JP2009536933A - Ah受容体アンタゴニスト - Google Patents
Ah受容体アンタゴニスト Download PDFInfo
- Publication number
- JP2009536933A JP2009536933A JP2009508326A JP2009508326A JP2009536933A JP 2009536933 A JP2009536933 A JP 2009536933A JP 2009508326 A JP2009508326 A JP 2009508326A JP 2009508326 A JP2009508326 A JP 2009508326A JP 2009536933 A JP2009536933 A JP 2009536933A
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- Prior art keywords
- formula
- acid
- skin
- compound
- uvb
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Abstract
【選択図】図1
Description
皮膚は人体の最大の器官である。その最も重要な機能は、一方で水の無制御なエスケープに対して、他方で有害な化学薬品又は細菌、及び太陽放射線の浸透に対して体を保護することである。
ヒト皮膚を持続的に太陽照射にさらすと、多種の損傷を生じさせうる。ここで言及しうる例は、日焼け、光誘導性皮膚老化及び皮膚癌である。太陽光のこの有害な作用は、とりわけ、太陽光のスペクトルに含まれるUVB放射線(280〜320nm)に起因する。特にオゾン層の継続的破壊による太陽光のスペクトルのUVB成分の強度の最近の多大な増加に照らし、できるだけ包括的にUVB放射線から皮膚を保護することが必要である。
皮膚上に保護層を形成してUV放射線に対して防護するため、通常の日焼け止めは、280〜400nmの範囲の放射線を吸収及び/又は反射する物質(UVフィルター)を含む。このような光防護物質の例は、酸化亜鉛のような無機酸化物、又はケイ皮酸誘導体若しくはジベンゾイルメタン誘導体のような有機UV吸収剤である。しかし、これらの化合物の欠点は、それらが形成する保護層が物理的な摩擦、水又は洗浄剤によって容易に破壊されうることである。従って、前記UVフィルターのみならず、皮膚内部で保護作用を発生する物質をも利用できることが望ましい。
UVB放射線が細胞膜に変化を引き起こし、この変化が上皮成長因子受容体(EGF-R)等の成長受容体の活性化と、引き続く腫瘍形成に寄与することを実証することもできた(Ashida et al. (2003) Exp. Dermatol. 12, 445; Lirvall et al. (1996) Biosci. Rep. 16, 227)。抗酸化性酵素によってこのEGF-R活性化を阻害できる(Lirvall et al. (1996) Biosci. Rep. 16, 227)。
UVB及びUVA光は、シクロオキシゲナーゼ-2及びマトリックスメタロプロテイナーゼの発現をも誘導する(Pentland et al. (1999) Carcinogenesis 20(10), 1939-44)。シクロオキシゲナーゼは炎症反応の重要な酵素に属する。シクロオキシゲナーゼは、アラキドン酸からのいくつかの炎症媒介物(プロスタグランジン、プロスタサイクリン、トロンボキサン)の合成の第1段階を触媒する。2つの形態があり、シクロオキシゲナーゼ-1(COX-1)は構成的な持続的に発現される形態であり、COX-2は細胞シグナルによる刺激後、例えば組織損傷又は炎症の結果としてのみ発現される。
MMPの含量は、若い皮膚内より老皮膚内に顕著に多いことが分かった(J.H. Chung et al., J. Invest. Dermatol. 2001, 117, 1218-1224)。MMPは、外来因子による早期皮膚老化でも確固とした役割を果たす。その例として、光から防護して老化した皮膚内より、光で老化した皮膚内の高レベルのMMPを検出することもできた(J.H. Chung et al., J. Invest. Dermatol. 2001, 117, 1218-1224)。UVA及びUVB放射線と赤外線の両方についてマトリックスメタロプロテイナーゼの誘導が実証されている。この誘導を培養ヒト皮膚線維芽細胞上in vitro及びUV-刺激ヒト皮膚上in vivoの両方で観察することができた。タバコの煙による刺激もヒト皮膚線維芽細胞内でのMMP発現の上方制御をもたらした。
さらに、AhRへの結合は細胞型に依存する。Zhangら((2003) Environ. Health Perspec. 111, 1877-1882)は、例えばケルセチンはヒトの乳癌細胞系MCF-7内でAhRの作用を阻止するが、ヒトの肝癌細胞系HepG2には作用しないことを見出した。ルテオリンについては反対の作用が見られた。すなわち、ルテオリンはMCF-7細胞に作用しないが、HepG2細胞内でAhRインヒビターとして作用する。ヒト細胞とげっ歯類細胞の間では、AhRのリガンド親和性にも差異が見られた(Ema et al. (1994) J. Biol. Chem. 269, 27337-43; Zhang et al. (2003) Environ. Health Perspec. 111, 1877-1882)。
さらにall-trans-レチノイン酸は、TCDDの非存在下でのAhR活性に影響を与えることなく、正常なヒトケラチノサイト内でTCDD-誘導AhR活性化を阻害することが知られている。all-trans-レチノイン酸は、MMP-1のTCDD-誘導発現をブーストするというかなりの欠点をも有し(Murphy et al. (2004) J. Biol. Chem. 279, 25284-25293)、かつ感光性である。
本発明の観点では、遺伝子は、割り当てられた誘導質の存在下で対応mRNAの濃度が有意に高い(p<0.05、スチューデントのt-検定)、すなわち該誘導質の非存在下におけるより少なくとも10%高い場合、誘導されたと称する。
R1及びR2は、相互独立に水素又はC1-C12-アルキルであり、
R3〜R11は、相互独立に水素、C1-C12-アルキル、ヒドロキシル又はC1-C12-アルコキシであり、かつ
破線は、二重結合又は2個の水素のどちらかを表す。)
下記式:
X=C1-3-アルキレン、CO、O、S、C1-2-オキシアルキレン又はC1-2-チオアルキレン、
R=OH、アルコキシ、アルケニルオキシ、アラルコキシ、カルボキシル、アルコキシカルボニル又はアミノカルボニル、かつ
n=1〜3)
