JP2010143938A - 滴定投与可能な経皮送達系 - Google Patents
滴定投与可能な経皮送達系 Download PDFInfo
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- JP2010143938A JP2010143938A JP2010018105A JP2010018105A JP2010143938A JP 2010143938 A JP2010143938 A JP 2010143938A JP 2010018105 A JP2010018105 A JP 2010018105A JP 2010018105 A JP2010018105 A JP 2010018105A JP 2010143938 A JP2010143938 A JP 2010143938A
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Abstract
【解決手段】この送達系は一又は複数の境界に沿って連結された複数のパッチ単位を含む。この複数のパッチ単位は、一又は複数の分離線を有する一又は複数の境界に沿って各単位に分割可能である。各パッチ単位は境界により囲まれている。この治療薬パッチは、少なくとも支持層と治療薬を含有する層とを含む。この経皮送達系により患者に送達される治療薬の投与量は、治療毎に貼付されるパッチ単位数に比例する。この送達系によって、医師の指示の下で患者による調整が可能である滴定可能な用量の治療薬を、皮膚または粘膜を通して全身的に投与することが可能になる。
【選択図】なし
Description
本発明は、一般に、治療薬を全身に送達するために宿主の皮膚または粘膜上に貼付される経皮送達系に関する。特に、本発明は、一又は複数の境界に沿って連結された複数のパッチ単位を含む滴定投与可能な経皮送達系に関する。この複数のパッチ単位は、一又は複数の分離線を有する一又は複数の境界に沿った各単位に分割可能である。この経皮送達系により提供される用量は、医師の決定に従って使用者により貼付される単位数に比例する。各パッチ単位は少なくとも支持層と少なくとも一つの治療薬が配合された薬剤層とを含む。この経皮送達系によって、宿主の皮膚または粘膜に、固体支持体上の滴定可能な用量の治療薬を投与することが可能になる。更に、本発明はこの経皮送達系を製造する方法に関する。なお更に、本発明は、本発明の経皮送達系を用いて、滴定可能な量の治療薬を宿主に供給する方法に関する。
治療薬の持続的送達の一つの方法は、経皮パッチなどの経皮送達系の使用である。一般に、経皮パッチは、治療薬と、この経皮デバイスを患者の皮膚に接着するための接着剤とを含有し、これによりこのデバイスから患者の皮膚経由で活性剤を通過させることが可能となる。経皮パッチを使用する種々の利点は、治療薬の一定の送達速度、長い作用時間(このパッチは皮膚に1、3、7日あるいは更に長い間接着する能力がある)、非侵襲的な貼付、患者のコンプライアンスの改善を包含するものであり、またこの送達系を引き剥がすことによりいつでも治療薬の供給を中断できる。この投与手段の重要性は、胃腸管を横断することなく、そして標的部位に到達するのに先立って肝臓系を通る「第1パス」を回避することなく、治療薬を血流に送達することができるという事実にある。これにより、胃腸における医薬の不適合性および胃腸管内での医薬の代謝による望ましくない破壊を回避できる。治療薬が、いったん皮膚層を透過すると、血流中に吸収され、そこで所望の薬理治療効果を発揮することができる。これらのメリットは、専門家が治療薬を投与することを要せずに、得られるだろう。経皮吸収は、このような不適合性と代謝に関する患者間および患者内の変動を最少限にする。経皮吸収により、体内でより一定の医薬濃度を提供し、より大きい医薬効率を実現することが可能となると考えられる。適当な経皮吸収により、治療薬の効果的な投与が可能である。
