WO2017102802A1 - Utilisation cosmétique des dérivés du résorcinol - Google Patents

Utilisation cosmétique des dérivés du résorcinol Download PDF

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WO2017102802A1
WO2017102802A1 PCT/EP2016/080911 EP2016080911W WO2017102802A1 WO 2017102802 A1 WO2017102802 A1 WO 2017102802A1 EP 2016080911 W EP2016080911 W EP 2016080911W WO 2017102802 A1 WO2017102802 A1 WO 2017102802A1
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radical
alkyl
saturated
unsaturated
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Xavier Marat
Chunyu MA
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LOreal SA
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LOreal SA
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/36—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • the present invention relates to the cosmetic use of resorcinol derivatives for depigmenting and/or bleaching the skin, and also to certain novel resorcinol derivatives.
  • spots are in particular due to a high concentration of melanin in the keratinocytes located at the surface of the skin.
  • the mechanism of formation of skin pigmentation i.e. the formation of melanin, is particularly complex and schematically involves the following main steps:
  • Tyrosinase (monophenol dihydroxyl phenylalanine: oxygen oxidoreductase EC 1.14.18.1) is the essential enzyme involved in this sequence of reactions. It in particular catalyzes the reaction for conversion of tyrosine into dopa (dihydroxyphenylalanine) by means of its hydroxylase activity, and the reaction for conversion of dopa into dopaquinone by means of its oxidase activity. This tyrosinase acts only when it is in mature form under the action of certain biological factors.
  • a substance is acknowledged as being depigmenting if it acts directly on the vitality of the epidermal melanocytes where melanogenesis takes place, and/or if it interferes with one of the steps of melanin biosynthesis, either by inhibiting one of the enzymes involved in melanogenesis, or by inserting itself as a structural analogue of one of the chemical compounds of the melanin synthesis chain, which chain can then be blocked, thus ensuring depigmentation.
  • Arbutin and kojic acid are known as skin depigmenting agents.
  • One subject of the invention is compounds of formula (I) as defined below for their dermatological use for depigmenting the skin.
  • a subject of the invention is also novel compounds of formula (II) as defined below.
  • a subject of the invention is also a non-therapeutic cosmetic treatment process for depigmenting, lightening and/or bleaching keratin materials, especially the skin, comprising the application to the skin of at least one compound of formula (I) as defined below.
  • a subject of the invention is also a composition comprising, in a physiologically acceptable medium, at least one compound of formula (II) as defined below.
  • a subject of the invention is also a non-therapeutic cosmetic process for depigmenting, lightening and/or bleaching keratin materials, especially the skin, comprising the application of the composition described previously.
  • the invention also relates to the non-therapeutic cosmetic use of at least one compound of formula (I) as defined below, as an agent for bleaching, lightening and/or depigmenting keratin materials, especially the skin.
  • They may also make it possible to depigment and/or lighten bodily hairs, the eyelashes, head hair, and also the lips and/or the nails.
  • One subject of the invention is thus compounds of formula (I) as follows, for their use for depigmenting, lightening and/or bleaching the skin:
  • Rl and R2 independently denote:
  • R6 denotes a saturated linear C1-C20 alkyl radical, an unsaturated linear C2-C20 alkyl radical, a branched saturated or unsaturated C 3 -C20 radical or a C 3 -C 8 cycloalkyl radical,
  • R3 denotes a saturated C1-C20 or unsaturated C2-C20, linear or branched C3-C20, or cyclic C 3 -C 8 alkyl radical
  • R4 and R5 independently denote
  • a saturated C1-C20 or unsaturated C2-C20 or branched C3-C20, or cyclic C3-C8 alkyl radical optionally interrupted with one or more non-adjacent heteroatoms or groups, especially one to three, chosen from N, O, -CO- and combinations thereof such as -NHCO-, -NHCONH-, and/or optionally substituted with one or more identical or different groups, especially one to three, chosen from:
  • a saturated or unsaturated non-aromatic (hetero)cyclic group said (hetero)cyclic group being optionally substituted with one or more hydroxyls, especially one to three, and/or with one or more Ci-Cs alkoxy and/or Ci-Cs alkyl radicals, especially one to three; one of the chain members of the (hetero)cyclic group possibly being a carbonyl group
  • R7 and R8 which may be identical or different, being chosen from H, a saturated linear C 1 -C 10 alkyl group, an unsaturated linear C 2 -C 10 alkyl group, a saturated or unsaturated branched C3-C 10 alkyl group, and a C3-C8 cycloalkyl group; a (Ci- C4)alkyl(C6)(hetero)aryl group optionally containing a nitrogen atom, especially a benzyl group; an acetyl radical;
  • R7 and R8 possibly forming with the nitrogen that bears them a 5- to 8- membered heterocycle, which may contain one or more heteroatoms or groups chosen from N, O, -CO-, especially one to three, and/or optionally substituted with a Ci-Cio hydrocarbon-based chain; c) NR9R10
  • R9 and RIO denoting a radical chosen from
  • Ci-Cio a saturated linear Ci-Cio or unsaturated C 2 -Cio or branched C3-C10 or cyclic C3-C8 alkyl group, optionally interrupted with one or more heteroatoms or groups chosen from N, O, -CO and combinations thereof such as -NHCO-, -NHCONH-, and/or optionally substituted with one or more identical or different Ci-Cs alkyl groups, especially one to three
  • a C 5 -Ci 2 (hetero)aryl group optionally containing one or more heteroatoms chosen from O, N and S, especially one to three, optionally substituted with one or more hydroxyls and/or with one or more Ci-Cs alkoxy radicals, especially one to three;
  • R9 and RIO possibly forming with the nitrogen that bears them a 5- to 8-membered heterocycle, which may contain one or more heteroatoms or groups chosen from N, O and -CO-, especially one to three, and/or optionally substituted with a C1-C10 hydrocarbon-based chain optionally containing one or more radicals chosen from hydroxyl and C1-C4 alkoxy, especially one to three;
  • Rll denoting a radical chosen from:
  • R4 and R5 possibly forming with the nitrogen that bears them a 5- to 8- membered heterocycle, which may contain one or more heteroatoms or groups chosen from N, O, -CO-, especially one to three, and/or optionally substituted with a C1-C10 hydrocarbon-based chain; and also the salts thereof, the solvates thereof and the optical and/or geometrical isomers thereof, including enantiomers and diastereoisomers, and the racemic mixtures thereof, alone or as a mixture.
