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  • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
  • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
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  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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  • C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
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  • 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
  • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
  • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
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  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
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  • C07C45/69—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
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  • C07C59/40—Unsaturated compounds
  • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
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  • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
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  • C07C67/00—Preparation of carboxylic acid esters
  • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
  • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
  • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
  • C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
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  • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
  • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
  • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
  • C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
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  • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
  • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
  • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
  • C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
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  • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
  • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
  • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
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  • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
  • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
  • C07C69/734—Ethers
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  • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
  • C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
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  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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Definitions

• the present invention relates to a process for the preparation of compounds derived from 3-hydroxy-cyclopentyl acetic acid as well as compounds derived from 3-hydroxy-cyclopentyl acetic acid and the use of compounds derived from 3-hydroxy-cyclopentyl acetic acid. to promote desquamation of the skin and / or stimulate epidermal renewal and / or fight against aging of the skin.
• the invention also relates to compositions, in particular cosmetic compositions, which can be used to promote desquamation of the skin and / or stimulate epidermal renewal and / or fight against intrinsic and / or extrinsic skin aging.
• the process according to the present invention is an environmentally friendly process, respecting the principles of Green Chemistry, among which may be mentioned a limited number of steps, an economy of atoms, the use of renewable solvents and the limited impact on the environment, a waste minimization more particularly in the case where steps a) and b) are carried out in the same reactor.
• R23 represents a linear or branched, saturated or unsaturated divalent hydrocarbon radical having 1 to 6 carbon atoms, optionally substituted with 1 to 3 -OH groups and / or optionally interrupted by 1 to 3 carbon atoms; non-adjacent oxygen, Ph representing a phenyl group;
• the transition metal introduced in a catalytic amount is a palladium complex associated with trimethylphosphine.
• the catalyst is Pd (OAc) 2 and the phosphine is PMe 3 . They are advantageously used in a molar ratio Pd (OAc) 2 / PMe 3 1/3.
• the residue can be purified according to a conventional method such as column chromatography on silica gel.
• the transition metal [Mt-b] introduced in a catalytic amount is a palladium complex associated with a phosphine, a rhodium complex associated with a phosphine, a ruthenium complex associated with a phosphine or an iridium complex. associated with a phosphine.
• the transition metal introduced in a catalytic amount is a rhodium complex associated with a phosphine chosen from bidentate phosphines, such as ethylenebis (diphenylphosphine) (dppe), 1,4-bis (diphenylphosphino) propane (dppp), the l, 4-bis (diphenylphosphino) butane (dppb), the l, 4-bis (diphenylphosphino) ferrocene ( ⁇ ) * l a l, l '-binaphthalene-2,2'-diyl) bis ( diphenylphosphine) (BINAP), 2,2'-bis (di-p-tolylphosphino) -1,1-benzaphthyl (tol-BINAP).
• a phosphine chosen from bidentate phosphines, such as ethylenebis (diphenylphosphine) (dppe), 1,4-
• reaction medium is stirred for a period ranging from 5 to 120 min and then 1 equivalent of cyclopentonone B previously dissolved in the reaction solvent is added dropwise.
• R2 denotes a radical chosen from:
• RI represents a hydrogen atom, a phenyl radical or a hydrocarbon radical, linear or branched, saturated or unsaturated having 1 to 8 carbon atoms,
• a radical -Ar-R22 with Ar is an aromatic nucleus chosen from phenyl or pyridyl groups, and R22 represents a substituent chosen from: hydrogen, - OR ', -NO 2 , halogens, -NH 2 , -CF 3 and -R ', with R' denoting a hydrogen atom, a linear hydrocarbon radical, branched or cyclic, saturated or unsaturated, containing 1 to 6 carbon atoms, or a phenyl radical;
• R2 is a -Ar-R22 radical with Ar is a phenyl or pyridyl aromatic ring and
• retinol vitamin A
• tocopherol vitamin E
• essential fatty acids ceramides
• essential oils salicylic acid and its derivatives.
• Step a A 1M solution of PMe 3 in toluene (0.30 equiv, 0.15 mmol, 1 mL) is added to Pd (OAc) 2 (0.1 equiv, 0.05 mmol, 11, 2 mg). The mixture is heated at 110 ° C under argon for 10 minutes, so that Pd (OAc) 2 is completely dissolved. After returning to ambient temperature, the reaction medium is diluted by adding 0.5 ml of water and then a mixture of 1-decyne (1 equiv., 0.5 mmol) and acrolein (5 equiv., 2.5 mmol) is added. . The mixture is heated at 60 ° C for 17h (complete disappearance of 1-decyne TLC).
• reaction mixture is stirred for 4 hours and then cooled to a temperature between -30 and 0 ° C.
• the excess of base is neutralized by adding a saturated aqueous solution of NH 4 Cl and adduct C-9 is extracted 3 times with ethyl acetate.
• the organic phases are combined, dried over Na 2 SO 4 and concentrated under reduced pressure.
• the residue is purified by column chromatography on silica gel to isolate intermediate C-9.
• reaction medium is stirred for 30 min and then 1 equivalent of cyclopentonone B-21 previously dissolved in the reaction solvent is added dropwise.
• Step b
• the malonate derivative is then treated, at 23 ° C., with 5 equivalents of a strong base: sodium methanolate.
• reaction medium is stirred for 6 hours and then 1 equivalent of cyclopentonone B-1 previously dissolved in the reaction solvent is added dropwise.

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• General Health & Medical Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• Dermatology (AREA)
• Birds (AREA)
• Emergency Medicine (AREA)
• Epidemiology (AREA)
• Pharmacology & Pharmacy (AREA)
• Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
• Medicinal Chemistry (AREA)
• General Chemical & Material Sciences (AREA)
• Bioinformatics & Cheminformatics (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Cosmetics (AREA)
• Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
• Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

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