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US3936446A Expired / Lapsed US ⏱️ 0.0 years remaining

Isocyanocephalosporanates

Assignee: Beecham Group PLC
•
Filing: 1974-02-19
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Granted: 1976-02-03
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Expires: 1994-02-19
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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

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