FR3027515B1 - USE OF ESTERS OF PHENYLALANINE AND POLYOLS AS A LIGHTENING AGENT FOR THE SKIN OF THE HUMAN BODY - Google Patents
USE OF ESTERS OF PHENYLALANINE AND POLYOLS AS A LIGHTENING AGENT FOR THE SKIN OF THE HUMAN BODY Download PDFInfo
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- FR3027515B1 FR3027515B1 FR1460295A FR1460295A FR3027515B1 FR 3027515 B1 FR3027515 B1 FR 3027515B1 FR 1460295 A FR1460295 A FR 1460295A FR 1460295 A FR1460295 A FR 1460295A FR 3027515 B1 FR3027515 B1 FR 3027515B1
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- 241000282414 Homo sapiens Species 0.000 title claims abstract description 20
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 title description 5
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 title description 5
- 229920005862 polyol Polymers 0.000 title description 3
- 150000003077 polyols Chemical class 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 117
- 150000001875 compounds Chemical class 0.000 claims abstract description 108
- 238000000034 method Methods 0.000 claims abstract description 30
- 230000008569 process Effects 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- -1 9-octadecenoyl Chemical group 0.000 claims description 85
- 239000002537 cosmetic Substances 0.000 claims description 22
- 238000009472 formulation Methods 0.000 claims description 16
- 230000000699 topical effect Effects 0.000 claims description 11
- 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 claims description 5
- 125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000012049 topical pharmaceutical composition Substances 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 51
- 210000003491 skin Anatomy 0.000 description 35
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- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 17
- 150000002148 esters Chemical class 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 12
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- RTBWWWVNZWFNBV-SFHVURJKSA-N (2s)-3-phenyl-2-(undec-10-enoylamino)propanoic acid Chemical class C=CCCCCCCCCC(=O)N[C@H](C(=O)O)CC1=CC=CC=C1 RTBWWWVNZWFNBV-SFHVURJKSA-N 0.000 description 8
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- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 7
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- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
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- BJRNKVDFDLYUGJ-RMPHRYRLSA-N hydroquinone O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-RMPHRYRLSA-N 0.000 description 6
- 210000002510 keratinocyte Anatomy 0.000 description 6
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- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 5
- XNWZOFXSPQXPRE-HNNXBMFYSA-N (2s)-2-(octanoylamino)-3-phenylpropanoic acid Chemical compound CCCCCCCC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 XNWZOFXSPQXPRE-HNNXBMFYSA-N 0.000 description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- BANXPJUEBPWEOT-UHFFFAOYSA-N 2-methyl-Pentadecane Chemical compound CCCCCCCCCCCCCC(C)C BANXPJUEBPWEOT-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
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- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 4
- COLNVLDHVKWLRT-UHFFFAOYSA-M phenylalaninate Chemical compound [O-]C(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-M 0.000 description 4
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- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 3
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
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- 239000001540 sodium lactate Substances 0.000 description 1
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- 229940005581 sodium lactate Drugs 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 229940045870 sodium palmitate Drugs 0.000 description 1
- NTVDGBKMGBRCKB-UHFFFAOYSA-M sodium;12-hydroxyoctadecanoate Chemical compound [Na+].CCCCCCC(O)CCCCCCCCCCC([O-])=O NTVDGBKMGBRCKB-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- GGXKEBACDBNFAF-UHFFFAOYSA-M sodium;hexadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCC([O-])=O GGXKEBACDBNFAF-UHFFFAOYSA-M 0.000 description 1
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- 238000002798 spectrophotometry method Methods 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229960005322 streptomycin Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003445 sucroses Chemical class 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 235000010491 tara gum Nutrition 0.000 description 1
- 239000000213 tara gum Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 229940061605 tetrasodium glutamate diacetate Drugs 0.000 description 1
- UZVUJVFQFNHRSY-OUTKXMMCSA-J tetrasodium;(2s)-2-[bis(carboxylatomethyl)amino]pentanedioate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CC[C@@H](C([O-])=O)N(CC([O-])=O)CC([O-])=O UZVUJVFQFNHRSY-OUTKXMMCSA-J 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
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- 150000003611 tocopherol derivatives Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
- LOIYMIARKYCTBW-UHFFFAOYSA-N trans-urocanic acid Natural products OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 235000001019 trigonella foenum-graecum Nutrition 0.000 description 1
- PJHKBYALYHRYSK-UHFFFAOYSA-N triheptanoin Chemical compound CCCCCCC(=O)OCC(OC(=O)CCCCCC)COC(=O)CCCCCC PJHKBYALYHRYSK-UHFFFAOYSA-N 0.000 description 1
- VXYADVIJALMOEQ-UHFFFAOYSA-K tris(lactato)aluminium Chemical compound CC(O)C(=O)O[Al](OC(=O)C(C)O)OC(=O)C(C)O VXYADVIJALMOEQ-UHFFFAOYSA-K 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000012178 vegetable wax Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000001643 venotonic effect Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
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- 235000013343 vitamin Nutrition 0.000 description 1
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- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019160 vitamin B3 Nutrition 0.000 description 1
- 239000011708 vitamin B3 Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 230000036642 wellbeing Effects 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- GDJZZWYLFXAGFH-UHFFFAOYSA-M xylenesulfonate group Chemical group C1(C(C=CC=C1)C)(C)S(=O)(=O)[O-] GDJZZWYLFXAGFH-UHFFFAOYSA-M 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011670 zinc gluconate Substances 0.000 description 1
- 235000011478 zinc gluconate Nutrition 0.000 description 1
- 229960000306 zinc gluconate Drugs 0.000 description 1
- 239000011576 zinc lactate Substances 0.000 description 1
- 235000000193 zinc lactate Nutrition 0.000 description 1
- 229940050168 zinc lactate Drugs 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 description 1
- AZOOXWWPWARTFV-UHFFFAOYSA-N zirconium hydrochloride Chemical compound Cl.[Zr] AZOOXWWPWARTFV-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/223—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of alpha-aminoacids
-
- 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
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Birds (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Emergency Medicine (AREA)
- Cosmetics (AREA)
Abstract
Utilisation d'un composé de formule (I) R'-O-CH2-CH(OH)-[CH2-O-CH2]s-[CH(OH)]p-CH2-O-R" (l) dans laquelle s est égal à 0 ou à 1 et p est égal à 0, 1, 2 ou 3 et R' et R" représentent soit un atome d'hydrogène, soit un radical monovalent de formule (II) : formule (II) dans laquelle le groupe R1(C=O) représente un radical acyle ou d'une composition (C1) comprenant pour 100% de sa masse de 99% massique à 20% massique d'au moins un composé de formule (la) : R'-O-CH2-CH(OH)-[CH2-O-CH2]s-[CH(OH)]p-CH2-O-H (la) dans laquelle s est égal à 0 ou à 1 et p est égal à 0, 1, 2 ou 3 et dans laquelle R' représente un radical monovalent de formule (II) et de 1% massique à 80% massique d'au moins un composé de formule (lb) : R-O-CH2-CH(OH)-[CH2-O-CH2]s-[CH(OH)]p-CH2-O-R, formule (lb) dans laquelle s est égal à 0 ou à 1 et p est égal à 0, 1, 2 ou 3, dans laquelle R représente un radical monovalent de formule (II), dans le but d'éclaircir la peau humaine. Procédé d'éclaircissement et composition thérapeutique.Use of a compound of formula (I) R'-O-CH 2 -CH (OH) - [CH 2 -O-CH 2] s- [CH (OH)] p -CH 2 -OR "(1) in which s is equal to 0 or 1 and p is 0, 1, 2 or 3 and R 'and R "represent either a hydrogen atom or a monovalent radical of formula (II): formula (II) in which the group R1 (C = O) represents an acyl radical or a composition (C1) comprising for 100% of its mass from 99% by weight to 20% by weight of at least one compound of formula (Ia): R'-O- CH 2 -CH (OH) - [CH 2 -O-CH 2] s- [CH (OH)] p -CH 2 -OH (la) in which s is 0 or 1 and p is 0, 1, 2 or 3 and in which R 'represents a monovalent radical of formula (II) and from 1% by mass to 80% by weight of at least one compound of formula (Ib): RO-CH 2 -CH (OH) - [CH 2 -O] -CH2] s- [CH (OH)] p-CH2-OR, formula (Ib) wherein s is 0 or 1 and p is 0, 1, 2 or 3, wherein R represents a radical monovalent of formula (II), for the purpose of lightening human skin. Lightening process and therapeutic composition
Description
La présente invention a pour objet l’utilisation d’esters de dérivés N-acylés d’acidesaminés et de polyols comme agents d’éclaircissements de la peau du corps humain, ainsique les procédés non thérapeutique d'éclaircissement de la peau humaine comprenant aumoins une étape d'application sur ladite peau humaine d'une formulation cosmétique àusage topique comprenant lesdits esters de dérivés N-acylés d’acides aminés et deglycérol.The subject of the present invention is the use of esters of N-acyl derivatives of amino acids and polyols as lightening agents for the skin of the human body, as well as non-therapeutic methods for lightening human skin comprising at least one step of applying to said human skin a topical cosmetic formulation comprising said esters of N-acyl derivatives of amino acids and deglycerol.
La peau humaine constitue la première image offerte au regard d’autrui, et parconséquent, l’amélioration de son aspect est un sujet de préoccupation constant pour lesêtres humains. La peau est le reflet d’un état de bien-être, souvent associé à la jeunesse,et a contrario d’un état de fatigue et/ou de vieillissement. Si dans de nombreux pays lesconsommateurs cherchent à brunir la peau, soit naturellement sous l’action desrayonnements UV du soleil soit artificiellement sous l’action de composés chimiques,certains consommateurs recherchent à éclaircir leur peau, pour procurer une imageexterne de pureté, ou dans certains pays d’Asie ou d’Afrique pour procurer une image debeauté. Pour les peaux caucasiennes, le besoin d’éclaircissement peut égalements’inscrire dans une volonté de masquer l’apparition de tâches pigmentaires (dites « tâchesde sénescence ») liées à l’âge.Human skin is the first image offered in the eyes of others, and as a result, the improvement of its appearance is a subject of constant concern for human beings. The skin is a reflection of a state of well-being, often associated with youth, and a contrario a state of fatigue and / or aging. While consumers in many countries seek to brown the skin, either naturally under the action of UV radiation from the sun or artificially under the action of chemical compounds, some consumers seek to clear their skin, to provide an external image of purity, or in some cases countries in Asia or Africa to provide a good image. For Caucasian skin, the need for clarification may also be part of a desire to mask the appearance of age-related pigment spots (so-called "senescence tasks").
La couleur et l’éclat du teint de la peau résultent de la combinaison de deuxcomposantes biologiques : la vascularisation et la pigmentation de la peau ; laditepigmentation de la peau étant la résultante des quantités de mélanines et de carotènesprésentes dans la peau humaine.The color and radiance of the complexion of the skin result from the combination of two biological components: the vascularization and the pigmentation of the skin; said pigmentation of the skin being the resultant of the amounts of melanins and carotenes present in human skin.
Les mélanines sont produites par des cellules épidermiques spécifiques : lesmélanocytes. Ceux-ci se retrouvent au niveau de la couche basale de l’épiderme ou dansles follicules pileux. Les mélanines sont des cellules de grande taille, présentant denombreux et longs prolongements que l’on nomme dendrites. Ces dendrites entrent encontact avec les kératinocytes environnants, pouvant se situer jusqu’à deux assisescellulaires supérieures, pour transmettre les mélanines regroupées dans desmélanosomes.Melanins are produced by specific epidermal cells: the melanocytes. These are found at the level of the basal layer of the epidermis or in the hair follicles. Melanins are large cells with many long extensions called dendrites. These dendrites enter encontact with the surrounding keratinocytes, which can be up to two upper cell layers, to transmit melanin grouped in melanosomes.
On désigne par Unité Epidermique de Mélanisation (UEM), l’ensemble composédes mélanocytes et des kératinocytes, interagissant ensemble pour donner la couleur à lapeau.Epidermal Unit of Melanization (EMU) is defined as the group consisting of melanocytes and keratinocytes, interacting together to give color to the skin.
Une UEM comprend notamment un mélanocyte et une quarantaine de kératinocytes. Leprocessus de mélanogenèse en lui-même comprend la synthèse des mélanines par lesmélanocytes, leur transfert et leur distribution aux kératinocytes avoisinants.An EMU comprises in particular a melanocyte and forty keratinocytes. The melanogenesis process itself comprises the synthesis of melanins by the melanocytes, their transfer and their distribution to neighboring keratinocytes.
La synthèse de mélanines se produit dans les mélanocytes, et plusparticulièrement dans des organites spécialisés, les mélanosomes. Cette synthèse se faità partir de la tyrosine et fait intervenir plusieurs enzymes, dont la tyrosinase qui est lapremière des enzymes à intervenir dans la chaîne réactionnelle.The synthesis of melanins occurs in melanocytes, and more particularly in specialized organelles, melanosomes. This synthesis is made from tyrosine and involves several enzymes, including tyrosinase which is the first enzyme to intervene in the reaction chain.
La pigmentation de la peau peut soit être constitutive soit induite. La pigmentationconstitutive repose sur le patrimoine génétique de l’individu, les facteurs hormonaux etl’âge. La pigmentation induite résulte principalement d’expositions aux rayonnementsultra-violets. Elle apparaît entre 48 heures et 72 heures après l’exposition de la peau auxrayonnements ultra-violets et disparaît rapidement après l’arrêt de l’exposition. Cetteinduction de la pigmentation résulte notamment d’une activation de la tyrosinase, d’uneaugmentation de la taille et du nombre de mélanocytes et d’un accroissement du transfertdes mélanosomes aux kératinocytes. Une action indirecte sur les kératinocytes entreégalement en jeu pour favoriser le processus de mélanogenèse par la sécrétion defacteurs solubles. A contrario, une inhibition de l’activité de la tyrosinase induira une diminution de laquantité des mélanines produites par les mélanocytes et conduira à sa manifestationvisible, à savoir l’éclaircissement naturel de la peau humaine.The pigmentation of the skin can either be constitutive or induced. The pigmentationconstitutive is based on the genetic heritage of the individual, hormonal factors and age. Induced pigmentation results mainly from ultraviolet radiation exposures. It appears between 48 hours and 72 hours after exposure of the skin to ultraviolet radiation and disappears quickly after the exposure has stopped. This induction of pigmentation results in particular from an activation of tyrosinase, an increase in the size and number of melanocytes and an increase in the transfer of melanosomes to keratinocytes. An indirect action on keratinocytes is also involved to promote the process of melanogenesis by the secretion of soluble agents. On the other hand, inhibition of tyrosinase activity will induce a decrease in the quantity of melanins produced by melanocytes and lead to its visible manifestation, namely the natural lightening of human skin.
De nombreuses formulations cosmétiques comprennent comme agentséclaircissants de la peau l’acide kojique, l'arbutine et/ou le magnésium ascorbylphosphate. L’hydroquinone, substance historiquement utilisée pour éclaircir la peau, estmaintenant interdite dans certains pays du fait de son action altérante de la peau et desdangers qu’elle induit pour la santé du consommateur.Many cosmetic formulations include kojic acid, arbutin and / or magnesium ascorbyl phosphate as skin lightening agents. Hydroquinone, a substance historically used to lighten the skin, is now prohibited in some countries because of its altering action on the skin and the dangers it brings to the health of the consumer.
