Shionogi Company Limited

Ikuo Adachi

Motohiko Ueda

Teruo Yamamori

Yoshiharu Hiramatsu

Masami Eigyo

Masami Doteuchi

Takefumi Gemba

Masaru Kawakami

Hatsuo Sato

Sadatoshi Kimoto

A method useful for the treatment or prevention of diseases caused by a massive release of cerebral glutamate, in particular epilepsy and dementia, and pharmaceutical formulations therefor, which comprise, as an active ingredient, a therapeutically effective amount of methyl (+)-(4S)-4,7-dihydro-3-isobutyl-6-methyl-4-(3-nitrophenyl)thieno[2,3-b]pyr idine-5-carboxylate (S-312-d).

Formulation useful for the inhibition of massive release of cerebral

Novel Ca-blockers, 4,7-dihydropyrazolo[3,4-b]pyridine derivatives having potent antihypertensive and coronary vasodilating actions and useful in treatment for diseases in circulatory system, but without systole inhibitory action.

4,7-dihydropyrazolo(3,4-b) pyridine derivatives

Highly effective calcium channel blockers having potent antihypertensive and coronary vasodilating actions, i.e. 4,7-dihydrothieno[2,3-b]pyridine derivatives of the formula: ##STR1## wherein R.sup.1 is straight or branched chain C.sub.1 -C.sub.4 alkyl, alkoxyalkyl, or arylalkyl; R.sup.2 is hydrogen, straight or branched chain C.sub.1 -C.sub.4 alkyl, or alkoxycarbonyl; R.sup.3 is hydrogen, straight or branched chain C.sub.1 -C.sub.4 alkyl, phenyl which may be substituted by one or more halogens or alkoxy groups, optionally substituted cycloalkyl, or optionally substituted cycloalkylalkyl; or R.sub.2 and R.sup.3 taken together may form an alkylene.

4,7-dihydrothieno[2,3-B]pyridine derivatives useful in the treatment of

1,6-Dialkyl-3-substituted-4-nitrophenyl-4,7-dihydropyrazolo[3,4-b]pyridine- 5-carboxylic acid esters as Ca blocker having potent antihypertensive and coronary vasodilating actions and useful in treatment of diseases in circulatory system such as angina pectoris, hypertension, cerebrovascular dysfunction, arrhythmia, etc. with no systole inhibitory action, prepared from nitrobenzylideneacetoacetic acid esters on reaction with 3-substituted-5-amino-1-alkylpyrazoles.

1,6-Dialkyl-3-su

Lower alkyl 2-chloro-2-hydroxyiminoacetates are produced by (A) reacting chloral with a lower alkanol and a hydroxylamine salt in the presence of a Lewis acid or a metal oxide which is convertible into said Lewis acid during the course of the reaction to give a lower alkyl 2-hydroxyiminoacetate and then chlorinating the resulting product or (B) reacting chloral oxime with a lower alkanol in the presence of a base to give a lower alkyl 2-hydroxyiminoacetate and finally chlorinating the thus formed product.

Process for the production of lower alkyl 2-chloro-2-hydroxyiminoacetates

3-Substituted-4-(5, 6, or 7)-(2-hydroxy-3-substituted aminopropoxy)-1,2-benzisoxazoles synthesized from 3-substituted-4 (5, 6, or 7)-(2,3-epoxypropoxy)-1,2-benzisoxazoles with a primary amine showing .beta.-blocking activity with low toxicity.

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Osaka, Japan

Ikuo Adachi