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US4588712A
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(8S)-8-fluoroerythromycin derivatives, the process for the preparation thereof and the pharmaceutical compositions containing them
Assignee: Pierrel SpA
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Filing: 1985-02-28
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Granted: 1986-05-13
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Expires: 2005-02-28
Abstract
Abstract (8S)-8-fluoroerythromycin derivatives of formula ##STR1## wherein R is an optionally substituted alkyl, alkenyl or phenyl group R' is hydrogen or methyl and R" is hydrogen or hydroxy, may be prepared by fluorination of the corresponding 8,9-anhydroerythromycin 6,9-hemiketals with perchloryl fluoride in the presence of a compound ROH in strictly anhydrous conditions. The new compounds as well as their pharmaceutically acceptable esters, salts and salt-esters may be employed as the active ingredients of pharmaceutical compositions for antibacterial use suitable for oral administration.
Inventors
- 👤 Luciano Toscano
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 07:23
CPC Classifications
C; C07; C07H; C07H17/00; C07H17/04; C07H17/08; A; A61; A61P; A61P31/00; A61P31/04
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
123 words
A compound of formula (1) ##STR6## wherein R is an unsubstituted C 1 -C 10 alkyl or unsubstituted C 3 -C 10 alkenyl or R is C 1 -C 10 alkyl or C 3 -C 10 alkenyl substituted with a radical which a member selected the group consisting of lower alkoxy, cycloalkoxy, phenyl, substituted phenyl and substituted amino of formula ##STR7## wherein R 3 and R 4 , each independently, are lower alkyl or benzyl or R 3 and R 4 together with the adjacent nitrogen atom form a pyrrolidine, piperidine, piperazine or morpholine ring; or R is phenyl or substituted phenyl; R' is hydrogen or methyl; and R" is hydrogen or hydroxy, pharmaceutically acceptable esters, organic acid addition salts, and salt-esters thereof.
Claim 2
Dependent Claim
123 words
A compound of formula (1) ##STR6## wherein R is an unsubstituted C 1 -C 10 alkyl or unsubstituted C 3 -C 10 alkenyl or R is C 1 -C 10 alkyl or C 3 -C 10 alkenyl substituted with a radical which a member selected the group consisting of lower alkoxy, cycloalkoxy, phenyl, substituted phenyl and substituted amino of formula ##STR7## wherein R 3 and R 4 , each independently, are lower alkyl or benzyl or R 3 and R 4 together with the adjacent nitrogen atom form a pyrrolidine, piperidine, piperazine or morpholine ring; or R is phenyl or substituted phenyl; R' is hydrogen or methyl; and R" is hydrogen or hydroxy, pharmaceutically acceptable esters, organic acid addition salts, and salt-esters thereof.
Claim 3
Dependent Claim
14 words
A compound according to claim 1 wherein R' is methyl and R" is hydroxy.
Claim 4
Dependent Claim
16 words
A compound according to claim 2 wherein R is said substituted (C 1 -C 10 )alkyl.
Claim 5
Dependent Claim
14 words
A compound according to claim 1 wherein the absolute configuration at C-9 is R.
Claim 6
Dependent Claim
18 words
A compound of claim 1 which is the (8S)-8-fluoroerythromycin A 6,9(R)-methylketal, its pharmaceutically acceptable esters, salts and salt-esters.
Claim 7
Dependent Claim
18 words
A compound of claim 1 which is the (8S)-8-fluoroerythromycin A 6,9(R)-ethylketal, its pharmaceutically acceptable esters, salts and salt-esters.
Claim 8
Dependent Claim
18 words
A compound of claim 1 which is the (8S)-8-fluoeroerythromycin A 6,9(R)-isopropylketal, its pharmaceutically acceptable esters, salts and salt-esters.
Claim 9
Dependent Claim
18 words
A compound of claim 1 which is the (8S)-8-fluoroerythromycin A 6,9(R)-butylketal, its pharmaceutically acceptable esters, salts and salt-esters.
Claim 10
Dependent Claim
96 words
A process for preparing a compound according to claim 1 which consists of fluorinating a solution of a 8,9-anhydroerythromycin 6,9-hemiketal or the corresponding N-oxide of formula (II) ##STR8## wherein R' and R" are as defined in claim 1 and x is 0 or 1 with perchloryl fluoride in the presence of at least an equimolar amount of a compound of formula ROH wherein R is as defined in claim, 1 in strict anhydrous conditions, and reducing the obtained intermediate when x is 1, and converting the obtained compound into a pharmaceutically acceptable ester, salt or salt-ester.
Claim 11
Dependent Claim
23 words
An antibiotic pharmaceutical composition for oral administration comprising a therapeutically effective amount of a compound of claim 1 and a pharmaceutical carrier therefor.
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) | 1989-05-12 | 1989-11-11 | 1990-05-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-05-12 | 1993-11-11 | 1994-05-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-05-12 | 1997-11-11 | 1998-05-13 | $7700.00 | Window Closed / Lapsed |