JP4795962B2 - ポリエチレンオキシドフィルムおよびそれからなる薬物送達系 - Google Patents
ポリエチレンオキシドフィルムおよびそれからなる薬物送達系 Download PDFInfo
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- JP4795962B2 JP4795962B2 JP2006535323A JP2006535323A JP4795962B2 JP 4795962 B2 JP4795962 B2 JP 4795962B2 JP 2006535323 A JP2006535323 A JP 2006535323A JP 2006535323 A JP2006535323 A JP 2006535323A JP 4795962 B2 JP4795962 B2 JP 4795962B2
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- film
- water
- drying
- polymer
- polyethylene oxide
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- 230000008035 nerve activity Effects 0.000 description 1
- 230000002232 neuromuscular Effects 0.000 description 1
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- 229960001597 nifedipine Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 1
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- 108020004707 nucleic acids Proteins 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/006—Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2371/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
- C08J2371/02—Polyalkylene oxides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Nutrition Science (AREA)
- Manufacturing & Machinery (AREA)
- Epidemiology (AREA)
- Physiology (AREA)
- Polymers & Plastics (AREA)
- Zoology (AREA)
- Materials Engineering (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Description
Vo=(2grr)(ρp-ρl)/9μ
のように説明される。
v/Vo=1/(1+κφ)
[式中κ=定数であり、φは、分散した相の体積分率である]
で表される。液相に懸濁した粒子がより多いと、速度が弱まる。粒子寸法は、粒子-粒子の流動相互作用に影響を及ぼすので、粒子の幾何学も重要な因子である。
μ/μo=1+2.5φ
[式中、μoは、連続相の粘度であり、φは、固体の体積分率である]で表すことができる。より高い体積分率では、分散液の粘度は、
μ/μo=1+2.5φ+C1φ2+C2φ3+.....
[式中、Cは定数である]で表すことができる。
τmax=3Vμ/2r
で与えられる。疑似可塑性流体では、このせん断応力領域の粘度は、ニュートン平坦域でゼロせん断速度の粘度になることがよくある。
α(n-1/n)=αo (n-1/n)-((n-1)/(2n-1))(τ/K)1/n(2π/λ)(3+n)/nh(2n+1)/nt
[式中、αは表面波振幅であり、αoは内部振幅であり、λは表面粗さの波長であり、「n」および「K」は、粘性力法則の係数である]のように導かれている。この例では、水平化挙動は、粘度と関連しており、nが減少するにつれて増加し、Kが増加するにつれて減少する。
ポリマーは、水溶性でも、水膨潤性でも、水に不溶性でもよく、または水溶性、水膨潤性、もしくは水に不溶性のポリマーの1種または複数の組合せでもよい。ポリマーは、セルロースまたはセルロース誘導体を含んでいてよい。有用な水溶性ポリマーの具体例としては、ポリエチレンオキシド(PEO)、プルラン、ヒドロキシプロピルメチルセルロース(HPMC)、ヒドロキシエチルセルロース(HPC)、ヒドロキシプロピルセルロース、ポリビニルピロリドン、カルボキシメチルセルロース、ポリビニルアルコール、ナトリウムアルギネート、ポリエチレングリコール、キサンタンガム、トラガカントゴム、グアーガム、アカシアゴム、アラビアゴム、ポリアクリル酸、メチルメタクリラートコポリマー、カルボキシビニルコポリマー、デンプン、ゼラチン、およびこれらの組合せが挙げられるがこの限りでない。有用な水に不溶性のポリマーの具体例としては、エチルセルロース、ヒドロキシプロピルエチルセルロース、セルロースアセテートフタレート、ヒドロキシプロピルメチルセルロースフタレート、およびこれらの組合せが挙げられるがこの限りでない。
