JP2012012409A - 皮膚の保存のためのクレアチンおよびクレアチン化合物の使用 - Google Patents
皮膚の保存のためのクレアチンおよびクレアチン化合物の使用 Download PDFInfo
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- JP2012012409A JP2012012409A JP2011217368A JP2011217368A JP2012012409A JP 2012012409 A JP2012012409 A JP 2012012409A JP 2011217368 A JP2011217368 A JP 2011217368A JP 2011217368 A JP2011217368 A JP 2011217368A JP 2012012409 A JP2012012409 A JP 2012012409A
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- creatine
- skin
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Abstract
【解決手段】本発明の方法で使用することができるクレアチン化合物としては、(1)クレアチン、クレアチンホスフェート、およびクレチンキナーゼに対して基質または基質アナログとして作用することができるこれらの化合物のアナログ;(2)クレアチンの生物学的な活性を模倣する分子;(3)クレアチンキナーゼシステムをモジューレートする分子を含む。
【選択図】なし
Description
クレアチンおよびクレアチン化合物については、米国特許第08/853,174号(これは、1997年5月7日に出願);米国特許第08/914,887号(これは、1997年8月19日に出願);米国特許第08/736,967号(これは、1996年10月25日に出願)および米国特許第09/285,395号(これは、1999年4月2日に出願)を含む関連出願に記載されている。これらの各出願の内容(それら出願に引用されている全ての文献を含む)は、本明細書の一部を構成する。
クレアチンキナーゼ/クレアチンホスフェートエネルギーシステムは、高くて変動性のエネルギーを必要とする組織にみられる同化エネルギー生成システムのほんの1構成成分である。クレアチンエネルギーシステムの構成成分としては、例えば酵素のクレアチンキナーゼ、基質のクレアチンおよびクレアチンホスフェート、並びにクレアチンのトランスポーターを含む。クレアチンキナーゼによって触媒される反応は、MgADP+PCr=+H+MgATP+Crである。このシステムに関連するいくつかの機能としては、変動性で高いエネルギーを要求する細胞におけるエネルギーの効率的な再生、細胞の異なる部分へのエネルギー輸送、ホスホリル転移活性、イオン運搬の調節およびシグナル形質転換経路の改善を含む。
本発明は、エネルギープールを貯蔵し、遊離ラジカルおよび酸化的ストレスから保護することによって、加齢に関連する損傷または侵襲(例えば、有害なUV放射、ストレスおよび疲労)から皮膚組織を保護する方法に関連する。このことは、皮膚の損傷または皮膚の加齢を防止し、減少し、または緩和するのに十分な量の、クレアチン化合物または、クレアチンキナーゼ/ホスホクレアチンシステムの1つ以上の構造的なまたは機能的な構成成分をモジュレートする化合物を投与することによって達成される。この目的に有効な化合物としては、様々な水和物または塩形態の天然のクレアチン化合物、およびクレアチンアナログを含む。それらの化合物は、皮膚表面上に容易に広げるために、クリーム剤、油、乳化剤などと一緒に混合することができる。あるいは、それら化合物をサプリメントの形態でパッケージすることもできる。
本発明の方法は、通常、被験者にある量の1つまたは複数のクレアチン化合物を投与することを含む。クレアチン化合物は、皮膚の加齢または損傷の症状を防止し、軽減し、または緩和するために十分な量のクレアチン/ホスホクレアチンシステムの構造的なまたは機能的な構成成分の1つ以上をモジュレートすると考えられている。モジュレートすることができるシステムの構成成分としては、例えば酵素のクレアチンキナーゼ、基質のクレアチンおよびクレアチンホスフェート、並びにクレアチンのトランスポーターを含む。用語「モジュレートする」、「モジュレート」または「モジュレートするため」とは、クレアチンキナーゼ/ホスホクレアチンシステムのうちのいずれかの構成成分の活性を増減することを含む。
