WO2007075876A3 - Process for preparing a synthetic intermediate for preparation of branched nucleosides - Google Patents

Process for preparing a synthetic intermediate for preparation of branched nucleosides Download PDF

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Publication number
WO2007075876A3
WO2007075876A3 PCT/US2006/048769 US2006048769W WO2007075876A3 WO 2007075876 A3 WO2007075876 A3 WO 2007075876A3 US 2006048769 W US2006048769 W US 2006048769W WO 2007075876 A3 WO2007075876 A3 WO 2007075876A3
Authority
WO
WIPO (PCT)
Prior art keywords
preparation
preparing
lactone
synthetic intermediate
branched nucleosides
Prior art date
Application number
PCT/US2006/048769
Other languages
French (fr)
Other versions
WO2007075876A2 (en
Inventor
Benjamin Alexander Mayes
Adel Moussa
Original Assignee
Idenix Pharmaceuticals Inc
Benjamin Alexander Mayes
Adel Moussa
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 Idenix Pharmaceuticals Inc, Benjamin Alexander Mayes, Adel Moussa filed Critical Idenix Pharmaceuticals Inc
Priority to JP2008547541A priority Critical patent/JP5254033B2/en
Priority to ES06847905T priority patent/ES2422290T3/en
Priority to EP06847905.4A priority patent/EP1976382B1/en
Priority to CA2634749A priority patent/CA2634749C/en
Publication of WO2007075876A2 publication Critical patent/WO2007075876A2/en
Publication of WO2007075876A3 publication Critical patent/WO2007075876A3/en
Priority to HK09103302.8A priority patent/HK1123682A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/24—Condensed ring systems having three or more rings
    • 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
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D309/30—Oxygen atoms, e.g. delta-lactones
    • 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
    • C07H19/048—Pyridine 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
    • C07H19/22—Pteridine radicals

Abstract

A process is provided for the preparation of a key intermediate in the preparation of 2'-branched nucleoside compounds. The process includes contacting a protected precursor 3,4-O-isopropylidene-2-C-substituted-D-arabinono-l,5-lactone with a fluorinating agent under anhydrous conditions and converting the precursor into a protected 2-deoxy-2-halo-2-C-disubstituted ribono-l,5-lactone and optionally into a 2- deoxy-2-halo-2-C-disubstituted ribono- 1 ,4-lactone.
PCT/US2006/048769 2005-12-23 2006-12-22 Process for preparing a synthetic intermediate for preparation of branched nucleosides WO2007075876A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2008547541A JP5254033B2 (en) 2005-12-23 2006-12-22 Process for the production of synthetic intermediates for the preparation of branched nucleosides
ES06847905T ES2422290T3 (en) 2005-12-23 2006-12-22 Procedure for preparing a synthetic intermediate for the preparation of branched nucleosides
EP06847905.4A EP1976382B1 (en) 2005-12-23 2006-12-22 Process for preparing a synthetic intermediate for preparation of branched nucleosides
CA2634749A CA2634749C (en) 2005-12-23 2006-12-22 Process for preparing a synthetic intermediate for preparation of branched nucleosides
HK09103302.8A HK1123682A1 (en) 2005-12-23 2009-04-07 Process for preparing a synthetic intermediate for preparation of branched nucleosides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US75350705P 2005-12-23 2005-12-23
US60/753,507 2005-12-23

Publications (2)

Publication Number Publication Date
WO2007075876A2 WO2007075876A2 (en) 2007-07-05
WO2007075876A3 true WO2007075876A3 (en) 2007-09-13

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2006/048769 WO2007075876A2 (en) 2005-12-23 2006-12-22 Process for preparing a synthetic intermediate for preparation of branched nucleosides

Country Status (7)

Country Link
US (1) US7781576B2 (en)
EP (1) EP1976382B1 (en)
JP (1) JP5254033B2 (en)
CA (1) CA2634749C (en)
ES (1) ES2422290T3 (en)
HK (1) HK1123682A1 (en)
WO (1) WO2007075876A2 (en)

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MY164523A (en) 2000-05-23 2017-12-29 Univ Degli Studi Cagliari Methods and compositions for treating hepatitis c virus
EP1736478B1 (en) 2000-05-26 2015-07-22 IDENIX Pharmaceuticals, Inc. Methods and compositions for treating flaviviruses and pestiviruses
AP2005003213A0 (en) * 2002-06-28 2005-03-31 Univ Cagliari 2'-C-methyl-3'-O-L-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections.
