CA2069063A1 - Processes for the diastereoselective synthesis of nucleosides - Google Patents

Processes for the diastereoselective synthesis of nucleosides

Info

Publication number
CA2069063A1
CA2069063A1 CA2069063A CA2069063A CA2069063A1 CA 2069063 A1 CA2069063 A1 CA 2069063A1 CA 2069063 A CA2069063 A CA 2069063A CA 2069063 A CA2069063 A CA 2069063A CA 2069063 A1 CA2069063 A1 CA 2069063A1
Authority
CA
Canada
Prior art keywords
processes
nucleosides
diastereoselective synthesis
diastereoselective
synthesis
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.)
Granted
Application number
CA2069063A
Other languages
French (fr)
Other versions
CA2069063C (en
Inventor
Tarek Mansour
Haolun Jin
Allan H. L. Tse
M. Arshad Siddiqui
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.)
Shire Canada Inc
Original Assignee
Individual
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=24825144&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA2069063(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Individual filed Critical Individual
Publication of CA2069063A1 publication Critical patent/CA2069063A1/en
Application granted granted Critical
Publication of CA2069063C publication Critical patent/CA2069063C/en
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • 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
    • C07D405/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings 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
    • C07D307/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings 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
    • C07D317/34—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C07D339/02—Five-membered rings
    • C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
    • 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
    • C07D409/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D411/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • 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
    • C07H19/16—Purine radicals

Abstract

The present invention relates to highly diastereoselective processes for production of cis-nucleosides and nucleoside analogues and derivatives in high optical purity and intermediates useful in those processes.
CA002069063A 1991-05-21 1992-05-20 Processes for the diastereoselective synthesis of nucleosides Expired - Lifetime CA2069063C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US70337991A 1991-05-21 1991-05-21
US07/703,379 1991-05-21

Publications (2)

Publication Number Publication Date
CA2069063A1 true CA2069063A1 (en) 1992-11-22
CA2069063C CA2069063C (en) 1997-07-15

Family

ID=24825144

Family Applications (2)

Application Number Title Priority Date Filing Date
CA002069024A Expired - Fee Related CA2069024C (en) 1991-05-21 1992-05-20 Processes for the diastereoselective synthesis of nucleosides
CA002069063A Expired - Lifetime CA2069063C (en) 1991-05-21 1992-05-20 Processes for the diastereoselective synthesis of nucleosides

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CA002069024A Expired - Fee Related CA2069024C (en) 1991-05-21 1992-05-20 Processes for the diastereoselective synthesis of nucleosides

Country Status (34)

Country Link
US (5) US5756706A (en)
EP (2) EP0515156B1 (en)
JP (3) JP3330972B2 (en)
KR (3) KR100232012B1 (en)
CN (6) CN1035555C (en)
AT (2) ATE157662T1 (en)
AU (4) AU1690892A (en)
BG (2) BG61695B1 (en)
CA (2) CA2069024C (en)
CZ (3) CZ285220B6 (en)
DE (2) DE69208144T2 (en)
DK (2) DK0515156T3 (en)
EE (1) EE03044B1 (en)
ES (2) ES2084937T3 (en)
FI (3) FI106377B (en)
GR (2) GR3018941T3 (en)
GT (1) GT199800047A (en)
HK (2) HK132196A (en)
HU (2) HU221850B1 (en)
IE (2) IE921618A1 (en)
IL (6) IL116109A (en)
MD (1) MD1155C2 (en)
MX (2) MX9202395A (en)
NO (2) NO300593B1 (en)
NZ (2) NZ242818A (en)
OA (1) OA10212A (en)
PL (3) PL176026B1 (en)
RO (1) RO116812B1 (en)
RU (4) RU2105009C1 (en)
SG (1) SG43863A1 (en)
SK (2) SK279438B6 (en)
TW (4) TW366350B (en)
WO (2) WO1992020696A1 (en)
ZA (2) ZA923641B (en)

