Novel glycoside compounds and production and use thereof

Details Novel glycoside compounds and production and use thereof Novel glycoside compounds and production and use thereof

C - Chemistry, Metallurgy

07

J

C07J 17/00 (2006.01) C07H 15/256 (2006.01) C07J 9/00 (2006.01) A61K 31/705 (1990.01)

Patent

CA 2113819

Novel glycosides, especially steroidal and non--steroidal glycosides, and a novel method of their production, are provided. For the novel method of producing novel glycosides, aglycon compounds are glycosylated with tri-O-acyl glucal using molecular or ionized halogen as a reaction catalyst. In this method an aglycon, which may be a nonsteroid or a steroid having a reactive functional group (e.g., -OH, -SH, -COOH, -NH2, - NHR1) such as a cholesterol, is glycosylated, such that the glycosylation is performed in a single step. For example, if a steroid, the resulting steryl pyranoside, is by oxidation converted to the corresponding 7-ketosteryl di-O--acyl-pyranoside. The latter pyranoside is selectively reduced to provide the corresponding 7-.beta.-hydroxysteryl 2,3--dideoxy-.alpha.-D-erythro-hex-2-enopyranoside. The steroidal and non-steroidal glycosides obtained in this way possess valuable pharmacological properties. In particular, the cholesterol glycoside in vivo exhibits a selective cell--destructive activity on malignant cells which activity is substantially free of side effects on normal cells. The glycosides possess useful properties, especially pharmacological properties which are the same as their respective unglycosylated aglycons. The properties may include a drive-enhancing (stimulating) activity and an anti-inflammatory (immunosuppressive or immunoregulatory) activity.

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