JP2009011847A - 大環状トリエン化合物を含むポリマー組成物 - Google Patents
大環状トリエン化合物を含むポリマー組成物 Download PDFInfo
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Abstract
【解決手段】ポリマー組成物は、大環状トリエン化合物の40−O−ヒドロキシアルキルラパマイシン誘導体を含むポリマー基材からなり、アルキル基は、7〜11の炭素原子を含む。この組成物は、ラパマイシンまたはエベロリウムスに応答する任意の状態を処置するのに有用であり、そしてポリマー組成物を使用する処置方法が、記載される。組成物は、標的部位での固形腫瘍、炎症または創傷の処置における使用のためであり、そして標的部位への注入によって局在され得る注入可能な粒子の懸濁液から構成される。
【選択図】なし
Description
本発明は、40−O−ヒドロキシアルキル置換ラパマイシン誘導体を含むポリマー基材から構成されるポリマー組成物に関し、ここでアルキルは7〜11個の炭素原子を有する。
ラパマイシンは、イースター島の土壌サンプルから単離されたStreptomyces属の菌種株(Streptomyces hygroscopicus)から初めに抽出された大環状トリエン化合物である(Vezinaら、J.Antibiot.28:721(1975);米国特許第3,929,992号;同第3,993,749号)。ラパマイシンは、以下の式I:
に示される構造を有する。本来、抗真菌剤(米国特許第3,929,992号)としての使用を記載され、次いで、癌および腫瘍の処置における使用(米国特許第4,885,171号)、実験的な免疫病理学の予防のための使用(実験的なアレルギー性脳炎およびアジュバント関節炎;Martel,R.,Can.J.Physio.,55:48(1977)、移植の拒絶反応の阻害(米国特許第5,100,899号)および平滑筋細胞増殖の阻害(Morris,R.,J.Heart Lung Transplant,11(pt.2)(1992))を含む他の状態および障害の効果的な薬剤であることが見出されている。
1つの局面において、本発明は、被験体の内部標的部位に対する大環状トリエン化合物の送達における使用のためのポリマー組成物を含む。組成物は、(i)20〜70重量%のポリマー基材および(ii)30〜80%重量%の以下:
の構造を有する大環状トリエン化合物を含み、
ここで、RはCH2−X−OHであり、ここでXは、6〜10個の炭素原子を含む直鎖または分枝鎖アルキルである。標的部位で細胞に対して配置される場合、組成物は、ラパマイシンまたはエベロリムス大環状トリエン化合物を含む同じポリマー基材によって達成されるよりも実質的に多くの、標的部位細胞中の化合物の取り込みのレベルを達成するのに効果的である。
(I.定義)
本明細書中で使用される場合、「ラパマイシン」とは、以下:
本発明は、40−O−ヒドロキシアルキル(C7−C11)置換ラパマイシン化合物を含むポリマー組成物に関する。上記のように、ラパマイシンおよびその誘導体の多くは、低いバイオアベイラビリティを有し、薬剤としてのその有用性が制限される。本発明において、ラパマイシンの特定の40−O−ヒドロキシアルキル誘導体は、ポリa−構造に処方される場合、処置のために組織と接触された場合に、改善されたバイオアベイラビリティを提供することが見出されている。ポリマー組成物で使用するためのラパマイシン化合物は、40−O位が以下のように修飾された化合物である:
ここで、Rは、CH2−X−OHであり、Xは、6〜10個の炭素原子を含む直鎖または分枝鎖のアルキル基である。一実施形態において、Xは、6〜10個の炭素原子を有する直鎖または分枝鎖のアルキルであるか、または別の実施形態において、7〜11個の炭素原子を有する直鎖または分枝鎖のアルキルである。好ましい実施形態において、Xは、6個の炭素原子を有する直鎖アルキルである。RがCH2−X−OHであり、Xが6、7、8、9または10炭素のアルキルである化合物は、本明細書中で、それぞれ、40−O−ヒドロキシヘプチル、40−O−ヒドロキシオクチル、40−O−ヒドロキシノニル、40−O−ヒドロキシデシルおよび40−O−ヒドロキシウンデシルと呼ばれる。
このy遮断値はlogであり、従って、40−O−ヒドロキシヘプチルラパマイシンは、40−O−ヒドロキシエチルラパマイシン(エベロシムス)の約7倍疎水性であり、この40−O−ヒドロキシエチルラパマイシンは、ラパマイシンより約1倍以上疎水性である。このデータに基づいて、これらの化合物の相対水溶性は、以下の順序である:
