WO2022210759A1 - 抗血栓性材料 - Google Patents
抗血栓性材料 Download PDFInfo
- Publication number
- WO2022210759A1 WO2022210759A1 PCT/JP2022/015625 JP2022015625W WO2022210759A1 WO 2022210759 A1 WO2022210759 A1 WO 2022210759A1 JP 2022015625 W JP2022015625 W JP 2022015625W WO 2022210759 A1 WO2022210759 A1 WO 2022210759A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- meth
- acrylate
- copolymer
- silicone
- acrylate copolymer
- Prior art date
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- 239000000463 material Substances 0.000 title claims abstract description 53
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 85
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
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- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-O vancomycin(1+) Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C([O-])=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)[NH2+]C)[C@H]1C[C@](C)([NH3+])[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-O 0.000 description 1
- 238000000214 vapour pressure osmometry Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
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- 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
- A61L33/00—Antithrombogenic treatment of surgical articles, e.g. sutures, catheters, prostheses, or of articles for the manipulation or conditioning of blood; Materials for such treatment
- A61L33/06—Use of macromolecular materials
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- A61L33/00—Antithrombogenic treatment of surgical articles, e.g. sutures, catheters, prostheses, or of articles for the manipulation or conditioning of blood; Materials for such treatment
- A61L33/06—Use of macromolecular materials
- A61L33/068—Use of 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
- A61L2300/42—Anti-thrombotic agents, anticoagulants, anti-platelet agents
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Abstract
Description
(2) (1)に記載の抗血栓性材料を含む医療機器。
この(メタ)アクリレート共重合体の重量平均分子量を、50,000以上1,500,000以下とすることは、該共重合体の精製、処理液の取り扱い、医療機器への適応性、塗膜の安定性などに関する特定の技術課題を達成する為には、非常に重要な技術要件でもある。
重量平均分子量を測定する方法としては、末端基定量法、浸透圧法、蒸気圧オスモメトリー、蒸気圧降下法、氷点降下法、沸点上昇法、ゲルパーミエーションクロマトグラフィー(GPC)法などがあるが、本発明においては操作の容易さの点でゲルパーミエーションクロマトグラフィー(GPC)法という慣用の手法を採用する。
このように、処理液に含まれる該共重合体は、血液に対する例えば抗血栓性、溶出防止のような機能を有する親水性モノマー、セグメント、又はブロックからなるものと、医療機器に対する、例えば親和性、固着性のような機能を有する疎水性モノマー、セグメント又はブロックから構成されているという、いわゆる異なる二面の界面機能を果たす二種類のモノマー成分から実質的に構成されているが、一方で、該共重合体を構成する、モノマー、セグメント、又はブロック同志がお互いに分子構造内で補完しあって、溶出、分散などに対して安定な分子も結合又は構造を形成しているようにも見える。
