Acylsulfonamide derivative

Details Acylsulfonamide derivative Acylsulfonamide derivative

2000-06-29

2003-04-29

Aulakh, Charanjit S. (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Nitrogen containing other than solely as a nitrogen in an...

C564S086000, C564S088000, C564S090000, C564S092000

Reexamination Certificate

active

06555584

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to acylsulfonamide derivatives, more particularly to a novel acylsulfonamide derivative which has the activity to inhibit acetyl-CoA carboxylase (also to be referred to as “ACC” hereinafter).
BACKGROUND ART
It has been revealed in recent years that excess accumulation of neutral fat, particularly triglyceride, in visceral fat tissue is an important risk-factor for various diseases such as hyperlipemia, hypertension, arteriosclerosis, myocardial infarction and glucose tolerance abnormality. That is, it is considered that fatty acid synthesis is activated in the visceral fat tissue, and the fatty acids accelerate insulin resistance when released in the portal vein and are further incorporated into the liver and used as materials of triglyceride which is then released into blood plasma to cause hypertriglyceridemia.
On the other hand, ACC is an enzyme which catalyzes synthesis of malonyl-CoA from acetyl-CoA and is a rate-limiting enzyme in the biosynthesis of long chain fatty acids. Also, it is known that the malonyl-CoA itself synthesized from acetyl-CoA by the action of ACC controls carnitine acyltransferase which is concerned in the consumption of free long chain fatty acids as energy source. In addition, it is considered that activation of ACC is concerned in the activation of fatty acid synthesis in the visceral fat tissue. In consequence, an agent capable of inhibiting the ACC activity inhibits biosynthesis of long chain fatty acids in the living body, while simultaneously accelerating their metabolism, and thereby reduces the amount of long chain fatty acids in the living body and inhibits biosynthesis of triglyceride as a result, so that it has a possibility as a drug for the treatment and prevention of various diseases caused by the accumulation of visceral fat.
SUMMARY OF THE INVENTION
Based on such a viewpoint, the present inventors have conducted intensive studies with the aim of finding an ACC activity inhibitor effective for the treatment of visceral fat syndrome which becomes the risk-factor for diseases of adult people such as myocardial infarction, cerebral infarction and diabetes, and have newly found as a result of the efforts that excellent ACC inhibition activity can be found in acylsulfonamide derivatives represented by a general formula (I) shown in the following. The invention has been accomplished based on this finding. Thus, the invention contemplates providing a novel acylsulfonamide derivative and a medicament, particularly an ACC activity inhibitor, which uses such compound as the active ingredient.
Accordingly, an object of the invention is to provide an acylsulfonamide derivative represented by a general formula 1
wherein R
1
represents a substituted or unsubstituted C
1
-C
12
alkyl group, a substituted or unsubstituted C
2
-C
12
alkenyl group, a substituted or unsubstituted C
2
-C
12
alkynyl group or a substituted or unsubstituted C
1
-C
12
alkoxy group, R
2
represents a hydrogen atom, a hydroxyl group, a mercapto group, a substituted or unsubstituted C
1
-C
6
alkoxy group, a substituted or unsubstituted C
1
-C
6
alkylthio group, a nitro group, a halogen atom, a trichloromethyl group, a trifluoromethyl group or a cyano group, R
3
represents a substituted or unsubstituted C
1
-C
20
alkyl group, a substituted or unsubstituted C
2
-C
20
alkenyl group, a substituted or unsubstituted C
2
-C
20
alkynyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted amino group, a substituted or unsubstituted C
1
-C
20
alkoxy group, a substituted or unsubstituted C
2
-C
20
alkenyloxy group, a substituted or unsubstituted C
2
-C
20
alkynyloxy group or a group represented by R
4
O— (wherein R
4
represents a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group), Y is a group represented by —CH═CH—, —N═CH— or —CH═N—, sulfur atom or oxygen atom, and ring A represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group or a substituted or unsubstituted cyclic alkyl group.
Other objects and advantages of the invention will be made apparent as the description progresses.


REFERENCES:
patent: 6235680 (2001-05-01), Ziemer et al.
patent: 1336983 (1973-11-01), None
Chemical Abstracts, vol. 131, (6), abst.No. 73368j pub.Aug. 9, 1999 which abstracts Jpn.Kokai Tokkyo Koho, Jp 11 171,856, 38 pages published Jun. 29, 1999.

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