Suntory Limited

Fumio Sato

Kunihiro Sumoto

Seiji Miyano

Minoru Morita

Hidetsura Cho

Takafumi Ishihara

Kazuo Aisaka

N-substituted 3,4-dihydropyrimidine derivatives of the formula: ##STR1## wherein X.sup.1, X.sup.2 and X.sup.3 are the same or different and are hydrogen, nitro, halogen, cyano, trifluoromethyl, methylthio or lower alkoxy;

2,6-Dimethyl-3N,5-disubstituted-4-(substituted

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

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.

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Nagaokakyo, Japan

Fumio Sato