Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1995-04-04
1996-12-31
Springer, David B.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546176, C07D40306, A61K 3147
Patent
active
055894844
DESCRIPTION:
BRIEF SUMMARY
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is based upon PCT application Ser. No. PCT/EP 93/02884, filed Oct, 19, 1993, which claims priority from U.S. application Ser. Nos. 07/967,008, filed on Oct. 27, 1992, and 08/069,804, filed Jun. 1, 1993, both of which are now abandoned.
BACKGROUND OF THE INVENTION
EP-0,371,564 (published Jun. 6, 1990) discloses (1H-azol-1-yl-methyl) substituted quinoline derivatives which suppress the plasma elimination of retinoic acids. The compounds of the present invention differ from the cited art compounds by the fact that the quinoline moiety is substituted at the 4-position with a (phenyl azolyl)methyl group and by their unexpected anti-Helicobacter activity.
Afflictions of the gastro-enteric tract are widespread. Modern medicine still fails to cure a lot of them, in particular those related to the presence in the gastric mucosa of the bacterium Helicobacter, e.g. chronic gastritis, duodenal ulcer and duodenal ulcer relapse. Dual therapies in the eradication of Helicobacter, comprising the separate administration of two antibiotic drugs, have not been satisfactory up till now, 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 complicated by side effects.
The present invention is concerned with novel quinoline compounds which are potent anti-Helicobacter agents and which may be used in a mono therapy in the eradication of Helicobacter pylori and related species.
DESCRIPTION OF THE INVENTION
The present invention is concerned with novel quinoline derivatives of formula ##STR2## the pharmaceutically acceptable acid addition salts thereof, the stereochemically isomeric forms thereof, the quaternized forms thereof and the N-oxides thereof, wherein --A-- represents a bivalent radical of formula independently represent hydrogen, halo, hydroxy, C.sub.1-4 alkyloxy, C.sub.1-4 alkyl, trifluoromethyl, amino, mono- or di-(C.sub.1-4 alkyl)amino or nitro, provided that when one substituent on a phenyl group is a nitro then the other substituents on said phenyl group are other than nitro.
As used in the foregoing definitions and hereinafter 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.
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) may form, e.g. the hydrates, alcoholates and the like.
The term stereochemically isomeric forms refers to those compounds with identical molecular formulae but differing in the arrangement of their atoms in space. Unless oth
REFERENCES:
patent: 5028606 (1991-07-01), Venet
patent: 5037829 (1991-08-01), Freyne
patent: 5185346 (1993-02-01), Sanz
Guillemont J er ome E. G.
Odds Frank C.
Venet Marc G.
Vernier Daniel F. J.
Janssen Pharmaceutica N.V.
Metz Charles J.
Springer David B.
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