Patent US4069379A successfully refreshed from Google Patents.
US4069379A
Expired / Lapsed
US
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Semi-synthetic oleandomycins
Assignee: Pfizer Inc
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Filing: 1976-07-29
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Granted: 1978-01-17
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Expires: 1996-07-29
Abstract
Abstract Disclosed herein is a novel series of semi-synthetic oleandomycins having an exocyclic methylene or a cyclopropyl group at the C 8 position. Processes for preparing the methylene compounds from the natural oleandomycins and the cyclopropyl compounds from the methylene compounds are also disclosed. The oleandomycin compounds of the present invention are effective in inhibiting the growth of microorganisms, especially Gram-positive microorganisms.
Inventors
- 👤 Frank C. Sciavolino
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 09:25
CPC Classifications
C; C07; C07H; C07H17/00; C07H17/04; C07H17/08
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
79 words
A compound of the formula ##STR8## and the pharmaceutically acceptable mineral or organic addition salts thereof wherein R is selected from the group consisting of hydrogen, and alkanoyl having from two to three carbon atoms; R 1 is selected from the group consisting of hydrogen alkanoyl having from two to three carbon atoms and tri-(lower-alkyl) silyl; and R 2 is selected from the group consisting of hydrogen, alkanoyl having from two to three carbon atoms, trifluoroacetyl and tri(lower alkyl)silyl.
Claim 2
Dependent Claim
79 words
A compound of the formula ##STR8## and the pharmaceutically acceptable mineral or organic addition salts thereof wherein R is selected from the group consisting of hydrogen, and alkanoyl having from two to three carbon atoms; R 1 is selected from the group consisting of hydrogen alkanoyl having from two to three carbon atoms and tri-(lower-alkyl) silyl; and R 2 is selected from the group consisting of hydrogen, alkanoyl having from two to three carbon atoms, trifluoroacetyl and tri(lower alkyl)silyl.
Claim 3
Dependent Claim
20 words
The compound of claim 1 wherein R and R 1 are acetyl and R 2 is acetyl, trifluoroacetyl or trimethylsilyl.
Claim 4
Dependent Claim
57 words
A compound of the formula ##STR9## and the non-toxic acid addition salts thereof wherein R is selected from the group consisting of hydrogen and alkanoyl having from two to three carbon atoms; and R 1 and R 2 are selected from the group consisting of hydrogen, alkanoyl having from two to three carbon atoms and tri-(lower alkyl)silyl.
Claim 5
Dependent Claim
57 words
A compound of the formula ##STR9## and the non-toxic acid addition salts thereof wherein R is selected from the group consisting of hydrogen and alkanoyl having from two to three carbon atoms; and R 1 and R 2 are selected from the group consisting of hydrogen, alkanoyl having from two to three carbon atoms and tri-(lower alkyl)silyl.
Claim 6
Dependent Claim
19 words
A compound of claim 3 wherein R and R 1 are hydrogen and R 2 is hydrogen or acetyl.
Claim 7
Dependent Claim
87 words
A process for preparing a compound of the formula ##STR10## wherein R, R 1 and R 2 are selected from the group consisting of hydrogen and alkanoyl having from two to three carbon atoms which comprises contacting a compound of the formula ##STR11## wherein R, R 1 and R 2 are as defined above in a water miscile, reaction-inert solvent with lower valence state transition metal ions selected from the group consisting of Cr +2 , Ti +3 and V +2 until the reaction is substantially complete.
Claim 8
Dependent Claim
87 words
A process for preparing a compound of the formula ##STR10## wherein R, R 1 and R 2 are selected from the group consisting of hydrogen and alkanoyl having from two to three carbon atoms which comprises contacting a compound of the formula ##STR11## wherein R, R 1 and R 2 are as defined above in a water miscile, reaction-inert solvent with lower valence state transition metal ions selected from the group consisting of Cr +2 , Ti +3 and V +2 until the reaction is substantially complete.
Claim 9
Dependent Claim
26 words
The process of claim 5 wherein said water miscible, reaction-inert solvent is selected from the group consisting of acetone, a lower alkanol, tetrahydrofuran and mixtures thereof.
Claim 10
Dependent Claim
114 words
A process for preparing a compound of the formula ##STR12## wherein R is alkanoyl having from two to three carbon atoms; R 1 is selected from the group consisting of hydrogen, alkanoyl having from two to three carbon atoms and tri-(lower alkyl) silyl; and R 2 is selected from the group consisting of alkanoyl having from two to three carbon atoms and tri-(lower alkyl)silyl which comprises, while stirring, reacting a compound of the formula ##STR13## wherein R, R 1 and R 2 are as defined above in a reaction-inert solvent with cooling in ice/water with at least a substantially equivalent amount of dimethylsulfoxonium methylide and then allowing the mixture to come to room temperature.
Claim 11
Dependent Claim
114 words
A process for preparing a compound of the formula ##STR12## wherein R is alkanoyl having from two to three carbon atoms; R 1 is selected from the group consisting of hydrogen, alkanoyl having from two to three carbon atoms and tri-(lower alkyl) silyl; and R 2 is selected from the group consisting of alkanoyl having from two to three carbon atoms and tri-(lower alkyl)silyl which comprises, while stirring, reacting a compound of the formula ##STR13## wherein R, R 1 and R 2 are as defined above in a reaction-inert solvent with cooling in ice/water with at least a substantially equivalent amount of dimethylsulfoxonium methylide and then allowing the mixture to come to room temperature.
Claim 12
Dependent Claim
21 words
The process of claim 7 wherein the reaction-inert solvent is selected from the group consisting of dimethylsulfoxide, tetrahydrofuran and mixtures thereof.
References Cited (Backward Citations)
US3853842A
Cited
US3975372A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-01-16 | 1981-07-18 | 1982-01-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-01-16 | 1985-07-18 | 1986-01-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-01-16 | 1989-07-18 | 1990-01-17 | $7700.00 | Window Closed / Lapsed |