# US 4,395,410 A · Quaternary ammonium antiarrhythmic drugs

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- Number: US 4,395,410 A
- Document ID: US4395410A
- Status: Granted
- Kind: A
- Application number: 06/273,822
- Filed: 1981-06-15
- Granted: 1983-07-26
- Earliest claimed: 1977-12-19
- Assignees: Eli Lilly and Company
- Inventors: Bryan B. Molloy; Mitchell I. Steinberg
- Web page: https://patentgrep.com/patent/US4395410A

## CPC

- A61K 31/33: Heterocyclic compounds
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)

## Abstract

Quaternary ammonium salts of certain phenylpropylamines and phenylbutylamines are useful antiarrhythmic drugs. A method for treating arrhythmia and prolonging the action potential of cardiac tissue is provided. Pharmaceutical formulations containing such quaternary ammonium salts are disclosed.

## Claims

### Claim 1

A compound having the general formula ##STR3## wherein: n is 1 or 2;
R.sup.1 is hydrogen or C.sub.1 -C.sub.2 alkyl;
R.sup.2 is hydrogen or C.sub.1 -C.sub.3 alkyl;
R.sup.3 is C.sub.1 -C.sub.4 alkyl or phenyl C.sub.1 -C.sub.4 alkyl;
R.sup.4 and R.sup.5 taken together with the adjacent nitrogen to which they are attached complete a heterocyclic ring having 4 to 7 carbon atoms;
R.sup.6 and R.sup.7 independently are hydrogen, hydroxy, halogen, nitro, C.sub.1 -C.sub.3 alkoxy, or C.sub.1 -C.sub.3 alkyl, provided that at least one of R.sup.6 and R.sup.7 is hydrogen, and
X is a therapeutically acceptable anion.

### Claim 2 (depends on 1)

The compound of claim 1 wherein R.sup.3 is C.sub.1 -C.sub.4 alkyl and R.sup.6 and R.sup.7 independently are hydrogen, halogen, nitro, C.sub.1 -C.sub.3 alkoxy, or C.sub.1 -C.sub.3 alkyl.

### Claim 3 (depends on 2)

The compound of claim 2 wherein n is 1.

### Claim 4 (depends on 1)

The compound of claim 1 wherein R.sup.6 is halogen or nitro.

### Claim 5 (depends on 1)

The compound of claim 1 wherein n is 2 and R.sup.6 is halogen or nitro.

### Claim 6 (depends on 1)

The compound of claim 1 wherein R.sup.1 is C.sub.1 -C.sub.2 alkyl and R.sup.2 is hydrogen.

### Claim 7 (depends on 1)

The compound according to claim 1 which is N-methyl-N-(4-phenylbutyl)hexahydroazepinium bromide.

### Claim 8 (depends on 1)

The compound according to claim 1 which is N-methyl-N-(4-phenylbutyl)-tetrahydropyrrolium bromide.

### Claim 9 (depends on 1)

The compound according to claim 1 which is N-methyl-N-(4-phenylbutyl)piperidinium methanesulfonate.

### Claim 10 (depends on 1)

A method of treating re-entrant arrhythmias in humans suffering from such arrhythmias and in need of treatment or in humans suspected of developing a re-entrant arrhythmia comprising administering to such subject an antiarrhythmically effective dose of a compound of claim 1.

### Claim 11 (depends on 10)

The method according to claim 10 employing a compound wherein R.sup.3 is C.sub.1 -C.sub.4 alkyl and R.sup.6 and R.sup.7 independently are hydrogen, halogen, nitro, C.sub.1 -C.sub.3 alkoxy, or C.sub.1 -C.sub.3 alkyl.

### Claim 12 (depends on 1)

A pharmaceutical formulation for the treatment of re-entrant arrhythmias in humans comprising as active ingredient an antiarrhythmic amount of a quaternary ammonium salt of claim 1 in combination with one or more pharmaceutically acceptable diluents or carriers therefor.

### Claim 13 (depends on 12)

The formulation of claim 12 employing a compound wherein R.sup.3 is C.sub.1 -C.sub.4 alkyl, and R.sup.6 and R.sup.7 independently are hydrogen, halogen, nitro, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 alkyl.