Thiazole compounds, a process for preparing same and a pharmaceu

Details Thiazole compounds, a process for preparing same and a pharmaceu Thiazole compounds, a process for preparing same and a pharmaceu

1982-09-13

1985-02-26

Gerstl, Robert

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

548185, 548195, 514371, 514825, A01K 31425, C07D41712

Patent

active

045017506

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

The present invention relates to new thiazole compounds which have immuno-modulating activity and are thus effective against immunodiseases such as chronic rheumatoid arthritis and also useful against viral diseases or for the immunotherapy of cancers, a process for preparing the compounds and medicinal compositions containing same.
A number of steroid-type and nonsteroid-type antiinflammatory 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 present inventors have carried out an extensive research on chemical substances, which give a peculiar effect to cells that take part in an immunity response and act to modulate the immunity response of the host. As a result, they have succeeded in obtaining thiazole derivatives which are extremely desirous as medicines having excellent immuno-modulating activity but little toxicity.


DISCLOSURE OF INVENTION

The present invention relates to thiazole compounds of the general formula (1): ##STR3## wherein R.sub.1 stands for a hydrogen or halogen atom or a lower alkyl, lower alkoxy, substituted or unsubstituted phenoxy, nitro or cyano group, R.sub.2 for a hydrogen atom or a lower alkyl or lower alkylthio group, and R for an .alpha.-halogenoalkyl group or the grouping: ##STR4## a process for preparing same and pharmaceutical compositions containing the thiazole compounds.
More particularly, the present invention provides the new thiazole compounds of the above general formula (1), which have immuno-modulating 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 show weak toxicity and are thus extremely desirous as medicines, a process for preparing the thiazole compounds and medicinal compositions containing the thiazole compounds.
The compounds concerned with the present invention represented by the general formula (1) show tautomerism between their amine-form and their imine-form. Thus, the compounds of the present invention include all of these tautomers.
Illustrative of the representative compounds of the present invention are as follows:
The compounds of the present invention represented by the general formula (1) can be prepared by reacting a 2-aminothiazole represented by the general formula: ##STR5## wherein R.sub.1 and R.sub.2 have the same definitions as given above, with halide of the general formula (3): stands for 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 halide of the general formula (3) to the solution or suspension. The reactants may sufficiently be used generally in stoichiometrically calculated amounts.
As suitable solvents to be used for the reaction may be mentioned, for example, benzene, toluene, xylene, acetone, ethyl methyl ketone, dioxane, 1,2-dimethoxyethane, tetrahydrofuran and N,N-dimethylformamide. For the sake of removing hydrogen chloride which will be produced in the course of the reaction, it may be possible to use an organic base such as pyridine or triethylamine or an inorganic base such as sodium carbonate, potassium carbonate or sodium hydrogen carbonate. The above reaction may proceed at temperatures below room temperature. However, it is possible to heat the reaction mixture to a temperature up to the boiling point of the solvent so as to accelerate the reaction.
Most of the 2-amino-4-phenylthiazoles, the starting materials, represented by the general formula (2) are known compounds. They are described in detail, for example, in technical publications [Jacques V. Metzger, ed. "The Chemistry of Heterocyclic Compounds", Vol. 34; "Thiazole and Its Derivatives", Part Two, (1979)].
The compounds of the present inve

REFERENCES:
patent: 3749775 (1973-07-01), Fancher
Gaugin et al., Pharmazie, 27, 164 (1972).
March, Advanced Org. Chem., pp. 382-383 (1977).

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