US3936446A
Expired / Lapsed
US
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Isocyanocephalosporanates
Assignee: Beecham Group PLC
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Filing: 1974-02-19
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Granted: 1976-02-03
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Expires: 1994-02-19
Abstract
Abstract Intermediates useful in the preparation of compounds having a penam or cephem ring structure, particularly penicillins and cephalosporins, and their preparation.
Inventors
- 👤 Peter Hubert Bentley
- 👤 John Peter Clayton
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 11:37
CPC Classifications
C; C07; C07D; C07D501/00; C07D501/14; C07D501/16; C07D499/00; C07D499/21
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
209 words
A compound of formula: ##SPC4## wherein the dotted line represents a double bond at either position 2- or 3-, n is zero of 1, X is a carboxylic acid group, a non-toxic salt thereof, or an esterified carboxylic acid group wherein the ester portion is selected from the group consisting of benzyl, para-methoxybenzyl, 2,2,2-trichloroethyl, tertbutyl, acetoxymethyl, pivaloyloxymethyl, phthalidyl and a lactone of the formula ##EQU6## wherein Z 1 is 1,2-phenylene or 4,5-dimethoxyphenyl-1,2-ene, R is hydrogen, an acetoxy group, a pyridinium group or a group of the formula -SR 2 , wherein R 2 represents a 5- or 6-membered heterocyclic ring containing one to four nitrogen heteroatoms, one oxygen heteroatom and one to three nitrogen heteroatoms or one sulphur heteroatom and one to three nitrogen heteroatoms, unsubstituted or substituted with one or two groups selected from alkyl, cycloalkyl, or alkenyl, each having up to four carbon atoms, alkoxy or alkoxyalkyl, each alkyl or alkoxy having one to four carbon atoms, CF 3 , NHR 3 , NR 2 3 , SCH 2 , halogen, amino, phenyl and benzyl wherein R 3 is alkyl of 1 to 4 carbon atoms; or X and R taken together represent the divalent radical ##EQU7## and R 1 is hydroxyloweralkyl, lowerakloxycarbonylloweralkyl, benzyloxycarbonylloweralkyl, benzyl or loweralkylthio.
Claim 2
Dependent Claim
209 words
A compound of formula: ##SPC4## wherein the dotted line represents a double bond at either position 2- or 3-, n is zero of 1, X is a carboxylic acid group, a non-toxic salt thereof, or an esterified carboxylic acid group wherein the ester portion is selected from the group consisting of benzyl, para-methoxybenzyl, 2,2,2-trichloroethyl, tertbutyl, acetoxymethyl, pivaloyloxymethyl, phthalidyl and a lactone of the formula ##EQU6## wherein Z 1 is 1,2-phenylene or 4,5-dimethoxyphenyl-1,2-ene, R is hydrogen, an acetoxy group, a pyridinium group or a group of the formula -SR 2 , wherein R 2 represents a 5- or 6-membered heterocyclic ring containing one to four nitrogen heteroatoms, one oxygen heteroatom and one to three nitrogen heteroatoms or one sulphur heteroatom and one to three nitrogen heteroatoms, unsubstituted or substituted with one or two groups selected from alkyl, cycloalkyl, or alkenyl, each having up to four carbon atoms, alkoxy or alkoxyalkyl, each alkyl or alkoxy having one to four carbon atoms, CF 3 , NHR 3 , NR 2 3 , SCH 2 , halogen, amino, phenyl and benzyl wherein R 3 is alkyl of 1 to 4 carbon atoms; or X and R taken together represent the divalent radical ##EQU7## and R 1 is hydroxyloweralkyl, lowerakloxycarbonylloweralkyl, benzyloxycarbonylloweralkyl, benzyl or loweralkylthio.
Claim 3
Dependent Claim
10 words
A compound according to claim 1 wherein n is zero.
Claim 4
Dependent Claim
14 words
A compound according to claim 1 wherein X is said esterified carboxylic acid group.
Claim 5
Dependent Claim
15 words
A compound according to claim 3 wherein the ester is benzyl, phthalidyl or t-butyl ester.
Claim 6
Dependent Claim
125 words
A compound according to claim 1 wherein X is said esterified carboxylic acid group and R is an acetoxy group or a group of formula -SR 2 wherein R 2 represents a 5- or 6-membered heterocyclic ring containing one to four nitrogen heteroatoms, one oxygen heteroatom and one to three nitrogen heteroatoms or one sulphur heteroatom and one to three nitrogen heteroatoms, unsubstituted or substituted with one or two groups selected from alkyl, cycloalkyl, or alkenyl, each having up to four carbon atoms, alkoxy or alkoxyalkyl, each alkyl or alkoxy having one to four carbon atoms, CF 3 , NHR 3 , NR 2 3 , SCH 2 , halogen, amino, phenyl and benzyl wherein R 3 is alkyl of 1 to 4 carbon atoms.
Claim 7
Dependent Claim
15 words
A compound according to claim 5 wherein R is a group of the formula: ##SPC5##
Claim 8
Dependent Claim
10 words
The compound according to claim 1 which is t-butyl 7α-benzyloxycarbonylethyl-7β-isocyanocephalosporanate.
Claim 9
Dependent Claim
10 words
The compound according to claim 1 which is t-butyl 7α-isocyano-7β-methylthiocephalosporanate.
References Cited (Backward Citations)
GB1328340A
Cited
DE2337105A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-02-02 | 1979-08-04 | 1980-02-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-02-02 | 1983-08-04 | 1984-02-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-02-02 | 1987-08-04 | 1988-02-03 | $7700.00 | Window Closed / Lapsed |