Families Citing this family (109)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6903224B2 (en) 1988-04-11 2005-06-07 Biochem Pharma Inc. Substituted 1,3-oxathiolanes
US5466806A (en) * 1989-02-08 1995-11-14 Biochem Pharma Inc. Processes for preparing substituted 1,3-oxathiolanes with antiviral properties
US6350753B1 (en) 1988-04-11 2002-02-26 Biochem Pharma Inc. 2-Substituted-4-substituted-1,3-dioxolanes and use thereof
US5684164A (en) * 1988-04-11 1997-11-04 Biochem Pharma Inc. Processes for preparing substituted 1,3-oxathiolanes with antiviral properties
PT674634E (en) * 1989-02-08 2003-09-30 Iaf Biochem Int PROCESSES FOR PREPARING 1,3-OXATIOLANOS SUBSTITUTED WITH ANTIVIRARY PROPERTIES
US5204466A (en) * 1990-02-01 1993-04-20 Emory University Method and compositions for the synthesis of bch-189 and related compounds
US5914331A (en) * 1990-02-01 1999-06-22 Emory University Antiviral activity and resolution of 2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane
US5276151A (en) * 1990-02-01 1994-01-04 Emory University Method of synthesis of 1,3-dioxolane nucleosides
US6703396B1 (en) 1990-02-01 2004-03-09 Emory University Method of resolution and antiviral activity of 1,3-oxathiolane nuclesoside enantiomers
US6346627B1 (en) 1990-02-01 2002-02-12 Emory University Intermediates in the synthesis of 1,3-oxathiolane nucleoside enantiomers
US5587480A (en) * 1990-11-13 1996-12-24 Biochem Pharma, Inc. Substituted 1,3-oxathiolanes and substituted 1,3-dithiolanes with antiviral properties
US5925643A (en) * 1990-12-05 1999-07-20 Emory University Enantiomerically pure β-D-dioxolane-nucleosides
US5444063A (en) * 1990-12-05 1995-08-22 Emory University Enantiomerically pure β-D-dioxolane nucleosides with selective anti-Hepatitis B virus activity
US6812233B1 (en) 1991-03-06 2004-11-02 Emory University Therapeutic nucleosides
US5817667A (en) * 1991-04-17 1998-10-06 University Of Georgia Research Foudation Compounds and methods for the treatment of cancer
ZA923641B (en) * 1991-05-21 1993-02-24 Iaf Biochem Int Processes for the diastereoselective synthesis of nucleosides
US6005107A (en) * 1992-12-23 1999-12-21 Biochem Pharma, Inc. Antiviral compounds
GB9226879D0 (en) * 1992-12-23 1993-02-17 Iaf Biochem Int Anti-viral compounds
US6444656B1 (en) 1992-12-23 2002-09-03 Biochem Pharma, Inc. Antiviral phosphonate nucleotides
GB9226927D0 (en) * 1992-12-24 1993-02-17 Iaf Biochem Int Dideoxy nucleoside analogues
TW374087B (en) * 1993-05-25 1999-11-11 Univ Yale L-2',3'-dideoxy nucleotide analogs as anti-hepatitis B(HBV) and anti-HIV agents
US5627160A (en) * 1993-05-25 1997-05-06 Yale University L-2',3'-dideoxy nucleoside analogs as anti-hepatitis B (HBV) and anti-HIV agents
GB9311709D0 (en) * 1993-06-07 1993-07-21 Iaf Biochem Int Stereoselective synthesis of nucleoside analogues using bicycle intermediate
US20020120130A1 (en) 1993-09-10 2002-08-29 Gilles Gosselin 2' or 3' -deoxy and 2', 3' -dideoxy-beta-L-pentofuranonucleo-side compounds, method of preparation and application in therapy, especially as anti- viral agents
EP0717628A4 (en) 1993-09-10 1999-05-26 Univ Emory Nucleosides with anti-hepatitis b virus activity
US5587362A (en) * 1994-01-28 1996-12-24 Univ. Of Ga Research Foundation L-nucleosides
IL113432A (en) 1994-04-23 2000-11-21 Glaxo Group Ltd Process for the diastereoselective synthesis of nucleoside analogues
GB9413724D0 (en) * 1994-07-07 1994-08-24 Wellcome Found Therapeutic nucleosides
