JP2016510775A - アルキルアミドチアゾール類と保存剤とからなる組合せ物 - Google Patents
アルキルアミドチアゾール類と保存剤とからなる組合せ物 Download PDFInfo
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- JP2016510775A JP2016510775A JP2015561998A JP2015561998A JP2016510775A JP 2016510775 A JP2016510775 A JP 2016510775A JP 2015561998 A JP2015561998 A JP 2015561998A JP 2015561998 A JP2015561998 A JP 2015561998A JP 2016510775 A JP2016510775 A JP 2016510775A
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- 239000003755 preservative agent Substances 0.000 title claims abstract description 15
- 239000002537 cosmetic Substances 0.000 claims abstract description 20
- 239000013543 active substance Substances 0.000 claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 53
- 238000002360 preparation method Methods 0.000 claims description 44
- -1 ethyl alginate Chemical compound 0.000 claims description 23
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 17
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 13
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 10
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Chemical compound CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 claims description 6
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 claims description 6
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims description 6
- CHHHXKFHOYLYRE-STWYSWDKSA-M potassium sorbate Chemical compound [K+].C\C=C\C=C\C([O-])=O CHHHXKFHOYLYRE-STWYSWDKSA-M 0.000 claims description 6
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 230000002087 whitening effect Effects 0.000 claims description 6
- NCZPCONIKBICGS-UHFFFAOYSA-N 3-(2-ethylhexoxy)propane-1,2-diol Chemical compound CCCCC(CC)COCC(O)CO NCZPCONIKBICGS-UHFFFAOYSA-N 0.000 claims description 5
- 239000005711 Benzoic acid Substances 0.000 claims description 5
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 5
- 235000010233 benzoic acid Nutrition 0.000 claims description 5
- 229960004365 benzoic acid Drugs 0.000 claims description 5
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 5
- 229960004889 salicylic acid Drugs 0.000 claims description 5
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 claims description 5
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims description 4
- 239000004287 Dehydroacetic acid Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 235000019258 dehydroacetic acid Nutrition 0.000 claims description 4
- 229940061632 dehydroacetic acid Drugs 0.000 claims description 4