US7608600B2 (en) * 2002-06-28 2009-10-27 Idenix Pharmaceuticals, Inc. Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections
HUE033832T2 (en) 2002-11-15 2018-01-29 Idenix Pharmaceuticals Llc 2'-methyl nucleosides in combination with interferon and flaviviridae mutation
CA2634749C (en) 2005-12-23 2014-08-19 Idenix Pharmaceuticals, Inc. Process for preparing a synthetic intermediate for preparation of branched nucleosides
US7951789B2 (en) 2006-12-28 2011-05-31 Idenix Pharmaceuticals, Inc. Compounds and pharmaceutical compositions for the treatment of viral infections
WO2012154321A1 (en) 2011-03-31 2012-11-15 Idenix Pharmaceuticals, Inc. Compounds and pharmaceutical compositions for the treatment of viral infections
JP2014526474A (en) 2011-09-12 2014-10-06 アイディニックス ファーマシューティカルズ インコーポレイテッド Compounds and pharmaceutical compositions for the treatment of viral infections
AR088441A1 (en) 2011-09-12 2014-06-11 Idenix Pharmaceuticals Inc SUBSTITUTED CARBONYLOXYMETHYLPHOSPHORAMIDATE COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS FOR THE TREATMENT OF VIRAL INFECTIONS
US8507460B2 (en) 2011-10-14 2013-08-13 Idenix Pharmaceuticals, Inc. Substituted 3′,5′-cyclic phosphates of purine nucleotide compounds and pharmaceutical compositions for the treatment of viral infections
WO2013177219A1 (en) 2012-05-22 2013-11-28 Idenix Pharmaceuticals, Inc. D-amino acid compounds for liver disease
WO2013177195A1 (en) 2012-05-22 2013-11-28 Idenix Pharmaceuticals, Inc. 3',5'-cyclic phosphate prodrugs for hcv infection
US9109001B2 (en) 2012-05-22 2015-08-18 Idenix Pharmaceuticals, Inc. 3′,5′-cyclic phosphoramidate prodrugs for HCV infection
CN103420955B (en) * 2012-05-23 2016-09-28 浙江瑞博制药有限公司 A kind of preparation method of fluoro ribose lactone
SG11201407336PA (en) 2012-05-25 2015-03-30 Janssen Sciences Ireland Uc Uracyl spirooxetane nucleosides
WO2014052638A1 (en) 2012-09-27 2014-04-03 Idenix Pharmaceuticals, Inc. Esters and malonates of sate prodrugs
US10513534B2 (en) 2012-10-08 2019-12-24 Idenix Pharmaceuticals Llc 2′-chloro nucleoside analogs for HCV infection
CN103724301A (en) 2012-10-10 2014-04-16 上海特化医药科技有限公司 (2R)-2-desoxy-2,2-disubstituted-1,4-ribonolactones, preparation method and purpose thereof
WO2014066239A1 (en) 2012-10-22 2014-05-01 Idenix Pharmaceuticals, Inc. 2',4'-bridged nucleosides for hcv infection
EP2935304A1 (en) 2012-12-19 2015-10-28 IDENIX Pharmaceuticals, Inc. 4'-fluoro nucleosides for the treatment of hcv
US9309275B2 (en) 2013-03-04 2016-04-12 Idenix Pharmaceuticals Llc 3′-deoxy nucleosides for the treatment of HCV
WO2014137930A1 (en) 2013-03-04 2014-09-12 Idenix Pharmaceuticals, Inc. Thiophosphate nucleosides for the treatment of hcv
EP2970357A1 (en) 2013-03-13 2016-01-20 IDENIX Pharmaceuticals, Inc. Amino acid phosphoramidate pronucleotides of 2'-cyano, azido and amino nucleosides for the treatment of hcv
US9187515B2 (en) 2013-04-01 2015-11-17 Idenix Pharmaceuticals Llc 2′,4′-fluoro nucleosides for the treatment of HCV
EP3004130B1 (en) 2013-06-05 2019-08-07 Idenix Pharmaceuticals LLC. 1',4'-thio nucleosides for the treatment of hcv
CN103288906A (en) * 2013-06-26 2013-09-11 湖南欧亚生物有限公司 A 3,5 - bis-O-benzoyl-2-C-methyl-C-methyl C-4 - (1,2,4 - triazolyl) uridine and a synthesis method thereof
EP3027636B1 (en) 2013-08-01 2022-01-05 Idenix Pharmaceuticals LLC D-amino acid phosphoramidate pronucleotides of halogeno pyrimidine compounds for liver disease
US10202411B2 (en) 2014-04-16 2019-02-12 Idenix Pharmaceuticals Llc 3′-substituted methyl or alkynyl nucleosides nucleotides for the treatment of HCV
