Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1995-03-09
2000-04-11
Gupta, Yogendra N.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514367, 514375, 514377, 548161, 548163, 548193, 548194, 548195, 548203, 548204, A61K 31425, C07D27738
Patent
active
060488832
DESCRIPTION:
BRIEF SUMMARY
This invention relates to certain novel compounds, to a process for preparing such compounds, to pharmaceutical compositions containing such compounds and to the use of such compounds and compositions in medicine.
European Patent Applications, Publication Numbers 0008203, 0139421, 0155845, 0177353, 0193256, 0207581, 0208420, 0306228 and International Patent Application Publication No. WO 9101337 relate to thiazolidinedione derivatives which are disclosed as having hypoglycaemic and hypolipidaemic activity. Chem. Pharm. Bull 1982, 30 (10) 3580-3600 relates to certain thiazolidinedione derivatives having hypoglycaemic and hypolipidaemic activities.
International Patent Application, Publication Number WO 91/19702 discloses compounds of formula (A) and (B): ##STR1## wherein A is ##STR2## n is 0 or 1; m is 0, 1 or 2; -C.sub.8)alkenyl, (C.sub.3 -C.sub.8)alkynyl, phenyl, (C.sub.7 -C.sub.8)phenylalkyl, (C.sub.2 -C.sub.8)alkanoyl, or one of said groups mono- or disubstituted with (C.sub.1 -C.sub.3)alkyl, trifluoromomethyl, hydroxy, (C.sub.1 -C.sub.3)alkoxy, fluoro or chloro; phenyl, or phenyl mono- or disubstituted with (C.sub.1 -.sub.3)alkyl, trifluoromethyl, (C.sub.1 -C.sub.3)alkoxy, phenyl, phenoxy, benzyl, benzyloxy, fluoro or chloro; (C.sub.1 -C.sub.4)alkanoylamino, (C.sub.1 -C.sub.4)alkanesulfonyl-amino, benzenesulfonylamino, naphthalenesulfonylamino, di[(C.sub.1 -C.sub.3)alkyl]aminosulfonylamino, or one of said groups mono- or disubstituted with (C.sub.1 -C.sub.3)alkyl, trifluoromethyl, hydroxy, (C.sub.1 -C.sub.3)alkoxy, fluoro or chloro; the pharmaceutically-acceptable cationic salts thereof when Y.sup.1 is hydroxy; and the pharmaceutically-acceptable acid addition salts thereof when the compounds contain a basic nitrogen atom.
The compounds of formula (A) are stated to be useful as hypoglycaemic and hypochlolesterolemic agents.
It has now surprisingly been discovered that certain novel compounds, structurally distinct from the abovementioned compounds, show particularly good blood-glucose lowering activity and are therefore of potential use in the treatment and/or prophylaxis of hyperglycaemia and are of particular use in the treatment of Type II diabetes.
These compounds are also indicated to be of potential use for the treatment and/or prophylaxis of other diseases including hyperlipidaemia and hypertension. They are also indicated to be of use in the treatment and/or prophylaxis of cardiovascular disease, especially atherosclerosis. In addition these compounds are considered to be useful for treating certain eating disorders, in particular the regulation of appetite and food intake in subjects suffering from disorders associated with under-eating, such as anorexia nervosa, and disorders associated with over-eating, such as obesity and anorexia bulimia.
Accordingly, the present invention provides a compound of formula (I): thereof, and/or a pharmaceutically acceptable solvate thereof, wherein: group; wherein R.sup.1 represents substituted or unsubstituted alkyl, aryl, aralkyl or alkylcarbonyl and m represents an integer in the range of from 1 to 5, or A.sup.3 represents a moiety of formula --(CH.sub.2).sub.m-1 --CH.dbd.C(OR.sup.1)-- wherein R.sup.1 and m are as defined above; aryl or aralkyl or R.sup.2 represents an aromatic heterocyclyl group or --NR.sup.4 R.sup.5 wherein R.sup.4 and R.sup.5 each independently represent hydrogen, alkyl or alkylcarbonyl or R.sup.4 and R.sup.5 together with the nitrogen atom to which they are attached form a heterocyclic ring, providing that R.sup.2 represents an aromatic heterocyclyl group only when Y as defined below represents a bond; acyl group, an aralkyl group wherein the aryl moiety may be substituted or unsubstituted, or a substituted or unsubstituted aryl group; bond only when R.sup.2 represents the above mentioned aromatic heterocyclyl group; and
Suitable aromatic heterocyclyl groups include substituted or unsubstituted, single or fused ring aromatic heterocyclyl groups comprising up to 4 hetero atoms in each ring selected from oxygen, sulphur or nitrogen.
Favou
REFERENCES:
CA 114:61509, 1991.
Advance Organic Chemistry, John Wiley & Sons Inc, 1985, Jerry March pp. 234-236.
Haigh David
Sime John Thomas
Gupta Yogendra N.
Kinzig Charles M.
SmithKline Beecham p.l.c.
Stercho Yuriy P.
Venetianer Stephen A.
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