Yoshitomi Pharmaceutical Industries, Ltd.

Michio Nakanishi

Takanori Oe

Mineo Tsuruda

Tetsuya Tahara

Kazuhiko Araki

Masami Shiroki

Tohru Nakao

Kazuhiro Goto

Tomio Muro

Hiroshi Yasuda

Toshihiro Kobayakawa

Kiyoshi Ogawa

Hiroshi Yuki

Pharmaceutical compositions containing 2-amino-6-benzyl-3-ethoxycarbonyl-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine hydrochloride and a method of using such compositions in treatment of liver dysfunction in mammals are disclosed.

Treatment of liver dysfunction with

Thienodiazepines of the formula: ##STR1## wherein Ar is mono- or di-substituted phenyl [the substituents(s) being H, halogen, C.sub.1.sub.-4 alkyl or C.sub.1.sub.-4 alkoxy] or pyridyl; R.sup.1 is H or C.sub.1.sub.-4 alkyl; R.sup.2 is H, halogen or C.sub.1.sub.-4 alkyl; or R.sup.1 and R.sup.2 combinedly form -(CH.sub.2).sub.4 -; each of R.sup.3 and R.sup.4 is C.sub.1.sub.-4 alkyl, or R.sup.3 and R.sup.4 together with the adjacent nitrogen atom form a heterocyclic group; A is C.sub.2.sub.-4 alkylene; and n is an integer of zero and 1; and pharmaceutically acceptable acid addition salts thereof are disclosed. They are useful as analgesics.

Thienodiazepines

Substituted phenylalkanoic acids and derivatives thereof of the formula: ##SPC1## Wherein each of R.sup.1 and R.sup.2 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; each of X.sup.1 and X.sup.2 is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms; Y is COOH, COOR (wherein R is an alkyl group having 1 to 4 carbon atoms), CONH.sub.2, CSNH.sub.2, CN or COZ--A--N(R.sup.3)(R.sup.4) (wherein Z is an oxygen atom or an imino group, A is an alkylene group having 2 to 4 carbon atoms and each of R.sup.3 and R.sup.4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, or R.sup.3 and R.sup.4 together with the adjacent nitrogen atom form a saturated heterocycle selected from pyrrolidine, piperidine, morpholine, piperazine and piperazine substituted by an alkyl group having 1 to 4 carbon atoms at the 4-position; and ring P represents a pyridine ring, a pyrimidine ring or a thiazole ring; and pharmaceutically acceptable salts thereof are useful as analgesics, anti-pyrestics and anti-inflammatory agents.

Substituted phenylalkanoic acids and derivatives

Tricycle substituted acetones

Triazolothienodiazepine compounds of the formula; ##SPC1## Wherein X is a member selected from the group consisting of a hydrogen atom, a methyl group, a methoxy group and a trifluoromethyl group; each of R.sup.1 and R.sup.2 is a member selected from the group consisting of a hydrogen atom and an alkyl group having 1 to 4 carbon atoms, or R.sup.1 and R.sup.2 together can form a tetramethylene group, i.e.--(CH.sub.2).sub.4 --; R is a member selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, --CONHR.sup.3 (R.sup.3 being an alkyl group having 1 to 4 carbon atoms) and -alk-N(R.sup. 4)(R.sup.5) (each of R.sup.4 and R.sup.5 being a member selected from the group consisting of a hydrogen atom and an alkyl group having 1 to 4 carbon atoms, or R.sup.4 and R.sup.5 and N can form a heterocyclic ring; and alk being an alkylene group having 2 to 4 carbon atoms); and Z is a member selected from the group consisting of an oxygen atom and a sulphur atom; and the pharmaceutically acceptable acid addition salts thereof are disclosed. These compounds are useful as minor tranquillizers (anti-anxiety drugs), sleep inducers, and anti-epileptics.

Triazolothienodiazepine compounds

Substituted pyrrolidinemethanols of the formula: ##SPC1## Wherein R.sup.1 and R.sup.2 are each H or C.sub.1.sub.-4 alkyl; R.sup.3, R.sup.4 and R.sup.5 are each H, halogen, C.sub.1.sub.-4 alkyl or C.sub.1.sub.-4 alkoxy, or R.sup.3 and R.sup.4 combinedly form methylenedioxy; and R is C.sub.1.sub.-10 alkyl or a group of the formula: ##SPC2## Where R.sup.6, R.sup.7 and R.sup.8 are each H, halogen, C.sub.1.sub.-4 alkyl or C.sub.1.sub.-4 alkoxy, or R.sup.6 and R.sup.7 combinedly form methylenedioxy; and pharmaceutically acceptable acid addition salts thereof are disclosed. They are useful as drugs for the treatment of diseases of the heart and circulation.

Substituted pyrrolidinemethanols

Heterocyclic compounds of the formula: ##SPC1## Wherein A is a carbonyl group, a methylene group or an alkylidene group having 2 to 4 carbon atoms; B is an oxygen atom, a sulfur atom or --N(R')-- (wherein R' is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms); each of R.sup.1 and R.sup.2 is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms or a phenyl group which may be substituted by a halogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms; X is an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or OM (wherein M is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a metal atom or NH.sub.4); and ring P represents a pyridine ring, are useful as anti-allergic agents.

Benzopyrano and benzothiopyrano [2,3-6] pyridines

Substituted alkanoic acids and derivatives thereof of the formula: ##SPC1## Wherein each of X.sup.1 and X.sup.2 is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms; each of R.sup.1 and R.sup.2 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; A is a carbonyl group, a methylene group or an alkylidene group having 2 to 4 carbon atoms; Y is --O--, --S-- or --N(R)-- [wherein R is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms]; Z is OH or Q--B--N(R.sup.3)(R.sup.4) [wherein Q is O (oxygen atom) or NH, B is an alkylene group having 1 to 4 carbon atoms and each of R.sup.3 and R.sup.4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, or R.sup.3 and R.sup.4 together with the adjacent nitrogen atom form a saturated heterocycle selected from the group consisting of pyrrolidine, piperidine, morpholine, piperazine and piperazine substituted by an alkyl group having 1 to 4 carbon atoms at the 4-position]; and ring P represents a pyridine or a pyridine N-oxide ring; and pharmaceutically acceptable salts thereof are useful as antirheumatics, analgesics, antipyretics and anti-inflammatory agents.

Growing community of inventors

Nakatsu, Japan

Michio Nakanishi