JPWO2015159942A1 - アニオン性薬物含有医療用デバイス - Google Patents
アニオン性薬物含有医療用デバイス Download PDFInfo
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- JPWO2015159942A1 JPWO2015159942A1 JP2016513826A JP2016513826A JPWO2015159942A1 JP WO2015159942 A1 JPWO2015159942 A1 JP WO2015159942A1 JP 2016513826 A JP2016513826 A JP 2016513826A JP 2016513826 A JP2016513826 A JP 2016513826A JP WO2015159942 A1 JPWO2015159942 A1 JP WO2015159942A1
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- meth
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Images
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- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
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Abstract
Description
(式中、
R1は水素原子又はCH3を表わし;
R2〜R4は、そのうち1〜3個がそれぞれ独立して下記一般式(II)
(式中、xは1〜3の整数を表わし;及び、R5〜R9はそれぞれ独立して水素原子又はC1〜C6の直鎖状若しくは分岐鎖状の炭化水素基を表わす)
で表わされる官能基を表わし、かつ、そのうち残りの2〜0個がC1〜C3の直鎖状若しくは分岐鎖状の炭化水素基を表わし;及び、
nは1〜4の整数を表わす)
で示される化合物である。
本発明のアニオン性薬物含有医療用デバイスは、(1)アニオン性薬物及び(2)共重合体を少なくとも含む。上記(2)の共重合体は、構成成分として、置換又は非置換のアラルキル基を有するアルキル4級アンモニウム化合物及び(メタ)アクリル酸の縮合物又はその塩を含むカチオン性モノマーと、これらと共重合可能なモノマーとを少なくとも含む。
(式中、
R1は水素原子又はCH3を表わし;
R2〜R4は、そのうち1〜3個がそれぞれ独立して下記一般式(II)
(式中、xは1〜3の整数を表わし;及び、R5〜R9はそれぞれ独立して水素原子又はC1〜C6の直鎖状若しくは分岐鎖状の炭化水素基を表わす)
で表わされる官能基を表わし、かつ、そのうち残りの2〜0個がC1〜C3の直鎖状若しくは分岐鎖状の炭化水素基を表わし;及び、
nは1〜4の整数を表わす)
で示される化合物が挙げられる。上記一般式(I)の化合物のうち、本発明に好適に用いられるものは、例えば、R1が水素原子又はCH3であり;R2〜R4はそのうち1個がベンジル基であり、残りの2個がCH3又はC2H5であり;nは1〜2の整数である化合物であり、より好ましくはメタクリルオキシエチルジメチルベンジルアンモニウムクロライドである。
アニオン性薬物含有医療用デバイスを構成するモノマーの混合物に重合開始剤を添加し、撹拌及び溶解することによりモノマー混合液を得る工程;得られたモノマー混合液を所望の成形型に入れ、共重合反応により共重合体を得る工程;共重合体を冷却及び成形型から剥離し、必要に応じて切削、研磨した後に、成形した共重合体を水和膨潤させてハイドロゲルを得る工程;及び、得られたハイドロゲルを、薬物を溶解させた溶液中に浸漬して、ハイドロゲルの内部に薬物を保持させたアニオン性薬物含有医療用デバイスを得る工程。
2−ヒドロキシエチルメタクリレート(HEMA)と、HEMA1モルに対し後述する表1に示す割合のメタクリルオキシエチルジメチルベンジルアンモニウムクロライド(MOEBAC)とを含む混合物に、モノマー総モルに対し1モル%のポリエチレングリコールジアクリレート(A−200)及びモノマーの総重量に対し3000ppm(外部)のアゾビスイソブチロニトリル(AIBN)を加え、撹拌混合してモノマー混合液を得た。得られたモノマー混合液を成形型に入れ、30〜110℃の範囲で17時間かけて昇温させて共重合反応に供することにより、重合体を得た。得られた重合体を室温に戻し、成形型より取出した後、60℃のエタノール含有リン酸緩衝液、次いでリン酸緩衝液中に各々1時間浸漬させ、さらに室温で純水に、2時間以上浸漬させることにより、水和膨潤したハイドロゲルを得た。得られたハイドロゲルを、実施例(1)〜(4)、(7)、(8)についてはデキサメタゾンリン酸エステルナトリウム(DSP)0.2wt%水溶液に、実施例(5)〜(6)についてはクロモグリク酸ナトリウム(DSCG)1.0wt%水溶液中に浸漬させた後、121℃、30分間高圧蒸気滅菌を行うことによって、実施例(1)〜(8)の定型デバイスを得た。
