JP6383732B2 - ビニルピロリドンポリマーおよび酸性ポリマーを含んでいる層を備えた、粒子が少ない潤滑性コーティング - Google Patents
ビニルピロリドンポリマーおよび酸性ポリマーを含んでいる層を備えた、粒子が少ない潤滑性コーティング Download PDFInfo
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- Y10T428/31573—Next to addition polymer of ethylenically unsaturated monomer
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Description
当該非仮出願は、出願人を同じくする仮出願である出願番号61/748,859(出願日:2013年1月4日、発明の名称:LUBRICIOUS COATINGS WITH LOW PARTICULATES)、および出願番号61/783,179(出願日:2013年3月14日、発明の名称:LUBRICIOUS COATING WITH LOW PARTICULATES)の利益を主張するものであり、これらの仮出願は、その全体が参照によって本明細書に引用される。また、2014年1月6日に作成された「SRM0161WO_Sequence_Listing_ST25.txt」というタイトルの、9キロバイトのサイズを有するASCIIテキストファイルの全体の内容は、参照によって本明細書に引用される。
本開示は、潤滑性コーティングに関する。より具体的には、本開示は、粒子の発生が少ない潤滑性の医療デバイスコーティング、並びにこれに関連する医療デバイスおよび方法に関する。
医療デバイスは、特に、慢性的に移植されているデバイス、一時的に移植されているデバイス、および、全く移植されていないデバイスを含む。多くのタイプの医療デバイスは、特にデバイスを挿入する間に、当該デバイスと、当該医療デバイスの周囲の環境との摩擦を減少させることにより、改善される。1つの例として、少なくとも一時的に、被験体の体内へ挿入されるカテーテルが挙げられる。摩擦の減少は、他にも利益をもたらすが、患者の痛みの緩和、介護者の処理の軽減、感染の機会の減少とともに、組織の破壊の減少をもたらし得る。医療デバイスと、当該医療デバイスの周囲の環境との摩擦を減少させるための1つのアプローチは、当該医療デバイスに潤滑性コーティングを塗布することである。
本開示の実施形態は、潤滑性コーティングを含む。一般的に、当該コーティングは、ビニルピロリドンポリマーおよび光反応性基を含んでいる第1のコート層と、酸性基含有ポリマーを含んでいる最上層コートである第2のコート層とを備えており、上記第1のコート層は、上記第2のコート層と基材の表面との間に存在する。
(b):
(c):
および(d):
本開示は、以下の図面とともに、より完全に理解され得る:
図1は、2つの成分のコーティングの一実施形態を示す概略図である。
上述したように、医療デバイスと、当該医療デバイスの周囲の環境との間の摩擦を低減するための1つのアプローチは、上記医療デバイスの上へ潤滑性コーティングを形成することである。しかしながら、潤滑性コーティングの多くは、上記デバイスと、上記デバイスの周囲の環境(一例として、血管内の空間)との間の摩擦を低減する効果が比較的低い。さらに、潤滑性コーティングの多くは十分な耐久性を有しておらず、使用中の摩擦の急速な増加をもたらす。最後に、潤滑性コーティングの多くは、水性の環境(患者の体内等)に曝された後に、好ましくない粒子状物質を放出する。
式(b):
式(c):
および式(d):
以下の試薬、コーティング溶液および基材が、実施例の生成において使用された。
N−アセチル化ポリ[アクリルアミド93.6%−co−ナトリウム−2−アクリルアミド−2−メチルプロパンスルホネート4.9%−co−N−(3−(4−ベンゾイルベンズアミド)プロピル)メタクリルアミド0.9%]−co−メトキシポリ(エチレングリコール)1000モノメタクリレート0.6%(パーセンテージはモル%である)を得た(PA−BBA−AMPS−PEG)。PA−BBA−AMPS−PEGの調製のための試薬および方法は、米国特許第4,979,959号;第5,002,582号;第5,263,992号;第5,414,075号;第5,512,329号;および第5,637,460号等の参考文献中に見出され得る。これらの教示は、参照によって本明細書に引用される。
