Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1996-09-20
1998-01-20
Shah, Mukund J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514318, 544360, 546193, 546194, C07D40310, C07D40714, A61K 31495
Patent
active
057101566
DESCRIPTION:
BRIEF SUMMARY
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is based upon PCT Application Ser. No. PCT/EP 95/01184, filed Mar. 29, 1995, which claims priority from European Patent Application Ser. No. 94.200.938.2, filed on Apr. 6, 1994.
The present invention is concerned with substituted azolone derivatives which are potent anti-Helicobacter agents.
U.S. Pat. No. 4,791,111 discloses azolones having a structure similar to that of the present compounds and which are intermediates in the preparation of -imidazoles and -1H-1,2,4-triazoles.
In U.S. Pat. No. 4,931,444 there are described substituted azolone derivatives having 5-lipoxy-genase inhibiting activity. The present compounds are distinguished therefrom by their useful anti-Helicobacter activity.
In the eradication of Helicobacter, dual therapies comprising the separate administration of two antibiotic drugs have not been satisfactory because of one or more of the following reasons: a low eradication rate, numerous side effects and development of resistance by Helicobacter. Triple therapies comprising the administration of two antibiotics and a bismuth compound have been shown to be effective, but are very demanding for the patients and are also compromised by side effects. The present compounds show the avantage that they may be used in a monotherapy in the eradication of Helicobacter pylori and related species.
The present invention is concerned with compounds having the formula ##STR3## the pharmaceutically acceptable acid addition salts and the stereochemically isomeric forms thereof, wherein alkyl; C.sub.1-4 alkyloxy, hydroxy, trifluoromethyl, trifluoromethyloxy or difluoromethyloxy; alkyloxyC.sub.1-6 alkyl, phenyl or phenylC.sub.1-4 alkyl; ##STR4## is a radical of formula ##STR5##
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, i.e. 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.
The term pharmaceutically acceptable acid addition salt as used hereinbefore defines the non-toxic, therapeutically active acid 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 inorganic acids such as hydrohalic acid, i.e. 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 term pharmaceutically acceptable acid addition salts also comprises the solvates which the compounds of formula (I) and the salts thereof may form, e.g. the hydrates, alcoholates and the like.
The term stereochemically isomeric forms as used hereinbefore defines the 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 conformationally isomeric forms, said mixtures containing all diastereomers, enantiomers and/or conformers of the basic molecular structure. All stereochemically isomeric forms of the compounds of formula (I) both in pure form or mixtures thereof are int
REFERENCES:
patent: 4791111 (1988-12-01), Heeres et al.
patent: 5202346 (1993-04-01), Butera et al.
patent: 5250528 (1993-10-01), Oku et al.
patent: 5254553 (1993-10-01), Heeres et al.
H. Rautelin et al., In Vitro Activity of Antigungal Azoles against Helicobacter pylori, Eur. J. clin. Microbiol. Infect. Dis., vol. 11, 1992, pp. 273-274.
Heeres Jan
Hendrickx Robert Jozef Maria
Mostmans Joseph Hector
Stokbroekx Raymond Antoine
Van de Aa Marcel Jozef Maria
Janssen Pharmaceutica N.V.
Metz Charles J.
Ngo Tamthom T.
Shah Mukund J.
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