JP6294456B2 - 修飾されたドセタキセルリポソーム製剤 - Google Patents
修飾されたドセタキセルリポソーム製剤 Download PDFInfo
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- JP6294456B2 JP6294456B2 JP2016502155A JP2016502155A JP6294456B2 JP 6294456 B2 JP6294456 B2 JP 6294456B2 JP 2016502155 A JP2016502155 A JP 2016502155A JP 2016502155 A JP2016502155 A JP 2016502155A JP 6294456 B2 JP6294456 B2 JP 6294456B2
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- Prior art keywords
- lipid
- peg
- liposome
- mol
- taxane
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Description
本出願は、2013年3月13日に出願された米国仮特許出願第61/779,902号の優先権の利益を主張し、当該出願の内容は、その全体が本明細書に参考として援用される。
適用されず
適用されず
本発明は、例えば、以下の項目も提供される。
(項目1)
リポソームタキサンを調製する方法であって、
a)ホスファチジルコリン脂質およびステロールを含む脂質二重層を有する第一のリポソームを形成し、ここで、該脂質二重層は水溶液を含む内部区画を封入し;
b)該第一のリポソームにタキサン、またはその薬学的に許容され得る塩を負荷して、負荷されたリポソームを形成し、ここで、該タキサンは2’−O−位でヘテロシクリル−(C 2−5 アルカノイル)基によってエステル化されたドセタキセルであり;次いで、
c)ポリ(エチレングリコール)−リン脂質コンジュゲート(PEG−脂質)の該脂質二重層への挿入を可能とするのに十分な条件下で、該負荷されたリポソームおよび該PEG−脂質を含む混合物を形成し;
それによりリポソームタキサンを形成することを含む、方法。
(項目2)
前記リポソームタキサンが、0.12〜0.25の薬物対脂質比を有する、項目1に記載の方法。
(項目3)
前記リポソームタキサンが、0.14〜0.19の薬物対脂質比を有する、項目1に記載の方法。
(項目4)
前記リポソームタキサンに存在する前記ステロールがコレステロールであって、脂質の量に対して約30重量%〜45重量%の量で存在する、項目1または2に記載の方法。
(項目5)
前記リポソームタキサンに存在する前記ステロールがコレステロールであって、脂質の量に対して約40重量%〜45重量%の量で存在する、項目1〜3のいずれか1項に記載の方法。
(項目6)
前記第一のリポソームが、DSPC/DSPE/Chol、45/10/45;DOPC/Chol、55/45;DOPC/Chol、65/35;HSPC/Chol、55/45;DSPC/Chol、55/45;DMPC/Chol、55/45;DSPC/Chol、65/35;DPPC/Chol、55/45;SOPC/Chol、55/45;POPC/Chol、55/45;HSPC/Chol、65/35よりなる群から選択される脂質コレステロールの組合せから形成され;前記PEG−脂質の挿入の結果、脂質、コレステロールおよびPEG−脂質の合わせた量に対して約1.9重量%〜約5.0重量%のPEG−脂質の量がもたらされる、項目1に記載の方法。
(項目7)
前記第一のリポソームが、SOPC/CholおよびPOPC/Cholよりなる群から選択される脂質コレステロールの組合せから形成され、コレステロールは約42〜48モル%の量で存在し、前記PEG−脂質の挿入の結果、脂質、コレステロールおよびPEG−脂質の合わせた量に対して約1.9重量%〜約5.0重量%のPEG−脂質の量がもたらされる、項目1に記載の方法。
(項目8)
前記第一のリポソームが、DOPC/Chol、HSPC/Chol、DSPC/Chol、およびDPPC/Cholよりなる群から選択される脂質コレステロールの組合せから形成され、コレステロールは約30〜48モル%の量で存在し、前記PEG−脂質の挿入の結果、脂質、コレステロールおよびPEG−脂質の合わせた量に対して約1.9重量%〜約5.0重量%のPEG−脂質の量がもたらされる、項目1に記載の方法。
(項目9)
前記ヘテロシクリル−(C 2−5 アルカノイル)基が、5−(4−メチルピペラジン−1−イル)−ペンタノイル、4−(4−メチルピペラジン−1−イル)−ブタノイル、3−(4−メチルピペラジン−1−イル)−プロピオノイル、2−(4−メチルピペラジン−1−イル)−エタノイル、5−モルホリノ−ペンタノイル、4−モルホリノ−ブタノイル、3−モルホリノ−プロピオノイル、2−モルホリノ−エタノイル、5−(ピペリジン−1−イル)ペンタノイル、4−(ピペリジン−1−イル)ブタノイル、3−(ピペリジン−1−イル)プロピオノイル、および2−(ピペリジン−1−イル)−エタノイルよりなる群から選択される、項目1に記載の方法。