例えば、還流塔を装着した攪拌可能な反応装置にモノマーと重合溶媒、開始剤を加え、窒素置換の後加熱することで重合を開始し、一定時間その温度を保つことで重合を進行させる。この重合の際に連鎖移動剤を併用し、分子量をコントロールすることも可能である。重合終了後の溶液より溶媒を除去し、粗(メタ)アクリレート共重合体を得る。引き続き、得られた粗(メタ)アクリレート共重合体を貧溶媒中で攪拌して精製処理を行う。精製処理を1~数回繰り返し(メタ)アクリレート共重合体の純度を上げる。このようにして得られた共重合体を乾燥する。
前記したような精製処理を1回、必要により2~8回行うことにより、未反応モノマー含有量が4,000ppm以下である水不溶性の(メタ)アクリレート共重合体を30質量%以上という高回収率で回収することが可能となる。該共重合体中に含まれる未反応モノマー、オリゴマー、重合残渣の含有量が多い場合には、それが血液中に溶出して、患者のショック症状などの原因物質となることが考えられる。それらの原因物質は精製処理で大部分は除去できるが、患者の安全を考慮すれば、その含有量を3,000ppm以下にするのがより好ましく、2,000ppm以下がさらに好ましく、1,000ppm以下が特に好ましい。
50mLバイアル中に試料1gを加えた後、エタノール99gを加え、十分混和させた。30分後、目視により溶解を確認した。エタノール不溶物が目視できなかった場合は○(良)と判断し、エタノール不溶物が目視できた場合は×(不良)と判断した。
アルコール可溶性○(良)と判断した溶液に水100gを加え混和した。30分間混和を継続しても白濁が解消しなかった場合は○(良)と判断し、30分間混和を継続すると白濁が解消した場合は×(不良)と判断した。
試料15mgをバイアル瓶に秤量し、GPC測定用移動相を3.0mL加えて一夜静置した。この溶解液を0.45μmの親水性PTFEメンブレンフィルターカートリッジ(Millex-LH、日本ミリポア社)でろ過した。GPC測定には515 HPLCポンプ、717plus自動注入装置(日本ウォーターズ社)を用い、カラムは2×PLgel 5μMIXED-D,7.5×300mm(アジレント・テクノロジー社)を用いた。カラム温度は40℃で行い、移動相は安定剤としてジブチルヒドロキシトルエンを含んだ液クロ用テトラヒドロフラン(富士フイルム和光純薬社)を用いた。RIにて検出を行い、20μL注入した。分子量校正は単分散ポリスチレン(Easi Cal PS-1, アジレント・テクノロジー社)で行った。
ガラス瓶に試料1gを測り取り、アセトン(富士フイルム和光純薬社)15mLを加えた。20分に1回手で振り混合させた。1~2時間後、溶解していることを目視で確認し、25mLのメスフラスコに移した。共洗いを行った後、アセトンを加え25mLとなるように調製した。その後、5μm径のフィルター(Merck社)でろ過を行ったものを試験溶液とした。粘度計定数C=0.003426(cSt/s)のウベローデ粘度計を使用し、30℃における試料溶液およびアセトンの落下時間を測定し、以下の式1により還元粘度を算出した。
(A/B-1)/C=(A/B-1)/(S/25×100)=(A/B-1)/(S×4)
A:試料溶液の落下秒数(秒)
B:アセトンの落下秒数(秒)
S:検体重量(g)
C:試料溶液濃度(g/dL)
105℃に設定した電気炉中に秤量瓶を入れて、30分乾燥させた。その後、デシケーター内で20分間放冷し、秤量瓶の質量を測定した。秤量瓶に試料0.5gを測り取った。同様に105℃に設定した電気炉中に秤量瓶を入れて、2時間乾燥させた。その後、デシケーター内で20分間放冷し、秤量瓶の質量を測定した。得られた各秤量瓶の質量から質量減少(%)を算出した。質量減少(%)が5%以下であれば試料が十分乾燥できたと判断した。
試料0.2gをアセトン(富士フイルム和光純薬社)2mLにて溶解後、適宜希釈した後GC測定により残留モノマーを定量した。測定装置はGC-2010Plus(島津社)を使用し、カラムはRtx-5(ジーエルサイエンス社)を使用した。注入口温度は150℃、検出器温度は280℃、オーブン温度は40℃に設定した。残留モノマーが4,000ppm以下であれば十分精製できたと判断した。
試料20mgを1mLの重クロロホルムに溶解し、400MHz超電導フーリエ変換核磁気共鳴装置(400-MR、Agilent社)にて1H-NMR測定を行った。
計100gとなるように試料にエタノールを加えて溶解することで、各濃度のエタノール溶液を調製し、処理液を得た。調製した濃度は表2に示した各濃度の試料である。処理液中にポリカーボネートシート(4cm×2cm×0.1cm)の半面部分(2cm×2cm×0.1cm)を10秒浸漬した後、ポリカーボネートシートを取り出し10mL/minの流量のエアで両面30秒ずつ乾燥させた。その後、室温で16時間乾燥させ、評価用シートとした。
ウサギ保存血液(型番:003-00053-01ジャパンバイオ・シーラム社)800μLを15mLの遠沈管へ添加した。80mM塩化カルシウム溶液66.6μLを加え、よく撹拌したものを試験血液溶液とした。評価用シートをプラスチックシャーレ上に置いた。プラスチックシャーレを37℃に設定した水浴上に置いた。評価用シートの未処理部分および処理部分に試験血液溶液を200μL添加した。その後37℃で25分間インキュベートした。インキュベート後の評価用シートを100mLの生理食塩液(大塚製薬社)中に沈め、軽く振とうした。生理食塩液から引き上げた評価用シート表面の血餅付着数を確認した。血餅付着が確認された評価用シートが10枚中4枚以下であれば血液適合性が良好と判断した。
