KR102694657B1 - 항균성 테트라펩티드 - Google Patents
항균성 테트라펩티드 Download PDFInfo
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- KR102694657B1 KR102694657B1 KR1020207015187A KR20207015187A KR102694657B1 KR 102694657 B1 KR102694657 B1 KR 102694657B1 KR 1020207015187 A KR1020207015187 A KR 1020207015187A KR 20207015187 A KR20207015187 A KR 20207015187A KR 102694657 B1 KR102694657 B1 KR 102694657B1
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- Prior art keywords
- alkyl group
- compound
- cosmetic composition
- group
- skin
- Prior art date
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- 230000000845 anti-microbial effect Effects 0.000 title description 3
- 239000003242 anti bacterial agent Substances 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 62
- 239000000203 mixture Substances 0.000 claims description 61
- -1 (1H-indol-3-yl)methyl Chemical group 0.000 claims description 60
- 239000002537 cosmetic Substances 0.000 claims description 60
- 150000001413 amino acids Chemical group 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 15
- 244000063299 Bacillus subtilis Species 0.000 claims description 12
- 235000014469 Bacillus subtilis Nutrition 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 claims description 11
- 239000004904 UV filter Substances 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 229960001679 octinoxate Drugs 0.000 claims description 10
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 9
- 239000004475 Arginine Substances 0.000 claims description 9
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 9
- 229960005193 avobenzone Drugs 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- TYYHDKOVFSVWON-UHFFFAOYSA-N 2-butyl-2-methoxy-1,3-diphenylpropane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C(OC)(CCCC)C(=O)C1=CC=CC=C1 TYYHDKOVFSVWON-UHFFFAOYSA-N 0.000 claims description 8
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 claims description 8
- RMGVATURDVPNOZ-UHFFFAOYSA-M potassium;hexadecyl hydrogen phosphate Chemical compound [K+].CCCCCCCCCCCCCCCCOP(O)([O-])=O RMGVATURDVPNOZ-UHFFFAOYSA-M 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- WSSJONWNBBTCMG-UHFFFAOYSA-N 2-hydroxybenzoic acid (3,3,5-trimethylcyclohexyl) ester Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C1=CC=CC=C1O WSSJONWNBBTCMG-UHFFFAOYSA-N 0.000 claims description 6
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 6
- UQPHVQVXLPRNCX-UHFFFAOYSA-N erythrulose Chemical compound OCC(O)C(=O)CO UQPHVQVXLPRNCX-UHFFFAOYSA-N 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
- XVAMCHGMPYWHNL-UHFFFAOYSA-N bemotrizinol Chemical compound OC1=CC(OCC(CC)CCCC)=CC=C1C1=NC(C=2C=CC(OC)=CC=2)=NC(C=2C(=CC(OCC(CC)CCCC)=CC=2)O)=N1 XVAMCHGMPYWHNL-UHFFFAOYSA-N 0.000 claims description 5
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 claims description 5
- 229940068171 ethyl hexyl salicylate Drugs 0.000 claims description 5
- 229960004881 homosalate Drugs 0.000 claims description 5
- FMJSMJQBSVNSBF-UHFFFAOYSA-N octocrylene Chemical group C=1C=CC=CC=1C(=C(C#N)C(=O)OCC(CC)CCCC)C1=CC=CC=C1 FMJSMJQBSVNSBF-UHFFFAOYSA-N 0.000 claims description 5
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- 239000004408 titanium dioxide Substances 0.000 claims description 5
- BLCJBICVQSYOIF-UHFFFAOYSA-N 2,2-diaminobutanoic acid Chemical compound CCC(N)(N)C(O)=O BLCJBICVQSYOIF-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 206010061218 Inflammation Diseases 0.000 claims description 3
- 125000005002 aryl methyl group Chemical group 0.000 claims description 3
- 229960000655 ensulizole Drugs 0.000 claims description 3
- UVCJGUGAGLDPAA-UHFFFAOYSA-N ensulizole Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 claims description 3
- 230000004054 inflammatory process Effects 0.000 claims description 3
- 210000004761 scalp Anatomy 0.000 claims description 3
- 239000011787 zinc oxide Substances 0.000 claims description 3
- OIQXFRANQVWXJF-QBFSEMIESA-N (2z)-2-benzylidene-4,7,7-trimethylbicyclo[2.2.1]heptan-3-one Chemical compound CC1(C)C2CCC1(C)C(=O)\C2=C/C1=CC=CC=C1 OIQXFRANQVWXJF-QBFSEMIESA-N 0.000 claims description 2
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 claims description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 2
- 230000036074 healthy skin Effects 0.000 claims description 2
- 230000013632 homeostatic process Effects 0.000 claims description 2
- 208000000069 hyperpigmentation Diseases 0.000 claims description 2
- 230000003810 hyperpigmentation Effects 0.000 claims description 2
