Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1995-10-05
1999-10-12
Morris, Patricia L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
548183, C07D41312, A61K 3142
Patent
active
059655895
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a novel thiazolidinedione derivative having hypoglycemic activity and blood lipid lowering activity, production thereof, and an antidiabetic agent containing it. The present invention is useful in the field of medicine.
BACKGROUND OF ART
As an agent for treating diabetes, various biguanide compounds and sulfonylurea compounds have been used. However, biguanide compounds are now hardly used because of their side effect of lactic acid acidosis. Although sulfonylurea compounds have potent hypoglycemic activity, they often cause serious hypoglycemia and must be used with care.
Thiazolidinedione derivatives having hypoglycemic activity and blood lipid lowering activity without the above disadvantages have been known. For example, JP-A 61-85372, JP-A 1-272573, JP-A 1-272574, JP-A 3-2173, JP-A 4-66579, JP-A 4-69383, JP-A 6-157522, etc., disclose 2,4-thiazolidinedione derivatives having at the 5-position a substituent such as a benzyl group or an arylmethyl group substituted by a substituted aromatic ring, etc.
DISCLOSURE OF INVENTION
The present inventors have intensively studied 2,4-thiazolidinedione derivatives. As a result, it has been found that a novel 2,4-thiazolidinedione derivative has hypoglycemic activity and blood lipid lowering activity, said 2,4-thiazolidinedione derivative having at the 5-position a substituent such as a 2-(substituted phenyl or substituted pyridyl)ethyl group, a 3-(substituted phenyl or substituted pyridyl)propyl group, a 4-(substituted phenyl or substituted pyridyl)butyl group, a 5-(substituted phenyl or substituted pyridyl)pentyl group, etc., and having a bivalent straight or branched hydrocarbon chain containing a substituted phenyl or substituted pyridyl group at the terminal (in the case of a branched hydrocarbon chain, a part of it and a substituent on the substituted phenyl group may be linked together to form a ring). Thus, the present invention has been completed.
The present invention provides a 2,4-thiazolidinedione derivative of the formula (I): ##STR2## wherein
R is an optionally substituted hydrocarbon group or a heterocyclic group which may be attached through a hydrocarbon chain;
n is 0 or 1;
X is CH or N;
Y is a bivalent hydrocarbon group;
R.sup.1 and R.sup.2 are the same or different and are a hydrogen atom, a halogen atom, an optionally substituted hydroxyl group or an optionally substituted hydrocarbon group, and either R.sup.1 or R.sup.2 and a part of Y may be linked together to form a ring; provided that ##STR3## is other than ##STR4## and
L and M are a hydrogen atom, or L and M are linked together to form a bond; or a salt thereof.
The present invention also provides a pharmaceutical composition which comprises a 2,4-thiazolidinedione derivative of the above formula (I) or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.
The present invention also provides a process for producing a 2,4-thiazolidinedione derivative of the formula (I-B2): ##STR5## wherein each symbol is as defined above, which comprises hydrolyzing an iminothiazolidinone compound of the formula (III): ##STR6## wherein each symbol is as defined above.
The present invention also provides a process for producing a 2,4-thiazolidinedione derivative of the formula (I-B2a): ##STR7## wherein
R' is an optionally substituted hydrocarbon group or a heterocyclic group which may be attached through a saturated hydrocarbon chain;
Y.sup.1 is a bivalent saturated hydrocarbon group;
either R.sup.1 or R.sup.2 and a part of Y.sup.1 may be linked together to form a ring;
provided that ##STR8## is other than ##STR9## and the other symbols are as defined above; which comprises reducing a compound of the formula (I-B1): ##STR10## wherein each symbol is as defined above.
The present invention also provides a process for producing a 2,4-thiazolidinedione derivative of the formula (I-D1): ##STR11## wherein R" is a heterocyclic group and the other symbols are as defined above, which comprises reacting a compound of the formula (V
REFERENCES:
patent: 4725610 (1988-02-01), Meguro et al.
patent: 5063240 (1991-11-01), Hindley
patent: 5130379 (1992-07-01), Clark et al., II
patent: 5330998 (1994-07-01), Clark et al., I
patent: 5468762 (1995-11-01), Malamas et al., II
patent: 5478852 (1995-12-01), Olefsky et al.
patent: 5532256 (1996-07-01), Malamas et al., I
Momose Yu
Odaka Hiroyuki
Sohda Takashi
Morris Patricia L.
Takeda Chemical Industries Ltd.
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