JP2012514121A - ポリイソブチレンおよび生分解性ポリマーセグメントを持つコポリマー - Google Patents
ポリイソブチレンおよび生分解性ポリマーセグメントを持つコポリマー Download PDFInfo
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Abstract
【解決手段】本発明の幾つかの局面によれば、コポリマーが提供され、該コポリマーは、複数のポリイソブチレンセグメントおよび複数の生分解性ポリマーセグメントを含む。本発明の幾つかの局面によれば、コポリマーが提供され、該コポリマーは、ウレタン結合、ウレア結合、アミド結合、エステル結合、無水物結合、カーボネート結合、通常「クリック」化学結合として記載される結合、およびこれら結合の2またはそれ以上の型の組合せを含む。
【選択図】なし
Description
ポリウレタンは、次式のウレタン結合を含む一群のコポリマーである:
ポリウレアは、以下の式で表されるウレア結合を持つ一群のコポリマーである:
ポリアミド(即ち、以下の式で表されるアミド結合:
実施例1:PLLA-b-PIB-b-PLLAの合成
異なる硬質ブロック:軟質ブロック(HB:SB)組成を持つ、得られた6種のトリブロックコポリマーを、以下の表1に記載する。
表1:PLLA-b-PIB-b-PLLAトリブロックコポリマーの合成
2: この重量法による収率は、沈殿法を利用して該ポリマーを生成した後に計算した;
3: 与えられた数値は、様々なポリマーセグメントに関する数平均分子量を表す。
表2:上記プリカーサおよびトリブロックコポリマーの分子量データ
2: MnPIB対MnPLLAの比を表す;3: PLLA-b-PIB-b-PLLAトリブロックコポリマーの設計された分子量を表す;4: 1H-NMR分光分析により測定した該トリブロックコポリマーのMn;
5: GPC分析により測定した該トリブロックコポリマーのMn。
実施例1において製造したトリブロックコポリマージオールを、Sn(Oct)2の存在下で、トルエン中で、高温度下にて、MDIにより連鎖延長させて、対応するマルチブロックコポリマーを得た。
表3:マルチブロックコポリマー(PLLA(1800)-b-PIB(6700)-b-PLLA(1800)=1eq.およびSn(Oct)2=トリブロックコポリマーの1モル%)の分子量およびPDI
該マルチブロックコポリマーの分子量および多分散性指数を、以下の表4に与える。該マルチブロックコポリマーのMnは、PDI=1.4-1.6に関して、43,400〜71,400なる範囲の値として得られた。
表4:連鎖延長されたPLLA-b-PIB-b-PLLAトリブロックコポリマーの分子量データ
1: これらのサンプルは、特に述べない限り、10℃/分なる加熱並びに冷却速度にて記録された;2: Tg1は、PIBブロックのガラス転移点に相当し、またTg2は、PLLAブロックのガラス転移点に相当する;3: M/Tは、対応するマルチブロック/トリブロックコポリマーのTgおよびTmを表す;4: これは結晶化温度を表す;5: 合成ポリマー自体の第一および第二加熱走査を表す;6: クロロホルム-流延/圧縮成型マルチブロックコポリマーの第一加熱走査を表す。
HO-アリル-PIB-アリル-OH(Mn = 3300)を巨大開始剤として使用し、また実施例1に記載の手順を使用して、L-ラクチドの開環重合により、約60-90質量%のPLLAを含むトリブロックコポリマーを合成した。
該トリブロックコポリマーの命名法および組成を、以下の表7に記載する。
表7:トリブロックコポリマーのPIBおよびPLLA含有率(質量%)およびMnのデータ
上記実施例3のトリブロックコポリマーの連鎖延長を、実施例2に記載のようにして、75℃にてMDIを用いて実施した(結果を以下の表8に示す)。
表8:マルチブロックコポリマーの分子量データ
表9:PLLA-PIBマルチブロックコポリマーの融点およびガラス転移点
表11:PLA-PIBマルチブロックコポリマーの静的引張特性
PBLG-b-PIB-b-PBLGトリブロックコポリマー(Mn=4,770、PDI=1.12)の合成は、NH2-アリル-PIB-アリル-NH2(PIBジアミン)巨大開始剤を使用して、γ-ベンジル-L-グルタメートN-カルボキシ無水物(Glu-NCA)の開環重合により行った。Mn=2,390およびPDI=1.09を持つPIBジアミン巨大開始剤は、U. Ojha等, Macromolecules, 2008, 41, 3832-3841において前に報告されたように、α,ω-クロロ-アリル官能性PIBとカリウムフタルイミドとの反応において得られる、α,ω-フタルイミド-官能性PIBの加ヒドラジン分解によって合成した。Glu-NCAの、従来のアミン重合(Biomacromolecules, 5(5), 1653, 2004)およびアンモニウム-媒介重合(Chem. Commun., 23, 2944, 2003)両者を実施した。以下において説明される、Glu-NCAのアンモニウム-媒介重合は、該従来のアミン重合と比較して、より良好な分子量の制御性およびより低いPDIを与えた。
容量100mLの3つ口丸底フラスコ中で、無水PBLG-b-PIB-b-PBLG(0.18g、0.0.383mM)を、無水THF/DMF(4mL/1mL)中に、窒素雰囲気下で溶解した。この溶液を40℃に加熱し、MDI(9.6mg、0.0384mM)を添加した。FT-IRによる反応に引続き、該溶液を40℃にて24時間攪拌した。この溶液を減圧下で濃縮し、次いで冷メタノール(20mL)中に注込み、目的のポリマーを沈殿させた。該ポリマーを濾別し、真空条件下で24時間に渡り乾燥して、白色固体として目的とする(ABA)nマルチブロックコポリマー(Mn=28500、PDI=2.8)を得た。