評価用シートをエタノール(99.5質量%)5mLに30分浸漬し抽出液を得た。得られた抽出液に40℃で窒素ガスを吹き付け、エタノール臭が無くなるまで乾固した。この操作を3回繰り返した。得られた乾固物全量にイソフタル酸ジメチル0.13mgを添加した後、0.6mLの重クロロホルムに溶解し、30℃で1H-NMR測定を実施した。得られたピーク面積からコート量を計算した。コート量は下記式を用いて算出した。
コート量=C×218.023×B×1000000÷19400÷A
A:試料重量
B:ジメチルイソフタレート重量
C:1,3-ジメチル-2-イミダゾリジノン由来ピークの積分値を100とした時の、メトキシトリエチレングリコールアクリレート由来ピークの積分値
評価用シートをアルコール浸漬処理液(メタノール:エタノール=80質量%:20質量%)150mL中に16時間浸漬させた。浸漬後、十分に乾燥した評価用シートに対して、上記の血液凝固試験、コート定量を同様に行った。
メトキシトリエチレングリコールアクリレート(MTEGA)(新中村化学工業社)471.8gおよびシリコーンメタクリレート(PDMSMA)(Gelest社、製品名;MCR-M11)78.0gおよび2-エチルヘキシルアクリレート(EHA)(東亜合成株式会社)694.5gにアゾビスイソブチロニトリル(AIBN)(富士フイルム和光純薬株式会社)1.2325gを加え、エタノール(キシダ化学株式会社)1628.3g中で85℃、3時間の条件で重合反応を行った。重合反応終了後85℃、2時間の条件で常圧乾燥した。その後60℃、1時間の条件で減圧乾燥して濃縮物を得た。濃縮物を濃縮物Aと濃縮物Bに二等分した。次に濃縮物A612.1gにメタノール(キシダ化学株式会社)3162.7gおよび水305.3g加え、30分間撹拌した。撹拌終了後1.5時間静置し、デカンテーションにより上清を除去した。この沈殿にメタノールを加えて30分間攪拌し、1.5時間静置後デカンテーションにより上清を除去する作業を同様に3回繰り返し、沈殿Aを得た。使用したメタノールの添加量は順に3161.7g、3161.4g、3163.9gであった。同様に、濃縮物B 614.4gにメタノール3162.3g、水303.1g加え、30分間撹拌した。撹拌終了後1.5時間静置し、デカンテーションにより上清を除去した。この沈殿にメタノールを加えて30分間攪拌し、1.5時間静置後デカンテーションにより上清を除去する作業を同様に3回繰り返し、沈殿Bを得た。使用したメタノールの添加量は順に3165.5g、3167.5g、3165.4gであった。得られた沈殿A及び沈殿Bを一つにまとめ、40℃、1.5時間の条件で減圧乾燥して共重合体1を得た。
メトキシトリエチレングリコールアクリレート(MTEGA)(新中村化学工業社)94.25gおよびシリコーンメタクリレート(PDMSMA)(Gelest社、製品名;MCR-M11)15.59gおよび2-エチルヘキシルアクリレート(EHA)(東亜合成株式会社)138.68gにアゾビスイソブチロニトリル(AIBN)(富士フイルム和光純薬株式会社)0.2469gを加え、エタノール(キシダ化学株式会社)165.18g中で85℃、3時間の条件で重合反応を行った。重合反応終了後85℃、1時間の条件で常圧乾燥した。その後60℃、1.5時間の条件で減圧乾燥して濃縮物を得た。濃縮物を濃縮物Aと濃縮物Bに二等分した。次に濃縮物A122.51gにメタノール(キシダ化学株式会社)631.97gを加え、60℃で30分間撹拌した。撹拌終了後1.5時間静置し、デカンテーションにより上清を除去した。この沈殿にメタノールを加えて60℃で30分間攪拌し、1.5時間静置後デカンテーションにより上清を除去する作業を同様に3回繰り返し、沈殿Aを得た。使用したメタノールの添加量は順に631.98g、632.03g、632.05gであった。同様に、濃縮物B122.50gにメタノール631.99gを加え、60℃で30分間撹拌した。撹拌終了後1.5時間静置し、デカンテーションにより上清を除去した。この沈殿にメタノールを加えて60℃で30分間攪拌し、1.5時間静置後デカンテーションにより上清を除去する作業を同様に3回繰り返し、沈殿Bを得た。使用したメタノールの添加量は順に631.98g、632.00g、632.01gであった。得られた沈殿A及び沈殿Bを一つにまとめ、沈殿を85℃、30分の条件で常圧乾燥し、その後40℃、1時間の条件で減圧乾燥して共重合体2を得た。
メトキシトリエチレングリコールアクリレート(MTEGA)(新中村化学工業社)94.25gおよびシリコーンメタクリレート(Gelest社、製品名;MCR-M11)15.59gおよび2-エチルヘキシルアクリレート(EHA)(東亜合成株式会社)138.68gにアゾビスイソブチロニトリル(AIBN)(富士フイルム和光純薬株式会社)0.247gを加え、エタノール(富士フイルム和光純薬株式会社)165.18g中で85℃、3時間の条件で重合反応を行った。重合反応終了後85℃、1時間の条件で常圧乾燥した。その後60℃、1.5時間の条件で減圧乾燥して濃縮物を得た。濃縮物にメタノール(富士フイルム和光純薬株式会社)696.35gを加え、30分撹拌した。撹拌終了後1時間静置し、上清をデカンテーションにより除去した。沈殿を85℃、30分の条件で常圧乾燥し、その後40℃、1時間の条件で減圧乾燥して共重合体3を得た。
