Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1995-12-13
1997-10-07
Bond, Robert T.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
540522, 540578, 540579, 546210, 514215, A61K 3155, C07D48704
Patent
active
056748663
DESCRIPTION:
BRIEF SUMMARY
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is based upon PCT Application Ser. No. PCT/EP 94/02287, filed Jul. 6, 1994, which claims priority from European Patent Application Ser. No. 93.202.154.6, filed on Jul. 13, 1993.
WO 92/22 551 and WO 92/22 553 describe imidazoazepines having antiallergic activity. In EP-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 88/03 138 there are described anti-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 is substituted by a carbonyl, hydroxy or hydroxyimino group. Their favorable antiallergic activity is evidenced by their lack of sedating properties at therapeutic dose levels.
The present invention is concerned with novel imidazoazepines of formula ##STR3## the pharmaceutically acceptable addition salts and stereochemically isomeric forms thereof, wherein phenylcarbonyl, C.sub.1-6 alkyl or C.sub.1-6 alkyl substituted with C.sub.1-4 alkyloxycarbonyl, hydroxycarbonyl, aryl, aryloxy or a radical of formula ##STR4## --D--Z-- is --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 --; and aryl is phenyl or phenyl substituted with halo, hydroxy or C.sub.1-4 alkyloxy.
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.-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.
The term pharmaceutically acceptable addition salt as used hereinbefore defines the non-toxic, therapeutically active addition salt forms which the compounds of formula (I) may form. The compounds of formula (I) having basic properties may be converted into the corresponding therapeutically active, non-toxic acid addition salt forms by treating the free base form with a suitable amount of an appropriate acid following conventional procedures. Examples of appropriate acids are for example, inorganic acids, for example, hydrohalic acid, e.g. hydrochloric, hydrobromic and the like acids, sulfuric acid, nitric acid, phosphoric acid and the like; or organic acids, such as, for example, acetic, propanoic, hydroxyacetic, 2-hydroxypropanoic, 2-oxopropanoic, ethanedioic, propanedioic, butanedioic, (Z)-2-butenedioic, (E)-2-butenedioic, 2-hydroxybutanedioic, 2,3-dihydroxybutanedioic, 2-hydroxy-1,2,3-propanetricarboxylic, methanesulfonic, ethanesulfonic, benzenesulfonic, 4-methylbenzenesulfonic, cyclohexanesulfamic, 2-hydroxybenzoic, 4-amino-2-hydroxybenzoic and the like acids.
The compounds of formula (I) having acidic properties may be converted in an analogous manner with a suitable base into the corresponding therapeutically active, non-toxic base addition salt forms. Examples of such base addition salt forms are, for example, the sodium, potassium, calcium salts, and also the salts with pharmaceutically acceptable amines such as, for example, ammonia, alkylamines, benzathine, N-methyl-D-glucamine, hydrabamine, amino acids, e.g. arginine, lysine. The term pharmaceutically acceptable addition salts also comprises the solvates which the compounds of formula (I) may form, e.g. the hydrates, alcoholates and the like.
The term stereochemically isomeric forms as used hereinbefore defines the possible different isomeric as well as conformational forms which the compounds of formula (I) may possess. Unless otherwise mentioned or indicated, the chemical designation of compounds denotes the mixture of all possible stereochemically and conf
REFERENCES:
patent: 5461050 (1995-10-01), Janssens et al.
patent: 5468743 (1995-11-01), Janssens et al.
Janssens Frans Eduard
Leenaerts Joseph Elisabeth
Bond Robert T.
Janssen Pharmaceutica N.V.
Metz Charles J.
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