Thiazolylurea derivatives, a process for preparing same and a ph

Details Thiazolylurea derivatives, a process for preparing same and a ph Thiazolylurea derivatives, a process for preparing same and a ph

1982-09-17

1984-12-25

Gerstl, Robert

Drug, bio-affecting and body treating compositions

Antigen, epitope, or other immunospecific immunoeffector

Bacterium or component thereof or substance produced by said...

424270, 546280, 548196, C07D27746, C07D41712, A61K 31425, A61K 3144

Patent

active

044903936

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

This invention relates to novel thiazolylurea derivatives, processes for preparing same and medicinal compositions containing same.
More particularly, this invention relates to thiazolylurea derivatives which possess immuno-modulating activity and are thus therapeutically effective against immunodiseases such as chronic rheumatoid arthritis and are also useful against viral diseases or for the immunotherapy of cancers, processes 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 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 thiazolylurea derivatives which are extremely desirous as medicines having excellent immuno-modulating activity but little toxicity.


DISCLOSURE OF INVENTION

The present invention provides thiazolylurea derivatives as new chemical substances which are represented by the general formula: ##STR3## wherein R.sup.1 stands for a lower alkyl group or a substituted or unsubstituted phenyl group, R.sup.2 for a hydrogen atom, a lower alkyl, lower alkoxy or lower alkylthio group, and R.sup.3 for a pyridyl or iso-oxazolyl group or a grouping of the general formula: ##STR4##
Illustrative of the representative compounds of the thiazolyl derivatives represented by the above general formula (I) in connection with the present invention are as follows:
As the new compounds of the present invention show tautomerism between their amine-form and their imine-form, the compounds of the present invention include all of these tautomers.
A first process provided by the present invention to prepare the novel compounds of this invention is characterized by reacting a 2-aminothiazole having the general formula: ##STR5## wherein R.sup.1 and R.sup.2 have the same meanings as defined above, with phosgene or a chloroformate represented by the general formula: ##STR6## wherein X stands for a chlorine atom or a lower alkoxy group, a benzyloxy group or a substituted or unsubstituted phenoxy group. The reaction can be carried out by either dissolving or suspending a starting material represented by the general formula (II), 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 (III) to the solution or suspension. Utilizable solvents include, for example, benzene, toluene, xylene, dioxane, 1,2-dimethoxyethane, tetrahydrofuran, and N,N-dimethylformamide. For the purpose 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.
This reaction may proceed at temperatures below room temperature. However, it is possible to heat the reaction mixture to a temperature in the range of from room temperature to the boiling point of the solvent to accelerate the reaction.
The 2-aminothiazoles represented by the general formula (II) as starting materials are known compounds and 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 present invention also provides as a process for preparing the novel compounds represented by the general formula (I) a method in which an N-thiazolylcarbamate represented by the general formula: ##STR7## wherein R.sup.1 and R.sup.2 have the same definitions as given above and R stands for a lower alkyl group, a benzyl group or a substituted or unsubstitu

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.
Sandler et al., Organic Functional Group Preparations, pp. 142-145 (1971).
Saikachi et al., Yakugakv Zasshi 88 (1189) 1968.

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