Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-12-02
2000-02-29
Stockton, Laura L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
548183, A61K 31425, C07D27734
Patent
active
060309903
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to novel N-benzyldioxothiazolidylbenzamide derivatives that improve the diabetes mellitus and the hyperlipidemia, and processes for preparing the same.
BACKGROUND TECHNOLIGIES
So far, as oral therapeutic drugs for diabetes mellitus, biguanide type and sulfonylurea type compounds have been used. However, with biguanide type compounds, lactic acidosis or hypoglycemia is caused and, with sulfonylurea type compounds, serious and prolonged hypoglycemia is caused, and the adverse effect thereof is posing a problem, hence the appearance of new therapeutic drug for diabetes mellitus without such defects is desired. It is also known that some of thiazolidine-2,4-dione derivatives exhibit hypoglycemic and lipid-lowering effects (Journal of Medicinal Chemistry, Vol. 35, P. 1853 (1992), Published Unexamined Patent Application No. Hei 1-272573), but, in all of these compounds, the substituted position of middle benzene ring that connects thiazolidine-2,4-dione ring and aromatic ring is p-position, or the middle benzene ring has no substituent, further the aromatic ring of the former is oxazol ring, the linkage of the latter is through sulfonamide, and the like, which differ structurally from compounds of the invention, N-benzyldioxothiazolidylbenzamide derivatives.
For the non-insulin dependent diabetes mellitus (NIDDM) accounting for the majority of diabetics, a blood sugar-lowering drug that improves the insulin resistance and has high safety and effectiveness is strongly desired.
As a result of diligent studies on a drug that improves the insulin resistance and has potent hypoglycemic effects and high safety, the inventors have found that novel N-benzyldioxothiazolidylbenzamide derivatives represented by a following general formula (1) have excellent hypoglycemic and lipid-lowering effects, leading to the completion of the invention.
DISCLOSURE OF THE INVENTION
Namely, the invention provides N-benzyldioxothiazolidylbenzamide derivatives represented by a general formula (1) ##STR2## [wherein R.sup.1 and R.sup.2 denote identically or differently hydrogen atoms, lower alkyl groups with carbon atoms of 1 to 4, lower alkoxy groups with carbon atoms of 1 to 3, lower haloalkyl groups with carbon atoms of 1 to 3, lower haloalkoxy groups with carbon atoms of 1 to 3, halogen atoms, hydroxyl groups, nitro groups, amino groups which may be substituted with lower alkyl group(s) with carbon atoms of 1 to 3 or hetero rings, or R.sup.1 and R.sup.2 link to form a methylenedioxy group, R.sup.3 denotes a lower alkoxy group with carbon atoms of 1 to 3, hydroxyl group or halogen atom, and dotted line indicates double bond or single bond in combination with solid line], and their pharmacologically acceptable salts.
The salts of compounds represented by the general formula (1) in the invention are of common use, and pharmacologically acceptable metal salts such as alkali metal salts (e.g. sodium salt, potassium salt, etc.), alkaline earth metal salts (e.g. calcium salt, magnesium salt, etc.) and aluminum salt can be mentioned.
Moreover, the general formula (1) in the invention sometimes includes stereoisomers based on double bond and optical isomers based on thiazolidine portion. Such isomers and their mixtures are all to be included in the scope of this invention.
In the general formula (1) of the invention, for "lower alkyl group", straight or branched chain groups with carbon atoms of 1 to 4 such as methyl, ethyl, propyl and butyl are mentioned.
For "lower alkoxy group", straight or branched chain groups with carbon atoms of 1 to 3 such as methoxy, ethoxy and propoxy are mentioned.
For "lower haloalkyl group", straight or branched chain groups with carbon atoms of 1 to 3 such as trifluoromethyl are mentioned.
For "lower haloalkoxy group", straight or branched chain groups with carbon atoms of 1 to 3 such as trifluoromethoxy are mentioned.
For "halogen atom", fluorine atom, chlorine atom, bromine atom and iodine atom are mentioned.
For "amino group which may be substituted with lower
Awano Katsuya
Kinoshita Susumu
Maeda Toshio
Murakami Koji
Nomura Masahiro
Kyorin Pharmaceutical Co. Ltd.
Stockton Laura L.
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