JP5144153B2 - 皮膚外用剤 - Google Patents
皮膚外用剤 Download PDFInfo
- Publication number
- JP5144153B2 JP5144153B2 JP2007191450A JP2007191450A JP5144153B2 JP 5144153 B2 JP5144153 B2 JP 5144153B2 JP 2007191450 A JP2007191450 A JP 2007191450A JP 2007191450 A JP2007191450 A JP 2007191450A JP 5144153 B2 JP5144153 B2 JP 5144153B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- glucoside
- skin
- polyoxyalkylene alkyl
- weight
- 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.)
- Active
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- 238000002360 preparation method Methods 0.000 title claims description 54
- 230000000699 topical effect Effects 0.000 title description 2
- -1 alkyl glucoside Chemical class 0.000 claims description 117
- 229930182478 glucoside Natural products 0.000 claims description 56
- 150000005846 sugar alcohols Polymers 0.000 claims description 32
- 229920002683 Glycosaminoglycan Polymers 0.000 claims description 29
- HOVAGTYPODGVJG-UVSYOFPXSA-N (3s,5r)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol Chemical compound COC1OC(CO)[C@@H](O)C(O)[C@H]1O HOVAGTYPODGVJG-UVSYOFPXSA-N 0.000 claims description 24
- HOVAGTYPODGVJG-UHFFFAOYSA-N methyl beta-galactoside Natural products COC1OC(CO)C(O)C(O)C1O HOVAGTYPODGVJG-UHFFFAOYSA-N 0.000 claims description 24
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 19
- 229920001451 polypropylene glycol Polymers 0.000 claims description 17
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 15
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- 235000011187 glycerol Nutrition 0.000 claims description 9
- 229940058015 1,3-butylene glycol Drugs 0.000 claims description 7
- 235000019437 butane-1,3-diol Nutrition 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 5
- WYUFTYLVLQZQNH-JAJWTYFOSA-N Ethyl beta-D-glucopyranoside Chemical compound CCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O WYUFTYLVLQZQNH-JAJWTYFOSA-N 0.000 claims description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 3
- 229940105990 diglycerin Drugs 0.000 claims description 3
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims description 3
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 claims description 3
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 claims description 3
- 230000000087 stabilizing effect Effects 0.000 claims description 3
- 229960005150 glycerol Drugs 0.000 claims 2
- JYKSTGLAIMQDRA-UHFFFAOYSA-N tetraglycerol Chemical compound OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO JYKSTGLAIMQDRA-UHFFFAOYSA-N 0.000 claims 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims 2
- 230000006641 stabilisation Effects 0.000 claims 1
- 238000011105 stabilization Methods 0.000 claims 1
- 210000003491 skin Anatomy 0.000 description 64
- 230000003020 moisturizing effect Effects 0.000 description 34