デキサメタゾン>>パクリタキセル>>>ラパマイシン>エベロリムス>>>>>40−O−ヒドロキシヘプチルラパマイシン。
例示的なポリマー組成物は、注射によって、またはカテーテルのようなデバイスを使用する堆積によってインビボで配置されるのに適したポリマー粒子の処方物である。このポリマー粒子は、ミクロ細孔性、マクロ細孔性または非細孔性であり得、そして難水溶性の40−O−ヒドロキシラパマイシン化合物を保持し得るポリマーから形成され得る。
別の実施形態において、ポリマー組成物は、粘膜組織に隣接した配置のために、粘膜接着特性を有するポリマー基材からなる。身体内の粘膜組織としては、眼の袋小路、頬空洞、鼻、直腸、膣、歯周ポケット、腸および結腸が挙げられる。粘膜接着送達システムは、粘膜接着性ポリマー内に含まれる化合物の投与のために、粘膜組織への接着を示す。
本発明において使用するための別の例示的なポリマー組成物は、拡張可能な脈管ステント上に担持されるポリマーコーティングである。図2および3は、40−O−置換されたラパマイシン化合物を担持するポリマー組成物でコーティングされた、脈管内ステントの概略図である。これらの図において、ステント20が、そのステントの収縮状態(図2)および拡張状態(図3)において示される。このステントは、図3および4を参照して以下にさらに記載されるように、構造部材または本体22、および化合物を保持および放出するための外側コーティングを備える。
別の一般的な実施形態において、ステント本体およびポリマーコーティングの両方が、生物侵食性ポリマーで形成され、経時的にステントが完全に再吸収されることを可能にする。ステントは、好ましくは、ステント本体を形成しているらせん状のリボンフィラメントを有する拡張可能なコイル型ステントである(示さず)。自己拡張可能なコイルステントは、血管中への移植についての米国特許第4,990,155号に記載されており、本明細書に参考として援用される。
ここで図面をより詳細に参照して、図5Aおよび5Bは、本発明に従うステントコーティングプロセスの概略図である。ポリマー溶液40を、ポリマーを親和的溶媒に溶解させることで作製する。40−O−置換ラパマイシン化合物および、所望の場合には第2の薬剤を、同じ溶媒または異なる溶媒を使用する懸濁液または溶液のいずれかとして、この溶液に加える。この完成した混合物を、耐圧性リザーバ42に入れる。リザーバを流体加圧ポンプ44に接続する。
40−O−ヒドロキシアルキル置換ラパマイシン化合物は、ラパマイシンまたはエベロリムスに対する任意の状態応答の処置における使用を意図される。これは、創傷治癒(例えば、血管移植手順または臓器移植手順を含む術後の手順)、腫瘍性疾患に関連する任意の状態を含み、ここで、例えば、ポリマー組成物は、癌(例えば、固形腫瘍)の部位に直接配置される。炎症および感染もまた、40−O−ヒドロキシアルキル置換ラパマイシン誘導体によって処置可能な状態である。この化合物はまた、血管処置方法、特に再狭窄に対して使用され得る。化合物は、被験体における内部標的部位への適用のためにポリマー基材へ処方され、例示的なポリマー基材処方物は、上述の通りである。拡張可能なステント上に適用されたポリマーコーティングのポリマー組成物は、再狭窄の処置に特に適している。
(エベロリムスおよびその誘導体の調製)
(工程A.2−(t−ブチルジメチルシリル)オキシエタノール(TBSグリコール)の合成)
154mlの乾燥THFおよび1.88gのNaHを、窒素雰囲気下で、500mLの丸底フラスコ冷却器中で攪拌する。4.4mLの乾燥エチレングリコールをこのフラスコに添加し、45分間の攪拌後に、大きい沈殿物を生じる。11.8gのtert−ブチルジメチルシリルクロリドをこのフラスコに添加し、そして激しい攪拌を45分間続ける。得られた混合物を950mLのエチルエーテルに注ぐ。このエーテルを420mLのブラインで洗浄し、そして溶液を硫酸ナトリウムで乾燥する。この生成物を、減圧下でのエーテルのエバポレーションによって濃縮し、そしてシリカゲルを充填された27×5.75cmのカラムを使用する、ヘキサン/Et2O(75:25 v/v)溶媒系を使用するフラッシュクロマトグラフィーによって精製する。その生成物を、0℃で保存する。
