JP2012505159A - カルボン酸置換イデベノン誘導体を含有する皮膚用剤ならびにその調製方法及び使用 - Google Patents
カルボン酸置換イデベノン誘導体を含有する皮膚用剤ならびにその調製方法及び使用 Download PDFInfo
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- JP2012505159A JP2012505159A JP2011530300A JP2011530300A JP2012505159A JP 2012505159 A JP2012505159 A JP 2012505159A JP 2011530300 A JP2011530300 A JP 2011530300A JP 2011530300 A JP2011530300 A JP 2011530300A JP 2012505159 A JP2012505159 A JP 2012505159A
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- Prior art keywords
- acid
- idebenone
- skin
- carboxylic acid
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- OENHQHLEOONYIE-JLTXGRSLSA-N β-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=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
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Abstract
【選択図】なし
Description
本実施例は、3−オキソ−3−(9−(2,4,5−トリメチル−3,6−ジオキソシクロヘキサ−1,4−ジエニル)モニルオキシ)プロパン−1,2−ジイルジパルミテート(化合物5、イデベノンジパルミトイルグリセラート)の合成法を提供し、この化合物は、本発明のカルボン酸置換イデベノン誘導体の代表例である。
本発明のカルボン酸置換イデベノン誘導体を含有する組成物には増感剤(例えばパラベン)がないのが好ましい。次に記載するように、さまざまな成分を用いて本発明による好適な組成物を調製してもよい。本実施例の各組成物に言及する「CA−Subイデベノン誘導体」は、イデベノンジパルミトイルグリセラートなどの本発明のカルボン酸置換イデベノン誘導体を示す。
マクシミゼーションテストを用い、イデベノンジパルミトイルグリセラート(ビヒクル+1%イデベノンジパルミトイルグリセラート)を含有する局所顔用クリームの接触刺激性を評価するために、試験を実施した。テストは連続パッチテストであった。48時間の誘導時間で5回、上腕外側、掌側前腕又は掌側後腕の同じ部位に閉鎖包帯下で試験物質を塗布し、10〜14日後に未感作の皮膚部位に1回抗原投与した。検査試料は、クリームAと符号化し、換言すると何も混入しない状態で供給して試験した。担当者の監督下で、周囲条件下の近づき難い場所に全試験物質を格納した。
約0.05mlのSLS水溶液(0.25%)を直径15mmのWebril綿布下の指定部位に貼付し、パッチを24時間閉鎖テープで皮膚に固定した。24時間後にSLSパッチを取り除き、試験物質0.05mlを同じ部位に貼付し、その部位を閉塞テープ(誘発パッチ)で再度覆った。誘導パッチを48時間留置(又は72時間、週末にかけて留置)し、その後、誘導パッチを取り除き、その部位で刺激試験を再実施した。刺激症状がみられない場合、水性SLSパッチ0.25%を24時間同じ部位に再び貼付した後、同じ場所に試験物質を含む新しい誘導パッチを再貼付した。この順番は、言い換えると、24時間のSLS前処理後に48時間試験物質を塗布し、合計5回の誘導曝露を続けた。上で示すように誘導段階のいずれの時点でも刺激症が発症した場合、24時間のSLS前処理パッチを省略した。試験物質を塗布しない24時間の休息期間後、同じ部位に再び塗布した。本試験のこの段階の目的は、角質層バリアへの浸透性を高めるために、少なくとも最小限の刺激を維持することである。
最後の誘導パッチを貼付けてから10日間の休息期間後に、被検者を上腕外側、掌側前腕又は後部の新しい皮膚部位に試験物質を1回塗布して抗原投与し、感作症を発症したかどうかを判断した。抗原投与前に、SLSで前処理を実施した。直径15mmのWebril綿下の新しい皮膚部位に約0.05mlの水溶液5.0%を貼り付け、閉塞テープで覆った。SLSパッチを1時間留置した。次に、SLSパッチを除去し、同じ部位に試験物質を塗布した。次に、抗原投与パッチを閉塞テープで覆い、48時間留置した。その後、パッチを除去し、15〜30分後にその部位を評点し、24時間後に再評点した。
0=未感作
1=軽度の感作(言わば紅斑及び水腫が少しみられる)