La demande de brevet européen publiée sous le numéro EP 1 471 881 divulgueque des dérivés N-acylés d'acides alpha-aminés et notamment le N-undécylénoylphénylalanine, présentent une affinité vis à vis du récepteur de la Mélanocyte SpécifiqueHormone (α-MSH) et induisent ainsi l'éclaircissement de la peau selon le mécanismebiochimique suivant : la compétition entre l'hormone α-MSH et la molécule présentant uneaffinité vis à vis du récepteur α-MSH, entraîne un moindre taux de fixation de laditehormone sur les récepteurs cellulaires ; cette compétition a pour conséquence uneinhibition de l'activité de l'adénylate cyclase qui entraîne une moindre transformation deΓΑΤΡ en AMP cyclique intracellulaire ; la diminution du taux d'AMP cyclique entraîne uneinhibition de l'enzyme Protéine Kinase A (PKA) ; l'inhibition de la Protéine Kinase A induitune moindre activation de la tyrosinase du fait de la moindre transformation de cette dernière en tyrosinase phosphorylée ; cette moindre activation de la tyrosinase entraîne ladiminution de la synthèse de mélanine d'où découle une moindre pigmentation de la peau.The European patent application published under the number EP 1 471 881 discloses that N-acylated derivatives of alpha-amino acids and in particular N-undecylenoylphenylalanine have an affinity for the specific melanocyte-hormone receptor (α-MSH) and thus induce the lightening of the skin according to the following biochemical mechanism: the competition between the α-MSH hormone and the molecule having an affinity towards the α-MSH receptor, results in a lower rate of attachment of said hormone to the cellular receptors; this competition results in an inhibition of the activity of the adenylate cyclase which causes a less transformation of ΓΑΤΡ into intracellular cyclic AMP; the decrease in cyclic AMP results in inhibition of Protein Kinase A (PKA) enzyme; inhibition of Protein Kinase A induces less activation of tyrosinase due to less transformation of tyrosinase into phosphorylated tyrosinase; this less activation of tyrosinase leads to a decrease in melanin synthesis, which results in less pigmentation of the skin.
La demande de brevet japonais N° 2000-229121 décrit l’utilisation des polyolsesters des N-acylamino acides comme tensioactifs performantsJapanese Patent Application No. 2000-229121 describes the use of polyolsesters of N-acylamino acids as effective surfactants
La demande internationale publiée sous le numéro WO 2010/034917 décrit lesmono-esters et les di-esters de polyols du N-(œ-undécylénoyl) phénylalanine, et plusparticulièrement les mono-esters et les di-esters résultant de la réaction du glycérol et duN-(co-undécylénoyl) phénylalanine, et leurs utilisations comme agents éclaircissants de lapeau humaine.The international application published under the number WO 2010/034917 describes the monoesters and di-esters of polyols of N- (undecylenoyl) phenylalanine, and more particularly the mono-esters and diesters resulting from the reaction of glycerol and duN- (co-undecylenoyl) phenylalanine, and their uses as lightening agents in the human skin.
Dans le cadre de leurs recherches de nouveaux actifs éclaircissant la peau,améliorés par rapport à ceux de l’état de la technique cités ci-dessus, les inventeurs sesont attachés à développer une nouvelle utilisation comme agent éclaircissants de dérivésN-acylés d’acides aminés. C’est pourquoi, selon un premier aspect, l’invention a pour objet l’utilisation d’uncomposé de formule (I) : R’-O-CH2-CH(OH)-[CH2-O-CH2]S-[CH(OH)]P-CH2-O-R”, danslaquelle s est égal à 0 ou à 1 et p est égal à 0, 1, 2 ou 3 et R’ et R", identiques oudifférents, représentent soit un atome d'hydrogène, soit un radical monovalent de formule(II):In the context of their search for new skin-brightening active agents, improved over those of the state of the art cited above, the inventors are attached to developing a new use as a lightening agent for N-acylated amino acid derivatives. . Therefore, according to a first aspect, the subject of the invention is the use of a compound of formula (I): R'-O-CH 2 -CH (OH) - [CH 2 -O-CH 2] S- [ CH (OH)] p-CH2-OR ", wherein s is 0 or 1 and p is 0, 1, 2 or 3 and R 'and R", which are the same or different, represent either a hydrogen atom or a monovalent radical of formula (II):
formule (II) dans laquelle le groupe R1(C=O) représente un radical acyle choisi parmi lesradicaux octanoyle, décanoyle, dodécanoyle, tétradécanoyle, et optionnellementhexadécanoyle, octadécanoyle, 9-octadécènoyle et octadéca-9,12-diènoyle, étant entendu que dans ladite formule (I), au moins un des radicaux R' ou R" nereprésente pas un atome d'hydrogène et que lorsqu'aucun des radicaux R' et R" nereprésente un atome d'hydrogène, R' et R" sont identiques, ou d’un mélange de composésde formule (I), ladite utilisation étant dans le but d’éclaircir la peau humaine et ladite utilisation étant dansune composition cosmétique.formula (II) in which the group R1 (C = O) represents an acyl radical chosen from octanoyl, decanoyl, dodecanoyl, tetradecanoyl and optionally hexadecanoyl, octadecanoyl, 9-octadecenoyl and octadeca-9,12-dienoyl, it being understood that in said formula (I), at least one of the radicals R 'or R "does not represent a hydrogen atom and that when none of the radicals R' and R" nerepresents a hydrogen atom, R 'and R "are identical, or a mixture of compounds of formula (I), said use being for the purpose of lightening human skin and said use being in a cosmetic composition.
Selon un premier aspect particulier l’invention a pour objet l’utilisation telle quedéfinie ci-dessus, d’une composition (C1) comprenant pour 100% de sa masse : - De 99% massique à 20% massique, plus particulièrement de 99% massique à50% massique, et encore plus particulièrement de 95% massique à 75% d’au moins uncomposé de formule (la) :According to a first particular aspect, the subject of the invention is the use as defined above of a composition (C1) comprising for 100% of its mass: from 99% by mass to 20% by weight, more particularly by 99% mass at 50% by weight, and even more particularly at 95% by mass at 75% of at least one compound of formula (Ia):
dans laquelle s est égal à 0 ou à 1 et p est égal à 0, 1, 2 ou 3 et dans laquelle R’représente un radical monovalent de formule (II) :in which s is 0 or 1 and p is 0, 1, 2 or 3 and wherein R 'is a monovalent radical of formula (II):
formule (II) dans laquelle le groupe R1(C=O) représente un radical acyle choisi parmi lesradicaux octanoyle, décanoyle, dodécanoyle, tétradécanoyle, hexadécanoyle,octadécanoyle, 9-octadécènoyle et octadéca-9,12-diènoyle ; et - De 1% massique à 80% massique, plus particulièrement de 1% massique à 50%massique, et encore plus particulièrement de 5% massique à 25% massique d’au moinsun composé de formule (lb) :formula (II) in which the group R 1 (C = O) represents an acyl radical chosen from the radicals octanoyl, decanoyl, dodecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, 9-octadecenoyl and octadeca-9,12-dienoyl; and from 1% by weight to 80% by weight, more particularly from 1% by weight to 50% by weight, and even more particularly from 5% by weight to 25% by weight of at least one compound of formula (Ib):
formule (lb) dans laquelle s est égal à 0 ou à 1 et p est égal à 0, 1,2 ou 3, dans laquelle Rreprésente un radical monovalent de formule (II) :formula (Ib) wherein s is 0 or 1 and p is 0, 1,2 or 3, wherein R represents a monovalent radical of formula (II):
formule (II) dans laquelle le groupe R1(C=O) représente un radical acyle choisi parmi lesradicaux octanoyle, décanoyle, dodécanoyle, tétradécanoyle, et optionnellement lesradicaux hexadécanoyle, octadécanoyle, 9-octadécènoyle et octadéca-9,12-diènoyle.formula (II) wherein the group R1 (C = O) is an acyl radical selected from octanoyl, decanoyl, dodecanoyl, tetradecanoyl, and optionally hexadecanoyl, octadecanoyl, 9-octadecenoyl and octadeca-9,12-dienoyl radicals.
Selon un aspect plus particulier l’invention a pour objet l’utilisation telle que définieprécédemment, pour laquelle, dans les formules (I), (la) ou (lb), s est égal à 0. Selon cetaspect particulier, le composé de formule (I) telle que définie ci-dessus est un ester duglycérol lorsque p est égal à 0, un ester de l’érythritol lorsque p est égal à 1, un ester duxylitol lorsque p est égal à 2 et un ester du sorbitol lorsque p est égal à 3. L’invention atout particulièrement pour objet l’utilisation telle que définie précédemment, pour laquelle,dans les formule (I), (la) ou (lb), s et p sont égaux à 0.According to a more particular aspect, the subject of the invention is the use as defined above, for which, in formulas (I), (la) or (Ib), s is equal to 0. According to this particular aspect, the compound of formula (I) as defined above is a glycerol ester when p is 0, an ester of erythritol when p is 1, a duxylitol ester when p is 2 and a sorbitol ester when p is The invention particularly relates to the use as defined above, for which, in formulas (I), (Ia) or (Ib), s and p are equal to 0.
Selon un aspect tout particulier, l’invention a pour objet, l’utilisation telle définieprécédemment, pour laquelle le composé de formule (I) est le N-octanoyl phénylalaninatede (2,3-dihydroxy) propyle, ou le N-cocoyl phénylalaninate de (2,3-dihydroxy) propyle oupour laquelle la composition (C1 ) comprend pour 100% de sa masse de 99% massique à20% massique, plus particulièrement de 99% massique à 50% massique, et encore plusparticulièrement de 95% massique à 75% massique de N-octanoyl phénylalaninate de(2,3-dihydroxy) propyle et de 1% massique à 80% massique, plus particulièrement de 1%massique à 50% massique, et encore plus particulièrement de 5% massique à 25%massique de bis(N-octanoyl phénylalaninate) de 2-hydroxy 1,3-propanediyle, ou pourlaquelle la composition (C1 ) comprend pour 100% de sa masse de 99% massique à 20%massique, plus particulièrement de 99% massique à 50% massique, et encore plusparticulièrement de 95% massique à 75% massique de N-cocoyl phénylalaninate de (2,3-dihydroxy) propyle et de 1% massique à 80% massique, plus particulièrement de 1%massique à 50% massique, et encore plus particulièrement de 5% massique à 25%massique de bis(N-cocoyl phénylalaninate) de 2-hydroxy 1,3-propanediyle.According to a very particular aspect, the subject of the invention is the use as defined above, for which the compound of formula (I) is N-octanoyl phenylalaninated (2,3-dihydroxy) propyl, or N-cocoyl phenylalaninate. (2,3-dihydroxy) propyl or for which the composition (C1) comprises for 100% of its mass from 99% by weight to 20% by weight, more particularly from 99% by weight to 50% by weight, and even more particularly from 95% by weight to 75% by weight. % by mass of (2,3-dihydroxy) propyl N-octanoyl phenylalaninate and 1% by mass at 80% by weight, more particularly from 1% by weight to 50% by mass, and even more particularly from 5% by mass to 25% by mass of bis (N-octanoylphenylalaninate) of 2-hydroxy-1,3-propanediyl, or for which the composition (C1) comprises for 100% of its mass of 99% by mass at 20% by mass, more particularly of 99% by weight at 50% by mass and even more particularly from 95% by weight to 75% by mass of N-cocoyl ph (2,3-dihydroxy) propyl enylalaninate and 1% by weight to 80% by weight, more particularly from 1% by mass to 50% by mass, and even more particularly from 5% by weight to 25% by mass of bis (N-cocoyl phenylalaninate) ) 2-hydroxy 1,3-propanediyl.
Par N-cocoyl phénylalaninate de (2,3-dihydroxy) propyle, on désigne dans lesdéfinitions des composées de formule (I) et (la) un mélange comprenant pour 100%molaire : - De 5% molaire à 15% molaire de N-octanoyl phénylalaninate de (2,3-dihydroxy)propyle, - De 5% molaire à 10% molaire de N-décanoyl phénylalaninate de (2,3-dihydroxy)propyle, - De 45% molaire à 55% molaire de N-dodécanoyl phénylalaninate de (2,3-dihydroxy) propyle, - De 10% molaire à 20% molaire de N-tétradécanoyl phénylalaninate de (2,3-dihydroxy) propyle, - De 5% molaire à 15% molaire de N-hexadécanoyl phénylalaninate de (2,3-dihydroxy) propyle, et - De 5% molaire à 10% molaire d’un mélange de N-octadécanoyl phénylalaninatede (2,3-dihydroxy) propyle de N-(9-octadécènoyl) phénylalaninate de (2,3-dihydroxy)propyle et de N-(octadéca-9,12-diènoyl) phénylalaninate de (2,3-dihydroxy) propyle.By N-cocoyl phenylalaninate of (2,3-dihydroxy) propyl, is meant in the definitions of the compounds of formula (I) and (la) a mixture comprising for 100 mol%: - 5 mol% to 15 mol% of N- (2,3-dihydroxy) propyl octanoyl phenylalaninate; - from 5 mol% to 10 mol% of (2,3-dihydroxy) propyl N-decanoyl phenylalaninate; - from 45 mol% to 55 mol% of N-dodecanoyl phenylalaninate of (2,3-dihydroxy) propyl; - from 10 mol% to 20 mol% of (2,3-dihydroxy) propyl N-tetradecanoyl phenylalaninate; - from 5 mol% to 15 mol% of N-hexadecanoyl phenylalaninate ( 2,3-dihydroxy) propyl, and - From 5 mol% to 10 mol% of a mixture of N- (9-octadecenoyl) phenylalaninate N-octadecanoyl phenylalaninated (2,3-dihydroxy) propyl dihydroxy) propyl and (2,3-dihydroxy) propyl N- (octadeca-9,12-dienoyl) phenylalaninate.
Par bis(N-cocoyl phénylalaninate) de 2-hydroxy 1,3-propanediyle, on désigne dansles définitions des composées de formule (I) et (lb) un mélange comprenant pour 100%molaire : - De 5% molaire à 15% molaire de bis(N-octanoyl phénylalaninate) de 2-hydroxy1,3-propanediyle, - De 5% molaire à 10% molaire de bis(N-décanoyl phénylalaninate) de 2-hydroxy1,3-propanediyle, - De 45% molaire à 55% molaire de bis(N-dodécanoyl phénylalaninate) de 2-hydroxy 1,3-propanediyle, - De 10% molaire à 20% molaire de bis(N-tétradécanoyl phénylalaninate) de 2-hydroxy 1,3-propanediyle, - De 5% molaire à 15% molaire de bis(N-hexadécanoyl phénylalaninate) de 2-hydroxy 1,3-propanediyle, et - De 5% molaire à 10% molaire d’un mélange de bis(N-octadécanoylphénylalaninate) de 2-hydroxy 1,3-propanediyle, de bis[N-(9-octadécènoyl)phénylalaninate] de 2-hydroxy 1,3-propanediyle, et de bis[N-(octadéca-9,12-diènoyl)phénylalaninate] de 2-hydroxy 1,3-propanediyle.By bis (N-cocoylphenylalaninate) of 2-hydroxy-1,3-propanediyl is meant in the definitions of the compounds of formula (I) and (Ib) a mixture comprising for 100 mol%: - 5 mol% to 15 mol% of 2-hydroxy-1,3-propanediyl bis (N-octanoyl phenylalaninate), - 5 mol% to 10 mol% of bis (N-decanoyl phenylalaninate) of 2-hydroxy-1,3-propanediyl, - 45 mol% to 55 mol% of bis (N-dodecanoyl phenylalaninate) of 2-hydroxy-1,3-propanediyl, - from 10 mol% to 20 mol% of bis (N-tetradecanoyl phenylalaninate) of 2-hydroxy-1,3-propanediyl, mol% to 15 mol% of bis (N-hexadecanoyl phenylalaninate) of 2-hydroxy 1,3-propanediyl, and - from 5 mol% to 10 mol% of a mixture of bis (N-octadecanoylphenylalaninate) of 2-hydroxy-1 3-propanediyl, 2-hydroxy-1,3-propanediyl bis [N- (9-octadecenoyl) phenylalaninate], and 2-hydroxy-1-bis [N- (octadeca-9,12-dienoyl) phenylalaninate], 3-propanediyl.
Le composé de formule (I) telle que définie précédemment peut être préparé selonun procédé de préparation comprenant : - Une étape a) d’estérification d’un composé de formule (IVa) :The compound of formula (I) as defined above can be prepared according to a preparation process comprising: a step a) of esterification of a compound of formula (IVa):
dans laquelle R1-C(=O)- est tel que défini dans la formule (lia), avec un composé de formule (V) : H-O-A-O-H (V), dans laquelle A représente un radical divalent de formule (III) telle que définieprécédemment, pour obtenir, soit le composé de formule (la), soit le composé de formule(lb), soit un mélange (M) du composé de formule (la) et du composé de formule (lb) ; et sinécessaire ou si désiré, - Une étape b) de séparation des composés de formule (la) et de formule (lb), à partir dududit mélange (M) obtenu à l'étape (a).in which R1-C (= O) - is as defined in formula (IIa), with a compound of formula (V): HOAOH (V), in which A represents a divalent radical of formula (III) as defined previously to obtain either the compound of formula (Ia) or the compound of formula (Ib) or a mixture (M) of the compound of formula (Ia) and the compound of formula (Ib); and, if necessary, - a step b) of separating the compounds of formula (Ia) and formula (Ib) from the said mixture (M) obtained in step (a).