平均分子量が約1,450kDaであり、ベンゾフェノン光反応性基を有するポリビニルピロリドンを、米国特許第5,637,460号に記載の方法に従って調製した。
架橋剤であるナトリウムビス(4−ベンゾイルフェニル)ホスフェートを、米国特許出願公開第2012/0046384号に記載の方法に従って調製した。
450kDaの平均分子量を有するポリ(アクリル酸)を、Sigma-Aldrichから得た。
50kDaの平均分子量を有するPVP−K30を、BASFから得た。
75%がイソプロピルアルコールであり、25%が水である溶媒において、18g/Lのフォト−PVP;および1g/LのBPPを共に混合することによって、コーティング溶液を調製した。
15%がイソプロピルアルコールであり、85%が水である溶媒において、10.5g/Lのフォト−PVP;10.5g/LのPA−BBA−AMPS−PEG;0.1g/LのBPPを共に混合することによって、コーティング溶液を調製した。
15%がイソプロピルアルコールであり、85%が水である溶媒において、10.5g/LのPAA;10.5g/LのPA−BBA−AMPS−PEG;0.1g/LのBPPを共に混合することによって、コーティング溶液を調製した。
15%がイソプロピルアルコールであり、85%が水である溶媒において、20g/LのPAAを溶解することによって、コーティング溶液を調製した。
15%がイソプロピルアルコールであり、85%が水である溶媒において、20g/LのPVP−K30を溶解することによって、コーティング溶液を調製した。
試験基材は、Minnesota MedTec, Maple Grove, MNから得た30%硫酸バリウムおよび40D PEBAX(登録商標)編組カテーテル材料(0.105''のO.D.、40PPI);Medicine Lake Extrusion, Plymouth, MNから得たPEBAX(登録商標)ロッド(O.D. 0.039'';72D);並びにSolomon Scientific, San Antonio, TXから得たポリウレタンカテーテル(O.D. 0.92'';カタログ番号PU−C70)を含む。
国際出願番号WO03/055611に記載の垂直ピンチ法を以下のように修正して用いた摩擦測定によって、実施例のコーティングされた基材の潤滑性/耐久性を評価した。コーティングされた基材のサンプルを、リン酸緩衝生理食塩水(PBS、pH7.4)中で1分間以上、水和させ、その後、ロッドホルダーの端部へ挿入した。当該ロッドホルダーをピンチテスターの2つの顎の間に配置して、そしてPBSのシリンダーへ浸漬した。上記ピンチテスターの顎を閉じてサンプルを移動速度1cm/sにて垂直方向へ10cm引っ張り、そしてコーティングされたサンプルが元の位置Aに戻った時点で顎を開いた。
本明細書の実施例における水溶液中に生成された粒子の試験は、次の手順によって実施された。ASTM F2394に記載の手順の派生として、基材を、以下に記載の水溶液中にて蛇行した経路を通過させた。
フォト−PVP溶液(20g/L、水)をPAA溶液へ加えた(40g/L、水)。溶液を混合したときに、調製物はゲルを形成した。このことから、これらのフォト−PVP溶液とPAA溶液との間に相互作用が存在することが実証された。
コーティングを、PEBAX(登録商標)編組カテーテル材料(40D、40PPI、30%BaSO4)に塗布した。具体的には、コーティング溶液Aを、ディップコート法を用いて基部コートとして基材へ塗布した。当該基材を5秒間の滞留時間にてコーティング溶液A中に浸漬した。その後、当該基材を、1.5cm/sの速度にて、溶液から抜き出した。その後、当該基部層を少なくとも10分間空気乾燥させた。さらに、コーティングされた基材を、400ワットメタルハライド電球を備えたDymax 2000−ECシリーズのUVフラッドランプの前で30秒間、光源から約20cmの位置で回転させることにより、上記基部層をUV硬化させた。1つのケースにおいて、上記基部コート層の塗布を、合計3コート分、反復した。次に、同様に0.3cm/sの速度のディップコーティングによって、コーティング溶液Bまたはコーティング溶液Cの層を基部コート層へ塗布して第2層を形成した。その後、上記基部コート層と同じ条件を用いて、上記第2層を空気乾燥させ、そしてUV硬化させた。その後、上で概説した試験手順に従い、コーティングの摩擦を調べた。結果を図3に示す。
