RU2428428C9 - Серусодержащие соединения, действующие как ингибиторы сериновой протеазы ns3 вируса гепатита с - Google Patents
Серусодержащие соединения, действующие как ингибиторы сериновой протеазы ns3 вируса гепатита с Download PDFInfo
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- RU2428428C9 RU2428428C9 RU2006134003/04A RU2006134003A RU2428428C9 RU 2428428 C9 RU2428428 C9 RU 2428428C9 RU 2006134003/04 A RU2006134003/04 A RU 2006134003/04A RU 2006134003 A RU2006134003 A RU 2006134003A RU 2428428 C9 RU2428428 C9 RU 2428428C9
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- pharmaceutically acceptable
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- stereoisomers
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- 150000001875 compounds Chemical class 0.000 title claims abstract 75
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims 13
- 239000005864 Sulphur Substances 0.000 title 1
- 108700012707 hepatitis C virus NS3 Proteins 0.000 title 1
- 239000003001 serine protease inhibitor Substances 0.000 title 1
- 108091005804 Peptidases Proteins 0.000 claims abstract 25
- 239000004365 Protease Substances 0.000 claims abstract 25
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims abstract 25
- 230000002401 inhibitory effect Effects 0.000 claims abstract 19
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 11
- 238000000034 method Methods 0.000 claims abstract 7
- 230000000694 effects Effects 0.000 claims abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 24
- 150000003839 salts Chemical class 0.000 claims 21
- 150000002148 esters Chemical class 0.000 claims 20
- 230000001747 exhibiting effect Effects 0.000 claims 17
- 125000004429 atom Chemical group 0.000 claims 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 12
- 125000004122 cyclic group Chemical group 0.000 claims 12
- 125000005842 heteroatom Chemical group 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 12
- 229910052760 oxygen Inorganic materials 0.000 claims 12
- 239000001301 oxygen Substances 0.000 claims 12
- 229910052717 sulfur Inorganic materials 0.000 claims 12
- 239000011593 sulfur Substances 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 9
- 229940079322 interferon Drugs 0.000 claims 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 6
- 125000001831 (C6-C10) heteroaryl group Chemical group 0.000 claims 6
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 6
- 102000014150 Interferons Human genes 0.000 claims 6
- 108010050904 Interferons Proteins 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 241000711549 Hepacivirus C Species 0.000 claims 4
- 239000003443 antiviral agent Substances 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 238000011282 treatment Methods 0.000 claims 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 150000002367 halogens Chemical group 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 229920001184 polypeptide Polymers 0.000 claims 3
- 102000004196 processed proteins & peptides Human genes 0.000 claims 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 102000006992 Interferon-alpha Human genes 0.000 claims 2
- 108010047761 Interferon-alpha Proteins 0.000 claims 2
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical group 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 2
- 125000003368 amide group Chemical group 0.000 claims 2
- 125000001769 aryl amino group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 125000005518 carboxamido group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 229960000329 ribavirin Drugs 0.000 claims 2
- 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 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 208000005176 Hepatitis C Diseases 0.000 claims 1
- 229930194542 Keto Natural products 0.000 claims 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims 1
- 125000005421 aryl sulfonamido group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000012634 fragment Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
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- QIIQFGQNDPHSQC-MKFJPJDMSA-N CCNC(C(C(CCC#C)NC([C@H](C[C@H](C1)C(C)C)N1C(C1(C(C)(C)C1C)NC(NC1(CS(C(C)(C)C)(=O)=O)CCCCC1)=O)=O)=O)=O)=O Chemical compound CCNC(C(C(CCC#C)NC([C@H](C[C@H](C1)C(C)C)N1C(C1(C(C)(C)C1C)NC(NC1(CS(C(C)(C)C)(=O)=O)CCCCC1)=O)=O)=O)=O)=O QIIQFGQNDPHSQC-MKFJPJDMSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
-
- A—HUMAN NECESSITIES
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| PL1730110T3 (pl) * | 2004-02-27 | 2010-11-30 | Merck Sharp & Dohme | Siarkowe związki jako inhibitory proteazy serynowej NS3 wirusa zapalenia wątroby typu C |
| ES2572980T3 (es) | 2005-06-02 | 2016-06-03 | Merck Sharp & Dohme Corp. | Combinación de inhibidores de la proteasa del VHC con un tensioactivo |
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| WO2000009543A2 (en) * | 1998-08-10 | 2000-02-24 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis c inhibitor tri-peptides |
| WO2002008244A2 (en) * | 2000-07-21 | 2002-01-31 | Schering Corporation | Peptides as ns3-serine protease inhibitors of hepatitis c virus |
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