Les composés de formules (IVa) sont connus ou sont synthétisables par N-acylation des α-amino acides correspondant selon des méthodes connues de l'homme dumétier.The compounds of formulas (IVa) are known or can be synthesized by N-acylation of the corresponding α-amino acids according to methods known to those skilled in the art.
Dans le procédé tel que défini ci-dessus, le rapport molaire composé de formule(IVa) sur composé de formule (V) est généralement compris entre 3/1 et 1/5, plusparticulièrement entre 1/1 et 1/5, et encore plus particulièrement entre 1/1 et 1/3.In the process as defined above, the compound molar ratio of formula (IVa) on compound of formula (V) is generally between 3/1 and 1/5, more particularly between 1/1 and 1/5, and even more particularly between 1/1 and 1/3.
Dans le procédé tel que défini ci-dessus, l’étape b) de séparation des composés deformule (la) et de formule (lb) est mise en œuvre par les méthodes classiques deséparation connues de l’homme du métier.In the process as defined above, the step b) of separating the compounds of formula (Ia) and of formula (Ib) is carried out by the conventional methods of separation known to those skilled in the art.
Le composé de formule (I) telle que définie précédemment peut être également préparéselon un procédé de préparation comprenant : - Une étape a1) d’estérification d’un composé de formule (IVa)The compound of formula (I) as defined above can also be prepared by a preparation process comprising: a step a1) of esterification of a compound of formula (IVa)
dans laquelle R1-C(=O)- est tel que défini dans la formule (lia), avec un alcool de formule(VI): R5-OH (VI), dans laquelle R5 représente un radical aliphatique linéaire comportant de 1 à 4 atomes decarbone, pour former un composé de formule (Vlla) :wherein R1-C (= O) - is as defined in formula (IIa), with an alcohol of formula (VI): R5-OH (VI), wherein R5 represents a linear aliphatic radical having from 1 to 4 decarbon atoms, to form a compound of formula (VIIa):
dans laquelle R1-C(=O)- et R5 sont tels que définis précédemment, - Une étape a2) de trans-estérification du composé de formule (VIla) obtenu à l'étape ai),par réaction avec le composé de formule (V), pour obtenir, soit le composé de formule (la),soit le composé de formule (lb), soit un mélange (M) du composé de formule (la) et ducomposé de formule (lb) ; et si nécessaire ou si désiré, - La mise en œuvre de l'étape b).in which R1-C (= O) - and R5 are as defined above, - a step a2) of trans-esterification of the compound of formula (VIla) obtained in step a1), by reaction with the compound of formula ( V) to obtain either the compound of formula (Ia) or the compound of formula (Ib) or a mixture (M) of the compound of formula (Ia) and the compound of formula (Ib); and if necessary or desired, - The implementation of step b).
Dans le procédé tel que décrit ci-dessus, l’étape a1) est généralement réalisée àune température d’environ comprise entre 60°C et 120°C, sous gaz inerte, et en présenced’un système catalytique acide. Par système catalytique acide on désigne les acides fortscomme l’acide sulfurique, l’acide chlorhydrique, l’acide phosphorique, l’acide nitrique,l’acide hypophosphoreux, l’acide méthanesulfonique, l’acide para-toluène sulfonique,l’acide trifluorométhane sulfonique, ou les résines échangeuses d'ions acides.In the process as described above, step a1) is generally carried out at a temperature of about 60 ° C to 120 ° C, under an inert gas, and in the presence of an acidic catalyst system. By acidic catalytic system are meant strong acids such as sulfuric acid, hydrochloric acid, phosphoric acid, nitric acid, hypophosphorous acid, methanesulfonic acid, para-toluene sulfonic acid, acid trifluoromethanesulfonic acid, or acidic ion exchange resins.
Dans l’étape a1) de la variante du procédé tel que décrit ci-dessus, le rapport molairecomposé de formule (IVa) sur alcool de formule (VI) est généralement compris entre 1/1 et1/10, plus particulièrement entre 1/1 et 1/8, et encore plus particulièrement entre 1/2 et1/8.In step a1) of the variant of the process as described above, the molar ratio compound of formula (IVa) on alcohol of formula (VI) is generally between 1/1 and 1/10, more particularly between 1/1 and 1/8, and even more particularly between 1/2 and 1/8.
Dans la variante du procédé de préparation des composés de formule (I) telle quedécrite ci-dessus, l’étape a2) de trans-estérification de l’ester de formule (Vlla) obtenu àl'étape a1) est généralement réalisée à une température d’environ comprise entre 80°C et180°C, plus particulièrement comprise entre 100°C et 150°C, encore plus particulièremententre 120°C et 150°C, sous gaz inerte, et en présence d’un système catalytique acide telque précédemment décrit, et avec distillation sous vide de l’alcool de formule (VI) formé in-situ.In the variant of the process for the preparation of the compounds of formula (I) as described above, step a2) of transesterification of the ester of formula (VIIa) obtained in step a1) is generally carried out at a temperature approximately between 80 ° C and 180 ° C, more particularly between 100 ° C and 150 ° C, even more particularly between 120 ° C and 150 ° C under an inert gas, and in the presence of an acid catalyst system such as previously described, and with vacuum distillation of the alcohol of formula (VI) formed in-situ.
Dans l’étape a2) de cette variante du procédé de préparation des composés deformule (I) telle que décrite ci-dessus, le rapport molaire composé de formule (Vlla) sur lecomposé de formule (V) est compris entre 3/1 et 1/5, plus particulièrement entre 1/1 et 1/5,et encore plus particulièrement entre 1/1 et 1/3.In step a2) of this variant of the process for the preparation of the compounds of the formula (I) as described above, the compound molar ratio of formula (Vlla) on the compound of formula (V) is between 3/1 and 1 / 5, more particularly between 1/1 and 1/5, and even more particularly between 1/1 and 1/3.
La composition (Cfl dont l’utilisation telle que précédemment définie est l’objet del’invention peut être préparée par diverses voies.The composition (Cf) whose use as defined above is the subject of the invention may be prepared by various routes.
Une première voie de préparation de la composition (Cfl consiste à mélanger dansles proportions massiques souhaitées, le composé de formule (la) tel que définie ci-dessus ou le mélange de composés de formule (la), avec le composé de formule (lb) telleque définie ci-dessus, ou le mélange de composés de formule (lb).A first route of preparation of the composition (Cfl comprises mixing in the desired mass proportions the compound of formula (Ia) as defined above or the mixture of compounds of formula (Ia) with the compound of formula (Ib) as defined above, or the mixture of compounds of formula (Ib).
Une seconde voie de préparation de la composition (Cfl consiste à mettre enœuvre le procédé de préparation du composé de formule (I) tel que décrit précédemment,en faisant réagir dans les proportions souhaitées, le composé de formule (V) avec lecomposé de formule (IVa) ou un mélange de composés de formule (IVa).A second route of preparation of the composition (Cfl consists of carrying out the process for the preparation of the compound of formula (I) as described above, by reacting in the desired proportions, the compound of formula (V) with the compound of formula ( IVa) or a mixture of compounds of formula (IVa).
Une troisième voie de préparation de la composition (Cfl consiste à mettre enœuvre la variante du procédé de préparation du composé de formule (I) telle que décriteprécédemment, en faisant réagir dans les proportions souhaitées, le composé de formule(V) avec le composé de formule (VIla) ou un mélange de composés de formule (VIla).A third route for the preparation of the composition (Cfl) consists in implementing the variant of the process for preparing the compound of formula (I) as described above, by reacting in the desired proportions, the compound of formula (V) with the compound of formula (VIla) or a mixture of compounds of formula (VIla).
Le composé de formule (I) et la composition (C1) tels que définis ci-dessus et dontl’utilisation telle que définie précédemment est l’objet de la présente invention, peuventêtre administrés par voie orale, topique ou parentérale, et plus particulièrement par voietopique. L’invention a aussi pour objet, un procédé dans le but d’éclaircir la peau humaine,comprenant au moins une étape d'application sur la peau humaine, d'une formulationcosmétique à usage topique comprenant au moins un excipient cosmétiquementacceptable et une quantité efficace du composé de formule (I) ou de la composition (C1)tels que définis précédemment.The compound of formula (I) and the composition (C1) as defined above and whose use as defined above is the subject of the present invention, may be administered orally, topically or parenterally, and more particularly by voietopique. The invention also relates to a method for lightening human skin, comprising at least one step of application to human skin, of a topical cosmetic formulation comprising at least one cosmetically acceptable excipient and an effective amount. of the compound of formula (I) or of the composition (C1) as defined above.
Dans le procédé cosmétique tel que décrit ci-dessus, la formulation cosmétique àusage topique est étalée sur la surface de la peau à traiter, puis la peau est masséequelques instants. L'expression "à usage topique" utilisée dans la définition de la formulationcosmétique mise en œuvre dans le procédé cosmétique objet de la présente invention,signifie que ladite formulation est mise en œuvre par application sur la peau, qu'il s'agissed'une application directe dans le cas d'une formulation cosmétique ou d'une applicationindirecte lorsque la formulation cosmétique selon l’invention est imprégnée sur un supportdestiné à être mis en contact avec la peau (papier, lingette, textile, dispositiftransdermique, etc...). L’expression « cosmétiquement acceptable » utilisée dans la définition de laformulation cosmétique à usage topique, mise en œuvre dans le procédé cosmétiqueobjet de la présente invention, signifie selon la directive du Conseil de la CommunautéEconomique Européenne N°76/768/CEE du 27 juillet 1976 modifiée par la directiveN°93/35/CEE du 14 juin 1993, que ladite formulation à usage topique comprend toutesubstance ou préparation destinée à être mise en contact avec les diverses parties ducorps humain (épiderme, système pileux et capillaire, ongles, lèvres et organes génitaux)ou avec les dents et les muqueuses buccales en vue, exclusivement et principalement, deles nettoyer, de les parfumer, d’en modifier l’aspect et/ou d’en corriger les odeurscorporelles et/ou de les protéger ou de les maintenir en bon état.In the cosmetic process as described above, the topical cosmetic formulation is spread on the surface of the skin to be treated, then the skin is massaged a few moments. The expression "for topical use" used in the definition of the cosmetic formulation used in the cosmetic process that is the subject of the present invention means that said formulation is implemented by application to the skin, whether it is a direct application in the case of a cosmetic formulation or aindirect application when the cosmetic formulation according to the invention is impregnated on a supportdestiné to be put in contact with the skin (paper, wipe, textile, transdermal device, etc ...) . The term "cosmetically acceptable" used in the definition of the cosmetic formulation for topical use, used in the cosmetic process object of the present invention, means according to the Council Directive of the European Economic Community No. 76/768 / EEC of July 27 1976 amended by Directive 93/35 / EEC of 14 June 1993, that the said formulation for topical use includes any substance or preparation intended to be put in contact with the various parts of the human body (epidermis, hair and capillary system, nails, lips and genitals) or with the teeth and oral mucosa in view, exclusively and principally, to clean, perfume, modify the appearance and / or correct body odor and / or protect or keep in good condition.
Par quantité efficace du composé de formule (I) ou d’une composition (C1) tellesque définies précédemment présente dans la formulation cosmétique à usage topiquemise en œuvre dans le procédé cosmétique objet de la présente invention, on entend pour100% de la masse de ladite formulation cosmétique à usage topique, entre 0,1% et 5%massique, plus particulièrement entre 0,1% et 3% massique, et encore plusparticulièrement entre 0,5% et 2% massique de composé de formule (I) ou de composition(C1).An effective amount of the compound of formula (I) or of a composition (C1) as defined previously present in the cosmetic formulation for topical use implemented in the cosmetic process that is the subject of the present invention, is understood to mean100% of the mass of said cosmetic formulation for topical use, between 0.1% and 5% by weight, more particularly between 0.1% and 3% by weight, and even more particularly between 0.5% and 2% by weight of compound of formula (I) or composition (C1).
Les formulations cosmétiques à usage topique mises en œuvre dans le procédécosmétique objet de la présente invention, se présentent généralement sous forme desolutions aqueuses ou hydro-alcooliques ou hydro-glycoliques, sous forme d’unesuspension, d’une émulsion, d’une microémulsion ou d’une nano-émulsion, qu'elles soientde type eau-dans-huile, huile-dans-eau, eau-dans-huile-dans-eau ou huile-dans-eau-dans-huile, ou sous forme d’une poudre. Ces formulations peuvent être conditionnées dans unflacon, dans un dispositif de type "flacon" pompe, sous forme pressurisées dans undispositif aérosol, dans un dispositif muni d'une paroi ajourée comme une grille ou dans undispositif muni d'un applicateur à billes (dit "roll-on").The cosmetic formulations for topical use implemented in the method of the present invention, are generally in the form of aqueous or hydro-alcoholic or hydro-glycolic solutions, in the form of suspension, an emulsion, a microemulsion or a nano-emulsion, whether water-in-oil, oil-in-water, water-in-oil-in-water or oil-in-water-in-oil, or in the form of a powder. These formulations may be packaged in a bottle, in a device of "pump" bottle type, in pressurized form in an aerosol device, in a device provided with a perforated wall such as a grid or in a device equipped with a ball applicator (called " roll-on ").
De façon générale, le composé de formule (I) ou à la composition (C1), présent,est associé à des additifs chimiques habituellement mis en œuvre dans le domaine desformulations à usage topique, comme les tensioactifs moussants et/ou détergents, lestensioactifs épaississants et/ou gélifiants, les agents épaississants et/ou gélifiants, lesagents stabilisants, les composés filmogènes, les solvants et co-solvants, les agentshydrotropes, les eaux thermales ou minérales les agents plastifiants, les agentsémulsionnants et co-émulsionnants, les agents opacificants, les agents nacrants, lesagents surgraissants, les séquestrants, les agents chélatants, les huiles, les cires, les agents antioxydants, les parfums, les huiles essentielles, les agents conservateurs, lesagents conditionneurs, les agents déodorants, les agents blanchissants destinés à ladécoloration des poils et de la peau, les principes actifs destinés à apporter une actiontraitante et/ou protectrice vis à vis de la peau ou des cheveux, les filtres solaires, lescharges minérales ou les pigments, les particules procurant un effet visuel ou destinées àl’encapsulation d’actifs, les particules exfoliantes, les agents de texture, les azurantsoptiques, les répulsifs pour les insectes.In general, the compound of formula (I) or the composition (C1) present, is associated with chemical additives usually used in the field offormulations for topical use, such as foaming surfactants and / or detergents, thickening surfactants and / or gelling agents, thickening and / or gelling agents, stabilizing agents, film-forming compounds, solvents and co-solvents, hydrotropic agents, thermal or mineral waters, plasticizing agents, emulsifying and co-emulsifying agents, opacifying agents, pearlescent agents, superfatting agents, sequestering agents, chelating agents, oils, waxes, antioxidants, perfumes, essential oils, preserving agents, conditioning agents, deodorants, whitening agents for hair dyeing and the skin, the active ingredients intended to provide a protective and / or protective action skin or hair screws, sunscreens, mineral fillers or pigments, particles providing a visual effect or intended for encapsulation of active ingredients, exfoliating particles, texture agents, optical brighteners, repellents for insects .
Comme exemples de tensioactifs moussants et/ou détergents que l’on peutassocier au composé de formule (I) ou à la composition (C1), on peut citer les tensioactifsmoussants et/ou détergents anioniques, cationiques, amphotères ou non ioniques.As examples of foaming and / or detergent surfactants which can be associated with the compound of formula (I) or with the composition (C1), mention may be made of anionic, cationic, amphoteric or nonionic surfactants and / or detergents.
