JP2002284662A - 皮膚外用剤組成物 - Google Patents
皮膚外用剤組成物Info
- Publication number
- JP2002284662A JP2002284662A JP2001089314A JP2001089314A JP2002284662A JP 2002284662 A JP2002284662 A JP 2002284662A JP 2001089314 A JP2001089314 A JP 2001089314A JP 2001089314 A JP2001089314 A JP 2001089314A JP 2002284662 A JP2002284662 A JP 2002284662A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- skin
- retinyl
- composition
- acetylglucosamine
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 229950006780 n-acetylglucosamine Drugs 0.000 claims description 28
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 claims description 27
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 claims description 26
- MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 claims description 26
- 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 claims description 25
- 229930002330 retinoic acid Natural products 0.000 claims description 25
- 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 claims description 16
- 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 claims description 11
- 150000004492 retinoid derivatives Chemical class 0.000 claims description 11
- 230000032683 aging Effects 0.000 claims description 5
- SHGAZHPCJJPHSC-NUEINMDLSA-N Isotretinoin Chemical compound OC(=O)C=C(C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-NUEINMDLSA-N 0.000 claims description 3
- 239000011717 all-trans-retinol Substances 0.000 claims description 3
- 229940100609 all-trans-retinol Drugs 0.000 claims description 3
- 235000019169 all-trans-retinol Nutrition 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 claims description 3
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- 238000000034 method Methods 0.000 claims description 3
- FPIPGXGPPPQFEQ-HWCYFHEPSA-N 13-cis-retinol Chemical compound OC/C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-HWCYFHEPSA-N 0.000 claims description 2
- FPIPGXGPPPQFEQ-DPZDGVIMSA-N dihydroretinol Natural products CC(=CCO)C=CC=C(C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-DPZDGVIMSA-N 0.000 claims 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 abstract description 35
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- 229960003160 hyaluronic acid Drugs 0.000 abstract description 35
- 238000004519 manufacturing process Methods 0.000 abstract description 18
- VYGQUTWHTHXGQB-FFHKNEKCSA-N Retinol Palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C VYGQUTWHTHXGQB-FFHKNEKCSA-N 0.000 description 32
- -1 fatty acid esters Chemical class 0.000 description 32
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- 229960001727 tretinoin Drugs 0.000 description 23
- 238000009472 formulation Methods 0.000 description 18
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- 210000001339 epidermal cell Anatomy 0.000 description 10
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 8
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 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 8
- 239000000126 substance Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000011607 retinol Substances 0.000 description 7
- 229960003471 retinol Drugs 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
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- 230000001737 promoting effect Effects 0.000 description 6
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- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 5
- 235000020944 retinol Nutrition 0.000 description 5
- 230000037303 wrinkles Effects 0.000 description 5
- 229940058015 1,3-butylene glycol Drugs 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229920002125 Sokalan® Polymers 0.000 description 4
- XWCYDHJOKKGVHC-UHFFFAOYSA-N Vitamin A2 Chemical compound OCC=C(C)C=CC=C(C)C=CC1=C(C)C=CCC1(C)C XWCYDHJOKKGVHC-UHFFFAOYSA-N 0.000 description 4
- 229960005070 ascorbic acid Drugs 0.000 description 4
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- 230000015572 biosynthetic process Effects 0.000 description 4
- 235000019437 butane-1,3-diol Nutrition 0.000 description 4
- 238000002481 ethanol extraction Methods 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 4
- 239000008213 purified water Substances 0.000 description 4
- QGNJRVVDBSJHIZ-QHLGVNSISA-N retinyl acetate Chemical compound CC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C QGNJRVVDBSJHIZ-QHLGVNSISA-N 0.000 description 4
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- 230000002195 synergetic effect Effects 0.000 description 4
- KJTLQQUUPVSXIM-ZCFIWIBFSA-N (R)-mevalonic acid Chemical compound OCC[C@](O)(C)CC(O)=O KJTLQQUUPVSXIM-ZCFIWIBFSA-N 0.000 description 3