コーティングを、PEBAX編組カテーテル材料(40D、40PPI、30%BaSO4)に塗布した。具体的には、コーティング溶液Aを、ディップコート法を用いて基部コートとして基材へ塗布した。当該基材を5秒間の滞留時間にて基部コートコーティング溶液中に浸漬した。その後、当該基材を、1.5cm/sの速度にて、溶液から抜き出した。その後、当該基部層を少なくとも10分間空気乾燥させた。さらに、上記基部層をUV硬化させた。具体的には、コーティングされた基材を、400ワットメタルハライド電球を備えたDymax 2000−ECシリーズのUVフラッドランプの前で30秒間、光源から約20cmの位置で回転させた。次に、同様に0.3cm/sの速度のディップコーティングによって、コーティング溶液Dまたはコーティング溶液Eの層を基部コート層へ塗布して第2層を形成した。その後、上記基部コート層と同じ条件を用いて、上記第2層を空気乾燥させ、そしてUV硬化させた。その後、上で概説した試験手順に従い、コーティングの摩擦を調べた。結果を図4に示す。
コーティングを、PEBAX(登録商標)編組カテーテル材料(40D、40PPI、30%BaSO4)に塗布した。具体的には、コーティング溶液Aを、ディップコート法を用いて基部コートとして基材へ塗布した。当該基材を5秒間の滞留時間にて基部コートコーティング溶液中に浸漬した。その後、当該基材を、1.5cm/sの速度にて、溶液から抜き出した。その後、当該基部層を少なくとも10分間空気乾燥させた。さらに、上記基部層をUV硬化させた。具体的には、コーティングされた基材を、400ワットメタルハライド電球を備えたDymax 2000−ECシリーズのUVフラッドランプの前で30秒間、光源から約20cmの位置で回転させた。次に、同様に0.3cm/sの速度のディップコーティングによって、コーティング溶液Dの層を基部コート層へ塗布して第2層を形成した。その後、全てのロッドにおいて上記第2層を空気乾燥させた。あるセットのロッドには、30秒間のUV硬化を施し、一方、他のセットのロッドにはUV硬化を施さなかった。その後、上で概説した試験手順に従い、コーティングの摩擦を調べた。結果を図5に示す。
厚さ0.5mmのPEBAX 6333 SA01シートを、Specialty Extrusions, Inc (Royersford, PA)から得た。アミノ酸配列がCKKRGDSP、GWQPPRARI、GYIGSR、GIKVAV、およびGSVVYGLRであるペプチドを、BioBasic, Inc. (Amherst, NY)にて95%の純度で合成した。コーティングの前に、PEBAXシートを1×8cmのストリップへと切断した。PEBAXストリップをコーティング溶液A中に浸し、その後、1.5cm/sの速度にて除去した。上記ストリップを10分間乾燥させ、その後、30秒間UVに曝露した。その後、ストリップをコーティング溶液D中に浸し、0.3cm/sの速度にて除去し、10分間乾燥させ、30秒間UVに曝露した。2−(N−モルホリノ)エタンスルホン酸(Sigma-Aldrich, Saint Loiuis, MO)を水中に0.1M(1L中に19.5g)にて溶解させ、pHを6.0に調整してMESバッファーを調製した。1−エチル−3−[3−ジメチルアミノプロピル]カルボジイミド(EDC)塩酸塩およびN−ヒドロキシスクシニミド(NHS)を両方ともThermo Scientific (Rockford, IL)から得た。EDCおよびNHSをMESバッファー中に各成分が1mg/mlの濃度となるように溶解させた。その後、EDCおよびNHSを含んでいるMESバッファーまたはMESバッファーのみを用いて、ペプチドをMESバッファー中に1mg/mlにて溶解させた。EDC/NHSあり、またはなしの、ペプチドを含んだMESバッファーを、PAAがコーティングされたPEBAXストリップとともに、一晩、室温にて振盪しながらインキュベートした。一晩の振盪後、PEBAXストリップを、0.05%Tween−20を含んでいるリン酸緩衝生理食塩水中で3回すすぎ、その後、水中ですすいだ。その後、上記ストリップを乾燥させた。細胞接着試験の前に、ストリップを30秒間UV光に曝露することによって滅菌した。