- 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 19
- 229920002674 hyaluronan Polymers 0.000 description 16
- 229960003160 hyaluronic acid Drugs 0.000 description 15
- 125000003342 alkenyl group Chemical group 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 13
- 125000003118 aryl group Chemical group 0.000 description 13
- 125000002252 acyl group Chemical group 0.000 description 12
- 239000003814 drug Substances 0.000 description 12
- 238000011156 evaluation Methods 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 229920002385 Sodium hyaluronate Polymers 0.000 description 10
- 239000002537 cosmetic Substances 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 229940010747 sodium hyaluronate Drugs 0.000 description 10
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(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- Chemical compound [Na+].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 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 125000005129 aryl carbonyl group Chemical group 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 150000003505 terpenes Chemical class 0.000 description 8
- 235000007586 terpenes Nutrition 0.000 description 8
- 125000003277 amino group Chemical group 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- WCDDVEOXEIYWFB-VXORFPGASA-N (2s,3s,4r,5r,6r)-3-[(2s,3r,5s,6r)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@@H]1C[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O)[C@H](O)[C@H]1O WCDDVEOXEIYWFB-VXORFPGASA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 206010013786 Dry skin Diseases 0.000 description 6
- 230000037336 dry skin Effects 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 229940014041 hyaluronate Drugs 0.000 description 6
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000008213 purified water Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 208000024891 symptom Diseases 0.000 description 6
- 229920001287 Chondroitin sulfate Polymers 0.000 description 5
- 235000006679 Mentha X verticillata Nutrition 0.000 description 5
- 235000002899 Mentha suaveolens Nutrition 0.000 description 5
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 5
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 5
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- RADKZDMFGJYCBB-UHFFFAOYSA-N pyridoxal hydrochloride Natural products CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 description 5
- 229930002330 retinoic acid Natural products 0.000 description 5
- 229960001727 tretinoin Drugs 0.000 description 5
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- LVYLCBNXHHHPSB-UHFFFAOYSA-N 2-hydroxyethyl salicylate Chemical compound OCCOC(=O)C1=CC=CC=C1O LVYLCBNXHHHPSB-UHFFFAOYSA-N 0.000 description 4
- SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- 108010076876 Keratins Proteins 0.000 description 4
