JP4855382B2 - 皮膚美白剤、組成物及び方法 - Google Patents
皮膚美白剤、組成物及び方法 Download PDFInfo
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- JP4855382B2 JP4855382B2 JP2007500107A JP2007500107A JP4855382B2 JP 4855382 B2 JP4855382 B2 JP 4855382B2 JP 2007500107 A JP2007500107 A JP 2007500107A JP 2007500107 A JP2007500107 A JP 2007500107A JP 4855382 B2 JP4855382 B2 JP 4855382B2
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- 239000000203 mixture Substances 0.000 title claims description 78
- 238000000034 method Methods 0.000 title claims description 33
- 239000007854 depigmenting agent Substances 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims description 68
- -1 dimethyl PABA octyl Chemical compound 0.000 claims description 45
- 239000002537 cosmetic Substances 0.000 claims description 32
- HSHNITRMYYLLCV-UHFFFAOYSA-N 4-methylumbelliferone Chemical compound C1=C(O)C=CC2=C1OC(=O)C=C2C HSHNITRMYYLLCV-UHFFFAOYSA-N 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000000516 sunscreening agent Substances 0.000 claims description 12
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 230000008901 benefit Effects 0.000 claims description 11
- 230000000475 sunscreen effect Effects 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 230000002087 whitening effect Effects 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000002015 acyclic group Chemical group 0.000 claims description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 claims description 5
- 229960001679 octinoxate Drugs 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 4
- 229920001273 Polyhydroxy acid Polymers 0.000 claims description 3
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical class CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 229940061720 alpha hydroxy acid Drugs 0.000 claims description 3
- 150000001280 alpha hydroxy acids Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 150000001277 beta hydroxy acids Chemical class 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 150000003700 vitamin C derivatives Chemical class 0.000 claims description 3
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 claims description 2
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
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- 150000004706 metal oxides Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 claims 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 2