ヒト冠状動脈内皮細胞(HCAECs)および内皮細胞増殖培地2微小血管(EGM−2MV)をLonza (Walkersville, MD)から得た。HCAECsを組織培養ポリスチレンフラスコ中にてコンフルエンシー(confluency)まで増殖させ、トリプシン処理によって収集した後、EGM−2MVを用いてトリプシンを中和した。コーティングされたPEBAX上に播く前に、細胞を、血球計を用いて数えた。PEBAXストリップ(1×1cm)を24ウェル細胞培養プレート中に配置し、その後、100,000個のHCAECsを含んでいる1mlのEGM−2MVを上記プレートへ加え、2時間インキュベートした。24ウェル細胞培養プレートの1ウェルあたり100,000個から1,563個までの範囲のHCAECsの標準曲線もまた、連続希釈法によって調製した。2時間のインキュベーションの後、PEBAXストリップをダルベッコリン酸緩衝生理食塩水(DPBS, Lonza)中で3回すすぎ、その後、1mlの新鮮なEGM−2MVを含んでいる新しい24ウェルプレートへ、移した。その後、0.2mLのCellTiter−Blue(登録商標)(Promega, Madison, WI)を、PEBAXおよび細胞標準を含んだプレートに加え、1.5時間インキュベートし、その後、収集して、蛍光プレートリーダーにて560nmの励起光および590nmの蛍光を用いて読み取った。その後、PEBAXをDPBS中にてすすぎ、さらに4日間、EGM−2MVを含んでいる新しい培養プレートへ配置し、この時点で、接着した細胞の数を、再度CellTiter−Blue(登録商標)を用いて定量した。初期の接着および4日目の定量の結果を図13Aおよび13Bに示す。コーティングされていないPEBAX、またはコーティング溶液Aのみを受けたPEBAX(BCのみ)もしくはコーティング溶液AおよびDのみを受けたPEBAX(BC PAAのみ)では、HCAECsは接着を示さなかった。全てのペプチドコーティングは細胞接着を増加させ、また、接着は、ペプチドコーティング溶液にEDC/NHSが含まれている場合(EDCあり)に、より増加した。
ポリ(アクリル酸)(PAA)最上層コーティングおよび比較コーティングを有するコーティングを、血液適合性について調べた。編組ニチノール塞栓防止デバイスを、IPA中で洗浄し、その後、熱い10%Valtron SP2200(Valtech, Corp., Pottstown, PA)の溶液によって洗浄した。メチルヒドロシロキサン−ジメチルシロキサンコポリマー(Gelest, Morrisville, PA)のつなぎ層を、ディッピングによってデバイス上に配置し、その後、120℃にて35分間乾燥させ、IPA中ですすいだ。フォト−PVPおよびBBPの基部コートを、それぞれ10mg/mlおよび0.2mg/mlにて、75%IPA/25%水中で調製し、EFDスプレイヤー(Nordson EFD, Westlake, OH)を用いたスプレーコーティングによって塗布した。スプレーコーティング後、部品を1分間UVに曝露した。その後、部品をPAAコーティング溶液D中に浸し、乾燥させ、そして1分間UVに曝露した。
Claims (16)
- ビニルピロリドンポリマーおよび光反応性基を含んでいる第1のコート層であって、上記光反応性基は、上記ビニルピロリドンポリマーからのペンダント基であるか、もしくは少なくとも2つの光反応性基を有する第1の架橋剤上に存在しているか、またはその両方である、第1のコート層と、
アクリル酸ポリマーを含んでいる最上層のコーティングである第2のコート層であって、上記第2のコート層は、上記第1のコート層と直接的に接しており、上記第1のコート層は、上記第2のコート層と基材の表面との間に存在する、第2のコート層と、を備えている潤滑性コーティング。 - 上記第2のコート層は、少なくとも1つの光反応性基を含んでいるアクリルアミドポリマーをさらに含んでいる、請求項1に記載のコーティング。
- 上記アクリルアミドポリマーは、アクリルアミド含有サブユニット、2−アクリルアミド−2−メチルプロパンスルホネート(AMPS)含有サブユニットおよびポリ(エチレングリコール)含有サブユニットを含んでいる、請求項2に記載のコーティング。
- 上記ビニルピロリドンポリマーおよび上記アクリルアミドポリマーは、それぞれ約3:1〜1:3(重量/重量)の範囲の重量比にて、上記コーティング中に存在している、請求項2に記載のコーティング。
- 第1の架橋剤を含んでおり、上記ビニルピロリドンポリマーおよび上記第1の架橋剤は、約8:1〜約20:1(重量/重量)の範囲の重量比にて、上記コーティング中に存在している、請求項1に記載のコーティング。