  • radical S* represents a monosaccharide radical, it may be in pyranose form (the sugar heterocycle which forms it is 6-membered) or furanose form (the sugar heterocycle which forms it is 5-membered); and
  • radical S* represents a polysaccharide radical, it comprises the sequence of 2 to 5 identical or different saccharide units which may be in furanose or pyranose form.
  • radical S* apply to the compounds of formula (I) and also to the compounds of formula (II) as defined below.
  • the polysaccharide is a disaccharide which results from the sequence of a saccharide unit in furanose form and a unit in pyranose form or the sequence of a saccharide unit in pyranose form and a unit in furanose form; whether it is for the monosaccharide or polysaccharide radical, each saccharide unit may be in levorotatory L or dextrorotatory D form, and in a or ⁇ anomeric form.
  • the monosaccharide is chosen from glucose, galactose, mannose, xylose, lyxose, fucose, arabinose, rhamnose, quinovose, fructose, sorbose, talose, N- acetylglucosamine and N-acetylgalactosamine, and preferably glucose, galactose, mannose, xylose, lyxose, fucose, arabinose, rhamnose and fructose.
  • the polysaccharide radical may be formed from 2 to 5 saccharide units, in particular from 2 to 3 and preferably 2 saccharide units, linked together via a l - 4 (CI of one saccharide unit ->C4 of the other saccharide unit) or 1 - ⁇ 3 (CI of one saccharide unit ->C3 of the other saccharide unit) or l - 6 (CI of one saccharide unit ->C6 of the other saccharide unit) oxygen atom (oxy) 5, each saccharide unit of which is formed from a heterocycle comprising 4 or 5 carbon atoms.
  • the polysaccharide radical is a disaccharide
  • it may be chosen from: lactose, maltulose, palatinose, lactulose, amygdalose, turanose, cellobiose, isomaltose, rutinose and maltose; and preferably it may be maltose.
  • the salts of the compounds of formula (I) and of formula (II) as defined below comprise the conventional non-toxic salts of said compounds such as those formed from acid or base.
  • salts obtained by addition of the compound of formula (I) or (II) to a mineral acid chosen especially from hydrochloric, boric, hydrobromic, hydriodic, sulfuric, nitric, carbonic, phosphoric and tetrafluoroboric acids;
  • salts obtained by addition of the compound of formula (I) or (II) (when it comprises an acid group) to a mineral base such as sodium hydroxide, potassium hydroxide, calcium hydroxide, ammonium hydroxide, magnesium hydroxide, lithium hydroxide, and sodium, potassium or calcium carbonate or hydrogen carbonate, for example;
  • a primary, secondary or tertiary alkylamine for example triethylamine or butylamine.
  • This primary, secondary or tertiary alkylamine may comprise one or more nitrogen and/or oxygen atoms and may thus comprise, for example, one or more alcohol functions; mention may be made in particular of 2-amino-2- methylpropanol, ethanolamine, triethanolamine, 2-dimethylaminopropanol, 2-amino-2-
  • salts of amino acids for instance lysine, arginine, guanidine, glutamic acid and aspartic acid.
  • the salts of the compound of formula (I) or (II) (when it comprises an acid group) may be chosen from alkali metal and alkaline-earth metal salts such as sodium, potassium, calcium or magnesium salts; ammonium salts.
  • the salts of the compound of formula (I) or (II) may be chosen from halides such as chloride or bromide; citrate, acetate, succinate, phosphate, lactate, tartrate.
  • the acceptable solvates of the compounds described in the present invention comprise conventional solvates such as those formed during the preparation of said compounds owing to the presence of solvents. Mention may be made, by way of example, of the solvates due to the presence of water or of linear or branched alcohols, such as ethano 1 or isopropanol.
  • optical isomers are in particular the enantiomers and the diastereoisomers.
  • (C x -C y )alkyl group denotes an alkyl group comprising from x to y carbon atoms.
  • Such an alkyl group may be linear and saturated and typically contain from 1 to 20 carbon atoms or from 1 to 10 carbon atoms. It may also be linear and typically contain from 2 to 20 carbon atoms or from 2 to 10 carbon atoms. It may also be branched and typically contain from 3 to 20 carbon atoms or from 3 to 10 carbon atoms.
  • An alkyl group may also be cyclic: it is then a cycloalkyl group which may typically contain from 3 to 8 carbon atoms.
  • a "(C x -C y )alkyl group” denotes a saturated linear alkyl group comprising from x to y carbon atoms.
  • the linear saturated or branched alkyl groups may be chosen 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.
  • the linear saturated or branched alkyl groups may be chosen from: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, 2-ethylhexyl and octyl.
  • the cycloalkyl group may be chosen from: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
  • a "(C x -Cy)alkoxy group” denotes a linear and, where appropriate, branched group of formula -0(C x -C y )alkyl which may typically contain from 1 to 8 carbon atoms or from 1 to 4 carbon atoms.
  • the alkoxy group may be chosen from methoxy, ethoxy, propoxy and butoxy and may more particularly be a methoxy group.
  • a "saturated or unsaturated nonaromatic (hetero)cyclic group” denotes a 5- to 12-membered and in particular 5- to 8-membered monocyclic or bicyclic carbocyclic group which may contain one to three heteroatoms or groups chosen from N, O, S and -C(O)-.
  • Such a (hetero)cyclic group may be chosen from cyclohexyl, piperidyl, morpholinyl, piperazinyl, imidazolyl and pyrrolidinyl. Preferentially, it is a piperidyl or morpholinyl ring.
  • (hetero)aryl group denotes an unsaturated or partially unsaturated monocyclic or bicyclic carbocyclic group containing from 5 to 12 carbon atoms and which may contain one to three heteroatoms chosen from N, O and S.
