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US3974150A Expired / Lapsed US ⏱️ 0.0 years remaining

7β-Isocyano cephalosporin esters and process of preparation

Assignee: Glaxo Laboratories Ltd
•
Filing: 1973-07-09
•
Granted: 1976-08-10
•
Expires: 1993-07-09
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Abstract

Abstract Novel 6β-isocyano penicillin and 7β-isocyano cephalosporin esters of value as intermediates in the synthesis of penicillin and cephalosporin antibiotics are provided. The novel compounds may be prepared by reaction of the corresponding 6β-formamido penicillin ester or 7β-formamido cephalosporin ester with an acid halide derived from phosphorus, sulphur or carbon or from an oxygen acid of one of said elements, suitable halides including thionyl chloride or phosgene, or with a trivalent phosphorus compound such as triphenylphosphine and a halogenated hydrocarbon such as carbon tetrachloride. The conversion of the novel products to 6β- and 7β- (α-hydroxy) arylacetamido penicillins and cephalosporins respectively by reaction under acidic conditions with an aromatic aldehyde followed by treatment with an aqueous medium is also described.

Inventors

  • 👤 Martin Christopher Cook
  • 👤 Brian Laundon

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 16:07
CPC Classifications
C; C07; C07D; C07D499/00

Claims Analysis

Total Claims: 7
Claim 1
Independent Claim 46 words
A cephalosporin compound having the formula ##SPC6## wherein R is a carboxyl blocking group and P is selected from the group consisting of lower alkyl, phenyl lower alkyl, chloromethyl, bromomethyl, iodomethyl, lower alkoxymethyl and lower alkanoyloxymethyl; and B is > S or > S → O.
Claim 2
Dependent Claim 46 words
A cephalosporin compound having the formula ##SPC6## wherein R is a carboxyl blocking group and P is selected from the group consisting of lower alkyl, phenyl lower alkyl, chloromethyl, bromomethyl, iodomethyl, lower alkoxymethyl and lower alkanoyloxymethyl; and B is > S or > S → O.
Claim 3
Dependent Claim 10 words
A compound of claim 1 wherein B is > S.
Claim 4
Dependent Claim 44 words
A compound selected from the group consisting of diphenylmethyl (6R,7R)-3-acetoxymethyl-7-formamido ceph-3-em-4-carboxylate; diphenylmethyl (2'ζ,6r,R,R)-7-(2'-hydroxy-2'-phenylacetamido)-3-methylceph-3-em-4-carboxylate; diphenylmethyl (6R,7R,2' R and S)-7-[2'-hydroxy2'-(p-nitrophenyl)acetamido]-3-methylceph-3-em-4-carboxylate; (6R,7R,2'S)-7-[2'-hydroxy-2'-(p-nitrophenyl) acetamido[-3-methylceph-3-em-4carboxylic acid; diphenylmethyl (6R, 7R, 2'R and S)-7[2'-hydroxy-2'-(thien-2-yl)acetamido]-3-metylceph-3-em-4-carboxylate; diphenylmethyl (6R,7R,2'R and S)-3-acetoxymethyl-7-[(2'-hydroxy-2'-(-nitrophenyl)acetamido]ceph-3-em-4-carboxylate; (6R,7R,2'R and S)-7-[2'-hydroxy-2'-(fur-2-yl) acetamido]-3-methylceph-3-em-4-carboxylic acid and the sodium salt and diphenylmethyl ester thereof.
Claim 5
Dependent Claim 44 words
A compound selected from the group consisting of diphenylmethyl (6R,7R)-3-acetoxymethyl-7-formamido ceph-3-em-4-carboxylate; diphenylmethyl (2'ζ,6r,R,R)-7-(2'-hydroxy-2'-phenylacetamido)-3-methylceph-3-em-4-carboxylate; diphenylmethyl (6R,7R,2' R and S)-7-[2'-hydroxy2'-(p-nitrophenyl)acetamido]-3-methylceph-3-em-4-carboxylate; (6R,7R,2'S)-7-[2'-hydroxy-2'-(p-nitrophenyl) acetamido[-3-methylceph-3-em-4carboxylic acid; diphenylmethyl (6R, 7R, 2'R and S)-7[2'-hydroxy-2'-(thien-2-yl)acetamido]-3-metylceph-3-em-4-carboxylate; diphenylmethyl (6R,7R,2'R and S)-3-acetoxymethyl-7-[(2'-hydroxy-2'-(-nitrophenyl)acetamido]ceph-3-em-4-carboxylate; (6R,7R,2'R and S)-7-[2'-hydroxy-2'-(fur-2-yl) acetamido]-3-methylceph-3-em-4-carboxylic acid and the sodium salt and diphenylmethyl ester thereof.
Claim 6
Dependent Claim 9 words
The compound of claim 1 which is diphenylmethyl (6R,7R)-7-isocyano-3-methylceph-3-em-4-carboxylate.
Claim 7
Dependent Claim 11 words
The compound of claim 1 which is diphenylmethyl (6R,7R and S)-7-isocyano-3-acetoxymethylceph-3em-4-carboxylate.

References Cited (Backward Citations)

US3763154A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-08-10 1980-02-09 1980-08-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-08-10 1984-02-09 1984-08-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-08-10 1988-02-09 1988-08-10 $7700.00 Window Closed / Lapsed

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