CA2557495C - Sulfur compounds as inhibitors of hepatitis c virus ns3 serine protease - Google Patents

Sulfur compounds as inhibitors of hepatitis c virus ns3 serine protease Download PDF

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Publication number
CA2557495C
CA2557495C CA2557495A CA2557495A CA2557495C CA 2557495 C CA2557495 C CA 2557495C CA 2557495 A CA2557495 A CA 2557495A CA 2557495 A CA2557495 A CA 2557495A CA 2557495 C CA2557495 C CA 2557495C
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CA
Canada
Prior art keywords
compound
pharmaceutically acceptable
ester
enantiomer
solvate
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
CA2557495A
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English (en)
French (fr)
Other versions
CA2557495A1 (en
Inventor
Frank Bennett
Raymond G. Lovey
Yuhua Huang
Siska Hendrata
Anil K. Saksena
Stephane L. Bogen
Yi-Tsung Liu
F. George Njoroge
Srikanth Venkatraman
Kevin X. Chen
Mousumi Sannigrahi
Ashok Arasappan
Viyyoor M. Girijavallabhan
Francisco Velazquez
Latha Nair
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Merck Sharp and Dohme LLC
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Merck Sharp and Dohme LLC
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Publication of CA2557495A1 publication Critical patent/CA2557495A1/en
Application granted granted Critical
Publication of CA2557495C publication Critical patent/CA2557495C/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
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
    • 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
    • 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
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D411/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—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
    • C07K5/02—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
    • A61K38/00—Medicinal preparations containing peptides

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)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Virology (AREA)
  • Oncology (AREA)
  • Molecular Biology (AREA)
  • Communicable Diseases (AREA)
  • Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biochemistry (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)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA2557495A 2004-02-27 2005-02-24 Sulfur compounds as inhibitors of hepatitis c virus ns3 serine protease Expired - Fee Related CA2557495C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US54867004P 2004-02-27 2004-02-27
US60/548,670 2004-02-27
PCT/US2005/005795 WO2005087731A1 (en) 2004-02-27 2005-02-24 Sulfur compounds as inhibitors of hepatitis c virus ns3 serine protease

Publications (2)

Publication Number Publication Date
CA2557495A1 CA2557495A1 (en) 2005-09-22
CA2557495C true CA2557495C (en) 2014-04-15

Family

ID=34961556

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2557495A Expired - Fee Related CA2557495C (en) 2004-02-27 2005-02-24 Sulfur compounds as inhibitors of hepatitis c virus ns3 serine protease

Country Status (30)

Country Link
US (1) US8067379B2 (enExample)
EP (1) EP1730110B9 (enExample)
JP (1) JP4714732B2 (enExample)
KR (2) KR101316137B1 (enExample)
CN (2) CN101076516A (enExample)
AR (1) AR048241A1 (enExample)
AT (1) ATE470660T1 (enExample)
AU (1) AU2005222060A1 (enExample)
BR (1) BRPI0508085A (enExample)
CA (1) CA2557495C (enExample)
CY (1) CY1111212T1 (enExample)
DE (1) DE602005021760D1 (enExample)
DK (1) DK1730110T3 (enExample)
EC (1) ECSP066791A (enExample)
ES (1) ES2346233T3 (enExample)
HR (1) HRP20100416T1 (enExample)
IL (1) IL177544A (enExample)
MY (1) MY145081A (enExample)
NO (1) NO20064358L (enExample)
NZ (1) NZ549223A (enExample)
PE (1) PE20051150A1 (enExample)
PL (1) PL1730110T3 (enExample)
PT (1) PT1730110E (enExample)
RS (1) RS51394B (enExample)
RU (1) RU2428428C9 (enExample)
SG (1) SG186041A1 (enExample)
SI (1) SI1730110T1 (enExample)
TW (2) TWI314927B (enExample)
WO (1) WO2005087731A1 (enExample)
ZA (1) ZA200607096B (enExample)

