JP5455897B2 - 色素沈着の調節化合物 - Google Patents
色素沈着の調節化合物 Download PDFInfo
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- JP5455897B2 JP5455897B2 JP2010511666A JP2010511666A JP5455897B2 JP 5455897 B2 JP5455897 B2 JP 5455897B2 JP 2010511666 A JP2010511666 A JP 2010511666A JP 2010511666 A JP2010511666 A JP 2010511666A JP 5455897 B2 JP5455897 B2 JP 5455897B2
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Description
本発明は、6−置換−7−メトキシ−2,2−ジメチルクロマン、及びこれらの化合物を含有する、皮膚、髪、及び/若しくは爪の治療、ケア、及び/若しくは洗浄、好ましくは皮膚及び髪の色素沈着の程度の減弱、又は爪表面の斑点の治療、或いは皮膚、髪、及び爪の光防護のための化粧品又は医薬品組成物に関する。
自然の皮膚色素沈着を変更することは、米国、アジア、又は欧州の多くの人々にとっていくつかの理由で望ましいことである。自然の皮膚色を変更する理由の一部としては、美の典型としてより明るい皮膚の探求、及びそばかす又は黒子など皮膚表面の斑点の除去又は減弱が挙げられる。
本発明は、皮膚、髪、及び/又は爪を治療、ケア、及び/又は洗浄するための簡単で、効果的で、且つリスクのない解決策であって、哺乳類の皮膚、髪、及び/又は爪に6−置換−7−メトキシ−2,2−ジメチルクロマンを適用するステップを含む解決策を提供する。本発明の目的は、少なくとも1種の式(1)の6−置換−7−メトキシ−2,2−ジメチルクロマン、及び化粧品又は医薬品として許容される媒体を含有する化粧品又は医薬品組成物でもある。
に関し、
式中、Xは、O又はSからなる群から選択され、
Rは、2〜23個の炭素原子(C2〜C23)を有する直鎖状若しくは分枝状の飽和若しくは不飽和脂肪族基、又は環式基である。
が、tert−ブタノイル、2−メチルヘキサノイル、ヘキサノイル、オクタノイル、デカノイル、ラウロイル、ミリストイル、パルミトイル、ステアロイル、オレオイル、又はリノレオイルからなる群から選択される脂肪族基であるものである。
が、−CO−(CH2)0〜6−フェニル、−CO−(CH2)0〜6−(1−ナフチル)、−CO−(CH2)0〜6−(2−ナフチル)、−CO−(CH2)0〜6−CH(フェニル)2、−CO−(2−フルオロフェニル)、−CO−シクロヘキシル、α−リポイル、L−プロリル、D−プロリル、ビオチニル−CO−(4−イミダゾリル)、−CO−(2−ピリジル)、−CO−(2−チエニル)、−CO−(2−フリル)、又は−CO−(3−フリル)からなる群から選択される脂環式、芳香族、又はヘテロ環式基であるものである。
式中、Xは、O又はSからなる群から選択され、
Rは、2〜23個の炭素原子(C2〜C23)を有する直鎖状若しくは分枝状の飽和若しくは不飽和脂肪族基、又は環式基であり、
Zは、遊離OH基、その反応性誘導体、又はハロゲンである。
また、本発明は、下記の[39]〜[50]を提供する。
[39] 上記一般式(1)の化合物、又はその化粧品若しくは医薬品として許容される塩の、皮膚、髪、及び/又は爪を治療、ケア、及び/又は洗浄するための化粧品又は医薬品組成物を調製するための使用。
