Sulfonic acid ester derivatives useful as antilipemic agents

Details Sulfonic acid ester derivatives useful as antilipemic agents Sulfonic acid ester derivatives useful as antilipemic agents

1986-05-07

1987-06-23

Chan, Nicky

Organic compounds -- part of the class 532-570 series

Organic compounds

Sulfonate esters

C07C14368

Patent

active

046754288

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

This invention relates to novel sulfonic acid ester derivatives, and more particularly to antilipemic sulfonate derivatives and a process for preparing the same.


BACKGROUND ART

Hyperlipidemia is known to be a risk factor leading to various adult diseases, such as arteriosclerosis, cardio- and nephro-vascular diseases, diabetes, etc. The drugs for preventing or alleviating hyperlipidemia must have high safety because such drugs are likely to be used for a prolonged period of time in view of the nature of the disease. However, reports have been made on various side effects of nicotinic acid and derivatives thereof, dextran sulfate, and clofibrate and derivatives thereof heretofore known as antilipemic agents. Nicotinic acid and its derivatives, for example, produce side effects, such as pruritus and cutaneous flushing due to vasodilatation, gastrointestinal disorders, abnormalities in liver function and glucose intolerance. These drugs have many side effects further because they must be given at a large dose of at least 3 g/day. Furthermore clofibrate, which is typical of antilipemic agents which are widely used throughout the world, has recently been reported as having a carcinogenic activity as a serous side effect. Although animal tests or immunological investigations are being carried out on clofibrate by research institutes, the ultimate conclusions still remain to be made, so that clofibrate is clinically in limited use in various countries. In addition to the carcinogenic activity, clofibrate causes an increased sterol discharge, which reportedly increases the likelihood of gallstone formation. Thus the drug is likely to pose the problem of another side effect.
In view of the foregoing situation, we have conducted intensive research in order to provide more useful compounds having outstanding antilipemic activity and found that the compounds represented by the general formula (I) below fulfill this object. Thus the present invention has been accomplished.


DISCLOSURE OF THE INVENTION

The sulfonic acid ester derivatives of the present invention are represented by the following general formula. ##STR4## wherein R.sub.1 is a hydrogen atom, alkyl having 1 to 4 carbon atoms or alkoxy having 1 to 4 carbon atoms, A is a group represented by the general formula: ##STR5## (wherein R.sub.2 and R.sub.3 are each alkyl having 1 to 4 carbon atoms) or by the general formula ##STR6## (wherein R.sub.4 and R.sub.5 are each alkyl having 1 to 4 carbon atoms or, when taken together with the carbon atom to which they are attached, form cycloalkyl having 4 to 6 carbon atoms), and l is an integer of from 1 to 3.
Examples of alkyl groups having 1 to 4 carbon atoms and represented by R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 of the general formula (I) are straight-chain or branched-chain alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl and the like. Examples of alkoxy groups represented by R.sub.1 and having 1 to 4 carbon atoms are straight-chain or branched-chain alkoxy groups such as methoxy, ethoxy, propyloxy, isopropyloxy, butoxy, isobutyloxy and the like. Examples of cycloalkyl groups which have 4 to 6 carbon atoms and which can be formed by R.sub.4 and R.sub.5 when they are taken together with the carbon atoms to which they are attached are cyclobutyl, cyclopentyl and cyclohexyl.
The compounds of the present invention represented by the general formula (I) include those having steric isomers. The invention includes all of these isomers.
Of the present compounds represented by the general formula (I), those wherein R.sub.1 is a hydrogen atom are preferred. Other preferred compounds are those wherein A is a group represented by ##STR7## and the conformation of R.sub.2 and R.sub.3 is a cis form, and those wherein A is a group represented by ##STR8## R.sub.4 and R.sub.5 being each alkyl having 1 to 3 carbon atoms or forming cyclopentyl or cyclohexyl when taken together with the carbon atom to which they are attached.
The compound of the invention represented by the general for

REFERENCES:
patent: 4411911 (1983-10-01), Fujii et al.
patent: 4452813 (1984-06-01), Fujii et al.
Fujii et al., Chem. Abstr., 96,51998w, (1982)-Abstract of FR. Demande FR 2,475,041.

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