Process for the preparation of sphingosine derivatives

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United States of America Patent

PATENT NO 4952683
SERIAL NO

07137957

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Abstract

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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-trans-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.

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Patent Owner(s)

Patent OwnerAddress
SOLCO BASEL AGGELLERSTRASSE 18 CH-4052 BASEL

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Inventor(s)

Inventor Name Address # of filed Patents Total Citations
Fraefel, Wolfgang Grolley, CH 3 85
Klager, Rudolf Eutingen, DE 1 33
Schmidt, Richard R Konstanz, DE 12 132
Tschannen, Roland Basel, CH 2 42
Zimmermann, Peter Villingen, DE 38 543

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