- HEOCBCNFKCOKBX-RELGSGGGSA-N (1s,2e,4r)-4,7,7-trimethyl-2-[(4-methylphenyl)methylidene]bicyclo[2.2.1]heptan-3-one Chemical compound C1=CC(C)=CC=C1\C=C/1C(=O)[C@]2(C)CC[C@H]\1C2(C)C HEOCBCNFKCOKBX-RELGSGGGSA-N 0.000 claims 1
- LALVCWMSKLEQMK-UHFFFAOYSA-N 1-phenyl-3-(4-propan-2-ylphenyl)propane-1,3-dione Chemical compound C1=CC(C(C)C)=CC=C1C(=O)CC(=O)C1=CC=CC=C1 LALVCWMSKLEQMK-UHFFFAOYSA-N 0.000 claims 1
- MEZZCSHVIGVWFI-UHFFFAOYSA-N 2,2'-Dihydroxy-4-methoxybenzophenone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1O MEZZCSHVIGVWFI-UHFFFAOYSA-N 0.000 claims 1
- TYYHDKOVFSVWON-UHFFFAOYSA-N 2-butyl-2-methoxy-1,3-diphenylpropane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C(OC)(CCCC)C(=O)C1=CC=CC=C1 TYYHDKOVFSVWON-UHFFFAOYSA-N 0.000 claims 1
- WSSJONWNBBTCMG-UHFFFAOYSA-N 2-hydroxybenzoic acid (3,3,5-trimethylcyclohexyl) ester Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C1=CC=CC=C1O WSSJONWNBBTCMG-UHFFFAOYSA-N 0.000 claims 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims 1
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- 229960005193 avobenzone Drugs 0.000 claims 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims 1
- 239000012965 benzophenone Substances 0.000 claims 1
- 229940111759 benzophenone-2 Drugs 0.000 claims 1
- WXNRYSGJLQFHBR-UHFFFAOYSA-N bis(2,4-dihydroxyphenyl)methanone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1O WXNRYSGJLQFHBR-UHFFFAOYSA-N 0.000 claims 1
- SODJJEXAWOSSON-UHFFFAOYSA-N bis(2-hydroxy-4-methoxyphenyl)methanone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=C(OC)C=C1O SODJJEXAWOSSON-UHFFFAOYSA-N 0.000 claims 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 1
- UVCJGUGAGLDPAA-UHFFFAOYSA-N ensulizole Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 claims 1
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- 229940102398 methyl anthranilate Drugs 0.000 claims 1
- 229960003921 octisalate Drugs 0.000 claims 1
- FMJSMJQBSVNSBF-UHFFFAOYSA-N octocrylene Chemical group C=1C=CC=CC=1C(=C(C#N)C(=O)OCC(CC)CCCC)C1=CC=CC=C1 FMJSMJQBSVNSBF-UHFFFAOYSA-N 0.000 claims 1
- 229960000601 octocrylene Drugs 0.000 claims 1
- WCJLCOAEJIHPCW-UHFFFAOYSA-N octyl 2-hydroxybenzoate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1O WCJLCOAEJIHPCW-UHFFFAOYSA-N 0.000 claims 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 claims 1
- 229960001173 oxybenzone Drugs 0.000 claims 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 1
