Shionogi Company Limited

Takashi Sasatani

Susumu Takada

Akira Matsushita

Yasuo Makisumi

Masami Eigyo

Makoto Adachi

Toshio Fujishita

Akira Murabayashi

Nobuo Chomei

Jun Sato

Hideaki Watanabe

Masanao Inagaki

Yoshiharu Hiramatsu

Hiroshi Hashizume

Natsuki Ishizuka

Yasuhiko Fujii

Susumu Mitsumori

Yoshikazu Fukui

Hirohisa Shindo

Masahide Odan

The present invention provides compounds having an agonistic activity to the cannabinoid receptor, which is represented by the formula (I): wherein R, R, R, R, and G are defined as herein, a pharmaceutically acceptable salt or a solvate thereof, and pharmaceutical compositions, atopic dermatitis treating agents, and anti-pruritus agents, especially anti-pruritus agents for oral used and for external application, which each contains the said compound as an active ingredient.

3-carbamoyl-2-pyridone derivatives

Having an affinity against serotonine receptors, compound (I) shown below is useful as a therapeutic agent against various kinds of diseases of central nervous systems;(wherein Ris hydrogen; Ris hydrogen or lower alkyl; Ris hydrogen, &#x2014;COORand so on; Ris hydrogen, lower alkyl and so on, or Rand Rtaken together may form &#x2550;O or &#x2550;S; Ris hydrogen, or Rand Rtaken together may form a bond; Ris hydrogen, &#x2014;COORand so on; Ris hydrogen, halogen, lower alkyl and so on; Ris hydrogen, lower alkyl, cycloalkyl and so on; R, Rand Rare each independently hydrogen, halogen, lower alkyl and so on).

Tricyclic indole compounds having affinity for serotonin receptor

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.

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

Tetrahydrothiopyrano[3,2-b]indole derivatives represented by the formula I: ##STR1## wherein R.sup.1 is hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, phenyl-C.sub.1-4 alkyl, C.sub.2-5 alkanoyl, or ##STR2## wherein Y is C.sub.1-4 alkylene or C.sub.1-4 oxoalkylene and R.sup.5 and R.sup.6 each is hydrogen or C.sub.1-4 alkyl;

Tetrahydrothiopyrano(3,2-b)-indole derivatives

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.

Tetrahydrothiopyrano[2,3-b]indole derivatives

3-Aminoisoxazoles of the formula: ##STR1## (wherein R is C.sub.1 -C.sub.6 alkyl, phenyl or halo-phenyl) are prepared by reacting a .beta.-ketonitrile of the formula:

Process for the production of 3-aminoisoxazoles

Urea derivatives of the formula ##STR1## (wherein Ar represents a residue of 5- or 6-membered heteroaromatic ring; R represents a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group; R.sup.1 represents a C.sub.1 -C.sub.6 alkyl group; and R.sup.2 represents a C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, or C.sub.1 -C.sub.6 alkoxy group) are produced by reacting an amine of the formula

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Nara, Japan

Takashi Sasatani