- KJTLQQUUPVSXIM-UHFFFAOYSA-N DL-mevalonic acid Natural products OCCC(O)(C)CC(O)=O KJTLQQUUPVSXIM-UHFFFAOYSA-N 0.000 description 3
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- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 3
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- 239000004359 castor oil Substances 0.000 description 3
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- 210000004027 cell Anatomy 0.000 description 3
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- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
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- 238000003756 stirring Methods 0.000 description 3
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- 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 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
- ABEXEQSGABRUHS-UHFFFAOYSA-N 16-methylheptadecyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C ABEXEQSGABRUHS-UHFFFAOYSA-N 0.000 description 2
- BGRXBNZMPMGLQI-UHFFFAOYSA-N 2-octyldodecyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCC(CCCCCCCC)CCCCCCCCCC BGRXBNZMPMGLQI-UHFFFAOYSA-N 0.000 description 2
- 208000002874 Acne Vulgaris Diseases 0.000 description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 2
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 description 2
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- ILKBHIBYKSHTKQ-UHFFFAOYSA-N Diisopropylamine dichloroacetate Chemical compound OC(=O)C(Cl)Cl.CC(C)NC(C)C ILKBHIBYKSHTKQ-UHFFFAOYSA-N 0.000 description 2
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- ANVAOWXLWRTKGA-XHGAXZNDSA-N all-trans-alpha-carotene Chemical compound CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1C(C)=CCCC1(C)C ANVAOWXLWRTKGA-XHGAXZNDSA-N 0.000 description 2
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- 125000000946 retinyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])=C([H])/C([H])=C(C([H])([H])[H])/C([H])=C([H])/C1=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 235000005713 safflower oil Nutrition 0.000 description 1
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- 231100000475 skin irritation Toxicity 0.000 description 1
- 229940080236 sodium cetyl sulfate Drugs 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- 229940010747 sodium hyaluronate Drugs 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
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- 235000011088 sodium lactate Nutrition 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- WTWSHHITWMVLBX-DKWTVANSSA-M sodium;(2s)-2-aminobutanedioate;hydron Chemical compound [Na+].[O-]C(=O)[C@@H](N)CC(O)=O WTWSHHITWMVLBX-DKWTVANSSA-M 0.000 description 1
- 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 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- 229960005078 sorbitan sesquioleate Drugs 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229940071136 stearoyl glutamate Drugs 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229940117986 sulfobetaine Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 229950009883 tocopheryl nicotinate Drugs 0.000 description 1
- KBPHJBAIARWVSC-XQIHNALSSA-N trans-lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C KBPHJBAIARWVSC-XQIHNALSSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
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- 239000008158 vegetable oil Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 1
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- FJHBOVDFOQMZRV-XQIHNALSSA-N xanthophyll Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C=C(C)C(O)CC2(C)C FJHBOVDFOQMZRV-XQIHNALSSA-N 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
- 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 1
Classifications
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7008—Compounds having an amino group directly attached to a carbon atom of the saccharide radical, e.g. D-galactosamine, ranimustine
-
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/07—Retinol compounds, e.g. vitamin A
-
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- 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
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A61K31/203—Retinoic acids ; Salts thereof
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- A61Q19/08—Anti-ageing preparations
Abstract
潤いを維持することのできる皮膚外用剤を提供する。 【解決手段】N−アセチルグルコサミンと、レチノイド
とを含有することを特徴とする皮膚外用剤組成物。
Description
コサミンとレチノイドとを含有する皮膚外用剤組成物に
関するものである。詳しくは、皮膚のハリや潤いを維持
して皺、乾燥肌、日焼け肌、老化肌を予防または改善す
ることのできる皮膚外用剤組成物に関する。
ジェリー状のマトリクスを形成することに基づく細胞の
保持、皮膚の潤滑性と柔軟性の保持、機械的障害などの
外力に対する抵抗力および細菌感染の防止など多くの機
能を有している(BIO INDUSTRY、8巻、3
46頁、1991年)。
酸染色強度が低下し(J.Invest.Dermat
ol.,102,385,1994)、また紫外線照射
による光弾力線維症(solar elastosi
s)部のヒアルロン酸は殆ど検出されない(臨皮、(5
増)51、53、1997;Nagoya Med.
