Classifications

• • 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
• • 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
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
• • 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
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/34—Alcohols
  • A61K8/347—Phenols
• • 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
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/35—Ketones, e.g. benzophenone
• • 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
• • 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
  • A61K8/41—Amines
  • A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
• • 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
  • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
• • 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
  • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
  • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
• • 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
  • A61K8/69—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing fluorine
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P17/00—Drugs for dermatological disorders
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P17/00—Drugs for dermatological disorders
  • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• • 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
• • 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
  • A61Q19/08—Anti-ageing preparations
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
  • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
  • C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
  • C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
  • C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
  • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
  • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
  • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
  • C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
  • C07C217/86—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical containing six-membered aromatic rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C233/00—Carboxylic acid amides
  • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
  • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
  • C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
  • C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C255/00—Carboxylic acid nitriles
  • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
  • C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
  • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
  • C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
  • C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C43/00—Ethers; Compounds having groups, groups or groups
  • C07C43/02—Ethers
  • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
  • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C43/00—Ethers; Compounds having groups, groups or groups
  • C07C43/02—Ethers
  • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
  • C07C43/295—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing hydroxy or O-metal groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
  • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
  • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
  • C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
  • C07C65/40—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups containing singly bound oxygen-containing groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
  • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
  • C07C69/94—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
  • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
  • C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
  • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
  • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• • 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
  • C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
  • C07D295/08—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
  • C07D295/096—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
• • 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
  • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
  • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
  • C07H15/20—Carbocyclic rings
  • C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2601/00—Systems containing only non-condensed rings
  • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Definitions

