JP2012510959A - 皮膚美白剤 - Google Patents
皮膚美白剤 Download PDFInfo
- Publication number
- JP2012510959A JP2012510959A JP2011538881A JP2011538881A JP2012510959A JP 2012510959 A JP2012510959 A JP 2012510959A JP 2011538881 A JP2011538881 A JP 2011538881A JP 2011538881 A JP2011538881 A JP 2011538881A JP 2012510959 A JP2012510959 A JP 2012510959A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- skin
- acid
- methyl
- och
- 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.)
- Granted
Links
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- 239000000203 mixture Substances 0.000 claims abstract description 52
- 239000002537 cosmetic Substances 0.000 claims abstract description 41
- 239000000126 substance Substances 0.000 claims abstract description 41
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- 208000012641 Pigmentation disease Diseases 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 16
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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
の物質の使用であって、式中、−R1、R2、R3およびR4は、独立して、水素(−H)、メチル(−CH3)、エチル(−CH2CH3)、C3アルキル、C4アルキル、C5アルキルおよびC6アルキルからなる群から選択され、および、−XおよびYは、独立して、水素(−H)、メチル(−CH3)、エチル(−CH2CH3)、C3アルキル、C4アルキル、C5アルキルおよびC6アルキル、ハロゲン、ニトロ(−NO2)、ヒドロキシ(−OH)、メトキシ(−OCH3)、エトキシ(−OCH2CH3)、C3アルコキシ、C4アルコキシ、C5アルコキシおよびC6アルコキシ、フェニル(−C6H5)、ベンジル(−CH2C6H5)、およびベンジルオキシ(−OCH2C6H5)からなる群から選択される物質の、(a)化粧品組成物および/または局所性組成物の製造のための使用および/または(b)化粧品組成物および/または局所性組成物における(i)皮膚のライトニングおよび/または(ii)皮膚の美白および/または(iii)皮膚の色素沈着の低減および/または(iv)皮膚の高色素沈着の低減および/または(v)皮膚におけるメラニン形成の阻害および/または(vi)老化の兆候の防止および/または遅延、および/または、老化皮膚の皮膚外観の改善のための使用。
Description
−R1、R2、R3およびR4は、独立して、水素(−H)、メチル(−CH3)、エチル(−CH2CH3)、C3アルキル、C4アルキル、C5アルキルおよびC6アルキルからなる群から選択され、および、
−XおよびYは、独立して、水素(−H)、メチル(−CH3)、エチル(−CH2CH3)、C3アルキル、C4アルキル、C5アルキルおよびC6アルキル、ハロゲン、ニトロ(−NO2)、ヒドロキシ(−OH)、メトキシ(−OCH3)、エトキシ(−OCH2CH3)、C3アルコキシ、C4アルコキシ、C5アルコキシおよびC6アルコキシ、フェニル(−C6H5)、ベンジル(−CH2C6H5)、およびベンジルオキシ(−OCH2C6H5)からなる群から選択される〕
で表される物質またはその塩の、
(a)化粧品組成物および/または局所性組成物の製造
のための、
および/または
(b)化粧品組成物および/または局所性組成物における
(i)皮膚のライトニングおよび/または
(ii)皮膚の美白および/または
(iii)皮膚の色素沈着の低減および/または
(iv)皮膚の高色素沈着の低減および/または
(v)皮膚におけるメラニン形成の阻害および/または