- WSDISUOETYTPRL-UHFFFAOYSA-N dmdm hydantoin Chemical compound CC1(C)N(CO)C(=O)N(CO)C1=O WSDISUOETYTPRL-UHFFFAOYSA-N 0.000 claims description 4
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 claims description 4
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 claims description 4
- RGUVUPQQFXCJFC-UHFFFAOYSA-N n-hydroxyoctanamide Chemical compound CCCCCCCC(=O)NO RGUVUPQQFXCJFC-UHFFFAOYSA-N 0.000 claims description 4
- AEIJTFQOBWATKX-UHFFFAOYSA-N octane-1,2-diol Chemical compound CCCCCCC(O)CO AEIJTFQOBWATKX-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- BTSZTGGZJQFALU-UHFFFAOYSA-N piroctone olamine Chemical compound NCCO.CC(C)(C)CC(C)CC1=CC(C)=CC(=O)N1O BTSZTGGZJQFALU-UHFFFAOYSA-N 0.000 claims description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 4
- GHBFNMLVSPCDGN-UHFFFAOYSA-N rac-1-monooctanoylglycerol Chemical compound CCCCCCCC(=O)OCC(O)CO GHBFNMLVSPCDGN-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 235000010199 sorbic acid Nutrition 0.000 claims description 4
- 239000004334 sorbic acid Substances 0.000 claims description 4
- 229940075582 sorbic acid Drugs 0.000 claims description 4
- 150000003557 thiazoles Chemical class 0.000 claims description 4
- 229940100555 2-methyl-4-isothiazolin-3-one Drugs 0.000 claims description 3
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 235000010323 ascorbic acid Nutrition 0.000 claims description 3
- 229960001950 benzethonium chloride Drugs 0.000 claims description 3
- 229940100524 ethylhexylglycerin Drugs 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- 239000004299 sodium benzoate Substances 0.000 claims description 3
- 235000010234 sodium benzoate Nutrition 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- 229940015975 1,2-hexanediol Drugs 0.000 claims description 2
- 229940031723 1,2-octanediol Drugs 0.000 claims description 2
- 229940043375 1,5-pentanediol Drugs 0.000 claims description 2
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 2
- 229940072056 alginate Drugs 0.000 claims description 2
- 235000010443 alginic acid Nutrition 0.000 claims description 2
- 229920000615 alginic acid Polymers 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 229960001617 ethyl hydroxybenzoate Drugs 0.000 claims description 2
- 239000004403 ethyl p-hydroxybenzoate Substances 0.000 claims description 2
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 claims description 2
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 229940087068 glyceryl caprylate Drugs 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 claims description 2