- 229960004889 salicylic acid Drugs 0.000 claims 1
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 claims 1
- 229960000368 sulisobenzone Drugs 0.000 claims 1
- 210000003491 skin Anatomy 0.000 description 34
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000194 fatty acid Substances 0.000 description 16
- 235000001671 coumarin Nutrition 0.000 description 15
- 229960000956 coumarin Drugs 0.000 description 15
- 235000014113 dietary fatty acids Nutrition 0.000 description 14
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 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 6
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- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 description 4
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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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/52—Unsaturated compounds containing hydroxy or O-metal groups a hydroxy or O-metal group being bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
- A61K2800/782—Enzyme inhibitors; Enzyme antagonists
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- Birds (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
R3は、直鎖又は分岐の、環式又は非環式の、飽和又は不飽和の、C1−C12アルキル、アルケニル、シクロアルキル、シクロアルケニル又はヘテロアルキル基を表す。好ましくは、R3は、アルキル基を表す。より好ましくは、R3は、C1アルキル基(すなわち、メチル基)を表し;及び
R5は、水素原子(H)又はR4を表す。好ましくは、R5は、水素を表す。
R4は、直鎖又は分岐の、環式又は非環式の、飽和又は不飽和の、複素原子含有又は非含有の、C1−C22アルキル、アルケニル、シクロアルキル、シクロアルケニル、ヘテロアルキル、アリール又はヘテロアリール基を表す。)を含む、B、C、D及びこれらの混合物からなる群から選択される一般式を有する化合物を作製する方法を提供する。
の化合物を与えるために、フェニル環の1,3−ヒドロキシ位の置換を含み得る。
本発明は、一般式Iの化合物、該化合物を含む組成物、及び特に、皮膚美白剤としてのこれらの化粧的使用に関する。前記組成物及び方法の具体的な利点は、他の皮膚美白化合物より(類似の構造を有する皮膚美白化合物でさえ)、一般式Iの化合物が皮膚に対する刺激性を低くすることができ、比較的製造が容易であるということである。
合成の手順
1.4−置換された−7−ヒドロキシクマリンの水素化
高圧反応容器に、適切な溶媒(例えば、酢酸、アルコール、有機溶媒及びこれらの混合物)中の、一般式Aの化合物(4−置換された−7−ヒドロキシクマリン(好ましくは、4−アルキル−7−ヒドロキシクマリン))を充填し、触媒(例えば、適切なマトリックスに付着されたPd及び/又はNi及びこれらの混合物などの同種又は異種の触媒)を添加する。前記反応器を水素で加圧し(例えば、690kPaないし5.5MPa[100ないし800psi])、適切な分析方法(例えば、TLC、GC、LC、水素消費及びこれらの組み合わせ)を用いてモニターした場合に、4−置換された−7−ヒドロキシクマリン(好ましくは、4−アルキル−7−ヒドロキシクマリン)の完全な消費が観察されるまで、25℃以上(例えば、25℃ないし60℃)で撹拌する。不溶性支持体(例えば、CeliteTM、シリカゲル及びこれらの組み合わせ)を通して、反応混合物をろ過し、減圧下で溶媒を除去し、例えば、再結晶、蒸留及びこれらの組み合わせなどの精製方法を用いて生成物を精製する。
7−ヒドロキシ−3,4−ジヒドロ−4−メチルクマリン(B1)
