Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ortho-hydroxybenzoic acid or derivative doai
Reexamination Certificate
1999-10-26
2001-07-03
Dodson, Shelley A. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ortho-hydroxybenzoic acid or derivative doai
C424S401000, C424S078020
Reexamination Certificate
active
06255297
ABSTRACT:
The present invention relates to novel salicylic acid derivatives and to the use thereof in particular in the cosmetic and/or dermatological fields. They can also be used in the pharmaceutical or veterinary field. More especially, these derivatives are used in a composition intended for human skincare, in particular to combat the signs of ageing of the skin and/or to improve the radiance of the complexion and/or to smooth out facial and/or body skin and/or to treat wrinkles and fine lines on the skin and/or to stimulate the process of epidermal renewal.
People are increasingly seeking to have a more youthful, less wrinkled appearance, by using cosmetic compositions containing active agents capable of combating ageing. In the course of the process of ageing, various-signs appear on the skin, which are very characteristic of this ageing, these being reflected in particular by a change in the skin structure and functions.
The main clinical signs of ageing of the skin are, in particular, the appearance of fine lines and deep wrinkles which increase with age. Disorganization of the “grain” of the skin is observed in particular, i.e. the micro-relief is less uniform and has an anisotropic nature. Moreover, the skin complexion is generally modified and appears paler and yellower. A loss of skin firmness and tonicity is also observed.
It is thus observed that the clinical signs of ageing of the skin result essentially from dysfunctioning of the main biological mechanisms involved in the skin.
Unfortunately, the anti-ageing active agents commonly used, such as retinoids and acidic active agents, for instance hydroxy acids, have the major drawback of causing stinging, itching and tightness of the skin after they have been applied, which may lead to discomfort or intolerance. Users with sensitive skin are thus often discouraged from using these compounds.
The Applicant has thus sought active agents having the same effect as the active agents of the prior art but without posing these problems of discomfort or of intolerance.
The Applicant has discovered, surprisingly, novel salicylic acid derivatives that are suitable for skincare and make it possible in particular to combat the signs of ageing, to improve the radiance of the skin complexion, to smooth out lines on the skin and to stimulate the process of epidermal renewal, without causing any skin irritation.
Hydroxysalicylic acid derivatives are known from document EP-A-649,648. These derivatives have a different structure from the compounds of the present invention and have essentially bleaching properties.
The subject of the invention is a compound of general formula (I):
where R
1
represents hydrogen, a mono- or disaccharide residue, a group R
4
—CO—, R
4
being chosen from linear, branched or cyclic C
1
to C
20
saturated alkyl groups or C
3
to C
20
unsaturated alkyl groups, the said alkyl groups optionally being substituted;
R
2
represents hydrogen or a group R
5
—CO—, R
5
being chosen from linear or branched, saturated or unsaturated, optionally substituted C
1
to C
20
alkyl groups;
R
3
represents hydrogen, a linear or branched, saturated or unsaturated, optionally substituted C
1
to C
20
alkyl group, or a mono- or disaccharide residue, on condition that at least one of the radicals R
1
or R
3
represents a mono- or disaccharide residue and that, when R
2
is hydrogen, R
1
is other than —COCH
3
.
Advantageously, R
1
is hydrogen and R
3
represents a mono- or disaccharide residue, and in particular a galactose residue.
R
2
can be in an ortho or para position relative to the group OR
1
. Preferably, R
2
is in the para position relative to the group OR
1
and represents hydrogen or a group R
5
—CO— where R
5
is a saturated alkyl group containing from 3 to 11 carbon atoms. R
5
can be chosen in particular from linear or branched octyl, decyl, hexyl and dodecyl groups.
As substituents on the alkyl groups R
3
, R
4
and R
5
, mention may be made of halogen atoms, the trifluoromethyl group, the hydroxyl group in free form or esterified with an acid having from 1 to 6 carbon atoms, or alternatively carboxyl groups, free or esterified with a lower alcohol having from 1 to 6 carbon atoms.
Preferably, the compound according to the invention is, in particular, 3,4,5,6-tetrahydroxytetrahydropyran-2-ylmethyl 2-hydroxybenzoate, 3,4,5,6-tetrahydroxytetrahydropyran-2-ylmethyl 2-hydroxy-5-octanoylbenzoate or 2-(1,2-dihydroethyl)-4,5-dihydroxytetrahydrofuran-3-yl 2-hydroxy-5-octanoylbenzoate.
The compounds of formula (I) are novel except for 2-O-&bgr;-D-glucopyranosylsalicylic acid and glucose salicylate, which are known as analgesics for treating stomach aches and ulcers in patent JP 59,152,328. They are obtained according to a standard synthetic process which consists in reacting the protected (for example in the form of acetonide or by benzylation) sugar and the acid chloride of the salicylic derivative, or in reacting the salicylic derivative, protected in ester form, and the acid chloride of the protected sugar, and then in deprotecting the compound obtained, for example in acidic medium in the case where the sugar was protected by an acetonide function, or by hydrogenolysis in the case where the sugar was perbenzylated.
The subject of the invention is also a composition comprising at least one compound as defined above. This composition is, in particular, a topical composition, in particular a cosmetic and/or dermatological composition. In this case, it contains a physiologically acceptable medium. The expression physiologically acceptable medium is understood to refer to a medium which is compatible with the skin, mucous membranes, the nails and/or the hair.
The compounds according to the invention can be present in a composition according to the invention in an amount ranging from 0.001 to 30%, preferably from 0.01 to 10% and better still from 0.1 to 5%, relative to the total weight of the composition.
The compositions containing a compound of formula (I) can be in any pharmaceutical form usually suitable for topical application, and, for example, in the form of an aqueous, alcoholic, aqueous-alcoholic or oily solution, an aqueous or oily gel, an anhydrous solid composition, a dispersion of the lotion or serum type, an emulsion of the water-in-oil (W/O), oil-in-water (O/W) or multiple (W/O/W or O/W/O) type, a microemulsion or a dispersion of vesicles of ionic and/or nonionic type. These compositions are prepared according to the usual methods.
These compositions can comprise at least one additive chosen from fatty substances, preserving agents, gelling agents, fragrances, silicones, surfactants, water, antioxidants, fillers, screening agents, physiologically acceptable active agents such as moisturizers, vitamins, anti-ageing active agents other than the compounds of formula (I), and mixtures thereof.
The fatty substances can be chosen from oils such as jojoba oil, liquid petroleum jelly, isopropyl palmitate, silicones (cyclopentadimethylsiloxane), waxes such as sipol wax, carnauba wax, fatty acids, fatty alcohols (stearyl alcohol) and mixtures thereof.
The amounts of the various constituents of the compositions according to the invention are those used conventionally in the fields considered.
These compositions especially constitute care creams or treatment creams for the face, for the hands or for the body (for example day creams or night creams), make-up products such as foundations, bodymilks for protection or care, and skincare lotions, gels or mousses.
The subject of the invention is also a use of the compound of formula (I) in and/or for the manufacture of a cosmetic and/or dermatological composition intended for skincare.
The subject of the invention is also a use of the compound of formula (I) in and/or for the manufacture of a cosmetic and/or dermatological composition intended to combat the signs of ageing of the skin and/or to improve the radiance of the complexion and/or to smooth out facial skin and/or body skin and/or to treat wrinkles and fine lines on the skin and/or to stimulate the process of epidermal r
Dalko Maria
Galey Jean-Baptiste
Dodson Shelley A.
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
George Konata M.
L'Oreal
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