• the invention relates to new anti-aging and depigmenting cosmetic compositions. They contain 1-aryl-2-aryloxyethanes representing a family of compounds with interesting biological properties.
• Certain 1-alyl-2-ylyloxyethanes are reaction intermediates in the preparation of phenoxypropanoamines, antagonist compounds of the ⁇ and ⁇ -forms of adrenaline (SN Louis, TL Nero, D. Iakovidis, Colagrande FM, GP Jackman, WJ Louis Eur J Med Che u, 1999, 919-937).
• An object of the invention is to use 1-alkyl-2-alkyloxyethanes or their derivatives in cosmetic compositions.
• Another object of the invention is to use 1-alkyl-2-alkyloxyethanes or their derivatives in cosmetic compositions intended for anti-aging and / or depigmenting care.
• Another object of the invention is to provide a process for the preparation of new l-aiyl-2- aryloxyéthanes.
• the subject of the invention is the use of the compounds of formula I
• N is 0 or 1
• m is 0 or 1
• n + m 1,
• R 1 and R 2 identical or different, represent
• halogen atoms selected from fluorine, chlorine, bromine or iodine
• ° linear or branched alkyl groups comprising from 1 to 10 carbon atoms, especially methyl groups, ethyl, isopropyl, optionally substituted by one or more halogens chosen (s) from fluorine, chlorine, bromine or iodine, by a -CF 3 group, with a hydroxy,
• ° linear or branched alkoxy groups comprising from 1 to 10 carbon atoms, including methoxy, ethoxy, optionally substituted with one or more halogens chosen (s) from fluorine, chlorine, bromine or iodine, in particular the trifluoromethoxy group -OCF,
• Ar represents an aromatic group having 6 to 12 carbon atoms optionally substituted by one or more atoms selected halogen (s) from fluorine, chlorine, bromine, or optionally substituted by one or more -OH groups in free or protected form, and in particular protected in the form of
• R a represents a hydrogen, a linear or branched alkyl group having from 1 to 6 carbon atoms
• R c represents a linear or branched alkyl group of 1 to 10 carbon atoms
• R a and R c have the meanings indicated above,
• R a represents a hydrogen or a linear or branched alkyl group having from 1 to 6 carbon atoms
• R c represents a linear or branched alkyl group of 1 to 10 carbon atoms
• R a and R c have the meanings indicated above,
• O -OH groups optionally coupled to osidic compounds that can be a- or ⁇ -furanose or a- or ⁇ -pyranose,
• R 1 and R 1 possibly forming a ring having 3 carbon atoms, ring having the following formula
• R a, R b, R a and R b identical or different, represent
• halogen atoms selected from fluorine, chlorine, bromine or iodine, ° linear or branched alkyl groups comprising from 1 to 10 carbon atoms, especially methyl groups, ethyl, isopropyl, optionally substituted by one or more halogens chosen (s) from fluorine, chlorine, bromine or iodine, by a -CF 3 group, with a hydroxy,
• halogen atoms selected from fluorine, chlorine, bromine,
• Linear, branched or cyclic alkyl groups comprising from 1 to 10 carbon atoms, especially methyl, ethyl or isopropyl groups, optionally substituted by one or more halogens chosen from fluorine, chlorine, bromine or the like ; iodine, with a -CF 3 group, with a hydroxy,
• Linear or branched alkoxy groups comprising from 1 to 10 carbon atoms, especially methoxy, ethoxy, isopropoxy or tert-butoxy groups, optionally substituted by one or more halogens chosen from fluorine, chlorine, bromine or iodine, and in particular the trifluoromethoxy group -OCF,
• x is equal to 0 or 1
• y varies from 0 to 4
• R b is hydrogen or acetyl -C (O) -CH, Groups derived from ethylene glycol of formula in which
• R a represents a linear or branched alkyl group having from 1 to 6 carbon atoms
• R c represents a linear or branched alkyl group of 1 to 10 carbon atoms
• R a and R c have the meanings indicated above,
• O -OH groups optionally coupled to an osidic compound which may be an ⁇ - or ⁇ -furanose or an ⁇ - or ⁇ -pyranose,
• halogen atom selected from fluorine, chlorine, bromine, a linear, branched or cyclic containing from 1 to 10 carbon atoms, including methyl, ethyl, isopropyl, optionally substituted by one or more halogens chosen (s) from fluorine, chlorine, bromine or iodine, a group -CF 3, hydroxy,
• a phenyl group optionally substituted with a halogen atom, a -CF group, a linear or branched alkyl group comprising from 1 to 10 carbon atoms, a linear or branched alkoxy group comprising from 1 to 10 carbon atoms,
• a linear or branched alkoxy group comprising from 1 to 10 carbon atoms, especially methoxy, ethoxy, isopropoxy or tert-butoxy groups, optionally substituted by one or more halogens chosen from fluorine, chlorine, bromine or iodine, and in particular the trifluoromethoxy group -OCF,
• an acyloxy group comprising from 2 to 10 linear carbon atoms
• x is equal to 0 or 1
• y varies from 0 to 4
• R b is hydrogen or acetyl -C (O) -CH
• R c is an alkyl group comprising 1 to 6 carbon atoms, in particular methyl or ethyl, or an aromatic group containing from 6 to 18 carbon atoms, optionally substituted by one or more halogen atoms, hydroxy or alkoxy group, nitro group,
• R a represents a linear or branched alkyl group having from 1 to 6 carbon atoms
• R c represents a linear or branched alkyl group of 1 to 10 carbon atoms
• R a and R c have the meanings indicated above,
• An -OH group optionally coupled to an osidic compound that may be an ⁇ - or ⁇ -furanose or an ⁇ - or ⁇ -pyranose,
• R e represents linear or branched alkyl groups having from 1 to 4 carbon atoms, optionally substituted with one or more halogen atoms, or carbon chains interrupted by oxygen or sulfur atoms, benzyl groups optionally substituted by a halogen atom, a hydroxy group, an alkoxy group having from 1 to 8 carbon atoms,
• R 1 represents a linear or branched alkyl group containing from 1 to 4 carbon atoms, a phthalimido group (in this case NH is replaced by N), a benzyl group optionally substituted by a halogen atom, a hydroxyl group, a alkoxy group and in particular substituted with the methoxy group in the para position,
• R g represents a linear or branched alkyl group comprising from 1 to 4 carbon atoms, optionally substituted by one or more halogen atoms, or a carbon chain interrupted by oxygen or sulfur atoms, a phenyl group, a group benzyl optionally substituted by a halogen atom, a hydroxy group, an alkoxy group and in particular substituted with the methoxy group in the para position,
• R 1 and R "1 do not simultaneously represent -OH groups or groups having a phenyl bonded oxygen atom, said compounds of formula I being used in racemic form or a single enantiomer for the preparation of cosmetic compositions having anti-aging and / or depigmenting and / or healing and / or anti-inflammatory properties.
• said compounds of formula I are used in racemic form or a single enantiomer for the preparation of cosmetic compositions for anti-aging and / or depigmenting.
• the compounds of formula I belong to a family of compounds called "1-aryl-2-aryloxyethanes".
• Aryl refers to an aromatic group having 6 carbon atoms, optionally substituted with the groups R “and R “ 1 , and attached to the ethane chain by the carbon 1.
• aryl group is a phenyl group, -Cc Hs.
• R "and R " 1 have the meanings indicated above and in particular represent H, -OH, -OCH, -F, -Br, -OC (O) CH.
• Aryloxy refers to an aryl group attached to carbon 2 of the ethane chain by an oxygen atom. It is optionally monosubstituted by a group R * represented in the general formula I and having the meanings designated above.
• R * may be equal to the hydrogen atom.
• the aryloxy group is a phenoxy group, -OCc Hs.
• R * may be different from the hydrogen atom.
