Solco Basel Ag

Roland Tschannen

Wolfgang Fraefel

Richard R Schmidt

Peter Zimmermann

Rudolf Klager

New compounds of the formula (I)-D and (I)-L as shown in the sheet of formulae are described, for example D- and L-erythro-1-(.beta.-D-glycopyranosyloxy)-3-hydroxy-2-palmitoylamino-4-tran s-octadecene, which exert actions promoting wound healing and cell and tissue regeneration, and can be used therapeutically for the treatment of wounds of any cause. They are prepared in good yield and in a stereochemically homogeneous form from ceramides of the formula (II)-D and/or (II)-L. The process comprises the protection of the 1-hydroxyl group, esterification of the 3-hydroxyl group, elimination of the 1-hydroxyl protective group, reaction with the trifluoroacetimidate or trichloroacetimidate of a 2,3,4,6-tetraacylated D-glucose and elimination of the O-acyl groups. When a D,L-ceramide (II) is used, the esterification of the 3-hydroxyl group is carried out by an optically active acid followed by separation into the diastereomers, or separation into the diastereomers is carried out after the reaction with the D-glucose derivative.

Process for the preparation of sphingosine derivatives

Glycolipids having cell- and tissue-regenerating properties are isolated from the blood or organ homogenates of mammals by subjecting the starting material to autolysis and dialysis against an alcoholic-aqueous medium. The glycolipids can be isolated, and purified, from the resulting crude product by precipitation with ethanol or extraction followed by chromatography. The process gives relatively high yields of active compounds; it is outstandingly suitable for industrial application.

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Basel, Switzerland

Roland Tschannen