Benzopyran derivatives

Details Benzopyran derivatives Benzopyran derivatives

1993-01-26

1995-05-02

Ramsuer, Robert W.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

544151, 544317, 544336, 544376, 546196, 548139, 548195, 548251, 5483114, 548525, 548953, 548964, 549399, 549405, 549407, C07D31158

Patent

active

054121175

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

This invention relates to a novel benzopyran derivative useful as pharmaceuticals.


BACKGROUND OF THE INVENTION

Benzopyran derivatives having various pharmacological activities have hitherto been known. For example, various benzopyran derivatives in which the carbon atom at the 4-position of the benzopyran ring is directly bonded to a nitrogen atom are disclosed in Japanese Patent Application Laid-Open Nos. 60-97974, 61-47416, 63-165317, 63-196581, 63-201182, 63-303977, 64-26578, 64-38087, and 2-129184, and Journal of Medical Chemistry, Vol. 33, No. 6, pp. 1529-1541 (1990). The literatures report that these compounds possess antihypertensive activity and are useful for the treatment of heart diseases.
Of the benzopyran derivatives disclosed, Cromakalim having formula: ##STR2## has recently attracted attention as a new type of hypotensires which acts on the K.sup.+ channel, similar to Nicorandil and Pinacidil.
Benzopyran derivatives in which the 4-carbon atom on the benzopyran ring is not bonded directly to a nitrogen atom are disclosed in Japanese Patent Application Laid-Open Nos. 63-303977 and 64-38087, Journal of Heterocyclic Chemistry, Vol. 11, No. 5, pp. 797-802 (1974), and Journal of Medical Chemistry, Vol. 33, No. 6, pp. 1529-1541 (1990).
Further, WO 90/14346 (published on Nov. 29, 1990, after the priority date of the present invention) discloses compounds having an amido group or a thioamido group at the position of the benzopyran ring thereof.


DISCLOSURE OF THE INVENTION

The inventors have conducted extensive and intensive investigations on synthesis of benzopyran derivatives with the 4-carbon atom on the benzopyran ring thereof being not bonded directly to a nitrogen atom which are equal or superior to Cromakalim in activity on the K.sup.+ channel and their activities on the K.sup.+ channel. As a result, they have found that un-reported, novel benzopyran derivatives described below possess the above-mentioned pharmacological activities and thus completed the present invention based on this finding.
The compounds according to the present invention are represented by formula (I): ##STR3## wherein X represents an oxygen atom, a sulfur atom, =N-Z, or =CHNO.sub.2, wherein Z represents a hydrogen atom, a lower alkyl group, an aryl group, a hydroxyl group, a lower alkoxy group, a cyano group, a carbamoyl group, or a sulfamoyl group; Y represents --NR.sub.8 R.sub.9, --OR.sub.10, or --SR.sub.11, wherein R.sub.8 and R.sub.9, which may be the same or different, each represent a hydrogen atom, a hydroxyl group, a lower alkoxy group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted lower alkyl group, a substituted or unsubstituted unsaturated lower alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted hetero-aryl group, or they are taken together with the nitrogen atom to form a substituted or unsubstituted heterocyclic ring, and R.sub.10 and R.sub.11 each represent a hydrogen atom, a lower alkyl group, or an aryl group; R.sub.1 represent a hydrogen atom, a lower alkyl group, or an aryl group, or it is directly bonded to R.sub.2 to form a single bond; R.sub.2 and R.sub.3, which may be the same or different, each represent a hydrogen atom or a hydroxyl group, or they are taken together to form =O, or R.sub.2 is directly bonded to R.sub.1 to form a single bond; R.sub.4 and R.sub.5, which may be the same or different, each represent a hydrogen atom or a lower alkyl group, or they are taken together to form a polymethylene group; and R.sub.6 and R.sub.7, which may be the same or different, each represent a hydrogen atom, a lower alkyl group, a lower haloalkyl group, a halogen atom, a lower alkoxy group, a lower haloalkoxy group, an amido group, an acylamino group, a nitro group, a cyano group, an ester group, a lower alkylsulfonyl group, or an arylsulfonyl group, or they are taken together to form =N--O--N=.
In the definition for symbols in formula (I), the term

REFERENCES:
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patent: 4935441 (1990-06-01), Rimbault
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H. E. Zaugg, J. E. Leonard, R. W. DeNet, D. L. Arendsen, "Substituted Chromans and Tetrahydrofuro[2,3-b] benzofurans (Trapped Tetrahedral Intermediates) from 3-Phenyl-2-benzofuranones", Journal of Heterocyclic Chemistry, vol. 11, No. 5, Oct. 1974, pp.:797-802.

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