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1. 发明授权

US4952683A Process for the preparation of sphingosine derivatives 失效
标题翻译：鞘氨醇衍生物的制备方法
公开(公告)号：US4952683A
公开(公告)日：1990-08-28
申请号：US137957
申请日：1987-12-24
申请人： Roland Tschannen , Wolfgang Fraefel , Richard R. Schmidt , Rudolf Klager , Peter Zimmermann
发明人： Roland Tschannen , Wolfgang Fraefel , Richard R. Schmidt , Rudolf Klager , Peter Zimmermann
IPC分类号： A61K31/70 , C07H15/10
CPC分类号： C07H15/10 , Y02P20/55
摘要： 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.
摘要翻译：描述了式（I）-D和（I）-L的新化合物，如式中所示，例如D-和L-赤式-1-（β-D-糖吡喃糖基氧基）-3-羟基-2 - 棕榈酰氨基-4-反式十八碳烯，其发挥促进伤口愈合和细胞和组织再生的作用，并且可以用于治疗任何原因的伤口。它们以良好的收率和立体化学均匀的形式由式（II）-D和/或（II）-L的神经酰胺制备。该方法包括1-羟基的保护，3-羟基的酯化，1-羟基保护基的消除，与3,4,4,6-四酰化D-葡萄糖的三氟乙酰亚胺酸酯或三氯乙酰亚胺酸酯的反应，以及消除O-酰基。当使用D，L-神经酰胺（II）时，3-羟基的酯化通过光学活性酸进行，然后分离成非对映异构体，或者在与D反应后进行非对映异构体的分离 - 葡萄糖衍生物。

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