1,4-thiazine derivative, and cardiotonic agent comprising it as

Details 1,4-thiazine derivative, and cardiotonic agent comprising it as 1,4-thiazine derivative, and cardiotonic agent comprising it as

1986-06-03

1989-01-24

Ford, John M.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

544 582, A61K 3154, C07D27912

Patent

active

048002011

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to a novel 1,4-thiazine derivative represented by the formula I, a pharmaceutically acceptable acid addition salt thereof, a process for preparation thereof and a cardiotonic agent comprising it as an effective component; ##STR2## wherein R.sub.1 and R.sub.2 represent respectively hydrogen atom, lower alkyl group, lower alkoxy group, amino group, lower alkyl-amino group, aryl-amino group, hydroxy group, aryl group or 5- or 6-membered heterocyclic residue; group when R.sub.1 and R.sub.2 represent hydrogen atom and R.sub.3 and R.sub.4 represent hydrogen atom or lower alkyl group.


BACKGROUND ART

Known process for synthesis of 1,4-thiazine derivative are for example a process starting with a thioglycol amide derivative as disclosed in Journal of the American Chemical Society, 70, 3517 (1948), a process starting with a tricyclic compound as disclosed in Japanese Patent Publication No. 16630/1967 and a process starting with a thiazolium compound as disclosed in Japanese Patent Publication No. 29182/1970.
The fact that pyridone derivatives and pyridazinone derivatives possess properties affecting the cardiovascular systems is described in for example Japanese Patent Provisional Publication No. 48675/1977, Journal of Medicinal Chemistry, 17, 273 (1974) and Japanese Patent Provisional Publication No. 109771/1982.
However, 1,4-thiazine derivatives having nitrogen-containing heterocyclic residue at position 6 are novel compounds and no technique is known for synthesis of such compounds. Furthermore, there is no report on cardiotonic activity of such compounds.


DISCLOSURE OF THE INVENTION

We, the inventors succeeded in synthesis of novel 1,4-thiazine derivatives as disclosed in prior Japanese Patent Application No. 170862/1983. As a result of our further intensive researches, we found that novel 1,4-thiazine derivatives having nitrogen-containing heterocyclic residue at position 6 have cardiotonic activity and completed the present invention. The present invention is directed to a novel 1,4-thiazine derivative having a nitrogen-containing heterocyclic residue at position 6, a pharmaceutically acceptable acid addition salt thereof, a process for preparation thereof and a cardiotonic agent comprising it as an effective component.
Terms used for definition of letters in the above formula I by which the compound of the present invention is represented are defined and exemplified in the following.
The term "lower" refers to group having 1 to 6 carbon atoms unless otherwise indicated.
The "lower alkyl group" may be alkyl group which are arranged as straight or branched chains and may be methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, n-pentyl, n-hexyl or the like.
The "lower alkoxy group" may be methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, tert-butoxy, n-pentyloxy, n-hexyloxy or the like.
The "aryl group" may be phenyl, tolyl, xylyl, mesityl, cumenyl, biphenyl or the like which may unsubstituted or may be substituted with lower alkyl group, lower alkoxy group, halogen atom, aldehyde group, acyl group, cyano group, nitro group, hydroxy group or the like.
The term "lower alkyl-amino group" means amino groups substituted with above-mentioned lower alkyl groups. The "lower alkyl-amino group" may be methylamino, dimethylamino, ethylamino, diethylamino, n-hexylamino or the like.
The term "arylamino group" means amino groups substituted with above-mentioned aryl group. The "arylamino" group may be anilino, toluidino, xylidino or the like.
The term "5- or 6-membered heterocyclic residue" means oxygen-, sulfur-, or nitrogen-containing 5- or 6-membered heterocyclic residue. The "5- or 6-membered heterocyclic residue" may be furyl, thienyl, pyrrolyl, pyrano, pyridinyl, pyridazino, pyrimidino, piperidino, piperazino or morpholino or the like.
The term "N-containing heterocyclic residue" means nitrogen-containing 5- or 6-membered mono or condensed heterocyclic residue which may be unsubstituted or may be substituted by lower alkyl group, lower al

REFERENCES:
patent: 3378555 (1968-04-01), Takamizawa et al.
patent: 4483983 (1984-11-01), Lang et al.
patent: 4565813 (1986-01-01), Takase et al.

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