JP2009527583A - ジケトピペラジン及び活性薬剤を含有する微粒子の製剤特性の改善方法 - Google Patents
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Abstract
【選択図】図1
Description
本願は、2006年2月22日に出願された米国仮特許出願第60/776,605号の、米国特許法施行規則第119条(e)の下の利益を主張するものであり、その内容は、その全体が本明細書に参照によって組み入れられる。
発明の分野
本発明は、乾燥粉末医薬の分野に関する。本発明は、改善された空気力学的性能を備えた粒子を得る方法、又は活性薬剤がより安定に存在し、効果的に送達される粒子を得る方法、を開示する。より具体的には、本発明は、乾燥方法に関し、特に、ジケトピペラジン−インシュリン(DKP−インシュリン)粒子を噴霧乾燥する方法に関する。本発明の乾燥粉末は、肺送達のための医薬製剤としての有用性を備える。
乾燥粉末組成物として粒子を調製するために、数多くの異なる方法が、当該技術分野において用いられている。これらの方法には、例えば、凍結乾燥、蒸発、相分離、及び噴霧乾燥(PCT特許出願:WO91/16038を参照されたい。)が含まれる。乾燥粉末医薬の製造において、ある方法では、溶液中の前記成分から開始し、溶媒を除去することにより粉末の粒子が形成される。別の方法においては、独立した、初期の段階で、例えば沈殿によって、粒子が形成され、懸濁液中の粒子を得ることができ、これは、次いで乾燥させる必要がある。特に、懸濁液中の粒子から溶媒を乾燥又は除去するために、凍結乾燥や蒸発のような方法がよく用いられる一方、噴霧乾燥は、より典型的には溶液から粒子を形成するために用いられてきた。例えば、米国特許第5,976,574号;第5,985,248号;第6,001,336号;第6,051,256号;第6,077,543号;第6,365,190号;第6,372,258号;第6,423,344号;第6,479,049号;第6,509,006号;第6,569,406号;第6,572,893号;第6,582,728号;第6,838,076号;及び、第6,896,906号を参照されたい。
本発明は、改善された粒子、及び/又は改善された乾燥粉末を獲得する方法に関する。本発明により意図されるこれらの粒子及び粉末は、活性薬剤と共にジケトピペラジン誘導体から成る。本発明の具体的な態様において、前記粒子は、前記噴霧乾燥工程により乾燥される際、凍結乾燥と比較して、改善された安定性、空気力学的特性、及び薬力学的特性を有しているジケトピペラジン−インシュリン粒子製剤である。別の態様において、噴霧乾燥されたジケトピペラジン−インシュリン粒子製剤又は乾燥粉末が提供される。
本発明は、改善された空気力学的性能を備え、活性薬剤がより安定に存在し、効率的に送達される粒子を獲得する方法を開示する。より詳細には、本発明は、ジケトピペラジン−インシュリン粒子を乾燥させる、特に噴霧乾燥させる方法に関する。前記乾燥粉末は、肺送達のための医薬製剤としての有用性を有している。他の態様においては、前記ジケトピペラジン−インシュリン乾燥粉末は、鼻腔内投与のために用いることができる。
本発明は、改善された、ある薬剤学的特性を備えた乾燥粉末をも提供し、その改善された特性とは、活性薬剤の改善された送達であり、それによって、より大きな糖処理が達成される。
以下の図面は、本願の一部を構成し、更に本発明の特定の局面を例示するために含まれている。本発明は、本明細書に示された特定の態様の詳細な記載と併せて、これらの図面の1つ、又は2つ以上を参照することにより、よりよく理解することができる。
いずれの医薬粒子でも、成功するかどうかは、疾患又は状態を治療する際の有効性のみに因るのではなく、他の公知の治療に対して優れた薬剤学的特性を有していることにも因る。乾燥粉末粒子中に見出される望ましい薬剤学的特性としては、改善された空気力学、薬力学、及び安定性が挙げられる。しかし、このような特性を有している粒子を製造することは、当該技術分野に於ける現在の課題である。当該技術分野に於けるこの目標を達成するためのアプローチの一つは、粒子を製造するために用いられる方法にある。