Parmi les tensioactifs anioniques moussants et/ou détergents que l’on peut associer aucomposé de formule (I) ou à la composition (C1), on peut citer les sels de métaux alcalins,de métaux alcalino-terreux, d’ammonium, d’amines, ou d’aminoalcoolsd'alkylethersulfates, d'alkylsulfates, d’alkylamidoéthersulfates, d’alkylarylpolyéthersulfates,de monoglycérides sulfates, d’alpha-oléfinesulfonates, de paraffinessulfonates,d’alkylphosphates, d’alkylétherphosphates, d’alkylsulfonates, d’alkylamidesulfonates,d’alkylarylsulfonates, d’alkylcarboxylates, d’alkylsulfosuccinates, d’alkyléthersulfosuccinates, d’alkylamidesulfosuccinates, d’alkylsulfoacétates, d’alkylsarcosinates, d’acyliséthionates, de N-acyltaurates, d’acyllactylates, de dérivés N-acylés d’acides aminés, de dérivés N-acylés de peptides, de dérivés N-acylés deprotéines, de dérivés N-acylés d’acides gras.Among the foaming and / or detergent anionic surfactants which may be combined with the compound of formula (I) or with the composition (C1), mention may be made of the alkali metal, alkaline earth metal, ammonium, amines, or aminoalcohols of alkyl ether sulfates, alkyl sulphates, alkylamido ether sulphates, alkylaryl polyether sulphates, monoglyceride sulphates, alpha-olefin sulphonates, paraffin sulphonates, alkyl phosphates, alkyl ether phosphates, alkyl sulphonates, alkyl amide sulphonates, alkylarylsulfonates, alkylcarboxylates, alkylsulfosuccinates, alkylethersulfosuccinates, alkylamidesulfosuccinates, alkylsulfoacetates, alkylsarcosinates, acylisethionates, N-acyltaurates, acyllactylates, N-acyl derivatives of amino acids , N-acyl derivatives of peptides, N-acylated protein derivatives, N-acyl derivatives of fatty acids.
Parmi les tensioactifs amphotères moussants et/ou détergents que l’on peutassocier au composé de formule (I) ou à la composition (C1), on peut citer lesalkylbétaïnes, les alkylamidobétaïnes, les sultaïnes, les alkylamidoalkylsulfobétaïnes, lesdérivés d’imidazolines, les phosphobétaïnes, les amphopolyacétates et lesamphopropionates.Among the foaming and / or detergent amphoteric surfactants which may be associated with the compound of formula (I) or with the composition (C1), mention may be made of alkylbetaines, alkylamidobetaines, sultaines, alkylamidoalkylsulfobetaines, derivatives of imidazolines, phosphobetaines , amphopolyacetates and amphopropionates.
Parmi les tensioactifs cationiques moussants et/ou détergents que l’on peutassocier au composé de formule (I) ou à la composition (C1), on peut citerparticulièrement les dérivés d’ammoniums quaternaires.Among the foaming and / or detergent cationic surfactants which may be associated with the compound of formula (I) or with the composition (C1), particular mention may be made of quaternary ammonium derivatives.
Parmi les tensioactifs non ioniques moussants et/ou détergents que l’on peutassocier au composé de formule (I) ou à la composition (C1), on peut citer plusparticulièrement les alkylpolyglycosides comportant un radical aliphatique, linéaire ouramifié, saturé ou insaturé, et comportant de 8 à 16 atomes de carbone, comme l’octylpolyglucoside, le décyl polyglucoside, l’undécylényl polyglucoside, le dodécyl polyglucoside, le tétradécyl polyglucoside, l’hexadécyl polyglucoside, le 1-12 dodécanediylpolyglucoside ; les dérivés d’huile de ricin hydrogénée éthoxylés comme le produitcommercialisé sous le nom INCI « Peg-40 hydrogenated castor oil » ; les polysorbatescomme le Polysorbate 20, le Polysorbate 40, le Polysorbate 60, le Polysorbate 70, lePolysorbate 80, le Polysorbate 85 ; les amides de coprah ; les N-alkylamines.Among the foaming and / or detergent nonionic surfactants which may be associated with the compound of formula (I) or with the composition (C1), mention may be made more particularly of alkylpolyglycosides comprising a linear, saturated, saturated or unsaturated aliphatic radical, and comprising from 8 to 16 carbon atoms, such as octyl polyglucoside, decyl polyglucoside, undecylenyl polyglucoside, dodecyl polyglucoside, tetradecyl polyglucoside, hexadecyl polyglucoside, 1-12-dodecanediyl polyglucoside; ethoxylated hydrogenated castor oil derivatives such as the product marketed under the INCI name "Peg-40 hydrogenated castor oil"; polysorbates such as Polysorbate 20, Polysorbate 40, Polysorbate 60, Polysorbate 70, Polysorbate 80, Polysorbate 85; coconut amides; N-alkylamines.
Comme exemples de tensioactifs épaississants et/ou gélifiants que l’on peutassocier au composé de formule (I) ou à la composition (C1), on peut citer les esters grasd’alkylpolyglycosides éventuellement alcoxylés, comme les esters de méthylpolyglucosideéthoxylés tels que le PEG 120 méthyl glucose trioléate et le PEG 120 méthyl glucosedioléate commercialisés respectivement sous les appellations GLUCAMATE™ LT etGLUMATE™ DOE120 ; les esters gras alcoxylés tels que le PEG 150 pentaérythrytyltétrastéarate commercialisé sous l’appellation CROTHIX™ DS53, le PEG 55 propylèneglycol oléate commercialisé sous l’appellation ANTIL™ 141 ; les carbamates depolyalkylène glycols à chaînes grasses comme le PPG-14 laureth isophoryl dicarbamatecommercialisé sous l’appellation ELFACOS™ T211, le PPG-14 palmeth-60 hexyldicarbamate commercialisé sous l’appellation ELFACOS™ GT2125.Examples of thickening and / or gelling surfactants that can be associated with the compound of formula (I) or with composition (C1) include fatty esters of optionally alkoxylated alkylpolyglycosides, such as methylpolyglucosideethoxylated esters such as PEG 120. methyl glucose trioleate and PEG 120 methyl glucosedioleate respectively marketed under the names GLUCAMATE ™ LT and GLUMATE ™ DOE120; alkoxylated fatty esters such as PEG 150 pentaerythritol tetrastearate marketed under the name CROTHIX ™ DS53, PEG 55 propylene glycol oleate sold under the name ANTIL ™ 141; fatty chain polyalkylene glycol carbamates, such as PPG-14 laureth isophoryl dicarbamat, marketed under the name ELFACOS ™ T211, PPG-14 palmeth-60-hexyldicarbamate sold under the name ELFACOS ™ GT2125.
Comme exemples d’agents épaississants et/ou gélifiants que l’on peut associer aucomposé de formule (I) ou à la composition (C1), on peut citer les polymères de typepolyélectrolytes, linéaires ou branchés ou réticulés, comme l’homopolymère de l’acideacrylique partiellement ou totalement salifié, l’homopolymère de l’acide méthacryliquepartiellement ou totalement salifié, l’homopolymère de l’acide-2-méthyl-[(1-oxo-2-propényl)amino]-1-propanesulfonique (AMPS) partiellement ou totalement salifié, lescopolymères de l’acide acrylique et de l’AMPS, les copolymères de l’acrylamide et del’AMPS, les copolymères de la vinylpyrolidone et de l’AMPS, les copolymères de l’AMPSet de l’acrylate de (2-hydroxyéthyle), les copolymères de l’AMPS et du méthacrylate de (2-hydroxyéthyle), les copolymères de l’AMPS et de l’hydroxyéthylacrylamide, lescopolymères de l’AMPS et du Ν,Ν-diméthyl acrylamide, les copolymères de l’AMPS et dutris(hydroxy- methyl)acrylamido methane (THAM), les copolymères de l’acide acrylique ouméthacrylique et de l’acrylate de (2-hydroxy éthyle), les copolymères de l’acide acryliqueou méthacrylique et du méthacrylate de (2-hydroxy éthyle), les copolymères de l’acideacrylique ou méthacrylique et de l’hydroxyéthylacrylamide, les copolymères de l’acideacrylique ou méthacrylique et du THAM, les copolymères de l’acide acrylique ouméthacrylique et du Ν,Ν-diméthyl acrylamide, les terpolymères de l’acide acrylique ouméthacrylique, de l’AMPS et de l’acrylate de (2-hydroxy éthyle), les terpolymères de l’acide acrylique ou méthacrylique, de l’AMPS et du méthacrylate de (2-hydroxy éthyle),les terpolymères de l’acide acrylique ou méthacrylique, de l’AMPS et du THAM, lesterpolymères de l’acide acrylique ou méthacrylique, de l’AMPS et du N,N-diméthylacrylamide, les terpolymères de l’acide acrylique ou méthacrylique, de l’AMPS et del’acrylamide, les copolymères de l’acide acrylique ou de l’acide méthacrylique etd’acrylates d’alkyle dont la chaîne carbonée comprend entre quatre et trente atomes decarbone et plus particulièrement entre dix et trente atomes de carbone, les copolymèresde l’AMPS et d’acrylates d’alkyle dont la chaîne carbonée comprend entre quatre et trenteatomes de carbone et plus particulièrement entre dix et trente atomes de carbone, lesterpolymère linéaire, branché ou réticulé d'au moins un monomère possédant une fonctionacide fort, libre, partiellement salifiée ou totalement salifiée, avec au moins un monomèreneutre, et au moins un monomère de formule (VIII) : CH2=C(R6)-C(=O)-[CH2-CH2-O]n-R7dans laquelle R6 représente un atome d'hydrogène ou un radical méthyle, R7 représenteun radical alkyle linéaire ou ramifié comportant de huit à trente atomes de carbone et nreprésente un nombre supérieur ou égal à un et inférieur ou égal à cinquante.Examples of thickening and / or gelling agents that can be combined with the compound of formula (I) or with the composition (C1) include polyelectrolytes, linear or branched or crosslinked polymers, such as homopolymer partially or totally salified acrylic acid, partially or totally salified methacrylic acid homopolymer, 2-methyl-[(1-oxo-2-propenyl) amino] -1-propanesulfonic acid (AMPS) homopolymer partially or fully salified, copolymers of acrylic acid and AMPS, copolymers of acrylamide and AMPS, copolymers of vinylpyrrolidone and AMPS, copolymers of AMPS and acrylate of (2-hydroxyethyl), copolymers of AMPS and (2-hydroxyethyl) methacrylate, copolymers of AMPS and hydroxyethylacrylamide, copolymers of AMPS and Ν, Ν-dimethyl acrylamide, copolymers of the AMPS and dutris (h ydroxy-methyl) acrylamido methane (THAM), copolymers of acrylic or methacrylic acid and (2-hydroxyethyl) acrylate, copolymers of acrylic or methacrylic acid and (2-hydroxyethyl) methacrylate, copolymers of acrylic or methacrylic acid and hydroxyethylacrylamide, copolymers of acrylic or methacrylic acid and THAM, copolymers of acrylic or methacrylic acid and Ν, Ν-dimethyl acrylamide, terpolymers of acrylic acid or methacrylic acid, AMPS and (2-hydroxyethyl) acrylate, terpolymers of acrylic or methacrylic acid, AMPS and (2-hydroxyethyl) methacrylate, terpolymers of acrylic or methacrylic acid, AMPS and THAM, terpolymers of acrylic or methacrylic acid, AMPS and N, N-dimethylacrylamide, terpolymers of acrylic or methacrylic acid, AMPS and acrylamid e, copolymers of acrylic acid or of methacrylic acid and of alkyl acrylates whose carbon chain comprises between four and thirty carbon atoms and more particularly between ten and thirty carbon atoms, the copolymers of AMPS and alkyl acrylates whose carbon chain comprises between four and three carbon trenteatomes and more particularly between ten and thirty carbon atoms, the linear, branched or crosslinked interpolymer of at least one monomer having a strong acid function, free, partially salified or totally salified, with at least one monomer, and at least one monomer of formula (VIII): CH2 = C (R6) -C (= O) - [CH2-CH2-O] n -R7in which R6 represents a hydrogen atom or a methyl radical, R7 representsa linear or branched alkyl radical having from eight to thirty carbon atoms and nrepresente a number greater than or equal to one and less than or equal to fifty.
Les polymères de type polyélectrolytes, linéaires ou branchés ou réticulés que l’onpeut associer au composé de formule (I) ou à la composition (C1), peuvent se présentersous la forme d’une solution, d’une suspension aqueuse, d’une émulsion eau-dans-huile,d’une émulsion huile-dans-eau, d’une poudre. Les polymères de type polyélectrolytes,linéaires ou branchés ou réticulés que l’on peut associer au composé de formule (I) ou à lacomposition (C1), peuvent être sélectionnés parmi les produits commercialisés sous lesappellations SIMULGEL™ EG, SIMULGEL™EPG, SEPIGEL™ 305, SIMULGEL™ 600,SIMULGEL™ NS, SIMULGEL™ INS 100, SIMULGEL™ FL, SIMULGEL™ A,SIMULGEL™ SMS 88, SEPINOV™EMT 10, SEPIPLUS™400, SEPIPLUS™265,SEPIPLUS™S, SEPIMAX™Zen, ARISTOFLEX™AVC, ARISTOFLEX™AVS,NOVEMER™EC-1, NOVEMER™EC 2, ARISTOFLEX™HMB, COSMEDIA™SP,FLOCARE™ET 25, FLOCARE™ET 75, FLOCARE™ET 26, FLOCARE™ET 30,FLOCARE™ET 58, FLOCARE™PSD 30, VISCOLAM™AT 64, VISCOLAM™AT 100.The polyelectrolytes polymers, linear or branched or crosslinked that can be associated with the compound of formula (I) or with the composition (C1), can be presentersous in the form of a solution, an aqueous suspension, a water-in-oil emulsion, an oil-in-water emulsion, a powder. The linear or branched or crosslinked polyelectrolytic polymers which can be combined with the compound of formula (I) or with the composition (C1) can be selected from the products sold under the names SIMULGEL ™ EG, SIMULGEL ™ EPG, SEPIGEL ™ 305, SIMULGEL ™ 600, SIMULGEL ™ NS, SIMULGEL ™ INS 100, SIMULGEL ™ FL, SIMULGEL ™ A, SIMULGEL ™ SMS 88, SEPINOV ™ EMT 10, SEPIPLUS ™ 400, SEPIPLUS ™ 265, SEPIPLUS ™ S, SEPIMAX ™ Zen, ARISTOFLEX ™ AVS, ARISTOFLEX ™ AVS, NOVEMER ™ EC-1, NOVEMER ™ EC 2, ARISTOFLEX ™ HMB, COSMEDIA ™ SP, FLOCARE ™ AND 25, FLOCARE ™ AND 75, FLOCARE ™ AND 26, FLOCARE ™ AND 30, FLOCARE ™ AND 58 , FLOCARE ™ PSD 30, VISCOLAM ™ AT 64, VISCOLAM ™ AT 100.
Comme exemples d’agents épaississants et/ou gélifiants que l’on peut associer aucomposé de formule (I) ou à la composition (C1), on peut citer les polysaccharidesconstitués uniquement d’oses, comme les glucanes ou homopolymères du glucose, lesglucomannoglucanes, les xyloglycanes, les galactomannanes dont le degré de substitution(DS) des unités de D-galactose sur la chaîne principale de D-mannose est compris entre 0et 1, et plus particulièrement entre 1 et 0,25, comme les galactomannanes provenant de la gomme de cassia (DS = 1/5), de la gomme de caroube (DS = 1/4), de la gomme de tara(DS = 1/3), de la gomme de guar (DS = 1/2), de la gomme de fenugrec (DS = 1 ).Examples of thickening and / or gelling agents which can be combined with the compound of formula (I) or with composition (C1) include polysaccharides composed solely of monosaccharides, such as glucans or homopolymers of glucose, glucomannoglucans, xyloglycans, galactomannans whose degree of substitution (DS) of D-galactose units on the main D-mannose chain is between 0 and 1, and more particularly between 1 and 0.25, such as galactomannans originating from gum of cassia (DS = 1/5), locust bean gum (DS = 1/4), tara gum (DS = 1/3), guar gum (DS = 1/2), fenugreek gum (DS = 1).
Comme exemples d’agents épaississants et/ou gélifiants que l’on peut associer aucomposé de formule (I) ou à la composition (C1), on peut citer les polysaccharidesconstitués de dérivés d’oses, comme les galactanes sulfatés et plus particulièrement lescarraghénanes et l’agar, les uronanes et plus particulièrement les algines, les alginates etles pectines, les hétéropolymères d’oses et d’acides uroniques et plus particulièrement lagomme xanthane, la gomme gellane, les exsudais de gomme de arabique et de gommede karaya, les glucosaminoglycanes.Examples of thickening and / or gelling agents which can be combined with the compound of formula (I) or with composition (C1) include polysaccharides composed of monosaccharides, such as sulphated galactans and more particularly agar, uronans and more particularly algin, alginates and pectins, heteropolymers of monosaccharides and uronic acids, and more particularly xanthan gum, gellan gum, exudates of arabic gum and karaya gum, glucosaminoglycans .
