JP2013507217A - ビス−(アルファ−アミノ−ジオール−ジエステル)を含有するポリエステルアミドを含むコーティング - Google Patents
ビス−(アルファ−アミノ−ジオール−ジエステル)を含有するポリエステルアミドを含むコーティング Download PDFInfo
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- JP2013507217A JP2013507217A JP2012533657A JP2012533657A JP2013507217A JP 2013507217 A JP2013507217 A JP 2013507217A JP 2012533657 A JP2012533657 A JP 2012533657A JP 2012533657 A JP2012533657 A JP 2012533657A JP 2013507217 A JP2013507217 A JP 2013507217A
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Abstract
(式中、R1は、(C2〜C20)アルキレン、(C2〜C20)アルケニレン、−(R9−CO−O−R10−O−CO−R9)−、−CHR11−O−CO−R12−COOCR11−、およびこれらの組合せからなる群から独立に選択され;個々のコモノマーmまたはpにおけるR3およびR4は、それぞれ、水素、(C1〜C6)アルキル、(C2〜C6)アルケニル、(C2〜C6)アルキニル、(C6〜C10)アリール、(C1C6)アルキル、−(CH2)SH、−(CH2)2S(CH3)、−CH2OH、−CH(OH)CH3、−(CH2)4NH3 +、−(CH2)3NHC(=NH2 +)NH2、−CH2COOH、(CH2)COOH、−CH2−CO−NH2、−CH2CH2−CO−NH2、−CH2CH2COOH、CH3−CH2−CH(CH3)−、式(a)、HO−p−Ph−CH2−、(CH3)2CH−CH2−、Ph−NH−、NH−(CH2)3−C−、NH−CH=N−CH=C−CH2−からなる群から独立に選択され;R5またはR6は、1,4:3,6−ジアンヒドロヘキシトールの二環部分からまたは(C2〜C20)アルキレン、(C2〜C20)アルケニレン、アルキルオキシ、Mwが44Da〜700Daまでの範囲にあるオリゴエチレングリコール、−CH2−CH−(CH2OH)2、CH2CH(OH)CH2からなる群から独立に選択され、R5およびR6は同一でなく、R7は、水素、(C6〜C10)アリール、(C1C6)アルキル、またはベンジル等の保護基であるか、または生物活性剤であり;R8は、独立に、(C1〜C20)アルキルまたは(C2〜C20)アルケニルであり;R9またはR10は、C2〜C12アルキレンまたはC2〜C12アルケニレンから独立に選択され;R11またはR12は、H、メチル、C2〜C12アルキレン、またはC2〜C12アルケニレンから独立に選択される)によって表される化学式を有する少なくとも1種のポリ(エステルアミド)(PEA)またはそのブレンドを含む、コーティングに関する。
Description
(式中、:
−mは、約0.1〜約0.9であり、pは、約0.9〜約0.1であり、nは、約50〜約150であり、
−R1は、それぞれ独立に、(C1〜C20)アルキレンであり、R2は、それぞれ独立に、水素または(C6〜C10)アリール(C1〜C6)アルキルであり、
−R3は、それぞれ独立に、水素、(C1〜C6)アルキル、(C2〜C6)アルケニル、(C2〜C6)アルキニル、または(C6〜C10)アリール(C1〜C6)アルキルであり、R4は、それぞれ独立に、(C2〜C20)アルキレンである)のポリエステルアミド(PEA)(さらにPEA−lとも称される)を含むコーティングに関するものである。
(式中、
−mは、約0.01〜約0.99であり、pは、約0.99〜約0.01であり、qは、約0.99〜0.01であり、nは、約5〜約100であり、
−R1は、(C2〜C20)アルキレン、(C2〜C20)アルケニレン、−(R9−CO−O−R10−O−CO−R9)−、−CHR11−O−CO−R12−COOCR11−、およびこれらの組合せからなる群から独立に選択され、
