JP7200211B2 - 皮膚、毛髪、爪および/または粘膜の処置および/またはケアに有用な化合物 - Google Patents
皮膚、毛髪、爪および/または粘膜の処置および/またはケアに有用な化合物 Download PDFInfo
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- JP7200211B2 JP7200211B2 JP2020500058A JP2020500058A JP7200211B2 JP 7200211 B2 JP7200211 B2 JP 7200211B2 JP 2020500058 A JP2020500058 A JP 2020500058A JP 2020500058 A JP2020500058 A JP 2020500058A JP 7200211 B2 JP7200211 B2 JP 7200211B2
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- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 229940068065 phytosterols Drugs 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- SRJOCJYGOFTFLH-UHFFFAOYSA-M piperidine-4-carboxylate Chemical compound [O-]C(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-M 0.000 description 1
- XIPFMBOWZXULIA-UHFFFAOYSA-N pivalamide Chemical compound CC(C)(C)C(N)=O XIPFMBOWZXULIA-UHFFFAOYSA-N 0.000 description 1
- 229940116828 plantago ovata seed extract Drugs 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920002189 poly(glycerol 1-O-monomethacrylate) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229940061570 polyglyceryl-10 stearate Drugs 0.000 description 1
- 229940048845 polyglyceryl-3 diisostearate Drugs 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068977 polysorbate 20 Drugs 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229940068988 potassium aspartate Drugs 0.000 description 1
- 239000001508 potassium citrate Substances 0.000 description 1
- 229960002635 potassium citrate Drugs 0.000 description 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 235000011082 potassium citrates Nutrition 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- XEIOPEQGDSYOIH-MURFETPASA-N propan-2-yl (9z,12z)-octadeca-9,12-dienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC(C)C XEIOPEQGDSYOIH-MURFETPASA-N 0.000 description 1
- NEOZOXKVMDBOSG-UHFFFAOYSA-N propan-2-yl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OC(C)C NEOZOXKVMDBOSG-UHFFFAOYSA-N 0.000 description 1
- ZPWFUIUNWDIYCJ-UHFFFAOYSA-N propan-2-yl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)C ZPWFUIUNWDIYCJ-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 230000002633 protecting effect Effects 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- 108010071967 protein K Proteins 0.000 description 1
- 230000007065 protein hydrolysis Effects 0.000 description 1
- 229940059546 prunus persica flower extract Drugs 0.000 description 1
- 235000019423 pullulan Nutrition 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ZUFQODAHGAHPFQ-UHFFFAOYSA-N pyridoxine hydrochloride Chemical compound Cl.CC1=NC=C(CO)C(CO)=C1O ZUFQODAHGAHPFQ-UHFFFAOYSA-N 0.000 description 1
- 229960004172 pyridoxine hydrochloride Drugs 0.000 description 1
- 235000019171 pyridoxine hydrochloride Nutrition 0.000 description 1
- 239000011764 pyridoxine hydrochloride Substances 0.000 description 1
- GHBFNMLVSPCDGN-UHFFFAOYSA-N rac-1-monooctanoylglycerol Chemical compound CCCCCCCC(=O)OCC(O)CO GHBFNMLVSPCDGN-UHFFFAOYSA-N 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229940108325 retinyl palmitate Drugs 0.000 description 1
- 235000019172 retinyl palmitate Nutrition 0.000 description 1
- 239000011769 retinyl palmitate Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 201000004700 rosacea Diseases 0.000 description 1
- 235000020748 rosemary extract Nutrition 0.000 description 1
- 235000015639 rosmarinus officinalis Nutrition 0.000 description 1
- 229940109850 royal jelly Drugs 0.000 description 1
- 150000003870 salicylic acids Chemical class 0.000 description 1
- 230000037390 scarring Effects 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 229940082941 sedum roseum root extract Drugs 0.000 description 1
- 230000037307 sensitive skin Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229940089952 silanetriol Drugs 0.000 description 1
- 230000037380 skin damage Effects 0.000 description 1
- 230000036559 skin health Effects 0.000 description 1
- 230000008491 skin homeostasis Effects 0.000 description 1