4.22gのTBSグリコールおよび5.2gの2,6−ルチジンを、冷却器を備えた100mLの二つ口フラスコ中で、窒素下で激しく攪拌しながら合わせる。10.74gのトリフルオロメタンスルホン酸無水物を、このフラスコに、35〜45分間かけてゆっくりと添加し、黄色がかった褐色溶液を得る。次いで、この反応を、1mLのブラインを添加することによってクエンチし、そしてこの溶液を、100mLのブライン中で5回洗浄して、最終pH値を6〜7にする。この溶液を硫酸ナトリウムを使用して乾燥し、そして減圧下での塩化メチレンのエバポレーションによって濃縮する。その生成物を、シリカゲルを充填した約24×3cmのフラッシュクロマトグラフィーカラムを使用して、ヘキサン/Et2O(85:15 v/v)溶媒系を使用して精製し、次いで、0℃で保存する。
400mgのラパマイシン、10mLのトルエン、および1.9mLの2,6−ルチジンを、55〜57℃に維持した50mLのフラスコ中で混合し、そして撹拌する。別の3mLのセプタムバイアル中で、940μLの2,6−ルチジンを1mLのトルエンに添加し、次いで、2.47gのTBSグリコールTrifを添加する。このバイアルの内容物を50mLフラスコに添加し、そして撹拌しながら、反応を1.5時間進行させる。480μLの2,6−ルチジンおよびさらなる1.236gのTBSグリコールTrifを、この反応フラスコに添加する。撹拌を、さらに1時間続ける。最後に、第二の部分の480μLの2,6−ルチジンおよび1.236gのTBSグリコールTrifをこの混合物に添加し、そしてこの混合物を、さらに1〜1.5時間攪拌する。得られる褐色の溶液を、多孔質ガラスフィルタを通して、減圧を使用して注ぐ。結晶様の沈澱物を、全ての色が除かれるまでトルエンで洗浄する。次いで、その濾液を、60mLの飽和NaHCO3溶液で2回洗浄し、次いで、ブラインで再度洗浄する。得られた溶液を硫酸ナトリウムで乾燥し、そして減圧下で濃縮する。少量のヘキサン/EtOAc(40:60v/v)溶媒を使用して生成物を溶解し、そしてシリカゲルを充填した33×2cmのフラッシュクロマトグラフィーカラムを使用し、そして同じ溶媒で展開して、精製を達成する。この溶媒を減圧下で除去し、そして生成物を5℃で保存する。
パイレックス(登録商標)ガラス皿(150×75mm)を、氷で満たし、そして撹拌プレート上に置く。少量の水を加えて、氷のスラリーを得る。第1に、60〜65mgのTBS−Rapを、8mLのメタノールを加えることによりガラスバイアル中で溶解する。0.8mL 1N HClを、バイアルに加え、この溶液を45分間撹拌し、次いで、3mL飽和NaHCO3水溶液を加えることにより中和する。5mLのブライン、続いて20mLのEtOAcを溶液に加え、その結果、二相が形成される。これらの相の混合後、分液ロートを使用して水層を除く。残る溶媒をブラインで洗って6〜7の最終pHにし、硫酸ナトリウムで乾燥する。硫酸ナトリウムを多孔性ガラスフィルターを使用して除き、そして溶媒を真空中で除去する。生じる濃縮物を、EtOAc/メタノール(97:3)中に溶解し、次いで、シリカゲルで充填された23×2cmフラッシュクロマトグラフィーカラムを使用し、同じ溶媒系を使用して展開して精製する。この溶媒を真空中で除去し、そして生成物を5℃で保存する。
(ポリ−dl−ラクチドコーティングにおけるエベロリムスを含むステントの調製)
100mgのポリ(dl−ラクチド)を、室温にて2mLアセトン中に溶解した。5mgのエベロリムスをバイアル中に置き、400μLのラクチド溶液を加えた。マイクロプロセッサ制御シリンジポンプを使用して、ステントストラット頂部表面にラクチド溶液を含む10μLの薬物を正確に分配した。溶媒の蒸発が、ステント上の単一ポリマー層を含む均一な薬物を生じた。
(ポリ−dl−ラクチドコーティングにおけるエベロリムスを含むステントからのインビトロでの薬物放出)
25%EtOHを含む2mLのpH7.4リン酸緩衝化生理食塩水溶液中にコーティングされたステントを配置し、0.05%(w/v)アジドナトリウムとともに保存し、37℃に保つことによりインビトロ薬物放出を、行なった。全緩衝液体積を薬物測定のために回収しながら、溶液を同じ体積の新鮮な緩衝液(無限の沈降)で置換することによりサンプリングを、定期的に行なった。図8は、この様式で微小分配される単一のポリマー層でコーティングされる2つの類似のステントからの薬物放出を例示する。
(動物移植試験)
(A.ブタにおける安全および用量設定試験のQCA結果)