• R * is in particular equal to -OH, -F, a nitrogen group, -CH, -O-CH, -O-CH 2 -PI1.
• R 1 and R 2 have the meanings indicated above and in particular represent hydrogen atoms or -OH.
• n and m are equal to 0 or 1. Their sum is always equal to 1.
• Cosmetic compositions means mixtures containing at least one active compound intended for the care of the body and in particular of the skin.
• Anti-aging properties refers to all the properties of the cosmetic compositions by which it is possible to combat aging of the skin, in particular by dermic strengthening and by the improvement of epidermal differentiation.
• Anti-inflammatory properties refers to the set of properties of the cosmetic compositions by which the secretion of molecules related to inflammation of the skin, such as the secretion of protaglandin PGE 2, can be controlled.
• Depigmenting properties refers to the set of properties of cosmetic compositions by which the melanogenesis or bio-synthesis of melanocytes can be reduced or inhibited.
• Heating properties refers to the set of properties of cosmetic compositions by which the proliferation and migration of fibroblasts and / or keratinocytes on a wound can be increased.
• a particular aspect of the invention relates to the use of the compounds of Fonmile II
• N is 0 or 1
• m is 0 or 1
• n + m 1,
• R 1 , R, R "and R " 1 have the meanings indicated above,
• ⁇ -NR 'a R "b * is a group having a nitrogen atom attached to the ring, possibly in its salt form, this group being selected from
• R d R e representing straight or branched alkyl groups having 1 to 4 carbon atoms, optionally substituted by one or more halogen atoms, or chains carbon atoms interrupted by oxygen or sulfur atoms, benzyl groups optionally substituted with a halogen atom, a hydroxy group or an alkoxy group containing from 1 to 8 carbon atoms,
• R 1 represents a linear or branched alkyl group containing from 1 to 4 carbon atoms, a phthalimido group (in this case NH is replaced by N), a benzyl group optionally substituted by a halogen atom, a hydroxyl group, a alkoxy group and in particular substituted with the methoxy group in the para position,
• R g represents a linear or branched alkyl group comprising from 1 to 4 carbon atoms, optionally substituted by one or more halogen atoms, or a carbon chain interrupted by oxygen or sulfur atoms, a phenyl group, a group benzyl optionally substituted by a halogen atom, a hydroxy group, an alkoxy group and in particular substituted by the methoxy group in the para position.
• Group comprising a nitrogen atom attached to the ring denotes a nitro, primary, secondary or tertiary amine function or their salts, an amide or carbamate function.
• This nitrogen group can occupy the ortho, meta or para positions.
• Another particular aspect of the invention relates to the use of compounds of formula
• halogen atoms selected from fluorine, chlorine, bromine or iodine, ° linear or branched alkyl groups comprising from 1 to 10 carbon atoms, especially methyl groups, ethyl, isopropyl, optionally substituted by one or more halogens chosen (s) from fluorine, chlorine, bromine or iodine, by a -CF 3 group, by a hydroxy
• the carbon 1 of the ethane chain bears a cyclopropyl group.
• This cyclopropyl group may itself be substituted by the groups R, R b, R a and R b, identical or different, whose meanings are given above.
• R a, R b, R a and R b include four hydrogen atoms.
• cyclopropyls have a -OH on the aromatic group at the ⁇ -position of carbon carrying the cyclopropyl group.
• This cyclopropyl group may itself be substituted by the groups R, R b, R a and R b, identical or different, whose meanings are given above.
• R a, R b, R a and R b include four hydrogen atoms.
• Another particular aspect of the invention relates to the use of compounds of formula
• N is 0 or 1
• m is 0 or 1
• n + m 1,
• R 1 , R, R "1 and R * have the meanings given above.
• Compounds IV are distinguished by a hydroxy group specifically ortho to phenyl.
• R 3 has the meaning as above.
• the compounds IVA are distinguished by a phenyl group specifically ortho to phenyl in which the groups R 1 , R 2 and R "1 are three hydrogen atoms, R 3 may occupy the ortho, meta or para positions.
• Another particular aspect of the invention relates to the use of the compounds of formula I
• N is 0 or 1
• m is 0 or 1
• n + m 1,
• R 1 , R 2 , R 1 and R 3 have the meanings indicated above,
• R "and R " 1 are both different from -OH or any form in which - OH is protected.
• Another particular aspect of the invention relates to the use of compounds of formula
• R 1 , R 2 , R 1 and R 3 have the meanings indicated above,
• R "and R " 1 are both different from -OH or any form in which - OH is protected.
• R "1 and R * may occupy the ortho, meta or para positions.
• Another particular aspect of the invention relates to the use of compounds of formula
• N is 0 or 1
• m is 0 or 1
• n + m 1,
• R 1 , R 2 , R "and R ⁇ have the meanings indicated above,
• ⁇ R c is a halogen atom chosen from fluorine, chlorine or bromine.
• the compounds of formula VI have a halogen attached to the -OAr group described in the following general formula:
• R "1 and R can occupy ortho, meta or para positions.
• N is 0 or 1
• m is 0 or 1
• n + m 1,
• R 1 , R 2 , R "and R ⁇ have the meanings designated above.
• formula compounds of formula VII are distinguished by a fluorine atom in para position.
• R "1 may occupy the ortho, meta or para positions.
• Another particular aspect of the invention relates to the use of the compounds of
• N is 0 or 1
• m is 0 or 1
• n + m 1,
• R 1 , R 2 , R "and R ⁇ have the meanings indicated above,
• ⁇ -OR d is a group chosen from
• Linear or branched alkoxy groups comprising from 1 to 10 carbon atoms, especially methoxy, ethoxy, isopropoxy or tert-butoxy groups, optionally substituted by one or more halogens chosen from fluorine, chlorine, bromine or iodine, and in particular the trifluoromethoxy group -OCF,
• x is equal to 0 or 1
• y varies from 0 to 4
• R b is hydrogen or acetyl -C (O) -CH
• R c is an alkyl group comprising from 1 to 6 carbon atoms, in particular methyl or ethyl, or an aromatic group containing from 6 to 18 carbon atoms, optionally substituted with one or more atoms halogen, hydroxy or alkoxy group, nitro,
• R a represents a linear or branched alkyl group having from 1 to 6 carbon atoms
• R c represents a linear or branched alkyl group of 1 to 10 carbon atoms
• R a and R c have the meanings indicated above,
• O -OH groups optionally coupled to an osidic compound which may be a- or ⁇ -furanose or a- or ⁇ -pyranose.
• This oxygenated group has the meanings indicated above. It represents in particular a hydroxy group, -OCH, -O-CH Ph.
• Another particular aspect of the invention relates to the use of compounds of formula
• the compounds of formula III are 1-alkyl-2-alkyloxy ketones.
• R "1 and R 3 have the meanings given above.
• ketones contain an OH in the ortho position on the aromatic group at carbonyl.
• R "1 may occupy the positions meta, para or the other ortho position of the cycle;
• R 3 may occupy the ortho, meta or para positions of the cycle.
• R 1 , R, R ", R “ 1 and R 3 have the meanings given above.
• Carbon 1 of the formula is a methylene group here: the compounds of formula X are 1-alkyl-2-alkyloxyethanes, optionally substituted with the groups R 1 and R 2 , the meaning of which is previously indicated, R 1 and R 2 being in particular equal to carbon atoms, hydrogen, ketones thus being excluded here. R "1 and R * may occupy the ortho, meta or para positions.
• R 1 , R 1 and R 3 have the meanings given above.
• R "1 may occupy the positions meta, para or the other ortho position of the cycle; R 3 may occupy the ortho, meta or para positions of the cycle.