- 244000005714 skin microbiome Species 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 230000008566 social perception Effects 0.000 description 1
- 229940047670 sodium acrylate Drugs 0.000 description 1
- 229940083608 sodium hydroxide Drugs 0.000 description 1
- ODFAPIRLUPAQCQ-UHFFFAOYSA-M sodium stearoyl lactylate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC(=O)OC(C)C(=O)OC(C)C([O-])=O ODFAPIRLUPAQCQ-UHFFFAOYSA-M 0.000 description 1
- 229940080352 sodium stearoyl lactylate Drugs 0.000 description 1
- 235000010956 sodium stearoyl-2-lactylate Nutrition 0.000 description 1
- KNYAZNABVSEZDS-UHFFFAOYSA-M sodium;2-octadecanoyloxypropanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC(=O)OC(C)C([O-])=O KNYAZNABVSEZDS-UHFFFAOYSA-M 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- KZQSXALQTHVPDQ-UHFFFAOYSA-M sodium;butanedioate;hydron Chemical compound [Na+].OC(=O)CCC([O-])=O KZQSXALQTHVPDQ-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000002047 solid lipid nanoparticle Substances 0.000 description 1
- 229950006451 sorbitan laurate Drugs 0.000 description 1
- 235000011067 sorbitan monolaureate Nutrition 0.000 description 1
- 229950004959 sorbitan oleate Drugs 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 150000003408 sphingolipids Chemical class 0.000 description 1
- WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 description 1
- 150000003410 sphingosines Chemical class 0.000 description 1
- 229940032094 squalane Drugs 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
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 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
- 210000000130 stem cell Anatomy 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 210000000438 stratum basale Anatomy 0.000 description 1
- 210000000437 stratum spinosum Anatomy 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000036561 sun exposure Effects 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229950006156 teprenone Drugs 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 210000001578 tight junction Anatomy 0.000 description 1
- 230000030968 tissue homeostasis Effects 0.000 description 1
- 125000002640 tocopherol group Chemical class 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- 108091006106 transcriptional activators Proteins 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 235000001019 trigonella foenum-graecum Nutrition 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
- 230000027285 ultradian rhythm Effects 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 125000005500 uronium group Chemical group 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 230000001643 venotonic effect Effects 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 230000037373 wrinkle formation Effects 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
- 239000001841 zingiber officinale Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/08—Peptides having 5 to 11 amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/10—Peptides having 12 to 20 amino acids
-
- 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
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
- C07K1/061—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K4/00—Peptides having up to 20 amino acids in an undefined or only partially defined sequence; Derivatives thereof
- C07K4/10—Peptides having up to 20 amino acids in an undefined or only partially defined sequence; Derivatives thereof from plants
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- General Health & Medical Sciences (AREA)
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- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Dermatology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Birds (AREA)
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- Genetics & Genomics (AREA)
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- Immunology (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Description
R1-Wm-Xn-AA1-AA2-AA3-AA4-AA5-AA6-AA7-AA8-AA9-Yp-Zq-R2(I)
で表される化合物、その立体異性体および/またはその化粧品的にもしくは薬学的に許容される塩であって、式中、
AA1が、Pheであり、
AA2が、Trpであり、
AA3が、Met、Leu、およびIleからなる群から選択され、
