Sumitomo Chemical Company, Limited

Sumitomo Pharmaceuticals Company Limited

Kao Soap Company, Ltd.

Toshio Atsumi

Yoshiaki Takebayashi

Hisao Yamamoto

Yuzo Tarumi

Takao Kiyohara

Kenji Kobayashi

Tetsutaro Sanjiki

Noboru Yoshida

Masaru Fukui

Shigeho Inaba

Yuzuru Sanemitsu

Yoshihiro Tanaka

Keiichi Ono

Atsuyuki Kojima

Masato Mizutani

Masami Muraoka

Ikutaro Saji

Takao Okuda

Hideki Okajima

Masao Enomoto

Yoshihiro Komuro

Michio Kimura

Katsuaki Ichise

Takeshi Nakajima

Norboru Yoshida

Tomoharu Tanio

An N-substituted triazole compound of the formula: ##STR1## wherein Ph is a phenyl group or a phenyl group substituted with one or two halogen atoms, R.sup.1 is a C.sub.1 -C.sub.3 alkyl group, R.sup.2 is a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group, R.sup.3 is a C.sub.1 -C.sub.8 alkyl group, a C.sub.4 -C.sub.8 cycloalkylalkyl group or a C.sub.3 -C.sub.6 cycloalkyl group and n is 0, 1 or 2, or an acid addition salt thereof, which is useful as an antifungal agent.

N-substituted triazole derivatives and fungicidal use thereof

A novel 2-pyridylthiazolidin-4-one derivative represented by the general formula ##STR1## wherein Ar denotes an aryl group unsubstituted or substituted with a halogen atom or with a lower alkoxy group; X denotes a straight-chain or branched-chain lower alkylene group or a single bond; R denotes a hydrogen atom, lower alkyl, lower alkenyl, lower alkynyl, cycloalkyl, acyloxy, di(lower alkyl) amino, hydroxyl or aryl group, or denotes an aryl group substituted with a lower alkoxy group; and Py denotes a pyridyl group, and the acid addition salt thereof, which have an excellent platelet activating factor antagonsm.

Novel thiazolidin-4-one derivatives and acid addition salts therof

A novel cyanoimidazole nucleoside and derivative thereof, particularly 4-cyanoimidazolium-5-olate nucleoside and acyl derivatives thereof, and pharmaceutically acceptable salts thereof which are useful as antitumor agents and immunosuppressants, are prepared by dehydrating carboxamide derivatives of the formula: ##STR1## wherein R is an acyl group, and then, if desired, deacylating.

Cyanoimidazole nucleoside derivatives

There are provided compounds of the formula: ##STR1## wherein either R.sub.1 or R.sub.2 is a hydrogen atom, a hydroxy group, an acyloxy group, a phthalimido group or an acetamido group and the other is a hydrogen atom; either R.sub.3 or R.sub.4 is a hydroxy group or an acyloxy group and the other is a hydrogen atom; either R.sub.5 or R.sub.6 is a hydroxy group or an acyloxy group and the other is a hydrogen atom; either R.sub.7 or R.sub.8 is a hydrogen atom, a methyl group, a hydroxymethyl group, an acyloxymethyl group, an alkoxycarbonyl group, a group of the formula: ##STR2## (wherein X.sub.1 and X.sub.2 are a hydrogen atom or a lower alkyl group), or a carboxyl group and the other is a hydrogen atom; either R.sub.11 or R.sub.12 is a hydrogen atom, a hydroxy group or an acyloxy group and the other is a hydrogen atom; either R.sub.13 or R.sub.14 is a hydroxy group or an acyloxy group and the other is a hydrogen atom; either R.sub.15 or R.sub.16 is a methyl group, a hydroxymethyl group or an acyloxymethyl group and the other is a hydrogen atom; and a process for producing them. These compounds are useful as antitumor agents.

4-Carbamoylimidazolium-5-olate derivatives

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 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

A new class of 4-homoisotwistane derivatives of the formula, ##STR1## wherein R.sub.1 is a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group, and R.sub.2 is an alkyl group, a phenyl group which may be either unsubstituted or substituted with a C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, nitro group or a halogen atom (hereinafter referred to as 'an optionally substituted phenyl group'), a group of the formula, --A--OH in which A is a C.sub.1 -C.sub.3 alkylene group; a group of the formula, --A--B in which A is as defined as above and B is a halogen atom, or a group of the formula, ##STR2## in which A is as defined above and R.sub.3 and R.sub.4 are independently a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group or R.sub.3 and R.sub.4 may, when taken together with the adjacent nitrogen atom to which R.sub.3 and R.sub.4 are linked, form pyrrolidine, piperidine, morpholine, phthalimide or piperazine, which have been found to possess potent antiviral activity, are prepared, for example by reacting a compound of the formula, ##STR3## wherein R.sub.1 is as defined above and X is halogen, with a compound of the formula,

4-Homoisotwistane derivatives

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.

Antitumor and immunosuppressive 4-carbamoyl imidazolium-5-olate

Novel 3-amino-4-homoisotwistane derivatives of the formula, ##STR1## wherein R.sub.1 is a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group or a C.sub.3 -C.sub.5 alkenyl group, and R.sub.2 is a C.sub.1 -C.sub.4 alkyl group or a C.sub.3 -C.sub.5 alkenyl group, or non-toxic pharmaceutically acceptable salts thereof, which are very valuable as medicines for the treatment of virus-caused diseases and as antiviral agents for animals and useful for the treatment of parkinsonean disease.