US6514949B1 (en) 1994-07-11 2003-02-04 University Of Virginia Patent Foundation Method compositions for treating the inflammatory response
US6448235B1 (en) 1994-07-11 2002-09-10 University Of Virginia Patent Foundation Method for treating restenosis with A2A adenosine receptor agonists
IL115156A (en) * 1994-09-06 2000-07-16 Univ Georgia Pharmaceutical compositions for the treatment of cancer comprising 1-(2-hydroxymethyl-1,3-dioxolan-4-yl) cytosines
US6391859B1 (en) 1995-01-27 2002-05-21 Emory University [5-Carboxamido or 5-fluoro]-[2′,3′-unsaturated or 3′-modified]-pyrimidine 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
US5808040A (en) * 1995-01-30 1998-09-15 Yale University L-nucleosides incorporated into polymeric structure for stabilization of oligonucleotides
US5869461A (en) * 1995-03-16 1999-02-09 Yale University Reducing toxicity of L-nucleosides with D-nucleosides
GB9506644D0 (en) * 1995-03-31 1995-05-24 Wellcome Found Preparation of nucleoside analogues
EP1655033A1 (en) 1995-06-07 2006-05-10 Emory University Nucleosides with anti-hepatitis B virus activity
CN1201463A (en) * 1995-11-02 1998-12-09 株式会社钟根堂 Novel nucleoside derivatives and process for preparing same
GB9600143D0 (en) 1996-01-05 1996-03-06 Wellcome Found Therapeutic compounds
EP0799834A1 (en) * 1996-04-04 1997-10-08 Novartis AG Modified nucleotides
US6005097A (en) * 1996-06-14 1999-12-21 Vion Pharmaceuticals, Inc. Processes for high-yield diastereoselective synthesis of dideoxynucleosides
US5753789A (en) * 1996-07-26 1998-05-19 Yale University Oligonucleotides containing L-nucleosides
US6022876A (en) 1996-11-15 2000-02-08 Yale University L-β-dioxolane uridine analogs and methods for treating and preventing Epstein-Barr virus infections
EP0970100B1 (en) 1997-02-13 2003-11-12 Glaxo Group Limited Benzimidazole derivatives
JP2001518899A (en) 1997-04-07 2001-10-16 トライアングル ファーマシューティカルズ，インコーポレイティド Use of MKC-442 in combination with other antiviral agents
ID24054A (en) 1997-06-10 2000-07-06 Glaxo Group Ltd Glaxo BENZIMIDAZOL DOWN
EP1000080A1 (en) 1997-07-30 2000-05-17 The Regents of The University of Michigan Lyxofuranosyl benzimidazoles as antiviral agents
US20030220234A1 (en) * 1998-11-02 2003-11-27 Selvaraj Naicker Deuterated cyclosporine analogs and their use as immunodulating agents
YU44900A (en) 1998-01-31 2003-01-31 Glaxo Group Limited 2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
CN1141305C (en) 1998-08-12 2004-03-10 三角药物公司 Manufacture of 1,3-oxathiolane nucleosides
US6979561B1 (en) * 1998-10-09 2005-12-27 Gilead Sciences, Inc. Non-homogeneous systems for the resolution of enantiomeric mixtures
EP1140937B1 (en) 1998-12-23 2003-11-12 Shire Biochem Inc. Antiviral nucleoside analogues
US7115584B2 (en) 1999-01-22 2006-10-03 Emory University HIV-1 mutations selected for by β-2′,3′-didehydro-2′,3′-dideoxy-5-fluorocytidine
US7635690B2 (en) 1999-01-22 2009-12-22 Emory University HIV-1 mutations selected for by β-2′,3′-didehydro-2′,3′-dideoxy-5-fluorocytidine
US6232297B1 (en) 1999-02-01 2001-05-15 University Of Virginia Patent Foundation Methods and compositions for treating inflammatory response
US7427606B2 (en) * 1999-02-01 2008-09-23 University Of Virginia Patent Foundation Method to reduce inflammatory response in transplanted tissue
US7378400B2 (en) * 1999-02-01 2008-05-27 University Of Virginia Patent Foundation Method to reduce an inflammatory response from arthritis
