CA2557304C - Ketoamides with cyclic p4's as inhibitors of ns3 serine protease of hepatitis c virus - Google Patents

Ketoamides with cyclic p4's as inhibitors of ns3 serine protease of hepatitis c virus Download PDF

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Publication number
CA2557304C
CA2557304C CA2557304A CA2557304A CA2557304C CA 2557304 C CA2557304 C CA 2557304C CA 2557304 A CA2557304 A CA 2557304A CA 2557304 A CA2557304 A CA 2557304A CA 2557304 C CA2557304 C CA 2557304C
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CA
Canada
Prior art keywords
compound
group
mmol
alkyl
solution
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
CA2557304A
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English (en)
French (fr)
Other versions
CA2557304A1 (en
Inventor
Kevin X. Chen
F. George Njoroge
Mousumi Sannigrahi
Latha G. Nair
Weiying Yang
Bancha Vibulbhan
Srikanth Venkatraman
Ashok Arasappan
Stephane L. Bogen
Frank Bennett
Viyyoor M. Girijavallabhan
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.)
Merck Sharp and Dohme LLC
Original Assignee
Merck Sharp and Dohme LLC
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Application filed by Merck Sharp and Dohme LLC filed Critical Merck Sharp and Dohme LLC
Publication of CA2557304A1 publication Critical patent/CA2557304A1/en
Application granted granted Critical
Publication of CA2557304C publication Critical patent/CA2557304C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/0202—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-X-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • 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
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/0205—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-(X)3-C(=0)-, e.g. statine or derivatives thereof
    • 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
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/70—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving virus or bacteriophage
    • C12Q1/701—Specific hybridization probes
    • C12Q1/706—Specific hybridization probes for hepatitis
    • C12Q1/707—Specific hybridization probes for hepatitis non-A, non-B Hepatitis, excluding hepatitis D

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Molecular Biology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Virology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Epidemiology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
CA2557304A 2004-02-27 2005-02-24 Ketoamides with cyclic p4's as inhibitors of ns3 serine protease of hepatitis c virus Expired - Fee Related CA2557304C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US54850604P 2004-02-27 2004-02-27
US60/548,506 2004-02-27
PCT/US2005/005924 WO2005085242A1 (en) 2004-02-27 2005-02-24 Novel ketoamides with cyclic p4's as inhibitors of ns3 serine protease of hepatitis c virus

Publications (2)

Publication Number Publication Date
CA2557304A1 CA2557304A1 (en) 2005-09-15
CA2557304C true CA2557304C (en) 2013-08-06

Family

ID=34919371

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2557304A Expired - Fee Related CA2557304C (en) 2004-02-27 2005-02-24 Ketoamides with cyclic p4's as inhibitors of ns3 serine protease of hepatitis c virus

Country Status (18)

Country Link
US (2) US7173057B2 (OSRAM)
EP (1) EP1730142B1 (OSRAM)
JP (1) JP4874227B2 (OSRAM)
KR (1) KR20070026394A (OSRAM)
CN (1) CN1946718A (OSRAM)
AR (1) AR048023A1 (OSRAM)
AT (1) ATE514691T1 (OSRAM)
AU (1) AU2005219824B2 (OSRAM)
BR (1) BRPI0508217A (OSRAM)
CA (1) CA2557304C (OSRAM)
EC (1) ECSP066792A (OSRAM)
IL (1) IL177628A0 (OSRAM)
NO (1) NO20064355L (OSRAM)
PE (1) PE20050999A1 (OSRAM)
RU (1) RU2006134000A (OSRAM)
TW (1) TW200529822A (OSRAM)
WO (1) WO2005085242A1 (OSRAM)
ZA (1) ZA200607048B (OSRAM)

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Also Published As

Publication number Publication date
EP1730142B1 (en) 2011-06-29
US20050222047A1 (en) 2005-10-06
CN1946718A (zh) 2007-04-11
NO20064355L (no) 2006-11-24
KR20070026394A (ko) 2007-03-08
US7173057B2 (en) 2007-02-06
TW200529822A (en) 2005-09-16
AU2005219824B2 (en) 2007-11-29
ATE514691T1 (de) 2011-07-15
CA2557304A1 (en) 2005-09-15
ECSP066792A (es) 2006-11-16
EP1730142A1 (en) 2006-12-13
AR048023A1 (es) 2006-03-22
US7619094B2 (en) 2009-11-17
WO2005085242A1 (en) 2005-09-15
JP2007525518A (ja) 2007-09-06
PE20050999A1 (es) 2005-12-01
RU2006134000A (ru) 2008-04-10
US20070093430A1 (en) 2007-04-26
BRPI0508217A (pt) 2007-07-17
IL177628A0 (en) 2006-12-31
ZA200607048B (en) 2008-06-25
AU2005219824A1 (en) 2005-09-15
JP4874227B2 (ja) 2012-02-15

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