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Title:
COMPOSITIONS COMPRISING SUGAR ESTER OF MYCOLIC ACID DERIVATIVES AND PROCESS THE PREPARATION THEREOF
Document Type and Number:
WIPO Patent Application WO/2010/086667
Kind Code:
A3
Abstract:
A method of preparing a compound of formula (III): wherein x is from 1 to 6, y is from 1 to 12, z is from 0 to 10, each M and each M' is independently a mycolic acid residue including a β-hydroxy acid moiety and each S is a monosaccharide unit; the method comprising reacting one or more mycolic acids with one or more saccharide units wherein the hydroxyl group of each β-hydroxy acid moiety is protected prior to reaction with the one or more saccharide units.

Inventors:
BAIRD, Mark Stephen (School of Chemistry, Bangor UniversityBangor, Gwynedd LL57 2DG, GB)
AL-DULAYYMI, Juma' a Raheem Najeem (School of Chemistry, Bangor UniversityBangor, Gwynedd LL57 2DG, GB)
GROOTEN, Johan Adriaan Marc (Department of Biomedical Molecular Biology, Ghent UniversityTechnolgiepark 927 Zwijnaard, Zwijnaarde Ghent, B-9052, BE)
VANDER BEKEN, Seppe (Department of Biomedical Molecular Biology, Ghent UniversityTechnologiepark 927 Zwijnaard, Zwijnaarde Ghent, B-9052, BE)
MAZA-INGLESIAS, Maximilliano (School of Chemistry, Bangor UniversityBangor, Gwynedd LL57 2DG, GB)
Application Number:
GB2010/050146
Publication Date:
August 05, 2010
Filing Date:
January 29, 2010
Export Citation:
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Assignee:
BANGOR UNIVERSITY (College Road, Bangor, Gwynedd LL57 2DG, GB)
BAIRD, Mark Stephen (School of Chemistry, Bangor UniversityBangor, Gwynedd LL57 2DG, GB)
AL-DULAYYMI, Juma' a Raheem Najeem (School of Chemistry, Bangor UniversityBangor, Gwynedd LL57 2DG, GB)
GROOTEN, Johan Adriaan Marc (Department of Biomedical Molecular Biology, Ghent UniversityTechnolgiepark 927 Zwijnaard, Zwijnaarde Ghent, B-9052, BE)
VANDER BEKEN, Seppe (Department of Biomedical Molecular Biology, Ghent UniversityTechnologiepark 927 Zwijnaard, Zwijnaarde Ghent, B-9052, BE)
MAZA-INGLESIAS, Maximilliano (School of Chemistry, Bangor UniversityBangor, Gwynedd LL57 2DG, GB)
International Classes:
C07H13/04; C07H23/00
Domestic Patent References:
WO2009130506A22009-10-29
WO2009130508A12009-10-29
Foreign References:
EP0261248A11988-03-30
JP2002179574A2002-06-26
JP2002179577A2002-06-26
US5721109A1998-02-24
Other References:
NISHIZAWA MUGIO ET AL: "Efficient Syntheses of a Series of Trehalose Dimycolate (TDM)/Trehalose Dicorynomycolate (TDCM) Analogues and Their Interleukin-6 Level Enhancement Activity in Mice Sera", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, EASTON.; US, vol. 72, no. 5, 8 February 2007 (2007-02-08), pages 1627 - 1633, XP009111529, ISSN: 0022-3263, DOI: DOI:10.1021/JO062018J
PARANT M ET AL: "Nonspecific immunostimulant activities of synthetic trehalose-6,6'-diesters (lower homologs of cord factor)", INFECTION AND IMMUNITY, AMERICAN SOCIETY FOR MICROBIOLOGY, WASHINGTON, US, vol. 20, no. 1, 1 April 1978 (1978-04-01), pages 12 - 19, XP002539259, ISSN: 0019-9567
POLONSKY JUDITH ET AL: "Cord factor, a toxic lipide from Mycobacterium tuberculosis. Synthesis of cord factor-active substances (esters of trehalose and synthetic branched chain acids)", BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, SOCIETE FRANCAISE DE CHIMIE. PARIS, FRANCE, 1 January 1956 (1956-01-01), pages 1471 - 1478, XP009149068, ISSN: 0037-8968
BROCHURE-FERREOL GENEVIEVE ET AL: "Substances with cord factor activity. Synthesis of 6,6'-diesters of trehalose", BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, SOCIETE FRANCAISE DE CHIMIE. PARIS, FRANCE, 1 January 1958 (1958-01-01), pages 714 - 717, XP009149072, ISSN: 0037-8968
KATO, MASAHIKO ET AL: "Chemical structure and biochemical activity of cord factor analogs 6,6'-dimycoloyl sucrose and methyl 6-mycoloyl-.alpha.-D-glucoside", EUROPEAN JOURNAL OF BIOCHEMISTRY , 22(3), 364-70 CODEN: EJBCAI; ISSN: 0014-2956, 1971, XP002640597
AL DULAYYMI J R ET AL: "The first unique synthetic mycobacterial cord factors", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 50, no. 26, 1 July 2009 (2009-07-01), pages 3702 - 3705, XP026120596, ISSN: 0040-4039, [retrieved on 20090405], DOI: DOI:10.1016/J.TETLET.2009.03.213
Attorney, Agent or Firm:
DELANEY, Jennifer Sarah (Appleyard Lees, 15 Clare RoadHalifax,Halifax, Yorkshire HX1 2HY, GB)
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