YU25500A (en) 1999-05-11 2003-08-29 Pfizer Products Inc. Process for the synthesis of nucleosite analogues
US6322771B1 (en) 1999-06-18 2001-11-27 University Of Virginia Patent Foundation Induction of pharmacological stress with adenosine receptor agonists
DE60011637T2 (en) * 1999-09-24 2004-11-11 Shire Biochem Inc., Laval DIOXOLAN NUCLEOSIDE ANALOGS FOR THE TREATMENT AND PREVENTION OF VIRAL INFECTIONS
CA2389745C (en) 1999-11-04 2010-03-23 Shire Biochem Inc. Method for the treatment or prevention of flaviviridae viral infection using nucleoside analogues
US6436948B1 (en) 2000-03-03 2002-08-20 University Of Georgia Research Foundation Inc. Method for the treatment of psoriasis and genital warts
CA2308559C (en) * 2000-05-16 2005-07-26 Brantford Chemicals Inc. 1,3-oxathiolan-5-ones useful in the production of antiviral nucleoside analogues
DK1574512T3 (en) * 2001-03-01 2008-03-03 Abbott Lab Polymorphic and other crystalline forms of cis-FTC
US6600044B2 (en) 2001-06-18 2003-07-29 Brantford Chemicals Inc. Process for recovery of the desired cis-1,3-oxathiolane nucleosides from their undesired trans-isomers
AU2002362443B2 (en) * 2001-10-01 2008-05-15 University Of Virginia Patent Foundation 2-propynyl adenosine analogs having A2A agonist activity and compositions thereof
NZ531944A (en) * 2001-10-19 2006-03-31 Isotechnika Inc Synthesis of cyclosporin analogs
ITMI20012317A1 (en) * 2001-11-06 2003-05-06 Recordati Ind Chimica E Farma DIASTEREOSELECTIVE PROCESS FOR THE PREPARATION OF THE ANTIVIRAL AGENT4-AMINO-1- (2R-IDROSSIMETIL- / 1,3 / OSSATIOLAN-5S-I1) -1H-PIRIMIDIN-2-ONE
EP1461041A4 (en) * 2001-12-14 2006-03-29 Pharmasset Ltd Preparation of intermediates useful in the synthesis of antiviral nucleosides
ATE548366T1 (en) * 2002-01-25 2012-03-15 Shire Biochem Inc METHOD FOR PRODUCING DIOXOLANE NUCLEOSIDE ANALOGO PRECURSORS
US7365173B2 (en) * 2002-02-04 2008-04-29 American National Red Cross Method for the production of pure virally inactivated butyrylcholinesterase
EP1534255B1 (en) 2002-08-06 2011-01-19 Pharmasset, Inc. Processes for preparing 1,3-dioxolane nucleosides
EP1583542B9 (en) 2003-01-14 2008-10-22 Gilead Sciences, Inc. Compositions and methods for combination antiviral therapy
ITMI20030578A1 (en) * 2003-03-24 2004-09-25 Clariant Lsm Italia Spa PROCESS AND INTERMEDIATES FOR THE PREPARATION OF EMTRICITABINE
CN105039489A (en) * 2004-02-03 2015-11-11 埃莫里大学 Methods to manufacture 1,3-dioxolane nucleosides
NZ585697A (en) * 2004-08-02 2011-12-22 Univ Virginia Patent Found 2-propynyl adenosine analogs with modified 5'-ribose groups having A2A agonist activity
WO2006023272A1 (en) * 2004-08-02 2006-03-02 University Of Virginia Patent Foundation 2-polycyclic propynyl adenosine analogs having a2a agonist activity
US7576069B2 (en) * 2004-08-02 2009-08-18 University Of Virginia Patent Foundation 2-polycyclic propynyl adenosine analogs having A2A agonist activity
US7970631B2 (en) * 2004-08-31 2011-06-28 Ethicon Endo-Surgery, Inc. Medical effector system
US7250416B2 (en) 2005-03-11 2007-07-31 Supergen, Inc. Azacytosine analogs and derivatives
TWI471145B (en) 2005-06-13 2015-02-01 Bristol Myers Squibb & Gilead Sciences Llc Unitary pharmaceutical dosage form
TWI375560B (en) 2005-06-13 2012-11-01 Gilead Sciences Inc Composition comprising dry granulated emtricitabine and tenofovir df and method for making the same
US7700567B2 (en) 2005-09-29 2010-04-20 Supergen, Inc. Oligonucleotide analogues incorporating 5-aza-cytosine therein
