2-(Aryl)-3-(dimethylamino)butyl-3,4,5-trimethoxybenzoates

Details 2-(Aryl)-3-(dimethylamino)butyl-3,4,5-trimethoxybenzoates 2-(Aryl)-3-(dimethylamino)butyl-3,4,5-trimethoxybenzoates

1972-05-08

1978-02-21

Raymond, Richard L.

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

Organic compounds

Carboxylic acid esters

560 39, 560 32, 560100, 2605706, 424300, 424308, 424330, 560104, 560 55, 560 38, 560107, 560106, C07C 6508

Patent

active

040752410

ABSTRACT:
The compounds 2-Aryl-3-amino-1-butanol derivatives of the formula ##STR1## wherein R represents hydrogen or acyl; R.sup.1 and R.sup.2 each independently represents hydrogen, phenyl lower alkyl, or lower alkoxy substituted phenyl lower alkyl, or both R.sup.1 and R.sup.2 are lower alkyl; and their pharmaceutically acceptable acid salts.
The compounds are crystalline solids or liquids which, having two asymmetry centers, can be obtained in their stereoisomeric forms as racemic mixtures or in their optically active forms. The compounds have cardiovascular activity as coronary dilators.
The compounds can be prepared by reacting an .alpha.-arylcrotonate with ammonia or with an amine followed by hydrogenation of the carbalkoxy group to give the corresponding butanol. The butanols are acylated in usual ways to give the compounds of formula (I) wherein R represents an acyl group.

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patent: 2983755 (1961-05-01), Kollonitsch et al.
patent: 3409672 (1968-11-01), Trepanier
patent: 3562262 (1971-02-01), Schmidt et al.
patent: 3714229 (1973-01-01), Saari et al.
Burger, Medicinal Chemistry, Wiley Interscience (1970) pp. 64, 71, 72.
March, Advanced Organic Chemistry, McGraw-Hill Co. (1968) pp. 589, 891, 319-320, 663.
Morsch, Monatsh, 61 299-313; C.A. 27 713.

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