(項目10)
前記ヘテロシクリル−(C 2−5 アルカノイル)基が4−(4−メチルピペラジン−1−イル)−ブタノイルである、項目1に記載の方法。
(項目11)
前記ホスファチジルコリン脂質が、ジパルミトイルホスファチジルコリン(DPPC)、ジステアロイルホスファチジルコリン(DSPC)、水素添加大豆ホスファチジルコリン(HSPC)、およびそれらの混合物よりなる群から選択され;前記ステロールがコレステロールである、項目1に記載の方法。
(項目12)
前記脂質二重層がDSPCおよびコレステロールを含み、DSPC:コレステロール比が約55:45(モル:モル)である、項目11に記載の方法。
(項目13)
前記脂質二重層がDSPCおよびコレステロールを含み、DSPC:コレステロール比が約70:30(モル:モル)である、項目11に記載の方法。
(項目14)
前記第一のリポソームの前記内部区画が水性硫酸アンモニウムを含む、項目1〜13のいずれか1項に記載の方法。
(項目15)
前記第一のリポソームの負荷が、該第一のリポソームの前記内部区画における前記タキサンの蓄積を可能とするのに十分な条件下で、該第一のリポソームおよび該タキサンもしくはその薬学的に許容され得る塩を含む水溶液を形成することを含む、項目14に記載の方法。
(項目16)
工程b)が、約50℃〜約70℃の温度で行われる、項目15に記載の方法。
(項目17)
工程b)が、前記タキサンの重量に対する前記ホスファチジルコリンおよび前記ステロールの合わせた重量の比が約1:0.01〜約1:1であるように行われる、項目15に記載の方法。
(項目18)
前記タキサンの重量に対する前記ホスファチジルコリンおよび前記ステロールの合わせた重量の比が約1:0.2である、項目17に記載の方法。
(項目19)
前記PEG−脂質がジアシル−ホスファチジルエタノールアミン−N−[メトキシ(ポリエチレングリコール)]である、項目1に記載の方法。
(項目20)
前記PEG−脂質が、ジステアロイル−ホスファチジルエタノールアミン−N−[メトキシ(ポリエチレングリコール)−2000](DSPE−PEG2000)およびジステアロイル−ホスファチジルエタノールアミン−N−[メトキシ(ポリエチレングリコール)−5000](DSPE−PEG5000)よりなる群から選択される、項目19に記載の方法。
(項目21)
工程c)が、前記PEG−脂質に対する合わせたホスファチジルコリンおよびステロールの比が約1000:1(モル:モル)〜約20:1(モル:モル)であるように行われる、項目1に記載の方法。
(項目22)
前記PEG−脂質に対する合わせたホスファチジルコリンおよびステロールの比が約35:1(モル:モル)〜約25:1(モル:モル)である、項目21に記載の方法。
(項目23)
前記PEG−脂質に対する合わせたホスファチジルコリンおよびステロールの比が約33:1(モル:モル)である、項目21に記載の方法。
(項目24)
前記PEG−脂質に対する合わせたホスファチジルコリンおよびステロールの比が約27:1(モル:モル)である、項目21に記載の方法。
(項目25)
工程c)が、約35℃〜約70℃の温度で行われる、項目1〜24のいずれか1項に記載の方法。
(項目26)
工程c)が、約50℃〜約55℃の温度で行われる、項目25に記載の方法。
(項目27)
工程c)における前記混合物からのリポソームタキサンを、封入されていないタキサンおよび挿入されていないPEG−脂質を実質的に含まない水溶液に交換することをさらに含む、項目1に記載の方法。
(項目28)
前記リポソームタキサンを凍結乾燥することをさらに含む、項目1〜27のいずれか1項に記載の方法。
(項目29)
項目1〜28のいずれか1項に記載の方法に従って調製されたリポソームタキサン。
(項目30)
がんを処置する方法であって、項目1〜28のいずれか1項に記載の方法に従って調製されたリポソームタキサンを、それを必要とする被験体に投与することを含む方法。
(項目31)
リポソームを含むがんの処置用の組成物であって、該リポソームが:
i)ホスファチジルコリン脂質;
ii)ステロール;
iii)PEG−脂質;および
iv)タキサンまたはその薬学的に許容され得る塩
を含み;
該タキサンが2’−O−位でヘテロシクリル−(C 2−5 アルカン酸)によってエステル化されたドセタキセルであって;
該PEG−脂質が該リポソーム中の全脂質の2〜8モル%を構成する、組成物。
(項目32)
前記ヘテロシクリル−(C 2−5 アルカン酸)が、5−(4−メチルピペラジン−1−イル)−ペンタン酸、4−(4−メチルピペラジン−1−イル)−ブタン酸、3−(4−メチルピペラジン−1−イル)−プロピオン酸、2−(4−メチルピペラジン−1−イル)−エタン酸、5−モルホリノ−ペンタン酸、4−モルホリノ−ブタン酸、3−モルホリノ−プロピオン酸、2−モルホリノ−エタン酸、5−(ピペリジン−1−イル)ペンタン酸、4−(ピペリジン−1−イル)ブタン酸、3−(ピペリジン−1−イル)プロピオン酸、および2−(ピペリジン−1−イル)エタン酸よりなる群から選択される、項目31に記載の組成物。
