Imidazole derivatives as anti-HIV agents
AssigneeShionogi & Co., Ltd.
InventorsHirohiko Sugimoto, Tamio Fujiwara
Life of this patent
Estimating the term…
Abstract
An imidazole derivative represented by general formula (I) or a salt thereof, having the effect of specifically inhibiting the growth of HIV as a pathogenic virus and being reduced in toxicity. In said formula R.sup.1 represents hydrogen, C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.7) alkenyl, C.sub.4 -C.sub.12 cycloalkylalkyl, etc.; R.sup.2 represents C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 acyl, hydroxyiminomethyl, hydrazonomethyl or --(CH.sub.2)n--R.sup.4 (R.sup.4 being halogeno, alkoxy, hydroxy, etc.; and n being an integer of 1 to 3); R.sup.3 represents substituted or unsubstituted C.sub.1 -C.sub.6 alkyl; X and Y represent each independently hydrogen, C.sub.1 -C.sub.3 alkyl, halogeno, or nitro; and Z represents S, SO, SO.sub.2 or CH.sub.2. ##STR1##
Claims20
A compound selected from the group consisting of an imidazole compound of the formula (I') or a pharmaceutically acceptable salt thereof:
- ##STR11## wherein R.sup.1 represents 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, provided that R.sup.1 does not represent a substituted or unsubstituted biphenylalkyl 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).sub.n --R.sup.4 wherein R.sup.4 represents halogen, an alkoxy group, hydroxy, cyano, an acyloxy group, an aryloxycarbonyloxy group, an alkoxycarbonyloxy group, carboxy, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted hydroxyalkyloxy group, a substituted or unsubstituted benzyloxy group, a substituted carbamoyloxy or thiocarbamoyloxy group, a substituted or unsubstituted amino group, or azido and n represents a whole number of 1 to 3, wherein R.sup.2 represents a group other than alkyl groups, either when Z is CH.sub.2, or when both X and Y are hydrogen;
- R.sup.3 represents a substituted or unsubstituted alkyl group of 1 to 6 carbon atoms;
- X and Y independently represent hydrogen, an alkyl group of 1 to 3 carbon atoms, halogen, or nitro;
- and
- Z represents S, SO, SO.sub.2 or CH.sub.2.
A method for preparing a pharmaceutical formulation for the treatment of HIV which comprises combining an anti-HIV effective amount of an imidazole compound of the formula (I'):
- ##STR12## wherein R.sup.1 represents 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, provided that R.sup.1 does not represent a substituted or unsubstituted biphenylalkyl 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).sub.n --R.sup.4 wherein R.sup.4 represents halogen, an alkoxy group, hydroxy, cyano, an acyloxy group, an aryloxycarbonyloxy group, an alkoxycarbonyloxy group, carboxy, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted hydroxyalkyloxy group, a substituted or unsubstituted benzyloxy group, a substituted carbamoyloxy or thiocarbamoyloxy group, a substituted or unsubstituted amino group, or azido and n represents a whole number of 1 to 3, wherein R.sup.2 represents a group other than alkyl groups, either when Z is CH.sub.2, or when both X and Y are hydrogen;
- R.sup.3 represents a substituted or unsubstituted alkyl group of 1 to 6 carbon atoms;
- X and Y independently represent hydrogen, an alkyl group of 1 to 3 carbon atoms, halogen, or nitro;
- and
- Z represents S, SO, SO.sub.2 or CH.sub.2 ;
- or a pharmaceutically acceptable salt thereof, as an active ingredient and a pharmaceutically acceptable carrier.
A method for treating AIDS which comprises administering to human beings an anti-HIV effective amount of an imidazole compound of the formula (I):
- ##STR13## wherein R.sup.1 represents 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, wherein R.sup.4 represents halogen, an alkoxy group, hydroxy, cyano, an acyloxy group, an aryloxycarbonyloxy group, an alkoxycarbonyloxy group, carboxy, a substituted or unsubstituted carbamoyl group, substituted or unsubstituted hydroxyalkyloxy group, a substituted or unsubstituted benzyloxy group, a substituted or unsubstituted carbamoyloxy or thiocarbamoyloxy group, a substituted or unsubstituted amino group, or azido, and n represents a whole number of 1 to 3;
- R.sup.3 represents a substituted or unsubstituted alkyl group of 1 to 6 carbon atoms;
- X and Y independently represent hydrogen, an alkyl group of 1 to 3 carbon atoms, halogen, or nitro;
- and
- Z represents S, SO, SO.sub.2 or CH.sub.2,
- or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.