JP5221552B2 - C型肝炎ウイルス阻害剤としての大環状ペプチド - Google Patents
C型肝炎ウイルス阻害剤としての大環状ペプチド Download PDFInfo
- Publication number
- JP5221552B2 JP5221552B2 JP2009537356A JP2009537356A JP5221552B2 JP 5221552 B2 JP5221552 B2 JP 5221552B2 JP 2009537356 A JP2009537356 A JP 2009537356A JP 2009537356 A JP2009537356 A JP 2009537356A JP 5221552 B2 JP5221552 B2 JP 5221552B2
- Authority
- JP
- Japan
- Prior art keywords
- tert
- mmol
- alkyl
- compound
- pharmaceutically acceptable
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- FVVKCIUZDXQPKF-UHFFFAOYSA-N CC(C)(C)NS(C1(C)CC1)(=O)=O Chemical compound CC(C)(C)NS(C1(C)CC1)(=O)=O FVVKCIUZDXQPKF-UHFFFAOYSA-N 0.000 description 1
- SPGDRXRIVPMUCK-UHFFFAOYSA-N CC(C)(C)NS(CCCCl)(=O)=O Chemical compound CC(C)(C)NS(CCCCl)(=O)=O SPGDRXRIVPMUCK-UHFFFAOYSA-N 0.000 description 1
- LKAQNSCCEAPRIA-DRPVAOMPSA-N CC(C)(C)OC(NC(CCN(CCCC=C)S(c1ccccc1[N+]([O-])=O)(=O)=O)C(N(C[C@@](C1)(c2cc(-c3ccccc3)ccc2)OC)[C@@H]1C(O)O)=O)=O Chemical compound CC(C)(C)OC(NC(CCN(CCCC=C)S(c1ccccc1[N+]([O-])=O)(=O)=O)C(N(C[C@@](C1)(c2cc(-c3ccccc3)ccc2)OC)[C@@H]1C(O)O)=O)=O LKAQNSCCEAPRIA-DRPVAOMPSA-N 0.000 description 1
- NBXGDPBFRRQZEV-UHFFFAOYSA-N CC(C)(C)OC(NS(C1CC1)(=O)=O)=O Chemical compound CC(C)(C)OC(NS(C1CC1)(=O)=O)=O NBXGDPBFRRQZEV-UHFFFAOYSA-N 0.000 description 1
- ZITSMHNTPLVPSI-YIDMKWSQSA-N CC(C)(C)OC(N[C@@H](CCCCC/C=C\[C@H](C1)[C@]1(C(O)=O)NC([C@H]1N2CCC1)=O)C2=O)=O Chemical compound CC(C)(C)OC(N[C@@H](CCCCC/C=C\[C@H](C1)[C@]1(C(O)=O)NC([C@H]1N2CCC1)=O)C2=O)=O ZITSMHNTPLVPSI-YIDMKWSQSA-N 0.000 description 1
- KMSVLDATEWKNNN-NSHDSACASA-N CC(C)(C)OC(N[C@@H](COCCCC=C)C(OC)=O)=O Chemical compound CC(C)(C)OC(N[C@@H](COCCCC=C)C(OC)=O)=O KMSVLDATEWKNNN-NSHDSACASA-N 0.000 description 1
- QBTGISUDWWHQPV-UHFFFAOYSA-N CC(C)(C)[O](C)C(N=C)=C Chemical compound CC(C)(C)[O](C)C(N=C)=C QBTGISUDWWHQPV-UHFFFAOYSA-N 0.000 description 1
- UDSUJFMZPGOEQG-VIFPVBQESA-N CC(C)(OC(N[C@](C1)(C(O)=O)C1=C)=O)S Chemical compound CC(C)(OC(N[C@](C1)(C(O)=O)C1=C)=O)S UDSUJFMZPGOEQG-VIFPVBQESA-N 0.000 description 1
- 0 CCCCCCCC(N(CCC1)*1C(CCC)=O)=O Chemical compound CCCCCCCC(N(CCC1)*1C(CCC)=O)=O 0.000 description 1
- RBWRJXSCWCACFO-HIBPNNMFSA-N CCOC([C@@](C1)([C@@H]1/C=C\CCCCC[C@@H](C(N(C1)[C@H]2C[C@]1(c(cc1)ccc1-c1ccccc1)OC)=O)N)NC2=O)=O Chemical compound CCOC([C@@](C1)([C@@H]1/C=C\CCCCC[C@@H](C(N(C1)[C@H]2C[C@]1(c(cc1)ccc1-c1ccccc1)OC)=O)N)NC2=O)=O RBWRJXSCWCACFO-HIBPNNMFSA-N 0.000 description 1
- GUQHLYHTAZNLQX-UHFFFAOYSA-N NS(CC1CCC1)(=O)=O Chemical compound NS(CC1CCC1)(=O)=O GUQHLYHTAZNLQX-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- 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
- C07K5/0812—Tripeptides with the first amino acid being neutral and aromatic or cycloaliphatic
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)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Virology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Gastroenterology & Hepatology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86612506P | 2006-11-16 | 2006-11-16 | |
| US60/866,125 | 2006-11-16 | ||
| US11/939,768 | 2007-11-14 | ||
| US11/939,768 US7763584B2 (en) | 2006-11-16 | 2007-11-14 | Hepatitis C virus inhibitors |
| PCT/US2007/084788 WO2008064061A1 (en) | 2006-11-16 | 2007-11-15 | Macrocyclic peptides as hepatitis c virus inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010510233A JP2010510233A (ja) | 2010-04-02 |
| JP2010510233A5 JP2010510233A5 (enExample) | 2011-01-06 |
| JP5221552B2 true JP5221552B2 (ja) | 2013-06-26 |
Family
ID=39245073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009537356A Expired - Fee Related JP5221552B2 (ja) | 2006-11-16 | 2007-11-15 | C型肝炎ウイルス阻害剤としての大環状ペプチド |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7763584B2 (enExample) |
