JP7305842B2 - 結晶性の医薬のジケトピペラジン組成物を含む乾燥粉末 - Google Patents
結晶性の医薬のジケトピペラジン組成物を含む乾燥粉末 Download PDFInfo
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Description
アンモニア水の中にジケトピペラジンを溶解させて、第1の溶液を形成する工程、
当該第1の溶液および約10.5%の酢酸を含む第2の溶液を、高圧下で約6.0未満のpHにある高剪断ミキサーに同時に供給する工程、
当該第1の溶液および当該第2の溶液を均質化して、懸濁液中においてジケトピペラジンの微結晶を含む懸濁液を形成する工程であって、当該懸濁液が直径において約0.05μmから約10μmの範囲の粒子サイズを有する微結晶のバイモーダル分布を有する、工程、
空気またはガス流下において当該懸濁液を噴霧する工程、および、
噴霧乾燥により粒子を再形成して、実質的に中空の球体を有する微結晶性粒子を含む乾燥粉末にする工程、を含む。
水酸化ナトリウム水溶液および任意に界面活性剤の中にジケトピペラジンを溶解させて、第1の溶液を形成する工程、
当該第1の溶液および約10.5%の酢酸を含む第2の溶液、ならびに、任意における界面活性剤を、高圧下で約6.0未満のpHにある高剪断ミキサーに同時に供給する工程、
当該第1の溶液および当該第2の溶液を均質化して、懸濁液中にジケトピペラジンの微結晶を含む懸濁液を形成する工程であって、当該懸濁液が直径において約0.05μmから約10μmの範囲の粒子サイズを有し、約45%から65%の範囲のトランス異性体含有量を含む微結晶のバイモーダル分布を有する、工程、
空気またはガス流下において当該懸濁液を噴霧する工程、および、
噴霧乾燥により粒子を再形成して、実質的に中空の球体を有する微結晶性粒子を含む乾燥粉末にする工程、を含む。
アンモニア水の中にジケトピペラジンを溶解させて、第1の溶液を形成する工程、
当該第1の溶液および約10.5%の酢酸を含む第2の溶液を、高圧下で約6.0未満のpHにある高剪断ミキサーに同時に供給して、懸濁液中にジケトピペラジンの微結晶を含む懸濁液を形成する工程であって、当該懸濁液が直径において約0.05μmから約10μmの範囲の粒子サイズを有する微結晶のバイモーダル分布を有する、工程、
空気またはガス流下において当該懸濁液を噴霧する工程、および、
噴霧乾燥により粒子を再形成して、実質的に中空の球体を有する微結晶性粒子を含む乾燥粉末にする工程、を含む。
約0.2%(w/w)から約6%(w/w)の量の界面活性剤を含む水中に、ジケトピペラジン塩を溶解して、第1の溶液を形成する工程、
当該第1の溶液を、約8%(w/w)から約12%(w/w)の酢酸を含む第2の溶液と、高圧下で約6.0未満のpHにある高剪断ミキサー内で同時に混ぜ合わせる工程、
当該第1の溶液および当該第2の溶液を均質化して、懸濁液中にジケトピペラジンの微結晶を含む懸濁液を形成する工程であって、当該懸濁液が直径において約0.05μmから約10μmの範囲の粒子サイズを有する微結晶のバイモーダル分布を有する、工程、
空気またはガス流下において当該懸濁液を噴霧する工程、および、
噴霧乾燥により粒子を再形成して、実質的に中空の球体を有するジケトピペラジン酸の微結晶性粒子を含む乾燥粉末にする工程、を含む。
薬物の不安定性および/または吸収不良等の医薬分野における問題を克服するために使用されている薬物送達剤の1つの種類に、2,5-ジケトジケトピペラジンがある。2,5-ジケトジケトピペラジンは、以下に示す一般式1の化合物によって表され、E1およびE2は、独立して、Nまたは特にNHである。他の実施の形態では、E1およびE2は、独立して、酸素または窒素であり、E1およびE2の置換基のいずれか1つが酸素であり他方が窒素である場合には、式は置換類似体ジケトモルホリンとなる。または、E1およびE2の両方が酸素である場合には、式は置換類似体ジケトジオキサンとなる。
