US4029883A
Expired / Lapsed
US
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Dehydroxylation of aminosugars
Assignee: Takeda Pharmaceutical Co Ltd
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Filing: 1973-12-20
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Granted: 1977-06-14
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Expires: 1993-12-20
Abstract
Abstract Dehydroxylation of aminoglycoside antibiotics is carried out by halogenation of phosphorylated aminoglycoside antibiotics followed by reduction of thus halogenated antibiotics. The dehydroxylation process is entirely new and gives the final product in a high yield. The resulting deoxyaminoglycoside antibiotics are effective against microorganisms including aminoglycoside antiobiotics-resistant microorganisms.
Inventors
- 👤 Kentaro Hiraga
- 👤 Tetsuya Okutani
- 👤 Kouichi Yoshioka
- 👤 Tsunehiko Asako
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 06:13
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/20; C07H15/22; C07H15/222; C07H15/226; C07H15/228; C07H15/23; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
20 words
A halogenated aminoglycoside antibiotic selected from the group consisting of 3'-chloro-3'-deoxyxylostasin, 3'-chloro-3'-deoxyneomycin B, 3'-chloro-3'-deoxyneomycin A, 3'-chloro-3'-deoxykanamycin B, 3'-chloro-3'-deoxyparomomycin and 3'-chloro-3'-deoxyribostamycin.
Claim 2
Dependent Claim
20 words
A halogenated aminoglycoside antibiotic selected from the group consisting of 3'-chloro-3'-deoxyxylostasin, 3'-chloro-3'-deoxyneomycin B, 3'-chloro-3'-deoxyneomycin A, 3'-chloro-3'-deoxykanamycin B, 3'-chloro-3'-deoxyparomomycin and 3'-chloro-3'-deoxyribostamycin.
Claim 3
Dependent Claim
1 words
5"-chloro-5"-deoxyribostamycin.
Claim 4
Dependent Claim
1 words
5"-chloro-5"-deoxyribostamycin.
Claim 5
Dependent Claim
9 words
A compound as claimed in claim 1, namely, 3'-chloro-3'-deoxyxylostasin.
Claim 6
Dependent Claim
10 words
A compound as claimed in claim 1, namely, 3'-chloro-3'-deoxyneomycin B.
Claim 7
Dependent Claim
10 words
A compound as claimed in claim 1, namely, 3'-chloro-3'-deoxyneomycin A.
Claim 8
Dependent Claim
10 words
A compound as claimed in claim 1, namely, 3'-chloro-3'-deoxykanamycin B.
Claim 9
Dependent Claim
9 words
A compound as claimed in claim 1, namely, 3'-chloro-3'-deoxyparomomycin.
Claim 10
Dependent Claim
9 words
A compound as claimed in claim 1, namely, 3'-chloro-3'-deoxyribostamycin.
Claim 11
Dependent Claim
1 words
3'-deoxyxylostasin.
Claim 12
Dependent Claim
1 words
3'-deoxyxylostasin.
Claim 13
Dependent Claim
2 words
3'-deoxyneomycin B.
Claim 14
Dependent Claim
2 words
3'-deoxyneomycin B.
Claim 15
Dependent Claim
1 words
3'-deoxyribostamycin.
Claim 16
Dependent Claim
1 words
3'-deoxyribostamycin.
Claim 17
Independent Claim
128 words
A method for the production of deoxyamino-glycoside antibiotics which consists essentially of (1) reacting a phosphorylated aminoglycoside antibiotic with a silylating agent selected from the group consisting of hexamethyldisilazane, trimethylchlorosilane, bis-(trimethylsilyl)-acetamide, bis-(trimethylsilyl)-trifluoroacetamide, trimethylsilylacetamide, N-methyl-N-trimethylsilylacetamide, N-trimethylsilylimidazole, N-(trimethylsilyl)diethylamine and halosilanes, or an acylating agent selected from the group consisting of acetic anhydride, acetyl chloride, benzoyl chloride and benzyloxycarbonyl chloride, (2) halogenating the thus obtained compound with a halogenating agent selected from the group consisting of halosilanes, thionyl chloride, trimethoxymethylphosphonium iodide, phosphorus oxychloride, phosphorus thiooxychloride, phosphorus pentachloride, oxalyl chloride and phosphorus pentabromide, (3) reducing the halogenated derivative, and (4) removing the introduced silyl group by protonization or the introduced acyl group by hydrolysis, removal of said groups being effected between steps (2) and (3), during step (3) or after step (3).
Claim 18
Independent Claim
128 words
A method for the production of deoxyamino-glycoside antibiotics which consists essentially of (1) reacting a phosphorylated aminoglycoside antibiotic with a silylating agent selected from the group consisting of hexamethyldisilazane, trimethylchlorosilane, bis-(trimethylsilyl)-acetamide, bis-(trimethylsilyl)-trifluoroacetamide, trimethylsilylacetamide, N-methyl-N-trimethylsilylacetamide, N-trimethylsilylimidazole, N-(trimethylsilyl)diethylamine and halosilanes, or an acylating agent selected from the group consisting of acetic anhydride, acetyl chloride, benzoyl chloride and benzyloxycarbonyl chloride, (2) halogenating the thus obtained compound with a halogenating agent selected from the group consisting of halosilanes, thionyl chloride, trimethoxymethylphosphonium iodide, phosphorus oxychloride, phosphorus thiooxychloride, phosphorus pentachloride, oxalyl chloride and phosphorus pentabromide, (3) reducing the halogenated derivative, and (4) removing the introduced silyl group by protonization or the introduced acyl group by hydrolysis, removal of said groups being effected between steps (2) and (3), during step (3) or after step (3).
References Cited (Backward Citations)
US3721664A
Cited
US3753973A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-06-13 | 1980-12-13 | 1981-06-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-06-13 | 1984-12-13 | 1985-06-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-06-13 | 1988-12-13 | 1989-06-14 | $7700.00 | Window Closed / Lapsed |