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WO2003105770A3 - Carbocyclic nucleoside analogs as rna-antivirals - Google Patents

Carbocyclic nucleoside analogs as rna-antivirals Download PDF

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Publication number
WO2003105770A3
WO2003105770A3 PCT/US2003/018841 US0318841W WO03105770A3 WO 2003105770 A3 WO2003105770 A3 WO 2003105770A3 US 0318841 W US0318841 W US 0318841W WO 03105770 A3 WO03105770 A3 WO 03105770A3
Authority
WO
WIPO (PCT)
Prior art keywords
rna
inhibitors
dependent rna
carbocyclic nucleoside
infection
Prior art date
Application number
PCT/US2003/018841
Other languages
French (fr)
Other versions
WO2003105770A2 (en
Inventor
Balkrishen Bhat
Neelima Bhat
Prasad Dande
Anne B Eldrup
David B Olsen
Malcolm Maccoss
Original Assignee
Merck & Co Inc
Isis Pharmaceuticals Inc
Balkrishen Bhat
Neelima Bhat
Prasad Dande
Anne B Eldrup
David B Olsen
Malcolm Maccoss
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 Merck & Co Inc, Isis Pharmaceuticals Inc, Balkrishen Bhat, Neelima Bhat, Prasad Dande, Anne B Eldrup, David B Olsen, Malcolm Maccoss filed Critical Merck & Co Inc
Priority to CA002488842A priority Critical patent/CA2488842A1/en
Priority to AU2003251524A priority patent/AU2003251524A1/en
Priority to JP2004512678A priority patent/JP2005533777A/en
Priority to EP03760371A priority patent/EP1515971A2/en
Publication of WO2003105770A2 publication Critical patent/WO2003105770A2/en
Publication of WO2003105770A3 publication Critical patent/WO2003105770A3/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H21/00Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • A61P31/14Antivirals for RNA viruses
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Virology (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Biotechnology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Genetics & Genomics (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

The present invention provides carbocyclic nucleoside compounds and certain derivatives thereof which are inhibitors of RNA-dependent RNA viral polymerase. These compounds are inhibitors of RNA-dependent RNA viral replication and are useful for the treatment of RNA-dependent RNA viral infection. They are particularly useful as inhibitors of hepatitis C virus (HCV) NS5B polymerase, as inhibitors of HCV replication, and/or for the treatment of hepatitis C infection. The invention also describes pharmaceutical compositions containing such carbocyclic nucleoside compounds alone or in combination with other agents active against RNA-dependent RNA viral infection, in particular HCV infection. Also disclosed are methods of inhibiting RNA-dependent RNA polymerase, inhibiting RNA-dependent RNA viral replication, and/or treating RNA-dependent RNA viral infection with the carbocyclic nucleoside compounds of the present invention
PCT/US2003/018841 2002-06-17 2003-06-14 Carbocyclic nucleoside derivatives as inhibitors of rna-dependent rna viral polymerase WO2003105770A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA002488842A CA2488842A1 (en) 2002-06-17 2003-06-14 Carbocyclic nucleoside analogs as rna-antivirals
AU2003251524A AU2003251524A1 (en) 2002-06-17 2003-06-14 Carbocyclic nucleoside analogs as RNA-antivirals
JP2004512678A JP2005533777A (en) 2002-06-17 2003-06-14 Carbocyclic nucleoside analogs as RNA antiviral agents
EP03760371A EP1515971A2 (en) 2002-06-17 2003-06-14 Carbocyclic nucleoside derivatives as inhibitors of rna-dependent rna viral polymerase

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US38916102P 2002-06-17 2002-06-17
US60/389,161 2002-06-17

Publications (2)

Publication Number Publication Date
WO2003105770A2 WO2003105770A2 (en) 2003-12-24
WO2003105770A3 true WO2003105770A3 (en) 2004-10-07

Family

ID=29736594

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2003/018841 WO2003105770A2 (en) 2002-06-17 2003-06-14 Carbocyclic nucleoside derivatives as inhibitors of rna-dependent rna viral polymerase

Country Status (5)

Country Link
EP (1) EP1515971A2 (en)
JP (1) JP2005533777A (en)
AU (1) AU2003251524A1 (en)
CA (1) CA2488842A1 (en)
WO (1) WO2003105770A2 (en)