Claims (23)
- 数平均分子量20,000またはそれ未満を持つ、複数のポリイソブチレンセグメントおよび複数の生分解性ポリマーセグメントを含む、ことを特徴とするコポリマー。
- 2〜50個のポリイソブチレンセグメントを含む、請求項1記載のコポリマー。
- 2〜50個の生分解性ポリマーセグメントを含む、請求項1記載のコポリマー。
- 前記コポリマーが、ポリエステルセグメント、ポリカーボネートセグメント、ポリオルトエステルセグメント、ポリ酸無水物セグメント、およびポリホスファジンセグメントから選択される複数の生分解性ポリマーセグメントを含む、請求項1記載のコポリマー。
- 前記コポリマーが、ポリ(アミノ酸)セグメントから選択される、複数の生分解性ポリマーセグメントを含む、請求項1記載のコポリマー。
- 前記コポリマーが、ポリヒドロキシ酸セグメント、ポリカーボネートセグメントおよびポリラクトンセグメント、およびこれらの混合物から選択される、複数の生分解性ポリマーセグメントを含む、請求項1記載のコポリマー。
- 前記コポリマーが、複数の硬質生分解性ポリマーセグメントを含む、請求項1記載のコポリマー。
- ポリエステル/ポリイソブチレン/ポリエステルトリブロック、ポリカーボネート/ポリイソブチレン/ポリカーボネートトリブロック、ポリオルトエステル/ポリイソブチレン/ポリオルトエステルトリブロック、ポリ酸無水物/ポリイソブチレン/ポリ酸無水物トリブロック、ポリホスファジン/ポリイソブチレン/ポリホスファジントリブロック、およびポリ(アミノ酸)/ポリイソブチレン/ポリ(アミノ酸)トリブロックから選択される、複数のトリブロックを含む、請求項1記載のコポリマー。
- ポリ(ヒドロキシ酸-b-イソブチレン-b-ヒドロキシ酸)トリブロック、ポリ(カーボネート-b-イソブチレン-b-カーボネート)トリブロック、ポリ(ラクトン-b-イソブチレン-b-ラクトン)トリブロック、およびこれらの組合せから選択される、複数のトリブロックを含む、請求項1記載のコポリマー。
- (a) 複数のジイソシアネート残基および(b) 複数のウレタン結合、複数のウレア結合、またはこれらの組合せを含む、請求項1記載のコポリマー。
- 前記ジイソシアネート残基が、非-芳香族系のジイソシアネート残基を含む、請求項10記載のコポリマー。
- 前記ジイソシアネート残基が、芳香族系のジイソシアネート残基を含む、請求項10記載のコポリマー。
- 前記ジイソシアネート残基が、4,4'-メチレンジフェニルジイソシアネート、トルエンジイソシアネート、1,5-ナフタレンジイソシアネート、p-フェニレンジイソシアネート、3,3'-トリデン-4,4'-ジイソシアネート、3,3'-ジメチル-ジフェニルメタン-4,4'-ジイソシアネート、およびこれらの組合せから選択される芳香族ジイソシアネートの残基を含む、請求項12記載のコポリマー。
- 更に、複数の連鎖延長剤残基をも含む、請求項10記載のコポリマー。
- 前記連鎖延長剤残基が、脂肪族ジオール残基、芳香族ジオール残基、脂肪族ジアミン残基および芳香族ジアミン残基から選択される、請求項14記載のコポリマー。
- 前記連鎖延長剤残基が、α,ω-C1-C10-アルカンジオール残基から選択される、請求項14記載のコポリマー。
- 請求項1記載のコポリマーを含む、ポリマー領域を含有することを特徴とする、医療用物品。
- 請求項1記載のコポリマーを含む、ポリマー領域を含有することを特徴とする、移植可能なまたは挿入可能な医療用デバイス。
- 前記医療用デバイスが、ステントカテーテル、誘導線、整形外科用ネジ、縫合糸、静脈弁、心臓弁、移植片、動脈瘤コイル、接着防止被膜、骨盤メッシュ、ヘルニアメッシュ、および脊椎板代替品から選択される、請求項18記載の移植可能なまたは挿入可能な医療用デバイス。
- 前記ポリマー領域が、更に治療薬をも含む、請求項18記載の移植可能なまたは挿入可能な医療用デバイス。
- 前記医療用デバイスがステントであり、かつ前記治療薬が再狭窄防止剤である、請求項20記載の移植可能なまたは挿入可能な医療用デバイス。
- ウレタン結合、アミド結合、エステル結合、カーボネート結合、無水物結合、1,2,3-トリアゾール部分を含む結合、およびこれらの組合せから選択される複数の結合を含む、請求項1記載のコポリマー。
- 前記ポリイソブチレンセグメントが、ウレタン結合、ウレア結合、アミド結合、エステル結合、カーボネート結合、無水物結合、1,2,3-トリアゾール部分を含む結合、およびこれらの組合せから選択される結合により、前記生分解性ポリマーセグメントに結合している、請求項1記載のコポリマー。
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US14201908P | 2008-12-31 | 2008-12-31 | |
US61/142,019 | 2008-12-31 | ||
PCT/US2009/069855 WO2010078451A1 (en) | 2008-12-31 | 2009-12-30 | Copolymers having polyisobutylene and biodegradable polymer segments |
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JP2012514121A true JP2012514121A (ja) | 2012-06-21 |
JP2012514121A5 JP2012514121A5 (ja) | 2013-02-21 |
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US (2) | US8911760B2 (ja) |
EP (2) | EP2373356B1 (ja) |