薬物溶出ステントのための問題のある処置条件は、ひどく損傷した血管であるが、それは、再狭窄(新脈管内膜形成)の程度が脈管損傷の程度と共に直接増加するためである。実験がブタにおいて行われ、薬物でコーティングされたステント移植物の標的であった脈管のかなりの数が、血管形成術バルーンを使用して重篤に損傷された(平均およそ36%過度に伸ばした脈管の損傷)。これは、脈管の内膜および中間層の重篤な引き裂きおよび伸びを引き起こし、移植後28日で極端な再狭窄を生じた。このように、薬物の種々の用量の相対有効性および移植後28日での再狭窄の減少についての同じ金属ステント/ポリマープラットフォームにおけるポリマーに対する薬物重量比を評価することが可能であった。
「剥き出しのステント」とは、波形の環設計の18.7mmの剥き出しの金属ステントをいう(すなわち、Biosensors Intl.,Inc.により製造されるような、現在市販される「S−ステント」)。
波形環設計の金属ワイヤメッシュ骨格を使用する薬物溶出ステント(すなわち、S−ステント)およびポリマーコーティングを、異なる用量の薬物エベロリムスまたは薬物シロリムスのいずれかを使用して、外で育った未成育のブタ(あるいは28日より長く続く移植研究についてはユカタンミニブタ(Yucatan Minipig))に移植した。移植の際に、Quantitative Coronary Angiography(QCA)を実施して、ステント移植の前および後の脈管の直径を測定した。28日目、または以下の表に具体的に示される場合にはそれより長期間にて、動物をステントの領域においてQCAを再び受けさせ、その後安楽死させる。
PCベースのシステムのためのA.G.Heinzeスライド顕微鏡を介してコンピューター化された画像化システムImage Pro Plus 4.0を、以下の組織形態計測測定のために使用した:
1.平均断面積および管腔厚(脈管内膜/新脈管内膜−管腔境界により制限される領域);新脈管内膜(管腔と内弾性板(IEL)との間の領域、IELが欠けている場合、管腔と中間弾性板または外弾性板(EEL)の残りとの間の領域);中間(IELとEELとの間の領域);管サイズ(外膜領域を除くEELにより制限される領域);および外膜領域(周辺外膜組織、脂肪組織および心筋層ならびにEELの間の領域)。
2.損傷スコア。脈管損傷の程度を定量化するために、異なる壁構造の裂け目の量および長さに基づくスコアが、使用された。損傷の程度は、以下のように計算された:
0=インタクトなIEL
1=表面媒体層に曝される裂かれたIEL(少ない損傷)
2=より深い媒体層に曝される裂かれたIEL(媒体切開)
3=外膜領域に曝された裂かれたEEL
以下の表は、追跡管理QCAでのQCA分析(再狭窄に起因する平均管腔喪失の測定)の結果を示す。以下の表の「新脈管内膜領域」と題される欄の下のデータは、追跡管理(f/u)でのブタから除かれたステントおよび管の形態計測分析の結果を報告する:
(表1:「高度損傷」実験の結果)
(B.低損傷研究)
どれほどのエベロリムスの用量が軽く損傷した脈管(合併症でない冠動脈疾患および1つの新しい損傷を有する患者に、より特有である)において最良であるかをさらに決定するために、エベロリムス溶出ステントを、中程度から低い過度伸長損傷(およそ15%)を作製するために移植した。農場のブタを30日の実験のために使用し、そして成体のユカタンミニブタを三ヶ月の安全研究のために移植した。血管造影法の結果は、以下の通りであった:
(表2:「低い損傷」実験のQCA結果)
ステント内に形成された、各々のステント内の全切断面領域および新しい組織(新脈管内膜)の切断面領域が、コンピューターにより測定され、狭窄領域の割合が、計算された。薬物およびポリマーの各々の形成に対する、平均的管損傷スコア、新脈管内膜領域、およびステントあたり3つのスライスを平均した狭窄領域の割合を、以下の表に示す。
形態計測分析は、ブタ冠動脈モデルにおけるステント内狭窄を測定する高度に正確な方法と考えられる。高度損傷モデルにおいて、C−High調合は、28日での「高度損傷」実験における新脈管内膜形成の最も低い量を作製した;しかし、C−Uhighは、群の最も高度な損傷スコアを有し、0.45の非常に低い狭窄領域の割合をなお管理した。従って、データは、QCA分析の発見を独立して確かめ、そしてヒト臨床試験のための好ましいい調合としてC−Uhighの選択を支持する。
(D.組織学的分析)
