Combination of a retinoid with a histidine derivative

Details Combination of a retinoid with a histidine derivative Combination of a retinoid with a histidine derivative

1999-05-25

2002-03-19

Page, Thurman K. (Department: 1615)

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Cosmetic, antiperspirant, dentifrice

C424S059000, C424S062000, C424S063000, C424S064000, C424S070100, C424S070900, C424S070270, C424S450000, C424S489000

Reexamination Certificate

active

06358514

ABSTRACT:

BACKGROUND OF THE INVENTION
Field of the Invention
The present invention relates to novel cosmetic and/or dermatological compositions, in particular compositions intended for skincare and comprising at least one compound of the retinoid family. More particularly, the invention relates to stable compositions comprising at least one compound of the retinoid family and at least one histidine derivative.
Description of the Background
Cosmetic and/or dermatological compositions based on retinoids have undergone considerable development in recent years. Among the retinoids, the use of retinoic acid in compositions for treating acne is well known.
However, it has been recognized that other derivatives of the retinoid family offer an advantage, both for treating acne and for skincare, in particular for limiting, or even eliminating, the effects of ageing on the skin: wrinkles, a weatherbeaten appearance, yellowing, the loss of elasticity, redness, dryness and the appearance of marks are the usual manifestations of ageing of the skin. These manifestations are proportionately more pronounced when the skin has been frequently exposed to the sun or is particularly sensitive to exposure to UV radiation.
Thus, the effects of intrinsic ageing of the skin (associated with age) and of light-induced ageing (due to exposure to the sun) can be cumulative. The manifestations of ageing usually appear at an advanced age; however, their prevention should be undertaken from the start of adult life, by means of appropriate care measures.
Treatment of the skin with derivatives of the retinoid family forms a part of these preventive or curative measures for caring for the manifestations of ageing, namely: wrinkles, weatherbeaten skin, yellowing, loss of elasticity, redness, dryness and marks.
Among the derivatives of the retinoid family, retinol, also known as vitamin A, and esterified derivatives of retinol are most particularly advantageous. In point of fact, retinol is a natural endogenous constituent of the human body. It is well tolerated when applied to the skin, up to levels much higher than those for retinoic acid. Retinol esters are converted into retinol by the human body.
However, when they are introduced into a cosmetic or dermatological composition intended for topical application, retinol and its esters rapidly degrade, under the effect of light, oxygen, metal ions, oxidizing agents, water or, in particular, under the effect of an increase in temperature. The thermal degradation of retinol was the subject of a study published in J. Soc. Cosm. Chem. 46, 191-198 (July-August 1995).
Various combinations of retinol or of other derivatives of the retinoid family with antioxidants are known, the retinoids being of improved stability in these combinations:
WO 93/00085 describes W/O emulsions comprising retinol and a stabilizing system consisting of a chelating agent such as, for example, EDTA, and an antioxidant which can be either a liposoluble antioxidant, for instance butyl hydroxytoluene (BHT) or vitamin E, or a water-soluble antioxidant, for instance vitamin C. According to this publication, W/O emulsions containing retinol stabilized with a system consisting of a liposoluble antioxidant and a water-soluble antioxidant can also be prepared.
EP 608,433 describes compositions containing retinol and a stabilizer chosen from chelating agents and polysaccharides, oils with an iodine number of greater than 70, polyethylene (propylene) glycols, hydroxycarboxylic acid salts, neutral amino acid salts, liposoluble antioxidants combined with EDTA and a benzophenone, liposoluble antioxidants combined with an acidic compound and a benzophenone, cyclodextrin derivatives in which an antioxidant or a UV screening agent is included, butanediol and/or liposoluble antioxidants, water-soluble benzophenone derivatives, basic amino acids and their salts, acidic amino acids and their salts, polar oils and hydrophilic mineral clays.
Lastly, the use of N-acyl carnosine and histidine derivatives as antioxidants, in particular as inhibitors of the formation of lipid peroxides, in the presence of which retinol is known to be unstable, is known from EP 500,332 and from the publication “Antioxidant and Emulsifying Activity of N-(long-chain-acyl) histidine and N-(long-chain-acyl) carnosine”, Hironobu Murase, J. Agric. Food Chem., Vol. 41, 1993, pp. 1601-1604.
However, none of these compounds whether they are described as antioxidants or more specifically as retinoid stabilizers, allow satisfactory stabilization of retinoids to be obtained. Accordingly, there remains a need for compositions containing retinoids which are stabilized from thermal degradation.
SUMMARY OF THE INVENTION
An object of the present invention is to provide compositions containing one or more retinoids, in which the retinoids have enhanced resistance to thermal degradation.
It is another object of the present invention to provide methods of enhancing the resistance of retinoids to thermal degradation.
The inventors have now discovered, surprisingly, that the combination of a retinoid chosen from vitamin A (or retinol) and bioconvertible precursors of vitamin A, with certain histidine derivatives, makes it possible to avoid the degradation, in particular the thermal degradation, of these retinoids. Thus, these retinoids can be introduced into cosmetic and/or dermatological compositions and can be stored for several months, without their efficiency being degraded.
Accordingly, the objects of the present invention, and others, may be accomplished with a composition containing:
(a) at least one retinoid chosen from: vitamin A (or retinol), retinal and bioconvertible precursors of vitamin A, and
(b) at least one histidine derivative represented by formula (I) below:
wherein
n is an integer ranging from 0 to 5,
n′ is an integer ranging from 1 to 16,
R represents a side chain of an amino acid,
X represents a radical chosen from the radicals of formulae, read from left to right:
—CO—, —O—CO—, —NH—CO—, —SO2—, —NH—CO—CO—, —O—CO—CO—,
R′ represents a linear or branched, saturated or unsaturated, optionally hydroxylated, C6 to C22 alkyl radical or C6 to C22 aminoalkyl radical, the amine function optionally being protected in the form of acetamide or substituted with one or two lower alkyl groups, with the proviso that R′ is an aminoalkyl radical as defined above when X=—CO—
Q
+
represents H
+
or an organic or inorganic cation,
as well as the addition salts of a compound of formula (I) with an organic or inorganic acid.
The term vitamin A means retinol of all-trans type or of 13-cis type.
The expression “bioconvertible precursor of vitamin A” denotes any compound which can be converted into vitamin A by the human body. Among these compounds, mention may be made of retinol esters, in particular C
1
-C
6
esters which are very rapidly degraded into retinol by the human body. Among the retinol esters, retinyl acetate and retinyl propionate are more particularly intended.
A subject of the invention is also a cosmetic or dermatological composition comprising the combination as described above and at least one physiologically acceptable support.
A subject of the invention is also the use of at least one histidine derivative of formula (I), as defined above, for improving the stability of a composition comprising a retinoid chosen from vitamin A (or retinol), retinal and bioconvertible precursors of vitamin A.
A subject of the invention is also a process for improving the stability of a composition comprising a retinoid chosen from vitamin A (or retinol), retinal and bioconvertible precursors of vitamin A, this process consisting in combining an effective amount of at least one histidine derivative of formula (I), as defined above, with the said retinoid.
The expression “effective amount of histidine derivative of formula (I)” means an amount which is sufficient to obtain an appreciable and significant improvement in the thermal stability of the retinoid(s) contained in the composition. This minimum amount of stabilizer to be used, w

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