Derivatives of 12,13-Epoxy-tylosin and processes of manufacture thereof

Method for manufacture of derivative of 12,13-epoxy-tylosin of the formula I ##STR8## wherein R stands for O, R.sup.1 stands for CHO or CH(OCH.sub.3).sub.2, R.sup.2 stands for H or mycarosyl, and -- has the meaning of a single bond,

• wherein R stands for NOH, R.sup.1 stands for CHO or CH(OCH.sub.3).sub.2, R.sup.2 stands for H or mycarosyl, and -- has the meaning of a single or a double bond,
• and the compounds of the formula II ##STR9## wherein R stands for H or mycarosyl characterized in that the compound of the formula III ##STR10## A) wherein R stands for CHO or CH(OCH.sub.3).sub.2, R.sup.1 stands for H or mycarosyl, R.sup.2 stands for N(CH.sub.3).sub.2 or N--O(CH.sub.3).sub.2 when R.sup.1 means H, is subjected to hydrogenation in an organic solvent, with 2-5% w/w palladium-on-charcoal and 0.2-0.5 MPa hydrogen pressure at ambient temperature for 5-8 hrs;
• and then optionally obtained compound of the formula I, wherein R stands for O, R.sup.1 stands for CH(OCH.sub.3).sub.2, R.sup.2 stands for H or mycarosyl, and -- has the meaning of a single bond, is subjected to oximation with 3-6 equivalent hydroxylamine hydrochloride in pyridine, or a lower alcohol with the addition of a base such as pyridine (or Na.sub.2 CO.sub.3) under nitrogen stream at ambient temperature or reflux temperature during 3-7 hrs, and then optionally to hydrolysis of acetal group;
• B) wherein R stands for CH(OCH.sub.3).sub.2, R.sup.1 stands for H or mycarosyl and R.sup.2 stands for N(CH.sub.3).sub.2 is subjected to oximation as previously described and the obtained products:
• the compound of the formula I, wherein R stands for NOH, R.sup.1 stands for CH(OCH.sub.3).sub.2, R.sup.2 stands for H or mycarosyl, and -- has the meaning of a double bond,
• and the compound of the formula II, wherein R stands for H or mycarosyl are chromatographically separated on a silicagel column and then optionally subjected to hydrolysis of acetal group.