JP6069492B2 - Ｃ型肝炎ウイルス阻害剤 - Google Patents
Ｃ型肝炎ウイルス阻害剤 Download PDFInfo
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- JP6069492B2 JP6069492B2 JP2015509101A JP2015509101A JP6069492B2 JP 6069492 B2 JP6069492 B2 JP 6069492B2 JP 2015509101 A JP2015509101 A JP 2015509101A JP 2015509101 A JP2015509101 A JP 2015509101A JP 6069492 B2 JP6069492 B2 JP 6069492B2
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- Prior art keywords
- alkyl
- compound
- methyl
- mmol
- optionally substituted
- Prior art date
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- 241000711549 Hepacivirus C Species 0.000 title claims description 58
- 239000003112 inhibitor Substances 0.000 title claims description 41
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- 125000000217 alkyl group Chemical group 0.000 claims description 213
- 238000000034 method Methods 0.000 claims description 77
- 239000000203 mixture Substances 0.000 claims description 75
- 229910052739 hydrogen Inorganic materials 0.000 claims description 74
- 239000001257 hydrogen Substances 0.000 claims description 73
- -1 —OR d Chemical group 0.000 claims description 67
- 239000008194 pharmaceutical composition Substances 0.000 claims description 60
- 125000005843 halogen group Chemical group 0.000 claims description 46
- 239000002777 nucleoside Substances 0.000 claims description 43
- 241000124008 Mammalia Species 0.000 claims description 42
- 150000002431 hydrogen Chemical class 0.000 claims description 39
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
- 108010050904 Interferons Proteins 0.000 claims description 34
- 102000014150 Interferons Human genes 0.000 claims description 34
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 30
- 239000003814 drug Substances 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 229940124597 therapeutic agent Drugs 0.000 claims description 27
- 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 description 25
- 101800001014 Non-structural protein 5A Proteins 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 229940047124 interferons Drugs 0.000 claims description 22
- 229960000329 ribavirin Drugs 0.000 claims description 22
- 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 description 22
- 208000010710 hepatitis C virus infection Diseases 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 229940124771 HCV-NS3 protease inhibitor Drugs 0.000 claims description 19
- 108700008776 hepatitis C virus NS-5 Proteins 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 230000002401 inhibitory effect Effects 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 230000010076 replication Effects 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 239000003937 drug carrier Substances 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
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- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 10
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 10
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 7
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- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 6
- 238000002560 therapeutic procedure Methods 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 3
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- 238000005481 NMR spectroscopy Methods 0.000 description 17
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
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- ATOLIHZIXHZSBA-BTSKBWHGSA-N methyl n-[(1r)-2-[(2s)-2-[5-[4-[6-[2-[(2s)-1-[(2s)-2-(methoxycarbonylamino)-3-methylbutanoyl]pyrrolidin-2-yl]-3h-benzimidazol-5-yl]thieno[3,2-b]thiophen-3-yl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C1=NC2=CC(C=3C=4SC=C(C=4SC=3)C=3C=CC(=CC=3)C=3N=C(NC=3)[C@H]3N(CCC3)C(=O)[C@H](NC(=O)OC)C=3C=CC=CC=3)=CC=C2N1 ATOLIHZIXHZSBA-BTSKBWHGSA-N 0.000 description 1
