EA020235B1 - Ингибиторы протеазы вируса гепатита с - Google Patents
Ингибиторы протеазы вируса гепатита с Download PDFInfo
- Publication number
- EA020235B1 EA020235B1 EA201071315A EA201071315A EA020235B1 EA 020235 B1 EA020235 B1 EA 020235B1 EA 201071315 A EA201071315 A EA 201071315A EA 201071315 A EA201071315 A EA 201071315A EA 020235 B1 EA020235 B1 EA 020235B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- compound
- heteroaryl
- mmol
- aryl
- alkyl
- Prior art date
Links
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 title description 2
- 239000000137 peptide hydrolase inhibitor Substances 0.000 title description 2
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- 125000003118 aryl group Chemical group 0.000 claims abstract description 33
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- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- LHHCSNFAOIFYRV-UHFFFAOYSA-N n-(4-amino-1-cyclobutyl-3,4-dioxobutan-2-yl)-3-[2-(tert-butylcarbamoylamino)-3,3-dimethylbutanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide Chemical compound CC(C)(C)NC(=O)NC(C(C)(C)C)C(=O)N1CC(C2(C)C)C2C1C(=O)NC(C(=O)C(N)=O)CC1CCC1 LHHCSNFAOIFYRV-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229960002429 proline Drugs 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000003753 real-time PCR Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000011986 second-generation catalyst Substances 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 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 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- BBAWEDCPNXPBQM-GDEBMMAJSA-N telaprevir Chemical compound N([C@H](C(=O)N[C@H](C(=O)N1C[C@@H]2CCC[C@@H]2[C@H]1C(=O)N[C@@H](CCC)C(=O)C(=O)NC1CC1)C(C)(C)C)C1CCCCC1)C(=O)C1=CN=CC=N1 BBAWEDCPNXPBQM-GDEBMMAJSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003441 thioacyl group Chemical group 0.000 description 1
- 238000000954 titration curve Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229940051021 yellow-fever virus Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/081—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing O or S as heteroatoms, e.g. Cys, Ser
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Gastroenterology & Hepatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5385708P | 2008-05-16 | 2008-05-16 | |
| PCT/US2008/082329 WO2009139792A1 (en) | 2008-05-16 | 2008-11-04 | Hcv protease inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201071315A1 EA201071315A1 (ru) | 2011-10-31 |
| EA020235B1 true EA020235B1 (ru) | 2014-09-30 |
Family
ID=41316739
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201071315A EA020235B1 (ru) | 2008-05-16 | 2008-11-04 | Ингибиторы протеазы вируса гепатита с |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US20090286814A1 (enExample) |
| EP (1) | EP2274281B1 (enExample) |
| JP (1) | JP5586588B2 (enExample) |
| KR (2) | KR20140048308A (enExample) |
| CN (1) | CN101580535B (enExample) |
| AU (1) | AU2008356226B2 (enExample) |
| CA (1) | CA2722056A1 (enExample) |
| DK (1) | DK2274281T3 (enExample) |
| EA (1) | EA020235B1 (enExample) |
| ES (1) | ES2542880T3 (enExample) |
| NZ (1) | NZ588189A (enExample) |
| TW (1) | TWI414306B (enExample) |
| WO (1) | WO2009139792A1 (enExample) |
| ZA (1) | ZA201008988B (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102046622A (zh) | 2008-04-15 | 2011-05-04 | 因特蒙公司 | 丙型肝炎病毒复制的新颖大环抑制剂 |
