Semi-synthetic glycosaminoglycans containing...

C - Chemistry – Metallurgy – 08 – B

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C08B 37/10 (2006.01) C08B 37/00 (2006.01)

Patent

CA 2093148

The synthesis of new semi-synthetic glycosaminoglycans is described in which one of the saccharide units characteristic of glycosaminoglycans with heparin or heparan structure, more specifically that of .alpha.-L-iduronic-2-O-sulfate acid, has undergone a structural modification, entirely or in part, with transformation into .alpha.-L-galacturonic acid substituted with nucleophilic radicals in position 3. These new semi-synthetic glycosaminoglycans of general formula IV (see fig. I) have good pharmaceutical properties in that they may also be absorbed orally and have good anti-thrombotic activity accompanied by low risk of hemorrhage and reduced anti-coagutating activity.

Description de la synthèse de nouveaux glycosaminoglycanes semi-synthétiques, dans lesquels l'une des unités saccharides, propres aux glycosaminoglycanes, à structure d'héparine ou d'héparane, plus spécifiquement celle d'acide alpha-L-iduronique 2-O-sulfaté, a subi une modification structurelle complète ou partielle, avec transformation complète ou partielle en acide alpha-L-galacturonique avec substitution par des radicaux nucléophiles en 3. Ces nouveaux glycosaminoglycanes semi-synthétiques de formule générale IV (voir fig. I) possèdent de bonnes propriétés pharmaceutiques, car ils peuvent être absorbés par voie orale et ont une activité antithrombotiques marquée, avec un faible risque d'hémorragie et une activité anti-coagulante réduite.

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