Suntory Limited

Sanwa Kagaku Kenkyusho Co., Ltd.

Suntori Limited

Seiji Miyano

Kunihiro Sumoto

Fumio Satoh

Toshio Tatsuoka

Kenji Suzuki

Masayasu Kurono

Kayoko Imao

Fumio Sato

Minoru Morita

Takashi Ito

Yasuaki Kondo

Kenji Miura

Ryoichi Unno

Toshinao Usui

Yukiharu Matsumoto

Hidetsura Cho

Takafumi Ishihara

Takuji Yamaguchi

Masato Fukushima

Hiromoto Kimura

Mitsuru Oka

Tsunemasa Suzuki

Kayoko Nomura

Noboru Kuboyama

Motohide Hayashi

Shinichi Ikeda

Yoshihiro Kumagai

A compound having the formula (I): ##STR1## wherein A is --CH.sub.2 --, --O--, or --S--; R.sup.1 is CH.sub.3 or OCH.sub.3 ; R.sup.2 is hydroxy or carboxy which may be optionally esterized or amidated; R.sup.3 is H or a lower alkyl; and n is 0 or an integer of 1 to 6 or a pharmaceutically acceptable salt thereof.

Compound effective as cerebral insufficiency improver

A compound having the formula (I): ##STR1## wherein A is --CH.sub.2 --, R.sup.1 is CH.sub.3 or OCH.sub.3 ; R.sup.2 is hydroxy or carboxy, carboxylic acid or carboxylic acid ester group; R.sup.3 is H or a lower alkyl; and n is 0 or an integer of 1 to 6 or a pharmaceutically acceptable salt thereof.

1. A compound having the formula (I): ##STR1## wherein A is --CH.sub.2 --, --O--, or --S--; R.sup.1 is CH.sub.3 or OCH.sub.3 ; R.sup.2 is hydroxy of carboxy which may be optionally esterized or amidated; R.sup.3 is H or a lower alkyl; and n is 0 or an integer of 1 to 6 or a pharmaceutically acceptable sale thereof.

Compounds effective as cerebral schemia treating agents

A hydroquinonylphenyl butyric acid amide derivative having the formula (I): ##STR1## wherein R.sup.1 represents an aromatic or heterocyclic group which may be substituted, R.sup.2 represents a hydrogen atom, a lower alkylcarbonyl group, an aromatic carbonyl or heterocyclic carbonyl group which may be substituted, and X represents an oxygen atom or sulfur atom or a pharmaceutically acceptable salt thereof, which has a cerebral insufficiency improving activity.

Hydroquinonlyphenyl butyric acid amide derivative

2-phenylbenzoxepin derivatives having a hypoglycemic activity, hypotensive activity, and platelet coagulation inhibiting activity, a process for production of the derivatives, and pharmaceutical compositions containing the derivatives.

2-phenylbenzoxepin derivative

A novel pyrrolizidine compound of the formula ##STR1## wherein R.sup.1 is an alkyl group of 1 to 4 carbon atoms or a phenyl group; and R.sup.2 and R.sup.3 are such that at least one of them is an alkyl group of 1 to 4 carbon atoms and the other, if not alkyl, being a hydrogen atom is produced by reacting .DELTA..sup.4(8) -dehydropyrrolizidine with a substituted malonic acid and the thus formed 2-substituted-8-pyrrolizidineacetic acid with a substituted aniline. The products are subjected to optical resolution and are potentantiarrhythmic agents.

Pyrrolizidine compounds, and their use as antiarrhythmic agents

A derivative of benzoquinonylphenyl alkanoic acid amide having the formula: ##STR1## wherein X represents an oxygen atom, sulfur atom, or methylated nitrogen atom, Me represents methyl, and n is 2 or 3. This derivative is effective as a cerebral insufficiency improver.

Derivative of benzoquinonylphenyl alkanoic acid amide

Novel pyrrolizidine compounds represented by the formula ##STR1## wherein R is a radical of ##STR2## R.sup.1 is hydrogen, halogen, alkyl group, alkoxy group, alkanoyl group, trifluoromethyl radical, trimethylsilyl radical or ##STR3## R.sup.2 and R.sup.3 are same or different and are hydrogen or alkyl group, respectively, R.sup.4 is hydrogen, halogen, alkyl group or alkoxy group and m is an integer of 0 to 5, salts thereof, a process for the preparation of same as well as a pharmaceutical agent comprising same.