[40] [39]に記載の一般式(I)の化合物、又はその化粧品若しくは医薬品として許容される塩の、色素沈着調節が必要である前記皮膚、髪、及び/又は爪の病態、障害、又は病状を治療するための化粧品又は医薬品組成物を調製するための使用。
[41] [39]又は[40]に記載の一般式(1)の化合物、又はその化粧品若しくは医薬品として許容される塩の、そばかす、黒子、肝斑、まだら症、アジソン病、白斑、紫外線への曝露による斑点、老化による斑点、光老化による斑点、炎症由来、特にレーザー治療後又は美容外科手術後の炎症由来の斑点、アクネ、湿疹、組織褐変症、瘢痕、及び/若しくはホルモン障害による斑点からなる群から選択される皮膚の病態、障害、又は病状を治療するための化粧品又は医薬品組成物を調製するための使用。
[42] [39]に記載の一般式(I)の化合物、又はその化粧品若しくは医薬品として許容される塩の、前記老化の徴候を低減又は遅延させる化粧品又は医薬品組成物を調製するための使用。
[43] [39]に記載の一般式(I)の化合物、又はその化粧品若しくは医薬品として許容される塩の、前記光老化の徴候を低減又は遅延させる化粧品又は医薬品組成物を調製するための使用。
[44] [39]に記載の一般式(I)の化合物、又はその化粧品若しくは医薬品として許容される塩の、前記皮膚、髪、及び/又は爪の光防護のための化粧品又は医薬品組成物を調製するための使用。
[45] [39]又は[40]に記載の一般式(I)の化合物、又はその化粧品若しくは医薬品として許容される塩の、化粧品又は医薬品組成物を調製するための使用であって、前記組成物は、局所適用又は経皮適用によって適用する部位における前記皮膚、髪、及び/又は爪の色素沈着の程度を調節する、使用。
[46] [44]に記載の一般式(I)の化合物、又はその化粧品若しくは医薬品として許容される塩の、化粧品又は医薬品組成物を調製するための使用であって、前記組成物は、局所適用又は経皮適用によって適用する部位における前記皮膚、髪、及び/又は爪の色を低減又は明るくする、使用。
[47] 前記局所適用又は経皮適用が、イオントフォレシス、ソノフォレシス、電気穿孔法、スチームラップ、マイクロインジェクション、又は圧力による無針注射によって行われる、[44]又は[45]に記載の使用。
[48] [39]又は[40]に記載の一般式(I)の化合物、又はその化粧品若しくは医薬品として許容される塩の、経口、経鼻、非経口、又は直腸内投与によって前記皮膚、髪、及び/又は爪の色素沈着の程度を調節する化粧品又は医薬品組成物を調製するための使用。
[49] [39]又は[40]に記載の一般式(I)の化合物、又はその化粧品若しくは医薬品として許容される塩の、顔毛又は体毛を明るく又は色素脱失するための化粧品又は医薬品組成物を調製するための使用。
[50] [39]又は[40]に記載の一般式(I)の化合物、又はその化粧品若しくは医薬品として許容される塩の、爪表面の斑点を治療するための化粧品又は医薬品組成物を調製するための使用。
試薬及び溶媒はすべて、合成用の品質であり、さらなる処理をすることなく、使用される。
DNA、デオキシリボ核酸;QSF、十分量;DCC、N,N−ジシクロヘキシルカルボジイミド;DMAP、ジメチルアミノピリジン;DMSO、ジメチルスルホキシド;DMEM、ダルベッコ変法イーグル培地;DPPC、ジパルミトイルホスファチジルコリン;equiv.、当量;ESI−MS、エレクトロスプレーイオン化質量分析;FBS、ウシ胎仔血清;HEPES、N−2−ヒドロキシエチルピペラジン−N’−2−エタンスルホン酸;HPLC、高速液体クロマトグラフィー;MAP、アスコルビル−2−リン酸マグネシウム塩;MLV、多層小胞;MW、分子量;PMA、酢酸1−メトキシ−2−プロピル;ULV、単層小胞;UV、紫外線;UVA、紫外線A型;UVB、紫外線B型.
