JP5409006B2 - 弱水溶性化合物のための可溶化剤としてのコポリマーの使用 - Google Patents
弱水溶性化合物のための可溶化剤としてのコポリマーの使用 Download PDFInfo
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- JP5409006B2 JP5409006B2 JP2008538334A JP2008538334A JP5409006B2 JP 5409006 B2 JP5409006 B2 JP 5409006B2 JP 2008538334 A JP2008538334 A JP 2008538334A JP 2008538334 A JP2008538334 A JP 2008538334A JP 5409006 B2 JP5409006 B2 JP 5409006B2
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- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
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- A—HUMAN NECESSITIES
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Description
i)30〜80重量%のN−ビニルラクタム、
ii)10〜50重量%の酢酸ビニル、及び
iii)10〜50重量%のポリエーテル
(ただし、i)、ii)及びiii)の総量は100重量%に等しい)
の混合物のフリーラジカル重合によって得られる水溶性又は水分散性コポリマーの使用により解決される。
i)30〜70重量%のN−ビニルラクタム、
ii)15〜35重量%の酢酸ビニル、及び
iii)15〜35重量%のポリエーテル
から得られ、特に好ましいポリマーは、以下:
i)40〜60重量%のN−ビニルラクタム、
ii)15〜35重量%の酢酸ビニル、及び
iii)15〜30重量%のポリエーテル
から得られる。
i)40〜60重量%のN−ビニルラクタム、
ii)15〜35重量%の酢酸ビニル、
iii)10〜30重量%のポリエーテル
からなる。
本発明に従って用いられるコポリマーは、原則として、水への可溶性が低い又はゼロしかない物質を水性調製物中で使用することを目的とする又は水性媒質においてそれらの効果を示すことを目的とする、全ての分野において利用することができる。従ってコポリマーは、弱水溶性物質、特に生物活性物質のための可溶化剤として用いられる。
本発明において、前記コポリマーは化粧品製剤中の可溶化剤として用いることができる。これらは、例えば化粧用油のための可溶化剤として好適である。これらは、脂肪及び油、例えば落花生油、ホホバ油、ヤシ油、アーモンド油、オリーブ油、パーム油、ヒマシ油、ダイズ油若しくはコムギ胚種油など、又はエッセンシャルオイル、例えばドワーフパイン油、ラベンダー油、ローズマリー油、スプルースニードル油、パインニードル油、ユーカリ油、ハッカ油、セージ油、ベルガモット油、テレビン油、メリッサ油、セージ油、杜松油、レモン油、アニス油、カルダモン油、ハッカ油、樟脳油など、あるいはこれらの油の混合物を良好に可溶化する能力を有する。
本発明のコポリマーは、100%純度の物質として、又は好ましくは水溶液として、化粧品製剤のための可溶化物を調製するために用いることができる。
本発明のコポリマーは同様に、弱水溶性又は水不溶性の1以上の薬物、並びにビタミン類及び/又はカロテノイド類を含みうる任意の種類の医薬調製物における可溶化剤として使用するために好適である。経口投与のための水溶液又は可溶化物は、この関係で特に重要なものである。したがって、本発明のコポリマーは、経口投与剤形、例えば錠剤、カプセル剤、散剤、溶剤などにおける使用に好適である。これらにおいて、コポリマーは弱溶性薬物のバイオアベイラビリティを高めうる。特に有効成分及び可溶化剤の固溶体を使用する。
化粧品及び医薬における用途の他、本発明のコポリマーは、食品分野において、弱水溶性又は水に不溶性の栄養物質、助剤又は添加物、例えば脂溶性ビタミン類又はカロテノイド類のための可溶化剤としても好適である。言及することができる例としては、カロテノイドで着色した飲料がある。
農芸化学における本発明のコポリマーの可溶化剤としての使用は、中でも農薬、除草剤、殺真菌剤又は殺虫剤を含む製剤、特に散布又は散水用の製剤として用いられる作物保護薬の調製物などを含みうる。
使用する略語:
VCap:N−ビニルカプロラクタム
VP:N−ビニルピロリドン
VAc:酢酸ビニル
PEG:ポリエチレングリコール
最初の投入分:165.0gの酢酸エチル
100.0gのPEG6000
20.0gの酢酸ビニル
10.50gのフィード2
フィード1:500gのビニルカプロラクタム
180gの酢酸ビニル
100gの酢酸エチル
フィード2:10.50gのt−ブチルペルエチルヘキサノエート(98重量%純度)
