Yoshitomi Pharmaceutical Industries, Ltd.

Shuzo Takehara

Tohru Nakao

Hiroshi Tanaka

Yasuto Morimoto

Tetsuya Tahara

Toru Nakao

Minoru Kawakami

Masao Hisadome

Kenji Morita

Masamitsu Sakamori

Hirotake Yamato

Takeshi Akagi

A fused pyridazine compound of the formula ##STR1## wherein each symbol is as defined in the description. The compounds of the present invention are useful as anxiolytic agents which selectively act on anxiety because of having less side effects (e.g. muscle-relaxation, sedation or interaction with alcohol/barbiturates).

Fused pyridazine compound

Thiophene compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen, nitro, amino, halogen or C.sub.1-4 alkyl; R.sup.2 is hydrogen, nitro, amino, halogen, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, acyl, C.sub.2-5 alkoxycarbonyl, C.sub.1-4 alkoxy-C.sub.1-4 alkyl, aryloxy-C.sub.1-4 alkyl, acyloxy-C.sub.1-4 alkyl, hydroxy-C.sub.1-4 alkyl, acyloxy-C.sub.2-5 alkanoyl, C.sub.1-4 alkoxy-C.sub.2-5 alkanoyl, hydroxy-C.sub.2-5 alkanoyl, aryloxy-C.sub.2-5 alkanoyl or C.sub.2-5 haloalkanoyl; R.sup.3 is hydrogen, C.sub.1-8 alkyl, hydroxy-C.sub.1-4 alkyl, C.sub.2-5 alkanoyloxy-C.sub.1-4 alkyl, aryl, aryl-C.sub.1-4 alkyl, heteroaryl, heteroaryl-C.sub.1-4 alkyl or aryl, aryl-C.sub.1-4 alkyl, heteroaryl or heteroaryl-C.sub.1-4 alkyl substituted by at least one substituent selected from the group consisting of halogen, hydroxy, amino, nitro, cyano, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.2-5 alkanoylamino, C.sub.1-4 haloalkyl, acyloxy, C.sub.2-5 alkoxycarbonyl and carboxyl on the aromatic ring; m is 0, 1 or 2; n is 1 or 2; the bond represented by   is a single bond or a double bond. Thiophene compounds (I) are useful as antianxiety drugs, hypnotics, antiepileptic drugs or nootropics. Thiophene compounds (II) are useful as intermediates for said thiophene compounds (I).

Intermediates for the preparation of pharmaceutical thiophene compounds

Thiophene compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen, nitro, amino, halogen or C.sub.1-4 alkyl; R.sup.2 is hydrogen, nitro, amino, halogen, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, acyl, C.sub.2-5 alkoxycarbonyl, C.sub.1-4 alkoxy-C.sub.1-4 alkyl, aryloxy-C.sub.1-4 alkyl, acyloxy-C.sub.1-4 alkyl, hydroxy-C.sub.1-4 alkyl, acyloxy-C.sub.2-5 alkanoyl, C.sub.1-4 alkoxy-C.sub.2-5 alkanoyl, hydroxy-C.sub.2-5 alkanoyl, aryloxy-C.sub.2-5 alkanoyl or C.sub.2-5 haloalkanoyl; R.sup.3 is hydrogen, C.sub.1-8 alkyl, hydroxy-C.sub.1-4 alkyl, C.sub.2-5 alkanoyloxy-C.sub.1-4 alkyl, aryl, aryl-C.sub.1-4 alkyl, heteroaryl, heteroaryl-C.sub.1-4 alkyl or aryl, aryl-C.sub.1-4 alkyl, heteroaryl or heteroaryl-C.sub.1-4 alkyl substituted by at least one substituent selected from the group consisting of halogen, hydroxy, amino, nitro, cyano, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.2-5 alkanoylamino, C.sub.1-4 haloalkyl, acyloxy, C.sub.2-5 alkoxycarbonyl and carboxyl on the aromatic ring; m is 0, 1 or 2; n is 1 or 2; the bond represented by.sub.---- is a single bond or a double bond. Thiophene compounds (I) are useful as antianxiety drugs, hypnotics, antiepileptic drugs or nootropics. Thiophene compounds (II) are useful as intermediates for said thiophene compounds (I).

Thiophene compounds and their pharmaceutical uses

Thienocycloheptapyridazine compounds and their pharmaceutical use

A fused thiophene compound of the formula: ##STR1## or a pharmaceutically acceptable acid addition salt thereof. In the above formula, one of E.sup.1, E.sup.2 and E.sup.3 is sulfur atom and other two of them are C--R.sup.1 and C--R.sup.2 respectively. R.sup.1 and R.sup.2 are the same or different and each is hydrogen, halogen, nitro, amino, cyano, hydroxyl, formyl, alkyl, alkoxy, haloalkyl, arylalkyl, acyl, alkoxyalkyl, acyloxyalkyl, hydroxyalkyl, acyloxyalkanoyl, alkoxyalkanoyl, hydroxyalkanoyl, aryloxyalkanoyl, haloalkanoyl, alkylthio, alkylsulfinyl, alkylsulfonyl, arylthio, arylsulfinyl, arylsulfonyl, hydroxysulfonyl, halosulfonyl, sulfamoyl, substituted sulfamoyl, carboxyl, acylamino, alkoxycharbonyl, carbamoyl, substituted carbamoyl or substituted amino. D is --CH.sub.2 -- or --S(O).sub.m -- (m is 0, 1 or 2). Q is straight or branched chain alkylene. T is primary amino, secondary amino or tertiary amino. A and B are the same or different and each is carbonyl or thiocarbonyl, or one of A and B is absent and the other of them is carbonyl or thiocarbonyl, or A is --CH.sub.2 -- and B is carbonyl or thiocarbonyl, and n is 1, 2 or 3 with the proviso that n is 2 or 3 when one of A and B is absent and the other of them is carbonyl or thiocarbonyl, and n is 1 or 2 when A and B are other combinations. In the above definitions, (hetero)aromatic ring and heterocyclic ring may optionally be substituted by 1 to 3 substituents. Said compounds have selective affinity for 5-HT.sub.1A receptor, or high affinity for 5-HT.sub.1A and dopamine D.sub.2 receptors so that they are useful as antianxietic drug, antipsychotic drug or drug for the disease of circulatory system. The intermediates for said fused thiophene compounds are also disclosed.

Fused thiophene compounds and uses thereof

Thienocinnoline compounds and their pharmaceutical use

Benzothiopyrano[4,3-c]pyridazine compounds, methods for preparing said

Benzo[h]cinnoline compound, a method of preparing said compound and a

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Nakatsu, Japan

Shuzo Takehara