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US7429572B2 (en) 2003-05-30 2008-09-30 Pharmasset, Inc. Modified fluorinated nucleoside analogues
US7456155B2 (en) 2002-06-28 2008-11-25 Idenix Pharmaceuticals, Inc. 2′-C-methyl-3′-O-L-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections
US7582618B2 (en) 2002-06-28 2009-09-01 Idenix Pharmaceuticals, Inc. 2′-C-methyl-3′-O-L-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections
US7598373B2 (en) 2002-12-12 2009-10-06 Idenix Pharmaceuticals, Inc. Process for the production of 2-C-methyl-D-ribonolactone
US7608597B2 (en) 2000-05-23 2009-10-27 Idenix Pharmaceuticals, Inc. Methods and compositions for treating hepatitis C virus
US7645745B2 (en) 2006-04-04 2010-01-12 Roche Palo Alto Llc Antiviral nucleosides
US7786110B2 (en) 2006-11-09 2010-08-31 Roche Palo Alto Llc Thiazole and oxazole-substituted arylamides as P2X3 and P2X2/3 antagonists
US7858654B2 (en) 2007-12-17 2010-12-28 Roche Palo Alto Llc Imidazole-substituted arylamides as P2X3 and P2X2/3 antagonists
US7989637B2 (en) 2007-12-17 2011-08-02 Roche Palo Alto Llc Triazole-substituted arylamides as P2X3 and P2X2/3 antagonists
US8048905B2 (en) 2007-12-17 2011-11-01 Roche Palo Alto Llc Tetrazole-substituted arylamides as P2X3 and P2X2/3 antagonists
US8440673B2 (en) 2007-12-17 2013-05-14 Roche Palo Alto Llc Pyrazole-substituted arylamides as P2X3 and P2X2/3 antagonists
US8841275B2 (en) 2010-11-30 2014-09-23 Gilead Pharmasset Llc 2′-spiro-nucleosides and derivatives thereof useful for treating hepatitis C virus and dengue virus infections
US8957046B2 (en) 2007-03-30 2015-02-17 Gilead Pharmasset Llc Nucleoside phosphoramidate prodrugs
US9045520B2 (en) 2008-12-23 2015-06-02 Gilead Pharmasset Llc Synthesis of purine nucleosides
US9243025B2 (en) 2011-03-31 2016-01-26 Idenix Pharmaceuticals, Llc Compounds and pharmaceutical compositions for the treatment of viral infections
US9393256B2 (en) 2011-09-16 2016-07-19 Gilead Pharmasset Llc Methods for treating HCV
US9549941B2 (en) 2011-11-29 2017-01-24 Gilead Pharmasset Llc Compositions and methods for treating hepatitis C virus