J.,41,27,1997)ことが報告されており、
その結果として皮膚の乾燥、ハリ、弾力性の低下、ひい
ては皺の増加を引き起こすと考えられている。このよう
な状態を改善すべく、ヒアルロン酸を配合した化粧料を
塗布することにより皮膚表面の保湿性を保つ方法がとら
れてきたが、高分子であるヒアルロン酸は皮膚を透過し
ないことから根本的改善は期待できない。したがって細
胞自身が元来もっているヒアルロン酸合成能を高めるこ
とにより皮膚機能を根本的に改善する物質の開発が期待
されている。
しては、従来、レチノイン酸が知られている。レチノイ
ン酸は元来表皮に存在し、表皮細胞の増殖や分化に関与
する必須な物質である。レチノイン酸は海外では各種の
皮膚障害、例えば尋常性ざ瘡、小皺、乾癬、老斑を処置
すべく皮膚性状回復剤もしくは更新剤として広範に使用
されている。
ついては多数報告されており、小皺の形成に対しての改
善効果が認められている(形成外科、42:801、1
999;J.Dematol.,122,91,199
0)。一方でレチノイン酸塗布によりヒアルロン酸など
のムコ多糖の沈着が増加し、光老化皮膚の組織学的変化
が改善される(J.Dermatol.Sci.,1
1,177,1996)ことが報告されている。したが
って、レチノイン酸の皮膚表面の平滑化効果には表皮マ
トリクス成分であるヒアルロン酸沈着とそれによる水分
増加が大きく寄与している可能性があり(日本皮膚科学
会誌、110巻12号、1878、2000)、表皮ヒ
アルロン酸産生促進剤が抗皺に有用であると考えられる
(FRAGRANCE JOURNAL、4、49、1
998)。
ており、刺激感を予防するためには低濃度のレチノイン
酸外用剤を処方することが必要となる。一方で刺激性が
低いレチノールもしくはレチニルエステルは、生体内で
活性体であるレチノイン酸へ代謝される必要があり、皮
膚に利益を与える際、レチノイン酸より効果が低い。し
たがって、レチノイン酸の効果を有しつつ、皮膚刺激性
という副作用がない皮膚外用剤が望まれていた。本発明
は、レチノイドとN-アセチルグルコサミンの組み合わせ
が表皮細胞のヒアルロン酸合成に相乗的向上をもたらす
という知見に基づいている。
は、レチノイドと組み合わせることにより相乗的にヒア
ルロン酸産生促進効果を示す皮膚外用剤組成物を提供す
ることをも目的とする。
解決に向けて広く種々の物質にヒアルロン酸産生促進能
を調べた結果、N−アセチルグルコサミンがヒアルロン
酸産生促進作用を有し、さらにN−アセチルグルコサミ
ンが、レチノイドが有するヒアルロン酸産生促進作用と
相乗作用を示すことを見い出し、これに基づいて本発明
を完成するに至った。
サミンとレチノイドとを含有してなる皮膚外用剤組成物
にある。
成物とは、一般に頭皮を含む皮膚に適用される組成物す
べてを指し、医薬品、医薬部外品、化粧料、入浴剤、養
毛料、スカルプトニック等を包含するものである。
膚外用剤組成物に有効量のN−アセチルグルコサミンを
含ませることにより該組成物の性能が実質的に向上す
る。或いは、それより低レベル(低濃度)のレチノイド
にN−アセチルグルコサミンを含ませることにより高レ
ベルのレチノイドを含む処方物と性能を等しくすること
もできる。
グルコサミンは、合成物や発酵産物、カニ、えびなどの
キチン分解から得られる分解産物等、いずれのものに限
定されるものではない。
成物への配合量は、組成物総量を基準として、0.00
1〜10質量%(以下、単に%と記する)とするのが好
ましく、特に好ましくは0.01〜5%である。
しては、レチノイン酸、レチナール、レチノールおよび
脂肪酸レチニルエステル、ならびにデヒドロレチノー
ル、デヒドロレチノール、脂肪酸デヒドロレチニルエス
テルを包含する。これらの中で効果の面より、レチノイ
ン酸が好ましい。
異性体を包含する:全trans−レチノイン酸、13
−cis−レチノイン酸、11−cis−レチノイン
酸、9−cis−レチノイン酸、3,4−デヒドロ−レ
チノイン酸である。尋常性ざ瘡や光老化の治療薬として
海外で広く使用されている全trans−レチノイン酸
あるいは13−cis−レチノイン酸が好適である。
体を包含する:全trans−レチノール、13−ci
s−レチノール、11−cis−レチノール、9−ci
s−レチノール、3,4−デヒドロ−レチノールであ
る。広く市販されているため全trans−レチノール
あるいは13−cis−レチノールが好適である。
脂肪酸エステルである。脂肪酸レチニルエステルは、特
に限定されないが以下のものを包含する:パルミチン酸
レチニル、ギ酸レチニル、酢酸レチニル、プロピオン酸
レチニル、酪酸レチニル、吉草酸レチニル、イソ吉草酸
レチニル、ヘキサン酸レチニル、ヘプタン酸レチニル、
オクタン酸レチニル、ノナン酸レチニル、デカン酸レチ
ニル、ウンデカン酸レチニル、ラウリン酸レチニル、ト
リデカン酸レチニル、ミリスチン酸エステル、ペンタデ
