US4124756A
Expired / Lapsed
US
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3-DE-O-Methylfortimicins
Assignee: Abbott Laboratories
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Filing: 1976-12-27
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Granted: 1978-11-07
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Expires: 1996-12-27
Abstract
Abstract Described are 3-de-O-methylfortimicins A and B and 4-N-acyl and 4-N-alkyl-3-de-O-methylfortimicin B derivatives, and their preparation, which compounds are useful as antibiotics or as intermediates for preparing other useful derivatives having antibacterial activity. The compounds have the following structural formula ##STR1## wherein R is hydrogen, acyl, aminoacyl, N-monoloweralkylaminoacyl, N.N-diloweralkylaminoacyl, hydroxy-substituted aminoacyl, alkyl, aminoalkyl, N-monoloweralkylaminoalkyl, N.N-diloweralkylaminoalkyl or hydroxy-substituted aminoalkyl and the pharmaceutically acceptable salts thereof, for example, salts formed from hydrochloric, sulfuric, and phosphoric acids.
Inventors
- 👤 Jerry R. Martin
- 👤 John S. Tadanier
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 06:13
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/20; C07H15/22; C07H15/222; C07H15/224; A; A61; A61P; A61P31/00; A61P31/04
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
43 words
A compound of the formula ##STR4## wherein R is a member of the group consisting of hydrogen, lower acyl, lower amino acyl, N-monoloweralkyl loweraminoacyl, N,N-di-loweralkyl loweraminoacyl, hydroxy-substituted loweraminoacyl, loweralkyl, loweraminoalkyl, N-monoloweralkyl loweraminoalkyl, N,N-diloweralkyl loweraminoalkyl, or hydroxysubstituted loweraminoalkyl and the pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
43 words
A compound of the formula ##STR4## wherein R is a member of the group consisting of hydrogen, lower acyl, lower amino acyl, N-monoloweralkyl loweraminoacyl, N,N-di-loweralkyl loweraminoacyl, hydroxy-substituted loweraminoacyl, loweralkyl, loweraminoalkyl, N-monoloweralkyl loweraminoalkyl, N,N-diloweralkyl loweraminoalkyl, or hydroxysubstituted loweraminoalkyl and the pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
43 words
A compound selected from the group consisting of 3-De-O-methylfortimicin B, 1, 2', 6'-Tri-N-benzyloxycarbonyl-3-de-O-methylfortimicin B, Tetra-N-benzyloxycarbonyl-3-de-O-methylfortimicin A, Tetra-N-benzyloxycarbonyl-3-de-O-methylfortimicin A, Tetra-N-benzyloxycarbonyl-3-de-O-methyl-4-N-sarcasylfortimicin B, 3-De-O-methylfortimicin A tetrahydrochloride, 3-De-O-methyl-4-N-sarcosylfortimicin B tetrahydrochloride, Tetra-N-benzyloxycarbonyl-3-de-O-methyl-4-N-(β-aminoethyl) fortimicin B, 3-de-O-methyl-4-N-(β-aminoethyl)fortimicin B tetrahydrochloride, 3-de-O-methyl-4-N-(β-aminoethyl) fortimicin B, 3-De-O-methylfortimicin B, 3-De-O-methylfortimicin A tetrahydrochloride, 3-De-O-methyl-4-N-sarcosylfortimicin B tetrahydrochloride.
Claim 4
Dependent Claim
43 words
A compound selected from the group consisting of 3-De-O-methylfortimicin B, 1, 2', 6'-Tri-N-benzyloxycarbonyl-3-de-O-methylfortimicin B, Tetra-N-benzyloxycarbonyl-3-de-O-methylfortimicin A, Tetra-N-benzyloxycarbonyl-3-de-O-methylfortimicin A, Tetra-N-benzyloxycarbonyl-3-de-O-methyl-4-N-sarcasylfortimicin B, 3-De-O-methylfortimicin A tetrahydrochloride, 3-De-O-methyl-4-N-sarcosylfortimicin B tetrahydrochloride, Tetra-N-benzyloxycarbonyl-3-de-O-methyl-4-N-(β-aminoethyl) fortimicin B, 3-de-O-methyl-4-N-(β-aminoethyl)fortimicin B tetrahydrochloride, 3-de-O-methyl-4-N-(β-aminoethyl) fortimicin B, 3-De-O-methylfortimicin B, 3-De-O-methylfortimicin A tetrahydrochloride, 3-De-O-methyl-4-N-sarcosylfortimicin B tetrahydrochloride.