本発明において用いられるように、噴霧乾燥は、液状媒質(溶媒)中懸濁液中の粒子を装填、そして/又は乾燥させるために用いられる熱処理方法である。本明細書の実施例に開示されるように、ジケトピペラジン粒子の懸濁液及びインシュリン溶液を混合する。その後、インシュリン分子のうちいくつか、又はすべてが、ジケトピペラジン粒子に結合する。種々の態様において、ジケトピペラジン−インシュリン粒子は、その後噴霧乾燥により装填そして/又は乾燥され、乾燥粉末が得られる。それに代わる態様においては、粒子が沈殿する前に、活性薬剤をジケトピペラジン溶液に加える。
噴霧乾燥は、呼吸可能な粒径を有し、低い含水量、及びエアロゾル化を可能にする他の特性を備えた、均質な組成の粉末が結果として得られる条件下で行われる。得られる粉末の粒径は、粒子の約98(質量)%超が約10μm以下の直径を有し、粒子の約90(質量)%が5μm未満の直径を有しているようなものが好ましい。あるいは、粒子の約95(質量)%が約10μmの未満直径を有し、粒子の約80(質量)%が5μm未満の直径を有している。特定の態様においては、乾燥粉末が、直径が1〜5μmの平均粒径を有している。先行する態様は、特に肺送達に於ける粉末の使用に関する。平均粒径は、気道のどの場所に粒子が沈着するかに影響し、そして、これらを大量処理する際の特性にも影響し得る。例えば、鼻腔内沈着は20μmを超える平均直径を有した粒子が好ましい。別の態様においては、粉末は、錠剤の形成に用いたり、カプセルに詰めたり、又は経口投与又は注射のために再懸濁させることができる。従って、種々の態様において、乾燥粉末は、約10μm、20μm、30μm、40μm、50μm、60μm、70μm、80μm、90μm、100μmを超える平均粒径を有した粒子を含むことができる。ある別の態様においては、前記乾燥粉末は約100μm〜約500μmの平均粒径を有した粒子を含むことができる。別の態様においては、乾燥粉末は約1mm未満の平均粒径を有した粒子を含むことができる。
「粉末」という用語は、吸入器中に分散させることができ、そして対象に吸入させることのできる細かい固体粒子よりなる組成物を意味する。好ましい態様において、前記粒子は肺、すなわち肺胞に到達する。このような粉末は「呼吸可能」と呼ばれる。好ましくは、この平均粒径は、直径約10ミクロン(μm)未満であり、比較的均一な球体の形状分布を備えている。より好ましくは、この直径は約7.5μm未満であり、最も好ましくは約5.0μm未満である。通常、粒径分布は直径約0.1μmと約8μmの間にあり、特に約0.3μmから約5μmである。
ジケトピペラジンを、活性薬剤を含ませた粒子、又は活性薬剤が吸着することのできる粒子、に形成することができる。本発明のジケトピペラジンには、以下に限定されないが、(E)−3,6−ビス[4−(N−カルボキシル−2−プロペニル)アミドブチル]−2,5−ジケトピペラジン(フマリルジケトピペラジン、又はFDKPとも呼ぶことができる)としても知られている、3,6−ジ(フマリル−4−アミノブチル)−2,5−ジケトピペラジンが包含される。
本発明の態様は、活性薬剤をジケトピペラジンと組み合わせた粒子を用いる。「活性薬剤」という用語は、本明細書において、本発明のジケトピペラジン中に又はジケトピペラジンに対して、カプセル化され、会合し、結合し、複合体を形成し又は捕捉された、治療薬、又は分子(例えば、タンパク質若しくはペプチド又は生体分子)を指す。概して、いずれの形態の薬剤も、本発明のジケトピペラジンと組み合わせることができる。本発明において考慮されるような活性薬剤は、電荷を帯びていてもいなくてもよい。
更なる態様において、本発明により、粒子製剤に含ませることのできるジケトピペラジンと活性薬剤を含む懸濁液又は溶液に含有させることのできる安定化剤の使用が考慮される。
本発明によって考慮される界面活性剤には、以下に限定されないが、ポリソルベート80(PS80)、レシチン、ホスファチジルコリン、DPPC、ドデシル硫酸ナトリウム、及びイオン性洗剤が含まれる。
本発明の好ましい態様を示すために、以下の実施例が含まれる。以下の実施例に開示される技術は、本発明の実施において、よく機能する、発明者によって明らかにされた技術を代表し、従ってその実施のための好ましい形態を構成すると考えられるということは当業者によってよく理解されるはずである。しかし、当業者は、本発明の開示の観点の下、本発明の精神と範囲を逸脱することなく、同様のもの又は同様の結果をもたらす、開示された特定の態様において、多くの変更をすることが可能であることをよく理解するはずである。