  • the aryl radicals may be chosen from phenyl, naphthyl, indenyl, fluorenyl and anthracenyl. Preferentially, it is a phenyl group.
  • heteroaryl group denotes a fused or nonfused, 5- to 22-membered monocyclic or polycyclic group, comprising from 1 to 6 heteroatoms chosen from nitrogen, oxygen and sulfur, and at least one ring of which is aromatic.
  • the heteroaryl radicals may be chosen from furyl, acridinyl, benzimidazolyl, benzobistriazolyl, benzopyrazolyl, benzopyridazinyl, benzoquinolyl, benzothiazolyl, benzotriazolyl, benzoxazolyl, pyridinyl, tetrazolyl, dihydrothiazolyl, imidazopyridinyl, imidazolyl, indolyl, isoquinolyl, naphthoimidazolyl, naphthooxazolyl, naphthopyrazolyl, oxadiazolyl, oxazolyl, oxazolopyridyl, phenazinyl, phenooxazolyl, pyrazinyl, pyrazolyl, pyrilyl, pyrazoyltriazyl, pyridyl, pyridinoimidazolyl, pyrrolyl, quino
  • the compounds of formula (I) are such that R4 denotes a hydrogen atom, Rl, R2, R3 and R5 having the definitions given previously or hereinbelow, in the preferences.
  • R4 denotes a hydrogen atom
  • Rl denotes a hydrogen atom
  • R2 denotes a hydrogen atom
  • R3 having the definitions given previously or hereinbelow
  • the compounds of formula (I) are such that R4 and R5 are identical, Rl, R2 and R3 having the definitions given previously or hereinbelow, in the preferences.
  • R4 and R5 are identical and represent a C1-C20 alkyl radical, preferably a C1-C10 alkyl radical, optionally substituted with a radical OR7 as defined previously.
  • the compounds of formula (I) are such that R4 and R5 are different and R4 denotes a radical chosen from methyl, ethyl and hydroxyethyl radicals, Rl, R2, R3 and R5 having the definitions given previously or hereinbelow, in the preferences.
  • the compounds of formula (I) are such that R4 and R5 form a 5- to 8-membered saturated or unsaturated non-aromatic heterocycle, which may contain one or more heteroatoms or groups chosen from N, O and -CO-, especially one to three, and/or optionally substituted with a C1-C10 hydrocarbon-based chain; such a heterocycle possibly being chosen from pyrrolidine, piperidine, morpholine and piperazine, Rl, R2 and R3 having the definitions given previously or hereinbelow, in the preferences.
  • the compound of formula (I) is compound 25 as defined herein after and illustrated in examples 21 and 58.
  • the compounds of formula (I) some are novel and constitute another subject of the invention, as do the compositions, in particular the cosmetic compositions, which contain th m; they are the compounds of formula (II) below:
  • R'l and R'2 independently denote a) H
  • R'6 denotes a saturated linear C1-C20 alkyl radical, an unsaturated linear C2-C20 alkyl radical, a branched saturated or unsaturated C3-C20 radical or a C3-C8 cycloalkyl radical
  • R'3 denotes a saturated C1-C20 or unsaturated C2-C20, linear or branched C3- C20, or cyclic C3-C8 alkyl radical
  • R'4 and R'5 independently denote a) -H
  • a saturated C1-C20 or unsaturated C2-C20 or branched C3-C20, or cyclic C3-C8 alkyl radical optionally interrupted with one or more non-adjacent heteroatoms or groups, chosen from N, O, -CO- and combinations thereof such as -NHCO-, -NHCONH-, especially one to three, and/or optionally substituted with one or more identical or different groups, especially one to three, chosen from:
  • a saturated or unsaturated non-aromatic (hetero)cyclic group said (hetero)cyclic group being optionally substituted with one or more hydroxyls, especially one to three, and/or with one or more Ci-Cs alkoxy or Ci-Cs alkyl radicals, especially one to three; one of the chain members possibly being a carbonyl group;
  • R'7 and R'8 which may be identical or different, being chosen from H, a saturated linear C1-C10 alkyl group, an unsaturated linear or branched C2-C10 alkyl group, a saturated or unsaturated branched C3-C10 alkyl group, and a C3-C8 cycloalkyl group; a (Ci- C4)alkyl(C6)(hetero)aryl group optionally containing a nitrogen atom, especially a benzyl group; an acetyl radical;
  • R'7 and R'8 possibly forming with the nitrogen that bears them a 5- to 8- membered heterocycle, which may contain one or more heteroatoms or groups chosen from N, O, -CO-, especially one to three, and/or optionally substituted with a C1-C10 hydrocarbon-based chain; c) NR'9R' 10
  • R'9 and R'lO denoting a radical chosen from
  • C 3 -C8 alkyl group optionally interrupted with one or more non-adjacent heteroatoms or groups chosen from N, O, -CO and combinations thereof such as -NHCO-, -NHCONH-, especially one to three, and/or optionally substituted with one or more identical or different Ci-Cs alkyl groups, especially one to three;
  • a C 5 -Ci 2 (hetero)aryl group optionally containing one or more non-adjacent heteroatoms chosen from O, N and S, especially one to three, optionally substituted with one or more hydroxyls and/or with one or more Ci-Cs alkoxy radicals, especially one to three;
  • R9 and RIO possibly forming with the nitrogen that bears them a 5- to 8-membered heterocycle, which may contain one or more heteroatoms or groups chosen from N, O and -CO-, especially one to three, and/or optionally substituted with a C 1 -C 10 hydrocarbon- based chain optionally containing one or more radicals chosen from hydroxyl and C 1 -C4 alkoxy, especially one to three;
  • R'l 1 denoting a radical chosen from:
  • R'4 and R'5 possibly forming with the nitrogen that bears them a 5- to 8- membered heterocycle, which may contain one or more heteroatoms or groups chosen from N, O, -CO-, especially one to three, and/or optionally substituted with a CI -CIO hydrocarbon-based chain and also the salts thereof, the solvates thereof and the optical and/or geometrical isomers thereof, including enantiomers and diastereoisomers, and the racemic mixtures thereof, with the exception of the following 3 compounds:
  • first cyclic radical optionally contains one or more heteroatoms or groups
  • the term "more” may mean two or three.