Claim 5
Dependent Claim
23 words
A compound selected from the group consisting of 3-de-O-metylfortimicin B, 3-de-O-methylfortimicin A tetrahydrochloride, 3-de- O-metyl-4-N-sarcosylfortimicin B tetrahydrochloride, 3-de-O-methyl-4-N-(β-aminoethyl)fortimicin B tetrahydrochloride, 3-de-O-methyl-4-N-(β-aminoethyl) fortimicin B.
Claim 6
Dependent Claim
23 words
A compound selected from the group consisting of 3-de-O-metylfortimicin B, 3-de-O-methylfortimicin A tetrahydrochloride, 3-de- O-metyl-4-N-sarcosylfortimicin B tetrahydrochloride, 3-de-O-methyl-4-N-(β-aminoethyl)fortimicin B tetrahydrochloride, 3-de-O-methyl-4-N-(β-aminoethyl) fortimicin B.
Claim 7
Dependent Claim
16 words
A compound selected from the group consisting of 3-de-O-methylfortimicin B, 3-de-O-methylfortimicin A tetrahydrochloride, 3-de-O-methyl-4-N-sarcosylfortimicin B tetrahydrochloride.
Claim 8
Dependent Claim
16 words
A compound selected from the group consisting of 3-de-O-methylfortimicin B, 3-de-O-methylfortimicin A tetrahydrochloride, 3-de-O-methyl-4-N-sarcosylfortimicin B tetrahydrochloride.
Claim 9
Dependent Claim
7 words
The compound of claim 4: 3-de-O-methylfortimicin B.
Claim 10
Dependent Claim
8 words
The compound of claim 4: 3-de-O-methylfortimicin A tetrahydrochloride.
Claim 11
Dependent Claim
8 words
The compound of claim 4: 3-de-O-methyl-4-N-sarcosylfortimicin B tetrahydrochloride.
Claim 12
Independent Claim
60 words
A method of preparing 3-de-O-methyl-4-N-acyl fortimicins comprising: reacting 3-de-O-methylfortimicin B with N-(benzyloxycarbonyloxy)succinimide to form the 1, 2', 6'-tri-N-benzyloxycarbonyl protected 3-de-O-methylfortimicins, reacting of said protected 3-de-O-methylfortimicins with suitable activated N-benzyloxycarbonyl protected amino acids to form the benzyloxycarbonyl-3-de-O-methyl-4-N-acylfortimicin, and removing the N-benzyloxycarbonyl groups by hydrogenolysis with a suitable catalyst in the presence of an acid to form the desired 3-de-O-methyl-4-N-acylfortimicin acid salts.
Claim 13
Independent Claim
60 words
A method of preparing 3-de-O-methyl-4-N-acyl fortimicins comprising: reacting 3-de-O-methylfortimicin B with N-(benzyloxycarbonyloxy)succinimide to form the 1, 2', 6'-tri-N-benzyloxycarbonyl protected 3-de-O-methylfortimicins, reacting of said protected 3-de-O-methylfortimicins with suitable activated N-benzyloxycarbonyl protected amino acids to form the benzyloxycarbonyl-3-de-O-methyl-4-N-acylfortimicin, and removing the N-benzyloxycarbonyl groups by hydrogenolysis with a suitable catalyst in the presence of an acid to form the desired 3-de-O-methyl-4-N-acylfortimicin acid salts.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-11-06 | 1982-05-08 | 1982-11-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-11-06 | 1986-05-08 | 1986-11-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-11-06 | 1990-05-08 | 1990-11-07 | $7700.00 | Window Closed / Lapsed |