ジケトピペラジン誘導体、3,6−ビス[N−フマリル−N−(n−ブチル)アミノ]−2,5−ジケトピペラジン(3,6−ジ(フマリル−4−アミノブチル)−2,5−ジケトピペラジン、フマリルジケトピペラジン又はFDKPとも称され;(E)−3,6−ビス[4−(N−カルボキシ−2−プロペニル)アミドブチル]−2,5−ジケトピペラジンとも呼ばれる)を沈殿させ、洗浄した。pHをおよそ4.45に調節することによりFDKP粒子上にインシュリンを装填し、FDKP−インシュリン粒子を噴霧乾燥させ、FDKP−インシュリン乾燥粉末を得た。pHを約4.45とすることにより、インシュリンのFDKP粒子への結合が増加することが明らかとなり、このことは、双方が2006年9月14日に出願された米国特許出願第11/532,063号及び第11/532,025号、並びに2005年9月14日に出願された米国仮特許出願番号第60/717,524号に開示されている。
上記のように調製された粒子を用いて、噴霧乾燥機の入り口温度及び工程の拡張性を、下記の表2に示されるように評価した。これらの実験において、入り口温度は105℃から140℃まで変化し、出口温度は75℃で一定に保たれた。ノズル圧力は0.6バールで一定に保たれた。
これらの実験において、既知量のジケトピペラジン粒子を水中に懸濁させた。既知濃度のインシュリン溶液を十分に該懸濁液に加え、理論上11.4%インシュリンの組成物を得た。フマリルジケトピペラジン−インシュリンスラリーを噴霧乾燥の前に滴定し、pHはおよそ4.45であった。
上記のデータは、以下を示す:1)霧化圧を増加させると一次粒子の凝集が減少する;2)入り口温度を増加させても粒子の空気力学にはほとんど影響がなかった;3)インシュリンの安定性に対して、入り口温度増加の負の影響は観察されなかった;4)入り口温度の増加により、一次粒子の凝集がより大きくなった;5)噴霧乾燥された粒子は、同じ組成の凍結乾燥された粒子と比較した場合、インシュリンの安定性を増加させた;及び6)噴霧乾燥された粒子は、凍結乾燥された粒子と同様の形態を有していた。
入り口温度及び霧化圧を、110、120及び130℃の入り口温度、及び0.7、0.9及び1.1バールの霧化圧を用いてさらに評価した(表3)。
表3に列挙されたサンプルはインシュリンの安定性及び粒子凝集について分析した。図7A及び7Bに示されるように、この結果は、噴霧乾燥されたサンプルが同等の凍結乾燥された粉末よりもインシュリンの減少が少ないことを示したという点において、実施例1〜3の結果と一致した(図7A及び7Bに於けるボトムバー;pH4.5に調整された凍結乾燥されたサンプルに用いられる粒子の装填は、上記実施例1で議論されたように、FDKP粒子へのインシュリンの結合を増加させる)。
ラット吹送調査によるデータは、噴霧乾燥されたFDKP−インシュリン粉末により、凍結乾燥された物質により提供されたものと少なくとも同等の糖処理が与えられることを示した。図8は、ラットへ凍結乾燥された11.4%FDKP−インシュリン粒子及び噴霧乾燥された11.4%FDKP−インシュリン粒子を吹送した後の薬力学的な分析結果(血糖減少)の比較を示す。噴霧乾燥されたFDKP−インシュリン粉末のグルコースを低下させる能力は、凍結乾燥されたFDKP−インシュリン粉末の能力と同等であることがわかった。
フマリルジケトピペラジン(FDKP)−インシュリン粒子を、上記と同様の方法で調製した。すなわち、粒子をインシュリン溶液と混合し、11.4重量%のインシュリンを含む粒子を得、該粒子へのインシュリンの吸着を促進するためにpHを調整した。得られた粒子懸濁液を、噴霧乾燥又は凍結乾燥のいずれかにより乾燥させた。表4は、工業規模の噴霧乾燥機を用いて調製された2つの200gのロットと凍結乾燥されたサンプルとの比較を示す。このバルク粉末は、空気力学的性能について試験した。インシュリン減少及びA21−デサミドインシュリンの形成についての評価の前に、バルク粉末の更なるサンプルを40℃/75%RHで15日間保管した。この噴霧乾燥された粉末は、平均的なフィル上の呼吸性分画(RF/フィル(%))62%を示し;凍結乾燥された粉末の平均値54%と比較した。噴霧乾燥された粉末はまた、すぐれた安定性を示した。噴霧乾燥された粉末のインシュリンの減少及びA−21形成は、凍結乾燥された粉末のそれらの約半分であった。