標準的なFDKP微粒子の製造
2.5%(w/w)FDKPを、アンモニア水(1.6%アンモニア)の塩基溶液中に溶解した。10.5%(w/w)酢酸原液を、高圧下で約2.0のpHにある高剪断ミキサー(Snolator)内へ添加し、粒子を製造した。形成された粒子を、脱イオン水中で洗浄した。ジケトピペラジン微粒子は、溶液中において界面活性剤を含まないと不安定であることが見いだされていたが、本実施例の粒子の製造においては、溶液または試薬のいずれにも界面活性剤は添加されていない。
ジケトピペラジン塩を使用する代替の方法による微結晶性FDKP粒子の製造
活性剤を含有する微結晶性FDKP粒子の製造
ジケトピペラジン塩を使用する代替の方法による微結晶性FDKP粒子の製造
2以上の活性剤を含有する微結晶性FDKP粒子の製造
2つの活性剤を含有する微結晶性FDKP粒子の製造
結晶性ジケトピペラジン粒子を含む乾燥粉末組成物の対象への投与
(付記1)
実質的に中空の球状構造を有し、かつ自己集合しないジケトピペラジンの微結晶を含むシェルを備える、実質的に均一なサイズの複数の微結晶性粒子を含み、前記粒子は5μm未満の体積平均幾何学的直径を有する、結晶性ジケトピペラジン組成物。
前記微結晶性粒子の92%までが、5.8μm以下の体積平均幾何学的直径を有する、付記1に記載の結晶性ジケトピペラジン組成物。
前記微結晶性粒子は、1または複数の活性成分をさらに含む、付記1に記載の結晶性ジケトピペラジン組成物。
前記1または複数の活性成分は、ペプチド、タンパク質、核酸分子または有機小分子である、付記3に記載の結晶性ジケトピペラジン組成物。
前記ペプチドは、内分泌ホルモンである、付記4に記載の結晶性ジケトピペラジン組成物。
前記内分泌ホルモンは、インスリン、副甲状腺ホルモン、カルシトニン、グルカゴン、グルカゴン様ペプチド-1、オキシントモジュリン、ペプチドYY、レプチンまたはこれらの内分泌ホルモンの類似体である、付記5に記載の結晶性ジケトピペラジン組成物。
前記ジケトピペラジンは、式2,5-ジケト-3,6-ビス(N-X-4-アミノブチル)ピペラジン(式中、Xは、フマリル、スクシニル、マレイル、マロニルおよびグルタリルからなる群から選択される)、または、その塩である、付記1に記載の結晶性ジケトピペラジン組成物。
前記ジケトピペラジンは、(ビス-3,6-(N-フマリル-4-アミノブチル)-2,5-ジケトピペラジンである、付記7に記載の結晶性ジケトピペラジン組成物。
a)約0.05μmから約10μmの範囲の粒子サイズにおけるバイモーダル分布を有する懸濁液中にジケトピペラジン粒子を形成する工程、
b)空気またはガス流下において噴霧乾燥機を使用して前記懸濁液を噴霧する工程、および、
c)噴霧乾燥により粒子を再形成して、実質的に中空の球体を有する微結晶性ジケトピペラジン粒子を含む乾燥粉末にする工程、
を含む、乾燥粉末で肺投与するのに適切な微結晶性ジケトピペラジン粒子の製造方法。
粒子サイズにおけるバイモーダル分布の粒子の第1のピークは約0.2μmから約2.4μmの平均値を有し、粒子の第2のピークは約2.1μmから約2.4μmの平均サイズを有する、付記9に記載の方法。
前記ジケトピペラジンは、式2,5-ジケト-3,6-ビス(N-X-4-アミノブチル)ピペラジン(式中、Xは、フマリル、スクシニル、マレイル、マロニルおよびグルタリルからなる群から選択される)である、付記9に記載の方法。
前記ジケトピペラジンは、(ビス-3,6-(N-フマリル-4-アミノブチル)-2,5-ジケトピペラジンである、付記11に記載の方法。
工程a)において、前記懸濁液に1または複数の活性剤を含む溶液を添加する工程をさらに含む、付記9に記載の方法。