カン酸レチニル、ヘプタデカン酸レチニル、ステアリン
酸レチニル、イソステアリン酸エステル、ノナデカン酸
レチニル、アラキドン酸レチニル、アラキドン酸レチニ
ル、リノール酸レチニル、オレイン酸レチニル。
入手しやすいパルミチン酸レチニル、酢酸レチニルおよ
びプロピオン酸レチニルから選択される。
成物総量を基準として、0.0001〜10%とするの
が好ましく、より好ましくは0.01〜1%である。
に、プロビタミンA活性をもつβ−カロチン、α−カロ
チン、クリプトキサンチンなどを用いることもできる。
ール系色素、ジメチルポリシロキサン、メチルフェニル
ポリシロキサン、環状シリコーン等のシリコーン油、ル
テイン、アスタキサンチン、フコキサンチンなどのカロ
チノイド系色素、酸化鉄などの着色顔料、パラベン、フ
ェノキシエタノールなどの防腐剤、パラフィン、ワセリ
ン等の炭化水素類、オリーブスクワラン、米スクワラ
ン、米胚芽油、ホホバ油、ヒマシ油、紅花油、オリーブ
油、マカデミアナッツ油、ヒマワリ油などの植物油、ミ
ツロウ、モクロウ、カルナバロウ等のロウ類、ミリスチ
ン酸オクチルドデシル、パルミチン酸セチル、イソステ
アリン酸イソステアリル、ミリスチン酸イソプロピル等
のエステル油、エタノール等の低級アルコール類、セタ
ノール、ベヘニルアルコール、ステアリルアルコール、
長鎖分岐脂肪族アルコール等の高級アルコール類、コレ
ステロール、フィトステロール、分岐脂肪酸コレステロ
ールエステル、マカデミアナッツ脂肪酸フィトステリル
エステル等のステロール類及び誘導体、硬化油等の加工
油類、ステアリン酸、ミリスチン酸、イソステアリン
酸、オレイン酸、イソ型長鎖脂肪酸、アンテイソ型長鎖
脂肪酸などの高級脂肪酸、リモネン、水素添加ビサボロ
ール等のテルペン類、トリカプリル・カプリン酸グリセ
リル、2−エチルヘキサン酸グリセリル、トリイソ型長
鎖脂肪酸グリセリル、トリパルミチン酸グリセリルなど
のトリグリセリド、セチル硫酸ナトリウム、N−ステア
ロイル−L−グルタミン酸塩などの陰イオン界面活性
剤、ポリオキシエチレンアルキルエーテル、ポリオキシ
エチレン脂肪酸エステル、ポリオキシエチレン多価アル
コール脂肪酸エステル、ポリオキシエチレン硬化ヒマシ
油、多価アルコール脂肪酸エステル、ポリオキシエチレ
ン編成シリコーン等の変性シリコーン、ポリグリセリン
脂肪酸エステル、蔗糖エステルなどの非イオン界面活性
剤、テトラアルキルアンモニウム塩などの陽イオン界面
活性剤、ベタイン型、スルホベタイン型、スルホアミノ
酸型などの両性界面活性剤、レシチン、リゾフォスファ
チジルコリン、セラミド、セレブロシドなどの天然系界
面活性剤、酸化チタン、酸化亜鉛などの顔料、ジブチル
ヒドロキシトルエンなどの抗酸化剤、塩化ナトリウム、
塩化マグネシウム、硫酸ナトリウム、硝酸カリウム、硫
酸ナトリウム、メタ珪酸ナトリウム、塩化カルシウム等
の無機塩類、クエン酸ナトリウム、酢酸カリウム、琥珀
酸ナトリウム、アスパラギン酸ナトリウム、乳酸ナトリ
ウム、ジクロロ酢酸、メバロン酸、グリチルリチン酸等
の有機酸及びその塩、塩酸エタノールアミン、硝酸アン
モニウム、塩酸アルギニン、ジイソプロピルアミン塩、
尿素、デカルボキシカルノシン等の有機アミン類及びそ
の塩、エデト酸等のキレート剤、キサンタンガム、カル
ボキシビニルポリマー、カラギーナン、ペクチン、アル
キル変性カルボキシビニルポリマー、寒天等の増粘剤、
水酸化カリウム、ジイソプロパノールアミン、トリエタ
ノールアミン等の中和剤、ヒドロキシメトキシベンゾフ
ェノンスルフォン酸塩等の紫外線吸収剤、ジプロピレン
グリコール、マルビトール、1,3−ブチレングリコー
ル、グリセリン、プロピレングリコール、ソルビトー
ル、ジグリセリン、ラフィノースなどの多価アルコー
ル、各種アミノ酸、アスコルビン酸、ビオチン、トコフ
ェロール等のビタミン類およびアスコルビン酸硫酸エス
テル塩、アスコルビン酸燐酸エステル塩、ニコチン酸ト
コフェロール等のビタミン誘導体等を本発明の目的を達
成する範囲内で適宜配合することができる。
キス等の真皮ヒアルロン酸産生促進剤、クリタケエキ
ス、クロカワエキス、モッキンエキス、アセンヤクエキ
ス、チョウジエキス等のヒアルロン酸分解抑制剤、ジイ
ソプロピルアミンジクロロ酢酸、ナイアシン、メバロン
酸、温泉水、メタケイ酸ナトリウム、ホモフルーツ等の
角化促進剤、β−ヒドロキシ−γ−アミノ酪酸、メバロ
ン酸等のバリアー増強剤等を目的を達成する範囲内で適
宜配合することにより皺予防効果はいっそう 高まる。
説明するが、本発明は以下の実施例に限定されるもので
はない。
ロン酸産生促進試験) ヒト正常表皮細胞(クラボウ社製)を24穴プレートに
播種し、コンフルエントまで増殖用培地にて培養後、5
mmol/LのN−アセチルグルコサミン、0.000
1%のパルミチン酸レチニル、0.0001%のパルミ
チン酸レチニルとともに5mmol/LのN−アセチル
