Drug – bio-affecting and body treating compositions – Topical sun or radiation screening – or tanning preparations
Reexamination Certificate
2000-05-08
2002-05-21
Dodson, Shelley A. (Department: 1616)
Drug, bio-affecting and body treating compositions
Topical sun or radiation screening, or tanning preparations
C424S060000, C424S400000, C424S401000, C514S859000
Reexamination Certificate
active
06391287
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a composition containing at least one bicyclic aromatic compound and at least one lipophilic sunscreen, to uses of the composition, and to a process for dissolving the compound with at least one lipophilic sunscreen.
2. Discussion of the Background
Bicyclic aromatic compounds with retinoid-type activity, which are useful in particular in preventing or treating various keratinization disorders, are described in EP 679 630. These compounds are cosmetic active agents of choice, in particular for repairing or combating chronological or actinic ageing of the skin, for example such as in anti-wrinkle products.
However, it has been observed that these compounds are difficult to dissolve in cosmetic compositions. Thus, these active agents have a tendency to recrystallize or to be degraded. This leads to a more or less pronounced loss of efficacy of the compositions containing them, depending on the degree of recrystallization and/or of degradation, which runs counter to the desired objective. In addition, this recrystallization or degradation can modify the overall stability of these compositions, as well as their appearance, which dissuades consumers from using these products.
There is thus a need to dissolve these compounds in a physiologically acceptable solubilizing agent.
It is also known from WO 97/31620 to use lipophilic screening agents, such as octocrylene and octyl methoxycinnamate, together with compounds with retinoid-type activity. These lipophilic screening agents are intended to modulate the irritation induced by the retinoids by delaying and/or modulating their release.
The retinoids to which reference is made in WO 97/31620 are retinol, retinal and retinoic acid, are irritant compounds. On the other hand, the bicyclic aromatic compounds mentioned above, which have retinoid-type activity similar to that of retinol or retinoic acid, have the advantage over the retinoids given as examples in WO 97/31620 of not being irritating.
Consequently, it was not obvious to a person skilled in the art that the combination of the bicyclic aromatic compounds described below with lipophilic sunscreens would be of any value.
SUMMARY OF THE INVENTION
The present Inventors have now discovered, surprisingly, that lipophilic sunscreens make it possible to dissolve the bicyclic aromatic compounds discussed above. The present invention is based on this discovery.
Thus, the present invention provides a composition comprising at least one bicyclic aromatic compound and at least one lipophilic sunscreen.
The present invention also provides a process for dissolving a bicyclic aromatic compound by mixing the bicyclic compound with at least one lipophilic sunscreen. The mixing can be carried out under a wide variety of conditions, e.g., cold conditions, at room temperature, or under warm conditions, for example at 80° C., generally with stirring.