| EP (1) | EP2086980B1 (enExample) |
| JP (1) | JP5221552B2 (enExample) |
| AT (1) | ATE492558T1 (enExample) |
| DE (1) | DE602007011488D1 (enExample) |
| NO (1) | NO20091845L (enExample) |
| WO (1) | WO2008064061A1 (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY140680A (en) | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
| WO2009099596A2 (en) * | 2008-02-04 | 2009-08-13 | Idenix Pharamaceuticals, Inc. | Macrocyclic serine protease inhibitors |
| US7964560B2 (en) * | 2008-05-29 | 2011-06-21 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8207341B2 (en) | 2008-09-04 | 2012-06-26 | Bristol-Myers Squibb Company | Process or synthesizing substituted isoquinolines |
| UY32099A (es) | 2008-09-11 | 2010-04-30 | Enanta Pharm Inc | Inhibidores macrocíclicos de serina proteasas de hepatitis c |
| US8044087B2 (en) * | 2008-09-29 | 2011-10-25 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| KR20110075019A (ko) * | 2008-10-15 | 2011-07-05 | 인터뮨, 인크. | 치료용 항바이러스성 펩티드 |
| US8283310B2 (en) * | 2008-12-15 | 2012-10-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| TW201040181A (en) | 2009-04-08 | 2010-11-16 | Idenix Pharmaceuticals Inc | Macrocyclic serine protease inhibitors |
| US8232246B2 (en) * | 2009-06-30 | 2012-07-31 | Abbott Laboratories | Anti-viral compounds |
| CA2769652A1 (en) | 2009-08-05 | 2011-02-10 | Idenix Pharmaceuticals, Inc. | Macrocyclic serine protease inhibitors useful against viral infections, particularly hcv |
| US20110082182A1 (en) * | 2009-10-01 | 2011-04-07 | Intermune, Inc. | Therapeutic antiviral peptides |
| JP2013173677A (ja) * | 2010-06-15 | 2013-09-05 | Kaneka Corp | (1r,2s)−1−アミノ−2−ビニルシクロプロパンカルボン酸エステルの製造法 |
| WO2012040242A1 (en) * | 2010-09-22 | 2012-03-29 | Intermune, Inc. | Substituted proline inhibitors of hepatitis c virus replication |
| JP5918264B2 (ja) | 2010-12-22 | 2016-05-18 | アッヴィ・インコーポレイテッド | C型肝炎阻害剤およびその使用 |
| CA2822556A1 (en) | 2010-12-30 | 2012-07-05 | Enanta Pharmaceuticals, Inc | Macrocyclic hepatitis c serine protease inhibitors |
| CN103380132B (zh) | 2010-12-30 | 2016-08-31 | 益安药业 | 菲啶大环丙型肝炎丝氨酸蛋白酶抑制剂 |
| TW201309690A (zh) | 2011-02-10 | 2013-03-01 | Idenix Pharmaceuticals Inc | 巨環絲胺酸蛋白酶抑制劑,其醫藥組合物及其於治療hcv感染之用途 |
| 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 |
| US8691757B2 (en) | 2011-06-15 | 2014-04-08 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| BR112015007887A2 (pt) | 2012-10-08 | 2017-07-04 | Abbvie Inc | compostos úteis para produzir inibidores hcv protease |
| SI2909205T1 (sl) | 2012-10-19 | 2017-02-28 | Bristol-Myers Squibb Company | 9-metil substituiran heksadekahidrociklopropa(e)pirolo(1,2-A)(1,4)diazaciklopentadecinil karbamat derivati kot nestrukturalni 3 (NS3) proteazni inhibitorji za zdravljenje hepatitis C virusnih infekcij |
| EP2914598B1 (en) | 2012-11-02 | 2017-10-18 | 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 |
| US9409943B2 (en) | 2012-11-05 | 2016-08-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| JP6342922B2 (ja) | 2013-03-07 | 2018-06-13 | ブリストル−マイヤーズ スクイブ カンパニーBristol−Myers Squibb Company | C型肝炎ウイルス阻害剤 |
| EP3089757A1 (en) | 2014-01-03 | 2016-11-09 | AbbVie Inc. | Solid antiviral dosage forms |
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| EP0475255A3 (en) | 1990-09-12 | 1993-04-14 | F. Hoffmann-La Roche Ag | Process for the preparation of optically pure (s)-alpha-((tert-butylsulfonyl)methyl)hydro cinnamic acid |
| DE69709671T2 (de) | 1996-10-18 | 2002-08-22 | Vertex Pharmaceuticals Inc., Cambridge | Inhibitoren von serinproteasen, insbesondere von ns3-protease des hepatitis-c-virus |
| JP4452401B2 (ja) | 1997-08-11 | 2010-04-21 | ベーリンガー インゲルハイム (カナダ) リミテッド | C型肝炎ウイルス阻害ペプチドアナログ |
