6'-N-alkyl-4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitols, method

Details 6'-N-alkyl-4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitols, method 6'-N-alkyl-4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitols, method

1976-03-15

1977-08-23

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,...

424181, 536 10, 536 17, A61K 3171, C07H 1522

Patent

active

040441237

ABSTRACT:
Described are 6'-N-alkyl derivatives of antibacterially active 4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitols having a primary carbinamine at C-5' of which a preferred group are 6'-N-alkyl derivatives having 2 to 4 carbon atoms of 4-O-aminoglycosyl-6-O-garosaminyl-2-deoxystreptamines having a primary carbinamine at C-5', a particularly preferred compound being 6'-N-ethylsisomicin.
The 6'-N-alkyl derivatives are prepared by the reaction of the corresponding 6'-N-unsubstituted aminoglycoside having protecting groups on all other amino functions with an aldehyde or a ketone, followed by the reaction in situ of the 6'-N-substituted intermediate thereby formed with a hydride reducing agent, then removal of any N-protecting groups.
Pharmaceutical formulations comprising 6'-N-alkylaminoglycosides of the invention are described and the method for their use in treating bacterial infections.

REFERENCES:
patent: 3832286 (1974-08-01), Weinstein et al.
patent: 3925353 (1975-12-01), Umezawa et al.
patent: 3929762 (1975-12-01), Umezawa et al.
patent: 3972930 (1976-08-01), Daum et al.

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