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 claims description 2
- 229960002216 methylparaben Drugs 0.000 claims description 2
- 229940100573 methylpropanediol Drugs 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 claims description 2
- 229960005323 phenoxyethanol Drugs 0.000 claims description 2
- 229940081510 piroctone olamine Drugs 0.000 claims description 2
- 235000010241 potassium sorbate Nutrition 0.000 claims description 2
- 239000004302 potassium sorbate Substances 0.000 claims description 2
- 229940069338 potassium sorbate Drugs 0.000 claims description 2
- 230000002335 preservative effect Effects 0.000 claims description 2
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 claims description 2
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 claims description 2
- 229960003415 propylparaben Drugs 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 150000000994 L-ascorbates Chemical class 0.000 claims 1
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 235000021317 phosphate Nutrition 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- 239000003643 water by type Substances 0.000 claims 1
- 235000021472 generally recognized as safe Nutrition 0.000 abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 20
- 208000012641 Pigmentation disease Diseases 0.000 description 20
- 210000003491 skin Anatomy 0.000 description 17
- 238000010992 reflux Methods 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 12
- 206010061218 Inflammation Diseases 0.000 description 11
- 239000012071 phase Substances 0.000 description 10
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 9
- FRZITBSDHBZGHN-UHFFFAOYSA-N [2-(2-bromoacetyl)-5-methoxycarbonyloxyphenyl] methyl carbonate Chemical compound COC(=O)OC1=CC=C(C(=O)CBr)C(OC(=O)OC)=C1 FRZITBSDHBZGHN-UHFFFAOYSA-N 0.000 description 9
- 210000002780 melanosome Anatomy 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000019612 pigmentation Effects 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 208000000069 hyperpigmentation Diseases 0.000 description 6
- 230000003810 hyperpigmentation Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000002562 thickening agent Substances 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- AHMIDUVKSGCHAU-LURJTMIESA-N L-dopaquinone Chemical compound [O-]C(=O)[C@@H]([NH3+])CC1=CC(=O)C(=O)C=C1 AHMIDUVKSGCHAU-LURJTMIESA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000010908 decantation Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 230000004054 inflammatory process Effects 0.000 description 4