要性が存在し、長い間認識されながら、現在もなお未達成である。この滴定投与可能な経皮送達系は、最適な用量の治療薬を提供しない経皮パッチの廃棄を最少限にする利点を有する。患者に送達される治療薬の用量の細かいコントロールを可能にする経皮系の必要性も存在する。本発明の経皮送達系は、単一の経皮送達系から調節可能な用量の治療薬を提供することによりこの問題を解決する。本発明は、薬剤師によりストックされる必要がある種々の用量強度を有する異なるタイプの経皮パッチの数を減少させる。例えば、上記に挙げた薬剤師は2つのタイプの本発明の経皮送達系をストックする必要があるのみである。一つのタイプはパッチ当たり25単位の用量を有し、第2のタイプは単位パッチ当たり75単位の用量を有する。これらの2つのタイプのパッチから、25、50、75、100、150単位などの種々の用量強度を送達することが可能である。例えば、50単位の強度を得るためには、単位パッチ当たり25単位の用量のパッチを2つ使用してもよい。100単位の強度を得るためには、同一タイプのパッチを4つ使用してもよい。150単位の強度を得るためには、単位パッチ当たり75単位の用量のパッチを2つ使用してもよい。異なる用量を含有する5種類の異なるパッチをストックする代わりに、2種類の異なるパッチのみをストックすればよい。
本発明は、滴定投与可能な経皮送達系により最適量の治療薬が宿主の皮膚または粘膜に送達されるという本発明者の観察に基づく。本発明の送達系は現状技術の3つの欠点に取り組むものである。第1に、経皮パッチの出現による、患者による自己投与が一般に関係する。貼付指示への患者の遵守が重要性をおびる。本発明の送達系は、本発明の送達系を使用することによって、医師からの簡単な指示に従って患者が治療薬の用量を調節する容易な方法を提供する。第2に、本発明の送達系は、薬剤師がストックする必要がある用量の異なる治療薬パッチの数を減少させる。第3に、本発明の送達系は、最適未満の用量の治療薬を有する経皮パッチの廃棄量を低減させる。
置された被覆層を含み、ここで、各パッチ単位はこの境界上の一又は複数の分離線により規定されている。
in-adhesive layer)を、この支持層の各単位の上面に配置し、それにより支持層上の全ての側部上に境界を残す。次に、被覆層をこの接着層の上面に配置する。
本発明の経皮送達系
一般に、本発明は、患者の皮膚または粘膜に滴定可能な用量の治療薬を送達することが
できる分割可能な経皮送達系に関する。本発明の送達系は、一又は複数の境界に沿って連結された複数のパッチ単位を含む。言い換えれば、この送達系は、分割可能な治療薬パッチの単位を含み、パッチ単位の数に比例した制御された量の治療薬を所望のように送達する。図1に図示するように、滴定可能な経皮送達系10は複数の単位を含む。この実施形態においては、系10には4つの単位20が2行2列に配列されている(すなわち、2×2フォーマット)。各単位20は、治療薬送達ゾーン40を囲む4つの境界30を含む。この複数の治療薬パッチは境界に沿って分割可能である。この境界にミシン目を付けて分離線を形成して、これによりこの治療薬パッチを一又は複数の用量の治療薬を含む一又は複数の単位に分割するのを容易にする。この実施形態においては、各単位20は2つの分離線50を有する。
図3aはマトリックスパッチを使用する本発明の送達系の実施形態を図示する。このマトリックスパッチは2つの相対する表面を含む支持層60を含む。この表面の一つは、治療薬を含有するマトリックス層である薬剤/マトリックス層(a drug with matrix layer)
70および接着層80と接触する。薬剤/マトリックス層70は、パッチ単位の全面積を被覆せず、図1および2に示すように薬剤送達ゾーン40に限定され、薬剤送達ゾーン40を囲む境界30を残す。分離線50は、隣接するパッチ単位20の境界30を分割する。この分離線は、この送達系の個別単位への分割を容易にする。分離線は、支持層中に作られたミシン目または脆弱個所により形成してもよい。
限とするために、不透過性層(図示せず)を、薬剤/マトリックス層70と接触する支持層60の表面上に包含することが必要である(例えば、米国特許第4,336,243号)。治療薬を含有する該マトリックスを、接着層80により皮膚に保持する。パッチと皮膚との接着を更に増すために、接着剤は、境界30の表面上にも存在してよい。
よびポリイソプレン;ポリ酢酸ビニル;尿素ホルムアルデヒド樹脂;フェノールホルムアルデヒド樹脂;レゾルシノールホルムアルデヒド樹脂;セルロース誘導体、例えばエチルセルロース、メチルセルロース、ニトロセルロース、セルロースアセテートブチレートおよびカルボキシメチルセルロース;および天然ガム、例えばグアー、アカシア、ペクチン、澱粉、デキストリン、アルブミン、ゼラチン、カゼイン、などを包含する。これらの接着剤を、当分野でよく知られた粘着剤および安定剤と混合してもよい。