実質的に全ての多細胞生物のライフサイクルに共通の特徴は、一生のうちの生産期が終わった後の、様々な生理学的なプロセスの効率の進行性低下である。データは、機能性能力の低下に二次的な老化細胞死は分子酸化的な損傷の蓄積が原因であるという仮説を支持する(Harmanによって1956年;Stadtmanによって1992年;Amesらによって1993年;Sohalによって1995年)。該仮説は、酸素が潜在的な毒性物質であって、好気性菌による使用はそれらの即時の生存にとっては必要ではあるが、長期間の生存にとっては危険であり得るという事実に基づいている。分子酸素はスーパーオキシド、過酸化水素およびヒドロキシルラジカルの前駆体である。更なる反応において、これらはマクロ分子に対して大規模な酸化的損傷を引き起こすような活性酸素種を生成することができる。脂質の過酸化、DNA損傷およびプロテインのカルボニル化はいくつかの荒廃的な影響である。加齢の間に酸化的なストレスの量が増加し、これにより活性酸素種の生成速度の増加、あるいは抗酸化上の防御の低下または損傷した分子の修復もしくは排除の効率の低下を引き起こし得る(Sohalらによる1996年)。加齢と共に、ミトコンドリアからのROSの生産が増加し、これにより内部のミトコンドリア膜の損傷が生じる。正のフィードバック機構によって、これはROSの更なる増加を生じる。ハエ(flies)のうち、より長い平均余命を有しているハエは、ミトコンドリアスーパーオキシド、過酸化水素の生産のより低い速度、プロテインの酸化的な損傷のより低い速度、より小さいDNAの酸化的損傷、SODおよびカタラーゼのより高い活性、グルタチオン(多用途の細胞内還元体)の増加を示すことが分かった。異種間における最大余命の変化は、代謝速度(酸素の消費の速度)、代謝能力(寿命の間の体重のグラム当りに消費したエネルギーの総量)および酸化的なストレスのレベルの違いに関連することが多い。最も高い程度の酸化的な損傷は、長期間生存している有糸分裂後の細胞で主に構成される組織(例えば、脳、心臓および骨格筋)において生じる。これらの組織は、酸化的なストレスが関与しているいくつかの加齢に関連する変性障害の標的でもある(Daviesによる1995年;Weindrushらによる1993年)。活性酸素種の生産を最小化する薬物は、保護的であると予想される。
細胞は、生存するのに、および生物学的な活性を特徴づける多数の仕事(task)を行なうのにエネルギーを必要とする。細胞エネルギーの要求および供給は、通常エネルギーの経済性および効率とバランスをとっており、そして密接に調節されている。クレアチンキナーゼは、高くて変動性のエネルギーの断続的な要求を有する細胞(例えば、骨格および心筋、脳および神経組織(例えば、網膜および精子を含む))のエネルギー代謝および電解質の使用において重要な役割を果たしている(Bessmanによる1985年;Wallimanによる1992年;WyssおよびKaddurah−Daoukによる1999年)。上記の通り、該酵素はクレアチンホスフェートからADPへのホスホリル基の可逆的な転移を触媒して、ATPを生成する。筋肉(CK−MM)、脳(CK−BB)およびミトコンドリア(CK−Mia、CK−Mib)イソ型を含む多くのクレアチンキナーゼ(CK)のイソ型が存在する。ミトコンドリアクレアチンキナーゼは主に内部および外部のミトコンドリア膜に存在し、そこではアデノシンヌクレオチド転移酵素および他のプロテインと一緒にATPをホスホクレアチンに形質転換し、エネルギーを使用するために、そのものを細胞の他の部位に輸送することができる。ミロコンドリアの8量体のクレアチンキナーゼは、ミトコンドリア透過性転移および細胞死プロセスに関与している(O’Gormanによる1997年)。クレアチンは酸化的ホスホリル化の優れた刺激物質であって、このものは8量体のミトコンドリアのクレアチンキナーゼの生成を誘発して、ミトコンドリアのポア開口を阻害すると考えられる。細胞質のイソ型はホフホクレアチンを利用して細胞の働きのためにATPを生産する。基質のクレアチンとホスホクレアチンによるミトコンドリアおよび細胞質イソ型との間の伝達は、エネルギー生産部位およびエネルギー消費部位の間との連結性を保証する。