Comme exemples d’agents épaississants et/ou gélifiants que l’on peut associer aucomposé de formule (I) ou à la composition (C1), on peut citer la cellulose, les dérivésde cellulose comme la méthyl-cellulose, l’éthyl-cellulose, l’hydroxypropyl cellulose, lessilicates, l’amidon, les dérivés hydrophiles de l’amidon, les polyuréthanes.Examples of thickening and / or gelling agents that can be combined with the compound of formula (I) or with the composition (C1) include cellulose, cellulose derivatives such as methylcellulose and ethylcellulose. , hydroxypropyl cellulose, silicates, starch, hydrophilic derivatives of starch, polyurethanes.
Comme exemples d’agents stabilisants que l’on peut associer au composé deformule (I) ou à la composition (C1), on peut citer les cires microcristallines, et plusparticulièrement l’ozokérite, les sels minéraux tels que le chlorure de sodium ou le chlorurede magnésium, les polymères siliconés tels que les copolymères polysiloxane polyalkylpolyéther.Examples of stabilizing agents that can be combined with the compound of Formula (I) or with the composition (C1) include microcrystalline waxes, and more particularly ozokerite, mineral salts such as sodium chloride or magnesium chloride, silicone polymers such as polysiloxane polyalkylpolyether copolymers.
Comme exemples de solvants que l’on peut associer au composé de formule (I) ouà la composition (C1), on peut citer l’eau, les solvants organiques comme le glycérol, lediglycérol, les oligomères du glycérol, l’éthylène glycol, le propylène glycol, le butylèneglycol, le 1,3-propanediol, le 1,2-propanediol, l’hexylèneglycol, le diéthylèneglycol, lexylitol, l’érythritol, le sorbitol, les alcools hydrosolubles tels que l’éthanol, l’isopropanol oule butanol, les mélanges d’eau et desdits solvants organiques.Examples of solvents that can be combined with the compound of formula (I) or with the composition (C1) include water, organic solvents such as glycerol, glycerol, oligomers of glycerol, ethylene glycol, propylene glycol, butylene glycol, 1,3-propanediol, 1,2-propanediol, hexylene glycol, diethylene glycol, lexylitol, erythritol, sorbitol, water-soluble alcohols such as ethanol, isopropanol or butanol, water mixtures and said organic solvents.
Comme exemples d’eaux thermales ou minérales que l’on peut associer aucomposé de formule (I) ou à la composition (C1), on peut citer les eaux thermales ouminérales ayant une minéralisation d'au moins 300 mg/l, en particulier l'eau d'Avene, l'eaude Vittel, les eaux du bassin de Vichy, l'eau d'Uriage, l'eau de la Roche Posay, l'eau de laBourboule, l'eau d'Enghien-les-bains, l'eau de Saint-Gervais-les bains, l'eau de Néris-les-bains, l'eau d'Allevard-les-bains, l'eau de Digne, l'eau des Maizieres, l'eau de Neyrac-les-bains, l'eau de Lons le Saunier, l'eau de Rochefort, l'eau de Saint Christau, l'eau desFumades et l'eau de Tercis-les-bains.Examples of thermal or mineral waters that can be combined with the compound of formula (I) or with the composition (C1) include thermal or mineral waters having a mineralization of at least 300 mg / l, particularly Avene water, the Vittel water, the waters of the Vichy basin, the water of Uriage, the water of the Roche Posay, the water of the Bourboule, the water of Enghien-les-bains, the water of Saint-Gervais-les Bains, the water of Neris-les-Bains, the water of Allevard-les-Bains, the water of Digne, the water of the Maizieres, the water of Neyrac- the baths, the water of Lons le Saunier, the water of Rochefort, the water of Saint Christau, the water of Fumades and the water of Tercis-les-bains.
Comme exemples d’agents hydrotropes que l’on peut associer au composé deformule (I) ou à la composition (C1), on peut citer les xylènes sulfonates, les cumènessulfonates, l’hexylpolyglucoside, le 2-éthylhexylpolyglucoside, le n-heptylpolyglucoside.Examples of hydrotropic agents that can be combined with the compound of Formula (I) or Composition (C1) include xylenesulfonates, cumenesulphonates, hexylpolyglucoside, 2-ethylhexylpolyglucoside, n-heptylpolyglucoside.
Comme exemples d’agents tensioactifs émulsionnants que l’on peut associer aucomposé de formule (I) ou à la composition (C1), on peut citer les tensioactifs nonioniques, des tensioactifs anioniques, des tensioactifs cationiques.Examples of emulsifying surfactants that can be combined with the compound of formula (I) or with the composition (C1) include nonionic surfactants, anionic surfactants and cationic surfactants.
Comme exemples de tensioactifs non-ioniques émulsionnants que l’on peutassocier au composé de formule (I) ou à la composition (C1), on peut citer les estersd’acides gras et de sorbitol, comme les produits commercialisés sous les appellationsMONTANE™40, MONTANE™60, MONTANE™70, MONTANE™80 et MONTANE™85 ;les compositions comprenant du stéarate de glycérol et l’acide stéarique éthoxylé entre 5moles et 150 moles d’oxyde d’éthylène, comme la composition comprenant de l’acidestéarique éthoxylé à 135 moles d’oxyde d’éthylène et du stéarate de glycérolcommercialisée sous l’appellation SIMULSOL™ 165 ; les esters de mannitan ; les estersde mannitan éthoxylés ; les esters de sucrose ; les esters de méthylglucoside ; lesalkylpolyglycosides comportant un radical aliphatique, linéaire ou ramifié, saturé ouinsaturé, et comportant de 14 à 36 atomes de carbone, comme le tétradécylpolyglucoside, l’hexadécyl polyglucoside, l’octadécyl polyglucoside, l’hexadécylpolyxyloside, l’octadécyl polyxyloside, l’eicosyl polyglucoside, le dodécosyl polyglucoside,le 2-octyldodécyl polyxyloside, le 12-hydroxystéaryl polyglucoside ; les compositionsd’alcools gras linéaires ou ramifiés, saturés ou insaturés, et comportant de 14 à 36 atomesde carbone, et d’ alkylpolyglycosides tels que décrits précédemment, par exemple lescompositions commercialisées sous le nom de marque MONTANOV™68,MONTANOV™82, MONTANOV™14, MONTANOV™202, MONTANOV™S,MONTANOV™WO 18, FLUIDANOV™20X et EASYNOV™.Examples of emulsifying nonionic surfactants that may be associated with the compound of formula (I) or with the composition (C1) include esters of fatty acids and of sorbitol, such as the products sold under the names MONTANE ™ 40, MONTANE ™ 60, MONTANE ™ 70, MONTANE ™ 80 and MONTANE ™ 85, the compositions comprising glycerol stearate and ethoxylated stearic acid between 5 mol and 150 moles of ethylene oxide, as the composition comprises ethoxylated acid estereal 135 moles of ethylene oxide and glycerol stearate marketed under the name SIMULSOL ™ 165; mannitan esters; ethoxylated mannitan esters; sucrose esters; methylglucoside esters; the alkylpolyglycosides having a linear or branched, saturated or unsaturated aliphatic radical containing from 14 to 36 carbon atoms, for instance tetradecylpolyglucoside, hexadecyl polyglucoside, octadecyl polyglucoside, hexadecylpolyxyloside, octadecylpolyxoside, eicosyl polyglucoside, dodecosyl polyglucoside, 2-octyldodecyl polyxyloside, 12-hydroxystearyl polyglucoside; compositions of saturated or unsaturated, linear or branched fatty alcohols containing from 14 to 36 carbon atoms, and of alkylpolyglycosides as described above, for example the compositions marketed under the tradename MONTANOV ™ 68, MONTANOV ™ 82, MONTANOV ™ 14, MONTANOV ™ 202, MONTANOV ™ S, MONTANOV ™ WO 18, FLUIDANOV ™ 20X and EASYNOV ™.
Comme exemples de tensioactifs anioniques que l’on peut associer au composéde formule (I) ou à la composition (C1), on peut citer le glycéryl stéarate citrate, lecétéarylsulfate, les savons comme le stéarate de sodium ou le stéarate detriéthanolammonium, les dérivés N-acylés d’acides aminés salifiés comme par exemple lestéaroyl glutamate.Examples of anionic surfactants that can be combined with the compound of formula (I) or with the composition (C1) include glyceryl stearate citrate, cetearyl sulphate, soaps such as sodium stearate or stearic acid detethanolammonium, N derivatives. acylated salified amino acids such as, for example, tetaroyl glutamate.
Comme exemples de tensioactifs cationiques émulsionnants que l’on peut associerau composé de formule (I) ou à la composition (C1), on peut citer les aminoxydes, lequaternium-82 et les tensioactifs décrits dans la demande internationale publiée sous le numéro WO 96 /00719 et principalement ceux dont la chaîne grasse comprend au moins16 atomes de carbone.As examples of emulsifying cationic surfactants that can be associated with the compound of formula (I) or with the composition (C1), mention may be made of the aminoxides, the quaternium-82 and the surfactants described in the international application published under the number WO 96 / 00719 and mainly those whose fatty chain comprises at least 16 carbon atoms.
Comme exemples d’agents opacifiants et/ou nacrants que l’on peut associer aucomposé de formule (I) ou à la composition (C1), on peut citer le palmitate de sodium, lestéarate de sodium, l’hydroxystéarate de sodium, le palmitate de magnésium, le stéaratede magnésium, l’hydroxystéarate de magnésium, le monostéarate d’éthylène glycol, ledistéarate d’éthylène glycol, le monostéarate de polyéthylène glycol, le distéarate depolyéthylène glycol, les alcools gras comportant de 12 à 22 atomes de carbone.Examples of opacifying and / or pearling agents which may be combined with the compound of formula (I) or with the composition (C1) include sodium palmitate, sodium latarate, sodium hydroxystearate and palmitate. magnesium stearate, magnesium hydroxystearate, ethylene glycol monostearate, ethylene glycol stearate, polyethylene glycol monostearate, polyethylene glycol distearate, and fatty alcohols having from 12 to 22 carbon atoms.
Comme exemples d’agents de texture que l’on peut associer au composé deformule (I) ou à la composition (C1), on peut citer des dérivés N-acylés d’acides aminés,comme la lauroyl lysine commercialisée sous l’appellation AMINOHOPE™LL, l’octenylstarch succinate commercialisé sous l’appellation DRYFLO™, le myristyl polyglucosidecommercialisé sous l’appellation MONTANOV™ 14, les fibres de cellulose, les fibres decoton, les fibres de chitosane, le talc, la séricite, le mica.Examples of texturizing agents that can be combined with the compound of formula (I) or with the composition (C1) include N-acyl derivatives of amino acids, such as lauroyl lysine marketed under the name AMINOHOPE. ™ LL, octenylstarch succinate marketed under the name DRYFLO ™, myristyl polyglucoside marketed under the name MONTANOV ™ 14, cellulose fibers, decoton fibers, chitosan fibers, talc, sericite, mica.
Comme exemples d’agents déodorants que l’on peut associer au composé deformule (I) ou à la composition (C1), on peut citer les silicates alcalins, les sels de zinccomme le sulfate de zinc, le gluconate de zinc, le chlorure de zinc, le lactate de zinc ; lessels d’ammonium quaternaires comme les sels de cétyltriméthylammonium, les sels decétylpyridinium ; les dérivés du glycérol comme le caprate de glycérol , le caprylate deglycérol, le caprate de polyglycérol ; le 1,2 décanediol ; le 1,3 propanediol ; l’acidesalicylique ; le bicarbonate de sodium ; les cyclodextrines ; les zéolithes métalliques ; leTRICLOSAN™ ; le bromohydrate d’aluminium, les chlorhydrates d’aluminium, le chlorured’aluminium, le sulfate d’aluminium, les chlorhydrates d’aluminium et de zirconium, letrichlorhydrate d’aluminium et de zirconium, le tétrachlorhydrate d’aluminium et dezirconium, le pentachlorhydrate d’aluminium et de zirconium, l’octochlorhydrated’aluminium et de zirconium, le sulfate d’aluminium, le lactate de sodium et d’aluminium,les complexes de chlorhydrate d’aluminium et de glycol, comme le complexe dechlorhydrate d’aluminium et de propylène glycol, le complexe de dichlorhydrated’aluminium et de propylène glycol, le complexe de sesquichlorhydrate d’aluminium et depropylène glycol, le complexe de chlorhydrate d’aluminium et de polyéthylène glycol, lecomplexe de dichlorhydrate d’aluminium et de polyéthylène glycol, le complexe desesquichlorhydrate d’aluminium et de polyéthylène glycol.Examples of deodorant agents that can be combined with the compound of formula (I) or with the composition (C1) include alkali silicates, zinc salts such as zinc sulfate, zinc gluconate, sodium chloride, and the like. zinc, zinc lactate; quaternary ammonium salts such as cetyltrimethylammonium salts, cetylpyridinium salts; glycerol derivatives such as glycerol caprate, caprylate deglycerol, polyglycerol caprate; 1,2 decanediol; 1,3 propanediol; acidalicylic acid; sodium bicarbonate; cyclodextrins; metallic zeolites; TRICLOSAN ™; aluminum bromohydrate, aluminum chlorohydrates, aluminum chlorides, aluminum sulphate, aluminum and zirconium chlorohydrates, aluminum and zirconium hydrochloride, aluminum and zirconium tetrachlorohydrate, pentachlorhydrate aluminum and zirconium, aluminum and zirconium octochlorhydrate, aluminum sulphate, sodium and aluminum lactate, aluminum and glycol hydrochloride complexes, such as aluminum chlorohydrate complex and propylene glycol complex, aluminum dihydrochloride complex and propylene glycol complex, the complex of aluminum sesquichlorohydrate and propylene glycol, the complex of aluminum hydrochloride and polyethylene glycol, the complex of aluminum dihydrochloride and polyethylene glycol, the complex desesquichlorhydrate aluminum and polyethylene glycol.