- 210000002752 melanocyte Anatomy 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
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- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 102000003425 Tyrosinase Human genes 0.000 description 3
- 108060008724 Tyrosinase Proteins 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 210000002615 epidermis Anatomy 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 210000002510 keratinocyte Anatomy 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- YFTGOBNOJKXZJC-UHFFFAOYSA-N 5,6-dihydroxyindole-2-carboxylic acid Chemical compound OC1=C(O)C=C2NC(C(=O)O)=CC2=C1 YFTGOBNOJKXZJC-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- AHMIDUVKSGCHAU-UHFFFAOYSA-N Dopaquinone Natural products OC(=O)C(N)CC1=CC(=O)C(=O)C=C1 AHMIDUVKSGCHAU-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 206010014970 Ephelides Diseases 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 2
- 208000003351 Melanosis Diseases 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 102000040945 Transcription factor Human genes 0.000 description 2
- 108091023040 Transcription factor Proteins 0.000 description 2
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 210000002468 fat body Anatomy 0.000 description 2
- BJRNKVDFDLYUGJ-RMPHRYRLSA-N hydroquinone O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-RMPHRYRLSA-N 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000008099 melanin synthesis Effects 0.000 description 2
- 230000003020 moisturizing effect Effects 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 1
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
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- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
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Abstract
Description
R1、R2、XおよびYは、異なって、部分的に同一、または完全に同一であってよく、かつ互いに独立して以下の意味を有してよい:
R1は、−C1〜C24−アルキル(直鎖状および分枝鎖状)、−C1〜C24−アルケニル(直鎖状および分枝鎖状)、−C1〜C8−シクロアルキル、−C1〜C8−シクロアルキル−アルキルヒドロキシ、−C1〜C24−アルキルヒドロキシ(直鎖状および分枝鎖状)、−C1〜C24−アルキルアミン(直鎖状および分枝鎖状)、−C1〜C24−アルキルアリール(直鎖状および分枝鎖状)、−C1〜C24−アルキルアリール−アルキル−ヒドロキシ(直鎖状および分枝鎖状)、−C1〜C24−アルキルヘテロアリール(直鎖状および分枝鎖状)、−C1〜C24−アルキル−O−C1〜C24−アルキル(直鎖状および分枝鎖状)、−C1〜C24−アルキル−モルホリノ、−C1〜C24−アルキルピペリジノ、−C1〜C24−アルキル−ピペラジノ、−C1〜C24−アルキル−ピペラジノ−N−アルキルを意味し、
