Novel benzothiazine derivatives

Details Novel benzothiazine derivatives Novel benzothiazine derivatives

1987-03-10

1988-11-22

Lee, Mary C.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

544 52, A61K 3154, C07D27910

Patent

active

047866357

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE ART

This invention relates to benzothiazine derivatives which possess anti-platelet aggregation and calcium antagonism effects and are useful for treatment of circulatory diseases.


BACKGROUND OF THE INVENTION

There were few studies on benzothiazine derivatives useful as therapeutic drugs. Especially, there is only one prior publication, Japanese Unexamined Patent Publication No. 148771/84 filed by the same inventors of this invention, disclosing the compounds useful for treatment of circulatory diseases of the present object. The inventors further advanced the previous study to find out novel and useful compounds. The characteristic of the chemical structure of the compounds of this invention is that phenyl group substituted at 2-position of benzothiazine ring has a side chain which has a substituted or unsubstituted phenyloxy group. Such structural characteristic has not been disclosed in the above Japanese Unexamined Patent Publication No. 148771/84.
As other prior arts concerning compounds having benzothiazine ring, there exists publications by J. Krapcho (U.S. Pat. No. 3166554), Stearns et al. (U.S. Pat. No. 3,555,155) and Stanley O. et al. (Can. Pat. No. 717979). The chemical structures of the compounds disclosed in the respective patents are different from those of this invention and the objects thereof are also different. The object of the patent of J. Krapcho is a treatment of Parkinsonism, the patent of Stearns et al. is on herbicides, and the patent of Stanley et al. is on medicines having anticholinergic activity and antihistaminic activity.
The object of this invention is to search and find more useful drugs for circulatory diseases based on the prior arts.


DISCLOSURE OF THE INVENTION

This invention relates to benzothiazine derivatives of the formula [I] and salts thereof, processes for preparing them and therapeutic drugs for circulatory diseases containing either of them as an active ingredient, ##STR3## wherein R.sup.1 is one or more groups selected from those consisting of hydrogen, lower alkyl, halogen, nitro, hydroxy, lower alkoxy, lower alkanoyloxy, amino, lower alkylamino and lower alkoxycarbonyloxy; lower alkyl, hydroxy, lower alkoxy, halogen, nitro, lower alkylenedioxy, lower alkanoyloxy, lower alkanoyl, amino, lower alkylamino, lower alkanoylamino and lower alkoxycarbonyloxy or ##STR4## R.sup.4 is hydrogen or lower alkyl; A and B are the same or different and are lower alkylene having 1 to 6 carbon atoms; and
The same shall be applied hereinafter.
The groups defined above are explained below more in detail:
Lower alkyl is an alkyl group having 1 to 6 carbon atoms exemplified by methyl, ethyl, propyl and hexyl; halogen is exemplified by fluorine, chlorine and bromine; lower alkoxy is an alkoxy group having 1 to 6 carbon atoms exemplified by methoxy, ethoxy, propoxy and hexyloxy; lower alkanoyloxy is an alkanoyloxy group having 1 to 6 carbon atoms exemplified by acetyloxy, propionyloxy and hexanoyloxy; (C.sub.3 -C.sub.6) cycloalkyl is a cycloalkyl group having 3 to 6 carbon atoms exemplified by cyclopropyl and cyclohexyl; lower alkylenedioxy is a group which have (C.sub.1 -C.sub.6) alkylene between two oxygen atoms exemplified by methylenedioxy and ethylenedioxy; lower alkanoyl is an alkanoyl group having 1 to 6 carbon atoms exemplified by acetyl, propionyl and hexanoyl.
The compounds of this invention can be prepared by the following methods. the formula [III] under basic conditions. ##STR5## wherein X is halogen or methanesulfonyloxy. The same shall be applied hereinafter. formula [V]. ##STR6## (3) A reaction of a compound of the formula [VI] with a compound of the formula [VII]. ##STR7##
The above reactions are usually carried out under basic conditions. Examples of a preferable base is inorganic or organic base such as sodium hydride, potassium carbonate, sodium carbonate, sodium hydroxide, sodium alcholate, triethylamine, pyridine or N,N-dimethylaniline. The reactions can be carried out using an excess amount of amine reactant without adding a base.
The compoun

REFERENCES:
patent: 4584300 (1986-04-01), Iwao et al.
patent: 4595685 (1986-06-01), Henning et al.
Morrison and Boyd, Organic Chemistry, 1978, pp. 555 and 742.
Chemische Berichte 30, pp. 809-813.

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