6−置換−7−メトキシ−2,2−ジメチルクロマンの調製。
ジクロロメタン中、DMAP(2.0mmol、0.083当量)及びDCC(24.0mmol、1当量)の存在下で、6−ヒドロキシ−7−メトキシ−2,2−ジメチルクロマン(5.0g;24.0mmol、1当量)と、1当量の対応するカルボン酸又はチオカルボン酸を室温で反応させ、薄層クロマトグラフィーで制御した。反応が進行を止めたことが観察されると、生成したジシクロヘキシル尿素を濾過し、蒸発乾固した。得られた化合物をシリカカラムクロマトグラフィーでn−ヘキサン及び酢酸エチルで溶離することによって精製し、ESI−MSで特徴付けた。
7−メトキシ−6−パルミトイル−2,2−ジメチルクロマンを含有する化粧品組成物の調製。
以下の製剤を、本発明に記載するように調製した。
A相の成分を十分大きい反応器に計量し、混合物を70℃に加熱して、ワックスを溶融する。B相の成分を内容物全体に適した容器に計量する。C相の成分をB相に添加し、激しく攪拌しながら、70℃に加熱する。次いで、直前の混合物に、攪拌しながらA相をゆっくりと添加し、混合物を攪拌しながら、70℃で30分間維持する。穏やかに攪拌しながら、放冷し、混合物が室温になると、キサンタンガム及び芳香剤を添加し、混合物を均質化し、必要なら、pHを、トリエタノールアミンで調整する。
7−メトキシ−6−パルミトイル−2,2−ジメチルクロマンを含有するリポソームの調製。
ジパルミトイルホスファチジルコリン(DPPC)、コレステロール、及び7−メトキシ−6−パルミトイル−2,2−ジメチルクロマンを計量し、クロロホルムに溶解する。リン脂質薄層を得るまで、溶媒を真空下で蒸発させ、これを、フェノニップ(Phenonip)(登録商標)を含有する水溶液で55℃において処理することによって水和し、MLVリポソームを得る。MLVリポソームを、55℃で超音波浴に2分間のサイクルで8回、5分間隔で浸すことによって、ULVリポソームを得る。サイズをはるかに低減するためには、高圧下で押出システムに通すことができる。
7−メトキシ−6−パルミトイル−2,2−ジメチルクロマンを含有するリポソームゲルの形の組成物の調製。
実施例3のリポソームを、穏やかに攪拌しながら、保存剤(EDTA、イミダゾリジニル尿素、及びフェノニップ(Phenonip)(登録商標))と一緒に、水に分散する。ヒスパゲル(Hispagel)(登録商標)200[INCI:アクア、グリセリン、及びポリアクリル酸グリセリル]を添加し、均質な混合物が得られるまで穏やかに攪拌する。
7−メトキシ−6−パルミトイル−2,2−ジメチルクロマンを含有するマニキュア液組成物の調製。
7−メトキシ−6−パルミトイル−2,2−ジメチルクロマンを、アクリラートコポリマーと共に計量し、激しく攪拌することによって、エタノールに溶解する。アセトンを添加し、蓋付きの容器に保存して、蒸発を最小限に抑制する。
体毛を色素脱失するための、7−メトキシ−6−パルミトイル−2,2−ジメチルクロマンを含有する組成物の調製。
A相及びB相を別々に、70〜75℃で加熱する。激しく攪拌しながら、AをBに添加する。室温で攪拌をしながら、放冷し、C相を添加し、トリエタノールアミンを用いて、pH6.5になるまで中和する。
インビトロでのマッシュルームチロシナーゼの作用に関する7−メトキシ−6−パルミトイル−2,2−ジメチルクロマンの活性比較アッセイ。
アッセイを96ウェルプレートで行い、試料は3回繰り返して行う。対照試料は、80μLの緩衝液(150mM HEPES)、10μLのマッシュルームチロシナーゼ(10μg/pL)、及び10μLの10mM L−ドーパ基質を含有する。正の対照は、さらにコウジ酸を0.1mMの濃度で含有する。7−メトキシ−6−パルミトイル−2,2−ジメチルクロマン及び6−ヒドロキシ−7−メトキシ−2,2−ジメチルクロマン(リポクロマン−6)の試料は、コウジ酸の代わりに、1mMの濃度で化合物を含有する。このようにして調製した試料を、37℃で10分間インキュベートする。次いで、試料の入ったプレートを氷上で5分間冷却して、酵素反応を止める。生成したメラニンを定量するために、プレートリーダーで492nmの波長において測定する。
ヒトメラノサイトから抽出された内因性チロシナーゼに関する7−メトキシ−6−パルミトイル−2,2−ジメチルクロマンの活性比較アッセイ。
10% FBS、1%ペニシリン/ストレプトマイシン、及び100nM PMAを補充したDMEM培地中で、ヒトメラノサイトを培養する。化合物の7−メトキシ−6−パルミトイル−2,2−ジメチルクロマンを、DMSO:滅菌水(1:1)に、最終濃度10mMで溶解する。
ヒトメラノサイト培養物における7−メトキシ−6−パルミトイル−2,2−ジメチルクロマンの色素脱失有効性の比較アッセイ。