AA4が、Lys、Arg、およびGlnからなる群から選択され、
AA5が、Argであり、
AA6が、Lysであり、
AA7が、Arg、Lys、およびHisからなる群から選択され、
AA8が、Val、Ile、Leu、およびMetからなる群から選択され、
AA9が、Proであり、
W、X、YおよびZが、それぞれ独立して、アミノ酸であり、
m、n、pおよびqが、それぞれ独立して、0または1であり、
m+n+p+qが、2以下であり、
R1が、H、ポリエチレングリコールに由来するポリマー、非環式脂肪族基、アリシクリル、ヘテロシクリル、ヘテロアリールアルキル、アリール、アラルキル、およびR5-CO-からなる群から選択され、ここで、R5は、H、非環式脂肪族基、アリシクリル、アリール、アラルキル、ヘテロシクリル、およびヘテロアリールアルキルからなる群から選択され、
R2が、-NR3R4、-OR3、-SR3からなる群から選択され、ここで、R3およびR4は、独立して、H、ポリエチレングリコールに由来するポリマー、非環式脂肪族基、アリシクリル、ヘテロシクリル、ヘテロアリールアルキル、アリール、およびアラルキルからなる群から選択され、
R1およびR2が、アミノ酸ではない、化合物、その立体異性体および/またはその化粧品的にもしくは薬学的に許容される塩を提供する。
特定の実施形態では、例えば、以下が提供される:
(項目1)
式(I):
R 1 -W m -X n -AA 1 -AA 2 -AA 3 -AA 4 -AA 5 -AA 6 -AA 7 -AA 8 -AA 9 -Y p -Z q -R 2 (I)
で表される化合物、その立体異性体および/またはその化粧品的にもしくは薬学的に許容される塩であって、式中、
AA 1 が、Pheであり、
AA 2 が、Trpであり、
AA 3 が、Met、Leu、およびIleからなる群から選択され、
AA 4 が、Lys、Arg、およびGlnからなる群から選択され、
AA 5 が、Argであり、
AA 6 が、Lysであり、
AA 7 が、Arg、Lys、およびHisからなる群から選択され、
AA 8 が、Val、Ile、Leu、およびMetからなる群から選択され、
AA 9 が、Proであり、
W、X、YおよびZが、それぞれ独立して、アミノ酸であり、
m、n、pおよびqが、それぞれ独立して、0または1であり、
m+n+p+qが、2以下であり、
R 1 が、H、ポリエチレングリコールに由来するポリマー、非環式脂肪族基、アリシクリル、ヘテロシクリル、ヘテロアリールアルキル、アリール、アラルキル、およびR 5 -CO-からなる群から選択され、ここで、R 5 は、H、非環式脂肪族基、アリシクリル、アリール、アラルキル、ヘテロシクリル、およびヘテロアリールアルキルからなる群から選択され、
R 2 が、-NR 3 R 4 、-OR 3 、-SR 3 からなる群から選択され、ここで、R 3 およびR 4 は、独立して、H、ポリエチレングリコールに由来するポリマー、非環式脂肪族基、アリシクリル、ヘテロシクリル、ヘテロアリールアルキル、アリール、およびアラルキルからなる群から選択され、
R 1 およびR 2 が、アミノ酸ではない、化合物、その立体異性体および/またはその化粧品的にもしくは薬学的に許容される塩。
(項目2)
AA 3 が、Metであり、任意に、AA 4 が、LysおよびArgからなる群から選択されるか、またはAA 4 が、Lysであるか、もしくはAA 4 が、Argである、項目1に記載の化合物、その立体異性体および/またはその化粧品的にもしくは薬学的に許容される塩。
(項目3)
AA 7 が、LysおよびArgからなる群から選択され、AA 8 が、Val、Ile、およびLeuからなる群から選択される、項目2に記載の化合物、その立体異性体および/またはその化粧品的にもしくは薬学的に許容される塩。
(項目4)
AA 3 が、Leuであり、任意に、AA 4 が、LysおよびArgからなる群から選択されるか、またはAA 4 が、Lysであるか、もしくはAA 4 が、Argである、項目1に記載の化合物、その立体異性体および/またはその化粧品的にもしくは薬学的に許容される塩。
(項目5)
AA 4 が、LysおよびArgからなる群から選択され、AA 7 が、LysおよびArgからなる群から選択され、AA 8 が、ValおよびIleからなる群から選択される、項目4に記載の化合物、その立体異性体および/またはその化粧品的にもしくは薬学的に許容される塩。
(項目6)
AA 3 が、Ileであり、任意に、AA 4 が、Glnである、項目1に記載の化合物、その立体異性体および/またはその化粧品的にもしくは薬学的に許容される塩。
(項目7)
AA 7 が、Hisであり、AA 8 が、Metである、項目6に記載の化合物、その立体異性体および/またはその化粧品的にもしくは薬学的に許容される塩。
(項目8)
前記化合物が、
R 1 -W m -X n -Phe-Trp-Met-Lys-Arg-Lys-Arg-Val-Pro-Y p -Z q -R 2 (ii)、
R 1 -W m -X n -Phe-Trp-Leu-Arg-Arg-Lys-Lys-Ile-Pro-Y p -Z q -R 2 (iii)、
R 1 -W m -X n -Phe-Trp-Ile-Gln-Arg-Lys-His-Met-Pro-Y p -Z q -R 2 (iv)、
R 1 -W m -X n -Phe-Trp-Leu-Lys-Arg-Lys-Arg-Val-Pro-Y p -Z q -R 2 (v)、
R 1 -W m -X n -Phe-Trp-Met-Arg-Arg-Lys-Arg-Val-Pro-Y p -Z q -R 2 (vi)、
R 1 -W m -X n -Phe-Trp-Met-Lys-Arg-Lys-Lys-Val-Pro-Y p -Z q -R 2 (vii)、
R 1 -W m -X n -Phe-Trp-Met-Lys-Arg-Lys-Arg-Ile-Pro-Y p -Z q -R 2 (viii)、および
R 1 -W m -X n -Phe-Trp-Met-Lys-Arg-Lys-Arg-Leu-Pro-Y p -Z q -R 2 (ix)からなる群から選択される式の化合物であり、
式中、R 1 、R 2 、W、X、Y、Z、ならびにm、n、p、およびqが、項目1の式(I)に定義される通りである、項目1に記載の化合物、その立体異性体および/またはその化粧品的にもしくは薬学的に許容される塩。
(項目9)
前記化合物が、式(ii)の化合物である、項目8に記載の化合物。
(項目10)
R 1 が、H、アセチル、パルミトイル、ラウロイル、またはミリストイルからなる群から選択され、R 2 が、-NR 3 R 4 または-OR 3 であり、ここで、R 3 およびR 4 は、独立して、HおよびC 1 -C 16 アルキルからなる群から選択される、項目1~9のいずれか一項に記載の化合物。
(項目11)
R 1 が、H、アセチルまたはパルミトイルからなる群から選択され、R 2 が、-NR 3 R 4 または-OR 3 であり、ここで、R 3 およびR 4 は、HおよびC 1 -C 16 アルキルからなる群から独立して選択される、項目10に記載の化合物。
(項目12)
R 3 が、Hであり、R 4 が、HおよびC 1 -C 16 アルキルからなる群から選択される、項目10または項目11に記載の化合物。
(項目13)
R 2 が、-NR 3 R 4 または-OR 3 であり、ここで、R 3 は、Hであり、R 4 は、HまたはC 1 -C 6 アルキルである、項目10~12のいずれか一項に記載の化合物。
(項目14)
m+n+p+qが、0である、項目1~13のいずれか一項に記載の化合物。
(項目15)
前記化合物が、
から選択される、項目1に記載の化合物。
(項目16)
皮膚、毛髪、爪および/または粘膜の化粧的であり非治療的な処置および/またはケアのための項目1~15のいずれか一項に記載の化合物の使用。
(項目17)
前記化粧的であり非治療的な処置および/またはケアが、皮膚の老化症状の処置および/または予防である、項目16に記載の使用。
(項目18)
前記皮膚の老化症状が、皮膚におけるミトコンドリア複合体Iの活性に起因する活性酸素種の生成および/または皮膚におけるミトコンドリア複合体IIの活性の減少に起因する、項目17に記載の使用。
(項目19)
前記化粧的であり非治療的な処置および/またはケアが、皮膚に活力を与えることである、項目16に記載の使用。
(項目20)
前記化粧的であり非治療的な処置および/またはケアが、皮膚のバリア機能の維持および/または改善である、項目16に記載の使用。
(項目21)
前記化粧的であり非治療的な処置および/またはケアが、皮膚の水和の維持および/または改善である、項目16に記載の使用。
(項目22)
前記化粧的であり非治療的な処置および/またはケアが、皮膚の微小循環および/または皮膚の色合いの維持および/または改善である、項目16に記載の使用。
(項目23)
前記化粧的であり非治療的な処置および/またはケアが、皮膚の疲労症状の処置および/または予防である、項目16に記載の使用。
(項目24)
前記化粧的であり非治療的な処置および/またはケアが、目袋の処置および/または予防である、項目16に記載の使用。
