JP2007515199A - 親水性添加剤を含むステント用コーティング - Google Patents
親水性添加剤を含むステント用コーティング Download PDFInfo
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Abstract
Description
δ=(ΔE/V)1/2
(式中、δは溶解性パラメータ(cal/cm3)1/2であり、ΔEは蒸発のエネルギー(cal/mole)であり、Vは、モル体積(cm3/mole)である。
〈実施例1〉
第1のポリマー溶液を調製した。溶液は、
(a)約154,000のMnを有する5質量%のポリ(n−ブチルメタクリレート)(PBMA)及び
(b)残部、約4:1のアセトンとシクロヘキサノンの質量比を有する混合物である、アセトンとシクロヘキサノンの溶媒混合物を含有する。
(a)約18,000のMnを有する約5質量%のポリ(エチレングリコール)(PEG)及び
(b)残部、約4:1のアセトンとシクロヘキサノンの質量比を有する混合物である、アセトンとシクロヘキサノンの溶媒混合物を含有する。
PBMA/PEGの溶液におけるPBMAとPEGの間の質量比を約19:1にした以外、実施例1に記載したように、PBMA/PEGの溶液を調製した。実施例1に記載したように、PBMA/PEGの溶液からスライドグラス上にポリマーの膜を形成した。実施例1に記載したように、乾燥したPBMA/PEG膜の光学顕微鏡写真を撮った。図2によって顕微鏡写真を示す。図2に見られるように、PBMA/PEG系はほとんど均一に見え、PEGにより形成された結晶性の若干の相が顕微鏡写真上の明るい点によって表された。
PBMA/PEGの溶液におけるPBMAとPEGの間の質量比を約10:1にした以外、実施例1に記載したように、PBMA/PEGの溶液を調製した。実施例1に記載したように、PBMA/PEGの溶液からスライドグラス上にポリマーの膜を形成した。実施例1に記載したように、乾燥したPBMA/PEG膜の光学顕微鏡写真を撮った。図3によって顕微鏡写真を示す。図3に見られるように、PBMA/PEG系は、目に見える結晶性領域を含む。実施例2で記載された膜に比べて、図3で示される膜は、PEGによって形成されたさらに実質的な量の結晶性の相を含んでいた。
以下の成分を混合することにより第1の組成物を調製した:
(a)約1.0質量%〜約15質量%の間、たとえば、2.0質量%のポリ(エチレン−co−ビニルアルコール)(EVAL)及び
(b)残部、DMAC溶媒。
(a)約2.0質量%のEVAL、
(b)約1.6質量%のエベロリムス、及び
(c)残部、DMAC溶媒。
(a)約154,000のMnの約2質量%のPBMA、
(b)約18,000のMnの約0.1質量%のPEG、及び
(c)残部、溶媒、アセトンとシクロヘキサノンの質量比1:1の混合物。
実施例4に記載したように、下塗り層及び薬剤/ポリマー層をステント上に形成することができるが、エベロリムスの代わりにラパマイシンを使用することができる。次いで、以下の成分を混合することにより上塗り組成物を調製することができる:
(a)約154,000のMnの約2質量%のPBMA、
(b)約18,000のMnの約0.05質量%のPEG、及び
(c)約40,000のMnを有する約0.05質量%のポリ(プロピレングリコール)(PPG)、及び
(d)残部、溶媒、アセトンとシクロヘキサノンの質量比1:1の混合物。
実施例4に記載したように、下塗り層及び薬剤/ポリマー層をステント上に形成することができる。次いで、以下の成分を混合することにより上塗り組成物を調製することができる:
(a)約1.0質量%〜約15質量%の間、たとえば、1.9質量%の、約125,000のMnを有するポリ(ヘキサフルオロプロペン−co−フッ化ビニリデン)(PHFP−VDF)、
(b)約0.04質量%〜約0.8質量%の間、たとえば、0.1質量%のF127プルロニックコポリマー、及び
(c)残部、溶媒混合物、約1:1の質量比でアセトンとシクロヘキサノンを含む溶媒混合物。
Claims (45)
- コーティングを含む埋め込み型医療用具であって、前記コーティングが少なくとも1種のポリ(メタ)アクリレート及び少なくとも1種のポリアルキレングリコールの混合物を含み、前記ポリ(メタ)アクリレート及び前記ポリアルキレングリコールの高分子鎖が物理的に絡み合った、又は相互貫入した系を形成する、用具。
- 前記用具がステントである、請求項1の用具。
- 前記ポリ(メタ)アクリレートと前記ポリアルキレングリコールとの間の比が約99:1〜約9:1の間である、請求項1の用具。