(vi)老化の兆候の防止および/または遅延、および/または、老化皮膚の皮膚外観の改善
のための使用を対象とする。
−R1、R2、R3およびR4は、独立して、水素(−H)、メチル(−CH3)、エチル(−CH2CH3)、n−プロピル(−CH2CH2CH3)、イソプロピル(−C(CH3)2)、n−ブチル(−CH2CH2CH2CH3)、イソブチル(−CH2C(CH3)2)、n−ペンチル(−CH2CH2CH2CH2CH3)、イソブチル(−CH2CH2C(CH3)2)およびn−ヘキシル(−CH2CH2CH2CH2CH2CH3)からなる群から選択される、および/または
−XおよびYは、独立して、水素(−H)、メチル(−CH3)、エチル(−CH2CH3)、n−プロピル(−CH2CH2CH3)、イソプロピル(−C(CH3)2)、n−ブチル(−CH2CH2CH2CH3)、イソブチル(−CH2C(CH3)2)、n−ペンチル(−CH2CH2CH2CH2CH3)、イソブチル(−CH2CH2C(CH3)2)、n−ヘキシル(−CH2CH2CH2CH2CH2CH3)、フルロイル(−F)、ブロミル(−Br)、クロリル(−Cl)、ニトロ(−NO2)、ヒドロキシ(−OH)、メトキシ(−OCH3)、エトキシ(−OCH2CH3)、フェニル(−C6H5)、ベンジル(−CH2C6H5)、およびベンジルオキシ(−OCH2C6H5)からなる群から選択される。
−R1、R2、R3およびR4は、独立して、水素(−H)、メチル(−CH3)、エチル(−CH2CH3)、n−プロピル(−CH2CH2CH3)およびイソプロピル(−C(CH3)2)からなる群から選択され、および/または、
−XおよびYは、独立して、水素(−H)、メチル(−CH3)、エチル(−CH2CH3)、フルロイル(−F)、ヒドロキシ(−OH)、メトキシ(−OCH3)およびエトキシ(−OCH2CH3)からなる群から選択される。
−R1=R2=H
−R3およびR4は同一であり、H、メチルおよびエチルからなる群から選択され、および、
−X=Y=H。
−R1=R2=R3=R4=X=Y=H。
・8〜22個の炭素原子を有する直鎖脂肪アルコールへの、12〜22個の炭素原子を有する脂肪酸への、アルキル基に8〜15個の炭素原子を有するアルキルフェノールへの、およびアルキル基に8〜22個の炭素原子を有するアルキルアミンへの、エチレンオキシド2〜30モルおよび/またはプロピレンオキシド0〜5モルの付加生成物;
・アルキル(アルケニル)基に8〜22個の炭素原子を有するアルキルおよび/またはアルケニルオリゴグリコシドおよびそのエトキシ化類似体;
・ヒマシ油および/または水素添加ヒマシ油へのエチレンオキシド1〜15モルの付加生成物;
・ヒマシ油および/または水素添加ヒマシ油へのエチレンオキシド15〜60モルの付加生成物;
・グリセロールおよび/またはソルビタンと、12〜22個の炭素原子を有する不飽和、直鎖または飽和、分枝鎖脂肪酸との、および/または、3〜18個の炭素原子を有するヒドロキシカルボン酸との部分エステル、およびそれらのエチレンオキシド1〜30モルとの付加物;
・ポリグリセロール(平均自己縮合度2〜8)、ポリエチレングリコール(分子量400〜5000)、トリメチロールプロパン、ペンタエリスリトール、糖アルコール(例えばソルビトール)、アルキルグルコシド(例えばメチルグルコシド、ブチルグルコシド、ラウリルグルコシド)、およびポリグルコシド(例えばセルロース)と、12〜22個の炭素原子を有する飽和および/または不飽和、直鎖または分枝鎖脂肪酸との、および/または、3〜18個の炭素原子を有するヒドロキシカルボン酸との部分エステル、およびそのエチレンオキシド1〜30モルの付加物;
・ペンタエリスリトール、脂肪酸、クエン酸および脂肪アルコールの混合エステルおよび/または6〜22個の炭素原子を有する脂肪酸、メチルグルコースおよびポリオール、好ましくはグリセロールまたはポリグリセロールの混合エステル、
・モノ−、ジ−およびトリアルキルホスフェート、およびモノ−、ジ−および/またはトリ−PEGアルキルホスフェートおよびその塩;
・羊毛脂アルコール;
・ポリシロキサン−ポリアルキル−ポリエーテルコポリマーおよび対応する誘導体;
・ブロックコポリマー、例えばポリエチレングリコール−30ジポリヒドロキシステアレート;
・ポリマー乳化剤、例えばGoodrich製のPemulenグレード(TR−1、TR−2);
・ポリアルキレングリコール、および、
・グリセロールカーボネート。
脂肪アルコール、脂肪酸、アルキルフェノールへの、またはヒマシ油への、エチレンオキシドおよび/またはプロピレンオキシドの付加生成物は既知であり、市販製品である。これらは、同族体混合物であり、その平均アルコキシ化度は、エチレンオキシドおよび/またはプロピレンオキシドと付加反応を行う基質との、物質量の比に相当する。エチレンオキシドのグリセロールへの付加生成物のC12/18−脂肪酸モノ−およびジエステルは、化粧品製剤のための再脂化剤として知られている。
