Benzopyran derivatives

Details Benzopyran derivatives Benzopyran derivatives

1994-07-18

1997-07-08

Trinh, Ba K.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549343, 549344, 549399, 549405, 549407, C07D31158

Patent

active

056463081

DESCRIPTION:

BRIEF SUMMARY
THIS APPLICATION IS A 371 OF PCT/JP93/00086, DATED JAN. 25, 1993.



FIELD OF THE INVENTION

The present invention relates to a novel benzopyran derivative which is useful as medicine.


PRIOR ART

Benzopyran derivatives having various pharmacological effects have been known. For example, various benzopyran derivatives in which the 4-position carbon atom of a benzopyran ring is directly linked to a nitrogen atom are disclosed in Japanese Laid-Open Patent Publications No. 97974/1985, No. 47416/1986, No. 165317/1988, No. 196581/1988, No. 201182/1988, No. 303977/1988, No. 26578/1989, No. 38087/1989, No. 129184/1990 and Journal of Medicinal Chemistry, Vol. 33, No. 6, pp, 1529-1541, 1990. In the above documents there is described that said compounds have an anti-hypertension effect and can be used for a treatment for heart diseases.
Among the benzopyran derivatives disclosed in the above documents, Cromakalim represented by the following formula has recently been remarked as a new kind of a hypotensive drug having an effect on K.sup.+ channel together with Nicorandil and Pinacidil. ##STR2##
Besides, derivatives in which the 4-position carbon atom of a benzopyran ring is not directly linked to a nitrogen atom are also disclosed in Japanese Laid-Open Patent Publications No. 303977/1988 and No. 38087/1989, Official Gazette of WO 90/14346, Journal of Heterocyclic Chemistry, Vol. 11 (5), pp. 797-802, 1974 and Journal of Medicinal Chemistry, Vol. 33, No. 6, pp. 1529-1541, 1990. Particularly, in the Official Gazette of WO 90/14346 is disclosed a similar compound to the compound containing an amide group or a thioamide group at the 4-position of a benzopyran ring of the present invention.
The present inventors have studied assiduously about the synthesis of a benzopyran derivative which has the equivalent or more excellent K.sup.+ channel opening activities than said similar compound and Cromakalim and in which the 4-position carbon atom of a benzopyran ring is not directly linked to a nitrogen atom and about K.sup.+ channel effect activities. As a result, they have found that a novel benzopyran derivative to be described below, which is disclosed in no document, has such pharmacological activities and accomplished the present invention on the basis of this finding.


DISCLOSURE OF THE INVENTION

The compound of the present invention is a novel compound represented by the following general formula (I) having excellent K.sup.+ channel opening activities: ##STR3## wherein
R.sub.1 represents a hydrogen atom or a hydroxyl group,
R.sub.2 and R.sub.3 represent, in common with each other or independently, a lower alkyl group, a substituted lower alkyl group containing a halogen atom or a lower alkoxy group as a substituent, or, in combination, a heterocycle containing an oxygen atom or a sulfur atom as a hetero atom; R.sub.2 and R.sub.3 do not represent a lower alkyl group simultaneously, though,
R.sub.4 and R.sub.5 represent, in common with each other or independently, a hydrogen atom, a lower alkyl group, a lower haloalkyl group, a halogen atom, a lower alkoxy group, a lower haloalkoxy group, an amino group, an acylamino group, a nitro group, a cyano group, an ester group, a lower alkylsulfonyl group or an arylsulfonyl group.
X represents .dbd.O, .dbd.S or .dbd.N--Z, wherein Z represents a hydrogen atom, a lower alkyl group, an aryl group, a hydroxy group, a lower alkoxy group, a cyano group, a carbamoyl group or a sulfamoyl group, and
Y represents --NR.sub.6 R.sub.7, --OR.sub.8 or --SR.sub.9, wherein R.sub.6 and R.sub.7 represent, in common with each other or independently, a hydrogen atom, a hydroxyl group, a lower alkoxy group, a cyano group, an optionally substituted amino group, a saturated or unsaturated lower alkyl group which is optionally substituted, an optionally substituted aryl group, an optionally substituted cycloalkyl group, an optionally substituted heteroaryl group, or R.sub.6 and R.sub.7, in combination, represent a heterocycle optionally substituted with a nitrogen atom, and R.sub.8 and R.sub.9 represent

REFERENCES:
patent: 4415741 (1983-11-01), Kabbe
patent: 5412117 (1995-05-01), Koga et al.

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