Comme exemples d’huiles que l’on peut associer au composé de formule (I) ou à lacomposition (C1), on peut citer les huiles minérales telles que l'huile de paraffine, l'huile de vaseline, les isoparaffines ou les huiles blanches minérales ; les huiles d’origine animale,telles que le squalène ou le squalane ;les huiles végétales, telles que le phytosqualane,l'huile d'amandes douces, l'huile de coprah, l'huile de ricin, l'huile de jojoba, l'huile d'olive,l'huile de colza, l'huile d'arachide, l'huile de tournesol, l'huile de germes de blé, l'huile degermes de maïs, l'huile de soja, l'huile de coton, l'huile de luzerne, l'huile de pavot, l'huilede potiron, l'huile d'onagre, l'huile de millet, l'huile d'orge, l'huile de seigle, l'huile decarthame, l'huile de bancoulier, l'huile de passiflore, l'huile de noisette, l'huile de palme, lebeurre de karité, l'huile de noyau d'abricot, l'huile de calophyllum, l'huile de sysymbrium,l'huile d'avocat, l'huile de calendula, les huiles issues de fleurs ou de légumes les huilesvégétales éthoxylées ; les huiles synthétiques comme les esters d'acides gras tels que lemyristate de butyle, le myristate de propyle, le myristate d’isopropyle, le myristate decétyle, le palmitate d’isopropyle, le palmitate d’octyle, le stéarate de butyle, le stéarated'hexadécyle, le stéarate d’isopropyle, le stéarate d'octyle, le stéarate d'isocétyle, l'oléatedodécyle, le laurate d'hexyle, le dicaprylate de propylèneglycol, les esters dérivés d'acidelanolique, tels que le lanolate d’isopropyle, le lanolate d'isocétyle, les monoglycérides,diglycérides et triglycérides d’acides gras comme le triheptanoate de glycérol, lesalkylbenzoates, les huiles hydrogénées, les poly(alpha-oléfine), les polyoléfines comme lepoly(isobutane), les isoalcanes de synthèse comme l'isohexadécane, l'isododécane, leshuiles perfluorées ; les huiles de silicone comme les diméthylpolysiloxanes, lesméthylphényl - polysiloxanes, les silicones modifiées par des amines, les siliconesmodifiés par des acides gras, les silicones modifiés par des alcools, les silicones modifiéspar des alcools et des acides gras, des silicones modifiés par des groupements polyéther,des silicones époxy modifiés, des silicones modifiées par des groupements fluorés, dessilicones cycliques et des silicones modifiées par des groupements alkyles. Par « huiles »,on entend dans la présente demande les composés et/ou les mélanges de composésinsolubles dans l’eau, se présentant sous un aspect liquide à une température de 25°C.Examples of oils which can be combined with the compound of formula (I) or with the composition (C1) include mineral oils such as paraffin oil, liquid petroleum jelly, isoparaffins or oils. mineral white; oils of animal origin, such as squalene or squalane, vegetable oils, such as phytosqualane, sweet almond oil, coconut oil, castor oil, jojoba oil, olive oil, rapeseed oil, peanut oil, sunflower oil, wheat germ oil, corn oil, soybean oil, oil cotton, alfalfa oil, poppy oil, pumpkin oil, evening primrose oil, millet oil, barley oil, rye oil, decartham oil , banana oil, passionflower oil, hazelnut oil, palm oil, shea butter, apricot kernel oil, calophyllum oil, sysymbrium oil, avocado oil, calendula oil, oils derived from flowers or vegetables, ethoxylated vegetable oils; synthetic oils such as fatty acid esters such as butyl emyristate, propyl myristate, isopropyl myristate, decetyl myristate, isopropyl palmitate, octyl palmitate, butyl stearate, steareate hexadecyl, isopropyl stearate, octyl stearate, isocetyl stearate, oléatedodecyl, hexyl laurate, propylene glycol dicaprylate, esters derived from anelanolic acid, such as isopropyl lanolate , isocetyl lanolate, monoglycerides, diglycerides and triglycerides of fatty acids such as glycerol triheptanoate, alkylbenzoates, hydrogenated oils, poly (alpha-olefin), polyolefins such as poly (isobutane), synthetic isoalkanes, isohexadecane, isododecane, perfluorinated oils; silicone oils such as dimethylpolysiloxanes, methylphenylpolysiloxanes, silicones modified with amines, silicones modified with fatty acids, silicones modified with alcohols, silicones modified with alcohols and fatty acids, silicones modified with polyether groups modified epoxy silicones, silicones modified with fluorinated groups, cyclic desilicones and silicones modified with alkyl groups. By "oils" is meant in the present application the compounds and / or mixtures of compounds insoluble in water, being in a liquid appearance at a temperature of 25 ° C.
Comme exemples de cires que l’on peut associer au composé de formule (I) ou àla composition (C1), on peut citer la cire d’abeille, la cire de carnauba, la cire de candelilla,la cire d’ouricoury, la cire du Japon, la cire de fibre de liège, la cire de canne à sucre, lescires de paraffines, les cires de lignite, les cires microcristallines, la cire de lanoline ;lOzokérite ; la cire de polyéthylène ; les cires de silicone ; les cires végétales ; les alcoolsgras et les acides gras solides à température ambiante ; les glycérides solides àtempérature ambiante. Par « cires », on entend dans la présente demande les composés et/ou les mélanges de composés insolubles dans l’eau, se présentant sous un aspectsolide à une température supérieure ou égale à 45°C.Examples of waxes that can be combined with the compound of formula (I) or with the composition (C1) include beeswax, carnauba wax, candelilla wax, ouricoury wax, Japanese wax, cork fiber wax, sugar cane wax, paraffin waxes, lignite waxes, microcrystalline waxes, lanolin wax, zokokerite; polyethylene wax; silicone waxes; vegetable waxes; alcohols and solid fatty acids at room temperature; solid glycerides at room temperature. By "waxes" is meant in the present application the compounds and / or mixtures of water-insoluble compounds, having a solid appearance at a temperature greater than or equal to 45 ° C.
Comme exemples de principes actifs que l’on peut associer au composé deformule (I) ou à la composition (C1), on peut citer les vitamines et leurs dérivés,notamment leurs esters, tels que le rétinol (vitamine A) et ses esters (palmitate de rétinylepar exemple), l'acide ascorbique (vitamine C) et ses esters, les dérives de sucre de l’acideascorbique (comme l’ascorbyl glucoside), le tocophérol (vitamine E) et ses esters (commel’acétate de tocophérol), les vitamines B3 ou B10 (niacinamide et ses dérivés) ; lescomposés montrant une action éclaircissante ou dépigmentante de la peau comme le ω-undecelynoyl phénylalanine commercialisé sous l’appellation SEPIWHITE™MSH, leSEPICALM™VG, le mono ester et/ou le diester de glycérol du ω-undecelynoylphénylalanine, les ω-undecelynoyl dipeptides, l’arbutine, l’acide kojique, l’hydroquinone ;les composés montrant une action apaisante notamment le SEPICALM™ S, l’allantoïne etle bisabolol ; les agents anti-inflammatoires ; les composés montrant une actionhydratante comme l’urée, les hydroxyurées, le glycérol, les polyglycérols, le glycérolglucoside, le diglycérol glucoside, les polyglycéryl glucosides, le xylityl glucoside ; lesextraits végétaux riches en polyphénols comme les extraits de raisin, les extraits de pin,les extraits de vin, les extraits d'olives ; les composés montrant une action amincissanteou lipolytique comme la caféine ou ses dérivés, l’ADIPOSLIM™, l’ADIPOLESS™, lafucoxanthine ; les protéines N-acylées ; les peptides N-acylés comme le MATRIXIL™ ; lesacides aminés N-acylés ; les hydrolysâts partiels de protéines N-acylés ; les acidesaminés ; les peptides ; les hydrolysâts totaux de protéines ; les extraits de soja, parexemple la Raffermine™ ; les extraits de blé par exemple la TENSINE™ ou laGLIADINE™ ; les extraits végétaux, tels que les extraits végétaux riches en tanins, lesextraits végétaux riches en isoflavones ou les extraits végétaux riches en terpènes ; lesextraits d'algues d'eau douce ou marines ; les extraits de plantes marines ; les extraitsmarins en général comme les coraux ; les cires essentielles ; les extraits bactériens ; lescéramides ; les phospholipides ; les composés montrant une action antimicrobienne ouune action purifiante, comme le LIPACIDE™ C8G, le LIPACIDE™ UG, leSEPICONTROL™ A5 ; l'OCTOPIROX™ ou le SENSIVA™ SC50 ; les composés montrantune propriété énergisante ou stimulante comme le PHYSIOGENYL™, le panthénol et sesdérivés comme le SEPICAP™ MP ; les actifs anti-âge comme le SEPILIFT™ DPHP, leLIPACIDE™ PVB, le SEPIVINOL™, le SEPIVITAL™, le MANOLIVA™, le PHYTO-AGE™,le TIMECODE™ ; le SURVICODE™ ; les actifs anti-photo vieillissement ; les actifs protecteurs de l’intégrité de la jonction dermo-épidermique ; les actifs augmentant lasynthèse des composants de la matrice extracellulaire comme le collagène, les élastines,les glycosaminoglycanes ; les actifs agissant favorablement sur la communicationcellulaire chimique comme les cytokines ou physiques comme les intégrines ; les actifscréant une sensation de « chauffe » sur la peau comme les activateurs de lamicrocirculation cutanée (comme les dérivés de l’acide nicotinique) ou des produits créantune sensation de « fraîcheur » sur la peau (comme le menthol et des dérivés) ; les actifsaméliorant la microcirculation cutanée, par exemple les veinotoniques ; les actifs drainants; les actifs à visée décongestionnante comme les extraits de ginko biloba, de lierre, demarron d'inde, de bambou, de ruscus, de petit houx, de centalla asiatica, de fucus, deromarin, de saule.Examples of active principles that can be combined with the compound of formula (I) or with the composition (C1) include vitamins and their derivatives, especially their esters, such as retinol (vitamin A) and its esters ( retinyl palmitate, for example), ascorbic acid (vitamin C) and its esters, sugar derivatives of ascorbyl glucoside (as ascorbyl glucoside), tocopherol (vitamin E) and its esters (as tocopherol acetate) vitamins B3 or B10 (niacinamide and its derivatives); compounds showing a lightening or depigmenting action on the skin, such as ω-undecelynoyl phenylalanine sold under the name SEPIWHITE ™ MSH, SEPICALM ™ VG, mono-undecelynoylphenylalanine glycerol monoester and / or diester, ω-undecelynoyl dipeptides, arbutin, kojic acid, hydroquinone, the compounds showing a soothing action including SEPICALM ™ S, allantoin and bisabolol; anti-inflammatory agents; compounds showing an actionhydrating agent such as urea, hydroxyureas, glycerol, polyglycerols, glycerolglucoside, diglycerol glucoside, polyglyceryl glucosides, xylityl glucoside; plant extracts rich in polyphenols such as grape extracts, pine extracts, wine extracts, olive extracts; compounds showing a slimming or lipolytic action such as caffeine or its derivatives, ADIPOSLIM ™, ADIPOLESS ™, fucoxanthin; N-acylated proteins; N-acylated peptides such as MATRIXIL ™; N-acylated amino acids; partial hydrolysates of N-acylated proteins; the amino acids; peptides; total hydrolysts of protein; soy extracts, for example Raffermine ™; wheat extracts, for example TENSINE ™ or GILADINE ™; plant extracts, such as tannin-rich plant extracts, plant extracts rich in isoflavones or plant extracts rich in terpenes; extracts of freshwater or marine algae; marine plant extracts; marine extracts in general such as corals; essential waxes; bacterial extracts; ceramides; phospholipids; compounds exhibiting antimicrobial action or purifying action, such as LIPACIDE ™ C8G, LIPACIDE ™ UG, SEPICONTROL ™ A5; OCTOPIROX ™ or SENSIVA ™ SC50; compounds showing an energizing or stimulating property such as PHYSIOGENYL ™, panthenol and its derivatives such as SEPICAP ™ MP; anti-aging actives like SEPILIFT ™ DPHP, LIPACIDE ™ PVB, SEPIVINOL ™, SEPIVITAL ™, MANOLIVA ™, PHYTO-AGE ™, TIMECODE ™; SURVICODE ™; anti-aging photo active ingredients; the active ingredients protecting the integrity of the dermal-epidermal junction; actives enhancing the synthesis of extracellular matrix components such as collagen, elastins, glycosaminoglycans; assets acting favorably on chemical cell communication such as cytokines or physical ones such as integrins; actives creating a sensation of "heating" on the skin, such as cutaneous micro-circulation activators (such as nicotinic acid derivatives) or products that create a sensation of "freshness" on the skin (such as menthol and derivatives); the active ingredients improving the microcirculation of the skin, for example the venotonic ones; draining assets; decongestant assets such as extracts of ginko biloba, ivy, indian corn, bamboo, ruscus, small holly, centalla asiatica, fucus, deromarin, willow.
Comme exemples d’agents antioxydants que l’on peut associer au composé deformule (I) ou à la composition (C1), on peut citer l’EDTA et ses sels, l’acide citrique,l’acide tartarique, l’acide oxalique, le BHA (butylhydroxyanisol), le BHT(butylhydroxytoluène), les dérivés de tocophérol tels que l’acétate de tocophérol, desmélanges de composés antioxydants tels que la DISSOLVINE™ GL 47S commercialisépar la société Akzo Nobel sous le le nom INCI : Tetrasodium Glutamate Diacetate.Examples of antioxidants that can be combined with the compound of Formula (I) or Composition (C1) include EDTA and its salts, citric acid, tartaric acid, oxalic acid , BHA (butylhydroxyanisol), BHT (butylhydroxytoluene), tocopherol derivatives such as tocopherol acetate, mixtures of antioxidant compounds such as DISSOLVINE ™ GL 47S sold by Akzo Nobel under the name INCI: Tetrasodium Glutamate Diacetate .
Comme exemples de filtres solaires que l’on peut associer au composé de formule(I) ou à la composition (C1), on peut citer tous ceux figurant dans la directive cosmétique76/768/CEE modifiée annexe Vil. Parmi les filtres organiques solaires que l’on peutassocier au composé de formule (I) ou à la composition (C1), on peut citer la famille desdérivés de l'acide benzoïque comme les acides para-aminobenzoïques (PABA),notamment les esters de monoglycérol de PABA, les esters éthyliques de N,N-propoxyPABA, les esters éthyliques de Ν,Ν-diéthoxy PABA, les esters éthyliques de Ν,Ν-diméthylPABA, les esters méthyliques de Ν,Ν-diméthyl PABA, les esters butyliques de Ν,Ν-diméthyl PABA; la famille des dérivés de l'acide anthranilique comme l'homomenthyl-N-acétyl anthranilate ; la famille des dérivés de l'acide salicylique comme le salicylated'amyle, le salicylate d'homomenthyle, le salicylate d'éthylhexyle, le salicylate de phényle,le salicylate de benzyle, le salicylate de p-isopropanolphényle ; la famille des dérivés del'acide cinnamique comme le cinnamate d'éthylhexyle, le cinnamate d'éthyl-4-isopropyle,le cinnamate de méthyl-2,5-diisopropyle, le cinnamate de p-méthoxypropyle, le cinnamatede p-méthoxyisopropyle, le cinnamate de p-méthoxyisoamyle, le cinnamate de p-méthoxyoctyle (le cinnamate de p-méthoxy 2-éthylhexyle), le cinnamate de p-méthoxy 2-éthoxyéthyle, le cinnamate de p-méthoxycyclohexyle, le cinnamate d'éthyl-a-cyano-β- phényle, le cinnamate de 2-éthylhexyl-la-cyano-p-phényle, le cinnamate dediparaméthoxy mono-2-éthylhexanoyl de glycéryle ; la famille des dérivés de labenzophénone comme la 2,4-dihydroxybenzophénone, la 2,2'-dihydroxy-4-méthoxybenzophénone, la 2,2',4,4'-tétrahydroxybenzophénone, la 2-hydroxy-4-méthoxybenzophénone, la 2-hydroxy-4-méthoxy-4'-méthylbenzophénone, la 2-hydroxy-4-méthoxybenzophénone-5-sulfonate, la 4-phénylbenzophénone, le 2-éthylhexyl-4'-phénylbenzophénone-2-carboxylate, la 2-hydroxy-4-n-octyloxybenzophénone, la 4-hydroxy-3-carboxybenzophénone ; le 3-(4'-méthylbenzylidène)-d,l-camphre, le 3-(benzylidène)-d,l-camphre, le benzalkonium méthosulfate camphre ; l'acide urocanique,l'urocanate d'éthyle ; la famille des dérivés de l’acide sulfonique comme l’acide sulfonique2-phénylbenzimidazole-5 et ses sels ; la famille des dérivés de la triazine commel’hydroxyphényl triazine, l’éthylhexyloxyhydroxyphényl-4-méthoxyphényltriazine, le 2,4,6-trianillino-(p-carbo-2’-éthylhexyl-1’-oxy)-1,3,5-triazine, le 4,4-((6-(((1,1 -diméthyléthyl)amino)carbonyl)phenyl)amino)-1,3,5-triazine-2,4-diyl diimino) bis-(2-éthylhexyl) ester del’acide benzoïque, le 2-phényl-5-méthylbenzoxazole, le 2,2'-hydroxy-5-méthylphénylbenzotriazole, le 2-(2'-hydroxy-5'-t-octylphényl)benzotriazole, le 2-(2'-hydroxy-5'-méthyphényl)benzotriazole; la dibenzazine; le dianisoylméthane, le 4-méthoxy-4"-t-butylbenzoylméthane ; la 5-(3,3-diméthyl-2-norbornylidène)-3-pentan-2-one ; la familledes dérivés du diphénylacrylate comme le 2-éthylhexyl-2-cyano-3,3-diphényl-2-propènoate, l’éthyl-2-cyano-3,3-diphényl-2-propènoate ; la famille des polysiloxanescomme le malonate de benzylidène siloxane.As examples of sunscreens that can be combined with the compound of formula (I) or with the composition (C1), mention may be made of all those appearing in the cosmetic directive76 / 768 / EEC modified as appendix VII. Among the solar organic filters which may be associated with the compound of formula (I) or with the composition (C1), mention may be made of the family of derivatives of benzoic acid such as para-aminobenzoic acids (PABA), in particular the esters of monoglycerol of PABA, the ethyl esters of N, N-propoxyPABA, the ethyl esters of Ν, Ν-diethoxy PABA, the ethyl esters of Ν, Ν-dimethylPABA, the methyl esters of Ν, Ν-dimethyl PABA, the butyl esters of Ν, Ν-dimethyl PABA; the family of anthranilic acid derivatives such as homomenthyl-N-acetyl anthranilate; the family of salicylic acid derivatives such as amyl salicylate, homomenthyl salicylate, ethylhexyl salicylate, phenyl salicylate, benzyl salicylate, p-isopropanolphenyl salicylate; the family of cinnamic acid derivatives such as ethylhexyl cinnamate, ethyl-4-isopropyl cinnamate, methyl-2,5-diisopropyl cinnamate, p-methoxypropyl cinnamate, p-methoxyisopropyl cinnamate, p-methoxyisoamyl cinnamate, p-methoxyoctyl cinnamate (p-methoxy 2-ethylhexyl cinnamate), p-methoxy 2-ethoxyethyl cinnamate, p-methoxycyclohexyl cinnamate, ethyl-a-cyano cinnamate -β-phenyl, 2-ethylhexyl-1-cyano-p-phenyl cinnamate, glycidyl mono-2-ethylhexanoyl diiparamethoxy cinnamate; the family of benzophenone derivatives such as 2,4-dihydroxybenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2 ', 4,4'-tetrahydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2 4-hydroxy-4-methoxy-4'-methylbenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonate, 4-phenylbenzophenone, 2-ethylhexyl-4'-phenylbenzophenone-2-carboxylate, 2-hydroxy-4 n-octyloxybenzophenone, 4-hydroxy-3-carboxybenzophenone; 3- (4'-methylbenzylidene) -d, 1-camphor, 3- (benzylidene) -d, 1-camphor, benzalkonium methosulfate camphor; urocanic acid, ethyl urocanate; the family of sulfonic acid derivatives such as sulfonic acid-2-phenylbenzimidazole-5 and its salts; the family of triazine derivatives such as hydroxyphenyl triazine, ethylhexyloxyhydroxyphenyl-4-methoxyphenyltriazine, 2,4,6-trianillino- (p-carbo-2'-ethylhexyl-1'-oxy) -1,3,5 triazine, 4,4 - ((6 - (((1,1-dimethylethyl) amino) carbonyl) phenyl) amino) -1,3,5-triazine-2,4-diyl diimino) bis- (2- ethylhexyl) benzoic acid ester, 2-phenyl-5-methylbenzoxazole, 2,2'-hydroxy-5-methylphenylbenzotriazole, 2- (2'-hydroxy-5'-t-octylphenyl) benzotriazole, 2- (2'-hydroxy-5'-methylphenyl) benzotriazole; dibenzazine; dianisoylmethane, 4-methoxy-4'-tert-butylbenzoylmethane, 5- (3,3-dimethyl-2-norbornylidene) -3-pentan-2-one, the family of diphenylacrylate derivatives such as 2-ethylhexyl-2 -cyano-3,3-diphenyl-2-propenoate, ethyl-2-cyano-3,3-diphenyl-2-propenoate, the family of polysiloxanes such as benzylidene malonate siloxane.
