JP6804692B2 - アニオン性薬剤含有眼用デバイス - Google Patents
アニオン性薬剤含有眼用デバイス Download PDFInfo
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- JP6804692B2 JP6804692B2 JP2020505928A JP2020505928A JP6804692B2 JP 6804692 B2 JP6804692 B2 JP 6804692B2 JP 2020505928 A JP2020505928 A JP 2020505928A JP 2020505928 A JP2020505928 A JP 2020505928A JP 6804692 B2 JP6804692 B2 JP 6804692B2
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- drug
- monomer
- anionic
- ophthalmic device
- hydrogel
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- 125000002091 cationic group Chemical group 0.000 claims description 57
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Images
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
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- A—HUMAN NECESSITIES
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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。
(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)
で示される化合物などが挙げられる。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化合物は、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る。上記一般式(I)の化合物のうち、本発明により好適に用いられる化合物は、3−((メタ)アクリルアミド)プロピルジメチルベンジルアンモニウムクロライドである。
アニオン性薬剤含有眼用デバイスの基材となる共重合体を構成するモノマー成分の混合物へ重合開始剤を添加した溶液を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て共重合反応に供することにより共重合体を得る工程;成形型を冷却し、及び成形型から共重合体を剥離し、得られた共重合体を、必要に応じて切削及び/又は研磨した後に、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、薬剤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剤を保持させたアニオン性薬剤含有眼用デバイスを得る工程。
(1)モノマー成分の混合物中に薬剤及び重合開始剤を添加及び混合して得られたモノマー混合液を共重合反応に供した後、得られた共重合体を膨潤し、任意に所定の溶液中に移送することを含む工程。ただし、該所定の溶液は、薬剤を含む溶液又は薬剤を含まない溶液であり得る。
(2)上記の共重合体を得る工程によって得られた共重合体を、薬剤溶液中にて薬剤の保持と膨潤とを一つの工程により行い、任意に所定の溶液中に移送する工程。ただし、該所定の溶液は、薬剤を含む溶液又は薬剤を含まない溶液であり得る。
(3)上記のハイドロゲルを得る工程で得られたハイドロゲルを、薬剤溶液中に浸漬して薬剤を保持した後、異なる所定の溶液中に移送する工程。ただし、該所定の溶液は、薬剤を含む溶液又は薬剤を含まない溶液であり得る。
(4)上記工程(1)〜(3)からなる群から選ばれる工程を適宜組み合わせる工程。
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(モル%)の3−(メタクリルアミド)プロピルジメチルベンジルアンモニウムクロライド(MAPBAC)とを含む混合物に、全モノマー成分の総重量に対し0.5%(外部)のエチレングリコールジメタクリレート(EDMA)及び全モノマー成分の総重量に対し2,500ppm(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した。共重合反応後に室温に戻した成形型より取出した共重合体を、60℃のエタノール含有リン酸緩衝液、次いで60℃の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)〜(2)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、実施例(3)〜(4)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)〜(4)の定型デバイスを得た。
MAPBACの代わりに表1に示す割合で特許文献3に記載の2−(メタクリロイルオキシ)エチルジメチルベンジルアンモニウムクロライド(MOEBAC)を用いたことを除いては、実施例(1)〜(4)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)〜(2)についてはDSCG 1.0wt%水溶液中に、比較例(3)〜(4)についてはDSP 0.2wt%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)〜(4)の定型デバイスを得た。