• R, R ⁇ R "1 and R ' have the meanings described above.
• the compounds XI are alcohols obtained from the ketones of formula IX
• the R "group particularly represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen chosen from fluorine, chlorine, bromine or iodine, and is especially a hydrogen atom.
• compounds of formula XI A are used.
• R ⁇ R "1 and R ' have the meanings given above.
• These alcohols contain a -OH in the ortho position on the -Ar group located in a carbon 1 of the
• R "1 may occupy the positions meta, para or the other ortho position of the cycle; R 3 may occupy the ortho, meta or para positions of the cycle.
• XIIA, XIIB and XIIC fonmile compounds are used.
• R 1 , R 2 , R 1 and R ' have the meanings indicated above,
• N is 0 or 1
• m is 0 or 1
• n + m 1.
• the compounds of formula XIIA, XIIB and XIIC belong to the family of 1-aryl-2-aryloxyethanes in which the aryl group in position 1 on the ethane chain of the formula
• R 1 , R, R 1 and R ' have the meanings given above, with the proviso that R “and R " 1 are both different from H,
• N is 0 or 1
• aryl in position 1 on the ethane chain of the formula is disubstituted by the groups R "and R " 1 , the meanings of which are defined above.
• R " is in the ortho position on the cycle, R “ 1 may occupy the meta, para or second ortho position of the cycle. R “and R “ 1 are different from the hydrogen atom.
• R 1 , R 2 , R 1 and R 3 have the meanings indicated above,
• N is 0 or 1
• the compounds of formulas XIIIA, XIIIB and XIIIC belong to the family of 1-aryl-2-aryloxyethanes in which the -OAr group in position 2 on the ethane chain of the formula is substituted by the group R 3 whose meanings are defined above.
• R 3 represents in particular a hydrogen atom, a halogen atom selected from fluorine, chlorine, bromine or iodine, -OH, an alkoxy group, an alkyl group optionally substituted by halogen, a nitrogen-containing group and is in particular a hydrogen atom, a fluorine or bromine atom, -OH, -OCH 3, -0-CH -C 6 H 5, -CH, -N0, -NH, -NH-C (0 ) -CH 3 .
• R 3 can occupy all the positions on the cycle:
• the invention relates to the use of compounds of the following formulas:
• the invention also relates to the use of the compounds of the following formulas
• Compound 137 The compounds listed above are used as active ingredients for the preparation of cosmetic compositions having anti-aging and / or depigmenting and / or cicatrizing and / or anti-inflammatory properties.
• the invention relates to the use of the compounds 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 1 10, 1 1 1, 1 12, 1 13, 1 14, 1 15, 1 16, 1 17,
• the invention also relates to the use of compounds 131, 132, 133, 134, 135, 136, or 137 described above for the preparation of cosmetic compositions having anti-aging properties and / or depigmenting and / or healing and / or anti -inflammatory.
• one or more compounds of formula I are used for the preparation of cosmetic compositions in which the anti-aging properties belong to the group consisting of the reinforcement of the half, the proliferation of dermal fibroblasts, the production of collagen, inhibition of gene expression "matrix metallopeptidase” MMP9 and protein "heat shock protein beta-1" 1 HSPB.
• MMP-9 The "metallopeptidase 9 matrix” (MMP-9) is an enzyme encoded by the MMP-9 gene. It is involved in the degradation of extracellular proteins. It is involved in the remodeling of the extracellular matrix and, in particular, in the degradation of type IV and type V collagens.
• Extracellular matrix refers to the set of extracellular macromolecules of the connective tissue.
• the "heat shock protein beta-1 HSPB1" protein plays a role in the regulation of cellular development, in the inhibition of apoptosis and, in particular, in cell differentiation.
• one or more compounds of formula I for the preparation of cosmetic compositions in which the anti-inflammatory properties belong to the group consisting of inhibition of leukocyte elastase or secretion inhibition of prostaglandins E2.
• Elastases are a subfamily of the serine protease responsible for the degradation of elastin.
• the cartilage proteoglycan, fibronectin, and collagen types I, II, III and IV there is, in addition to elastin, the cartilage proteoglycan, fibronectin, and collagen types I, II, III and IV.
• elastase On the skin, inhibition of elastase helps to fight against the effects of photo-induced aging or not and to limit the appearance of wrinkles and stretch marks.
• PGE2 Prostaglandins E2
• the migration and proliferation phases of cells are major phases of healing that occur after the inflammation phase. They are necessary for the recolonization of the wound. An increase in cell migration and proliferation allows improved healing.
• the biological model consists of normal human dermal fibroblasts (NHDF) whose culture conditions are 37 ° C and 5% CO in DMEM.
• the assay involves inoculating normal human fibroblasts into 96-well plates suitable for migration studies.
• the supports are pretreated with a solution of collagen and a cache is placed at the center of each well, preventing the adhesion of the cells in this zone and thereby forming an artificial wound.
• the caches are removed and then the cells are treated with the compounds or reference.
• the cell migration is microscopically followed for 72 hours with snapshots at 0 h, 24h, 48 h and 72 h. The results, expressed as a percentage of recovery, are compared to the untreated control.
• the biological model consists of normal human epidermal keratinocytes (NHEK) whose culture conditions are 37 ° C and 5% CO in a medium of keratinocytes-SFM.
• the assay involves inoculating normal human keratinocytes into 96-well plates suitable for migration studies.
• the supports are pretreated with a solution of collagen and a cache is placed at the center of each well, preventing the adhesion of the cells in this zone and thereby forming an artificial wound.
• the caches are removed and then the cells are treated with the compounds or reference.
• the cell migration is microscopically followed for 72 hours with snapshots at 0 h, 24h, 48 h and 72 h.
• the "anti-melanogenesis activity” makes it possible to reduce the production of melanin, the main pigment responsible for the color of the skin.
• the tyrosine involved in the manufacture of melanin allows an inhibition of the production of melanin and, consequently, a depigmenting action.
• the depigmenting effect was evaluated on a NDP-MSH-stimulated B-type melanocyte line, (natural melanogenesis stimulating hormone, Melanocyte Stimulate Hormone, [Nie, DPhe] -a-MSH). The synthesis of melanin has been evaluated.
• the invention relates to cosmetic compositions containing as active substance one or more compounds of formula I
• R 1 and R 2 identical or different, represent
• halogen selected halogen (s) from fluorine, chlorine, bromine or iodine
• ° linear or branched alkyl groups comprising from 1 to 10 carbon atoms, especially methyl groups, ethyl, isopropyl, optionally substituted by one or more halogens chosen (s) from fluorine, chlorine, bromine or iodine, by a -CF 3 group, with a hydroxy,
• ° linear or branched alkoxy groups comprising from 1 to 10 carbon atoms, including methoxy, ethoxy, optionally substituted with one or more halogens chosen (s) from fluorine, chlorine, bromine or iodine, in particular the trifluoromethoxy group -OCF,
• Ar represents an aromatic group having 6 to 12 carbon atoms optionally substituted by one or more atoms selected halogen (s) from fluorine, chlorine, bromine, or optionally substituted by one or more -OH groups in free or protected form, and in particular protected form
• R a represents a hydrogen or a linear or branched alkyl group having from 1 to 6 carbon atoms