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
The bicyclic aromatic compounds according to the invention have, specifically, the general formula (I) below:
where
R
1
represents a hydrogen atom, a radical —CH
3
, a radical —CH
2
—O—R
3
, a radical —CH
2
—O—CO—R
4
, a radical —O—R
5
, a radical —O—(CH
2
)
m
—(CO)
n
—R
6
, a radical —CO—O—R
8
or a radical —S(O)
p
—R
9
, the values m, n and p and the various radicals R
3
to R
9
having the meaning described below,
R
2
represents a hydrogen atom or a halogen atom, a lower alkyl radical, an —NO
2
radical, a radical —O—COR
4
, a radical —OR
9
or a radical:
the radicals R
4
, R
9
and R
10
having the meaning described below, Ar represents a radical chosen from the radicals of formulae (a)-(e) below:
in which R
2
is described above and R
9
has the meaning described below, X represents —O—, —S(O)
t
— or a radical —NR
9
—, the value t and the radical R
9
having the meaning described below,
Y and Z represent —O—, —S(O)
t
— or a radical —CR
11
R
12
, the value t and the radicals R
11
and R
12
having the meaning described below, it being understood that, in all of the text hereinabove:
m is an integer equal to 1, 2 or 3, n is an integer equal to 0 or 1, p is an integer equal to 0, 1, 2 or 3 and t is an integer equal to 0, 1 or 2,
R
3
, R
5
, R
9
, R
10
, R
11
, and R
12
represent, independently of each other, a hydrogen atom or a lower alkyl radical,
R
4
represents a lower alkyl radical,
R
6
represents a lower alkyl radical or a heterocycle,
R
7
represents a hydrogen atom, a lower alkyl radical or a radical:
in which R′ and R″, which may be identical or different, represent a hydrogen atom, a lower alkyl radical, a mono- or polyhydroxyalkyl radical, an optionally substituted aryl radical or an amino acid or peptide or sugar residue, or alternatively, taken together, form a heterocycle,
R
8
represents a hydrogen atom, a linear or branched alkyl radical containing from 1 to 20 carbon atoms, an alkenyl radical, a mono- or polyhydroxyalkyl radical, an optionally substituted aryl or aralkyl radical, a sugar residue or an amino acid or peptide residue,
Y and Z cannot simultaneously represent an oxygen atom or a radical —S(O)
t
—.
The invention is also directed towards the salts of the compounds of formula (I) above when the radical R
1
represents a carboxylic acid function or a sulfonic acid function or bears an amine function, or alternatively when the radical R
2
represents an amine function, as well as the chiral analogues of the said compounds. When the compounds according to the invention are in the form of salts, they are preferably salts of an alkali metal or alkaline-earth metal, or alternatively of zinc or of an organic amine.
According to the present invention, the term “lower alkyl radical” refers to a radical containing from 1 to 6 carbon atoms, preferably methyl, ethyl, isopropyl, butyl, tert-butyl and hexyl radicals.
The term “linear or branched alkyl radical containing from 1 to 20 carbon atoms” refers to methyl, ethyl, propyl, 2-ethylhexyl, octyl, dodecyl, hexadecyl and oxadecyl radicals.
The term “monohydroxyalkyl radical” refers to radical preferably containing 2 or 3 carbon atoms, in particular a 2-hydroxyethyl, 2-hydroxypropyl or 3-hydroxypropyl radical.
The term “polyhydroxyalkyl radical” refers to radical preferably containing from 3 to 6 carbon atoms and from 2 to 5 hydroxyl groups, such as 2,3-dihydroxypropyl, 2,3,4-trihydroxybutyl and 2,3,4,5-tetrahydroxypentyl radicals or a pentaerythritol residue.
The term “aryl radical” preferably refers to a phenyl radical optionally substituted with at least one halogen atom, a hydroxyl or a nitro function.
The term “aralkyl radical” preferably refers to a benzyl or phenethyl radical optionally substituted with at least one halogen atom, a hydroxyl or a nitro function.
The term “alkenyl radical” refers to a radical preferably containing from 2 to 5 carbon atoms and containing one or more ethylenic unsaturations, such as, more particularly, an allyl radical.
The term “sugar residue” refers to a residue derived in particular from glucose, galactose or mannose, or alternatively from glucuronic acid.
The term “amino acid residue” in particular refers to a residue derived from lysine, glycine or aspartic acid, and the expression “peptide residue” more particularly means a dipeptide or tripeptide residue resulting from the combination of amino acids.
The term “heterocycle” preferably means a piperidino, morpholino, pyrrolidino or piperazino radical, optionally substituted in position 4 with a C
1
-C
6
alkyl or mono- or polyhydroxyalkyl radical as defined above.
When the radical R
2
represents a halogen atom, it is preferably a fluorine, chlorine or bromine atom.
In the present invention, the compounds of formula (I) which are more particularly preferred are those for which at least one, and preferably all, of the conditions below are satisfied:
R
1
i
Baldo Francine
Guiramand Carole
Dodson Shelley A.
L'Oreal
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