の物質は、JP-O4,134,043(1992)からUV吸収剤として既知であるが、AhRアンタゴニストとしては既知でない。
驚くべきことに、式(I)の化合物、特に式(Ia)及び(Ib)の当該化合物は、皮膚ライトニング作用をも有する。
本発明の好ましい化合物は、式中、R1及びR2が相互独立にメチルである当該化合物である。好ましくは、R1とR2が同時に両方ともメチルである。他の好ましい化合物は、式中、基R3〜R11の多くて4個が水素でなく、基R3〜R11の少なくとも1個、かつ最大4個が相互独立に好ましくはヒドロキシル、C1-C4-アルキル(分岐若しくは不分岐)又はC1-C4-アルコキシである当該化合物である。好ましい実施形態では、前記基の1個がヒドロキシル又はC1-C4-アルコキシの場合、残りの基、すなわち最高3個の基はH又はC1-C4-アルキル(分岐若しくは不分岐)でよく、さらに好ましくはR1とR2が両方とも同時にメチルである。このように置換されている化合物が特に有効なAhRアンタゴニストであることが判った。
特に好ましい化合物は、(E)及び/又は(Z)異性体として存在しうる下記式(Ia)、(Ib)、(Ic)及び(Id)の当該化合物である。
本発明の化粧用及び治療用製剤は、それ自体既知の常法によって調製される。常法では、式(I)の化合物、好ましくは式(Ia)、(Ib)、(Ic)及び/又は(Id)、特に式(Ia)及び/又は(Ib)の化合物を、通常の組成の化粧用又は皮膚科用製剤に組み入れる。また、その皮膚ライトニング及び毛髪ライトニング作用とは別に、皮膚又は毛髪を処理し、ケアし、及びきれいにするために使用することもできる。
特に好ましくは、本発明の製剤は、エマルション、特にW/O、O/W、W/O/W又はO/W/O型、PITエマルション、ピカリングエマルション、低油含量のエマルション、又はマイクロエマルション若しくはナノエマルション、ゲル(ヒドロゲル、水系分散液ゲル、オレオゲルを含む)、溶液(例えば油(脂肪油又は脂肪酸エステル、特にC6-C32脂肪酸C2-C30エステル)又はシリコーン油中)、又はスプレー(例えば、ポンプスプレー又は噴霧剤を有するスプレー)の形態を取る。
補助物質及び添加剤は、製剤の総質量に基づいて5〜99wt.%、好ましくは10〜80wt.%の量で存在しうる。当業者は、簡単な試行錯誤を用いて、個々の製品タイプに従って各場合に使用すべき化粧用又は皮膚科用の補助物質と添加剤及び香料の量を容易に決定できる。
製剤は、該製剤の総質量に基づいて99.99wt.%まで、好ましくは5〜80wt.%の量の水を含有することもできる。
エマルション、溶液、分散液、懸濁液、クリーム、ローション、ミルク、ゲル、スプレー、フォーム、美容組織用の含浸液、洗浄製品、石鹸、合成洗剤、洗浄製剤、シャワー製剤、浴用製剤、浴用製品、発泡性製剤、スキンケア製品、軟膏、ペースト、油、トナー、バルサム、セラム、パウダー、マスク、ペンシル、スティック、ロールオン、ポンプ、エアロゾル、脱臭剤、制汗剤、うがい薬、マウスウォッシュ、フットケア製品、昆虫忌避薬、日焼け止め、自己日焼け製品、アフターサン製剤、皮膚トナー、髭剃り製品、髭剃り後バルム、髭剃り前ローション、髭剃り後ローション、脱毛剤、ヘアケア製品、シャンプー、コンディショナー、ヘアトリートメント、ヘアトニック、ヘアリンス、スタイリングクリーム、ポマード、パーマ製品、定着液、ヘアセットローション、スタイリング助剤、ヘアスムージング製品、漂白剤、ヘア着色剤、ヘアトナー、ヘアライトナー、ヘアコンディショナー、ヘアムース、アイケア製品、メーキャップ、メーキャップリムーバー及びベビー製品
を含む群から選択され、
及び/又は
式(I)の化合物、好ましくは式(Ia)、(Ib)、(Ic)及び/又は(Id)、特に式(Ia)及び/又は(Ib)の化合物に加え、以下の補助物質及び添加剤:
研磨剤、フケ防止剤、抗炎症薬、抗酸化剤、制汗剤、結合剤、緩衝液、キレート剤、脱毛剤、表面活性物質、乳化剤、酵素、エーテル油、植物エキス、繊維、膜形成剤、固定液、泡立て剤、泡安定剤、消泡剤、泡ブースター、ゲル化薬、ヘアケア剤、ヘア変形剤、ヘアスムージング剤、スキン及びヘアライトナー、モイスチャライザー、保湿剤、昆虫忌避薬、蛍光増粘剤、潤沢剤、光沢剤、ポリマー、タンパク質、過脂肪剤、皮膚鎮静剤、皮膚スムージング剤、しわ防止剤、日焼け止め、ビタミン、油、ワックス、脂肪、リン脂質、飽和脂肪酸とその塩、一不飽和若しくは多不飽和脂肪酸とその塩、α-ヒドロキシ酸、ポリヒドロキシ脂肪酸、ポリオール、アルカンジオール、シリコーン及びシリコーン誘導体
を含む群から選択される1種以上の補助物質及び添加剤を含み、
及び/又は
毛髪及び/又は皮膚への適用を意図した製剤である。
1種以上のUVフィルター(日焼け止め、UV吸収剤)を含有する本発明の製剤は、該製剤の総質量に基づいて好ましくは0.1〜30wt.%、特に好ましくは0.2〜20wt.%、非常に特に好ましくは0.5〜15wt.%の範囲の総比率のUVフィルターを有する。特に好ましくは、本発明の製剤は、特に後述するタイプの1種以上のUVBフィルターを含有する。本発明の式(I)、好ましくは式(Ia)、(Ib)、(Ic)及び/又は(Id)特に式(Ia)及び/又は(Ib)の物質は、有利には、UVBフィルターと相互作用して、UVB誘導皮膚損傷、皮膚変化及び皮膚癌を阻止することが分かった。
別の好ましい実施形態では、本発明の製剤は、本発明の製剤が2以上(好ましくは5以上)の光防護係数を有するような総量で、日焼け止め、すなわち特にUVフィルター及び/又は無機顔料(UV-フィルタリング顔料)を含有する。本発明のこのような製剤は、特に皮膚及び毛髪を保護するために好適である。
有利には、本発明の製剤は、少なくとも1種のUVAフィルター及び/又は少なくとも1種のUVBフィルター及び/又は広帯域フィルター及び/又は少なくとも1種の無機顔料を含む。本発明の製剤は、好ましくは少なくとも1種のUVBフィルター又は広帯域フィルターを含み、特に好ましくは少なくとも1種のUVAフィルターと少なくとも1種のUVBフィルターを含む。
本発明の目的のため使用可能な以下に挙げるUVフィルターが好ましいが、当然、限定するものではない。
UVBフィルター、例えば
・p-アミノ安息香酸
・エトキシル化p-アミノ安息香酸エチル(25モルのEO)(INCI名:PEG-25 PABA)
・p-ジメチルアミノ安息香酸2-エチルヘキシル
・N-プロポキシル化p-アミノ安息香酸エチル(2モルのPO)
・p-アミノ安息香酸グリセリル
・サリチル酸ホモメンチル(ホモサレート)(Neo Heliopan(登録商標) HMS)
・サリチル酸2-エチルヘキシル(Neo Heliopan(登録商標) OS)
・サリチル酸トリエタノールアミン
・サリチル酸4-イソプロピルベンジル
