公开(公告)号：DE4025316A1

公开(公告)日：1992-02-13

申请号：DE4025316

申请日：1990-08-09

Applicant: BASF AG

Inventor： SCHMIDT RICHARD R PROF DR ,  BIRK ROLF

IPC: C07D303/36

Abstract: Epoxy-sphingosine derivs. of formula (I) are new:. In (I) X = N3 or NH2. (I) are prepd. by: (a) Gringard alkylation of 2,4-0-benzylidene-D------ (8); (b) sepn. of the prods. into diastensomers (Ia) and (1b); (c) conversion of the 3-hydroxyl gp. into an azide deriv. (3) via a reactive ester (2); (d) contension of the pure hydroxyl gp. into a reactive ester (4); (e) removal of the benzylidene protecting gp. under acid conditions to give (5a); (f) formation of (I; X=N3) under basic conditions; and (g) opt. conversion of (I; X=N3) to (I;X=NH2) with triphenylphosphine in the presence of water. R=C8-16 H17-33; Pg=protecting gp. USE - (I) are useful as modulators of intercellular communication and thus in control of differentiation and proliferation, esp. of malignant cells. They may also be used as modulators of immune reactions and as controllers of coagulation. (I) are also useful as intermediates in the prepn. of ceramides and glycosphingolipids. Admin. is oral, buccel, parenterel or topical. Systemic admin. is e.g. 1-100mg/kg/day.