US4002608A
Expired / Lapsed
US
⏱️ 0.0 years remaining
1-N-alkyl-aminoglycoside-XK-88 derivatives and methods for their manufacture
Assignee: Merck Sharp & Dohme LLC
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Filing: 1975-11-04
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Granted: 1977-01-11
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Expires: 1995-11-04
Abstract
Abstract 1-N-Alkyl-Aminoglycoside-XK-88 derivatives, valuable as antibacterial agents, are prepared by the reaction of an acid addition salt of the corresponding 1-N-unsubstituted-Aminoglycoside-XK-88 antibacterial derivative or of a 2''-N-alkanoyl-Aminoglycoside-XK-88-5 derivative in an inert solvent, preferably a protic solvent containing water, with one equivalent of a hydride-donor reducing agent and with at least one equivalent of an aldehyde.
Inventors
- 👤 John J. Wright
- 👤 Peter J. L. Daniels
- 👤 Alan K. Mallams
- 👤 Tattanahalli L. Nagabhushan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 02:28
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/20; C07H15/22; C07H15/222; C07H15/226; C07H15/234
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
90 words
A 1-N-X-4,6-di-O-(aminoglycosyl)-2-deoxystreptamine selected from the group consisting of 1-N-X-Aminoglycoside-XK-88-1, 1-N-X-Aminoglycoside-XK-88-3, and 1-N-X-Aminoglycoside-XK-88-5; wherein X is an alkyl substituent selected from the group consisting of alkyl, alkenyl, aralkyl, hydroxyalkyl, cycloalkylalkyl, aminoalkyl, alkylaminoalkyl, aminohydroxyalkyl, and alkylaminohydroxyalkyl, said alkyl substituent having up to 8 carbon atoms, the carbon in said alkyl substituent adjacent to the aminoglycoside nitrogen being unsubstituted, and when said alkyl substituent is substituted by both hydroxyl and amino functions, only one of said functions can be attached at any one carbon atom; and the pharmaceutically acceptable acid addition salts thereof.
Claim 2
Dependent Claim
90 words
A 1-N-X-4,6-di-O-(aminoglycosyl)-2-deoxystreptamine selected from the group consisting of 1-N-X-Aminoglycoside-XK-88-1, 1-N-X-Aminoglycoside-XK-88-3, and 1-N-X-Aminoglycoside-XK-88-5; wherein X is an alkyl substituent selected from the group consisting of alkyl, alkenyl, aralkyl, hydroxyalkyl, cycloalkylalkyl, aminoalkyl, alkylaminoalkyl, aminohydroxyalkyl, and alkylaminohydroxyalkyl, said alkyl substituent having up to 8 carbon atoms, the carbon in said alkyl substituent adjacent to the aminoglycoside nitrogen being unsubstituted, and when said alkyl substituent is substituted by both hydroxyl and amino functions, only one of said functions can be attached at any one carbon atom; and the pharmaceutically acceptable acid addition salts thereof.
Claim 3
Dependent Claim
16 words
A compound of claim 1 wherein X is an alkyl having up to 4 carbon atoms.
Claim 4
Dependent Claim
15 words
A compound of claim 1 which is 1-N-X-Aminoglycoside-XK-88-5, X being as defined in claim 1.
Claim 5
Dependent Claim
19 words
A compound of claim 1 which is 1-N-X-Aminoglycoside-XK-88-5 wherein X is an alkyl having 2 to 4 carbon atoms.
Claim 6
Dependent Claim
4 words
1-N-ethyl-Aminoglycoside-XK-88-5 of claim 4.
Claim 7
Dependent Claim
4 words
1-N-propyl-Aminoglycoside-XK-88-5 of claim 4.
Claim 8
Dependent Claim
4 words
1-N-(γ-aminopropyl)-Aminoglycoside-XK-88-5 of claim 4.
Claim 9
Dependent Claim
4 words
1-N-(δ-aminobutyl)-Aminoglycoside-XK-88-5 of claim 4.
References Cited (Backward Citations)
US3350387A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-01-11 | 1980-07-12 | 1981-01-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-01-11 | 1984-07-12 | 1985-01-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-01-11 | 1988-07-12 | 1989-01-11 | $7700.00 | Window Closed / Lapsed |