The present invention relates to selected metabolites of pirmenol, i.e., (+,-)-cis-.alpha.-[3-(2,6-dimethyl-1-piperidinyl)propyl]-.alpha.-phenyl-2- pyridinemethanol or N-[4-phenyl]-4-(2-pyridyl)-4-hydroxybutyl]-cis-2,6-dimethylpiperidine. The pharmacological activity of both pirmenol and the metabolites that are the present invention is antiarrhythmia. Thus, pharmaceutical compositions and use therefor comprising an antiarrhythmic effective amount of the metabolites are also within the scope of the invention.
Pirmenol is the starting material for synthetic preparation of the present invention metabolites. Therefore, U.S. Pat. No. 4,112,103, describing pirmenol, is incorporated by reference herein.
Precursors for pirmenol are disclosed in CA 97(11):92158m. These include .alpha.-[3-(2,6-dimethyl-1-piperidinyl)-1-propenyl]-.alpha.-phenyl[1(Z),2. alpha.,6.alpha.]-2-pyridinemethanol and .alpha.-[3-(2,6-dimethyl-1-piperidinyl)-1-propynyl]-.alpha.-phenyl[1(Z)-2. alpha.,6.alpha.]-2-pyridinemethanol. These disclosed precursors are different from the present invention because each precursor includes an unsaturated hydrocarbon chain. Also, the present compounds differ from both pirmenol and these precursors in the 2,6-dimethylpiperidine moiety.