JP2009542831A - ポリウレタンエラストマー - Google Patents
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
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Abstract
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 (16)
- (a)ポリエチレングリコール(PEG)またはポリプロピレングリコール(PPG)、
(b)PEG−PPG−PEGブロック共重合体またはPPG−PEG−PPGブロック共重合体、
(c)二官能性化合物、及び
(d)二官能性イソシアネーを共に反応して得られる線状ポリマー。 - ポリエチレングリコールが、分子量400〜2000の線状ポリエチレングリコールである請求項1に記載の線状ポリマー。
- ポリプロピレングリコールが、分子量400〜2000の線状ポリプロピレングリコールである請求項1に記載の線状ポリマー。
- ブロック共重合体の分子量が200〜14,000である先行するいずれかの請求項に記載の線状ポリマー。
- 二官能性化合物(c)がジオールである先行するいずれかの請求項に記載の線状ポリマー。
- ジオールが、炭素数5〜20のジオールである請求項5に記載の線状ポリマー。
- ジオールが、炭素数8〜15のジオールである請求項6に記載の線状ポリマー。
- 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6に記載の線状ポリマー。
- 二官能性イソシアネート(d)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先行するいずれかの請求項に記載の線状ポリマー。
- (a):(b):(c):(d)の組成比が、当量換算でそれぞれ0.01〜1:0.01〜1:1:1.02〜3の範囲内である先行するいずれかの請求項に記載の線状ポリマー。
- ポリエチレングリコール(PEG)またはポリプロピレングリコール(PPG)、及びブロック共重合体を、二官能性化合物と共に真空下85〜100℃で、溶解、乾燥し、その後二官能性イソシアネートを添加することを含む先行するいずれかの請求項に記載の線状ポリマーの製造方法。
- 請求項1に記載の線状ポリマーと活性剤を含む放出制御組成物。
- 固形製剤に加工された請求項12に記載の組成物。
- 固形製剤が、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13に記載の組成物。
- 固形製剤が、インプラントである請求項13に記載の組成物。
- 活性剤の分子量が、200〜20,000である請求項12〜15のいずれかに記載の組成物。
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Application Number | Priority Date | Filing Date | Title |
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GB0613638.6 | 2006-07-08 | ||
GBGB0613638.6A GB0613638D0 (en) | 2006-07-08 | 2006-07-08 | Polyurethane elastomers |
PCT/GB2007/002415 WO2008007046A1 (en) | 2006-07-08 | 2007-06-27 | Polyurethane elastomers |
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JP2013043282A Division JP5639673B2 (ja) | 2006-07-08 | 2013-03-05 | 放出制御組成物 |
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JP2009542831A5 JP2009542831A5 (ja) | 2012-09-20 |
JP5307710B2 JP5307710B2 (ja) | 2013-10-02 |
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JP2013043282A Active JP5639673B2 (ja) | 2006-07-08 | 2013-03-05 | 放出制御組成物 |
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EP (1) | EP2038325B1 (ja) |
JP (2) | JP5307710B2 (ja) |
CN (1) | CN101484495B (ja) |
AT (1) | ATE498643T1 (ja) |
AU (1) | AU2007274119B2 (ja) |
BR (1) | BRPI0713481B8 (ja) |
CA (1) | CA2656788C (ja) |
DE (1) | DE602007012545D1 (ja) |
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013543763A (ja) * | 2010-11-12 | 2013-12-09 | ザ ユニバーシティ オブ ユタ リサーチ ファウンデーション | 潤滑剤の制御送達のための膣内デバイス |
JP2014520896A (ja) * | 2011-07-20 | 2014-08-25 | エフ. カイザー,パトリック | 薬物送達のための膣内デバイス |
JPWO2013137290A1 (ja) * | 2012-03-13 | 2015-08-03 | 住友精化株式会社 | 化粧料組成物 |
KR20160097288A (ko) * | 2013-12-10 | 2016-08-17 | 루브리졸 어드밴스드 머티어리얼스, 인코포레이티드 | 고탄성 열가소성 폴리우레탄 |
KR20170080671A (ko) * | 2014-11-07 | 2017-07-10 | 훼링 비.브이. | 퀴나골라이드를 포함하는 약물-디바이스 유닛 |
WO2019111839A1 (ja) * | 2017-12-04 | 2019-06-13 | 住友精化株式会社 | 揮発性物質放散用組成物 |
JP2022091999A (ja) * | 2014-04-01 | 2022-06-21 | ポリ-メッド インコーポレイテッド | 避妊具及び関連した器具 |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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Also Published As
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PL2038325T3 (pl) | 2011-07-29 |
AU2007274119B2 (en) | 2013-01-31 |
CN101484495A (zh) | 2009-07-15 |
ATE498643T1 (de) | 2011-03-15 |
PT2038325E (pt) | 2011-05-02 |
EP2038325A1 (en) | 2009-03-25 |
US20120329883A1 (en) | 2012-12-27 |
EP2038325B1 (en) | 2011-02-16 |
US8361273B2 (en) | 2013-01-29 |
JP2013151517A (ja) | 2013-08-08 |
AU2007274119A1 (en) | 2008-01-17 |
GB0613638D0 (en) | 2006-08-16 |
DK2038325T3 (da) | 2011-05-30 |
CA2656788A1 (en) | 2008-01-17 |
US8361272B2 (en) | 2013-01-29 |
CA2656788C (en) | 2015-01-27 |
BRPI0713481A2 (pt) | 2012-11-06 |
JP5639673B2 (ja) | 2014-12-10 |
US20090324692A1 (en) | 2009-12-31 |
BRPI0713481B8 (pt) | 2021-05-25 |
WO2008007046A1 (en) | 2008-01-17 |
BRPI0713481B1 (pt) | 2019-08-13 |
DE602007012545D1 (de) | 2011-03-31 |
CN101484495B (zh) | 2011-12-28 |
JP5307710B2 (ja) | 2013-10-02 |
ES2363704T3 (es) | 2011-08-12 |
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