(項目25)
前記化粧的であり非治療的な処置および/またはケアが、皮膚の明度の維持および/または改善である、項目16に記載の使用。
(項目26)
前記皮膚が早朝の皮膚であるか、または前記皮膚が、概日リズムが変化した対象の皮膚である、項目16~23または16~25のいずれか一項に記載の使用。
(項目27)
前記化粧的であり非治療的な処置および/またはケアが、
(i)皮膚におけるJARID1Aタンパク質の発現が1日の最大より低く、皮膚におけるCRY2、PER2および/またはPER3時計遺伝子の発現が1日の最大より低く、皮膚に存在するセラミドの量が、1日の最大より低く、かつ/または皮膚細胞膜に取り込まれるDHAの量が、1日の最大より低い、皮膚の概日リズムの時点にある皮膚、
または(ii)皮膚におけるJARID1Aタンパク質の発現が1日の最大より低くなり、皮膚におけるCRY2、PER2および/またはPER3時計遺伝子の発現が1日の最大より低くなり、皮膚に存在するセラミドの量が、1日の最大より低くなり、かつ/または皮膚細胞膜に取り込まれるDHAの量が、1日の最大より低くなるように皮膚の概日リズムが変化した皮膚の化粧的であり非治療的な処置および/またはケアである、項目16~24または16~26のいずれか一項に記載の使用。
(項目28)
項目1~15のいずれか一項に記載の式(I)の化合物、その立体異性体および/またはその化粧品的にもしくは薬学的に許容される塩の化粧品的に有効な量、ならびに少なくとも1つの化粧品的に許容される賦形剤またはアジュバントを含む化粧品組成物。
(項目29)
対象の皮膚、毛髪、爪および/または粘膜の化粧的であり非治療的な処置および/またはケアの方法であって、項目1~15のいずれか一項に記載の化合物、その立体異性体、および/もしくはその化粧品的に許容される塩の化粧品的に有効な量、または前記化合物、その立体異性体、および/もしくはその化粧品的に許容される塩の化粧品的に有効な量を含む化粧品組成物を前記対象に投与することを含む、方法。
本発明の文脈において、「皮膚」は、それを構成する、最上層または角質層から最下層または皮下組織までの複数の層(最上層または角質層および最下層または皮下組織の両方を含めて)であると理解される。これらの層は、例えば、とりわけケラチノサイト、線維芽細胞、メラノサイト、マスト細胞、ニューロンおよび/または脂肪細胞などの異なる種類の細胞から構成される。用語「皮膚」は、頭皮も含む。用語「皮膚」は、哺乳動物の皮膚を含み、ヒトの皮膚を含む。同様に、用語「毛髪、爪、および粘膜」は、哺乳動物、例えば、ヒトの毛髪、爪、および粘膜を含む。
-(CH2)1-6-チエニル、-(CH2)1-6-フリル、-(CH2)1-6-ピロリジニル、および同様のものが挙げられる。
本発明の化合物
R1-Wm-Xn-AA1-AA2-AA3-AA4-AA5-AA6-AA7-AA8-AA9-Yp-Zq-R2(I)
で表される化合物、その立体異性体および/またはその化粧品的にもしくは薬学的に許容される塩であって、式中、
AA1が、Pheであり、
AA2が、Trpであり、
AA3が、Met、Leu、およびIleからなる群から選択され、
AA4が、Lys、Arg、およびGlnからなる群から選択され、
AA5が、Argであり、
AA6が、Lysであり、
AA7が、Arg、Lys、およびHisからなる群から選択され、
AA8が、Val、Ile、Leu、およびMetからなる群から選択され、
AA9が、Proであり、
W、X、YおよびZが、それぞれ独立して、アミノ酸であり、
m、n、pおよびqが、それぞれ独立して、0または1であり、
m+n+p+qが、2以下であり、
R1が、H、ポリエチレングリコールに由来するポリマー、非環式脂肪族基、アリシクリル、ヘテロシクリル、ヘテロアリールアルキル、アリール、アラルキル、およびR5-CO-からなる群から選択され、ここで、R5は、H、非環式脂肪族基、アリシクリル、アリール、アラルキル、ヘテロシクリル、およびヘテロアリールアルキルからなる群から選択され、
R2が、-NR3R4、-OR3、-SR3からなる群から選択され、ここで、R3およびR4は、独立して、H、ポリエチレングリコールに由来するポリマー、非環式脂肪族基、アリシクリル、ヘテロシクリル、ヘテロアリールアルキル、アリール、およびアラルキルからなる群から選択され、
R1およびR2が、アミノ酸ではない、化合物、その立体異性体および/またはその化粧品的にもしくは薬学的に許容される塩を提供する。
本発明の化合物、それらの立体異性体、これらの混合物および/またはそれらの化粧品的にもしくは薬学的に許容される塩の合成は、固相ペプチド合成法[Stewart J.M.and Young J.D.,「Solid Phase Peptide Synthesis,2nd edition」,(1984),Pierce Chemical Company,Rockford,Illinois、Bodanzsky M.and Bodanzsky A.,「The practice of Peptide Synthesis」,(1994),Springer Verlag,Berlin、Lloyd-Williams P.et al.,「Chemical Approaches to the Synthesis of Peptides and Proteins」,(1997),CRC,Boca Raton,FL,USA]、溶液中での合成、酵素合成[Kullmann W.“Proteases as catalysts for enzymic syntheses of opioid peptides”,(1980),J.Biol.Chem.,255(17),8234-8238]またはこれらの任意の組合せなどの先行技術において既知の従来の方法に従って実施され得る。本発明の化合物は、合成物であり得、例えば、固層ペプチド合成によって合成され得る。また本発明の化合物は、所望の配列を産生する目的での遺伝子操作により改変されたか、もしくは改変されていない細菌株の発酵により、または所望の配列を含む遊離ペプチド断片をもたらす、動物もしくは植物起源、例えば、微生物もしくは藻類、好ましくは植物起源のタンパク質の制御された加水分解により得られ得る。
-保護されたN末端の端および遊離のC末端の端を有するアミノ酸を、遊離のN末端の端および保護されたかまたは固体支持体と結合したC末端の端を有するアミノ酸とカップリングすることと、
-N末端の端の保護基を除去することと、
-所望のペプチド配列が得られるまで、配列のカップリングおよびN末端の端の保護基の除去を反復することと、
-C末端の端の保護基を除去または固体支持体を開裂することとを含む。
本発明は、式(I)の化合物は、皮膚の概日リズムを調節するのに有効であり、この能力を使用して皮膚の美容上の特性を改善することができるという発見に部分的に基づく。特に、本発明は、皮膚におけるJARID1Aタンパク質の発現、皮膚におけるCRY2、PER2および/またPER3時計遺伝子の発現、皮膚に存在するセラミドの量、および/または皮膚の細胞膜に取り込まれるDHAの量における変動に現れる皮膚の概日リズムに関する。概日リズムに関連する皮膚の美容上の特性には、バリア機能および皮膚の水和が含まれる。本発明の化合物は、JARID1Aタンパク質の発現の増加、CRY2、PER2および/またはPER3時計遺伝子の発現の増加、セラミドの量の増加、および/または皮膚の細胞膜に取り込まれるドコサヘキサエン酸(DHA)の量の増加を引き起こすことによって皮膚の概日リズムを調節すると考えられる。したがって、本発明の化合物は、皮膚におけるJARID1Aタンパク質の発現が1日の最大より低く、皮膚におけるCRY2、PER2および/またはPER3時計遺伝子の発現が1日の最大より低く、皮膚に存在するセラミドの量、および/または皮膚細胞膜に取り込まれるDHAの量が、1日の最大より低い、皮膚の概日リズムの時点にある皮膚の処置に有用である。JARID1Aタンパク質の発現は、ケラチノサイトおけるJARID1Aタンパク質の発現によって示され得る。皮膚におけるCRY2、PER2および/またはPER3時計遺伝子の発現は、表皮ケラチノサイトにおけるCRY2、PER2および/またはPER3時計遺伝子の発現によって示され得る。皮膚の細胞膜に取り込まれるDHAの量は、皮膚におけるPC-DHA/PC比によって示され得る。
本発明の化合物は、本発明の化合物を含有する組成物の形態で、本発明の化合物と対象の身体、好ましくは哺乳動物、好ましくはヒトの身体における作用部位との間に接触を引き起こす任意の手段によって、本発明の化合物を適用するために投与され得る。
