Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-03-03
1999-10-12
Higel, Floyd D.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
5483361, 5483401, 5483411, 5483435, 5483461, 514399, 514400, C07D23358, C07D23360, C07D23361, A61K 31415
Patent
active
059657430
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
The present invention relates to novel imidazole derivatives effectual as an antihyperlipemic agent and therapeutic and preventive drugs for arteriosclerosis and methods for manufacturing the said imidazole derivatives.
BACKGROUND ART
In recent years, antihyperlipemic agents, which inhibit the biosynthesis of cholesterol and neutral lipids, which are both influential as the inducing cause of arteriosclerosis and other diseases, have attracted considerable attention.
As the representative drugs for such diseases, pravastatin and simvastatin are presently known.
As the similar compounds to the compounds of the present invention, the following compounds are disclosed as an antimicrobial agent in Japanese Patent Publication No. Sho 60-18654, ##STR4## and the following compound is disclosed as an preventive agent for decoloration in Japanese Patent Laid-opened No. Hei 2-197839, ##STR5## and further, the following compound is disclosed as an anti-allergic agent in Japanese Patent Laid-opened No. Hei 6-199791. ##STR6##
It is an object of the present invention to provide novel imidazole derivatives, which are excellently effective on hyperlipemia, having therapeutic and preventive effect on arteriosclerosis, safe, and causing less side effect, and to provide advantageous methods for manufacturing the said imidazole derivatives in an industrial scale.
DISCLOSURE OF THE INVENTION
The present invention is directed to the compounds represented by the following general formula [I]; ##STR7## wherein R.sup.1 is hydrogen or lower alkyl, n is 0 or 1, X is N-r.sup.1 wherein r.sup.1 is hydrogen or lower alkyl, O, S, SO, SO.sub.2, CH.sub.2, CH(CH.sub.3), CONH or C(r.sup.2).dbd.NO wherein r.sup.2 is hydrogen or lower alkyl, m denotes 0 or an integer of from 1 to 12, and A is methyl or a group represented by the following general formula; ##STR8## wherein Y is N-r.sup.3 wherein r.sup.3 is hydrogen or lower alkyl, N(r.sup.4)SO.sub.2 wherein r.sup.4 is hydrogen or lower alkyl, O, S, SO, SO.sub.2, CH.sub.2, CH(CH.sub.3), CONH or C(r.sup.5).dbd.NO wherein r.sup.5 is hydrogen or lower alkyl, R.sup.2 is halogen, lower alkyl, lower alkoxy, cycloalkyl or COOr.sup.6 wherein r.sup.6 is hydrogen or lower alkyl, and l is 0, 1, 2 or 3, however m denotes an integer of from 6 to 9 when A is methyl, or m denotes 0 or an integer of from 1 to 6 when A is a group represented by the following general formula; ##STR9## and X and Y is each independently CH.sub.2 when m is 0, the pharmaceutically-acceptable salts thereof and methods for manufacturing the said compounds and the said pharmaceutically acceptable salts.
For examples of the pharmaceutically-acceptable salts of the present invention, inorganic acids, such as hydrochloric acid, sulfuric acid, nitric acid and phosphoric acid, organic acids, such as acetic acid, propionic acid, lactic acid succinic acid, tartaric acid, citric acid, benzoic acid, salicylic acid, nicotitic acid and heptagluconic acid, can be given.
In the present invention, for examples of the lower alkyl represented by the substituents, R.sup.1, R.sup.2, r.sup.1, r.sup.2, r.sup.3, r.sup.4, r.sup.5 and r.sup.6, straight-chain or branched alkyl having 1 to 6 carbon atoms, preferably methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and t-butyl, can be given. The halogen represented by the substituent R.sup.2 may be any of fluorine, chlorine, bromine and iodine, and the lower alkoxy represented by the substituent R.sup.2 is straight-chain or branched alkoxy having 1 to 6 carbon atoms, preferably any of methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, t-butoxy and sec-butoxy. And, the cycloalkyl represented by R.sup.2 is the ones containing 3 to 7 carbon atoms.
The compounds of the present invention can be manufactured according to the following manufacturing methods. where in n is 0; ##STR10## wherein X' is N-r.sup.1, O, S or C(r.sup.2).dbd.NO and Hal denotes an halogen atom.
The reaction represented by the reaction formula as shown hereinabove is carried out for from 30 min. to se
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Ichihara Hiromi
Kumita Izumi
Miyamoto Hiroyuki
Mochizuki Nobuo
Uchida Seiichi
Higel Floyd D.
Nippon Soda Co. Ltd.
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