CN105418547A (en) * 2015-11-17 2016-03-23 海门慧聚药业有限公司 Preparation for sofosbuvir key intermediate
CN106083961B (en) * 2016-07-13 2019-02-22 南通常佑药业科技有限公司 A kind of preparation method of the fluoro- 2 '-methylurea glycosides of (2 ' R) -2 '-deoxidations -2 ' -
CN106366057B (en) * 2016-08-25 2019-05-14 安徽华昌高科药业有限公司 A kind of synthetic method of Suo Feibuwei intermediate

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5021562A (en) * 1989-05-15 1991-06-04 Monsanto Company Method for azide displacement of α-triflates of 1,5-lactones
US6448415B1 (en) * 2000-07-22 2002-09-10 Hanchem Co., Ltd. Chirality conversion method in lactone sugar compounds
US20050009737A1 (en) * 2003-05-30 2005-01-13 Jeremy Clark Modified fluorinated nucleoside analogues
US20050020825A1 (en) * 2002-12-12 2005-01-27 Richard Storer Process for the production of 2'-branched nucleosides
US20050059632A1 (en) * 2003-06-30 2005-03-17 Richard Storer Synthesis of beta-L-2'-deoxy nucleosides

Family Cites Families (151)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6458772B1 (en) 1909-10-07 2002-10-01 Medivir Ab Prodrugs
US3074929A (en) * 1955-08-11 1963-01-22 Burroughs Wellcome Co Glycosides of 6-mercaptopurine
GB924246A (en) 1958-12-23 1963-04-24 Wellcome Found Purine derivatives and their preparation
US3116282A (en) 1960-04-27 1963-12-31 Upjohn Co Pyrimidine nucleosides and process
GB984877A (en) 1962-08-16 1965-03-03 Waldhof Zellstoff Fab Improvements in and relating to 6-halonucleosides
FR1498856A (en) 1965-11-15 1968-01-10
GB1163103A (en) 1965-11-15 1969-09-04 Merck & Co Inc Ribofuranosyl Purine Derivatives
FR1521076A (en) 1966-05-02 1968-04-12 Merck & Co Inc Substituted purine nucleosides
DE1695411A1 (en) 1966-05-02 1971-04-15 Merck & Co Inc Substituted purine nucleosides and processes for their preparation
US3480613A (en) 1967-07-03 1969-11-25 Merck & Co Inc 2-c or 3-c-alkylribofuranosyl - 1-substituted compounds and the nucleosides thereof
DE2122991C2 (en) * 1971-05-04 1982-06-09 Schering Ag, 1000 Berlin Und 4619 Bergkamen Process for the preparation of cytosine and 6-azacytosine nucleosides
USRE29835E (en) 1971-06-01 1978-11-14 Icn Pharmaceuticals 1,2,4-Triazole nucleosides
US3798209A (en) * 1971-06-01 1974-03-19 Icn Pharmaceuticals 1,2,4-triazole nucleosides
US4022889A (en) * 1974-05-20 1977-05-10 The Upjohn Company Therapeutic compositions of antibiotic U-44,590 and methods for using the same
DE2508312A1 (en) 1975-02-24 1976-09-02 Schering Ag NEW PROCESS FOR THE PRODUCTION OF NUCLEOSIDES
US4058602A (en) 1976-08-09 1977-11-15 The United States Of America As Represented By The Department Of Health, Education And Welfare Synthesis, structure, and antitumor activity of 5,6-dihydro-5-azacytidine
DE2757365A1 (en) * 1977-12-20 1979-06-21 Schering Ag NEW PROCESS FOR THE PRODUCTION OF NUCLEOSIDES
DE2852721A1 (en) 1978-12-06 1980-06-26 Basf Ag METHOD FOR REPRESENTING POTASSIUM RIBONATE AND RIBONOLACTONE
US4239753A (en) 1978-12-12 1980-12-16 The Upjohn Company Composition of matter and process
US4522811A (en) * 1982-07-08 1985-06-11 Syntex (U.S.A.) Inc. Serial injection of muramyldipeptides and liposomes enhances the anti-infective activity of muramyldipeptides
FR2562543B1 (en) 1984-04-10 1987-09-25 Elf Aquitaine NOVEL CYCLIC PHOSPHONITES, THEIR PREPARATION AND APPLICATIONS
NL8403224A (en) * 1984-10-24 1986-05-16 Oce Andeno Bv DIOXAPHOSPHORINANS, THEIR PREPARATION AND THE USE FOR SPLITTING OF OPTICALLY ACTIVE COMPOUNDS.