WO2007077505A2 (en) * 2005-12-30 2007-07-12 Ranbaxy Laboratories Limited Crystalline l-menthyl (2r, 5s)-5-(4-amino-5-fluoro-2-oxo-2h-pyrimidin-1-yl)[1, 3]oxathiolan-2-carboxylate and process for preparation thereof
WO2007120972A2 (en) * 2006-02-10 2007-10-25 University Of Virginia Patent Foundation Method to treat sickle cell disease
US8188063B2 (en) * 2006-06-19 2012-05-29 University Of Virginia Patent Foundation Use of adenosine A2A modulators to treat spinal cord injury
US20110257396A1 (en) * 2006-10-30 2011-10-20 Lupin Limited Process for the manufacture of cis(-)-lamivudine
KR20100072230A (en) 2007-09-26 2010-06-30 마운트 시나이 스쿨 오브 메디신 오브 뉴욕 유니버시티 Azacytidine analogues and uses thereof
AU2008331166B2 (en) * 2007-11-29 2013-10-10 Ranbaxy Laboratories Limited Process for the preparation of substituted 1,3-oxathiolanes
AU2008331167A1 (en) * 2007-11-29 2009-06-04 Ranbaxy Laboratories Limited Process and intermediates for the preparation of substituted 1, 3-oxathiolanes, especially lamivudine
US8350030B2 (en) 2007-12-07 2013-01-08 Matrix Laboratories Limited Process for producing 5-fluoro-1-(2R, 5S)-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine
US8058259B2 (en) * 2007-12-20 2011-11-15 University Of Virginia Patent Foundation Substituted 4-{3-[6-amino-9-(3,4-dihydroxy-tetrahydro-furan-2-yl)-9H-purin-2-yl]-prop-2-ynyl}-piperidine-1-carboxylic acid esters as A2AR agonists
EA022950B1 (en) 2008-05-02 2016-03-31 Джилид Сайэнс, Инк. Use of silicon dioxide carrier particles to improve the processability of a pharmaceutical agent
US20110282046A1 (en) 2009-01-19 2011-11-17 Rama Shankar Process for preparation of cis-nucleoside derivative
DK2393485T3 (en) 2009-02-06 2015-10-26 Gilead Sciences Inc Bilayer COVERING ELVITEGRAVIR, COBICISTAT, emtricitabine and tenofovir
US20140046062A1 (en) * 2010-01-08 2014-02-13 Bandi Parthasaradhi Reddy Process for nucleosides
HUE037812T2 (en) 2010-01-27 2018-09-28 Viiv Healthcare Co Antiviral therapy
US20120295930A1 (en) * 2010-02-03 2012-11-22 Shankar Rama Novel process for the preparation of cis-nucleoside derivative
CA2792044A1 (en) 2010-03-04 2011-09-09 Ranbaxy Laboratories Limited A process for stereoselective synthesis of 5-fluoro-1-(2r,5s)-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine
EP2377862A1 (en) 2010-03-29 2011-10-19 Esteve Química, S.A. Process for obtaining emtricitabine
WO2011141805A2 (en) 2010-05-14 2011-11-17 Lupin Limited An improved process for the manufacture of lamivudine
CN103221037A (en) 2010-11-12 2013-07-24 葛兰素惠尔康制造业私人有限公司 Novel pharmaceutical compositions
WO2013021290A1 (en) 2011-08-05 2013-02-14 Lupin Limited A stereoselective process for preparation of 1,3-oxathiolane nucleosides
MX359314B (en) 2011-08-30 2018-09-25 Astex Pharmaceuticals Inc Star Decitabine derivative formulations.
CN103242243B (en) * 2013-01-08 2015-08-19 北京大学 A kind of base triacetin ether-ether molecule, its chemical synthesis process and the application in field of gene thereof
CN103288806A (en) * 2013-07-02 2013-09-11 山东大学 Synthesis method of troxacitabine
WO2017004538A1 (en) 2015-07-02 2017-01-05 Otsuka Pharmaceutical Co., Ltd. Lyophilized pharmaceutical compositions
CN105037340B (en) * 2015-07-14 2018-08-10 福建广生堂药业股份有限公司 A kind of preparation method of lamivudine key intermediate chiral isomer impurity
RU2020108580A (en) 2017-08-03 2021-09-03 Оцука Фармасьютикал Ко., Лтд. MEDICINAL COMPOUNDS AND METHODS OF ITS PURIFICATION

