JP6976672B2 - 制汗剤 - Google Patents
制汗剤 Download PDFInfo
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- JP6976672B2 JP6976672B2 JP2020510691A JP2020510691A JP6976672B2 JP 6976672 B2 JP6976672 B2 JP 6976672B2 JP 2020510691 A JP2020510691 A JP 2020510691A JP 2020510691 A JP2020510691 A JP 2020510691A JP 6976672 B2 JP6976672 B2 JP 6976672B2
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- Japan
- Prior art keywords
- group
- formula
- antiperspirant
- sweat
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 230000001166 anti-perspirative effect Effects 0.000 title claims description 95
- 239000003213 antiperspirant Substances 0.000 title claims description 95
- 150000001875 compounds Chemical class 0.000 claims description 70
- 210000004243 sweat Anatomy 0.000 claims description 39
- 230000028327 secretion Effects 0.000 claims description 34
- 239000004480 active ingredient Substances 0.000 claims description 5
- BQENDLAVTKRQMS-SBBGFIFASA-L Carbenoxolone sodium Chemical compound [Na+].[Na+].C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C([O-])=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](OC(=O)CCC([O-])=O)C1(C)C BQENDLAVTKRQMS-SBBGFIFASA-L 0.000 claims description 4
- 229960000530 carbenoxolone Drugs 0.000 claims description 3
- 102000036770 Islet Amyloid Polypeptide Human genes 0.000 claims 1
- 108010041872 Islet Amyloid Polypeptide Proteins 0.000 claims 1
- 210000000106 sweat gland Anatomy 0.000 description 119
- 125000004432 carbon atom Chemical group C* 0.000 description 86
- 210000004027 cell Anatomy 0.000 description 56
- 125000000217 alkyl group Chemical group 0.000 description 55
- 230000003248 secreting effect Effects 0.000 description 47
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 38
- 125000001424 substituent group Chemical group 0.000 description 37
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 30
- -1 n-Heptyloxy group Chemical group 0.000 description 30
- 239000002953 phosphate buffered saline Substances 0.000 description 19
- 125000003545 alkoxy group Chemical group 0.000 description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 14
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 102000008186 Collagen Human genes 0.000 description 9
- 108010035532 Collagen Proteins 0.000 description 9
- 229920001436 collagen Polymers 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- 239000011148 porous material Substances 0.000 description 9
- 125000004423 acyloxy group Chemical group 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- MPDGHEJMBKOTSU-YKLVYJNSSA-N 18beta-glycyrrhetic acid Chemical compound C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C(O)=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-YKLVYJNSSA-N 0.000 description 7
- 125000002252 acyl group Chemical group 0.000 description 7
- 239000013068 control sample Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 239000012128 staining reagent Substances 0.000 description 6
- 230000035900 sweating Effects 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- MPDGHEJMBKOTSU-UHFFFAOYSA-N Glycyrrhetinsaeure Natural products C12C(=O)C=C3C4CC(C)(C(O)=O)CCC4(C)CCC3(C)C1(C)CCC1C2(C)CCC(O)C1(C)C MPDGHEJMBKOTSU-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- JFSHUTJDVKUMTJ-QHPUVITPSA-N beta-amyrin Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C JFSHUTJDVKUMTJ-QHPUVITPSA-N 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 5
