Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1992-10-26
1994-05-03
Gerstl, Robert
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
548181, C07D41710, A61K 31435
Patent
active
053088565
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to novel thiazolidine-2,4-dione derivatives possessing blood sugar-lowering action and aldose reductase-inhibitory action, their salts, their preparation processes and a drug containing them.
BACKGROUND TECHNIQUES
As therapeutic agents for diabetes, various biguanide type and sulfonylurea type compounds have been used so far. However, the biguanide type compounds cause the lactic acid acidosis and the sulfonylurea type compounds cause serious hypoglycemia posing a problem on their adverse effect, thus the advent of therapeutic agent for diabetes without such defect is desired.
On the other hand, it has been made clear that the aldose reductase takes part in the crisis of diabetic complication (J. H. Kinoshita et al, J. Am. Med. Assoc. 246, 257 (1981)). Thus inhibition of the aldose reductase may bring prevention and therapy of diseases occurring as diabetic complications.
Compounds possessing blood sugar-lowering action and compounds possessing inhibitory action of aldose reductase have been extensively searched each separately, and, with regard to particular thiazolidine-2,4-dione derivatives, compounds having aldose reductase-inhibitory action or blood sugar-lowering action are known.
For example, as the aldose reductase-inhibitory agents, particular thiazolidine-2,4-dione derivatives are already publicly known (Japanese Unexamined Patent Publication No. Sho 57-28073, Chem. Pharm. Bull. 30(10), 3601, (1982)). Namely, it is publicly known that 5-phenylthiazolidine-2,4-dione derivatives represented by a general formula ##STR2## [wherein R denotes a hydrogen atom, lower alkyl group, hydroxyl group, alkoxy group, nitro group, amino group, lower acylamino group, halogen or trifluoromethyl group], have aldose reductase-inhibitory action.
However, thiazolidine-2,4-dione derivatives of the present invention represented by a general formula (1) ##STR3## [wherein R.sup.1 and R.sup.2 each independently represent hydrogen atoms, halogens, lower alkyl groups, hydroxyl groups, lower alkoxy groups, nitro groups or amino groups (said amino group may be substituted with lower alkyl group or lower alkanoyl group), R.sup.3 denotes a hydrogen atom or lower alkyl group, A denotes a lower alkylene or carbonyl group, and B and W denote differently lower alkylenes, carbonyl groups or bonding hands], were not known at all, and also it could not be anticipated that thiazolidine-2,4-dione derivatives of the present invention had superior blood sugar-lowering action together with strong aldose reductase-inhibitory action.
The purpose of the present invention is to provide compounds having superior blood sugar-lowering action and simultaneously strong aldose reductase-inhibitory action and being useful as effective and highly-safe drugs capable of preventing and treating diabetes and complication thereof.
DISCLOSURE OF THE INVENTION
As a result of diligent studies for solving such problems, the inventors have found that thiazolidine-2,4-dione derivatives represented by the general formula (1) ##STR4## [wherein R.sup.1 and R.sup.2 each identically represent hydrogen atoms, halogens, lower alkyl groups, hydroxyl groups, lower alkoxy groups, nitro groups or amino groups (said amino group may be substituted with lower alkyl group or lower alkanoyl group), R.sup.3 denotes a hydrogen atom or lower alkyl group, A denotes a lower alkylene or carbonyl group, and B and W denote differently lower alkylenes, carbonyl groups or bonding hands], or their salts have superior blood sugar-lowering action and aldose reductase-inhibitory action in combination, leading to the completion of the invention.
For the "lower alkyl" shown in the present invention, straight chain or branched ones with carbon atoms of 1 to 6 such as methyl, ethyl, n-propyl and i-propyl are exemplified. For "halogen", fluorine, chlorine, bromine and iodine are exemplified. For "lower alkoxy", straight chain or branched ones with carbon atoms of 1 to 6 such as methoxy, ethoxy, n-propoxy and i-propoxy are exemplified. For "lower
Hirata Yoshihiro
Murakami Koji
Ohashi Mitsuo
Ohnota Michiro
Okamura Kyuya
Gerstl Robert
Kyorin Pharmaceutical Co. Ltd.
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