Novel compounds of the gentamicin class
AssigneeSterling Drug Inc.
InventorDavid Rosi
Life of this patent
Estimating the term…
Abstract
5-Deoxygentamicin C.sub.2b and 6'-N-methyl-2-hydroxy- and 6'-N-methyl-5-deoxygentamicins C.sub.2b are prepared, as the major fermentation products, by culturing a nutrient medium containing carbohydrates, a source of assimilable nitrogen, essential salts and either D-streptamine or 2,5-dideoxystreptamine with a mutant of Micromonospora purpurea and isolating the fermentation products from the nutrient medium. The fermentation products are acylated with an ester of an .omega.-[N-(benzyloxycarbonyl)amino]-.alpha.-hydroxy-lower-alkanoic acid after first blocking the primary amino group at the 2'-position with an amine-protecting group, followed by catalytic hydrogenolysis of the benzyloxycarbonyl group and removal of the amine-protecting group to prepare the 1-(.omega.-amino-.alpha.-hydroxy-lower-alkanoyl) derivatives.
Claims5
A member of the group consisting of
- (A) a compound having the formula:
- ##STR3## where R.sub.1 is hydrogen or the group, H.sub.2 N(CH.sub.2).sub.n CHOHCO--, where n is one of the integers 1 or 2;
- R.sub.2 and R.sub.5 are either both hydroxy or both hydrogen;
- and R.sub.6 is hydrogen or methyl, R.sub.2 being hydroxy only when R.sub.6 is methyl;
- and
- (B) acid-addition salts thereof.
A process for preparing a compound having the formula:
- ##STR4## which comprises culturing micromonospora purpurea ATCC 31,849 in a nutrient medium containing carbohydrates, a source of assimilable nitrogen, essential salts and either D-streptamine, to prepare, as a major component, the compound where R.sub.2 and R.sub.5 are both hydroxy and R.sub.6 is hydrogen and, as a minor component, the compound where R.sub.2 and R.sub.5 are both hydroxy and R.sub.6 is methyl, or 2,5-dideoxystreptamine, to prepare, as the major component, the compound where R.sub.2, R.sub.5 and R.sub.6 are each hydrogen and, as a minor component, the compound where R.sub.2 and R.sub.5 are both hydrogen and R.sub.6 is methyl and isolating the said compounds from the nutrient medium.
Dependencies are inferred from the claim text.