Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Patent
1981-06-29
1982-06-08
Killos, Paul J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
562459, 260408, 260413, 260415, 424308, 424317, 424318, 560 51, 560 53, C07C 6232
Patent
active
043340890
DESCRIPTION:
BRIEF SUMMARY
The invention relates to substituted oxocarboxylic acids, processes for their preparation, their use and medicaments containing them.
.alpha.-Keto-acid esters which can be used as intermediate products for the preparation of aminoacids or heterocyclic compounds are described in German Offenlegungsschrift No. 2,365,755. A process for the preparation of .alpha.-keto-acids is known from Belgian Pat. No. 779,821, the keto-acids being mentioned as intermediate products in metabolism or as precursors of aminoacids. 5-(4-Methoxyphenyl)-2-oxovaleric acid has been prepared by L. F. Fieser and H. L. Holmes [J. Amer. Chem. Soc. 58(1936)2319]. Certain substituted oxocarboxylic acids have now been discovered as pharmaceutical active compounds with a specific action.
The invention relates to substituted oxocarboxylic acids of the general formula I ##STR2## wherein R.sup.1 denotes a hydrogen atom, a halogen atom, a hydroxyl group, a lower alkyl group, a lower alkoxy group or a trifluoromethyl group, from 3 to 8,
Possible lower alkyl groups are straight-chain or branched alkyl radicals with 1 to 4 carbon atoms. Examples of straight-chain alkyl radicals are the methyl, ethyl, n-propyl and n-butyl radical, of which those with 1 and 2 carbon atoms are preferred. Examples of branched alkyl radicals are the isopropyl, isobutyl and sec.-butyl radical, of which the radical with 3 carbon atoms is preferred. Possible alkyl radicals in lower alkoxy groups are both straight-chain and branched lower alkyl groups. The methoxy group is the preferred lower alkoxy group.
Halogen atoms are fluorine, chlorine and bromine atoms, of which fluorine and, in particular, chlorine are preferred.
The substituents R.sup.1 and R.sup.2 are preferably in the meta-position or para-position to the ketocarboxylic acid radical.
Possible salts are salts with inorganic and organic bases. Pharmacologically unacceptable salts are converted into pharmacologically, that is to say biologically, acceptable salts, which are the preferred salts according to the invention, by methods which are known per se. Above all cations of alkali metals, alkaline earth metals or earth metals are used as cations for the salt formation, but cations corresponding to organic nitrogen bases, such as amines, aminoalkanols, aminosugars, basic aminoacids and the like, can also be used.
Examples which may be mentioned are the salts of ethylenediamine, dimethylamine, diethylamine, morpholine, piperidine, piperazine, N-lower alkyl-piperazine (for example N-methylpiperazine), methylcyclohexylamine, benzylamine, ethanolamine, diethanolamine, triethanolamine, tris-(hydroxymethyl)-aminomethane, 2-amino-2-methylpropanol, 2-amino-2-methyl-1,3-propanediol, glucamine, N-methylglucamine, glucosamine, N-methylglucosamine, lysine, ornithine, arginine and quinoline and preferably of lithium, sodium, potassium, magnesium, calcium and aluminium.
Substituted oxocarboxylic acids of the general formula I* ##STR3## wherein R.sup.1 * denotes a hydrogen atom, a chlorine atom, a methyl group, a methoxy group or a trifluoromethyl group,
R.sup.2 * denotes a hydrogen atom or a chlorine atom and
Substituted oxocarboxylic acids of the general formula I** ##STR4## wherein R.sup.1 ** and R.sup.2 ** are in the meta-position or para-position to the ketocarboxylic acid radical, and bases form a preferred embodiment of the invention.
Examples which may be mentioned of representatives of the acids according to the invention are 6-(2,4-dichlorophenyl)-2-oxocaproic acid, 2-oxo-6-(3-trifluoromethylphenyl)-caproic acid, 5-(3,4-dichlorophenyl)-2-oxovaleric acid, 7-(3-chlorophenyl)-2-oxoheptanoic acid, 7-(4-methoxyphenyl)-2-oxoheptanoic acid, 7-(4-bromophenyl)-2-oxoheptanoic acid, 8-(4-n-butoxyphenyl)-2-oxo-octanoic acid, 8-(3-fluorophenyl)-2-oxooctanoic acid, 2-oxo-8-(3-trifluoromethylphenyl)-octanoic acid, 7-(4-methylphenyl)-2-oxo-heptanoic acid, 8-(4-hydroxyphenyl)-2-oxo-octanoic acid, 9-(4-chlorophenyl)-2-oxo-nonanoic acid, 9-(3-trifluoromethylphenyl)-2-oxo-nonanoic acid, 10-(2,4-dichlorophenyl)-2-oxo-decanoic acid and 10-
REFERENCES:
patent: 3182061 (1965-05-01), Goldschmidt
patent: 3592846 (1971-07-01), Raymond
patent: 3855245 (1974-12-01), Koyama et al.
patent: 4029699 (1977-06-01), Murata et al.
Fieser, L. F. et al., JACS 58 (1936), pp. 2319-2322.
Krass Ekkehard
Wolf Horst
Byk Gulden Lomberg Chemische Fabrik Gesellschaft
Killos Paul J.
LandOfFree
Substituted oxocarboxylic acids, processes for their preparation does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Substituted oxocarboxylic acids, processes for their preparation, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Substituted oxocarboxylic acids, processes for their preparation will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-554026