Imidazo [1,2-A] (pyrrolo, thieno or furano) [2,3-D] azepine deri

Details Imidazo [1,2-A] (pyrrolo, thieno or furano) [2,3-D] azepine deri Imidazo [1,2-A] (pyrrolo, thieno or furano) [2,3-D] azepine deri

1995-05-08

1997-05-13

Richter, Johann

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

540578, A61K 3155, C07D48714, C07D491147, C07D49514

Patent

active

056293089

DESCRIPTION:

BRIEF SUMMARY
CROSS-REFERENCE TO RELATED APPLICATIONS

This application is based upon PCT application Ser. No. PCT/EP 93/03321, filed Nov. 25, 1993, which claims priority from European Application Serial No. 92.203.778.3, filed on Dec. 4, 1992.
The present invention is concerned with novel imidazo[1,2-a](pyrrolo, thieno or furano)[2,3-d]azepine derivatives having antiallergic 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 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.
In WO 92/06981 there are described substituted imidazobenzazepines and imidazopyridoazepines having and allergic and and-inflammatory activity. 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 andallergic activity.
The present invention is concerned with novel imidazo[1,2-a](pyrrolo, thieno or furano)[2,3-d]azepines of formula ##STR2## the pharmaceutically acceptable addition salts and stereochemically isomeric forms thereof, wherein with hydroxycarbonyl or C.sub.1-4 alkyloxycarbonyl, hydroxyC.sub.1-4 alkyl, formyl, hydroxycarbonyl or hydroxycarbonylC.sub.1-4 alkyl; 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, C.sub.1-4 alkyloxy, hydroxycarbonyl, C.sub.1-4 alkyloxycarbonyl, C.sub.1-4 alkylaminocarbonyl, C.sub.1-4 alkyloxycarbonylamino, C.sub.1-4 alkyloxycarbonylC.sub.1-4 alkyloxy, hydroxycarbonylC.sub.1-4 alkyloxy, C.sub.1-4 alkylaminocarbonylamino, C.sub.1-4 alkylaminothiocarbonylamino, aryl and aryloxy; 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 or aminocarbonyl; 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 with 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; 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## 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 or CH.sub.2 -CH.sub.2 -CH.sub.2 -CH.sub.2.
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 and the like.
The term pharmaceutically acceptable addition salt as used hereinbefore defines

REFERENCES:
patent: 5461050 (1995-10-01), Janssens et al.
Thornber et al., Isoterism and Molecular Modification in Drug Design, Chemical Society Reviews, vol. 8, pp. 563-580. 1979.

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