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WO2001002424A3 - Peptide boronic acid inhibitors of hepatitis c virus protease - Google Patents

Peptide boronic acid inhibitors of hepatitis c virus protease Download PDF

Info

Publication number
WO2001002424A3
WO2001002424A3 PCT/US2000/018655 US0018655W WO0102424A3 WO 2001002424 A3 WO2001002424 A3 WO 2001002424A3 US 0018655 W US0018655 W US 0018655W WO 0102424 A3 WO0102424 A3 WO 0102424A3
Authority
WO
WIPO (PCT)
Prior art keywords
hepatitis
boronic acid
acid inhibitors
virus protease
peptide boronic
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.)
Ceased
Application number
PCT/US2000/018655
Other languages
French (fr)
Other versions
WO2001002424A2 (en
Inventor
Charles A Kettner
Sharada Jagannathan
Timothy Patrick Forsyth
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.)
Bristol Myers Squibb Pharma Co
Original Assignee
DuPont Merck Pharmaceutical Co
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 DuPont Merck Pharmaceutical Co filed Critical DuPont Merck Pharmaceutical Co
Priority to EP00943413A priority Critical patent/EP1196436A2/en
Priority to CA002376965A priority patent/CA2376965A1/en
Priority to AU57888/00A priority patent/AU5788800A/en
Publication of WO2001002424A2 publication Critical patent/WO2001002424A2/en
Publication of WO2001002424A3 publication Critical patent/WO2001002424A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/005—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from viruses
    • 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
    • A61K31/69—Boron compounds
    • 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
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • 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
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds
    • 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
    • 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
    • C07K5/0827—Tripeptides containing heteroatoms different from O, S, or N
    • 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
    • C07K5/10—Tetrapeptides
    • C07K5/1027—Tetrapeptides containing heteroatoms different from O, S, or N
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/14—Hydrolases (3)
    • C12N9/48—Hydrolases (3) acting on peptide bonds (3.4)
    • C12N9/50—Proteinases, e.g. Endopeptidases (3.4.21-3.4.25)
    • C12N9/503—Proteinases, e.g. Endopeptidases (3.4.21-3.4.25) derived from viruses
    • C12N9/506—Proteinases, e.g. Endopeptidases (3.4.21-3.4.25) derived from viruses derived from RNA viruses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N2770/00—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA ssRNA viruses positive-sense
    • C12N2770/00011—Details
    • C12N2770/24011—Flaviviridae
    • C12N2770/24211—Hepacivirus, e.g. hepatitis C virus, hepatitis G virus
    • C12N2770/24222—New viral proteins or individual genes, new structural or functional aspects of known viral proteins or genes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Virology (AREA)
  • Biochemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biophysics (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Zoology (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Epidemiology (AREA)
  • General Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Communicable Diseases (AREA)
  • Biomedical Technology (AREA)
  • Oncology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)

Abstract

The present invention relates generally to novel α-aminoboronic acids and corresponding peptide analogs represented by structural Formula (I) or pharmaceutically acceptable salt forms thereof, wherein R?1, R2, R3, Y1, Y2¿, and A are described herein. The invention is also concerned with pharmaceutical formulations comprising these novel compounds as active ingredients and the use of the novel compounds and their formulations in the treatment of hepatitis C viral infections. The compounds of the invention are inhibitors of hepatitis C viral protease.
PCT/US2000/018655 1999-07-07 2000-07-07 Peptide boronic acid inhibitors of hepatitis c virus protease Ceased WO2001002424A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP00943413A EP1196436A2 (en) 1999-07-07 2000-07-07 Peptide boronic acid inhibitors of hepatitis c virus protease
CA002376965A CA2376965A1 (en) 1999-07-07 2000-07-07 Peptide boronic acid inhibitors of hepatitis c virus protease
AU57888/00A AU5788800A (en) 1999-07-07 2000-07-07 Peptide boronic acid inhibitors of hepatitis c virus protease

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US14256199P 1999-07-07 1999-07-07
US60/142,561 1999-07-07

Publications (2)

Publication Number Publication Date
WO2001002424A2 WO2001002424A2 (en) 2001-01-11
WO2001002424A3 true WO2001002424A3 (en) 2001-07-19

Family

ID=22500325

Family Applications (2)

Application Number Title Priority Date Filing Date
PCT/US2000/018655 Ceased WO2001002424A2 (en) 1999-07-07 2000-07-07 Peptide boronic acid inhibitors of hepatitis c virus protease
PCT/US2000/018590 Ceased WO2001002601A2 (en) 1999-07-07 2000-07-07 Cell-based assay systems for examining hcv ns3 protease activity

Family Applications After (1)