(1)含水率の測定
高圧蒸気滅菌後の実施例(1)〜(4)及び比較例(1)〜(4)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、各定型デバイスを60℃の乾燥機にて24時間乾燥させた後、乾燥状態のデバイスの重量(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。結果を表1に示す。
含水率(重量%)=[(W1−W2)/W1]×100
高圧蒸気滅菌後の実施例(1)〜(2)及び比較例(1)〜(2)の定型デバイスについて、パネラーであるヒト10人を対象として、8時間装用した際の異物感の評価を行った。装用中に異常を感じたと0〜2人が回答した場合の定型デバイスは「○」、異常を感じたと3〜5人が回答した場合の定型デバイスは「△」、6人以上が異常を感じたと回答した場合の定型デバイスは「×」と評価した。結果を表1に示す。
高圧蒸気滅菌後の実施例(1)〜(4)及び比較例(1)〜(4)の定型デバイスを生理食塩水中に室温にて浸漬し、内包したアニオン性薬剤を生理食塩水中へ放出(徐放)させ、経時的に生理食塩水中のアニオン性薬剤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)を用いて定量した。得られた値から単位デバイスあたりのアニオン性薬剤の取込量(μg/g)を算出した。結果を図1及び図2に示す。
アニオン性薬剤の取込量を測定した後の実施例(1)〜(2)及び比較例(1)〜(2)の定型デバイスについて、直径(mm)及び曲率半径(mm)を、オプティメックアナライザー(Optimic社製is830)を用いて経時的に計測した。
また、得られた計測結果から、下式に従い、アニオン性薬剤をt分間徐放したときのデバイスの直径及び曲率半径の変化率を算出した。直径の実測値の結果を表2及び図3に示し、直径の変化率の結果を表2及び図4に示す。また、曲率半径の実測値の結果を表3及び図5に示し、曲率半径の変化率の結果を表3及び図6に示す。
変化率(%)=[徐放時間(0分)]÷[(徐放時間(t分)]×100
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
MAPBAC:3−(メタクリルアミド)プロピルジメチルベンジルアンモニウムクロライド
EDMA:エチレングリコールジメタクリレート
AIBN:アゾビスイソブチルニトリル
DSCG:クロモグリク酸ナトリウム
DSP:デキサメタゾンリン酸エステルナトリウム
DIA:直径
B.C.:曲率半径
図1及び図2は、実施例(1)〜(4)及び比較例(1)〜(4)について、アニオン性薬剤の取込量を表わしたグラフである。図1から、アニオン性薬剤であるDSCGの取込量は、同一のモル比である場合に、実施例(1)〜(2)と、(比較例(1)〜(2)との間で差異は見られなかった。なお、実施例(1)〜(2)は(メタ)アクリル酸及び置換又は非置換のアラルキル基を有するアミノアルキル4級アンモニウム化合物との縮合物であるMAPBACを使用しているのに対して、比較例(1)〜(2)は(メタ)アクリル酸及び置換又は非置換のアラルキル基とカルボキシル基とを有するアルキル4級アンモニウム化合物の縮合物であるMOEBACを使用している。
さらに、アニオン性薬剤をDSPとした場合の取込量についても、MAPBACを使用した実施例(3)〜(4)と、MOEBACを使用した比較例(3)〜(4)との間で、差異は見られなかった。実施例(1)〜(4)は比較例(1)〜(4)と同程度のアニオン性薬剤の取込量を示すことが確認された。
Claims (5)
- (1)アニオン性薬剤;及び
(2)3−(メタクリルアミド)プロピルジメチルベンジルアンモニウムクロライドであるカチオン性モノマーと、該カチオン性モノマーと共重合可能なモノマーとを含むモノマー混合物の共重合体
を含む、アニオン性薬剤含有眼用デバイスであって、
前記カチオン性モノマーと共重合可能なモノマーは、カチオン性モノマーを除くモノマーであり、
前記モノマー混合物は、3−(メタクリルアミド)プロピルジメチルベンジルアンモニウムクロライド以外のカチオン性モノマーを含まず、及び
前記眼用デバイスは、眼内に装着可能である、前記眼用デバイス。 - 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、前記アニオン性薬剤含有眼用デバイスがハイドロゲルである、請求項1に記載の眼用デバイス。
- 前記(2)の共重合体が構成成分にアニオン性モノマーを含まず、かつ、前記アニオン性薬剤含有眼用デバイスがハイドロゲルである、請求項1に記載の眼用デバイス。
- 前記カチオン性モノマーの含有量が、親水性モノマー1モルに対し、0.5〜20モル%である、請求項2に記載の眼用デバイス。
- 前記アニオン性薬剤が、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1〜4のいずれか1項に記載の眼用デバイス。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2018120663 | 2018-06-26 | ||
JP2018120663 | 2018-06-26 | ||
PCT/JP2019/025070 WO2020004362A1 (ja) | 2018-06-26 | 2019-06-25 | アニオン性薬剤含有眼用デバイス |
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WO2020004362A1 (ja) | 2020-01-02 |
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