図3bはリザーバータイプのパッチを使用する本発明の送達系の実施形態を図示する。このリザーバータイプのパッチのデザインは、支持層60と、好ましくは、半透過性膜(図示せず)により皮膚から分離されている、溶液または懸濁液の形の薬剤層75を入れたリザーバー小室90とを特徴とする(例えば、米国特許第4,615,699号)。リザーバー小室90は支持層60と連続している。リザーバー小室90内の保護容積を規定する側壁35を有するように支持層60を成型および成形する。リザーバー小室90内に入れてもよい薬剤の量は、リザーバー小室90の寸法と側壁35の高さにより規定される。支持層60は上面65、側壁35を有し、これにより、図1および2に示すような薬剤送達ゾーン40と、薬剤送達ゾーン40全体に広がるリザーバー小室90とが規定される。接着層80を薬剤層75の上面および支持層65の表面上に配置する。これは、境界30を形成するリザーバー境界の周りにも延び、これにより皮膚とのシールを形成し、この経皮系の望ましい数の単位パッチを貼付する皮膚または粘膜に接してリザーバーを保持しうる。この境界では、分離線50は、支持層60により形成された高くなった壁100を通って延びる。
た、ポリエチレングリコールによってエーテル化も可能である。
図3cはモノリシックな薬剤含有接着剤タイプのパッチを使用する本発明の送達系の実施形態を図示する。このモノリシックな薬剤含有接着剤タイプのパッチのデザインは、皮膚に接触する接着層中に治療薬製剤を含有する薬剤含有接着層100、支持層60、および好ましくは剥離ライナー(図示せず)により特徴付けられる。この接着剤は治療薬を放出し、かつまたパッチを皮膚に接着させる。この薬剤含有接着剤タイプ送達系は別個の接着層を必要とせず、パッチの厚さが最小化される(例えば、米国特許第4,751,087号)。それゆえ、薬剤含有接着剤タイプのパッチは薄く、快適である。図1および2に図示されるように、この経皮系の各単位は、薬剤送達ゾーン40を囲む支持層により形成される一又は複数の境界を含む。薬剤含有接着層100は、このパッチ単位の全面積を被覆せず、図1および2に示すように薬剤送達ゾーン40に限定され、薬剤送達ゾーン40を囲む境界30を残す。治療パッチ単位を皮膚に更に固着するために、境界30を接着剤により被覆する。いずれのパッチデザインにおけると同様に、複数の治療パッチを境界に沿って分離できる。この境界にミシン目を付けて分離線50を形成してもよく、これによりこの治療パッチを、一又は複数の投与量の治療薬を含む一又は複数の単位に分割するのが容易になる。
図3dはマルチラミネートの薬剤含有接着剤タイプのパッチを使用する本発明の送達系の実施形態を図示する。このマルチラミネート薬剤含有接着剤タイプパッチのデザインでは、単一支持層60下で、2つ以上の異なる薬剤含有接着層100の間に、追加の半透過性膜200を更に組み入れる(Peterson,T.A.and Dreyer,S.J.Proceed.Intern.Symp.Control.Rel.Bioact.Mater:21:477−478)。各々の薬剤含有接着層100または半透過性の膜200は、パッチ単位の全面積を被覆せず、図1および2に示すように薬剤送達ゾーンに制限され、これにより薬剤送達ゾーンを囲む境界30を残す。各々の半透過性膜200の縁150を支持フィルム60に固着し、これにより薬剤含有接着層を所定の位置に保持する。治療薬パッチ単位を皮膚により固着するために、境界30を接着剤により被覆する。いずれのパッチ設計におけると同様に、複数の治療薬パッチはこの境界に沿って分離しうる。この境界にミシン目を付けて分離線50を形成してもよく、これによりこの治療薬パッチを一又は複数の投与量の治療薬をそれぞれ含む一又は複数の単位に分割するのが容易になる。
Synthetic Polymer Membranes,McGraw Hill,Chapters 4 and 5,1971;1.D.Ferry,Ultrafiltration Membranes,Chemical Review,Vol.18, p.373,1934で記述されているように、いくつかの異なる方法により製造され得る。最も有利な結果を得るためには、当分野で既知の方法に従って、この材料を所望の形態の構造物に成形して、薬剤の所望の放出速度を得なければならない。加えて、本発明のパッチの要素として使用する場合,この材料は、使用される薬剤に対して適切な耐薬品性を有し、かつ非毒性でなければならない。
この経皮パッチ上に配置することができる利用可能な治療薬は、いかなる治療物質または薬剤でもよい。この治療薬は、種々の物理的な状態、例えば、分子分散形、結晶形またはクラスター形のものでよい。治療薬をリポソームによりカプセル化してもよい。本発明で有用な治療薬を含むリポソームを、当分野で既知の多数の方法で製造しうる。例えば、ポリマー性材料の壁または膜を有するマイクロカプセルの製造のためのマイクロカプセル化法は、Microencapsulation and Related Drug Processes by P.D.Deasy,Marcel Dekker Inc.New York(1984)などの文献に記述されている。
