Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1991-10-25
1994-01-18
Morris, Patricia L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514 63, 514397, 514399, 546278, 548110, 5483151, 5483361, A61K 3144, A61K 31415, C07D40906, C07D23361
Patent
active
052800334
DESCRIPTION:
BRIEF SUMMARY
This application is a continuation (i.e., the U.S. national phase) of PCT International Application No. PCT/EP91/00351, filed Feb. 26, 1991.
The present invention relates to new 1-(alkoxy-iminoalkyl) imidazole derivatives, to a process for their preparation, to pharmaceutical compositions containing them and to their use as therapeutic agents.
The present invention provides novel compounds having the general formula (I) ##STR2## wherein
R is hydrogen or C.sub.1 -C.sub.4 alkyl;
A is a C.sub.1 -C.sub.4 alkylene chain unsubstituted or substituted by a phenyl ring unsubstituted or substituted by one or two substituents chosen independently from halogen and trifluoromethyl;
R.sub.1 is a) hydrogen or a straight or branched, saturated or unsaturated C.sub.1 -C.sub.10 hydrocarbon radical; b) an aryl or aryl-C.sub.1 -C.sub.4 alkyl group, wherein the aryl group or the aryl moiety is unsubstituted or substituted either by one to four substitutents independently chosen from halogen, trihalomethyl, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.3 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio and C.sub.1 -C.sub.4 alkylsulfonyl or by a substituent chosen from C.sub.5 -C.sub.8 alkyl, C.sub.4 -C.sub.8 alkenyl, C.sub.5 -C.sub.8 alkoxy, C.sub.5 -C.sub.8 alkylthio and phenyl, in which the phenyl ring is unsubstituted or substituted by a substituent chosen from halogen, trihalomethyl and 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.4 alkyl group, wherein the cycloalkyl group or moiety is unsubstituted or substituted by one to three C.sub.1 -C.sub.4 alkyl groups;
T is a straight or branched, saturated or unsaturated C.sub.1 -C.sub.6 hydrocarbon chain, or a phenylene radical;
X is a bond or a divalent group consisting of --O--CH.sub.2 --, --C(R' R")--, --Si(R' R")--, vinylene or isopropenylene, wherein each of R' and R" being the same or different is hydrogen, fluorine or C.sub.1 -C.sub.4 alkyl;
R.sub.2 is an --OR.sub.3 or --N(R.sub.3 R.sub.4) group, wherein each of R.sub.3 and R.sub.4 independently is hydrogen, C.sub.1 -C.sub.6 alkyl, phenyl or benzyl; and the pharmaceutically acceptable salts thereof.
The invention also includes within its scope all the possible isomers, stereoisomers and their mixtures and the metabolites and the metabolic precursors or bioprecursors of the compounds of formula (I).
In particular the compounds of formula (I) exhibit either E or Z isomerism about the oximic double bond. Both the single E and Z isomers of the compounds of formula (I) and their mixtures are also included within the scope of the present invention.
The alkylene chain A may be, independently, a straight or branched chain, unsubstituted or substituted, as defined above. Typically --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --CH.sub.2, ##STR3## CH.sub.2 --CH(CH.sub.2 Ph)-- and --CH--CH.sub.2 --CH(CH.sub.3)--Ph, wherein Ph represents a phenyl ring as defined above.
When R.sub.1 is a C.sub.1 -C.sub.10 hydrocarbon radical as defined above under a), it is preferably a C.sub.1 -C.sub.8 alkyl or C.sub.2 -C.sub.9 alkenyl radical, for example C.sub.2 -C.sub.8 alkenyl, in particular pentyl, hexyl and heptyl or propenyl and butenyl, respectively.
When R.sub.3 and/or R.sub.4 is a C.sub.1 -C.sub.6 alkyl group it is, e.g., methyl, ethyl, propyl, isopropyl, butyl or tert.butyl, more preferably methyl or ethyl.
When R.sub.1 is an aryl or arylalkyl group as defined above under b), the aryl group or the aryl moiety may be an aromatic or heteroaromatic group, for example phenyl, pyridyl, thienyl and naphthyl, in particular phenyl, pyridyl and thienyl. According to the definition of R.sub.1 as an aryl or arylalkyl group given hereabove, a pyridyl group is preferably a 2- or 3-pyridyl group; a thienyl group is preferably a 2-thienyl group and a naphthyl group is preferably a 1- or 2-naphthyl group.
Accordingly, an arylalkyl group, as defined above, is preferably a phenyl-, thienyl- or pyridyl-C.sub.1 -C.sub.2 alkyl group, in particular a ben
REFERENCES:
patent: 4352804 (1982-10-01), van Zorge
patent: 4599348 (1986-07-01), Schmetzer et al.
patent: 4797412 (1989-01-01), Knobs et al.
Cozzi Paolo
Ferti Corrado
Menichincheri Marla
Rossi Arsenia
Salvati Patricia
Farmitalia Carlo Erba S RL
Morris Patricia L.
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