2-Isopropyl-2-(2-methylphenyl)-5-(N-methyl-N-homoveratrylamino)-valeronitrile and method for producing same

2-Isopropyl-2-phenyl-5-(N-methyl-2-phenylethylamino)-valeronitrile derivatives of the general formula I wherein R is a methyl, chlorine, bromine, C1 to C4 alkoxyl or methylthio group, preferably administered in the form of soluble acid addition salts, notably the 2-methylphenyl analog as its hydroch...

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Hauptverfasser: HELFERT, IVAN, BLAHA, LUEDVIK, TRCKA, VACLAV, RAJSNER, MIROSLAV
Format: Patent
Sprache:eng
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Zusammenfassung:2-Isopropyl-2-phenyl-5-(N-methyl-2-phenylethylamino)-valeronitrile derivatives of the general formula I wherein R is a methyl, chlorine, bromine, C1 to C4 alkoxyl or methylthio group, preferably administered in the form of soluble acid addition salts, notably the 2-methylphenyl analog as its hydrochloride, possess significant calcium-antagonistic and cardiac antiarrythmic activity. Preparation is by alkylation of the corresponding butyronitrile derivative (obtained from the respective substituted benzylcyanide by alkylation with isopropylbromide) by 3,3-diethoxypropylchloride, subsequent acidic hydrolysis of the 5,5-diethoxy-2-isopropyl-2-phenylvaleronitrile derivative obtained to the appropriate aldehyde, and reductive alkylation of this aldehyde with N-methylhomoveratrylamine by catalytic hydrogenation over a platinum or palladium catalyst or chemical reduction using formic acid. The resulting base is optionally neutralized with a pharmaceutically acceptable organic or inorganic acid, e.g. hydrochloric or fumaric acid, into the corresponding acid addition salt.