・アントラニル酸メンチル(Neo Heliopan(登録商標) MA)
・ジイソプロピルケイ皮酸エチル
・p-メトキシケイ皮酸2-エチルヘキシル(Neo Heliopan(登録商標) AV)
・ジイソプロピルケイ皮酸メチル
・p-メトキシケイ皮酸イソアミル(Neo Heliopan(登録商標) E 1000)
・p-メトキシケイ皮酸ジエタノールアミン
・p-メトキシケイ皮酸イソプロピル
・2-フェニルベンゾイミダゾールスルホン酸と塩(Neo Heliopan(登録商標) Hydro)
・メチルスルホン酸3-(4'-トリメチルアンモニウム)ベンジリデンボルナン2-オン
・β-イミダゾール-4(5)-アクリル酸(ウロカニン酸)
・3-(4'-スルホ)ベンジリデンボルナン2-オンと塩
・3-(4'-メチルベンジリデン)-D,L-カンファー(Neo Heliopan(登録商標) MBC)
・3-ベンジリデン-D,L-カンファー
・N-[(2及び4)-[2-(オキソボルン-3-イリデン)メチル]ベンジル]アクリルアミドポリマー
・4,4'-[(6-[4-(1,1-ジメチルアミノカルボニル)フェニルアミノ]-1,3,5-トリアジン-2,4-ジイル)ジイミノ]ビス(安息香酸2-エチルヘキシル) (Uvasorb(登録商標) HEB)
・ベンジリデンマロネート-ポリシロキサン(Parsol(登録商標) SLX)
・グリセリル エチルヘキサノエート ジメトキシシナメート
・ジプロピレングリコール サリチレート
・トリス(2-エチルヘキシル) 4,4′,4′′-(1,3,5-トリアジン-2,4,6-トリイルトリイミノ)トリベンゾエート(=2,4,6-トリアニリノ(p-カルボ-2'-エチルヘキシル-1'-オキシ)-1,3,5-トリアジン)(Uvinul(登録商標) T150)
・2-シアノ-3,3-ジフェニルアクリル酸2-エチルヘキシル(Neo Heliopan(登録商標) 303)
・2-シアノ-3,3'-ジフェニルアクリル酸エチル
・2-ヒドロキシ-4-メトキシベンゾフェノン(Neo Heliopan(登録商標) BB)
・2-ヒドロキシ-4-メトキシベンゾフェノン-5-スルホン酸
・ジヒドロキシ-4-メトキシベンゾフェノン
・2,4-ジヒドロキシベンゾフェノン
・テトラヒドロキシベンゾフェノン
・2,2'-ジヒドロキシ-4,4'-ジメトキシベンゾフェノン
・2-ヒドロキシ-4-n-オクチルオキシベンゾフェノン
・2-ヒドロキシ-4-メトキシ-4'-メチルベンゾフェノン
・ヒドロキシメトキシベンゾフェノンスルホン酸ナトリウム
・二ナトリウム 2,2’-ジヒドロキシ-4,4’-ジメトキシ-5,5’-ジスルホ-ベンゾフェノン
・2-(2H-ベンゾトリアゾール-2-イル)-4-メチル-6-(2-メチル-3-(1,3,3,3-テトラメチル-1-(トリメチルシリル)オキシ)ジシロキサニル)プロピルフェノール(Mexoryl(登録商標) XL)
・2,2'-メチレンビス(6-(2H-ベンゾトリアゾール-2-イル)-4-(1,1,3,3-テトラメチルブチル)フェノール)(Tinosorb(登録商標) M)
・2,4-ビス[4-(2-エチルヘキシルオキシ)-2-ヒドロキシフェニル]-1,3,5-トリアジン
・2,4-ビス[{4-(2-エチルヘキシルオキシ)-2-ヒドロキシ}フェニル]-6-(4-メトキシフェニル)-1,3,5-トリアジン(Tinosorb(登録商標) S)
・2,4-ビス[{(4-(3-スルホナト)-2-ヒドロキシプロポキシ)-2-ヒドロキシ}フェニル]-6-(4-メトキシフェニル)-1,3,5-トリアジン ナトリウム塩
・2,4-ビス[{(3-(2-プロポキシ)-2-ヒドロキシプロポキシ)-2-ヒドロキシ}フェニル]-6-(4-メトキシフェニル)-1,3,5-トリアジン
・2,4-ビス[{4-(2-エチルヘキシルオキシ)-2-ヒドロキシ}フェニル]-6-[4-(2-メトキシエチルカルボニル)フェニルアミノ]-1,3,5-トリアジン
・2,4-ビス[{4-(3-(2-プロポキシ)-2-ヒドロキシプロポキシ)-2-ヒドロキシ}-フェニル]-6-[4-(2-エチルカルボキシル)フェニルアミノ]-1,3,5-トリアジン
・2,4-ビス[{4-(2-エチルヘキシルオキシ)-2-ヒドロキシ}フェニル]-6-(1-メチルピロール-2-イル)-1,3,5-トリアジン
・2,4-ビス[{4-トリス(トリメチルシロキシシリルプロポキシ)-2-ヒドロキシ}フェニル]-6-(4-メトキシフェニル)-1,3,5-トリアジン
・2,4-ビス[{4-(2''-メチルプロペニルオキシ)-2-ヒドロキシ}フェニル]-6-(4-メトキシフェニル)-1,3,5-トリアジン
・2,4-ビス[{4-(1',1',1',3',5',5',5'-ヘプタメチルシロキシ-2''-メチルプロポキシ)-2-ヒドロキシ}フェニル]-6-(4-メトキシフェニル)-1,3,5-トリアジン
UVAフィルター、例えば
・4-イソプロピルジベンゾイルメタン
・テレフタリリデンジボルナンスルホン酸と塩(Mexoryl(登録商標) SX)
・4-t-ブチル-4'-メトキシジベンゾイルメタン(アボベンゾン(avobenzone))(Neo Heliopan(登録商標) 357)
・フェニレンビスベンゾイミダジル四スルホン酸二ナトリウム(Neo Heliopan(登録商標) AP)
・2,2'-(1,4-フェニレン)ビス(1H-ベンゾイミダゾール-4,6-ジスルホン酸)一ナトリウム
・2-(4-ジエチルアミノ-2-ヒドロキシベンゾイル)安息香酸ヘキシル(Uvinul(登録商標) A Plus)
・DE 100 55 940(=WO 02/38537)に記載のインダニリデン化合物。
・p-アミノ安息香酸
・メチルスルホン酸3-(4'-トリメチルアンモニウム)ベンジリデンボルナン2-オン
・サリチル酸ホモメンチル(Neo Heliopan(登録商標) HMS)
・2-ヒドロキシ-4-メトキシベンゾフェノン(Neo Heliopan(登録商標) BB)
・2-フェニルベンゾイミダゾールスルホン酸(Neo Heliopan(登録商標) Hydro)
・テレフタリリデンジボルナンスルホン酸と塩(Mexoryl(登録商標) SX)
・4-tert-ブチル-4'-メトキシジベンゾイルメタン(Neo Heliopan(登録商標) 357)
・3-(4'-スルホ)ベンジリデンボルナン2-オンと塩
・2-シアノ-3,3-ジフェニルアクリル酸2-エチルヘキシル(Neo Heliopan(登録商標) 303)
・N-[(2及び4)-[2-(オキソボルン-3-イリデン)メチル]ベンジル]アクリルアミドポリマー
・p-メトキシケイ皮酸2-エチルヘキシル(Neo Heliopan(登録商標) AV)
