DK2274281T3 - HCV protease inhibitors - Google Patents
HCV protease inhibitors Download PDFInfo
- Publication number
- DK2274281T3 DK2274281T3 DK08874317.4T DK08874317T DK2274281T3 DK 2274281 T3 DK2274281 T3 DK 2274281T3 DK 08874317 T DK08874317 T DK 08874317T DK 2274281 T3 DK2274281 T3 DK 2274281T3
- Authority
- DK
- Denmark
- Prior art keywords
- compound
- cycloalkyl
- heteroaryl
- aryl
- alkyl
- Prior art date
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- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 title description 4
- 239000000137 peptide hydrolase inhibitor Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 85
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 18
- -1 nitro, cyano, amino Chemical group 0.000 claims description 14
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 239000003443 antiviral agent Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 230000002519 immonomodulatory effect Effects 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 125000006546 (C4-C10) cycloalkyl group Chemical group 0.000 claims description 2
- 101800001019 Non-structural protein 4B Proteins 0.000 claims description 2
- 101800001014 Non-structural protein 5A Proteins 0.000 claims description 2
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- 208000010710 hepatitis C virus infection Diseases 0.000 claims description 2
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- 125000001475 halogen functional group Chemical group 0.000 claims 4
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- 241000711549 Hepacivirus C Species 0.000 description 30
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- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-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
- 229910052757 nitrogen Inorganic materials 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
- 239000000346 nonvolatile oil Substances 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
- 230000002018 overexpression Effects 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000008188 pellet 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
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 229920000136 polysorbate Polymers 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
- 238000012545 processing Methods 0.000 description 1
- 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 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
- 238000003753 real-time PCR Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 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
- 230000003381 solubilizing effect Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000004434 sulfur atom Chemical group 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
- 230000002459 sustained effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229960002935 telaprevir 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
- 108010017101 telaprevir Proteins 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
- 229940126585 therapeutic drug 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000003612 virological effect Effects 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)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Pharmacology & Pharmacy (AREA)
- Virology (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (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 (1)
| Publication Number | Publication Date |
|---|---|
| DK2274281T3 true DK2274281T3 (en) | 2015-07-20 |
Family
ID=41316739
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK08874317.4T DK2274281T3 (en) | 2008-05-16 | 2008-11-04 | HCV protease inhibitors |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US20090286814A1 (https=) |
| EP (1) | EP2274281B1 (https=) |
