4-methyl-5-(2-(4-phenylpiperazin-1-yl)ethyl)thiazole derivatives

Details 4-methyl-5-(2-(4-phenylpiperazin-1-yl)ethyl)thiazole derivatives 4-methyl-5-(2-(4-phenylpiperazin-1-yl)ethyl)thiazole derivatives

1991-04-11

1992-06-09

Shen, Cecilia

Harness for working animal

Thill tugs

544369, A61K 31495, C07D41706

Patent

active

051207362

DESCRIPTION:

BRIEF SUMMARY
The present invention relates, by way of novel products, to the products of the following general formula: ##STR2## in which R is selected from a hydrogen atom, an alkyl radical having from 2 to 7 carbon atoms and an aralkyl radical of which the aryl moiety preferably consists of phenyl and of which the alkyl moiety has from 1 to 4 carbon atoms, it being possible for said products to take the form of pharmaceutically acceptable salts.
In formula (I), the alkyl or aralkyl radicals can have a linear or branched chain.
An alkyl group having from 2 to 7 carbon atoms is, for example, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, neopentyl, isopentyl, hexyl or heptyl.
An aralkyl radical is, for example, benzyl, ethylphenyl, propylphenyl or methylnaphthyl, preferably benzyl.
The salts of the products of formula (I) are obtained in known manner by bringing a product of formula (I) into contact with an appropriate amount of a pharmaceutically acceptable acid such as, for example, a mineral acid like hydrochloric acid or sulfuric acid, or an organic acid like citric, tartaric, maleic or methanesulfonic acid.
4-Methyl-5-[2-(4-phenylpiperazin-1-yl)ethyl]-thiazole is described in French patent application no. 2 594 335.
Derivatives of this compound have also been described in the publications Acta-Pol. Pharm. 40(2), page 159 and Pol. Pl. 78 185, 19 May 1975. However, the products of formula (I) and their salts have never been described in the literature.
The present invention further relates to a method of preparing products of formula (I), said method consisting in reacting, with one equivalent of 4-methyl-5-.beta.-chloroethylthiazole, either two equivalents of 4-phenylpiperazine substituted in the 2-position on the phenyl by a group OR, in which R is as defined above, or one equivalent of 4-picoline and one equivalent of substituted 4-phenylpiperazine, or one equivalent of substituted 4-phenylpiperazine and an excess of anhydrous sodium carbonate, and, if desired, in converting the resulting product to one of its pharmaceutically acceptable salts. Said reaction is generally carried out with heating and in a solvent medium.
The present invention further relates to a pharmaceutical composition containing at least one product of formula (I) as the active product, it being possible for said composition to be useful especially in the field of urology.
According to this feature, the invention also aims to cover a method of preparing drugs useful especially in the field of urology, which comprises incorporating at least one product of formula (I), as the active product, into a pharmaceutically acceptable vehicle, excipient or carrier.
4-Methyl-5-[2-(4-phenylpiperazin-1-yl)ethyl]-thiazole, described in French patent application 2 594 335, is also recommended as an active ingredient in drugs useful in the field of urology.
However, as will be demonstrated below, all the compounds according to the present invention possess very valuable pharmacological properties and, in particular, have a 50% effective dose (ED.sub.50) which is very appreciably lower than that of this compound known in the prior art.
It has been discovered, unexpectedly, that the particular family of 4-methyl-5-[2-(4-phenylpiperazin-1-yl)ethyl]thiazole derivatives containing a hydroxyl or alkoxy group in the 2-position on the terminal phenyl ring have very valuable pharmacological properties and that the toxicity of these derivatives is sufficiently low to enable them to be used in therapeutics.
The same also applies to the derivative containing a methoxy group in the 2-position on the phenyl ring. This compound is not claimed as a novel product since it has been described in the afore-mentioned publication ACTA Pol. Pharm. 40(2), page 159. However, the known activity of said compound is quite different from the activity demonstrated by the Applicant.
It is for this reason that the invention further relates to the use of the compounds of aforementioned formula (I), in which the radical R is as defined above and can also be a methyl radical, in the prep

REFERENCES:
Chemical Abstracts, vol. 85, No: 11, Sep. 13, 1976, (Columbus, Ohio, US), see p. 550, abstract 78164f.
Chemical Abstracts, vol. 100, No: 19, May 7, 1984, (Columbus, Ohio, US), M. Bogdal et al.: "Thiazole derivatives. IV. Synthesis and pharmacological screening of 2-methyl-5-)2-N-substituted-aminoethyl) thiazoles", see p. 529, abstract 156531t.

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