- 前記ポリ(メタ)アクリレートが、ポリ(メチルメタクリレート)、ポリ(エチルメタクリレート)、ポリ(n−プロピルメタクリレート)、ポリ(イソ−プロピルメタクリレート)、ポリ(n−ブチルメタクリレート)、ポリ(イソ−ブチルメタクリレート)、ポリ(tert−ブチルメタクリレート)、ポリ(メチルアクリレート)、ポリ(エチルアクリレート)、ポリ(n−プロピルアクリレート)、ポリ(イソ−プロピルアクリレート)、ポリ(n−ブチルアクリレート)、ポリ(イソ−ブチルアクリレート)、及びこれらの混合物から成る群から選択される、請求項1の用具。
- 前記ポリアルキレングリコールが、ポリ(エチレングリコール)、ポリ(エチレンオキシド)、ポリ(プロピレングリコール)、ポリ(エチレンオキシド−co−ポリプロピレンオキシド)、ポリ(トリメチレングリコール)、ポリ(テトラメチレングリコール)及びこれらの混合物から成る群から選択される、請求項1の用具。
- 前記コーティングがさらに薬剤を含む、請求項1の用具。
- 前記薬剤が、ラパマイシン、40−O−(2−ヒドロキシ)エチル−ラパマイシン、40−O−(3−ヒドロキシ)プロピル−ラパマイシン、40−O−[2−(2−ヒドロキシ)エトキシ]エチル−ラパマイシン、40−O−テトラゾール−ラパマイシン及びこれらの組み合わせから成る群から選択される、請求項6の用具。
- コーティングを含む埋め込み型医療用具であって、前記コーティングが少なくとも1種の疎水性ポリマー及び少なくとも1種の高分子親水性化合物の混合物を含み、前記疎水性ポリマー及び前記親水性化合物の高分子鎖が物理的に絡み合った、又は相互貫入した系を形成する用具。
- 用具がステントである、請求項8の用具。
- 前記疎水性ポリマーが約10.7(cal/cm3)1/2未満のヒルデブランドの溶解性パラメータを有する、請求項8の用具。
- 前記疎水性ポリマーが室温にて約10質量%未満の水の平衡吸着量を有する、請求項8の用具。
- 前記疎水性ポリマーが、ポリ(メタ)アクリレート、ビニルポリマー、ポリオレフィン、ハロゲン化ポリマー、ウレタン基を有するポリマー、ポリブチラール、ナイロン、シリコーン、ポリカーボネート又はポリスルホンを含む、請求項8の用具。
- 前記ポリ(メタ)アクリレートが、ポリ(メチルメタクリレート)、ポリ(エチルメタクリレート)、ポリ(n−プロピルメタクリレート)、ポリ(イソ−プロピルメタクリレート)、ポリ(n−ブチルメタクリレート)、ポリ(イソ−ブチルメタクリレート)、ポリ(tert−ブチルメタクリレート)、ポリ(メチルアクリレート)、ポリ(エチルアクリレート)、ポリ(n−プロピルアクリレート)、ポリ(イソ−プロピルアクリレート)、ポリ(n−ブチルアクリレート)、ポリ(イソ−ブチルアクリレート)、及びこれらの混合物から成る群から選択される、請求項12の用具。
- 前記ビニルポリマーが、ポリ(エチレン−co−ビニルアルコール)、ポリ(エチレン−co−ビニルアセテート)、ポリ(ビニルアセテート)、ポリスチレン、ポリ(スチレン−co−イソ−ブチレン)、ポリ(スチレン−co−エチレン−co−ブチレン−co−スチレン)ターポリマー及びポリ(スチレン−co−ブタジエン−co−スチレン)ターポリマー及びこれらの混合物から成る群から選択される、請求項12の用具。
- 前記ポリオレフィンがアタクチックポリプロピレンである、請求項12の用具。
- ハロゲン化ポリマーが、ポリ(フッ化ビニル)、ポリ(フッ化ビニリデン)、ポリヘキサフルオロプロペン、ポリ(ヘキサフルオロプロペン−co−フッ化ビニリデン)、ポリ(エチレン−co−ヘキサフルオロプロペン)、ポリテトラフルオロエチレン、ポリ(塩化ビニル)及びポリ(塩化ビニリデン)及びこれらの混合物から成る群から選択される、請求項12の用具。
- 前記ウレタン基を有するポリマーが、ポリエーテルウレタン、ポリエステルウレタン、ポリウレタンウレア、ポリカーボネートウレタン、シリコーンウレタン及びこれらの混合物から成る群から選択される、請求項12の用具。
- 前記高分子親水性化合物が、ポリアルキレングリコール、ヒアルロン酸、コンドロイチン硫酸、キトサン、グルコサミノグルカン、デキストラン、デキストリン、デキストラン硫酸、セルロースアセテート、カルボキシメチルセルロース、ヒドロキシエチルセルロース、セルロース誘導体、ポリペプチド、ポリ(2−ヒドロキシエチルメタクリレート)、ポリアクリルアミド、ポリアクリルイミド、ポリ(エチレンアミン)、ポリ(アリルアミン)、ポリ(ビニルピロリドン)、ポリ(ビニルアルコール)、ポリ(アクリル酸)、ポリ(メタクリル酸)、アクリル酸コポリマー、メタクリル酸コポリマー、ビニルアルキルエーテル、非イオン性四官能性ブロックコポリマー界面活性剤、ゼラチン、コラーゲン、アルブミン、キチン、ヘパリン、エラスチン、フィブリン及びこれらの混合物から成る群から選択される、請求項8の用具。
