CA2300874A1 - Solution phase synthesis of oligonucleotides - Google Patents

Solution phase synthesis of oligonucleotides Download PDF

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Publication number
CA2300874A1
CA2300874A1 CA002300874A CA2300874A CA2300874A1 CA 2300874 A1 CA2300874 A1 CA 2300874A1 CA 002300874 A CA002300874 A CA 002300874A CA 2300874 A CA2300874 A CA 2300874A CA 2300874 A1 CA2300874 A1 CA 2300874A1
Authority
CA
Canada
Prior art keywords
group
phosphonate
alkyl
oligonucleotide
protecting group
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.)
Abandoned
Application number
CA002300874A
Other languages
English (en)
French (fr)
Inventor
Colin Bernard Reese
Quanlai Song
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.)
Avecia Ltd
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
Application filed by Individual filed Critical Individual
Publication of CA2300874A1 publication Critical patent/CA2300874A1/en
Abandoned legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00Processes for the preparation of sugar derivatives
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D265/00Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/281,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/301,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • C07D265/321,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings with oxygen atoms directly attached to ring carbon atoms
    • C07D265/33Two oxygen atoms, in positions 3 and 5
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/46Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
    • C07D207/48Sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/06Phosphorus compounds without P—C bonds
    • C07F9/16Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165Esters of thiophosphoric acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/06Phosphorus compounds without P—C bonds
    • C07F9/16Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165Esters of thiophosphoric acids
    • C07F9/18Esters of thiophosphoric acids with hydroxyaryl compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H11/00Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
    • C07H11/04Phosphates; Phosphites; Polyphosphates
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06Pyrimidine radicals
    • C07H19/10Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16Purine radicals
    • C07H19/20Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • 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
    • 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
    • C07H21/04Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids with deoxyribosyl as saccharide radical
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
CA002300874A 1997-08-13 1998-08-10 Solution phase synthesis of oligonucleotides Abandoned CA2300874A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB9717158.1 1997-08-13
GBGB9717158.1A GB9717158D0 (en) 1997-08-13 1997-08-13 Solution synthesis of oligonucleotides and their phosphorothioate analogues
PCT/GB1998/002407 WO1999009041A2 (en) 1997-08-13 1998-08-10 Solution phase synthesis of oligonucleotides

Publications (1)

Publication Number Publication Date
CA2300874A1 true CA2300874A1 (en) 1999-02-25

Family

ID=10817430

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002300874A Abandoned CA2300874A1 (en) 1997-08-13 1998-08-10 Solution phase synthesis of oligonucleotides

Country Status (21)

Country Link
US (3) US6506894B1 (h)
EP (2) EP1325927A3 (h)
JP (1) JP2001515086A (h)
KR (1) KR20010022840A (h)
CN (1) CN1231492C (h)
AT (1) ATE236916T1 (h)
BR (1) BR9811166A (h)
CA (1) CA2300874A1 (h)
DE (1) DE69813243T2 (h)
DK (1) DK1003758T3 (h)
EA (1) EA003091B1 (h)
ES (1) ES2197491T3 (h)
GB (1) GB9717158D0 (h)
HU (1) HUP0002684A3 (h)
IL (1) IL134517A (h)
IN (1) IN190784B (h)
NO (1) NO20000690L (h)
NZ (1) NZ502684A (h)
PL (1) PL338888A1 (h)
TR (1) TR200000384T2 (h)
WO (1) WO1999009041A2 (h)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9924285D0 (en) * 1999-10-14 1999-12-15 Avecia Ltd Process
GB0004889D0 (en) * 2000-03-01 2000-04-19 Avecia Ltd Synthesis of oligonucleotides
WO2003045969A1 (en) * 2001-11-21 2003-06-05 Avecia Biotechnology Inc. Coupling reagent for h-phosphonate chemistry
AU2003217706A1 (en) * 2002-02-22 2003-09-09 Honeywell International Inc. Methods of producing phosphitylated compounds
GB0209539D0 (en) 2002-04-26 2002-06-05 Avecia Ltd Monomer Polymer and process
WO2005077966A1 (en) * 2004-02-10 2005-08-25 Isis Pharmaceuticals, Inc. Substituted pixyl protecting groups for oligonucleotide synthesis
CA2744987C (en) 2008-12-02 2018-01-16 Chiralgen, Ltd. Method for the synthesis of phosphorus atom modified nucleic acids
US8272150B2 (en) * 2008-12-12 2012-09-25 Speedplay, Inc. Shoe sole mounting standard for bicycle cleat
WO2010072831A1 (en) 2008-12-23 2010-07-01 Girindus America, Inc Sulfurizing reagents and their use for oligonucleotides synthesis
AU2010270714B2 (en) 2009-07-06 2015-08-13 Wave Life Sciences Ltd. Novel nucleic acid prodrugs and methods use thereof
KR20130029108A (ko) 2010-06-30 2013-03-21 기린두스 아메리카 인코포레이티드 올리고뉴클레오타이드 합성을 위한 n-thio 화합물의 새로운 사용 방법
WO2012039448A1 (ja) 2010-09-24 2012-03-29 株式会社キラルジェン 不斉補助基
EP2734208B1 (en) 2011-07-19 2017-03-01 Wave Life Sciences Ltd. Methods for the synthesis of functionalized nucleic acids
US20140179875A1 (en) 2011-07-29 2014-06-26 Girindus America, Inc. Sulfurization reagents on solid supports
ES2940887T3 (es) 2012-07-13 2023-05-12 Wave Life Sciences Ltd Método de preparación de oligonucleótidos quirales
RU2677639C2 (ru) 2012-07-13 2019-01-18 Шин Ниппон Биомедикал Лэбораториз, Лтд. Хиральный адъювант нуклеиновой кислоты
ES2862073T3 (es) 2012-07-13 2021-10-06 Wave Life Sciences Ltd Grupo auxiliar asimétrico
WO2014085471A1 (en) * 2012-11-28 2014-06-05 Prognosdx Health, Inc. Acid-activated compositions for the treatment of cancers, methods of their use and methods of their preparation
WO2015108047A1 (ja) 2014-01-15 2015-07-23 株式会社新日本科学 免疫誘導活性を有するキラル核酸アジュバンド及び免疫誘導活性剤
WO2015108048A1 (ja) 2014-01-15 2015-07-23 株式会社新日本科学 抗腫瘍作用を有するキラル核酸アジュバンド及び抗腫瘍剤
JPWO2015108046A1 (ja) 2014-01-15 2017-03-23 株式会社新日本科学 抗アレルギー作用を有するキラル核酸アジュバンド及び抗アレルギー剤
KR20220106232A (ko) 2014-01-16 2022-07-28 웨이브 라이프 사이언시스 리미티드 키랄 디자인
WO2018215049A1 (en) * 2017-05-23 2018-11-29 F. Hoffmann-La Roche Ag Process for galnac oligonucleotide conjugates