Parr水素添加装置(1L)に、7−ヒドロキシ−4−メチルクマリン、すなわち、式A1の化合物、(60g、0.34mol)及び酢酸(350mL)を充填した。酢酸(150mL)中の10% Pd/C(6.0g)の懸濁液を添加し、前記反応器を密封し、脱気し、窒素をパージ(4×)した。水素を用いて、2.2MPa(320psi)まで反応器を加圧し、30℃で16時間撹拌したが、この時点では、水素は全く消費されておらず、出発材料を消費して生成物がきれいに形成されることが、TLC(4%メタノール:クロロホルム)によって示された。反応器を排気し、窒素をパージし、前記混合物をCeliteTMに通してろ過した。溶媒を除去して、白色固体(60.5g、100%)を得た。酢酸エチル:ヘキサンからの再結晶によって、純粋な生成物が白色固体として得られた。融点109−110℃;1H NMR(DMSO−d6)d1.19(d,JJ=6.7,3H),2.52(dd,JJ=15.9,7.3,1H),2.84(dd,JJ=15.9,5.5,1H),3.08(m,1H),6.46(d,JJ=2.4,1H),6.58(dd,JJ=8.2,2.4,1H),7.10(d,JJ=8.2,1H),9.66(s,1H);13C(DMSO−d6)d19.84,27.87,36.45,103.17,111.38,118.29,127.17,151.45,157.17,168.11;m/z(EI;TMS誘導化;M+)250;IR(neat;cm−1)3379.6,2969.2,2930.2,2871.5,1748.0,1630.7,1601.4,1518.4,1454.89,1352.3,1283.9,1249.7,1239.9,1152.0,1117.8,1078.7,1020.1,995.7,942.0,854.0,814.9。
一般式Bの化合物、すなわち、4−置換された−3,4−ジヒドロ−7−ヒドロキシクマリンを、水の中に懸濁し、水酸化物イオン均等物試薬(例えば、水酸化ナトリウム、水酸化カリウム、ポリマー結合された炭酸塩及びこれらの組み合わせ)を添加する。出発材料が完全に消費されるまで、適切な分析方法(例えば、TLC、GC、LC及びこれらの組み合わせ)を用いて、反応をモニターする。反応混合物を冷却し(例えば、0ないし10℃の温度)、溶液のpHが1以下に達するまで、水素イオン均等物試薬(例えば、塩酸)で酸性化する。適切な有機溶媒(例えば、ジエチルエーテル)を用いて溶液を抽出し、不溶性の乾燥剤(例えば、硫酸ナトリウム)を用いて有機層を乾燥し、ろ過し、溶媒を除去する。例えば、再結晶、蒸留、クロマトグラフィー又はこれらの組み合わせなどの精製方法を用いて、生成物を精製する。
3−(2,4−ジヒドロキシフェニル)−酪酸(一般式IIの化合物)
7−ヒドロキシ−3,4−ジヒドロ−4−メチルクマリン(式B1の化合物)(8.0g、45mmol)の水中(40mL)懸濁液に、水酸化ナトリウム(5.0M、27mL、135mmol)を室温(20℃)で添加し、得られた溶液を20分間撹拌した。この時点で、出発材料を消費して、生成物がきれいに形成されることが、TLC(4%メタノール:クロロホルム)によって示された。溶液を5℃まで冷却し、添加全体を通じて、温度を常に15℃未満に保ちながら、pHが1未満になるように、濃HClを用いて慎重に酸性化した。ジエチルエーテル(4×100mL)で溶液を抽出し、飽和NaCl(4×50mL)で有機層を洗浄し、一つにまとめ、乾燥させ(Na2SO4)、ろ過し、溶媒を除去して、薄いオレンジ色の油を得た。シリカゲルの短いパッドを通してろ過することによってさらに精製し、酢酸エチルで溶出することによって、純粋な生成物を白色固体として得た(8.3g、94%)。融点92−94℃;1H NMR((DMSO−d6)d1.13(d,JJ=7.0,3H),2.33(dd,JJ=15.0,8.9,1H),2.52(dd,JJ=15.5,7.3,1H),3.32(m,1H),6.16(dd,JJ=8.2,2.4,1H),6.28(d,JJ=2.4,1H),6.84(d,JJ=8.2,1H),9.08(s,1H),9.59(s,1H),11.87(s,1H);13C NMR(DMSO−d6)d20.39,28.97,41.0,102.58,106.01,122.55,127.27,155.19,156.18,173.74;m/z(EI;TMS誘導化:M+)412;IR(neat;cm−1)3360.1,2974.1,2935.1,2876.4,1748.0,1713.8,1625.9,1606.3,1518.4,1459.8,1381.6,1347.4,1283.9,1254.6,1239.9,1156.9,1117.8,1025.0,981.0,937.1,849.1,810.1。
一般式Bの化合物、すなわち、4−置換された−3,4−ジヒドロ−7−ヒドロキシクマリンを、選択したアルコール中に溶解するか、又は該クマリンとアルコールを適切な溶媒(例えば、テトラヒドロフラン)中に溶解する。酸触媒を添加し(例えば、硫酸、酸性樹脂又はこれらの組み合わせ)、出発材料が完全に消費されるまで、適切な分析方法(例えば、TLC、GC、LC又はこれらの組み合わせ)を用いて、反応をモニターする。穏やかな塩基(例えば、炭酸水素ナトリウム水溶液)を用いて、この反応混合物を(4ないし7のpHになるように)部分的に中和し、適切な有機溶媒(例えば、ジエチルエーテル)と水の間に分配した。不溶性の乾燥剤(例えば、硫酸ナトリウム)を用いて、有機層を乾燥し、ろ過し、減圧下で溶媒を除去する。例えば、再結晶、蒸留、クロマトグラフィー及び/又はこれらの組み合わせなどの精製方法を用いて、生成物を精製する。
3−(2,4−ジヒドロキシフェニル)−酪酸メチル(D1)