JPS61204193A (en) 1985-03-05 1986-09-10 Takeda Chem Ind Ltd Production of cytosine nuceoside
US6448392B1 (en) 1985-03-06 2002-09-10 Chimerix, Inc. Lipid derivatives of antiviral nucleosides: liposomal incorporation and method of use
US5223263A (en) * 1988-07-07 1993-06-29 Vical, Inc. Liponucleotide-containing liposomes
US4605659A (en) 1985-04-30 1986-08-12 Syntex (U.S.A.) Inc. Purinyl or pyrimidinyl substituted hydroxycyclopentane compounds useful as antivirals
US4754026A (en) * 1985-06-04 1988-06-28 Takeda Chemical Industries, Ltd. Conversion of uracil derivatives to cytosine derivatives
DE3714473A1 (en) 1987-04-30 1988-11-10 Basf Ag CONTINUOUS PROCESS FOR EPIMERIZING SUGAR, ESPECIALLY FROM D-ARABINOSE TO D-RIBOSE
GB8719367D0 (en) 1987-08-15 1987-09-23 Wellcome Found Therapeutic compounds
US5246924A (en) 1987-09-03 1993-09-21 Sloan-Kettering Institute For Cancer Research Method for treating hepatitis B virus infections using 1-(2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil
US4880784A (en) 1987-12-21 1989-11-14 Brigham Young University Antiviral methods utilizing ribofuranosylthiazolo[4,5-d]pyrimdine derivatives
US5122517A (en) * 1988-06-10 1992-06-16 Regents Of The University Of Minnesota Antiviral combination comprising nucleoside analogs
GB8815265D0 (en) * 1988-06-27 1988-08-03 Wellcome Found Therapeutic nucleosides
US6599887B2 (en) 1988-07-07 2003-07-29 Chimerix, Inc. Methods of treating viral infections using antiviral liponucleotides
US6252060B1 (en) * 1988-07-07 2001-06-26 Nexstar Pharmaceuticals, Inc. Antiviral liponucleosides: treatment of hepatitis B
SE8802687D0 (en) 1988-07-20 1988-07-20 Astra Ab NUCLEOSIDE DERIVATIVES
US5744600A (en) * 1988-11-14 1998-04-28 Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic Phosphonomethoxy carbocyclic nucleosides and nucleotides
US5616702A (en) 1988-11-15 1997-04-01 Merrell Pharmaceuticals Inc. 2-'-ethenylidene cytidine, uridine and guanosine derivatives
US5705363A (en) * 1989-03-02 1998-01-06 The Women's Research Institute Recombinant production of human interferon τ polypeptides and nucleic acids
US5194654A (en) * 1989-11-22 1993-03-16 Vical, Inc. Lipid derivatives of phosphonoacids for liposomal incorporation and method of use
US5411947A (en) * 1989-06-28 1995-05-02 Vestar, Inc. Method of converting a drug to an orally available form by covalently bonding a lipid to the drug
US5463092A (en) 1989-11-22 1995-10-31 Vestar, Inc. Lipid derivatives of phosphonacids for liposomal incorporation and method of use
US6060592A (en) * 1990-01-11 2000-05-09 Isis Pharmaceuticals, Inc. Pyrimidine nucleoside compounds and oligonucleoside compounds containing same
US5200514A (en) * 1990-01-19 1993-04-06 University Of Georgia Research Foundation, Inc. Synthesis of 2'-deoxypyrimidine nucleosides
US5204466A (en) * 1990-02-01 1993-04-20 Emory University Method and compositions for the synthesis of bch-189 and related compounds
FR2662165B1 (en) 1990-05-18 1992-09-11 Univ Paris Curie BRANCHED NUCLEOSIDE DERIVATIVES, THEIR PREPARATION PROCESS AND THEIR USE AS MEDICAMENTS.