−個々のコモノマーmまたはpにおけるR3およびR4は、それぞれ、水素、(C1〜C6)アルキル、(C2〜C6)アルケニル、(C2〜C6)アルキニル、(C6〜C10)アリール、(C1〜C6)アルキル、−(CH2)SH、−(CH2)2S(CH3)、−CH2OH、−CH(OH)CH3、−(CH2)4NH3 +、−(CH2)3NHC(=NH2 +)NH2、−CH2COOH、−(CH2)COOH、−CH2−CO−NH2、−CH2CH2−CO−NH2、−CH2CH2COOH、CH3−CH2−CH(CH3)−、(CH3)2−CH−CH2−、H2N−(CH2)4−、Ph−CH2−、CH=C−CH2−、HO−p−Ph−CH2−、(CH3)2−CH−、Ph−NH−、
からなる群から独立に選択され、
−R5またはR6は、1,4:3,6−ジアンヒドロヘキシトールの二環部分からまたは(C2〜C20)アルキレン、(C2〜C20)アルケニレン、アルキルオキシ、Mwが44Da〜700Daまでの範囲にあるオリゴエチレングリコール、−CH2−CH−(CH2OH)2、CH2CH(OH)CH2からなる群から独立に選択され、R5およびR6は同一ではなく、R5またはR6の少なくとも一方は1,4:3,6−ジアンヒドロヘキシトールの二環部分であり、
−R7は、水素、(C6〜C10)アリール、(C1〜C6)アルキル、またはベンジル等の保護基、または生物活性剤であり、
−R8は、独立に、(C1〜C20)アルキルまたは(C2〜C20)アルケニルであり、
−R9またはR10は、C2〜C12アルキレンまたはC2〜C12アルケニレンから独立に選択され、
−R11またはR12は、H、メチル、C2〜C12アルキレン、またはC2〜C12アルケニレンから独立に選択される)で表される化学式を有する少なくとも1種のポリ(エステルアミド)(PEA)またはそのブレンドを含み、留置器具(implantable device)用コーティングとして好適なコーティングを提供することにより達成される。
(式中、
−mは、約0.01〜約0.99であり、pは、約0.99〜約0.01であり、−qは、約0.99〜0.01であり、nは、約5〜約100であり、
−R1は、(C2〜C10)アルキレン((CH2)4や(CH2)8等)または(C2〜C20)アルケニレンおよびこれらの組合せからなる群から独立に選択され、
−個々のコモノマーmまたはpにおけるR3およびR4は、は、それぞれ、水素、(C1〜C6)アルキル、(C2〜C6)アルケニル、(C2〜C6)アルキニル、(C6〜C10)アリール(C1〜C6)アルキル、および−(CH2)2S(CH3)からなる群から独立に選択され、
−R5は、構造式(III)
の1,4:3,6−ジアンヒドロヘキシトールの二環部分から選択され、
−R6は、(C2〜C20)アルキレン(シクロヘキサンジオール等)、(C2〜C20)アルケニレン、またはアルキルオキシからなる群から選択され、
−R7は、ベンジルであり、
−R8は、独立に、(C3〜C6)アルキルまたは(C3〜C6)アルケニルである)で表される化学構造を有するPEA共重合体組成物を含むコーティングを提供する。
[材料および方法]
リン酸緩衝生理食塩水(PBS)をBiochrom AGより購入した。
Cfm Oskar Tropitzsch e.Kより入手したラパマイシンを使用した。
金属合金ステントを37℃のPBS緩衝液2ml中、静止状態でインキュベートする。所定の時間が経過したら緩衝液を交換する。278nmのUV吸光度測定により薬物(ラパマイシン)の放出を求める。
ラパマイシンおよび式IVの3Bzポリマー(PEA III)を容易に蒸発する溶剤に溶解させることによりコーティング剤を調製する。コーティング剤をステントにスプレーコーティングし、室温で乾燥する。結果として得られたコーティングのポリマー/薬物比は60/40(重量%/重量%)であり、コーティング厚さは約5〜6μmである。
ラパマイシンおよび式VのPEA−2Bz(PEA II)ポリマーを容易に蒸発する溶剤に溶解させることによりコーティング剤を調製する。コーティング剤をステントにスプレーコーティングし、室温で乾燥する。結果として得られたコーティングのポリマー/薬物比は60/40(重量%/重量%)であり、コーティング厚さは約7μmである。
PEA IIおよびPEA IIIから同等の条件下で調製したラパマイシンを含むステントコーティングでは、PEA IIを用いた方が放出がより速かった。PEA IIのコーティングはラパマイシンを約20日間放出することができたが、一方、PEAIIIのコーティングはラパマイシンを約45日間放出することができた。これらの結果を図1に示す。図1は、PEA IIおよびPEA IIIコーティングに関する4回の測定結果の平均値である。
Claims (11)
- 少なくとも1種の生分解性ポリマーおよび分散された生物活性剤を含むコーティングであって、前記ポリマーが、式(II)
(式中、
