Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – C-o-group doai
Reexamination Certificate
2000-02-16
2002-06-18
Badio, Barbara P. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
C-o-group doai
Reexamination Certificate
active
06407142
ABSTRACT:
The present invention relates to the use of 3,5-dihydroxystilbene or 3-hydroxystilbene and/or derivatives thereof as deodorant active agents in the preparation of a cosmetic composition, to the deodorant cosmetic composition containing these compounds and to the use of the composition for human topical application. The invention also relates to a process for treating human underarm odors, which comprises applying an effective amount of the composition to the armpit area.
In the cosmetics field, it is a well-known practice to use, in topical application, deodorant products containing active substances of antiperspirant type or of bactericidal type to reduce or even eliminate underarm odors, which are generally unpleasant. Antiperspirants have the effect of limiting the flow of sweat. They generally consist of aluminium salts, which, on the one hand, are skin irritants and, on the other hand, reduce the flow of sweat by modifying the skin physiology, which is unsatisfactory. Bactericides inhibit the growth of the skin flora responsible for underarm odors. Among bactericidal products, the one most commonly used is Triclosan (2,4,4′-trichloro-2′-hydroxydiphenyl ether), which has the drawback of considerably modifying the ecology of the skin flora and of being inhibited by certain compounds such as, for example, nonionic surfactants, commonly used in the formulation of cosmetic compositions. Moreover, the insoluble nature of Triclosan in water does not allow it to be incorporated into essentially aqueous formulations.
With the aim of obtaining long-term efficacy, novel products are sought that exert a deodorant action, i.e., products capable of modifying, reducing and/or eliminating or preventing the development of body odor (this definition is given in the book “Cosmetic Science and Technology Series”—1988/Volume 7, chapter 10-IIIc, incorporated by reference herein). In addition, products are sought that do not have the drawbacks of the active substances used in the prior art. It is known that certain stilbene compounds, such as 4-hydroxystilbene and 3,5,4′-stilbene (or Resveratrol), make it possible to limit the development of sweat odor. However, the efficacy of these molecules is very markedly insufficient.
After considerable research conducted in this matter, the inventors have now discovered, surprisingly and unexpectedly, that the compounds of formula (I) defined below have the property of preventing the development of body odor, without the drawbacks of the active substances previously used in deodorant compositions, and with the advantage, for some of these compounds, of being water-soluble in proportions that are advantageous and sufficient to be easy to place in formulation, especially in water-based cosmetic compositions for human topical application. This discovery forms the basis of the present invention.
A first subject of the present invention is thus the use of compounds of formula (I) below as deodorant active agents in cosmetic compositions:
in which:
A denotes a hydrogen atom or a radical OR
2
,
R
1
and R
2
, which may be identical or different, denote a hydrogen atom; a C
1
-C
4
alkyl radical; an acyl radical R
3
CO in which R
3
denotes a linear or branched, saturated or unsaturated, hydroxylated or non-hydroxylated, carboxylated or non-carboxylated C
1
-C
30
hydrocarbon-based radical; a radical PO(OX
1
)(OX
2
) or a radical SO
2
(OX
3
) in which X
1
, X
2
and X
3
, which may be identical or different, denote a hydrogen atom or a monovalent alkali metal or NH
4
+
cation, in which X
1
and/or X
2
can also denote a divalent metal cation; a glycosyl radical; or a uronyl radical; and
R
4
and R
5
, which are identical, denote a hydrogen atom or a hydroxyl radical.
A second subject of the invention is a deodorant cosmetic composition comprising at least one compound of formula (I) described above. Another subject of the invention is the use of the composition in or for the manufacture of deodorant cosmetic products intended for human topical application. Yet another subject of the invention is the use of at least one compound of formula (I) described above, as a selective inhibitor of certain bacterial species constituting the human skin flora, and, in particular,
Corynebacterium xerosis
. Still another subject of the invention is a process for treating human underarm odors, which comprises applying an effective amount of the composition to the armpit area.
