3-[2-(4-arylpiperazin-1-yl)ethoxy]-p-cymene, the method of prepa

Details 3-[2-(4-arylpiperazin-1-yl)ethoxy]-p-cymene, the method of prepa 3-[2-(4-arylpiperazin-1-yl)ethoxy]-p-cymene, the method of prepa

1990-12-12

1992-05-05

Shen, Cecilia

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

544392, 544394, A61K 31495, C07D29500

Patent

active

051108160

DESCRIPTION:

BRIEF SUMMARY
The present invention relates, by way of novel products, to 3-[2-(4-phenylpiperazin-1-yl)ethoxy]-p-cymene and its derivatives which are ortho-, meta- and para-monosubstituted or --disubstituted on the phenyl ring and to a method of preparing these derivatives; it further relates to the drugs in which at least one of said compounds is present as the active principle.
The chemical products according to the invention have the general formula ##STR2## R.sub.1 and R.sub.2, which are identical or different, being selected from a hydrogen atom, a halogen atom, a hydroxyl radical, an alkyl radical having from 1 to 4 carbon atoms, an alkoxy radical having from 1 to 5 carbon atoms or a phenoxy, benzyloxy, trifluoromethyl or acetyl radical.
In formula I, the alkyl or alkoxy groups can have a linear or branched chain.
An alkyl group having from 1 to 5 carbon atoms is for example a methyl, ethyl, propyl, isopropyl, butyl, sec-butyl or tert-butyl group, preferably a methyl group.
An alkoxy group having from 1 to 5 carbon atoms is for example a methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, neopentoxy, pentoxy or isopentoxy group, preferably an ethoxy or isopropoxy group.
A halogen atom is preferably a chlorine atom.
The products according to the invention can also take the form of the salts of the products of formula (I) with a pharmaceutically acceptable mineral acid such as, for example, hydrochloric acid or sulfuric acid, or a pharmaceutically acceptable organic acid such as, for example, citric, tartaric, malic, maleic, fumaric or methanesulfonic acid.
The derivatives of p-cymene which are disubstituted in the 3-position and in the 6-position are already known and have cardiovascular and antiallergic activities. References which may be mentioned are the patents FR-2 570 376 and EP-179009, in which the substituent in the 3-position is an alkoxy substituted by a phenylpiperazine and in which the substituent in the 6-position is an aminohydroxyalkoxy, whereas in the patent EP-173634, the substituent in the 6-position is a hydroxyl.
In the present invention, the p-cymene is substituted only in the 3-position by an alkoxy. It is therefore a thymol derivative and consequently the compound is novel.
The products of the invention are manufactured from 3-(2-chloroethoxy)-p-cymene of formula (II) and the 1-(substituted phenyl)piperazine of formula (III) according to the following general reaction scheme: ##STR3## R.sub.1 and R.sub.2 being defined above.
The number of mol of compound (III) is approximately twice the number of mol of compound (II).
The pharmaceutically acceptable salts, for example the hydrochlorides, are obtained in known manner by bringing a solution of the product of formula (I) into contact with the acid in question (for example by bubbling hydrochloric acid into a solution of the product of formula (I)). Furthermore, these salts can contain one or two mol of salifying acid per mol of product of formula (I).
The present invention further relates to the drugs containing at least one product of formula (I) as the active product; said drugs can be useful especially in the field of urology.
The non-limiting Examples which follow illustrate the methods of preparing the products according to the invention.
The AgNO.sub.3 test is a test for product purity.


EXAMPLE 1



Synthesis of 3-[2-(4-p-fluorophenylpiperazin-1-yl)ethoxy]-p-cymene
dihydrochloride. Codename=B 1055. Product of formula (I) where R.sub.1 =4-fluoro, in the form of the dihydrochloride.


1. Preparation of 3-[2-(4-p-fluorophenylpiperazin-1-yl)ethoxyl]-p-cymene

The following are introduced into a 100 ml three-necked flask fitted with a condenser, a magnetic stirrer and a thermometer:
21.27 g (0.1 mol) of 3-(2-chloroethoxy)-p-cymene
43.2 g (0.24 mol) of 1-p-fluorophenylpiperazine.
The mixture is heated at 140.degree. C. for 10 hours.
After cooling to room temperature, the reaction medium is poured into a 10% solution of sodium bicarbonate. The aqueous phase obtained is extracted twice with 100 ml of methylene chloride. The combined organi

REFERENCES:
patent: 4698343 (1987-10-01), Creuzet et al.
patent: 4721715 (1988-01-01), Creuzet et al.

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