2-(2-Chloro-4-cyclopropyl-phenyl-imino)-imidazolidine, and acid

Details 2-(2-Chloro-4-cyclopropyl-phenyl-imino)-imidazolidine, and acid 2-(2-Chloro-4-cyclopropyl-phenyl-imino)-imidazolidine, and acid

1981-04-15

1982-07-27

Schwartz, Richard A.

Drug, bio-affecting and body treating compositions

Antigen, epitope, or other immunospecific immunoeffector

Parasitic organism or component thereof or substance...

548315, 564105, 564245, 564271, 564276, A61K 31415, C07D23350

Patent

active

043417884

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to 2-(2-chloro-4-cyclopropyl-phenylimino)-imidazolidine of the formula: ##STR1## and the physiologically acceptable acid addition salts thereof, having valuable therapeutical properties.
The compound of formula I and the acid addition salts thereof may be prepared by one of the following processes (a) to (c):
(a) reacting a compound of the formula: ##STR2## (wherein A represents a cyano group or the radical ##STR3## in which Y represents an alkoxy or alkylthio group having 1 to 4 carbon atoms or a sulfhydryl or amino group) with ethylene diamine or an acid addition salt thereof.
The reaction is effected at a temperature of from 100.degree. to 250.degree. C. Polar protic, polar aprotic or non-polar solvents may be used as solvent. The reaction may, however be effected without the use of a solvent in which case the reaction is effected at an elevated temperature. The reaction time varies from a few minutes to several hours.
(b) reaction of a compound of the formula: ##STR4## (wherein X and Z, which may be the same or different, each represent a halogen atom or an alkoxy or alkylthio group with 1 to 4 carbon atoms) with ethylene diamine or an acid addition salt thereof. If X and Z represent a halogen atom, preferably a chlorine atom, the reaction is effected at a temperature of from 0.degree. C. to ambient temperature. Inert solvents such as for example ethers, ketones, esters or aliphatic or aromatic hydrocarbons may be used as solvent.
If X and Z represent alkoxy or alkylthio group, the reaction is effected at an elevated temperature, preferably at the reflux temperature of the reaction mixture. Polar protic, polar aprotic or non-polar solvents may be used as solvent.
(c) deacylation of a compound of the formula: ##STR5## (wherein Acyl represents an aliphatic or aromatic acyl group) by reaction with an aliphatic alcohol or a dilute mineral acid.
Compounds of formula II may be obtained reacting 2-chloro-4-cyclopropylaniline with a cyanate or thiocyanate, a urea or thiourea being formed. The urea or thiourea may then be converted into the corresponding isouronium salt or isothiouronium salt for example, by the use of an alkylating agent. The corresponding isourea or isothiourea may be obtained from these acid addition compounds with bases. By dehydration of the urea or by removal of H.sub.2 S from the thiourea in the presence of lead or mercury salts 2-chloro-4-cyclopropyl-phenylcyanamide is obtained, with which ammonia may be reacted to form 2-chloro-4-cyclopropyl-phenyl-guanidine.
The isocyanide dichloride of formula III may be obtained by reaction of 2-chloro-4-cyclopropylaniline with formic acid followed by reaction of the formanilide obtained with a mixture of thionyl chloride and sulphuryl chloride.
Other starting compounds of formula III may be obtained by reacting the isocyanide dichloride with an alcohol or thioalcohol.
The starting compounds of formula IV may be prepared by reacting 2-chloro-4-cyclopropylaniline with an N-acyl-imidazolidinone-(2) in the presence of phosphorus oxychloride.
The 2-phenylimino-imidazolidine of the present invention may, if desired, be converted into a physiologically compatible acid addition salt by convertional methods. Acids suitable for salt formation include for example hydrochloric acid, hydrobromic acid, hydroiodic acid, hydrofluoric acid, sulphuric acid, phosphoric acid, nitric acid, acetic acid, propionic acid, butyric acid, caproic acid, valeric acid, oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, lactic acid, tartaric acid, citric acid, malic acid, benzoic acid, p-hydroxybenzoic acid, p-aminobenzoic acid, phthalic acid, cinnamic acid, salicyclic acid, ascorbic acid, methanesulphonic acid and 8-chlorotheophylline.
The novel compound of formula I and the physiologically compatible acid addition salts possess a strong bradycardiac activity and are suitable for the treatment of coronary diseases. The influence of the said compound on the heart beat frequency has been investigated in rabbits and in pithed rats as

REFERENCES:
patent: 4290971 (1981-09-01), Georgien et al.

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