JP2013151517A - 放出制御組成物 - Google Patents
放出制御組成物 Download PDFInfo
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- JP2013151517A JP2013151517A JP2013043282A JP2013043282A JP2013151517A JP 2013151517 A JP2013151517 A JP 2013151517A JP 2013043282 A JP2013043282 A JP 2013043282A JP 2013043282 A JP2013043282 A JP 2013043282A JP 2013151517 A JP2013151517 A JP 2013151517A
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- polymer
- diol
- diisocyanate
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Abstract
【解決手段】ポリエチレングリコール、ポリプロピレングリコール、ジオール、及びジイソシアネートを反応させて得られる水膨潤性線状ポリマーと薬学的活性剤からなる薬剤放出制御組成物に関する。また、ポリエチレングリコール、ポリプロピレングリコール、ジオール、及びジイソシアネートを反応させて得られる水膨潤性線状ポリマーと薬学的活性剤を含み、上記成分のモル比(i):(ii):(iii):(iv)が、1:1:1:3である放出制御組成物に関する。
【選択図】なし
Description
ここで、PEGはポリエチレングリコールを意味し、PPGはポリプロピレングリコールを意味する。
(a)ポリエチレングリコールまたはポリプロピレングリコール、
(b)PEG−PPG−PEG共重合体とまたはPPG−PEG−PPGブロック共重合体と
(c)二官能性化合物、
(d)二官能性イソシアネート
を共に反応させることにより得られる親水性で熱可塑性のポリウレタンエラストマーポリマーを提供する。
種々のポリエチレングリコール、ポリプロピレングリコール、PEG−PPG−PEG、PPG−PEG−PPG、ジオール、ジイソシアネートを理論混合比の範囲で用い、親水性線状ポリウレタンエラストマーポリマーに対する効果を検証した。PEG400、PEG900、PEG1000、及びPEG2000は、それぞれ分子量400、900、1000、及び2000g/molのポリエチレングリコールである。PPG1000及びPPG2000は、それぞれ分子量1000及び2000g/molのポリプロピレングリコールである。PEG−PPG−PEG1100及びPEG−PPG−PEG4400は、それぞれ分子量1100及び4400g/molのブロック共重合体である。PPG−PEG−PPG2000は、分子量2000g/molのブロック共重合体である。DDは1,10−デカンジオール、DDDは1,12−ドデカンジオール、DMDIはジシクロヘキシルメタン−4,4−ジイソシアネート、HMDIは1,6−ヘキサメチレン−ジイソシアネート、FECl3は塩化第二鉄、DABCOはトリエチレンジアミン、SnOct2はオクタン酸第一錫である。
重合時間が製造されるポリマーに及ぼす効果を、トリプル検出SEC(triple detection Size Exclution Chromatography)で調査した。ポリマーB及びCについて、重合時間に応じた分子量を測定した。結果を図1に示す。ポリマーの分子量は、レオロジー(rheology)、溶融流れ(melt flow)、及び力学的特性を決定するので、分子量測定が重要であることは明らかである。
実施例1において重合触媒は塩化第二鉄を用いたが、ポリマーNではDABCOとSnOct2、ポリマーMではDABCOが用いられ、ポリマーHでは触媒なしで重合が行われた(表1参照)。
ジシクロヘキシルメタン−4,4−ジイソシアネート(DMDI)の代わりに、ポリマーF、G、H、I、K、L、M、N、O、P、Q及びRでは1,6−ヘキサメチレン−ジイソシアネート(HMDI)を用いて実施例1と同様に重合を行なった(表1参照)。
表1に記載したポリマーについて適当な溶媒を見付けるために、異なる溶媒に溶解した。溶解度試験は、室温で24時間実施した。選択したポリマーの溶解度の結果を表2に示す。