・エトキシル化p-アミノ安息香酸エチル(25モルのEO)(INCI名:PEG-25 PABA)
・p-メトキシケイ皮酸イソアミル(Neo Heliopan(登録商標) E1000)
・2,4,6-トリアニリノ(p-カルボ-2'-エチルヘキシル-1'-オキシ)-1,3,5-トリアジン(Uvinul(登録商標) T150)
・2-(2H-ベンゾトリアゾール-2-イル)-4-メチル-6-(2-メチル-3-(1,3,3,3-テトラメチル-1-(トリメチルシリル)オキシ)ジシロキサニル)プロピルフェノール(Mexoryl(登録商標)XL)
・4,4'-[(6-[4-(1,1-ジメチル)アミノカルボニル]フェニルアミノ]-1,3,5-トリアジン-2,4-ジイル)ジイミノ]ビス(安息香酸2-エチルヘキシル)(Uvasorb HEB)
・3-(4'-メチルベンジリデン)-D,L-カンファー(Neo Heliopan(登録商標) MBC)
・3-ベンジリデンカンファー
・サリチル酸2-エチルヘキシル(Neo Heliopan(登録商標) OS)
・4-ジメチルアミノ安息香酸2-エチルヘキシル(Padimate O)
・ヒドロキシ-4-メトキシベンゾフェノン-5-スルホン酸とNa塩
・2,2'-メチレンビス(6-(2H-ベンゾトリアゾール-2-イル)-4-(1,1,3,3-テトラメチルブチル)フェノール)(Tinosorb(登録商標) M)
・フェニレンビスベンゾイミダジル四スルホン酸二ナトリウム(Neo Heliopan(登録商標) AP)
・2,4-ビス[{4-(2-エチルヘキシルオキシ)-2-ヒドロキシ}フェニル]-6-(4-メトキシフェニル)-1,3,5-トリアジン(Tinosorb(登録商標) S)
・ベンジリデンマロネート-ポリシロキサン(Parsol(登録商標) SLX)
・アントラニル酸メンチル(Neo Heliopan(登録商標) MA)
・2-(4-ジエチルアミノ-2-ヒドロキシベンゾイル)安息香酸ヘキシル(Uvinul(登録商標) A Plus)
・DE 100 55 940(=WO 02/38537)に記載のインダニリデン化合物
本発明の製剤、特に皮膚科用製剤は、特に装飾用化粧品の分野で使用される場合、有利には染料及び/又は着色顔料をも含有しうる。化粧品規制によって承認されている適切なリスト又は化粧品用着色剤のECリストから染料及び着色顔料を選択することができる。多くの場合、染料及び着色顔料は食品で使うために許可されている染料と同一である。有利な着色顔料の例は、二酸化チタン、マイカ、酸化鉄(例えば Fe2O3、Fe3O4、FeO(OH))及び酸化スズである。有利な染料の例は、カーミン、ベルリンブルー、酸化クロムグリーン、ウルトラマリンブルー及び/又はマンガンバイオレットである。
非常に特に好ましい冷却剤は、L-メントール、メントングリセロールアセタール(商標名:Frescolat(登録商標) MGA)及び乳酸メンチル(好ましくは乳酸L-メンチル、特にL-乳酸L-メンチル(商標名:Frescolat(登録商標) ML)である。
物質によって、使用すべき冷却剤の使用濃度は、完成した(すぐに使える)、好ましくは局所用の化粧用又は治療用(医薬)製剤の総質量に基づいて、好ましくは0.01〜20wt.%、特に好ましくは0.1〜5wt.%の範囲である。
本発明の製剤中の上述した典型的な(他の)皮膚及び毛髪ライトニング化合物(1種以上の化合物)の量は、該製剤の総質量に基づいて、好ましくは0.005〜30wt.%、特に好ましくは0.01〜20wt.%、非常に特に好ましくは0.01〜5wt.%である。
他の有利な染料は、油溶性の天然染料、例えばパプリカエキス、β-カロテン又はコチニールである。
1.天然の真珠光沢顔料、例えば
−パールエッセンス(魚のうろこ由来のグアニジン/ヒポキサンチン混晶)及び
−真珠母貝(グランウドイガイ(ground mussel)の殻)
2.単結晶真珠光沢顔料、例えばオキシ塩化ビスマス(BiOCl)
3.シート顔料、例えばマイカ/金属酸化物
当然、真珠光沢顔料の上記リストは限定を意味するものではない。本発明の目的のために有利な真珠光沢顔料は、それ自体既知の多くの方法で得られる。例えばマイカ以外の基材、例えばシリカ等を他の金属酸化物でコーティングすることもできる。例えば、Merckによって市販され、かつ特に微細なしわの視覚的減少に特に好適な、TiO2とFe2O3でコーティングしたSiO2粒子(「Ronaspheres」)は有利である。
さらに、マイカのような基材と完全に調剤することが有利だろう。マイカを使用せずに調製する鉄の真珠光沢顔料を与えることが特に好ましい。このような顔料は、例えばBASFから商標名Sicopearl Kupfer 1000で得られる。
Flora Techから商標名Metasomes Standard/Glitterで異なる色(黄、赤、緑、青)で得られる有効な顔料も特に有利である。ここで、Glitter粒子は、種々の補助物質及び染料(例えばCIN 19140、77007、77289、77491の染料)との混合物の形態を取る。
染料及び顔料は個々に存在するか又は混合物で存在してよく、相互にコーティングしてよく、通常、異なるコーティング厚によって異なる色彩効果が生じる。染料と着色顔料の総量は、有利には、各場合、(化粧)製剤の総量に基づいて、0.1wt.%〜30wt.%、好ましくは0.5〜15wt.%、特に好ましくは1.0〜10wt.%の範囲内で選択される。
を含む群から選択される。
本発明の製剤中の抗酸化剤(1種以上の化合物)の量は、該製剤の総質量に基づいて、好ましくは0.01〜20wt.%、特に好ましくは0.05〜10wt.%、非常に特に好ましくは0.2〜5wt.%である。
抗酸化剤がビタミンE及び/又はその誘導体から成る場合、製剤の総質量に基づいて、それらのそれぞれ0.001〜10wt.%の範囲の濃度を選択することが有利である。
抗酸化剤がビタミンA若しくはビタミンA誘導体、又はカロテン若しくはその誘導体から成る場合、製剤の総質量に基づいて、それらのそれぞれ0.001〜10wt.%の範囲の濃度を選択することが有利である。
本発明の製剤中の抗刺激剤(1種以上の化合物)の量は、該製剤の総質量に基づいて、好ましくは0.01〜20wt.%、特に好ましくは0.03〜10wt.%、非常に特に好ましくは0.05〜5wt.%である。
C2〜C40の鎖長を有する脂肪アルコール、アルデヒド及び酸(アリール置換又はアリールオキシ置換され、不分岐又はモノアルキル分岐及びポリアルキル分岐した飽和又は一不飽和〜五不飽和(混合エン/イン化合物を含め、5個までの二重結合又は三重結合))。
