Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1994-01-28
1996-09-24
Higel, Floyd D.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
514255, 514272, 514341, 514365, 514397, 514398, 514399, 514400, 544324, 544370, 5462727, 5462751, 5462741, 5462704, 5483111, 5483124, 5483144, 5483151, 5483154, 5483261, 5483355, 5483391, 548171, A61K 31415, C07D23364, C07D23384, C07D40112, C07D40312, C07D41712
Patent
active
055591132
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel imidazole derivatives, to their preparation and to their therapeutic applications.
The imidazole derivatives in accordance with the invention show useful antagonist properties for histamine H.sub.3 receptors which control the release and synthesis of histamine. Their antagonist activity on the H.sub.3 receptors makes them useful in therapeutics, in particular as a medicament possessing sedative, sleep regulating, anticonvulsant, psychostimulating, cerebral circulation modulating and anti-ulcer effects.
The derivatives in accordance with the invention correspond to the general formula IA or IB ##STR2## in which the chain A represents a saturated or unsaturated, straight or branched hydrocarbon chain containing 1 to 6 carbon atoms, it being possible for the saturated hydrocarbon chain to be interrupted by a hetero atom such as a sulphur atom, --NHCONH--, --NH--CS--NH--, --NHCS--, --O--CO--, --CO--O--, --OCONH--, --OCON(alkyl)--, --OCONH--CO--, --CONH--, --CON(alkyl)--, --SO--, --CO--, --CHOH-- or --NR--C(.dbd.NR")--NR'--, R and R' denoting a hydrogen atom or a lower alkyl radical and R" a hydrogen atom or another powerful electronegative group, such as a cyano or COY.sub.1 group, Y.sub.1 denoting an alkoxy group,
the chain B represents a straight alkylene chain --(CH.sub.2).sub.n --, n being an integer which can vary between 0 and 5 or a branched alkylene chain containing from 2 to 8 carbon atoms, it being possible for the alkylene chain to be interrupted by one or a number of oxygen or sulphur atoms, or a group --(CH.sub.2).sub.n --O-- or --(CH.sub.2).sub.n --S-- where n is an integer equal to 1 or 2,
Y represents a straight or branched alkyl group containing 1 to 8 carbon atoms, a cycloalkyl containing 3 to 6 carbon atoms, a bicycloalkyl group, a cycloalkenyl group, an aryl group such as an optionally substituted phenyl group, a 5- or 6-membered heterocyclic radical containing one or two heteroatoms chosen from nitrogen and sulphur atoms, the said heterocyclic radical optionally being substituted, or also a bicyclic radical resulting from the fusion of a benzene ring to a heterocycle as defined above.
The chain A can be a straight alkylene chain --(CH.sub.2).sub.n --, n representing an integer between 0 and 6 carbon atoms, preferably between 1 and 4 carbon atoms, or a branched alkylene chain, preferably a chain substituted by one or a number of methyl or ethyl radicals.
The chain A can also be a straight or branched alkylene chain, and can be, for example, the allyl group.
When Y represents a cycloalkyl group, the latter can be, for example, cyclopentyl, cyclohexyl or a bicycloalkyl group.
When Y represents a substituted phenyl group, the phenyl group can be mono- or polysubstituted, for example, by a halogen, by a lower alkyl, for example CH.sub.3, by CF.sub.3, CN, COCH.sub.3, COOR.sub.1 or OR.sub.1, R.sub.1 representing a lower alkyl, for example COOCH.sub.3, the NO.sub.2 group or the group NR.sub.2 R.sub.3, R.sub.2 and R.sub.3 representing a hydrogen atom and/or a lower alkyl radical ("lower alkyl" means an alkyl radical containing at most 6 carbon atoms).
When Y represents a heterocyclic radical, the latter can be, for example, the pyridyl radical, the pyridyl N-oxide radical or the pyrazinyl radical, optionally mono- or polysubstituted by NO.sub.2, CF.sub.3, CH.sub.3, NH.sub.2, a halogen such as Cl, the COOCH.sub.3 group or also the imidazolyl or thiazolyl radical.
When Y represents a bicyclic radical resulting from the fusion of a benzene ring to a heterocycle, the radical can be, for example, the benzothiazyle radical.
The compounds which correspond to the formula IA or IB are novel compounds, with the exception, however: --(CH.sub.2).sub.2 -- group, the chain B the --(CH.sub.2).sub.2 --O-- group or the group --(CH.sub.2).sub.n --S-- and Y the phenyl or p-chloro phenyl group, the --(CH.sub.2).sub.2 -- group and Y the methyl group (formula IB) or the chain B and Y (formula IA) represent a straight alkylene chain --(CH.sub.2).sub.n --, n being between 1 and 4, th
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European Search Report No.--9212285.
Arrang Jean-Michel
Fkyerat Abdellatif
Ganellin Charon R.
Garbarg Monique
Lecomte Jeanne-Marie
Higel Floyd D.
Institut National de la Sante et de la Recherche Medicale
Societe Civile Bioprojet
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