用語「制御放出」とは、予め選択された速度または所望される速度での活性物の放出を意味するものである。この速度は、その適用に応じて様々となる。望ましい速度として、速いまたは中程度の放出プロフィールだけでなく、遅延型、持続型、または連続の放出が挙げられる。活性物の最初の大量放出に続く低レベルの持続放出など、放出パターンの組合せを企図する。拍動による薬物放出も企図する。
活性物をフィルムに導入するとき、単位区域あたりの活性物量は、フィルムの均一な分布によって決まる。例えば、フィルムを切断して個々の剤形にするとき、その剤形中の活性物量を相当な正確さで知ることができる。これは、所与の区域中の活性物量が、フィルムの別の部分の同じ寸法の区域中の活性物量と実質的に同一であるために実現される。投与量の正確さは、活性物が薬剤、すなわち薬物であるときに特に有利である。
本発明のフィルム製品は、広い範囲の量の活性成分を収容することができる。フィルムは、必要な用量が多かろうがごく少なかろうが、正確な用量を提供することができる(フィルムの大きさ、およびもとのポリマー/水配合物中の活性物の濃度に応じて決まる)。したがって、フィルムに組み込まれる活性物または薬剤組成物の種類に応じて、活性物の量は、約300mgもの多い量、望ましくは約150mgまでの量、またはマイクログラムの範囲の少ない量、またはこれらの間の量でよい。
消泡および/もしくは脱泡成分も、本発明のフィルムと共に使用してよい。これらの成分は、閉じ込められた空気など、フィルム形成組成物からの空気の除去を助ける。上述のように、そうした閉じ込められた空気は、均一でないフィルムをもたらしかねない。シメチコンは、特に有用な消泡および/もしくは脱泡剤の1つである。しかし、本発明は、そのように限定せず、他の消泡および/もしくは脱泡剤も適切に使用してよい。
他の様々な成分およびフィラーも本発明のフィルムに加えることができる。これらには、限定するものではないが、界面活性剤;ポリアルコール;フィルムから酸素を放出してより滑らかなフィルム表面にしやすくする、シリコーン含有化合物などの消泡剤;成分の分散の維持を助ける、ペクチン、カラギーナン、ゼラチンなどの熱硬化性ゲル;および所定の活性化合物の溶解性および/または安定性を向上させる、シクロデキストリンやかご分子などの包接化合物が含まれる。
本発明のフィルムは、乾燥させる前にシートに成形しなければならない。所望の成分を合わせて、ポリマー、水、および活性物もしくは所望される他の成分を含む多成分マトリックスを生成した後、この配合物を、多成分マトリックスの押出、コーティング、塗布、流延、延伸など、当業界で知られている方法によってシートまたはフィルムに成形する。多層フィルムが所望される場合、これは、組成が同じでも異なるものでもよい2つ以上の成分配合物の同時押出によって実現される。多層フィルムは、すでに生成されたフィルム層上に配合物をコーティング、延伸、または流延して得ることもできる。
乾燥工程も、フィルム組成物の均一性の維持に寄与する因子である。制御された乾燥工程は、粘度を増大させる組成物、または例えばポリマーの選択によって粘度が制御されている組成物がなく、フィルム内の成分が凝集または塊状化する傾向が増大しているかもしれないときに特に重要である。制御型の乾燥工程を必要としない、正確な用量を含むフィルムを形成する代替法は、所定のウェルでフィルムの流延を行うものになるはずである。この方法では、成分が凝集することがあったとしても、各ウェルがそれ自体剤形の境界を画定しているので、活性物が隣接する剤形に移動することにならない。
フィルム製造工程の際に、本発明のフィルムの化学的および物理的な均一性を試験することが望ましいであろう。特に、フィルムのサンプルを取り出し、様々なサンプル同士を比べてフィルム成分の均一性を試験することができる。フィルムの厚みおよび全体的な概観からも均一性を確認することができる。特に薬剤活性成分を含有するフィルムでは、安全性および有効性の点から均一なフィルムが求められる。
本発明の薄型フィルムは、多くの用途に適する。このフィルムは、成分が高度に均一になるので、医薬品を組み込むのに特によく適するようになっている。さらに、フィルムの構築に使用するポリマーを選択して、一定範囲のフィルム崩壊時間を可能にすることができる。フィルムの崩壊にかかる時間を変動または延長させると、活性物が放出される速度の制御を実現することができ、これによって持続放出送達系が可能となり得る。また、このフィルムを使用して、いろいろな体の表面、特に、口、肛門、膣、眼、創傷面(皮膚表面上または手術の際などの体内)、および同様の表面など、粘膜を含む表面のいずれかに活性物を投与することができる。