CA2083961A1 (en) * 1990-05-29 1991-11-30 Henk Van Den Bosch Synthesis of glycerol di- and triphosphate derivatives
US5627165A (en) 1990-06-13 1997-05-06 Drug Innovation & Design, Inc. Phosphorous prodrugs and therapeutic delivery systems using same
US5372808A (en) 1990-10-17 1994-12-13 Amgen Inc. Methods and compositions for the treatment of diseases with consensus interferon while reducing side effect
US5543390A (en) 1990-11-01 1996-08-06 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University Covalent microparticle-drug conjugates for biological targeting
US5827819A (en) 1990-11-01 1998-10-27 Oregon Health Sciences University Covalent polar lipid conjugates with neurologically active compounds for targeting
US5256641A (en) 1990-11-01 1993-10-26 State Of Oregon Covalent polar lipid-peptide conjugates for immunological targeting
US5149794A (en) 1990-11-01 1992-09-22 State Of Oregon Covalent lipid-drug conjugates for drug targeting
US5543389A (en) 1990-11-01 1996-08-06 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education On Behalf Of The Oregon Health Sciences University, A Non Profit Organization Covalent polar lipid-peptide conjugates for use in salves
IL100502A (en) 1991-01-03 1995-12-08 Iaf Biochem Int Pharmaceutical compositions containing cis-4-amino-1(hydroxymethyl-1,3-oxathiolan-5-yl)-1H-pyrimid-2-one nucleoside or its derivatives
JPH04266880A (en) 1991-02-22 1992-09-22 Japan Tobacco Inc Production of 3-dpa-lactone
US5157027A (en) 1991-05-13 1992-10-20 E. R. Squibb & Sons, Inc. Bisphosphonate squalene synthetase inhibitors and method
JPH0525152A (en) * 1991-07-22 1993-02-02 Japan Tobacco Inc Production of 3-dpa-lactone
US5554728A (en) 1991-07-23 1996-09-10 Nexstar Pharmaceuticals, Inc. Lipid conjugates of therapeutic peptides and protease inhibitors
TW224053B (en) 1991-09-13 1994-05-21 Paul B Chretien
US5676942A (en) 1992-02-10 1997-10-14 Interferon Sciences, Inc. Composition containing human alpha interferon species proteins and method for use thereof
US5821357A (en) 1992-06-22 1998-10-13 Eli Lilly And Company Stereoselective glycosylation process for preparing 2'-deoxy-2',2'-difluoropurine and triazole nucleosides
US5256797A (en) 1992-06-22 1993-10-26 Eli Lilly And Company Process for separating 2-deoxy-2,2-difluoro-D-ribofuranosyl alkylsulfonate anomers
US5401861A (en) * 1992-06-22 1995-03-28 Eli Lilly And Company Low temperature process for preparing alpha-anomer enriched 2-deoxy-2,2-difluoro-D-ribofuranosyl sulfonates
US5606048A (en) * 1992-06-22 1997-02-25 Eli Lilly And Company Stereoselective glycosylation process for preparing 2'-Deoxy-2', 2'-difluoronucleosides and 2'-deoxy-2'-fluoronucleosides
US5371210A (en) 1992-06-22 1994-12-06 Eli Lilly And Company Stereoselective fusion glycosylation process for preparing 2'-deoxy-2',2'-difluoronucleosides and 2'-deoxy-2'-fluoronucleosides
DE4224737A1 (en) 1992-07-27 1994-02-03 Herbert Prof Dr Schott New cytosine analogues with lipophilic protected amino gps. - for treatment of cancer and virus diseases e.g. AIDS, are more protected against enzymatic des-amination and can be used in higher doses than unprotected cpds.
