US4008229A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Halo substituted β-lactam antibiotics
Assignee: Eli Lilly and Co
•
Filing: 1974-07-11
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Granted: 1977-02-15
•
Expires: 1994-07-11
Abstract
Abstract Imino chlorides of 6-aminopenicillanic esters and 7-aminocephalosporanic esters are reacted at a temperature between -80° and -25° C. with a strong base such as an alkali metal amide of a secondary amine and the generated anion is halogenated to provide the corresponding 6- or 7-halo-N(α-haloalkylidene) or N(α-halo-α-arylmethylidene)-6-aminopenicillanic or 7-aminocephalosporanic esters, respectively. The 6-halopenicillins and 7-halocephalosporins are converted to 6-methoxypenicillins and 7-methoxycephalosporins.
Inventors
- 👤 Wayne A. Spitzer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 13:50
CPC Classifications
C; C07; C07D; C07D499/00
Claims Analysis
Total Claims: 5
Claim 1
Independent Claim
73 words
A compound of the formula ##STR8## wherein R is C 2 -C 7 1-alkenyl; phenyl; substituted phenyl, in which the substituent is halo, C 1 -C 4 alkoxy, nitro, C 1 -C 4 alkyl, or phenyl; furyl; thienyl; naphthyl; styryl; or substituted styryl, in which the substituent is halo or nitro; R 1 is a carboxyl protecting ester forming group; R 2 is halo; Y is: ##STR9## Wherein Q is methyl or acetoxymethyl.
Claim 2
Dependent Claim
73 words
A compound of the formula ##STR8## wherein R is C 2 -C 7 1-alkenyl; phenyl; substituted phenyl, in which the substituent is halo, C 1 -C 4 alkoxy, nitro, C 1 -C 4 alkyl, or phenyl; furyl; thienyl; naphthyl; styryl; or substituted styryl, in which the substituent is halo or nitro; R 1 is a carboxyl protecting ester forming group; R 2 is halo; Y is: ##STR9## Wherein Q is methyl or acetoxymethyl.
Claim 3
Dependent Claim
20 words
The compound of claim 1 in which R 1 is 2,2,2-trichloroethyl, p-nitrobenzyl, benzhydryl, benzyl, t-butyl, p-methoxybenzyl, 3,5-dimethoxybenzyl, tetrahydropyranyl, or phenacyl.
Claim 4
Dependent Claim
10 words
The compound of claim 2 wherein R 2 is fluoro.
Claim 5
Dependent Claim
10 words
The compound of claim 3, said compound being 2,2,2-trichloroethyl 7-fluoro-7-[N-(α)-chloro-p-nitrobenzylidene)amino]deacetoxycephalosporanate.
References Cited (Backward Citations)
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US3658792A
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ZA713229B
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US3875146A
Cited
US3832347A
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US3843641A
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US3890310A
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-02-15 | 1980-08-16 | 1981-02-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-02-15 | 1984-08-16 | 1985-02-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-02-15 | 1988-08-16 | 1989-02-15 | $7700.00 | Window Closed / Lapsed |