dromanil[INCI:加水分解Caesalpinia Spinosaガム、Caesalpinia Spinosaガム];Aquarich(登録商標)[INCI:Avena Strigosa種子エキス]、CellActive(登録商標)-Hydro[INCI:Pyrus Malus(Apple)果実エキス、ペクチン、Chlorella Vulgaris/Lupinus Albusタンパク発酵物]、CellActive(登録商標)-Men[INCI:タウリン、Chlorella Vulgaris/Lupinus Albusタンパク発酵物、Acanthopanax Senticosus(エゾウコギ)根エキス]、Hydractin(登録商標)-LMF[INCI:Polypodium Vulgare根茎エキス、Cetraria Islandica(アイスランドゴケ)葉状体エキス、Sphagnum Magellanicumエキス]、Rahnにより販売されるMyramaze(登録商標)[INCI:Myrothamnus Flabellifoliaエキス、アスコルビン酸]、もしくはReforcyl(登録商標)[INCI:グルタミン、デシルグルコシド、フェネチルアルコール、Cistus Incanus花/葉/茎エキス、Gynostemma Pentaphyllum葉/茎エキス];Sederma/Crodaにより販売されるAqualance(商標)[INCI:エリトリトール、ホマリンHCl]、Hydraprotectol(商標)[INCI:ポリメタクリル酸グリセリル、アロイリット酸、酵母エキス(Faex)、糖タンパク質]、Moist 24(商標)[INCI:Imperata Cylindrica根エキス]、Optim Hyal(商標)[INCI:加水分解酵母エキス、セチルヒドロキシエチルセルロース、ポリグルクロン酸]、Osmocide(登録商標)4[INCI:グリセリン、(アクリレーツ/C10-30アクリル酸アルキル)クロスポリマー]、Renovage(商標)[INCI:トリ(カプリル酸/カプリン酸)グリセリル、テプレノン]、Revidrate(商標)[INCI:パルミチン酸エチルヘキシル、オレイン酸ソルビタン、ラウリン酸ソルビタン、ミリスチルリンゴ酸ホスホン酸]、Subliskin(商標)[INCI:Sinorhizobium Meliloti培養液、セチルヒドロキシエチルセルロース];Seppicにより販売されるAquaxyl(商標)[INCI:キシリチルグルコシド無水キシリトール、キシリトール]もしくはSepicalm(商標)S[INCI:ココイルアミノ酸Na、サルコシン、アスパラギン酸カリウム、アスパラギン酸マグネシウム];Silabにより販売されるCohesium(登録商標)[INCI:Ophiopogon Japonicus根エキス];Solianceにより販売されるHydreis[INCI:加水分解β-グルカン]、Hydrintense[INCI:Porphyridium Cruentumエキス]もしくはRenovHyal[INCI:ヒアルロン酸ナトリウム];Symriseにより販売されるSymLift(商標)[INCI:トレハロース、β-グルカン、Hordeum Vulgare種子エキス、ヒアルロン酸ナトリウム];ペトロラタム;鉱油;鉱ろうおよび合成ろう;蜜蝋(cera alba);パラフィン;または植物起源の油および蝋、例えば、とりわけ、カンデリラ蝋(トウダイグサ属cerifera)、カルナウバ蝋(Copernicia cerifera)、シアバター(Butirospermum parkii)、ココアバター(Theobroma cacao)、ヒマシ油(Ricinus communis)、ひまわり油(Helianthus annuus)、オリーブ油(Olea europaea)、ヤシ油(Cocos nucifera)、パーム油(Elaeis guineensis)、コムギの胚種油(Triticum vulgare)、甘扁桃油(Prunus amygdalus dulces)、ジャコウバラ種子油(Rosa moschata)、ツルマメ油(Glycine soja)、ブドウ種子油(Vitis vinifera)、キンセンカ油(Calendula officinalis)、ホホバ油(Simmonsis chinensis)、マンゴー油(Mangifera indica)、アボカード油(Persea gratissima)、ならびに/またはこれらの混合物により形成される化粧品的または薬学的アジュバントの群から選択される少なくとも1つの化合物、油またはワックスの化粧品的または薬学的に有効な量を含み得る。
全ての試薬および溶媒は、合成品質であり、いかなる追加の処理も行わずに使用される。
アミノ酸に使用される略語は、Eur.J.Biochem.(1984)138:9-37に概説される、1983年IUPAC-IUB生化学的命名法に関する共同委員会の推奨に従う。
全ての合成プロセスは、多孔性ポリエチレンディスクが装着されたポリプロピレンシリンジにおいて行う。全ての試薬および溶媒は、合成品質であり、いかなる追加の処理も行わずに使用する。溶媒および可溶性試薬を、サクションによって除去する。Fmoc基を、ピペリジン-DMF(2:8、v/v)(1×1分間、1×5分間、5mL/g樹脂)を用いて除去する[Lloyd-Williams P.et al.(1997)「Chemical Approaches to the Synthesis of Peptides and Proteins」 CRC,Boca Raton (FL,USA)]。脱保護、カップリングおよび再度の脱保護段階の間の洗浄を、毎回10mL溶媒/gの樹脂を使用してDMF(3×1分間)により行う。カップリング反応を、3mL溶媒/gの樹脂を用いて実施する。カップリングの制御を、ニンヒドリン試験[Kaiser E.et al.,Anal.Biochem.(1970),34:595-598]またはクロラニル試験[Christensen T.,ActaChem.Scand.,(1979),33B,763-766]の実施により行う。全ての合成反応および洗浄を、25℃で行う。
・アミノ酸のLysおよびTrpについてBoc(tert-ブチルオキシカルボニル);
・アミノ酸のArgについてPbf(2,2,4,6,7-ペンタメチルジヒドロベンゾフラン-5-スルホニル);および
・アミノ酸のGlnおよびHisについてTrt(トリチル)。
HPLCクロマトグラフィー分析を、30℃に温度自動調節された(thermostatized)逆相カラム(50×4.6mm、Kromasil C18、3.5μm、Akzo Nobel、スウェーデン)を使用してShimadzu装置(日本、京都)により行う。溶出を、流速1.6mL/分で水(+0.1%TFA)中のアセトニトリル(+0.07%TFA)の勾配を使用して行い、検出を、220nmにて行う。エレクトロスプレーイオン化質量分析を、WATERS Alliance ZQ 2000検出器において、移動相としてMeCN:H2Oが4:1(+0.1%TFA)の混合物を使用して流速0.3mL/分で行う。
H-AA9-O-2-ClTrt-(R)(式中、AA9は、L-Proである)の取得。
重量は、正規化された。0.83当量のDIEAが添加された20mLのDCMに溶解した、3.2mmol(1当量)のFmoc-L-Pro-OHを、1.6mmol/gの官能基が付与された乾燥2-クロロトリチル樹脂(3.2mmol)にカップリングさせる。混合物を5分間撹拌し、その後、1.63当量のDIEAを添加する。この混合物を40分間反応させる。残留する塩素基を、2mLのMeOHで処理することによってブロックする。
Fmoc-AA1-AA2-AA3-AA4-AA5-AA6-AA7-AA8-AA9-O-2-ClTrt-(R)(式中、AA1は、L-Pheであり、AA2は、L-Trpであり、AA3は、L-Metであり、AA4は、L-Lysであり、AA5は、L-Argであり、AA6は、L-Lysであり、AA7iは、Argであり、AA8iは、L-Valであり、AA9は、L-Proである)の取得。
重量は、正規化された。1.19mmol/g(0.09mmol)の官能基が付与された76mgのH-L-Pro-O-2-Cl-Trt樹脂を、一般方法に記載のようにして洗浄する。記載されているプロトコールに従い、5当量のFmoc-Val-OH(Fmoc-AA8-OH)を、5.5当量のDIPCDIおよび5当量のHOBtの存在下で、DMFを溶媒として使用してペプチジル樹脂に60分間カップリングさせる。
Fmoc-Wm-Xn-AA1-AA2-AA3-AA4-AA5-AA6-AA7-AA8-AA9-Yp-Zq-AM-MBHA-(R)(式中、AA1は、L-Pheであり、AA2は、L-Trpであり、AA3は、L-Metであり、AA4は、L-Lysであり、AA5は、L-Argであり、AA6は、L-Lysであり、AA7は、Argであり、AA8は、L-Valであり、AA9は、L-Proであり、m、n、pおよびqは、各々0である)の取得。
重量は、正規化された。Fmoc基を除去するために、記載されている一般プロトコールに従って、0.51mmol/gの官能基を付与された240mg(0.12mmol)のFmoc-AM-pMBHA樹脂を、ピペリジン:DMFで処理する。5当量のFmoc-L-Pro-OH(Fmoc-AA9-OH)を、5.5当量のDIPCDIおよび5当量のHOBtの存在下で、DMFを溶媒として使用して、脱保護された樹脂に1時間取り込ませる。
FmocN末端保護基の除去の一般的方法。
実施例1、2および3で得られたペプチジル樹脂のN末端Fmoc基を、一般方法に記載のようにして脱保護する(DMF中20%ピペリジン、1×1分間+1×5分間)。ペプチジル樹脂をDMF(5×1分間)、DCM(3×1分間)、ジエチルエーテル(3×1分間)で洗浄し、真空下で乾燥させる。
実施例4で得られたペプチジル樹脂にR1パルミトイル基を導入する方法。