- 210000003491 skin Anatomy 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- FSLPMRQHCOLESF-SFMCKYFRSA-N alpha-amyrin Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C FSLPMRQHCOLESF-SFMCKYFRSA-N 0.000 description 4
- 210000004292 cytoskeleton Anatomy 0.000 description 4
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 4
- WCGUUGGRBIKTOS-GPOJBZKASA-N (3beta)-3-hydroxyurs-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C WCGUUGGRBIKTOS-GPOJBZKASA-N 0.000 description 3
- NWJZWHGSBTVTGM-UHFFFAOYSA-N 1-[bis(aziridin-1-yl)phosphoryl]-3-phenylurea Chemical compound C1CN1P(=O)(N1CC1)NC(=O)NC1=CC=CC=C1 NWJZWHGSBTVTGM-UHFFFAOYSA-N 0.000 description 3
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 3
- MIJYXULNPSFWEK-GTOFXWBISA-N 3beta-hydroxyolean-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C MIJYXULNPSFWEK-GTOFXWBISA-N 0.000 description 3
- JKLISIRFYWXLQG-UHFFFAOYSA-N Epioleonolsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4CCC3C21C JKLISIRFYWXLQG-UHFFFAOYSA-N 0.000 description 3
- YBRJHZPWOMJYKQ-UHFFFAOYSA-N Oleanolic acid Natural products CC1(C)CC2C3=CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CCC2(C1)C(=O)O YBRJHZPWOMJYKQ-UHFFFAOYSA-N 0.000 description 3
- MIJYXULNPSFWEK-UHFFFAOYSA-N Oleanolinsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C MIJYXULNPSFWEK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 210000004207 dermis Anatomy 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229940100243 oleanolic acid Drugs 0.000 description 3
- HZLWUYJLOIAQFC-UHFFFAOYSA-N prosapogenin PS-A Natural products C12CC(C)(C)CCC2(C(O)=O)CCC(C2(CCC3C4(C)C)C)(C)C1=CCC2C3(C)CCC4OC1OCC(O)C(O)C1O HZLWUYJLOIAQFC-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- 229940096998 ursolic acid Drugs 0.000 description 3
- PLSAJKYPRJGMHO-UHFFFAOYSA-N ursolic acid Natural products CC1CCC2(CCC3(C)C(C=CC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1C)C(=O)O PLSAJKYPRJGMHO-UHFFFAOYSA-N 0.000 description 3
- 229940011671 vitamin b6 Drugs 0.000 description 3
- QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 2
- FMIMFCRXYXVFTA-FUAOEXFOSA-N (4as,6ar,6as,6br,8ar,12ar,14bs)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1h-picene-4a-carboxylic acid Chemical compound C1CC(=O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C FMIMFCRXYXVFTA-FUAOEXFOSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- 239000007995 HEPES buffer Substances 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- QCHFTSOMWOSFHM-UHFFFAOYSA-N SJ000285536 Natural products C1OC(=O)C(CC)C1CC1=CN=CN1C QCHFTSOMWOSFHM-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- FSLPMRQHCOLESF-UHFFFAOYSA-N alpha-amyrenol Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C)CCC(C)C(C)C5C4=CCC3C21C FSLPMRQHCOLESF-UHFFFAOYSA-N 0.000 description 2
- SJMCNAVDHDBMLL-UHFFFAOYSA-N alpha-amyrin Natural products CC1CCC2(C)CCC3(C)C(=CCC4C5(C)CCC(O)CC5CCC34C)C2C1C SJMCNAVDHDBMLL-UHFFFAOYSA-N 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- QQFMRPIKDLHLKB-UHFFFAOYSA-N beta-amyrin Natural products CC1C2C3=CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CCC2(C)CCC1(C)C QQFMRPIKDLHLKB-UHFFFAOYSA-N 0.000 description 2
- PDNLMONKODEGSE-UHFFFAOYSA-N beta-amyrin acetate Natural products CC(=O)OC1CCC2(C)C(CCC3(C)C4(C)CCC5(C)CCC(C)(C)CC5C4=CCC23C)C1(C)C PDNLMONKODEGSE-UHFFFAOYSA-N 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
