5-Epi-4,6-di-O-(aminoglycosyl)-2-deoxystreptamines, methods for

Details 5-Epi-4,6-di-O-(aminoglycosyl)-2-deoxystreptamines, methods for 5-Epi-4,6-di-O-(aminoglycosyl)-2-deoxystreptamines, methods for

1975-09-08

1976-12-28

Brown, Johnnie R.

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 10, A61K 3171, C07H 1522

Patent

active

040002616

ABSTRACT:
5-Epi-4,6-di-O-(aminoglycosyl)-2-deoxystreptamines and 1-N-alkyl-5-epi-4,6-di-O-(aminoglycosyl)-2-deoxystreptamines, valuable as antibacterial agents, are prepared from the corresponding 5-O-hydrocarbonsulfonyl (or substituted hydrocarbonsulfonyl)-4,6-di-O-(aminoglycosyl)-2-deoxystreptamine wherein amino and hydroxyl functions are protected by groups susceptible to reductive cleavage or to basic or mild acid hydrolysis, by the reaction thereof with dimethylformamide at elevated temperatures, followed by removal of the protecting groups. Alternatively, 5-epi-4,6-di-O-(aminoglycosyl)-2-deoxystreptamines and their 1-N-alkyl derivatives are prepared by oxidation of the corresponding 4,6-di-O-(aminoglycosyl)-2-deoxystreptamine wherein the amino and hydroxyl functions other than the 5-hydroxyl function are protected by groups susceptible to reductive cleavage or to basic or mild acid hydrolysis, with ruthenium tetroxide, chromic acid in acetone or chromium trioxide-pyridine complex in methylene chloride, thence reaction of the thereby produced 5-dehydro-4,6-di-O-(aminoglycosyl)-2-deoxystreptamine or 1-N-alkyl derivative thereof (novel intermediates) with an alkali metal borohydride followed by removal of the amino and hydroxyl protecting groups.
In addition to the foregoing, methods are described whereby the 1-N-alkyl-5-epi-4,6-di-O-(aminoglycosyl)-2-deoxystreptamines are prepared from the corresponding 1-N-unsubstituted-5-epi-4,6-di-O-(aminoglycosyl)-2-deoxystreptamines.
Pharmaceutical compositions comprising 5-epi-4,6-di-O-(aminoglycosyl)-2-deoxystreptamines or 1-N-alkyl-5-epi-4,6-di-O-(aminoglycosyl)-2-deoxystreptamines elicit an antibacterial response in a warm blooded animal having a susceptible bacterial infection.

REFERENCES:
patent: 3828021 (1974-08-01), Beattie et al.
patent: 3920628 (1975-11-01), Daniels

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