Resorcinol derivatives for their cosmetic use
阅读说明：本技术 针对其化妆品用途的间苯二酚衍生物 (Resorcinol derivatives for their cosmetic use ) 是由 X.马拉 C.马 于 2018-05-30 设计创作，主要内容包括：本发明涉及式(I)的间苯二酚衍生的化合物以及其盐、其溶剂化物和其光学和/或几何异构体(包括对映异构体和非对映异构体)、其外消旋混合物,单独地或作为混合物。本发明还涉及一种使用这些化合物(I)使角蛋白材料、特别是皮肤脱色、增亮和/或漂白的美容方法。(The present invention relates to resorcinol-derived compounds of formula (I) as well as salts thereof, solvates thereof and optical and/or geometric isomers thereof (including enantiomers and diastereomers), racemic mixtures thereof, alone or as a mixture. The invention also relates to a cosmetic process for depigmenting, lightening and/or bleaching keratin materials, in particular the skin, using these compounds (I).)
1. A compound of formula (I):
wherein:
R1and R2Which may be the same or different, represent:
a) a hydrogen atom(s) H, or a hydrogen atom,
b) group COR8Wherein R is8Represents a saturated straight chain C1-C20Hydrocarbyl, unsaturated straight chain C2-C20Hydrocarbyl, branched saturated or unsaturated C3-C20Radical or C3-C8A cyclic hydrocarbon group,
c) radical S*Denotes a monosaccharide sugar radical or a polysaccharide sugar radical comprising 2 to 5 sugar units, preferably 2 to 3 sugar units, preferably a sugar radical comprising 1 or 2 sugar units (mono-or disaccharide), the mono-or polysaccharide radical S*To the remainder of the molecule via a bond between the carbon atoms C1 of one of the saccharides in the monosaccharide or polysaccharide group, which bond may be alpha or beta anomeric,
R3represents saturated C1-C20Or unsaturated C2-C20Straight or branched chain C3-C20Or cyclic C3-C8A hydrocarbon group,
r represents:
the group OR5Wherein R is5Represents H or saturated straight chain C1-C20Hydrocarbyl, unsaturated straight chain C2-C20Hydrocarbyl, saturated or unsaturated branched C3-C20Hydrocarbyl or C3-C8Cycloalkyl, which is optionally substituted by one or more hydroxyl groups and/or by one or more heterocycles, and/or which is optionally interrupted by one or more, in particular one to three, non-adjacent heteroatoms or groups selected from N, O, -CO-, or combinations thereof, such as-NHCO-,
-group NR6R7Wherein R is6And R7Independently represent:
a) a hydrogen atom(s) H, or a hydrogen atom,
b) saturated C1-C20Or unsaturated C2-C20Or branched C3-C20Or cyclic C3-C8Hydrocarbyl optionally interrupted by one or more, especially one to three, non-adjacent heteroatoms or groups selected from N, O, -CO-, and combinations thereof, such as-NHCO-, -NHCONH-, and/or optionally substituted by one or more identical or different groups selected from:
i)-OR9
ii)-SR9
iii)-NR9R10
iv)-CONR9R10
v)-COOR9
vi)-NHCONHR9
vii) -C (O) alkyl (C)1-C4)
viii) saturated or unsaturated nonaromatic (hetero) cyclic groups, which are optionally substituted by one or more, especially one to three, hydroxyl groups and/or by one or more, especially one to three, C1-C8Alkoxy and/or C1-C8Alkyl substitution; one of the chain members of the (hetero) cyclic group may be a carbonyl group
ix)C5-C12(hetero) aryl optionally substituted by one or more, especially one to three, hydroxyl groups and/or by one or more, especially one to three, C1-C8Alkoxy and/or C1-C8Alkyl substitution
x)-NH-C＝NH(NH2) (guanidine group)
R9And R10May be the same or different and is selected from H, saturated straight chain C1-C10Hydrocarbyl, unsaturated straight chain C2-C10Hydrocarbyl, saturated or unsaturated branched C3-C10A hydrocarbon group and C3-C8A cyclic hydrocarbon group; (C)1-C4) Alkyl radical (C)6) (hetero) aryl optionally containing a nitrogen atom, in particular benzyl; acetyl;
R9and R10Possibly forming, with the nitrogen bearing them, a 5-to 8-membered heterocyclic ring which may contain one or more, in particular one to three, heteroatoms or groups selected from N, O, -CO-, and/or optionally be C-based1-C10A hydrocarbon chain, in particular alkyl substitution;
c) group NR11R12Wherein R is11And R12Independently represents a group selected from:
i)-H
ii) saturated straight chain C1-C10Or unsaturated C2-C10Or branched C3-C10Or cyclic C3-C8A hydrocarbon group, which is optionalIs interrupted by one or more heteroatoms or groups selected from N, O, -CO and combinations thereof, such as-NHCO-, -NHCONH-, and/or is optionally interrupted by one or more, especially one to three, identical or different C1-C8Alkyl substitution