- 230000003020 moisturizing effect Effects 0.000 claims description 2
- 230000008591 skin barrier function Effects 0.000 claims description 2
- 244000005714 skin microbiome Species 0.000 claims description 2
- 229960001295 tocopherol Drugs 0.000 claims description 2
- 229930003799 tocopherol Natural products 0.000 claims description 2
- 235000010384 tocopherol Nutrition 0.000 claims description 2
- 239000011732 tocopherol Substances 0.000 claims description 2
- 229940042585 tocopherol acetate Drugs 0.000 claims description 2
- 229960001296 zinc oxide Drugs 0.000 claims description 2
- 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 claims description 2
- 210000003491 skin Anatomy 0.000 description 30
- 108090000765 processed proteins & peptides Proteins 0.000 description 20
- 239000000047 product Substances 0.000 description 16
- 239000000839 emulsion Substances 0.000 description 14
- 239000003995 emulsifying agent Substances 0.000 description 13
- 241000186427 Cutibacterium acnes Species 0.000 description 12
- 229940055019 propionibacterium acne Drugs 0.000 description 12
- 229910019142 PO4 Inorganic materials 0.000 description 11
- 241000191967 Staphylococcus aureus Species 0.000 description 11
- 235000001014 amino acid Nutrition 0.000 description 11
- 235000021317 phosphate Nutrition 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 239000008194 pharmaceutical composition Substances 0.000 description 10
- 239000010452 phosphate Substances 0.000 description 10
- 239000012071 phase Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 8
- 230000000813 microbial effect Effects 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 8
- 208000002874 Acne Vulgaris Diseases 0.000 description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical group OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
- 206010000496 acne Diseases 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 241000894006 Bacteria Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 102000004196 processed proteins & peptides Human genes 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 208000012868 Overgrowth Diseases 0.000 description 5
- 208000012641 Pigmentation disease Diseases 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
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- 239000006071 cream Substances 0.000 description 5
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- 230000002401 inhibitory effect Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
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- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
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- 239000000243 solution Substances 0.000 description 5
- 230000000699 topical effect Effects 0.000 description 5
- 229910052721 tungsten Inorganic materials 0.000 description 5
- CENPSTJGQOQKKW-UHFFFAOYSA-N 2,4,6-tris(4-phenylphenyl)-1,3,5-triazine Chemical compound C1=CC=CC=C1C1=CC=C(C=2N=C(N=C(N=2)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 CENPSTJGQOQKKW-UHFFFAOYSA-N 0.000 description 4
- OGNSCSPNOLGXSM-UHFFFAOYSA-N 2,4-diaminobutyric acid Chemical compound NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 4
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 4
- OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- UPOYFZYFGWBUKL-UHFFFAOYSA-N amiphenazole Chemical compound S1C(N)=NC(N)=C1C1=CC=CC=C1 UPOYFZYFGWBUKL-UHFFFAOYSA-N 0.000 description 4
- 229950001798 amiphenazole Drugs 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
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- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical class NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 3
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- FDATWRLUYRHCJE-UHFFFAOYSA-N diethylamino hydroxybenzoyl hexyl benzoate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1O FDATWRLUYRHCJE-UHFFFAOYSA-N 0.000 description 3
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- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000003860 topical agent Substances 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical class [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- ZGYICYBLPGRURT-UHFFFAOYSA-N tri(propan-2-yl)silicon Chemical compound CC(C)[Si](C(C)C)C(C)C ZGYICYBLPGRURT-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines 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
- 229940072029 trilaureth-4 phosphate Drugs 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 229940035936 ubiquinone Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1024—Tetrapeptides with the first amino acid being heterocyclic