DMF(1mL)に予め溶解させた180mg(0.7mmol;5当量)または154mg(0.6mmol、5当量)のパルミチン酸を、107mg(0.7mmol;5当量)または92mg(0.6mmol、5当量)のHOBtおよび127μlのDIPCDI(0.77mmol;5.5当量)または102μlのDIPCDI(0.66mmol、5.5当量)の存在下で、実施例4で得られた、それぞれ0.14mmolまたは0.12mmolのペプチジル樹脂の各々に添加する。混合物を3時間反応させ、その後、樹脂をDMF(3×1分間)、DCM(3×1分間)、ジエチルエーテル(3×1分間)で洗浄し、真空下で乾燥させる。
実施例4で得られたペプチジル樹脂にR1アセチル基を導入する方法。
実施例4で得られた0.12mmolまたは0.14mmolのペプチジル樹脂を、2mLのDMFを溶媒として使用して、25当量のDIEAの存在下で25当量の無水酢酸により処理する。混合物を30分間反応させ、その後、樹脂をDMF(3×1分間)、DCM(3×1分間)、ジエチルエーテル(3×1分間)で洗浄し、真空下で乾燥させる。
実施例4、5および6で得られたペプチジル樹脂のポリマー支持体からの開裂方法。
実施例4、5および6で得られた乾燥ペプチジル樹脂の各々を、撹拌下で、3mLのTFA:H2O(95:5、v/v)で室温にて2時間処理する。次いで、それを多孔性ポリエチレンディスクを装着したポリプロピレンシリンジを通して濾過する。20mLの冷ジエチルエーテル上に濾液を収集し、10mLジエチルエーテルで5回洗浄する。最終沈殿物を真空下で乾燥させる。
ポリマー支持体からの開裂方法およびR2置換アミンによる官能基付与:H-Wm-Xn-AA1-AA2-AA3-AA4-AA5-AA6-AA7-AA8-AA9-Yp-Zq-NH-(CH2)5-CH3の取得(式中、AA1は、L-Pheであり、AA2は、L-Trpであり、AA3は、L-Metであり、AA4は、L-Lysであり、AA5は、L-Argであり、AA6は、L-Lysであり、AA7は、L-Argであり、AA8は、L-Valであり、AA9は、結合またはL-Proであり、m、n、pおよびqは、各々0である)。
完全に保護された側鎖を有するペプチドH-Wm-Xn-AA1-AA2-AA3-AA4-AA5-AA6-AA7-AA8-AA9-Yp-Zq-OHを、KOHの存在下で真空下で既に乾燥させておいた、実施例4で得られた299mgのペプチジル樹脂H-Wm-Xn-AA1-AA2-AA3-AA4-AA5-AA6-AA7-AA8-AA9-Yp-Zq-O-2-ClTrt-(R)を処理することによって得る。2.03mlのAcOHで2時間処理し、液相を濾過により分離する。濾液を収集し、次いで、樹脂を1mlのAcOH(1×1分間)で洗浄する。全ての液相を合わせ、凍結乾燥させる。
ポリマー支持体からの開裂方法およびR2置換アミンによる官能基付与:H-Wm-Xn-AA1-AA2-AA3-AA4-AA5-AA6-AA7-AA8-AA9-Yp-Zq-NH-(CH2)15-CH3(式中、AA1は、L-Pheであり、AA2は、L-Trpであり、AA3は、L-Metであり、AA4は、L-Lysであり、AA5は、L-Argであり、AA6は、L-Lysであり、AA7は、L-Argであり、AA8は、L-Valであり、AA9は、結合またはL-Proであり、m、n、pおよびqは、各々0である)の取得。
完全に保護された側鎖を有するペプチドH-Wm-Xn-AA1-AA2-AA3-AA4-AA5-AA6-AA7-AA8-AA9-Yp-Zq-OHを、KOHの存在下で真空下で既に乾燥させておいた、299mgの実施例4のペプチジル樹脂H-Wm-Xn-AA1-AA2-AA3-AA4-AA5-AA6-AA7-AA8-AA9-Yp-Zq-O-2-ClTrt-(R)の各々を処理することによって得る。2.03mlのAcOHで2時間処理し、液相を濾過により分離する。濾液を収集し、次いで、樹脂を1mlのAcOH(1×1分間)で洗浄する。全ての液相を合わせ、凍結乾燥させる。
成人由来の同期されたヒト表皮ケラチノサイト(HEKa)におけるJARID1A遺伝子発現のリアルタイムPCRアレイを使用したインビトロ研究。
概日時計に関与するタンパク質は、JARID1Aと称されるヒストンリジンデメチラーゼタンパク質である。JARID1Aタンパク質は、CLOCK-BMAL1と複合体を形成し、PER遺伝子の転写を活性化する。Jarid1Aの発現減少は、PER遺伝子の発現の低下および概日リズムの変化を引き起こした。それゆえ、早朝でのJarid1Aおよび時計遺伝子発現の活性化は、概日周期の前進を引き起こし、昼間の皮膚機能を付与し得る。したがって、この研究の主な目的は、いくつかのペプチドの同期されたヒトケラチノサイトにおけるJarid1Aの発現を早朝に増加させる能力を評価することである。
比色検出法に基づくELISAアッセイを使用した、同期されたヒトケラチノサイトでのペプチドH-Phe-Trp-Met-Lys-Arg-Lys-Arg-Val-Pro-NH2(PEP-1)によるJARID1Aタンパク質増加タンパク質レベルのインビトロ研究。
多くの皮膚機能が概日リズムに従い、皮脂分泌は、正午頃のピークを有し、静電容量(皮膚の水和の尺度)は、1日の早い段階ではより低い。皮膚血流および皮膚のバリア機能も、概日リズムおよび縮日リズム(1日より短い繰り返される期間を有する)を示し、皮膚血流は、1日の早い段階では低く、午後遅くおよび夜遅くにピークを有する。
JARID1Aタンパク質を、製造者のプロトコールに従って酵素結合免疫吸着測定法を使用して定量化する(ヒトリジン特異的デメチラーゼ5A(KDM5A)(CUSABIO)。要約すると、JARID1Aタンパク質を、キットで提供される抗体を用いて検出し、比色反応により定量化する。吸光度による定量化を、450nmおよび570nmに設定したマイクロプレートリーダー(ClarioStar(登録商標)、BMG)を使用して行う。波長補正のために、450nmでの測定値から570nmでの測定値を減算した。
細胞可溶化物の総タンパク質濃度を、Pierce BCA Protein Assay Kit(Thermo Scientific)を使用して測定する。要約すると、標準物質および試料を分配し、Working Reagentを試料に添加する。60℃にて30分間のインキュベーション後、色の変化を、吸光度マイクロプレートリーダー(Clariostar(登録商標)、BMG)を用いて562nmで測定する。総タンパク質量を使用して、試料のELISA試験により得られたJARID1Aタンパク質濃度のレベルを正規化する。
比色検出法に基づくアッセイを使用したミトコンドリア複合体Iの活性の阻害。
ミトコンドリアは細胞内のエネルギー生成を担う重要な細胞小器官であり、ATP(アデノシン三リン酸)形態の細胞エネルギーのおよそ90%を生成する。このプロセスは、ミトコンドリアの内膜(この構造を横切るプロトン流により電子伝達系(ETC)をATP合成に共役させる複雑な構造)内で起こる。ETCは、NADHおよびFADH2(解糖系およびクエン酸回路において生成される)から酸素分子への電子伝達を担い、この過程の末に酸素分子のH2Oへの還元を引き起こす。ECTは、4つの異なるタンパク質複合体によって構成される。複合体I(NADHデヒドロゲナーゼ)において、電子がNADHから電子伝達系に渡され、ここで、電子が残りの複合体内を通る。結果として、ミトコンドリア複合体Iの活性は、NADHのNADへの酸化を引き起こす。
比色検出法に基づくアッセイを使用したミトコンドリア複合体IIの活性の増加の測定。
ATP生成は、細胞におけるエネルギーの約90%を産生する特化した細胞小器官であるミトコンドリアの内膜で起こる。このプロセスは、電子伝達系(ETC)をATP合成に共役させるミトコンドリアの内膜で起こる。ETCは、NADHおよびFADH2(解糖系およびクエン酸回路において生成される)から酸素分子への電子伝達を担い、この過程の末に酸素分子のH2Oへの還元を引き起こす。ECTは、4つの異なるタンパク質複合体によって構成される。コハク酸-補酵素Qレダクターゼ(SDH)としても既知のミトコンドリア複合体IIは、コハク酸からユビキノン(Q)への電子伝達を触媒し、ユビキノール(QH2)の生成を引き起こす。
免疫蛍光アッセイによりヒト皮膚の線維芽細胞(HDFa)におけるミトコンドリア膜電位を増加させるインビトロ研究。
ミトコンドリアは、細胞代謝において不可欠な役割を果たす細胞内小器官である。ミトコンドリア膜電位(MMP)は、内部ミトコンドリア膜における電子伝達系の正常機能により作り出される内部ミトコンドリア膜を横切る電位の尺度である。MMPは、多くのミトコンドリアによるプロセスに高度に連関する。具体的に、MMPは、アデノシン三リン酸(ATP)合成(細胞における主なエネルギー源)の直接的なバイオマーカーである。このために、MMPを増加させる能力を有する製品は、細胞に活力を与え、皮膚機能を改善することができる。この実験の主な目的は、ペプチドH-Phe-Trp-Met-Lys-Arg-Lys-Arg-Val-Pro-NH2(PEP-1)のヒト皮膚の線維芽細胞におけるミトコンドリア膜電位を増加させる能力を評価することである。
蛍光手法によるヒト皮膚の線維芽細胞(HDFa)における活性酸素種(ROS)レベルの評価。