- 前記ポリアルキレングリコールが、ポリ(エチレングリコール)、ポリ(エチレンオキシド)、ポリ(プロピレングリコール)、ポリ(エチレンオキシド−co−ポリプロピレンオキシド)、ポリ(トリメチレングリコール)、ポリ(テトラメチレングリコール)及びこれらの混合物から成る群から選択される、請求項18の用具。
- 前記疎水性ポリマーと前記高分子親水性添加剤との間の比が約99:1〜約9:1の間である、請求項8の用具。
- 前記コーティングがさらに薬剤を含む、請求項8の用具。
- 前記薬剤が、ラパマイシン、40−O−(2−ヒドロキシ)エチル−ラパマイシン、40−O−(3−ヒドロキシ)プロピル−ラパマイシン、40−O−[2−(2−ヒドロキシ)エトキシ]エチル−ラパマイシン、40−O−テトラゾール−ラパマイシン及びこれらの組み合わせから成る群から選択される、請求項21の用具。
- 埋め込み型基材及びコーティングを含む医療品であって、前記コーティングが、
(a)バルクポリマー、
(b)コーティングにおいて前記バルクポリマーより量が少なく、前記バルクポリマーと絡まり合う又は相互貫入する添加ポリマー、及び
(c)薬剤を含み、
前記添加ポリマーが前記コーティングからの薬剤の放出速度を変化させる医療品。 - バルクポリマーに対する添加ポリマーの比を高めることによって薬剤の放出速度を高める、請求項23の医療品。
- 前記バルクポリマーが前記添加ポリマーよりも疎水性である、請求項23の医療品。
- 前記バルクポリマーがポリ(メタ)アクリレートを含む、請求項23の医療品。
- 前記ポリ(メタ)アクリレートが、ポリ(メチルメタクリレート)、ポリ(エチルメタクリレート)、ポリ(n−プロピルメタクリレート)、ポリ(イソ−プロピルメタクリレート)、ポリ(n−ブチルメタクリレート)、ポリ(イソ−ブチルメタクリレート)、ポリ(tert−ブチルメタクリレート)、ポリ(メチルアクリレート)、ポリ(エチルアクリレート)、ポリ(n−プロピルアクリレート)、ポリ(イソ−プロピルアクリレート)、ポリ(n−ブチルアクリレート)、ポリ(イソ−ブチルアクリレート)、及びこれらの混合物から成る群から選択される、請求項23の医療品。
- 前記添加ポリマーがポリアルキレングリコールを含む、請求項23の医療品。
- 前記ポリアルキレングリコールが、ポリ(エチレングリコール)、ポリ(エチレンオキシド)、ポリ(プロピレングリコール)、ポリ(エチレンオキシド−co−ポリプロピレンオキシド)、ポリ(トリメチレングリコール)、ポリ(テトラメチレングリコール)及びこれらの混合物から成る群から選択される、請求項28の医療品。
- 前記添加ポリマーの全長が、前記バルクポリマーの全長の約10%〜約100%の間である、請求項23の医療品。
- 埋め込み型医療用具用のコーティングを作製する方法であって、前記用具上にコーティングを形成することを含み、前記コーティングは、少なくとも1種の疎水性ポリマー及び少なくとも1種の高分子親水性化合物の混合物を含み、疎水性ポリマー及び親水性化合物の高分子鎖が、物理的に絡み合った又は相互貫入した系を形成する、方法。
- 前記用具がステントである、請求項31の方法。
- 前記疎水性ポリマーが約10.7(cal/cm3)1/2未満のヒルデブランドの溶解性パラメータを有する、請求項31の方法。
- 前記疎水性ポリマーが室温にて約10質量%未満の水の平衡吸着量を有する、請求項31の方法。
- 前記疎水性ポリマーが、ポリ(メタ)アクリレート、ビニルポリマー、ポリオレフィン、ハロゲン化ポリマー、ウレタン基を有するポリマー、ポリブチラール、ナイロン、シリコーン、ポリカーボネート又はポリスルホンを含む、請求項31の方法。
- 前記ポリ(メタ)アクリレートが、ポリ(メチルメタクリレート)、ポリ(エチルメタクリレート)、ポリ(n−プロピルメタクリレート)、ポリ(イソ−プロピルメタクリレート)、ポリ(n−ブチルメタクリレート)、ポリ(イソ−ブチルメタクリレート)、ポリ(tert−ブチルメタクリレート)、ポリ(メチルアクリレート)、ポリ(エチルアクリレート)、ポリ(n−プロピルアクリレート)、ポリ(イソ−プロピルアクリレート)、ポリ(n−ブチルアクリレート)、ポリ(イソ−ブチルアクリレート)、及びこれらの混合物から成る群から選択される、請求項35の方法。