CA2105112C (en) 1992-09-01 2005-08-02 Thomas C. Britton A process for anomerizing nucleosides
GB9226729D0 (en) 1992-12-22 1993-02-17 Wellcome Found Therapeutic combination
GB9307043D0 (en) 1993-04-05 1993-05-26 Norsk Hydro As Chemical compounds
US6156501A (en) 1993-10-26 2000-12-05 Affymetrix, Inc. Arrays of modified nucleic acid probes and methods of use
US5587362A (en) 1994-01-28 1996-12-24 Univ. Of Ga Research Foundation L-nucleosides
US5696277A (en) 1994-11-15 1997-12-09 Karl Y. Hostetler Antiviral prodrugs
DK0747389T3 (en) 1994-12-13 2004-01-26 Taiho Pharmaceutical Co Ltd 3'-substituted nucleoside derivatives
DE19513330A1 (en) * 1995-04-03 1996-10-10 Schering Ag New process for the production of nucleosides
US5977061A (en) 1995-04-21 1999-11-02 Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic N6 - substituted nucleotide analagues and their use
CA2231442A1 (en) 1995-09-07 1997-03-13 University Of Georgia Research Foundation, Inc. Therapeutic azide compounds
US5908621A (en) * 1995-11-02 1999-06-01 Schering Corporation Polyethylene glycol modified interferon therapy
US5980884A (en) 1996-02-05 1999-11-09 Amgen, Inc. Methods for retreatment of patients afflicted with Hepatitis C using consensus interferon
GB9609932D0 (en) * 1996-05-13 1996-07-17 Hoffmann La Roche Use of IL-12 and IFN alpha for the treatment of infectious diseases
CA2267279A1 (en) * 1996-10-16 1998-04-23 Devron Averett Monocyclic l-nucleosides, analogs and uses thereof
CA2269213A1 (en) * 1996-10-28 1998-05-07 The University Of Washington Induction of viral mutation by incorporation of miscoding ribonucleoside analogs into viral rna
US6248878B1 (en) * 1996-12-24 2001-06-19 Ribozyme Pharmaceuticals, Inc. Nucleoside analogs
US6472373B1 (en) 1997-09-21 2002-10-29 Schering Corporation Combination therapy for eradicating detectable HCV-RNA in antiviral treatment naive patients having chronic hepatitis C infection
US6172046B1 (en) * 1997-09-21 2001-01-09 Schering Corporation Combination therapy for eradicating detectable HCV-RNA in patients having chronic Hepatitis C infection
CA2322008C (en) * 1998-02-25 2011-06-28 Emory University 2'-fluoronucleosides
US6312662B1 (en) * 1998-03-06 2001-11-06 Metabasis Therapeutics, Inc. Prodrugs phosphorus-containing compounds
KR100389853B1 (en) * 1998-03-06 2003-08-19 삼성전자주식회사 Method for recording and reproducing catalog information
US6833361B2 (en) * 1998-05-26 2004-12-21 Ribapharm, Inc. Nucleosides having bicyclic sugar moiety
JP3839667B2 (en) * 1998-06-08 2006-11-01 エフ．ホフマン−ラ ロシュ アーゲー Use of Peg-INF-alpha and ribavirin for the treatment of chronic hepatitis C
DE122007000062I1 (en) 1998-08-10 2007-12-20 Idenix Cayman Ltd Beta-L-2'-deoxynucleosides for the treatment of hepatitis B virus
US6444652B1 (en) 1998-08-10 2002-09-03 Novirio Pharmaceuticals Limited β-L-2'-deoxy-nucleosides for the treatment of hepatitis B
US6277830B1 (en) 1998-10-16 2001-08-21 Schering Corporation 5′-amino acid esters of ribavirin and the use of same to treat hepatitis C with interferon
CA2252144A1 (en) 1998-10-16 2000-04-16 University Of Alberta Dual action anticancer prodrugs
US6458773B1 (en) 1998-11-05 2002-10-01 Emory University Nucleoside with anti-hepatitis B virus activity
EP1155017B1 (en) 1999-02-22 2003-01-15 Shire Biochem Inc. [1,8] naphthyridine derivatives having antiviral activity
US6831069B2 (en) 1999-08-27 2004-12-14 Ribapharm Inc. Pyrrolo[2,3-d]pyrimidine nucleoside analogs
WO2001018013A1 (en) * 1999-09-08 2001-03-15 Metabasis Therapeutics, Inc. Prodrugs for liver specific drug delivery
US6566365B1 (en) * 1999-11-04 2003-05-20 Biochem Pharma Inc. Method for the treatment of Flaviviridea viral infection using nucleoside analogues
MXPA02006156A (en) 1999-12-22 2003-09-22 Metabasis Therapeutics Inc Novel bisamidate phosphonate prodrugs.
