CA2237730C - Method and compositions for the synthesis of dioxolane nucleosides with .beta.-configuration - Google Patents

Method and compositions for the synthesis of dioxolane nucleosides with .beta.-configuration Download PDF

Info

Publication number
CA2237730C
CA2237730C CA002237730A CA2237730A CA2237730C CA 2237730 C CA2237730 C CA 2237730C CA 002237730 A CA002237730 A CA 002237730A CA 2237730 A CA2237730 A CA 2237730A CA 2237730 C CA2237730 C CA 2237730C
Authority
CA
Canada
Prior art keywords
process according
group
formula
alkyl
hydrogen
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.)
Expired - Lifetime
Application number
CA002237730A
Other languages
English (en)
French (fr)
Other versions
CA2237730A1 (en
Inventor
Tarek Mansour
Alex Cimpoia
Krzysztof Bednarski
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.)
Shire Canada Inc
Original Assignee
Shire BioChem Inc
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 Shire BioChem Inc filed Critical Shire BioChem Inc
Publication of CA2237730A1 publication Critical patent/CA2237730A1/en
Application granted granted Critical
Publication of CA2237730C publication Critical patent/CA2237730C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • 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)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CA002237730A 1995-12-14 1996-12-13 Method and compositions for the synthesis of dioxolane nucleosides with .beta.-configuration Expired - Lifetime CA2237730C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB9525606.1 1995-12-14
GBGB9525606.1A GB9525606D0 (en) 1995-12-14 1995-12-14 Method and compositions for the synthesis of dioxolane nucleosides with › - configuration
PCT/CA1996/000845 WO1997021706A1 (en) 1995-12-14 1996-12-13 METHOD AND COMPOSITIONS FOR THE SYNTHESIS OF DIOXOLANE NUCLEOSIDES WITH β-CONFIGURATION

Publications (2)

Publication Number Publication Date
CA2237730A1 CA2237730A1 (en) 1997-06-19
CA2237730C true CA2237730C (en) 2001-12-04

Family

ID=10785435

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002237730A Expired - Lifetime CA2237730C (en) 1995-12-14 1996-12-13 Method and compositions for the synthesis of dioxolane nucleosides with .beta.-configuration

Country Status (27)