前記溶液または前記懸濁液に界面活性剤を添加する工程をさらに含む、付記9に記載の方法。
前記界面活性剤は、ポリソルベート80である、付記14に記載の方法。
前記1または複数の活性剤は、ペプチド、タンパク質、核酸分子または有機小分子である、付記13に記載の方法。
前記ペプチドは、内分泌ホルモンである、付記16に記載の方法。
前記内分泌ホルモンは、インスリン、副甲状腺ホルモン、カルシトニン、グルカゴン、グルカゴン様ペプチド-1、オキシントモジュリン、ペプチドYY、レプチンまたはこれらの内分泌ホルモンの類似体である、付記17に記載の方法。
前記ジケトピペラジンは、ジケトピペラジンの二ナトリウム塩、マグネシウム塩、リチウム塩、カルシウム塩またはカリウム塩である、付記9または11に記載の方法。
約0.2%(w/w)から約6%(w/w)の量の界面活性剤を含む水中に、ジケトピペラジン塩を溶解して、第1の溶液を形成する工程、
前記第1の溶液を、約8%(w/w)から約12%(w/w)の酢酸を含む第2の溶液と、高圧下で約6.0未満のpHにある高剪断ミキサー内で、同時に混ぜ合わせる工程、
前記第1の溶液および前記第2の溶液を均質化(ホモジナイズ)して、懸濁液中にジケトピペラジンの微結晶を含む懸濁液を形成する工程であって、前記懸濁液が直径において約0.05μmから約10μmの範囲の粒子サイズを有する微結晶のバイモーダル分布を有する、工程、
空気またはガス流下において前記懸濁液を噴霧する工程、および、
噴霧乾燥により粒子を再形成して、実質的に中空の球体を有する微結晶性粒子を含む乾燥粉末にする工程、
を含む、乾燥粉末組成物の製造方法。
前記懸濁液の噴霧は、窒素ガス下における、高効率サイクロン分離器を装着した噴霧乾燥器内に挿入されている外部混合2流体ノズルを使用することを含む、付記19に記載の方法。
付記4に記載の結晶性ジケトピペラジン組成物を、治療を必要とする対象に投与することを含む、疾患または障害の治療方法。
付記6に記載の結晶性ジケトピペラジン組成物を、治療を必要とする患者に投与することを含む、高血糖症および/または糖尿病の治療方法。
付記1に記載の結晶性ジケトピペラジン組成物を含む、乾燥粉末。
1または複数の活性剤をさらに含み、前記1または複数の活性剤は、ペプチド、タンパク質、核酸分子、有機小分子またはそれらの類似体である、付記24に記載の乾燥粉末。
Claims (9)
- 結晶性の医薬のジケトピペラジン組成物を含み、
前記結晶性の医薬のジケトピペラジン組成物は、
実質的に中空の球状構造を有し、かつ自己集合しないジケトピペラジンの微結晶を含むシェルを備える、実質的に均一なサイズの複数の微結晶性粒子を含み、
前記粒子は、5μm未満の体積平均幾何学的直径を有し、1または複数の活性成分をさらに含む、
乾燥粉末。 - 前記1または複数の活性成分は、ペプチド、タンパク質、核酸分子または有機小分子である、請求項1に記載の乾燥粉末。
- 前記1または複数の活性成分は、血管作用剤、オピオイドアゴニストおよびアンタゴニストを含む神経活性剤、ホルモン、抗凝固剤、免疫調節剤、細胞毒性剤、抗生物質、抗ウイルス剤、抗原、感染因子、炎症仲介物質、細胞表面受容体アゴニストおよびアンタゴニスト、または細胞表面抗原を含む、請求項1に記載の乾燥粉末。
- 前記1または複数の活性成分は、前記神経活性剤を含む、請求項3に記載の乾燥粉末。
- 肺への投与用である、請求項1に記載の乾燥粉末。
- 前記1または複数の活性成分は、血管作用剤を含む、請求項1に記載の乾燥粉末。
- 前記1または複数の活性成分は、プロスタグランジンを含む、請求項1に記載の乾燥粉末。
- 前記プロスタグランジンは、PG-I2を含む、請求項7に記載の乾燥粉末。
- 肺の病気の治療用である、請求項5に記載の乾燥粉末。
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