Application Number Title Priority Date Filing Date
PCT/US2000/018590 Ceased WO2001002601A2 (en) 1999-07-07 2000-07-07 Cell-based assay systems for examining hcv ns3 protease activity

Country Status (4)

Country Link
EP (1) EP1196436A2 (en)
AU (2) AU5788800A (en)
CA (1) CA2376965A1 (en)
WO (2) WO2001002424A2 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7378422B2 (en) 2003-09-05 2008-05-27 Vertex Pharmaceuticals Incorporated Inhibitors of serine proteases, particularly HCV NS3-NS4A protease
US11814367B2 (en) 2021-03-15 2023-11-14 Maze Therapeutics, Inc. Inhibitors of glycogen synthase 1 (GYS1) and methods of use thereof

Families Citing this family (49)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6653295B2 (en) 2000-12-13 2003-11-25 Bristol-Myers Squibb Company Inhibitors of hepatitis C virus NS3 protease
WO2002048116A2 (en) * 2000-12-13 2002-06-20 Bristol-Myers Squibb Pharma Company Inhibitors of hepatitis c virus ns3 protease
US6586615B1 (en) 2001-01-10 2003-07-01 Bristol-Myers Squibb Company α-aminoboronic acids prepared by novel synthetic methods
EP3078667B1 (en) 2001-01-25 2018-11-21 The United States of America, represented by the Secretary, Department of Health and Human Services Formulation of boronic acid compounds
US7119072B2 (en) 2002-01-30 2006-10-10 Boehringer Ingelheim (Canada) Ltd. Macrocyclic peptides active against the hepatitis C virus
US7091184B2 (en) 2002-02-01 2006-08-15 Boehringer Ingelheim International Gmbh Hepatitis C inhibitor tri-peptides
US6642204B2 (en) 2002-02-01 2003-11-04 Boehringer Ingelheim International Gmbh Hepatitis C inhibitor tri-peptides
US7112572B2 (en) 2002-09-09 2006-09-26 Trigen Limited Multivalent metal salts of boronic acids
AU2003263328A1 (en) 2002-09-09 2004-03-29 Trigen Limited Boronic acid salts useful in parenteral formulations for selective thrombin inhibition
US20050075279A1 (en) 2002-10-25 2005-04-07 Boehringer Ingelheim International Gmbh Macrocyclic peptides active against the hepatitis C virus
AU2011203054B2 (en) * 2003-04-11 2012-04-26 Vertex Pharmaceuticals, Incorporated Inhibitors of Serine Proteases, Particularly HCV NS3-NS4A Protease
US20050090450A1 (en) * 2003-04-11 2005-04-28 Farmer Luc J. Inhibitors of serine proteases, particularly HCV NS3-NS4A protease
PE20050204A1 (en) 2003-05-21 2005-05-04 Boehringer Ingelheim Int INHIBITING COMPOUNDS OF HEPATITIS C
US7405210B2 (en) 2003-05-21 2008-07-29 Osi Pharmaceuticals, Inc. Pyrrolopyridine-2-carboxylic acid amide inhibitors of glycogen phosphorylase
US20050136394A1 (en) * 2003-06-23 2005-06-23 Hong Fang Cell-based assay for identifying peptidase inhibitors
US7576206B2 (en) 2003-08-14 2009-08-18 Cephalon, Inc. Proteasome inhibitors and methods of using the same
US7223745B2 (en) 2003-08-14 2007-05-29 Cephalon, Inc. Proteasome inhibitors and methods of using the same
MXPA06003141A (en) 2003-09-22 2006-06-05 Boehringer Ingelheim Int Macrocyclic peptides active against the hepatitis c virus.
CA2549851C (en) 2004-01-21 2012-09-11 Boehringer Ingelheim International Gmbh Macrocyclic peptides active against the hepatitis c virus
DE602005023965D1 (en) 2004-03-08 2010-11-18 Prosidion Ltd PYRROLOPYRIDINE-2-CARBOXYLIC HYDRAZIDE AS INHIBITORS OF GLYCOPE PHOSPHORYLASE
WO2006085932A2 (en) * 2004-06-14 2006-08-17 Anacor Pharmaceuticals, Inc. Anti-viral uses of borinic acid complexes
UY29016A1 (en) 2004-07-20 2006-02-24 Boehringer Ingelheim Int ANALOGS OF INHIBITING DIPEPTIDES OF HEPATITIS C
JP4914355B2 (en) 2004-07-20 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 Hepatitis C inhibitor peptide analog
JP2008521873A (en) 2004-12-02 2008-06-26 プロシディオン・リミテッド Pyrrolopyridine-2-carboxylic acid amides
US7468383B2 (en) 2005-02-11 2008-12-23 Cephalon, Inc. Proteasome inhibitors and methods of using the same
CA2603589A1 (en) * 2005-04-01 2006-10-05 Methylgene Inc. Inhibitors of histone deacetylase
EP1915382A2 (en) * 2005-08-01 2008-04-30 Phenomix Corporation Hepatitis c serine protease inhibitors and uses therefor
RU2419626C2 (en) 2006-05-23 2011-05-27 Айрм Ллк Compounds and compositions as canal activating protease inhibitors
EP1886685A1 (en) 2006-08-11 2008-02-13 INSERM (Institut National de la Santé et de la Recherche Médicale) Methods, uses and compositions for modulating replication of hcv through the farnesoid x receptor (fxr) activation or inhibition
US20100120716A1 (en) * 2006-12-06 2010-05-13 Phenomix Corporation Macrocyclic hepatitis c serine protease inhibitors and uses therefor
CA2677487A1 (en) 2007-02-09 2008-08-14 Irm Llc Compounds and compositions as channel activating protease inhibitors
US7442830B1 (en) 2007-08-06 2008-10-28 Millenium Pharmaceuticals, Inc. Proteasome inhibitors
US7838673B2 (en) 2007-10-16 2010-11-23 Millennium Pharmaceuticals, Inc. Proteasome inhibitors
CN102066386A (en) 2008-06-17 2011-05-18 米伦纽姆医药公司 Borate compound and its pharmaceutical composition
AR075090A1 (en) 2008-09-29 2011-03-09 Millennium Pharm Inc ACID DERIVATIVES 1-AMINO-2-CYCLLOBUTILETILBORONICO PROTEOSOMA INHIBITORS, USEFUL AS ANTI-BANKER AGENTS, AND PHARMACEUTICAL COMPOSITIONS THAT UNDERSTAND THEM.
WO2011087822A1 (en) 2009-12-22 2011-07-21 Cephalon, Inc. Proteasome inhibitors and processes for their preparation, purification and use
WO2011103063A1 (en) * 2010-02-19 2011-08-25 Glaxo Group Limited Therapeutic compounds
PH12012501943A1 (en) 2010-03-31 2017-08-23 Millennium Pharm Inc Derivatives of 1-amino-2-cyclopropylethylboronic acid
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WO2012107589A1 (en) 2011-02-11 2012-08-16 INSERM (Institut National de la Santé et de la Recherche Médicale) Methods and pharmaceutical compositions for the treatment and prevention of hcv infections
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MX354676B (en) 2011-08-19 2018-03-15 Glaxo Group Ltd Benzofuran compounds for the treatment of hepatitis c virus infections.
US10092574B2 (en) 2012-09-26 2018-10-09 Valorisation-Recherche, Limited Partnership Inhibitors of polynucleotide repeat-associated RNA foci and uses thereof
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CN109476637B (en) 2016-06-21 2022-02-01 奥瑞恩眼科有限责任公司 Heterocyclic prolinamide derivatives
JP7164521B2 (en) 2016-06-21 2022-11-01 オリオン・オフサルモロジー・エルエルシー carbocyclic prolinamide derivatives