C2〜C40、特に好ましくはC4〜C12の鎖長を有するアルカンジオール、ジアルデヒド及びジカルボン酸(アリール置換又はアリールオキシ置換され、不分岐又はモノアルキル分岐及びポリアルキル分岐した飽和又は一不飽和〜五不飽和(混合エン/イン化合物を含め、5個までの二重結合又は三重結合))。
C2〜C40の鎖長を有するカルボン酸(不分岐又はモノアルキル分岐及びポリアルキル分岐した飽和又は一不飽和〜五不飽和(混合エン/イン化合物を含め、5個までの二重結合又は三重結合)、かつ任意にアリール置換又はアリールオキシ置換されていてもよい)と、C2〜C40の鎖長を有する一価〜六価脂肪アルコール(不分岐又はモノアルキル分岐及びポリアルキル分岐した飽和又は一不飽和〜五不飽和(混合エン/イン化合物を含め、5個までの二重結合又は三重結合)、かつ任意にアリール置換又はアリールオキシ置換されていてもよい)との脂肪酸エステル。
ラノリン、ラノリンアルコール及びラノリン酸のモノグリセリド及びオリゴグリセリド(例えばラノリン酸グリセリル、ネオセライト(neocerite))、グリシルレチン酸と誘導体(例えばステアリン酸グリシルレチニル)、天然及び合成カルデノリド(例えばジギトキシン、ジゴキシン、ジゴキシゲニン(digoxygenin)、ギトキシゲニン(gitoxygenin)、ストロファンチン及びストロファンチジン)、天然及び合成ブファジェノリド(例えばシラレンA、シラレニン(scillarenin)及びブフォタリン、サポゲニン及びステロイドサポゲニン(例えばアミリン、オレアノール酸、ジギトニン、ギトゲニン(gitogenin)、チゴゲニン(tigogenin)及びジオスゲニン)、及び植物及び動物起源のステロイドアルカロイド例えばトマチジン(tomatidine)、ソラニン、ソラニジン(solanidine)、コッセイン(conessine)、バトラコトキシン及びホモバトラコトキシン)。
モノハロゲン化及びポリハロゲン化ニトリル、ジニトリル、トリニトリル又はテトラニトリル。
C2〜C24の鎖長を有するモノ-及びオチゴヒドロキシ脂肪酸(例えば乳酸、2-ヒドロキシパルミチン酸)、そのオリゴマー及び/又はポリマー並びにそれらを含有する植物性及び動物性素材。
C2〜C40の鎖長と1〜150個のEO及び/又はPO単位を有する、化粧用のエトキシル化、プロポキシル化又は混合エトキシル化/プロポキシル化脂肪アルコール、脂肪酸及び脂肪エステル。
a)単糖、特にペントース及びヘキソース、
b)二糖、特にスクロース、マルトース及びラクトビオース、
c)オリゴ糖、特に三糖及び四糖、並びに
d)多糖、特にデンプン、グリコーゲン、セルロース、デキストラン、ツニシン(tunicin)、イヌリン、キチン、特にキトサン、キチン加水分解物、アルギン酸とアルギナート、植物ゴム、粘液、ペクチン、マンナン、ガラクタン、キシラン、アラバン、ポリオース(polyose)、コンドロイチン硫酸、ヘパリン、ヒアルロン酸及びグリコサミノグリカン、ヘミセルロース、置換セルロース及び置換デンプン、特にそれぞれヒドロキシアルキル-置換多糖。
スフィンゴ脂質、例えばスフィンゴシン;N-モノアルキル化スフィンゴシン;N,N-ジアルキル化スフィンゴシン;スフィンゴシン-1-ホスフェート;スフィンゴシン-1-スルフェート;サイコシン(スフィンゴシンβ-D-ガラクトピラノシド);スフィンゴシルホスホリルコリン(sphingosylphosphorylcholine);リソスルファチド(lysosulfatide)(スフィンゴシルガラクトシルスルフェート(sphingosyl galactosylsulfate);リソセレブロシドスルフェート(lysocerebroside sulfate);レシチン;スフィンゴミエリン;スフィンガニン(sphinganin)。
エーテル油中で見つかる抗菌作用のある重要な物質は、例えばアネトール、カテコール、カンフェン(camphene)、カルバクロール、オイゲノール、ユーカリプトール、フェルラ酸、ファルネソール、ヒノキチオール、トロポロン、リモネン、メントール、サリチル酸メチル、チモール、テルピネオール、ベルベノン、ベルベリン、クルクミン、カリオフィレンオキシド、ネロリドール(nerolodol)及びゲラニオールである。
前記活性系又は活性物質の混合物、並びにこれらの活性物質を含有する配合物を使用することもできる。
製剤中の抗菌物質の量は、該製剤の総質量に基づいて、好ましくは0.01〜20wt.%、特に好ましくは0.05〜10wt.%である。
製剤中の脱臭及び/又は制汗物質の量は、該製剤の総質量に基づいて、好ましくは0.01〜20wt.%、特に好ましくは0.05〜10wt.%である。
アニオン性界面活性剤は、一般的に官能基としてカルボン酸、硫酸又はスルホン酸基を含む。水溶液では、アニオン性界面活性剤は、酸性又は中性媒体中で負に荷電した有機イオンを形成する。カチオン性界面活性剤は、事実上排他的に四級アンモニウム基の存在によって特徴づけられる。水溶液では、カチオン性界面活性剤は、酸性又は中性媒体中で正に荷電した有機イオンを形成する。両性界面活性剤は、アニオン基とカチオン基の両方を含有するので、水溶液中では、pHによってアニオン性又はカチオン性界面活性剤のように振舞う。両性界面活性剤は、強酸媒体中では正電荷を有し、アルカリ性媒体中では負電荷を有する。一方、中性のpH範囲では、双性イオン性である。ポリエーテル鎖は非イオン性界面活性剤の典型である。非イオン性界面活性剤は水性媒体中ではイオンを形成しない。
有利に使用できるアニオン性界面活性剤は、アシルアミノ酸(及びその塩)、例えば
-アシルグルタメート、例えばナトリウムアシルグルタメート、ジ-TEAパルミトイルアスパルテート及びナトリウムカプリル酸/カプリン酸グルタメート、
-アシルペプチド、例えばパルミトイル-加水分解乳タンパク質、ナトリウムココイル-加水分解大豆タンパク質及びナトリウム/カリウムココイル-加水分解コラーゲン、
-サルコシネート、例えばミリストイルサルコシン、TEAラウロイルサルコシネート、ナトリウムラウロイルサルコシネート及びナトリウムココイルサルコシネート、
-タウレート、例えばナトリウムラウロイルタウレート及びナトリウムメチルココイルタウレート、
-アシルラクチレート、ラウロイルラクチレート及びカプロイルラクチレート、
-アラニネート;
カルボン酸と誘導体、例えば
-ラウリン酸、ステアリン酸アルミニウム、マグネシウムアルカノレート及びウンデシレン酸亜鉛、
-エステル-カルボン酸、例えばカルシウムテアロイルラクチレート、ラウレス-6シトレート及びナトリウムPEG-4ラウラミド(lauramido)カルボキシレート、
-エーテル-カルボン酸、例えばナトリウムラウレス-13カルボキシレート及びナトリウムPEG-6コカミドカルボキシレート;