- 229960000735 docosanol Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229960003720 enoxolone Drugs 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 159000000003 magnesium salts Chemical class 0.000 description 2
- 229940043348 myristyl alcohol Drugs 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- 238000012758 nuclear staining Methods 0.000 description 2
- 229940055577 oleyl alcohol Drugs 0.000 description 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229960001416 pilocarpine Drugs 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 235000008160 pyridoxine Nutrition 0.000 description 2
- 239000011677 pyridoxine Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229940012831 stearyl alcohol Drugs 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- PRDFBSVERLRRMY-UHFFFAOYSA-N 2'-(4-ethoxyphenyl)-5-(4-methylpiperazin-1-yl)-2,5'-bibenzimidazole Chemical compound C1=CC(OCC)=CC=C1C1=NC2=CC=C(C=3NC4=CC(=CC=C4N=3)N3CCN(C)CC3)C=C2N1 PRDFBSVERLRRMY-UHFFFAOYSA-N 0.000 description 1
- FMIMFCRXYXVFTA-UHFFFAOYSA-N 3-Oxo-12-oleanen-28-oic acid Natural products C1CC(=O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C FMIMFCRXYXVFTA-UHFFFAOYSA-N 0.000 description 1
- GXINOXZNGFTYEQ-UHFFFAOYSA-N CCC(C(C)(CCC(CCC1)C(C)(C)C1OC(C(C(C1O)O)OC(C(C(C2O)O)O)OC2C(O)=O)OC1C(O)=O)C(C)(CCC(C)(CC1)C2CC1(C)C(O)=O)C2=C1)C1=O Chemical compound CCC(C(C)(CCC(CCC1)C(C)(C)C1OC(C(C(C1O)O)OC(C(C(C2O)O)O)OC2C(O)=O)OC1C(O)=O)C(C)(CCC(C)(CC1)C2CC1(C)C(O)=O)C2=C1)C1=O GXINOXZNGFTYEQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VTAJIXDZFCRWBR-UHFFFAOYSA-N Licoricesaponin B2 Natural products C1C(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2)C(O)=O)C)(C)CC2)(C)C2C(C)(C)CC1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O VTAJIXDZFCRWBR-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241001290864 Schoenoplectus Species 0.000 description 1
- 206010051788 Sticky skin Diseases 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003943 azolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
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- 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000004410 cyclooctyloxy group Chemical group C1(CCCCCCC1)O* 0.000 description 1
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 description 1
- DGLRDKLJZLEJCY-UHFFFAOYSA-L disodium hydrogenphosphate dodecahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].OP([O-])([O-])=O DGLRDKLJZLEJCY-UHFFFAOYSA-L 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- FFDHYUFECJTEAY-UHFFFAOYSA-N epimacherinic acid Natural products CC1(C)CCC2(CCC3(C)C(CCC4C5(C)CCCC(C)(C)C5CCC34C)C2C1)C(=O)O FFDHYUFECJTEAY-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
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- LPLVUJXQOOQHMX-UHFFFAOYSA-N glycyrrhetinic acid glycoside Natural products C1CC(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2=O)C(O)=O)C)(C)CC2)(C)C2C(C)(C)C1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O LPLVUJXQOOQHMX-UHFFFAOYSA-N 0.000 description 1
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- 239000001685 glycyrrhizic acid Substances 0.000 description 1
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- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
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- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006610 n-decyloxy group Chemical group 0.000 description 1