Families Citing this family (67)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IN183120B (enExample) 1996-10-18 1999-09-11 Vertex Pharma
ATE470660T1 (de) * 2004-02-27 2010-06-15 Schering Corp Schwefelverbindungen als inhibitoren der ns3- serinprotease des hepatitis-c-virus
US7816326B2 (en) * 2004-02-27 2010-10-19 Schering Corporation Sulfur compounds as inhibitors of hepatitis C virus NS3 serine protease
GB0426661D0 (en) * 2004-12-06 2005-01-05 Isis Innovation Pyrrolidine compounds
US20060276406A1 (en) * 2005-06-02 2006-12-07 Schering Corporation Methods of treating hepatitis C virus
US20070237818A1 (en) * 2005-06-02 2007-10-11 Malcolm Bruce A Controlled-release formulation of HCV protease inhibitor and methods using the same
US20060276407A1 (en) * 2005-06-02 2006-12-07 Schering Corporation Methods of treating hepatitis C virus
AU2006252623A1 (en) * 2005-06-02 2006-12-07 Schering Corporation Controlled-release formulation useful for treating disorders associated with hepatitis C virus
EP1919478B1 (en) * 2005-06-02 2016-03-23 Merck Sharp & Dohme Corp. Combination of hcv protease inhibitors with a surfactant
WO2006130626A2 (en) * 2005-06-02 2006-12-07 Schering Corporation Method for modulating activity of hcv protease through use of a novel hcv protease inhibitor to reduce duration of treatment period
US20060276404A1 (en) * 2005-06-02 2006-12-07 Anima Ghosal Medicaments and methods combining a HCV protease inhibitor and an AKR competitor
NZ563361A (en) 2005-06-02 2011-02-25 Schering Corp HCV protease inhibitors in combination with food
US20070021351A1 (en) * 2005-06-02 2007-01-25 Schering Corporation Liver/plasma concentration ratio for dosing hepatitis C virus protease inhibitor
US20060275366A1 (en) * 2005-06-02 2006-12-07 Schering Corporation Controlled-release formulation
AR055395A1 (es) 2005-08-26 2007-08-22 Vertex Pharma Compuestos inhibidores de la actividad de la serina proteasa ns3-ns4a del virus de la hepatitis c
US7816348B2 (en) 2006-02-03 2010-10-19 Boehringer Ingelheim International Gmbh Viral polymerase inhibitors
WO2007106317A2 (en) * 2006-03-03 2007-09-20 Schering Corporation Pharmaceutical combinations of hcv-protease and -ires inhibitors
KR101398259B1 (ko) 2006-03-16 2014-05-26 버텍스 파마슈티칼스 인코포레이티드 입체 화합물의 제조 방법 및 이를 위한 중간체
CA2647158C (en) * 2006-03-23 2012-07-31 Schering Corporation Combinations of hcv protease inhibitor(s) and cyp3a4 inhibitor(s), and methods of treatment related thereto
US7825152B2 (en) 2006-04-11 2010-11-02 Novartis Ag Organic compounds and their uses
DE102006059317A1 (de) 2006-07-04 2008-01-10 Evonik Degussa Gmbh Verfahren zur Herstellung von β-Amino-α-hydroxy-carbonsäureamiden
MX2009000882A (es) 2006-08-17 2009-02-04 Boehringer Ingelheim Int Inhibidores de la polimerasa virica.
US20100081672A1 (en) * 2006-12-07 2010-04-01 Schering Corporation Ph sensitive matrix formulation
MX2009006878A (es) 2006-12-22 2009-07-07 Schering Corp Derivados indolicos con anillo unido en las posiciones 4,5 para tratar o prevenir infecciones virales por virus de la hepatitis c e infecciones virales relacionadas.
US8268803B2 (en) 2006-12-22 2012-09-18 Merck Sharp & Dohme Corp. 5, 6-ring annulated indole derivatives and use thereof
KR20090094154A (ko) 2006-12-22 2009-09-03 쉐링 코포레이션 Ｈｃｖ 및 관련 바이러스 감염을 치료 또는 예방하기 위한 4,5-환 환상 인돌 유도체
WO2008078563A1 (ja) * 2006-12-22 2008-07-03 Sumitomo Seika Chemicals Co., Ltd. ３－ベンジルオキシベンゼンチオールの製造方法
EP2188274A4 (en) 2007-08-03 2011-05-25 Boehringer Ingelheim Int VIRAL POLYMERASE HEMMER
TW200924751A (en) 2007-08-29 2009-06-16 Schering Corp 2,3-substituted indole derivatives and methods of use thereof
CN101821252A (zh) 2007-08-29 2010-09-01 先灵公司 取代的吲哚衍生物及其使用方法
KR20100065167A (ko) 2007-08-29 2010-06-15 쉐링 코포레이션 바이러스 감염 치료용 2,3-치환된 아자인돌 유도체
NZ583825A (en) * 2007-09-14 2012-06-29 Schering Corp Method of treating hepatitis C patients comprising an HCV protease inhibitor, an antiviral compound and an interferon
CN101868452B (zh) 2007-10-10 2014-08-06 诺华股份有限公司 螺环吡咯烷类与其对抗hcv和hiv感染的应用
US8765757B2 (en) 2007-11-16 2014-07-01 Merck Sharp & Dohme Corp. 3-heterocyclic substituted indole derivatives and methods of use thereof
MX2010005355A (es) 2007-11-16 2010-06-02 Schering Corp Derivados de indol sustituidos con 3-aminosulfonilo y metodos de uso de los mismos.
US8476257B2 (en) 2007-12-19 2013-07-02 Boehringer Ingelheim International Gmbh Viral polymerase inhibitors