94.50gの酢酸エチル
最初の投入分:165gの酢酸エチル
100.0gのPEG6000
22.0gの酢酸ビニル
10.50gのフィード2
フィード1:480gのビニルカプロラクタム
198gの酢酸ビニル
100gの酢酸エチル
フィード2:10.50gのt−ブチルペルエチルヘキサノエート(98重量%純度)
94.50gの酢酸エチル
最初の投入分:25gの酢酸エチル
104.0gのPEG6000
1.0gのフィード2
フィード1:240gの酢酸ビニル
フィード2:456gのビニルカプロラクタム
240gの酢酸エチル
フィード3:10.44gのt−ブチルペルピバレート(75重量%純度、脂肪族化合物の混合物)
67.90gの酢酸エチル
最初の投入分:25gの酢酸エチル
112.0gのPEG6000
1.0gのフィード2
フィード1:408gのビニルカプロラクタム
280gの酢酸ビニル
240gの酢酸エチル
フィード2:10.32gのt−ブチルペルピバレート(75重量%純度、脂肪族化合物の混合物)
67.10gの酢酸エチル
最初の投入分:25gの酢酸エチル
112.0gのPEG6000
1.0gのフィード2
フィード1:428.0gのビニルカプロラクタム
260.0gの酢酸ビニル
240gの酢酸エチル
フィード2:10.32gのt−ブチルペルピバレート(75重量%純度、脂肪族化合物の混合物)
67.10gの酢酸エチル
最初の投入分:50gの酢酸ブチル、150.0gのPEG6000、1.0gのフィード3
フィード1:500gのVCap、120.0gの酢酸ブチル
フィード2:350.0gのVAc、80.0gの酢酸ブチル
フィード3:12.75gのt−ブチルペルピバレート(75重量%純度、脂肪族化合物の混合物)、117.25gの酢酸ブチル
最初の投入分:40gの酢酸エチル、120.0gのPEG6000、1.28gのフィード2
フィード1:400gのVCap、280.0gの酢酸ビニル、225.0gの酢酸エチル
フィード2:10.2gのt−ブチルペルピバレート(75重量%純度、脂肪族化合物の混合物)、118.4gの酢酸エチル
湯浴温度85℃にてt−ブチルペルエチルヘキサノエートを用いて、実施例18と同様に行った。
以下のフィードを用いて、実施例19と同様に行った:
最初の投入分:120.0gのPEG6000
フィード1:160gのVCap、280.0gの酢酸ビニル、50.0gの酢酸エチル
フィード2:10.2gのt−ブチルペルピバレート(75重量%純度、脂肪族化合物の混合物)、91.80gの酢酸エチル
フィード3:240gのVCap、242.0gの酢酸エチル
モノマー組成(重量%)を15 PEG/55 VCap/30 Vacとして、実施例19と同様に行った。
溶媒としてt−ブタノールを用いて、実施例19と同様に行った。
実施例18と同様に行って、さらなる重合の終了後に、81.6gの酢酸エチル中の9.07gのt−ブチルペルピバレートを添加し、その後さらに2時間重合を行って残渣のモノマーを低減させた。
モノマー組成(重量%)を15 PEG/50 VCap/35 VAcとして、二倍量で、90℃にて加圧装置において、実施例21と同様に行った。この場合、0.2MPaの領域の圧力に設定した。
噴霧乾燥
実施例18と同様に調製したポリマーを噴霧乾燥した。乾燥は直接行った:
噴霧器:二流体ノズル、1.3mmテフロン(登録商標)
添加物:なし
固形分:15重量%
入口温度:121℃
出口温度:55℃
収率:77%
色:白色
粉末特性:わずかに塊がある
実施例1のように得られたポリマー水溶液を、実施例25と同様に噴霧乾燥によって処理した。
比較例A:70重量%のVAc、30重量%のPEG6000
比較例B:70重量%のVAc、30重量%のPEG1500
これらのポリマーは顕著な粘着性を示した。
ポリマー−有効成分混合物は、重量比1:1の有効成分とポリマーを適当なガラス容器(それぞれ2g)に計量投入し、続いて16mlのジメチルホルムアミドを溶媒として添加することによって作製した。混合物を磁性撹拌器で20℃にて24時間撹拌した。次に溶液を120μmナイフを用いてガラスプレートに塗布した。このプレートをドラフト内で室温にて0.5時間乾燥した後、乾燥炉内で50℃で10mbarにてさらに0.5時間乾燥して、定量的に溶媒を除去した。その後、サンプルを目視検査した。膜が透明であり、有効成分が7日後に結晶化しなかった場合には、有効成分がポリマー中に安定に溶解したものとして評価した(表1に50と表示)。50重量%の有効成分含量では固溶体が得られない場合には、33重量%の有効成分の投入によって実験を反復実施し、安定な固溶体の形成を上記と同じように評価した(表に33と表示)。
2gのコポリマーをガラスビーカーに計量投入した。次に各混合物に薬物を投入し、以下のように過飽和溶液を得た。投入した塊が培地に溶解した場合、堆積物が形成されるまでその重量を増加させた。
Claims (11)
- 以下:
i)40〜60重量%のN−ビニルカプロラクタム、
ii)15〜35重量%の酢酸ビニル、及び