- 125000006609 n-nonyloxy group Chemical group 0.000 description 1
- 125000006608 n-octyloxy group Chemical group 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
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- PGSADBUBUOPOJS-UHFFFAOYSA-N neutral red Chemical compound Cl.C1=C(C)C(N)=CC2=NC3=CC(N(C)C)=CC=C3N=C21 PGSADBUBUOPOJS-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/191—Carboxylic acids, e.g. valproic acid having two or more hydroxy groups, e.g. gluconic acid
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- 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
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic 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
- A61K8/60—Sugars; Derivatives thereof
- A61K8/602—Glycosides, e.g. rutin
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
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- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/63—Steroids; Derivatives thereof
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
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- 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
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Description
で表わされる基または式(III):
で表わされる基、R6は前記式(III)で表わされる基または式(V):
で表わされる基、R8およびR9はそれぞれ独立して水素原子、水酸基または炭素数1〜6のアルキル基、R10は炭素数1〜6のアルキル基またはカルボキシル基、R11は水素原子、水酸基、炭素数1〜6のアルキル基またはカルボキシル基、R12は水素原子、炭素数1〜6のアルキル基またはカルボキシル基、R13は水素原子または炭素数1〜6のアルキル基、R14は前記式(III)で表わされる基または式(VI):
で表わされる化合物、前記式(I)で表わされる化合物の誘導体、式(VII):
で表わされる化合物および前記式(VII)で表わされる化合物の誘導体からなる群より選ばれた少なくとも1種の五環式化合物を汗腺による汗の分泌を制御するための有効成分として含有することを特徴とする制汗剤に関する。
で表わされる基または式(III):
で表わされる基、R6は式(III)で表わされる基または式(V):
で表わされる基、R8およびR9はそれぞれ独立して水素原子、水酸基または炭素数1〜6のアルキル基、R10は炭素数1〜6のアルキル基またはカルボキシル基、R11は水素原子、水酸基、炭素数1〜6のアルキル基またはカルボキシル基、R12は水素原子、炭素数1〜6のアルキル基またはカルボキシル基、R13は水素原子または炭素数1〜6のアルキル基、R14は式(III)で表わされる基または式(VI):
で表わされる化合物、式(I)で表わされる化合物の誘導体、式(VII):
で表わされる化合物および式(VII)で表わされる化合物の誘導体からなる群より選ばれた少なくとも1種の五環式化合物を汗腺による汗の分泌を制御するための有効成分として含有することを特徴とする。
<略語の説明>
HEPES:2−[4−(2−ヒドロキシエチル)ピペラジン−1−イル]エタンスルホン酸
PBS:リン酸緩衝化生理食塩水
5×PBS:5倍濃度のリン酸緩衝化生理食塩水
PBS500μLに細胞骨格染色試薬〔サイトケラチン(Cytoskelton)社製、商品名:Acti−stain 488、Acti−stain 488の濃度:14μM〕3.5μLと、細胞膜染色試薬〔サーモフィッシャーサイエンティフィック(Thermo Fisher Scientific)社製、商品名:CellMask〕4μLと、核染色試薬〔Hoechst33342〕1μLとを添加し、染色試薬混合液を得た。
コラーゲン タイプI−A液(コラーゲン タイプI−Aの含有率:3質量%)〔新田ゼラチン(株)製〕700μLと、5×PBS〔組成:685mM塩化ナトリウム、13.5mM塩化カリウム、50mMリン酸水素二ナトリウム十二水和物および9mMリン酸二水素カリウム、pH7.4〕200μLと、コラーゲン再構成緩衝液〔組成:50mM水酸化ナトリウム、260mM HEPESおよび200mM炭酸水素ナトリウム、pH10.0〕100μLとを混合することにより、コラーゲン含有液を得た。
汗腺収縮誘導試薬であるピロカルピンをその濃度が100mMとなるようにPBSに添加し、汗腺刺激剤を得た。
式(VIII)で表わされる化合物をその濃度が100mMとなるようにPBSに添加し、制汗剤を得た。
以下において、PBSを比較例1の対照試料として用いた。
(1)全汗腺の単離
皮膚組織として、生体から摘出後すぐに冷蔵され、4℃で15時間保存された皮膚組織を用いた。皮膚組織を10μM染色剤〔ニュートラルレッド(Neutral Red)〕含有PBSに浸すことにより、当該皮膚組織中の汗腺に染色剤を取り込ませた。つぎに、染色剤を取り込んだ皮膚組織の真皮部分を細かく裁断し、真皮細片を得た。光学顕微鏡下にピンセットを用い、真皮細片から全汗腺を採取した。
試験例1(1)で得られた全汗腺を製造例1で得られた染色試薬混合液中に室温(24℃)で30分間浸漬させることにより、全汗腺を染色した。染色された全汗腺をPBSで洗浄した。
実体顕微鏡〔ライカ(Leica)社製、商品名:M125〕下において、試験例1(2)で得られた洗浄後の全汗腺をガラスボトムディッシュに静置した。ガラスボトムディッシュに静置された全汗腺に、製造例2で得られたコラーゲン含有液Aを滴下した。つぎに、前記ガラスボトムディッシュを37℃で5分間インキュベーションすることにより、前記全汗腺にコラーゲン含有液に含まれるコラーゲン タイプI−Aをゲル化させた。その後、全汗腺が乾燥しないように、前記全汗腺上にPBS300μLを添加した。これにより、全汗腺が位置ずれしないように、コラーゲン タイプI−Aによって前記全汗腺を支持体であるガラスボトムディッシュに保持させて観察試料を得た。
観察試料において、ゲル化したコラーゲン タイプI−Aによって全汗腺がガラスボトムディッシュに接着していることを実体顕微鏡下で確認しながら、ダルベッコリン酸緩衝液〔ギブコ(Gibco)社製、カタログ番号:14190−144〕適量を支持体であるガラスボトムディッシュに添加した。
