CA2348470C - Nucleosides with anti-hepatitis b virus activity - Google Patents

Nucleosides with anti-hepatitis b virus activity Download PDF

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Publication number
CA2348470C
CA2348470C CA002348470A CA2348470A CA2348470C CA 2348470 C CA2348470 C CA 2348470C CA 002348470 A CA002348470 A CA 002348470A CA 2348470 A CA2348470 A CA 2348470A CA 2348470 C CA2348470 C CA 2348470C
Authority
CA
Canada
Prior art keywords
acyl
alkyl
monophosphate
triphosphate
composition
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
CA002348470A
Other languages
English (en)
French (fr)
Other versions
CA2348470A1 (en
Inventor
Gilles Gosselin
Jean-Louis Imbach
Jean-Pierre Sommadossi
Raymond F. Schinazi
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.)
Centre National de la Recherche Scientifique CNRS
Emory University
UAB Research Foundation
Original Assignee
Centre National de la Recherche Scientifique CNRS
Emory University
UAB Research Foundation
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 Centre National de la Recherche Scientifique CNRS, Emory University, UAB Research Foundation filed Critical Centre National de la Recherche Scientifique CNRS
Publication of CA2348470A1 publication Critical patent/CA2348470A1/en
Application granted granted Critical
Publication of CA2348470C publication Critical patent/CA2348470C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
    • 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
    • A61P31/20—Antivirals for DNA viruses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Virology (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
CA002348470A 1998-11-05 1999-11-05 Nucleosides with anti-hepatitis b virus activity Expired - Fee Related CA2348470C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US10711698P 1998-11-05 1998-11-05
US60/107,116 1998-11-05
US11565399P 1999-01-13 1999-01-13
US60/115,653 1999-01-13
PCT/US1999/026157 WO2000026225A2 (en) 1998-11-05 1999-11-05 Nucleosides with anti-hepatitis b virus activity

Publications (2)

Publication Number Publication Date
CA2348470A1 CA2348470A1 (en) 2000-05-11
CA2348470C true CA2348470C (en) 2007-06-05

Family

ID=26804401

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002348470A Expired - Fee Related CA2348470C (en) 1998-11-05 1999-11-05 Nucleosides with anti-hepatitis b virus activity

Country Status (13)

Country Link
US (1) US6458773B1 (OSRAM)
EP (1) EP1124839B1 (OSRAM)
JP (2) JP2002528554A (OSRAM)
KR (1) KR100618028B1 (OSRAM)
CN (1) CN1216893C (OSRAM)
AT (1) ATE315574T1 (OSRAM)
AU (1) AU774720B2 (OSRAM)
BR (1) BR9915555A (OSRAM)
CA (1) CA2348470C (OSRAM)
DE (1) DE69929460D1 (OSRAM)
IL (2) IL142983A0 (OSRAM)
MX (1) MXPA01004504A (OSRAM)
WO (1) WO2000026225A2 (OSRAM)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL138037A0 (en) * 1998-02-25 2001-10-31 Univ Emory 2'-fluoronucleosides
MY164523A (en) 2000-05-23 2017-12-29 Univ Degli Studi Cagliari Methods and compositions for treating hepatitis c virus
CZ301182B6 (cs) * 2000-05-26 2009-12-02 Idenix (Cayman) Limited Použití nukleosidových derivátu pro výrobu farmaceutických prostredku pro lécení infekcí vyvolaných flaviviry a pestiviry
US7589077B2 (en) 2001-05-18 2009-09-15 Rakesh Kumar Antiviral nucleosides
US7608600B2 (en) * 2002-06-28 2009-10-27 Idenix Pharmaceuticals, Inc. Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections
CN101172993A (zh) 2002-06-28 2008-05-07 埃迪尼克斯(开曼)有限公司 用于治疗黄病毒感染的2′－c－甲基－3′－o－l－缬氨酸酯核糖呋喃基胞苷
WO2004002422A2 (en) 2002-06-28 2004-01-08 Idenix (Cayman) Limited 2’-c-methyl-3’-o-l-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections
US20040067877A1 (en) 2002-08-01 2004-04-08 Schinazi Raymond F. 2', 3'-Dideoxynucleoside analogues for the treatment or prevention of Flaviviridae infections
DE60329211D1 (de) * 2002-10-31 2009-10-22 Metabasis Therapeutics Inc Cytarabin-monophosphate prodrugs
ES2624353T3 (es) 2002-11-15 2017-07-13 Idenix Pharmaceuticals Llc 2'-Metil nucleósidos en combinación con interferón y mutación de Flaviviridae
RU2005121904A (ru) 2002-12-12 2006-01-20 Айденикс (Кайман) Лимитед (Ky) Способ получения 2`-разветвленных нуклеозидов
JP5254033B2 (ja) 2005-12-23 2013-08-07 イデニク プハルマセウティカルス，インコーポレイテッド 分岐型ヌクレオシドを調製するための合成中間体の製造方法
WO2015123352A1 (en) 2014-02-13 2015-08-20 Ligand Pharmaceuticals, Inc. Prodrug compounds and their uses
US9994600B2 (en) 2014-07-02 2018-06-12 Ligand Pharmaceuticals, Inc. Prodrug compounds and uses therof
AU2019207625A1 (en) 2018-01-09 2020-07-30 Ligand Pharmaceuticals, Inc. Acetal compounds and therapeutic uses thereof