アルキルおよび/またはアルケニルオリゴグリコシド、その製造およびその使用は、先行技術から既知である。これらは、特に、グルコースまたはオリゴ糖と8〜18個の炭素原子を有する第一級アルコールとを反応させることによって製造される。グリコシド基に関して、環状糖基がグリコシド結合によって脂肪アルコールに結合しているモノグリコシドならびに好ましくは約8までのオリゴマー化度を有するオリゴマーグリコシドの両方が適している。ここで、オリゴマー化度は統計学的平均値であり、この値は、上記のような工業用グレード製品に一般的な同族体分布に基づいている。
適当な部分グリセリドの代表例は、ヒドロキシステアリン酸モノグリセリド、ヒドロキシステアリン酸ジグリセリド、イソステアリン酸モノグリセリド、イソステアリン酸ジグリセリド、オレイン酸モノグリセリド、オレイン酸ジグリセリド、リシノール酸モノグリセリド、リシノール酸ジグリセリド、リノール酸モノグリセリド、リノール酸ジグリセリド、リノレン酸モノグリセリド、リノレン酸ジグリセリド、エルカ酸モノグリセリド、エルカ酸ジグリセリド、酒石酸モノグリセリド、酒石酸ジグリセリド、クエン酸モノグリセリド、クエン酸ジグリセリド、リンゴ酸モノグリセリド、リンゴ酸ジグリセリド、および製造工程の微量生成物として少量のトリグリセリドを含み得るそれらの工業用グレードの混合物である。前記部分グリセリドへの1〜30mol、好ましくは5〜10molのエチレンオキシドの付加生成物も、同様に適する。
適当なソルビタンエステルは、ソルビタンモノイソステアレート、ソルビタンセスキイソステアレート、ソルビタンジイソステアレート、ソルビタントリイソステアレート、ソルビタンモノオレエート、ソルビタンセスキオレエート、ソルビタンジオレエート、ソルビタントリオレエート、ソルビタンモノエルケート、ソルビタンセスキエルケート、ソルビタンジエルケート、ソルビタントリエルケート、ソルビタンモノリシノレエート、ソルビタンセスキリシノレエート、ソルビタンジリシノレエート、ソルビタントリリシノレエート、ソルビタンモノヒドロキシステアレート、ソルビタンセスキヒドロキシステアレート、ソルビタンジヒドロキシステアレート、ソルビタントリヒドロキシステアレート、ソルビタンモノタルトレート、ソルビタンセスキタルトレート、ソルビタンジタルトレート、ソルビタントリタルトレート、ソルビタンモノシトレート、ソルビタンセスキシトレート、ソルビタンジシトレート、ソルビタントリシトレート、ソルビタンモノマレエート、ソルビタンセスキマレエート、ソルビタンジマレエート、ソルビタントリマレエート、およびこれらの工業用グレード混合物である。前記ソルビタンエステルの、エチレンオキシドの1〜30mol、好ましくは5〜10mol付加生成物も、同様に適する。
適当なポリグリセロールエステルの代表例は、ポリグリセリル−2 ジポリヒドロキシステアレート(Dehymuls(登録商標)PGPH)、ポリグリセロール−3 ジイソステアレート(Lameform(登録商標)TGI)、ポリグリセリル−4 イソステアレート(Isolan(登録商標)GI 34)、ポリグリセリル−3 オレエート、ジイソステアロイルポリグリセリル−3ジイソステアレート(Isolan(登録商標)PDI)、ポリグリセリル−3 メチルグルコースジステアレート(Tego Care(登録商標)450)、ポリグリセリル−3 蜜ろう(Cera Bellina(登録商標))、ポリグリセリル−4 カプレート(Polyglycerol Caprate T2010/90)、ポリグリセリル−3 セチルエーテル(Chimexane(登録商標)NL)、ポリグリセリル−3 ジステアレート(Cremophor(登録商標)GS 32)およびポリグリセリルポリリシノレエート(Admul(登録商標)WOL 1403)、ポリグリセリルダイマレートイソステアレート、およびそれらの混合物である。さらに適当なポリオールエステルの例は、トリメチロールプロパンまたはペンタエリスリトールとラウリン酸、ヤシ脂肪酸、獣脂脂肪酸、パルミチン酸、ステアリン酸、オレイン酸、ベヘン酸などとの、エチレンオキシド1〜30モルと任意に反応した、モノ−、ジ−およびトリエステルである。
通常のアニオン性乳化剤は、12〜22個の炭素原子を有する脂肪族脂肪酸、例えば、パルミチン酸、ステアリン酸またはベヘン酸、および12〜22個の炭素原子を有するジカルボン酸、例えば、アゼライン酸またはセバシン酸である。