(項目33)
前記ヘテロシクリル−(C 2−5 アルカン酸)が、4−(4−メチルピペラジン−1−イル)−ブタン酸である、項目31に記載の組成物。
(項目34)
前記ホスファチジルコリン脂質が、ジパルミトイルホスファチジルコリン(DPPC)、ジステアロイルホスファチジルコリン(DSPC)、水素添加大豆ホスファチジルコリン(HSPC)、およびそれらの混合物よりなる群から選択され;前記ステロールがコレステロールである、項目31に記載の組成物。
(項目35)
前記PEG−脂質が、ジアシル−ホスファチジルエタノールアミン−N−[メトキシ(ポリエチレングリコール)]である、項目31に記載の組成物。
(項目36)
前記PEG−脂質が、ジステアロイル−ホスファチジルエタノールアミン−N−[メトキシ(ポリエチレングリコール)−2000]およびジステアロイル−ホスファチジルエタノールアミン−N−[メトキシ(ポリエチレングリコール)−5000]よりなる群から選択される、項目31に記載の組成物。
(項目37)
前記リポソームが、約50モル%〜約70モル%の、DPPCおよびDSPCよりなる群から選択されるホスファチジルコリン脂質、ならびに約25モル%〜約45モル%のコレステロールを含む、項目31に記載の組成物。
(項目38)
前記リポソームが、約53モル%のDSPC、約44モル%のコレステロール、および約3モル%のPEG−脂質を含み、前記PEG−脂質がジステアロイル−ホスファチジルエタノールアミン−N−[メトキシ(ポリエチレングリコール)−2000]である、項目37に記載の組成物。
(項目39)
前記リポソームが、約66モル%のDSPC、約30モル%のコレステロール、および約4モル%のPEG−脂質を含み、前記PEG−脂質がジステアロイル−ホスファチジルエタノールアミン−N−[メトキシ(ポリエチレングリコール)−2000]である、項目37に記載の組成物。
(項目40)
がんを処置する方法であって、項目31〜39のいずれか1項に従って調製されたリポソームタキサンを、それを必要とする被験体に投与することを含む方法。
本発明は、新規なリポソームタキサン、ならびにタキサンのリポソーム中への封入、およびそれに続くポリ(エチレングリコール)官能化脂質のリポソーム中への組込みのための多工程のワンポット法を提供する。本明細書中に記載される方法によって調製されるリポソームタキサンは、貯蔵安定性、イン・ビボ循環時間、およびイン・ビボ有効性の増大を含めたいくつかの利点を示す。リポソームタキサンは、本明細書中において記載されるようにがんの処置に有用である。
本明細書中で用いる場合、用語「リポソーム」は、脂質二重層によって包まれたあらゆる区画を含む。用語リポソームは、単一の脂質二重層よりなり、一般に約20〜約400nmの範囲の直径を有する単層小胞を含む。リポソームは、一般に1〜10μmの範囲の直径を有する多層であってもよい。いくつかの実施態様において、リポソームは、多層小胞(MLV;大きさが約1μm〜約10μm)、大型単層小胞(LUV;大きさが数百ナノメートル〜約10μm)、および小型単層小胞(SUV;大きさが約20nm〜約200nm)を含むことができる。
第一の態様において、本発明は、がんの処置用の組成物を提供する。該組成物は、ホスファチジルコリン脂質、ステロール、PEG−脂質、およびタキサンまたはその薬学的に許容され得る塩を含有するリポソームを含む。タキサンは、ヘテロシクリル−(C2−5アルカン酸)でエステル化されており、PEG−脂質はリポソーム中の全脂質の2〜8モル%を構成する。
本発明のリポソームは、上記のようにカチオン性脂質、双性イオン性脂質、中性脂質、またはアニオン性脂質を含めたあらゆる適切な脂質も含有することができる。適切な脂質は、脂肪、ワックス、ステロイド、コレステロール、脂溶性ビタミン、モノグリセリド、ジグリセリド、リン脂質、スフィンゴ脂質、糖脂質、カチオン性またはアニオン性脂質、誘導体化脂質等を含むことができる。
本発明のリポソームは、診断剤を含有してもよい。本発明で用いられる診断剤は、例えば、以下の文献中に提供される当該分野で既知のいかなる診断剤も含むことができる:Armstrongら、Diagnostic Imaging、第5版、Blackwell Publishing(2004);Torchilin,V.P.編、Targeted Delivery of Imaging Agents、CRC Press(1995);Vallabhajosula,S.、Molecular Imaging:Radiopharmaceuticals for PET and SPECT、Springer(2009)。診断剤は、限定されるものではないが、ガンマ線放射性、放射性、エコー源性、光学的、蛍光性、吸収性、磁性または断層撮影法シグナルを含む検出可能なシグナルを提供する、および/または増強する剤としての方法を含めた、種々の方法によって検出することができる。診断剤を撮像するための技術は、限定されるものではないが、単光子放射型コンピュータ断層撮影法(SPECT)、磁気共鳴映像法(MRI)、光学的撮像、陽電子放射型断層撮影法(PET)、コンピュータ断層撮影法(CT)、x線撮像、ガンマ線撮像等を含むことができる。診断剤は、例えば、リポソームに包埋する、または封入することを含めた、種々の方法で治療リポソームと会合させることができる。