Parmi les filtres inorganiques solaires, également appelés "écrans minéraux", quel’on peut associer au composé de formule (I) ou à la composition (C1), on peut citer lesoxydes de titane, les oxydes de zinc, l’oxyde de cérium, l’oxyde de zirconium, les oxydesde fer jaune, rouge ou noir, les oxydes de chrome. Ces écrans minéraux peuvent êtremicronisés ou non, avoir subi ou non des traitements de surface et être éventuellementprésentés sous formes de pré-dispersions aqueuses ou huileuses. L'invention a aussi pour objet un composé de formule (I) ou une composition (C1)tels que définis précédemment, pour son utilisation comme médicament à activitééclaircissante de la peau humaine.Among the inorganic solar filters, also called "inorganic screens", which can be associated with the compound of formula (I) or with the composition (C1), mention may be made of titanium oxides, zinc oxides, cerium oxide , zirconium oxide, iron oxides yellow, red or black, chromium oxides. These inorganic screens can be micronized or not, have undergone or not surface treatments and may bepresented in the form of aqueous or oily pre-dispersions. The subject of the invention is also a compound of formula (I) or a composition (C1) as defined above, for its use as a skin-brightening drug of human skin.
Les exemples suivants illustrent l'invention sans toutefois la limiter.The following examples illustrate the invention without limiting it.
Exemple 1 : préparation d’une composition (C1A) selon l’invention comprenant lescomposés de formules (la) et (lb).EXAMPLE 1 Preparation of a Composition (C1A) According to the Invention Comprising Compounds of Formulas (Ia) and (Ib)
On introduit 500 grammes de phénylalanine soit un équivalent molaire dans unmélange hydro-alcoolique constitué de 1800 grammes d’eau et de 200 grammesd’isopropanol à une température de 20°C. Le pH du milieu est ajusté à 10 par ajout d’unesolution de soude à 30%. 393,8 grammes de chlorure d’octanoyle soit 0,8 équivalentmolaire sont ensuite ajoutés progressivement sur le milieu maintenu entre 20°C et 40 ; età un pH 10 et 10,5.500 grams of phenylalanine is introduced, one molar equivalent in a hydro-alcoholic mixture consisting of 1800 grams of water and 200 grams of isopropanol at a temperature of 20 ° C. The pH of the medium is adjusted to 10 by adding 30% sodium hydroxide solution. 393.8 grams of octanoyl chloride or 0.8 mol equivalents are then gradually added to the medium maintained between 20 ° C and 40; and at pH 10 and 10.5.
Le milieu réactionnel est ensuite maintenu sous agitation pendant deux heures puischauffé jusqu’à atteindre 70°C puis additionné de 413,5 grammes d’une solution d’acidephosphorique à 75% pour atteindre progressivement une valeur de pH du milieuréactionnel d’environ 2,0. La phase aqueuse du est milieu décantée et soutirée et la phaseorganique restant dans le réacteur est ensuite lavée plusieurs fois à la saumure à 5% àtempérature ambiante sous agitation. A l’issue puis du séchage par distillation sous videde l’eau résiduelle, on obtient la phase organique comprenant 641,5 g de N-OctanoylPhénylalanine souhaitée.The reaction medium is then stirred for two hours and then heated to 70 ° C., then 413.5 grams of a 75% strength phosphoric acid solution are added to gradually reach a pH value of about 2%. 0. The aqueous phase of the medium is decanted and withdrawn and the organic phase remaining in the reactor is then washed several times with brine at 5% at room temperature with stirring. At the end and then drying by distillation under water, the organic phase comprising 641.5 g of N-octanoyl-phenylalanine desired.
Une quantité de 42,9 grammes de glycérol soit un équivalent molaire de glycérolest introduite dans le réacteur comprenant 135 grammes du milieu réactionnel séché,obtenu à l’étape précédente dans lequel se trouve 0,8 équivalent molaire de N-octanoylphényl alanine. La température est portée à 120°C, 0,38 grammes d’acide sulfurique à98% et 0,39 g d’acide hypophosphoreux à 50% sont ensuite ajoutés au mélange et lemélange résultant est porté à une température de 125°C, sous un vide partiel avec unbarbotage d’azote. Le mélange réactionnel est ensuite maintenu pendant 11 heures sousagitation et à cette température, puis neutralisé par ajout d’une solution de soude à 30%de façon à obtenir un pH de la Composition (C1A), diluée à 5% dans l’eau, compris entre3,0 et 6,0.An amount of 42.9 grams of glycerol is a molar equivalent of glycerol is introduced into the reactor comprising 135 grams of the dried reaction medium, obtained in the previous step in which there is 0.8 molar equivalent of N-octanoylphenyl alanine. The temperature is raised to 120 ° C., 0.38 grams of 98% sulfuric acid and 0.39 grams of 50% hypophosphorous acid are then added to the mixture and the resulting mixture is heated to a temperature of 125 ° C. a partial vacuum with nitrogen bubbling. The reaction mixture is then maintained for 11 hours under stirring and at this temperature, then neutralized by addition of a 30% sodium hydroxide solution so as to obtain a pH of the Composition (C1A), diluted to 5% in water, between 3.0 and 6.0.
Les caractéristiques analytiques de la composition (C1A) obtenue sont lessuivantes :The analytical characteristics of the composition (C1A) obtained are the following:
Indice acide (selon NFT 60-204) = 12,2pH 5% de la composition (C1A) dans l’eau (selon la méthode NFT 73-206) = 4,7Indice d’Hydroxyle (selon U.S. Pharmacopeia XXI NF XVI 01/011985) = 322,0Indice d’ester (calculé par la différence entre l’indice de saponification mesuré selon laméthode NFT 60-110 et l’indice d’acide mesuré selon la méthode NFT 60-204) = 147,7Indice de saponification (selon NFT 60-206) = 159,9 mg KOH/gAcid value (according to NFT 60-204) = 12.2 μH 5% of the composition (C1A) in water (according to the method NFT 73-206) = 4.7 Hydroxyl value (according to US Pharmacopeia XXI NF XVI 01 / 011985) = 322.0 Ester number (calculated as the difference between the saponification number measured according to the method NFT 60-110 and the acid number measured according to the method NFT 60-204) = 147.7 saponification index ( according to NFT 60-206) = 159.9 mg KOH / g
Exemple 2 : préparation d’une composition (C1B) selon l’invention comprenant lescomposés de formules (la) et (lb).Example 2 Preparation of a Composition (C1B) According to the Invention Comprising Compounds of Formulas (Ia) and (Ib)
On procède comme à l’exemple 1 en remplaçant le 0,8 équivalent molaire dechlorure d’octanoyle par 0,8 équivalent (542,3 grammes) de chlorure de cocoylecomprenant pour 100% de sa masse 8% massique de chlorure d’octanoyle, 8% massiquede chlorure de décanoyle, 50% massique de chlorure de lauroyle, 17% massique dechlorure de myristoyle, 8% massique de chlorure de palmitoyle, 3% massique de chlorurede stéaroyle, 4% massique de chlorure d’oléoyle (9-octadécènoyle) et 2% massique dechlorure de linoléoyle (octadéca-9,12-diènoyle).The procedure is as in Example 1, replacing the 0.8 molar equivalent of octanoyl chloride with 0.8 equivalents (542.3 grams) of cocoyl chloride, which comprises 100% of its weight of 8% by weight of octanoyl chloride. 8% by weight of decanoyl chloride, 50% by weight of lauroyl chloride, 17% by weight of myristoyl chloride, 8% by weight of palmitoyl chloride, 3% by weight of stearoyl chloride, 4% by weight of oleoyl chloride (9-octadecenoyl) and 2% by weight of linoleoyl chloride (octadeca-9,12-dienoyl).
Les caractéristiques analytiques de la composition (C1B) sont les suivantes :Indice acide (selon NFT 60-204) = 10,1pH 5% de la composition (C1B) dans l’eau (selon la méthode NFT 73-206) = 5,7Indice d’Hydroxyle (selon U.S. Pharmacopeia XXI NFXVI 01/011985) = 269,0Indice d’ester (calculé par la différence entre l’indice de saponification mesuré selon laméthode NFT 60-110 et l’indice d’acide mesuré selon la méthode NFT 60-204) = 125,3Indice de saponification (selon NFT 60-206) = 135,4 mg KOH/gThe analytical characteristics of the composition (C1B) are as follows: acid number (according to NFT 60-204) = 10.1 phr 5% of the composition (C1B) in water (according to the method NFT 73-206) = 5, 7Hydroxyl Index (US Pharmacopeia XXI NFXVI 01/011985) = 269.0 Ester Index (calculated as the difference between the saponification number measured according to NFT method 60-110 and the acid number measured according to the method NFT 60-204) = 125.3Saponification index (according to NFT 60-206) = 135.4 mg KOH / g
Exemple 3 : préparation d’une composition (D) comparative comprenant lesproduits de la réaction d’estérification du N-hexadécanoyl phénylalanine et duglycérol.Example 3: Preparation of a comparative composition (D) comprising the products of the esterification reaction of N-hexadecanoyl phenylalanine and glycerol.
On procède comme à l’exemple 1 en remplaçant le 0,8 équivalent molaire dechlorure d’octanoyle par 0,8 équivalent de chlorure d’hexadécanoyle pour obtenir laComposition D dont les caractéristiques analytiques sont les suivantes :The procedure is as in Example 1, replacing the 0.8 molar equivalent of octanoyl chloride with 0.8 equivalent of hexadecanoyl chloride to obtain the Composition D, the analytical characteristics of which are as follows:
Indice acide (selon NFT 60-204) = 12,4 pH 5% de la composition D dans l’eau (selon la méthode NFT 73-206) = 6,0Acid value (according to NFT 60-204) = 12.4 pH 5% of composition D in water (according to the NFT 73-206 method) = 6.0
Indice d’Hydroxyle (selon U.S. Pharmacopeia XXI NF XVI 01/011985) = 230,1Hydroxyl number (according to U.S. Pharmacopeia XXI NF XVI 01/011985) = 230.1
Indice d’ester (calculé par la différence entre l’indice de saponification mesuréselon la méthode NFT 60-110 et l’indice d’acide mesuré selon la méthode NFT 60-204) =112,9Ester number (calculated as the difference between the saponification number measured by the NFT method 60-110 and the acid number measured by the NFT 60-204 method) = 112.9
Indice de saponification (selon NFT 60-206) = 125,3 mg KOH/gSaponification number (according to NFT 60-206) = 125.3 mg KOH / g
Exemple 4 : préparation d’une composition (E) comparative comprenant lesproduits de la réaction d’estérification du N-undécylènoyl phénylalanine et duglycérol.Example 4: Preparation of a Comparative Composition (E) Comprising the Products of the Esterification Reaction of N-Undecylenoyl Phenylalanine and Glycerol
On introduit 780g de N-undécylènoyl phénylalanine, soit un équivalent molaire,dans un réacteur en verre à double enveloppe, dans laquelle circule un fluide caloporteur,muni d’une agitation efficace et d’un dispositif de barbotage d’azote par le fond duréacteur, à 125°C pour permettre la fonte totale du N-undécylènoyl phénylalanine. Onintroduit par la suite 218g de glycérol, soit un équivalent molaire, sur le N-undécylènoylphénylalanine à une température d’environ 120°C. Le mélange ainsi préparé est maintenuà 120°C pendant 30 minutes, puis aditionné de 2,2g d’acide hypophosphoreux à 50% et2,2g d’acide sulfurique à 98% et placé sous un vide partiel à 120°C et laissé pendant 20heures avec évacuation de l'eau formée. Le milieu réactionnel est ensuite vidangé et l’obtient la composition (E) attendue, dont les caractéristiques analytiques sont les suivantes :Aspect à 20°C : liquide trouble780 g of N-undecylenoyl phenylalanine, ie a molar equivalent, are introduced into a jacketed glass reactor, in which a heat transfer fluid is circulated, provided with efficient stirring, and a device for bubbling nitrogen through the reactor medium. at 125 ° C to allow the total melting of N-undecylenoyl phenylalanine. Subsequently, 218 g of glycerol, ie one molar equivalent, is introduced into N-undecylenoylphenylalanine at a temperature of about 120 ° C. The mixture thus prepared is maintained at 120 ° C. for 30 minutes, then supplemented with 2.2 g of 50% hypophosphorous acid and 2.2 g of 98% sulfuric acid and placed under a partial vacuum at 120 ° C. and left for 20 hours. with evacuation of the formed water. The reaction medium is then drained and obtains the composition (E) expected, whose analytical characteristics are as follows: Appearance at 20 ° C: cloudy liquid
Indice d’acide (selon NFT 60-204) = 15,3mg KOH/gAcid value (according to NFT 60-204) = 15.3 mg KOH / g
Indice d’Hydroxyle (selon U.S. Pharmacopeia XXI NF XVI 01/011985) = 278,3mg KOH/gIndice de saponification (selon NFT 60-206) = 147,2 mg KOH/gHydroxyl number (according to U.S. Pharmacopeia XXI NF XVI 01/011985) = 278.3 mg KOH / gSaponification index (according to NFT 60-206) = 147.2 mg KOH / g
Indice d’iode (selon NFT 60-203) = 64g l2/100 gIodine value (according to NFT 60-203) = 64g l2 / 100 g
Etude de l'activité éclaircissante de la composition (C1) dans des cultures demélanocytes B16/F1Study of the lightening activity of the composition (C1) in B16 / F1 demanocyte cultures
La mise en évidence de l’activité éclaircissante a été réalisée par la mise en œuvred’un modèle d’étude de la production de la mélanine sur une lignée de mélanocytesmurins B16/F1. Ce test est couramment utilisé dans le secteur de la cosmétique etpharmaceutique.Demonstration of the lightening activity was achieved by the implementation of a study model of the production of melanin on a line of melanocytesmurins B16 / F1. This test is commonly used in the field of cosmetics and pharmaceuticals.