US6455508B1 (en) 2000-02-15 2002-09-24 Kanda S. Ramasamy Methods for treating diseases with tirazole and pyrrolo-pyrimidine ribofuranosyl nucleosides
US6495677B1 (en) 2000-02-15 2002-12-17 Kanda S. Ramasamy Nucleoside compounds
US7056895B2 (en) * 2000-02-15 2006-06-06 Valeant Pharmaceuticals International Tirazole nucleoside analogs and methods for using same
EA200200778A1 (en) * 2000-02-18 2003-06-26 Шайре Байокем Инк. METHOD OF TREATMENT OR PREVENTION OF HEPATITIS C INFECTION IN THE ORGANISM ORGANISM, PHARMACEUTICAL COMPOSITION AGAINST FLAVIVIRUS, CONNECTION OF FORMULA Ib - AN ACTIVE AGENT FOR THE TREATMENT OR PREVENTION OF EFFECTECH EFFECTURES Ib - AN ACTIVE AGENT FOR THE TREATMENT OR PREVENTION INEKEKHEKUSA Ib - AN ACTIVE AGENT FOR THE TREATMENT OR PROTECTION
DE60136620D1 (en) * 2000-04-13 2009-01-02 Pharmasset Inc 3 OR 2 HYDROXYMETHYL SUBSTITUTED NUCLEOSIDE DERIVATIVES AND THEIR USE FOR THE TREATMENT OF VIRUS INFECTIONS
EP1282632A1 (en) * 2000-04-20 2003-02-12 Schering Corporation Ribavirin-interferon alfa combination therapy for eradicating detectable hcv-rna in patients having chronic hepatitis c infection
MY164523A (en) * 2000-05-23 2017-12-29 Univ Degli Studi Cagliari Methods and compositions for treating hepatitis c virus
IL153078A0 (en) * 2000-05-26 2003-06-24 Idenix Cayman Ltd Methods for treating hepatitis delta virus infection with beta-l-2' deoxy nucleosides
US6787526B1 (en) 2000-05-26 2004-09-07 Idenix Pharmaceuticals, Inc. Methods of treating hepatitis delta virus infection with β-L-2′-deoxy-nucleosides
EP1736478B1 (en) * 2000-05-26 2015-07-22 IDENIX Pharmaceuticals, Inc. Methods and compositions for treating flaviviruses and pestiviruses
US6875751B2 (en) * 2000-06-15 2005-04-05 Idenix Pharmaceuticals, Inc. 3′-prodrugs of 2′-deoxy-β-L-nucleosides
US6815542B2 (en) * 2000-06-16 2004-11-09 Ribapharm, Inc. Nucleoside compounds and uses thereof
US20030008841A1 (en) * 2000-08-30 2003-01-09 Rene Devos Anti-HCV nucleoside derivatives
AU2002213343A1 (en) 2000-10-18 2002-04-29 Schering Corporation Ribavirin-pegylated interferon alfa HCV combination therapy
WO2002033128A2 (en) 2000-10-18 2002-04-25 Pharmasset Limited Multiplex quantification of nucleic acids in diseased cells
CN101862345B (en) * 2000-10-18 2014-06-04 吉利德制药有限责任公司 Modified nucleosides for treatment of viral infections and abnormal cellular proliferation
EP1366055A2 (en) 2000-12-15 2003-12-03 Pharmasset Limited Antiviral agents for treatment of flaviviridae infections
WO2002057287A2 (en) * 2001-01-22 2002-07-25 Merck & Co., Inc. Nucleoside derivatives as inhibitors of rna-dependent rna viral polymerase
US7105499B2 (en) * 2001-01-22 2006-09-12 Merck & Co., Inc. Nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase
NZ540956A (en) 2001-03-01 2007-01-26 Pharmasset Inc Method for the synthesis of 2',3'-dideoxy-2',3'-didehydronucleosides
GB0112617D0 (en) * 2001-05-23 2001-07-18 Hoffmann La Roche Antiviral nucleoside derivatives
GB0114286D0 (en) 2001-06-12 2001-08-01 Hoffmann La Roche Nucleoside Derivatives
WO2003000200A2 (en) 2001-06-22 2003-01-03 Pharmasset Ltd. β-2'-OR 3'-HALONUCLEOSIDES
WO2003024461A1 (en) * 2001-09-20 2003-03-27 Schering Corporation Hcv combination therapy
US20040006002A1 (en) * 2001-09-28 2004-01-08 Jean-Pierre Sommadossi Methods and compositions for treating flaviviruses and pestiviruses using 4'-modified nucleoside
EP1569652A4 (en) * 2001-12-14 2008-07-02 Pharmasset Inc N sp 4 /sp-acylcytosine nucleosides for treatment of viral iinfections
CN1646534A (en) * 2002-02-14 2005-07-27 法玛塞特有限公司 Modified fluorinated nucleoside analogues
WO2003072757A2 (en) * 2002-02-28 2003-09-04 Biota, Inc. Nucleotide mimics and their prodrugs
US7247621B2 (en) * 2002-04-30 2007-07-24 Valeant Research & Development Antiviral phosphonate compounds and methods therefor
EP1501850A2 (en) * 2002-05-06 2005-02-02 Genelabs Technologies, Inc. Nucleoside derivatives for treating hepatitis c virus infection
AP2005003213A0 (en) * 2002-06-28 2005-03-31 Univ Cagliari 2'-C-methyl-3'-O-L-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections.