X:634.662μm
Y:634.662μm
Z:30μm
Zインターバル:1.5μm
Z枚数:21枚
タイムインターバル:30秒間
全フレーム数:61フレーム
全観察時間:1800秒間
Xn+1-Xn (XI)
(式中、nは1〜61の整数を示す)
Yn+1-Yn (XII)
(式中、nは前記と同じ)
にしたがって求めた。つぎに、三平方の定理(a2+b2=c2)にしたがい、式(XIII):
(Xn+1−Xn)2+(Yn+1−Yn)2 (XIII)
(式中、nは前記と同じ)
の平方根を算出することにより、連続するフレーム間毎の細胞の核の間の移動値を求めた。さらに、実際の移動距離を求めるため、取得画像の大きさ〔634.662μm×634.662μm〕とピクセル(512×512)から、座標1あたりの単位(μm/ピクセル)を求めた。移動値と座標1あたりの大きさを乗じて実際の細胞の核の移動距離(μm)を算出した。つぎに、各細胞の核の移動距離を用いて分泌管の管腔内の細胞の核の移動距離の平均値および分泌管の外縁部の細胞の核の移動距離の平均値を調べた。
18α−グリチルレチン酸をその濃度が10mMとなるようにPBSに添加し、制汗剤を得た。
18β−グリチルレチン酸をその濃度が10mMとなるようにPBSに添加し、制汗剤を得た。
ウルソール酸をその濃度が10mMとなるようにPBSに添加し、制汗剤を得た。
オレアノール酸をその濃度が100μMとなるようにPBSに添加し、制汗剤を得た。
α―アミリンをその濃度が2mMとなるようにPBSに添加し、制汗剤を得た。
β−アミリンをその濃度が2mMとなるようにPBSに添加し、制汗剤を得た。
ピロカルピンをその濃度が10mMとなるようにPBSに添加し、汗腺刺激剤を得た。
試験例1において、実施例1で得られた制汗剤を用いる代わりに実施例2〜7で得られた各制汗剤を用いたこと、製造例3で得られた汗腺刺激剤を用いる代わりに製造例4で得られた汗腺刺激剤を用いたことおよび全汗腺のタイムラプス撮影画像中の分泌管の管腔内の細胞群と分泌管の外縁部の細胞群とから各5個の細胞を選択する代わりに全汗腺のタイムラプス撮影画像中の分泌管の細胞群から5個の細胞を選択したことを除き、試験例1と同様の操作を行ない、実施例2〜7で得られた各制汗剤と全汗腺とを接触させたときの汗腺の分泌管の細胞の核の移動距離の平均値の経時的変化を調べた。
<<評価基準>>
汗腺の分泌管の細胞の核の移動距離の平均値の最大値が1μm以下:汗腺の分泌管の細胞の核が移動していない。
汗腺の分泌管の細胞の核の移動距離の平均値の最大値が1μmを超える:汗腺の分泌管の細胞の核が移動している。
評価技能の習熟度が同じである専門パネラー10名それぞれの脇下に実施例1で得られた制汗剤を塗布した後、専門パネラーに軽い運動を行なわせる。その後、専門パネラーに、以下の評価基準に基づいて発汗の度合いの得点をつけさせる。また、前記において、実施例1で得られた制汗剤を用いる代わりに比較例1の対照試料を用いることを除き、前記と同様に、専門パネラーに、発汗の度合いの得点をつけさせる。専門パネラーによってつけられた得点の平均値を求める。
<評価基準>
0点:大量の汗をかいている。
1点:汗をかいている。
2点:わずかに汗をかいている。
3点:ほとんど汗をかいていない。
4点:汗をかいていない。
Claims (1)
- 汗の分泌を抑制するための制汗剤であって、カルベノキソロン、カルベノキソロン2ナトリウム、α−アミリンおよびβ−アミリンからなる群より選ばれた少なくとも1種の五環式化合物を汗の分泌を抑制するための有効成分として含有することを特徴とする制汗剤。
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PCT/JP2019/011137 WO2019188486A1 (ja) | 2018-03-28 | 2019-03-18 | 制汗剤 |
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EP (1) | EP3777824A4 (ja) |
JP (1) | JP6976672B2 (ja) |
KR (1) | KR102321738B1 (ja) |
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DE2523866C3 (de) * | 1975-05-30 | 1980-09-25 | Rainer Dr. 2360 Bad Segeberg Greve | Schweißhemmendes Mittel |
FR2535203A1 (fr) * | 1982-10-28 | 1984-05-04 | Jean Daniel | Nouvelle composition therapeutique a base d'une association d'un acide amine avec un triterpene et son procede de preparation |
FR2541895B1 (fr) * | 1983-03-04 | 1985-08-16 | Jean Daniel | Composition deodorante et antitranspirante a base d'acide triterpenique |
JPH03193727A (ja) * | 1989-12-22 | 1991-08-23 | Kao Corp | 腋臭防止剤 |
JPH05814A (ja) | 1990-10-26 | 1993-01-08 | Taimei Kagaku Kogyo Kk | 塩基性塩化アルミニウム粉末およびこれの製造方法 |
JP3614455B2 (ja) * | 1993-11-29 | 2005-01-26 | 東洋ビューティ株式会社 | 収斂・結着性化合物および医療用・化粧用製剤 |
JPH0967253A (ja) * | 1995-09-04 | 1997-03-11 | Lion Corp | 生体タンパク質変性抑制剤 |
DE19625015A1 (de) * | 1996-06-22 | 1998-01-02 | Wella Ag | Haarbehandlungsmittel mit Depotwirkung |
JP2001181174A (ja) * | 1999-12-24 | 2001-07-03 | Koki Kk | 化粧料組成物 |
WO2005039610A1 (en) * | 2003-10-24 | 2005-05-06 | Cognis France, S.A.S. | A plant extract and its pharmaceutical and cosmetic use |
DE102013215936A1 (de) * | 2013-08-12 | 2015-02-12 | Beiersdorf Ag | Deodorant- und/oder Antitranspirantzubereitungen umfassend polyzyklische Michael-Akzeptoren |
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CN111032010A (zh) | 2020-04-17 |
WO2019188486A1 (ja) | 2019-10-03 |
KR20200032171A (ko) | 2020-03-25 |
US20210361549A1 (en) | 2021-11-25 |
EP3777824A4 (en) | 2022-03-09 |
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