(1) Field of the Invention
The present invention relates to novel pyridylaminobenzamide compounds, their use as antihypertensive agents, and a method for their preparation.
(2) Information Disclosure Statement
2-(4-Pyridinylamino)benzoic acid [Ferrier and Campbell, Chemistry & Industry 1089 (1958)], an intermediate for the compounds of the instant invention, is inactive as an antihypertensive agent.
2-(Phenylamino)benzamide [Juby et al., J. Med. Chem. 11, 111 (1968)], a phenyl analog of the compounds of the instant invention, is inactive as an antihypertensive agent.
E. S. Schipper (Shulton Inc.) U.S. Pat. No. 3,226,394, issued Dec. 28, 1965 discloses a series of pyridylethylaminobenzamides having central nervous system depressant activity. Individual compounds disclosed include 2.beta.-(4-pyridyl)ethylaminobenzamide (Example 2) and 2.beta.-(4-pyridyl)ethylamino-N-(n-propyl)benzamide (Example 6).
B. E. Graham and W. Veldkamp (Upjohn) U.S. Pat. No. 3,632,761, issued Jan. 4, 1972 discloses a series of 4-quinolinylaminobenzamides having antihypertensive and anti-anxiety activity. Preparation 3 describes the preparation of 1-[4-(7-chloro-4-quinolinylamino)benzoyl]piperidine.
M. E. Konshin and N. P. Khokhryakova (Perm. Gos. Farm. Inst., Perm, USSR) Deposited Document 1981 VINITI 2966-81 (June 1, 1981) describe the synthesis and antimicrobial activity of arylamides of N-(4-pyridyl)anthranilic acid.
Information on the pharmacological properties of the preferred species of the present invention has been published in The Pharmacologist, Vol. 25, No. 3, p. 101 (1983) under the following titles: Antihypertensive Activity of Win 48049 (1-[2-(4-pyridinylamino)benzoyl]piperidine) in the Hypertensive Rat, Dog and Monkey, by Harlan Lape, Albert DeFelice and Denis Bailey; and Direct Vasodilator and Sympatholytic Activities of Win 48049, a New Antihypertensive, in Experimental Animals, by A. DeFelice and H. Lape (Sterling-Winthrop Research Institute, Rensselaer, N.Y.).