AU1439888A - Desazapurine-nucleoside derivatives, processes for the preparation thereof, pharmaceutical compositions containing them and the use thereof for nucleic acid sequencing and as antiviral agents - Google Patents

Desazapurine-nucleoside derivatives, processes for the preparation thereof, pharmaceutical compositions containing them and the use thereof for nucleic acid sequencing and as antiviral agents

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Publication number
AU1439888A
AU1439888A AU14398/88A AU1439888A AU1439888A AU 1439888 A AU1439888 A AU 1439888A AU 14398/88 A AU14398/88 A AU 14398/88A AU 1439888 A AU1439888 A AU 1439888A AU 1439888 A AU1439888 A AU 1439888A
Authority
AU
Australia
Prior art keywords
group
denotes
desazapurine
hydrogen
processes
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
AU14398/88A
Other versions
AU597483B2 (en
Inventor
Hans-George Batz
Werner Bourgeois
Klaus Kaiser
Klaus Muhlegger
Heinz-Peter Muth
Frank Seela
Herbert Von Der Eltz
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.)
Roche Diagnostics GmbH
Original Assignee
Boehringer Mannheim GmbH
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 Boehringer Mannheim GmbH filed Critical Boehringer Mannheim GmbH
Publication of AU1439888A publication Critical patent/AU1439888A/en
Application granted granted Critical
Publication of AU597483B2 publication Critical patent/AU597483B2/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • C07H19/14—Pyrrolo-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
    • 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
    • C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Virology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)

Abstract

Novel deazapurine nucleosides of the formula I <IMAGE> in which X denotes nitrogen or a methine group, W denotes nitrogen or the group <IMAGE> R<1>, R<2>, R<3> and R<4> can be the same or different, and denote hydrogen, halogen, a lower alkyl, hydroxyl, mercapto, lower alkylthio, lower alkyloxy, aralkyl, aralkyloxy, aryloxy or an optionally mono- or disubstituted amino group, R<5> denotes hydrogen or a hydroxyl group, R<6> and R<7> each denote hydrogen or one of the two radicals R<6> and R<7> denotes halogen, a cyano, azido or an optionally mono- or disubstituted amino group, where one of the radicals R<6> and R<7> can also represent a hydroxyl group if X denotes a methine group, and R<5> and R<7> together can additionally represent a further bond between C-2' and C-3' and Y represents hydrogen, a monophosphate, diphosphate or triphosphate group, and possible tautomers and salts and nucleic acids which contain one or more compounds of the formula I as building block. The compounds according to the invention exhibit antiviral properties and can further be used in DNA sequencing, where they lead to chain termination and/or prevent band compression.
AU14398/88A 1987-04-10 1988-04-08 Desazapurine-nucleoside derivatives, processes for the preparation thereof, pharmaceutical compositions containing them and the use thereof for nucleic acid sequencing and as antiviral agents Ceased AU597483B2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE3712280 1987-04-10
DE3712280 1987-04-10
DE3739366 1987-11-20
DE19873739366 DE3739366A1 (en) 1987-04-10 1987-11-20 DESAZA-PURIN-NUCLEOSIDE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE IN NUCLEIC ACID SEQUENCING AND AS AN ANTIVIRAL AGENT

Publications (2)

Publication Number Publication Date
AU1439888A true AU1439888A (en) 1988-10-13
AU597483B2 AU597483B2 (en) 1990-05-31

Family

ID=25854556

Family Applications (1)

Application Number Title Priority Date Filing Date
AU14398/88A Ceased AU597483B2 (en) 1987-04-10 1988-04-08 Desazapurine-nucleoside derivatives, processes for the preparation thereof, pharmaceutical compositions containing them and the use thereof for nucleic acid sequencing and as antiviral agents

Country Status (11)