(参考例A〜I)
本発明の水溶性の薄膜組成物は、表1に記載の量を用いて調製する。
分解時間が調整され、水溶性および水不溶性ポリマーの組合せを含むフィルムと活性物の制御放出が可能な水溶性フィルムを、概ね表3に記載された量を用いて調製する。
正確な投薬を提供するフィルムを調製する代替法は、参考例組成物A〜Iのいずれにも用いることができる。その方法は、まず混合してその成分を合わせることで始まる。次いで成分を合わせたものを、個々の穴または型の中に分配する。そのような方法では、乾燥中での成分の凝集は、個々の穴によって防止される。
組成物P〜Wは、本発明に関連しているので、フィルム生産の種々の条件間での相互作用を実証するために調製した。下記表6の成分を組み合わせ、下記表7にリストしたプロセスパラメータを用いてフィルムに形成し、フィルムの下部乾燥を組み込むように設計された6mの乾燥トンネル中で調製した。それぞれ参考例は、得られたフィルム製品に及ぼす異なる成分配合および処理技術の影響を示している。
消泡剤/脱泡剤(すなわちシメチコン)の混合により、フィルム製品中の気泡を実質的に減少または排除した均一なフィルムを提供するばかりでなく、また他の利点も与えるフィルムを提供した。このフィルムは、より望ましい感覚的な性状を示した。フィルムは、「紙のようでない」改善された食感を持ち、その使用者により良好な口あたりを提供した。
本発明の以下の参考例では、界面活性剤としてエトキシ化ヒマシ油を用いる、またはこれに対して界面活性剤、可塑剤および/または多価アルコールを用いないフィルムとフィルム形成組成物を記述する。本発明のフィルムまたはフィルム形成組成物には、基本的に界面活性剤が存在しないことが望ましい。さらに、本発明のフィルムまたはフィルム形成組成物は、基本的に界面活性剤が存在しないように配合されることが望ましい。さらに、本発明のフィルムまたはフィルム形成組成物は、可塑剤が基本的に存在しないように配合されることが望ましい。またさらに、本発明のフィルムまたはフィルム形成組成物は、多価アルコールが基本的に存在しないように配合されることが望ましい。さらに、本発明のフィルムまたはフィルム形成組成物は、界面活性剤と可塑剤が基本的に存在しないように配合されることが望ましい。さらにまた、本発明のフィルムまたはフィルム形成組成物は、界面活性剤、可塑剤および多価アルコールが基本的に存在しないように配合されることが望ましい。
本発明の以下の参考例は、着香料および味マスキング補助物をも含む、味をマスキングした、薬剤として活性な物質を用いるフィルムおよびフィルム形成組成物を記載する。味マスキング着香料は、味覚受容体に作用して、異なる典型的な不快な風味を伝える受容体を遮蔽する成分である。
参考例の薄膜組成物を、表14に記載した量を用いて調製した。
参考例のフィルム組成物は、表15に記載された量を用いて調製した。
表15の成分を、CHに関し記載した量で、混合して合わせ、次いで350ミクロンのスムーズバーにより、K-Control Coaterを用いて、放出紙上の3枚のフィルムに流延した。フィルムを、均一に熱を分布させるファーナスフィルタで裏張りしたトレイ上で、80℃の空気乾燥機中で9分間乾燥した。フィルムは水分約2.20%まで乾燥した。図17で示すように、乾燥フィルム200は条痕がなくて均一だった、すなわち粒子凝集は生じなかった。活性粒子は乾燥フィルム中で無傷なようであった。フィルムは十分な強度を示し、亀裂なしで180°曲げ試験に合格し、フィルムは圧力により半分に折れ曲がった。
参考例の薄膜組成物を、表16に記載された量を用いて調製した。
以下の実施例は、ポリエチレンオキサイド(PEO)を単独で、またはヒドロキシプロピルセルロース(HPC)もしくはヒドロキシプロピルメチルセルロース(HPMC)と組み合わせて含有する、水溶性ポリマーを含む本発明のフィルム組成物を記載する。薄膜組成物を表19に記載したポリマー量を用いて調製した。
以下の本発明の参考例は、PEOまたはPEO重合体混合物と活性成分を含むフィルムを記載する。これらの成分を持つ薄膜組成物を、表21で記載される量を用いて調製した。
以下の本発明の実施例は、PEOまたはPEO-HPCポリマー混合物を含むフィルムを記載する。このフィルム組成物は様々な分子量のPEOを含んでいる。これらの成分を持つ薄膜組成物を、表22(ポリマー成分の重量パーセントで記載された)で記載された量を用いて調製した。
以下の参考例は、PEOとポリビニルピロリドン(PVP)重合体混合物を含むフィルムを記載する。これらの成分を持つ薄膜組成物を、表24に記載された量を用いて調製した。特に、フィルムのポリマー成分は、約80%のPEOおよび20%のPVP、すなわち、PEO対PVPの比率4:1を含んでいた。
以下の本発明の実施例は、PEO系ポリマー成分を含む押出成形フィルムを記載する。フィルム組成物をECの表25およびEDの表26に記載された量を用いて調製した。
以下の本発明の実施例は、抗膨張剤を含むフィルムを記載する。PEO重合体混合物および抗膨張剤(シメチコン)を含む薄膜組成物を、表28に記載された量を用いて調製した。
