2-Thiazolamine derivatives, process for preparing same, and phar

Details 2-Thiazolamine derivatives, process for preparing same, and phar 2-Thiazolamine derivatives, process for preparing same, and phar

1982-10-22

1984-09-25

Gerstl, Robert

Drug, bio-affecting and body treating compositions

Antigen, epitope, or other immunospecific immunoeffector

Parasitic organism or component thereof or substance...

548195, 548196, C07D27748, C07D41712, A61K 31425

Patent

active

044735774

DESCRIPTION:

BRIEF SUMMARY
DESCRIPTION

1. Technical Field
This invention relates to novel 2-thiazolamine derivatives, a process for preparing the same, and pharmaceutical compositions comprising the same. More particularly, it relates to novel 2-thiazolamine derivatives which have such immunomodulatory activity as to make them effective against immune diseases (e.g., rheumatoid arthritis) and also useful in the treatment of viral diseases and in the immunotherapy of cancer and, moreover, are very desirable for therapeutic purposes because of their low toxicity, a process for preparing the same, and pharmaceutical compositions comprising the same.
2. Background Art
Conventionally, a large number of steroidal and non-steroidal anti-inflammatory agents have been used in the clinical treatment of autoimmune diseases such as rheumatism and the like. However, these numerous drugs are still not entirely satisfactory, judging from their pharmacological actions, side effects, toxicity, and the like.


DISCLOSURE OF THE INVENTION

It is an object of the present invention to provide a novel 2-thiazolamine derivative which exerts a specific effect on the cells participating in immune responses and thereby serves to modify the immune responses of the host, and a process for preparing this compound.
It is another object of the present invention to provide a pharmaceutical composition characterized by immunomodulatory activity and low toxicity.
In accordance with one feature of the present invention, there is provided a 2-thiazolamine derivative having the general formula ##STR4## where R.sub.1 and R.sub.2 independently represent lower alkyl radicals having 1 to 4 carbon atoms and X represents a lower alkyl radical, a lower alkoxy radical, a lower alkoxycarbonyl radical, a halogenalkoxy radical, a radical of the formula ##STR5## or a radical of the formula ##STR6##
In accordance with another feature of the present invention, compounds of the general formula (1) can be prepared by reacting a 2-(2-aminothiazol-4-yl)-2-syn-oxyiminoacetic acid ester of the general formula ##STR7## where R.sub.1 and R.sub.2 are as defined for the general formula (1), with a compound of the general formula represents a halogen atom, a lower alkyl radical, a lower alkoxy radical, a halogenoalkoxy radical, or a radical of the formula --CO--A.
In accordance with still another feature of the present invention, a pharmaceutical composition having immunomodulatory activity comprises a compound of the general formula (1) and a pharmaceutically acceptable carrier.


BEST MODE FOR CARRYING OUT THE INVENTION

Specific examples of the 2-thiazolamine derivatives represented by the general formula (1) include 2-[(2-acetylamino)thiazol-4-yl]-2-syn-methoxyiminoacetic acid methyl ester, 2-[(2-propionylamino)thiazol-4-yl]-2-syn-methoxyiminoacetic acid methyl ester, 2-[(2-propionylamino)thiazol-4-yl]-2-syn-methoxyiminoacetic acid ethyl ester, 2-[(2-propionylamino)thiazol-4-yl]-2-syn-ethoxyiminoacetic acid ethyl ester, 2-[(2-propionylamino)thiazol-4-yl]-2-syn-ethoxyiminoacetic acid methyl ester, 2-[(2-n-butyrylamino) thiazol-4-yl]-2-syn-methoxyiminoacetic acid methyl ester, 2-[(2-isobutyrylamino)thiazol-4-yl]-2-syn-methoxyiminoacetic acid methyl ester, 2-[(2-n-pentanoylamino)thiazol-4-yl]-2-syn-methoxyiminoacetic acid methyl ester, 2-[2-(.alpha.-methylbutyryl)amino)thiazol-4-yl]-2-syn-methoxyiminoacetic acid methyl ester, 2-[(2-(.beta.-methylbutyryl)amino)thiazol-4-yl]-2-syn-methoxyiminoacetic acid methyl ester, 2-[(2-(.alpha.,.alpha.-dimethylpropionyl)amino)thiazol-4-yl]-2-syn-methoxy iminoacetic acid methyl ester, 2-[(2-methoxycarbonylamino)thiazol-4-yl]-2-syn-methoxyiminoacetic acid methyl ester, 2-[(2-ethoxycarbonylamino)thiazol-4-yl]- 2-syn-methoxyiminoacetic acid methyl ester, 2-[(2-.beta.,.beta.,.beta.-trichloroethoxycarbonylamino)thiazol-4-yl]-2-sy n-methoxyiminoacetic acid methyl ester, 2-[(2-.beta.-chloroethoxycarbonylamino)thiazol-4-yl]-2-syn-methoxyiminoace tic acid methyl ester, 2-[(2-.beta.-bromoethoxycarbonylamino)thiazol-4-yl]-2-syn-methoxyiminoacet ic acid methyl ester,

REFERENCES:
patent: 4203899 (1980-03-01), Ochiai
patent: 4278793 (1981-07-01), Durckheimer et al.
patent: 4279818 (1981-07-01), Takaya
patent: 4304720 (1981-12-01), Takaya

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