いくつかの場合において、標的部位におけるリポソームの蓄積は、がん組織などのある種の組織の増強された透過性および滞留特性によるものであり得る。そのような様式での蓄積は、しばしば、部分的にはリポソームの大きさのためもたらされ、特殊な標的化の機能性を必要としないことがある。他の場合には、本発明のリポソームは、標的化剤を含むこともできる。一般に、本発明の標的化剤は、器官、組織、細胞、細胞外マトリックス、または細胞内領域と関連する標的などの関心対象であるいかなる標的とも関連させることができる。ある実施態様において、標的は、がん性疾患などの特定の病状と関連させることができる。いくつかの実施態様において、標的化成分は、受容体などのただ1つの標的に対して特異的であり得る。適切な標的は、限定されるものではないが、DNA、RNAなどの核酸、またはその修飾された誘導体を含むことができる。適切な標的は、限定されるものではないが、細胞外タンパク質、受容体、細胞表面受容体、腫瘍マーカー、膜貫通タンパク質、酵素、または抗体などのタンパク質も含むことができる。適切な標的は、例えば、細胞の表面に存在し得る単糖、二糖、または多糖などの炭水化物を含むことができる。
第二の態様において、本発明は、リポソームタキサンを調製する方法を提供する。当業者に知られた多数の技術を用いて、リポソームを調製し、タキサンを負荷することができる。脂質小胞は、例えば、(適切な容器中で脂質と有機溶媒との混合物の蒸発によって調製された)乾燥した脂質フィルムを水または水性緩衝液で水和させることによって調製することができる。脂質フィルムの水和は、典型的には、多層小胞(MLV)の懸濁液をもたらす。別法として、MLVは、C1−4アルカノールなどの適切な溶媒中の脂質の溶液を水または水性緩衝液で希釈することによって形成することができる。単層小胞は、超音波処理、または規定された細孔径を持つ膜を通す押出しによってMLVから形成することができる。タキサンの封入は、薬物を、MLV形成中にフィルム水和または脂質希釈に用いる水溶液に含めることによって行うことができる。タキサンは、「遠隔負荷」技術を用いて、予め形成された小胞中に封入することもできる。遠隔負荷は、タキサンを外部溶液から小胞の内部へ駆動する、小胞膜のいずれかの側でのpHまたはイオン勾配の確立を含む。
別の態様において、本発明は、がんを処置する方法を提供する。該方法は、上記のリポソームタキサンを含有する組成物を、それを必要とする被験体に投与することを含む。がんの処置のための治療的使用において、本発明のリポソーム組成物は、タキサンの初期投与量が1日当たり約0.001mg/kg〜約1000mg/kgの範囲であるように投与することができる。約0.01〜500mg/kg、または約0.1〜200mg/kg、または約1〜100mg/kg、または約10〜50mg/kg、または約10mg/kg、または約5mg/kg、または約2.5mg/kg、または約1mg/kgの日投与量を用いることができる。
ストロメリシン阻害剤、スルフィノシン、スロフェヌル(sulofenur)、超活性血管作用性腸ペプチドアンタゴニスト、スラジスタ、スラミン、スワインソニン、合成グリコサミノグリカン、タリソマイシン、タリムスチン、タモキシフェンメチオダイド、タウロムスチン、タザロテン、テコガランナトリウム、テガフール、テルラピリリウム、テロメラーゼ阻害剤、塩酸テロキサントロン、テモポルフィン、テモゾロミド、テニポシド、テロキシロン、テストラクトン、テトラクロロデカオキシド、テトラゾミン、サリブラスチン、サリドマイド、チアミプリン、チオコラリン、チオグアニン、チオテパ、トロンボポエチン、トロンボポエチンミメティック、チマルファシン、チモポエチン受容体アゴニスト、チモトリナン、甲状腺刺激ホルモン、チアゾフリン、スズエチルエチオプルプリン、チラパザミン、二塩化チタノセン、塩酸トポテカン、トプセンチン、トレミフェン、クエン酸トレミフェン、全能性幹細胞因子、翻訳阻害剤、酢酸トレストロン、トレチノイン、トリアセチルウリジン、トリシリビン、リン酸トリシリビン、トリメトトレキセート、グルクロン酸トリメトトレキセート、トリプトレリン、トロピセトロン、塩酸ツブロゾール、ツロステリド、チロシンキナーゼ阻害剤、チルフォスチン、UBC阻害剤、ウベニメクス、ウラシルマスタード、ウレデパ、尿生殖洞由来成長阻害因子、ウロキナーゼ受容体アンタゴニスト、バプレオチド、バリオリンB、ベラレソール、ベラミン、ベルジン、ベルテポルフィン、硫酸ビンブラスチン、硫酸ビンクリスチン、ビンデシン、硫酸ビンデシン、硫酸ビネピジン、硫酸ビングリシネート、硫酸ビンロイロシン、ビノレルビン、酒石酸ビノレルビン、硫酸ビンロシジン、ビンキサルチン、硫酸ビンゾリジン、ビタキシン、ボロゾール、ザノテロン、ゼニプラチン、ジラスコルブ、ジノスタチン、ジノスタチンスチマラマー、または塩酸ゾルビシンを含むことができる。
