2-Isopropyl-2-(2-methylphenyl)-5-(N-methyl-N-homoveratr ylamino)

Details 2-Isopropyl-2-(2-methylphenyl)-5-(N-methyl-N-homoveratr ylamino) 2-Isopropyl-2-(2-methylphenyl)-5-(N-methyl-N-homoveratr ylamino)

1987-07-17

1989-07-11

Sneed, H. M. S.

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitriles

558359, C07D31760

Patent

active

048474037

ABSTRACT:
2-Isopropyl-2-(2-methylphenyl)-5-(N-methylhomoveratrylamino)-valeronitrile ("mepamil") of the Formula I: ##STR1## preferably administered in the form of water-soluble acid addition salts such as e.g. hydrochloride. The claimed compound is advantageously prepared by alkylation of 2-(2-methylphenyl)-3-methylbutyronitrile with 3,3-diethoxypropylchloride. Subsequently, the obtained 5,5-diethoxy-2-isopropyl-2-(2-Methylphenyl)-valeronitrile is mildly, acidically hydrolisized to yield the appropriate aldehye, i.e. 2-isopropyl-2-(2-methylphenyl)-5-oxovaleronitrile. This aldehyde is then reacted with N-methylhomoveratrylamine under conditions of reductive alkylation, suitably by catalytic hydrogenation over a platinum or palladium catalyst or by chemical reduction with the use of formic acid as a reducing agent. The resulting base is optionally converted by neutralization with a pharmaceutically acceptable organic or inorganic acid, i.e. hydrochloric or fumaric acid, into the corresponding acid addition salt.

REFERENCES:
patent: 4350636 (1982-09-01), Kastner et al.
B. N. Singh et al., Drugs 15, 169-97, 1978, "Verapamil: A Review of its Pharmacological Properties and Therapeutic Use".
R. Mannhold et al., Arch. Pharmacol. 302, 217-226, 1978 Investigations on the Structure-Activity Relationships of Verapamil.
H. D. Hoeltje, Arch. Pharmazie 315, 317-23, 1982 "Theoretische Untersuchung zu Struktur-Wirkungsbeziehungen von ringsubstituier-ten Verapamil-Derivaten".

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