細胞代謝は、細胞の成長および複製、それらの構造の維持、ならびに環境の変化への反応を可能にする広範囲の化学反応を含む。酸素代謝の結果として、細胞は、活性酸素種(ROS)と称されるいくつかの天然の副産物を生成する。ROSは、ヒドロキシルラジカル、スーパーオキシドアニオン、過酸化水素および過酸化亜硝酸を含む高反応性の酸素分子である。細胞のROSレベルは、化学物質の曝露、電離放射線、および細菌またはウィルス感染を含む異なる外部源により増加し得る。
同期されたヒト全層皮膚モデルにおける水和レベルの測定。
多くの基本的な皮膚機能が概日リズムに従い、皮脂分泌は、正午頃のピークを有し、皮膚血流および皮膚のバリア機能は、早朝では低く、午後遅くにピークに達する。皮膚の温度および水和も、1日に沿った時間依存的パターンを示す。早朝において低レベルの皮膚の水和は、正午頃に増加する。皮膚の水和は、皮膚組織の恒常性を維持するためのより重要な要素の1つである。皮膚の適切な含水量は、ケラチノサイト層内での多くの重要な機能、例えば、脂質層の完全性、皮膚のバリア機能ならびに角質層の機能的および構造的な組成の強化などを制御する。日光への曝露、不健康な食事、およびスキンケア習慣は、皮膚の乾燥、老化の加速、コラーゲンの破壊、ならびに表情線および皺の形成を引き起こす。結果として乾燥皮膚は、活力のない、暗い外観を呈する。
リアルタイムPCRアレイを使用した、成人由来の同期されたヒト表皮ケラチノサイト(HEKa)における時計遺伝子発現のインビトロ研究。
多くの皮膚機能が概日リズムに従い、皮脂分泌は、正午頃のピークを有し、静電容量(皮膚の水和の尺度)は、1日の早い段階ではより低い。皮膚血流および皮膚のバリア機能も、概日リズムおよび縮日リズムを示し、皮膚血流量は、日中の早い段階では低く、午後遅くおよび夜遅くピークに達する。
リアルタイムPCRアレイを使用した若齢および老齢のヒト表皮ケラチノサイト(HEKa)におけるPER遺伝子発現のインビトロ研究。
哺乳動物では、概日時計は、全組織の大部分で見出され、CLOCK-BMAL1複合体が日中に概日時計遺伝子(PERおよびCRYなど)の転写を駆動する調節のフィードバックループに基づく。哺乳動物の概日時計の破壊は老化の加速をもたらし、更に概日リズムは加齢と共に障害される。PER遺伝子のノックアウトによる概日リズムの遺伝子的破壊は、様々な加齢に関連する症状および早期老化の可視的な徴候を引き起こす。PER遺伝子の発現レベルは、加齢と共にヒト皮膚細胞において大きく減少する。したがって、この研究の主な目的は、リアルタイムPCRアレイを使用して、26歳のドナーおよび54歳のドナーに由来するヒトケラチノサイトのPER2およびPER3遺伝子発現を増加させるペプチドH-Phe-Trp-Met-Lys-Arg-Lys-Arg-Val-Pro-NH2(PEP-1)の能力を評価することである。
同期されたヒト全層皮膚モデルにおけるリピドミクスプロファイルの解析。
脂質は、皮膚において必須の役割を果たす。角質層(皮膚の外層)は、表皮細胞の分化の終点と称される、特化した構造である角化膜を含む。この構造は、脂質エンベロープによって囲まれたケラチンの高度に架橋された網目組織からなる。角化膜は、外来性の粒子、病原体および表皮の水分喪失に対する物理的障壁として機能し、皮膚の恒常性を調節する。セラミド(角化膜内の主な脂質成分)は、スフィンゴシンおよび脂肪酸により構成される分子のファミリーである。皮膚におけるセラミドの量は、皮膚の水不透過性を提供し、これにより、皮膚乾燥の発生を回避している。Ω-3脂肪酸ファミリーもまた皮膚の機能において重要な役割を果たす。特に、ドコサヘキサエン酸(DHA)は、その二重層の細胞膜への取込み(DHAと結合したホスファチジルコリンと全ホスファチジルコリンレベルとの間の比率、すなわちPC-DHA/PCとも称される)が、適切な細胞膜流動性を維持するのを助ける長鎖不飽和脂肪酸である。DHAの食事による補給は、その皮膚取込みを増加させ、経皮水分損失の減少、したがって、皮膚の水和の増加により測定される皮膚のバリア機能を改善する。
ペプチドH-Phe-Trp-Met-Lys-Arg-Lys-Arg-Val-Pro-NH2(PEP-1)を含むマイクロエマルションの調製
適切な容器内で、ペプチドH-Phe-Trp-Met-Lys-Arg-Lys-Arg-Val-Pro-NH2(PEP-1)を、水[INCI:水(AQUA)](相A1)に溶解させ、次に、別個の容器内で予め混合しておいた相A2の成分の混合物(2-フェノキシエタノール[INCI:フェノキシエタノール]、Structure(登録商標)XL[INCI:ヒドロキシプロピルデンプンリン酸]、Zemea(商標)[INCI:プロパンジオール]、Amigel(登録商標)[INCI:スクレロチウムガム]、およびヒアルロン酸ナトリウム[INCI:ヒアルロン酸ナトリウム];表16参照)を導入する。得られた混合物を、穏やかに撹拌しながら70℃で加熱し、次いでCola(登録商標)Fax CPE-K[INCI:セチルリン酸カリウム]を添加する(相A3)。
実施例20のマイクロエマルションを含む脂質ナノ粒子組成物の調製
実施例20で調製したマイクロエマルションを、適切な容器に導入する(相A)。
ペプチドH-Phe-Trp-Met-Lys-Arg-Lys-Arg-Val-Pro-NH2(PEP-1)を含むリポソームの調製
適切な容器内で、相Aを、水[INCI:水(AQUA)]、Zemea(商標)[INCI:プロパンジオール]中にペプチドH-Phe-Trp-Met-Lys-Arg-Lys-Arg-Val-Pro-NH2(PEP-1)を溶解させることによって調製し、2-フェノキシエタノール[INCI:フェノキシエタノール](相B)を、相Aに添加する。
カチオン性ポリマーに結合した実施例22のリポソームの調製
実施例22で得られたリポソームを、ゆっくり撹拌しながら、SENSOMER(登録商標)CI-50[INCI:水(AQUA);塩化ヒドロキシプロピルトリモニウムデンプン;尿素;乳酸ナトリウム;塩化ナトリウム;安息香酸ナトリウム]に、リポソーム:カチオン性ポリマー比95:5(w/w)で添加する。
ペプチドH-Phe-Trp-Met-Lys-Arg-Lys-Arg-Val-Pro-NH2(PEP-1)を含有する化粧品組成物(液体エマルション)の調製
適切な容器内で、相A1の成分:水[INCI:水(AQUA)]、Zemea(商標)[INCI:プロパンジオール]、グリセリン[INCI:グリセリン]、Genencare(商標)OSMS BA[INCI:ベタイン]、Dissolvine(登録商標)NA2[INCI:EDTA二ナトリウム]、ソルビン酸カリウム[INCI:ソルビン酸カリウム]を溶解させる。
ペプチドH-Phe-Trp-Met-Lys-Arg-Lys-Arg-Val-Pro-NH2(PEP-1)を含有する化粧品組成物(クリーム)の調製
適切な容器内で、相A1の成分:水[INCI:水(AQUA)]、Zemea(商標)[INCI:プロパンジオール]、Hydrolite(登録商標)5[INCI:ペンチレングリコール]、およびDissolvine(登録商標)NA2[INCI:EDTA二ナトリウム]を溶解させる。
H-Phe-Trp-Met-Lys-Arg-Lys-Arg-Val-Pro-NH2(PEP-1)を含有する化粧品組成物(ローション)の調製
適切な容器内で、相A1の成分:水[INCI:水(AQUA)]、Zemea(商標)[INCI:プロパンジオール]、グリセリン[INCI:グリセリン]、ソルビン酸カリウム[INCI:ソルビン酸カリウム]、およびDissolvine(登録商標)NA2[INCI:EDTA二ナトリウム]を、溶解させる。
ゲルクリーム組成物(プラシーボ)の調製物
適切な容器内で、相Aの成分:水[INCI:水(AQUA)]、Zemea(商標)[INCI:プロパンジオール]、Phenoxetol(登録商標)[INCI:フェノキシエタノール]、Dissolvine(登録商標)NA2[INCI:EDTA二ナトリウム]、およびソルビン酸カリウム顆粒[ソルビン酸カリウム]を、分散させる。
5%(w/w)のH-Phe-Trp-Met-Lys-Arg-Lys-Arg-Val-Pro-NH2(PEP-1)を含むゲルクリーム組成物の調製物
適切な容器内で、相Aの成分:水[INCI:水(AQUA)]、Zemea(商標)[INCI:プロパンジオール]、Phenoxetol(登録商標)[INCI:フェノキシエタノール]、Dissolvine(登録商標)NA2[INCI:EDTA二ナトリウム]、およびソルビン酸カリウム顆粒[ソルビン酸カリウム]を、分散させる。
本発明による有効成分の白人皮膚タイプの女性ボランティアにおける短期適用の活力を与える効果の評価のためのインビボ研究。
皮膚は、体内時計を有する。その基本的特性は、概日制御および顔の外観が最も良く見えるその正午頃に従う。しかし、勤務シフトまたは睡眠不足のような条件は、生物学的皮膚機能の脱同期を引き起こし得る。本発明のペプチドを含む組成物が、皮膚の微小循環、目袋のボリューム、および皮膚のバリア機能の測定によって評価されるように、活力を与える効果を有し、我々の皮膚の生体時計を前進させることができることを実証するために、この実施例が実施された。
