NO20060469L - Syntese av -L-2-deoksynukleosider - Google Patents

Syntese av -L-2-deoksynukleosider

Info

Publication number
NO20060469L
NO20060469L NO20060469A NO20060469A NO20060469L NO 20060469 L NO20060469 L NO 20060469L NO 20060469 A NO20060469 A NO 20060469A NO 20060469 A NO20060469 A NO 20060469A NO 20060469 L NO20060469 L NO 20060469L
Authority
NO
Norway
Prior art keywords
anhydro
deoxynucleosides
furanosyl
preparation
good yields
Prior art date
Application number
NO20060469A
Other languages
English (en)
Inventor
Richard Storer
Adel Moussa
Steven Mathieu
Jing Yang Wang
Narayan Chaudhun
Alistair Stewart
Original Assignee
Idenix Cayman Ltd
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 Cayman Ltd filed Critical Idenix Cayman Ltd
Publication of NO20060469L publication Critical patent/NO20060469L/no

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • 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
    • C07H19/06—Pyrimidine radicals
    • C07H19/09—Pyrimidine radicals with arabinosyl as the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
    • 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
    • C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring 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
    • C07H19/06—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
    • C07H19/06—Pyrimidine radicals
    • C07H19/073—Pyrimidine radicals with 2-deoxyribosyl as the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
    • C07H9/02—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing only oxygen as ring hetero atoms
    • C07H9/04—Cyclic acetals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
    • C07H9/06—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing nitrogen as ring hetero atoms
    • Y—GENERAL 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

En forbedret fremgangsmåte for fremstilling av 2'-modifiserte nukleosider og 2'-deoksynukleosider, slik som ß-L-2'-deoksy-tymidin (LdT) er tilveiebrakt. Særlig er den forbedrede fremgangsmåten rettet mot syntese av et 2'-deoksynukleosid som kan anvende forskjellige utgangsmaterialer, men som skjer via et klor-sukker intermediat eller via et 2,2'-anhydro-1-furanosyl-nukleobase intermediat. Der et 2,2'-anhydro-1-furanosylbase intermediat anvendes blir et reduksjonsmiddel, slik som Red-Al, og et sekvesteringsmiddel, slik som 15-kron-5 eter, som forårsaker en intramolekylær substitusjonsreaksjon og dannelse av det ønskede nukleosid produktet i gode utbytter anvendt. En altemativ fremgangsmåte ifølge oppfinnelsen anvender et 2,2'-anhydro-1furanosylbase intermediat uten et sekvesteringsmiddel for å gi 2'-deoksynukleosider i gode utbytter. Forbindelsene fremstilt ifølge foreliggende oppfinnelse kan anvendes som intermediater ved frernstilling av andre nukelosidanaloger, eller kan anvendes direkte som antivirale og/eller antineoplastiske midler.
NO20060469A 2003-06-30 2006-01-30 Syntese av -L-2-deoksynukleosider NO20060469L (no)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US48371103P 2003-06-30 2003-06-30
US55861604P 2004-04-01 2004-04-01
PCT/US2004/021281 WO2005003374A2 (en) 2003-06-30 2004-06-30 SYNTHESIS OF β-L-2-DEOXY NUCLEOSIDES

Publications (1)

Publication Number Publication Date
NO20060469L true NO20060469L (no) 2006-03-30

Family

ID=33567697

Family Applications (1)

Application Number Title Priority Date Filing Date
NO20060469A NO20060469L (no) 2003-06-30 2006-01-30 Syntese av -L-2-deoksynukleosider

Country Status (12)

Country Link
US (1) US20050059632A1 (no)
EP (2) EP2157095A3 (no)
JP (1) JP2007527396A (no)
KR (1) KR20060035652A (no)
AU (1) AU2004254620A1 (no)
BR (1) BRPI0412031A (no)
CA (1) CA2531412A1 (no)
MX (1) MXPA06000162A (no)
NO (1) NO20060469L (no)
NZ (1) NZ544634A (no)
RU (2) RU2361875C2 (no)
WO (1) WO2005003374A2 (no)

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CN101180287B (zh) * 2005-05-25 2011-10-19 默克专利股份有限公司 通过还原消除相应的4-卤素衍生物而制备2,5-取代的四氢吡喃衍生物的方法
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CN101511375B (zh) * 2005-12-02 2012-09-05 耶鲁大学 L-胞嘧啶核苷类似物在制备用于治疗癌症和其它病症或疾病状态的药物中的应用
JP5254033B2 (ja) * 2005-12-23 2013-08-07 イデニク プハルマセウティカルス，インコーポレイテッド 分岐型ヌクレオシドを調製するための合成中間体の製造方法
KR20080104314A (ko) * 2006-03-15 2008-12-02 노파르티스 아게 Ｌ-핵산 유도체 및 그의 중간체의 제조 방법
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CN101531639B (zh) * 2009-04-16 2011-10-26 药源药物化学（上海）有限公司 三价铁的无机盐催化2-嘧啶酮及其衍生物的5位碘代方法
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CN104744538A (zh) * 2013-12-26 2015-07-01 康普药业股份有限公司 一种替比夫定的制备方法
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Also Published As

Publication number Publication date
EP2157095A2 (en) 2010-02-24
EP1639121A2 (en) 2006-03-29
EP2157095A3 (en) 2010-09-08
RU2006102518A (ru) 2006-07-27
RU2009115775A (ru) 2010-10-27
BRPI0412031A (pt) 2006-09-19
AU2004254620A1 (en) 2005-01-13
MXPA06000162A (es) 2006-03-21
EP1639121A4 (en) 2008-04-16
KR20060035652A (ko) 2006-04-26
WO2005003374A3 (en) 2005-09-01
US20050059632A1 (en) 2005-03-17
NZ544634A (en) 2009-10-30
RU2361875C2 (ru) 2009-07-20
CA2531412A1 (en) 2005-01-13
JP2007527396A (ja) 2007-09-27
WO2005003374A2 (en) 2005-01-13

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