実施例1 リポソームタキサンの調製
緩衝液および試薬の調製
300mMスクロース透析溶液の調製。102.69gのスクロースを秤量し、1Lメスフラスコに加えた。該フラスコにDI水を4分の3充填し、固体が溶解するまで振盪することによって混合した。DI水を室温で加えて、スクロースを所望の濃度とし、蓋をしたフラスコを繰り返し倒立させることによって混合した。溶液を真空によって0.2μmの47mmナイロン膜を通して濾過し、2〜5℃で貯蔵した。
1L丸底フラスコをロータリーエバポレーターから取り出した。加熱された85mLの硫酸アンモニウム/スクロースを、激しく渦を巻いている状態で、フラスコに排出した。混合物を、ロータリーエバポレーター浴上のフラスコ中で、60℃で30分間回転させた。次いで、フラスコを取り出し、直ちに押出しを開始した。
遠隔負荷手法。ドセタキセル誘導体TD−1(386mg、WO 2009/141738 A2に記載されたように調製)を、2つのゴムストッパー、温度制御熱電対用のアダプター、および撹拌棒を嵌合させた500mLの3ツ口丸底フラスコ中に秤量した。TD−1を190mLの10mM酢酸緩衝化スクロース溶液(pH5.5)に溶解させ、溶液のpHを、水酸化ナトリウム水溶液を用いて5.5〜5.6に調整した。適度に撹拌しつつ、加熱マントルを用いて、溶液を65℃まで加熱した。
熱挿入工程としてのDSPE−PEG(2000)の組込みは、薬物負荷後に最もよく確立されることが判明した。DSPE−PEG(2000)の挿入のための温度および時間の注意深い制御は、適切なPEG化を提供することが判明し、種々のロットからの詳細を表3に記載する。全ての場合において、PEG化TD−1リポソームの最終滅菌は、全ての入ってくる原料を注意深く制御して、0.2ミクロンフィルターを通す濾過によって行った。
2つの薬物動態および組織分布の研究を、腫瘍を持つマウスにおいて完了し、PEG化TD−1リポソームをドセタキセルと比較する。
設計 血漿中薬物動態および分布を、各々、PC3細胞(ヒト前立腺がん)を皮下移植した雄無胸腺ヌードマウスで研究した。一旦腫瘍が100〜300mm3の体積に到達したところで、動物を5つの群に無作為に分けた。各動物には、表5に示されるように、単一の静脈内投与量のドセタキセル、封入されていないTD−1、非PEG化TD−1リポソーム、またはPEG化TD−1リポソームが与えられた。
TD−1の血漿中濃度は、図1Aに示されるように、経時的に減少した。どの形態の封入薬物と比較しても、封入されていないTD−1は、低い全身曝露(AUC)、迅速なクリアランスおよび大体積の分布を示した(表6)。
血漿薬物動態および分布を、各々、A549細胞(ヒト非小細胞肺がん)を皮下移植した雌無胸腺ヌードマウスにおいて研究した。一旦腫瘍が100〜300mm3の体積に到達したところで、動物を4つの群に無作為に分けた。各動物には、表8に示されるように、単一の静脈内投与量のドセタキセルまたはPEG化TD−1リポソームを与えた。
上記の血漿中レベルおよび薬物動態計算に加えて、組織分布も評価した。表5に記載された各動物から採取され、かつ分析前に凍結された組織は:腫瘍、肝臓、脾臓、および腎臓を含むものであった。ドセタキセルで処置されたマウスからの組織を、ドセタキセルレベルについて分析した。TD−1、TD−1リポソームおよびPEG化TD−1リポソームで処置されたマウスからの組織を、ドセタキセルおよびTD−1レベルの両方について分析した。
血漿中レベルおよび薬物動態計算に加えて、組織分布の評価を、(表8におけるように)PEG化TD−1リポソームの投与後に、A549ヒトNSCLC腫瘍を持つマウスで行った。TD−1は、長期間にわたって、A549腫瘍に蓄積した(図4A)。TD−1の濃度は、注射後の最初の24時間にわたってゆっくりと増加した。24時間後に、TD−1の濃度は、低投与量では経時的に下方に移行する傾向があった。高い投与量では、濃度は、投与後ほぼ14日にわたって幾分安定なままであり、次いで、増加する傾向があったが、変動も増加した。TD−1の濃度は、21日の観測期間にわたって、定量の下限(2.0μg/g)を超えたままであった。
一連の研究を完了し、免疫不全マウスに移植された種々の腫瘍細胞系に対する活性を調べ、PEG化TD−1リポソームの活性をドセタキセルと比較した。研究は大まかには同様の設計のものであった。腫瘍細胞系をヌード(免疫不全)マウスの脇腹に皮下移植し、一定の大きさまで成長させた。腫瘍が成長しなかったマウスは除いた。マウスを、生理食塩水(対照、全ての研究で含めた)またはドセタキセルまたはPEG化TD−1リポソームのいずれかを受けるように割り当て、ゆっくりとしたボーラス静脈内注射によって設計された処置を投与した。それぞれの場合において、可能な場合、投与量は、同等のレベルの毒性/耐性を提供するものとして選択した。TD−1の最高投与量は、通常、投与できる体積によって制限された。腫瘍の体積を分析して、腫瘍の成長の遅延(TGD)および部分的退行を決定した。マウスが最初の体重から20%減少するか、または瀕死の状態になった場合、あるいはマウスの腫瘍体積が2500mm3を超え、または腫瘍が潰瘍となった場合、マウスを研究から取り除いた。マウスの最初のコーホートの半分未満が残っていれば、その群は、グラフ化せず、あるいはさらなる腫瘍の分析に含めなかった。しかしながら、全ての残存する動物を、生存中観察期間の完了まで追跡し、生存分析に含めた。これらの研究の様々な特徴を表13にまとめる。