iii)C5-C12(hetero) aryl optionally containing one or more, especially one to three, heteroatoms selected from O, N and S, optionally substituted by one or more, especially one to three, hydroxyl groups and/or by one or more, especially one to three, C1-C8Alkoxy substitution; r11And R12Possibly forming, with the nitrogen bearing them, a 5-to 8-membered heterocyclic ring which may contain one or more, in particular one to three, heteroatoms or groups selected from N, O and-CO-, and/or which is optionally C-based1-C10Chain substitution of hydrocarbons, said chain optionally containing one or more, especially one to three, groups selected from hydroxyl and C1-C4A group of alkoxy groups;
d) group OR13Wherein R is13Represents a group selected from:
i)-H
ii) saturated straight chain C1-C10Or branched C3-C10Or cyclic C3-C8A hydrocarbon group,
R6and R7Possibly forming, with the nitrogen bearing them, a 5-to 8-membered heterocyclic ring which may contain one or more, in particular one to three, heteroatoms or groups selected from N, O, -CO-, and/or optionally be C-based1-C10Chain substitution of hydrocarbons;
and salts thereof, solvates thereof and optical and/or geometric isomers thereof including enantiomers and diastereomers, racemic mixtures thereof, alone or as mixtures, but wherein R is1＝R2H, R-Me and R4Except for OH compounds (I).
2. The compound according to the preceding claim, wherein:
R1and R2Independently of each otherRepresents:
a)H，
b) group COR8Wherein R is8Represents a saturated straight chain C1-C20Hydrocarbyl, unsaturated straight chain C2-C20Hydrocarbyl, branched saturated or unsaturated C3-C20Radical or C3-C8Cycloalkyl, and preferably saturated C1-C4Hydrocarbyl groups, such as methyl.
3. The compound of any one of the preceding claims, wherein:
R3represents saturated C1-C20Or unsaturated C2-C20A hydrocarbon group which is a straight chain or a branched chain C3-C20Or cyclic C3-C8(ii) a More preferably, R3Represents saturated C1-C10Or unsaturated C2-C10Hydrocarbyl, and even more preferably, R3Represents saturated C1-C4Hydrocarbyl groups, such as methyl.
4. The compound of any one of the preceding claims, wherein:
r represents:
the group OR5Wherein R is5Represents H or saturated straight chain C1-C20Hydrocarbyl, unsaturated straight chain C2-C20Hydrocarbyl, saturated or unsaturated branched C3-C20Hydrocarbyl or C3-C8Cycloalkyl, which is optionally substituted by one or more hydroxyl groups and/or by one or more heterocycles, and/or which is optionally interrupted by one or more, in particular one to three, non-adjacent heteroatoms or groups selected from N, O, -CO-, or combinations thereof, such as-NHCO-,
-group NR6R7Wherein R is6And R7Independently represent:
a) a hydrogen atom(s) H, or a hydrogen atom,
b) saturated C1-C20Or unsaturated C2-C20Or branched C3-C20Or cyclic C3-C8Hydrocarbyl optionally interrupted by one or more, especially one to three, non-adjacent heteroatoms or groups selected from N, O, -CO-, and combinations thereof, such as-NHCO-, -NHCONH-, and/or optionally substituted by one or more identical or different groups selected from:
i)-OR9
ii)-COOR9
iii) saturated or unsaturated nonaromatic (hetero) cyclic groups, optionally substituted by one or more, especially one to three, hydroxyl groups and/or by one or more, especially one to three, C1-C8Alkoxy and/or C1-C8Alkyl substitution; one of the chain members of the (hetero) cyclic group may be a carbonyl group,
iv)C5-C12(hetero) aryl optionally substituted by one or more, especially one to three, hydroxyl groups, and/or by one or more, especially one to three, C1-C8Alkoxy and/or C1-C8The substitution of the alkyl group is carried out,
R9and R10May be the same or different and is selected from H, saturated straight chain C1-C10Hydrocarbyl, unsaturated straight chain C2-C10Hydrocarbyl, saturated or unsaturated branched C3-C10A hydrocarbon group and C3-C8A cyclic hydrocarbon group; (C)1-C4) Alkyl radical (C)6) (hetero) aryl optionally containing a nitrogen atom, in particular benzyl; acetyl; in particular an alkyl group, and in particular,