グルコサミン、1.0μmol/Lのレチノイン酸、あ
るいは1.0μmol/Lレチノイン酸とともに5mm
ol/LのN−アセチルグルコサミンを添加した。添加
より24時間培養後、培地中に放出されたヒアルロン酸
を測定した。ヒアルロン酸の測定は、市販のヒアルロン
酸測定キット(中外製薬社製)を用いておこなった。
質を添加しない培地で培養したヒト正常表皮細胞のウェ
ル当たりのヒアルロン酸量を100とした時の、試験物
質含有培地で培養した表皮細胞のヒアルロン酸量と定義
した。結果を以下に示す。
ンを細胞培養系に添加することにより、表皮細胞のヒア
ルロン酸産生量は無添加群の1.55倍に増加し、N−
アセチルグルコサミンがヒト表皮細胞のヒアルロン酸産
生を促進することを初めて見出した。0.0001%パ
ルミチン酸レチニル、あるいは既にヒアルロン酸産生促
進作用が知られているレチノイン酸は、それぞれ単独の
添加で無添加群の1.23倍あるいは2.5倍の産生量
を示した。一方、0.0001%パルミチン酸レチニル
と5mmol/L N−アセチルグルコサミンを表皮細
胞培養系に同時添加することによりヒアルロン酸産生量
は無添加群の2.64倍と顕著に増加し、1.0μmo
l/L レチノイン酸の作用を越えるレベルまでヒアル
ロン酸産生量を増大させた。また1.0μmol/L
レチノイン酸を5mmol/LN−アセチルグルコサミ
ンと同時に添加することにより無添加群の6.32倍の
ヒアルロン酸産生量を示し、両物質のヒアルロン酸産生
促進作用の明らかな相乗的効果が観測された。
ルロン酸産生促進剤の処方例を挙げる。
を下記の組成でそれぞれを配合し、スキンクリームを調
製した。すべて%である。
後混合して、攪拌しつつ冷却し、30℃まで冷却して、
スキンクリームを調製した。
を下記の組成で配合し、ローションを調製した。
調製した。
を下記の組成でそれぞれを配合し、ジェルを調製した。
後混合して、攪拌しつつ冷却し、30℃まで冷却して、
クリームを調製した。
を下記の組成で配合し、親油クリームを調製した。
後混合して、攪拌しつつ冷却し、30℃まで冷却して、
親油クリームを調製した。
とレチノイドとを組み合わせることで、相乗的なヒアル
ロン酸産生促進作用が発揮される。本発明の皮膚外用剤
を塗布することにより、細胞マトリクス成分であるヒア
ルロン酸の産生が促進され、ヒト皮膚の老化防止(皮膚
のハリや弾力性、潤いの維持)に適応され得る。
Claims (3)
- 【請求項1】 N−アセチルグルコサミンと、レチノイ
ドとを含有することを特徴とする皮膚外用剤組成物。 - 【請求項2】 レチノイドが、全トランスレチノール、
13−cisレチノール、全トランスレチノイン酸およ
び13−シスレチノイン酸からなる群より選択される少
なくとも一種以上のものである請求項1に記載の皮膚外
用剤組成物。 - 【請求項3】 請求項1に記載の外用剤を皮膚に施すこ
とを特徴とする皺肌、乾燥肌、日焼け肌または老化肌の
外観を予防または改善するための化粧方法。
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CNB028100816A CN1220492C (zh) | 2001-03-27 | 2002-03-11 | 皮肤外用剂组合物 |
EP02705098A EP1384482A4 (en) | 2001-03-27 | 2002-03-11 | EXTERNAL SKIN COMPOSITIONS |
KR1020037012642A KR100615369B1 (ko) | 2001-03-27 | 2002-03-11 | 피부외용제 조성물 |
PCT/JP2002/002271 WO2002076470A1 (en) | 2001-03-27 | 2002-03-11 | External skin compositions |
US10/473,293 US20050002879A1 (en) | 2001-03-27 | 2002-03-11 | External skin compositions |
TW091104803A TWI245633B (en) | 2001-03-27 | 2002-03-14 | A composition for external application of skin |
US12/016,911 US20080287393A1 (en) | 2001-03-27 | 2008-01-18 | External Skin Composition |
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ID=18944260
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US (2) | US20050002879A1 (ja) |
EP (1) | EP1384482A4 (ja) |