0.1mMのコウジ酸又は7−メトキシ−6−パルミトイル−2,2−ジメチルクロマンを含有する新たな培地を毎日添加して、コンフルエントの状態で播種したヒトメラノサイトを5日間培養する。メラニン内容物は、倍率40倍のレンズを使用した顕微鏡によって直接見られた。メラニンを含む細胞の数及び細胞の総数をカウントすることによって、色素脱失有効性を決定し、得られた結果を、対照試料の美白有効性に対して標準化した。
ヒトケラチノサイト培養物における7−メトキシ−6−パルミトイル−2,2−ジメチルクロマンの光保護有効性のアッセイ。
96ウェルプレート中、ヒトケラチノサイトを培養状態で24時間維持して、単層を形成し、細胞を、150μg/mLの7−メトキシ−6−パルミトイル−2,2−ジメチルクロマン又はリン酸緩衝生理食塩水(対照)と共に、37℃で、5%のCO2を含む加湿空気中、暗所で1時間プレインキュベートした。次いで、太陽光シミュレーションランプを用いて、37J/cm2のエネルギーを、細胞に室温で150分間照射した。同時に暗所で、対照プレートを室温で維持した。照射時間後に、細胞の培地を新たな培地で置換し、細胞をさらに24時間インキュベートした。ニュートラルレッド色素によって、細胞生存率を決定し、分光光度計で、540nmにおける光学密度を測定した。
Claims (20)
- Rが、2〜23個の炭素原子を有する飽和又は不飽和脂肪族基である、請求項1に記載の化合物。
- Rが、脂環式基、芳香族環式基、又はヘテロ環式基である、請求項1に記載の化合物。
- 請求項1〜3のいずれか一項に記載の一般式(I)の化合物、又はその化粧品若しくは医薬品として許容される塩を得る方法であって、6−ヒドロキシ−7−メトキシ−2,2−ジメチルクロマンを、一般式(II)の化合物
[式中、Xは、O又はSからなる群から選択され、
Rは、2〜23個の炭素原子を有する直鎖状若しくは分枝状の飽和若しくは不飽和脂肪族基、又は環式基であり、これらの基は、ヒドロキシ、アルコキシ、アミノ、カルボキシル、シアノ、ニトロ、アルキルスルホニル、若しくはハロゲン原子からなる群から選択される置換基、又は環式基を含有することができ、
Zは、遊離OH基、その反応性誘導体、又はハロゲンである]
と反応させる、
ことを特徴とする方法。 - 化粧品として有効な量の請求項1〜3のいずれか一項に記載の少なくとも1種の一般式(I)の化合物、又はその化粧品として許容される塩を含む化粧品組成物であって、少なくとも1種の化粧品として許容される賦形剤又はアジュバントを含むことを特徴とする化粧品。
- 前記一般式(I)の化合物、又はその化粧品として許容される塩が、リポソーム、ミリカプセル、マイクロカプセル、ナノカプセル、海綿、小胞、ミセル、ミリスフェア、マイクロスフェア、ナノスフェア、リポスフェア、マイクロエマルジョン、ナノエマルジョン、ミリ粒子、マイクロ粒子、及び/又はナノ粒子からなる群から選択される化粧品として許容される徐放システム又は担体に組み込まれていることを特徴とする、請求項5に記載の化粧品組成物。
- さらに、色素脱失する又は美白剤、抗伸展線剤、抗シワ剤、酸化防止剤、抗糖化剤、NO合成酵素阻害剤、老化防止剤、目の下のたるみを低減若しくはなくすことができる物質、剥脱剤、乳化剤、柔軟剤、有機溶媒、液体噴射剤、スキンコンディショナー、湿潤化剤、水分保持物質、αヒドロキシ酸、保湿剤、ビタミン、顔料若しくは着色剤、染料、ゲル化ポリマー、粘稠化剤、界面活性剤、軟化剤、真皮若しくは表皮分子合成を刺激及び/又はそれらの分解を予防若しくは阻害するための物質、コラーゲン合成刺激剤、デコリン合成刺激剤、エラスチン合成刺激剤、ラミニン合成刺激剤、コラーゲン分解阻害剤、エラスチン分解阻害剤、線維芽細胞及び/若しくはケラチノサイト増殖を刺激又はケラチノサイト分化を刺激するための物質、脂質合成及び角質層の成分の合成刺激剤、グリコサミノグリカン合成刺激剤、DNA修復剤、DNA保護剤、デフェンシン合成刺激剤、シャペロン合成刺激剤、抗掻痒剤、敏感肌治療剤、収斂剤、皮脂産生調節剤、抗セルライト剤、脂肪分解刺激剤、真皮−表皮接合を改善するための物質、皮膚緩和剤、リアファーミング剤、大気汚染防止剤及び/若しくはラジカル捕捉剤、毛細血管循環及び/若しくは微小循環作用剤、鎮静剤、抗炎症剤、抗菌剤、抗真菌剤、殺菌剤、細胞代謝作用剤、キレート剤、並びに/或いは紫外線A及び/若しくはBに対して活性な有機又は無機光保護剤からなる群から選択される追加の化粧品として有効な量の少なくとも1種の活性剤又はその混合物を含むことを特徴とする、請求項5又は6に記載の化粧品組成物。
- 請求項1〜3のいずれか一項に記載の少なくとも一種の一般式(I)の化合物、又はその化粧品として許容される塩の、皮膚、髪、及び/又は爪を治療、ケア、及び/又は洗浄するための化粧品組成物を調製するための使用。