更に改善された工程おいては、FDKP溶液の供給温度を管理した。フマリルジケトピペラジン(FDKP)の貯蔵液を調製し、l1℃、13℃、15℃、17℃又は19℃へと冷却し、FDKP粒子を沈殿させた。粒子を装填及び乾燥させるために、2つの異なる方策を用いた。1つの方策においては、沈殿したジケトピペラジン粒子を洗浄し、インシュリン溶液を加え、インシュリンの該粒子への吸着を促進するためにpHを調整し、この混合物を、液体窒素に滴下することにより凍結させ、そして、得られるペレットを凍結乾燥(lyophilize)(凍結乾燥(freeze-dry))させ、ジケトピペラジン−インシュリン乾燥粉末を得た。もう一つの対応する手順においては、沈殿したジケトピペラジン粒子を洗浄し、インシュリン溶液を加え、pHを調整し、そして、ジケトピペラジン−インシュリン粒子懸濁液を噴霧乾燥し、ジケトピペラジン−インシュリン乾燥粉末を得た。
特許請求の範囲に於ける「又は」という用語は、別の選択肢のみを言及するように明確に述べられていない限り、即ちそれぞれが相互に排他的でない場合、「及び/又は」を意味するものとして用いられるが、本開示においては、別の選択肢のみと「及び/又は」に言及する定義が支持されている。
本発明の他の目的、特徴及び長所は、本明細書に提供された詳細な記載により明らかとなるであろう。しかし、本発明の精神及び範囲内での種々の改変及び修正が、詳細な説明により当業者にとって明らかになるであろうから、詳細な説明及び特定の実施例は、本発明の特定の態様を示している一方、例示としてのみ与えられることを理解すべきである。
Claims (31)
- 以下の工程:
ジケトピペラジンの溶液を提供し;
活性薬剤の溶液を提供し;
ジケトピペラジンの粒子を形成し;
前記ジケトピペラジン及び前記活性薬剤を組み合わせ;そして、その後、
噴霧乾燥により溶媒を取り除き、乾燥粉末を得ること;
を含み、前記乾燥粉末は、凍結乾燥により溶媒を取り除くことにより得られる乾燥粉末と比較して改善された薬剤学的特性を備えている、改善された薬剤学的特性を備えた乾燥粉末医薬の調製方法。 - 前記改善された薬剤学的特性が、活性薬剤の改善された安定性、粉末の密度の増加、及び乾燥粉末の改善された空気力学的性能、より成る群から選択される、請求項1に記載の方法。
- 活性薬剤が、インシュリン、カルシトニン、副甲状腺ホルモン1−34、副甲状腺ホルモンの生理活性フラグメント、オクトレオチド、ロイプロリド、並びにRSVペプチド、フェルバメイト、カンナビノイドアンタゴニスト及び/又はアゴニスト、ムスカリンアンタゴニスト及び/又はアゴニスト、ヘパリン、低分子量ヘパリン、クロモリン、シルデナフィル、バルデナフィル、タダラフィル、成長ホルモン、AZT、DDI、GCSF、ラモトリジン、絨毛性ゴナドトロピン放出因子、黄体形成ホルモン放出ホルモン、β−ガラクトシダーゼ、GLP−1、エキセンディン1−4、グレリン、及びこれらのフラグメントより成る群から選択される、請求項1に記載の方法。
- 前記活性薬剤がペプチド又はタンパク質である、請求項1に記載の方法。
- 前記活性薬剤がインシュリン又はその類似体である、請求項3に記載の方法。
- 前記インシュリンが前記乾燥粉末製剤の約3重量%乃至約50重量%の範囲内である、請求項5に記載の方法。
- 前記インシュリンが前記乾燥粉末製剤の約7重量%乃至約19重量%の範囲内である、請求項6に記載の方法。
- 前記インシュリンが前記乾燥粉末製剤の約11重量%である、請求項7に記載の方法。
- 前記インシュリンが前記乾燥粉末製剤の約15重量%である、請求項7に記載の方法。
- 前記ジケトピペラジンは、化学式2,5−ジケト−3,6−ジ(4−X−アミノブチル)ピペラジンを有し、ここで、Xはスクシニル、グルタリル、マレイル、及びフマリルより成る群から選択される、請求項1に記載の方法。
- 前記ジケトピペラジンがフマリルジケトピペラジンである、請求項10に記載の方法。
- 前記改善された薬剤学的特性が、前記粒子の前記活性薬剤の改善された安定性である、請求項1に記載の方法。
- 前記改善された薬剤学的特性が、前記粒子の改善された空気力学的性能である、請求項1に記載の方法。
- 前記改善された薬剤学的特性が、前記粉末の密度の増加である、請求項1に記載の方法。
- 前記空気力学的性能が、カートリッジフィル上の呼吸性分画のパーセントによって測定されるものである、請求項13に記載の方法。