- 第1の架橋剤または第2の架橋剤を含んでおり、上記第1の架橋剤および上記第2の架橋剤の少なくとも一方は、式「フォト1−LG−フォト2」で表される化合物であり、上記フォト1および上記フォト2は、独立して少なくとも1つの光反応性基を表し、LGは、少なくとも1つのケイ素原子または少なくとも1つのリン原子を含んでいる連結基を表し、上記少なくとも1つの光反応性基と上記連結基との間には共有結合が存在し、上記少なくとも1つの光反応性基と上記連結基との間の共有結合には、少なくとも1つのヘテロ原子が介在しており、
上記第1の架橋剤および上記第2の架橋剤の少なくとも一方は、
(ここで、R1、R2、R8およびR9は、任意の置換基であり;R3、R4、R6およびR7は、アルキル基、アリール基、またはそれらの組み合わせであり;R5は、任意の置換基であり;かつ、Xは、それぞれ独立してO、N、Se、S、もしくはアルキル基、またはそれらの組み合わせである);
(ここで、R1およびR5は、任意の置換基であり;R2およびR4は、OHを除く任意の置換基であってもよく;R3は、アルキル基、アリール基、またはそれらの組み合わせであってもよく;かつ、Xは、それぞれ独立してO、N、Se、S、アルキル基またはそれらの組み合わせである);
(ここで、R1、R2、R4およびR5は、任意の置換基であり;R3は、任意の置換基であり;R6およびR7は、アルキル基、アリール基、またはそれらの組み合わせであり;かつ、Xは、それぞれ独立してO、N、Se、S、アルキル基、またはそれらの組み合わせである);および、
から選択される式で表される化合物である、請求項1に記載のコーティング。 - 上記第1の架橋剤および上記第2の架橋剤の少なくとも一方は、ナトリウムビス(4−ベンゾフェニル)ホスフェートである、請求項6に記載のコーティング。
- 上記アクリル酸ポリマーは、150kDa以上の平均分子量を有する、請求項1に記載のコーティング。
- 上記コーティングは、10ミクロンを超える3,000個未満の粒子を放出する、請求項1に記載のコーティング。
- 上記第1のコート層および上記第2のコート層を合わせた厚さは、乾燥状態において約100〜1000nmである、請求項1に記載のコーティング。
- (a)上記コーティングは、少なくとも10回の連続した試験サイクルの間、湿潤状態において0〜30グラムの力の潤滑性を示すか、もしくは(b)上記コーティングは、試験の1〜5回目のサイクルの平均と試験の10〜15回目のサイクルの平均との間で測定された摩擦において30パーセント未満の増加がある潤滑性の耐久性を示すか、または(a)および(b)の両方である、請求項1に記載のコーティング。
- 上記第1のコート層のみを有する対照コーティングと比較して、(a)上記コーティングは、血小板の集積の減少を示すか、(b)上記コーティングは、フィブリンの集積の減少を示すか、または(a)および(b)の両方である、請求項1に記載のコーティング。
- 請求項1に記載のコーティングを備えた、医療デバイス。
- 上記基材は、ポリアミド、ポリイミド、ポリエーテルブロックアミド(PEBAX)、ポリエーテルエーテルケトン(PEEK)、高密度ポリエチレン(HDPE)、ポリエチレン、ポリウレタン、またはポリエチレンビニルアセテートを含んでいる、請求項13に記載の医療デバイス。
- 上記医療デバイスは、カテーテルを備えている、請求項14に記載の医療デバイス。
- 医療デバイス上にコーティングを形成する方法であって、以下の工程を含む方法:
医療デバイスの表面上に直接的または間接的に第1のコーティング溶液を塗布し、そして第1のコーティング溶液を乾燥させる工程であって、上記第1のコーティング溶液は、ビニルピロリドンポリマーおよび光反応性基、並びに第1の溶媒、を含んでおり、上記光反応性基は、上記ビニルピロリドンポリマーからのペンダント基であるか、もしくは少なくとも2つの光反応性基を有する第1の架橋剤上に存在している、工程;
上記第1のコーティング溶液を化学線に曝露して第1の層を形成する工程;
上記第1の層上に第2のコーティング溶液を塗布し、そして第2のコーティング溶液を乾燥させる工程であって、上記第2のコーティング溶液は、アクリル酸ポリマーおよび第2の溶媒、並びに任意に、少なくとも2つの光反応性基を含んでいる第2の架橋剤を含んでいる、工程;および、
上記第2のコーティング溶液を化学線に曝露して第2の層を形成する工程。
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