選択したポリマーについて、水、エタノール、イソプロピルアルコール(IPA)、及びIPAと水の50%混合物中で、ポリマーに吸収される溶媒の量を測定する膨潤測定を行なった。10試料の膨潤の平均値として算出した結果を表3に示す。算出に使用した式は下記の通りである。
膨潤率(%)={(膨潤重量−乾燥重量)/乾燥重量}×100
製造したポリマーのショア硬度をタイプAとタイプDのデュロメータ(Durometer)を用い測定した。デュロメータAとDは、それぞれ軟質と硬質のゴムの弾力性を測定するために一般に用いられる。これらの測定は当業者によく知られている。4回測定した平均値の結果を表4に示す。
表1から選択したポリマーを加工前に真空下で一晩乾燥した。圧縮成形機の上部板と下部板の温度を目的の加工温度に設定した。型と熱した板の間に二枚のテフロン(登録商標)シートを配置した。3〜5分間溶融した後、170〜200barsの加圧下に30〜120秒間保持した。所定量のポリマーを型に満たした。室温まで冷却した後、試料(大きさ30mm×10mm×1mmのペッサリー)を機械的に型抜きし、分析用として冷凍庫に保存した。フィルム加工条件を表5に示す。
2つの異なる薬物であるフルコナゾール(fluconazole)とオキシブチニン(oxybutynin)を、選択したポリマーに担持した。実験用16mm同方向回転二軸押出機によりポリマーに担持した。薬物担持条件を表6に示す。
押出成形した担持ポリマーのインビトロでの薬物放出特性を、溶出試験により測定した。押出成形した担持ポリマーから放出したフルコナゾールとオキシブチニンの量を、短期放出の場合は米国薬局方(USP)のパドル法、長期放出の場合はエルレンマイヤーボトル(Erlenmeyer bottle)を用いた振とう培養法に基づく溶出試験により検討した。米国薬局方(USP)のパドル法の技術は、Distek社の溶出試験機(型番;model 2100C)(回転速度50rpmのパドル)が蠕動ポンプ(Icalis peristaltic pump)を介して分光光度計(Unicam UV500)に接続している自動UV(紫外)溶出システムで構成される。このシステムをDsolve(ソフトウエア)を用いて操作した。振とう培養法では、試料は手動で扱われ、分光光度計(Unicam UV500)により試料を測定した。実験条件は温度:37℃、溶出液:脱イオン化し脱気した水500ml。
薬物の種類を変えると、異なるプロファイルが得られた。フルコナゾールとオキシブチニンをポリマーAに担持した。標準化した溶出プロファイルを図3に示す。実施例10と同様の溶出試験法を用い、放出曲線を測定した。
溶出試験により、担持量増加の影響を検討した。異なる薬物量がポリマーAの放出特性に及ぼす影響を調査した。結果を図4に示す。フルコナゾールの担持量を20重量%から50重量%に増やした。実施例10と同様の溶出試験法を用い、放出曲線を測定した。
ポリマーAとポリマーCから得られたフルコナゾール放出プロファイルを、架橋ポリマー及び線状高膨潤ポリウレタンポリマーから得られた放出プロファイルと比較した結果を図5に示す。拡散担持架橋ポリマー(架橋17重量%フルコナゾール(crosslinked 17wt% fluconazole))は欧州特許出願公開第0016652号及び欧州特許出願公開第0016654号の特許明細書に記載がある。一方、線状高膨潤ポリマーは国際公開公報第2004/029125号パンフレットの特許明細書に記載されており、押出技術(高膨潤率20重量%フルコナゾール(high %SW 20wt% fluconazole))と同様に、拡散を用い担持された(高膨潤率17重量%フルコナゾール(high %SW 17wt% fluconazole))。実施例10と同様の溶出試験法を用い、放出曲線を測定した。これらの新規のポリマーは、図5に示すように、薬物放出を非常に良好に制御することが可能である。
Claims (18)
- (I)
(i)ポリエチレングリコール、
(ii)ポリプロピレングリコール、
(iii)ジオール、及び
(iv)ジイソシアネート
を反応して得られる水膨潤性線状ポリマーと、
(II)薬学的活性剤
を含む、放出制御組成物。 - ポリエチレングリコールが、分子量400〜2000g/molの線状ポリエチレングリコールである請求項1に記載の組成物。
- ポリプロピレングリコールが、分子量400〜2000g/molの線状ポリプロピレングリコールである請求項1に記載の組成物。