JP (1) | JP2002284662A (ja) |
KR (1) | KR100615369B1 (ja) |
CN (1) | CN1220492C (ja) |
TW (1) | TWI245633B (ja) |
WO (1) | WO2002076470A1 (ja) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2004039859A1 (ja) | 2002-10-30 | 2004-05-13 | Sumitomo Chemical Company, Limited | 高分子化合物およびそれを用いた高分子発光素子 |
JP2004359573A (ja) * | 2003-06-03 | 2004-12-24 | Nikko Chemical Co Ltd | ヒアルロン酸産生促進剤、及び該ヒアルロン酸産生促進剤を用いた皮膚外用剤、及び化粧料 |
JP2006528935A (ja) * | 2003-07-25 | 2006-12-28 | ザ プロクター アンド ギャンブル カンパニー | N−アシルアミノ酸組成物を用いた哺乳類のケラチン組織の調整 |
JP2007519689A (ja) * | 2004-01-29 | 2007-07-19 | ピエール ファーブル デルモ−コスメティック | ヒアルロン酸ナトリウムの断片とレチノイドを組み合わせる局所用組成物 |
JP2008024704A (ja) * | 2006-06-23 | 2008-02-07 | Rohto Pharmaceut Co Ltd | ヒアルロン酸産生促進能及び/又は線維芽細胞増殖促進能を有する組成物 |
JP2008529964A (ja) * | 2003-06-25 | 2008-08-07 | トポターゲット ジャーマニー アーゲー | 皮膚疾患の予防または治療用のバルプロ酸の局所使用 |
JP2008195629A (ja) * | 2007-02-09 | 2008-08-28 | Naris Cosmetics Co Ltd | 皮膚光老化改善剤 |
JP2011042627A (ja) * | 2009-08-21 | 2011-03-03 | Unitika Ltd | ヒアルロン酸合成促進剤 |
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US20020182237A1 (en) * | 2001-03-22 | 2002-12-05 | The Procter & Gamble Company | Skin care compositions containing a sugar amine |
ITTO20070210A1 (it) | 2007-03-22 | 2008-09-23 | Rottapharm Spa | Composizioni contenenti n-acetilglucosamina per l'impiego in dermocosmesi e medicina estetica |
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FR3022780B1 (fr) * | 2014-06-30 | 2018-03-30 | Nutricos Technologies | Produits de combinaison et compositions cosmetiques pour lutter contre les desordres de la peau et son vieillissement affectant les fibroblastes et le derme |
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US5391373A (en) * | 1992-07-01 | 1995-02-21 | Chanel, Inc. | Skin cream composition |
FR2714600B1 (fr) * | 1993-12-30 | 1996-02-09 | Oreal | Composition protectrice, nutritive et/ou raffermissante pour le traitement simultané des couches superficielles et profondes de la peau, son utilisation. |
FR2715565B1 (fr) * | 1994-01-31 | 1996-03-15 | Oreal | Composition cosmétique ou dermatologique stabilisée contenant plusieurs précurseurs d'un même actif pour maximaliser sa libération, son utilisation. |