- 請求項1〜3のいずれか一項に記載の少なくとも一種の一般式(I)の化合物、又はその化粧品として許容される塩の、局所適用又は経皮適用によって適用する部位における皮膚、髪、及び/又は爪の色素沈着を調節するための化粧品組成物を調製するための使用。
- 請求項1〜3のいずれか一項に記載の少なくとも一種の一般式(I)の化合物、又はその化粧品として許容される塩の、皮膚を美白又は明るくするための化粧品組成物を調製するための使用。
- 請求項1〜3のいずれか一項に記載の少なくとも一種の一般式(I)の化合物、又はその医薬品として許容される塩の、色素沈着調節が必要である皮膚色素沈着障害又は病状を治療するための医薬品組成物を調製するための使用。
- 請求項1〜3のいずれか一項に記載の少なくとも一種の一般式(I)の化合物、又はその化粧品として許容される塩の、老化の徴候を低減又は遅延するための化粧品組成物を調製するための使用。
- 請求項1〜3のいずれか一項に記載の少なくとも一種の一般式(I)の化合物、又はその化粧品として許容される塩の、皮膚、髪、及び/又は爪を光保護するための化粧品組成物を調製するための使用。
- 請求項1〜3のいずれか一項に記載の少なくとも一種の一般式(I)の化合物、又はその化粧品として許容される塩の、顔毛及び/又は体毛を明るく又は色素脱失するための化粧品組成物を調製するための使用。
- 医薬品として有効な量の請求項1〜3のいずれか一項に記載の少なくとも1種の一般式(I)の化合物、又はその医薬品として許容される塩を含む医薬品組成物であって、少なくとも1種の医薬品として許容される賦形剤又はアジュバントを含むことを特徴とする医薬品組成物。
- 前記一般式(I)の化合物、又はその医薬品として許容される塩が、リポソーム、ミリカプセル、マイクロカプセル、ナノカプセル、海綿、小胞、ミセル、ミリスフェア、マイクロスフェア、ナノスフェア、リポスフェア、マイクロエマルジョン、ナノエマルジョン、ミリ粒子、マイクロ粒子、及び/又はナノ粒子からなる群から選択される医薬品として許容される徐放システム又は担体に組み込まれていることを特徴とする、請求項15に記載の医薬品組成物。
- さらに、色素脱失する又は美白剤、抗伸展線剤、抗シワ剤、酸化防止剤、抗糖化剤、NO合成酵素阻害剤、老化防止剤、目の下のたるみを低減若しくはなくすことができる物質、剥脱剤、乳化剤、柔軟剤、有機溶媒、液体噴射剤、スキンコンディショナー、湿潤化剤、水分保持物質、αヒドロキシ酸、保湿剤、ビタミン、顔料若しくは着色剤、染料、ゲル化ポリマー、粘稠化剤、界面活性剤、軟化剤、真皮若しくは表皮分子合成を刺激及び/又はそれらの分解を予防若しくは阻害するための物質、コラーゲン合成刺激剤、デコリン合成刺激剤、エラスチン合成刺激剤、ラミニン合成刺激剤、コラーゲン分解阻害剤、エラスチン分解阻害剤、線維芽細胞及び/若しくはケラチノサイト増殖を刺激又はケラチノサイト分化を刺激するための物質、脂質合成及び角質層の成分の合成刺激剤、グリコサミノグリカン合成刺激剤、DNA修復剤、DNA保護剤、デフェンシン合成刺激剤、シャペロン合成刺激剤、抗掻痒剤、敏感肌治療剤、収斂剤、皮脂産生調節剤、抗セルライト剤、脂肪分解刺激剤、真皮−表皮接合を改善するための物質、皮膚緩和剤、リアファーミング剤、大気汚染防止剤及び/若しくはラジカル捕捉剤、毛細血管循環及び/若しくは微小循環作用剤、鎮静剤、抗炎症剤、抗菌剤、抗真菌剤、殺菌剤、細胞代謝作用剤、キレート剤、並びに/或いは紫外線A及び/若しくはBに対して活性な有機又は無機光保護剤からなる群から選択される追加の医薬品として有効な量の少なくとも1種の活性剤又はその混合物を含むことを特徴とする、請求項15又は16に記載の医薬品組成物。
- 請求項1〜3のいずれか一項に記載の少なくとも一種の一般式(I)の化合物、又はその医薬品として許容される塩の、皮膚、髪、及び/又は爪を治療、ケア、及び/又は洗浄するための医薬品組成物を調製するための使用。
- 請求項1〜3のいずれか一項に記載の少なくとも一種の一般式(I)の化合物、又はその医薬品として許容される塩の、局所適用又は経皮適用によって適用する部位における皮膚、髪、及び/又は爪の色素沈着を調節するための医薬品組成物を調製するための使用。
- 請求項1〜3のいずれか一項に記載の少なくとも一種の一般式(I)の化合物、又はその医薬品として許容される塩の、皮膚、髪、及び/又は爪を光保護するための医薬品組成物を調製するための使用。
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ES200701663A ES2310142B1 (es) | 2007-06-15 | 2007-06-15 | Compuestos reguladores de la pigmentacion. |
