US4048157A
Expired / Lapsed
US
⏱️ 0.0 years remaining
4(Formylthio)-azetidin-2-ones and ozonization process therefor
Assignee: Eli Lilly and Co
•
Filing: 1975-10-29
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Granted: 1977-09-13
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Expires: 1995-10-29
Abstract
Abstract Ozonolysis of 3-bromomethyl-2-cephem-4-carboxylic acid esters provides 1-(1-protected carboxy-2-hydroxy-3-bromo-1-propenyl)-3-amido(or imido)-4-formylthio-azetidin-2-ones, useful as intermediates in the preparation of cephalosporin antibiotics.
Inventors
- 👤 Robin D. G. Cooper
- 👤 Douglas O. Spry
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 15:16
CPC Classifications
C; C07; C07D; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D205/09; C07D205/095
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
39 words
A compound of the formula ##STR12## wherein: R 1 is a readily removable carboxylic acid protecting group which is substantially unreactive toward ozone; and R 2 is phthalamido or a group having the formula ##STR13## wherein: R 3 is
Claim 2
Dependent Claim
39 words
A compound of the formula ##STR12## wherein: R 1 is a readily removable carboxylic acid protecting group which is substantially unreactive toward ozone; and R 2 is phthalamido or a group having the formula ##STR13## wherein: R 3 is
Claim 3
Dependent Claim
131 words
hydrogen, C 1 -C 3 alkyl, halomethyl, benzyloxy, 4-nitrobenzyloxy, tert.-butyloxy, 2,2,2-trichloroethoxy, 4-methoxybenzyloxy, 4-protected amino-4-protected carboxybutyl in which the amino protecting group and carboxy protecting group are substantially unreactive toward ozone; or 2. a group of the formula R.sub.4 --(O).sub.m --CH.sub.2 -- wherein: m is 0 or 1; and R 4 is phenyl or phenyl substituted with 1 or 2 halogens, nitro, cyano, trifluoromethyl, C 1 -C 4 alkyl, C 1 -C 2 alkoxy, protected hydroxy in which the hydroxy protecting group is substantially unreactive toward ozone; or 3. a group of the formula ##STR14## wherein: R 4 is as defined above and W is protected hydroxy, protected carboxy, or protected amino in which the hydroxy protecting group, the carboxy protecting group and the amino protecting group are substantially unreactive toward ozone.
Claim 4
Dependent Claim
131 words
hydrogen, C 1 -C 3 alkyl, halomethyl, benzyloxy, 4-nitrobenzyloxy, tert.-butyloxy, 2,2,2-trichloroethoxy, 4-methoxybenzyloxy, 4-protected amino-4-protected carboxybutyl in which the amino protecting group and carboxy protecting group are substantially unreactive toward ozone; or 2. a group of the formula R.sub.4 --(O).sub.m --CH.sub.2 -- wherein: m is 0 or 1; and R 4 is phenyl or phenyl substituted with 1 or 2 halogens, nitro, cyano, trifluoromethyl, C 1 -C 4 alkyl, C 1 -C 2 alkoxy, protected hydroxy in which the hydroxy protecting group is substantially unreactive toward ozone; or 3. a group of the formula ##STR14## wherein: R 4 is as defined above and W is protected hydroxy, protected carboxy, or protected amino in which the hydroxy protecting group, the carboxy protecting group and the amino protecting group are substantially unreactive toward ozone.
Claim 5
Dependent Claim
29 words
The compound of claim 1 wherein R 1 is selected from the group consisting of C 4 -C 6 tert. alkyl, benzyl, nitrobenzyl, methoxybenzyl, benzhydryl, phenacyl, phthalimidomethyl, and succinimidomethyl.
Claim 6
Dependent Claim
10 words
The compound of claim 2 wherein R 2 is phthalimido.
Claim 7
Dependent Claim
10 words
The compound of claim 2 wherein R 2 is ##STR15##
Claim 8
Dependent Claim
16 words
The compound of claim 4 wherein R 3 is R 4 --(O) m --CH 2 --.
Claim 9
Dependent Claim
9 words
The compound of claim 5, said compound being 1-(1-tert.-butoxycarbonyl-2-hydroxy-3-bromo-1-propenyl)-3-phenoxyacetamido-4-formylthio-azetidin-2-one.
Claim 10
Dependent Claim
9 words
The compound of claim 5, said compound being 1-(1-tert.-butoxycarbonyl-2-hydroxy-3-bromo-1-propenyl)-3-phenylacetamido-5-formylthio-azetidin-2-one.
Claim 11
Dependent Claim
20 words
The compound of claim 4 wherein R 3 is other than R 4 ---(O) m CH 2 -- or ##STR16##
Claim 12
Dependent Claim
10 words
The compound of claim 4 wherein R 3 is ##STR17##
References Cited (Backward Citations)
US3950352A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-09-12 | 1981-03-14 | 1981-09-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-09-12 | 1985-03-14 | 1985-09-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-09-12 | 1989-03-14 | 1989-09-13 | $7700.00 | Window Closed / Lapsed |