リン酸エステルと塩と塩、例えばDEオレス-10ホスフェート、ジラウレス-4ホスフェート及びセチルホスフェート誘導体(例えばWO 2004/075868に記載のもの);
スルホン酸と塩、例えば
-アシルイセチオネート、例えばナトリウム/アンモニウムココイルイセチオネート、
-アルキルアリールスルホネート、
-アルキルスルホネート、例えば ナトリウムココモノグリセリドスルフェート、ナトリウムC12-14-オレフィンスルホネート、ナトリウムラウリルスルホアセテート及びマグネシウムPEG-3コカミドスルフェート、
-スルホスクシネート、例えばナトリウムジオクチルスルホスクシネート、二ナトリウムラウレススルホスクシネート、二ナトリウムラウリルスルホスクシネート及び二ナトリウムMEAウンデシレンアミドスルホスクシネート;
並びに
硫酸エステル、例えば
-アルキルエーテルスルフェート、例えばナトリウム、アンモニウム、マグネシウム、MIPA及びTIPAラウレススルフェート、ナトリウムミレス(myreth)スルフェート及びナトリウムC12-13パレス(pareth)スルフェート、
-アルキルスルフェート、例えばナトリウム、アンモニウム及びTEAラウリルスルフェート。
有利に使用できるカチオン性界面活性剤は、以下の通りである。
-アルキルアミン、
-アルキルイミダゾール、
-エトキシル化アミン及び
-四級界面活性剤:
RNH2CH2CH2COO-(pH 7で)
RNHCH2CH2COO- B+(pH 12で)、B+=任意のカチオン、例えばNa+
-エステルクアット
有利に使用できる両性界面活性剤は、以下の通りである
-アシル-/ジアルキルエチレンジアミン、例えばナトリウムアシルアンホアセテート、二ナトリウムアシルアンホジプロピオネート、二ナトリウムアルキルアンホジアセテート、ナトリウムアシルアンホヒドロキシプロピルスルホネート、二ナトリウムアシルアンホジアセテート及びナトリウムアシルアンホプロピオネート、
-N-アルキルアミノ酸、例えばアミノプロピルアルキルグルタミド、アルキルアミノプロピオン酸、ナトリウムアルキルイミドジプロピオネート及びラウロアンホカルボキシグリシネート(glycinate)。
有利に使用できる非イオン性界面活性剤は以下の通りである。
-アルコール、
-アルカノールアミド、例えばコカミド(cocamide)MEA/DEA/MIPA、
-アミンオキシド、例えばコカミドプロピルアミンオキシド、
-カルボン酸とエチレンオキシド、グリセロール、ソルビタン又は他のアルコールとのエステル化によって形成されるエステル、
-エーテル、例えばエトキシル化/プロポキシル化アルコール、エトキシル化/プロポキシル化エステル、エトキシル化/プロポキシル化グリセロールエステル、エトキシル化/プロポキシル化コレステロール、エトキシル化/プロポキシル化トリグリセリドエステル、エトキシル化/プロポキシル化ラノリン、エトキシル化/プロポキシル化ポリシロキサン、プロポキシル化POEエーテル、及びアルキルポリグリコシド、例えばラウリルグルコシド、デシルグリコシド及びココグリコシド、
-スクロースエステル及びエーテル、
-ポリグリセロールエステル、ジグリセロールエステル及びモノグリセロールエステル、
-ヒドロキシ酸のメチルグルコースエステル及びエステル。
アニオン性及び/又は両性界面活性剤と1種以上の非イオン性界面活性剤の併用も有利である。
本発明の製剤中に、表面活性物質(界面活性剤)又は表面活性物質の組合せは、該製剤の総質量に基づいて、1〜98wt.%の濃度で存在しうる。
本発明の製剤(特に局所化粧製剤)中の油相(脂質相)は、有利には下記物質群から選択される:
-鉱油(有利にはパラフィン油)及び鉱蝋;
-脂肪油、脂肪、蝋並びに他の天然及び合成脂肪物質、好ましくは脂肪酸と低C数のアルコール、例えばイソプロパノール、プロピレングリコール若しくはグリセロールとのエステル、又は脂肪アルコールと低C数のアルカン酸又は脂肪酸とのエステル;
-アルキルベンゾエート(例えばn-ドデシル、n-トリデシル、n-テトラデシル又はn-ペンタデシルベンゾエートの混合物);
-環式又は直鎖シリコーン油、例えばジメチルポリシロキサン、ジエチルポリシロキサン、ジフェニルポリシロキサン及びその混合形。
-脂肪アルコールエトキシレート(ethoxylate)、
-エトキシル化羊毛蝋アルコール、
-一般式R-O-(-CH2-CH2-O-)n-R'のポリエチレングリコールエーテル、
-一般式R-COO-(-CH2-CH2-O-)n-Hの脂肪酸エトキシレート
-一般式R-COO-(-CH2-CH2-O-)n-R'のエーテル化脂肪酸エトキシレート、
-一般式R-COO-(-CH2-CH2-O-)n-C(O)-Rのエステル化脂肪酸エトキシレート、
-ポリエチレングリコールグリセロール脂肪酸エステル、
-エトキシル化ソルビタンエステル、
-コレステロールエトキシレート、
-エトキシル化トリグリセリド、
-一般式R-COO-(-CH2-CH2-O-)n-OOH(式中、nは5〜30の数)のアルキルエーテルカルボン酸、
-ポリオキシエチレンソルビトール脂肪酸エステル、
-一般式R-O-(-CH2-CH2-O-)n-SO3-Hのアルキルエーテルスルフェート、
-一般式R-O-(-CH2-CH(CH3)-O-)n-Hの脂肪アルコールプロポキシレート、
-一般式R-O-(-CH2-CH(CH3)-O-)n-R'のポリプロピレングリコールエーテル、
-プロポキシル化羊毛蝋アルコール、
-エーテル化脂肪酸プロポキシレートR-COO-(-CH2-CH(CH3)-O-)n-R'、
-一般式R-COO-(-CH2-CH(CH3)-O-)n-C(O)-R'のエステル化脂肪酸プロポキシレート、
-一般式R-COO-(-CH2-CH(CH3)-O-)n-Hの脂肪酸プロポキシレート
-ポリプロピレングリコールグリセロール脂肪酸エステル、
-プロポキシル化ソルビタンエステル、
-コレステロールプロポキシレート、
-プロポキシル化トリグリセリド、
-一般式R-O-(-CH2-CH(CH3)-O-)n-CH2-COOHのアルキルエーテルカルボン酸、
-一般式R-O-(-CH2-CH(CH3)-O-)n-SO3-Hのアルキルエーテルスルフェート、又はこれらのスルフェートを基礎とする酸、
-一般式R-O-Xn-Ym-Hの脂肪アルコールエトキシレート/プロポキシレート、
-一般式R-O-Xn-Ym-R'のポリプロピレングリコールエーテル、
-一般式R-COO-Xn-Ym-R'のエーテル化脂肪酸プロポキシレート、
-一般式R-COO-Xn-Ym-Hの脂肪酸エトキシレート/プロポキシレート。
ポリエチレングリコール(n)ステアリルエーテル(ステアレス-n)(n=13〜20)、
ポリエチレングリコール(n)セチルエーテル(セテス-n)(n=13〜20)、
ポリエチレングリコール(n)イソセチルエーテル(イソセテス-n)(n=13〜20)、
