Yamanouchi Pharmaceutical Company Ltd.

Shinji Usuda

Toshinari Tamura

Shin-ichi Tsukamoto

Hitoshi Nagaoka

Masatomi Harada

Masuo Murakami

Kozo Takahashi

Shiro Tachikawa

Mutsuo Takashima

Sumio Iwanami

Yoshihisa Nozaki

Yasufumi Hirata

Masaaki Takeda

Osamu Hasegawa

Takashi Fujikura

Kunihiro Niigata

Tadao Kojima

Soichi Kagami

Yuji Kawashima

Hydrochloride salts of heterocyclic spiro compounds are provided and can be represented by the following general formula: ##STR1## wherein A represents piperidine or N alkyl piperidine or N alkylene attached to a non adjacent piperidine ring carbon, X is S or O, Y is carbonyl, thiocarbonyl, methylene, R.sup.5 methylene, ##STR2## alk in which R.sup.1 to R.sub.3,R.sub.6,R.sub.7 are H or alkyl, R.sub.4 is H, alkyl, COOH, or ester, or --C alkyl, R.sub.5 is halo, OH,SH, O alkyl, S alkyl, O acyl or S acyl, and Z, and Z.sub.2 are O or S. The above compounds act upon muscarinic acetylcholine receptors, thereby activating the acetylcholine nervous functions in the central nervous system.

Hydrochloride salts of heterocyclic spiro compounds

Heterocyclic spiro compounds represented by the following general formula and salts thereof: ##STR1## wherein A represents piperidine or N alkyl piperidine or N alkylene attached to a non adjacent piperidine ring carbon, X is S or O, Y is carbonyl, thiocarbonyl, methylene, R.sup.5 methylene, ##STR2## in which R.sup.1 to R.sub.3, R.sub.6, R.sub.7 are H or alkyl, R.sub.4 is H, alkyl, --COOH, or ester, or ##STR3## R.sub.5 is halo, OH, SH, O alkyl, S alkyl, O acyl or S acyl, and Z.sub.1 and Z.sub.2 are O or S. The above compounds act upon muscarinic acetylcholine receptors, thereby activating the acetylcholine nervous functions in the central nervous system.

Heterocyclic spiro compounds and methods for preparing the same

Heterocyclic spiro compounds represented by the following general formula and salts thereof ##STR1## The above compounds act upon muscarinic acetylcholine receptors, thereby activating the acetylcholine nervous functions in the central nervous system.

Heterocyclic spiro compounds represented by the following general formula and salts thereof: ##STR1## The above compounds act upon muscarinic acetylcholine receptors, thereby activating the acetylcholine nervous functions in the central nervous system.

Benzamide derivatives represented by the formula ##STR1## wherein X represents a lower alkoxy group; Y represents a mono- or di-lower alkylamino group; Z represents a halogen atom; R.sub.1 represents a lower alkyl group; and R.sub.2 represents a hydrogen atom or a halogen atom, and their pharmacologically acceptable nontoxic salts, which are strong central nervous system depressants, in particular strong antipsychotics.

Benzamide derivatives

##STR1## wherein R represents a hydrogen atom or a lower alkyl group; X represents a lower alkoxy group; Y represents a hydrogen atom, an amino group, or mono- or di-lower alkylamino group; Z represents a halogen atom, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, a sulfamoyl group, or a lower alkylsulfamoyl group; said Y and Z may combine to form --N.dbd.N--NH--; W represents a group shown by the formula ##STR2## (wherein A represents a phenyl group, a cyclohexyl group, a furyl group, or a pyridyl group; R.sub.1, R.sub.2, and R.sub.4, which may be the same or different, each represents a hydrogen atom, a lower alkyl group, or a phenyl group; R.sub.3 represents a lower alkyl group, a phenyl lower alkyl group, or a di-lower alkylamino lower alkyl group; R.sub.5, R.sub.6, and R.sub.7, which may be the same or different, each represents a hydrogen atom, a halogen atom, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, or a trifluoromethyl group; R.sub.8 represents a lower alkyl group; and n represents 1 or 2), a 1-ethyl-5-phenyl-2-pyrrolidinylmethyl group, a 1-ethyl-2-isoindolinylmethyl group, a 2-ethyl-1,2,3,4-tetrahydro-4-isoquinolyl group, a 2-(2-phenylpyrrolidino)ethyl group, a 2-(2-isoindolinyl)ethyl group, or a 2-(1,2,3,4-tetrahydro-2-isoquinolyl)ethyl group and the pharmaceutically acceptable nontoxic salts thereof. The compounds of this invention are strong central nervous system depressants, in particular strong antipsychotics.

N-1-Benzyl-3-pyrrolidinyl-4-dimethylamino benzamide derivatives

2-(Indenyloxymethyl) morpholine derivatives are disclosed. These derivatives are excellent in methamphetamine stereotyped increasing and antireserpine activities which are useful as antidepression agents.

2-(Indenyloxymethyl) morpholine derivatives

##STR1## wherein R represents a hydrogen atom or a lower alkyl group; X represents a lower alkoxy group; Y represents a hydrogen atom, an amino group, or a mono- or di-lower alkylamino group; Z represents a halogen atom, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, a sulfamoyl group, or a lower alkylsulfamoyl group; said Y and Z may combine to form --N.dbd.N--NH--; W represents a group shown by the formula ##STR2## (wherein A represents a phenyl group, a cyclohexyl group, a furyl group, or a pyridyl group; R.sub.1, R.sub.2, and R.sub.4, which may be the same or different, each represents a hydrogen atom, a lower alkyl group, or a phenyl group; R.sub.3 represents a lower alkyl group, a phenyl lower alkyl group, or a di-lower alkylamino lower alkyl group; R.sub.5, R.sub.6, and R.sub.7, which may be the same or different, each represents a hydrogen atom, a halogen atom, a lower alkoxy group, a lower alkylthio group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, or a trifluoromethyl group; R.sub.8 represents a lower alkyl group; and n represents 1 or 2), a 1-ethyl-5-phenyl-2-pyrrolidinylmethyl group, a 1-ethyl-2-isoindolinylmethyl group, a 2-ethyl-1,2,3,4-tetrahydro-4-isoquinolyl group, a 2-(2-phenylpyrrolidino)ethyl group, a 2-(2-isoindolinyl)ethyl group, or a 2-(1,2,3,4-tetrahydro-2-isoquinolyl)-ethyl group and the pharmaceutically acceptable nontoxic salts thereof. The compounds of this invention are strong central nervous system depressants, in particular strong antipsychotics.

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Ibaragi, Japan

Shinji Usuda