Family Cites Families (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1445013A (en) * 1964-07-09 1966-07-08 Thomae Gmbh Dr K Process for making new dioxolano-2-carboxylic acids
US4383114A (en) * 1977-02-09 1983-05-10 Regents Of The University Of Minnesota Adenosine deaminase resistant antiviral purine arabinonucleosides
US4231945A (en) * 1978-11-08 1980-11-04 Schering Corporation S-5-(Azidomethyl or aminomethyl)-2-lower-alkoxytetrahydrofurans
US4479942A (en) * 1981-08-10 1984-10-30 Fujisawa Pharmaceutical Co., Ltd. Tetrahydrofurnancarboxylic acid derivatives, processes for preparation thereof and pharmaceutical compositions thereof
US4855304A (en) * 1985-01-10 1989-08-08 Repligen Corporation Dinucleoside pyrophosphates and pyrophosphate homologs as plant antivirals
DK363987A (en) * 1986-08-08 1988-02-09 Hoffmann La Roche pyrimidine
GB8621268D0 (en) * 1986-09-03 1986-10-08 Univ Strathclyde Separation of substances
US4997818A (en) * 1987-09-21 1991-03-05 The University Hospital Therapeutic method for selectively treating terminal deoxynucleotidyl transferase-positive neoplastic leukemias and lymphomas
SE8704298D0 (en) * 1987-11-03 1987-11-03 Astra Ab COMPOUNDS FOR USE IN THERAPY
US4997926A (en) * 1987-11-18 1991-03-05 Scripps Clinic And Research Foundation Deaminase-stable anti-retroviral 2-halo-2',3'-dideoxy
JPH022349A (en) * 1988-02-17 1990-01-08 Takeda Chem Ind Ltd Pyrimidine analogue-tolerated gene dna and use thereof
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
US5047407A (en) * 1989-02-08 1991-09-10 Iaf Biochem International, Inc. 2-substituted-5-substituted-1,3-oxathiolanes with antiviral properties
GB8815265D0 (en) * 1988-06-27 1988-08-03 Wellcome Found Therapeutic nucleosides
DE3823127A1 (en) * 1988-07-08 1990-01-11 Rheinische Braunkohlenw Ag DEVICE AND METHOD FOR PURIFYING WASTE WATER
US4987224A (en) * 1988-08-02 1991-01-22 University Of Georgia Research Foundation, Inc. Method of preparation of 2',3'-dideoxynucleosides
DE3827134A1 (en) * 1988-08-10 1990-03-15 Bayer Ag SUBSTITUTED TRIAZOLYL OR IMIDAZOLYL-HYDROXYALKYLDIOXOLANE, METHOD FOR THE PRODUCTION THEREOF AND THE USE THEREOF AS MICROBICIDES, OXIRANYLDIOXOLANES, DIOXOLANYLKETONE, OXIRANYLKETONE AND (ALPHA) -HALOGENICENETHENO ZERO DETECTED
US5075225A (en) * 1989-04-06 1991-12-24 The Texas A&M University System Process for the enzymatic synthesis of nucleosides
NZ233197A (en) * 1989-04-13 1991-11-26 Richard Thomas Walker Aromatically substituted nucleotide derivatives, intermediates therefor and pharmaceutical compositions
NZ234534A (en) * 1989-07-17 1994-12-22 Univ Birmingham Pyrimidine 4'-thionucleoside derivatives and their preparation; intermediates therefor
IE904378A1 (en) * 1989-12-20 1991-07-03 Abbott Lab Analogs of oxetanyl purines and pyrimidines
US5204466A (en) * 1990-02-01 1993-04-20 Emory University Method and compositions for the synthesis of bch-189 and related compounds
GB9009861D0 (en) * 1990-05-02 1990-06-27 Glaxo Group Ltd Chemical compounds
GB9014090D0 (en) * 1990-06-25 1990-08-15 Zaadunie Bv Improvements in or relating to organic compounds
WO1992010496A1 (en) * 1990-12-05 1992-06-25 University Of Georgia Research Foundation, Inc. ENANTIOMERICALLY PURE β-L-(-)-1,3-OXATHIOLANE NUCLEOSIDES
NZ250842A (en) * 1991-02-22 1996-03-26 Univ Emory Resolution of a racemic mixture of nucleoside enantiomers such as 2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane (ftc)
WO1992018517A1 (en) * 1991-04-17 1992-10-29 Yale University Method of treating or preventing hepatitis b virus
GB9109506D0 (en) * 1991-05-02 1991-06-26 Wellcome Found Therapeutic nucleosides
ZA923641B (en) * 1991-05-21 1993-02-24 Iaf Biochem Int Processes for the diastereoselective synthesis of nucleosides

