# US 4,397,861 A · N- And carboxyl derivatives of thienamycin

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- Number: US 4,397,861 A
- Document ID: US4397861A
- Status: Granted
- Kind: A
- Application number: 06/321,497
- Filed: 1981-11-16
- Granted: 1983-08-09
- Earliest claimed: 1975-11-21
- Assignees: Merck & Co., Inc.
- Inventors: Burton G. Christensen; John Hannah; William J. Leanza; David H. Shih
- Web page: https://patentgrep.com/patent/US4397861A

## CPC

- C07D 477/20: Sulfur atoms
- A61P 31/04: Antibacterial agents
- C07D 205/08: with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Disclosed are N-acyl and carboxyl derivatives of the antibiotic thienamycin, which has the following structure: ##STR1## Such derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such derivatives, pharmaceutical compositions comprising such derivatives and methods of treatment comprising administering such derivatives and compositions when an antibiotic effect is indicated.

## Claims

### Claim 1

A compound having the structural formula: ##STR92## wherein R is a member selected from the group consisting of loweralkyl which may be substituted with loweralkoxy, mono- and diloweralkylamino, loweralkanoyloxy, loweralkanoylthio, loweralkanoylamino, loweralkylthio and pivaloxy; loweralkenyl; benzyl which may be substituted with loweralkyl, loweralkoxy, phenoxy, halo, nitro and pivaloxy; benzhydryl, phenyl, nitrophenyl, phenacyl and bromophenacyl; and R' is a member selected from the group consisting of: ##STR93## wherein R" is a member selected from the group consisting of hydrogen; loweralkyl (R" is not methyl) which may be substituted by hydroxy, loweralkoxy, phenyl, phenoxy, halo, amino, diloweralkylamino and guanidino; loweralkenyl, thionitrophenyl, benzyloxy, nitrobenzyloxy, loweralkoxybenzyloxy, loweralkoxy, haloloweralkoxy, loweralkylamino, loweralkylthio and thiophenyl.

### Claim 2 (depends on 1)

The compound of claim 1 wherein R is pivaloyloxymethyl and R' is glycyl.

### Claim 3 (depends on 1)

An antibiotic pharmaceutical composition consisting essentially of a therapeutically effective amount of a compound according to claim 1 and a pharmaceutical carrier therefor.

### Claim 4 (depends on 1)

An antibiotic pharmaceutical composition consisting essentially of in unitary dosage form, a therapeutically effective amount of a compound according to claim 1 and a pharmaceutical carrier therefor.