Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1987-07-17
1989-06-27
Daus, Donald G.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
544234, 549 23, A61K 3150, C07D49504
Patent
active
048430757
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to novel and pharmaceutically useful benzothiopyrano[4,3-c]pyridazine compounds, methods for preparing said compounds and pharmaceutical compositions containing said compounds.
BACKGROUND ART
European Patent Application No. 124314A discloses such compounds possessing potent cardiotonic and antihypertensive activities as 2,4,4a,5-tetrahydro-7-(1H-imidazol-1-yl)-3H-indeno[1,2-c]pyridazin-3-one, and Journal of Medicinal Chemistry (J. Med. Chem.), vol. 24, P. 830 (1981) discloses immunosuppressive 2-(4-chlorophenyl)benzothiopyrano[4,3-c]pyrazol-3-one and so on.
DISCLOSURE OF THE INVENTION
The present inventors have made intensive investigations in order to synthesize effective compounds and develop useful drugs, and then conceived a benzothiopyrano[4,3-c]pyridazine skeleton which has not been known in the prior art including the above-mentioned literatures.
As a result of such investigations, the present inventors have found that novel benzothiopyrano[4,3-c]pyridazine compounds of the following formula (I) possess useful activities such as anti-anxietic activity, and completed the present invention.
The present invention relates to benzothiopyran[4,3-c]pyridazine compounds of the formula: ##STR2## R.sup.1 and R.sup.2 are the same or different and each is hydrogen, halogen, trifluoromethyl, hydroxy, amino, nitro, cyano, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, or C.sub.2-5 alkanoylamido, 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, pyridyl, aryl, aryl-C.sub.1-4 alkyl, or aryl or aryl-C.sub.1-4 alkyl substituted by at least one substituent selected from the group consisting of halogen, trifluoromethyl, hydroxy, amino, nitro, cyano, C.sub.1-4 alkyl, C.sub.1-4 alkoxy and C.sub.2-5 alkanoylamido on the aromatic ring, n is 0, 1 or 2, and the bond between the 4-position and the 4a-position is a single bond or double bond; and also relates to methods for preparing said compounds and pharmaceutical compositions containing said compounds.
In explaining each symbol of the formula (I) in accordance with the definitions, halogen includes fluorine, chlorine, bromine and iodine; C.sub.1-4 alkyl includes, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl; C.sub.1-4 alkoxy includes, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy and tert-butoxy; C.sub.2-5 alkanoylamido includes, for example, acetylamido, propionylamido, butyrylamido and pivaloylamido; hydroxy-C.sub.1-4 alkyl includes, for example, hydroxymethyl, hydroxyethyl, hydroxypropyl and hydroxybutyl; C.sub.2-5 alkanoyloxy-C.sub.1-4 alkyl includes, for example, acetoxymethyl, acetoxyethyl, acetoxypropyl, acetoxybutyl, propionyloxymethyl, propionyloxyethyl, propionyloxypropyl and propionyloxybutyl; C.sub.1-8 alkyl means straight or branched chain alkyl and includes, for example, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl and decyl; aryl-C.sub.1-4 alkyl includes, for example, benzyl, phenylethyl, phenylpropyl, phenylbutyl, naphthylmethyl, naphthylethyl, naphthylpropyl and naphthylbutyl; and aryl includes, for example, phenyl and naphthyl.
The compounds of the formula (I) having a chiral carbon atom can be prepared as a racemate or an optically active isomer, and the compound (I) having at least two chiral atoms can be obtained as an individual diastereomer or a mixture thereof. The present invention also embraces the mixture thereof and the individual isomers. Furthermore, the present invention embraces stereomers, too.
Preferred compounds of the formula (I) are the compounds wherein R.sup.1 and R.sup.2 are the same or different, and each is hydrogen, halogen, trifluoromethyl, hydroxy, amino, nitro, cyano, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or C.sub.2-5 alkanoylamido, R.sup.3 is aryl or aryl substituted by at least one substituent selected from the group consisting of halogen, trifluoromethyl, hydroxy, nitro, C.sub.1-4 alkyl and C.
REFERENCES:
Lombardino et al., J. Med. Chem. 24, p. 830 (1981).
Kawakami Minoru
Morimoto Yasuto
Nakao Toru
Tahara Tetsuya
Takehara Shuzo
Bernhardt E.
Daus Donald G.
Yoshitomi Pharmaceutical Industries Ltd.
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