Shionogi Company Limited

Susumu Takada

Takashi Sasatani

Nobuo Chomei

Akira Matsushita

Masami Eigyo

Makoto Adachi

Toshio Fujishita

Masaaki Uenaka

Yasuo Makisumi

Natsuki Ishizuka

Tsuyoshi Kihara

Kazuo Kawasaki

Hirohisa Shindo

Cyanoiminoquinoxaline derivatives

A process for the preparation of 3-isoxazolecarboxlic acid which is an intermediate for prepearing useful compounds is provided, said process being characterized in that a compound of formula (I) is reacted with hydroxylamine to obtain a compound of formula (II), and the compound thus obtained is treated with an alkali: ##STR1## wherein R.sup.1 is a lower alkyl, R.sup.2 is a carboxy protecting group, X is a halogen atom, and Y is a hydrogen atom, or X and Y together may form a single bond.

Process for the preparation of 3-isoxazolecarboxylic acid

An oxopyridinylquinoxaline derivative represented by the following Formula I or pharmaceutically acceptable salts thereof: ##STR1## wherein R.sup.1 is hydrogen, halogen, nitro, or trihalomethyl; R.sup.2 is hydrogen, halogen, nitro, cyano, trihalomethyl, carbamoyl, carbamoyl substituted with lower alkyl, sulfamoyl, or sulfamoyl substituted with lower alkyl; R.sup.3 is hydrogen, nitro, or halogen; R.sup.4 is hydrogen, lower alkyl, substituted lower alkyl, lower cycloalkyl, or substituted lower cycloalkyl; R.sup.5 's are substituents independently selected from the group consisting of halogen, nitro, cyano, lower alkyl, carbamoyl, and carbamoyl substituted with lower alkyl; and n is an integer of 0 to 4. The derivative works as an antagonistic agent against both the NMDA receptors and the AMPA receptors, so that it is effective as a therapeutic agent for neurological disorders caused by excitatory amino acids binding to the receptors.

Oxopyridinylquinoxaline derivative

A compound of the formula: ##STR1## wherein R is an optionally substituted phenyl group, 5-membered; the A ring is a 5 to 7 membered alicyclic group in which said A ring may have an alkyl group as a substituent, or a pharmaceutically acceptable salt thereof, and is useful as a psychotropic agent.

Condensed imidazopyridine derivatives

A compound of the formula: ##STR1## wherein R is an optionally substituted aryl group or an optionally substituted aromatic heterocycle group; A ring is a 5 to 9 membered alicyclic group, in which one or more of carbon atoms constituting said A ring may be replaced by O, or S and said A ring may have alkyl as a substituent, or a pharmaceutically acceptable salt thereof.

The present invention relates to preparation of imidazoles which are useful as pharmaceutical and agricultural chemicals. Specifically, the present invention relates to a process for preparing imidazoles of the formula (I): ##STR1## which comprises conducting condensation among an .alpha.,.alpha.-dihaloaldehyde compound of the formula (II): ##STR2## an aldehyde compound of the formula: R.sup.2 --CHO and aqueous ammonia.

Preparation of imidazoles

2-Substituted carbonylimidazo[4,5-c]quinolines of formula: ##STR1## having a high affinity for benzodiazepin receptor and showing an excellent psychostimulating action orally at a dose of 0.1-500 mg are provided through several routes.

2-substituted carbonylimidazo[4,5-c]quinolines

A compound of the formula: ##STR1## (wherein R is phenyl optionally substituted by one or two members selected from the group consisting of trifluoromethyl, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, C.sub.1 -C.sub.5 alkylthio, nitro, amino C.sub.1 -C.sub.5 alkanoylamino and C.sub.1 -C.sub.5 alkoxycarbonyl or 5- or 6-membered heterocyclic group optionally substituted by one or two members selected from the group consisting of halogen, C.sub.1 -C.sub.5 alkyl and C.sub.1 -C.sub.5 alkoxy,

Condensed imidazopyridine derivatives useful as psychotropic agents

Compounds of the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 each is hydrogen, alkyl, alkoxycarbonyl, carboxy, halogen, nitro or trifluoromethyl, or R.sup.1 and R.sup.2 taken together may form alkylene; R.sup.3 is hydrogen, alkyl, alkanoyl or alkylsulfonyl; R.sup.4 is hydrogen, alkoxycarbonyl, carboxy or halogen; X is hydrogen, alkyl, alkoxy, halogen or hydroxy; and Y is methine or nitrogen or salts thereof are provided. The compounds (I) show potent psychotropic activity.

Pyrazolo[4,3-c]quinoline-3-one and imidazo[4,3-c]cinnolin-3-one

Tetrahydrothiopyrano[2,3-b]indole derivative represented by the formula I: ##STR1## wherein R.sup.1 is hydrogen, alkyl, hydroxyalkyl, alkenyl, aralkyl, aryl, --COR.sup.5 (wherein R.sup.5 is alkyl, alkenyl, aryl or alkoxy) or ##STR2## (wherein Y is alkylene, oxoalkylene, hydroxyalkylene and R.sup.6 and R.sup.7 are each hydrogen or alkyl): R.sup.2 is hydrogen or alkyl; R.sup.3 is hydrogen, alkyl, hydroxyalkyl, alkenyl, aralkyl, aryl or dialkylaminoalkyl or ##STR3## is pyrrolidino, piperidino, piperazino, 4-alkylpiperazino, 4-arylpiperazino or morpholino; R.sup.4 is hydrogen or alkyl; A is methylene, alkylmethylene, ethylene, alkylethylene; X is hydrogen or one or two groups selected from the group consisting of halogen, alkyl, alkoxy, hydroxy and halogenoalkyl; and n is an integer of 0 to 2 and its pharmaceutically acceptacle salts; synthesized from 2-propargylthioindole or 2-(4-hydroxy-2-butynylthio)-indole; useful as analgesic and anti-inflammatory agent.

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Kawanishi, Japan

Susumu Takada