# US 4,396,622 A · Certain 1-(trifluoromethylphenyl sulfonamidoalkyl) azacycloalkanes and their use as anti-arrhythmic agents

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- Number: US 4,396,622 A
- Document ID: US4396622A
- Status: Granted
- Kind: A
- Application number: 06/348,212
- Filed: 1982-02-12
- Granted: 1983-08-02
- Earliest claimed: 1979-05-23
- Assignees: Johann A. Wuelfing
- Inventors: Ljerka Jozic
- Web page: https://patentgrep.com/patent/US4396622A

## CPC

- C07D 295/13: to an acyclic saturated chain
- A61P 9/06: Antiarrhythmics
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Pharmaceutical compositions which comprise a compound of the formula (I): ##STR1## or a salt thereof wherein NR.sub.2 represents a piperidyl, pyrrolidyl, morpholino or N-methyl-piperazyl group any of which may substituted by one or two methyl groups; R.sup.1 represents fluorine, chlorine, bromine, iodine, lower alkoxyl, hydroxyl, acetoxyl, nitro, cyano, amino, dimethylamino, lower alkyl, trifluoromethyl, methylthio, ethylthio, methoxycarbonyl, ethoxycarbonyl, acetamido or carboxamido; R.sup.2 represents hydrogen, fluorine, chlorine, bromine, iodine, lower alkoxyl, hydroxyl, lower alkyl; R.sup.3 represents hydrogen, chlorine or lower alkyl; or R.sup.1 and R.sup.2 when on adjacent carbon atoms may together represent a polymethylene group containing from 3 to 5 carbon atoms; and n is 2, 3 or 4; and a pharmaceutically acceptable carrier, compounds of formula (I) except those wherein R.sup.1 is a 2-methoxyl group, and 2,4-dimethyl-1-[2-(4-bromophenylsulphonamido)ethyl]pyrrolidine and 2,4-dimethyl-1-[2-(4-bromophenylsulphonamido)ethyl]pyrrolidine, a process for the preparation of compounds of the formula (I) and 2,4-dimethyl-1-[2-(4-bromophenylsulphonamido)ethyl]pyrrolidine and 2,4-dimethyl-1[2-(4-iodophenylsulphonamido)ethyl]pyrrolidine as antiarrhythymic agents.

## Claims

### Claim 1

A compound selected from the group consisting of sulfonamide of the formula: ##STR70## and the pharmaceutically acceptable salts thereof wherein A is a cyclic amino radical selected from the group consisting of pyrrolidino, 2,4-dimethylpyrrolidino, 2,5-dimethylpyrrolidino, 2,4-dimethylpiperidino and 4-methylpiperazine; and
n has a value of 2 or 3.

### Claim 2 (depends on 1)

A compound according to claim 1 wherein n is 2 and A is pyrrolidino, 2,4-dimethylpyrrolidino or 2,5-dimethypyrrolidino.

### Claim 3 (depends on 1)

A compound according to claim 1 wherein said sulfonamide is 2,4-dimethyl-1-[2-(3-trifluoromethylbenzenesulfonamido)ethyl]pyrrolidine.

### Claim 4 (depends on 3)

A compound according to claim 3 wherein the conformation of the methyl groups is cis.

### Claim 5 (depends on 1)

A compound according to claim 1 wherein said sulfonamide is 2,5-dimethyl-1-[2-(3-trifluoromethylbenzenesulfonamido)ethyl]pyrrolidine.

### Claim 6 (depends on 5)

A compound according to claim 5 wherein the conformation of the methyl groups is cis.

### Claim 7 (depends on 1)

The method of effecting an anti-arrhythmic response in humans and other animals which comprises administering thereto an effective amount of a compound according to claim 1.

### Claim 8 (depends on 1)

A pharmaceutical composition comprising an amount of a compound according to claim 1 sufficient to effect an anti-arrhythmic response in combination with a pharmaceutical carrier.