Anthracycline glycosides

Details Anthracycline glycosides Anthracycline glycosides

C - Chemistry, Metallurgy

07

H

260/208.2

C07H 15/252 (2006.01)

Patent

CA 1237714

Title ANTHRACYCLINE GLYCOSIDES Abstract of the disclosure Disclosed is a process for preparing the glycoside antitumor anthracyclines 7-0-(2,6-dideoxy-?-L-arabino-hexopyranosyl)- daunomycinone (Ia); 4-demethoxy-7-0-(2,6-dideoxy-?-L-arabino- hexopyranosyl)-daunomycinone (Ib); 7-0-(2,6-dideoxy-?-L- -arabino-hexopyranosyl)-adriamycinone (Ic); 4-demethoxy-7-0- -(2,6-dideoxy-?-L-arabino-hexopyranosyl)-adriamycinone (Id); 7-0-(2,3,6-trideoxy-?-L-erythro-hex-2-enopyranosyl)-daunomyci- none (IIa); 4-demethoxy-7-0-(2,3,6-trideoxy-?-L-erythro-hex-2- -enopyranosyl)-daunomycinone (IIb); 7-0-(2,3,6-trideoxy-?-L- erythro-hex-2-enopyranosyl)-adriamycinone (IIc); and 4-deme- thoxy-7-0-(2,3,6-trideoxy-?-L-erythro-hex-2-enopyranosyl)- adriamycinone (IId). The derivatives Ia, Ib, IIa, IIb are prepared by condensing daunomycinone and 4-demethoxydaunomycinone with 3,4-di-0- acetyl-2,6-dideoxy-?-L-arabino-hexopyranosyl chloride in an inert solvent in the presence of silver triflate (silver tri- fluoromethansulfonate), as catalyst, and by removing the protecting groups. Analogously the derivatives Ic, Id, IIc and IId are prepared by condensing a novel reactive protected derivative of adri- amycinone and 4-demethoxyadriamycinone in the presence of mercuric bromide/mercuric oxide with the above mentioned sugar halide. The new compounds of the invention are useful in treating certain tumors in experimental animals. -2-

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