R2は、H、−C1〜C24−アルキル(直鎖状および分枝鎖状)、−C1〜C24−アルケニル(直鎖状および分枝鎖状)、−C1〜C8−シクロアルキル、−C1〜C24−ヒドロキシアルキル(直鎖状および分枝鎖状)、−C1〜C24−アルキルアリール(直鎖状および分枝鎖状)、−C1〜C24−アルキルヘテロアリール(直鎖状および分枝鎖状)を意味し、
Xは、−H、−C1〜C24−アルキル(直鎖状および分枝鎖状)、−C1〜C24−アルケニル(直鎖状および分枝鎖状)、−C1〜C8−シクロアルキル、−C1〜C24−アリール(場合により−OH、−F、−Cl、−Br、−I、−OMe、−NH2、−CNで一置換または多置換されている)、−C1〜C24−ヘテロアリール(場合により、−OH、−F、−Cl、−Br、−I、−OMe、−NH2、−CNで一置換または多置換されている)、−C1〜C24−アルキルアリール(直鎖状および分枝鎖状)、−C1〜C24−アルキルヘテロアリール(直鎖状および分枝鎖状)、−アリール(場合により、−OH、−F、−Cl、−Br、−I、−OMe、−NH2、−CNで一置換または多置換されている)、−フェニル、−2,4−ジヒドロキシフェニル、−2,3−ジヒドロキシフェニル、−2,4−ジメトキシフェニル、−2,3−ジメトキシフェニルを意味し、
Yは、H、−C1〜C24−アルキル(直鎖状および分枝鎖状)、−C1〜C24−アルケニル(直鎖状および分枝鎖状)、−C1〜C8−シクロアルキル、−C1〜C24−アリール、−C1〜C24−ヘテロアリール、−C1〜C24−アルキルアリール(直鎖状および分枝鎖状)、−C1〜C24−アルキルヘテロアリール(直鎖状および分枝鎖状)、−アリール、−フェニル、−2,4−ジヒドロキシフェニル、−2,3−ジヒドロキシフェニル、−2,4−ジメトキシフェニル、−2,3−ジメトキシフェニル、−COO−アルキル、−COO−アルケニル、−COO−シクロアルキル、−COO−アリール、−COO−ヘテロアリールを意味し、
かつX、Yは、場合によりまた縮合された芳香族を意味してよく、
その際、XおよびYは、互いに、n個までの環を形成する原子を有する芳香族または脂肪族の同素環式または複素環式の環系を形成してよく、かつ数nは、5〜8の値を取ることができ、かつそれぞれの環系は、更にn−1個までのアルキル基、ヒドロキシル基、カルボキシル基、アミノ基、ニトリル官能基、硫黄含有置換基、エステル基、および/またはエーテル基で置換されていてよい]の物質である。
Xは、
Yは、Hであり、
R1は、−C1〜C24−アルキル(直鎖状および分枝鎖状)、−C1〜C24−アルケニル(直鎖状および分枝鎖状)、−C1〜C8−シクロアルキル、−C1〜C8−シクロアルキル−アルキルヒドロキシ、−C1〜C24−アルキルヒドロキシ(直鎖状および分枝鎖状)、−C1〜C24−アルキルアミン(直鎖状および分枝鎖状)、−C1〜C24−アルキルアリール(直鎖状および分枝鎖状)、−C1〜C24−アルキルアリール−アルキル−ヒドロキシ(直鎖状および分枝鎖状)、−C1〜C24−アルキルヘテロアリール(直鎖状および分枝鎖状)、−C1〜C24−アルキル−O−C1〜C24−アルキル(直鎖状および分枝鎖状)、−C1〜C24−アルキル−モルホリノ、−C1〜C24−アルキル−ピペリジノ、−C1〜C24−アルキル−ピペラジノ、−C1〜C24−アルキル−ピペラジノ−N−アルキルを意味し、
R2は、H、−C1〜C24−アルキル(直鎖状および分枝鎖状)であり、
Zは、−H、−OH、−F、−Cl、−Br、−I、−OMe、−NH2、−CN、アセチルである化合物が好ましい。
Xは、
Yは、Hであり、
R1は、−C1〜C24−アルキル(直鎖状および分枝鎖状)、−C1〜C24−アルケニル(直鎖状および分枝鎖状)、−C1〜C8−シクロアルキル、−C1〜C8−シクロアルキル−アルキルヒドロキシ、−C1〜C24−アルキルヒドロキシ(直鎖状および分枝鎖状)、−C1〜C24−アルキルアミン(直鎖状および分枝鎖状)、−C1〜C24−アルキルアリール(直鎖状および分枝鎖状)、−C1〜C24−アルキルアリール−アルキル−ヒドロキシ(直鎖状および分枝鎖状)、−C1〜C24−アルキルヘテロアリール(直鎖状および分枝鎖状)、−C1〜C24−アルキル−O−C1〜C24−アルキル(直鎖状および分枝鎖状)、−C1〜C24−アルキル−モルホリノ、−C1〜C24−アルキル−ピペリジノ、−C1〜C24−アルキル−ピペラジノ、−C1〜C24−アルキル−ピペラジノ−N−アルキルを意味し、
R2は、Hである化合物が好ましい。
チアゾールの有効性は、L−ドーパのヒトチロシナーゼによるL−ドーパキノンへの転化を測定した酵素試験で裏付けた。この文献公知の方法(Winder, A.J.およびHarris, H.、チロシナーゼのおよびドーパオキシダーゼ活性のための新たなアッセイ(New assays for the tyrosine hydroxylase and dopa oxidwase activities of tyrosinase). Eur. J. Biochem. (1991)、198、317〜26)では、反応生成物のL−ドーパキノンは、MBTH(3−メチル−2−ベンゾチアゾリンヒドラゾン)と反応してピンク色の物質に変わり、その増大を経時的に490nmの吸収によって測定する。第1表に、特許請求の範囲に記載の物質の幾つかについての有効性データが例示されている。そのデータから、本発明による物質は極めて有効な色素沈着阻害物質であると推定できる。
− 鉱油、鉱蝋
− 油、例えばカプリン酸またはカプリル酸のトリグリセリド、更に天然油、例えばヒマシ油
− 脂肪、蝋ならびに別の天然および合成の脂肪体、好ましくは脂肪酸と少ない炭素数のアルコールとのエステル、例えばイソプロパノール、プロピレングリコールもしくはグリセリンとのエステル、または脂肪アルコールと少ない炭素数のアルカン酸もしくは脂肪酸とのエステル
