Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1998-06-09
1999-11-16
Higel, Floyd D.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
514396, 514397, C07D40506, A61K 31415, A61K 3136
Patent
active
059861037
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to new imidazole derivatives, their preparation process, the new intermediates obtained, their use as medicaments, the pharmaceutical compositions containing them and the new use of imidazole derivatives.
A subject of the present invention is the products of formula (I): ##STR2## in which: R.sub.1 represents a linear or branched alkyl radical containing 2 to 6 carbon atoms, or salified tetrazolyl radical, or a linear or branched alkyl, alkoxy or alkylthio radical containing at most 4 carbon atoms and substituted by a free, salified or esterified carboxy radical or by a free or salified tetrazolyl radical, 4, radical, or a free or salified tetrazolyl radical, optionally by a halogen atom, or by an alkyl or alkoxy radical containing at most 4 carbon atoms, enantiomeric and diastereoisomeric isomer forts, as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).
In the products of formula (I) and in what follows: radicals: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, isohexyl and also heptyl, octyl, nonyl and decyl as well as their linear or branched position isomers, radicals: methoxy, ethoxy, propoxy, isopropoxy, linear, secondary or tertiary butoxy, pentoxy or hexoxy as well as their linear or branched position isomers, represent a fluorine, bromine or iodine atom, Hal.sub.1 preferably represents a fluorine atom.
The carboxy radical or radicals of the products of formula (I) can be salified or esterified by various groups known to a man skilled in the art amongst which there can be mentioned, for example: equivalent of sodium, potassium, lithium, calcium, magnesium or ammonium or organic bases such as, for example, methylamine, propylamine, trimethylamine, diethylamine, triethylamine, N,N-dimethylethanolamine, tris (hydroxymethyl) amino methane, ethanolamine, pyridine, picoline, dicyclohexylamine, morpholine, benzylamine, procaine, lysine, arginine, histidine, N-methylglucamine, alkoxy carbonyl groups such as, for example, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl or benzyloxycarbonyl, these alkyl radicals being able to be substituted by radicals chosen for example from halogen atoms, the following radicals: hydroxyl, alkoxy, acyl, acyloxy, alkylthio, amino or aryl such as, for example, in the following groups: chloromethyl, hydroxypropyl, methoxymethyl, propionyloxymethyl, methylthiomethyl, dimethylaminoethyl, benzyl or phenethyl.
The addition salts with mineral or organic acids of the products of formula (I) can be, for example, the salts formed with the following acids: hydrochloric, hydrobromic, hydroiodic, nitric, sulphuric, phosphoric, propionic, acetic, formic, benzoic, maleic, fumaric, succinic, tartaric, citric, oxalic, glyoxylic, aspartic, ascorbic, alkylmonosulphonic such as for example methanesulphonic, ethanesulphonic, propanesulphonic, alkyldisulphonic such as for example methanedisulphonic, alpha, beta-ethanedisulphonic, arylmonosulphonic such as benzenesulphonic and aryldisulphonic.
Therefore a subject of the present invention is the products of formula (I) as defined above in which: terbutyl radical, at most 4 carbon atoms and substituted by a free, salified or esterified carboxy radical, free or salified tetrazolyl radical, optionally by a halogen atom, enantiomeric and diastereoisomeric isomer forms, as well as the addition salts with mineral and organic acids or with mineral and organic bases of said products of formula (I).
A particular subject of the present invention is the following products: )-2-propyl-1H-imidazole-5-carboxylic acid, )-2-(1-methylethyl)-1H-imidazole-5-carboxylic acid, 2-propyl 1H-imidazole 5-carboxylic acid.
In the products of formula (I) and in what follows: radical is as defined above such as for example in methylthio, ethylthio, propylthio, isopropylthio, butylthio, sec-butylthio, tert-butylthio, isopentylthio, isohexylthio, but also heptylthio, octylthio, nonylthio or decylthio as well as their lin
Heckmann Bertrand
Jouquey Simone
Vevert Jean-Paul
Zhang Jidong
Higel Floyd D.
Hoechst Marion Roussel
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