# US 4,396,621 A · Certain 2-oxo-2,3-dihydro-3-benzothiophene-carboxamides and their pharmaceutical compositions

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- Number: US 4,396,621 A
- Document ID: US4396621A
- Status: Granted
- Kind: A
- Application number: 06/204,747
- Filed: 1980-11-07
- Granted: 1983-08-02
- Earliest claimed: 1976-04-09
- Assignees: Ciba-Geigy Corporation
- Inventors: Raymond Bernasconi; Pier G. Ferrini; Richard Goschke; Jacques Gosteli
- Web page: https://patentgrep.com/patent/US4396621A

## CPC

- C07D 333/36: Nitrogen atoms
- C07D 333/64: Oxygen atoms
- C07D 333/68: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D 333/70: attached in position 2
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Oxothia compounds, especially 2-oxo-2,3-dihydro-benzo[b]-thiophene compounds of the formula ##STR1## in which Ph represents an optionally substituted 1,2-phenylene radical, X represents oxygen or sulphur, R.sub.1 represents an organic radical bonded via a carbon atom and R.sub.2 denotes hydrogen or an optionally substituted hydrocarbon radical of aliphatic character, and their salts are useful as peripheral analgetics and/or as antiphlogistic uricosuric and/or thrombolytic agents.

## Claims

### Claim 1

An compound of the formula ##STR10## in which Ph represents 1,2-phenylene which is optionally substituted by lower alkyl, lower alkoxy, halogen, trifluoromethyl and/or nitro, X represents oxygen or sulphur, R.sub.1 represents pyridinyl or 6-membered di-azaaryl which radicals are optionally substituted by lower alkyl, lower alkoxy, halogen, trifluoromethyl and/or nitro, or furyl, thienyl, a 5-membered oxaza- or thiaza-aryl which radicals are optionally substituted by lower alkyl, lower alkoxy, halogen, trifluoromethyl and/or nitro and R.sub.2 represents hydrogen or lower alkyl, or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

A compound of the formula I as claimed in claim 1, in which Ph represents 1,2-phenylene which is optionally substituted by lower alkyl, lower alkoxy, halogen with an atomic number of up to 35, trifluoromethyl, X represents oxygen, R.sub.1 denotes pyridyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl or isothiazolyl which are optionally substituted by lower alkyl and R.sub.2 represents hydrogen, or a pharmaceutically acceptable salt thereof.

### Claim 3 (depends on 1)

A compound of the formula I as claimed in claim 1, in which Ph represents 1,2-phenylene which can optionally be substituted by lower alkyl, lower alkoxy and/or halogen with an atomic number of up to 35, X represents oxygen, R.sub.1 denotes or pyridyl, thienyl, isoxazolyl, thiazolyl or isothiazolyl which are optionally substituted by lower alkyl and R.sub.2 represents hydrogen.

### Claim 4 (depends on 1)

A compound as claimed in claim 1 being N-[3-(5-Methylisoxazolyl)]-2-oxo-2,3-dihydro-3-benzo[b]thiophene-carboxami de or a pharmaceutically usable salt thereof with a base.

### Claim 5 (depends on 1)

A compound as claimed in claim 1 being N-(2-Pyridyl)-2-oxo-2,3-dihydro-3-benzo[b]thiophene-carboxamide or a pharmaceutically usable salt thereof with a base.

### Claim 6 (depends on 1)

A compound as claimed in claim 1 being N-(2-Thiazolyl)-5-chloro-2-oxo-2,3-dihydro-3-benzo[b]thiophene-carboxamide or a pharmaceutically usable salt thereof with a base.

### Claim 7 (depends on 1)

A compound as claimed in claim 1 being N-(2-Thienyl)-2-oxo-2,3-dihydro-3-benzo[b]thiophencarboxamide or a pharmaceutically usable salt thereof with a base.

### Claim 8 (depends on 1)

A compound as claimed in claim 1 being N-(2-Pyridyl)-6-chloro-2-oxo-2,3-dihydro-3-benzo[b]thiophen-carboxamide or a pharmaceutically usable salt thereof with a base.

### Claim 9 (depends on 1)

A compound as claimed in claim 1 being N-(2-Thiazolyl)-6-chloro-2-oxo-2,3-dihydro-3-benzo[b]thiophen-carboxamide or a pharmaceutically usable salt thereof with a base.

### Claim 10 (depends on 1)

A pharmaceutical preparation containing an analgetically effective amount of a compound claimed in claim 1 and conventional carriers and/or auxiliaries.