| UY32099A (es) | 2008-09-11 | 2010-04-30 | Enanta Pharm Inc | Inhibidores macrocíclicos de serina proteasas de hepatitis c |
| AR075584A1 (es) | 2009-02-27 | 2011-04-20 | Intermune Inc | COMPOSICIONES TERAPEUTICAS QUE COMPRENDEN beta-D-2'-DESOXI-2'-FLUORO-2'-C-METILCITIDINA Y UN DERIVADO DE ACIDO ISOINDOL CARBOXILICO Y SUS USOS. COMPUESTO. |
| US8232246B2 (en) | 2009-06-30 | 2012-07-31 | Abbott Laboratories | Anti-viral compounds |
| US20110178107A1 (en) * | 2010-01-20 | 2011-07-21 | Taigen Biotechnology Co., Ltd. | Hcv protease inhibitors |
| JP2014502620A (ja) | 2010-12-30 | 2014-02-03 | エナンタ ファーマシューティカルズ インコーポレイテッド | 大環状ｃ型肝炎セリンプロテアーゼ阻害剤 |
| WO2012092411A2 (en) | 2010-12-30 | 2012-07-05 | Enanta Pharmaceuticals, Inc. | Phenanthridine macrocyclic hepatitis c serine protease inhibitors |
| US8957203B2 (en) | 2011-05-05 | 2015-02-17 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US10201584B1 (en) | 2011-05-17 | 2019-02-12 | Abbvie Inc. | Compositions and methods for treating HCV |
| CN102911254A (zh) * | 2011-08-02 | 2013-02-06 | 上海唐润医药科技有限公司 | Hcv蛋白酶抑制剂 |
| JP6038179B2 (ja) | 2012-01-11 | 2016-12-07 | アッヴィ・インコーポレイテッド | Ｈｃｖプロテアーゼ阻害剤の製造方法 |
| CN104822682A (zh) | 2012-10-08 | 2015-08-05 | 艾伯维公司 | 用于制备hcv蛋白酶抑制剂的化合物 |
| WO2014062196A1 (en) | 2012-10-19 | 2014-04-24 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| WO2014071007A1 (en) | 2012-11-02 | 2014-05-08 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| EP2914613B1 (en) | 2012-11-02 | 2017-11-22 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| US9643999B2 (en) | 2012-11-02 | 2017-05-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| WO2014070974A1 (en) | 2012-11-05 | 2014-05-08 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| EP2964664B1 (en) | 2013-03-07 | 2017-01-11 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| CN104557954A (zh) * | 2013-10-16 | 2015-04-29 | 上海唐润医药科技有限公司 | 抗hcv的大环化合物 |
| EP3089757A1 (en) | 2014-01-03 | 2016-11-09 | AbbVie Inc. | Solid antiviral dosage forms |
| CN104447952A (zh) * | 2014-12-11 | 2015-03-25 | 上海唐润医药科技有限公司 | 丙肝病毒蛋白酶抑制剂及其合成方法 |
| CN105859748B (zh) * | 2015-02-05 | 2018-06-08 | 爱博新药研发(上海)有限公司 | 多环化合物钠盐及其多晶型、制备方法及应用 |
| CN105884779B (zh) * | 2015-02-13 | 2018-06-12 | 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 |
| CN107074876B (zh) * | 2016-04-08 | 2019-12-20 | 上海长森药业有限公司 | 一类抑制丙肝病毒的大环状杂环化合物及其制备和用途 |
| TW201805289A (zh) * | 2016-08-11 | 2018-02-16 | 廣東東陽光藥業有限公司 | 作為丙型肝炎病毒抑制劑的鹽 |
| CN107722109B (zh) * | 2016-08-11 | 2020-12-18 | 广东东阳光药业有限公司 | 作为丙型肝炎病毒抑制剂的晶型 |
| WO2018222172A1 (en) * | 2017-05-30 | 2018-12-06 | Taigen Biotechnology Co., Ltd. | Solid dispersion formulation |
| US12083099B2 (en) | 2020-10-28 | 2024-09-10 | Accencio LLC | Methods of treating symptoms of coronavirus infection with viral protease inhibitors |
| CN113337624A (zh) * | 2021-05-24 | 2021-09-03 | 温州医科大学 | 同时检测沙眼衣原体、淋病奈瑟氏球菌和解脲支原体的组合物及方法 |
| CN114773302B (zh) * | 2022-04-29 | 2024-04-02 | 中国药科大学 | 一种苯并呋喃衍生物及其医药用途 |
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| RU2197226C2 (ru) * | 1996-12-06 | 2003-01-27 | Фудзисава Фармасьютикал Ко., Лтд. | Лекарственные композиции |
| WO2003053349A2 (en) * | 2001-12-20 | 2003-07-03 | Bristol-Myers Squibb Company | Inhibitors of hepatitis c virus |
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| US5876984A (en) * | 1996-09-25 | 1999-03-02 | Shionogi & Co., Ltd | Sequiterpene derivatives having antiviral activity |
| US6323180B1 (en) * | 1998-08-10 | 2001-11-27 | Boehringer Ingelheim (Canada) Ltd | Hepatitis C inhibitor tri-peptides |