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4681933A (en) 1986-05-01 1987-07-21 University Of Georgia Research Foundation, Inc. 2',3'-dideoxy-5-substituted uridines and related compounds as antiviral agents
US5084445A (en) 1986-05-01 1992-01-28 University Of Georgia Research Foundation, Inc. 3'-azido-2',3'-dideoxy-5-methylcytidine
US4916122A (en) 1987-01-28 1990-04-10 University Of Georgia Research Foundation, Inc. 3'-Azido-2',3'-dideoxyuridine anti-retroviral composition
US5077279A (en) 1986-05-01 1991-12-31 University Of Georgia Research Foundation, Inc. 3'-azido-2',3'-dideoxy-5-methylcytidine anti-viral composition
US4841039A (en) 1986-05-01 1989-06-20 Emory University 2',3'-dideoxy-5-substituted uridines and related compounds as antiviral agents
US5190926A (en) 1987-01-28 1993-03-02 University Of Georgia Research Foundation, Inc. 3'-azido-2',3'-dideoxypyrimidines and related compounds as antiviral agents
US5047407A (en) 1989-02-08 1991-09-10 Iaf Biochem International, Inc. 2-substituted-5-substituted-1,3-oxathiolanes with antiviral properties
US5041449A (en) 1988-04-11 1991-08-20 Iaf Biochem International, Inc. 4-(nucleoside base)-substituted-1,3-dioxolanes useful for treatment of retroviral infections
NZ228645A (en) 1988-04-11 1991-09-25 Iaf Biochem Int 1,3-dioxolane derivatives substituted in the 5th position by a purine or pyrimidine radical; treatment of viral infections
DD293498A5 (de) * 1989-07-20 1991-09-05 Zi Fuer Molekularbiologie Der Adw,De Verfahren zur herstellung eines mittels fuer die behandlung oder prophylaxe von hepatits-infektionen bei mensch und tier
US5204466A (en) 1990-02-01 1993-04-20 Emory University Method and compositions for the synthesis of bch-189 and related compounds
DE4224737A1 (de) * 1992-07-27 1994-02-03 Herbert Prof Dr Schott Neue Cytosinnucleosidanaloga, Verfahren zu ihrer Herstellung und ihre Verwendung
FR2709754B1 (fr) 1993-09-10 1995-12-01 Centre Nat Rech Scient Composés 2' ou 3'-déoxy- et 2', 3'-didéoxy-beta-L-pentofuranonucléosides, procédé de préparation et application thérapeutique, notamment anti-virale.
CA2171550C (en) * 1993-09-10 2008-08-26 Raymond F. Schinazi Nucleosides with anti-hepatitis b virus activity
DE4418690A1 (de) 1994-05-28 1996-01-11 Boehringer Mannheim Gmbh Neue Lipidester von Nucleosid-Monophosphaten und deren Verwendung als immunsuppressive Arzneimittel
US5559101A (en) 1994-10-24 1996-09-24 Genencor International, Inc. L-ribofuranosyl nucleosides
US5703058A (en) 1995-01-27 1997-12-30 Emory University Compositions containing 5-fluoro-2',3'-didehydro-2',3'-dideoxycytidine or a mono-, di-, or triphosphate thereof and a second antiviral agent
ATE346651T1 (de) 1995-06-07 2006-12-15 Univ Emory Nucleoside mit anti-hepatitis b virus wirksamkeit
WO1997009052A1 (en) 1995-09-07 1997-03-13 University Of Georgia Research Foundation, Inc. Therapeutic azide compounds
JP2002503212A (ja) 1996-10-16 2002-01-29 アイ・シー・エヌ・フアーマシユーテイカルズ・インコーポレイテツド 単環式ヌクレオシド、その類似体および使用

Also Published As

Publication number Publication date
HK1036069A1 (en) 2001-12-21
WO2000026225A3 (en) 2000-10-05
KR100618028B1 (ko) 2006-08-30
WO2000026225A2 (en) 2000-05-11
MXPA01004504A (es) 2005-04-19
IL142983A (en) 2006-07-05
EP1124839B1 (en) 2006-01-11
DE69929460D1 (de) 2006-04-06
AU774720B2 (en) 2004-07-08
EP1124839A2 (en) 2001-08-22
AU1608500A (en) 2000-05-22
KR20020013474A (ko) 2002-02-20
CN1329618A (zh) 2002-01-02
BR9915555A (pt) 2002-01-15
CN1216893C (zh) 2005-08-31
JP2002528554A (ja) 2002-09-03
US6458773B1 (en) 2002-10-01
JP2011246469A (ja) 2011-12-08
IL142983A0 (en) 2002-04-21
ATE315574T1 (de) 2006-02-15
CA2348470A1 (en) 2000-05-11

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Effective date: 20141105