US7964560B2 (en) * 2008-05-29 2011-06-21 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
MX2010013630A (es) 2008-06-13 2010-12-21 Schering Corp Derivados triciclicos de indol y metodos de uso de los mismos.
WO2010017432A1 (en) * 2008-08-07 2010-02-11 Schering Corporation Pharmaceutical formulations of an hcv protease inhibitor in a solid molecular dispersion
US8188137B2 (en) 2008-08-15 2012-05-29 Avila Therapeutics, Inc. HCV protease inhibitors and uses thereof
AR074582A1 (es) 2008-12-12 2011-01-26 Schering Corp Compuestos deuterados como inhibidores del virus de la hepatitis c (hcv)
MX2011007195A (es) 2009-01-07 2013-07-12 Scynexis Inc Derivado de ciclosporina para el uso en el tratamiento de infección de virus de hepatitis c (vhc) y virus de inmunodeficiencia humana (vih).
US8512690B2 (en) 2009-04-10 2013-08-20 Novartis Ag Derivatised proline containing peptide compounds as protease inhibitors
EP2435424B1 (en) 2009-05-29 2015-01-21 Merck Sharp & Dohme Corp. Antiviral compounds composed of three linked aryl moieties to treat diseases such as hepatitis c
EP2459525B1 (en) * 2009-07-29 2017-03-01 Merck Sharp & Dohme Corp. Enantio- and stereo-specific syntheses of -amino- - hydroxy amides
US20120276047A1 (en) 2009-11-25 2012-11-01 Rosenblum Stuart B Fused tricyclic compounds and derivatives thereof useful for the treatment of viral diseases
EP2516430B1 (en) 2009-12-22 2014-11-05 Merck Sharp & Dohme Corp. Fused tricyclic compounds and methods of use thereof for the treatment of viral diseases
BR112012022125A2 (pt) 2010-03-09 2016-11-01 Merck Sharp & Dhme Corp composto, sal de dicloridrato, composição farmacêutica, uso do composto, e, método para tratar um paciente
JP2013541499A (ja) 2010-07-26 2013-11-14 メルク・シャープ・エンド・ドーム・コーポレイション 置換されたビフェニレン化合物およびウイルス性疾患の治療のためのその使用方法
US9133116B2 (en) 2010-09-28 2015-09-15 Panacea Biotec Ltd. Bicyclic compounds
AU2011314168A1 (en) 2010-09-29 2013-04-04 Merck Sharp & Dohme Corp. Fused tetracycle derivatives and methods of use thereof for the treatment of viral diseases
WO2012073249A1 (en) 2010-12-01 2012-06-07 Arch Pharmalabs Limited A novel process for the preparation of 3-(benzyloxy)- benzenethiol, a key intermediate for the preparation of pharmaceutical drugs.
WO2012142075A1 (en) 2011-04-13 2012-10-18 Merck Sharp & Dohme Corp. 2'-azido substituted nucleoside derivatives and methods of use thereof for the treatment of viral diseases
EA201391519A1 (ru) 2011-04-13 2014-03-31 Мерк Шарп И Доум Корп. 2'-замещенные нуклеозидные производные и способы их применения для лечения вирусных заболеваний
WO2013033901A1 (en) 2011-09-08 2013-03-14 Merck Sharp & Dohme Corp. Heterocyclic-substituted benzofuran derivatives and methods of use thereof for the treatment of viral diseases
WO2013033899A1 (en) 2011-09-08 2013-03-14 Merck Sharp & Dohme Corp. Substituted benzofuran compounds and methods of use thereof for the treatment of viral diseases
WO2013033900A1 (en) 2011-09-08 2013-03-14 Merck Sharp & Dohme Corp. Tetracyclic heterocycle compounds and methods of use thereof for the treatment of viral diseases
EP2755981A4 (en) 2011-09-14 2015-03-25 Merck Sharp & Dohme SILICULAR HETEROCYCLIC DERIVATIVES AND METHOD FOR THEIR USE FOR THE TREATMENT OF VIRUS DISEASES
US10167298B2 (en) 2013-10-30 2019-01-01 Merck Sharp & Dohme Corp. Pseudopolymorphs of an HCV NS5A inhibitor and uses thereof
WO2017059446A1 (en) * 2015-10-01 2017-04-06 Memorial Sloan-Kettering Cancer Center Anthranilyl-adenosinemonosulfamate analogs and uses thereof
CA3000709A1 (en) * 2015-10-01 2017-04-06 Memorial Sloan-Kettering Cancer Center Inhibitors of menaquinone biosynthesis
EA201990070A1 (ru) 2016-06-21 2019-06-28 ОРИОН ОФТАЛМОЛОДЖИ ЭлЭлСи Производные алифатического пролинамида
US12435088B2 (en) 2018-12-21 2025-10-07 Memorial Sloan-Kettering Cancer Center Salicyl-adenosinemonosulfamate analogs and uses thereof
WO2021209563A1 (en) 2020-04-16 2021-10-21 Som Innovation Biotech, S.A. Compounds for use in the treatment of viral infections by respiratory syndrome-related coronavirus
US11351149B2 (en) 2020-09-03 2022-06-07 Pfizer Inc. Nitrile-containing antiviral compounds
US12083099B2 (en) 2020-10-28 2024-09-10 Accencio LLC Methods of treating symptoms of coronavirus infection with viral protease inhibitors
EP4653420A1 (en) 2023-01-17 2025-11-26 Shenyang Haisco Pharmaceutical Co., Ltd. Method for preparing chiral amino alcohol pharmaceutical intermediates

