2513092A1 (en) * | 2009-12-14 | 2012-10-24 | F. Hoffmann-La Roche AG | Heterocyclic antiviral compounds |
| MX2012006776A (es) * | 2009-12-14 | 2012-10-05 | Merck Patent Gmbh | Inhibidores de la esfingosina quinasa. |
| WO2011106574A2 (en) | 2010-02-24 | 2011-09-01 | Oryzon Genomics, S.A. | Inhibitors for antiviral use |
| US9186337B2 (en) | 2010-02-24 | 2015-11-17 | 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 |
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| 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 |
| PH12013500105A1 (en) | 2010-07-16 | 2013-02-25 | Abbvie Bahamas Ltd | Process for preparing antiviral compounds |
| LT2598482T (lt) | 2010-07-29 | 2018-07-10 | Oryzon Genomics, S.A. | Demetilazės lsd1 inhibitoriai arilciklopropilamino pagrindu ir jų medicininis panaudojimas |
| US9006449B2 (en) | 2010-07-29 | 2015-04-14 | 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 |
| 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 |
| EP3736265A1 (en) | 2011-10-20 | 2020-11-11 | Oryzon Genomics, S.A. | (hetero)aryl cyclopropylamine compounds as lsd1 inhibitors |
| SI2776394T1 (sl) | 2011-10-20 | 2019-05-31 | Oryzon Genomics, S.A. | Spojine (hetero)aril ciklopropilamina kot inhibitorji LSD1 |
| DE202012012956U1 (de) | 2011-10-21 | 2014-10-16 | Abbvie Inc. | Kombination aus mindestens zwei direkt wirkenden antiviralen Wirkstoffen für die Verwendung zur Behandlung von HCV, umfassend Ribavirin aber nicht Interferon |
| SG2014011670A (en) * | 2011-10-21 | 2014-10-30 | Abbvie Inc | Combination treatment (eg. with abt-072 or abt -333) of daas for use in treating hcv |
| 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 |
| JP6469571B2 (ja) | 2012-08-21 | 2019-02-13 | アッヴィ・アイルランド・アンリミテッド・カンパニー | 抗ウイルス性化合物を調製するための方法 |
| CN104853752B (zh) * | 2012-10-18 | 2018-10-23 | 艾伯维公司 | 嘧啶二酮衍生物化合物的制剂 |
| 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 |
| EA039557B1 (ru) * | 2016-03-17 | 2022-02-10 | Фмк Корпорейшн | Способ превращения s-энантиомера в его рацемическую форму |
| US11192914B2 (en) | 2016-04-28 | 2021-12-07 | 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 |
| US12274700B1 (en) | 2020-10-30 | 2025-04-15 | Accencio LLC | Methods of treating symptoms of coronavirus infection with RNA polymerase inhibitors |
| CN117466847A (zh) * | 2022-07-22 | 2024-01-30 | 中国医药工业研究总院有限公司 | 一种利非斯特中间体苯并呋喃-6-羧酸的制备方法 |
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 (enExample) * | 1990-05-04 | 1991-12-02 | Duphar Int Res | |
| EP0489480A1 (en) * | 1990-12-05 | 1992-06-10 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
| JPH05213755A (ja) | 1992-02-07 | 1993-08-24 | Nikko Kyodo Co Ltd | 肝臓障害治療薬 |
| DE19528305A1 (de) | 1995-08-02 | 1997-02-06 | Bayer Ag | Substituierte Phenyluracile |
| US6380387B1 (en) * | 1999-12-06 | 2002-04-30 | Hoffmann-La Roche Inc. | 4-Pyrimidinyl-n-acyl-l phenylalanines |
| DK1237878T3 (da) | 1999-12-06 | 2007-07-30 | Hoffmann La Roche | 4-pyrimidinyl-N-acyl-L-phenylanin |
| 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 |
| EP1480982A4 (en) * | 2002-02-14 | 2007-08-01 | Pharmasset Inc | MODIFIED FLUORINATED NUCLEOSIDE ANALOGUES |
| CN1717396A (zh) * | 2002-11-28 | 2006-01-04 | 舍林股份公司 | Chk－、Pdk－和Akt－抑制嘧啶,其制备及作为药物的用途 |
| TW200505872A (en) * | 2003-06-13 | 2005-02-16 | Lg Life Science Ltd | Hepatitis C virus inhibitors |
| CN1829709A (zh) * | 2003-08-01 | 2006-09-06 | 健亚生物科技公司 | 对抗黄病毒的双环咪唑衍生物 |
| US7163937B2 (en) | 2003-08-21 | 2007-01-16 | Bristol-Myers Squibb Company | Cyclic derivatives as modulators of chemokine receptor activity |
| EA200700243A1 (ru) * | 2004-07-14 | 2007-08-31 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Способы лечения гепатита с |
| EP1953147A1 (en) * | 2005-11-21 | 2008-08-06 | Japan Tobacco, Inc. | Heterocyclic compound and medicinal application thereof |
| ES2368879T3 (es) * | 2007-09-17 | 2011-11-23 | Abbott Laboratories | Pirimidinas antiinfecciosas y usos de las mismas. |
| US8178548B2 (en) | 2007-09-17 | 2012-05-15 | Abbott Laboratories | Anti-infective agents and uses thereof |
| EP2725015A1 (en) | 2007-09-17 | 2014-04-30 | AbbVie Bahamas Ltd. | Uracil or thymine derivative for treating hepatitis c |
| JP2011528686A (ja) | 2008-07-23 | 2011-11-24 | エフ．ホフマン−ラ ロシュ アーゲー | ヘテロ環式抗ウイルス性化合物 |
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