CA2615921C - Hepatitis c inhibitor peptide analogs with a quinoline or a thienopyridine moiety - Google Patents

Hepatitis c inhibitor peptide analogs with a quinoline or a thienopyridine moiety Download PDF

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Publication number
CA2615921C
CA2615921C CA2615921A CA2615921A CA2615921C CA 2615921 C CA2615921 C CA 2615921C CA 2615921 A CA2615921 A CA 2615921A CA 2615921 A CA2615921 A CA 2615921A CA 2615921 C CA2615921 C CA 2615921C
Authority
CA
Canada
Prior art keywords
compound according
alkyl
formula
hepatitis
compound
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
Application number
CA2615921A
Other languages
English (en)
French (fr)
Other versions
CA2615921A1 (en
Inventor
Murray D. Bailey
Pasquale Forgione
Montse Llinas-Brunet
Marc Andre Poupart
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Boehringer Ingelheim International GmbH
Original Assignee
Boehringer Ingelheim International GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Boehringer Ingelheim International GmbH filed Critical Boehringer Ingelheim International GmbH
Publication of CA2615921A1 publication Critical patent/CA2615921A1/en
Application granted granted Critical
Publication of CA2615921C publication Critical patent/CA2615921C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

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
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
    • 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
    • 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
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
    • 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
    • C07K5/06—Dipeptides
    • C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N

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)
  • Virology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
CA2615921A 2005-07-20 2006-07-17 Hepatitis c inhibitor peptide analogs with a quinoline or a thienopyridine moiety Expired - Fee Related CA2615921C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US70095005P 2005-07-20 2005-07-20
US60/700,950 2005-07-20
PCT/CA2006/001160 WO2007009227A1 (en) 2005-07-20 2006-07-17 Hepatitis c inhibitor peptide analogs

Publications (2)

Publication Number Publication Date
CA2615921A1 CA2615921A1 (en) 2007-01-25
CA2615921C true CA2615921C (en) 2011-09-13

Family

ID=37668388

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2615921A Expired - Fee Related CA2615921C (en) 2005-07-20 2006-07-17 Hepatitis c inhibitor peptide analogs with a quinoline or a thienopyridine moiety

Country Status (5)

Country Link
US (1) US20080200497A1 (US07652168-20100126-C00055.png)
EP (1) EP1910378B1 (US07652168-20100126-C00055.png)
JP (1) JP2009501732A (US07652168-20100126-C00055.png)
CA (1) CA2615921C (US07652168-20100126-C00055.png)
WO (1) WO2007009227A1 (US07652168-20100126-C00055.png)