• R c represents a linear or branched alkyl group of 1 to 10 carbon atoms
• R a and R c have the meanings indicated above,
• R a represents a hydrogen or a linear or branched alkyl group having from 1 to 6 atoms of carbon
• R c represents a linear or branched alkyl group of 1 to 10 carbon atoms
• R a and R c have the meanings indicated above,
• O -OH groups optionally coupled to osidic compounds that can be a- or ⁇ -furanose or a- or ⁇ -pyranose,
• R 1 and R 1 possibly forming a ring having 3 carbon atoms, ring having the following formula
• R a, R b, R a and R b identical or different, represent
• halogen atoms selected from fluorine, chlorine, bromine or iodine, ° linear or branched alkyl groups comprising from 1 to 10 carbon atoms, especially methyl groups, ethyl, isopropyl, optionally substituted by one or more halogens chosen (s) from fluorine, chlorine, bromine or iodine, by a -CF 3 group, with a hydroxy,
• halogen atoms selected from fluorine, chlorine, bromine, ° linear alkyl groups, branched or cyclic containing from 1 to 10 carbon atoms, especially methyl groups, ethyl, isopropyl, optionally substituted by one or more selected halogen (s) from fluorine, chlorine, bromine or iodine, with a -CF 3 group, by a hydroxy,
• Linear or branched alkoxy groups comprising from 1 to 10 carbon atoms, especially methoxy, ethoxy, isopropoxy or tert-butoxy groups, optionally substituted by one or more halogens chosen from fluorine, chlorine, bromine or iodine, and in particular the trifluoromethoxy group -OCF 3,
• x is equal to 0 or 1
• y varies from 0 to 4
• R 1 is hydrogen or acetyl -C (O) -CH
• R a represents a linear or branched alkyl group having from 1 to 6 carbon atoms
• R c represents a linear or branched alkyl group of 1 to 10 carbon atoms
• R a and R c have the meanings indicated above,
• O -OH groups optionally coupled to an osidic compound which may be an ⁇ - or ⁇ -furanose or an ⁇ - or ⁇ -pyranose,
• halogen atom selected from fluorine, chlorine, bromine,
• a linear, branched or cyclic alkyl group comprising from 1 to 10 carbon atoms, including methyl, ethyl, isopropyl, optionally substituted by one or more halogens chosen (s) from fluorine, chlorine, bromine or iodine, a group -CF 3, hydroxy,
• a linear or branched alkoxy group comprising from 1 to 10 carbon atoms, especially methoxy, ethoxy, isopropoxy or tert-butoxy groups, optionally substituted by one or more halogens chosen from fluorine, chlorine, bromine or iodine, and in particular the trifluoromethoxy group -OCF 3,
• acyloxy group comprising from 2 to 10 carbon atoms, linear or branched,
• x is equal to 0 or 1
• y varies from 0 to 4
• R b is hydrogen or acetyl -C (O) -CH
• R c is an alkyl group having 1 to 6 carbon atoms, in particular methyl or ethyl, or an aromatic group containing from 6 to 18 carbon atoms, optionally substituted by one or more halogen atoms, hydroxy or alkoxy group, nitro group,
• R a represents a linear or branched alkyl group having from 1 to 6 carbon atoms
• R c represents a linear or branched alkyl group of 1 to 10 carbon atoms
• R a and R c have the meanings indicated above,
• An -OH group optionally coupled to an osidic compound that may be an ⁇ - or ⁇ -furanose or an ⁇ - or ⁇ -pyranose,
• R e represents linear or branched alkyl groups having from 1 to 4 carbon atoms, optionally substituted with one or more halogen atoms, or carbon chains interrupted by oxygen or sulfur atoms, benzyl groups optionally substituted by a halogen atom, a hydroxy group, an alkoxy group having from 1 to 8 carbon atoms,
• R 1 represents a linear or branched alkyl group containing from 1 to 4 carbon atoms, a phthalimido group (in this case NH is replaced by N), a benzyl group optionally substituted by a halogen atom, a hydroxyl group, a alkoxy group and in particular substituted with the methoxy group in the para position,
• R g represents a linear or branched alkyl group comprising from 1 to 4 carbon atoms, optionally substituted by one or more halogen atoms, or a carbon chain interrupted by oxygen or sulfur atoms, a phenyl group, a group benzyl optionally substituted by a halogen atom, a hydroxy group, an alkoxy group and in particular substituted with the methoxy group in the para position,
• R / and R "1 do not simultaneously represent -OH groups or groups having a phenyl-bonded oxygen atom
• said active substance being in association with a cosmetically acceptable vehicle.
• the invention relates to a cosmetic composition containing as active substance one or more compounds of formula I
• N is 0 or 1
• m is 0 or 1
• n + m 1,
• R 3 represents:
• - a linear, branched or cyclic containing from 2 to 10 carbon atoms, especially ethyl, isopropyl, optionally substituted by one or more halogens chosen (s) from fluorine, chlorine, bromine or iodine, by a -CF 3 group, with a hydroxy,
• said active substance being in association with a cosmetically acceptable vehicle.
• the compounds according to the invention find use in therapeutics as depigmenting agents of the skin, anti-aging agents, cicatrizants, anti-inflammatories.
• compositions containing as active ingredient at least one of the compounds of general formulas I in combination or in admixture with an inert, non-toxic, cosmetically acceptable excipient or carrier.
• Suitable excipients for such administrations are oils, water and alcohol as well as surfactants, additives such as preservatives, antioxidants, dyes, perfumes.
• the invention relates to cosmetic compositions consisting of a mixture comprising at least one compound of formula I as active principle in combination with one or more compounds having anti-aging and / or depigmenting and / or healing and / or anti-inflammatory properties. , particularly in combination with fatty acids such as linoleic acid or azelaic acid, and / or with antioxidants such as vitamin C and / or derivatives tocopherol, and / or with peeling aids such as retinoic acid or glycolic acid,
• composition having anti-aging and / or depigmenting and / or cicatrizing and / or anti-inflammatory properties.
• the cosmetic compositions may contain a mixture of compound of formula I associated, in varying proportions, with one or more other compounds already known for their anti-aging and / or depigmenting and / or healing and / or anti-inflammatory and / or antioxidant.
• the cosmetic compositions may thus possibly contain another agent known for its depigmenting properties such as:
• Linoleic acid a deficiency of which causes a dry skin
• Azelaic acid a tyrosinase inhibitor, having a depigmenting effect on melasma, chloasma, post-inflammatory hyperpigmentations,
• antioxidant such as vitamin C or a tocopherol derivative.
• the cosmetic compositions have a content of compounds of formula I of 0.001% to 10% by weight.
• the dosage may vary depending on the form. If a mixture of compounds I is used, the proportions of compounds of formula I of this mixture may vary, so that the overall percentage by weight is from 0.001% to 10%.
• the cosmetic compositions are in the form of cream, ointment, gel, ointment, lotion, patch, oil, serum, milk, spray, balm, emulsion, microemulsion.
• compositions will be presented under one of the cosmetic forms suitable for dermal administration. In this respect, mention may be made of creams, ointments, gels, oils, seines, milks, sprays, emulsions and encapsulations.
• the cosmetic compositions contain as active substance one or more compounds of formula II
• N is 0 or 1
• m is 0 or 1
• n + m 1,
• R 1 , R, R "and R " 1 have the meanings indicated above,
• ⁇ -NR 'a R "b * is a group having a nitrogen atom attached to the ring, possibly in its salt form, this group being selected from