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69133617D1 (de) 1990-04-04 2009-07-23 Novartis Vaccines & Diagnostic Protease von Hepatitis C Virus
US5922757A (en) 1996-09-30 1999-07-13 The Regents Of The University Of California Treatment and prevention of hepatic disorders
IN183120B (enExample) 1996-10-18 1999-09-11 Vertex Pharma
GB9623908D0 (en) 1996-11-18 1997-01-08 Hoffmann La Roche Amino acid derivatives
PT1012180E (pt) 1997-08-11 2005-04-29 Boehringer Ingelheim Ca Ltd Analogos de peptidos inibidores da hepatite c
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
US6608027B1 (en) 1999-04-06 2003-08-19 Boehringer Ingelheim (Canada) Ltd Macrocyclic peptides active against the hepatitis C virus
JP4806154B2 (ja) 2000-04-03 2011-11-02 バーテックス ファーマシューティカルズ インコーポレイテッド セリンプロテアーゼ、特にｃ型肝炎ウイルスｎｓ３プロテアーゼのインヒビター
NZ521455A (en) 2000-04-05 2004-06-25 Schering Corp Macrocyclic NS3-Serine protease inhibitors of hepatitis C virus comprising N-Cyclic P2 Moieties
BR0110104A (pt) 2000-04-19 2003-01-07 Schering Corp Inibidores de ns-3 serina rotease macrocìclica do vìrus da hepatite c compreendendo porções de alquil e aril alanina p2
AR029851A1 (es) 2000-07-21 2003-07-16 Dendreon Corp Nuevos peptidos como inhibidores de ns3-serina proteasa del virus de hepatitis c
WO2002008251A2 (en) 2000-07-21 2002-01-31 Corvas International, Inc. Peptides as ns3-serine protease inhibitors of hepatitis c virus
MY139078A (en) 2000-07-21 2009-08-28 Schering Corp Peptides as ns3-serine protease inhibitors of hepatitis c virus
WO2002008187A1 (en) 2000-07-21 2002-01-31 Schering Corporation Novel peptides as ns3-serine protease inhibitors of hepatitis c virus
US7244721B2 (en) * 2000-07-21 2007-07-17 Schering Corporation Peptides as NS3-serine protease inhibitors of hepatitis C virus
SV2003000617A (es) * 2000-08-31 2003-01-13 Lilly Co Eli Inhibidores de la proteasa peptidomimetica ref. x-14912m
EP1343807B1 (en) 2000-12-12 2009-04-29 Schering Corporation Diaryl peptides as ns3-serine protease inhibitors of hepatits c virus
WO2003035060A1 (en) * 2001-10-24 2003-05-01 Vertex Pharmaceuticals Incorporated Inhibitors of serine protease, particularly hepatitis c virus ns3-ns4a protease, incorporating a fused ring system
US7816326B2 (en) 2004-02-27 2010-10-19 Schering Corporation Sulfur compounds as inhibitors of hepatitis C virus NS3 serine protease
ATE470660T1 (de) * 2004-02-27 2010-06-15 Schering Corp Schwefelverbindungen als inhibitoren der ns3- serinprotease des hepatitis-c-virus
EP1919478B1 (en) 2005-06-02 2016-03-23 Merck Sharp & Dohme Corp. Combination of hcv protease inhibitors with a surfactant

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