- 前記呼吸性分画のパーセントが約40%を超える、請求項15に記載の方法。
- 前記呼吸性分画のパーセントが約50%を超える、請求項15に記載の方法。
- 前記呼吸性分画のパーセントが約60%を超える、請求項15に記載の方法。
- 請求項1に記載の方法に従って調製された乾燥粉末。
- 活性薬剤がインシュリン又はその類似体である、請求項19に記載の乾燥粉末。
- インシュリンを必要としている患者にインシュリンを送達する方法であって、該患者に有効量の請求項19に記載の乾燥粉末を投与することを含む、前記方法。
- ジケトピペラジン溶液を提供すること;
前記ジケトピペラジンを含有する粒子を形成する工程;及び、
噴霧乾燥により溶媒を取り除き、乾燥粉末を得ること;
を含み、前記乾燥粉末は、凍結乾燥により溶媒を取り除くことにより得られる乾燥粉末と比較して改善された薬剤学的特性を備えている、改善された薬剤学的特性を備えた乾燥粉末医薬の調製方法。 - 前記溶媒を取り除く工程の前に、粒子に活性薬剤を添加する工程を更に含む、請求項22に記載の方法。
- 以下の工程:
ある管理された温度下で溶液からジケトピペラジンを沈殿させて、粒子を形成させ;
前記温度に基づいて乾燥方法を選択し;及び、
前記粒子を乾燥させること;
を含む、ジケトピペラジン乾燥粉末の空気力学的性能を最適化する方法。 - 粒子に活性薬剤を添加する工程を更に含む、請求項24に記載の方法。
- 前記ジケトピペラジンがフマリルジケトピペラジンであり、前記管理された温度は約15℃〜約18℃の間であり、そして前記選択された乾燥方法は噴霧乾燥である、請求項24に記載の方法。
- 前記管理された温度は約17℃である、請求項26に記載の方法。
- 前記ジケトピペラジンがフマリルジケトピペラジンであり、前記管理された温度は13℃以下又は19℃以上であり、そして前記選択された乾燥方法は凍結乾燥である、請求項24に記載の方法。
- 請求項24に記載の方法により作製された乾燥粉末。
- 活性薬剤を更に含有する、請求項29に記載の乾燥粉末。
- 前記活性薬剤がインシュリン又はその類似体である、請求項30に記載の乾燥粉末。
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- 2019-06-26 US US16/453,875 patent/US20190314276A1/en not_active Abandoned
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2023
- 2023-09-12 US US18/367,118 patent/US20230414500A1/en active Pending
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Cited By (6)
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JP2009533476A (ja) * | 2006-04-14 | 2009-09-17 | マンカインド コーポレイション | グルカゴン様ペプチド1(glp−1)医薬製剤 |
JP2017110026A (ja) * | 2010-11-09 | 2017-06-22 | マンカインド コーポレイション | ジケトピペラジンを含む治療のための組成物 |
JP2016515522A (ja) * | 2013-03-15 | 2016-05-30 | マンカインド コーポレイション | 微結晶性ジケトピペラジン組成物および方法 |
JP2021054850A (ja) * | 2013-03-15 | 2021-04-08 | マンカインド コーポレイション | 微結晶性ジケトピペラジン粒子の製造方法 |
JP7071488B2 (ja) | 2013-03-15 | 2022-05-19 | マンカインド コーポレイション | 微結晶性ジケトピペラジン粒子の製造方法 |
JP2016525123A (ja) * | 2013-07-18 | 2016-08-22 | マンカインド コーポレイション | 熱安定性乾燥粉末医薬組成物及び方法 |
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