Country Link
EP (1) EP0286028B1 (en)
JP (2) JPH0662663B2 (en)
KR (1) KR880012631A (en)
CN (1) CN88102038A (en)
AT (1) ATE124415T1 (en)
AU (1) AU597483B2 (en)
CA (1) CA1311201C (en)
DE (2) DE3739366A1 (en)
DK (1) DK194688A (en)
ES (1) ES2076146T3 (en)
HU (1) HU199871B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
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AU613907B2 (en) * 1987-04-15 1991-08-15 Boehringer Mannheim Gmbh New pyrazolo (3,4-d) pyrimidines, processes for the preparation thereof and pharmaceutical compositions containing them
AU614947B2 (en) * 1986-10-24 1991-09-19 Warner-Lambert Company 7-deazaguanines as immunomodulators
US6093807A (en) * 1999-03-19 2000-07-25 Isis Pharmaceuticals, Inc. Sugar-modified 7-deaza-7-substituted oligonucleotides

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IE60433B1 (en) * 1986-08-26 1994-07-13 Warner Lambert Co Novel 9-deazaguanines
WO1990006312A1 (en) * 1988-11-29 1990-06-14 Institut Für Molekularbiologie Und Analytik (Ima) Gmbh 2',3'-dideoxyribofuranosides and process for producing them
GB8902041D0 (en) * 1989-01-31 1989-03-22 Tanabe Seiyaku Co Antiviral agent and novel nucleoside
JP2619710B2 (en) * 1989-02-27 1997-06-11 日本製紙 株式会社 Method for producing 2 ', 3'-dideoxypurine nucleosides
US5721356A (en) * 1989-09-15 1998-02-24 Gensia, Inc. Orally active adenosine kinase inhibitors
US5661148A (en) * 1989-09-19 1997-08-26 Teijin Limited Pyrrolo[2,3-d]pyrimidine derivatives, process for producing the same and pharmaceutical preparation comprising the same as active ingredient
KR970009225B1 (en) * 1989-09-19 1997-06-09 데이진 가부시끼가이샤 Pyrrole£2,3-d|pyrimidine derivatives, process for preparing the same, and pharmaceutical preparation covering diketopyrrolupyrrole pigments
JPH0637391B2 (en) * 1989-09-29 1994-05-18 日本製紙株式会社 Anti-AIDS virus agent
US5459255A (en) * 1990-01-11 1995-10-17 Isis Pharmaceuticals, Inc. N-2 substituted purines
EP1418179A3 (en) * 1990-01-11 2006-03-08 Isis Pharmaceuticals, Inc. Compositions and methods for detecting and modulating rna activity and gene expression
US6262241B1 (en) * 1990-08-13 2001-07-17 Isis Pharmaceuticals, Inc. Compound for detecting and modulating RNA activity and gene expression
US5594121A (en) * 1991-11-07 1997-01-14 Gilead Sciences, Inc. Enhanced triple-helix and double-helix formation with oligomers containing modified purines
US6235887B1 (en) 1991-11-26 2001-05-22 Isis Pharmaceuticals, Inc. Enhanced triple-helix and double-helix formation directed by oligonucleotides containing modified pyrimidines
TW393513B (en) * 1991-11-26 2000-06-11 Isis Pharmaceuticals Inc Enhanced triple-helix and double-helix formation with oligomers containing modified pyrimidines
DE4140463A1 (en) 1991-12-09 1993-06-17 Boehringer Mannheim Gmbh 2'-DESOXY-ISOGUANOSINE, THE ISOSTERAL ANALOGS AND THE APPLICATION THEREOF
US5231174A (en) * 1992-02-27 1993-07-27 University Of Iowa Research Foundation 2'isodideoxy-β-D-nucleosides as stable antiviral agents
US5633360A (en) * 1992-04-14 1997-05-27 Gilead Sciences, Inc. Oligonucleotide analogs capable of passive cell membrane permeation
CA2159630A1 (en) * 1993-03-30 1994-10-13 Philip D. Cook 7-deazapurine modified oligonucleotides