Country Link
US (4) US5922867A (en, 2012)
EP (1) EP0970074B1 (en, 2012)
JP (1) JP3229990B2 (en, 2012)
KR (1) KR100406159B1 (en, 2012)
CN (1) CN1080263C (en, 2012)
AP (1) AP879A (en, 2012)
AT (1) ATE214699T1 (en, 2012)
AU (1) AU706328B2 (en, 2012)
BR (1) BR9612351A (en, 2012)
CA (1) CA2237730C (en, 2012)
DE (1) DE69620042T2 (en, 2012)
DK (1) DK0970074T3 (en, 2012)
EA (1) EA000844B1 (en, 2012)
ES (1) ES2172697T3 (en, 2012)
GB (1) GB9525606D0 (en, 2012)
HU (1) HU224076B1 (en, 2012)
IL (3) IL124663A (en, 2012)
IN (1) IN187349B (en, 2012)
MX (1) MX9804701A (en, 2012)
NO (1) NO309901B1 (en, 2012)
NZ (1) NZ323855A (en, 2012)
OA (1) OA11094A (en, 2012)
PL (1) PL188447B1 (en, 2012)
PT (1) PT970074E (en, 2012)
TW (1) TW341574B (en, 2012)
WO (1) WO1997021706A1 (en, 2012)
ZA (1) ZA9610544B (en, 2012)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU6898498A (en) 1997-04-07 1998-10-30 Triangle Pharmaceuticals, Inc. Use of mkc-442 in combination with other antiviral agents
MXPA01001552A (es) 1998-08-12 2004-08-23 Triangle Pharmaceuticals Inc Metodo de elaboracion de 1,3-oxatiolan-nucleosidos.
US6979561B1 (en) 1998-10-09 2005-12-27 Gilead Sciences, Inc. Non-homogeneous systems for the resolution of enantiomeric mixtures
HUP0104827A3 (en) 1998-12-23 2002-08-28 Shire Biochem Inc Laval Antiviral nucleoside analogues
CA2362570A1 (en) * 1999-02-11 2000-08-17 Shire Biochem Inc. Stereoselective synthesis of nucleoside analogues
ATE269081T1 (de) * 1999-09-24 2004-07-15 Shire Biochem Inc Dioxolan nukleosidanalogen zur behandlung und vorbeugung von viralen infektionen
US6566365B1 (en) 1999-11-04 2003-05-20 Biochem Pharma Inc. Method for the treatment of Flaviviridea viral infection using nucleoside analogues
BR0104461A (pt) * 2000-02-10 2002-08-06 Mitsui Chemicals Inc Processo seletivo para produzir um anÈmero a partir de um derivado de sacarìdeo 1-fosforilado e processo para produzir um nucleosìdeo
AU3144801A (en) 2000-02-11 2001-08-20 Shire Biochem Inc. Stereoselective synthesis of nucleoside analogues
WO2002051852A1 (fr) * 2000-12-27 2002-07-04 Mitsui Chemicals, Inc. Procede de production d'un derive de saccharide non naturel
ES2253544T3 (es) 2001-03-01 2006-06-01 Gilead Sciences, Inc. Formas poliformicas y otras cristalinas de cis-ftc.
AU2002329970A1 (en) * 2001-09-04 2003-03-18 Isis Pharmaceuticals, Inc. Pyrrolo(2,3-d)pyrimidines for inhibiting rna-dependent rna viral polymerase
AU2002336864B2 (en) * 2001-11-02 2006-08-17 Shire Biochem Inc. Pharmaceutical compositions for the treatment of leukemia comprising dioxolane nucleosides analogs
CA2470255C (en) 2001-12-14 2012-01-17 Kyoichi A. Watanabe N4-acylcytosine nucleosides for treatment of viral infections
JP4441265B2 (ja) * 2002-01-25 2010-03-31 シャー バイオケム インコーポレイティッド ジオキソランヌクレオシド類似体の製造方法
MXPA05001451A (es) 2002-08-06 2005-09-30 Pharmasset Ltd Procesos para preparar nucleosidos de 1,3-dioxolano.
CN101724110B (zh) 2002-10-15 2013-03-27 埃克森美孚化学专利公司 用于烯烃聚合的多催化剂体系和由其生产的聚合物
DE10335061B4 (de) 2003-07-31 2005-11-17 Wacker-Chemie Gmbh Verfahren zur Herstellung von OH-geschützten [4-(2,6-damino-9H-purin-9-yl)-1,3-dioxolan-2-yl]methanol-Derivaten
CN105039489A (zh) * 2004-02-03 2015-11-11 埃莫里大学 制备1,3-二氧戊环核苷的方法
US7749531B2 (en) * 2005-06-08 2010-07-06 Indicator Systems International Apparatus and method for detecting bacterial growth beneath a wound dressing
BRPI0813036A2 (pt) * 2007-07-30 2017-10-24 Rfs Pharma Llc processo estereosseletivo para preparar derivados do nucleosídeo dioxolana de purina.
CN101862676B (zh) * 2009-04-17 2012-01-25 中国石油化工股份有限公司 大孔径sba-15介孔材料-三氟甲磺酸铜复合催化剂、制备方法及应用
CN103288806A (zh) * 2013-07-02 2013-09-11 山东大学 一种曲沙他滨的合成方法
WO2018022263A1 (en) 2016-07-29 2018-02-01 Exxonmobil Chemical Patents Inc. Polymerization processes using high molecular weight polyhydric quenching agents
WO2019245444A1 (en) 2018-06-21 2019-12-26 Medivir Ab Base-modified cytidine nucleotides for leukemia therapy
JP7337539B2 (ja) * 2018-06-21 2023-09-04 メディヴィル・アクチエボラーグ 白血病療法のための塩基修飾シチジンヌクレオチド

