3',4'-dideoxykanamycin a and

Abstract

3',4'-Dideoxy derivative and 1-N-((S)-.alpha.-hydroxy-.omega.-aminoalkanoyl)-3',4'-dideoxy derivative of kanamycin A are now synthetized from kanamycin A and show a wider and/or higher antibacterial activity than the parent kanamycin A so that they are useful in therapeutic treatment of infections by gram-negative and gram-positive bacteria, including drug-resistant strains thereof. The production of these new derivatives may be made by preparing a protected kanamycin A derivative having its 3'- and 4'-hydroxyl groups unprotected and having its all or substantially all other functional groups protected from the initial material, kanamycin A, sulfonylating the 3'- and 4'-hydroxyl groups, removing the 3'- and 4'-sulfonyloxy groups from the resulting 3',4'-di-sulfonic acid ester product to give a 3'-eno-kanamycin A derivative, hydrogenating the 3'-eno-kanamycin A derivative to saturate the 3',4'-unsaturated bond and to yield a protected 3',4'-dideoxykanamycin A product, followed by removal of the remainiing protective groups, and optionally further followed by 1-N-acylation of the 1-amino group of the resulting 3',4'-dideoxykanamycin A with an (S)-.alpha.-hydroxy-.omega.-aminoalkanoic acid or its reactive equivalent.