  • the compounds of formula (I) are such that:
  • radical S* as defined previously and in particular a glucosyl, xylosyl, mannosyl, fucosyl or maltosyl radical
  • R6 denotes a saturated linear C1-C15 alkyl radical, an unsaturated linear C2-C15 alkyl radical or a branched saturated or unsaturated C3-C15 alkyl radical,
  • R3 denotes a saturated linear C1-C10 alkyl radical, an unsaturated linear C2-C10 alkyl radical, a branched saturated or unsaturated C3-C10 alkyl radical or a C3-C6 cycloalkyl radical,
  • R4 and R5 independently denote a) -H
  • a saturated linear C1-C15 alkyl radical an unsaturated linear C 2 -C15 alkyl radical, a saturated or unsaturated branched C3-C15 alkyl radical or a C3-C8 cycloalkyl radical, optionally interrupted with one or more non-adjacent heteroatoms or groups chosen from N, O and -CO- and combinations thereof such as -NHCO-, -NHCONH-, especially one to three, and/or optionally substituted with one or more identical or different groups, especially one or two, chosen from:
  • R7 and R8 which may be identical or different, being chosen from H, a saturated linear C 1 -C 1 0 alkyl group, an unsaturated linear C 2 -C 1 0 alkyl group, a saturated or unsaturated branched C3-C 1 0 alkyl group, and a C3-C8 cycloalkyl group; a (Ci- C 4 )alkyl(C6)(hetero)aryl group optionally containing a nitrogen atom, especially a benzyl group; an acetyl radical;
  • R7 and R8 possibly forming with the nitrogen that bears them a 5- to 8- membered heterocycle, which may contain one or more heteroatoms or groups chosen from N, O, -CO-, and/or optionally substituted with a C 1 -C 1 0 hydrocarbon-based chain, especially one to three;
  • R4 and R5 possibly forming with the nitrogen that bears them a 5- to 8- membered heterocycle, which may contain one or more heteroatoms or groups chosen from N, O, -CO-, and/or optionally substituted with a Ci-Cio hydrocarbon-based chain such as pyrrolidine, piperidine, morpholine or piperazine.
  • the compounds of formula (II) are such that:
  • Ci-Cio alkyl radical an unsaturated linear or branched C 2 - Cio alkyl radical, a branched saturated or unsaturated C 3 -C10 alkyl group or a C 3 -C 6 cycloalkyl group,
  • R'6 denotes a saturated linear C1-C15 alkyl group or an unsaturated linear C 2 - Ci5 alkyl group it being understood that R'l and R'2 cannot simultaneously denote a methyl radical
  • R'3 denotes a saturated linear C1-C10 alkyl radical, an unsaturated linear C 2 -Cio alkyl radical, a branched saturated or unsaturated C 3 -C10 alkyl radical or a C 3 -C 6 cycloalkyl radical
  • R'4 and R'5 independently denote
  • a linear C1-C15 alkyl radical an unsaturated linear C2-C15 alkyl radical, a saturated or unsaturated branched C3-C15 radical or a C3-C8 cycloalkyl radical, optionally interrupted with one or more heteroatoms or groups chosen from N, O and -CO- and a combination thereof such as -NHCO-, -NHCONH-, especially one to three, and/or optionally substituted with one or more identical or different groups, especially one to three, chosen from:
  • R'7 and R'8 which may be identical or different, being chosen from H, a saturated linear C1-C10 alkyl group, an unsaturated linear or branched C2-C10 alkyl radical, a saturated or unsaturated branched C3-C10 alkyl radical, and a C3-C8 cycloalkyl radical; a (Ci-C 4 )alkyl(C6)(hetero)aryl group optionally containing a nitrogen atom, especially a benzyl group; an acetyl radical; R'7 and R'8 possibly forming with the nitrogen that bears them a 5- to 8- membered heterocycle, which may contain one or more heteroatoms or groups chosen from N, O, -CO-, especially one to three, and/or optionally substituted with a Ci-Cio hydrocarbon-based chain;
  • R'4 and R'5 possibly forming with the nitrogen that bears them a 5- to 8- membered heterocycle, which may contain one or more heteroatoms or groups chosen from N, O and -CO-, especially one or two, and/or optionally substituted with a Ci-Cio hydrocarbon-based chain such as pyrrolidine, piperidine, morpholine or piperazine; and with the exception of the following compound:
  • Ci-C 6 alkyl radical an unsaturated linear C 2 -C 6 alkyl radical or a branched saturated or unsaturated C3-C6 alkyl radical, such as ethyl, isopropyl and n-propyl radicals
  • R6 denotes a saturated linear C 1 -C 15 alkyl radical, such as a methyl or hexyl radical
  • R3 denotes a saturated linear Ci-C 6 alkyl radical, a saturated or unsaturated branched C3-C6 alkyl radical or a C3-C6 cycloalkyl radical, such as a methyl, ethyl or isopropyl radical
  • R4 and R5 independently denote
  • a linear C 1 -C 1 5 alkyl group a branched saturated or unsaturated C3-C 1 5 alkyl group or a C3-C8 cycloalkyl group, optionally interrupted with one or more non-adjacent heteroatoms or groups chosen from N, O and -CO- and combinations thereof such as -NHCO-, -NHCONH-, especially one to three, and/or optionally substituted with one or more identical or different groups, especially one to three, chosen from:
  • a saturated or unsaturated non-aromatic (hetero)cyclic group such as cyclohexyl, optionally substituted with one or more hydroxyl radicals, especially one to three, and/or with one or more C 1 -C4 alkoxy or C 1 -C4 alkyl radicals, especially one to three; one of the chain members possibly being a carbonyl group
  • a C 5 -Ci 2 (hetero)aryl group such as a phenyl, imidazolyl and indolyl radical, optionally substituted with one or more hydroxyl radicals, especially one to three, and/or with one or more Ci-Cs alkoxy and/or Ci-Cs alkyl radicals, especially one to three
  • R7 and R8 which may be identical or different, being chosen from H, a saturated linear Ci-C 6 alkyl group, a branched saturated or unsaturated C3-C6 alkyl group and a (Ci-C4)alkyl(C 6 )(hetero)aryl group optionally containing a nitrogen atom, especially a benzyl group; an acetyl radical;
  • R7 and R8 possibly forming with the nitrogen that bears them a 5- to 8- membered heterocycle, which may contain one or more heteroatoms or groups chosen from N, O, -CO-, especially one to three, and/or optionally substituted with a Ci-Cio hydrocarbon-based chain;
  • R4 and R5 possibly forming with the nitrogen that bears them a heterocycle chosen from pyrrolidine, piperidine, morpholine and piperazine.
