Drug – bio-affecting and body treating compositions – Face or body powders for grooming – adorning – or absorbing
Reexamination Certificate
1998-07-31
2001-08-28
Low, Christopher S. F. (Department: 1653)
Drug, bio-affecting and body treating compositions
Face or body powders for grooming, adorning, or absorbing
C424S600000, C424S601000, C514S063000, C514S075000, C514S080000, C514S095000
Reexamination Certificate
active
06280715
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a cosmetic composition notably useful for the skin whitening, containing a compound of the general formula (I) as described hereafter, in association with any suitable excipient, the present invention relates also to a melanogenesis inhibiting agent containing such a cosmetic composition.
The compounds (I) according to the invention have the general formula:
wherein
R
1
represents a hydrogen atom, a linear or branched alkyl group or a thiazoline group,
R
2
represents a hydrogen atom, a linear or branched alkyl group or a linear or branched alkyl group substituted by a carboxyl, a hydroxyl, an amine or a thiol group,
R
3
represents a hydrogen atom, a linear or branched alkyl group, an arylalkyl group, an acyl group or an acyloxy group,
R
4
represents a hydrogen atom or a linear or branched alkyl group,
R
5
represents a hydrogen atom or a hydroxyl group or a linear or branched alkyl group.
BACKGROUND OF THE INVENTION
For several years, there has been a growing interest, in the field of cosmetics, for depigmenting products: age spots (lentigo senile), chloasma, freckles, pigmentation spots that appear on mature skins after a prolonged exposure to the sun, are badly tolerated by affected people.
Fashion phenomena favouring light complexions in Asia and Africa are also factors in favour of the development of depigmenting products.
Melanin is a pigment synthesized by melanocytes which are specific cells of the epidermal basal layer.
Hyperpigmentations are often caused by hyperactivity of the melanocytes, eventually associated to an increase of their number.
Within melanocytes, oxidation reactions that lead to the formation of melanin are mainly catalyzed by tyrosinase. Resulting pigments are uniformly distributed over the epidermis surface, except when the mechanism is disrupted: melanin is then anarchically accumulated in some areas.
The depigmenting properties of some substances have been known for long: as soon as 1936, Oettel noticed a decrease of pigmentation among black cats hair which had been given hydroquinone (Hemsworth B. N. , J.Soc Cosmet. Chem., 1973, 24, 727-733).
Some substances showed a depigmenting action but cannot be used in cosmetic because of their toxicity (for example, mercury salts), of the cutaneous irritation they induce (mercaptoamines, oxidizing products such as hydrogen peroxide) or because of the excessive slowness of their action (ascorbic acid or ascorbic acid derivatives).
Other compounds such as phenolic derivatives, corticosteroids, analogs of vitamin A, some vegetal extracts are used as components in many depigmenting preparations now on the market.
However, these compounds show some side-effects: among phenolic derivatives, hydroquinone, which is an inhibitor of tyrosinase, induces quite a few secondary reactions (inflammatory reactions, burns, prickling sensations, irreversible dyschromia in spots); corticosteroids induce such secondary reactions and cannot be used in cosmetic; analogs of vitamin A (beta carotene, canthaxanthine) are able to block the melanocyte activity but the problem with these substances is making them to penetrate into the cells without being metabolized by the cell enzymes. Plant extracts, containing either arbutin (glucose hydroquinone) or flavonoids or also cinnamic derivatives, are also used as depigmenting agents but have a very slow action.
Generally speaking, the problem with these depigmenting agents of the prior art is that it will take at least a two months treatment before seeing the first results in vivo.
SUMMARY OF THE INVENTION
To notably remedy these drawbacks, one purpose of the present invention is to suggest the use, for skin whitening, of compounds whose structure and manufacturing process are known, but have a surprising effect in skin whitening.
One purpose of the present invention is to propose a cosmetic composition useful notably in the skin whitening, characterized in that it contains, in association with any suitable excipient, at least one compound of the following general formula (I):
wherein
R
1
represents a hydrogen atom, a linear or branched alkyl group or a thiazoline group,
R
2
represents a hydrogen atom, a linear or branched alkyl group or a linear or branched alkyl group substituted by a carboxyl, a hydroxyl, an amine or a thiol group,
R
3
represents a hydrogen atom, a linear or branched alkyl group, an arylalkyl group, an acyl group or an acyloxy group,
R
4
represents a hydrogen atom or a linear or branched alkyl group,
R
5
represents a hydrogen atom, a hydroxyl group or a linear or branched alkyl group.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
Preferably, the compound of formula (I) is such as R
1
represents a hydrogen atom, a (C
1
-C
4
) alkyl group or a thiazoline group, R
2
and R
3
represent each one a hydrogen atom, and R
5
represents a hydrogen atom or a hydroxyl group.
Advantageously, the compound of formula (I) is such as R
1
represents a (C
1
-C
4
) alkyl group, R
2
and R
3
represent each one a hydrogen atom, and R
5
represents a hydrogen atom.
According to a preferred embodiment, the compound of formula (I) is the 1-amino-ethylphosphinic acid.
According to another preferred embodiment of the invention, the compound of formula (I) is the 1-amino-3-methylbutylphosphinic acid.
Preferably, the cosmetic composition according to the invention contains, in addition to compounds of general formula (I), anti-inflammatory agents, other skin whitening agents and/or antioxidants.
Advantageously, the content of compound of general formula (I) is included between 0.1 and 20% in weight in relation to the total weight of the composition and preferably between 0.5 and 5% in weight in relation with the total weight of the composition.
According to a special embodiment, the composition according to the invention contains in addition an organo-silicon compound of the following general formula:
wherein:
at least one of the radicals R
6
, R
7
, R
8
or R
9
represents a hydroxyl group or an alkoxy, acyloxy, aryloxy or amine group, or a halogen atom, and at least one other of said radicals R
6
, R
7
, R
8
or R
9
represents an alkyl group.
According to a special embodiment of the invention, the cosmetic composition contains in addition a pseudo-dipeptide such as one of the type obtained by the coupling between histamine and an aminoacid.
Preferably, this pseudo-dipeptide is the &bgr;-alanyl-histamine.
Preferably, the excipient used in the cosmetic composition according to the invention, is a micro-dispersion without surfactant.
Advantageously, the cosmetic composition according to the invention is in the form of liposomes, microparticles or nanoparticles.
According to an advantageous alternative of the invention, the cosmetic composition is in the form of a cream, a milk, a lotion, or a gel.
Another purpose of the invention is to propose a melanogenesis inhibiting agent, characterized in that it contains a cosmetic composition as described above.
The present invention will be better understood through the following description and examples, which illustrate the invention in a non restrictive way.
The compounds of general formula (I) are commercially available or can be prepared according to the methods described in the prior art, notably according to the procedure described in J. Chem. Perkin. trans. I, 1984 by BAYLIS and al.
The compounds of formula (I) preferred are those in which R
1
represents a hydrogen atom, a (C
1
-C
4
) alkyl group or a thiazoline group, R
2
and R
3
represent each one a hydrogen atom, and R
5
represents a hydrogen atom or a hydroxyl group.
Among these compounds, aminophosphinic acids, that is to say compounds of formula (I) in which R
5
represents a hydrogen atom are particularly preferred.
The compounds according to the invention are alpha-amino phosphonic or alpha-amino phosphinic acids and have thus a structure close to the structure of a natural alpha-amino acid.
The compounds used for compositions according to the invention have in themselves an inhibiting action on melanogenesis.
Babizhayev Mark A.
Seguin Marie-Christine
EXSYMOL S.A.M.
Gupta Anish
Low Christopher S. F.
Lydon James C.
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