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 agentsInfo
- 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
Links
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)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Preparation Of Compounds By Using 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.
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
Families Citing this family (55)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
ATE271064T1 (en) * | 1990-01-11 | 2004-07-15 | Isis Pharmaceuticals Inc | OLIGONUCLEOTIDE DERIVATIVES FOR DETECTING AND MODULATING RNA ACTIVITY AND GENE EXPRESSION |
US5459255A (en) * | 1990-01-11 | 1995-10-17 | Isis Pharmaceuticals, Inc. | N-2 substituted purines |
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 |
AU6589094A (en) * | 1993-03-30 | 1994-10-24 | Sterling Winthrop Inc. | 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 |
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 |
US6004939A (en) * | 1995-07-06 | 1999-12-21 | Ctrc Research Foundation Board Of Regents | Methods for modulation and inhibition of telomerase |
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 |
JP3619017B2 (en) * | 1998-06-24 | 2005-02-09 | 日本臓器製薬株式会社 | New arabinosyladenine derivatives |
US6143206A (en) * | 1998-06-24 | 2000-11-07 | Tdk Corporation | Organic positive temperature coefficient thermistor and manufacturing method therefor |
US6452476B1 (en) | 1999-01-28 | 2002-09-17 | Tdk Corporation | Organic positive temperature coefficient thermistor |
ES2272322T3 (en) | 1999-08-30 | 2007-05-01 | Roche Diagnostics Gmbh | 2-AZAPURINE COMPOUNDS AND ITS 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 |
CA2492607A1 (en) * | 2002-07-25 | 2004-02-05 | Micrologix Biotech Inc. | Anti-viral 7-deaza d-nucleosides and uses thereof |
DE10238723A1 (en) | 2002-08-23 | 2004-03-11 | Bayer Ag | Phenyl substituted pyrazolyprimidines |
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 |
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 |
CA2623522C (en) * | 2005-09-26 | 2015-12-08 | Pharmasset, Inc. | Modified 4'-nucleosides 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 |
EP2334684B1 (en) | 2008-09-08 | 2017-08-02 | Boehringer Ingelheim International GmbH | 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 |
MA33152B1 (en) | 2009-03-31 | 2012-03-01 | Boehringer Ingelheim Int | 1-HETEROCYCLYL-1,5-DIHYDRO-PYRAZOLO [3,4-D] PYRIMIDIN-4-ONE DERIVATIVES AND THEIR USE AS MODULATORS OF PDE9A |
EP2494073B1 (en) | 2009-10-26 | 2017-11-29 | AGCT GmbH | Nucleotide conjugates and methods of uses thereof |
KR101918909B1 (en) | 2010-08-12 | 2018-11-15 | 베링거 인겔하임 인터내셔날 게엠베하 | 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 |
US9994894B2 (en) | 2011-04-27 | 2018-06-12 | Agct Gmbh | Method and components for detecting nucleic acid chains |
DE102012008759A1 (en) | 2011-05-04 | 2012-11-08 | Genovoxx Gmbh | Nucleoside-triphosphate conjugates and methods for their use |
GB201718804D0 (en) * | 2017-11-14 | 2017-12-27 | Nuclera Nucleics Ltd | Novel use |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4315000A (en) * | 1980-07-07 | 1982-02-09 | Warner-Lambert Company | β-D-Arabinofuranosylimidazo(4,5-c)pyridine compounds and methods for their production |
US4352795A (en) * | 1981-01-29 | 1982-10-05 | Warner-Lambert Company | 7-β-D-Arabinofuranosyl-7H-pyrrolo[2,3-d]pyrimidine compounds and methods for their production |
FI87783C (en) * | 1985-05-15 | 1993-02-25 | Wellcome Found | FRAME FOR THE PREPARATION OF THERAPEUTIC ANALYTICAL BAR 2 ', 3'-DIDEOXINUCLEOSIDER |
DE3529478A1 (en) * | 1985-08-16 | 1987-02-19 | Boehringer Mannheim Gmbh | 7-DESAZA-2'DESOXYGUANOSINE NUCLEOTIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR NUCLEIC ACID SEQUENCING |
ZA867013B (en) * | 1985-09-17 | 1988-04-27 | Wellcome Found | Therapeutic nucleosides |
IN164556B (en) * | 1986-03-06 | 1989-04-08 | Takeda Chemical Industries Ltd | |
US5047519A (en) * | 1986-07-02 | 1991-09-10 | E. I. Du Pont De Nemours And Company | Alkynylamino-nucleotides |
JPS63130599A (en) * | 1986-11-20 | 1988-06-02 | Sekisui Chem Co Ltd | Modified nucleotide |
-
1987
- 1987-11-20 DE DE19873739366 patent/DE3739366A1/en not_active Withdrawn
-
1988
- 1988-03-31 DE DE3854060T patent/DE3854060D1/en not_active Expired - Lifetime
- 1988-03-31 ES ES88105277T patent/ES2076146T3/en not_active Expired - Lifetime
- 1988-03-31 EP EP88105277A patent/EP0286028B1/en not_active Expired - Lifetime
- 1988-03-31 AT AT88105277T patent/ATE124415T1/en not_active IP Right Cessation
- 1988-04-08 CN CN88102038A patent/CN88102038A/en active Pending
- 1988-04-08 AU AU14398/88A patent/AU597483B2/en not_active Ceased
- 1988-04-08 DK DK194688A patent/DK194688A/en not_active Application Discontinuation
- 1988-04-08 CA CA000563635A patent/CA1311201C/en not_active Expired - Lifetime
- 1988-04-08 JP JP63085533A patent/JPH0662663B2/en not_active Expired - Lifetime
- 1988-04-08 HU HU881786A patent/HU199871B/en not_active IP Right Cessation
- 1988-04-09 KR KR1019880004081A patent/KR880012631A/en not_active Application Discontinuation
-
1994
- 1994-03-31 JP JP6063020A patent/JP2675749B2/en not_active Expired - Lifetime
Cited By (3)
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 |
---|---|
CN88102038A (en) | 1988-10-26 |
JPS63275598A (en) | 1988-11-14 |
EP0286028A3 (en) | 1990-05-30 |
DE3739366A1 (en) | 1988-10-27 |
EP0286028A2 (en) | 1988-10-12 |
HU199871B (en) | 1990-03-28 |
CA1311201C (en) | 1992-12-08 |
DK194688D0 (en) | 1988-04-08 |
JP2675749B2 (en) | 1997-11-12 |
DK194688A (en) | 1988-10-11 |
AU597483B2 (en) | 1990-05-31 |
JPH0748396A (en) | 1995-02-21 |
ATE124415T1 (en) | 1995-07-15 |
ES2076146T3 (en) | 1995-11-01 |
DE3854060D1 (en) | 1995-08-03 |
JPH0662663B2 (en) | 1994-08-17 |
HUT46703A (en) | 1988-11-28 |
KR880012631A (en) | 1988-11-28 |
EP0286028B1 (en) | 1995-06-28 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |