JP5933434B2 - 薬剤送達バルーンの製造方法 - Google Patents
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- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/14—Materials characterised by their function or physical properties, e.g. lubricating compositions
- A61L29/16—Biologically active materials, e.g. therapeutic substances
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- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/04—Macromolecular materials
- A61L29/06—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/416—Anti-neoplastic or anti-proliferative or anti-restenosis or anti-angiogenic agents, e.g. paclitaxel, sirolimus
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
- A61L2300/606—Coatings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
- A61L2300/62—Encapsulated active agents, e.g. emulsified droplets
- A61L2300/622—Microcapsules
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
- A61L2300/63—Crystals
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Description
a)非晶形にある薬剤のコーティングを適用する適用工程と、
b)コーティングされたバルーンをアニーリングして、バルーン上においてインサイチューで前記薬剤の結晶形を生成する工程と
を有する。
バルーン材料の成分の核形成剤としてのブルーミングを誘発するためにバルーンの蒸気前処理を伴う特定の実施形態を含む、バルーンに核を形成する様々な技術が記載される。
米国特許第5102402号明細書、ドロール(Dror)ら(メドトロニック インコーポレイテッド(Medtronic,Inc.));
米国特許第5370614号明細書、アマンドソン(Amundson)ら(メドトロニック インコーポレイテッド);
米国特許第5954706号明細書、サハトジアン(Sahatjian)(ボストン サイエンティフィック コーポレイション(Boston Scientific Corp));
国際公開第WO00/32267号公報、シメッド ライフ システムズ(SciMed Life Systems)、セントエリザベス メディカルセンター(St Elizabeth’s Medical Center)(パラシス(Palasis)ら);
国際公開第WO00/45744号公報、シメッド ライフ システムズ(ヤン(Yang)ら);
アール.チャールズら、「Ceramide−Coated Balloon Catheters Limit Neointimal Hyperplasia After Stretch Injury in Cartoid Arteries」、Circ.Res.2000、第87巻、第282〜288頁;
米国特許第6306166号明細書、バリー(Barry)ら、(シメッド ライフ システムズ インコーポレイテッド);
米国特許出願第2004/0073284号明細書、ベイツ(Bates)ら(クック インコーポレイテッド(Cook,Inc)、MED インスト インコーポレイテッド(MED Inst,Inc.));
米国特許出願第2006/0020243号明細書、スペック(Speck);
国際公開第WO2008/003298号公報、ヘモテック アーゲー(Hemoteq AG)(ホフマン(Hoffman)ら);
国際公開第WO2008/086794号公報、ヘモテック アーゲー(Hemoteq AG)(ホフマン(Hoffman)ら);
米国特許出願第2008/0118544号明細書、ワン(Wang);
米国特許出願第20080255509号明細書、ワン(Wang)(ルトニックス(Lutonix));
米国特許出願第20080255510号明細書、ワン(Wang)(ルトニックス(Lutonix))。
本発明の実施形態によれば、前記薬剤は、所定比率の前記形態型(morphological forms)を生じるように制御された方法で装置上に提供される。
(a)扇状結晶形態