− アルキルベンゾエート
− シリコーン油、例えばジメチルポリシロキサン、ジエチルポリシロキサン、ジフェニルポリシロキサン、ならびにそれらの混合形から選択することができる。
Claims (15)
- 1種以上のアルキルアミドチアゾールと、1種以上の化粧用または皮膚用に一般に安全と認められる保存剤とからなる作用物質の組合せ物。
- 前記1種以上の保存剤は、エチルパラベン(120−47−80)、プロピルパラベン(94−13−3)、メチルイソチアゾリノン(2682−20−4)、メチルプロパンジオール(2163−42−0)、ブチレングリコール(107−88−0)、プロピレングリコール(57−55−6、4254−14−2、4254−15−3)、エチルヘキシルグリセリン(70445−33−9)、安息香酸ナトリウム(532−32−1)、1,2−ヘキサンジオール(6920−22−5)、1,3−ブタンジオール(107−88−0)、1,2−オクタンジオール(1117−86−8)、ソルビン酸カリウム(24634−61−5/590−00−1)、DMDMヒダントイン(6440−58−0)、ベンジルアルコール(100−51−6)、フェノキシエタノール(122−99−6)、デヒドロ酢酸(520−45−6)、ピロクトンオラミン(68890−66−4)、メチルパラベン(99−76−3)、アルコール(64−17−5)、オクタンヒドロキサム酸(7377−03−9)、ベンゼトニウムクロリド(121−54−0)、グリセリルカプリレート(26402−26−6)、ペンチレングリコール(111−29−5)、ラウロイルエチルアルギネート(60372−77−2)、サリチル酸(69−72−7)、安息香酸(65−85−0)、プロピオン酸(79−09−4)、ソルビン酸(110−44−1)の群から選択され、その際、サリチル酸、安息香酸およびデヒドロ酢酸が好ましく、これらの酸の生理学的に認容性の水溶性金属塩を使用することが好ましいこともあることを特徴とする、請求項1に記載の作用物質の組合せ物。
- 前記1種以上のアルキルアミドチアゾールは、一般式
R1、R2、XおよびYは、異なって、部分的に同一、または完全に同一であってよく、かつ互いに独立して以下の意味を有してよい:
R1は、−C1〜C24−アルキル(直鎖状および分枝鎖状)、−C1〜C24−アルケニル(直鎖状および分枝鎖状)、−C1〜C8−シクロアルキル、−C1〜C8−シクロアルキル−アルキルヒドロキシ、−C1〜C24−アルキルヒドロキシ(直鎖状および分枝鎖状)、−C1〜C24−アルキルアミン(直鎖状および分枝鎖状)、−C1〜C24−アルキルアリール(直鎖状および分枝鎖状)、−C1〜C24−アルキルアリール−アルキル−ヒドロキシ(直鎖状および分枝鎖状)、−C1〜C24−アルキルヘテロアリール(直鎖状および分枝鎖状)、−C1〜C24−アルキル−O−C1〜C24−アルキル(直鎖状および分枝鎖状)、−C1〜C24−アルキル−モルホリノ、−C1〜C24−アルキルピペリジノ、−C1〜C24−アルキル−ピペラジノ、−C1〜C24−アルキル−ピペラジノ−N−アルキルを意味し、
R2は、H、−C1〜C24−アルキル(直鎖状および分枝鎖状)、−C1〜C24−アルケニル(直鎖状および分枝鎖状)、−C1〜C8−シクロアルキル、−C1〜C24−ヒドロキシアルキル(直鎖状および分枝鎖状)、−C1〜C24−アルキルアリール(直鎖状および分枝鎖状)、−C1〜C24−アルキルヘテロアリール(直鎖状および分枝鎖状)を意味し、
Xは、−H、−C1〜C24−アルキル(直鎖状および分枝鎖状)、−C1〜C24−アルケニル(直鎖状および分枝鎖状)、−C1〜C8−シクロアルキル、−C1〜C24−アリール(場合により−OH、−F、−Cl、−Br、−I、−OMe、−NH2、−CNで一置換または多置換されている)、−C1〜C24−ヘテロアリール(場合により、−OH、−F、−Cl、−Br、−I、−OMe、−NH2、−CNで一置換または多置換されている)、−C1〜C24−アルキルアリール(直鎖状および分枝鎖状)、−C1〜C24−アルキルヘテロアリール(直鎖状および分枝鎖状)、−アリール(場合により、−OH、−F、−Cl、−Br、−I、−OMe、−NH2、−CNで一置換または多置換されている)、−フェニル、−2,4−ジヒドロキシフェニル、−2,3−ジヒドロキシフェニル、−2,4−ジメトキシフェニル、−2,3−ジメトキシフェニルを意味し、
Yは、H、−C1〜C24−アルキル(直鎖状および分枝鎖状)、−C1〜C24−アルケニル(直鎖状および分枝鎖状)、−C1〜C8−シクロアルキル、−C1〜C24−アリール、−C1〜C24−ヘテロアリール、−C1〜C24−アルキルアリール(直鎖状および分枝鎖状)、−C1〜C24−アルキルヘテロアリール(直鎖状および分枝鎖状)、−アリール、−フェニル、−2,4−ジヒドロキシフェニル、−2,3−ジヒドロキシフェニル、−2,4−ジメトキシフェニル、−2,3−ジメトキシフェニル、−COO−アルキル、−COO−アルケニル、−COO−シクロアルキル、−COO−アリール、−COO−ヘテロアリールを意味し、
かつX、Yは、場合によりまた縮合された芳香族を意味してよく、
その際、XおよびYは、互いに、n個までの環を形成する原子を有する芳香族または脂肪族の同素環式または複素環式の環系を形成してよく、かつ数nは、5〜8の値を取ることができ、かつそれぞれの環系は、更にn−1個までのアルキル基、ヒドロキシル基、カルボキシル基、アミノ基、ニトリル官能基、硫黄含有置換基、エステル基、および/またはエーテル基で置換されていてよい]の物質であり、前記1種以上のアルキルアミドチアゾールは、遊離塩基としても、化粧用に、および皮膚用に使用可能な塩としても存在しうることを特徴とする、請求項1または2に記載の作用物質の組合せ物。 - Xは、置換されたフェニル基の群から選択され、かつY、R1およびR2は、請求項3に定義される特性を有しうることを特徴とする、請求項3に記載の作用物質の組合せ物。