  • radicals R4 mention may be made, for example, of H, methyl, ethyl, n-butyl and -(CH 2 ) x OMe radicals with x denoting an integer ranging from 1 to 4, limits inclusive, in particular -(CH 2 ) 2 0Me.
  • radicals R5 mention may be made, for example, of a hydrogen atom, the radicals: n-butyl; -(CH 2 ) x OT with x denoting an integer ranging from 1 to 4, limits inclusive, and T denoting a methyl or ethyl radical, in particular - (CH 2 ) 3 OMe, -(CH 2 ) 3 OEt, -(CH 2 ) 2 OMe, ethyl; n-propyl; n-pentyl; n-hexyl; isopropyl; isobutyl; -(CH 2 )x-iPr, x having the same definition as previously; cyclohexyl; -CH 2 - cyclohexyl; a radical of formula (III)
  • Wl denotes a saturated linear or branched Ci-C 6 alkyl radical optionally substituted with a phenyl radical and W2 denotes H or a saturated linear or branched C 1 -C4 alkyl radical, such as the radicals of formulae (a) to (i) below:
  • p being equal to 0, 1, 2 or 3,
  • the compounds of formula (I) denote compounds 1 to listed in Table 1 below, and also the salts and/or solvates thereof.
  • R'l and R'2 independently denote a) H; b) a saturated linear Ci-C 6 alkyl group or an saturated or unsaturated branched C3-C6 alkyl group such as ethyl, isopropyl and n-propyl radicals
  • R'6 denoting a saturated linear C1-C15 alkyl radical or an unsaturated linear C2-C15 group, preferably a saturated linear C1-C15 alkyl radical, such as a methyl or hexyl radical it being understood that R'l and R'2 cannot simultaneously denote a methyl radical
  • R'3 denotes a saturated linear Ci-C 6 alkyl radical, an unsaturated linear C2-C10 alkyl radical, a saturated or unsaturated branched C3-C6 alkyl radical or a C3-C6 cycloalkyl radical, such as a methyl, ethyl or isopropyl radical
  • a saturated linear C1-C15 alkyl radical an unsaturated linear C2-C15 alkyl radical, a saturated or unsaturated branched C3-C15 radical or a C3-C8 cycloalkyl radical, optionally interrupted with one or more non-adjacent heteroatoms or groups chosen from N, O and -CO- and combinations thereof such as -NHCO-, -NHCONH-, especially one to three, and/or optionally substituted with one or more identical or different groups, especially one to three, chosen from:
  • a saturated or unsaturated non-aromatic (hetero)cyclic group such as cyclohexyl, optionally substituted with one or more hydroxyl radicals, especially one to three, and/or with one or more C 1 -C4 alkoxy or C 1 -C4 alkyl radicals, especially one to three;
  • R'7 and R'8 which may be identical or different, being chosen from H, a saturated linear C 1 -C 10 alkyl group, an unsaturated linear C 2 -Cio alkyl group, a saturated or unsaturated branched C3-C 10 alkyl group, and a C3-C8 cycloalkyl group; a (Ci- C4)alkyl(C6)(hetero)aryl group optionally containing a nitrogen atom, especially a benzyl group; an acetyl radical;
  • R'7 and R'8 possibly forming with the nitrogen that bears them a 5- to 8- membered heterocycle, which may contain one or more heteroatoms or groups, especially one or two chosen from N, O, -CO- and/or optionally substituted with a C 1 -C 10 hydrocarbon-based chain;
  • R'4 and R'5 possibly forming with the nitrogen that bears them a heterocycle chosen from pyrrolidine, piperidine, morpholine and piperazine.
  • radicals R'4 mention may be made, for example, of H, methyl, ethyl, n-butyl and -(CH 2 ) x OMe radicals with x denoting an integer ranging from 1 to 4, limits inclusive, in particular -(CH 2 ) 2 OMe.
  • radicals R'5 mention may be made, for example, of the radicals: n-butyl; -(CH 2 ) x OT with x denoting an integer ranging from 1 to 4, limits inclusive, and T denoting a methyl or ethyl radical, in particular -(CH 2 ) 3 OMe, -(CH 2 ) 3 OEt, -(CH 2 ) 2 OMe, -(CH 2 ) 2 0Me; ethyl; n-propyl; n-pentyl; n-hexyl; isopropyl; isobutyl; -(CH 2 )x-iPr, x having the same definition as previously; cyclohexyl; -CH 2 -cyclohexyl; a radical of formula (III)
  • Wl denotes a saturated linear or branched Ci-C 6 alkyl radical optionally substituted with a phenyl radical and W2 denotes H or a saturated linear or branched C 1 -C4 alkyl radical, such as the radicals of formulae (a) to (i) below:
  • p being equal to 0, 1, 2 or 3,
  • the compounds of formula (II) denote compounds 1 listed in Table 1 below, and also the salts and/or solvates thereof.
  • compositions of the invention may be prepared according to scheme 1 below.
  • Resorcinol A can react in the presence of a beta-keto ester B to give the coumarin C.
  • This coumarin is reduced by catalytic hydrogenation under the conditions known to those skilled in the art to give D.
  • D may also be obtained from resorcinol A in the presence of an alpha,beta- unsaturated ester E.
  • the lactone function of D is then opened in the presence of an amine NHR4R5 optionally with prior modifications of the phenol functions via strategies known to those skilled in the art in terms of reaction and protection/deprotection (formation of esters, ethers or glycosylations).