FR2732215B1 (fr) * | 1995-03-28 | 1997-04-30 | Sederma Sa | Nouvelles compositions cosmetiques depigmentantes |
US5985177A (en) * | 1995-12-14 | 1999-11-16 | Shiseido Co., Ltd. | O/W/O type multiple emulsion and method of preparing the same |
US6468564B1 (en) * | 1997-02-21 | 2002-10-22 | Clientele Beauty, Inc. | Topical compositions containing lotus for skin treatment |
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IT1288257B1 (it) * | 1996-11-29 | 1998-09-11 | Paoli Ambrosi Gianfranco De | Composizione per uso cosmetico,farmaceutico o dietetico a base di un aminozucchero e/o di un acido poliidrossilico |
US5804594A (en) * | 1997-01-22 | 1998-09-08 | Murad; Howard | Pharmaceutical compositions and methods for improving wrinkles and other skin conditions |
JP2000136147A (ja) * | 1998-10-29 | 2000-05-16 | Lion Corp | 生体ヒアルロン酸合成促進剤 |
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JP4249853B2 (ja) * | 1999-08-09 | 2009-04-08 | 焼津水産化学工業株式会社 | 経口用皮膚潤い改善剤 |
JP4093735B2 (ja) * | 2000-06-13 | 2008-06-04 | 花王株式会社 | 乳化型皮膚外用剤 |
US6623728B2 (en) * | 2000-06-30 | 2003-09-23 | Unilever Home & Personal Care Usa Division Of Conopco, Inc. | Cosmetic skin care compositions and containing gum mastic |
EP1374904A1 (en) * | 2002-06-20 | 2004-01-02 | Baas, Fhilipus Albert | Preparation containing polymethyl-siloxane for nails, cartilage, bone joint, muscle and tendon disorders |
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2001
- 2001-03-27 JP JP2001089314A patent/JP2002284662A/ja active Pending
-
2002
- 2002-03-11 US US10/473,293 patent/US20050002879A1/en not_active Abandoned
- 2002-03-11 CN CNB028100816A patent/CN1220492C/zh not_active Expired - Fee Related
- 2002-03-11 KR KR1020037012642A patent/KR100615369B1/ko not_active IP Right Cessation
- 2002-03-11 WO PCT/JP2002/002271 patent/WO2002076470A1/ja active Application Filing
- 2002-03-11 EP EP02705098A patent/EP1384482A4/en not_active Withdrawn
- 2002-03-14 TW TW091104803A patent/TWI245633B/zh not_active IP Right Cessation
-
2008
- 2008-01-18 US US12/016,911 patent/US20080287393A1/en not_active Abandoned