R9and R10Possibly forming, with the nitrogen bearing them, a 5-to 8-membered heterocyclic ring which may contain one or more, in particular one to three, heteroatoms or groups selected from N, O, -CO-, and/or optionally be C-based1-C10A hydrocarbon chain, in particular alkyl substitution;
c) group NR11R12Wherein R is11And R12Independently represents a group selected from:
i)-H
ii) saturated straight chain C1-C10Or unsaturated C2-C10Or branched C3-C10Or cyclic C3-C8A hydrocarbyl group optionally interrupted by one or more heteroatoms or groups selected from N, O, -CO, and combinations thereof, such as-NHCO-, -NHCONH-, and/or optionally interrupted by one or more, especially one to three, identical or different C1-C8Alkyl substitution
d) Group OR13Wherein R is13Represents a group selected from:
i)-H
R6and R7Possibly forming, with the nitrogen bearing them, a 5-to 8-membered heterocyclic ring which may contain one or more, in particular one to three, heteroatoms or groups selected from N, O, -CO-, and/or optionally be C-based1-C10Chain substitution of hydrocarbons.
5. The compounds according to any one of the preceding claims, selected from:
6. the compounds according to any one of the preceding claims, selected from:
7. compound according to any one of the preceding claims, characterized in that the group based on branched or saturated linear hydrocarbons is selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, 2-ethylhexyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl.
8. Compound according to any one of the preceding claims, characterized in that the group based on branched or saturated linear hydrocarbons is selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, 2-ethylhexyl and octyl.
9. Compound according to any one of the preceding claims, characterized in that the group based on branched or saturated linear hydrocarbons is chosen from methyl, ethyl, propyl, butyl and hexyl groups.
10. Compound according to any one of the preceding claims, characterized in that the cycloalkyl is chosen from cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
11. A cosmetic composition comprising, in a physiologically acceptable medium, a compound of formula (I) according to any one of the preceding claims.
12. Composition according to claim 11, characterized in that the compound (I) is present in a content ranging from 0.01% to 10% by weight, preferably ranging from 0.1% to 5% by weight and preferably ranging from 0.5% to 3% by weight relative to the total weight of the composition.
13. Composition according to either of claims 11 and 12, characterized in that it comprises at least one adjuvant chosen from the group formed by: organic solvents, especially C2-C6 alcohols; oils, especially hydrocarbon-based oils and silicone oils; waxes, pigments, fillers, dyes, surfactants, emulsifiers; cosmetic active agents, organic or inorganic photo-protecting agents, polymers, thickeners, preservatives, fragrances, bactericides, ceramides, odor absorbers, antioxidants.
14. The composition according to any one of claims 11 to 13, characterized in that it comprises at least one active agent chosen from: a desquamation agent; sedatives, organic or inorganic photoprotective agents, moisturizers; a decolorizing agent; an anti-glycation agent; an NO-synthase inhibitor; an agent for stimulating the synthesis of dermal or epidermal macromolecules and/or for preventing their degradation; an agent for stimulating fibroblast and/or keratinocyte proliferation or for stimulating keratinocyte differentiation; a tensioning agent; anti-fouling agents and/or radical scavengers; an agent that acts on capillary circulation; an agent that acts on cellular energy metabolism; and mixtures thereof.
15. A non-therapeutic cosmetic process for depigmenting, lightening and/or bleaching keratin materials, comprising the application of a compound of formula (I) as defined according to any one of claims 1 to 10 or a composition containing said compound according to any one of claims 11 to 14.
16. Method according to the preceding claim, for depigmenting, lightening and/or bleaching the skin.
17. Non-therapeutic cosmetic use of a compound of formula (I) according to any one of claims 1 to 10 or of a composition containing said compound according to any one of claims 11 to 14 as an agent for bleaching, lightening and/or depigmenting keratin materials.