Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1996-07-18
2000-04-04
Higel, Floyd D.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
424 165, 424 941, 4241841, 424532, 435121, 514397, 514398, 514399, 514400, 5483381, C07D23364, E12P 1710, A61K 31415, A61K 742
Patent
active
060463406
DESCRIPTION:
BRIEF SUMMARY
The present invention concerns the pseudodipeptide products, and especially a new pseudodipeptide product possessing an imidazole group or an imidazole N-substituted, as well as applications of such product in the therapeutic, cosmetic and food fields.
The object of the invention is a new pseudodipeptide product having as a general formula: ##STR4## in which
A is: ##STR5## wherein
B represents an amine which nitrogen atom is directly linked to the carbon atom and is choosen from the group consisting of: fluoroalkyl, or acyl radical, or an amine ##STR6## in which Y or Y' is an hydrocarbon, acyl or acyloxy radical, 5) imine of formula ##STR7## in which Y is an hydrocarbon radical and Y' is an hydrogen atom or an hydrocarbon radical, and ##STR8## W--
in which Y, Y', Y" is an hydrocarbon radical and the ion W is an halide, sulfate, phosphate, bicarbonate, a para-toluene-sulfonate, or a compound bearing a carboxylic acid group, sulfate, phosphate or carboxylic acid, an acyl radical, a linear alkyl chain that can be substituted by one or several functional groups, alkenyl or aryl radicals that can be substituted by one or several functional groups. fluoro-alkyl radical, ##STR9## wherein
R is an atom of hydrogen or fluorine, or a fluoro-alkyl or an acyl radical, or an hydrocarbon radical that can be subtituted by one or several functional groups and
R" is an acyl radical or an hydrocarbon radical that can be substituted by one or several functional groups.
In the case in which the general formula of the pseudodipeptide product is of the form a) with B being a lactam more particularly .delta.- or .gamma.-lactam, or cyclic tertiary amine which can be advantageously ##STR10##
In the case in which the general formula of the pseudodipeptide product is of the form a) being an ammonium, or when the imidazole ring involves an additionnal hydrogen atom on the nitrogen atom, the ion W can be an halide, sulfate, phosphate, bicarbonate, a para-toluene-sulfonate group, a compound bearing a carboxylic acid group such as an acetate,a trifluoracetate, a citrate, a gluconate, a picrate, or an amino acid such as aspartate or glutamate.
In the case in which the general formula of the pseudodipeptide product is of the form a) or b) with R, R' or R" being an hydrocarbon radical, this latter can be substituted by one or several functional groups such as alcohol, amine, carboxylic acid, alkoxy, thiolether, thiol, phosphate or sulphate.
Some elements of this compound family are capable of forming stable complexes with atoms belonging to the family of transition metals, the "chelates" consisting of an association of metal atom such as zinc, copper, iron, cobalt, manganese, or nickel, zinc being preferably choosen, with one or several pseudodipeptide molecules, this depending on the preparation mode and on the pseudodipeptide kind.
Examples of pseudodipeptide products especially representative of the invention are quoted here-below:
Products corresponding to the general formula having the form a) are:
R'=H
R=CH.sub.2 --CH.sub.2 --COOH
B=NH.sub.2
R'=CH.sub.2 --CH.sub.2 --COOH
R=H
B=NH.sub.2
R'=H
R=CH.sub.2 --CH.sub.3
X=CH.sub.3
R=R'=CH.sub.3
B=NH.sub.2
R'=H
R=CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.3
B=NH.sub.2
R'=H
R=CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.3
B=NH.sub.2
R'=H
R=CH.sub.2 --CH.sub.2 --CH.sub.3
B=tert-Butyl--O--C.dbd.O
R'=H
R=Phenyl
B=NH.sub.2
R'=H
R=CH.sub.2 --CH.sub.2 --CH.sub.2 --NH.sub.2
B=NH.sub.2
R'=H
R= ##STR11##
B=NH.sub.2
R'=H
R=CH.sub.2 --CH.sub.3 ##STR12## N-phenacetyl-2-aminobutyryl-histamine
R'=H
R=CH.sub.2 --CH.sub.3 ##STR13## L-Arginyl-histamine
R'=H
R= ##STR14##
Products corresponding to the general formula having the form b) are
R=H
R"=CH.sub.2 --CH.sub.2 --CH.sub.2 ##STR15## 4-hydroxy-L-prolyl-histamine
R=H
R"= ##STR16## given A= ##STR17## L-pyroglutamyl-histamine ##STR18## The pseudodipeptide product according to the invention can be considered as a condensation product between an alpha amino acid and the histamine or methyl substituted histamine such as the 1-methyl-histamine or the 3-
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Arold et al, Zeitschrift fur Chemie, vol. 9, No. 9, p. 144, 1969.
Modder et al. J. Org. Chem., vol. 56, No. 19, pp. 5606-5610, 1991.
Babizhayev Marc
Seguin Marie-Christine
Exsymol Societe Anonyme Monegasque
Higel Floyd D.
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