メタノール(1L)中の7−ヒドロキシ−3,4−ジヒドロ−4−メチルクマリン(B1)(75.8g、430mmol)の溶液に、濃硫酸(1.2mL、43mmol)を、室温で添加し、この溶液を16時間撹拌した。この時点で、出発材料を消費して、生成物がきれいに形成されることが、TLC(8%メタノール:クロロホルム)によって示された。7% NaHCO3(50mL)を用いて、溶液を中和し、溶媒(750mL)の大半を減圧下で除去した。溶液を酢酸エチル(1L)で希釈し、飽和NaHCO3:飽和NaCl(1:1、200mL)、飽和NaCl(2×200mL)で連続的に洗浄し、乾燥し(Na2SO4)、ろ過し、溶媒を除去して、オレンジ色の油を得た。シリカゲルの短いパッドを通してろ過することによってさらに精製し、クロロホルム中の5%メタノールで溶出することによって、純粋な生成物を薄いオレンジ色のゲルとして得た(87g、98%)。1H NMR(DMSO−d6)d1.13(d,JJ=7.0,3H),2.42(dd,JJ=15.0,8.9,1H),2.58(dd,JJ=15.0,5.8,1H),3.37(m,1H),3.55(s,3H),6.15(dd,JJ=8.6,2.4,1H),6.28(d,JJ=2.4,1H),6.84(d,JJ=8.2,1H),8.93(s,1H),9.11(s,1H);13C NMR(DMSO−d6)d20.16,29.09,40.77,51.00,102.55,106.02,122.09,127.04,155.18,156.27,172.55;m/z(EI;TMS誘導化;M+)354;IR(neat;cm−1)3384.5,2969.3,1708.9,1621.0,1606.3,1518.4,1454.9,1367.0,1303.5,1220.4,1166.7,1108.1,976.2,839.4,810.1。
好ましい化粧組成物は、本発明の方法に従って、ヒトの皮膚に適用するのに適している化粧組成物であり、該組成物は、必要に応じて、しかし、好ましくは、クマリン由来化合物に加えて皮膚有益剤を含む。
化粧として許容されるビヒクルは、組成物が皮膚に適用されたときに皮膚有益成分の配分を促進するために、前記組成物中の皮膚有益成分のための、希釈剤(dilutant)、分散剤又は担体として作用し得る。
(1)10ないし20個の炭素原子を有する脂肪酸のアルケニル又はアルキルエステルがある。その例には、ネオペンタン酸イソアラキジル、イソナノン酸イソノニル、ミリスチン酸オレイル、ステアリン酸オレイル及びオレイン酸オレイルが含まれる。
本発明の化粧組成物中には、可塑剤;カラミン;抗酸化剤;キレート剤;及び日焼け止め剤を必要に応じて添加することができる。
本発明の方法は、主として、皮膚の美白を行うため、皮膚中の色素沈着の程度を軽減するため、及び/又は肌の色合いを均一にするために、ヒトの皮膚に局所適用するためのパーソナルケア製品を使用することを目的とする。
本発明の化粧組成物は、4,000から10,000mPasまでの粘度(20℃で)を有するローションとして、10,000から20,000mPasまでの粘度(20℃で)を有する液体クリームとして、又は20,000から100,000mPasまで若しくはこれ以上の粘度(20℃で)を有するクリームとして、調合することが可能である。その粘度及び消費者による意図した使用に適合させるために、組成物は、適切な容器中に梱包することが可能である。例えば、ローション又は液体クリームは、瓶又は回転ボール式塗布器又は噴射剤によって駆動されるエアロゾル装置又は指による操作に適したポンプが装着された容器中に詰めることが可能である。組成物がクリームである場合には、単に、チューブ又は蓋のあるジャーなどの変形しない瓶又は圧搾容器中に保存することが可能である。組成物が固体又は半固体のスティックである場合には、手動で又は機械的に組成物を排出し、又は押し出すための適切な容器中に詰めることができる。
以下に記載されている実施例を通じて、本実施例に記載されている手順に従って調製された以下の化合物を使用した。
本発明の範囲に属する化粧組成物を調製した。
本発明の範囲に属するさらなる化粧組成物を調製した。
2.別の容器中で、相Bを75℃まで加熱する
3.BをAに添加し、加熱を停止して、30分間混合する
4.50℃で、相Cを添加し、10分間混合する。
本発明の範囲に属する、本発明の方法において有用なさらなる組成物の群が調製され、下表に列記されている。本組成物は、実施例3に記載されている方法を用いて調製した。
本実施例は、前記方法に従い、皮膚美白剤として、4−メチル 7−ヒドロキシクマリン由来レゾルシノール化合物を使用することの皮膚美白効果を示す。本実験は、細胞に基づいたアッセイを用いて実施した。
マッシュルームチロシナーゼ阻害は、メラニン合成の減少の指標であり、これによって、皮膚美白効果を示す。本実験は、本発明のクマリン由来レゾルシノール誘導体の効力を示す。
Claims (16)
- 前記化合物が、4−メチル−7−ヒドロキシクマリンから得られる、請求項1ないし2の何れかに記載の化合物。
- a.請求項1ないし3の何れか一項に記載の化合物の0.000001ないし50重量%と、
b.化粧として許容される担体と、
を含む、化粧組成物。 - 前記化合物が前記組成物の0.00001%ないし10重量%を占める、請求項4に記載の化粧組成物。
- 前記化合物が前記組成物の0.001%ないし7重量%を占める、請求項5に記載の化粧組成物。
- 前記化合物が前記組成物の0.01%ないし5重量%を占める、請求項6に記載の化粧組成物。