  • Production of the derivatives C and D via reaction between A and B or A and E may be performed especially in the presence of an organic solvent that may be chosen from toluene, tetrahydrofuran, heptane, isooctane, methyltetrahydrofuran, methyl ethyl ketone, methyl isobutyl ketone, dioxane, ethyl acetate, isopropyl acetate and isododecane, and mixtures thereof, especially at a temperature of between 15 and 200°C, optionally in the presence of a catalyst (acid or basic) as described in the publications: Synthesis of 7- hydroxycoumarins by Pechmann reaction using Nafion resin/silica nanocomposites as catalysts: Laufer MC, Hausmann H, Holderich WF, J of Catalysis, 2003, 218, 315-320; Synthesis of 7-hydroxycoumarins catalysed by solid acid catalysts Hoefnagel A, Gunn
  • the compounds of formulae (I) and (II) for which Rl and/or R2 (R'l and/or R'2) denote a group COR6 (COR'6) may be obtained by acetylation/esterification.
  • the acetylation/esterification reaction may be performed with acetic anhydride (or anhydride R6COOCOR6) or acetyl chloride (or R6COC1), especially in the presence of an aprotic solvent such as toluene, pyridine or tetrahydrofuran.
  • the acetylation reaction may be selective by employing protecting groups on the functions that do not need to be acetylated and by performing a deprotection reaction after acetylation, according to the known techniques of organic synthesis.
  • the opening reaction of the lactone D with amines NHR4R5 may optionally be performed in the presence of an organic solvent, especially tetrahydrofuran, dioxane, dimethylformamide, dimethyl sulfoxide, 2-methyltetrahydrofuran, dichloromethane; toluene, methanol or ethanol; optionally in the presence of a catalyst chosen from Lewis or Bronsted acid catalysts and basic catalysts, such as potassium carbonate, triethylamine or diisopropylethylamine; optionally by heating to a temperature of between 15°C and 200°C, especially between 20°C and 150°C.
  • an organic solvent especially tetrahydrofuran, dioxane, dimethylformamide, dimethyl sulfoxide, 2-methyltetrahydrofuran, dichloromethane; toluene, methanol or ethanol
  • a catalyst chosen from Lewis or Bronsted acid catalysts and basic catalysts, such as potassium carbonate, trie
  • the final compounds (I) and (II) bear a free carboxylic acid on radicals R4 and/or R5 (R'4 and/or R'5)
  • the latter may be obtained by saponification using mineral bases, for instance NaOH or LiOH in the presence of protic or aprotic solvents, for instance ethanol or tetrahydrofuran or water at temperatures ranging between 0 and 100°C.
  • the salts obtained are then reacidified in the presence of standard mineral or organic acids, for instance: hydrochloric acid, citric acid.
  • the present application also relates to a process for preparing a compound of formula (II) as defined previously, whi h consists in
  • step (ii) reacting the compound obtained in step (i) with a compound of formula HNR4R5, in the presence of an organic solvent, especially tetrahydrofuran, dioxane, dimethylformamide, dimethyl sulfoxide, 2-methyltetrahydrofuran, dichloromethane; toluene, methanol or ethanol; optionally in the presence of a catalyst chosen from Lewis or Bronsted acid catalysts and basic catalysts, such as potassium carbonate, triethylamine or diisopropylethylamine; optionally by heating to a temperature of between 15°C and 200°C, especially between 20°C and 150°C, to give the compound of formula G , in which R3', R4' and R5' are as defined above, said compound of formula G being able subsequently to undergo modification of the hydroxyl groups to give said compound of formula (I).
  • an organic solvent especially tetrahydrofuran, dioxane, dimethylformamide, dimethyl sul
  • the glycoside of formula (I) or (II) may be obtained by performing the Schmidt glycosylation reaction in the presence of the trichloroacetimidate glycosyl donor 9, which is reacted with compound 2 to give the anomer 10 followed by a nucleophilic substitution and then removal of the benzyl groups.
  • the glycoside of formula (I) or (II) may be obtained by performing the Schmidt glycosylation reaction.
  • the beta anomer is obtained.
  • An anomeric effect is observed due to the neighboring position of the acetyl group in compound 13.
  • the subsequent deprotection is advantageously performed under very mild conditions.
  • the beta anomer of glycoside 18 was synthesized via the Mitsunobu reaction starting with the protected glucopyranose alpha anomer 8 and the mono-benzyl resorcinol compound 17.
  • Scheme 10 illustrates a synthetic route in which the compound in accordance with the invention shows yet another example of meaning for the radical R5.
  • the compounds of formula (I) or (II) according to the invention find a most particular application in the cosmetic field.
  • composition according to the invention comprises, in a physiologically acceptable medium, a compound of formula (I) or (II) as described previously.
  • physiologically acceptable medium is intended to mean a medium that is compatible with human keratin materials such as the skin of the body or of the face, the lips, the mucous membranes, the eyelashes, the nails, the scalp and/or the hair.
  • Compound (I) or (I) may be present in the composition according to the invention in an amount that may be between 0.01% and 10% by weight, preferably between 0.1 %> and 5% by weight, especially between 0.5%> and 3%> by weight, relative to the total weight of the composition.
  • composition according to the invention is advantageously a cosmetic composition: it may comprise adjuvants usually used in the cosmetic field.
  • organic solvents especially C2-C6 alcohols
  • oils especially hydrocarbon-based oils and silicone oils
  • waxes, pigments, fillers, dyes, surfactants, emulsifiers cosmetic active agents, UV-screening agents, polymers, thickeners, preserving agents, fragrances, bactericides, ceramides, odor absorbers, antioxidants.
  • optional cosmetic adjuvants may be present in the composition in a proportion of from 0.001% to 80%> by weight and especially from 0.1 % to 40%> by weight relative to the total weight of the composition.
  • these adjuvants, and the proportions thereof, will be chosen by those skilled in the art such that the advantageous properties of the compounds according to the invention are not, or are not substantially, adversely affected by the envisaged addition.