- 102000011782 Keratins Human genes 0.000 description 4
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 4
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 229940059329 chondroitin sulfate Drugs 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- ALEXXDVDDISNDU-JZYPGELDSA-N cortisol 21-acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O ALEXXDVDDISNDU-JZYPGELDSA-N 0.000 description 4
- 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 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 239000010642 eucalyptus oil Substances 0.000 description 4
- 229940044949 eucalyptus oil Drugs 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000003205 fragrance Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 4
- 229960001067 hydrocortisone acetate Drugs 0.000 description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 4
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 4
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 4
- 229960003495 thiamine Drugs 0.000 description 4
- 229960001295 tocopherol Drugs 0.000 description 4
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- 229930003799 tocopherol Natural products 0.000 description 4
- 239000011732 tocopherol Substances 0.000 description 4
- 229940088594 vitamin Drugs 0.000 description 4
- 229930003231 vitamin Natural products 0.000 description 4
- 235000013343 vitamin Nutrition 0.000 description 4
- 239000011782 vitamin Substances 0.000 description 4
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 4
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 3
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
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- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- KXKPYJOVDUMHGS-OSRGNVMNSA-N chondroitin sulfate Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](OS(O)(=O)=O)[C@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](C(O)=O)O1 KXKPYJOVDUMHGS-OSRGNVMNSA-N 0.000 description 3
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 3
- 150000002170 ethers Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229960000304 folic acid Drugs 0.000 description 3
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- 239000011724 folic acid Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 3
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
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- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- 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 2
- POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 229920002567 Chondroitin Polymers 0.000 description 2
- 241000723346 Cinnamomum camphora Species 0.000 description 2
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Description
従って、保湿効果が高く、しかも、不快な臭いがなく使用感触が良好な皮膚外用剤が望まれている。
すなわち本発明は、下記(1)〜(3)に掲げる皮膚外用剤である、
(1)ポリオキシアルキレンアルキルグルコシドと水溶性多価アルコールとムコ多糖類を含有し、
A)水溶性多価アルコールの含有量が、ポリオキシアルキレンアルキルグルコシドの5〜30重量倍、
