Sphingosine derivatives, their preparation and...

Details Sphingosine derivatives, their preparation and... Sphingosine derivatives, their preparation and...

C - Chemistry, Metallurgy

07

H

167/199, 260/228

C07H 15/04 (2006.01) A61K 31/70 (2006.01) C07H 15/10 (2006.01)

Patent

CA 1259610

Sphingosine Derivatives, Their Preparation and Pharmaceutical Formulation Abstract of the Disclosure 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-(.delta.-D-glucopyranosyloxy)-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 pro- tective 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 separ- ation into the diastereomers is carried out after the reaction with the D-glucose derivative.

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