Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1993-11-29
1995-11-21
Datlow, Philip I.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
540579, C07D48704, A61K 3155
Patent
active
054687438
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
In WO 88/03138 there are described benzo[5,6]cycloheptapyridines which possess antiallergic and anti-inflammatory activity. In EP-A-0,339,978 there are described (benzo- or pyrido)cyclohepta heterocyclics which are useful as PAF antagonists, antihistaminics and/or anti-inflammatory agents.
In WO 92/06981 there are described 6,11-dihydro-11-(4-piperidinylidene)-5H-imidazo[2,1-b][3]benzazepine and 1-acetyl-4-(5,6-dihydro-11H-imidazol[1,2-b][3]-benzazepine-11-ylidene)pipe ridine, the latter of which is useful as a PAF antagonist.
In the J. Med. Chem., 26 (1983), 974-980 there are described some 1-methyl-4-piperidinylidene-9-substituted pyrrolo[2,1-b][3]benzazepine derivatives having neuroleptic properties.
The compounds of the present invention differ structurally from the cited art-known compounds by the fact that the central 7-membered ring invariably contains a nitrogen atom of a fused imidazole ring, and by their favorable antiallergic activity.
DESCRIPTION OF THE INVENTION
The present invention is concerned with novel imidazo[2,1-b][3]benzazepines of formula ##STR2## the pharmaceutically acceptable addition salts and stereochemically isomeric forms thereof, wherein hydroxycarbonyl or C.sub.1-4 alkyloxycarbonyl, C.sub.1-4 alkyl substituted with hydroxycarbonyl or C.sub.1-4 alkyloxycarbonyl, hydroxyC.sub.1-4 alkyl, formyl or hydroxycarbonyl; phenyl or halo; one substituent selected from the group consisting of hydroxy, halo, C.sub.1-4 alkyloxy, hydroxycarbonyl, C.sub.1-4 alkyloxycarbonyl, C.sub.1-4 alkyloxycarbonylC.sub.1-4 alkyloxy, hydroxycarbonyl-C.sub.1-4 alkyloxy, C.sub.1-4 alkyloxycarbonylamino, C.sub.1-4 alkylaminocarbonyl, C.sub.1-4 alkylaminocarbonylamino, C.sub.1-4 alkylaminothiocarbonylamino, aryl, aryloxy and arylcarbonyl; C.sub.1-6 alkyl substituted with both hydroxy and aryloxy; C.sub.3-6 alkenyl; C.sub.3-6 alkenyl substituted with aryl; hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkyloxy, aminocarbonyl or phenyl substituted with C.sub.1-4 alkyloxycarbonyl or hydroxycarbonyl; or, oxazolyl, thiazolyl or imidazolyl each optionally substituted with one or two C.sub.1-4 alkyl substituents; pyrrolyl or pyrazolyl optionally substituted with formyl, hydroxyC.sub.1-4 alkyl, hydroxycarbonyl, C.sub.1-4 alkyloxycarbonyl or one or two C.sub.1-4 alkyl substituents; thiadiazolyl or oxadiazolyl optionally substituted with amino or C.sub.1-4 alkyl; pyridinyl, pyrimidinyl, pyrazinyl or pyridazinyl each optionally substituted with C.sub.1-4 alkyl, C.sub.1-4 alkyloxy, amino, hydroxy or halo; imidazo[4,5-c]pyridin-2-yl; and with C.sub.1-4 alkyl, 2-oxo-3-oxazolidinyl, 2,3-dihydro-2-oxo-1H-benzimidazol-1-yl or a radical of formula ##STR3## R.sup.6 represents hydrogen or C.sub.1-4 alkyl; and A-Z represents --S--CH.dbd.CH--, --S--CH.sub.2 --CH.sub.2 --, --S--CH.sub.2 --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH--CH.dbd.CH--, --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --, --N(CH.sub.3)--C(CH.sub.3).dbd.CH-- or --CH.dbd.C(CH.sub.3)--O--; 6,11-dihydro-11-(4-piperidinylidene)-5H-imidazo[2,1-b][3]benzazepine is ecxluded.
As used in the foregoing definitions halo defines fluoro, chloro, bromo and iodo; C.sub.1-4 alkyl defines straight and branched chain saturated hydrocarbon radicals having from 1 to 4 carbon atoms such as, for example, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl; C.sub.1-6 alkyl defines C.sub.1-4 alkyl radicals as defined hereinbefore and the higher homologs thereof having from 5 to 6 carbon atoms such as, for example, pentyl and hexyl; C.sub.3-6 alkenyl defines straight and branched chain hydrocarbon radicals containing one double bond and having from 3 to 6 carbon atoms such as, for example, 2-propenyl, 2-butenyl, 3-butenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 3,3-dimethyl-2-propenyl, hexenyl and the like; C.sub.1-4 alkanediyl defines bivalent straight or branched chain hydrocarbon radicals containing from 1 to 4 carbon atoms such as, for example, methylene, 1,1-ethanediyl, 1,2-ethanediyl, 1,3-propanediyl, 1,4-butanediyl
REFERENCES:
patent: 5008268 (1991-04-01), Janssens et al.
patent: 5393753 (1995-02-01), Friary
Diels Gaston S. M.
Janssens Frans E.
Leenaerts Joseph E.
Datlow Philip I.
Janssen Pharmaceutica N.V.
Metz Charles J.
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