Substituted phenoxyalkyl quaternary ammonium compounds as antiarrhythemic agents
AssigneeThe Dow Chemical Company
InventorStanley J. Strycker
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Abstract
Quaternary ammonium compounds such as [2-(4-amino-2,6-dibromophenoxy)ethyl]dimethyl (allyl) ammonium bromide are prepared by the reaction of a tertiary amine such as 3,5-dibromo-.beta.-dimethylamino-p-phenetidine with a substituted organic compound such as allyl bromide. The quaternary ammonium compounds are useful in alleviating or inhibiting cardiac arrhythmias when the quaternary ammonium compounds, or compositions comprising the same are administered to animals.
Claims8
A composition useful as an antiarrhythmic comprising a pharmaceutical carrier and from about 0.01 to about 98 percent by weight of a quaternary ammonium compound corresponding to the formula:
- ##STR8## wherein Y represents amino, loweralkylamino or diloweralkylamino;
- R.sub.1 and R.sub.2 taken together represent an aliphatic hydrocarbon moiety of 5 carbon atoms, substituted with zero, one or two lower alkyl substituents;
- R.sub.3 independently is selected from the group consisting of lower alkenyl, phenacyl, mono-, di-, or trihalophenacyl, lower alkynyl, substituted lower alkyl, substituted lower alkenyl and substituted lower alkynyl substituted with a substituent selected from the group consisting of halogen, phenyl, halophenyl dihalophenyl, trihalophenyl, nitrilo, and hydroxy;
- X.sub.1 and X.sub.2 both represent halogen;
- A.sup.- represents a stoichiometric equivalent quantity of a pharmaceutically-acceptable anion;
- n represents one of the integers 2, 3 or 4;
- HX represents a stoichiometric equivalent quantity of a pharmaceutically-acceptable acid;
- and m represents one of the integers zero and one.
A method for combatting cardiac arrhythmias which comprises administering to an animal a cardiac antiarrhythmic amount of a quaternary ammonium compound corresponding to the formula ##STR9## wherein Y represents amino, loweralkylamino or diloweralkylamino;
- R.sub.1 and R.sub.2 taken together represent an aliphatic hydrocarbon moiety of 5 carbon atoms substituted with zero, one or two lower alkyl substituents;
- R.sub.3 independently is selected from the group consisting of lower alkenyl, phenacyl, mono-, di-, or trihalophenacyl, lower alkynyl, substituted lower alkyl, substituted lower alkenyl and substituted lower alkynyl substituted with a substituent selected from the group consisting of halogen, phenyl, halophenyl, dihalophenyl, trihalophenyl, nitrilo and hydroxy [and carboxyalkyl and keto;
- R.sub.1, R.sub.2 and R.sub.3 independently taken together represent a quinuclidine, pyridine, picoline or lutidine residue];
- X.sub.1 and X.sub.2 both represent halogen;
- A.sup.- represents a stoichiometric equivalent quantity of a pharmaceutically-acceptable anion;
- n represents one of the integars 2, 3 or 4;
- HX represents a stoichiometric equivalent quantity of a pharmaceutically-acceptable acid;
- and m represents one of the integers zero and one.
Dependencies are inferred from the claim text.