MOEBACの代わりに表1に示す割合でメタクリルアミドプロピルトリメチルアンモニウムクロライド(MAPTAC)を用いたことを除いては、実施例(1)〜(8)と同様にして水和膨潤したハイドロゲルを得た。得られたハイドロゲルを、比較例(1)〜(4)、(7)についてはDSP 0.2wt%水溶液に、比較例(5)〜(6)についてはDSCG 1.0wt%水溶液中に浸漬させた後、121℃、30分間高圧蒸気滅菌を行うことによって、比較例(1)〜(7)の定型デバイスを得た。なお、比較例(8)については定型のデバイスを構成することができなかった。
(1)含水率の測定
アニオン性薬物取込後の実施例(1)〜(8)及び比較例(1)〜(7)の定型デバイスを薬液から取出し、余分な水分を拭き取った後、含水状態のデバイスの質量(W1)を測定した。その後、60℃の乾燥機にて24時間乾燥させた後のデバイスの重量(W2)を測定し、各々の重量から下式に従い、含水率を算出した。
含水率(重量%)=[(W1−W2)/W1]×100
アニオン性薬物取込後の実施例(1)〜(8)及び比較例(1)〜(7)の定型デバイスを生理食塩水中に浸漬し、室温にて72時間静置し、内包したアニオン性薬物を生理食塩水中へ徐放させた。徐放後の生理食塩水中のアニオン性薬物を常法に従って高速液体クロマトグラフィー(HPLC、日本分光(株)社製)を用いて定量し、得られた値から単位デバイスあたりのアニオン性薬物取込量(μg/g)とした。
「プラスチックの引っ張り試験法(JIS K 7113)」に基づき試験片を調整し、薬剤を取り込んだ膨潤後の実施例(1)〜(8)及び比較例(1)〜(7)の定型デバイスをサンプルとして強度を測定した。
○:1.5MPa以上
×:1.5MPa未満
薬物徐放後の実施例(1)〜(8)及び比較例(1)〜(7)の定型デバイスの形状を、ディメンジョンアナライザーを用いて目視で確認した。
○:真円、かつ、面上に凹凸がない。
×:真円でない、あるいは、面上に凹凸がある。
HEMA:2−ヒドロキシエチルメタクリレート
MOEBAC:メタクリルオキシエチルジメチルベンジルアンモニウムクロライド
MAPTAC:メタクリルアミドプロピルトリメチルアンモニウムクロライド
A−200:ポリエチレングリコールジアクリレート
AIBN:アゾビスイソブチロニトリル
DSP:デキサメタゾンリン酸エステルナトリウム
DSCG:クロモグリク酸ナトリウム
Claims (5)
- (1)アニオン性薬物;及び
(2)構成成分として、置換又は非置換のアラルキル基を有するアルキル4級アンモニウム化合物及び(メタ)アクリル酸の縮合物又はその塩を含むカチオン性モノマーと、これらと共重合可能なモノマーとを含む共重合体
を含む、アニオン性薬物含有医療用デバイス。 - 前記置換又は非置換のアラルキル基を有するアルキル4級アンモニウム化合物及び(メタ)アクリル酸の縮合物が、下記一般式(I)
(式中、
R1は水素原子又はCH3を表わし;
R2〜R4は、そのうち1〜3個がそれぞれ独立して下記一般式(II)
(式中、xは1〜3の整数を表わし;及び、R5〜R9はそれぞれ独立して水素原子又はC1〜C6の直鎖状若しくは分岐鎖状の炭化水素基を表わす)
で表わされる官能基を表わし、かつ、そのうち残りの2〜0個がC1〜C3の直鎖状若しくは分岐鎖状の炭化水素基を表わし;及び、
nは1〜4の整数を表わす)
で示される化合物である、請求項1に記載のアニオン性薬物含有医療用デバイス。 - 前記(2)の共重合体が、構成成分として親水性モノマーをさらに含み、かつ、前記アニオン性薬物含有医療用デバイスがハイドロゲルである、請求項1に記載のアニオン性薬物含有医療用デバイス。
- 前記カチオン性モノマーの配合量が、親水性モノマー1モルに対し、0.5〜20モル%である、請求項1に記載のアニオン性薬物含有医療用デバイス。
- 前記アニオン性薬物が、デキサメタゾンリン酸エステルナトリウム又はクロモグリク酸ナトリウムである、請求項1に記載のアニオン性薬物含有医療用デバイス。
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