Drug – bio-affecting and body treating compositions – Bleach for live hair or skin
Reexamination Certificate
2000-01-24
2001-05-08
Page, Thurman K. (Department: 1615)
Drug, bio-affecting and body treating compositions
Bleach for live hair or skin
C424S401000, C514S640000
Reexamination Certificate
active
06228350
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a method of using, in a topical cosmetic composition, or for the manufacture of a topical dermatological composition, at least one compound comprising a phenyloxime fragment depigmenting and/or bleaching human skin, body hair or head hair.
2. Description of the Background
The color of human skin depends on various factors and in particular on the seasons of the year, race and sex, and it is mainly determined by the nature and concentration of melanin produced by the melanocytes. Melanocytes are specialized cells which synthesize melanin, via specific organelles, the melanosomes. In addition, at various periods in their life, certain individuals develop darker and/or more colored marks on the skin, and more especially on the hands, making the skin non-uniform. These marks are also due to a large concentration of melanin in the keratinocytes located at the surface of the skin.
Similarly, the color of body hair and head hair is due to melanin, and when the body hair or head hair is dark, certain individuals wish to make them lighter. This is particularly advantageous for body hair which is less visible when it is light than when it is dark.
The substances most commonly used as depigmenting agents are, more particularly, hydroquinone and its derivatives, in particular its ethers such as hydroquinone monomethyl ether and monoethyl ether. Unfortunately, although these compounds have a certain level of efficacy, they are not free of side effects on account of their toxicity, which can make them problematic or even hazardous to use. This toxicity arises from the fact that they intervene in fundamental mechanisms of melanogenesis by killing cells which then create the risk of disrupting their biological environment and consequently oblige the skin to remove them by producing toxins.
Thus, hydroquinone is a compound which is particularly irritant and cytotoxic to melanocytes, and its total or partial replacement has been envisaged by many authors.
The use of harmless topical depigmenting substances which have good efficacy is most particularly desired in order to treat regional hyperpigmentations caused by melanocyte hyperactivity, such as idiopathic melasmas occurring during pregnancy (“pregnancy mask” or chloasma) or during oestro-progestative contraception, localized hyperpigmentations caused by hyperactivity and proliferation of benign melanocytes, such as senile pigmentation marks known as actinic lentigo, accidental hyperpigmentations or depigmentations, which may be due to light-sensitization or to post-lesional cicatrization, as well as certain leukodermias, such as vitiligo. For the latter pigmentation conditions (it being possible for cicatrizations to result in a scar giving the skin a whiter appearance, and leukodermias), failing the ability to repigment the damaged skin, the approach finally adopted is to depigment the regions of residual normal skin in order to give the skin as a whole a uniform white shade.
Thus, a need exists for a novel agent for bleaching human skin, body hair and/or head hair, which acts as effectively as the known agents but does not have their drawbacks, i.e. which is non-irritant, non-toxic and/or non-allergenic to the skin and is stable in a composition.
SUMMARY OF THE INVENTION
The inventors have now discovered, unexpectedly, that compounds comprising a phenyloxime fragment have depigmenting activity, even at low concentrations, without showing any cytotoxicity.
