Sumitomo Chemical Company, Limited

Takao Kiyohara

Toshio Atsumi

Tetsutaro Sanjiki

Shigeo Ogino

Noboru Yoshida

Yoshiaki Takebayashi

Yuzo Tarumi

Akinori Seta

There are provided compounds of the formula: ##STR1## wherein R is a mono-substituted benzoyl group wherein the substituent is a phenyl group, an alkanoyl group, a formyl group, a halogeno-alkyl group, an aralkyloxy group, a phenoxy group, an alkoxycarbonyl group, an aralkyloxycarbonyl group, an alkanoyloxy group, a benzoyl group, a carboxyl group, a hydroxy group, a group of the formula: ##STR2## (wherein X.sub.1 and X.sub.2 are a hydrogen atom or a lower alkyl group), an aralkyloxycarbonylamino group, a lower alkoxycarbonylamino group, a carboxyamino group or a carbamoyl group; a cinnamoyl group which may be substituted at the .alpha. position or the phenyl ring with an alkyl group, an alkoxy group, an aryl group, a nitro group, a methylenedioxy group, a formyl group, a halogeno-alkyl group, a halogen atom, a hydroxy group, a carboxyl group, an amino group or a cyano group; or a benzoyl group substituted with from two to five of the same or different substituents selected from the group consisting of alkyl groups, alkoxy groups, aralkyloxy groups, nitro group, halogen atoms, hydroxy group, alkanoyloxy groups, formyl group, carboxyl group, alkylthio groups, alkylsulfonyl groups, groups of the formula: ##STR3## (wherein X.sub.1 and X.sub.2 are a hydrogen atom or a lower alkyl group), sulfo group and sulfamoyl group; or its non-toxic salt, and a process for producing them. The compounds are useful as antitumor agents and immunosuppressants.

Antitumor and immunosuppressive 4-carbamoylimidazolium-5-olate

There are provided compounds of the formula: ##STR1## wherein R is an alkyl sulfonyl group or a benzenesulfonyl group which may be substituted with a lower alkyl group, a lower alkoxy group, a nitro group or a halogen atom, and a process producing them, useful as antitumor agents and immunosuppressants.

Antitumor and immunosuppressive 4-carbamoyl imidazolium-5-olate

There are provided compounds of the formula: ##STR1## wherein R is an adamantoyl group substituted with a lower alkyl group, a lower alkoxy group, a hydroxy group, a lower alkanoyloxy group, an aroyloxy group, a halogen atom, an acetamido group, a nitro group, an azide group, a trifluoromethyl group or a phenyl group which may be substituted with a nitro group, a halogen atom, a lower alkyl group or a lower alkoxy group and a process producing them. These compounds are useful as antitumor agents and immunosuppressants.

Antitumor and immunosuppresive 4-carbamoyl imidazolium-5-olate

There are provided compounds of the formula: ##STR1## wherein R is a heteroaroyl group containing a nitrogen, sulfur or oxygen atom which may be substituted with a lower alkyl group, an aralkyl group, an acyl group or a halogen atom; or a cycloalkanoyl group which may be substituted with a lower alkyl group, a lower alkenyl group, a halogen atom, a halogeno-lower alkenyl group, a phenyl group, a halogenophenyl group, a lower alkoxyphenyl group, a lower alkylphenyl group, a formyl group, a hydroxy group, an amino group, a carboxyl group, an aminomethyl group or an oxo group, its non toxic salt and a process for producing them. These compounds are useful as antitumor agents and immunosuppressants.

Imidazole derivatives represented by the formula: ##STR1## wherein Y is a hydroxy group, a lower alkoxy group or an amino group, and their non-toxic, pharmaceutically acceptable salts, which have a potent immunostimulating activity and are useful for the immunostimulatory therapy of various diseases, and their preparation and use.

Imidazole acetic acid derivatives

Antitumor substances are prepared by culturing a microorganism, Acinetobacter calcoaceticus. The antitumor substances have potent antitumor activity as well as immunostimulatory activity and are effective in a very small amount without harmful effects such as toxicity.

Novel anti-tumor substance and preparation thereof

4-Carbamoyl-5-hydroxyimidazole representable by the following formula: ##STR1## and pharmaceutically acceptable salts thereof have been found to be useful as therapeutic agents for the treatment of rheumatism and nephritis.

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Takarazuka, Japan

Takao Kiyohara