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US4068075A Expired / Lapsed US ⏱️ 0.0 years remaining

O-2-isocephem-4-carboxylic acid derivatives as antibacterial agents

Assignee: Bristol Myers Co
•
Filing: 1976-08-19
•
Granted: 1978-01-10
•
Expires: 1996-08-19
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Abstract

Abstract There is described the stereoselective total synthesis of novel Δ 2 ,3 -1,4-morpholine-2-carboxylic acids possessing a fused β-lactam ring in the 1,6-position and carrying a substituent cis to carbon 5 in the 7-position of the fused ring system represented by the general formula ##STR1## wherein Z is halo, hydroxyl, etherified hydroxyl or hydroxyl esterified with a carboxylic acid residue or a sulfonic acid residue and X is amino, azido or acylamino. Also included in the invention are compounds of formula I in which the carboxyl group at the 2-position is protected as by an easily cleavable ester group and salts of both the free acids and carboxyl-protected compounds of formula I. The compounds of formula I are potent antibacterial agents or are of use as intermediates in the preparation of such antibacterial agents.

Inventors

  • 👤 Marcel Menard
  • 👤 Gary M. F. Lim
  • 👤 Terry T. Conway

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 02:41
CPC Classifications
C; C07; C07D; C07D309/00; C07D309/02; C07D309/08; C07D309/10; C07D309/12; A; A61; A61P; A61P31/00; A61P31/04; C07C; C07C59/00; C07C59/40; C07C59/58; C07C59/64; C07C59/66; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D205/085; C07D317/00; C07D317/08; C07D317/10; C07D317/14; C07D317/28

Claims Analysis

Total Claims: 6
Claim 1
Independent Claim 64 words
A compound having the formula ##STR166##wherein Z is esterified hydroxyl of the formula --OSO.sub.2 R.sub.2 in which R 2 ' is (lower)alkyl, trifluoromethyl or p-tolyl and R" is hydrogen or an esily cleavable ester carboxyl-protecting group selected from the group consisting of benzhydryl, benzyl, p-nitrobenzyl, p-methoxybenzyl, trichloroethyl, trimethylsilyl, phenacyl, acetonyl, (lower)alkyl, triphenylmethyl, methoxymethyl, indanyl, phthalidyl, pivaloyloxymethyl and acetoxymethyl, or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim 64 words
A compound having the formula ##STR166##wherein Z is esterified hydroxyl of the formula --OSO.sub.2 R.sub.2 in which R 2 ' is (lower)alkyl, trifluoromethyl or p-tolyl and R" is hydrogen or an esily cleavable ester carboxyl-protecting group selected from the group consisting of benzhydryl, benzyl, p-nitrobenzyl, p-methoxybenzyl, trichloroethyl, trimethylsilyl, phenacyl, acetonyl, (lower)alkyl, triphenylmethyl, methoxymethyl, indanyl, phthalidyl, pivaloyloxymethyl and acetoxymethyl, or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim 11 words
A compound of claim 1 wherein R 2 ' is methyl.
Claim 4
Dependent Claim 14 words
The acid of claim 2 having the formula ##STR167##or a pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim 9 words
The acid of claim 2 having the formula ##STR168##
Claim 6
Dependent Claim 14 words
A compound of claim 2 wherein R" is pivaloyloxymethyl, methoxymethyl, indanyl, phthalidyl or acetoxymethyl.

References Cited (Backward Citations)

US3835130A Cited
GB1377715A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-01-09 1981-07-11 1982-01-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-01-09 1985-07-11 1986-01-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-01-09 1989-07-11 1990-01-10 $7700.00 Window Closed / Lapsed

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