- 前記ビニルポリマーが、ポリ(エチレン−co−ビニルアルコール)、ポリ(ビニルアセテート)、ポリスチレン、ポリ(スチレン−co−イソブチレン)、ポリ(スチレン−co−エチレン−co−ブチレン−co−スチレン)ターポリマー及びポリ(スチレン−co−ブタジエン−co−スチレン)ターポリマー及びこれらの混合物から成る群から選択される、請求項35の方法。
- 前記ポリオレフィンがアタクチックポリプロピレンである、請求項35の方法。
- 前記ハロゲン化ポリマーが、ポリ(フッ化ビニル)、ポリ(フッ化ビニリデン)、ポリヘキサフルオロプロペン、ポリ(ヘキサフルオロプロペン−co−フッ化ビニリデン)、ポリ(エチレン−co−ヘキサフルオロプロペン)、ポリテトラフルオロエチレン、ポリ(塩化ビニル)及びポリ(塩化ビニリデン)及びこれらの混合物から成る群から選択される、請求項35の方法。
- 前記ウレタン基を有するポリマーが、ポリエーテルウレタン、ポリエステルウレタン、ポリウレタンウレア、ポリカーボネートウレタン、シリコーンウレタン及びこれらの混合物から成る群から選択される、請求項35の方法。
- 前記高分子親水性化合物が、ポリアルキレングリコール、ヒアルロン酸、コンドロイチン硫酸、キトサン、グルコサミノグルカン、デキストラン、デキストリン、デキストラン硫酸、セルロースアセテート、カルボキシメチルセルロース、ヒドロキシエチルセルロース、セルロース誘導体、ポリペプチド、ポリ(2−ヒドロキシエチルメタクリレート)、ポリアクリルアミド、ポリアクリルイミド、ポリ(エチレンアミン)、ポリ(アリルアミン)、ポリ(ビニルピロリドン)、ポリ(ビニルアルコール)、ポリ(アクリル酸)、ポリ(メタクリル酸)、アクリル酸コポリマー、メタクリル酸コポリマー、ビニルアルキルエーテル、非イオン性四官能性ブロックコポリマー界面活性剤、ゼラチン、コラーゲン、アルブミン、キチン、ヘパリン、エラスチン、フィブリン及びこれらの混合物から成る群から選択される、請求項31の方法。
- 前記ポリアルキレングリコールが、ポリ(エチレングリコール)、ポリ(エチレンオキシド)、ポリ(プロピレングリコール)、ポリ(エチレンオキシド−co−ポリプロピレンオキシド)、ポリ(トリメチレングリコール)、ポリ(テトラメチレングリコール)及びこれらの混合物から成る群から選択される、請求項41の方法。
- 前記疎水性ポリマーと前記高分子親水性添加剤との間の比が約99:1〜約9:1の間である、請求項31の方法。
- 前記コーティングがさらに薬剤を含む、請求項31の方法。
- 前記薬剤が、ラパマイシン、40−O−(2−ヒドロキシ)エチル−ラパマイシン、40−O−(3−ヒドロキシ)プロピル−ラパマイシン、40−O−[2−(2−ヒドロキシ)エトキシ]エチル−ラパマイシン、40−O−テトラゾール−ラパマイシン及びこれらの組み合わせから成る群から選択される、請求項44の方法。
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US10/431,711 US7279174B2 (en) | 2003-05-08 | 2003-05-08 | Stent coatings comprising hydrophilic additives |
US10/431,711 | 2003-05-08 | ||
PCT/US2004/009011 WO2004101018A1 (en) | 2003-05-08 | 2004-03-23 | Stent coatings comprising hydrophilic additives |
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WO2004101018A8 (en) | 2005-12-29 |
US20040224001A1 (en) | 2004-11-11 |
US8673334B2 (en) | 2014-03-18 |
EP1626753B1 (en) | 2014-10-15 |
ES2526806T3 (es) | 2015-01-15 |
EP1626753A1 (en) | 2006-02-22 |
JP5117724B2 (ja) | 2013-01-16 |
US7279174B2 (en) | 2007-10-09 |
US9175162B2 (en) | 2015-11-03 |
US20080118543A1 (en) | 2008-05-22 |
WO2004101018A1 (en) | 2004-11-25 |
US20080021008A1 (en) | 2008-01-24 |
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