WO1994024144A2 (en) * 1993-04-19 1994-10-27 Gilead Sciences, Inc. Enhanced triple-helix and double-helix formation with oligomers containing modified purines
US6150510A (en) 1995-11-06 2000-11-21 Aventis Pharma Deutschland Gmbh Modified oligonucleotides, their preparation and their use
DE4438918A1 (en) * 1994-11-04 1996-05-09 Hoechst Ag Modified oligonucleotides, their preparation and their use
SE9500342D0 (en) 1995-01-31 1995-01-31 Marek Kwiatkowski Novel chain terminators, the use thereof for nucleic acid sequencing and synthesis and a method of their preparation
US6004939A (en) * 1995-07-06 1999-12-21 Ctrc Research Foundation Board Of Regents Methods for modulation and inhibition of telomerase
AU6485996A (en) * 1995-07-06 1997-02-05 Board Of Regents, The University Of Texas System Methods and compositions for modulation and inhibition of teomerase
US6291164B1 (en) 1996-11-22 2001-09-18 Invitrogen Corporation Methods for preventing inhibition of nucleic acid synthesis by pyrophosphate
EP0866070A1 (en) * 1997-03-20 1998-09-23 Amersham Pharmacia Biotech Inc Derivatives of 7 deaza 2' deoxy guanosine 5' triphosphate, preparation and use thereof
US6143206A (en) * 1998-06-24 2000-11-07 Tdk Corporation Organic positive temperature coefficient thermistor and manufacturing method therefor
JP3619017B2 (en) * 1998-06-24 2005-02-09 日本臓器製薬株式会社 New arabinosyladenine derivatives
US6452476B1 (en) 1999-01-28 2002-09-17 Tdk Corporation Organic positive temperature coefficient thermistor
ATE342271T1 (en) 1999-08-30 2006-11-15 Roche Diagnostics Gmbh 2-AZAPURINE COMPOUNDS AND THEIR USE
US6660845B1 (en) 1999-11-23 2003-12-09 Epoch Biosciences, Inc. Non-aggregating, non-quenching oligomers comprising nucleotide analogues; methods of synthesis and use thereof
WO2002018383A2 (en) 2000-09-01 2002-03-07 Chiron Corporation Aza heterocyclic derivatives and their therapeutic use
EP1236804A1 (en) 2001-03-02 2002-09-04 Boehringer Mannheim Gmbh A method for determination of a nucleic acid using a control
US6962991B2 (en) 2001-09-12 2005-11-08 Epoch Biosciences, Inc. Process for the synthesis of pyrazolopyrimidines
AU2003254657A1 (en) * 2002-07-25 2004-02-16 Micrologix Biotech Inc. Anti-viral 7-deaza d-nucleosides and uses thereof
DE10238722A1 (en) 2002-08-23 2004-03-11 Bayer Ag Improving attention, concentration, cognition, learning and/or memory performance, using selective phosphodiesterase 9A inhibitors, preferably 4H-pyrazolo-(3,4-d)-pyrimidin-4-one derivatives
DE10238723A1 (en) 2002-08-23 2004-03-11 Bayer Ag Phenyl substituted pyrazolyprimidines
DE10238724A1 (en) 2002-08-23 2004-03-04 Bayer Ag New 6-alkyl-1,5-dihydro-4H-pyrazolo-(3,4-d)-pyrimidin-4-ones useful as selective phosphodiesterase 9A inhibitors for improving attention, concentration, learning and/or memory performance
US8044060B2 (en) 2003-05-09 2011-10-25 Boehringer Ingelheim International Gmbh 6-cyclylmethyl- and 6-alkylmethyl pyrazolo[3,4-D]pyrimidines, methods for their preparation and methods for their use to treat impairments of perception, concentration learning and/or memory
DE10320785A1 (en) 2003-05-09 2004-11-25 Bayer Healthcare Ag 6-arylmethyl substituted pyrazolopyrimidines
