# US 4,397,862 A · Gastrointestinal sparing thioester drugs

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- Number: US 4,397,862 A
- Document ID: US4397862A
- Status: Granted
- Kind: A
- Application number: 06/310,554
- Filed: 1981-10-13
- Granted: 1983-08-09
- Earliest claimed: 1981-10-13
- Assignees: Syntex (U.S.A.) Inc.
- Inventors: Edward Mroszczak; Richard Runkel
- Web page: https://patentgrep.com/patent/US4397862A

## CPC

- C07D 487/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Compounds of the formula: R'--CH.sub.2 --S--A wherein: R' is hydrogen, alkyl, --COOH or its pharmaceutically acceptable salts, --alkylene--COOH or its pharmaceutically acceptable salts, --alkylene-SO.sub.2 H or its pharmaceutically acceptable salts, --alkylene-SO.sub.3 H or its pharmaceutically acceptable salts, or --alkylene CH.sub.2 OH; and A is the acyl moiety of a pharmaceutically acceptable carboxylic acid, said acid having antiinflammatory properties; are gastrointestinal tract sparing drugs for antiinflammatory pharmaceuticals.

## Claims

### Claim 1

A compound of the formula:
R'--CH.sub.2 --S--A
wherein
R' is hydrogen, alkyl, -COOH or its pharmaceutically acceptable salts, --alkylene-COOH or its pharmaceutically acceptable salts, --alkylene-SO.sub.2 H or its pharmaceutically acceptable salts, --alkylene-SO.sub.3 H or its pharmaceutically acceptable salts, or --alkylene-CH.sub.2 OH; and
A is the acyl moiety of a pharmaceutically acceptable carboxcylic acid of the formula: ##STR4## wherein R.sup.3 is hydrogen, halo, or lower alkyl; and Ar is selected from the group consisting of: ##STR5## in which X is O or S; R is hydrogen, methyl, chloro or bromo;
R.sup.1 is hydrogen, a lower alkyl group having 1 to 4 carbon atoms; a lower alkoxy group having from 1 to 4 carbon atoms, chloro, fluoro or bromo; and
R.sup.2 is hydrogen or a lower alkyl group having from 1 to 4 carbon atoms.

### Claim 2 (depends on 1)

The compound of claim 1 wherein R' is hydrogen.

### Claim 3 (depends on 1)

The compound of claim 1 wherein R' is --COOH, or its pharmaceutically acceptable salts.

### Claim 4 (depends on 3)

The compound of claim 3 wherein
Ar is phenyl;
R.sup.1 is hydrogen; and
R.sup.3 is hydrogen,
namely carboxymethyl benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-thiocarboxylate.

### Claim 5 (depends on 1)

A pharmaceutical composition for inhibiting inflammation in human beings which comprises a therapeutically effective amount of a compound of claim 1 or a pharmaceutically acceptable acid addition salt thereof in admixture with a pharmaceutically acceptable excipient.

### Claim 6 (depends on 1)

A method for inhibiting inflammation in human beings which method comprises administering to a subject in need of such treatment a therapeutically effective amount of, or a pharmaceutical composition containing a therapeutically effective amount of, the compound of claim 1 or a pharmaceutically acceptable acid addition salt thereof.