Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1995-08-15
1997-09-09
Dentz, Bernard
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546121, A16K 31435, C07D47104
Patent
active
056657307
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP94/00335 filed Feb. 7, 1994.
FIELD OF THE INVENTION
The invention relates to novel imidazopyridines which are intended for use in the pharmaceutical industry as active substances for producing pharmaceuticals.
BACKGROUND OF THE INVENTION
European Patent Application EP-A-O 033 094 describes imidazo[1,2-a]pyridines which have in position 8 an aryl substituent which is preferably a phenyl, thienyl or pyridyl radical or a phenyl radical which is substituted by chlorine, fluorine, methyl, tert.-butyl, trifluoromethyl, methoxy or cyano. Aryl radicals mentioned as particularly interesting in EP-A-0 033 094 are 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, EP-A-0 228 006, EP-A-0 268 989 and EP-A-0 308 917 describe imidazo[1,2-a]pyridines which have in position 3 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 position 8 by an alkenyl, alkyl or cycloalkylalkyl radical.
DESCRIPTION OF THE INVENTION
It has now been found that the compounds which are described in detail hereinafter and which differ from the compounds of the prior art, in particular by the substitution in position 3 or 8, have surprising and particularly advantageous properties.
The invention relates to compounds of the formula I (see the end of this specification)
1-4C-alkyl represents straight-chain or branched alkyl radicals with 1 to 4 carbon atoms. Examples which may be mentioned are the butyl, iso-butyl, sec.-butyl, tert.-butyl, propyl, isopropyl, ethyl and, in particular, the methyl radical.
1-4C-alkoxy represents an oxygen atom to which one of the abovementioned 1-4C-alkyl radicals is bonded. The methoxy radical is preferred.
Suitable salts for compounds of the formula I are preferably all acid addition salts. Particular mention may be made of the pharmacologically compatible salts of the inorganic and organic acids customarily used in pharmaceutical technology. Pharmacologically incompatible salts which may, for example, be the initial products of the processes for the preparation of the compounds according to the invention on an industrial scale are converted into pharmacologically compatible salts by processes known to the skilled worker. Suitable as such are water-soluble and water-insoluble acid addition salts with acids, such as 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 for the preparation of the salts in a ratio of amounts which is equimolar or different therefrom--depending on whether the acid is mono- or polybasic and depending on which salt is required.
Examples of preferred compounds which may be mentioned are the compounds 3-hydroxymethyl-8-(2-methoxycarbonylamino-6-methylbenzylamino)-2-methyl-im idazo[1,2-a]pyridine, 3-hydroxymethyl-8-(2-methoxycarbonylamino-6-methylbenzyloxy)-2-methylimida zo[1,2-a]pyridine, 8-(2-methoxycarbonylamino-6-methylbenzylamino)-2,3-dimethylimidazo[1,2-a]p yridine and 8-(2-methoxycarbonylamino-6-methylbenzyloxy)-2,3-dimethylimidazo[1,2-a]pyr idine and the salts thereof.
The invention further relates to a process for the preparation of the compounds of the formula I and the salts thereof. The process comprises denotes hydroxymethyl, reducing compounds of the formula II (see attached sheet of formulae), in which R1, R2, R3 and A have the abovementioned meanings, or comprises denotes methyl, reacting compounds of the formula III (see attached sheet of formulae), in w
Grundler Gerhard
Rainer Georg
Senn-Bilfinger Jorg
ByK Gulden Lomberg Chemische Fabrik GmbH
Dentz Bernard
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