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3444300A (en) * 1964-05-05 1969-05-13 Chevron Res N-polyhaloalkylthio compounds as fungicidal agents
FR1519704A (fr) * 1967-02-14 1968-04-05 Roussel Uclaf Nouveaux composés dithiocarbamiques hétérocycliques et procédé de préparation
US3546185A (en) 1968-03-20 1970-12-08 Monsanto Co Inhibiting premature vulcanization of diene rubbers
US5149798A (en) * 1989-04-06 1992-09-22 Worcester Foundation For Experimental Biology Process for synthesizing oligonucleotides and their analogs adaptable to large scale syntheses
CN1122137A (zh) 1993-01-08 1996-05-08 海布里顿公司 二聚体块的合成及其在装配寡核苷酸中的应用
GB9501465D0 (en) * 1995-01-25 1995-03-15 King S College London Nucleoside phosphorothioate derivatives,synthesis and use thereof
GB0004889D0 (en) * 2000-03-01 2000-04-19 Avecia Ltd Synthesis of oligonucleotides

Also Published As

Publication number Publication date
WO1999009041A2 (en) 1999-02-25
HUP0002684A3 (en) 2001-11-28
ES2197491T3 (es) 2004-01-01
IN190784B (h) 2003-08-23
EP1325927A3 (en) 2008-07-02
HUP0002684A2 (hu) 2000-12-28
DK1003758T3 (da) 2003-07-21
IL134517A (en) 2004-02-19
US7019127B2 (en) 2006-03-28
WO1999009041A3 (en) 1999-05-06
EP1325927A2 (en) 2003-07-09
AU8738698A (en) 1999-03-08
EP1003758A2 (en) 2000-05-31
NO20000690L (no) 2000-04-11
AU749343B2 (en) 2002-06-27
NZ502684A (en) 2002-12-20
US6506894B1 (en) 2003-01-14
US20050240015A1 (en) 2005-10-27
JP2001515086A (ja) 2001-09-18
TR200000384T2 (tr) 2000-11-21
CN1274361A (zh) 2000-11-22
DE69813243T2 (de) 2004-01-29
EA003091B1 (ru) 2002-12-26
EA200000211A1 (ru) 2000-08-28
DE69813243D1 (de) 2003-05-15
GB9717158D0 (en) 1997-10-22
NO20000690D0 (no) 2000-02-11
KR20010022840A (ko) 2001-03-26
PL338888A1 (en) 2000-11-20
BR9811166A (pt) 2000-07-25
ATE236916T1 (de) 2003-04-15
EP1003758B1 (en) 2003-04-09
US20030083490A1 (en) 2003-05-01
CN1231492C (zh) 2005-12-14
IL134517A0 (en) 2001-04-30

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Legal Events

Date Code Title Description
EEER Examination request
FZDE Discontinued