Also Published As

Publication number Publication date
NZ242818A (en) 1994-04-27
CN1229078A (en) 1999-09-22
BG61696B1 (en) 1998-03-31
FI20001900A (en) 2000-08-29
DE69221936T2 (en) 1998-01-02
CA2069063C (en) 1997-07-15
TW366350B (en) 1999-08-11
KR0160144B1 (en) 1998-11-16
ZA923640B (en) 1993-02-24
HU9303297D0 (en) 1994-03-28
IL101932A (en) 1997-04-15
GR3018941T3 (en) 1996-05-31
CZ280857B6 (en) 1996-04-17
ATE133958T1 (en) 1996-02-15
US5744596A (en) 1998-04-28
US5663320A (en) 1997-09-02
HK132196A (en) 1996-07-26
DK0515156T3 (en) 1996-06-17
DE69208144T2 (en) 1996-09-05
IL116109A0 (en) 1996-01-31
EP0515157A1 (en) 1992-11-25
CZ285220B6 (en) 1999-06-16
AU668086B2 (en) 1996-04-26
CN1067245A (en) 1992-12-23
IL116176A0 (en) 1996-01-31
JPH05186465A (en) 1993-07-27
EP0515156A1 (en) 1992-11-25
NO921988D0 (en) 1992-05-20
OA10212A (en) 1997-10-07
WO1992020696A1 (en) 1992-11-26
HU221850B1 (en) 2003-02-28
PL170869B1 (en) 1997-01-31
FI935150A0 (en) 1993-11-19
DE69221936D1 (en) 1997-10-09
CA2069024A1 (en) 1992-11-22
ZA923641B (en) 1993-02-24
IL101931A0 (en) 1992-12-30
CN1229079A (en) 1999-09-22
HU9303296D0 (en) 1994-03-28
DK0515157T3 (en) 1997-09-29
IE921618A1 (en) 1992-12-02
SK279438B6 (en) 1998-11-04
RU2105009C1 (en) 1998-02-20
CZ249293A3 (en) 1994-03-16
SK281954B6 (en) 2001-09-11
AU655973B2 (en) 1995-01-19
US5696254A (en) 1997-12-09
AU1690892A (en) 1992-12-30
JP2001354667A (en) 2001-12-25
CZ222496A3 (en) 1999-04-14
ES2104832T3 (en) 1997-10-16
PL176026B1 (en) 1999-03-31
JP3330972B2 (en) 2002-10-07
MX9202395A (en) 1993-02-01
BG61695B1 (en) 1998-03-31
CN1067654A (en) 1993-01-06
CN1050603C (en) 2000-03-22
FI106377B (en) 2001-01-31
GR3024617T3 (en) 1997-12-31
RU2223960C2 (en) 2004-02-20
KR920021576A (en) 1992-12-18
DE69208144D1 (en) 1996-03-21
AU1639592A (en) 1992-11-26
CN1116204A (en) 1996-02-07
JP3704055B2 (en) 2005-10-05
NO300593B1 (en) 1997-06-23
US5756706A (en) 1998-05-26
BG98311A (en) 1994-08-30
US5693787A (en) 1997-12-02