- VABAPQQVXRSMBS-ROUUACIJSA-N methyl n-[(2s)-1-[(2s)-2-[5-(4-bromophenyl)-1h-imidazol-2-yl]-4-methyl-2,5-dihydropyrrol-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CC(C)=C[C@H]1C1=NC=C(C=2C=CC(Br)=CC=2)N1 VABAPQQVXRSMBS-ROUUACIJSA-N 0.000 description 1
- YMCAVGXTSCNFDE-BBACVFHCSA-N methyl n-[(2s)-1-[(2s)-2-[5-[4-[4-[2-[(8s)-7-[(2s)-2-(methoxycarbonylamino)-3-methylbutanoyl]-1,4-dioxa-7-azaspiro[4.4]nonan-8-yl]-1h-imidazol-5-yl]phenyl]phenyl]-1h-imidazol-2-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C1=NC=C(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2NC(=NC=2)[C@H]2N(CC3(C2)OCCO3)C(=O)[C@@H](NC(=O)OC)C(C)C)N1 YMCAVGXTSCNFDE-BBACVFHCSA-N 0.000 description 1
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- VYCWVBNONSJPFM-INIZCTEOSA-N tert-butyl (2s)-2-[5-(4-bromophenyl)-1h-imidazol-2-yl]-4-methyl-2,5-dihydropyrrole-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC(C)=C[C@H]1C1=NC(C=2C=CC(Br)=CC=2)=CN1 VYCWVBNONSJPFM-INIZCTEOSA-N 0.000 description 1
- YVSDPHOCDJWOPA-XEGCMXMBSA-N tert-butyl (2s)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C(O)CCC[C@H]1CO[Si](C(C)(C)C)(C=1C=CC=CC=1)C1=CC=CC=C1 YVSDPHOCDJWOPA-XEGCMXMBSA-N 0.000 description 1
- DXIIYUFMHGBZIN-SJCJKPOMSA-N tert-butyl (2s,4s)-2-(7-bromo-3h-benzo[e]benzimidazol-2-yl)-4-methylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C[C@@H](C)C[C@H]1C(N1)=NC2=C1C=CC1=CC(Br)=CC=C21 DXIIYUFMHGBZIN-SJCJKPOMSA-N 0.000 description 1
- XDLXXJCQOZNLCI-SJCJKPOMSA-N tert-butyl (2s,4s)-2-[(2-amino-6-bromonaphthalen-1-yl)carbamoyl]-4-methylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C[C@@H](C)C[C@H]1C(=O)NC1=C(N)C=CC2=CC(Br)=CC=C12 XDLXXJCQOZNLCI-SJCJKPOMSA-N 0.000 description 1
- GOWWWXDJMJKQIF-GUYCJALGSA-N tert-butyl (2s,5s)-2-[5-(4-bromophenyl)-1h-imidazol-2-yl]-5-methylpiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C[C@@H](C)CC[C@H]1C1=NC=C(C=2C=CC(Br)=CC=2)N1 GOWWWXDJMJKQIF-GUYCJALGSA-N 0.000 description 1
- CZJGSDMEPZRKKA-CYBMUJFWSA-N tert-butyl (3r)-4-[5-[[4-bromo-2-chloro-5-(trifluoromethoxy)phenyl]carbamoyl]pyridin-2-yl]-3-methylpiperazine-1-carboxylate Chemical compound C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1C1=CC=C(C(=O)NC=2C(=CC(Br)=C(OC(F)(F)F)C=2)Cl)C=N1 CZJGSDMEPZRKKA-CYBMUJFWSA-N 0.000 description 1
- FMLPQHJYUZTHQS-UHFFFAOYSA-N tert-butyl 3-methylpiperazine-1-carboxylate Chemical compound CC1CN(C(=O)OC(C)(C)C)CCN1 FMLPQHJYUZTHQS-UHFFFAOYSA-N 0.000 description 1
- IYWRCNFZPNEADN-CXODAYGWSA-N tert-butyl n-[(2s)-1-[(2s,4r)-2-[[(1r,2s)-1-(cyclopropylsulfonylcarbamoyl)-2-ethenylcyclopropyl]carbamoyl]-4-(6-methoxyisoquinolin-1-yl)oxypyrrolidin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC=1C2=CC=C(C=C2C=CN=1)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C IYWRCNFZPNEADN-CXODAYGWSA-N 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- UOBYJVFBFSLCTQ-UHFFFAOYSA-N tmc647055 Chemical compound C12=CC=C(C(NS(=O)(=O)N(C)CCOCCN(C)C3=O)=O)C=C2N2CC3=CC3=CC(OC)=CC=C3C2=C1C1CCCCC1 UOBYJVFBFSLCTQ-UHFFFAOYSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 238000003146 transient transfection Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000017613 viral reproduction Effects 0.000 description 1
- 229940100050 virazole Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
- A61P31/12—Antivirals
-
- 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
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261637956P | 2012-04-25 | 2012-04-25 | |
| US61/637,956 | 2012-04-25 | ||
| US201361773977P | 2013-03-07 | 2013-03-07 | |
| US61/773,977 | 2013-03-07 | ||
| PCT/US2013/037934 WO2013163270A1 (en) | 2012-04-25 | 2013-04-24 | Hepatitis c virus inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015515494A JP2015515494A (ja) | 2015-05-28 |
| JP2015515494A5 JP2015515494A5 (enExample) | 2016-04-21 |
| JP6069492B2 true JP6069492B2 (ja) | 2017-02-01 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015509101A Expired - Fee Related JP6069492B2 (ja) | 2012-04-25 | 2013-04-24 | Ｃ型肝炎ウイルス阻害剤 |
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| Country | Link |