2=中等度の感作(水疱形成の有無に関わらず、パッチの境界を超えて紅斑が浸潤し、***し、拡大する)
3=重度の感作(水疱反応が大きい)
接触アレルギーの症例は、抗原投与パッチを貼り付けてから48時間又は72時間後に27例の被検者いずれにも記録されなかった。成功を収めた化合物は、被検者から反応又は応答を引き起こさない化合物であると考えられる。
イデベノンジパルミトイルグリセラートを含有するクリームAには、検出可能な接触刺激性がなく、このため、通常の使用条件下で接触過敏反応を引き起こさないと思われる。
二重盲検法による臨床評価を6週間実施し、赤茶色に色素が沈着した皮膚を治療するために、対照ビヒクルをイデベノンジパルミトイルグリセラートと比較した。中等度の色素過剰及び皮膚の発赤を認める40〜70歳の女性を約36例選択し、試験に参加させた。被検者を無作為に3群に割り当てた。第I群には、イデベノン活性成分を含まない製品(ビヒクル)を投与した。第II群には、イデベノン0.5%を添加した同じビヒクル(ヒドロキシデシルユビキノン)を投与した。第III群には、イデベノンジパルミトイルグリセラート0.5%を添加した同じビヒクルを投与した。1日に2回(朝夕)6週間、顔面に製品を塗布するように被検者に指示した。治療前及び6週間使用後に、Canfield VISIA−CR RBX画像を撮影して、分析した。また、被検者の距離と位置を標準化して、製品塗布前後のデジタル写真とUV写真を撮った。
臨床感作性試験は、(本発明の化合物と比較して)分子量が比較的低い2つのイデベノンエステル、イデベノンリノール酸エステル及びイデベノンリン酸エステルに関して実施し、このようなイデベノンエステルの構造を次に示す。
上記の実施例は、本発明のカルボン酸置換イデベノン誘導体は、皮膚耐性が増大させて皮膚の変化を治療するのに、予想外にも大きな効果がある化合物であることを示す。特に、このような実施例とデータは、このようなカルボン酸置換イデベノン誘導体に有利な抗酸化性があり、皮膚耐性が増大するという特に有利な属性があることを示す。
Claims (21)
- 空白
- 1又は複数のカルボン酸は、脂肪酸である請求項1に記載の化合物。
- 1又は複数の脂肪酸は、共役脂肪酸である請求項2に記載の化合物。
- 一般式Iの化合物は、イデベノンジパルミトイルグリセラートである請求項1に記載の化合物。
- 1又は複数のカルボン酸は脂肪酸である請求項6に記載の方法。
- 1又は複数の脂肪酸は共役脂肪酸である請求項7に記載の方法。
- イデベノンジパルミトイルグリセラートを調製する方法であって、
(a)アクリル酸ベンジルをジヒドロキシル化反応させ、2,3−ジヒドロキシプロパン酸ベンジルを生成するステップと、
(b)2,3−ジヒドロキシプロパン酸ベンジルを塩化パルミトイルと反応させて3−(ベンジルオキシ)−3−オキソプロパン−1,2ジイルジパルミテートを生成するステップと、
(c)3−(ベンジルオキシ)−3−オキソプロパン−1、2ジイルジパルミテートを酢酸エチルと反応させて2,3−ビス(パルミトイルオキシ)プロパン酸を生成するステップと、
(d)2,3−ビス(パルミトイルオキシ)プロパン酸をイデベノンと反応させてイデベノンジパルミトイルグリセラートを生成するステップとを含む方法。 - 前記組成物は、クリーム、ローション、溶液、美容液、無水製剤、エマルジョン、マイクロエマルジョン、マルチプルエマルジョン、ゲル、ソリッドスティック、軟膏剤及びエアゾールから選択される形態で提供される請求項10に記載の組成物。
- 前記少なくとも1つの添加剤は、界面活性剤、化粧助剤、顔料、UVAフィルター、UVBフィルター、噴射剤、増粘剤、乳化剤、溶剤、水、抗酸化剤、香料、染料、脱臭剤、抗菌性材料、背過脂肪剤、錯化剤及び金属イオン封鎖剤、パール光沢剤、植物抽出物、ビタミンならびにその組み合わせから選択される請求項10に記載の組成物。
- 式Iの化合物は、イデベノンジパルミトイルグリセラートである請求項14に記載の方法。
- 前記治療有効量は、組成物の全重量に対して、0.0001〜30重量%である請求項14に記載の方法。
- 前記皮膚の変化は、皮膚の老化である請求項14に記載の方法。
- 前記皮膚の変化は、色素過剰である請求項14に記載の方法。
- 前記皮膚の変化は、UV損傷によって引き起こされる請求項14に記載の方法。
- 前記皮膚の変化は、紅斑症候群を含む請求項14に記載の方法。
- 前記皮膚の変化は、蜂巣炎である請求項14に記載の方法。
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WO2016153938A1 (en) * | 2015-03-25 | 2016-09-29 | Biosynthetic Technologies, Llc | Ester compounds including triesters having terminal vicinal acyl groups |
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