−mは、約0.01〜約0.99であり、pは、約0.99〜約0.01であり、qは、約0.99〜0.01であり、nは、約5〜約100であり、
−R1は、(C2〜C20)アルキレン、(C2〜C20)アルケニレン、−(R9−CO−O−R10−O−CO−R9)−、−CHR11−O−CO−R12−COOCR11−、およびこれらの組合せからなる群から独立に選択され、
−個々のコモノマーmまたはpにおけるR3およびR4は、それぞれ、水素、(C1〜C6)アルキル、(C2〜C6)アルケニル、(C2〜C6)アルキニル、(C6〜C10)アリール、(C1〜C6)アルキル、−(CH2)SH、−(CH2)2S(CH3)、−CH2OH、−CH(OH)CH3、−(CH2)4NH3 +、−(CH2)3NHC(=NH2 +)NH2、−CH2COOH、−(CH2)COOH、−CH2−CO−NH2、−CH2CH2−CO−NH2、−CH2CH2COOH、CH3−CH2−CH(CH3)−、
HO−p−Ph−CH2−、(CH3)2−CH−、Ph−NH−、NH−(CH2)3−C−、NH−CH=N−CH=C−CH2−からなる群から独立に選択され、
−R5またはR6は、1,4:3,6−ジアンヒドロヘキシトールの二環部分からまたは(C2〜C20)アルキレン、(C2〜C20)アルケニレン、アルキルオキシ、Mwが44Da〜700Daまでの範囲にあるオリゴエチレングリコール、−CH2−CH−(CH2OH)2、CH2CH(OH)CH2からなる群から独立に選択され、R5およびR6は同一でなく、R5またはR6の少なくとも一方は1,4:3,6−ジアンヒドロヘキシトールの二環部分であり、
−R7は、水素、(C6〜C10)アリール、(C1〜C6)アルキル、またはベンジル等の保護基であるか、または生物活性剤であり、
−R8は、独立に、(C1〜C20)アルキルまたは(C2〜C20)アルケニルであり、
−R9またはR10は、C2〜C12アルキレンまたはC2〜C12アルケニレンから独立に選択され、
−R11またはR12は、H、メチル、C2〜C12アルキレン、またはC2〜C12アルケニレンから独立に選択される)で表される化学構造を有する少なくとも1種のポリ(エステルアミド)(PEA)またはそのブレンドを含む、留置器具のコーティングに好適な、コーティング。 - R1が、−(CH2)4または−(CH2)8から選択される、請求項1に記載のコーティング。
- R5が、1,4:3,6−ジアンヒドロソルビトール(DAS)である、請求項1〜2のいずれか一項に記載のコーティング。
- 前記R3またはR4が、水素、−CH2−CH(CH3)2、−CH3、−CH(CH3)2、−CH(CH3)−CH2−CH3、−CH2−C6H5、−(CH2)4NH2、または−(CH2)2SCH3から選択される、請求項1〜3のいずれか一項に記載のコーティング。
- 前記R8が、−(CH2)4−である、請求項1〜4のいずれか一項に記載のコーティング。
- さらに生物活性剤を含む、請求項1〜5のいずれか一項に記載のコーティング。
- 前記生物活性剤が、成長因子(VEGF、FGF、MCP−1、PIGF、抗菌薬、抗炎症化合物、血栓形成抑制化合物、跛行改善薬、抗不整脈薬、抗動脈硬化薬、抗ヒスタミン物質、抗癌薬、血管薬、眼科用薬、アミノ酸、ビタミン類、ホルモン類、神経伝達物質、神経ホルモン、酵素、造影剤、シグナル伝達分子、および向精神薬から選択される、請求項6に記載のコーティング。
- 前記生物活性剤が、微粒子、ナノ粒子、またはミセル形態で存在することができる、請求項6〜7のいずれか一項に記載のコーティング。
- 厚みが約2〜15μmである、請求項1〜8のいずれか一項に記載のコーティング。
- 請求項1〜9のいずれか一項に記載のコーティングを備える留置器具。
- 前記器具が、心臓ペースメーカーおよび除細動器、前述のものに用いるためのリードおよび電極、神経、膀胱、括約筋、および横隔膜刺激装置等の器官刺激装置(organ stimulator)、装具、ロッド、人工血管、自己拡張型ステント、バルーン拡張型ステント、ステントグラフト、グラフト、カテーテル、人工心臓弁、ならびに髄液シャントを含む、請求項10に記載の留置器具。
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US10538864B2 (en) | 2012-10-24 | 2020-01-21 | Dsm Ip Assets, B.V. | Fibers comprising polyesteramide copolymers for drug delivery |
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