Thus, the present invention provides a method of depigmenting and/or bleaching human skin, body hair or head hair, comprising applying to human skin, body hair or head hair at least one compound represented by formula (I):
where
R represents a group chosen from:
a hydrogen atom;
a linear, branched or cyclic, saturated or unsaturated C
1
-C
24
alkyl group, optionally hydroxylated with one or more hydroxyl functions;
an aryl group, which may be unsubstituted or substituted with one or more functions chosen from —OH; NH
2
; —COOH; —NO
2
; —OR
5
with R
5
=C
1
-C
24
alkyl; —COOR
6
with R
6
=C
1
-C
24
alkyl; —NR
7
R
8
with R
7
=H or C
1
-C
24
alkyl, R
8
=H or C
1
-C
24
alkyl; and
a group —COR
9
, R
9
representing a linear, branched or cyclic, saturated or unsaturated C
1
-C
24
alkyl group, optionally hydroxylated with one or more hydroxyl functions, or an aryl group which may be unsubstituted or substituted with one or more functions chosen from —OH, —NH
2
, —COOH, —NO
2
, —OR
5
, —COOR
6
and —NR
7
R
8
in which R
5
, R
6
, R
7
and R
8
have the same definition as above;
R
1
and R
2
, which may be identical or different, represent a group chosen from:
a hydrogen atom;
a linear, branched or cyclic, saturated or unsaturated C
1
-C
24
alkyl group, optionally hydroxylated with one or more hydroxyl functions;
an aryl group, which may be unsubstituted or substituted with one or more functions chosen from —OH, —NH
2
, —COOH, —NO
2
, —OR
5
, —COOR
6
and —NR
7
R
8
in which R
5
, R
6
, R
7
and R
8
have the same definition as above;
a group chosen from: —OH; —OQ
1
; —COQ
2
; —COOQ
3
; —NQ
4
Q
5
; —CONQ
6
Q
7
; —SQ
8
; —CH
2
OQ
9
; Q
1
, Q
2
, Q
3
, Q
4
, Q
5
, Q
6
, Q
7
, Q
8
and Q
9
, which may be identical or different, being chosen from a hydrogen atom, linear, branched or cyclic, saturated or unsaturated C
1
-C
24
alkyl groups, optionally substituted with one or more hydroxyl groups, aryl groups which may be unsubstituted or substituted with one or more functions chosen from: —OH, —NH
2
, —COOH, —NO
2
, —OR
5
, —COOR
6
and —NR
7
R
8
in which R
5
, R
6
, R
7
and R
8
have the same definition as above; and
amino acid residues and cyclic or non-cyclic carbohydrate residues;
R
3
represents a group chosen from:
a hydrogen atom;
a linear, branched or cyclic, saturated or unsaturated C
1
-C
24
alkyl group, optionally hydroxylated with one or more hydroxyl functions; and
an aryl group, which may be unsubstituted or substituted with one or more functions chosen from —OH, —NH
2
, —COOH, —NO
2
, —OR
5
, —COOR
6
and —NR
7
R
8
in which R
5
, R
6
, R
7
and R
8
have the same definition as above.
A subject of the present invention is also the use of at least one compound of formula (I) above for the manufacture of a dermatological composition intended for depigmenting and/or bleaching human skin and/or for removing pigmentation marks from the skin and/or for depigmenting body hair and/or head hair, comprising a dermatologically acceptable medium and intended for topical application to the skin and/or its body hair or head hair.
Accordingly, the present invention provides a method of depigmenting and/or bleaching human skin, body hair or head hair, comprising applying to human skin, body hair or head hair at least one compound represented by formula (I).
The present invention also provides a cosmetic and/or dermatological composition, comprising a cosmetically and/or dermatologically acceptable carrier and at least one compound represented by formula (I).
The present invention also provides a method of making the cosmetic and/or dermatological composition.
A more complete appreciation of the invention and many of the attendant advantages thereof will be readily obtained as the same becomes better understood by reference to the following detailed description.
DETAILED DESCRIPTION OF THE INVENTION
Some of the compounds represented by formula (I) are described as photoprotective compounds intended for protecting the skin against light-induced ageing and solar erythema (WO 95/01157), as tyrosinase inhibitors in oral compositions for treating cancer, in combination with interferon (U.S. Pat. No. 4,762,705) or as lipoxygenase inhibitors, in anti-inflammatory compositions (U.S. Pat. No. 4,816,487). Each of these publications is incorporated herein by reference. However, these compounds have not been described as depigmenting agents or in depigmenting compositions.
These compounds have the advantage of being easy to synthesize. They can be obtained, for example, by reacting hydroxyl
Philippe Michel
Tuloup Remy
Fubara Blessing
L'Oreal
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
Page Thurman K.
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