- 前記組成物が日焼け止め剤をさらに含む、請求項4ないし7の何れか一項に記載の化粧組成物。
- 前記日焼け止め剤が微粉化された金属酸化物である、請求項8に記載の化粧組成物。
- 前記日焼け止め剤が、ベンゾフェノン−3、ベンゾフェノン−4、ベンゾフェノン−8、DEA、メトキシ桂皮酸エステル、ジヒドロキシプロピル−PABAエチル、PABAグリセリル、ホモサラート、アントラニル酸メチル、オクトクリレン、ジメチルPABAオクチル、メトキシ桂皮酸オクチル(PARSOLTM MXC)、サリチル酸オクチル、PABA、2−フェニルベンズイミダゾール−5−スルホン酸、サリチル酸TEA、3−(4−メチルベンジリデン)−ショウノウ、ベンゾフェノン−1−、ベンゾフェノン−2、ベンゾフェノン−6、ベンゾフェノン−12、4−イソプロピルジベンゾイルメタン、ブチルメトキシジベンゾイルメタン(PARSOLTM 1789)、エトクリレン及びこれらの混合物からなる群から選択される有機日焼け止め剤である、請求項8に記載の化粧組成物。
- 前記組成物が、α−ヒドロキシ酸、β−ヒドロキシ酸、ポリヒドロキシ酸、ヒドロキノン、t−ブチルヒドロキノン、ビタミンC誘導体、二酸、レチノイド、レゾルシノール誘導体及びこれらの混合物からなる群から選択される皮膚有益剤をさらに含む、請求項4ないし10の何れか一項に記載の化粧組成物。
- 請求項4ないし11の何れか一項に記載の組成物を皮膚に適用することを含む、皮膚美白の美容方法。
- 皮膚美白のための、請求項1ないし3の何れか一項に記載の化合物の使用。
- (i)一般式Aの化合物
の化合物を、触媒の存在下で水素と反応させる工程を含むプロセスによって、式Bの化合物
(ii)前記式Bの化合物を、式R4OH(R4は、直鎖又は分岐の、環式又は非環式の、飽和又は不飽和の、複素原子含有又は非含有の、C1−C22アルキル、アルケニル、シクロアルキル、シクロアルケニル、ヘテロアルキル、アリール又はヘテロアリール基を表す。)を有する化合物と反応させる工程と;
を含む、一般式Dの化合物
- (iii)請求項14に記載の方法によって一般式Cを有する化合物を作製する工程、又は請求項15に記載の方法によって一般式Dを有する化合物を作製する工程と;次いで、
(iv)前記一般式C又はDを有する化合物のフェニル環の1−ヒドロキシ位、3−ヒドロキシ位、又は1及び3−ヒドロキシ位の両方を置換する工程と;
を含み、
R1及びR2の両方が、直鎖若しくは分岐の、飽和若しくは不飽和の、C1−C12アルキル、アルケニル、アシル若しくはヘテロアルキル基を表し、又はR1及びR2の一方が水素原子(H)を表し、R1及びR2の他方が、直鎖若しくは分岐の、飽和若しくは不飽和の、C1−C12アルキル、アルケニル、アシル又はヘテロアルキル基を表す、
一般式(I’)
の化合物を作製する方法。
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US10/789,293 | 2004-02-27 | ||
US10/789,293 US7300646B2 (en) | 2004-02-27 | 2004-02-27 | Skin lightening agents, compositions and methods |
PCT/EP2005/001595 WO2005085169A1 (en) | 2004-02-27 | 2005-02-16 | Skin lightening agents, compositions and methods |
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EP (1) | EP1718594B1 (ja) |
JP (1) | JP4855382B2 (ja) |
AU (1) | AU2005219510B2 (ja) |
BR (1) | BRPI0507222B1 (ja) |
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US7300646B2 (en) * | 2004-02-27 | 2007-11-27 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Skin lightening agents, compositions and methods |
US7365125B2 (en) * | 2004-08-16 | 2008-04-29 | General Electric Company | Polycarbonate compositions, articles, and method of manufacture |
WO2011084703A2 (en) | 2009-12-21 | 2011-07-14 | Advanced Liquid Logic, Inc. | Enzyme assays on a droplet actuator |
US20090263513A1 (en) * | 2008-04-18 | 2009-10-22 | Jan Marini | Cosmetic skin lightening formulation |
