BRPI0412031A - sìntese de beta-l-2'-deóxi-nucleosìdeos - Google Patents

sìntese de beta-l-2'-deóxi-nucleosìdeos

Info

Publication number
BRPI0412031A
BRPI0412031A BRPI0412031-0A BRPI0412031A BRPI0412031A BR PI0412031 A BRPI0412031 A BR PI0412031A BR PI0412031 A BRPI0412031 A BR PI0412031A BR PI0412031 A BRPI0412031 A BR PI0412031A
Authority
BR
Brazil
Prior art keywords
synthesis
furanosyl
deoxynucleoside
hydro
preparation
Prior art date
Application number
BRPI0412031-0A
Other languages
English (en)
Inventor
Richard Storer
Adel Moussa
Jing Yang Wang
Narayan Chaudhuri
Steven Mathieu
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 BRPI0412031A publication Critical patent/BRPI0412031A/pt

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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

"SìNTESE DE <225>-L-2<39> -DEóXI-NUCLEOSìDEOS". um processo aperfeiçoado para o preparo de nucleosídeos 2<39>-modificados e 2<39>-deóxi-nucleosídeos, tais como <225>-L-2<39>-deóxi-timidina (LdT) é proporcionado. Em particular, o processo aperfeiçoado é dirigido à síntese de um 2<39> -deóxinucleosídeo que pode utilizar diferentes materiais de iniciação, mas que se processa via um intermediário de cloro-açúcar ou via um intermediário de 2,2<39>-anidro-1-furanosil-nucleobase. Onde um intermediário de base de 2,2<39>-anidro-1-furanosila é utilizado, um agente de redução, tal como Red-A1, e um agente de captura, tal como 15-crown-5-éter, que causa uma reação de substituição intramolecular e formação do produto de nucleosídeo desejado em bons rendimentos são empregados. Um processo alternativo da presente invenção utiliza um intermediário de base de 2,2<39>-anidro--furanosila sem um agente de captura a fim de proporcionar 2<39>-deóxinucleosídeo em bons rendimentos. Os compostos feitos de acordo com a presente invenção podem ser usados como intermediários no preparo de outros análogos de nucleosídeo ou podem ser usados diretamente como agentes antivirais ou antineoplásicos.
BRPI0412031-0A 2003-06-30 2004-06-30 sìntese de beta-l-2'-deóxi-nucleosìdeos BRPI0412031A (pt)

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
BRPI0412031A true BRPI0412031A (pt) 2006-09-19

Family

ID=33567697

Family Applications (1)

Application Number Title Priority Date Filing Date
BRPI0412031-0A BRPI0412031A (pt) 2003-06-30 2004-06-30 sìntese de beta-l-2'-deóxi-nucleosìdeos

Country Status (12)

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

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005289964A (ja) * 2004-03-12 2005-10-20 Ajinomoto Co Inc ２−デオキシ−ｌ−リボース化合物の製造方法
JP5260279B2 (ja) * 2005-05-25 2013-08-14 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 対応する４−ハロゲン誘導体の還元的脱離による２，５−２置換テトラヒドロピラン誘導体類の調製方法
BRPI0613796A2 (pt) 2005-06-07 2011-02-15 Univ Yale composicões farmacêuticas e seus usos, e métodos de tratamento de cáncer e outras condições ou estados patológicos, por meio do uso de clevudina (lfmau) e telbivudina (ldt)
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
US7781576B2 (en) * 2005-12-23 2010-08-24 Idenix Pharmaceuticals, Inc. Process for preparing a synthetic intermediate for preparation of branched nucleosides
US20090018325A1 (en) * 2006-03-15 2009-01-15 Jacques Cercus Process for preparing l-nucleic acid derivatives and intermediates thereof
GB2443410B (en) * 2006-10-31 2012-05-16 Cb Fleet Co Inc A process for the preparation of 6-bromo-6-deoxy-2,3-anhydro-D-manno-1,4-lactone
US7964580B2 (en) 2007-03-30 2011-06-21 Pharmasset, Inc. Nucleoside phosphoramidate prodrugs
CN101302239B (zh) * 2007-05-11 2011-05-11 上海医药工业研究院 汰比夫定及其中间体的合成方法
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
EA201690473A1 (ru) 2013-08-27 2017-03-31 ГАЙЛИД ФАРМАССЕТ ЭлЭлСи Комбинированный состав двух противовирусных соединений
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
JP6768796B2 (ja) * 2015-09-23 2020-10-14 メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． ４’−置換ヌクレオシド逆転写酵素阻害剤及びその調製
CN105732732B (zh) * 2016-04-14 2018-04-06 四川理工学院 一种制备2‑脱氧‑d‑核糖的方法
WO2021016220A2 (en) * 2019-07-19 2021-01-28 Bp Corporation North America Inc. Synthesis of substituted furans