記載された遠隔負荷技術によるリポソームTD−1(MP−3528)の調製を、一連の脂質組成物について評価してきた。これらの組成物は、TD−1の有意な喪失または加水分解なしにDSPE−PEGの挿入を可能としつつ、封入TD−1を供給する広範囲な製剤を評価するために選択された。これらの製剤の調製のための方法論は以下のようにまとめることができる:
1)封入された硫酸アンモニウムを含有する小胞の調製
a.脂質をアルコール(EtOHに溶解させ、これを、次いで、硫酸アンモニウムの水溶液に加えた。
b.得られた小胞を押し出して、よく規定された粒径を得た。
c.透析濾過を行って、封入されていない硫酸アンモニウムを除去した。
2)MP−3528の硫酸アンモニウム小胞への遠隔負荷
3)遠隔負荷されたMP−3528を含有する小胞へのDSPE−PEGの挿入
4)ヒスチジン/食塩水緩衝液に対する透析濾過
1)薬物対全脂質比よって測定されたMP−3528の封入。より高い値は、小胞への遠隔負荷のより高いレベルを示す(0.1未満の値は、最適未満の遠隔負荷、またはDSPE−PEG挿入工程の間における薬物の喪失のいずれかを示す)。
2)製剤から放出されたMP−3528の%(%遊離)。%遊離のより高い値は、薬物の滞留が乏しいことを示唆する(>25%)。
3)ドセタキセルの%。低い値は、プロドラッグの有意な加水分解(>5%)なしに調製が成功したことを示す。
4)加工の間における小胞完全性の示度としての小胞の粒径(120nmよりも大きな粒径は、加工の間における許容できない変化を示唆する)
5)DSPE−PEGの、MP−3528の遠隔負荷後における小胞への組込み(低値<1モル%は乏しい組込みを示す)
約45%(モル)以上のコレステロールを含有する調製された全ての製剤は、結果として、上記基準を満足する組成物をもたらした(実施例1、2、5、6、7、8、10)。混合された不飽和、飽和PC(SOPCおよびPOPC)は、%遊離薬物に関して許容され得る結果(実施例11〜13)を与え、負電荷を持つDSPGを含有するもの(実施例16)も同様であった。
Claims (33)
- リポソームタキサンを調製する方法であって、該方法は、
a)ホスファチジルコリン脂質およびステロールを含む脂質二重層を有する第一のリポソームを形成し、ここで、該脂質二重層は水溶液を含む内部区画を封入し;
b)該第一のリポソームにタキサン、またはその薬学的に許容され得る塩を負荷して、負荷されたリポソームを形成し、ここで、該タキサンは2’−O−位でヘテロシクリル−(C2−5アルカノイル)基によってエステル化されたドセタキセルであり;次いで、
c)該負荷されたリポソームおよびポリ(エチレングリコール)−リン脂質コンジュゲート(PEG−脂質)を含む混合物を形成し、ここで、ホスファチジルコリン脂質およびステロールの合計と該PEG−脂質との比が、約1000:1(モル:モル)〜約20:1(モル:モル)であり、該PEG−脂質の該脂質二重層への挿入を可能とするために、約30〜60分間約50℃〜約60℃まで該混合物を加熱し;
それによりリポソームタキサンを形成することを含み、
ここで、該ステロールがコレステロールであり、該リポソームが、35モル%〜50モル%のコレステロールを含有し、
該PEG−脂質の挿入の結果、該リポソーム中の全脂質の2モル%〜8モル%のPEG脂質をもたらされる、方法。 - 前記リポソームタキサンが、0.12〜0.25の薬物対脂質比を有する、請求項1に記載の方法。
- 前記リポソームタキサンが、0.14〜0.19の薬物対脂質比を有する、請求項1に記載の方法。
- 前記コレステロールが、脂質の量に対して約35重量%〜45重量%の量で存在する、請求項1または2に記載の方法。
- 前記コレステロールが、脂質の量に対して約40重量%〜45重量%の量で存在する、請求項1〜3のいずれか1項に記載の方法。
- リポソームタキサンを調製する方法であって、該方法は、
a)ホスファチジルコリン脂質およびコレステロールを含む脂質二重層を有する第一のリポソームを形成し、ここで、該脂質二重層は水溶液を含む内部区画を封入し;
b)該第一のリポソームにタキサン、またはその薬学的に許容され得る塩を負荷して、負荷されたリポソームを形成し、ここで、該タキサンは2’−O−位でヘテロシクリル−(C 2−5 アルカノイル)基によってエステル化されたドセタキセルであり;次いで、
c)該負荷されたリポソームおよびポリ(エチレングリコール)−リン脂質コンジュゲート(PEG−脂質)を含む混合物を形成し、ここで、ホスファチジルコリン脂質およびコレステロールの合計と該PEG−脂質との比が、約1000:1(モル:モル)〜約20:1(モル:モル)であり、該PEG−脂質の該脂質二重層への挿入を可能とするために、約30〜60分間約50℃〜約60℃まで該混合物を加熱し;
