Yoshitomi Pharmaceutical Industries, Ltd.

Masami Shiroki

Tetsuya Tahara

Kazuhiko Araki

Michio Nakanishi

Kazuhiro Goto

Yutaka Maruyama

Hideo Matsuki

Penicillamine compounds of the formula: ##STR1## and of the formula: ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, A and B are as defined hereinafter, and pharmaceutically acceptable acid addition salts thereof are disclosed. II are the products of hydrolysis or alcoholysis of I, and I are in turn the products of dehydration of II or alcohol removal form II. I and II are useful for the treatment of rheumatoid arthritis.

Penicillamine compounds

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

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

Thiophene derivatives of the formula: ##SPC1## Wherein R.sup.1 is H or CH.sub.3 ; R.sup.2 is CH.sub.3 or C.sub.2 H.sub.5, or R.sup.1 and R.sup.2 combinedly represent --(CH.sub.2).sub.4 --; each of R.sup.3 and R.sup.4 is H, alkyl of from 1 to 4 carbon atoms or cyclohexyl, or R.sup.3 and R.sup.4 together with the adjacent nitrogen atom form 1-pyrrolidinyl, piperidino, 4-methyl-1-piperazinyl or morpholino; X is H, halogen or OCH.sub.3 ; A is -CH= or --C(CH.sub.3)=, and B is =N-- or =CH--; or A is --C(CH.sub.2 OH)= or --N=, and B is =N--, and pharmaceutically acceptable acid addition salts thereof possess excellent pharmacological properties such as sedative, anxiolytic and anticonvulsant effects and protective effects against hypoxia or anoxia.

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Yoshitomi, Japan

Masami Shiroki