ト、ベタメタゾンバレレート、フルオシノロンアセトニド;フルオロメトロン;および塩酸プラモキシン;新生物抑制剤、例えばメトトレキセート、および抗菌剤、例えばバシトラシン、ネオマイシン、エリトロマイシン、塩酸テトラサイクリン、塩酸クロロテトラサイクリン、クロラムフェニコール、オキシテトラサイクリン、ポリミキシンB、ニトロフラクソン、マフェニド(アルファ−アミノ−p−トルエンスルホンアミド)、ヘキサクロロフェン、ベンザルコニウムクロリド、セタルコニウムクロリド、メチルベンゼトニウムクロリド、および硫酸ネオマイシン、を包含する。
ルアミンビスホスフェート)などを包含する。ニトログリセリンが好ましい冠状血管拡張薬である。また、好適なのは、プロパノールオルなどのベータアドレナリン作用性遮断薬である。
エーテル、エステル、アミド、アセタール、塩など、あるいはこれらの薬剤の組成物を製造および使用することができる。上述の薬剤は、1又は複数の他の薬剤と組み合わせて使用可能である。
例えば鉱物油、及びシリコーンであって、乳化剤、例えば脂肪酸のモノ若しくはジグリセリド、またはホスファチド、例えばレシチンを加えたもの、グリコール、ポリアルキレングリコール、懸濁剤、例えばナトリウムカルボキシメチルセルロース、アルギン酸ナトリウム、ポリビニルピロリドンなどを含有する水性媒体、それ単独、あるいはさらに好適な分散剤、例えばレシチン、ステアリン酸ポリオキシエチレンを加えたもの、を包含する。このキャリアは、また、保存剤、安定剤、湿潤剤、乳化剤などの補助剤も含有してよい。
90,Pharm.Tech.14(9):132−140,これを参照してこの明細書に組み込む)。本発明の目的に好適な透過増進剤は、宿主、薬剤に悪影響を及ぼさず、あるいは経皮送達系を形成する材料に変化又は悪影響を及ぼさない。この透過増進剤を単独で使用するか、あるいは許容しうるキャリアなどと混和することができる。
908,213号、および第4,943,435号で開示されているように、活性剤が皮膚まで拡散するポリマーマトリックスフィルム中に治療薬を溶解あるいは懸濁する。
なる治療薬を有する一つ以上の被膜をパッチに塗布してもよく、それにより一つ以上の治療薬および/またはキャリアをパッチ上に組み込んでもよい。用いる治療薬の拡散あるいは溶離速度、並びにこの治療薬を体組織に送達する所望の速度により、この異なる層の配置を決めうる。
本発明は、また、この経皮送達系を製造する方法にも関する。本発明のこの方法は、一般に、上面と下面を有する支持層を形成することを伴う。この支持層を一又は複数の分離線で一つ以上の単位に分割する。薬剤層をこの支持層の各単位の上面に配置し、支持層上の各単位のすべての側部上に境界を残す。接着手段を使用して、患者の皮膚または粘膜上にこの経皮送達系を取り付ける。
。医師の指示通りに使用者が経皮送達系を所望の数の単位に比較的きれいに分離することができる限り、この分離線は種々の形状であってよい。また、患者がこの線に沿って引き裂くか、あるいははさみで切断することができるように、この分離線は、支持体の脆弱箇所または分離線の印刷であってもよい。好ましい分離線はミシン目の線である。この支持体の脆弱箇所は、支持体中に成形あるいは形成された支持体の薄くした部分であってよい。ある場合には、最適な用量を投与するため、経皮送達系を所望の単位の数に確実にきれいに分離するために、脆弱箇所による線とミシン目とを組み合わせることも望ましい。この分離線を構築する他の有用な方法は、米国特許第5,496,605号に記述されている。この分離線によって、経皮送達系を適用毎に所望の数の単位に容易に分割できることが重要である。この経皮送達系を一又は複数の分離線を有する経皮送達系と記述したが、当業者ならば、もう一つの態様において、本発明の特徴として、経皮送達パッチの複数の単位が、同一の1又は複数の分離線に沿って相互に連結されうることを理解するであろう。この特徴に関係なく、本発明は、単一の経皮送達系を用いて種々の投与量の治療薬または薬剤を送達するための経皮送達系および方法を提供する。
し、この組成物を、支持層上の各単位の上面に配置することにより、この薬剤含有接着層を形成する。経皮送達系の各単位が別々に保護されるように、被覆層をこの薬剤含有接着層上に配置する。
本発明の方法を使用して、治療薬または薬剤を、患者の皮膚または粘膜を通して全身的に送達することができる。
