N-phenyl amidines

Details N-phenyl amidines N-phenyl amidines

1977-07-25

1980-04-01

Randolph, John D.

Drug, bio-affecting and body treating compositions

Antigen, epitope, or other immunospecific immunoeffector

Allergen or component thereof

424278, 544 56, 544 98, C07D29564, C07D27910, A61K 3134, A61K 3138, A61K 31535, A61K 3154

Patent

active

041962125

ABSTRACT:
N-Phenyl amidines which have diuretic, antithrombogenic, smooth muscle relaxant, anti-inflammatory and antiarrhythmic properties have been discovered. They are prepared by reacting a substituted aniline with a carboxamide selected from the group consisting of amides and lactams in the presence of phosphorus oxychloride. Typical examples of substituted N-phenyl amidines thus obtained are 5-methyl-2-(N-phenylbenzylamino)-1-pyrroline, 2-(N-phenylbenzylamino)-1-pyrroline, 3-[(N-1-pyrrolin-]-yl-p-anisidino)methyl]indole and 4,5,6,7,8,9-hexahydro-2-(N-phenylphenethylamino)-3H-azonine. Indole substituted N-phenyl amidines can be rearranged to provide iminopyrrolinidinyl-indoles which are useful as diuretic, antithrombogenic and smooth muscle relaxant agents. In the case of 3-[(N-1-pyrrolin-2-yl-p-anisidino)methyl]indole, the rearranged product is 3-[[2-(p-methoxyphenylimino)-1-pyrrolidinyl]methyl]indole.

REFERENCES:
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Laboratoires Dausse, S.A., Chem. Abstracts, vol. 55, cols. 22345 to 22346 (1961).
Grunfeld, Chemical Abstracts, vol. 31, cols. 5774 to 5775 (1937).
Mandel et al., Chemical Abstracts, vol. 49, cols. 10225 to 10227 (1955).
Burger, Medicinal Chemistry, 2nd ed., frontispage and pp. 79-81, Interscience Publishers, NY 1960.

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