Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1996-06-24
1998-02-17
Rotman, Alan L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546121, A61C 31485, C07D47104
Patent
active
057191611
DESCRIPTION:
BRIEF SUMMARY
This application is the national phase of PCT/EP94/03326 filed Oct. 8, 1994.
FIELD OF APPLICATION OF THE INVENTION
The invention relates to novel compounds which are intended for use in the pharmaceutical industry as active compounds for the production of medicaments.
KNOWN TECHNICAL BACKGROUND
European Patent Application EP-A-0,033,094 describes which is preferably a phenyl radical, thienyl radical, pyridyl radical or a phenyl radical substituted by chlorine, fluorine, methyl, tert-butyl, trifluoromethyl, methoxy or cyano. Aryl radicals of particular interest mentioned 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, in the 3-position carry an unsaturated aliphatic radical, in particular a (substituted) alkynyl radical.--European Patent Application EP-A-0,266,890 by an alkenyl, alkyl or cycloalkylalkyl radical.
DESCRIPTION OF THE INVENTION
It has now been found that the compounds described below in greater detail, which differ from the compounds of the prior art, in particular, by the substitution in the 3- or in the 8-position, have surprising and particularly advantageous properties. formula sheet), in which
1-4C-Alkyl is straight-chain or branched alkyl radicals 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.
1-4C-Alkoxy is an oxygen atom to which one of the abovementioned 1-4C-alkyl radicals is bonded. The methoxy radical is preferred. 2-4C-Alkoxy is an oxygen atom to which a 2-4C-alkyl radical (selected from the abovementioned 1-4C-alkyl radicals) is bonded. 1-4C-Alkoxy-2-4C-alkoxy is a 2-4C-alkoxy radical to which a 1-4C-alkoxy radical is bonded. The 2-methoxyethoxy radical is preferred.
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 intolerable salts, which may be initially obtained as process products, for example in the preparation of the compounds according to the invention on an industrial scale, are converted into pharmacologically tolerable salts by processes known to the person skilled in the art. Those suitable are water-soluble and water-insoluble acid addition salts with acids, for example hydrochloric acid, hydrobromic acid, phosphoric acid, nitric acid, sulphuric acid, acetic acid, citric acid, D-gluconic acid, benzoic acid, 2-(4-hydroxybenzoyl)benzoic acid, burytic acid, sulphosalicylic acid, maleic acid, lauric acid, malic acid, fumaric acid, succinic acid, oxalic acid, tartaric acid, embonic acid, stearic acid, toluenesulphonic acid, methanesulphonic acid or 3-hydroxy-2-naphthoic acid, where the acids are employed in salt preparation--depending on whether a mono- or polybasic acid is concerned and on which salt is desired--in an equimolar quantitative ratio or one differing therefrom.
Exemplary compounds which may be mentioned are the compounds ,2-a!pyridine-3-methanol, and their salts.
To be emphasized are those compounds of the formula I in which R4 is hydroxymethyl and A is O (oxygen) and R1, R2 and R3 have the meanings indicated above, and their salts.
The invention further relates to a process for the preparation of the compounds of the formula I and their salts. The process is characterized in that R1, R4 and A have the meanings indicated above, or their salts, are reacted with compounds of the formula III (see attached formula sheet), in which R2 and R3 have the meanings indicated above and X is a suitable reactive leaving group, or their salts, or in that hydroxymethyl, compounds of the formula IV (see attached formula sheet), in which R1, R2, R3 and A have the meanings indicated above, are reduced then converted into their salts, or
REFERENCES:
patent: 4831041 (1989-05-01), Shiokawa
patent: 4920129 (1990-04-01), Shiokawa
ByK Gulden Lomberg Chemische Fabrik GmbH
Huang Evelyn
Rotman Alan L.
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