95/5(wt/wt)のTHF/IPA中におけるパクリタキセル/PVP(55K MW)(95/5 wt/wt)の20%溶液を調製する。カンタム マーヴェリック(Quantum Maverick)バルーン(直径3.0mm×長さ16mm、Pebax(登録商標)7233)を、膨張した状態で、前記パクリタキセル溶液中に浸漬し、取り出し、室温かつ真空下において乾燥させることによって被覆して、約450μgのドライコート重量を得る。この時点におけるコーティングは非晶質ガラスである。バルーンカテーテルを9リットルのガラスチャンバ内に配置する。前記チャンバは、16gの190プルーフのエタノールで充填される。前記チャンバの底部におけるエタノールの表面積は176cm2である。前記カテーテルをエタノールの上方に吊り下げる(液体エタノールと接触させない)。次に、前記チャンバを密閉し、室温で4〜16時間にわたって蒸気アニール工程を進行させて、パクリタキセルの結晶化を引き起こす。前記薬剤の結晶形はパクリタキセル二水和物である。
(b)小さな棒状結晶形態
未被覆のカンタム マーヴェリック バルーン(直径3.0mm×長さ16mm)を、飽和エタノール蒸気を含む密封されたチャンバ内に一晩配置する。次にバルーンを(a)で上述したように浸漬被覆する。この時点におけるコーティングは非晶質ガラスである。被覆したバルーンカテーテルを、(a)で上述したようにエタノール中で蒸気アニーリングする。
図5cは、折り畳み状態からの膨張後における、実施例1bの方法で製造されたバルーンの表面を示している。折り畳み状態からの膨張後における表面上の均一な結晶構造に注目されたい。
この例は、管内留置卓上試験を用いて、インビトロの性能に対するパクリタキセル結晶の大きさの影響を示す。バルーンは、下記手順を用いて、折り畳まれ、親水性ポリウレタン内に留置される。管を37℃の水中に配置する。折り畳んだバルーンを前記管内に配置し、1分間浸漬した後に膨張させる。前記管はバルーンの留置中に20%の過剰拡張を生ずるような大きさに形成されている。膨張を1分間維持し、15秒間にわたって真空に引いて、バルーンを管から取り出す。前記管を水から取り出し、乾燥させ、撮像する。前記管上に留置された薬剤の画像を図7aおよび図7bに示す。
下記方法を用いて、薬剤被覆バルーンカテーテルについて微粒子試験を行なった。バルーンカテーテル(各型についてN=3)を、湾曲ガラス動脈モデルを介して親水性ポリウレタン管(人工動脈)内へ追従させた(tracked)。前記動脈モデルは、試験中に水流(流量:70mL/分)が維持される閉ループシステムの一部である。前記流動ループはレーザー粒子計数器に接続される。バルーンをポリウレタン動脈まで追従させる間に粒子数を得る。留置の前に2分間にわたって粒子数を得る。バルーンを12気圧で30秒間にわたって留置する。次に、留置後の2分間にわたって粒子数を得る。10〜25μm、25〜50μmおよび50〜125μm粒子サイズビンに対する合計粒子数を測定する。3つの型を試験した。「Ptx扇(Ptx Fan)」は、コーティングの後適用蒸気アニーリングによって非晶質パクリタキセルコーティングから調製された、Pebax(登録商標)7233バルーン上において扇状形態を有するパクリタキセルコーティング(賦形剤なし)であった。「Ptx棒(Ptx Rod)」は、バルーンの蒸気前処理、非晶質パクリタキセルコーティングの適用、および次いでコーティングを結晶化させるための後処理によって調製されたPebax(登録商標)7233バルーン上において棒状形態を有するパクリタキセル(賦形剤なし)であった。「シークエント プリーズ(Sequent Please)」は、パクリタキセル/イオプラミド(iopramide)コーティングを有するビー.ブラウン(B.Braun)によって販売されている従来技術の薬剤送達バルーンカテーテルであった。すべてのバルーンは約3μg/mm2のパクリタキセル薬剤含量を有した。図8a〜図8cは粒子数の結果を示している。2つのパクリタキセル粒子形態のうち、棒状形態は追従/留置の間に、より少数の粒子を生じる。双方のパクリタキセル形態(棒および扇)は、市販の比較対照よりも大幅に少ない粒子数を与える。前記結果は、蒸気アニールによる非結晶コーティングの結晶化によって結晶性コーティングを形成することにより、改善されたコーティング特性をもたらすことを示していると考えられる。
薬剤被覆バルーンカテーテルを、媒体(80%のデュベッコの改変イーグル培地(Dubecco’s Modified Eagle media);20%ウシ胎児血清)中、37℃、40mL/分の流動条件下で、体外培養されたブタ動脈内に留置した(1分間の膨張)。留置後、0時間、1時間後および4時間後、動脈をLC−MSによって全薬剤含量について分析した。以下のコーティング製剤:パクリタキセル結晶体(扇状);パクリタキセル結晶体(棒状);パクリタキセル/クエン酸アセチルトリブチル混合物(85/15 wt/wt)−(扇状);およびパクリタキセル/クエン酸アセチルトリブチル混合物(85/15 wt/wt)(棒状)をPebax(登録商標)7233バルーン上で試験した。薬剤含量はすべての製剤について約3μg/mm2であった。薬剤組織の結果を図9に示す。
Claims (12)
