Triazolobenzazepine derivatives

Details Triazolobenzazepine derivatives Triazolobenzazepine derivatives

1996-05-08

1999-08-03

McKane, Joseph

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

540578, C07D22318

Patent

active

059325690

DESCRIPTION:

BRIEF SUMMARY
The present invention is concerned with triazolobenzazepine 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 WO 92/06981 there are described substituted imidazobenzazepines and imidazopyridoazepines having antiallergic and anti-inflammatory activity.
In J. Med. Chem., 26(1983), 974-980 there are described some derivatives having neuroleptic properties.
In DE-27,35,158 there are described triazolobenzazepine derivatives having analgesic 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 triazole ring, and by their favorable antiallergic activity.
The present invention is concerned with novel triazolobenzazepines of formula ##STR2## the pharmaceutically acceptable addition salts and stereochemically isomeric forms thereof, wherein
each of the dotted lines independently represents an optional bond;
R.sup.1 represents hydrogen, halo, C.sub.1-4 alkyl, hydroxy or C.sub.1-4 alkyloxy;
R.sup.2 represents hydrogen, halo, C.sub.1-4 alkyl, hydroxy or C.sub.1-4 alkyloxy;
R.sup.3 represents hydrogen, C.sub.1-4 alkyl or halo;
--B.dbd.D-- is a bivalent radical of formula ##STR3##
R.sup.4 represents hydrogen, C.sub.1-4 alkyl, ethenyl substituted with 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;
R.sup.5 represents hydrogen, C.sub.1-4 alkyl, ethenyl substituted with 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, hydroxycarbonyl, phenyl or pyridinyl;
L represents hydrogen; C.sub.1-6 alkyl; C.sub.1-6 alkyl substituted with one substituent selected from the group consisting of hydroxy, 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 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,
L represents a radical of formula ##STR4##
Alk represents C.sub.1-4 alkanediyl;
Y represents O, S or NH;
Het.sup.1, Het.sup.2 and Het.sup.3 each represent furanyl, thienyl, 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; and Het.sup.3 may also represent 4,5-dihydro-5-oxo-1H-tetrazolyl substituted with C.sub.1-4 alkyl, 2-oxo-3-oxazolidinyl, 2,3-dihydro-2-oxo-1H-benzimidazol-1-yl or a radical of formula ##STR5## --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 r

REFERENCES:
patent: 5468743 (1995-11-01), Janssens et al.

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