Sumitomo Chemical Company, Limited

Sumitomo Pharmaceuticals Company Limited

Sumitono Pharmaceutical Company, Limited

Isamu Maruyama

Hisao Yamamoto

Kikuo Sasajima

Masaru Nakao

Shigeho Inaba

Shigenari Katayama

Kikuo Ishizumi

Junki Katsube

Keiichi Ono

Michihiro Yamamoto

Kazuo Mori

Toshiyuki Hirohashi

Mitsuhiro Akatsu

Yoshiharu Kume

Takahiro Izumi

Masaharu Takayama

Fujio Antoku

Yoshihiro Tanaka

Naohito Ohashi

Atsuyuki Kojima

Shunji Aono

Shoji Nagata

Tsuyoshi Kobayashi

Hiroyuki Mizote

Yoshinori Takashima

Tadashi Okamoto

Shigeru Sakai

Sumio Kitagawa

Izumi Yanagihara

Atuyuki Kojima

A succinimide derivative of the formula: ##STR1## wherein R is a pyridyl or pyrimidinyl group substituted with at least one member selected from the group consisting of halogen, lower alkyl, lower alkoxy, cyano, benzyloxy, hydroxyl and amino, and n is an integer of 1 or 2, or a pharmaceutically acceptable acid addition salt thereof. The succinimide derivatives are useful as an anti-anxiety drugs.

Succinimide derivatives, and their production and use

A compound of the formula: ##STR1## wherein A is a carbonyl group or a sulfonyl group;

Imide derivatives and compositions for use as antipsychotic agents

A process for the optical resolution of DL-.alpha.-methyl-.beta.-acylthiopropionic acid, which comprises contacting a DL-.alpha.-methyl-.beta.-acylthiopropionic acid of the formula, ##STR1## wherein R.sub.1 is acetyl or benzoyl which may be substituted with a C.sub.1 -C.sub.3 alkyl or a halogen atom, with an optically active amine of the formula, ##STR2## wherein R.sub.2 is methyl, isopropyl or isobutyl, to form diastereoisomeric salts, subjecting the formed diastereoisomeric salts to the fractional crystallization in a solvent to separate the D-acid salt from the L-acid salt, and then contacting the individual diastereoisomeric salt with acid to give D-.alpha.-methyl-.beta.-acylthiopropionic acid and L-.alpha.-methyl-.beta.-acylthiopropionic acid, the former being useful as an intermediate for synthesizing captopril useful as an antihypertensive agent.

Optical resolution of acylthiopropionic acid

Quinazoline compounds of the formula: ##STR1## wherein A is ##STR2## wherein n is an integer of 1 or 2, or ##STR3## wherein X is O or CH.sub.2, and n and m are independently an integer of 1 or 2, and its non-toxic pharmaceutically acceptable salts, having an excellent antihypertensive activity without causing adverse effects such as orthostatic hypotension.

Antihypertensive quinazoline compounds

Novel .gamma.-piperidinobutyrophenone derivatives of the formula, ##STR1## wherein R.sup.1 is halogen, amino, alkanoylamino, alkylamino or N-(alkanoyl)alkylamino;

.gamma.-Piperidinobutyrophenones

Novel N-substituted heterocyclic derivatives represented by the formula, ##STR1## wherein R is hydrogen or lower alkanoyl; R.sub.1 is hydrogen, lower alkyl, lower alkoxy, halogen, nitro, trifluoromethyl, amino or N-lower alkanoylamino; R.sub.2 is hydrogen, halogen, amino or N-lower alkanoylamino; W is oxygen, sulfur, sulfinyl or sulfonyl; and Y is ##STR2## (wherein R.sub.3 is hydrogen, lower alkyl or lower alkanoyl; and R.sub.4 is hydrogen, halogen or lower alkyl), and pharmaceutically acceptable salts thereof, which have excellent anti-inflammatory, analgesic, sedative, anti-convulsive or anti-hypertensive activities.

N-substituted heterocyclic derivatives and preparation thereof

Novel 1-substituted benzodiazepine derivatives and salt thereof having the formula, ##STR1## wherein R.sub.1 is a hydrogen atom, a halogen atom, a nitro group, a cyano group, a lower alkoxy group or a trifluoromethyl group; R.sub.2 is a pyridyl group or a group of the formula ##STR2## wherein R.sub.5 and R.sub.6 represent individually a hydrogen atom, a halogen atom, a lower alkyl group or a trifluoromethyl group); R.sub.3 is a hydrogen atom or a lower alkyl group; R.sub.4 is a lower alkyl, cycloalkyl, cycloalkylalkyl, aryl or aralkyl group; m is 1 or 2; and n is an integer of 1 to 4, and a process for preparation thereof and pharmaceutical use of the same. The benzodiazepine derivatives are effective as tranquillizers, muscle-relaxants and hypnotics.

Benzodiazepine derivatives

Acylhydrazone compounds having excellent pyschotropic activity which are represented by the formula: ##STR1## wherein Z is selected from the groups having the formulas: ##STR2## wherein n is an integer of from 0 to 2 and R.sup.1 -R.sup.12 are as defined hereinbelow.