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WO2004039859A1 (ja) | 2002-10-30 | 2004-05-13 | Sumitomo Chemical Company, Limited | 高分子化合物およびそれを用いた高分子発光素子 |
EP2325225A1 (en) | 2002-10-30 | 2011-05-25 | Sumitomo Chemical Company, Limited | Complex aryl copolymer compounds and polymer light emitting devices made by using the same |
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EP2325224A1 (en) | 2002-10-30 | 2011-05-25 | Sumitomo Chemical Company, Limited | Aryl copolymer compounds and polymer light emitting devices made by using the same |
JP2004359573A (ja) * | 2003-06-03 | 2004-12-24 | Nikko Chemical Co Ltd | ヒアルロン酸産生促進剤、及び該ヒアルロン酸産生促進剤を用いた皮膚外用剤、及び化粧料 |
JP2008529964A (ja) * | 2003-06-25 | 2008-08-07 | トポターゲット ジャーマニー アーゲー | 皮膚疾患の予防または治療用のバルプロ酸の局所使用 |
JP2006528935A (ja) * | 2003-07-25 | 2006-12-28 | ザ プロクター アンド ギャンブル カンパニー | N−アシルアミノ酸組成物を用いた哺乳類のケラチン組織の調整 |
JP2007519689A (ja) * | 2004-01-29 | 2007-07-19 | ピエール ファーブル デルモ−コスメティック | ヒアルロン酸ナトリウムの断片とレチノイドを組み合わせる局所用組成物 |
US8968751B2 (en) | 2004-01-29 | 2015-03-03 | Pierre Fabre Dermo Cosmetique | Topical compositions associating sodium hyaluronate fragments and retinoid useful for cosmetic and medical dermatology |
JP2008024704A (ja) * | 2006-06-23 | 2008-02-07 | Rohto Pharmaceut Co Ltd | ヒアルロン酸産生促進能及び/又は線維芽細胞増殖促進能を有する組成物 |
JP2008195629A (ja) * | 2007-02-09 | 2008-08-28 | Naris Cosmetics Co Ltd | 皮膚光老化改善剤 |
JP2011042627A (ja) * | 2009-08-21 | 2011-03-03 | Unitika Ltd | ヒアルロン酸合成促進剤 |
JP2013523701A (ja) * | 2010-04-02 | 2013-06-17 | リブラジェン | N−アセチル−グルコサミン−6−ホスファートを含む化粧品および医薬組成物 |
JP2013203731A (ja) * | 2012-03-29 | 2013-10-07 | Nof Corp | ヒアルロン酸産生促進剤 |
JP2015163642A (ja) * | 2015-06-03 | 2015-09-10 | ユニチカ株式会社 | ヒアルロン酸合成促進剤 |
Also Published As
Publication number | Publication date |
---|---|
KR100615369B1 (ko) | 2006-08-25 |
WO2002076470A8 (fr) | 2002-10-24 |
EP1384482A4 (en) | 2004-06-30 |
US20050002879A1 (en) | 2005-01-06 |
WO2002076470A1 (en) | 2002-10-03 |
CN1509179A (zh) | 2004-06-30 |
US20080287393A1 (en) | 2008-11-20 |
TWI245633B (en) | 2005-12-21 |
CN1220492C (zh) | 2005-09-28 |
KR20040021595A (ko) | 2004-03-10 |
EP1384482A1 (en) | 2004-01-28 |
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