クレアチン含有物およびクレアチンキナーゼシステムの効率は加齢と共に減少する。加齢およびいくつかの侵襲は、酸化的ストレスを引き起こし、且つエネルギーを損なわせる。ここで、クレアチンキナーゼシステムのモジュレートにより、酸化的な損傷に関連する分子の生産速度は最小化されることが示されている。それら最小化とエネルギーの追加効果とを組合せることにより、加齢または侵襲への曝露の間での組織への損傷が遅延される。クレアチンキナーゼによるATP合成の速度を改変するクレアチンおよびクレアチンアナログは、エネルギー生産、ミトコンドリアの機能を維持し、且つ遊離ラジカル生産から保護することができる。それらの効果は加齢または侵襲に関連する皮膚の損傷について正のインパクトを有し得る。
本発明に有用なクレアチン化合物は、クレアチンキナーゼ/ホスホクレアチンシステムにおける1つ以上の構造的または機能的な構成成分をモジュレートする化合物を含む。この目的に有効な化合物としては、例えばクレアチン、クレアチンホスフェートおよびそれらのアナログ、それらの活性を模倣する化合物、並びに上で定義するこれらの化合物の塩を含む。典型的なクレアチン化合物を以下に記載する。
a)Yは、−CO2H、−NHOH、−NO2、−SO3H、−C(=O)NHSO2Jおよび−P(=O)(OH)(OJ)からなる群から選ばれて、Jは水素、C1〜C6の直鎖アルキル、C3〜C6の分枝アルキル、C2〜C6のアルケニル、C3〜C6の分枝アルケニルおよびアリールからなる群から選ばれる。
b)Aは、C、CH、C1〜C5のアルキル、C2〜C5のアルケニル、C2〜C5のアルキニルおよびC1〜C5のアルコイル鎖からなる群から選ばれ、その各々は独立して、
1)K(ここで、KはC1〜C6の直鎖アルキル、C2〜C6の直鎖アルケニル、C1〜C6の直鎖アルコイル、C3〜C6の分枝アルキル、C3〜C6の分枝アルケニルおよびC4〜C6の分枝アルコイルからなる群から選ばれ、該Kは独立してブロモ、クロロ、エポキシおよびアセトキシからなる群から選ばれる0〜2個の置換基を有している);
2)アリール基(ここで、アリール基は、1〜2環の炭素環および1〜2環のヘテロ環からなる群から選ばれ、該アリール基は独立して−CH2Lおよび−COCH2Lからなる群から選ばれる置換基を0〜2個有している。Lは独立してブロモ、クロロ、エポキシおよびアセトキシからなる群から選ばれる);および
3)−NH−M(ここで、Mは水素、C1〜C4のアルキル、C2〜C4のアルケニル、C1〜C4のアルコイル、C3〜C4の分枝アルキル、C3〜C4の分枝アルケニルおよびC4の分枝アルコイルからなる群から選ばれる)
からなる群から選ばれる置換基を0〜2個有している。
c)XはNR1、CHR1、CR1、OおよびSからなる群から選ばれる。ここで、R1は群:
1)水素;
2)K(ここで、KはC1〜C6の直鎖アルキル、C2〜C6の直鎖アルケニル、C1〜C6の直鎖アルコイル、C3〜C6の分枝アルキル、C3〜C6の分枝アルケニルおよびC4〜C6の分枝アルコイルからなる群から選ばれる。該Kは独立して、ブロモ、クロロ、エポキシおよびアセトキシからなる群から選ばれる置換基を0〜2個有している);
3)アリール基(ここで、アリール基は、1〜2環の炭素環および1〜2環のヘテロ環からなる群から選ばれ、該アリール基は独立して、−CH2Lおよび−COCH2Lからなる群から選ばれる置換基を0〜2個有している。Lは独立して、ブロモ、クロロ、エポキシおよびアセトキシからなる群から選ばれる);
4)w−メチル炭素によって連結した、C5〜C9α−アミノ−w−メチル−w−アデノシルカルボン酸;
5)w−メチル炭素によって連結した、C5〜C9α−アミノ−w−アザ−w−メチル−w−アデノシルカルボン酸;
6)w−メチル炭素によって連結した、C5〜C9α−アミノ−w−チア−w−メチル−w−アデノシルカルボン酸
からなる群から選ばれる。
d)Z1およびZ2は独立して=O、−NHR2、−CH2R2、−NR2OHからなる群から選ばれる。ここでZ1およびZ2は共に=Oでなくてもよく、R2は、
1)水素;
2)K(ここで、KはC1〜C6の直鎖アルキル、C2〜C6の直鎖アルケニル、C1〜C6の直鎖アルコイル、C3〜C6の分枝アルキル、C3〜C6の分枝アルケニルおよびC4〜C6の分枝アルコイルからなる群から選ばれる。該Kは独立して、ブロモ、クロロ、エポキシおよびアセトキシからなる群から選ばれる置換基を0〜2個有している);
3)アリール基(ここで、アリール基は、1〜2環の炭素環および1〜2環のヘテロ環からなる群から選ばれ、該アリール基は独立して、−CH2Lおよび−COCH2Lからなる群から選ばれる置換基を0〜2個有している。Lは独立して、ブロモ、クロロ、エポキシおよびアセトキシからなる群から選ばれる);