Maibach,Marcel Dekker,Inc.,New York,pp.111−119)。
(1) 複数のパッチ単位を含む経皮送達系であって、それぞれのパッチ単位が、
(a)上面と下面を有する支持層;
(b)前記支持層の上面上に配置された不透過性層;
(c)前記不透過性層上に配置され、治療薬のない前記支持層の境界によって囲まれた薬剤層;および
(d)前記薬剤層上及び前記支持層の境界上に配置された接着層 を含み、ここで前記薬剤層は薬剤含有マトリックス層であり、前記複数のパッチ単位は該パッチ単位の一又は複数の境界に沿って互いに連結されており、各パッチ単位が前記パッチ単位の境界上の一又は複数の分離線により規定される、上記経皮送達系;
(2) 前記接着層上に配置された被覆層を更に含む上記(1)に記載の経皮送達系;
(3) 放出制限層を更に含む上記(1)に記載の経皮送達系;
(4) 前記薬剤層が抗菌剤、抗炎症剤、麻酔薬、鎮痛剤、麻酔剤、鎮静剤、トランキライザー、ホルモン、抗糖尿病薬、強心配糖体、鎮痙薬、冠状血管拡張薬、アドレナリン性遮断剤、および栄養剤からなる群から選ばれる薬剤を含む上記(1)に記載の経皮送達系;
(5) 前記薬剤層がフェンタニル、エトルフィン、ブプレノルフィンおよびリドカインからなる群から選ばれる薬剤を含む上記(4)に記載の経皮送達系;
(6) 前記薬剤層中の薬剤がマイクロカプセルによりカプセル化されている上記(4)に記載の経皮送達系;
(7) 前記薬剤層が約0.1から90重量%の薬剤を含有する上記(4)に記載の経皮送達系;
(8) 前記薬剤層が約10から45重量%の薬剤を含有する上記(7)に記載の経皮送達系;
(9) 前記薬剤層が約25から40重量%の薬剤を含有する上記(7)に記載の経皮送達系;
(10)前記薬剤層がドデカノール、ウンデカノール、オクタノール、およびカルボン酸のエステルからなる群から選ばれる軟化剤を更に含む上記(1)に記載の経皮送達系;
(11)前記薬剤層が透過増進剤を更に含む上記(1)に記載の経皮送達系;
(12)前記接着層から前記被覆層を分離することを容易にするために、前記被覆層が切り目を含む上記(2)に記載の経皮送達系;
(13)前記経皮送達系が再封可能な小袋中に貯蔵される上記(1)に記載の経皮送達系;
(14)前記分離線が相互に平行および/または垂直である上記(1)に記載の経皮送達系;
(15)前記分離線がミシン目の線である上記(14)に記載の経皮送達系;
(16)前記分離線が規則的な間隔で配置されている上記(14)に記載の経皮送達系;
(17)前記分離線が約1cmから6cm離れている上記(14)に記載の経皮送達系;
(18)前記経皮送達系中に2から5個のパッチ単位が直列に連結されている上記(14)に記載の経皮送達系;
(19)前記経皮送達系中に4個のパッチ単位が2行および2列で配置されている上記(14)に記載の経皮送達系;
(20)上記(1)に記載の経皮送達系を製造する方法であって、
(a)上面と下面を有する支持層を形成すること、ただし該支持層は一又は複数の分離線により1つ以上のパッチ単位に分割されている;
(b)前記支持層の各パッチ単位の上面上に不透過性層を配置すること;
(c)前記不透過性層上に薬剤含有マトリックス層を配置して、前記支持層のすべての側部上に境界を残すこと;および
(d)前記薬剤含有マトリックス層上及び治療薬のない前記支持層の境界上に接着層を配置すること
を含む、上記製造方法;
(21)更に、前記接着層の上面に被覆層を配置することを含む、上記(20)に記載の経皮送達系の製造方法。
Claims (21)
- 複数のパッチ単位を含む経皮送達系であって、それぞれのパッチ単位が、
(a)上面と下面を有する支持層;
(b)前記支持層の上面上に配置された不透過性層;
(c)前記不透過性層上に配置され、治療薬のない前記支持層の境界によって囲まれた薬剤層;および
(d)前記薬剤層上及び前記支持層の境界上に配置された接着層 を含み、ここで前記薬剤層は薬剤含有マトリックス層であり、前記複数のパッチ単位は該パッチ単位の一又は複数の境界に沿って互いに連結されており、各パッチ単位が前記パッチ単位の境界上の一又は複数の分離線により規定される、上記経皮送達系。 - 前記接着層上に配置された被覆層を更に含む請求項1に記載の経皮送達系。
- 放出制限層を更に含む請求項1に記載の経皮送達系。
- 前記薬剤層が抗菌剤、抗炎症剤、麻酔薬、鎮痛剤、麻酔剤、鎮静剤、トランキライザー、ホルモン、抗糖尿病薬、強心配糖体、鎮痙薬、冠状血管拡張薬、アドレナリン性遮断剤、および栄養剤からなる群から選ばれる薬剤を含む請求項1に記載の経皮送達系。