| JP (1) | JP5586588B2 (https=) |
| KR (2) | KR20110011663A (https=) |
| CN (1) | CN101580535B (https=) |
| AU (1) | AU2008356226B2 (https=) |
| CA (1) | CA2722056A1 (https=) |
| DK (1) | DK2274281T3 (https=) |
| EA (1) | EA020235B1 (https=) |
| ES (1) | ES2542880T3 (https=) |
| NZ (1) | NZ588189A (https=) |
| TW (1) | TWI414306B (https=) |
| WO (1) | WO2009139792A1 (https=) |
| ZA (1) | ZA201008988B (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009142842A2 (en) | 2008-04-15 | 2009-11-26 | Intermune, Inc. | Novel macrocyclic inhibitors of hepatitis c virus replication |
| 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 |
| KR20140003521A (ko) | 2010-12-30 | 2014-01-09 | 이난타 파마슈티칼스, 인코포레이티드 | 페난트리딘 매크로사이클릭 ｃ형 간염 세린 프로테아제 억제제 |
| EP2658859A4 (en) | 2010-12-30 | 2014-07-30 | Enanta Pharm Inc | MACROCYCLIC HEPATITIS C SERIN 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 |
| CA2863002A1 (en) | 2012-01-11 | 2013-07-18 | Abbvie Inc. | Processes for making hcv protease inhibitors |
| EP2903988A1 (en) | 2012-10-08 | 2015-08-12 | AbbVie Inc. | Compounds useful for making hcv protease inhibitors |
| EA025560B1 (ru) | 2012-10-19 | 2017-01-30 | Бристол-Майерс Сквибб Компани | Ингибиторы вируса гепатита с |
| WO2014071007A1 (en) | 2012-11-02 | 2014-05-08 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| US9643999B2 (en) | 2012-11-02 | 2017-05-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| WO2014070964A1 (en) | 2012-11-02 | 2014-05-08 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| EP2914614B1 (en) | 2012-11-05 | 2017-08-16 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| WO2014137869A1 (en) | 2013-03-07 | 2014-09-12 | 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 |
| WO2016127859A1 (en) * | 2015-02-13 | 2016-08-18 | Sunshine Lake Pharma Co., Ltd. | Compounds as hepatitis c inhibitors and uses thereof in medicine |
| 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 |
| 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 |
| 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 |
| 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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| Publication number | Priority date | Publication date | Assignee | Title |
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| US4555508A (en) * | 1984-03-02 | 1985-11-26 | Usv Pharmaceutical Corp. | Antihypertensive spiro-cyclic compounds |
| US5876984A (en) * | 1996-09-25 | 1999-03-02 | Shionogi & Co., Ltd | Sequiterpene derivatives having antiviral activity |
| ZA9710927B (en) * | 1996-12-06 | 1998-06-15 | Fujisawa Pharmaceutical Co | Pharmaceutical composition. |
| 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 |
| IL159087A0 (en) * | 2001-07-11 | 2004-05-12 | Vertex Pharma | Bridged bicyclic compounds and pharmaceutical compositions containing the same |
| US6867185B2 (en) * | 2001-12-20 | 2005-03-15 | Bristol-Myers Squibb Company | Inhibitors of hepatitis C virus |
| CN100352819C (zh) * | 2002-01-23 | 2007-12-05 | 先灵公司 | 作为ns3－丝氨酸蛋白酶抑制剂的脯氨酸化合物用于制备治疗丙型肝炎病毒感染的药物 |
| 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 |
| MY140680A (en) * | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
| ES2320771T3 (es) * | 2003-04-16 | 2009-05-28 | Bristol-Myers Squibb Company | Inhibidores peptidicos de isoquinolina macrociclicos del virus de la hepatitis c. |
| US7176208B2 (en) * | 2003-04-18 | 2007-02-13 | Enanta Pharmaceuticals, Inc. | Quinoxalinyl macrocyclic hepatitis C serine protease inhibitors |
| RS20060197A (sr) * | 2003-09-22 | 2008-09-29 | Boehringer Ingelheim International Gmbh., | Makrociklični peptidi koji su aktivni protiv hepatitisa c virusa |
| JP4525982B2 (ja) * | 2003-09-26 | 2010-08-18 | シェーリング コーポレイション | Ｃ型肝炎ウイルスのｎｓ３セリンプロテアーゼの大環状インヒビター |