FR2939136B1 (fr) | 2008-12-02 | 2010-12-03 | Galderma Res & Dev | Nouveaux composes 4-(heterocycloalkyl)-benzene-1,3-diol comme inhibiteurs de la tyrosinase, leur procede de preparation et leur utilisation en medecine humaine ainsi qu'en cosmetique |
FR2939135B1 (fr) | 2008-12-02 | 2010-12-03 | Galderma Res & Dev | Nouveaux composes 4-(azacycloalkyl)-benzene-1,3-diol comme inhibiteurs de la tyrosinase, leur procede de preparation et leur utilisation en medecine humaine ainsi qu'en cosmetique |
US9044623B2 (en) | 2009-01-27 | 2015-06-02 | Isp Investments Inc. | Polymer-bound UV absorbers in personal care compositions |
CA3045407C (en) | 2009-07-29 | 2024-03-12 | Elise A. Olsen | Compositions and methods for inhibiting hair growth |
FR2953834B1 (fr) | 2009-12-10 | 2012-01-13 | Galderma Res & Dev | Nouveaux composes 4-(azacycloalkyl)-benzene-1,3-diol comme inhibiteurs de la tyrosinase, leur procede de preparation et leur utilisation en medecine humaine ainsi qu'en cosmetique |
US9513253B2 (en) | 2011-07-11 | 2016-12-06 | Advanced Liquid Logic, Inc. | Droplet actuators and techniques for droplet-based enzymatic assays |
KR101457370B1 (ko) * | 2012-09-06 | 2014-11-03 | (주)에이씨티 | 신규 벤젠 디올 유도체 화합물 및 이를 이용한 화장료 조성물 |
US20140256830A1 (en) | 2013-03-08 | 2014-09-11 | Ampere Life Sciences, Inc. | Resorcinol compounds for dermatological use |
WO2017025105A1 (en) * | 2015-08-12 | 2017-02-16 | Nmetics Ivs | 3-(4-hydroxyphenyl)propanoic acid amide for use in tissue repair and/or skin brightening |
FR3045039B1 (fr) | 2015-12-15 | 2017-12-22 | Oreal | Derives de resorcinol pour leur utilisation cosmetique |
FR3045600B1 (fr) * | 2015-12-16 | 2018-01-26 | L'oreal | Derives de resorcinol pour leur utilisation cosmetique |
FR3067027B1 (fr) * | 2017-05-31 | 2019-06-21 | L'oreal | Derives de resorcinol pour leur utilisation cosmetique |
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US7723537B2 (en) | 2010-05-25 |
EP1718594A1 (en) | 2006-11-08 |
US20080039636A1 (en) | 2008-02-14 |
US20050191250A1 (en) | 2005-09-01 |
JP2007523932A (ja) | 2007-08-23 |
NZ549358A (en) | 2010-01-29 |
AU2005219510B2 (en) | 2008-05-15 |
TW200531706A (en) | 2005-10-01 |
AU2005219510A1 (en) | 2005-09-15 |
TWI391145B (zh) | 2013-04-01 |
WO2005085169A1 (en) | 2005-09-15 |
BRPI0507222B1 (pt) | 2015-09-08 |
US7300646B2 (en) | 2007-11-27 |
BRPI0507222A (pt) | 2007-06-19 |
ES2543980T3 (es) | 2015-08-26 |
ZA200607017B (en) | 2008-04-30 |
EP1718594B1 (en) | 2015-06-10 |
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