メトキシトリエチレングリコールアクリレート(MTEGA)(新中村化学工業社)94.27gおよびシリコーンメタクリレート(PDMSMA)(Gelest社、製品名;MCR-M11)15.60gおよび2-エチルヘキシルアクリレート(EHA)(東亜合成株式会社)138.66gにアゾビスイソブチロニトリル(AIBN)(富士フイルム和光純薬株式会社)0.2465gを加え、エタノール(キシダ化学株式会社)580.03g中で85℃、3時間の条件で重合反応を行った。重合反応終了後85℃、1時間の条件で常圧乾燥した。その後60℃、1.5時間の条件で減圧乾燥して濃縮物を得た。濃縮物を濃縮物Aと濃縮物Bに二等分した。次に濃縮物A122.53gにメタノール(キシダ化学株式会社)632.00gを加え、室温で30分間撹拌した。撹拌終了後1.5時間静置し、デカンテーションにより上清を除去した。この沈殿にメタノールを加えて室温で30分間攪拌し、1.5時間静置後デカンテーションにより上清を除去する作業を同様に3回繰り返し、沈殿Aを得た。使用したメタノールの添加量は順に632.09g、632.09g、632.32gであった。得られた沈殿Aを85℃、30分の条件で常圧乾燥し、その後40℃、1時間の条件で減圧乾燥して共重合体4を得た。
Claims (2)
- 下記一般式1で示されるアルキル(メタ)アクリレート単位及び下記一般式2で示されるシリコーン(メタ)アクリレート単位及び下記一般式3で示されるメトキシポリエチレングリコール(メタ)アクリレート単位を80~20/10~0.01/10~79.99のモル比で共重合させた、重量平均分子量が50,000以上1,500,000以下である(メタ)アクリレート共重合体であって、水不溶性(ここで、水不溶性であるとは、(メタ)アクリレート共重合体を該共重合体1質量%に対して99質量%の37℃生理食塩水に30日間静置した際、該共重合体の質量減少率が1質量%以下であることを指す)で、かつ室温で粘性液状であり、炭素数1~6のアルコールのいずれかに可溶であり、残留モノマー量が4,000ppm以下であり、還元粘度(ηsp/c)が0.18dl/g以上3.00dl/g以下である(メタ)アクリレート共重合体を含むことを特徴とする抗血栓性材料。
- 請求項1に記載の抗血栓性材料を含むことを特徴とする医療機器。
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EP22780970.4A EP4316540A1 (en) | 2021-03-31 | 2022-03-29 | Antithrombotic material |
CN202280025881.5A CN117157114A (zh) | 2021-03-31 | 2022-03-29 | 抗血栓性材料 |
KR1020237036656A KR20230160907A (ko) | 2021-03-31 | 2022-03-29 | 항혈전성 재료 |
JP2023511408A JPWO2022210759A1 (ja) | 2021-03-31 | 2022-03-29 | |
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Publication number | Priority date | Publication date | Assignee | Title |
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JP2002356519A (ja) * | 2001-05-30 | 2002-12-13 | Nof Corp | ホスホリルコリン類似基含有重合体および用途 |
JP2008266225A (ja) * | 2007-04-23 | 2008-11-06 | Toyobo Co Ltd | 抗血栓性抗菌性組成物および医療用具 |
JP2008289864A (ja) * | 2007-04-24 | 2008-12-04 | Toyobo Co Ltd | 抗血栓性材料 |
JP2009261437A (ja) * | 2008-04-22 | 2009-11-12 | Toyobo Co Ltd | カテーテル |
WO2019142710A1 (ja) * | 2018-01-22 | 2019-07-25 | テルモ株式会社 | 医療用コーティング材料および該医療用コーティング材料を利用した医療用具 |
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Publication number | Priority date | Publication date | Assignee | Title |
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JP2002356519A (ja) * | 2001-05-30 | 2002-12-13 | Nof Corp | ホスホリルコリン類似基含有重合体および用途 |
JP2008266225A (ja) * | 2007-04-23 | 2008-11-06 | Toyobo Co Ltd | 抗血栓性抗菌性組成物および医療用具 |
JP2008289864A (ja) * | 2007-04-24 | 2008-12-04 | Toyobo Co Ltd | 抗血栓性材料 |
JP4793700B2 (ja) | 2007-04-24 | 2011-10-12 | 東洋紡績株式会社 | 抗血栓性材料 |
JP2009261437A (ja) * | 2008-04-22 | 2009-11-12 | Toyobo Co Ltd | カテーテル |
WO2019142710A1 (ja) * | 2018-01-22 | 2019-07-25 | テルモ株式会社 | 医療用コーティング材料および該医療用コーティング材料を利用した医療用具 |
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JPWO2022210759A1 (ja) | 2022-10-06 |
US20240115776A1 (en) | 2024-04-11 |
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