4)w−炭素によって連結した、C4〜C8のα−アミノ−カルボン酸;
5)B(ここで、Bは−CO2H、−NHOH、−SO3H、−NO2、OP(=O)(OH)(OJ)および−P(=O)(OH)(OJ)からなる群から選ばれ、Jは水素、C1〜C6の直鎖アルキル、C3〜C6の分枝アルキル、C2〜C6のアルケニル、C3〜C6の分枝アルケニルおよびアリールからなる群から選ばれる。また、Bは場合により、C1〜C2のアルキル、C2のアルケニルおよびC1〜C2のアルコイルからなる群から選ばれる連結基によって窒素と結合していてよい);
6)−D−E(ここで、Dは、C1〜C3の直鎖アルキル、C3の分枝アルキル、C2〜C3の直鎖アルケニル、C3の分枝アルケニル、C1〜C3の直鎖アルコイル、アリールおよびアロイルからなる群から選ばれる。そして、
Eは、−(PO3)nNMP(ここでnは0〜2であり、NMPは5’−ホスフェート、3’−ホスフェートまたは塩基の芳香環によって結合したリボヌクレオチド・モノリン酸塩である);−[P(=O)(OCH3)(O)]m−Q(ここで、mは0〜3であって、Qはリボースまたは塩基の芳香環によって結合したリボヌクレオシドである);−[P(=O)(OH)(CH2)]m−Q(ここで、mは0〜3であって、Qはリボースまたは塩基の芳香環によって結合したリボヌクレオシドである)からなる群から選ばれる。
該アリール基は、独立してCl、Br、エポキシ、アセトキシ、−OG、−C(=O)Gおよび−CO2Gからなる群から選ばれる置換基を0〜3個有しており、ここでGは独立して、C1〜C6の直鎖アルキル、C2〜C6の直鎖アルケニル、C1〜C6の直鎖アルコイル、C3〜C6の分枝アルキル、C3〜C6の分枝アルケニル、C4〜C6の分枝アルコイルからなる群から選ばれる。
また、Eはいずれの位置でDと結合することができて、Dがアルキルまたはアルケニルである場合には、Dはアミド結合によって一方の末端または両方の末端で結合することができる);
7)−E(ここで、Eは、−(PO3)nNMP(ここでnは0〜2であり、NMPは5’−ホスフェート、3’−ホスフェートまたは塩基の芳香環によって結合したリボヌクレオチド・モノリン酸塩である);−[P(=O)(OCH3)(O)]m−Q(ここで、mは0〜3であって、Qはリボースまたは塩基の芳香環によって結合したリボヌクレオシドである);−[P(=O)(OH)(CH2)]m−Q(ここで、mは0〜3であって、Qはリボースまたは塩基の芳香環によって結合したリボヌクレオシドである)からなる群から選ばれる。
該アリール基は、独立してCl、Br、エポキシ、アセトキシ、−OG、−C(=O)Gおよび−CO2Gからなる群から選ばれる置換基を0〜3個有しており、ここでGは独立してC1〜C6の直鎖アルキル、C2〜C6の直鎖アルケニル、C1〜C6の直鎖アルコイル、C3〜C6の分枝アルキル、C3〜C6の分枝アルケニル、C4〜C6の分枝アルコイルからなる群から選ばれる。
そして、Eがアリールである場合には、Eはアミド結合によって連結していてもよい)
からなる群から選ばれる。
e)R1および少なくとも1つのR2基が存在する場合には、R1はR2基に単結合もしくは二重結合によって連結して、5〜7員の環を形成してもよい。
f)2つのR2基が存在する場合には、それらは単結合もしくは二重結合によって連結して、4〜7員の環を形成してもよい。
g)R1が存在していて、Z1またはZ2が−NHR2、−CH2R2および−NR2OHからなる群から選ばれる場合には、R1はZ1またはZ2のいずれかの炭素または窒素と単結合または二重結合によって結合して、4〜7員の環を形成してもよい]
クレアチン化合物を、苦しんでいる個体に、単独で、または別のクレアチンアナログもしくは他の薬剤と組み合わせて投与することができる。その他の薬剤としては、認可された治療薬、酸化的損傷を防止するサプリメント、エネルギー増強剤、糖類、代謝の中間体および栄養剤などであり得る。クレアチン化合物を、医薬的に許容し得る担体中の医薬的に許容し得る塩として投与することができる。該化合物を、様々な経路によって被験者に投与することができ、該経路としては、例えば、局所、経口(食事)、経皮または非経口(例えば、皮下、筋肉内、静脈注射、ボーラス注入または連続注入)の投与経路を含むが、必ずしもこれらに限定されない。クレアチンアナログを含有する組成物の有効な量(すなわち、個体における所望の効果を得るのに十分な量)をその個体に投与する。投与する薬物の実際の量は、例えば、個体の大きさおよび年齢などの因子に加えて、症状の重症度、他の医学的状態および所望する処置の目標に依存するであろう。上記の通り、化合物は局所投与することが好ましい。