3-Amino-4-homoisotwistane derivatives

There are provided compounds of the formula: ##STR1## wherein R is an adamantyl group, or a phenyl group unsubstituted or substituted with a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a halogen atom, a nitro group, a cyano group, a methylenedioxy group or an acetamido group, useful as anti-transplanted-tumor agents and immunosuppressants.

5-Carbamoyl imidazoles

Compounds of the formula, ##STR1## wherein R is C.sub.2 -C.sub.17 alkyl group, C.sub.3 -C.sub.7 cycloalkyl group, 1-adamantyl group, pyridyl group, pyridine N-oxide, diphenylmethyl group, benzyl group which may or may not be substituted with nitro group, halogen atom, C.sub.1 -C.sub.3 alkyl group or C.sub.1 -C.sub.3 alkoxy group, or phenyl group which may or may not be substituted with nitro group, halogen atom, hydroxy group, C.sub.1 -C.sub.3 alkyl group, C.sub.1 -C.sub.3 alkoxy group, carboxy group, C.sub.2 -C.sub.4 alkoxycarbonyl group, phenoxycarbonyl group, carbamoyl group, N-phenylcarbamoyl group, N-adamantylcarbamoyl group, benzoylamino group, trifluoromethyl group, C.sub.2 -C.sub.4 alkanoyloxy group, 1-adamantoyloxy group or benzoyloxy group and salts thereof have an anticancer activity and an immunostimulating activity.

2-Substituted 5-hydroxy-1H-imidazole-4-carboxamide derivatives and use

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

N-Substituted imidazolecarboxamide compounds represented by the formula; ##STR1## wherein R.sub.1 is hydrogen atom, lower alkyl, lower alkenyl, aralkyl, R.sub.2 is hydrogen atom, lower alkyl, lower alkenyl, aralkyl, 1-adamantyl, R.sub.3 is hydrogen atom, lower alkyl, aralkyl; with the proviso that one of R.sub.1, R.sub.2 or R.sub.3 is not hydrogen when the other two are hydrogen, are produced by reacting aminomalonamide derivative with orthoformate derivative in high yields. The compounds (I) exhibit anti-tumor activity against experimental tumors such as Sarcoma 180 in mice.

N-Substituted imidazolecarboxamide derivatives

An analgesic composition comprising an analgesically effective amount of at least one 6,7-benzomorphan derivative of the formula: ##SPC1## Wherein R is a hydrogen atom, a hydroxyl group, a C.sup.1 - C.sup.3 alkoxy group or a C.sup.1 - C.sup.8 alkanoyloxy group; R.sub.1 is a hydrogen atom, a C.sup.1 - C.sup.5 alkyl group, a phenyl group, a halophenyl group, an alkylphenyl group wherein the alkyl moiety has 1 to 3 carbon atoms, an alkoxyphenyl group wherein the alkoxy moiety has 1 to 3 carbon atoms, a trifluoromethylphenyl group, an alkylthiophenyl group wherein the alkylthio moiety has 1 to 3 carbon atoms or a group of the formula (C.sub.m H.sub.2m.sub.-p.sub.+1) - (R.sub.9).sub.p wherein m is an integer of 1 - 6, p is an integer of 1 - 2 and R.sub.9 is a C.sup.1 - C.sup.3 alkoxy group; R.sub. 2 is a hydrogen atom or a C.sup.1 - C.sup.3 alkyl group; R.sub.3 is a hydrogen atom, a C.sup.1 - C.sup.3 alkyl group, a phenyl group or an alkoxyphenyl group wherein the alkoxy moiety has 1 to 3 carbon atoms; R.sub.4 is a hydrogen atom or a hydroxyl group, or R.sub.3 and R.sub.4 may form a C.sup.1 - C.sup.3 alkylidene group or a carbonyl group together with a carbon atom to which these substituents are bonded; R.sub.5 is a hydrogen atom or C.sup.1 - C.sup.3 alkyl group; R.sub.6 is a hydrogen atom or a methyl group; R.sub.7 and R.sub.8 are independently a hydrogen atom or a C.sup.1 - C.sup.2 alkyl group; and n is an integer of 0 - 2; or an acid addition salt thereof, and a pharmaceutically acceptable carrier or diluent, is disclosed.

Analgesic compositions containing 2-cyanoalkylbenzomorphan derivatives

A novel process for preparing 2-benzoylalkylbenzomorphan derivatives and salts thereof, represented by the formula ##SPC1## Wherein n, R, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined in the specification. The process comprises reacting a pyridinium derivative of the formula, ##SPC2## Wherein X is a halogen atom and Y' is an ethylenedioxy group; with a Grignard reagent of the formula, ##SPC3## Wherein R' is a hydrogen atom or a C.sub.1 -C.sub.3 alkoxy group and Z is a halogen atom, to yield a 1,2-dihydropyridine derivative of the formula; ##SPC4## And then reducing the said 1,2-dihydropyridine derivative to give a 1,2,5,6-tetrahydropyridine derivative of the formula, ##SPC5## Wherein Y is an oxygen atom or an ethylenedioxy group, and further cyclizing the obtained 1,2,5,6-tetrahydropyridine derivative.

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Kawanishi, Japan

Toshio Atsumi