C−Uhighおよびsirolimus−lowについてのスライドを、経験を積んだ心臓病理学者に提出した。彼は、炎症、フィブリンおよび新しく治療した血管管腔の内皮化を示す証拠について管断面を再調査した。シロリムス溶出ステントとエベロリムス溶出ステントとにより引き起こされた組織学的変化の間の違いは、見出せなかった。一般に、良く定着した内皮層を有する管は、良く治療されており、完治の証拠であり、28日での管恒常性であると見られる。図14は、移植後28日での管腔内部の内皮層の治療および定着を示す倍率91倍の管断面図の例である。
Carterらは、ブタにおいてPalmaz Schatz金属ステントを使用してシロリムスでコーティングしたステントの結果を発表した。発表されたCarterの結果の本明細書中のポリマーでコーティングしたステントを使用する実験結果に対して比較する表を、下に示す:
(表4)
(実施例5)
(高度な薬物装填を有するステントの調製)
長さ14.6mmの市販の金属波形環ステント(S−ステント、波形環設計:Biosensors Intl)を、血漿堆積プロセスを使用してパリレン「C」プライマーコーティングのおよそ2ミクロンの厚さの層でコーティングした。パリレンでコーティングしたステントを周囲温度で終夜キシレン中においた。50μg/μlのポリ乳酸(PDLA)を含むPDLA溶液を、2mLアセトン中100mgのPDLAに溶解することにより調製した。
Claims (17)
- 血管損傷部位で再狭窄を阻害するために、該部位での配置のための脈管内ステントであって、該脈管内ステントは、以下:
半径方向に拡張可能な、接続されたフィラメントの格子から形成される管状部材であって、各フィラメントは、外側の支持体表面、側面の支持体表面および内側の支持体表面を有する、管状部材、および
再狭窄阻害薬物を含む薬物放出層であって、該層は、該フィラメントの外面がコーティングされているが、内面はコーティングされていない、薬物放出層
を含む、脈管内ステント。 - 前記層が、前記フィラメントの外面および側面をコーティングする、請求項1に記載のステント。
- 前記フィラメントと前記薬物放出層との間に堆積される下層をさらに含む、請求項1に記載のステント。
- 前記層が、(i)20〜60重量%のポリdl−ラクチドポリマー基材および(ii)40〜80重量%の抗再狭窄化合物から構成され、そして前記下層がポリマー下層である、請求項3に記載のステント。
- 前記層に含まれる前記再狭窄阻害薬物が、大環状トリエン免疫抑制化合物である、請求項1に記載のステント。
- R’がHであり、そしてXが−CH2である、請求項6に記載のステント。
- 前記ステント本体の内面が、第2の薬物を含む第2の薬物放出層でコーティングされている、請求項1に記載のステント。
- 前記フィラメントの外面上の前記層の深さが、不均一である、請求項1に記載のステント。
- 血管損傷部位で再狭窄を阻害する際に使用するための薬物溶出ステントを形成する方法であって、該方法は、以下:
半径方向に拡張可能な、接続されたフィラメントの格子から形成される管状部材を支持する工程であって、各フィラメントは、外側の支持体表面、側面の支持体表面および内側の支持体表面を有する、工程、および
該フィラメントの内面ではなく外面に硬化するのに有効な流体組成物を堆積し、該フィラメント上に堆積した後、再狭窄阻害薬物を含む薬物放出層を形成する工程、
を包含する、方法。 - 前記堆積する工程は、前記フィラメントの外面および側面の両方に前記組成物を堆積する工程を包含する、請求項10に記載の方法。
- 前記堆積する工程は、前記ステント本体が送達管に対して動く間、直接的に送達管から前記フィラメントの外面に減圧下で、前記流体組成物を排出する工程を包含する、請求項10に記載の方法。
- 前記管が、移動可能なアーム上に保存され、そしてアームの移動がコンピューターの制御下にある、請求項12に記載の方法。
- 請求項10に記載の方法であって、前記流体組成物が、適切な溶媒中に非溶媒成分として、以下:(i)20〜60重量%のポリ−dl−ラクチドポリマー基材および(ii)40〜80重量%の抗再狭窄化合物を含む溶液である、方法。
- 前記流体組成物が適用される前記ステント本体フィラメントの外面が、ポリマー下層でコーティングされる、請求項10に記載の方法。
- 前記ステント本体フィラメントの内面に第2の薬物を含む第2の層を適用する工程をさらに包含する、請求項10に記載の方法。
- 前記堆積する工程が行われ、その結果前記ステントフィラメントの外面に不均一なコーティングを生成する、請求項10に記載の方法。
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