• R d R e representing straight or branched alkyl groups having 1 to 4 carbon atoms, optionally substituted by one or more halogen atoms, or carbon chains interrupted by oxygen or sulfur atoms, benzyl groups optionally substituted with a halogen atom, a hydroxy group, an alkoxy group having from 1 to 8 carbon atoms,
• R 1 represents a linear or branched alkyl group containing from 1 to 4 carbon atoms, a phthalimido group (in this case NH is replaced by N), a benzyl group optionally substituted by a halogen atom, a hydroxyl group, a alkoxy group and in particular substituted with the methoxy group in the para position,
• R g represents a linear or branched alkyl group comprising from 1 to 4 carbon atoms, optionally substituted by one or more halogen atoms, or a carbon chain interrupted by oxygen or sulfur atoms, a phenyl group, a group benzyl optionally substituted by a halogen atom, a hydroxy group, an alkoxy group and in particular substituted with the methoxy group in the para position,
• the cosmetic compositions contain at least as active substance one or more compounds of formula
• halogen atoms selected from fluorine, chlorine, bromine or iodine
• ° linear or branched alkyl groups comprising from 1 to 10 carbon atoms, especially methyl groups, ethyl, isopropyl, optionally substituted by one or more halogens chosen (s) from fluorine, chlorine, bromine or iodine, by a -CF 3 group, with a hydroxy,
• the cosmetic compositions contain as active substance one or more compounds of formula IV
• R 1 , R 2 , R "1 and R ' have the meanings indicated above,
• N is 0 or 1
• m is 0 or 1
• n + m 1,
• the cosmetic compositions contain as active substance one or more compounds of formula IVA
• R 3 has the meaning indicated above
• the cosmetic compositions contain as active substance one or more compounds of formula V
• R ⁇ R "1 and R 3 have the meanings given above,
• the cosmetic compositions contain as active substance one or more of the compounds of formulas 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 1, 1, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106
• the cosmetic compositions contain as active substance one or more of the compounds of formulas 131, 132, 133, 134, 135, 136 or 137 mentioned above, in association with a cosmetically acceptable vehicle.
• the cosmetic compositions contain a mixture comprising one or more compounds belonging to the list of compounds 1, 2, 3, 4, 5 , 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108
• composition having anti-aging and / or depigmenting and / or cicatrizing and / or anti-inflammatory properties.
• the cosmetic compositions contain a mixture comprising one or more compounds belonging to the list of compounds 131, 132, 133, 134, 135, 136, or 137 mentioned previously as active principle, in combination with one or more compounds having anti-aging properties and / or depigmenting and / or healing and / or anti-inflammatory drugs, particularly in combination with fatty acids such as linoleic acid or azelaic acid, and / or antioxidants such as vitamin C and / or tocopherol derivatives, and / or with peeling aids such as retinoic acid or glycolic acid,
• composition having anti-aging and / or depigmenting and / or cicatrizing and / or anti-inflammatory properties.
• the invention also relates to compounds of formula I
• N is 0 or 1
• m is 0 or 1
• n + m 1,
• ⁇ R 1 and R 2 have the meanings mentioned above ⁇ R "and R -1 , identical or different, represent:
• R 3 represents:
• - a linear, branched or cyclic containing from 2 to 10 carbon atoms, especially ethyl, isopropyl, optionally substituted by one or more halogens chosen (s) from fluorine, chlorine, bromine or iodine, by a -CF 3 group, with a hydroxy,
• the invention also relates to a compound of formula X
• N 0, and m is 1,
• R 1 and R have the meanings mentioned above,
• ⁇ and R5 represents:
• - a linear, branched or cyclic containing from 2 to 10 carbon atoms, especially ethyl, isopropyl, optionally substituted by one or more halogens chosen (s) from fluorine, chlorine, bromine or iodine, by a -CF 3 group, with a hydroxy,
• alkynyl group comprising from 2 to 6 carbon atoms, linear or branched and having at least one triple bond C
• the invention relates to compounds of formula II
• N is 0 or 1
• m is 0 or 1
• n + m 1,
• ⁇ -NR 'a R "b * is a group having a nitrogen atom attached to the ring, possibly in its salt form, this group being selected from
• R d R e representing straight or branched alkyl groups having 1 to 4 carbon atoms, optionally substituted by one or more halogen atoms, or carbon chains interrupted by oxygen or sulfur atoms, benzyl groups optionally substituted with a halogen atom, a hydroxy group, an alkoxy group having from 1 to 8 carbon atoms,
• R 1 represents a linear or branched alkyl group containing from 1 to 4 carbon atoms, a phthalimido group (in this case NH is replaced by N), a benzyl group optionally substituted by a halogen atom, a hydroxyl group, a alkoxy group and in particular substituted with the methoxy group in the para position,
• R g represents a linear or branched alkyl group comprising from 1 to 4 carbon atoms, optionally substituted by one or more halogen atoms, or a carbon chain interrupted by oxygen or sulfur atoms, a phenyl group, a group benzyl optionally substituted by a halogen atom, a hydroxy group, an alkoxy group and in particular substituted by the methoxy group in the para position.
• N is 0 or 1
• m is 0 or 1
• n + m 1,
• R 1 and R 2 have the meanings indicated above,
• R 'and R ⁇ have the meanings described above, with the exception of atoms hydrogen,
• R * b represents a group comprising a nitrogen atom attached to the ring, optionally in its salt form, this group being chosen from
• R d R e representing straight or branched alkyl groups having 1 to 4 carbon atoms, optionally substituted by one or more halogen atoms, or carbon chains interrupted by oxygen or sulfur atoms, benzyl groups optionally substituted with a halogen atom, a hydroxy group, an alkoxy group having from 1 to 8 carbon atoms,
• R 1 represents a linear or branched alkyl group containing from 1 to 4 carbon atoms, a phthalimido group (in this case NH is replaced by N), a benzyl group optionally substituted by a halogen atom, a hydroxyl group, a alkoxy group and in particular substituted with the methoxy group in the para position,
• R g represents a linear or branched alkyl group comprising from 1 to 4 carbon atoms, optionally substituted by one or more halogen atoms, or a carbon chain interrupted by oxygen or sulfur atoms, a phenyl group, a group benzyl optionally substituted by a halogen atom, a hydroxy group, an alkoxy group and in particular substituted by the methoxy group in the para position.
• the invention relates to compounds of formula II
• N is 0 or 1
• m is 0 or 1
• n + m 1,
• R 1 and R 2 have the meanings indicated above,
• R ' represents a hydroxyl group and R "1 has the meanings indicated above,
• R * b represents a group comprising a nitrogen atom attached to the ring, optionally in its salt form, this group being chosen from
• R d R e representing straight or branched alkyl groups having 1 to 4 carbon atoms, optionally substituted by one or more halogen atoms, or carbon chains interrupted by oxygen or sulfur atoms, benzyl groups optionally substituted with a halogen atom, a hydroxy group, an alkoxy group having from 1 to 8 carbon atoms,
• R 1 represents a linear or branched alkyl group containing from 1 to 4 carbon atoms, a phthalimido group (in this case NH is replaced by N), a benzyl group optionally substituted by a halogen atom, a hydroxyl group, a alkoxy group and in particular substituted with the methoxy group in the para position,