| US7491794B2 (en) * | 2003-10-14 | 2009-02-17 | Intermune, Inc. | Macrocyclic compounds as inhibitors of viral replication |
| JP2007532479A (ja) * | 2003-11-20 | 2007-11-15 | シェーリング コーポレイション | Ｃ型肝炎ウイルスｎｓ３プロテアーゼの脱ペプチド化インヒビター |
| BRPI0416902A (pt) * | 2003-12-11 | 2007-01-16 | Schering Corp | inibidores de ns3/ns4a serina protease do vìrus da hepatite c |
| EP1730167B1 (en) * | 2004-01-21 | 2011-01-12 | Boehringer Ingelheim International GmbH | Macrocyclic peptides active against the hepatitis c virus |
| US7375218B2 (en) * | 2004-09-17 | 2008-05-20 | Boehringer Ingelheim International Gmbh | Process for preparing macrocyclic HCV protease inhibitors |
| US20070207949A1 (en) * | 2005-06-02 | 2007-09-06 | Anima Ghosal | Medicaments and methods combining a HCV protease inhibitor and an AKR competitor |
| US20070237818A1 (en) * | 2005-06-02 | 2007-10-11 | Malcolm Bruce A | Controlled-release formulation of HCV protease inhibitor and methods using the same |
| US8012939B2 (en) * | 2005-07-29 | 2011-09-06 | Tibotec Pharmaceuticals Ltd. Co | Macrocyclic inhibitors of hepatitis C virus |
| US7605126B2 (en) * | 2006-08-11 | 2009-10-20 | Enanta Pharmaceuticals, Inc. | Acylaminoheteroaryl hepatitis C virus protease inhibitors |
| WO2008022006A2 (en) * | 2006-08-11 | 2008-02-21 | Enanta Pharmaceuticals, Inc. | Arylalkoxyl hepatitis c virus protease inhibitors |
| US20080267917A1 (en) * | 2007-04-26 | 2008-10-30 | Deqiang Niu | N-functionalized amides as hepatitis c serine protease inhibitors |
| US20090005387A1 (en) * | 2007-06-26 | 2009-01-01 | Deqiang Niu | Quinoxalinyl macrocyclic hepatitis c virus serine protease inhibitors |
| US20090111757A1 (en) * | 2007-10-25 | 2009-04-30 | Taigen Biotechnology Co., Ltd. | Hcv protease inhibitors |
-
2008
- 2008-10-28 CN CN2008101743025A patent/CN101580535B/zh active Active
- 2008-11-04 NZ NZ588189A patent/NZ588189A/xx not_active IP Right Cessation
- 2008-11-04 EA EA201071315A patent/EA020235B1/ru not_active IP Right Cessation
- 2008-11-04 EP EP08874317.4A patent/EP2274281B1/en not_active Not-in-force
- 2008-11-04 ES ES08874317.4T patent/ES2542880T3/es active Active
- 2008-11-04 AU AU2008356226A patent/AU2008356226B2/en not_active Ceased
- 2008-11-04 KR KR1020107027553A patent/KR20110011663A/ko not_active Ceased
- 2008-11-04 WO PCT/US2008/082329 patent/WO2009139792A1/en not_active Ceased
- 2008-11-04 DK DK08874317.4T patent/DK2274281T3/en active
- 2008-11-04 JP JP2011509462A patent/JP5586588B2/ja not_active Expired - Fee Related
- 2008-11-04 KR KR1020147005119A patent/KR20140048308A/ko not_active Withdrawn
- 2008-11-04 US US12/264,508 patent/US20090286814A1/en not_active Abandoned
- 2008-11-04 CA CA2722056A patent/CA2722056A1/en not_active Abandoned
- 2008-11-06 TW TW097142922A patent/TWI414306B/zh not_active IP Right Cessation
-
2010
- 2010-12-14 ZA ZA2010/08988A patent/ZA201008988B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA201008988B (en) | 2012-01-25 |
| EP2274281B1 (en) | 2015-05-27 |
| CA2722056A1 (en) | 2009-11-19 |
| EA201071315A1 (ru) | 2011-10-31 |
| US20090286814A1 (en) | 2009-11-19 |
| CN101580535B (zh) | 2012-10-03 |
| EA020235B1 (ru) | 2014-09-30 |
| WO2009139792A1 (en) | 2009-11-19 |
| TWI414306B (zh) | 2013-11-11 |
| AU2008356226B2 (en) | 2012-04-12 |
| CN101580535A (zh) | 2009-11-18 |
| JP2011523411A (ja) | 2011-08-11 |
| ES2542880T3 (es) | 2015-08-12 |
| HK1148739A1 (en) | 2011-09-16 |
| EP2274281A4 (en) | 2011-08-17 |
| TW200948375A (en) | 2009-12-01 |
| KR20110011663A (ko) | 2011-02-08 |
| JP5586588B2 (ja) | 2014-09-10 |
| NZ588189A (en) | 2012-08-31 |
| KR20140048308A (ko) | 2014-04-23 |
| AU2008356226A1 (en) | 2009-11-19 |
| EP2274281A1 (en) | 2011-01-19 |
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