Family Cites Families (48)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1191307B (de) 1958-02-25 1965-04-15 David Berreklouw Jun Klemme zum Festhalten von Gegenstaenden geringer Breite, z. B. Naegeln, Schrauben oder Draehten
US3116282A (en) * 1960-04-27 1963-12-31 Upjohn Co Pyrimidine nucleosides and process
DE2122991C2 (de) * 1971-05-04 1982-06-09 Schering Ag, 1000 Berlin Und 4619 Bergkamen Verfahren zur Herstellung von Cytosin- und 6-Azacytosinnucleosiden
DE2508312A1 (de) 1975-02-24 1976-09-02 Schering Ag Neues verfahren zur herstellung von nucleosiden
DE2757365A1 (de) * 1977-12-20 1979-06-21 Schering Ag Neues verfahren zur herstellung von nucleosiden
DE3401949A1 (de) * 1984-01-20 1985-08-01 Bayer Ag, 5090 Leverkusen Norbornan- und norbornencarbonsaeureamide, verfahren zu deren herstellung sowie die verwendung von norbornan- und norbornencarbonsaeureamiden als arzneimittel
JPS61124534A (ja) 1984-11-22 1986-06-12 Nippon Steel Corp 熱処理炉用ロ−ル
JPS61204193A (ja) * 1985-03-05 1986-09-10 Takeda Chem Ind Ltd シトシンヌクレオシド類の製造法
US4754026A (en) * 1985-06-04 1988-06-28 Takeda Chemical Industries, Ltd. Conversion of uracil derivatives to cytosine derivatives
GB8719367D0 (en) 1987-08-15 1987-09-23 Wellcome Found Therapeutic compounds
US4914233A (en) 1988-03-01 1990-04-03 Ethyl Corporation Synthesis of beta-thymidine
US5008384A (en) 1988-07-12 1991-04-16 Pfizer Inc. Process for the production of O.sup. 2,2'-anhydro-1-(β-D-arabinofuranosyl)thymine
SE8802687D0 (sv) 1988-07-20 1988-07-20 Astra Ab Nucleoside derivatives
US6060592A (en) * 1990-01-11 2000-05-09 Isis Pharmaceuticals, Inc. Pyrimidine nucleoside compounds and oligonucleoside compounds containing same
US5200514A (en) * 1990-01-19 1993-04-06 University Of Georgia Research Foundation, Inc. Synthesis of 2'-deoxypyrimidine nucleosides
US5204466A (en) * 1990-02-01 1993-04-20 Emory University Method and compositions for the synthesis of bch-189 and related compounds
US5212293A (en) 1990-08-06 1993-05-18 American Cyanamid Company Process for the preparation of deoxynucleosides
US5414078A (en) 1991-04-05 1995-05-09 Emory University Preparation of 3'-substituted-2',3'-dideoxynucleosides and 2'-deoxynucleosides from acyclic, achiral precursors
GB9218810D0 (en) * 1992-09-04 1992-10-21 Univ Birmingham Antiviral pyrimidine nucleosides
JP3693357B2 (ja) 1993-04-09 2005-09-07 峯郎 実吉 逆転写酵素阻害剤
FR2709754B1 (fr) 1993-09-10 1995-12-01 Centre Nat Rech Scient Composés 2' ou 3'-déoxy- et 2', 3'-didéoxy-beta-L-pentofuranonucléosides, procédé de préparation et application thérapeutique, notamment anti-virale.
EP0683171B1 (en) 1994-05-20 1998-12-23 Council of Scientific and Industrial Research A process for the preparation of beta-thymidine
JPH10501809A (ja) * 1994-06-22 1998-02-17 ネクスター ファーマスーティカルズ，インコーポレイテッド 分子内求核置換による公知および新規２′−ヌクレオシドの新規製造方法
DE4423647A1 (de) 1994-07-06 1996-01-11 Thomas Mueller Fahrrad
AT400953B (de) 1994-08-25 1996-05-28 Joern Saischek Pentofuranosid-derivate, deren herstellung und verwendung
RU2108339C1 (ru) * 1994-09-27 1998-04-10 Закрытое акционерное общество Производственно-коммерческая ассоциация "АЗТ" Способ получения 2'-дезоксиксилотимидина, производные d-ксилофуранозы, производные ксилотимидина
US5559101A (en) 1994-10-24 1996-09-24 Genencor International, Inc. L-ribofuranosyl nucleosides