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US3708508P | 2008-03-17 | 2008-03-17 | |
US61/037,085 | 2008-03-17 | ||
PCT/ES2008/000230 WO2008152159A2 (es) | 2007-06-15 | 2008-04-11 | Compuestos reguladores de la pigmentación |
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EP2316416B1 (de) | 2009-10-28 | 2015-12-23 | PM-International AG | Hautaufhellende kosmetische Zusammensetzung |
KR101688815B1 (ko) * | 2010-08-13 | 2016-12-23 | (주)아모레퍼시픽 | 프로판노이드 유도체를 함유하는 백모 방지용 및 백반증 치료용 조성물 |
JP6005397B2 (ja) * | 2012-05-18 | 2016-10-12 | 株式会社コーセー | 皮膚外用剤 |
CN102670480B (zh) * | 2012-06-08 | 2013-05-22 | 钟春燕 | 一种控油保湿修复体膜及制备方法 |
CN102697702B (zh) * | 2012-06-08 | 2013-04-17 | 钟春燕 | 一种美白保湿修复体膜及制备方法 |
DE102012222970A1 (de) * | 2012-12-12 | 2014-06-12 | Henkel Ag & Co. Kgaa | Wirkstoffkombination zur Hautaufhellung I |
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AU2015324179A1 (en) * | 2014-09-29 | 2017-04-27 | Elc Management Llc | Actives for stimulating differentiation of keratinocytes to lighten hyperpigmented skin |
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FR3036617B1 (fr) * | 2015-05-27 | 2018-08-31 | L'oreal | Derives (1-phenyl-2-phenyl) ethylene polyhydroxyles a titre d'agent anti-age et photoprotecteur |
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CN101730689A (zh) | 2010-06-09 |
CL2008001278A1 (es) | 2009-04-17 |
CN101730689B (zh) | 2013-08-14 |
HK1140476A1 (en) | 2010-10-15 |
USRE46228E1 (en) | 2016-12-06 |
KR101463286B1 (ko) | 2014-11-27 |
ES2310142A1 (es) | 2008-12-16 |
KR20100040857A (ko) | 2010-04-21 |
US20100247587A1 (en) | 2010-09-30 |
EP2159223B1 (en) | 2014-03-12 |
TWI407976B (zh) | 2013-09-11 |
JP2010529978A (ja) | 2010-09-02 |
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MY148437A (en) | 2013-04-30 |
US8110207B2 (en) | 2012-02-07 |
TW200904481A (en) | 2009-02-01 |
ES2468368T3 (es) | 2014-06-16 |
EP2159223A2 (en) | 2010-03-03 |
WO2008152159A2 (es) | 2008-12-18 |
WO2008152159A3 (es) | 2009-01-29 |
ES2310142B1 (es) | 2009-12-04 |
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