US4889929A
Expired / Lapsed
US
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Preparation of 1'-ethoxycarbonyl-oxyethyl esters of penicillins
Assignee: Astra Lakemedel AB
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Filing: 1987-03-26
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Granted: 1989-12-26
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Expires: 2007-03-26
Abstract
Abstract Process for the preparation of 1'-ethoxy carbonyloxy ethyl esters of penicillins, wherein a compound of the formula ##STR1## in which A is phenyl, phenoxy or 4-hydroxyphenyl, B is hydrogen, an amino group or a protected amino group and Z is hydrogen or a cation selected from the group of alkali metal, tri (lower alkyl ) ammonium and tetra (lower alkyl) ammonium, is reacted with 1-bromoethyl ethyl carbonate in an organic solvent and when B is a protected amino group the protecting group is split off to yield a primary amino group. There are also provided novel compounds of the formula ##STR2## in which Ph is phenyl and R is CH 3 -- or C 2 H 5 --.
Inventors
- 👤 Jacob Vaya
- 👤 David Ladkani
- 👤 Clara Schoenberger
- 👤 Joseph Kaspi
- 👤 Gad Salemnick
- 👤 Haim Yellin
- 👤 Stephan Cherkez
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 15:03
CPC Classifications
C; C07; C07D; C07D499/00; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 5
Claim 1
Independent Claim
47 words
A process for the preparation of 1'-ethoxycarbonyloxy ethyl benzyl penicillinate having the formula: ##STR14## wherein benzyl penicillin having the formula: ##STR15## or a salt thereof, is reached with 1-bromoethyl ethyl carbonate: ##STR16## in a non-hydroxylic polar solvent at a temperature of from 20° C. to 50° C.
Claim 2
Dependent Claim
47 words
A process for the preparation of 1'-ethoxycarbonyloxy ethyl benzyl penicillinate having the formula: ##STR14## wherein benzyl penicillin having the formula: ##STR15## or a salt thereof, is reached with 1-bromoethyl ethyl carbonate: ##STR16## in a non-hydroxylic polar solvent at a temperature of from 20° C. to 50° C.
Claim 3
Dependent Claim
32 words
A process according to claim 1, characterized in that the potassium salt of benzyl penicillin is reacted with 1-bromoethyl ethyl carbonate in acetone at a temperature of 35° C. to 45° C.
Claim 4
Dependent Claim
15 words
A process according to claim 1 wherein the reaction is carried out at 40° C.
Claim 5
Dependent Claim
23 words
A process according to claim 1 wherein the reaction is carried out in the presence of a catalytic amount of tetrabutyl ammonium bromide.
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) | 1992-12-25 | 1993-06-26 | 1993-12-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-12-25 | 1997-06-26 | 1997-12-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-12-25 | 2001-06-26 | 2001-12-26 | $7700.00 | Window Closed / Lapsed |