New histidine derivatives, preparation process, and their use as free antiradical agents
AssigneeL'oreal
InventorsMichel Philippe, Thierry Bordier
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Abstract
The invention relates to novel histidine derivatives corresponding to the general formula (I) below: 1 in which: R denotes a linear or branched, saturated or unsaturated alkyl radical containing from 6 to 22 carbon atoms, n is an integer ranging from 1 to 16, Q+ represents H+ or an organic or inorganic cation, and the addition salts with an acid. The invention also relates to a process for preparing the compounds of formula (I), as well as to the use of these compounds in cosmetics and pharmacy.
Claims24
Histidine derivative of general formula (I) below:
- 9
- in which:
- R denotes a linear or branched, saturated or unsaturated alkyl radical containing from 6 to 22 carbon atoms,
- n is an integer ranging from 1 to 16,
- Q+ represents H+ or an organic or inorganic cation, and the addition salts with an acid.
Histidine derivative according to either of the preceding claims, in which n is an integer ranging from 1 to 11.
Histidine derivative according to one of the preceding claims, in which the organic cation is chosen from ammoniums containing a residue chosen from basic amino acids and amino alcohols.
Histidine derivative according to any one of the preceding claims, chosen from:
- N-octyloxycarbonyl-β-alanyl-L-histidine,
- N-dodecyloxycarbonyl-β-alanyl-L-histidine,
- N-2-ethylhexyloxycarbonyl-β-alanyl-L-histidine hydrochloride,
- N-hexadecyloxycarbonyl-β-alanyl-L-histidine.
Process for preparing the compounds of general formula (I) below:
- 10
- in which:
- R denotes a linear or branched, saturated or unsaturated alkyl radical containing from 6 to 22 carbon atoms,
- n is an integer ranging from 1 to 16,
- Q+ represents H+ or an organic or inorganic cation, characterized in that it consists in reacting, in an inert solvent, a compound of formula (II)
- 11
- X representing a halogen atom or a radical derived from an azole,
- either (A) with carnosine,
- or (B), in a first step, with an amino acid of formula:
- H2N—(CH2)n—COOH
- to form a compound of formula (IV) below:
- 12
- and, in a second step, in reacting histidine with the compound of formula (IV) in the presence of a coupling agent.
Dependencies are inferred from the claim text.