Pyrrolizidine compounds, salts thereof, process for the preparation of

The present invention relates to a novel oxabicycloheptane derivative of the following formula and a pharmaceutically acceptable salt thereof: ##STR1## where D is a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group, an arylalkoxy group, an acyloxy group, a dialkylcarbamoyloxy group or an amidoalkyloxy group; B is a substituted or unsubstituted phenyl, thienyl or furyl group; A is the group ##STR2## (where l is 0 or 1; m and n are each 1 or more, provided that m+n is an interger of 2-8; R.sup.1 is an alkylamino group, a dialkylamino group, an arylalkylamino group, a morpholino group, a thiomorpholino group, a 1-pyrrolidinyl group, a piperidino group, an N-alkylpiperazinyl group, an N-hydroxyalkylpiperazinyl or a pyrrolizidinyl group; and R.sup.2 is a lower alkyl group or a hydroxl group), or the group ##STR3## (where l, m, n, R.sup.1 and R.sup.2 are each the same as defined above), or the group ##STR4## (where R.sup.3 and R.sup.4 which may be the same or different each represents a hydrogen atom, a lower alkyl group, an alkoxycarbonyl group or an acyl group), or the group ##STR5## (where m, l, n, R.sup.1 and R.sup.2 are each the same as defined above). The oxabicycloheptane derivative having the formula defined above and pharmaceutically acceptable salts thereof are effective in ameliorating or eliminating the symptoms that appear either as a result of organic disorders in the brain or on account of pathergasia. These compouds also have antidepressant effects and the useful as psychopharmaceuticals.

Oxabicycloheptane derivatives

Novel 2-oxopyrrolidine compounds represented by the formula ##STR1## wherein R.sup.1 and R.sup.2 are hydrogen or alkyl group, respectively, A is alkylene group or phenyl substituted alkylene group, and B is alkylene group, or a salt thereof, a process for the preparation thereof, and a pharmaceutical agent comprising the compound or salt as an effective component.

Novel 2-oxopyrrolidine compounds, salts thereof process for the

Novel 8-substituted pyrrolizidines and quaternary ammonium salts thereof of the formula ##STR1## wherein R is a C.sub.4`-C.sub.10 alkyl, aralkyl or aryl group; a lower alkoxycarbonyl or a lower alkoxycarbonylmethyl group; a lower aliphatic carboxyl group amidated with pyridinylamine, aniline, cyclohexylamine, phenylbenzylamine or methoxyphenylbenzylamine; a lower hydroxyalkyl group which has one or two phenyl, a trihalomethylphenyl or a halophenyl group; a lower alkyl group which has a hydroxyl group esterified with acetic, benzoic, cinnamic, xanthene-carboxylic or methoxybenzoic acid, or etherified with a C.sub.2 -C.sub.13 alcohol; a lower alkyl group having a primary amino, a lower alkylamino, guanidino, benzylamino, hydroxylbenzylamino, methoxybenzylamino, aminobenzylamino, acetamino, benzoylamino, hydroxybenzoylamino, methoxybenzoylamino, or aminobenzoylamino group; or a lower alkyl group bearing benzoyl, methoxybenzoyl or halobenzoyl group; Y stands for an alkyl group quaternizing the nitrogen of the pyrrolizidine nucleus, which may optionally be substituted with halogen, an aryl, phenacyl or phenylphenacyl group; X stands for halogen. These compounds have various pharmacological activities such as atropine-like activity, papaverine-like activity, neuromuscular-blocking activity, etc.

8-substituted pyrrolizidine and quaternary ammonium salts thereof

A novel 1-substituted pyrrolizidine derivative having the formula: ##STR1## (wherein R.sup.1 is hydrogen or a lower alkyl group; R.sup.2 is hydrogen, a lower alkyl or lower alkoxy group, or a halogen; R.sup.3 is hydrogen, a lower alkyl, lower alkoxy or amino group, or a halogen), which can be produced by reacting 1-chlorocarbonyl (or alkoxycarbonyl)pyrrolizidine with a corresponding substituted aniline (or an alkali metal salt thereof). The pyrrolizidine derivative has antiarrhythmic activity.

1-substituted pyrrolizidine derivatives and antiarrhythmic use thereof

An 8-substituted pyrrolizidine derivative representable by the formula: ##STR1## (wherein R.sup.1 stands for hydrogen or a lower alkyl group, R.sup.2 stands for hydrogen, a lower alkyl group, a lower alkoxy group or halogen, and R.sup.3 stand for a lower alkyl group, a lower alkoxy group, amino group or halogen), which can be produced by reacting a corresponding substituted anilin with 8-halocarbonylmethyl pyrrolizidine or reacting an alkali metal salt of the corresponding substituted anilin with 8-alcoxycarbonylmethyl pyrrolizidine. The derivative is useful as an antiarrhythmic agent.

Growing community of inventors

Fukuoka, Japan

Seiji Miyano