  • composition according to the invention may be in any galenical form normally used in the cosmetic field, and especially in the form of an aqueous or aqueous- alcoholic solution, which is optionally gelled, a dispersion of the lotion type, which is optionally a two-phase lotion, an oil-in-water or water-in-oil or multiple (for example W/O/W or 0/W/O) emulsion, an aqueous gel, a dispersion of oil in an aqueous phase by means of spherules, these spherules possibly being polymer nanoparticles such as nanospheres and nanocapsules or, better still, lipid vesicles of the ionic and/or nonionic type; aqueous or oily gels.
  • These compositions are prepared according to the usual methods.
  • a composition in the form of an emulsion, in particular an oil-in-water emulsion, is preferably used according to this invention.
  • the composition according to the invention may constitute a skincare composition, and especially a cleansing, protecting, treating or care cream for the face, the hands, the feet, the major anatomical folds or the body (for example day creams, night creams, makeup-removing creams, foundation creams or anti-sun creams); a fluid foundation, a makeup-removing milk, a protective or care body milk or an anti-sun milk; a skincare lotion, gel or mousse, such as a cleansing lotion.
  • a cleansing, protecting, treating or care cream for the face, the hands, the feet, the major anatomical folds or the body for example day creams, night creams, makeup-removing creams, foundation creams or anti-sun creams
  • a fluid foundation for example day creams, night creams, makeup-removing creams, foundation creams or anti-sun creams
  • a fluid foundation for example day creams, night creams, makeup-removing creams, foundation creams or anti-sun creams
  • a fluid foundation for example day creams, night creams,
  • Resorcinol (1.1 g, 10 mmol) was added to a mixture of ethyl isobutyrylacetate (2.37 g, 15 mmol) and concentrated H 2 SO 4 (9.8 g, 100 mmol) at 0°C. The mixture was stirred at 0°C for 1 hour and then stirred at room temperature for 3 hours. After this, the mixture was poured into ice-water and extracted three times with ethyl acetate. The organic layer was concentrated and dried under vacuum.
  • 1,3-Dihydroxybenzene (1.1 g, 10 mmol) was added to a mixture of ethyl propionylacetate (2.16 g, 15 mmol) and concentrated H 2 SO 4 (9.8 g, 100 mmol) at 0°C. The mixture was stirred at 0°C for 1 hour and then stirred at room temperature for 3 hours. After this, the mixture was poured into ice water and stirred at 0°C for 30 minutes, resulting in the precipitation of a white solid. The solid was collected by filtration and dried under vacuum. The solid was then washed twice with dichloromethane to give 1.58 g of 7-hydroxy-4-ethylcoumarin in the form of a white solid in a yield of 83%.
  • Example 7 synthesis of compound 11 / ethyl 2-(3-(2,4- dihydroxyphenyl)butanamido)-3-phenylpropanoate
  • Example 8 synthesis of compound 12 / 3-(2,4-dihydroxyphenyl)-N,N- diethylbutanamide
  • Example 11 synthesis of compound 15 / 3-(2,4-dihydroxyphenyl)-N- pentylbutanamideTo a solution of 7-hydroxy-4-methyl-3,4-dihydrocoumarin (900 mg, 5.0 mmol) in 20 ml of THF was added amylamine (870 mg, 10.0 mmol). The reaction mixture was stirred at room temperature for 15 hours. The mixture was then poured into 100 ml of water and extracted three times with EtOAc. The combined organic layers were washed three times with water, concentrated and dried under vacuum.
  • Example 12 synthesis of compound 16 / 3-(2,4-dihydroxyphenyl)-N- hexylbutanamide
  • Example 13 synthesis of compound 17 / 3-(2,4-dihydroxyphenyl)-N-(3- ethoxypropyl)butanamide
  • Example 14 synthesis of compound 18 / 3-(2,4-dihydroxyphenyl)-N- isopropylbutanamide
  • Example 15 synthesis of compound 19 / 3-(2,4-dihydroxyphenyl)-N- isopropylbutanamide
  • Example 16 synthesis of compound 20 / 3-(2,4-dihydroxyphenyl)-N- isopentylbutanamide
  • Example 17 synthesis of compound 21 / 3-(2,4-dihydroxyphenyl)-N-(4- methylpentyl)butanamide
  • Example 19 synthesis of compound 23 / N-(cyclohexylmethyl)-3-(2,4- dihydroxyphenyl)butanamide
  • Example 20 synthesis of compound 24 / N-(4-hydroxy-3- methoxyphenethyl)-3-(2,4-dihydroxyphenyl)butanamide
  • MS and NMR spectra are in accordance with the desired product.
  • Example 21 synthesis of compound 25 / ethyl 2-(3-(2,4- dihydroxyphenyl)butanamido)propanoate
  • Example 23 synthesis of compound 26 / 3-(2,4-dihydroxyphenyl)-N,N- bis(2-methoxyethyl)butanamide
  • Example 24 synthesis of compound 27 / ethyl 2-(3-(2,4-dihydroxyphenyl)- N-methylbutanamido)acetate
  • Example 25 synthesis of compound 28 / 3-(2,4-dihydroxyphenyl)-N-(3- heptanyl)butanamide
  • Example 26 synthesis of compound 30 / 3-(2,4-dihydroxyphenyl)-N-(2- hydroxyethyl)butanamide
  • Example 27 synthesis of compound 31 / ethyl 2-(3-(2,4- dihydroxyphenyl)butanamido)acetate
  • Example 28 synthesis of compound 32 / 2-(3-(2,4- dihydroxyphenyl)butanamido)acetic acid
  • Example 29 synthesis of compound 29 / N-ethyl-3-(2-hydroxy-4- ((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2- yloxy)phenyl)butanamide
  • Example 31 synthesis of compound 34 / N-ethyl-3-(2-hydroxy-4- ((3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2- yloxy)phenyl)butanamide
  • Example 32 synthesis of compound 35 / 4-(4-(ethylamino)-4-oxobutan-2- yl)-l,3-phenylene diacetate The synthetic route shown in scheme 9 given in the description was used.