A subject of the invention is also novel compounds of formula (I) as defined above, in which A denotes a hydrogen atom or a radical OR
2
, R
1
and R
2
, which may be identical or different, denote an acyl radical R
3
CO in which R
3
denotes a linear or branched, saturated or unsaturated, hydroxylated or non-hydroxylated, carboxylated or non-carboxylated C
4
-C
30
hydrocarbon-based radical; a radical PO(OX
1
)(OX
2
) or a radical SO
2
(OX
3
) in which X
1
, X
2
and X
3
, which may be identical or different, denote a hydrogen atom or a monovalent alkali metal or NH
4
+
cation, in which X
1
and/or X
2
can also denote a divalent metal cation; or a uronyl radical, and R
4
and R
5
, which are identical, denote a hydrogen atom or a hydroxy radical.
Another subject of the invention is a cosmetic composition comprising at least one compound of formula (I) defined above, in which A denotes a hydrogen atom or a radical OR
2
, R
1
and R
2
, which may be identical or different, denote an acyl radical R
3
CO in which R
3
denotes a linear or branched, saturated or unsaturated, hydroxylated or non-hydroxylated, carboxylated or non-carboxylated C
1
-C
30
hydrocarbon-based radical; a radical PO(OX
1
)(OX
2
) or a radical SO
2
(OX
3
) in which X
1
, X
2
and X
3
, which may be identical or different, denote a hydrogen atom or a monovalent alkali metal or NH
4
+
cation, in which X
1
and/or X
2
can also denote a divalent metal cation; or a uronyl radical, and R
4
and R
5
, which are identical, denote a hydrogen atom or a hydroxyl radical.
In formula (I) described above, the alkyl radicals can be linear or branched and, in particular, denote methyl, ethyl, propyl, isopropyl, n-propyl, butyl, n-butyl or tert-butyl radicals. Preferably, the alkyl radical denotes a methyl radical and the glycosyl radical denotes a saccharose or saccharide radical, such as arabinose, glucose, fructose or sucrose. More preferably, the glycosyl radical denotes a glucosyl radical; also preferably the uronyl radical denotes a mannuronyl or glucuronyl radical.
Among the compounds of formula (I) used according to the present invention, particular examples include 3,5-dihydroxystilbene (or Pinosylvine), its monomethyl and dimethyl ethers, 3,5,3′,4′-tetrahydroxystilbene, and the corresponding mono- and diglycoside forms. Mention may also be made of 3-hydroxystilbene and its methyl ether.
In the present invention, the glucoside and glucuronide forms of these compounds of formula (I) are particularly advantageous since, on account of their water-solubility, they have the advantage of being easy to place in formulation in essentially an aqueous medium. In addition, they can release the active substance in situ under the action of glycosidases of bacterial origin, which are present under the armpits.
According to the invention, it is even more particularly preferred to use 3,5-dihydroxystilbene (or Pinosylvine), which, in comparison with Triclosan that is well known in the field under consideration, has the advantage of being more effective regarding deodorant activity, of being odorless at working concentrations, and of being more respectful to the skin's bacterial flora, since its bactericidal action is selective on
Corynebacterium xerosis
, the main strain producing perspiration odors.
The compounds of formula (I) according to the invention preferably represent 0.001 to 10% by weight approximately relative to the total weight of the deodorant cosmetic composition, more particularly, from 0.01 to 5%, and, even more particularly, from 0.1 to 5% by weight approximately relative to this weight
Courbriere Christophe
Kravtchenko Sylvain
Pruche Francis
Badio Barbara P.
Finnegan Henderson Farabow Garrett & Dunner LLP
L'Oreal (S.A.)
LandOfFree
Use of stilbene derivatives substituted in position 3 as... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Use of stilbene derivatives substituted in position 3 as..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Use of stilbene derivatives substituted in position 3 as... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2897083