JP2006505537A (en) 2002-09-30 2006-02-16 ジェネラブス テクノロジーズ，インコーポレイテッド Nucleoside derivatives for treating hepatitis C virus infection
US7094768B2 (en) * 2002-09-30 2006-08-22 Genelabs Technologies, Inc. Nucleoside derivatives for treating hepatitis C virus infection
HUE033832T2 (en) * 2002-11-15 2018-01-29 Idenix Pharmaceuticals Llc 2'-methyl nucleosides in combination with interferon and flaviviridae mutation
TWI332507B (en) * 2002-11-19 2010-11-01 Hoffmann La Roche Antiviral nucleoside derivatives
WO2004084453A2 (en) 2003-03-20 2004-09-30 Microbiologica Quimica E Farmaceutica Ltd. METHODS OF MANUFACTURE OF 2'-DEOXY-β-L-NUCLEOSIDES
US20040259934A1 (en) 2003-05-01 2004-12-23 Olsen David B. Inhibiting Coronaviridae viral replication and treating Coronaviridae viral infection with nucleoside compounds
US20040229839A1 (en) 2003-05-14 2004-11-18 Biocryst Pharmaceuticals, Inc. Substituted nucleosides, preparation thereof and use as inhibitors of RNA viral polymerases
ES2276311T3 (en) * 2003-06-19 2007-06-16 F. Hoffmann-La Roche Ag PROCESS TO PRADERATE DERIVATIVES OF 4 '-AZIDONUCLEOSIDO.
US7144868B2 (en) * 2003-10-27 2006-12-05 Genelabs Technologies, Inc. Nucleoside compounds for treating viral infections
US20050137141A1 (en) * 2003-10-24 2005-06-23 John Hilfinger Prodrug composition
CA2543090A1 (en) 2003-10-27 2005-06-16 Genelabs Technologies, Inc. Nucleoside compounds for treating viral infections
US7157434B2 (en) * 2003-10-27 2007-01-02 Genelabs Technologies, Inc. Nucleoside compounds for treating viral infections
CN101023094B (en) 2004-07-21 2011-05-18 法莫赛特股份有限公司 Preparation of alkyl-substituted 2-deoxy-2-fluoro-d-ribofuranosyl pyrimidines and purines and their derivatives
DE602005015466D1 (en) * 2004-08-23 2009-08-27 Hoffmann La Roche ANTIVIRAL 4'-AZIDONUCLEOSIDE
PL3109244T3 (en) * 2004-09-14 2019-09-30 Gilead Pharmasset Llc Preparation of 2'fluoro-2'-alkyl-substituted or other optionally substituted ribofuranosyl pyrimidines and purines and their derivatives
US7414031B2 (en) * 2004-11-22 2008-08-19 Genelabs Technologies, Inc. 5-nitro-nucleoside compounds for treating viral infections
EP1853317A2 (en) 2005-02-09 2007-11-14 Migenix Inc. Compositions and methods for treating or preventing flaviviridae infections
DE102005012681A1 (en) 2005-03-18 2006-09-21 Weber, Lutz, Dr. New 1,5-dihydro-pyrrol-2-one compounds are HDM2 inhibitors, useful for treating e.g. stroke, heart infarct, ischemia, multiple sclerosis, Alzheimer's disease, degenerative disease, viral infection and cancer
AR056327A1 (en) 2005-04-25 2007-10-03 Genelabs Tech Inc NUCLEOSID COMPOUNDS FOR THE TREATMENT OF VIRAL INFECTIONS
CA2634749C (en) 2005-12-23 2014-08-19 Idenix Pharmaceuticals, Inc. Process for preparing a synthetic intermediate for preparation of branched nucleosides

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5021562A (en) * 1989-05-15 1991-06-04 Monsanto Company Method for azide displacement of α-triflates of 1,5-lactones
US6448415B1 (en) * 2000-07-22 2002-09-10 Hanchem Co., Ltd. Chirality conversion method in lactone sugar compounds
US20050020825A1 (en) * 2002-12-12 2005-01-27 Richard Storer Process for the production of 2'-branched nucleosides
US20050009737A1 (en) * 2003-05-30 2005-01-13 Jeremy Clark Modified fluorinated nucleoside analogues
US20050059632A1 (en) * 2003-06-30 2005-03-17 Richard Storer Synthesis of beta-L-2'-deoxy nucleosides

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