Imidazol-2-yl derivatives of substituted bicyclic compounds

Details Imidazol-2-yl derivatives of substituted bicyclic compounds Imidazol-2-yl derivatives of substituted bicyclic compounds

1992-07-24

1994-10-18

Morris, Patricia L.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514399, 5483114, 5483381, 5483411, 5483415, A61K 31415, C07D40502, C07D23360

Patent

active

053569202

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to new imidazol-2-yl derivatives of bicyclic compounds, in particular to imidazol-2-yl derivatives of 2H-1-benzopyran and 1,2-dihydronaphthalene, to a process for their preparation and to pharmaceutical compositions containing them.
WO-A-89/08646 discloses imidazol-2-yl derivatives having related chemical structure and analogous biological activity. However the compounds according to the present invention are more active than said prior-art compounds as shown by the comparative test data herein reported.
The invention provides compounds having the following general formula (I) ##STR2## wherein Z is --O-- or --CH.sub.2 --; -C.sub.3 alkyl group wherein the phenyl ring is unsubstituted or substituted by a substituent chosen from halogen, C.sub.1 -C.sub.4 alkyl and trihalo-C.sub.1 -C.sub.4 alkyl; group wherein the aryl moiety is unsubstituted or substituted by one to three substitutents chosen independently from C.sub.1 -C.sub.4 alkyl, halogen and trihalo-C.sub.1 -C.sub.4 alkyl; or c) a C.sub.5 -C.sub.8 cycloalkyl or C.sub.5 -C.sub.8 cycloalkyl-C.sub.1 -C.sub.3 alkyl group wherein the cycloalkyl ring is optionally substituted by one or two C.sub.1 -C.sub.4 alkyl groups, which may be the same or different; alkyl, or taken together with the carbon atom to which they are linked form a C.sub.3 -C.sub.6 cycloalkyl ring; ##STR3## wherein each of R' and R" independently is hydrogen or C.sub.1 -C.sub.8 alkyl, or one is hydrogen or C.sub.1 -C.sub.8 alkyl and the other is a") a C.sub.5 -C.sub.8 cycloalkyl ring unsubstituted or substituted by 1, 2 or 3 C.sub.1 -C.sub.4 alkyl groups, which may be the same or different; or b") a phenyl ring unsubstituted or substituted by 1 to 3 substitutents independently chosen from C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen and trihalo-C.sub.1 -C.sub.4 alkyl; is unsubstituted or substituted by 1 to 3 substituents independently chosen from C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen and trihalo-C.sub.1 -C.sub.4 alkyl; or -C.sub.3 alkyl group wherein the cycloalkyl ring is unsubstituted or substituted by one or two C.sub.1 -C.sub.4 alkyl groups, which may be the same or different; and the pharmaceutically acceptable salts thereof, and wherein, when at the same time Q is --OR' in which R' is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.1 is hydrogen or C.sub.1 -C.sub.6 alkyl, R.sub.2 is C.sub.1 -C.sub.8 alkyl, R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl and n is an integer of 1 to 3, then R.sub.3, being as defined above, is other than methyl.
The above proviso excludes from the scope of the compounds of formula (I) the prior art compounds disclosed in WO-A-89/08646.
The invention also includes within its scope all the possible isomers, stereoisomers and their mixtures and the metabolites and the metabolic precursors or bio-precursors of the compounds of formula (I). Pharmaceutically acceptable salts of the compounds of formula (I) include acid addition salts, with inorganic, e.g. nitric, hydrochloric, hydrobromic, sulphuric, perchloric and phosphoric acids, or organic, e.g. acetic, propionic, glycolic, lactic, oxalic, malonic, malic, maleic, tartaric, citric, benzoic, cinnamic, mandelic, fumaric, methanesulfonic and salicylic acids, and salts with inorganic, e.g. alkali metal, especially sodium or potassium, bases or alkaline-earth metal, especially calcium or magnesium, or with organic bases, e.g. alkylamines, preferably triethylamine, or basic naturally occurring aminoacids, preferably arginine. The alkyl groups may be branched or straight chain groups. A C.sub.1 -C.sub.8 alkyl group is e.g. a C.sub.1 -C.sub.6 alkyl group, in particular methyl, propyl, butyl or hexyl.
A C.sub.1 -C.sub.4 alkyl group is preferably methyl, ethyl, propyl, isopropyl or butyl, in particular methyl, ethyl or isopropyl. A C.sub.1 -C.sub.4 alkoxy group is preferably methoxy, ethoxy, propoxy or isopropoxy, in particular methoxy or ethoxy. A halogen atom is e.g. chlorine, bromine or fluorine, in particular chlorine or fluorine.
A trihalo-C.sub.1 -C.sub.4 alkyl

REFERENCES:
patent: 4510149 (1985-04-01), Cozzi et al.
patent: 4985440 (1991-01-01), Cozzi et al.

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