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KR20030036189A (en) 2000-05-26 2003-05-09 이데닉스(케이만)리미티드 Methods and compositions for treating flaviviruses and pestiviruses
TW200500374A (en) * 2002-06-28 2005-01-01 Idenlx Cayman Ltd 2' and 3' -nucleoside produrgs for treating flavivridae infections
AU2003256619A1 (en) 2002-07-24 2004-02-09 Isis Pharmaceuticals, Inc. Pyrrolopyrimidine thionucleoside analogs as antivirals
PT1576138T (en) 2002-11-15 2017-05-03 Idenix Pharmaceuticals Llc 2'-methyl nucleosides in combination with interferon and flaviviridae mutation
CN103304541A (en) 2004-02-20 2013-09-18 贝林格尔.英格海姆国际有限公司 Viral polymerase inhibitors
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
KR101177590B1 (en) 2004-09-14 2012-08-27 파마셋 인코포레이티드 Preparation of 2'-fluoro-2'-alkyl-substituted or other optionally substituted ribofuranosyl pyrimidines and purines and their derivatives
KR20070073805A (en) * 2004-09-24 2007-07-10 이데닉스 (케이만) 리미티드 Methods and compositions for treating flaviviruses, pestiviruses and hepaciviruses
US7951789B2 (en) 2006-12-28 2011-05-31 Idenix Pharmaceuticals, Inc. Compounds and pharmaceutical compositions for the treatment of viral infections
ES2758027T3 (en) 2007-08-02 2020-05-04 Millennium Pharm Inc Intermediates for the synthesis of E1 activity activating enzyme inhibitors
CA2724523A1 (en) 2008-06-06 2010-01-07 Scynexis, Inc. Novel macrocyclic peptides
TWI409265B (en) * 2008-08-20 2013-09-21 Merck Sharp & Dohme Substituted pyridine and pyrimidine derivatives and their use in treating viral infections
SG172359A1 (en) 2008-12-23 2011-07-28 Pharmasset Inc Nucleoside phosphoramidates
NZ617066A (en) 2008-12-23 2015-02-27 Gilead Pharmasset Llc Nucleoside analogs
TWI576352B (en) 2009-05-20 2017-04-01 基利法瑪席特有限責任公司 Nucleoside phosphoramidates
US8618076B2 (en) 2009-05-20 2013-12-31 Gilead Pharmasset Llc Nucleoside phosphoramidates
EP2445889B1 (en) 2009-06-22 2016-08-10 F.Hoffmann-La Roche Ag Novel benzoxazolone -substituted arylamides
JP5540087B2 (en) 2009-06-22 2014-07-02 エフ.ホフマン−ラ ロシュ アーゲー Novel indoles, indazoles and benzimidazole arylamides as P2X3 and / or P2X2 / 3 antagonists
EP2445868B1 (en) 2009-06-22 2013-12-18 F.Hoffmann-La Roche Ag Biphenyl amides useful as p2x3 and/or p2x2/3 receptors modulators
KR20120104239A (en) 2009-11-14 2012-09-20 에프. 호프만-라 로슈 아게 Biomarkers for predicting rapid response to hcv treatment
AU2010326781A1 (en) 2009-12-02 2012-04-19 F. Hoffmann-La Roche Ag Biomarkers for predicting sustained response to HCV treatment
PL2552930T3 (en) 2010-03-31 2016-02-29 Gilead Pharmasset Llc Crystalline (s)-isopropyl 2-(((s)-(((2r,3r,4r,5r)-5-(2,4-dioxo-3,4-dihydropyrimidin-1-(2h)-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate
TW201136945A (en) 2010-03-31 2011-11-01 Pharmasset Inc Purine nucleoside phosphoramidate
EP2552203B1 (en) 2010-04-01 2017-03-22 Idenix Pharmaceuticals LLC. Compounds and pharmaceutical compositions for the treatment of viral infections
EP2755983B1 (en) 2011-09-12 2017-03-15 Idenix Pharmaceuticals LLC. 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
US9109001B2 (en) 2012-05-22 2015-08-18 Idenix Pharmaceuticals, Inc. 3′,5′-cyclic phosphoramidate prodrugs for HCV infection
WO2013177219A1 (en) 2012-05-22 2013-11-28 Idenix Pharmaceuticals, Inc. D-amino acid compounds for liver disease
US9296778B2 (en) 2012-05-22 2016-03-29 Idenix Pharmaceuticals, Inc. 3′,5′-cyclic phosphate prodrugs for HCV infection
KR20150014457A (en) 2012-05-25 2015-02-06 얀센 알 앤드 디 아일랜드 Uracyl spirooxetane nucleosides
US9192621B2 (en) 2012-09-27 2015-11-24 Idenix Pharmaceuticals Llc Esters and malonates of SATE prodrugs
WO2014058801A1 (en) 2012-10-08 2014-04-17 Idenix Pharmaceuticals, Inc. 2'-chloro nucleoside analogs for hcv infection
EP2909222B1 (en) 2012-10-22 2021-05-26 Idenix Pharmaceuticals LLC 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
SG10201706949VA (en) 2013-01-31 2017-09-28 Gilead Pharmasset Llc Combination formulation of two antiviral compounds
US9309275B2 (en) 2013-03-04 2016-04-12 Idenix Pharmaceuticals Llc 3′-deoxy nucleosides for the treatment of HCV
US9339541B2 (en) 2013-03-04 2016-05-17 Merck Sharp & Dohme Corp. Thiophosphate nucleosides for the treatment of HCV
US20140271547A1 (en) 2013-03-13 2014-09-18 Idenix Pharmaceuticals, Inc. Amino acid phosphoramidate pronucleotides of 2'-cyano, azido and amino nucleosides for the treatment of hcv
RU2534613C2 (en) 2013-03-22 2014-11-27 Александр Васильевич Иващенко Alkyl2-{[(2r,3s,5r)-5-(4-amino-2-oxo-2h-pyrimidine-1-yl)- -hydroxy- tetrahydro-furan-2-ylmethoxy]-phenoxy-phosphorylamino}-proptonates, nucleoside inhibitors of rna-polymerase hcv ns5b, methods for producing and using them
EP2981542B1 (en) 2013-04-01 2021-09-15 Idenix Pharmaceuticals LLC 2',4'-fluoro nucleosides for the treatment of hcv
CN104151360B (en) * 2013-05-14 2019-02-22 北京美倍他药物研究有限公司 Phosphoric acid/phosphonate derivative and its medical usage
EP3004130B1 (en) 2013-06-05 2019-08-07 Idenix Pharmaceuticals LLC. 1',4'-thio nucleosides for the treatment of hcv
US20150037282A1 (en) 2013-08-01 2015-02-05 Idenix Pharmaceuticals, Inc. D-amino acid phosphoramidate pronucleotides of halogeno pyrimidine compounds for liver disease
SI3038601T1 (en) 2013-08-27 2020-07-31 Gilead Pharmasset Llc Combination formulation of two antiviral compounds
CN103524423B (en) 2013-09-18 2015-11-04 苏州乔纳森新材料科技有限公司 The preparation method of 4,6-dichloro-pyrimidine-5-acetaldehyde
CN103554035B (en) * 2013-10-29 2015-07-15 苏州乔纳森新材料科技有限公司 Preparation method of 4,6-dihalogenated pyridine-5-aldehyde
WO2015161137A1 (en) 2014-04-16 2015-10-22 Idenix Pharmaceuticals, Inc. 3'-substituted methyl or alkynyl nucleosides for the treatment of hcv
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Cited By (19)