B)ムコ多糖類の含有量が、ポリオキシアルキレンアルキルグルコシドの0.075〜2重量倍である皮膚外用剤、
(2)ポリオキシアルキレンアルキルグルコシドの含有量が0.01〜5重量%である(1)に記載の皮膚外用剤。
(3)ポリオキシアルキレンアルキルグルコシドが、プロピレン付加型である(1)〜(2)のいずれかに記載の皮膚外用剤。
(4)ポリオキシアルキレンアルキルグルコシドを含有する皮膚外用剤において、水溶性多価アルコールをポリオキシアルキレンアルキルグルコシドの5重量倍以上配合することを特徴とするポリオキシアルキレンアルキルグルコシドの安定化方法。
アルケニル基としては、炭素数2〜12のアルケニル基が挙げられ、好ましくは炭素数2〜6のアルケニル基である。具体例としては、ビニル基、アリル基等が挙げられる。
これらアルキル基及びアルケニル基は置換されていても良く、その置換基としては、炭素数1〜6のアルコキシ基(例、メトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、ブトキシ基、s−ブトキシ基、t−ブトキシ基、イソブトキシ基、ペンチルオキシ基、ヘキシルオキシ基等)、ハロゲン原子(例、フッ素原子、塩素原子、臭素原子、ヨウ素原子)、アミノ基、ヒドロキシ基等が挙げられる。
アリールカルボニル基としては炭素数7〜15のアリールカルボニル基が挙げられ、好ましくは炭素数7〜12のアリールカルボニル基である。具体例としては、ベンゾイル基、ナフチルカルボニル基(1−ナフチルカルボニル基、2−ナフチルカルボニル基)等が挙げられる。また、アリールカルボニル基は置換されていても良く、その置換基としては、炭素数1〜6のアルキル基(例、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、s−ブチル基、t−ブチル基、イソブチル基、ペンチル基、ヘキシル基等)、炭素数1〜6のアルコキシ基(例、メトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、ブトキシ基、s−ブトキシ基、t−ブトキシ基、イソブトキシ基、ペンチルオキシ基、ヘキシルオキシ基等)、ハロゲン原子(例、フッ素原子、塩素原子、臭素原子、ヨウ素原子)、アミノ基、ヒドロキシ基等が挙げられる。
エーテル誘導体の置換基として例示した「アルキル基」、「アルケニル基」及び「アリール基」としては、前記エステル誘導体の置換基として例示した「アルキル基」、「アルケニル基」及び「アリール基」とそれぞれ同様のものが挙げられる。
アミド誘導体の置換基として例示した「アルカノイル基」及び「アリールカルボニル基」としては、前記エステル誘導体の置換基として例示した「アルカノイル基」及び「アリールカルボニル基」とそれぞれ同様のものが挙げられる。
アミン誘導体の置換基として例示した「アルキル基」、「アルケニル基」及び「アリール基」としては、前記エステル誘導体の置換基として例示した「アルキル基」、「アルケニル基」及び「アリール基」とそれぞれ同様のものが挙げられる。
本発明に用いられるムコ多糖類としては、好ましくは、溶解度及び安定性の観点から、ヒアルロン酸ナトリウム、コンドロイチン硫酸ナトリウム等が挙げられる。
本発明に用いるポリオキシアルキレンアルキルグルコシドは、医薬品、医薬部外品、化粧品の分野で通常使用されるものであれば特に制限されずに使用できる。本発明において、ポリオキシアルキレンアルキルグルコシドは、1種単独で使用しても、また2種以上を任意に組み合わせて使用してもよい。
本発明に用いるポリオキシアルキレンアルキルグルコシドとしては、保湿性の観点からポリオキシアルキレンメチルグルコシド類が好ましく、ポリオキシエチレンメチルグルコシド及びポリオキシプロピレンメチルグルコシドが特に好ましく、ポリオキシプロピレンメチルグルコシドが更に好ましい。本発明に用いるポリオキシアルキレンアルキルグルコシドとして、マクビオブライド(商標)MG-10E、マクビオブライドMG-20E、マクビオブライドMG-10P、マクビオブライドMG-20P (以上、日本油脂製)や、グルカムE-10、E-20、P-10、P-20(以上、ノベオン製)等が用いることができる。
皮膚の乾燥に起因する症状の具体例としては、皮膚表面の落屑、粉ふき、けばだち、かさつき、ひび、あかぎれ、ひじ・ひざ・かかと・くるぶし等の角化、顔の小じわ、皮膚柔軟性の低下、手指のあれ、痒み、乾燥肌(ドライスキン)、敏感肌、皮膚のかぶれ、紅斑、アトピー肌、肌荒れ等がある。
これらの症状を示す具体的な疾患としては、乾皮症、老人性乾皮症、尋常性鱗癬(鮫肌)、小児乾燥性皮膚、アトピー性皮膚炎、アレルギー性皮膚炎、皮脂減少性湿疹、敏感肌、季節性乾皮症、水性掻痒症が挙げられる。
実施例1
ポリオキシプロピレンメチルグルコシド 1g
1,3-ブチレングリコール 5g
濃グリセリン 6g
ヒアルロン酸ナトリウム 0.3g
精製水 適量
合計 100g
表1の処方に従い、各製剤を調製し、蓋つきガラス容器(50ml)に40gずつ充填した後に密閉して、加速試験(条件1:60℃2週間、条件2:50℃1ヶ月)を実施した。加速試験終了後に開封し、開封直後に臭いを嗅いで、不快な臭いの有無を評価した。
実施例1と同様にして、表2に示す処方にて皮膚外用液剤を調製し、実施例8〜11又は比較例6〜10とした。
健常人10名の前腕内部に、各皮膚外用液剤を2.5μl/cm2となるように塗布し、それぞれの塗布部分について、塗布前、30分後の被検部位と無塗布のコントロール部位の高周波伝導度(μS)を表皮角層水分測定装置(Skicon-200EX、IBS社製)で測定した。測定は各被験部位において行い、3回の平均値を算出した。高周波伝導度(μS)の平均値を表2に示す。なお高周波伝導度の値が大きいほど角質水分量が多く保湿効果が高いことを示す。さらに、下記の基準で、◎、○、△、×の4段階に評価した。角質水分量及び評価の結果を表2に示す。
<評価>
◎:塗布30分後の角質水分量が、150μSを超える
○:塗布30分後の角質水分量が、100μSを超え、150μS以下
△:塗布30分後の角質水分量が、50μSを超え、100μS以下
×:塗布30分後の角質水分量が、50μS以下
健常者10名の腕に、試験例2で調製した実施例8〜11又は比較例6〜10の皮膚外用液剤を塗布してもらい、「保湿感」「ベタツキ」の各項目について、塗布直後及び塗布10分後に観察し、結果を総合して下記の評価基準に従い4段階で評点してもらった。さらに、評点の合計から、◎、○、△、×の4段階に評価した。評点の合計及び評価の結果を表2に示す。
