2-phenyl-1,4-benzothiazin-3-one derivatives

Details 2-phenyl-1,4-benzothiazin-3-one derivatives 2-phenyl-1,4-benzothiazin-3-one derivatives

1986-11-04

1988-04-19

Jiles, Henry R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Chalcogen in the nitrogen containing substituent

C07D27910, A61K 3138

Patent

active

047390506

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE ART

This invention relates to 2-arylbenzothiazine derivatives which possess calcium antagonisum and anti-platelet aggregation effects and are useful for treating circulatory diseases.


BACKGROUND OF THE INVENTION

As the prior art concerning benzothiazone compounds which are useful for treating circulatory diseases, there exists the publication of European Patent Application (publication No. 116368) disclosing the compounds having 3-oxo-2H-1,4-benzothiazine as the main structure, which appears in the compounds of the present application.
However, such publication discloses only 2-mono substitutes and does not represent 2,2-disubstituted benzothiazine or benzothiazine derivatives having the substituent(s) at 5 to 8 position(s) as in the present application.
There was few studies on 2,2-disubstituted benzothiazine or benzothiazine derivatives having the substituent(s) at 5 to 8 position(s), so the necessity arose studing methods of synthesis and efficacy of such derivatives.
We synthesized a series of 2,2-disubstituted benzothiazine and benzothiazine derivatives having the substituent(s) at 5 to 8 position(s), and examined the efficacy thereof.


DISCLOSURE OF THE INVENTION

This invention relates to 2-arylbenzothiazine derivatives and salts thereof represented by the formula[I], processes of preparation and therapeutic drugs comprising them for treating circulatory diseases, ##STR4## wherein R.sup.1 and R.sup.2 are the same or different and are hydrogen, lower alkyl, hydroxy, lower alkoxy, acyloxy, tetrahydropyranyloxy, halogen, nitro, amino, lower alkylamino or ##STR5## and the lower alkoxy group may be substituted by halogen, formyl, lower alkoxy or epoxy; mercapto, lower alkylthio, arylthio, halogen, cyano, formyl-lower alkyl, lower alkoxy-lower alkyl or ##STR6## R.sup.5, R.sup.6, R.sup.7 and R.sup.8 are the same or different and are hydrogen, lower alkyl, cycloalkyl, acyl, phenyl, pyridyl or substituted lower alkyl, and the phenyl or pyridyl group may be substituted by lower alkyl, hydroxy, lower alkoxy, lower alkylenedioxy, halogen, nitro, cyano, lower alkanoyloxy or halogeno-lower alkyl, and the substituent(s) of the substituted lower alkyl is(are) hydroxy, phenyl, phenyloxy, phenylcarbonyl or pyridyl, and such phenyl ring of the phenyl, phenyloxy or phenylcarbonyl group and the pyridyl group may further be resubstituted by lower alkyl, hydroxy, lower alkoxy, lower alkylenedioxy, halogen, nitro, cyano, lower alkanoyloxy or halogeno-lower alkyl; piperazine or morpholine ring, and the piperidine or piperazine ring may be substituted by lower alkly, phenyl, hydroxy-lower alkyl, phenyl-lower alkyl, phenylcarbonyl, phenylcarbonyl-lower alkyl, phenyl-(hydroxy)lower alkyl, phenyl-lower alkenylcarbonyl or naphthoxy-(hydroxy)lower alkyl, and such phenyl ring of the phenyl, phenyl-lower alkyl, phenylcarbonyl, phenylcarbonyl-lower alkyl, phenyl-(hydroxy)lower alkyl or phenyl-lower alkenylcarbonyl group may further be resubstituted by lower alkyl, lower alkoxy, alkylenedioxy or halogen; halogeno-lower alkyl or lower alkanoyloxy; hydroxy; and atom at the same time.
The above mentioned groups are described more in detail as follows.
Lower alkyl means alkyl group having 1 to 6 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl and hexyl; lower alkoxy means alkoxy group having 1 to 6 carbon atoms such as methoxy, ethoxy, propoxy, butoxy and hexyloxy; acyloxy means alkanoyloxy group having 1 to 6 carbon atoms such as acetoxy, propionyloxy, butanoyloxy and pentanoyloxy, and aromatic carbonyloxy such as benzoyloxy; halogen means fluorine, chlorine, bromine and iodine; cycloalkyl means cycloalkyl group having 3 to 6 carbon atoms such as cyclopropane and cyclohexane; aryl means aromatic group such as phenyl and toryl; acyl means alkanoyl group having 1 to 6 carbon atoms such as acetyl, propionyl, butanoyl and pentanoyl, or aromatic carbonyl such as benzoyl; lower alkylenedioxy means alkylenedioxy group having 1 to 3 carbon atoms such as methylenedioxy, ethylenedioxy and propylenedioxy; l

REFERENCES:
patent: 3089872 (1963-05-01), Krapcho
patent: 3401166 (1968-09-01), Krapcho
patent: 3622572 (1971-11-01), Krapcho
patent: 4595685 (1986-06-01), Henning et al.
Chemical Abstracts, vol. 95, No. 115577x.
"Non-stereospecific Ring Expansion Reactions of Benzothiazoline Sulfoxides", Chemical Pharmaceutical Bulletin, vol. 32, No. 7, 1984, by Hiroshi Shimizu et al., pp. 2571-2590.

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