さらに、双性イオン性界面活性剤を乳化剤として使用することができる。「双性イオン性界面活性剤」の用語は、少なくとも1つの第四級アンモニウム基および少なくとも1つのカルボキシレートおよび1つのスルホネート基を分子中に有する表面活性化合物を意味する。特に適当な双性イオン性界面活性剤は、いわゆるベタイン、例えば、N−アルキル−N,N−ジメチルアンモニウムグリシネート、例えばココアルキルジメチルアンモニウムグリシネート、N−アシルアミノプロピル−N,N−ジメチルアンモニウムグリシネート、例えばココアシルアミノプロピル−ジメチルアンモニウムグリシネート、および2−アルキル−3−カルボキシメチル−3−ヒドロキシエチルイミダゾリンであり(いずれの場合にも、アルキルまたはアシル基に8〜18個の炭素原子を有する)、およびココアシルアミノエチルヒドロキシエチルカルボキシメチルグリシネートである。特に好ましくは、CTFA名コカミドプロピルベタインの名称で既知の脂肪酸アミド誘導体である。両性界面活性剤も同様に適当な乳化剤である。「両性界面活性剤」という用語は、C8/18−アルキルまたはアシル基は別として、少なくとも1つの遊離のアミノ基および少なくとも1つの−COOHまたは−SO3H基を分子中に含有し、内部塩を形成することができる表面活性化合物を意味する。両性界面活性剤の適当な例は、いずれの場合にも、約8〜18個の炭素原子をアルキル基に有する、N−アルキルグリシン、N−アルキルアミノプロピオン酸、N−アルキルアミノ酪酸、N−アルキルイミノジプロピオン酸、N−ヒドロキシエチル−N−アルキルアミドプロピルグリシン、N−アルキルタウリン、N−アルキルサルコシン、2−アルキルアミノプロピオン酸およびアルキルアミノ酢酸である。特に好ましい両性界面活性剤は、N−ココアルキルアミノプロピオネート、ココアシルアミノエチルアミノプロピオネートおよびC12/18−アシルサルコシンである。最後に、カチオン性界面活性剤も乳化剤として適当であり、エステルクォート型のもの、好ましくはメチル−四級化ジ脂肪酸トリエタノールアミンエステル塩、が特に好ましい。
・3−ベンジリデンカンファーまたは3−ベンジリデンノルカンファーおよびその誘導体、例えば3−(4−メチルベンジリデン)カンファー;
・4−アミノ安息香酸誘導体、好ましくは4−(ジメチルアミノ)安息香酸2−エチルヘキシル、4−(ジメチルアミノ)安息香酸2−オクチルおよび4−(ジメチルアミノ)安息香酸アミル;
・ケイ皮酸のエステル、好ましくは4−メトキシケイ皮酸2−エチルヘキシル、4−メトキシケイ皮酸プロピル、4−メトキシケイ皮酸イソアミル、2−シアノ−3,3−フェニルケイ皮酸2−エチルヘキシル(オクトクリレン);
・サリチル酸のエステル、好ましくはサリチル酸2−エチルヘキシル、サリチル酸4−イソプロピルベンジル、サリチル酸ホモメンチル;
・ベンゾフェノンの誘導体、好ましくは2−ヒドロキシ−4−メト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、2,2’−ジヒドロキシ−4−メトキシベンゾフェノン;
・ベンザルマロン酸のエステル、好ましくは4−メトキシベンザルマロン酸ジ−2−エチルヘキシル;
・トリアジンの誘導体、例えば2,4,6−トリアニリノ(p−カルボ−2’−エチル−1’−ヘキシルオキシ)−1,3,5−トリアジンおよびオクチルトリアゾンまたはジオクチルブタアミドトリアゾン(Uvasorb(登録商標)HEB);
・プロパン−1,3−ジオン、例えば1−(4−tert−ブチルフェニル)−3−(4’−メトキシフェニル)−プロパン−1,3−ジオン;
・ケトトリシクロ(5.2.1.0)デカン誘導体。
・2−フェニルベンズイミダゾール−5−スルホン酸およびそのアルカリ金属、アルカリ土類金属、アンモニウム、アルキルアンモニウム、アルカノールアンモニウムおよびグルクアンモニウム塩;
・ベンゾフェノンのスルホン酸誘導体、好ましくは2−ヒドロキシ−4−メトキシベンゾフェノン−5−スルホン酸およびその塩;
・3−ベンジリデンカンファーのスルホン酸誘導体、例えば4−(2−オキソ−3−ボルニリデンメチル)−ベンゼンスルホン酸および2−メチル−5−(2−オキソ−3−ボルニリデン)スルホン酸およびその塩。
・グリセロール;
・アルキレングリコール、例えば、エチレングリコール、ジエチレングリコール、プロピレングリコール、ブチレングリコール、へキシレングリコール、および100〜1000ダルトンの平均分子量を有するポリエチレングリコール;
・1.5〜10の自己縮合度を有する工業用グレードのオリゴグリセロール混合物、例えば、40〜50重量%のジグリセロール含量を有する工業用グレードのジグリセロール混合物;
・メチロール化合物、例えば、特に、トリメチロールエタン、トリメチロールプロパン、トリメチロールブタン、ペンタエリスリトールおよびジペンタエリスリトール;
・低アルキルグルコシド、特に、アルキル基に1〜8個の炭素原子を有するアルキルグルコシド、例えば、メチルおよびブチルグルコシド;
