Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1994-12-12
1996-12-31
Northington-Davis, Zinna
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514347, 514274, 514275, 514375, 544318, 544332, 5462717, 546294, 546301, 546334, 548222, C07D41312, C07D21374, A61K 3142, A61K 3144
Patent
active
055894925
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/GB/93/00735 filed Apr. 7, 1993 and published as WO93/21166 Oct. 28, 1993.
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, 155845, 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. Chem. Pharm. Bull 1982, 30 (10) 3563 also relates to certain ethyl 2-chloro propionate derivatives having hypoglycaemic and hypolipidaemic activities.
It has now surprisingly been discovered that certain novel .alpha.-thiocarbonyl and .alpha.-halocarbonyl derivatives show 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, hypertension, cardiovascular disease and certain eating disorders.
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 a halogen atom or a moiety of formula S(O).sub.p A.sup.4 wherein A.sup.4 represents hydrogen, substituted or unsubstituted alkyl, aryl, aralkyl, alkylcarbonyl or an aromatic heterocyclyl group and p represents zero or an integer 1 or 2 and m represents zero or an integer in the range of from 1 to 5, or A.sup.3 represents a moiety of formula --CH.dbd.CR.sup.1 -- wherein R.sup.1 is as defined above; aryl or aralkyl, or R.sup.2 represents --NR.sup.4 R.sup.5 wherein R.sup.4 and R.sup.5 each independently represent hydrogen or alkyl or R.sup.4 and R.sup.5 together with the nitrogen atom to which they are attached form a heterocyclic ring; group, an acyl group, an aralkyl group wherein the aryl moiety may be substituted or unsubstituted, or a substituted or unsubstituted aryl 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.
Favoured aromatic heterocyclyl groups include substituted or unsubstituted single ring aromatic heterocyclyl groups having 4 to 7 ring atoms, preferably 5 or 6 ring atoms.
In particular, the aromatic heterocyclyl group comprises 1, 2 or 3 heteroatoms, especially 1 or 2, selected from oxygen, sulphur or nitrogen.
Suitable values for A.sup.1 when it represents a 5-membered aromatic heterocyclyl group include thiazolyl and oxazolyl, especially oxazolyl.
Suitable values for A.sup.1 when it represents a 6- membered aromatic heterocyclyl group include pyridyl or pyrimidinyl, especially pyridyl.
A particular pyridyl group is a 2-pyridyl group.
Preferably, A.sup.1 represents a moiety of formula (a), (b) or (c): ##STR1## wherein:
R.sup.6 and R.sup.7 each independently represents a hydrogen or halogen atom, an alkyl or alkoxy group or a substituted or unsubstituted aryl group or when R.sup.6 and R.sup.7 are each attached to adjacent carbon atoms, then R.sup.6 and R.sup.7 together with the carbon atoms to which they are attached form a benzene ring wherein each carbon atom represented by R.sup.6 and R.sup.7 together may be substituted or unsubstituted; and in the moiety of formula (a)
Aptly, A.sup.1 represents a moiety of the above defined formula (a).
Aptly, A.sup.1 represents a moiety of the above defined formula (b).
Aptly, A.sup.1 represents a moiety of the above defined formula (c).
In one favoured aspect R.sup.6 and R.sup.7 together represent a moi
REFERENCES:
Takashi Sohda, et al., Chemical and Pharmaceutical Bulletin, vol. 30, No. 10, pp. 3563-3573 (1982).
Takashi Sohda, et al., Chemical and Pharmaceutical Bulletin, vol. 30, No. 10, pp. 3580-3600 (1982).
King William T.
Lentz Edward T.
Northington-Davis Zinna
SmithKline Beecham Plc
Stein-Fernandez Nora
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