ポリエチレングリコール(n)セチルステアリルエーテル(セテアレス-n)(n=13〜20)、
ポリエチレングリコール(m)イソステアリルエーテル(イソステアレス-m)(m=12〜20)、
ポリエチレングリコール(k)オレイルエーテル(オレス-k)(k=12〜15)、
ポリエチレングリコール(12)ラウリルエーテル(ラウレス-12)、
ポリエチレングリコール(12)イソラウリルエーテル(イソラウレス-12)。
ポリエチレングリコール(n)ステアレート(n=20〜25)、
ポリエチレングリコール(m)イソステアレート(m=12〜25)、
ポリエチレングリコール(k)オレエート(k=12〜20)。
エトキシル化アルキルエーテルカルボン酸又はその塩としてナトリウムラウレス-11カルボキシレートを有利に使用できる。アルキルエーテルスルフェートとしてナトリウムラウレス1-4スルフェートを有利に使用できる。エトキシル化コレステロール誘導体としてポリエチレングリコール(30)コレステリルエーテルを有利に使用できる。ポリエチレングリコール(25)ソヤステロールも有用であると判明した。
エトキシル化トリグリセリドとしてポリエチレングリコール(60)マツヨイグサグリセリドを有利に使用できる。
同様にポリエチレングリコール(20)ソルビタンモノラウレート、ポリエチレングリコール(20)ソルビタンモノステアレート、ポリエチレングリコール(20)ソルビタンモノイソステアレート、ポリエチレングリコール(20)ソルビタンモノパルミテート及びポリエチレングリコール(20)ソルビタンモノオレエートを含む群からソルビタンエステルを選択することが好ましい。
前記活性系の混合物をも使用できる。
使用のため、本発明の局所製剤、特に皮膚及び毛髪を明るくするための製剤は、化粧製剤にとって十分な量かつ慣習的方法で皮膚及び/又は毛髪に適用される。
他の好ましい混合物、特に化粧製剤又は医薬製剤は、相乗的に活性量で以下の物質を含有するものである:(a)AhRの細胞核内への転位置を低減又は阻止するため、(b)UVB-誘導遺伝子発現を低減又は阻止するため、(c)多環式芳香族炭化水素、好ましくはTCDDによって誘導されるか又は誘導可能な遺伝子発現を低減又は阻止するため、及び/又は(d)UVB-誘導されるか又はUVB-誘導可能な皮膚損傷、特に皮膚癌、皮膚老化、皮膚炎症及び日焼けを低減又は阻止するため、或いはUV防護をブーストするためか又は皮膚を明るくするための1種以上のUVB及び/又はUVAフィルター、1種以上の抗酸化剤、1種以上の皮膚ライトナー或いは2種以上のこれらの物質の混合物。
以下、実施例の助けを借りて本発明をさらに詳細に述べる。ここで、実施例は、請求項によって定義される保護の範囲を制限することを意図しない。特に断らない限り、すべてのデータは質量による。本発明の(Ia)、(Ib)、(Ic)及び(Id)の化合物を調製するために使用するインダノンは、DE 100 55 940と同様に調製される。
11g(0.17mol)の固体水酸化カリウムを100gのジエチレングリコールジメチルエーテルに懸濁させ、89g(0.40mol)の3,3-ジメチル-5,6-ジメトキシ-1-インダノンを加える。80℃に加熱後、65g(0.60mol)のベンズアルデヒドを1時間にわたって計り入れて混合物を前記温度でさらに3時間撹拌する。これをRTに冷まし、400gの氷水に加えて30gの10%の塩酸で中性にする。400gのメチルtert-ブチルエーテルで抽出後、生成物をメタノールから再結晶させる。収率:理論の76%(E/Z混合物)。反復再結晶によって純粋な(E)異性体を単離できた。
出発原料として3,3-ジメチル-1-インダノンと3,4-ジメトキシベンズアルデヒドを用いて実施例1と同様に調製する。収率:理論の50%(E/Z混合物)。
出発原料として3,3-ジメチル-1-インダノンとアニスアルデヒドを用いて実施例1と同様に調製する。収率:理論の50%(E/Z 混合物)。
出発原料として3,3,6-トリメチル-5-ブトキシ-1-インダノンとアニスアルデヒドを用いて実施例1と同様に調製する。収率:理論の70%(E/Z混合物)。
〔細胞培養及び刺激〕
10%の胎児ウシ血清を含有するDMEM中でHaCaTケラチノサイトを培養した。PBS(リン酸緩衝食塩水)中UVBで細胞を刺激した。UVBによる刺激のため、我々は4本の平行管(Philips, Eindhoven, The Netherlands)を含み、かつUVB範囲(290〜320nm)内でそのエネルギーの大部分を発光するTL20W/12RSランプを用いた。ランプの発光ピークは少なくとも310nmである。コントロール細胞を同じ処理に供したが、刺激しなかった。AhRを阻害するため、刺激の1時間前に試験物質で細胞を処理した。
区画化した顕微鏡スライドガラス上に5×104細胞/区画の細胞密度でHaCaT細胞を蒔いた。いくつかを試験物質で1時間前処理した。24時間後、FuGene6トランスフェクション試薬(Roche, Mannheim, Germany)を製造業者の使用説明書に従って用いてこれらをプラスミドpEGFP-AhRでトランスフェクトした。さらに24時間後、トランスフェクトされた細胞を100J/m2のUVBで刺激した。40分後、細胞を10分間4%のパラホルムアルデヒドで固定してPBSで洗浄した。スライドガラスを乾燥させてVectashield封入剤(Vector Laboratories, Burlingame, CA, USA)で覆った。蛍光顕微鏡(Olympus, Hamburg, Germany)を利用してGFP-結合AhRを可視化し、ColorView XSデジタルカメラ(Olympus)で撮影した。
100J/m2のUVBでHaCaT細胞を刺激した。刺激1時間前に試験物質でいくつかの細胞を前処理した。4時間後、RNeasyキット(Qiagen, Hilden, Germany)で製造業者の使用説明書に従ってRNAを調製した。記載通りに逆転写を行った(Arch. Toxicol. (2005) PMID 16205913)。LightCycler(Roche, Mannheim, Germany)で実時間PCRを用いてPCRフラグメントを増幅した。PCRミックスは、最終体積20μl中、体積で1/10のQuantiTect(登録商標)SYBR Green PCR Master Mix(Qiagen, Hilden, Germany)、0.5μmol/lの適切なプライマー、2μlのcDNA及びDEPC-処理(ジエチルピロカーボネート処理)したH2Oで構成された。15分間95℃で加熱してDNAポリメラーゼを活性化することによってPCRが開始した。PCR条件は以下の通りだった:40サイクル(変性のため94℃で15秒、プライマー付着のため60℃で25秒、伸展のため72℃で30秒及び蛍光測定のため72℃で2秒)。ヒトCYP1A1用のPCRプライマーは以下の配列を有し:フォワードプライマーでは5′-TAGACACTGATCTGGCTGCAG及びリバースプライマーでは5′-GGGAAGGCTCCATCAGCATC(Cancer Res. 1990, 50, 4315)、増幅後146bpフラグメントを形成した。LightCyclerソフトウェア3を用い、フラグメント特異性検量線によりPCR産物を数量化した。102〜106のCYP1A1 cDNAコピー/μlで検量線を確立し、上述したように増幅した。