• R g represents a linear or branched alkyl group having from 1 to 4 carbon atoms, optionally substituted by one or more halogen atoms, or a chain carbonated interrupted by oxygen or sulfur atoms, a phenyl group, a benzyl group optionally substituted by a halogen atom, a hydroxy group, an alkoxy group and in particular substituted by the methoxy group in the para position.
• the invention relates to the compounds of formula
• halogen atoms selected from fluorine, chlorine, bromine or iodine
• ° linear or branched alkyl groups comprising from 1 to 10 carbon atoms, especially methyl groups, ethyl, isopropyl, optionally substituted by one or more halogens chosen (s) from fluorine, chlorine, bromine or iodine, by a -CF 3 group, by a hydroxy
• the invention relates to formula compounds
• the invention relates more particularly to compounds of formula:
• the invention relates to a process for the preparation of Fonmile XA compounds
• R 1 , R 2 , R "1 and R 3 have the meanings indicated above,
• R 1 and R 2 are both hydrogen atoms.
• This method is applicable to prepare compounds having a -OH group ortho on the
• the phenolic alcohol XIV reacts with the mesyl chionire to give the dimesylated compound.
• This step is a way to protect the phenolic -OH on the one hand and to activate the -OH carried by the ethane chain on the other hand.
• the first step thus provides the dimesyl compound XV which, in the second step, undergoes a substitution by reaction with the phenol XVI to give the compound XVII, belonging to the family of 1-alkyl-2-alkyloxyethanes.
• Basic hydrolysis is the last step and liberates the phenolic -OH compound XA.
• the invention also relates to a process for the preparation of compounds of formula V
• R 1 , R 2 , R 1 and R 3 have the meanings indicated above,
• R "and R “ 1 are both different from -OH or any form in which - OH is protected, comprising a Mitsunobu-type reaction carried out on an allyl alcohol of formula
• R 1 , R 2 , R 1 and R * have the meanings indicated above,
• R 1 and R 2 are both hydrogen atoms.
• the invention also relates to a process for the preparation of the compounds of formula III
• R a , R lb , R a and R b identical or different, representing
• halogen atoms selected from fluorine, chlorine, bromine or iodine
• ° linear or branched alkyl groups comprising from 1 to 10 carbon atoms, especially methyl groups, ethyl, isopropyl, optionally substituted by one or more halogens chosen (s) from fluorine, chlorine, bromine or iodine, by a -CF 3 group, with a hydroxy,
• R "1, R a, R b, R a and R b have the meanings designated above,
• R, R b, R a and R b being four hydrogen atoms.
• the invention also relates to a process for the preparation of compounds of formula IIA
• R 1 and R 2 being two hydrogen atoms.
• the invention also relates to a process for the preparation of compounds of formula IIB
• the invention relates to a process for preparing the compounds of Fonmile IIC
• R 1 , R 2 , R "1 and R f have the meanings indicated above,
• R 1 and R 2 are both hydrogen atoms. This route makes it possible to obtain compounds bearing an amide function.
• the molecules of formula XVIA can be obtained by direct amidation of raminophénol by a derivative anhydride or acid chloride, as described by David Rely in Helv. Chim. Acta 1939, 22 p89, Palm et al., J. Med. Chem. 1998, 41 (27), 5382-5392, Deng W et al., Bioorg. Med. Chem. Lett. 2006, 16 (2), 469-472.
• the invention relates to a process for the preparation of compounds of formula I
• R " is a -OH group coupled to a saccharide compound which may be an ⁇ - or ⁇ -furanose or an ⁇ - or ⁇ -pyranose,
• a sugar which may be a- or ⁇ -furanose or a- or ⁇ -pyranose, the -OH being protected, in particular in the form of acetates, and the anomeric position being previously activated in the form of bromine or trichoroacetimidate,
• NDP-MSH [Nie, DPhe] -a-MSH
• DMEM Dulbecco / Vogt Modified Eagle's minimal essential medium.
• Eagle's essential minimum medium (cell culture medium developed by Harry Eagle, it is used to maintain the cells of a tissue culture). The techniques of analysis are:
• the LC / MS analysis corresponds to a coupling of the HPLC analysis and the mass spectrometry analysis. It is performed on a Alliance Waters 2695-ZQ2000 aircraft.
• stage 1 protection / activation
• the diol XIV (1 equiv) was diluted in dichloromethane (5 volumes) and then TEA (2.2 equivalents) is added.
• the reaction medium is cooled to 5 ° C.
• methanesulfonyl chloride (2.2 equivalents) diluted in dichloromethane (5 volumes) was added while controlling the temperature.
• the reaction medium is then stirred at room temperature for one night.
• the reaction medium is poured into an ice-water / HCI mixture. After three extractions with dichloromethane, the organic phases are washed with saturated NaCl solution.
• the products obtained are monomésylates of formula XII, oils or solids according to the natures of R 1 , R 2 , R "1 and R ⁇ purified in particular by chromatography on silica or by trituration in isopropyl ether / pentane mixtures of variable composition.
• Stage 1 is carried out according to the procedure described in Example 1 from compound XIVA. After filtration and drying under vacuum, compound XVA is isolated. It is a white solid obtained with 92% yield. He is engaged in the next stage. ⁇ Stage 2: substitution
• Stage 2 is carried out according to the procedure described in Example 1 using 4-fluorophenol.
• the residue is purified on silica gel column eluted with a gradient heptane - ethyl acetate.
• the monomatesate XIIA is obtained. It is a yellow oil, obtained with 55-65% yield. He is engaged in the next stage.
• Stage 3 is carried out according to the procedure described in Example 1.
• the residue was purified on silica gel column eluted with a gradient heptane - ethyl acetate.
• Compound 1 is a colorless oil obtained with 60-70% yield.
• the phenol derivative may be in particular 4-fluorophenol.
• the derivative XVIII may especially be 2-hydroxyphenylethanol.
• Compound 21 is obtained, after crystallization from dichloromethane, in the form of a beige solid in 60% yield.
• R 1 , R, R "1 and R * have the meanings designated above.
• Step 1 Coupling of the saccharide derivative activated in the form of trichloroacetimidate
• dichloromethane 7 vol
• the activated osidic derivative in the form of trichloroacetimidate 1.3 equivalent
• a solution of BF 2 2 equivalents
• the reaction medium is stirred for 2 hours. It is then poured on a saturated solution of NaHCCh.
• Step 1 coupling of the activated osidic derivative
• This stage 1 is carried out according to the procedure described in Example 7 starting from the compound 1.
• Stage 2 is carried out according to the procedure described in Example 7 starting from the compound 30.
• stage 1 protection / activation
• Phenols derivatives (1.2 equivalents) are added as well as CO (1.2 equivalents).
• reaction medium is refluxed for 4 hours.
• reaction mixture is hydrolysed by 25 volumes of distilled water.
• organic phases are washed with saturated NH 4 Cl solution, dried over MgSO 4, filtered and concentrated in vacuo.
• the residue obtained is purified by chromatography on silica gel eluted with a heptane / chloroform or heptane / isopropyl ether or heptane / isopropanol gradient, depending on the polarity of the compounds.
• the residue is purified by chromatography on silica gel eluted with a gradient heptane / ethyl acetate.
• the reaction yield is 45-70%.
• Example 10 Summary Table of the Molecules Obtained in Examples 1 to 9
• Aromatic H 7.12 (m, 1 ⁇ , aromatic H);
• Aromatic H 7.1 1 -7.14 (m, 3 ⁇ , aromatic H); 7.23-
• Aromatic H 7.21 -7.31 (m, 4 ⁇ , aromatic H)
• Aromatic H 7.16-7.27 (m, 4 ⁇ , aromatic H)

