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

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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
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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
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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
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Shire BioChem Inc
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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

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/02Heterocyclic 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
    • C07D405/04Heterocyclic 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
    • 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
    • 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

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  • 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 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
EP (1) EP0970074B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
JP (1) JP3229990B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
KR (1) KR100406159B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CN (1) CN1080263C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
AP (1) AP879A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
AT (1) ATE214699T1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
AU (1) AU706328B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
BR (1) BR9612351A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CA (1) CA2237730C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DE (1) DE69620042T2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DK (1) DK0970074T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
EA (1) EA000844B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
ES (1) ES2172697T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
GB (1) GB9525606D0 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
HU (1) HU224076B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
IL (3) IL124663A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
IN (1) IN187349B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
MX (1) MX9804701A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
NO (1) NO309901B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
NZ (1) NZ323855A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
OA (1) OA11094A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
PL (1) PL188447B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
PT (1) PT970074E (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
TW (1) TW341574B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
WO (1) WO1997021706A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
ZA (1) ZA9610544B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6410546B1 (en) 1997-04-07 2002-06-25 Triangle Pharmaceuticals, Inc. Use of MKC-442 in combination with other antiviral agents
AU771779B2 (en) 1998-08-12 2004-04-01 Emory University Method of manufacture of 1,3-oxathiolane nucleosides
US6979561B1 (en) 1998-10-09 2005-12-27 Gilead Sciences, Inc. Non-homogeneous systems for the resolution of enantiomeric mixtures
NZ513094A (en) 1998-12-23 2004-05-28 Shire Biochem Inc Antiviral nucleoside analogues
JP2002538780A (ja) * 1999-02-11 2002-11-19 シェア バイオケム インコーポレーテッド ヌクレオシド類似体の立体選択的合成
ES2218216T3 (es) * 1999-09-24 2004-11-16 Shire Biochem Inc. Analogos de nucleosidos de dioxolano para el tratamiento o la prevencion de infecciones viricas.
WO2001032153A2 (en) * 1999-11-04 2001-05-10 Shire Biochem Inc. Method for the treatment or prevention of flaviviridae viral infection using nucleoside analogues
ATE397001T1 (de) * 2000-02-10 2008-06-15 Mitsui Chemicals Inc Verfahren zur selektiven herstellung eines 1- phosphoryliertem zuckerderivativ-anomers und verfahren zur herstellung von nukleosiden
CA2399062C (en) * 2000-02-11 2010-01-12 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
PT1574512E (pt) * 2001-03-01 2008-03-05 Abbott Lab Formas polimórficas e outras formas cristalinas de cis-ftc
WO2003020222A2 (en) * 2001-09-04 2003-03-13 Merck & Co., Inc. PYRROLO[2,3-d]PYRIMIDINES FOR INHIBITING RNA-DEPENDENT RNA VIRAL POLYMERASE
EP1441733A1 (en) * 2001-11-02 2004-08-04 Shire Biochem Inc. Pharmaceutical compositions for the treatment of leukemia comprising dioxolane nucleosides analogs
JP2005519916A (ja) * 2001-12-14 2005-07-07 フアーマセツト・リミテツド ウィルス感染治療用n4−アシルシトシンヌクレオシド類
CA2473736C (en) * 2002-01-25 2011-10-11 Shire Biochem Inc. Process for producing dioxolane nucleoside analogues
US6855821B2 (en) 2002-08-06 2005-02-15 Pharmasset, Ltd. Processes for preparing 1,3-dioxolane nucleosides
AU2003302033A1 (en) 2002-10-15 2004-06-15 Exxonmobil Chemical Patents Inc. Multiple catalyst system for olefin polymerization and polymers produced therefrom
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
CN101044122A (zh) * 2004-02-03 2007-09-26 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
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
WO2019245444A1 (en) 2018-06-21 2019-12-26 Medivir Ab Base-modified cytidine nucleotides for leukemia therapy

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
PL299413A1 (en) * 1992-06-22 1994-03-07 Lilly Co Eli Stereoselective glycozilation process effected by means o anions

Also Published As

Publication number Publication date
WO1997021706A1 (en) 1997-06-19
JP2000501714A (ja) 2000-02-15
NZ323855A (en) 1999-11-29
US20030060476A1 (en) 2003-03-27
KR100406159B1 (ko) 2004-11-16
ZA9610544B (en) 1997-07-29
IL144155A (en) 2003-07-06
DK0970074T3 (da) 2002-07-15
JP3229990B2 (ja) 2001-11-19
NO982716D0 (no) 1998-06-12
CN1080263C (zh) 2002-03-06
IL144155A0 (en) 2002-05-23
CA2237730A1 (en) 1997-06-19
EP0970074B1 (en) 2002-03-20
EP0970074A1 (en) 2000-01-12
US20020058670A1 (en) 2002-05-16
NO309901B1 (no) 2001-04-17
EA000844B1 (ru) 2000-06-26
HUP9901050A3 (en) 2001-05-28
NO982716L (no) 1998-06-12
DE69620042D1 (de) 2002-04-25
CN1208414A (zh) 1999-02-17
PT970074E (pt) 2002-09-30
OA11094A (en) 2003-03-13
AU1089397A (en) 1997-07-03
EA199800555A1 (ru) 1999-02-25
IL124663A (en) 2001-10-31
PL188447B1 (pl) 2005-02-28
MX9804701A (es) 1998-10-31
AP9801252A0 (en) 1998-06-30
AP879A (en) 2000-10-02
ATE214699T1 (de) 2002-04-15
US5922867A (en) 1999-07-13
PL327443A1 (en) 1998-12-07
KR19990072141A (ko) 1999-09-27
ES2172697T3 (es) 2002-10-01
TW341574B (en) 1998-10-01
HUP9901050A2 (hu) 2001-04-28
HK1017886A1 (en) 1999-12-03
DE69620042T2 (de) 2002-10-17
GB9525606D0 (en) 1996-02-14
BR9612351A (pt) 1999-07-13
HU224076B1 (hu) 2005-05-30
US6069250A (en) 2000-05-30
IL124663A0 (en) 1998-12-06
IN187349B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 2002-03-30
AU706328B2 (en) 1999-06-17

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