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MY140680A (en) 2002-05-20 2010-01-15 Bristol Myers Squibb Co Hepatitis c virus inhibitors
US7741281B2 (en) 2005-11-03 2010-06-22 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
US7935670B2 (en) 2006-07-11 2011-05-03 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
KR101512477B1 (ko) 2006-07-13 2015-04-15 아칠리온 파르마세우티칼스 인코포레이티드 바이러스 복제 억제제로서 사용되는 4-아미노-4-옥소부타노일 펩티드
US8343477B2 (en) 2006-11-01 2013-01-01 Bristol-Myers Squibb Company Inhibitors of hepatitis C virus
US7772180B2 (en) 2006-11-09 2010-08-10 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
US7763584B2 (en) 2006-11-16 2010-07-27 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
US7888464B2 (en) 2006-11-16 2011-02-15 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
US8003604B2 (en) 2006-11-16 2011-08-23 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
CA2679377A1 (en) 2007-02-26 2008-09-04 Achillion Pharmaceuticals, Inc. Tertiary amine substituted peptides useful as inhibitors of hcv replication
WO2009005690A2 (en) * 2007-06-29 2009-01-08 Gilead Sciences, Inc. Antiviral compounds
JP2010540549A (ja) 2007-09-24 2010-12-24 アキリオン ファーマシューティカルズ，インコーポレーテッド ウイルス複製阻害剤としての尿素含有ペプチド
US8383583B2 (en) 2007-10-26 2013-02-26 Enanta Pharmaceuticals, Inc. Macrocyclic, pyridazinone-containing hepatitis C serine protease inhibitors
CN101903351B (zh) 2007-12-19 2014-09-10 贝林格尔.英格海姆国际有限公司 病毒聚合酶抑制剂
RU2515318C2 (ru) 2007-12-21 2014-05-10 Авила Терапьютикс, Инк. Ингибиторы протеазы вируса гепатита с и их применение
US8202996B2 (en) 2007-12-21 2012-06-19 Bristol-Myers Squibb Company Crystalline forms of N-(tert-butoxycarbonyl)-3-methyl-L-valyl-(4R)-4-((7-chloro-4-methoxy-1-isoquinolinyl)oxy)-N- ((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)-L-prolinamide
US8309685B2 (en) 2007-12-21 2012-11-13 Celgene Avilomics Research, Inc. HCV protease inhibitors and uses thereof
US8293705B2 (en) 2007-12-21 2012-10-23 Avila Therapeutics, Inc. HCV protease inhibitors and uses thereof
RU2523790C2 (ru) 2007-12-21 2014-07-27 Авила Терапьютикс, Инк. Ингибиторы протеазы вируса гепатита с и их применение
EP2250174B1 (en) 2008-02-04 2013-08-28 IDENIX Pharmaceuticals, Inc. Macrocyclic serine protease inhibitors
JP5490778B2 (ja) 2008-03-20 2014-05-14 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 Ｃ型肝炎ウイルス阻害剤としてのフッ素化大環状化合物
US8163921B2 (en) 2008-04-16 2012-04-24 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
US7964560B2 (en) 2008-05-29 2011-06-21 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
EP2300491B1 (en) 2008-05-29 2016-01-06 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
US8563505B2 (en) 2008-09-29 2013-10-22 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
US8044087B2 (en) 2008-09-29 2011-10-25 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
PL2364309T3 (pl) 2008-12-10 2015-03-31 Achillion Pharmaceuticals Inc Nowe peptydy 4-amino-4-oksobutanoilowe jako inhibitory wirusowej replikacji
US8283310B2 (en) 2008-12-15 2012-10-09 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
RU2011127080A (ru) 2009-01-07 2013-02-20 Сайнексис, Инк. Производное циклоспорина для применения в лечении заражения вирусом гепатита с и вич
WO2010118078A1 (en) 2009-04-08 2010-10-14 Idenix Pharmaceuticals, Inc. Macrocyclic serine protease inhibitors
TW201117812A (en) 2009-08-05 2011-06-01 Idenix Pharmaceuticals Inc Macrocyclic serine protease inhibitors
EP2658859A4 (en) 2010-12-30 2014-07-30 Enanta Pharm Inc MACROCYCLIC HEPATITIS C SERIN PROTEASE INHIBITORS
KR20140003521A (ko) 2010-12-30 2014-01-09 이난타 파마슈티칼스, 인코포레이티드 페난트리딘 매크로사이클릭 ｃ형 간염 세린 프로테아제 억제제
AR085352A1 (es) 2011-02-10 2013-09-25 Idenix Pharmaceuticals Inc Inhibidores macrociclicos de serina proteasa, sus composiciones farmaceuticas y su uso para tratar infecciones por hcv
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
AU2012392557B2 (en) 2012-10-19 2017-06-01 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
US9334279B2 (en) 2012-11-02 2016-05-10 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
WO2014070974A1 (en) 2012-11-05 2014-05-08 Bristol-Myers Squibb Company Hepatitis c virus inhibitors
CN105164148A (zh) 2013-03-07 2015-12-16 百时美施贵宝公司 丙型肝炎病毒抑制剂
EP2970195B1 (en) 2013-03-14 2017-08-02 Achillion Pharmaceuticals, Inc. Processes for producing sovaprevir
WO2014145507A1 (en) 2013-03-15 2014-09-18 Achillion Pharmaceuticals, Inc. A process for making a 4-amino-4-oxobutanoyl peptide cyclic analogue, an inhibitor of viral replication, and intermediates thereof
US9085607B2 (en) 2013-03-15 2015-07-21 Achillion Pharmaceuticals, Inc. ACH-0142684 sodium salt polymorph, composition including the same, and method of manufacture thereof
BR112015023351A2 (pt) 2013-03-15 2017-07-18 Achillion Pharmaceuticals Inc forma cristalina de sovaprevir, composição farmacêutica, e, método para tratar um distúrbio
WO2015103490A1 (en) 2014-01-03 2015-07-09 Abbvie, Inc. Solid antiviral dosage forms

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4883914A (en) * 1987-08-17 1989-11-28 American Cyanamid Company Benzenesulfonyl carboxamide compounds useful as herbicidal agents
EP0303863A3 (en) * 1987-08-17 1991-10-23 American Cyanamid Company Benzenesulfonyl carboxamide compounds, intermediate compounds and methods of preparation thereof and use of said compounds and intermediate compounds as herbicidal agents
US6323180B1 (en) * 1998-08-10 2001-11-27 Boehringer Ingelheim (Canada) Ltd Hepatitis C inhibitor tri-peptides
JP3889708B2 (ja) * 2000-11-20 2007-03-07 ブリストル−マイヤーズ スクイブ カンパニー Ｃ型肝炎トリペプチド阻害剤
CA2474156C (en) * 2002-02-01 2011-09-20 Boehringer Ingelheim International Gmbh Tripeptides having a hydroxyproline ether of a substituted quinoline for the inhibition of ns3 (hepatitis c)
US6642204B2 (en) * 2002-02-01 2003-11-04 Boehringer Ingelheim International Gmbh Hepatitis C inhibitor tri-peptides
JP4271148B2 (ja) * 2002-05-20 2009-06-03 ブリストル−マイヤーズ スクイブ カンパニー 置換シクロアルキルｐ１’ｃ型肝炎ウイルスインヒビター
MY140680A (en) * 2002-05-20 2010-01-15 Bristol Myers Squibb Co Hepatitis c virus inhibitors
DE60334205D1 (en) * 2002-05-20 2010-10-28 Bristol Myers Squibb Co Heterocyclische sulfonamid-hepatitis-c-virus-hemmer
US20050075279A1 (en) * 2002-10-25 2005-04-07 Boehringer Ingelheim International Gmbh Macrocyclic peptides active against the hepatitis C virus
US7132504B2 (en) * 2003-11-12 2006-11-07 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
JP4914348B2 (ja) * 2004-06-28 2012-04-11 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Ｃ型肝炎インヒビターペプチド類似体

Also Published As

Publication number Publication date
WO2007009227A1 (en) 2007-01-25
EP1910378A4 (en) 2009-04-29
CA2615921A1 (en) 2007-01-25
EP1910378A1 (en) 2008-04-16
EP1910378B1 (en) 2012-06-20
US20080200497A1 (en) 2008-08-21
JP2009501732A (ja) 2009-01-22

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Effective date: 20140717