1.FALSマウスにおいて、1%クレアチン補給が3−ニトロチロシン/チロシン濃度に及ぼす影響
酸化的損傷は、一酸化窒素産生および過酸化亜硝酸産生の活性化(これらは、プロテインのニトロ化を生じる)に関与している。プロテインのニトロ化は、チロシンに対する3−ニトロチロシンの比率を測定することによって決定することができた。FALSマウスは、家族性ALS(筋萎縮性側索硬化症)を有する患者においてみられる、Cu/Znスーパーオキシドジスムターゼ由来の変異体を発現するトランスジェニック動物である。これらの動物は、運動ニューロンの損失および筋肉の脱力感を徐々に伴なってALSを発症し、135日以内に死亡する。酸化的ストレスは、運動ニューロンの死と関連している。3−ニトロチロシンのレベルは、これらのマウスの脊髄において有意に増加する(Ferranteによる1997年)。記載の通り、G93A突然変異を有するトランスジェニックマウスおよび同腹仔コントロール(各群は8匹のマウスである)に、70日齢にて1%のクレアチン食かまたは非補給食を与え、その後、3−ニトロチロシンの測定のために120日齢で屠殺した(Ferranteによる1997年)。図1(左のパネル)は、クレアチンがトランスジェニックFALSの下方脊髄におけるより高レベルな3−ニトロチロシン/チロシンを有意に阻害することができることを示す。また、右パネルは、クレアチンが上方脊髄における3−ニトロチロシン/チロシンの産生の活性化を阻害することができることを示している。
インビボにおける遊離ラジカル産生のレべルは、微量透析法(Matthewsらによる1998年)を用いて測定することができる。ミトコンドリアの毒素である3−ニトロプロピオン酸を投与することにより、線条体におけるサリチル酸の2,3−DHBAへの変換が有意に増加し、この変換はCu、Zn SODを過剰発現するマウスにおいて遮断される(Bogdanovらによる、1998年)。本明細書において、我々は、3−ニトロプロピオン酸(3−NP)を全身投与することにより、非補給食を与えたG93Aトランスジェニックマウスにおいて4−HBAの3,4−DHBAへの変換が有意に増加することを示す(図2)。1%のクレアチン補給食を与えた動物の場合には、3−NPを投与後の3,4−DHBA/4HBAの有意な増加はなかった。このことは、クレアチンが加齢に関連する損傷に関与しているヒドロキシラジカルの産生を最小限とすることができることを示している。
マロン酸を注入後の線条体の組織におけるヒドロキシラジカルのレベルを側定するために、サリチル酸ヒドロキシラジカルをトラップする方法を使用した。マロン酸の線条体内注入を行なう前に、各群の8匹の動物に標準食かまたは1%のクレアチンもしくは1%のシクロクレアチンを補給した食餌を2週間与えた。マロン酸の注入を行なう直前に、動物に200mg/kgのサリチル酸を注射して、約1時間後に屠殺した。次いで、線条体を2mmの厚さのスライスですぐに解剖して、このものを冷却した0.1M過塩素酸(0.25mL)中にいれた。続いて、試料を超音波処理し、すぐに凍結し、解凍して2回遠心分離した。上清のアリコートを16−電極電気化学的検出を用いたHPLCによる分析を行なった(Bealらによる1990年)。サリチル酸、2,3および2,5DHBA、チロシン、3−ニトロチロシンについて、それぞれ20.5、9.4、6.3、10.5、18.2分の保持時間で、840、240、120、600および800mVでの酸化によって電気化学的に測定を行なった。異なる脳のサリチル酸濃度についてDHBA濃度を規格化するために、該データをサリチル酸に対する2,3および2,5DHBAの比率として表わす。同様に、3−ニトロチロシンレベルをチロシンレベルに規格化させた。我々はまた、2週間の1%クレアチン補給が3−NPによって誘発される3−ニトロチロシンレベルの増加に与える影響についても調べた。雄性スプレーグドーリーラットについて、20mg/kgの用量で3−NPを腹腔内処理した後、3時間で屠殺した。各群について10匹の動物を調べた。該線条体を解剖して、冷却した0.1Mの過塩素酸中にいれた。3−ニトロチロシンおよびチロシンの濃度を、電気化学検出を用いたHPLCによって測定を行なった(Matthewsによる、1998年)。統計学上の比較を、独立スチューデントt−検定または一元分散分析を行い、続いて事後比較のために、フィッシャープロテクト(protected)最小有意差検定によって行なった。
