N-(4-Phenyl-2-thiazolyl)carbamate derivatives

Details N-(4-Phenyl-2-thiazolyl)carbamate derivatives N-(4-Phenyl-2-thiazolyl)carbamate derivatives

1982-09-08

1985-04-16

Gerstl, Robert

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

548196, 514885, C07D27748, A01K 31425

Patent

active

045115745

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND AND FIELD OF THE INVENTION

This invention relates to N-(4-phenyl-2-thiazolyl)carbamate derivatives, a process for preparing same and medicinal compositions containing same.
More particularly, this invention relates to N-(4-phenyl-2-thiazolyl)carbamate derivatives, which derivatives have immunomodulating activity and are thus effective against immunodiseases such as chronic rheumatoid arthritis and also useful against viral diseases or for the immunotherapy of cancers but display only a low toxicity, and are thus extremely desirous as medicines, a process for preparing same and medicinal compositions containing same.
A number of steroid-type and nonsteroid-type anti-inflammatory drugs have heretofore been clinically employed against autoimmune diseases such as rheumatism. However, these drugs are not quite satisfactory in their pharmacological effects, side effects and toxicity. The compounds of the present invention give a peculiar effect to cells participating in an immunity response so as to modulate the immunity response of the host. Although the disclosure of Japanese Laid-open Patent Appln. No. Sho. 54-61172 is known, which relates to compounds having a comparatively similar structure, the compounds of this invention have substituents different from those contained in such prior art compounds and possess important characteristics from a pharmacological standpoint.


DETAILED DESCRIPTION OF THE INVENTION

The present invention provides new chemical substances, i.e. N-(4-phenyl-2-thiazolyl)carbamates of the general formula (1): ##STR1## wherein R.sub.1 denotes a lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, nitro or amino group, and R.sub.2 represents a lower alkyl or halogeno-lower alkyl group, a process for preparing these compounds and medical compositions containing the same.
In the above general formula, the term "lower alkyl group" means groups having 1-4 carbon atoms. As the compounds of the general formula (1) show tautomerism between their amine form and their imine form, the compounds of the general formula (1) in connection with the present invention embrace such tautomers.
Illustrative of the carbamate derivatives of the above general formula (1) concerned with the present invention wherein R.sub.2 represents a lower alkyl group are, for example, lower alkyl esters of the following carbamic acids:
On the other hand, examples wherein R.sub.2 in the formula represents a halogeno-lower alkyl group include the following compounds:
These compounds represented by the general formula (1) are obtained by reacting 2-amino-4-phenylthiazoles represented by the general formula (2): ##STR2## wherein R.sub.1 has the same significance as defined in the general formula (1) with chloroformates having the general formaula (3): (1) and X is a halogen atom.
The reaction may be carried out by either dissolving or suspending a starting material represented by the general formula (2)--which may optionally be in the form of a suitable acid addition salt--in a solvent and then adding dropwise or in a similar manner a compound of the general formula (3) to the solution or suspension. As suitable solvents used in this case are, for example, benzene toluene, xylene, acetone, ethyl methyl ketone, dioxane, 1,2-dimethoxyethane, tetrahydrofuran, and N,N-dimethylformamide. An organic base such as pyridine or triethylamine or an inorganic base such as sodium carbonate, potassium carbonate or sodium hydrogen carbonate can be used for the purpose of removing hydrogen halide formed in the course of the reaction.
The above reaction may proceed at temperatures below room temperature. However, it is possible to heat the reaction mixture up to the boiling point of the solvent in order to accelerate the reaction.
Most of the starting materials, namely, 2-amino-4-phenylthiazoles represented by the general formula (2) are known to the public and described in detail, for example, in a publication [Jacques V. Metzger, ed. "The Chemistry of Heterocyclic Compounds", Vol. 34; "Thiazole and Its Derivatives", Part Tw

REFERENCES:
patent: 4027031 (1977-05-01), DeBaun et al.
patent: 4217355 (1980-08-01), Harbert et al.
patent: 4225610 (1980-09-01), Tarayre et al.
Metzger, Thiazole & its Derivatives, 232-235(1979).

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