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US4001208A Expired / Lapsed US ⏱️ 0.0 years remaining

1-N-[(S)-α-hydroxy-ω-aminoacyl]

Assignee: Microbial Chemistry Research Foundation
•
Filing: 1973-10-01
•
Granted: 1977-01-04
•
Expires: 1993-10-01
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Abstract

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.

Inventors

  • 👤 Hamao Umezawa
  • 👤 Sumio Umezawa
  • 👤 Kenji Maeda
  • 👤 Osamu Tsuchiya
  • 👤 Shinichi Kondo
  • 👤 Shunzo Fukatsu

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 16:28
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/20; C07H15/22; C07H15/222; C07H15/224; C07H15/226; C07H15/228; C07H15/23; C07H15/234; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55

Claims Analysis

Total Claims: 10
Claim 1
Independent 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 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.

References Cited (Backward Citations)

US3296246A Cited
US3156617A Cited
US3781268A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-01-04 1980-07-05 1981-01-04 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-01-04 1984-07-05 1985-01-04 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-01-04 1988-07-05 1989-01-04 $7700.00 Window Closed / Lapsed

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