「保湿感」
3点:しっとりしている
2点:ややしっとりしている
1点:あまりしっとりしていない
0点:乾燥している
「ベタツキ」
3点:ベタツキを全く感じない
2点:わずかにベタツキがあるが、使用上問題のない範囲である
1点:少しベタツキがある
0点:著しくベタツキがある
<評価>
「保湿感」「ベタツキ」
◎:評点の合計が、22.5点を超え、30点以下
○:評点の合計が、15点を超え、22.5点以下
△:評点の合計が、7.5を超え、15点以下
×:評点の合計が、7.5以下
◎:評価項目がすべて◎の場合
○:評価項目が1つ以上○、残りが◎の場合
△:評価項目が1つ以上△、残りが◎又は○の場合
×:評価項目が1つ以上×、残りが◎、○又は△の場合
下記のA相及びB相の各成分を秤量し、A相、B相に分けて室温にて均一に溶解した後、A相にB相を加え均一に混合して化粧水を得た。ポリオキシプロピレンメチルグルコシドは、プロピレンオキシド付加モル数が10のものを使用した。
A相
精製水 73.75g
1,3-ブチレングリコール 10g
グリセリン 7g
ヒアルロン酸ナトリウム 0.5g
ポリオキシプロピレンメチルグルコシド 3g
B相
エタノール 5g
POE(20)ソルビタンモノラウリン酸エステル 0.5g
オレイルアルコール 0.1g
メチルパラベン 0.1g
香料 0.05g
実例11に準じて製造した。ポリオキシエチレンメチルグルコシドは、エチレンオキシド付加モル数が10のものを使用した。
A相
精製水 81.2g
1,3-ブチレングリコール 6g
ジプロピレングリコール 5g
PEG4000 3g
ポリオキシエチレンメチルグルコシド 2g
ヒアルロン酸ナトリウム 0.3g
B相
ホホバ油 0.5g
POE(20)ソルビタンモノステアリン酸エステル 1.5g
POE(5)オレイルアルコールエーテル 0.3g
メチルパラベン 0.15g
香料 0.05g
A相、B相をそれぞれ混合・加熱溶解して70℃に保つ。A相にB相を徐々に加え、乳化機にて乳化する。乳化物を終温25℃まで冷却し、乳液を得た。ポリオキシプロピレンメチルグルコシドは、プロピレンオキシド付加モル数が20のものを使用した。
A相
ミツロウ 2g
流動パラフィン 20g
スクワラン 10g
モノステアリン酸グリセリン 3g
POE(20)ソルビタンモノオレイン酸エステル 1g
エチルパラベン 0.2g
香料 0.05g
B相
1,3-ブチレングリコール 7g
ポリオキシプロピレンメチルグルコシド 1g
ヒアルロン酸ナトリウム 0.2g
精製水 55.55g
処方例13に準じて製造した。ポリオキシエチレンメチルグルコシドは、エチレンオキシド付加モル数が20のものを使用した。
A相
ステアリルアルコール 6g
ステアリン酸 2g
スクワラン 9g
オクチルドデカノール 10g
POE(25)セチルアルコールエーテル 3g
モノステアリン酸グリセリン 2g
メチルパラベン 0.1g
プロピルパラベン 0.05g
B相
1.3-ブチレングリコール 6g
PEG1500 4g
ポリオキシエチレンメチルグルコシド 1g
ヒアルロン酸ナトリウム 0.2g
アセチル化ヒアルロン酸ナトリウム 0.05g
精製水 56.6g
A相、B相をそれぞれ混合・加熱溶解して70℃に保ち、B相にA相を徐々に加える。次に70℃に加熱溶解したC相を徐々に添加する。終温25℃まで冷却し、ファンデーションを得た。ポリオキシプロピレンメチルグルコシドは、プロピレンオキシド付加モル数が10のものを使用した。
A相
タルク 3g
二酸化チタン 5g
ベンガラ 0.5g
黄酸化鉄 1.4g
黒酸化鉄 0.1g
B相
ベントナイト 0.5g
モノステアリン酸ポリオキシエチレンソルビタン 0.9g
ジプロピレングリコール 10g
ポリオキシプロピレンメチルグルコシド 1g
ヒアルロン酸ナトリウム 0.1g
精製水 58.1g
C相
ステアリン酸 2.2g
イソヘキサデシルアルコール 7g
モノステアリン酸グリセリン 2g
流動パラフィン 8g
メチルパラベン 0.2g
Claims (5)
- 水溶性多価アルコール、ムコ多糖類、及びポリオキシアルキレンアルキルグルコシドを含有し、
A)水溶性多価アルコールの含有量が、ポリオキシアルキレンアルキルグルコシドの5〜30重量倍、
B)ムコ多糖類の含有量が、ポリオキシアルキレンアルキルグルコシドの0.075〜2重量倍である皮膚外用剤であって、
ここで該ポリオキシアルキレンアルキルグルコシドは、ポリオキシプロピレンメチルグルコシド、ポリオキシプロピレンエチルグルコシド、およびポリオキシプロピレンプロピルグルコシドからなる群より選択される1種または2種以上であり、
該水溶性多価アルコールは、ジプロピレングリコール、1,3−ブチレングリコール、1,4−ブチレングリコール、プロピレングリコール、1,2−ペンタンジオール、1,2−ヘキシレングリコール、グリセリン、ジグリセリン、トリグリセリン、およびテトラグリセリンからなる群より選択される1種または2種以上である皮膚外用剤。 - 前記ポリオキシアルキレンアルキルグルコシドの含有量が0.01〜5重量%である請求項1に記載の皮膚外用剤。
- 前記水溶性多価アルコールの含有量が、0.0001〜50重量%である、請求項1または2に記載の皮膚外用剤。
- 前記ムコ多糖類の含有量が、0.0001〜10重量%である、請求項1〜3のいずれか1項に記載の皮膚外用剤。
- ポリオキシアルキレンアルキルグルコシドを含有する皮膚外用剤において、水溶性多価アルコールをポリオキシアルキレンアルキルグルコシドの5〜30重量倍配合し、ムコ多糖類をポリオキシアルキレンアルキルグルコシドの0.075〜2重量倍配合することを特徴とするポリオキシアルキレンアルキルグルコシドの安定化方法であって、
ここで該ポリオキシアルキレンアルキルグルコシドは、ポリオキシプロピレンメチルグルコシド、ポリオキシプロピレンエチルグルコシド、およびポリオキシプロピレンプロピルグルコシドからなる群より選択される1種または2種以上であり、
該水溶性多価アルコールは、ジプロピレングリコール、1,3−ブチレングリコール、1,4−ブチレングリコール、プロピレングリコール、1,2−ペンタンジオール、1,2−ヘキシレングリコール、グリセリン、ジグリセリン、トリグリセリン、およびテトラグリセリンからなる群より選択される1種または2種以上である安定化方法。
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