それによりリポソームタキサンを形成することを含み、
前記第一のリポソームが、DSPC/DSPE/Chol、45/10/45;DOPC/Chol、55/45;DOPC/Chol、65/35;HSPC/Chol、55/45;DSPC/Chol、55/45;DMPC/Chol、55/45;DSPC/Chol、65/35;DPPC/Chol、55/45;SOPC/Chol、55/45;POPC/Chol、55/45;HSPC/Chol、65/35よりなる群から選択される脂質コレステロールの組合せから形成され;前記PEG−脂質の挿入の結果、脂質、コレステロールおよびPEG−脂質の合わせた量に対して約1.9重量%〜約5.0重量%のPEG−脂質の量がもたらされる、方法。 - 前記第一のリポソームが、SOPC/CholおよびPOPC/Cholよりなる群から選択される脂質コレステロールの組合せから形成され、コレステロールは約42〜48モル%の量で存在し、前記PEG−脂質の挿入の結果、脂質、コレステロールおよびPEG−脂質の合わせた量に対して約2重量%〜約6重量%のPEG−脂質の量がもたらされる、請求項1に記載の方法。
- リポソームタキサンを調製する方法であって、該方法は、
a)ホスファチジルコリン脂質およびコレステロールを含む脂質二重層を有する第一のリポソームを形成し、ここで、該脂質二重層は水溶液を含む内部区画を封入し;
b)該第一のリポソームにタキサン、またはその薬学的に許容され得る塩を負荷して、負荷されたリポソームを形成し、ここで、該タキサンは2’−O−位でヘテロシクリル−(C 2−5 アルカノイル)基によってエステル化されたドセタキセルであり;次いで、
c)該負荷されたリポソームおよびポリ(エチレングリコール)−リン脂質コンジュゲート(PEG−脂質)を含む混合物を形成し、ここで、ホスファチジルコリン脂質およびコレステロールの合計と該PEG−脂質との比が、約1000:1(モル:モル)〜約20:1(モル:モル)であり、該PEG−脂質の該脂質二重層への挿入を可能とするために、約30〜60分間約50℃〜約60℃まで該混合物を加熱し;
それによりリポソームタキサンを形成することを含み、
前記第一のリポソームが、DOPC/Chol、HSPC/Chol、DSPC/Chol、およびDPPC/Cholよりなる群から選択される脂質コレステロールの組合せから形成され、コレステロールは約35〜48モル%の量で存在し、前記PEG−脂質の挿入の結果、脂質、コレステロールおよびPEG−脂質の合わせた量に対して約2重量%〜約6重量%のPEG−脂質の量がもたらされる、方法。 - 前記ヘテロシクリル−(C2−5アルカノイル)基が、5−(4−メチルピペラジン−1−イル)−ペンタノイル、4−(4−メチルピペラジン−1−イル)−ブタノイル、3−(4−メチルピペラジン−1−イル)−プロピオノイル、2−(4−メチルピペラジン−1−イル)−エタノイル、5−モルホリノ−ペンタノイル、4−モルホリノ−ブタノイル、3−モルホリノ−プロピオノイル、2−モルホリノ−エタノイル、5−(ピペリジン−1−イル)ペンタノイル、4−(ピペリジン−1−イル)ブタノイル、3−(ピペリジン−1−イル)プロピオノイル、および2−(ピペリジン−1−イル)−エタノイルよりなる群から選択される、請求項1に記載の方法。
- 前記ヘテロシクリル−(C2−5アルカノイル)基が4−(4−メチルピペラジン−1−イル)−ブタノイルである、請求項1に記載の方法。
- 前記ホスファチジルコリン脂質が、ジパルミトイルホスファチジルコリン(DPPC)、ジステアロイルホスファチジルコリン(DSPC)、水素添加大豆ホスファチジルコリン(HSPC)、およびそれらの混合物よりなる群から選択される、請求項1に記載の方法。
- 前記脂質二重層がDSPCおよびコレステロールを含み、DSPC:コレステロール比が約55:45(モル:モル)である、請求項11に記載の方法。
- 前記第一のリポソームの前記内部区画が水性硫酸アンモニウムを含む、請求項1〜12のいずれか1項に記載の方法。
- 前記第一のリポソームの負荷が、該第一のリポソームの前記内部区画における前記タキサンの蓄積を可能とするのに十分な条件下で、該第一のリポソームおよび該タキサンもしくはその薬学的に許容され得る塩を含む水溶液を形成することを含む、請求項13に記載の方法。
- 工程b)が、約50℃〜約70℃の温度で行われる、請求項14に記載の方法。
- 工程b)が、前記タキサンの重量に対する前記ホスファチジルコリンおよび前記ステロールの合わせた重量の比が約1:0.01〜約1:1であるように行われる、請求項14に記載の方法。
- 前記タキサンの重量に対する前記ホスファチジルコリンおよび前記ステロールの合わせた重量の比が約1:0.2である、請求項16に記載の方法。
- 前記PEG−脂質がジアシル−ホスファチジルエタノールアミン−N−[メトキシ(ポリエチレングリコール)]である、請求項1に記載の方法。
