Abstract A new and useful 1-N-[(S)-α-hydroxy-ω-aminoacyl]derivative of an aminoglycosidic antiobiotic, 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 antibiotic. The new 1-N-[(S)-α-hydroxy-ω-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)-α-hydroxy-ω-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.
A compound of the formula: ##STR19## wherein R is hydrogen or alkyl of 1-4 carbon atoms; B is hydrogen or β-D-ribofuranosyl; at least one of X and Y is hydrogen and the other of X and Y is hydrogen or hydroxyl; n is 2 or 3; and the pharmaceutically acceptable acid addition salts thereof.
Claim 2
Dependent Claim
54 words
A compound of the formula: ##STR19## wherein R is hydrogen or alkyl of 1-4 carbon atoms; B is hydrogen or β-D-ribofuranosyl; at least one of X and Y is hydrogen and the other of X and Y is hydrogen or hydroxyl; n is 2 or 3; and the pharmaceutically acceptable acid addition salts thereof.
Claim 3
Dependent Claim
14 words
A compound according to claim 1, wherein R, X and Y are each hydrogen.
Claim 4
Dependent Claim
10 words
A compound according to claim 1, wherein B is hydrogen.
Claim 5
Dependent Claim
7 words
A compound according to claim 3, 1-N-[(S)-4-amino-2-hydroxybutyryl]-3',4'-dideoxyneamine.
Claim 6
Dependent Claim
10 words
A compound according to claim 1, wherein B is β-D-ribofuranosyl.
Claim 7
Dependent Claim
7 words
A compound according to claim 5, 1-N-[(S)-4-amino-2-hydroxybutyryl]-3',4'-dideoxyribostamycin.
Claim 8
Dependent Claim
10 words
A compound according to claim 1, wherein Y is hydroxyl.
Claim 9
Dependent Claim
7 words
A compound according to claim 7, 1-N-[(S)-4-amino-2-hydroxybutyryl]-3'-deoxyneamine.
Claim 10
Dependent Claim
7 words
A compound according to claim 7, 1-N-[(S)-4-amino-2-hydroxybutyryl]-3'-deoxyribostamycin.