DERIVATIVES OF 10,11,12,13-TETRAHYDRO-DESMYCOSINE, PROCEDURES FOR THEIR PREPARATION AND PROCEDURES FOR THE PREPARATION OF THE PHARMACEUTICAL PREPARATIONS

摘要

The invention refers to the 10,11,12,13-tetra-hydro-desmycosine derivatives, new semisynthetic antibiotics from the tylosine group with an anti-bacterial activity, to their pharmaceutically acceptable salts with organic and inorganic acids, to the procedures for their preparation and for the preparation of pharmaceutical preparations. In accordance with this invention the acetalization of C-20 position is carried out in the first stage. By means of trimethylchlorsilane the obtained 10,11,12,13-tetrahydro-desmycosine diethylacetal is transformed into 3,2',4''-tri-O-trimethylsilyl-10,11,12,13-tetrahydro-desmycosine diethylacetal which is then transformed into 4'-methansulphonyl-3,2',4''-tri-O-trimethylsilyl-10,11,12,13-tetrahydro-desmycosi diethylacetal by means of methansulphochloride, and its reaction with NaJ is transformed into 4'-deoxy-4'-iodine-3,2',4''-tri-O-trimethyl-silyl-10,11,12,13-tetrahydro-desmycosine diethylacetal, which is submitted to the hydrolysis of the protective groups in the mixture of acetonitrile and 0,2 N HCl. Raw 4'-deoxy-4'-iodine-10,11,12,13-tetrahydro-desmycosine is obtained which is purified on the silica gel column. A deiodization with catalytic amount of palladium on charcoal is carried out and a pure 4'-deoxy-10,11,12,13-tetrahydro-desmycosine is isolated.