1)蛍光顕微鏡
標準的な3-メトキシ-4-ニトロフラボンは、UVB光の存在下及び非存在下でAhRの細胞核内への転位置を阻害したので、文献によって予測される作用を示した。
2)CYP1A1-mRNAの定量によるAhR阻害の数量化
〔光安定性試験〕
(手順)
式(I)の各試験化合物の低揮発性溶媒(例えばミリスチン酸イソプロピル、ミグリオール(miglyol)又はグリセロール)中の1〜3wt.%溶液20μlをピペットで顕微鏡スライドガラス上に一様に分散させる。これらを載せたスライドガラスを太陽シミュレーター内40W/m2の強度で刺激する(各場合2時間又は4時間)。
刺激が終了したら、有機溶媒(メタノール、イソプロパノール等)を含有するガラス皿内にスライドガラスをそれぞれ別々に置き、その上に存在する有機物質を超音波浴内で引き離す。結果として生じた溶液をそれぞれ10ml又は25mlのメスフラスコに移して目盛線まで溶媒で補う。参照として非刺激スライドガラスを同様に処理する。
(評価)
サンプル(それぞれのメスフラスコの中身)をHPLC定量化によって評価する。これらの値を非刺激参照値と比較し、刺激中の分解速度を、合計[E異性体+Z異性体]に対して単位時間当たりの[wt.%]で記録する。
(実施例)
図2は、(E)又は(Z)異性体の形態で別々に各化合物(Ib)のUV吸収スペクトルを示す(エタノール中1%溶液、1cm路程)。
B16Vマウスメラノーマ細胞を96-ウェル微量定量プレート内に5×103細胞/ウェルの濃度で接種する。10%の胎児ウシ血清で富化したRPMI培地内で24時間37℃及び5%のCO2にて培養後、種々の濃度の試験物質、0.3mMのチロシン及び10nMのα-MSH(α-メラニン細胞刺激ホルモン)を加えてインキュベーションを96時間続ける。標準物質をチロシン及びα-MSHと共に、0.01mM、0.1mM及び1mMの濃度のコウジ酸とインキュベートする。コントロールにはチロシンとα-MSHだけを加える。インキュベーション後、ナトリウムラウリルスルフェート及び水酸化ナトリウム溶液(最終濃度:それぞれ1mM及び1M)を培養基に添加し、3時間後に400nmにおける吸収(A)を測定する。
試験化合物又はコウジ酸の存在下における色素沈着の阻害を下記式を用いて計算した。
色素沈着の阻害(%)=100−[(A試験化合物/Aコントロール)×100]
いくつかの希釈度の試験化合物における色素沈着の阻害(%)を用いて各試験化合物のIC50を計算する。これは、色素沈着が50%阻害されるときの試験化合物の濃度である。
製剤1:UVA/B広帯域防護のある「油中水」エマルション
製剤2:UVA/B広帯域防護のある「水中油」エマルション
製剤3:UVA/B広帯域防護のある「水中油」エマルション
製剤4:UVA/B広帯域防護のあるオイルフリーサンスプレー
製剤5:UVA/UVB防護のあるバルム
製剤6:UVA/UVB防護のあるエアロゾルフォーム
製剤7:非エアロゾルフォーム
製剤8:細胞のUVB防護のあるシャンプー
製剤9:UVB/UVA防護のあるヘアコンディショナー
製剤10:細胞のUVB防護のあるO/W昼用クリーム
製剤11:細胞のUVB防護のあるW/O夜用クリーム
Claims (12)
- R1及びR2が相互独立にC1-C12-アルキルである、式(I)の化合物。
- R1及びR2がメチルである、請求項3に記載の化合物。
- (a)AhRの細胞核内への転位置を低減又は阻止するため、(b)UVB-誘導遺伝子発現を低減又は阻止するため、(c)多環式芳香族炭化水素、好ましくはTCDDによって誘導されるか又は誘導可能な遺伝子発現を低減又は阻止するため、及び/又は(d)UVB-誘導されるか又はUVB-誘導可能な皮膚損傷、特に皮膚癌、皮膚老化、皮膚炎症及び日焼けを低減又は阻止するため十分な量の式(I)、好ましくは式(Ia)、(Ib)、(Ic)又は(Id)の化合物を含む製剤。
- 1種以上のUVフィルター、特に1種以上のUVBフィルター及び/又は1種以上のUVAフィルターをも含む、請求項6に記載の製剤。
- 式(I)、好ましくは式(Ia)、(Ib)、(Ic)若しくは(Id)の化合物、又は請求項6若しくは7に記載の製剤の、皮膚保護剤、光防護剤及び/又はAhRアンタゴニストとしての使用。
- 式(I)、好ましくは式(Ia)、(Ib)、(Ic)若しくは(Id)の化合物、又は請求項6若しくは7に記載の製剤の、薬物の調製のための使用。
- 式(I)、好ましくは式(Ia)、(Ib)、(Ic)又は(Id)の化合物の、(a)AhRの細胞核内への転位置を低減又は阻止するため、(b)UVB-誘導遺伝子発現を低減又は阻止するため、(c)多環式芳香族炭化水素、好ましくはTCDDによって誘導されるか又は誘導可能な遺伝子発現を低減又は阻止するため、及び/又は(d)UVB-誘導されるか又はUVB-誘導可能な皮膚損傷、特に皮膚癌、皮膚老化、皮膚炎症及び日焼けを低減又は阻止するための製剤の調製のための使用。
- 皮膚を保護する化粧方法であって、保護すべき皮膚に、式(I)、好ましくは式(Ia)、(Ib)、(Ic)若しくは(Id)の化合物、又は請求項6若しくは7に記載の製剤を適用することを特徴とする方法。
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CN101466363B (zh) | 2011-11-23 |
WO2007128723A1 (en) | 2007-11-15 |
ES2421191T3 (es) | 2013-08-29 |
JP5474533B2 (ja) | 2014-04-16 |
US20090208433A1 (en) | 2009-08-20 |
US7855310B2 (en) | 2010-12-21 |
EP2023910B1 (en) | 2013-06-19 |
CN101466363A (zh) | 2009-06-24 |
EP2023910A1 (en) | 2009-02-18 |
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