iii)10〜30重量%のポリエーテル
(ただし、成分i)、ii)及びiii)の総量は100重量%に等しい)
の混合物のフリーラジカル重合によって得られる水溶性又は水分散性コポリマーの、医薬調製物における弱水溶性有効成分のための可溶化剤としての使用であって、前記医薬調製物において前記有効成分及び前記可溶化剤が固溶体として存在する、前記使用。 - コポリマーが成分iii)としてポリエチレングリコールを含む、請求項1に記載の使用。
- コポリマーが成分iii)として分子量1000ダルトン〜10000ダルトンのポリエチレングリコールを含む、請求項1又は2に記載の使用。
- コポリマーのK値が10〜60である、請求項1〜3のいずれか1項に記載の使用。
- コポリマーのK値が15〜40である、請求項1〜3のいずれか1項に記載の使用。
- 弱水溶性有効成分が生物活性物質である、請求項1〜5のいずれか1項に記載の使用。
- 以下:
i)40〜60重量%のN−ビニルカプロラクタム、
ii)15〜35重量%の酢酸ビニル、及び
iii)10〜30重量%のポリエーテル
(ただし、成分i)、ii)及びiii)の総量は100重量%に等しい)
の混合物のフリーラジカル重合によって得られる水溶性又は水分散性コポリマーを可溶化剤として含む弱水溶性有効成分の医薬調製物。 - 弱水溶性有効成分がコポリマー中に固溶体の形態で存在する、請求項7記載の医薬調製物。
- 弱水溶性有効成分として生物活性物質を含む、請求項7又は8記載の医薬調製物。
- 弱水溶性有効成分として有効医薬成分を含む、請求項7〜9のいずれか1項に記載の医薬調製物。
- 経口投与可能な剤形の形態である、請求項10記載の医薬調製物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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DE102005053066A DE102005053066A1 (de) | 2005-11-04 | 2005-11-04 | Verwendung von Copolymeren als Solubilisatoren für in Wasser schwerlöslichen Verbindungen |
DE102005053066.4 | 2005-11-04 | ||
PCT/EP2006/067747 WO2007051743A2 (de) | 2005-11-04 | 2006-10-25 | Verwendung von copolymeren als solubilisatoren für in wasser schwerlösliche verbindungen |
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JP2009515000A JP2009515000A (ja) | 2009-04-09 |
JP5409006B2 true JP5409006B2 (ja) | 2014-02-05 |
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JP2008538334A Active JP5409006B2 (ja) | 2005-11-04 | 2006-10-25 | 弱水溶性化合物のための可溶化剤としてのコポリマーの使用 |
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US (2) | US8158686B2 (ja) |
EP (1) | EP1945183B1 (ja) |
JP (1) | JP5409006B2 (ja) |
CN (1) | CN101299994B (ja) |
DE (1) | DE102005053066A1 (ja) |
WO (1) | WO2007051743A2 (ja) |
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EP1945183A2 (de) | 2008-07-23 |
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CN101299994A (zh) | 2008-11-05 |
WO2007051743A2 (de) | 2007-05-10 |
EP1945183B1 (de) | 2016-03-23 |
JP2009515000A (ja) | 2009-04-09 |
US8632763B2 (en) | 2014-01-21 |
WO2007051743A3 (de) | 2007-07-26 |
US20080293828A1 (en) | 2008-11-27 |
US8158686B2 (en) | 2012-04-17 |
CN101299994B (zh) | 2011-04-06 |
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