Les mélanocytes murins de la lignée B16/F1 cultivés en monocouches, sontensemencés dans des plaques de culture de 96 puits à la densité de 5000 cellules/puits.Les cellules sont cultivées dans un milieu de culture (milieu MCM) à 37°C, dans uneatmosphère humide contenant 5% de CO2. Le milieu MCM a la composition suivante :Milieu DMEM (Dulbecco's Modified Eagle's Medium) contenant 4,5 g/l de glucoseadditionné de L-Glutamine (2 mM), de pénicilline (50 Ul / ml), de streptomycine (50 pg /ml) et de sérum de veau fœtal (10% v/v). Les produits objets de l’étude sont testés à 10 pg/ ml (0,001%) et à 50pg/ml (0,005%) dans le milieu MCM. Les cultures de mélanocytessont incubées en présence du produit à l’essai ou des produits de référence pendant 72heures à 37°C, dans une atmosphère humide contenant 5% de CO2. Des cultures témoinssont incubées, en absence de produit, dans le milieu MCM. Ces cultures témoins sont réalisées sur chaque plaque de culture. Chaque essai est réalisé trois fois (triplicate, n =3).The murine melanocytes of the B16 / F1 line grown in monolayers are seeded in 96-well culture plates at the density of 5000 cells / well. The cells are cultured in a culture medium (MCM medium) at 37 ° C., in a humid atmosphere containing 5% CO2. The MCM medium has the following composition: Medium DMEM (Dulbecco's Modified Eagle's Medium) containing 4.5 g / l of glucosadditioned L-Glutamine (2 mM), penicillin (50 IU / ml), streptomycin (50 μg / ml) ) and fetal calf serum (10% v / v). The products under study are tested at 10 μg / ml (0.001%) and at 50 μg / ml (0.005%) in MCM medium. The melanocyte cultures are incubated in the presence of the test product or reference products for 72 hours at 37 ° C in a humid atmosphere containing 5% CO 2. Control cultures are incubated, in the absence of product, in the MCM medium. These control cultures are carried out on each culture plate. Each test is performed three times (triplicate, n = 3).
Evaluation des effets :Effects evaluation:
Après 72 heures d’incubation, les milieux d’incubation des cellules (n = 3) sontprélevés et stockés à - 80°C jusqu’au moment de l’évaluation des effets. Les tapiscellulaires sont lysés dans une solution de PBS (Phosphate Buffered Saline) à l’aide d’unetige de sonication et la mélanine intracellulaire est évaluée en parallèle de la quantité deprotéines. La mélanine (extracellulaire et intracellulaire) est quantifiée parspectrophotométrie à 450 nm. Une gamme d'étalonnage de mélanine est réalisée enparallèle. Les protéines sont quantifiées à l’aide d’un kit BCA (Bicinchoninic Acid Assay) etexprimées en mg/mL. Les résultats de mélanine sont exprimés en pg/ml pour la mélanineextracellulaire et en pg/mg de protéines pour la mélanine intracellulaire. Une analysestatistique à l’aide du test de Student a été effectuée afin de comparer chacune desconditions à la condition témoin.After 72 hours of incubation, cell incubation media (n = 3) are harvested and stored at -80 ° C until the effects are evaluated. The tapiscellulars are lysed in a solution of PBS (Phosphate Buffered Saline) using a sonic seal and intracellular melanin is evaluated in parallel with the amount of proteins. Melanin (extracellular and intracellular) is quantified by spectrophotometry at 450 nm. A melanin calibration range is made in parallel. The proteins are quantified using a BCA kit (Bicinchoninic Acid Assay) and expressed in mg / mL. The melanin results are expressed in μg / ml for melanintracellular and in μg / mg protein for intracellular melanin. A statistical analysis using the Student's test was performed to compare each condition with the control condition.
Les résultats obtenus sont consignés dans le Tableau 1 ci-dessous :The results obtained are shown in Table 1 below:
Tableau 1: évaluation de l’inhibition de la production de la mélanine extracellulaire descomposés selon l’invention et des composés de l’état de la technique.Table 1: evaluation of the inhibition of the production of extracellular melanin compounds according to the invention and compounds of the state of the art.
Les résultats indiqués dans le Tableau 1 mettent en évidence une plus forteinhibition de la production de la mélanine extracellulaire pour la composition (C1A),comprenant les produits de la réaction d’estérification entre le glycérol et le N-octanoylphényl alanine, et de la composition (C1B), comprenant les produits de la réactiond’estérification entre le glycérol et le N-cocoyl phényl alanine, comparativement auxThe results indicated in Table 1 show a stronger inhibition of the production of extracellular melanin for the composition (C1A), comprising the products of the esterification reaction between glycerol and N-octanoylphenyl alanine, and of the composition. (C1B), comprising the products of the esterification reaction between glycerol and N-cocoyl phenyl alanine, compared with
compositions (D) et (E), comprenant respectivement des esters de glycérol et de N-hexadécanoyl phényl alanine et des esters de glycérol et de N-undécylènoyl phénylalanine. Il est à noter que la composition (E), qui ne se différencie des compositions (C1A)et (C1B) selon l’invention que par la longueur de la chaîne du groupement N-acyle (16atomes de carbone), montre une performance d’inhibition de la production de la mélanineextracellulaire plus faible que la composition (E) de l’état de la technique, à base d’esterde glycérol et N-undécylénoyl phénylalanine, décrite dans la publication internationale WO2010/034917.compositions (D) and (E), comprising respectively glycerol and N-hexadecanoyl phenylalanine esters and esters of glycerol and N-undecylenoyl phenylalanine. It should be noted that the composition (E), which is different from the compositions (C1A) and (C1B) according to the invention that the length of the chain of the N-acyl group (16atoms of carbon), shows a performance d inhibition of the production of melanintracellular lower than the composition (E) of the state of the art, based on glycerol ester and N-undecylenoyl phenylalanine, described in the international publication WO2010 / 034917.
Exemples de formulations cosmétiquesExamples of cosmetic formulations
Dans les exemples suivants les proportions sont exprimées en pourcentagespondéraux.In the following examples the proportions are expressed in percentagesponderal.
Exemple 5 : Emulsion-Soin éclaircissant pour peau mature MONTANOV™ 202 02,00% MONTANOV™ 68 02,00%EXAMPLE 5 Emulsion-Lightening Care for Mature Skin MONTANOV ™ 202 02.00% MONTANOV ™ 68 02.00%
Caprylic capric triglycérides 10,00%Caprylic Capric Triglycerides 10.00%
Squalane 10,00%Squalane 10.00%
Eau QSP 100%Water QSP 100%
Composition (A) 01,00% SEPIGEL™ 305 00,70%Composition (A) 01.00% SEPIGEL ™ 305 00.70%
Magnésium ascorbyl phosphate 02,00% SEPICIDE™ HB 00,30% SEPICIDE™ Cl 00,20%Magnesium Ascorbyl Phosphate 02.00% SEPICIDE ™ HB 00.30% SEPICIDE ™ Cl 00.20%
Parfum 0,50%Perfume 0,50%
Exemple 6 : Emulsion-Soin raffermissant éclaircissant MONTANOV™ 202 03, 00%EXAMPLE 6 Emulsion-Lightening Firming Treatment MONTANOV ™ 202 03, 00%
Soude à 24% qs pHSoda at 24% qs pH
Ethyl hexyl méthoxycinnamate 06,00% LANOL™1688 08,00%Ethyl hexyl methoxycinnamate 06.00% LANOL ™ 1688 08.00%
Benzophénone-3 04,00%Benzophenone-3 04.00%
Eau QSP 100%Water QSP 100%
Composition (A) 02,00% SIMULGEL™ NS 00,50% SEPILIFT™ DPHP 00,50%Composition (A) 02.00% SIMULGEL ™ NS 00.50% SEPILIFT ™ DPHP 00.50%
Diméthicone 02,00%Dimethicone 02.00%
Cyclométhicone 02,00%Cyclomethicone 02.00%
Arbutine 0.3% SEPICIDE™ HB 00,30% SEPICIDE™ Cl 00,20%Arbutin 0.3% SEPICIDE ™ HB 00.30% SEPICIDE ™ Cl 00.20%
Parfum 00,10%Perfume 00.10%
Exemple 7 : Gel-crème éclaircissant aux alpha-hydroxyacidesExample 7 Gel-cream lightening with alpha-hydroxyacids
Hydroxyéthylcellulose 0,80%Hydroxyethylcellulose 0.80%
Ethylhexyl octanoate 05,00%Ethylhexyl octanoate 05.00%
Sodium lactate à 60% 14,00%Sodium lactate 60% 14.00%
Eau QSP 100%Water QSP 100%
Composition (B) 03,00% SEPIGEL™ 305 04,20% SEPICIDE™ HB 02,00% SEPICIDE™ Cl 03,00%Composition (B) 03.00% SEPIGEL ™ 305 04.20% SEPICIDE ™ HB 02.00% SEPICIDE ™ Cl 03.00%
Parfum 00,10%Perfume 00.10%
Exemple 8 : Emulsion- Soin éclaircissant MONTANOV™ L 01,00%Example 8: Emulsion - Lightening care MONTANOV ™ L 01.00%
Cetyl alcool 02,00%Cetyl alcohol 02.00%
Isodecyl neopentanoate 12,00%Isodecyl neopentanoate 12.00%
Cetearyl octanoate 10,00%Cetearyl octanoate 10.00%
Glycérine 03,00%Glycerin 03.00%
Eau QSP 100%Water QSP 100%
Composition (A) 01,00% SIMULGEL™ EG 02,00%Composition (A) 01.00% SIMULGEL ™ EG 02.00%
Acide kojique 01,00% SEPICIDE™ HB 00,30% SEPICIDE™ Cl 00,20%Kojic Acid 01.00% SEPICIDE ™ HB 00.30% SEPICIDE ™ Cl 00.20%
Parfum 00,10%Perfume 00.10%
Exemple 9 : Lotion éclaircissante ORAMIX™ CG110 05,00% KATHON™ CG 00,08%Example 9: Lightening Lotion ORAMIX ™ CG110 05.00% KATHON ™ CG 00.08%
Eau QSP 100%Water QSP 100%
Composition (A) 01,00%Composition (A) 01.00%
Parfum 00,10%Perfume 00.10%
Cette lotion peut être vendue en flacons ou imprégnée sur des lingettes.This lotion can be sold in bottles or impregnated on wipes.
Les définitions des produits commerciaux utilisés dans les exemples sont lessuivantes : SEPILIFT™ DPHP : (Dénomination INCI : Dipalmitoyl hydroxyproline), commercialisé parla société SEPPIC ; SEPICIDE™ Cl : Imidazoline urée, (agent conservateur) commercialisé par la sociétéSEPPIC ; SEPICIDE™ HB : Mélange de phénoxyéthanol, de méthylparaben, d'éthylparaben, depropyl-paraben et de butylparaben, (agent conservateur) commercialisé par la sociétéSEPPIC ; KATHON™ CG (Dénomination INCI : méthyl isothiazolinone / Méthylchloroisothiazolinone) ; SIMULGEL™ EG : Latex inverse auto-inversible de copolymère tel que ceux décrits dansla publication internationale WO 99/36445 (dénomination INCI : Sodium acrylate/Sodiumacryloyldimethyl taurate copolymer et Isohexadecane et Polysorbate 80) commercialisépar la société SEPPIC ; SIMULGEL™ NS : Latex inverse auto-inversible de copolymère tel que ceux décrits dansla publication internationale WO 99/36445 (dénomination INCIhydroxyethylacrylate/Sodium acryloyldimethyl taurate copolymer et squalane etPolysorbate 60) commercialisé par la société SEPPIC ; SEPIGEL™ 305 : Latex inverse auto-inversible (dénomination INCI : Polacrylamide / C13-14 Isoparaffin / Laureth-7) ; LANOL™ 1688 : Ethylhexanoate de cétéaryle commercialisé par la société SEPPIC ;MONTANOV™ L : Agent émulsionnant à base d'alcool en C14-C22 et d’alkylpolyglucoside en C12-C20 tel que ceux décrits dans la demande de brevet européen EP 0995 487 ; MONTANOV™ 202 est un agent émulsionnant à base d'alcool arachidylique d’alcoolbéhènylique et d’arachidyl polyglucoside. LANOL™ 1688 est du cétéaryl ethylhexanoatel commercialisé par la société SEPPIC. MONTANOV™ 68 est un agent émulsionnant à base d'alcool cétéarylique et cétéarylpolyglucoside ORAMIX™ CG110 est un agent moussant à base d’octyl polyglucosides et de décylpolyglucosides.The definitions of the commercial products used in the examples are the following: SEPILIFT ™ DPHP: (INCI name: Dipalmitoyl hydroxyproline), sold by the company SEPPIC; SEPICIDE ™ Cl: imidazoline urea (preservative) sold by the company ESPIC; SEPICIDE ™ HB: Mixture of phenoxyethanol, methylparaben, ethylparaben, propyl paraben and butylparaben (preservative) sold by the company ESPIC; KATHON ™ CG (INCI name: methyl isothiazolinone / methylchloroisothiazolinone); SIMULGEL ™ EG: self-invertible inverse copolymer latex such as those described in the international publication WO 99/36445 (INCI name: Sodium acrylate / Sodiumacryloyldimethyl taurate copolymer and Isohexadecane and Polysorbate 80) marketed by the company SEPPIC; SIMULGEL ™ NS: self-invertible inverse copolymer latex such as those described in the international publication WO 99/36445 (INCIhydroxyethylacrylate / Sodium acryloyldimethyltaurate copolymer and squalane and Polysorbate 60) marketed by the company SEPPIC; SEPIGEL ™ 305: Self-Invertible Inverse Latex (INCI Name: Polacrylamide / C13-14 Isoparaffin / Laureth-7); LANOL ™ 1688: cetearyl ethylhexanoate marketed by the company SEPPIC, MONTANOV ™ L: emulsifying agent based on C14-C22 alcohol and C12-C20 alkylpolyglucoside such as those described in the European patent application EP 0995 487; MONTANOV ™ 202 is an emulsifier based on arachidyl alcohol of alkenyl alcohol and arachidyl polyglucoside. Lanol ™ 1688 is cetearyl ethylhexanoatel marketed by the company SEPPIC. MONTANOV ™ 68 is an emulsifier based on cetearyl alcohol and cetearyl polyglucoside. ORAMIX ™ CG110 is a foaming agent based on octyl polyglucosides and decylpolyglucosides.
Bibliographie : (1) Karleskind A., 1992. Manuel des corps gras, Lavoisier, Vol. 1 et 2 : 65-78, 115-241,1072-1089, 1433-1459.Bibliography: (1) Karleskind A., 1992. Manual of fatty substances, Lavoisier, Vol. 1 and 2: 65-78, 115-241, 1072-1089, 1433-1459.
Claims (5)
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FR2835252B1 (en) * | 2002-01-25 | 2005-08-05 | Seppic Sa | USE OF A PROTEIN KINASE A INACTIFYING COMPOUND IN A COMPOSITION CONTAINING A COSMETICALLY ACCEPTABLE MEDIUM FOR LAMINATING THE SKIN |
FR2936152B1 (en) * | 2008-09-24 | 2010-11-12 | Seppic Sa | MONOGLYCERIDE OF N-UNDECYLENOYL PHENYLALANINE, PROCESS FOR THE PREPARATION AND USE OF GLYCERIC ESTERS OF N-UNDECYLENOYL PHENYLALANINE AS A SKINLIGHTENING AGENT |
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