Acylhydrazones and anti-psychotic compositions thereof

Novel tricyclic compounds of the formula: ##STR1## wherein A is --CH.sub.2 --CH.sub.2 --, --CH=CH-- or ##STR2## X is hydrogen, halogen, nitro, trifluoromethyl, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy, R.sub.1 and R.sub.2 are each hydrogen or C.sub.1 -C.sub.4 alkyl and R.sub.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.5 alkenyl, C.sub.3 -C.sub.5 alkynyl, C.sub.3 -C.sub.6 cycloalkyl (C.sub.1 -C.sub.3)alkyl, ar(C.sub.1 -C.sub.3)alkyl, polyhalo(C.sub.1 -C.sub.2)alkyl, C.sub.1 -C.sub.4 alkoxy(C.sub.1 -C.sub.3)alkyl or hydroxy(C.sub.1 -C.sub.3)alkyl, and non-toxic salts thereof which are useful as antidepressants and can be prepared by reduction of a compound of the formula: ##STR3## wherein A, X, R.sub.1, R.sub.2 and R.sub.3 are each as defined above.

2-Morpholinyl tricyclic dibenzazepine compounds

An N-(.omega.-amino)alkylaniline derivative of the formula: ##STR1## and its pharmaceutically acceptable salts, which are useful as neuroleptic agents and can be prepared by reacting a compound of the formula: ##STR2## with a compound of the formula:

N-(.omega.-Amino)alkylaniline derivatives

Novel olefinic aryl ketone compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen, halogen, C.sub.1-4 alkyl, or C.sub.1-4 alkoxy, R.sup.2 is hydrogen or halogen, and X is a group of the formula: ##STR2## and their non-toxic salts, which possess various useful pharmacological activities and can be produced by reaction of an acetylenic alcohol of the formula: ##STR3## wherein R.sup.1 and R.sup.2 are each as defined above with formaldehyde and an piperidine compound of the formula: , or its non-toxic salt; reduction of the resultant acetylenic aryl alcohol; and oxidation of the resultant olefinic aryl alcohol.

Aryl ketones and production thereof

Novel olefinic aryl ketone compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen, halogen, C.sub.1.sub.-4 alkyl, or C.sub.1.sub.-4 alkoxy, R.sup.2 is hydrogen or halogen, and R.sup.3 and R.sup.4 are each hydrogen, halogen, C.sub.1.sub.-4 alkyl or trifluoromethyl, and their non-toxic salts, which possess various useful pharmacological activities and can be produced by reaction of an acetylenic alcohol of the formula: ##STR2## wherein R.sup.1 and R.sup.2 are each as defined above, with formaldehyde and an amine of the formula: ##STR3## wherein R.sup.3 and R.sup.4 are each as defined above; reduction of the resultant acetylenic aryl alcohol; and oxidation of the resultant olefinic aryl alcohol.

Novel 1-substituted benzodiazepine derivatives and salt thereof having the formula, ##STR1## wherein R.sub.1 is a hydrogen atom, a halogen atom, a nitro group, a cyano group, a lower alkoxy group or a trifluoromethyl group; R.sub.2 is a pyridyl group or a group of the formula ##STR2## wherein R.sub.5 and R.sub.6 represent individually a hydrogen atom, a halogen atom, a lower alkyl group or a trifluoromethyl group); R.sub.3 is a hydrogen atom or a lower alkyl group; R.sub.4 is a lower alkyl, cycloalkyl, cycloalkylalkyl, aryl or aralkyl group; m is 1 or 2; and n is an integer of 1 to 4, and a process for preparation thereof and pharmaceutical use of the same.

Benzodiazepinones

A phenoxyalkylamine derivative of the formula: ##STR1## and its pharmaceutically acceptable salts, which are useful as neuroleptic agents and a process for their preparation by reacting a compound of the formula: ##STR2## with a compound of the formula: ##STR3## wherein R.sub.1 and R.sub.2 are each hydrogen, halogen, C.sub.1 -C.sub.7 alkyl or C.sub.1 -C.sub.7 alkoxy, X is oxygen, sulfur, sulfinyl or NR (in which R is hydrogen or C.sub.1 -C.sub.7 alkyl), m and n are each an integer of 2, 3 or 4, and Y and Y' are each amino or halogen but they are different from each other.

Phenoxyalkylamine derivatives and preparation thereof

Novel butyrophenone derivatives of the formula: ##STR1## wherein R.sub.1 represents a hydroxyl group or ##STR2## (wherein R.sub.6 and R.sub.7 are each a hydrogen atom or a lower alkyl group or, when taken together with the adjacent nitrogen atom, may form a heterocyclic group), R.sub.2 represents an optionally substituted phenyl group or ##STR3## (wherein R.sub.8 and R.sub.9 are each a hydrogen atom or a lower alkyl group or, when taken together with the adjacent nitrogen atom, may form a heterocyclic group), R.sub.4 represents a hydrogen atom, a lower alkyl group or an optionally substituted phenyl group, R.sub.5 represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group or a trifluoromethyl group, R.sub.10 represents a hydrogen atom or an acyl group represented by R.sub.3 CO- (wherein R.sub.3 is a hydrogen atom, a lower alkyl group or an optionally substituted phenyl group) and Z represents two hydrogen atoms or an oxygen atom, provided that when Z is an oxygen atom and R.sub.1 is ##STR4## R.sub.10 can not be a hydrogen atom, and their acid addition salts, which are useful as central and autonomic nervous system depressants.

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Minoo, Japan

Isamu Maruyama