N-Phenyl amidines

Details N-Phenyl amidines N-Phenyl amidines

1979-11-19

1981-03-31

Rollins, Alton D.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

A61K 31395, C07D22500

Patent

active

042592380

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-1-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 arranged to provide iminopyrrolinidinylindoles 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:
patent: 3255181 (1966-06-01), Gatzi
patent: 3378438 (1968-04-01), Gatzi
patent: 3634401 (1972-01-01), Gatzi
patent: 4072675 (1978-02-01), Wu et al.

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