- 前記PEG−脂質が、ジステアロイル−ホスファチジルエタノールアミン−N−[メトキシ(ポリエチレングリコール)−2000](DSPE−PEG2000)およびジステアロイル−ホスファチジルエタノールアミン−N−[メトキシ(ポリエチレングリコール)−5000](DSPE−PEG5000)よりなる群から選択される、請求項18に記載の方法。
- 前記PEG−脂質に対する合わせたホスファチジルコリンおよびステロールの比が約35:1(モル:モル)〜約25:1(モル:モル)である、請求項1に記載の方法。
- 前記PEG−脂質に対する合わせたホスファチジルコリンおよびステロールの比が約33:1(モル:モル)である、請求項1に記載の方法。
- 前記PEG−脂質に対する合わせたホスファチジルコリンおよびステロールの比が約27:1(モル:モル)である、請求項1に記載の方法。
- 工程c)における前記混合物からのリポソームタキサンを、封入されていないタキサンおよび挿入されていないPEG−脂質を実質的に含まない水溶液に交換することをさらに含む、請求項1に記載の方法。
- 前記リポソームタキサンを凍結乾燥することをさらに含む、請求項1〜23のいずれか1項に記載の方法。
- リポソームを含むがんの処置用の組成物であって、該リポソームが:
i)ホスファチジルコリン脂質;
ii)ステロール;
iii)PEG−脂質;および
iv)タキサンまたはその薬学的に許容され得る塩
を含み;
該タキサンが2’−O−位でヘテロシクリル−(C2−5アルカン酸)によってエステル化されたドセタキセルであって;
該PEG−脂質が該リポソーム中の全脂質の2モル%〜8モル%を構成し、
ここで、該ステロールがコレステロールであり、該リポソームが、35モル%〜50モル%のコレステロールを含有し、
5℃で貯蔵した場合、該リポソームからのドセタキセルの放出が、該PEG−脂質を有さないリポソームと比較して約1/20に減少する、組成物。 - 前記ヘテロシクリル−(C2−5アルカン酸)が、5−(4−メチルピペラジン−1−イル)−ペンタン酸、4−(4−メチルピペラジン−1−イル)−ブタン酸、3−(4−メチルピペラジン−1−イル)−プロピオン酸、2−(4−メチルピペラジン−1−イル)−エタン酸、5−モルホリノ−ペンタン酸、4−モルホリノ−ブタン酸、3−モルホリノ−プロピオン酸、2−モルホリノ−エタン酸、5−(ピペリジン−1−イル)ペンタン酸、4−(ピペリジン−1−イル)ブタン酸、3−(ピペリジン−1−イル)プロピオン酸、および2−(ピペリジン−1−イル)エタン酸よりなる群から選択される、請求項25に記載の組成物。
- 前記ヘテロシクリル−(C2−5アルカン酸)が、4−(4−メチルピペラジン−1−イル)−ブタン酸である、請求項26に記載の組成物。
- 前記ホスファチジルコリン脂質が、ジパルミトイルホスファチジルコリン(DPPC)、ジステアロイルホスファチジルコリン(DSPC)、水素添加大豆ホスファチジルコリン(HSPC)、およびそれらの混合物よりなる群から選択され;前記ステロールがコレステロールである、請求項25に記載の組成物。
- 前記PEG−脂質が、ジアシル−ホスファチジルエタノールアミン−N−[メトキシ(ポリエチレングリコール)]である、請求項25に記載の組成物。
- 前記PEG−脂質が、ジステアロイル−ホスファチジルエタノールアミン−N−[メトキシ(ポリエチレングリコール)−2000]およびジステアロイル−ホスファチジルエタノールアミン−N−[メトキシ(ポリエチレングリコール)−5000]よりなる群から選択される、請求項25に記載の組成物。
- リポソームを含むがんの処置用の組成物であって、該リポソームが:
i)ホスファチジルコリン脂質;
ii)ステロール;
iii)PEG−脂質;および
iv)タキサンまたはその薬学的に許容され得る塩
を含み;
該タキサンが2’−O−位でヘテロシクリル−(C 2−5 アルカン酸)によってエステル化されたドセタキセルであって;
該PEG−脂質が該リポソーム中の全脂質の2モル%〜8モル%を構成し、
ここで、該ステロールがコレステロールであり、
前記リポソームが、約50モル%〜約70モル%の、DPPCおよびDSPCよりなる群から選択されるホスファチジルコリン脂質、ならびに約35モル%〜約45モル%のコレステロールを含み、
5℃で貯蔵した場合、該リポソームからのドセタキセルの放出が、該PEG−脂質を有さないリポソームと比較して約1/20に減少する、組成物。 - 前記リポソームが、約53モル%のDSPC、約44モル%のコレステロール、および約3モル%のPEG−脂質を含み、前記PEG−脂質がジステアロイル−ホスファチジルエタノールアミン−N−[メトキシ(ポリエチレングリコール)−2000]である、請求項31に記載の組成物。
- がんの処置を必要とする被験体において、がんを処置するための、請求項25〜32のいずれか1項に記載の組成物。
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JP2016513655A (ja) | 2016-05-16 |
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