  • Example 33 synthesis of compound 36 / 4-(4-(ethylamino)-4-oxobutan-2- yl)-l,3-phenylene diheptanoate
  • Example 34 synthesis of compound 37 / 2-(3-(2,4- dihydroxyphenyl)butanamido)-4-methylpentanoic acid
  • Example 35 synthesis of compound 38 / 2-(3-(2,4-dihydroxyphenyl)-N- methylbutanamido)acetic acid
  • Example 36 synthesis of compound 39 / 2-(3-(2,4- dihydroxyphenyl)butanamido)propanoic acid
  • Example 37 synthesis of compound 40 / 2-(3-(2,4- dihydroxyphenyl)butanamido)-3-phenylpropanoic acid
  • Example 39 synthesis of compound 42 / ethyl (S)-2-(3-(2,4- dihydroxyphenyl)butanamido)propanoate
  • Example 40 synthesis of compound 43 / ethyl (R)-2-(3-(2,4- dihydroxyphenyl)butanamido)propanoate
  • Example 41 synthesis of compound 44 / (S)-2-(3-(2,4- dihydroxyphenyl)butanamido)propanoic acid
  • Example 42 synthesis of compound 45 / (R)-2-(3-(2,4- dihydroxyphenyl)butanamido)propanoic acid
  • Example 43 synthesis of compound 46 / methyl 2-(3-(2,4- dihydroxyphenyl)butanamido)-4-methylpentanoate
  • Example 45 synthesis of compound 48 / ethyl (R)-2-(3-(2,4- dihydroxyphenyl)butanamido)-3-phenylpropanoate
  • Example 46 synthesis of compound 6 / 3-(2,4-dihydroxyphenyl)-N- ethylbutanamide
  • Example 47 synthesis of compound 49 / 3-(2-ethoxy-4-hydroxyphenyl)-N- ethylbutanamide The synthetic route shown in scheme 9 given in the description was used.
  • Example 48 synthesis of compound 50 / 3-(4-ethoxy-2-hydroxyphenyl) ethylbutanamide
  • Example 49 synthesis of compound 51 / (R)-2-(3-(2,4- dihydroxyphenyl)butanamido)-3-phenylpropanoic acid
  • Example 50 synthesis of compound 52 / 3-(2,4-diisopropoxyphenyl) ethylbutanamide
  • Example 51 synthesis of compound 53 / 3-(2,4-dipropoxyphenyl)-N- ethylbutanamide
  • Example 52 synthesis of compound 54 / N-ethyl-3-(4-hydroxy-2- isopropoxyphenyl)butanamide
  • Example 54 synthesis of compound 56 / N-ethyl-3-(2-hydroxy-4- isopropoxyphenyl)butanamide
  • Example 55 synthesis of compound 57 / N-ethyl-3-(2-hydroxy-4- propoxyphenyl)butanamide
  • Example 56 synthesis of compound 58 / 3-(2,4-dihydroxyphenyl)-N-ethyl- N-(2-hydroxyethyl)butanamide
  • Example 57 synthesis of compound 59 / 3-(2,4-dihydroxyphenyl)-l- (morpholin-4-yl)butan-l-one
  • the measurement of the depigmenting activity (reduction of melanin production) of compounds of formula (I) was performed by assaying normal human melanocytes in vitro as follows.
  • normal human melanocytes are cultured and dispensed into 384 wells. After 24 hours, the culture medium was replaced with a medium containing compounds of formula (I) to be evaluated. The cells were incubated for 72 hours before measurement of the final optical density, which measures the amount of melanin produced by the melanocytes. A dose effect is performed using a wide concentration range of the compounds evaluated. Thus, by making the concentrations and the melanin measurements correspond, it is possible to determine an IC50 in ⁇ : concentration at which 50% decrease in melanin synthesis is achieved.
  • the compounds of formulae (I) and/or (II) showed a strong depigmenting effect.
  • IC50 value is 0.241 ⁇ .
  • a skin depigmenting composition comprising (in grams)
  • Example 60 gel
  • a skin depigmenting gel comprising (% by weight):
  • Carbomer (Carbopol 981 from Lubrizol) 1%
  • composition applied to the skin makes it possible to attenuate brown spots.

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Abstract

La présente invention concerne un composé de formule (I) utilisé pour la dépigmentation, l'éclaircissement et/ou le blanchiment de la peau, R1 et R2 représentant indépendamment H, un radical alkyle, un radical S* représentant un radical sucre monosaccharide ou un radical sucre polysaccharide, un radical COR6 ; R3 représente un radical alkyle en C1-C20 ; R4 et R5 représentent indépendamment H, un radical alkyle saturé en C1-C20 ou insaturé en C2-C20 ou ramifié en C3-C20 ou cyclique en C3-C8, éventuellement interrompu et/ou éventuellement substitué ; R7 et R8, qui peuvent être identiques ou différents, sont choisis parmi H, un groupe alkyle linéaire insaturé en C1-C10, un groupe alkyle linéaire insaturé en C2-C10, un groupe alkyle ramifié saturé ou insaturé en C3-C10 et un groupe cycloalkyle en C3-C8 ; un groupe aryle (C1-C4)alkyl(hétéro)(C6) contenant éventuellement un atome d'azote, en particulier un groupe benzyle ; un radical acétyle, et aussi leurs sels, leurs solvates et leurs isomères optiques et/ou géométriques, et leurs mélanges racémiques, seuls ou en mélange. La présente invention concerne également de nouveaux composés (II), ainsi que leur procédé de préparation et un procédé cosmétique pour dépigmenter la peau au moyen desdits composés (I) ou (II).
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FR3085375B1 (fr) * 2018-08-28 2021-01-29 Greentech Nouveaux derives alkylresorcinols et leur utilisation en cosmetique
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CN111153947A (zh) * 2019-08-21 2020-05-15 云南巅青生物科技有限公司 芳环化合物
CN111153947B (zh) * 2019-08-21 2021-03-09 云南巅青生物科技有限公司 芳环化合物
CN116217423A (zh) * 2022-12-06 2023-06-06 南京工业大学 一种生物基双酚和生物基环氧树脂单体的制备方法和应用

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