US3929762A
Expired / Lapsed
US
⏱️ 0.0 years remaining
3{40 -Deoxy derivatives of neamine and its related aminoglycosidic antibiotics, and the production thereof
Assignee: Microbial Chemistry Research Foundation
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Filing: 1973-12-05
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Granted: 1975-12-30
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Expires: 1993-12-05
Abstract
Abstract The 3''-hydroxyl group of neamine and related aminoglycosidic antibiotics is preferentially sulfonylated with an alkylsulfonyl halide, arylsulfonyl halide or benzylsulfonyl halide and the resultant 3''-sulfonic ester group halogenated with a concentrated solution of alkali metal bromide or iodide in an aprotic solvent to yield halogenated intermediates which can be hydrogenated to form corresponding 3''-deoxy derivatives which exhibit useful antibacterial activity even against bacteria resistant to the parent aminoglycosidic antibiotics.
Inventors
- 👤 Hamao Umezawa
- 👤 Sumio Umezawa
- 👤 Osamu Tsuchiya
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 09:35
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/20; C07H15/22; C07H15/222; C07H15/224
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
16 words
A PROCESS FOR THE PRODUCTION OF A 3''-DEOXY DERIVATIVE OF AN AMINOGLYCOSIDIC ANTIBIOTIC OF THE FORMULA:
Claim 2
Dependent Claim
16 words
A PROCESS FOR THE PRODUCTION OF A 3''-DEOXY DERIVATIVE OF AN AMINOGLYCOSIDIC ANTIBIOTIC OF THE FORMULA:
Claim 3
Dependent Claim
55 words
A process according to claim 1 wherein said sulfonylating agent is one in which R3 is alkyl of 1-4 carbon atoms and X is bromide or iodide, wherein the reaction a) is effected with up to 1.5 moles of sulfonylating agent per mole of said protected aminoglycoside at a temperature of up to 50* C.
Claim 4
Dependent Claim
42 words
A process according to claim 1, wherein said sulfonylating agent is one in which R3 is benzyl, phenyl or p-tolyl and X is bromide or iodide, wherein the reaction a) is effected with at least an equimolar amount of said sulfonylating agent.
Claim 5
Dependent Claim
36 words
A process according to claim 1 wherein said 3'' sulfonic ester is removed in step (b) by 3''-iodination or 3''-bromination with a concentrated solution of alkali metal iodide or alkali metal bromide in an aprotic solvent.
Claim 6
Dependent Claim
16 words
A process according to claim 1 wherein said reduction step (c) is effected by catalytic hydrogeneration.
Claim 7
Dependent Claim
22 words
A process according to claim 1 further comprising removing said protective groups to form a free 3''-deoxy aminoglycoside wherein R is hydrogen.
Claim 8
Dependent Claim
27 words
A process according to claim 6 further comprising 6''-N-alkylating the resultant free 3''-deoxy amidoglycoside to form a 3''-deoxy compound wherein R is alkyl of 1-4 carbon atoms.
Claim 9
Dependent Claim
54 words
A process according to claim 6 further comprising (a) 6''-N-methylating said 3''-deoxy compound with a 6''-N-carboxylating agent selected from the group consisting of benzyloxycarboxyl chloride, benzyl p-nitrophenyl carbonate and N-(benzyloxycarboxyloxy)succinimide to form a corresponding 6''-N-benzyloxycarboxyl-3''-deoxy compound; and (b) reducing the resultant 6''-N-benzyloxycarboxylation product with lithium aluminum hydride or diborane to form said 6''-N-methyl-3''-deoxy compound.
Claim 10
Dependent Claim
30 words
A process according to claim 6 wherein said protected aminoglycoside is a compound of formula iii or iv as defined therein, whereby the resultant 3-deoxy compound is 3''-deoxykanamycin Beta .
Claim 11
Dependent Claim
8 words
A 3''-deoxy kanamycin B derivative of the formula:
Claim 12
Dependent Claim
8 words
A 3''-deoxy kanamycin B derivative of the formula:
Claim 13
Dependent Claim
8 words
A compound according to claim 10, 3''-deoxykanamycin B.
Claim 14
Dependent Claim
8 words
A compound according to claim 10, 3''-deoxy-6''-N-methylkanamycin B.
Claim 15
Dependent Claim
6 words
A 3''-deoxyvistamycin derivative of the formula:
Claim 16
Dependent Claim
6 words
A 3''-deoxyvistamycin derivative of the formula:
Claim 17
Dependent Claim
7 words
A compound according to claim 13, 3''-deoxyvistamycin.
Claim 18
Dependent Claim
7 words
A compound according to claim 13, 3''-deoxy-6''-N-methylvistamycin.
Claim 19
Dependent Claim
5 words
A 3''-deoxy-6''-N-alkylneamine of the formula:
Claim 20
Dependent Claim
5 words
A 3''-deoxy-6''-N-alkylneamine of the formula:
Claim 21
Dependent Claim
7 words
A compound according to claim 16, 3''-deoxy-6''-N-methylneamine.
References Cited (Backward Citations)
US3753973A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-12-29 | 1979-06-30 | 1979-12-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-12-29 | 1983-06-30 | 1983-12-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-12-29 | 1987-06-30 | 1987-12-30 | $7700.00 | Window Closed / Lapsed |