GB1494129A — Derivatives of diaminocyclitols and methods for their preparation

USPTO Abstract

The 1-N-X-substituted 4,6-di(aminoglycosyl)-1,3-diaminocyclitols gentamicin A, gentamicin B, gentamicin B1, gentamicin C1, gentamicin C1a, gentamicin C2, gentamicin C2a, gentamicin X2, sisomicin, verdamicin, antibiotic G-418, antibiotic 66-40B, antibiotic 66-40D, antibiotic JI-20A, antibiotic JI-20B and antibiotic G-52, in which X is the S-3-amino-2-hydroxypropionyl or S-4-amino-2-hydroxybutyl group, are prepared. (In the case of gentamicins C1, C1a and C2, X is restricted to S-3-amino-2-hydroxypropionyl.) Owing to the presence of the 1-N-substituent, these compounds have greater activity. The process comprises reacting a 1-N-unsubstituted 4,6-di(aminoglycosyl)-1,3-diaminocyclitol, which may be in the form of a partially neutralised acid addition salt, with an appropriate acid in the presence of a carbodiimide or with a functional derivative of this acid. During the process it is possible for amino groups and/or the hydroxyl group, with the exception of the 1-amino group, in the starting materials to undergo intermediate protection.