WO2003080613A1 - Procedes pour la preparation d'intermediaires dans la synthese de derives de 2-(purine-9-yl)-tertrahydrofuran-3,4-diol - Google Patents

Procedes pour la preparation d'intermediaires dans la synthese de derives de 2-(purine-9-yl)-tertrahydrofuran-3,4-diol Download PDF

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Publication number
WO2003080613A1
WO2003080613A1 PCT/EP2003/003027 EP0303027W WO03080613A1 WO 2003080613 A1 WO2003080613 A1 WO 2003080613A1 EP 0303027 W EP0303027 W EP 0303027W WO 03080613 A1 WO03080613 A1 WO 03080613A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
formula
compound
salt
group
Prior art date
Application number
PCT/EP2003/003027
Other languages
English (en)
Inventor
Philip Blatcher
Original Assignee
Glaxo Group Limited
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 Glaxo Group Limited filed Critical Glaxo Group Limited
Priority to AU2003212376A priority Critical patent/AU2003212376A1/en
Publication of WO2003080613A1 publication Critical patent/WO2003080613A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
    • C07D473/16—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two nitrogen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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

Definitions

  • R 3 represents C 1-3 alkyl, cyclopropyl or -CH 2 OH; a and b independently represent an integer 0 to 4 provided that a + b is in the range 3 to
  • L represents acetyloxy.
  • the two hydroxy groups are protected as acetyloxy.
  • Example 1 (15.0g, 0.94eq) was suspended in ethyl acetate (102ml) and BSA (17.4ml, 1.7eq) was added. After 30min TMSOTf (18.1ml, 2eq) was added. The mixture was heated to 60°C and a solution of Intermediate 4 (17.05g, 1eq) in ethyl acetate (32ml) was added over 45 minutes. The solution was stirred at 60°C for 1.5 hours, cooled to 15°C and quenched by the slow addition of water (85ml). Ethyl acetate (35ml) was added and the phases were separated. The aqueous phase was re-extracted with ethyl acetate (51ml). The organic extracts were combined and washed with 10% potassium bicarbonate solution (85ml, then 2 x 35ml). The solvent was removed in vacuo to give the title compound as a dry foamed residue.

Abstract

L'invention concerne un procédé de préparation d'un composé de formule (II) qui comprend la mise en réaction d'un composé de formule (IV), dans laquelle P1 représente un groupe protecteur qui est un éther cyclique relié à un noyau de purine comportant de l'azote en position 2, ou un de ses sels, avec un composé de formule (V). Ladite réaction est suivie de la déprotection et d'une éventuelle conversion en sel afin d'éliminer le composé de formule (II) ou un de ses sels.
PCT/EP2003/003027 2002-03-21 2003-03-19 Procedes pour la preparation d'intermediaires dans la synthese de derives de 2-(purine-9-yl)-tertrahydrofuran-3,4-diol WO2003080613A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003212376A AU2003212376A1 (en) 2002-03-21 2003-03-19 Process for the preparation of intermediates in the synthesis of 2- (purin-9-yl) - tetrahydrofuran-3,4-diol derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB0206655.3A GB0206655D0 (en) 2002-03-21 2002-03-21 Novel process
GB0206655.3 2002-03-21

Publications (1)

Publication Number Publication Date
WO2003080613A1 true WO2003080613A1 (fr) 2003-10-02

Family

ID=9933422

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2003/003027 WO2003080613A1 (fr) 2002-03-21 2003-03-19 Procedes pour la preparation d'intermediaires dans la synthese de derives de 2-(purine-9-yl)-tertrahydrofuran-3,4-diol

Country Status (3)

Country Link
AU (1) AU2003212376A1 (fr)
GB (1) GB0206655D0 (fr)
WO (1) WO2003080613A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005116037A1 (fr) 2004-05-24 2005-12-08 Glaxo Group Limited Dérivé de purine
WO2007009757A1 (fr) * 2005-07-19 2007-01-25 Glaxo Group Limited Derives de purine agonistes du recepteur de l'adenosine a2a

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999038877A2 (fr) * 1998-01-31 1999-08-05 Glaxo Group Limited Derives de 2-(purine-9-yl)-tetrahydrofurane-3,4-diol
WO1999067265A1 (fr) * 1998-06-23 1999-12-29 Glaxo Group Limited Derives du 2-(purin-9-yl)-tetrahydrofuran-3,4 diol

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999038877A2 (fr) * 1998-01-31 1999-08-05 Glaxo Group Limited Derives de 2-(purine-9-yl)-tetrahydrofurane-3,4-diol
WO1999067265A1 (fr) * 1998-06-23 1999-12-29 Glaxo Group Limited Derives du 2-(purin-9-yl)-tetrahydrofuran-3,4 diol

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
FIORINI M T ET AL: "Solution-Phase Synthesis of 2,6,9-Trisubstituted Purines", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 39, no. 13, 26 March 1998 (1998-03-26), pages 1827 - 1830, XP004108488, ISSN: 0040-4039 *
FRANCIS J E ET AL: "Highly selctive adenosine A2 receptor agonists in a series of N-alkylated 2-aminoadenosines", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 34, 1991, pages 2570 - 2579, XP002138750, ISSN: 0002-7863 *
HAVLICEK L ET AL: "Cytokinin-derived cyclin-dependent kinase inhibitors: synthesis and cdc2 inhibitory activity of olomoucine and related compounds", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 4, no. 40, 14 February 1997 (1997-02-14), pages 408 - 12, XP002079219, ISSN: 0022-2623 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005116037A1 (fr) 2004-05-24 2005-12-08 Glaxo Group Limited Dérivé de purine
JP2008500378A (ja) * 2004-05-24 2008-01-10 グラクソ　グループ　リミテッド プリン誘導体
US7737126B2 (en) 2004-05-24 2010-06-15 Glaxo Group Limited Purine derivative
WO2007009757A1 (fr) * 2005-07-19 2007-01-25 Glaxo Group Limited Derives de purine agonistes du recepteur de l'adenosine a2a
JP2009501746A (ja) * 2005-07-19 2009-01-22 グラクソ グループ リミテッド アデノシンａ２ａ受容体のアゴニストであるプリン誘導体
US7985740B2 (en) * 2005-07-19 2011-07-26 Glaxo Group Limited Purine derivatives as agonists of the adenosine A2A receptor

Also Published As

Publication number Publication date
GB0206655D0 (en) 2002-05-01
AU2003212376A1 (en) 2003-10-08

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