1-N-[(S)-.alpha.-hydroxy-.omega.-aminoacyl] derivatives of 3',4'

Details 1-N-[(S)-.alpha.-hydroxy-.omega.-aminoacyl] derivatives of 3',4' 1-N-[(S)-.alpha.-hydroxy-.omega.-aminoacyl] derivatives of 3',4'

1976-07-23

1978-08-15

Trousof, Natalie

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

424180, C07H 1522, A61K 3170

Patent

active

041074246

ABSTRACT:
A new and useful 1-N-[(S)-.alpha.-hydroxy-.omega.-aminoacyl] derivative of an aminoglycosidic antibiotic, including its deoxy derivative, such as kanamycin B, 3'-deoxyneamine, 3',4'-dideoxyneamine, 3',4'-dideoxyribostamycin or 3',4'-dideoxykanamycin B is now synthetized from the parent substance, aminoglycosidic antiobiotic. The new 1-N-[(S)-.alpha.-hydroxy-.omega.-aminoacyl] derivative shows a wider and/or higher antibacterial activity than the parent substance and is useful in the treatment of infections by gram-negative and gram-positive bacteria, including drug-resistant strains thereof. The preparation of this new derivative may be made by 1-N-acylating the parent aminoglycosidic antibiotic with (S)-.alpha.-hydroxy-.omega.-aminocarboxylic acid with the amino group being protected, and chromatographically separating the acylated products to isolate the desired 1-N-acyl derivative, followed by the removal of the amino-protecting group.

REFERENCES:
patent: 3753973 (1973-08-01), Umezawa et al.
patent: 3781268 (1973-12-01), Kawaguchi
Umezawa, "3',4'-Dideoxy Kanamycin B ... Aeruginosa", J. of Antibiotics, 24, No. 7, pp. 485-487.
Journal of Antibiotics, vol. 26, No. 11, Jul. 1973, pp. 412-414 and 705-707.

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