Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-05-16
2000-09-26
Ford, John M.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546121, C07D47104, C07D40110, C07D40112, A61K 31415
Patent
active
061243132
DESCRIPTION:
BRIEF SUMMARY
This is a 371 of PCT/EP95/02954, filed 26 July 1995.
FIELD OF APPLICATION OF THE INVENTION
The invention relates to novel imidazopyridine azolidinones which are intended to be used in the pharmaceutical industry as active compounds for the production of medicaments.
KNOWN TECHNICAL BACKGROUND
European Patent Application EP-A-0 033 094 (partially equivalent to U.S. Pat. No. 4,450,164) describes imidazo[1,2-a]pyridines which in the 8-position carry an aryl substituent which is preferably a phenyl, thienyl, pyridyl, or chlorine-, fluorine-, methyl-, tert-butyl-, trifluoromethyl-, methoxy- or cyano-substituted phenyl radical. As aryl radicals of particular interest, EP-A-0 033 094 mentions the radicals phenyl, o- or p-fluorophenyl, p-chlorophenyl and 2,4,6-trimethylphenyl, of which the radicals phenyl, o- or p-fluorophenyl and 2,4,6-trimethylphenyl are particularly preferred.--European Patent Applications EP-A-0 204 285 (equivalent to U.S. Pat. No. 4,725,601), EP-A-0 228 006, EP-A-0 268 989 (equivalent to U.S. Pat. No. 4,831,041) and EP-A-0 308 917 (equivalent to U.S. Pat. No. 4,920,129) describe imidazo[1,2-a]pyridines which in the 3-position carry an unsaturated aliphatic radical, in particular a (substituted) alkynyl radical.--European Patent Application EP-A-0 266 890 describes imidazo[1,2-a]pyridines which are substituted in the 8-position by an alkenyl, alkyl or cycloalkylalkyl radical.
DESCRIPTION OF THE INVENTION
It has now been found that the compounds described in greater detail below, which in particular differ from the compounds of the prior art by the substitution in the 8-position, have surprising and particularly advantageous properties.
The invention relates to compounds of the formula I (see attached formula sheet I), in which identical or different substituents selected from the group consisting of halogen, 1-4C-alkoxy and 1-4C-alkoxy-1-4C-alkoxy,
1-4C-Alkyl is a straight-chain or branched alkyl radical having 1 to 4 carbon atoms. Examples which may be mentioned are the butyl, isobutyl, sec-butyl, tert-butyl, propyl, isopropyl, ethyl and, in particular, the methyl radical.
Halogen within the meaning of the invention is bromine, fluorine and in particular chlorine.
1-4C-Alkoxy is an oxygen atom to which one of the abovementioned 1-4C-alkyl radicals is bonded. Examples which may be mentioned are the methoxy and the ethoxy radical.
1-4C-Alkoxy-1-4C-alkoxy is one of the abovementioned 1-4C-alkoxy radicals which is substituted by a further 1-4C-alkoxy radical. An example which may be mentioned is the methoxyethoxy radical.
Suitable salts of compounds of the formula I are preferably all acid addition salts. Particular mention may be made of the pharmacologically tolerable salts of the inorganic and organic acids customarily used in pharmacy. Pharmacologically nontolerable salts which can initially be obtained as process products, for example, in the preparation of the compounds according to the invention on the industrial scale are converted into pharmacologically tolerable salts by the processes known to the person skilled in the art. Those suitable are water-soluble and water-insoluble acid addition salts with acids, such as, for example, hydrochloric acid, hydrobromic acid, phosphoric acid, nitric acid, sulfuric acid, acetic acid, citric acid, D-gluconic acid, benzoic acid, 2-(4-hydroxybenzoyl)benzoic acid, butyric acid, sulfosalicylic acid, maleic acid, lauric acid, malic acid, fumaric acid, succinic acid, oxalic acid, tartaric acid, embonic acid, stearic acid, toluenesulfonic acid, methanesulfonic acid or 3-hydroxy-2-naphthoic acid, the acids being employed in salt preparation--depending on whether it is a mono- or polybasic acid and depending on which salt is desired--in an equimolar quantitative ratio or one differing therefrom.
Compounds to be emphasized are those of the FIG. 1 (compounds I), in which selected from the group consisting of halogen, 1-4C-alkoxy and 1-4C-alkoxy-1-4C-alkoxy,
Compounds to be particularly emphasized are those compounds I, in which selected from the group
REFERENCES:
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patent: 4725601 (1988-02-01), Ueda
patent: 4831041 (1989-05-01), Shiokawa
patent: 4920129 (1990-04-01), Shiokawa
Chemical Abstracts, vol. 115, No. 21, abstract No. 232239f, 1991 (Fujisawa JP-A-02 270 873).
Grundler Gerhard
Rainer Georg
Senn-Bilfinger Jorg
Thibaut Ulrich
ByK Gulden Lomberg Chemische Fabrik GmbH
Ford John M.
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