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5276151A (en) * 1990-02-01 1994-01-04 Emory University Method of synthesis of 1,3-dioxolane nucleosides
JPH0673086A (ja) * 1992-06-22 1994-03-15 Eli Lilly & Co 立体選択的な陰イオングリコシル化法

Also Published As

Publication number Publication date
US6069250A (en) 2000-05-30
EP0970074B1 (en) 2002-03-20
OA11094A (en) 2003-03-13
AP879A (en) 2000-10-02
ZA9610544B (en) 1997-07-29
HUP9901050A3 (en) 2001-05-28
US5922867A (en) 1999-07-13
IL124663A (en) 2001-10-31
JP3229990B2 (ja) 2001-11-19
WO1997021706A1 (en) 1997-06-19
IL144155A (en) 2003-07-06
DE69620042T2 (de) 2002-10-17
ES2172697T3 (es) 2002-10-01
AU706328B2 (en) 1999-06-17
NO982716D0 (no) 1998-06-12
EP0970074A1 (en) 2000-01-12
PL188447B1 (pl) 2005-02-28
EA000844B1 (ru) 2000-06-26
AP9801252A0 (en) 1998-06-30
IN187349B (en, 2012) 2002-03-30
HK1017886A1 (en) 1999-12-03
DK0970074T3 (da) 2002-07-15
NO982716L (no) 1998-06-12
GB9525606D0 (en) 1996-02-14
IL124663A0 (en) 1998-12-06
CA2237730A1 (en) 1997-06-19
PL327443A1 (en) 1998-12-07
KR100406159B1 (ko) 2004-11-16
HUP9901050A2 (hu) 2001-04-28
NZ323855A (en) 1999-11-29
JP2000501714A (ja) 2000-02-15
US20030060476A1 (en) 2003-03-27
CN1208414A (zh) 1999-02-17
IL144155A0 (en) 2002-05-23
AU1089397A (en) 1997-07-03
ATE214699T1 (de) 2002-04-15
CN1080263C (zh) 2002-03-06
DE69620042D1 (de) 2002-04-25
NO309901B1 (no) 2001-04-17
MX9804701A (es) 1998-10-31
BR9612351A (pt) 1999-07-13
HU224076B1 (hu) 2005-05-30
EA199800555A1 (ru) 1999-02-25
TW341574B (en) 1998-10-01
KR19990072141A (ko) 1999-09-27
US20020058670A1 (en) 2002-05-16
PT970074E (pt) 2002-09-30

Similar Documents

Publication Publication Date Title
CA2237730C (en) Method and compositions for the synthesis of dioxolane nucleosides with .beta.-configuration
KR0160144B1 (ko) 뉴클레오시드의 부분 입체 이성체를 선택적으로 합성하는 방법
FI112078B (fi) Nukleosidianalogien stereoselektiivinen synteesi kaksirenkaista välituotetta käyttämällä
KR20070085075A (ko) 1,3-디옥솔란 뉴클레오시드 제조방법
HU223100B1 (hu) Eljárás nukleozidanalógok előállítására és a köztitermékek
HK1017886B (en) METHOD AND INTERMEDIATE FOR THE SYNTHESIS OF DIOXOLANE NUCLEOSIDE WITH β-CONFIGURATION
WO2003010179A1 (en) Process for the preparation of 2'-3'-dideoxy-2',3'-didehydro-nucleosides
WO2003040139A1 (en) Diastereoselective process for the preparation of the antiviral agent4-amino-1-(2r-hydroxymethyl-[1,3]oxathiolan-5s-yl)-1h-pyrimidin-2-one
HK1008673B (en) Stereoselective synthesis of nucleoside analogues using bicyclic intermediate

Legal Events

Date Code Title Description
EEER Examination request
MKEX Expiry

Effective date: 20161213