US4071512A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Preparation of 1-oxapenicillins and intermediates therefor
Assignee: Queen's University
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Filing: 1975-06-17
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Granted: 1978-01-31
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Expires: 1995-06-17
Abstract
Abstract The invention provides a novel process for opening the ring of 2-R-6-(1'-R 1 -oxycarbonyl-2'-methyl-prop-1'-enyl)-1-oxa-3,6-diaza-4S,5R-bicyclo[3,2,0]hept-2-en-7-one by treatment with a sulfonic acid salt thereby forming R 1 2-(2'R-R-oxy-3'S-amino-4'-oxo)azetidinyl-3-methyl-2-butenoate sulphonic acid salts which can provide oxapenicillins by two different routes depending on the substituent desired on the carboxamido group of the 1-oxapenicillins. In the alternate processes, new intermediates are also provided.
Inventors
- 👤 Saul Wolfe
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 18:07
CPC Classifications
C; C07; C07D; C07D263/00; C07D263/52; C07D263/54; C07D263/58; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D205/085; C07D265/00; C07D265/04; C07D265/06; C07D265/28; C07D265/34; C07D265/36; C07D503/00
Claims Analysis
Total Claims: 4
Claim 1
Independent Claim
46 words
The compound of the formula ##STR28## wherein A is the residue of a sulfonic acid selected from the group consisting of benzenesulfonic acid and toluenesulfonic acid, R is benzyl phenoxymethyl, thienylmethyl, allylthionylmethyl, or pentyl, R 1 is loweralkyl of 1 to 10 carbon atoms, or benzyl.
Claim 2
Dependent Claim
46 words
The compound of the formula ##STR28## wherein A is the residue of a sulfonic acid selected from the group consisting of benzenesulfonic acid and toluenesulfonic acid, R is benzyl phenoxymethyl, thienylmethyl, allylthionylmethyl, or pentyl, R 1 is loweralkyl of 1 to 10 carbon atoms, or benzyl.
Claim 3
Dependent Claim
11 words
The compound of claim 1 which is the methyl 2-(2'R-phenylacetoxy-3'-S-amino-4'-oxo)azetidinyl-3-methyl-2-butenoate p-toluenesulfonate.
Claim 4
Dependent Claim
11 words
The compound of claim 1 which is the benzyl 2-(2'R-phenylacetoxy-3'S-amino-4'-oxo)azetidinyl-3-methyl-2-butenoate p-toluenesulfonate.
References Cited (Backward Citations)
US3860577A
Cited
GB1355980A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-01-30 | 1981-08-01 | 1982-01-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-01-30 | 1985-08-01 | 1986-01-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-01-30 | 1989-08-01 | 1990-01-31 | $7700.00 | Window Closed / Lapsed |