- ジオールが、炭素数5〜20のジオールである請求項1に記載の組成物。
- ジオールが、炭素数8〜15のジオールである請求項1に記載の組成物。
- ジオールが、1,6−へキサンジオール、1,10−デカンジオール、1,12−ドデカンジオールまたは1,16−ヘキサデカンジオールである請求項1に記載の組成物。
- ジイソシアネートが、ジシクロヘキシルメタン−4,4−ジイソシアネート、ジフェニルメタン−4,4−ジイソシアネートまたは1,6−へキサメチレンジイソシアネートである請求項1に記載の組成物。
- (i):(ii):(iii):(iv)のモル比が、それぞれ0.3:0.3:0.3:0.9である請求項1に記載の組成物。
- 成分(iv)のモル量が、成分(i)、成分(ii)、及び成分(iii)を合わせたモル量と等しい請求項1に記載の組成物。
- 固形投与製剤用である請求項1に記載の組成物。
- 固形投与製剤が座剤、膣リングもしくはペッサリー、口腔挿入剤、または経皮吸収型パッチである請求項10に記載の組成物。
- インプラントとして用いられる請求項10に記載の組成物。
- (I)
(i)ポリエチレングリコール、
(ii)ポリプロピレングリコール、
(iii)ジオール、及び
(iv)ジイソシアネート
を反応して得られる水膨潤性線状ポリマーと、
(II)薬学的活性剤
を含み、
上記成分のモル比(i):(ii):(iii):(iv)が、1:1:1:3である放出制御組成物。 - ポリエチレングリコールの分子量が、900g/molである請求項13に記載の組成物。
- ポリエチレングリコールの分子量が、2000g/molである請求項13に記載の組成物。
- ポリプロピレングリコールの分子量が、1000g/molである請求項13に記載の組成物。
- ポリプロピレングリコールの分子量が、2000g/molである請求項13に記載の組成物。
- ジオールが、1,12−ドデカンジオールある請求項13に記載の組成物。
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JP2015110770A (ja) * | 2013-11-11 | 2015-06-18 | 三洋化成工業株式会社 | 水等価ファントム材用ポリウレタン樹脂 |
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BRPI0713481B8 (pt) | 2021-05-25 |
DE602007012545D1 (de) | 2011-03-31 |
ATE498643T1 (de) | 2011-03-15 |
ES2363704T3 (es) | 2011-08-12 |
AU2007274119A1 (en) | 2008-01-17 |
CN101484495A (zh) | 2009-07-15 |
EP2038325A1 (en) | 2009-03-25 |
US20120329883A1 (en) | 2012-12-27 |
CN101484495B (zh) | 2011-12-28 |
BRPI0713481A2 (pt) | 2012-11-06 |
US8361273B2 (en) | 2013-01-29 |
CA2656788A1 (en) | 2008-01-17 |
GB0613638D0 (en) | 2006-08-16 |
US20090324692A1 (en) | 2009-12-31 |
AU2007274119B2 (en) | 2013-01-31 |
EP2038325B1 (en) | 2011-02-16 |
CA2656788C (en) | 2015-01-27 |
US8361272B2 (en) | 2013-01-29 |
JP2009542831A (ja) | 2009-12-03 |
PL2038325T3 (pl) | 2011-07-29 |
WO2008007046A1 (en) | 2008-01-17 |
JP5307710B2 (ja) | 2013-10-02 |
BRPI0713481B1 (pt) | 2019-08-13 |
DK2038325T3 (da) | 2011-05-30 |
JP5639673B2 (ja) | 2014-12-10 |
PT2038325E (pt) | 2011-05-02 |
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