Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Radical -xh acid – or anhydride – acid halide or salt thereof...
Patent
1999-02-02
2000-11-07
Reamer, James H.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Radical -xh acid, or anhydride, acid halide or salt thereof...
514569, 514464, 514461, 562459, 562462, 549436, 549501, A61K 3119
Patent
active
061437875
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to pharmaceutical compositions containing 4-oxobutanoic acids, which are useful in particular in the treatment of diabetes.
The subject of the present invention is thus pharmaceutical compositions comprising, as, active principle, a compound of formula: ##STR2## in which the groups A and B are chosen, independently of each other, from: a mono-, bi- or tricyclic aryl group having from 6 to 14 carbon atoms; thienyl groups; tetrahydropyranyl, piperidyl and pyrrolidinyl groups; from a C.sub.1 -C.sub.6 alkyl group, C.sub.1 -C.sub.6 alkoxy group, C.sub.6 -C.sub.14 aryl group, a heteroaryl group chosen from pyridyl, pyrimidyl, pyrrolyl, furyl and thienyl, a (C.sub.6 -C.sub.14)aryl(C.sub.1 -C.sub.6)alkyl group, a (C.sub.6 -C.sub.14)aryl(C.sub.1 -C.sub.6)alkyl(C.sub.6 -C.sub.14)aryl group, halogen, a trifluoromethyl, trifluoromethoxy, cyano, hydroxyl, nitro, amino, carboxyl, (C.sub.1 -C.sub.6)alkoxycarbonyl, carbamoyl, (C.sub.1 -C.sub.6) alkylsulphonyl, sulphoamino, (C.sub.1 -C.sub.6)alkylsulphonylamino, sulphamoyl or (C.sub.1 -C.sub.6)alkylcarbonylamino group, salt of this acid with a pharmaceutically acceptable base.
In a preferred embodiment of the invention, the compositions comprise, as active principles, a compound of formula I in which A and B are chosen from aryl groups.
Examples of aryl groups which may be mentioned are phenyl, .alpha.-naphthyl, .beta.-naphthyl and fluorenyl groups.
The C.sub.1 -C.sub.6 alkyl groups may be linear or branched. Examples which may be mentioned are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl and pentyl groups.
The C.sub.1 -C.sub.6 alkoxy groups may similarly be linear or branched.
Examples which may be mentioned are methoxy, ethoxy, propoxy, isopropoxy, butoxy, and isobutoxy groups.
The halogens may be chosen from fluorine, chlorine, bromine and iodine.
The present invention encompasses compositions which contain the tautomeric forms, the enantiomers, the diastereoisomers and the epimers of the compounds of formula I.
Examples of pharmaceutically acceptable salts which may be mentioned are the sodium salts, potassium salts, magnesium salts, calcium salts, amine salts and other salts of the same type (aluminium, iron, bismuth, etc.).
In a preferred embodiment, the compositions according to the invention comprise a compound chosen from: bases.
Certain compounds of formula I are known (Bioorg. Chem. 14, 148, 1986; Biochemistry 23, 2083, 1984; J.A.C.S. 100, 7750, 1978; EP-A-310918 and DE-A-3 839 401)
The subject of the present invention is also the novel compounds of formula I, that is to say the compounds of formula: ##STR3## in which the groups A and B are chosen, independently of each other, from: a mono-, bi- or tricyclic aryl group having from 6 to 14 carbon atoms; thienyl groups; tetrahydropyrranyl, piperidyl and pyrrolidinyl groups; from a C.sub.1 -C.sub.6 alkyl group, C.sub.1 -C.sub.6 alkoxy group, C.sub.6 -C.sub.14 aryl group, a heteroaryl group chosen from pyridyl, pyrimidyl, pyrrolyl, furyl and thienyl, a (C.sub.6 -C.sub.14)aryl(C.sub.1 -C.sub.6)alkyl group, a (C.sub.6 -Cl.sub.4)aryl(C.sub.1 -C.sub.6)alkyl(C.sub.6 -C.sub.14)aryl group, halogen, a trifluoromethyl, trifluoromethoxy, cyano, hydroxyl, nitro, amino, carboxyl, (C.sub.1 -C.sub.6)alkoxycarbonyl, carbamoyl, (C.sub.1 -C.sub.6) alkylsulphonyl, sulphoamino, (C.sub.1 -C.sub.6)alkylsulphonylamino, sulphamoyl or (C.sub.1 -C.sub.6)alkylcarbonylamino group, unsubstituted phenyl group and A is a phenyl, 4-methoxyphenyl, 4-chlorophenyl or cyclohexyl group,
The novel compounds include the salts of the acids with pharmaceutically acceptable bases or other bases which give salts which may serve to identify, purify or resolve the compounds of formula I.
The compounds of formula I may be prepared according to a malonic synthesis which consists in reacting a compound of formula: ##STR4## in which X is a halogen as defined above and A has the meaning given above, ##STR5## in which R and R' are C.sub.1 -C.sub.6 alkyl groups and B has the meaning given above, order to form a compound
REFERENCES:
patent: 5055466 (1991-10-01), Weller, III et al.
Galardy et al, Chemical Abstracts, vol. 100, No. 152956n, 1984.
Doare Liliane
Kergoat Micheline
Maizeray Philippe
Mesangeau Didier
Moinet Gerard
Merck Patent Gesellschaft mit
Reamer James H.
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