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WO1999007733A2 (en) * 1997-08-11 1999-02-18 Boehringer Ingelheim (Canada) Ltd. Hepatitis c inhibitor peptides

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US6280940B1 (en) * 1998-08-05 2001-08-28 Agouron Pharmaceuticals, Inc. Reporter gene system for use in cell-based assessment of inhibitors of the Hepatitis C virus protease
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WO1998017679A1 (en) * 1996-10-18 1998-04-30 Vertex Pharmaceuticals Incorporated Inhibitors of serine proteases, particularly hepatitis c virus ns3 protease
WO1998022496A2 (en) * 1996-11-18 1998-05-28 F. Hoffmann-La Roche Ag Antiviral peptide derivatives
WO1999007733A2 (en) * 1997-08-11 1999-02-18 Boehringer Ingelheim (Canada) Ltd. Hepatitis c inhibitor peptides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7378422B2 (en) 2003-09-05 2008-05-27 Vertex Pharmaceuticals Incorporated Inhibitors of serine proteases, particularly HCV NS3-NS4A protease
US11814367B2 (en) 2021-03-15 2023-11-14 Maze Therapeutics, Inc. Inhibitors of glycogen synthase 1 (GYS1) and methods of use thereof

Also Published As

Publication number Publication date
WO2001002424A2 (en) 2001-01-11
AU5920400A (en) 2001-01-22
CA2376965A1 (en) 2001-01-11
WO2001002601A3 (en) 2001-07-26
AU5788800A (en) 2001-01-22
WO2001002601A2 (en) 2001-01-11
EP1196436A2 (en) 2002-04-17

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