|---|---|
| US (2) | US9066944B2 (enExample) |
| EP (1) | EP2850072B1 (enExample) |
| JP (1) | JP6069492B2 (enExample) |
| CN (1) | CN104302636B (enExample) |
| CA (1) | CA2869908C (enExample) |
| ES (1) | ES2599665T3 (enExample) |
| WO (1) | WO2013163270A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2624846T3 (es) * | 2012-04-25 | 2017-07-17 | Theravance Biopharma R&D Ip, Llc | Compuestos de piperazina-piperidina como inhibidores del virus de la hepatitis C |
| GB202013383D0 (en) * | 2020-08-26 | 2020-10-07 | Givaudan Sa | Process |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US7659270B2 (en) | 2006-08-11 | 2010-02-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8329159B2 (en) | 2006-08-11 | 2012-12-11 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8303944B2 (en) | 2006-08-11 | 2012-11-06 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8147818B2 (en) | 2008-02-13 | 2012-04-03 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8729077B2 (en) | 2008-11-28 | 2014-05-20 | Glaxosmithkline Llc | Anti-viral compounds, compositions, and methods of use |
| WO2010094977A1 (en) * | 2009-02-23 | 2010-08-26 | Arrow Therapeutics Limited | Novel biphenyl compounds useful for the treatment of hepatitis c |
| WO2010096777A1 (en) | 2009-02-23 | 2010-08-26 | Presidio Pharmaceuticals, Inc. | Inhibitors of hcv ns5a |
| BRPI1010795B1 (pt) | 2009-05-13 | 2018-12-11 | Gilead Pharmasset Llc | compostos antivirais, seu uso e composição farmacêutica compreendendo os mesmos |
| US8822700B2 (en) | 2009-09-11 | 2014-09-02 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US9156818B2 (en) | 2009-09-11 | 2015-10-13 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US8377980B2 (en) | 2009-12-16 | 2013-02-19 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| PE20130244A1 (es) * | 2010-01-25 | 2013-03-10 | Enanta Pharm Inc | Inhibidores del virus de la hepatitis c |
| CN102918049A (zh) | 2010-03-09 | 2013-02-06 | 默沙东公司 | 稠合三环甲硅烷基化合物及其用于治疗病毒性疾病的方法 |
| EP2575819A4 (en) | 2010-06-04 | 2013-11-27 | Enanta Pharm Inc | INHIBITORS OF HEPATITIS C VIRUS |
| AU2010358561B2 (en) * | 2010-08-04 | 2016-06-02 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8697704B2 (en) * | 2010-08-12 | 2014-04-15 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| ES2548286T3 (es) * | 2010-11-04 | 2015-10-15 | Theravance Biopharma R&D Ip, Llc | Nuevos inhibidores del virus de la hepatitis C |
| CA2852700A1 (en) | 2011-11-03 | 2013-05-10 | Theravance, Inc. | Rod-like hepatitis c virus inhibitors containing the fragment {2-[4-(biphenyl-4-yl)-1h-imidazo-2-yl]pyrrolidine-1-carbonlymethyl}amine |
| US8883135B2 (en) * | 2012-05-03 | 2014-11-11 | Theravance Biopharma R&D Ip, Llc | Crystalline form of a pyridyl-piperazinyl hepatitis C virus inhibitor |
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2013
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- 2013-04-24 CA CA2869908A patent/CA2869908C/en not_active Expired - Fee Related
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- 2013-04-24 CN CN201380022245.8A patent/CN104302636B/zh not_active Expired - Fee Related
- 2013-04-24 US US13/869,228 patent/US9066944B2/en not_active Expired - Fee Related
- 2013-04-24 JP JP2015509101A patent/JP6069492B2/ja not_active Expired - Fee Related
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2015
- 2015-05-21 US US14/718,296 patent/US9365549B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN104302636B (zh) | 2017-03-29 |
| US20130287731A1 (en) | 2013-10-31 |
| CN104302636A (zh) | 2015-01-21 |
| US9365549B2 (en) | 2016-06-14 |
| JP2015515494A (ja) | 2015-05-28 |
| EP2850072A1 (en) | 2015-03-25 |
| US9066944B2 (en) | 2015-06-30 |
| EP2850072B1 (en) | 2016-08-31 |
| CA2869908C (en) | 2018-02-20 |
| US20150252023A1 (en) | 2015-09-10 |
| CA2869908A1 (en) | 2013-10-31 |
| WO2013163270A1 (en) | 2013-10-31 |
| ES2599665T3 (es) | 2017-02-02 |
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