- 前記薬剤層がフェンタニル、エトルフィン、ブプレノルフィンおよびリドカインからなる群から選ばれる薬剤を含む請求項4に記載の経皮送達系。
- 前記薬剤層中の薬剤がマイクロカプセルによりカプセル化されている請求項4に記載の経皮送達系。
- 前記薬剤層が約0.1から90重量%の薬剤を含有する請求項4に記載の経皮送達系。
- 前記薬剤層が約10から45重量%の薬剤を含有する請求項7に記載の経皮送達系。
- 前記薬剤層が約25から40重量%の薬剤を含有する請求項7に記載の経皮送達系。
- 前記薬剤層がドデカノール、ウンデカノール、オクタノール、およびカルボン酸のエステルからなる群から選ばれる軟化剤を更に含む請求項1に記載の経皮送達系。
- 前記薬剤層が透過増進剤を更に含む請求項1に記載の経皮送達系。
- 前記接着層から前記被覆層を分離することを容易にするために、前記被覆層が切り目を含む請求項2に記載の経皮送達系。
- 前記経皮送達系が再封可能な小袋中に貯蔵される請求項1に記載の経皮送達系。
- 前記分離線が相互に平行および/または垂直である請求項1に記載の経皮送達系。
- 前記分離線がミシン目の線である請求項14に記載の経皮送達系。
- 前記分離線が規則的な間隔で配置されている請求項14に記載の経皮送達系。
- 前記分離線が約1cmから6cm離れている請求項14に記載の経皮送達系。
- 前記経皮送達系中に2から5個のパッチ単位が直列に連結されている請求項14に記載の経皮送達系。
- 前記経皮送達系中に4個のパッチ単位が2行および2列で配置されている請求項14に記載の経皮送達系。
- 請求項1に記載の経皮送達系を製造する方法であって、
(a)上面と下面を有する支持層を形成すること、ただし該支持層は一又は複数の分離線により1つ以上のパッチ単位に分割されている;
(b)前記支持層の各パッチ単位の上面上に不透過性層を配置すること;
(c)前記不透過性層上に薬剤含有マトリックス層を配置して、前記支持層のすべての側部上に境界を残すこと;および
(d)前記薬剤含有マトリックス層上及び治療薬のない前記支持層の境界上に接着層を配置すること
を含む、上記製造方法。 - 更に、前記接着層の上面に被覆層を配置することを含む、請求項20に記載の経皮送達系の製造方法。
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JP5721761B2 (ja) | 2015-05-20 |
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CY1108687T1 (el) | 2014-04-09 |
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JP2015028071A (ja) | 2015-02-12 |
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DK2002826T3 (da) | 2012-11-26 |
JP5977791B2 (ja) | 2016-08-24 |
ES2313995T3 (es) | 2009-03-16 |
JP2004521085A (ja) | 2004-07-15 |
AU2002241792A1 (en) | 2002-06-03 |
US9289397B2 (en) | 2016-03-22 |
JP5501782B2 (ja) | 2014-05-28 |
WO2002041878A2 (en) | 2002-05-30 |
EP2002826A1 (en) | 2008-12-17 |
WO2002041878A3 (en) | 2003-03-13 |
CY1116758T1 (el) | 2017-03-15 |
EP2269595A1 (en) | 2011-01-05 |
DK1333818T3 (da) | 2009-02-02 |
US20140303571A1 (en) | 2014-10-09 |
PT2002826E (pt) | 2012-11-21 |
EP2269595B1 (en) | 2018-01-31 |
ATE410153T1 (de) | 2008-10-15 |
ES2392697T3 (es) | 2012-12-13 |
US20040081685A1 (en) | 2004-04-29 |
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