US8637650B2 (en) 2003-11-05 2014-01-28 Genovoxx Gmbh Macromolecular nucleotide compounds and methods for using the same
DE102004001873A1 (en) 2004-01-14 2005-09-29 Bayer Healthcare Ag Cyanopyrimidinone
BRPI0616738A2 (en) * 2005-09-26 2011-06-28 Pharmasset Inc 4'-nucleosides modified as antiviral agents
JP5498392B2 (en) 2007-11-30 2014-05-21 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング 1,5-Dihydro-pyrazolo [3,4-D] pyrimidin-4-one derivatives and their use as PDE9A modulators for the treatment of CNS disorders
CN101220071B (en) * 2008-01-17 2011-04-06 南京长澳医药科技有限公司 Stable 6-methoxy-2',3'-dideoxy guanine nucleoside, method for preparing the same and medicament composition containing the same
UA105362C2 (en) 2008-04-02 2014-05-12 Бьорингер Ингельхайм Интернациональ Гмбх 1-heterocyclyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their use as pde9a modulators
NZ590788A (en) 2008-09-08 2012-11-30 Boehringer Ingelheim Int Pyrazolopyrimidines and their use for the treatment of cns disorders
CN101768197A (en) * 2008-12-29 2010-07-07 北京德众万全药物技术开发有限公司 Preparation method for nelarabine
AP2011005819A0 (en) 2009-03-31 2011-08-31 Boehringer Ingelheim Int 1-heterocyclyl-1, 5-dihydropyrazolo[3,4-D] pyrimidin -4-one derivatives and their use as PDE9A modulators.
DE102010049607A1 (en) 2009-10-26 2011-06-30 Becker, Claus, Prof., 76470 Conjugates of nucleotides and methods for their use
EP2603511B1 (en) 2010-08-12 2017-03-15 Boehringer Ingelheim International GmbH 6-cycloalkyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their use as pde9a inhibitors
US8809345B2 (en) 2011-02-15 2014-08-19 Boehringer Ingelheim International Gmbh 6-cycloalkyl-pyrazolopyrimidinones for the treatment of CNS disorders
EP2702171A1 (en) 2011-04-27 2014-03-05 Cherkasov, Dmitry Method and components for detecting nucleic acid chains
WO2012150035A1 (en) 2011-05-04 2012-11-08 Genovoxx Gmbh Nucleoside-triphosphate conjugate and methods for the use thereof
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU614947B2 (en) * 1986-10-24 1991-09-19 Warner-Lambert Company 7-deazaguanines as immunomodulators
AU613907B2 (en) * 1987-04-15 1991-08-15 Boehringer Mannheim Gmbh New pyrazolo (3,4-d) pyrimidines, processes for the preparation thereof and pharmaceutical compositions containing them
US6093807A (en) * 1999-03-19 2000-07-25 Isis Pharmaceuticals, Inc. Sugar-modified 7-deaza-7-substituted oligonucleotides

Also Published As

Publication number Publication date
DE3739366A1 (en) 1988-10-27
CN88102038A (en) 1988-10-26
AU597483B2 (en) 1990-05-31
JPH0662663B2 (en) 1994-08-17
ES2076146T3 (en) 1995-11-01
CA1311201C (en) 1992-12-08
EP0286028A3 (en) 1990-05-30
HUT46703A (en) 1988-11-28
DK194688A (en) 1988-10-11
EP0286028A2 (en) 1988-10-12
ATE124415T1 (en) 1995-07-15
JPS63275598A (en) 1988-11-14
DE3854060D1 (en) 1995-08-03
KR880012631A (en) 1988-11-28
JPH0748396A (en) 1995-02-21
JP2675749B2 (en) 1997-11-12
EP0286028B1 (en) 1995-06-28
HU199871B (en) 1990-03-28
DK194688D0 (en) 1988-04-08

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MK14 Patent ceased section 143(a) (annual fees not paid) or expired