Bisoxadiazolidine derivative

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

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Details

5462691, 548132, C07D41314, A61K 3141

Patent

active

056439318

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/JP9400696 filed Apr. 26, 1994.


TECHNICAL FIELD

This invention relates to a novel bisoxadiazolidine derivative and pharmaceutically acceptable salts thereof which are useful as medicines, particularly as a hypoglycemic drug (insulin sensitivity-increasing drug) and to a pharmaceutical composition containing the same.


BACKGROUND ART

Sulfonylurea compounds and biguanide compounds are currently used clinically as synthetic hypoglycemic drugs for the treatment of diabetes. Biguanide compounds, however, are rarely used because it induces lactic acidosis and their application is therefore restricted. On the other hand, sulfonylurea compounds show secure hypoglycemic action and hardly generate side effects, but it is necessary to take great caution in using them because they sometimes cause hypoglycemia.
In recent years, insulin sensitivity-increasing drugs capable of showing hypoglycemic action by increasing insulin sensitivity in peripheral tissues have been drawing attention as a successor for the aforementioned synthetic hypoglycemic drugs.
Compounds having the insulin sensitivity-increasing action have been synthesized as disclosed, for example, in International Patent Publication No. 92/03425 pamphlet (1992).
Under such circumstances, the inventors of the present invention have previously found that a bisoxa or thiazolidine derivative has excellent insulin sensitivity-increasing action and have filed a patent application [cf. International Patent Publication No. 93/03021 pamphlet (1993)].


DISCLOSURE OF THE INVENTION

The inventors of the present invention conducted intensive studies on substances having insulin sensitivity-increasing action and found that a bisoxadiazolidine derivative represented by the following general formula (I) has excellent insulin sensitivity-increasing action, hence resulting in the accomplishment of the present invention.
That is, according to the present invention, there is provided a bisoxadiazolidine derivative represented by a general formula (I) ##STR4## [symbols in the formula represent the following meanings; ##STR5## the same or different from each other and each represents a phenylene group which may be substituted, ##STR6## (3) a group represented by the formula --S(O).sub.n --, (4) a group represented by the formula --CO--, ##STR7## (6) an alkylene group or an alkenylene group which may respectively be interrupted with an oxygen atom and/or a sulfur atom and which may respectively be substituted, or ##STR8## R.sup.1 : a hydrogen atom or a lower alkyl group, n: 0, 1 or 2, represents ##STR9## (R.sup.1 is as defined in the foregoing), (3) a group represented by the formula --S(O).sub.n -- (n is as defined in the foregoing), ##STR10## (R.sup.2 is as defined in the foregoing), or (6) an alkylene group, an alkenylene group or a pyridinediyl group which may respectively be interrupted with an oxygen atom and/or a sulfur atom and which may respectively be substituted, and ##STR11## a cycloalkanediyl group, an arylene group or a pyridinediyl group, which may respectively be substituted],
or a pharmaceutically acceptable salt thereof.
The compound of the present invention is a novel compound whose structure is entirely different from any prior art compounds having insulin sensitivity-increasing action, because it has a unique chemical structure as a bis form in which (1,3,4-oxadiazolidine-3,5-dione-2-yl)methyl groups are linked to both ends of a connecting group ##STR12##
The following describes the compound of the present invention in detail.
Unless otherwise noted, the term "lower" as used herein in the definition of the general formulae means a straight or branched carbon chain having 1 to 6 carbon atoms.
In consequence, illustrative examples of the "lower alkyl group" include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl, 1,2-dimethylpropyl, hexyl, isohexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbu

REFERENCES:
patent: 4598153 (1986-07-01), United States
patent: 5420146 (1995-05-01), Malamas
Journal of Medicinal Chemistry, vol. 34, No. 5, May 1991 Washington, D.C., US, pp. 1538-1544, R. L. Dow, et al.

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