| EP1003775B1 (en) | 1997-08-11 | 2005-03-16 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis c inhibitor peptides |
| AR022061A1 (es) | 1998-08-10 | 2002-09-04 | Boehringer Ingelheim Ca Ltd | Peptidos inhibidores de la hepatitis c, una composicion farmaceutica que los contiene, el uso de los mismos para preparar una composicion farmaceutica, el uso de un producto intermedio para la preparacion de estos peptidos y un procedimiento para la preparacion de un peptido analogo de los mismos. |
| US6323180B1 (en) | 1998-08-10 | 2001-11-27 | Boehringer Ingelheim (Canada) Ltd | Hepatitis C inhibitor tri-peptides |
| UA74546C2 (en) | 1999-04-06 | 2006-01-16 | Boehringer Ingelheim Ca Ltd | Macrocyclic peptides having activity relative to hepatitis c virus, a pharmaceutical composition and use of the pharmaceutical composition |
| US7244721B2 (en) | 2000-07-21 | 2007-07-17 | Schering Corporation | Peptides as NS3-serine protease inhibitors of hepatitis C virus |
| ATE461207T1 (de) | 2000-07-21 | 2010-04-15 | Schering Corp | Peptide als inhibitoren der ns3-serinprotease des hepatitis c virus |
| PE20020707A1 (es) | 2000-11-20 | 2002-08-11 | Bristol Myers Squibb Co | Compuestos tripeptidicos como inhibidores de la proteasa ns3 del virus de hepatitis c |
| US6867185B2 (en) | 2001-12-20 | 2005-03-15 | Bristol-Myers Squibb Company | Inhibitors of hepatitis C virus |
| CA2369711A1 (en) | 2002-01-30 | 2003-07-30 | Boehringer Ingelheim (Canada) Ltd. | Macrocyclic peptides active against the hepatitis c virus |
| CA2370396A1 (en) | 2002-02-01 | 2003-08-01 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis c inhibitor tri-peptides |
| CA2369970A1 (en) | 2002-02-01 | 2003-08-01 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis c inhibitor tri-peptides |
| US6828301B2 (en) | 2002-02-07 | 2004-12-07 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions for hepatitis C viral protease inhibitors |
| PL215228B1 (pl) | 2002-05-20 | 2013-11-29 | Bristol Myers Squibb Co | Zwiazki tripeptydowe, ich zastosowanie i kompozycja farmaceutyczna je zawierajaca oraz jej zastosowanie |
| DE60334205D1 (en) | 2002-05-20 | 2010-10-28 | Bristol Myers Squibb Co | Heterocyclische sulfonamid-hepatitis-c-virus-hemmer |
| MY140680A (en) | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
| US20060199773A1 (en) | 2002-05-20 | 2006-09-07 | Sausker Justin B | Crystalline forms of (1R,2S)-N-[(1,1-dimethylethoxy)carbonyl]-3-methyl-L-valyl-(4R)-4-[(6-methoxy-1-isoquinolinyl)oxy]-L-prolyl-1-amino-N-(cyclopropylsulfonyl)-2-ethenyl-cyclopropanecarboxamide, monopotassium salt |
| DE60324552D1 (en) | 2002-05-20 | 2008-12-18 | Bristol Myers Squibb Co | Substituierte cycloalkyl p1' hepatitis c virus inhibitoren |
| US20040033959A1 (en) | 2002-07-19 | 2004-02-19 | Boehringer Ingelheim Pharmaceuticals, Inc. | Pharmaceutical compositions for hepatitis C viral protease inhibitors |
| US20050075279A1 (en) | 2002-10-25 | 2005-04-07 | Boehringer Ingelheim International Gmbh | Macrocyclic peptides active against the hepatitis C virus |
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| KR20050108420A (ko) | 2003-04-02 | 2005-11-16 | 베링거 인겔하임 인터내셔날 게엠베하 | C형 간염 바이러스 프로테아제 억제제를 위한 약제학적조성물 |
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|---|---|
| US7763584B2 (en) | 2010-07-27 |
| WO2008064061A1 (en) | 2008-05-29 |
| EP2086980B1 (en) | 2010-12-22 |
| DE602007011488D1 (de) | 2011-02-03 |
| JP2010510233A (ja) | 2010-04-02 |
| NO20091845L (no) | 2009-06-15 |
| US20080145334A1 (en) | 2008-06-19 |
| ATE492558T1 (de) | 2011-01-15 |
| EP2086980A1 (en) | 2009-08-12 |
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