・5〜12個の炭素原子を有する糖アルコール、例えば、ソルビトールまたはマンニトール、
・5〜12個の炭素原子を有する糖、例えば、グルコースまたはスクロース;
・アミノ糖、例えば、グルカミン;
・ジアルコールアミン、例えば、ジエタノールアミンまたは2−アミノ−1,3−プロパンジオール。
メラノサイト(B16セルライン)を、ウシ胎仔血清(FCS)を含む標準の細胞培養培地に接種した。37℃およびCO2=5%で3日間インキュベートした後、増殖培地を、試験する化合物を広範な濃度で含む標準培地および成分を含まない対照と交換した。3日間のインキュベートの後、メラニンのレベルを、475nmにおいて光学密度を記録することによって測定した。細胞をバランス塩によって洗浄し、0.1M NaOH溶液中でホモジナイズした後、生存細胞数を、細胞タンパク質レベルの評価(Bradford法)によって測定した。
チロシナーゼは、メラニン生合成経路において、初期段階:チロシンのジヒドロキシフェニルアラニン(DOPA)への酸化、および、DOPAのドーパキノンへの酸化を触媒する重要な酵素である。
Claims (8)
- 式(I):
−R1、R2、R3およびR4は、独立して、水素(−H)、メチル(−CH3)、エチル(−CH2CH3)、C3アルキル、C4アルキル、C5アルキルおよびC6アルキルからなる群から選択され、および、
−XおよびYは、独立して、水素(−H)、メチル(−CH3)、エチル(−CH2CH3)、C3アルキル、C4アルキル、C5アルキルおよびC6アルキル、ハロゲン、ニトロ(−NO2)、ヒドロキシ(−OH)、メトキシ(−OCH3)、エトキシ(−OCH2CH3)、C3アルコキシ、C4アルコキシ、C5アルコキシおよびC6アルコキシ、フェニル(−C6H5)、ベンジル(−CH2C6H5)、およびベンジルオキシ(−OCH2C6H5)からなる群から選択される〕
で表される物質またはその塩の、
(a)化粧品組成物および/または局所性組成物の製造
のための、
および/または
(b)化粧品組成物および/または局所性組成物における
(i)皮膚のライトニングおよび/または
(ii)皮膚の美白および/または
(iii)皮膚の色素沈着の低減および/または
(iv)皮膚の高色素沈着の低減および/または
(v)皮膚におけるメラニン形成の阻害および/または
(vi)老化の兆候の防止および/または遅延、および/または、老化皮膚の皮膚外観の改善
のための使用。 - 式(I)の物質またはその塩が、組成物の総量に基づいて0.0001〜10重量%の量で存在する、請求項1に記載の使用。
- −R1、R2、R3およびR4は、独立して、水素(−H)、メチル(−CH3)、エチル(−CH2CH3)、n−プロピル(−CH2CH2CH3)およびイソプロピル(−C(CH3)2)からなる群から選択され、および/または、
−XおよびYは、独立して、水素(−H)、メチル(−CH3)、エチル(−CH2CH3)、フルロイル(−F)、ヒドロキシ(−OH)、メトキシ(−OCH3)およびエトキシ(−OCH2CH3)からなる群から選択される、
請求項1または2に記載の使用。 - −R1=R2=水素(−H)
−R3およびR4は同一であり、水素(−H)、メチル(−CH3)、エチル(−CH2CH3)からなる群から選択され、および、
−X=Y=水素(−H)
である、請求項1〜3のいずれかに記載の使用。 - R1=R2=R3=R4=X=Y=水素(−H)である、請求項1〜4のいずれかに記載の使用。
- 皮膚の色素沈着における異常症に関する疾患の治療のための、請求項1〜5のいずれかに記載される式(I)の物質またはその塩。
- 前記疾患が異常メラニン合成および/または分泌を示す、請求項6に記載の物質。
- 請求項1〜5のいずれかに記載される式(I)の物質またはその塩を含有する化粧品および/または局所性組成物。
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EP08021156A EP2193779A1 (en) | 2008-12-05 | 2008-12-05 | Skin whitener |
EP08021156.8 | 2008-12-05 | ||
PCT/EP2009/008463 WO2010063415A1 (en) | 2008-12-05 | 2009-11-26 | Skin whitener |
Publications (3)
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JP2012510959A true JP2012510959A (ja) | 2012-05-17 |
JP2012510959A5 JP2012510959A5 (ja) | 2013-01-17 |
JP5781936B2 JP5781936B2 (ja) | 2015-09-24 |
