Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-01-09
1998-03-17
Northington-Davis, Zinna
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
544295, 544364, 544366, 544370, C07D40104, A61K 31495, A61K 3141, A61K 3144
Patent
active
057287007
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP95/02619 filed Jul. 5, 1995, published as WO96/01818 Jan. 25, 1996.
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 are described substituted azolone derivatives having 5-lipoxygenase 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 advantage 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 ##STR4## the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein
Y is CH or N;
R.sup.1, R.sup.2 and R.sup.3 each independently are hydrogen or C.sub.1-4 alkyl;
R.sup.4 and R.sup.5 each independently are hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkyloxy, hydroxy, trifluoromethyl, trifluoromethyloxy or difluoromethyloxy;
R.sup.6 is C.sub.1-4 alkyl; or phenyl optionally substituted with halo, C.sub.1-4 alkylcarbonylamino, C.sub.1-4 alkyloxy, C.sub.1-4 alkyl or nitro;
Z is C.dbd.O or CHOH; and ##STR5## is a radical of formula ##STR6##
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: 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 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. Appropriate acids comprise, for example, inorganic acids such as hydrohalic acids, e.g. hydrochloric or hydrobromic acid; sulfuric; nitric; phosphoric and the like acids; or organic acids such as, for example, acetic, propanoic, hydroxyacetic, lactic, pyruvic, oxalic, malonic, succinic, maleic, fumaric, malic, tartaric, citric, methane-sulfonic, ethanesulfonic, benzenesulfonic, p-toluenesulfonic, cyclamic, salicylic, p-aminosalicylic, pamoic and the like acids. The term addition salt as used hereinabove also comprises the solvates which the compounds of formula (I) as well as the salts thereof, are able to form. Such solvates are for example 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 in admixture with each other ar
REFERENCES:
patent: 4791111 (1988-12-01), Heeres et al.
patent: 4931444 (1990-06-01), Van Wauwe et al.
patent: 5571811 (1996-11-01), Heeres et al.
Heeres Jan
Mostmans Joseph Hector
Stokbroekx Raymond Antoine
Van der Veken Louis Jozef Elisabeth
Janssen Pharmaceutica N.V.
Metz Charles J.
Northington-Davis Zinna
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