Alfa Wassermann S.p.a.

Alfa Wassernann S.p.a.

Fabrizio Ungarelli

Silvano Piani

Egidio Marchi

Gianfranco Tamagnone

New heparin and heparan sulfate derivatives having antithrombotic activity, also endowed with reduced haemorrhagic and anticoagulant activity, are obtained by nucleophilic addition to heparin and heparan sulfate derivatives containing 2,3-anhydrogulonic acid residues. The compounds have the formula IV ##STR1## The glycosaminoglycan derivatives obtained through this treatment show a structural modification in the unit of .alpha.-L-iduronic acid 2-O-sulfate with the partial or total selective substitution of the O-sulfate group in position 2 with a nucleophilic residue. The structural modifications produce an improvement of the biological properties of the heparin and heparan sulfate, substantially keeping the antithrombotic activity while diminishing the haemorragic effect in vivo and the anticoagulant activity in vitro.

Semi-synthetic glycosaminoglycans with heparin or heparan structure of

A process for the synthesis of glycosaminoglycans in which one of the .alpha.-L-iduronic-2-O-sulfate acid saccharide units, which is characteristic of glycosaminoglycans with heparin or heparan structure, has undergone a structural modification, entirely or in part, with transformation into .alpha.-L-galacturonic acid substituted in position 3 with nucleophilic groups, is described. The process is carried out by treating glycosaminoglycans having heparin or heparan structure with a nucleophilic reagent in alkaline solution.

Process for the synthesis of glycosaminoglycans containing

A process for the synthesis of glycosaminoglycans with heparin or heparan structure modified in position 2 of the .alpha.-L-iduronic-2-O-sulfate acid in which the sulfate group is, entirely or in part, substituted with a nucleophilic group, is described. The process is carried out by treating glycosaminoglycans having heparin or heparan structure with a nucleophilic reagent in alkaline solution.

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Bologna, Italy

Fabrizio Ungarelli