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US (1) | US20110236326A1 (ja) |
EP (2) | EP2193779A1 (ja) |
JP (1) | JP5781936B2 (ja) |
KR (1) | KR20110091530A (ja) |
CN (1) | CN102238936B (ja) |
ES (1) | ES2545786T3 (ja) |
WO (1) | WO2010063415A1 (ja) |
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JP2013044719A (ja) * | 2011-08-26 | 2013-03-04 | Pola Chem Ind Inc | スクリーニング方法 |
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US8293218B2 (en) | 2010-07-29 | 2012-10-23 | Conopco, Inc. | Skin care compositions comprising substituted monoamines |
US8476251B2 (en) | 2010-07-29 | 2013-07-02 | Conopco, Inc. | Skin care compositions comprising substituted diamines |
WO2014069555A1 (ja) * | 2012-11-02 | 2014-05-08 | 株式会社成和化成 | プロピルフェニルエーテル誘導体、並びにそれを含むメラニン生成抑制剤、美白剤、抗菌剤及び化粧料 |
CN106031854B (zh) * | 2015-03-20 | 2018-03-20 | 中国石油化工股份有限公司 | 一种阴离子型低聚表面活性剂及其制备方法 |
US10966912B2 (en) * | 2016-03-21 | 2021-04-06 | Symrise Ag | Medicament |
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2008
- 2008-12-05 EP EP08021156A patent/EP2193779A1/en not_active Withdrawn
-
2009
- 2009-11-26 JP JP2011538881A patent/JP5781936B2/ja not_active Expired - Fee Related
- 2009-11-26 ES ES09771299.6T patent/ES2545786T3/es active Active
- 2009-11-26 US US13/132,680 patent/US20110236326A1/en not_active Abandoned
- 2009-11-26 CN CN200980148275.7A patent/CN102238936B/zh not_active Expired - Fee Related
- 2009-11-26 EP EP09771299.6A patent/EP2352486B1/en active Active
- 2009-11-26 WO PCT/EP2009/008463 patent/WO2010063415A1/en active Application Filing
- 2009-11-26 KR KR1020117012812A patent/KR20110091530A/ko not_active Application Discontinuation
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CN102238936B (zh) | 2014-09-17 |
JP5781936B2 (ja) | 2015-09-24 |
EP2352486B1 (en) | 2015-07-29 |
US20110236326A1 (en) | 2011-09-29 |
KR20110091530A (ko) | 2011-08-11 |
WO2010063415A1 (en) | 2010-06-10 |
ES2545786T3 (es) | 2015-09-15 |
EP2352486A1 (en) | 2011-08-10 |
CN102238936A (zh) | 2011-11-09 |
EP2193779A1 (en) | 2010-06-09 |
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