以下の本発明の実施例は、PEOまたはPEO重合体混合物を含むフィルムを記載する。特に、PEOに、ポリビニルピロリドン(PVP)、デンプン(プレゼラチン化加工コーンスターチ)、カルボキシルメチルセルロースナトリウム(CMC)、ヒドロキシプロピルセルロース(HPC)、ヒドロキシプロピルメチルセルロース(HPMC)またはポリビニルアルコール(PVA)を組み込んで、フィルムのポリマー成分を形成した。これらの成分を持つ薄膜組成物を、本発明の方法に従い、図38に記載された量を用いて調製した。
以下の本発明の実施例は、PEOまたはPEO重合体の混合物(HPCと共に)および種々の活性成分を含むフィルムを記載する。これらの成分を持つ薄膜組成物を本発明の方法に従い、表30および31に記載された量を用いて調製した。
Claims (19)
- ポリエチレンオキシドを親水性セルロースポリマーとの組合せとして含む水溶性ポリマーの少なくとも1種を含む、経口投与用フィルム製品であって、
前記親水性セルロースポリマーが、ヒドロキシプロピルメチルセルロース、ヒドロキシプロピルセルロース、及びそれらの組合せからなる群から選択され、
前記水溶性ポリマーが50から70重量%のポリエチレンオキシドを含む、
経口投与用フィルム製品。 - 界面活性剤およびポリアルコールが加えられていない、請求項1に記載のフィルム製品。
- 美容成分、薬剤、生理活性物質、およびこれらの組合せからなる群から選択される活性成分をさらに含む、請求項1に記載のフィルム製品。
- 前記活性成分がロラタジンである、請求項3に記載のフィルム製品。
- 前記生理活性物質が、酵素、抗原、およびアレルゲンからなる群から選択される、請求項3に記載のフィルム製品。
- 高密度化剤をさらに含む、請求項1に記載のフィルム製品。
- 前記高密度化剤がシメチコンである、請求項6に記載のフィルム製品。
- 溶解性増強剤をさらに含む、請求項1に記載のフィルム製品。
- PEOを第2のポリマー成分との組合せとして含む水溶性ポリマーの少なくとも1種を含む、経口投与用フィルム製品であって、
前記水溶性ポリマーが50から75重量%のPEOを含む、
経口投与用フィルム製品。 - 50%〜75重量%のポリエチレンオキシド、ヒドロキシプロピルメチルセルロース、およびヒドロキシプロピルセルロースを含む水溶性ポリマーの少なくとも1種;
活性成分;
スクラロース;
沈降炭酸カルシウム;
少なくとも1種の着香剤;
シメチコン;
水;および
少なくとも1種の着色剤を含み、
可塑剤、界面活性剤、およびポリアルコールが加えられていない、経口投与用フィルム製品。 - ポリエチレンオキシドをヒドロキシプロピルメチルセルロースおよびヒドロキシプロピルセルロースからなる群から選択されたポリマーとの組合せとして含む水溶性ポリマーの少なくとも1種を含み、
有機溶媒、可塑剤、界面活性剤、およびポリアルコールを含まない、経口投与用水溶性フィルム組成物であって、
前記水溶性ポリマーが50から75重量%のポリエチレンオキシドを含む、
経口投与用水溶性フィルム組成物。 - 美容成分、薬剤、生理活性物質、およびこれらの組合せからなる群から選択される活性成分をさらに含む、請求項11に記載の組成物。
- 経口投与用フィルムの製造方法であって、
(a)ポリエチレンオキシドを親水性セルロースポリマーとの組合せとして含む水溶性ポリマーの少なくとも1種、溶媒、および活性成分を混ぜ合わせて、マトリックスを生成する工程であって、前記親水性セルロースポリマーがヒドロキシプロピルメチルセルロース、ヒドロキシプロピルセルロース、及びそれらの組合せからなる群から選択され、前記水溶性ポリマーが50から70重量%のポリエチレンオキシドを含む、工程と、
(b)前記マトリックスからフィルムを形成させる工程と、
(c)前記フィルムを乾燥させる工程
を含み、前記フィルムは可塑剤を加えられていない方法。 - 前記マトリックスからフィルムを形成させる工程が、上部側面および下部側面を有する表面に前記マトリックスを流延することをさらに含む、請求項13に記載の方法。
- 前記フィルムを乾燥させる工程が、前記表面の前記下部側面に熱を当てることをさらに含む、請求項13に記載の方法。
- 成分が均一に分布しているフィルムの製造方法であって、
(a)ポリエチレンオキシドを親水性セルロースポリマーとの組合せとして含む水溶性ポリマーの少なくとも1種、および活性成分を混ぜ合わせる工程であって、前記親水性セルロースポリマーがヒドロキシプロピルメチルセルロース、ヒドロキシプロピルセルロース、及びそれらの組合せからなる群から選択され、前記水溶性ポリマーが50から70重量%のポリエチレンオキシドを含む、工程と、
(b)前記マトリックスを押出してフィルムを形成させる工程
を含む、方法。 - 前記押し出されたフィルムを冷却する工程をさらに含む、請求項16に記載の方法。