PL168910B1 (en) 1996-05-31
MD1155C2 (en) 1999-10-31
RU2163909C2 (en) 2001-03-10
GT199800047A (en) 1999-08-26
BG98310A (en) 1994-01-03
MX9202404A (en) 1993-08-31
IE76741B1 (en) 1997-11-05
FI935150A (en) 1993-11-19
NO921988L (en) 1992-11-23
JP3229013B2 (en) 2001-11-12
CN1038591C (en) 1998-06-03
HK1002431A1 (en) 1998-08-21
CN1109030C (en) 2003-05-21
IL101931A (en) 1996-12-05
IE921619A1 (en) 1992-12-02
EP0515156B1 (en) 1996-02-07
TW366349B (en) 1999-08-11
EE03044B1 (en) 1997-10-15
KR100232012B1 (en) 1999-12-01
HUT67726A (en) 1995-04-28
AU1691392A (en) 1992-12-30
SK129393A3 (en) 1994-07-06
WO1992020669A1 (en) 1992-11-26
KR920021575A (en) 1992-12-18
MD950172A (en) 1996-08-30
KR100242921B1 (en) 2000-03-15
IL116176A (en) 1998-02-08
HU223838B1 (en) 2005-02-28
JPH05186463A (en) 1993-07-27
MD1155B2 (en) 1999-02-28
FI935151A0 (en) 1993-11-19
CZ249393A3 (en) 1994-04-13
SG43863A1 (en) 1997-11-14
TW467907B (en) 2001-12-11
CN1083450C (en) 2002-04-24
NO301010B1 (en) 1997-09-01
CZ284975B6 (en) 1999-04-14
ATE157662T1 (en) 1997-09-15
CN1229080A (en) 1999-09-22
IL116109A (en) 1998-12-27
EP0515157B1 (en) 1997-09-03
NO921989D0 (en) 1992-05-20
CN1035555C (en) 1997-08-06
NO921989L (en) 1992-11-23
NZ242817A (en) 1995-03-28
TWI245046B (en) 2005-12-11
CA2069024C (en) 1997-09-23
RU2140925C1 (en) 1999-11-10
ES2084937T3 (en) 1996-05-16
FI935151A (en) 1993-11-19
IL101932A0 (en) 1992-12-30
FI109025B (en) 2002-05-15
CN1097049C (en) 2002-12-25
AU1639492A (en) 1992-11-26
HUT67471A (en) 1995-04-28
SK129493A3 (en) 1994-11-09
RO116812B1 (en) 2001-06-29

Similar Documents

Publication Publication Date Title
AU1639492A (en) Processes for the diastereoselective synthesis of nucleosides
RU93058554A (en) WAYS OF DIASTEROSELECTIVE SYNTHESIS OF NUCLEOSIDES
RU93058362A (en) METHODS FOR DIASTEROSELECTIVE SYNTHESIS OF NUCLEOSIDES, INTERMEDIATE COMPOUNDS, METHODS FOR PRODUCING INTERMEDIATE COMPOUNDS

Legal Events

Date Code Title Description
EEER Examination request
MKEX Expiry