生成物適用の7日後に、ランダムに選択された1つの眼での目袋のボリュームを、Primos lite 3D(Canfield)システムにより測定する。結果を、表29に示す。
皮膚のバリア機能に関連する3つの異なるパラメータを、有効成分適用の7日後に測定する。水和をCorneometer(商標)CM825(Courage + Khazaka)により、経皮水分喪失(TEWL)をVapometer(Delfin Technologies)により、および皮脂含量をSebumeter(商標)SM810(Courage + Khazaka)により測定する。皮膚のバリア機能の程度を、水和および皮脂を測定することによって得られた値を加算すること、およびTEWL値を減算することにより、算出する。結果を、表30に示す。
白人皮膚タイプの女性ボランティアにおける長期適用後での活力を与える効果および老化防止効果の評価のためのインビボ研究。
老化および「時差ぼけ」は、内部時計の概日リズムを設定する皮膚の能力を減少させ、1日に沿った生物学的皮膚機能の脱同期を引き起こす。この研究は、本発明による有効成分が我々の皮膚の生物時計を前進させ、抗老化特性をもたらすことができることを証明することを目的とした。
生成物適用の28日後に、ランダムに選択された1つの眼での目袋のボリュームを、Primos lite 3D(Canfield)システムにより測定する。結果を、表33に示す。
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Claims (14)
- 式(I):
R1-Wm-Xn-AA1-AA2-AA3-AA4-AA5-AA6-AA7-AA8-AA9-Yp-Zq-R2(I)
で表される化合物、その立体異性体および/またはその化粧品的にもしくは薬学的に許容される塩であって、式中、
AA1が、Pheであり、
AA2が、Trpであり、
AA3が、Met、Leu、およびIleからなる群から選択され、
AA4が、Lys、Arg、およびGlnからなる群から選択され、
AA5が、Argであり、
AA6が、Lysであり、
AA7が、Arg、Lys、およびHisからなる群から選択され、
AA8が、Val、Ile、Leu、およびMetからなる群から選択され、
AA9が、Proであり、
W、X、YおよびZが、それぞれ独立して、アミノ酸であり、
m、n、pおよびqが、それぞれ独立して、0であり、
R1が、H、アセチル、パルミトイル、ラウロイル、またはミリストイルからなる群から選択され、
R2が、-NR3R4または-OR3であり、ここで、R3およびR4は、独立して、HおよびC1-C16アルキルからなる群から選択され、
R1およびR2が、アミノ酸ではない、化合物、その立体異性体および/またはその化粧品的にもしくは薬学的に許容される塩。 - AA3が、Metであり、任意に、AA4が、LysおよびArgからなる群から選択されるか、またはAA4が、Lysであるか、もしくはAA4が、Argである、請求項1に記載の化合物、その立体異性体および/またはその化粧品的にもしくは薬学的に許容される塩。
- AA7が、LysおよびArgからなる群から選択され、AA8が、Val、Ile、およびLeuからなる群から選択される、請求項2に記載の化合物、その立体異性体および/またはその化粧品的にもしくは薬学的に許容される塩。
- AA3が、Leuであり、任意に、AA4が、LysおよびArgからなる群から選択されるか、またはAA4が、Lysであるか、もしくはAA4が、Argである、請求項1に記載の化合物、その立体異性体および/またはその化粧品的にもしくは薬学的に許容される塩。
- AA4が、LysおよびArgからなる群から選択され、AA7が、LysおよびArgからなる群から選択され、AA8が、ValおよびIleからなる群から選択される、請求項4に記載の化合物、その立体異性体および/またはその化粧品的にもしくは薬学的に許容される塩。
- AA3が、Ileであり、任意に、AA4が、Glnである、請求項1に記載の化合物、その立体異性体および/またはその化粧品的にもしくは薬学的に許容される塩。
- 前記化合物が、
R1-Wm-Xn-Phe-Trp-Met-Lys-Arg-Lys-Arg-Val-Pro-Yp-Zq-R2 (ii)、
R1-Wm-Xn-Phe-Trp-Leu-Arg-Arg-Lys-Lys-Ile-Pro-Yp-Zq-R2 (iii)、
R1-Wm-Xn-Phe-Trp-Ile-Gln-Arg-Lys-His-Met-Pro-Yp-Zq-R2 (iv)、
R1-Wm-Xn-Phe-Trp-Leu-Lys-Arg-Lys-Arg-Val-Pro-Yp-Zq-R2 (v)、
R1-Wm-Xn-Phe-Trp-Met-Arg-Arg-Lys-Arg-Val-Pro-Yp-Zq-R2 (vi)、
R1-Wm-Xn-Phe-Trp-Met-Lys-Arg-Lys-Lys-Val-Pro-Yp-Zq-R2 (vii)、
R1-Wm-Xn-Phe-Trp-Met-Lys-Arg-Lys-Arg-Ile-Pro-Yp-Zq-R2 (viii)、および
R1-Wm-Xn-Phe-Trp-Met-Lys-Arg-Lys-Arg-Leu-Pro-Yp-Zq-R2 (ix)からなる群から選択される式の化合物であり、
式中、R1、R2、W、X、Y、Z、ならびにm、n、p、およびqが、請求項1の式(I)に定義される通りである、請求項1に記載の化合物、その立体異性体および/またはその化粧品的にもしくは薬学的に許容される塩。 - R1が、H、アセチルまたはパルミトイルからなる群から選択され、R2が、-NR3R4または-OR3であり、ここで、R3およびR4は、HおよびC1-C16アルキルからなる群から独立して選択される、請求項1~7のいずれか一項に記載の化合物。
- 皮膚、毛髪、爪および/または粘膜の化粧的であり非治療的な処置および/またはケアのための請求項1~9のいずれか一項に記載の化合物を含む組成物。
- 前記化粧的であり非治療的な処置および/またはケアが、皮膚の老化症状の処置および/または予防;皮膚に活力を与えること;皮膚のバリア機能の維持および/または改善;皮膚の水和の維持および/または改善;皮膚の微小循環および/または皮膚の色合いの維持および/または改善;皮膚の疲労症状の処置および/または予防;目袋の処置および/または予防;あるいは皮膚の明度の維持および/または改善である、請求項10に記載の組成物。
- 前記皮膚が早朝の皮膚であるか、または前記皮膚が、概日リズムが変化した対象の皮膚である、請求項10または請求項11に記載の組成物。
- 請求項1~9のいずれか一項に記載の式(I)の化合物、その立体異性体および/またはその化粧品的にもしくは薬学的に許容される塩の化粧品的に有効な量、ならびに少なくとも1つの化粧品的に許容される賦形剤またはアジュバントを含む化粧品組成物。
- 対象の皮膚、毛髪、爪および/または粘膜の化粧的であり非治療的な処置および/またはケアのための組成物であって、請求項1~9のいずれか一項に記載の化合物、その立体異性体、および/もしくはその化粧品的に許容される塩の化粧品的に有効な量を含む、組成物。
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JP2012531414A (ja) | 2009-06-23 | 2012-12-10 | イーエルシー マネージメント エルエルシー | 概日遺伝子活性化剤を含む皮膚修復組成物およびsirt1遺伝子活性化剤の相乗的組合せ |
JP2014510090A (ja) | 2011-03-25 | 2014-04-24 | リポテック,エセ.ア. | 皮膚及び/又は粘膜の治療及び/又はケアに有用なペプチド並びに化粧品若しくは医薬組成物におけるそれらの使用 |
JP2015514722A (ja) | 2012-04-16 | 2015-05-21 | ルブリゾル アドバンスド マテリアルズ, インコーポレイテッド | 皮膚および/または粘膜の処置および/またはケアのための組成物ならびに化粧品組成物または医薬組成物におけるその使用 |
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BR112020000123A2 (pt) | 2020-07-07 |
US20200214960A1 (en) | 2020-07-09 |
EP3648784B1 (en) | 2021-12-22 |
JP2020525529A (ja) | 2020-08-27 |
ES2904249T3 (es) | 2022-04-04 |
AU2018295515A1 (en) | 2020-01-30 |
WO2019008452A1 (en) | 2019-01-10 |
EP3648784A1 (en) | 2020-05-13 |
KR20200024235A (ko) | 2020-03-06 |
CN110997694A (zh) | 2020-04-10 |
US11896704B2 (en) | 2024-02-13 |
AU2018295515B2 (en) | 2024-07-11 |
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