- (a)ポリエチレンオキシドを親水性セルロースポリマーとの組合せとして含む水溶性ポリマーの少なくとも1種、溶媒、および活性成分を混ぜ合わせる工程であって、前記親水性セルロースポリマーがヒドロキシプロピルメチルセルロース、ヒドロキシプロピルセルロース、及びそれらの組合せからなる群から選択され、前記水溶性ポリマーが50から70重量%のポリエチレンオキシドを含む、工程と、
(b)前記マトリックスからフィルムを形成させる工程と、
(c)前記フィルムを乾燥させる工程
によって生成され、
可塑剤が加えられていない、経口投与用フィルム製品。 - フィルムとして堆積し乾燥すると活性成分の経口投与用送達系になる、親水性セルロースポリマーとポリエチレンオキシドとのプレミックスであって、
前記親水性セルロースポリマーがヒドロキシプロピルメチルセルロース、ヒドロキシプロピルセルロース、及びそれらの組合せからなる群から選択され、
前記水溶性ポリマーが50から70重量%のポリエチレンオキシドを含む、
プレミックス。
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AU (2) | AU2004319243B2 (ja) |
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CA (1) | CA2544776C (ja) |
NO (1) | NO20056060L (ja) |
WO (1) | WO2006031209A1 (ja) |
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- 2004-05-28 JP JP2006535323A patent/JP4795962B2/ja not_active Expired - Lifetime
- 2004-05-28 EP EP04753818A patent/EP1663178A1/en not_active Withdrawn
- 2004-05-28 CN CN2012101343508A patent/CN102670568A/zh active Pending
- 2004-05-28 WO PCT/US2004/017076 patent/WO2006031209A1/en active Application Filing
- 2004-05-28 BR BRPI0410956-2A patent/BRPI0410956A/pt not_active Application Discontinuation
- 2004-05-28 EP EP17151005.0A patent/EP3210601A1/en not_active Withdrawn
- 2004-05-28 AU AU2004319243A patent/AU2004319243B2/en not_active Expired
- 2004-05-28 EP EP13189513.8A patent/EP2716284A3/en not_active Withdrawn
- 2004-05-28 CA CA2544776A patent/CA2544776C/en not_active Expired - Lifetime
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2005
- 2005-12-20 NO NO20056060A patent/NO20056060L/no not_active Application Discontinuation
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Also Published As
Publication number | Publication date |
---|---|
WO2006031209A1 (en) | 2006-03-23 |
JP2007500252A (ja) | 2007-01-11 |
EP3210601A1 (en) | 2017-08-30 |
AU2004319243A8 (en) | 2008-08-07 |
CA2544776C (en) | 2014-04-15 |
AU2010214780A1 (en) | 2010-09-23 |
CN1812773A (zh) | 2006-08-02 |
AU2004319243B2 (en) | 2010-06-03 |
AU2004319243A1 (en) | 2006-01-12 |
CA2544776A1 (en) | 2006-03-23 |
CN102670568A (zh) | 2012-09-19 |
EP2716284A2 (en) | 2014-04-09 |
EP2716284A3 (en) | 2014-11-05 |
NO20056060L (no) | 2006-02-07 |
CN1812773B (zh) | 2012-06-27 |
BRPI0410956A (pt) | 2006-07-04 |
EP1663178A1 (en) | 2006-06-07 |
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