1-N-alkyl-4,6-di-(aminoglycosyl)-1,3-diaminocyclitols, methods f

Details 1-N-alkyl-4,6-di-(aminoglycosyl)-1,3-diaminocyclitols, methods f 1-N-alkyl-4,6-di-(aminoglycosyl)-1,3-diaminocyclitols, methods f

1974-07-30

1977-01-11

Gotts, Lewis

Drug, bio-affecting and body treating compositions

Conjugate or complex of monoclonal or polyclonal antibody,...

Conjugated via claimed linking group, bond, chelating agent,...

536 17, 536 14, A61K 3170

Patent

active

040027422

ABSTRACT:
1-N-Alkyl-4,6-di-(aminoglycosyl)-1,3-diaminocyclitols, valuable as antibacterial agents, are prepared by treating an acid addition salt of a 4,6-di-(aminoglycosyl)-1,3-diamonocyclitol antibacterial agent in an inert solvent, preferably a protic solvent containing water, with one equivalent of a hydride donor reducing agent and with at least one equivalent of an aldehyde.
The 1-N-alkyl-4,6-di-(aminoglycosyl)-1,3-diaminocyclitols are also prepared by treating the corresponding 1-N-acyl-4,6-di-(aminoglycosyl)-1,3-diaminocyclitol with an amide-reducing hydride reagent in an inert organic solvent.
Other methods of preparing 1-N-alkyl-4,6-di-(aminoglycosyl)-1,3-diaminocyclitols include carrying out the foregoing processes with partially N-protected intermediates. Another useful process involves preparing a Schiff base of the 1-amino function of a partially N-protected 4,6-di-(aminoglycosyl)-1,3-diaminocyclitol followed by reduction of said Schiff base and removal of the N-protecting groups.
Pharmaceutical compositions comprising 1-N-alkyl-4,6-di-(aminoglycosyl)-1,3-diaminocyclitols are described as well as the method of using said compositions to elicit an antibacterial response in a warm blooded animal having a susceptible bacterial infection.

REFERENCES:
patent: 3651042 (1972-03-01), Marquez et al.
patent: 3832286 (1974-08-01), Weinstein et al.
Journal of Antibiotics, vol. 21, 1968, pp. 340-349.

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