JPH08149398A (ja) 1994-11-21 1996-06-07 Matsushita Electric Ind Co Ltd 画像表示装置
DE19513330A1 (de) 1995-04-03 1996-10-10 Schering Ag Neues Verfahren zur Herstellung von Nucleosiden
ES2276404T3 (es) 1995-06-07 2007-06-16 Emory University Nucleosidos con actividad antivirus de la hepatitis-b.
JPH0959293A (ja) * 1995-08-23 1997-03-04 Yamasa Shoyu Co Ltd ２位炭素鎖置換アデノシン誘導体の製造法
JPH0959292A (ja) 1995-08-25 1997-03-04 Yamasa Shoyu Co Ltd ４−アミノピリミジンヌクレオシドの製造法
EP0877554A1 (en) * 1995-10-31 1998-11-18 Merck & Co., Inc. Triterpene derivatives with immunosuppressant activity
US5760208A (en) 1996-08-14 1998-06-02 The Board Of Governors For Higher Education, State Of Rhode Island And Providence Plantations Process to prepare pyrimidine nucleosides
EA200700564A1 (ru) 1998-02-25 2007-08-31 Эмори Юниверсити 2`-фторнуклеозиды
US6444652B1 (en) * 1998-08-10 2002-09-03 Novirio Pharmaceuticals Limited β-L-2'-deoxy-nucleosides for the treatment of hepatitis B
US6395716B1 (en) 1998-08-10 2002-05-28 Novirio Pharmaceuticals Limited β-L-2′-deoxy-nucleosides for the treatment of hepatitis B
US6399765B1 (en) * 1999-03-17 2002-06-04 Isis Pharmaceuticals, Inc. Methods for removing dimethoxytrityl groups from oligonucleotides
KR100367986B1 (ko) 2000-03-27 2003-01-14 국제약품공업주식회사 광학활성을 갖는 시아노부탄트리올 유도체 및 그의 제조방법
DE10020275A1 (de) * 2000-04-25 2001-10-31 Manfred Schneider Enantiomere Bausteine der 2-Deoxy-L-Ribose und 2-Deoxy-D-Ribose, Verfahren zu ihrer Herstellung sowie Verwendung zur Synthese von natürlichen und nicht natürliche L- und D-Nucleinsäuren, L- und D- konfigurierten Oligonucleotiden, L- und D-konfigurierter DNA und davon abgeleiteten pharmazeutischen Wirkstoffen
US6875751B2 (en) 2000-06-15 2005-04-05 Idenix Pharmaceuticals, Inc. 3′-prodrugs of 2′-deoxy-β-L-nucleosides
MY141594A (en) 2000-06-15 2010-05-14 Novirio Pharmaceuticals Ltd 3'-PRODRUGS OF 2'-DEOXY-ß-L-NUCLEOSIDES
JP2002322192A (ja) * 2000-08-10 2002-11-08 Sankyo Co Ltd ２’−ｏ，４’−ｃ−架橋ヌクレオシドトリリン酸体
CN102241720B (zh) 2000-11-29 2014-01-29 三井化学株式会社 L-核酸衍生物及其合成方法
MXPA03006514A (es) * 2001-01-22 2004-12-02 Merck & Co Inc Derivados de nucleosidos como inhibidores de polimerasa de acido ribonucleico viral dependiente de acido ribonucleico.
US6539837B2 (en) 2001-05-17 2003-04-01 Delphi Technologies, Inc. Apparatus and method of attaching a connecting member and a tube member to a housing of a vacuum brake booster
DE10216426A1 (de) 2002-04-12 2003-10-23 Boehringer Ingelheim Pharma Verfahren zur Herstellung von beta-L-2'Deoxy-Thymidin
US7582748B2 (en) * 2003-03-20 2009-09-01 Microbiologica Quimica E Farmaceutical Ltd. Methods of manufacture of 2′-deoxy-β-L-nucleosides

Also Published As

Publication number Publication date
US20050059632A1 (en) 2005-03-17
EP2157095A3 (en) 2010-09-08
EP2157095A2 (en) 2010-02-24
MXPA06000162A (es) 2006-03-21
AU2004254620A1 (en) 2005-01-13
JP2007527396A (ja) 2007-09-27
EP1639121A4 (en) 2008-04-16
NZ544634A (en) 2009-10-30
RU2009115775A (ru) 2010-10-27
RU2361875C2 (ru) 2009-07-20
EP1639121A2 (en) 2006-03-29
NO20060469L (no) 2006-03-30
RU2006102518A (ru) 2006-07-27
KR20060035652A (ko) 2006-04-26
WO2005003374A3 (en) 2005-09-01
WO2005003374A2 (en) 2005-01-13
CA2531412A1 (en) 2005-01-13

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