EA033622B1 - Ингибиторы полимеразы вируса гепатита c - Google Patents

Info

Publication number

EA033622B1

EA033622B1 EA201792094A EA201792094A EA033622B1 EA 033622 B1 EA033622 B1 EA 033622B1 EA 201792094 A EA201792094 A EA 201792094A EA 201792094 A EA201792094 A EA 201792094A EA 033622 B1 EA033622 B1 EA 033622B1

Authority

EA

Eurasian Patent Office

Prior art keywords

mmol

compound

ethoxy

fluorophenyl

cyclopropyl

Prior art date

2015-03-23

Links

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• Global Dossier
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• 241000711549 Hepacivirus C Species 0.000 title claims abstract description 74
• 239000003112 inhibitor Substances 0.000 title abstract description 15
• 150000001875 compounds Chemical class 0.000 claims abstract description 890
• 238000000034 method Methods 0.000 claims abstract description 72
• 239000000203 mixture Substances 0.000 claims abstract description 70
• 208000015181 infectious disease Diseases 0.000 claims abstract description 41
• 150000003839 salts Chemical class 0.000 claims abstract description 31
• 239000003814 drug Substances 0.000 claims abstract description 20
• 208000010710 hepatitis C virus infection Diseases 0.000 claims abstract description 9
• -1 —C (O) NH 2 Chemical group 0.000 claims description 293
• 125000000217 alkyl group Chemical group 0.000 claims description 40
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 39
• 241000700605 Viruses Species 0.000 claims description 33
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
• 230000001225 therapeutic effect Effects 0.000 claims description 26
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
• 229910052739 hydrogen Inorganic materials 0.000 claims description 16
• 125000002947 alkylene group Chemical group 0.000 claims description 15
• 239000001257 hydrogen Substances 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 4
• 150000001721 carbon Chemical group 0.000 claims description 3
• 229910052731 fluorine Inorganic materials 0.000 claims description 3
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 2
• 239000011737 fluorine Substances 0.000 claims description 2
• 125000001153 fluoro group Chemical group F* 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 2
• 125000005843 halogen group Chemical group 0.000 claims 1
• 230000007420 reactivation Effects 0.000 claims 1
• 238000011282 treatment Methods 0.000 abstract description 14
• 230000007419 viral reactivation Effects 0.000 abstract description 5
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 411
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 242
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• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 204
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• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 23
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• 239000012359 Methanesulfonyl chloride Substances 0.000 description 18
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 18
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 18
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• 239000004480 active ingredient Substances 0.000 description 16
• 230000000694 effects Effects 0.000 description 15
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 15
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• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
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• 239000008346 aqueous phase Substances 0.000 description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
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