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
-
- 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
- A61Q5/00—Preparations for care of the hair
- A61Q5/006—Antidandruff preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Birds (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Cosmetics (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP17199080.7 | 2017-10-30 | ||
| EP17199080 | 2017-10-30 | ||
| PCT/EP2018/079522 WO2019086361A1 (en) | 2017-10-30 | 2018-10-29 | Antimicrobial tetrapeptides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20200073278A KR20200073278A (ko) | 2020-06-23 |
| KR102694657B1 true KR102694657B1 (ko) | 2024-08-13 |
Family
ID=60409114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020207015187A Active KR102694657B1 (ko) | 2017-10-30 | 2018-10-29 | 항균성 테트라펩티드 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20200308222A1 (enExample) |
| EP (1) | EP3704134B1 (enExample) |
| JP (1) | JP7231307B2 (enExample) |
| KR (1) | KR102694657B1 (enExample) |
| CN (1) | CN111278846B (enExample) |
| BR (1) | BR112020008175A2 (enExample) |
| WO (1) | WO2019086361A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2025524352A (ja) * | 2022-06-15 | 2025-07-30 | ディーエスエム アイピー アセッツ ビー．ブイ． | にきびの処置のためのｕｖフィルターの使用 |
| WO2025174058A1 (ko) * | 2024-02-15 | 2025-08-21 | (주)뉴트리 | 탈모 유발 유해균에 대한 항균 효과를 갖는 두피 유래 펩타이드 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014081845A2 (en) | 2012-11-21 | 2014-05-30 | University Of Cincinnati | Skin care compositions and methods comprising selective agonists of melanocortin 1 receptor |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2466492A1 (en) | 1979-10-03 | 1981-04-10 | Elf Aquitaine | Dyeing keratin substances, e.g. skin, nails, hair, fur - with compsns. contg. ketone or aldehyde dye and sulphoxy-aminoacid |
| FR2651126B1 (fr) | 1989-08-29 | 1991-12-06 | Oreal | Association de dihydroxyacetone et de derives indoliques pour conferer a la peau une coloration similaire au bronzage naturel et procede de mise en óoeuvre. |
| FR2661673B1 (fr) | 1990-05-07 | 1992-08-21 | Oreal | Association de dihydroxyacetone et de monohydroxyindoles pour conferer a la peau une coloration similaire au bronzage naturel, dispositif a plusieurs compartiments et procede de mise en óoeuvre. |
| DE19603018C2 (de) | 1996-01-17 | 1998-02-26 | Lancaster Group Gmbh | Kosmetisches Selbstbräunungsmittel mit Lichtschutzwirkung |
| FR2746391B1 (fr) | 1996-03-22 | 1998-04-17 | Oreal | Compositions cosmetiques a base de pyrazolin-4,5-diones, nouvelles pyrazolin-4,5 diones, procedes de preparation et utilisations |
| FR2761595B1 (fr) | 1997-04-04 | 1999-09-17 | Oreal | Compositions comprenant des santalines, santarubines pour la coloration artificielle de la peau et utilisations |
| FR2768733B1 (fr) | 1997-09-19 | 1999-10-29 | Oreal | Nouveaux composes 4,4-dihydroxypyrazolin-5-ones ; leurs procedes de preparation et utilisations cosmetiques |
| FR2780281B1 (fr) | 1998-06-26 | 2000-08-18 | Oreal | Compositions comprenant des nanopigments d'oxydes de fer pour la coloration artificielle de la peau et utilisations |
| WO2012158960A2 (en) | 2011-05-17 | 2012-11-22 | H. Lee Moffitt Cancer Center & Research Institute, Inc. | Melanocortin 1 receptor ligands and methods of use |
-
2018
- 2018-10-29 US US16/759,851 patent/US20200308222A1/en not_active Abandoned
- 2018-10-29 BR BR112020008175-2A patent/BR112020008175A2/pt unknown
- 2018-10-29 KR KR1020207015187A patent/KR102694657B1/ko active Active
- 2018-10-29 JP JP2020520812A patent/JP7231307B2/ja active Active
- 2018-10-29 EP EP18795520.8A patent/EP3704134B1/en active Active
- 2018-10-29 WO PCT/EP2018/079522 patent/WO2019086361A1/en not_active Ceased
- 2018-10-29 CN CN201880070344.6A patent/CN111278846B/zh active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014081845A2 (en) | 2012-11-21 | 2014-05-30 | University Of Cincinnati | Skin care compositions and methods comprising selective agonists of melanocortin 1 receptor |
Also Published As
| Publication number | Publication date |
|---|---|
| EP3704134B1 (en) | 2021-12-22 |
| CN111278846A (zh) | 2020-06-12 |
| WO2019086361A1 (en) | 2019-05-09 |
| KR20200073278A (ko) | 2020-06-23 |
| JP7231307B2 (ja) | 2023-03-01 |
| CN111278846B (zh) | 2023-10-27 |
| US20200308222A1 (en) | 2020-10-01 |
| JP2021501133A (ja) | 2021-01-14 |
| EP3704134A1 (en) | 2020-09-09 |
| BR112020008175A2 (pt) | 2020-10-20 |
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