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Publication number Priority date Publication date Assignee Title
US7608597B2 (en) 2000-05-23 2009-10-27 Idenix Pharmaceuticals, Inc. Methods and compositions for treating hepatitis C virus
US7456155B2 (en) 2002-06-28 2008-11-25 Idenix Pharmaceuticals, Inc. 2′-C-methyl-3′-O-L-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections
US7582618B2 (en) 2002-06-28 2009-09-01 Idenix Pharmaceuticals, Inc. 2′-C-methyl-3′-O-L-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections
US7598373B2 (en) 2002-12-12 2009-10-06 Idenix Pharmaceuticals, Inc. Process for the production of 2-C-methyl-D-ribonolactone
US7429572B2 (en) 2003-05-30 2008-09-30 Pharmasset, Inc. Modified fluorinated nucleoside analogues
US7645745B2 (en) 2006-04-04 2010-01-12 Roche Palo Alto Llc Antiviral nucleosides
US7786110B2 (en) 2006-11-09 2010-08-31 Roche Palo Alto Llc Thiazole and oxazole-substituted arylamides as P2X3 and P2X2/3 antagonists
US8957046B2 (en) 2007-03-30 2015-02-17 Gilead Pharmasset Llc Nucleoside phosphoramidate prodrugs
US9585906B2 (en) 2007-03-30 2017-03-07 Gilead Pharmasset Llc Nucleoside phosphoramidate prodrugs
US7989637B2 (en) 2007-12-17 2011-08-02 Roche Palo Alto Llc Triazole-substituted arylamides as P2X3 and P2X2/3 antagonists
US8048905B2 (en) 2007-12-17 2011-11-01 Roche Palo Alto Llc Tetrazole-substituted arylamides as P2X3 and P2X2/3 antagonists
US8440673B2 (en) 2007-12-17 2013-05-14 Roche Palo Alto Llc Pyrazole-substituted arylamides as P2X3 and P2X2/3 antagonists
US7858654B2 (en) 2007-12-17 2010-12-28 Roche Palo Alto Llc Imidazole-substituted arylamides as P2X3 and P2X2/3 antagonists
US9045520B2 (en) 2008-12-23 2015-06-02 Gilead Pharmasset Llc Synthesis of purine nucleosides
US8841275B2 (en) 2010-11-30 2014-09-23 Gilead Pharmasset Llc 2′-spiro-nucleosides and derivatives thereof useful for treating hepatitis C virus and dengue virus infections
US9394331B2 (en) 2010-11-30 2016-07-19 Gilead Pharmasset Llc 2′-spiro-nucleosides and derivatives thereof useful for treating hepatitis C virus and dengue virus infections
US9243025B2 (en) 2011-03-31 2016-01-26 Idenix Pharmaceuticals, Llc Compounds and pharmaceutical compositions for the treatment of viral infections
US9393256B2 (en) 2011-09-16 2016-07-19 Gilead Pharmasset Llc Methods for treating HCV
US9549941B2 (en) 2011-11-29 2017-01-24 Gilead Pharmasset Llc Compositions and methods for treating hepatitis C virus

Also Published As

Publication number Publication date
JP2005533777A (en) 2005-11-10
EP1515971A2 (en) 2005-03-23
AU2003251524A1 (en) 2003-12-31
CA2488842A1 (en) 2003-12-24
WO2003105770A2 (en) 2003-12-24

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