Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-05-30
1999-06-08
Raymond, Richard L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514398, 5483111, 5483164, A01N 4350, C07D23340, C07D23328
Patent
active
059105062
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a novel imidazole derivative and a medicinal composition comprising it as an active ingredient.
BACKGROUND OF THE INVENTION
AIDS (acquired immune deficiency syndrome) is a serious social problem spread over the world as a refractory viral disease caused by HIV and the research and development of anti-HIV drugs have been undertaken on a worldwide scale. To this day, nucleic acid derivatives such as azidodeoxythymidine (AZT), dideoxyinosine (DDI), dideoxycytidine (DDC), dideoxydidehydrothymidine (D4T), and 3'-thiacytidine (3TC) have been developed as major target and put to use clinically, but severe adverse reactions and decreace of the efficacy due to occurrence of resistant strains have produced new problems and, therefore, the development of new therapeutic drugs has been eagerly awaited.
The pathologic picture of AIDS has not been fully elucidated yet, and recently it has been found that even in asymptomatic patients whose clinical stage is considered to be at a latent period, virologically the virus is actively proliferated in the lymph node. Therefore, development of an improved anti-HIV drug is an important social need today.
Meanwhile, explorations into various imidazole derivatives have been undertaken with the view of utilizing them as medicines.
U.S. Pat. No. 3,968,228 describes imidazole derivatives effective for the therapy of coccidiosis in animals as well as a variety of imidazole derivatives as intermediates for their synthesis. In the imidazole derivatives disclosed, however, the substituent attached directly to the inidazole ring via a --S--, --SO--, or --SO.sub.2 -- moiety is limited to alkyl groups.
U.S. Pat. No. 4,592,774 discloses imidazole derivatives which are of use as herbicides. However, all the disclosed imidazole derivatives necessarily have an opionally substituted phenylmethyl in the 2-position of the imidazole ring.
Japanese Kokai Hei-2-83373 discloses a series of imidazole derivatives of value as agrochemicals, medicines, perfumes, or polymer materials. These imidazole derivatives are substituted by hydrogen, cyano, carbamoyl, thiocarbamoyl, or a group of the formula COOR.sup.2 (those represented by substituent Y in the publication) in the 4- and/or 5-position(s).
Japanese Kokai Hei-5-252270 describes imidazole derivatives having anti-HIV activity In the disclose,, imidazole derivative, however, the substituent in the 1-position of the imidazole ring is limited to groups of the formula --(CH.sub.2)n--O--R.sub.3 having an ether linkage.
SUMMARY OF THE INVENTION
In view of the above state of the art, the present invention has for its object to provide a compound having the activity to specifically inhibit proliferation of the causative virus HIV in the lymph node and yet a low toxic potential.
The inventors of the present invention discovered that a series of imidazole derivatives having herein-defined substituent groups meet the above object and completed the present invention Thus, the present invention is essentially directed to any of such imidazole derivatives and medicinal compositions comprising them as active ingredient
DETAILED DISCLOSURE OF THE INVENTION
The present invention is now described in detail
The imidazole derivatives of the present invention have the following formula (I) ##STR2## (wherein R.sup.1 represents hydrogen, an alkyl group of 1 to 20 carbon atoms, an alkenyl group of 2 to 7 carbon atoms, a cycloalkylalkyl group of 4 to 12 carbon atoms, a haloalkyl group of 1 to 6 carbon atoms, an oxoalkyl group of 1 to 6 carbon atoms, an aroylalkyl group of 8 to 13 carbon atoms, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted heteroarylalkyl group, a substituted or unsubstituted carbamoyloxyalkyl, carbamoylalkyloxyalkyl, or acyloxyalkyl group, or a branched hydroxyalkyl group;
R.sup.2 represents an alkyl group of 1 to 6 carbon atoms, an acyl group of 1 to 6 carbon atoms, hydroxyiminomethyl, hydrazonomethyl, or a group of the formula --(CH.sub.2)n--R.sup.4 (where R.sup.4 repres
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Masaichiro Masui et al.; "Reactions of N-(1-cyanoalkyl)alkylideneamine N-oxides with dipolarophles and nucleophiles", Part I; Journal of the Chemical Society, Perkin Transactions 1, 1972, pp. 1955-1960, pp. 1957 and 1959, compound llld.
Masaichiro Masui et al.; "Convenient syntheses of 2,4(5)-dialkylimidazoles and 1-methyl-2,4-dialkyl-imidazoles", Journal of the Chemical Society, Perkins Transactions 1, 1972, pp. 1960-1963.
Fujiwara Tamio
Sugimoto Hirohiko
Ngo Tamthom T.
Raymond Richard L.
Shionogi & Co. Ltd.
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