本発明において、加齢または侵襲に関連する皮膚の損傷の予防または治療のために、クレアチン化合物を個体(例えば、哺乳動物)に単独でまたは別の化合物と組合せて投与することができる。皮膚保存のための薬物として、クレアチン化合物は、クレアチンキナーゼ/ホスホクレアチン機能、エネルギー状態、酸化的損傷および/または細胞の生存を改変し、その結果、加齢、UV放射への曝露、ストレス、疲労または他の侵襲における皮膚損傷への直接的および/または間接的な影響を防止、寛解、抑止または排除することができる。クレアチン化合物と一緒に投与することができる他の化合物としては、例えば抗酸化剤、ビタミン、エネルギー増強剤およびスキンケアのために用いられる他の薬物を含む。
本明細書に記載の本発明のある実施態様についての多数の均等物は、1つ以上の通常の実験操作を用いて、当該分野の当業者によって認識されるかまたは確認され得るであろう。該均等物は特許請求の範囲に包含されることを意図する。
Claims (12)
- 治療学的に有効な量のクレアチンアスコルベート、および医薬的に許容し得る担体を含有する、被験者における日光の放射、ストレス、疲労、もしくは遊離ラジカルから生じる皮膚の損傷の処置のための、局所投与用の医薬組成物。
- 該皮膚の損傷が遊離ラジカルに関連している、請求項1記載の医薬組成物。
- 該皮膚の損傷が日光の放射に関連している、請求項1記載の医薬組成物。
- 該皮膚の損傷がストレスまたは疲労に関連している、請求項1記載の医薬組成物。
- 該被験者が皮膚のしわに悩んでいる、請求項1記載の医薬組成物。
- 該被験者が皮膚の損傷の危険な状態である、請求項1記載の医薬組成物。
- 該皮膚の損傷を処置することにより、少なくとも1つの予め存在する皮膚の損傷の症状を軽減させるかまたは排除する、請求項1記載の医薬組成物。
- 該症状が皮膚のしわまたは皮膚の弾性の低下である、請求項1記載の医薬組成物。
- 該皮膚の損傷の処置に皮膚の損傷の予防が含まれる、請求項1記載の医薬組成物。
- 治療学的に有効な量のクレアチンアスコルベート、および医薬的に許容し得る担体を含有する、被験者における加齢に関連している少なくとも1つの症状を軽減させるかまたは排除するための、局所投与用の医薬組成物。
- 該症状が皮膚のしわである、請求項10記載の医薬組成物。
- 該症状が皮膚の弾性の低下である、請求項10記載の医薬組成物。
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JP2003503348A (ja) | 2003-01-28 |
EP1198230A1 (en) | 2002-04-24 |
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HK1047885A1 (zh) | 2003-03-14 |
CA2376943A1 (en) | 2001-01-04 |
EP2397127A1 (en) | 2011-12-21 |
US20050186195A1 (en) | 2005-08-25 |
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JP2014240406A (ja) | 2014-12-25 |
WO2001000203A1 (en) | 2001-01-04 |
US20100329997A1 (en) | 2010-12-30 |
US20050227996A1 (en) | 2005-10-13 |
US20020049253A1 (en) | 2002-04-25 |
US20070253944A1 (en) | 2007-11-01 |
US20110085993A1 (en) | 2011-04-14 |
US20110008272A1 (en) | 2011-01-13 |
US20120141391A1 (en) | 2012-06-07 |
US20050186194A1 (en) | 2005-08-25 |
US7186754B2 (en) | 2007-03-06 |
US20100226870A1 (en) | 2010-09-09 |
EP1198230A4 (en) | 2004-06-16 |
AU783758B2 (en) | 2005-12-01 |
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