- 前記1種以上のアルキルアミドチアゾールは、以下の構造を有し、式中、
Xは、
Yは、Hであり、
R1は、−C1〜C24−アルキル(直鎖状および分枝鎖状)、−C1〜C24−アルケニル(直鎖状および分枝鎖状)、−C1〜C8−シクロアルキル、−C1〜C8−シクロアルキル−アルキルヒドロキシ、−C1〜C24−アルキルヒドロキシ(直鎖状および分枝鎖状)、−C1〜C24−アルキルアミン(直鎖状および分枝鎖状)、−C1〜C24−アルキルアリール(直鎖状および分枝鎖状)、−C1〜C24−アルキルアリール−アルキル−ヒドロキシ(直鎖状および分枝鎖状)、−C1〜C24−アルキルヘテロアリール(直鎖状および分枝鎖状)、−C1〜C24−アルキル−O−C1〜C24−アルキル(直鎖状および分枝鎖状)、−C1〜C24−アルキル−モルホリノ、−C1〜C24−アルキル−ピペリジノ、−C1〜C24−アルキル−ピペラジノ、−C1〜C24−アルキル−ピペラジノ−N−アルキルを意味し、
R2は、H、−C1〜C24−アルキル(直鎖状および分枝鎖状)であり、
Zは、−H、−OH、−F、−Cl、−Br、−I、−OMe、−NH2、−CN、アセチルであることを特徴とする、請求項1から6までのいずれか1項に記載の作用物質の組合せ物。 - 前記1種以上のアルキルアミドチアゾールは、以下の構造を有し、式中、
Xは、
Yは、Hであり、
R1は、−C1〜C24−アルキル(直鎖状および分枝鎖状)、−C1〜C24−アルケニル(直鎖状および分枝鎖状)、−C1〜C8−シクロアルキル、−C1〜C8−シクロアルキル−アルキルヒドロキシ、−C1〜C24−アルキルヒドロキシ(直鎖状および分枝鎖状)、−C1〜C24−アルキルアミン(直鎖状および分枝鎖状)、−C1〜C24−アルキルアリール(直鎖状および分枝鎖状)、−C1〜C24−アルキルアリール−アルキル−ヒドロキシ(直鎖状および分枝鎖状)、−C1〜C24−アルキルヘテロアリール(直鎖状および分枝鎖状)、−C1〜C24−アルキル−O−C1〜C24−アルキル(直鎖状および分枝鎖状)、−C1〜C24−アルキル−モルホリノ、−C1〜C24−アルキル−ピペリジノ、−C1〜C24−アルキル−ピペラジノ、−C1〜C24−アルキル−ピペラジノ−N−アルキルを意味し、
R2は、Hであることを特徴とする、請求項1から7までのいずれか1項に記載の作用物質の組合せ物。 - 前記1種以上のアルキルアミドチアゾールは、ハロゲン化物、炭酸塩、アスコルビン酸塩、硫酸塩、酢酸塩、および/またはリン酸塩として存在しうることを特徴とする、請求項1から9までのいずれか1項に記載の作用物質の組合せ物。
- 請求項1から10までのいずれか1項に記載の作用物質の組合せ物の含分を有する、化粧用調製物または皮膚用調製物。
- 請求項11に記載の調製物であって、その調製物の全質量に対して、0.000001〜10質量%の、特に0.0001〜3質量%の、殊に0.001〜1質量%の1種以上のアルキルアミドチアゾールを含有することを特徴とする調製物。
- 請求項11に記載の調製物であって、保存剤の全量は、該調製物の全質量に対して、0.00001質量%〜10質量%、好ましくは0.001質量%〜5質量%、特に0.005質量%〜3質量%であることを特徴とする調製物。
- 請求項1から13までのいずれか1項に記載の調製物または作用物質の組合せ物の、ヒトの皮膚の美白のための、非治療的な化粧用の使用。
- ヒトの皮膚の治療的美白のための、請求項1から13までのいずれか1項に記載の作用物質の組合せ物および調製物。
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JP2022040191A (ja) * | 2017-07-20 | 2022-03-10 | ダイヤ製薬株式会社 | 含水組成物、含水組成物を構成した貼付剤、化粧品又は外皮用医薬品、並びに、これらの製造方法 |
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US9610234B2 (en) | 2017-04-04 |
JP6444324B2 (ja) | 2018-12-26 |
ES2729374T3 (es) | 2019-11-04 |
CN105050575A (zh) | 2015-11-11 |
CN105050575B (zh) | 2019-10-01 |
BR112015022148B1 (pt) | 2020-03-24 |
KR102143561B1 (ko) | 2020-08-11 |
MX2015011990A (es) | 2015-12-01 |
KR20150130358A (ko) | 2015-11-23 |
US20160015615A1 (en) | 2016-01-21 |
WO2014139757A1 (de) | 2014-09-18 |
EP2968100A1 (de) | 2016-01-20 |
EP2968100B1 (de) | 2019-04-10 |
PL2968100T3 (pl) | 2019-08-30 |
DE102013204081A1 (de) | 2014-09-11 |
MX362140B (es) | 2018-12-24 |
BR112015022148A2 (pt) | 2017-07-18 |
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