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• General Health & Medical Sciences (AREA)
• Veterinary Medicine (AREA)
• Public Health (AREA)
• Animal Behavior & Ethology (AREA)
• Epidemiology (AREA)
• Birds (AREA)
• Emergency Medicine (AREA)
• Dermatology (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Pharmacology & Pharmacy (AREA)
• Medicinal Chemistry (AREA)
• Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
• General Chemical & Material Sciences (AREA)
• Gerontology & Geriatric Medicine (AREA)
• Genetics & Genomics (AREA)
• Biochemistry (AREA)
• Biotechnology (AREA)
• Bioinformatics & Cheminformatics (AREA)
• Molecular Biology (AREA)
• Rheumatology (AREA)
• Pain & Pain Management (AREA)
• Cosmetics (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
• Saccharide Compounds (AREA)
• Pyrrole Compounds (AREA)
• Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
• Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Applications Claiming Priority (2)

Publications (1)

Family

ID=47505260

Family Applications (1)

Country Status (9)

Citations (2)

Family Cites Families (23)

• 2011
  • 2011-12-22 FR FR1162289A patent/FR2984730A1/fr not_active Withdrawn
• 2012
  • 2012-12-18 CA CA2859894A patent/CA2859894A1/fr not_active Abandoned
  • 2012-12-18 WO PCT/FR2012/052964 patent/WO2013093320A1/fr active Application Filing
  • 2012-12-18 BR BR112014015389A patent/BR112014015389A8/pt not_active Application Discontinuation
  • 2012-12-18 CN CN201280070132.0A patent/CN104203927B/zh not_active Expired - Fee Related
  • 2012-12-18 JP JP2014548148A patent/JP2015502391A/ja active Pending
  • 2012-12-18 US US14/367,712 patent/US20150004110A1/en not_active Abandoned
  • 2012-12-18 EP EP12810398.3A patent/EP2794578A1/de not_active Withdrawn
  • 2012-12-18 KR KR1020147020635A patent/KR20140113984A/ko not_active Application Discontinuation

Patent Citations (2)

Non-Patent Citations (3)

Also Published As

Similar Documents

Legal Events