- 薬剤を含有するコーティングを上部に有する薬剤送達バルーンを製造する方法であって、前記バルーンはバルーン材料から形成され、同バルーン材料はポリエーテル−ブロック−アミドコポリマーを含み、前記薬剤はパクリタキセルを含み、かつ同薬剤は特有な非晶形および結晶形を有し、前記方法は、
a)非晶形にある薬剤のコーティングを前記バルーン材料に適用する適用工程と、
b)前記コーティングを適用した後に、工程a)にて適用されたコーティングを溶媒蒸気であってC1アルコール〜C4アルコールから選択されるアルコールを含む溶媒蒸気を用いてアニーリングして、前記バルーン上に前記薬剤の結晶形を生成するアニーリング工程と、を含み、
前記適用工程a)において、前記薬剤のコーティングは、前記アニーリング工程において薬剤結晶の形成を誘発するための核形成部位を有するバルーン表面に施され、前記核形成部位は前記バルーン材料中の成分の結晶化であるブルーミングによって前記バルーン材料の表面に形成されたものである、方法。 - 前記ブルーミングは、薬剤コーティングを適用する前のバルーン表面の前処理によって促進され、前記前処理はC1アルコール〜C4アルコールから選択されるアルコールを用いたバルーンの溶媒蒸気アニーリングを含む、請求項1に記載の方法。
- 前記薬剤は賦形剤を有する製剤として前記バルーンに適用される、請求項1または2に記載の方法。
- 前記賦形剤は、水可溶性ポリマー、糖、造影剤、クエン酸エステル、短鎖モノカルボン酸のグリセロールエステルおよび医薬として許容される塩から成る群のうちの1つである、請求項3に記載の方法。
- 前記アニーリング工程において、前記バルーンはアニーリングチャンバ内に配置され、前記アニーリングチャンバにおいて、前記溶媒蒸気は、前記バルーンが該チャンバに入れられる時点で、前記チャンバの温度および圧力において飽和状態に満たない蒸気圧にある、請求項1に記載の方法。
- 前記チャンバは周囲圧力および周囲温度で維持される、請求項5に記載の方法。
- 前記バルーンは、5分〜24時間の範囲にある時間にわたって前記溶媒蒸気によってアニーリングされる、請求項5に記載の方法。
- 前記アニーリング工程において、前記溶媒蒸気は、35〜75mL/cm2の範囲にあるチャンバ容積対溶媒表面積の比を有するアニーリングチャンバ内に提供される、請求項1に記載の方法。
- 前記バルーン表面は、バルーンの表面上の微粒子核形成剤によって核を形成され、前記微粒子核形成剤は10nm〜20μmの寸法範囲にある主要寸法を有する、請求項1に記載の方法。
- 前記微粒子核形成剤は、10粒子/mm2〜5000粒子/mm2のバルーン上における密度を有する、請求項9に記載の方法。
- 前記微粒子核形成剤は、100粒子/mm2〜2000粒子/mm2のバルーン上における密度を有する、請求項9に記載の方法。
- 前記薬剤は、賦形剤を有さない製剤として前記バルーンに適用される、請求項1または2に記載の方法。
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US27116709P | 2009-07-17 | 2009-07-17 | |
US61/271,167 | 2009-07-17 | ||
PCT/US2010/038532 WO2011008393A2 (en) | 2009-07-17 | 2010-06-14 | Nucleation of drug delivery balloons to provide improved crystal size and density |
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JP2012533338A JP2012533338A (ja) | 2012-12-27 |
JP2012533338A5 JP2012533338A5 (ja) | 2013-08-01 |
JP5933434B2 true JP5933434B2 (ja) | 2016-06-08 |
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US (1) | US10080821B2 (ja) |
EP (2) | EP2962707B1 (ja) |
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- 2010-06-14 EP EP15180475.4A patent/EP2962707B1/en active Active
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EP2962707A1 (en) | 2016-01-06 |
WO2011008393A2 (en) | 2011-01-20 |
US10080821B2 (en) | 2018-09-25 |
WO2011008393A3 (en) | 2011-03-24 |
JP2012533338A (ja) | 2012-12-27 |
EP2962707B1 (en) | 2019-07-24 |
US20110015664A1 (en) | 2011-01-20 |
EP2453938A2 (en) | 2012-05-23 |
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