| SV2003000617A (es) * | 2000-08-31 | 2003-01-13 | Lilly Co Eli | Inhibidores de la proteasa peptidomimetica ref. x-14912m |
| DE60217114T2 (de) * | 2001-07-11 | 2007-10-25 | Vertex Pharmaceuticals Inc., Cambridge | Verbrückte bizyklische serinproteaseinhibitoren |
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| US7119072B2 (en) * | 2002-01-30 | 2006-10-10 | Boehringer Ingelheim (Canada) Ltd. | Macrocyclic peptides active against the hepatitis C virus |
| DE60324552D1 (en) * | 2002-05-20 | 2008-12-18 | Bristol Myers Squibb Co | Substituierte cycloalkyl p1' hepatitis c virus inhibitoren |
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-
2008
- 2008-10-28 CN CN2008101743025A patent/CN101580535B/zh active Active
- 2008-11-04 EP EP08874317.4A patent/EP2274281B1/en not_active Not-in-force
- 2008-11-04 KR KR1020147005119A patent/KR20140048308A/ko not_active Withdrawn
- 2008-11-04 DK DK08874317.4T patent/DK2274281T3/en active
- 2008-11-04 EA EA201071315A patent/EA020235B1/ru not_active IP Right Cessation
- 2008-11-04 US US12/264,508 patent/US20090286814A1/en not_active Abandoned
- 2008-11-04 JP JP2011509462A patent/JP5586588B2/ja not_active Expired - Fee Related
- 2008-11-04 WO PCT/US2008/082329 patent/WO2009139792A1/en not_active Ceased
- 2008-11-04 NZ NZ588189A patent/NZ588189A/xx not_active IP Right Cessation
- 2008-11-04 KR KR1020107027553A patent/KR20110011663A/ko not_active Ceased
- 2008-11-04 ES ES08874317.4T patent/ES2542880T3/es active Active
- 2008-11-04 CA CA2722056A patent/CA2722056A1/en not_active Abandoned
- 2008-11-04 AU AU2008356226A patent/AU2008356226B2/en not_active Ceased
- 2008-11-06 TW TW097142922A patent/TWI414306B/zh not_active IP Right Cessation
-
2010
- 2010-12-14 ZA ZA2010/08988A patent/ZA201008988B/en unknown
Patent Citations (5)
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| RU2197226C2 (ru) * | 1996-12-06 | 2003-01-27 | Фудзисава Фармасьютикал Ко., Лтд. | Лекарственные композиции |
| WO2003053349A2 (en) * | 2001-12-20 | 2003-07-03 | Bristol-Myers Squibb Company | Inhibitors of hepatitis c virus |
| WO2004094452A2 (en) * | 2003-04-16 | 2004-11-04 | Bristol-Myers Squibb Company | Macrocyclic isoquinoline peptide inhibitors of hepatitis c virus |
| WO2005028501A1 (en) * | 2003-09-22 | 2005-03-31 | Boehringer Ingelheim International Gmbh | Macrocyclic peptides active against the hepatitis c virus |
| WO2005070955A1 (en) * | 2004-01-21 | 2005-08-04 | Boehringer Ingelheim International Gmbh | Macrocyclic peptides active against the hepatitis c virus |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101580535B (zh) | 2012-10-03 |
| DK2274281T3 (en) | 2015-07-20 |
| NZ588189A (en) | 2012-08-31 |
| KR20140048308A (ko) | 2014-04-23 |
| TWI414306B (zh) | 2013-11-11 |
| EP2274281B1 (en) | 2015-05-27 |
| KR20110011663A (ko) | 2011-02-08 |
| JP2011523411A (ja) | 2011-08-11 |
| ES2542880T3 (es) | 2015-08-12 |
| TW200948375A (en) | 2009-12-01 |
| JP5586588B2 (ja) | 2014-09-10 |
| EP2274281A1 (en) | 2011-01-19 |
| CN101580535A (zh) | 2009-11-18 |
| AU2008356226A1 (en) | 2009-11-19 |
| EA201071315A1 (ru) | 2011-10-31 |
| HK1148739A1 (en) | 2011-09-16 |
| CA2722056A1 (en) | 2009-11-19 |
| US20090286814A1 (en) | 2009-11-19 |
| AU2008356226B2 (en) | 2012-04-12 |
| ZA201008988B (en) | 2012-01-25 |
| WO2009139792A1 (en) | 2009-11-19 |
| EP2274281A4 (en) | 2011-08-17 |
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