JP (1) | JP5775822B2 (ja) |
CN (1) | CN102341134B (ja) |
CA (1) | CA2748494A1 (ja) |
WO (1) | WO2010078451A1 (ja) |
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EP2373356B1 (en) * | 2008-12-31 | 2015-03-04 | Boston Scientific Scimed, Inc. | Copolymers having polyisobutylene and biodegradable polymer segments |
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KR20120112383A (ko) * | 2009-10-16 | 2012-10-11 | 바스프 에스이 | 폴리이소부텐 블록 및 올리고아미드 블록으로 제조된 열가소성 엘라스토머로서의 블록 공중합체 |
US20110196464A1 (en) * | 2010-02-09 | 2011-08-11 | Leonard Pinchuk | Pacemaker Lead and Method of Making Same |
GB201221246D0 (en) * | 2012-11-26 | 2013-01-09 | Ecole Polytechnique Federale De Lausanne | Polymer blends |
US9243203B2 (en) | 2012-11-30 | 2016-01-26 | Chevron Oronite Company Llc | Copolymers of polyaminopolyolefins and polyanhydrides and methods of their preparation |
CN102977319B (zh) * | 2012-12-17 | 2014-09-03 | 中国科学院长春应用化学研究所 | 可降解聚乳酸两嵌段共聚物、制备方法及其在改性聚乳酸中的应用 |
JP6564369B2 (ja) | 2013-12-09 | 2019-08-21 | デュレクト コーポレイション | 薬学的活性剤複合体、ポリマー複合体、ならびにこれらを伴う組成物及び方法 |
KR20160023973A (ko) * | 2014-08-21 | 2016-03-04 | 삼성정밀화학 주식회사 | 투명 생분해성 고분자 |
US20160122464A1 (en) * | 2014-10-30 | 2016-05-05 | Cardiac Pacemakers, Inc. | Solvent free polyisobutylene based polyurethanes |
KR101648487B1 (ko) * | 2015-06-23 | 2016-08-17 | 주식회사 아모그린텍 | 주사기용 안전필터 |
KR101675865B1 (ko) * | 2015-06-23 | 2016-11-15 | 주식회사 아모라이프사이언스 | 안전필터, 그 제조방법 및 이를 구비한 주사기 |
US10111986B2 (en) * | 2015-10-17 | 2018-10-30 | Cardiac Pacemakers, Inc. | Production of in situ crosslinkable polyisobutylene-polyurethane nanofibers and coatings |
CN107007620B (zh) * | 2017-04-19 | 2021-03-02 | 川北医学院 | 对氧环己酮与l-苯丙氨酸共聚物及其应用 |
EP3740253B1 (en) | 2018-01-17 | 2023-08-16 | Cardiac Pacemakers, Inc. | End-capped polyisobutylene polyurethane |
US10882945B2 (en) | 2018-03-26 | 2021-01-05 | Medtronic, Inc. | Modified polyisobutylene-based polymers, methods of making, and medical devices |
CN111748086B (zh) * | 2020-07-20 | 2022-08-05 | 万华化学(四川)有限公司 | 聚异丁烯基聚碳酸酯共聚物及其制备方法 |
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JP5775822B2 (ja) | 2015-09-09 |
US9631042B2 (en) | 2017-04-25 |
EP2373356B1 (en) | 2015-03-04 |
EP2898904A1 (en) | 2015-07-29 |
US8911760B2 (en) | 2014-12-16 |
US20100166820A1 (en) | 2010-07-01 |
EP2373356A1 (en) | 2011-10-12 |
CN102341134B (zh) | 2014-09-10 |
WO2010078451A1 (en) | 2010-07-08 |
US20150203622A1 (en) | 2015-07-23 |
CN102341134A (zh) | 2012-02-01 |
CA2748494A1 (en) | 2010-07-08 |
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