JP2012031180A - 少なくとも1種の有効薬剤成分を含有する多構成要素固相 - Google Patents
少なくとも1種の有効薬剤成分を含有する多構成要素固相 Download PDFInfo
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- JP2012031180A JP2012031180A JP2011195630A JP2011195630A JP2012031180A JP 2012031180 A JP2012031180 A JP 2012031180A JP 2011195630 A JP2011195630 A JP 2011195630A JP 2011195630 A JP2011195630 A JP 2011195630A JP 2012031180 A JP2012031180 A JP 2012031180A
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Abstract
【解決手段】2種以上の独立した分子実体間の分子間相互作用により維持される固相を含む多構成要素相組成物であって、該2種以上の独立した分子実体のうち少なくとも1種が薬剤分子である、多構成要素相組成物。望ましい超分子シントンを形成するために、相補的化学官能基を同定する方法。該方法においては、前記多構成要素固相組成物を調製する段階を更に含む。
【選択図】なし
Description
本出願は、2002年3月1日に出願された、米国特許仮出願第60/360,768号の恩典を主張するものであり、従ってあらゆる図、表、または図面を含む、その全体が本明細書に参照として組入れられている。
過去10年間で、分子および超分子集合体の理解、およびそれを操作する能力において途方もなく進歩した(Moulton, B.ら、Chem. Rev.、101:1629-1658(2001):非特許文献1)。新世代の機能性物質および分子のデザインおよび合成に関係する新たなパラダイムが存在する。このような進歩は、環境科学から分子生物学、薬学、材料科学までの、多くの分子の科学の局面における分子間相互作用、構造および協同性の基本的重要さの結果である。従って現在、特に非共有結合およびナノ技術に関連した領域における分子レベルでの物質の制御および操作に関する期待は、実に桁外れなものである。しかし、結晶構造決定は、1920年代から科学者により使用されてきた道具であるにもかかわらず、結晶構造予測には未だ対処されていない大きい目標がある(Ball, P.、Nature、381:648-650(1996):非特許文献2;Gavezzotti, A.、Acc. Chem. Res.、27:309-314(1994):非特許文献3)。更に、典型的には多形または溶媒和物の形での、所定の分子化合物の1種よりも多い結晶形の存在は、問題点と好機の両方を示している(Desiraju, G.R、Science、278:404-405(1997):非特許文献4;Bernstein, J.ら、Angew. Chem., Int. Ed Engl.、38:3441-3461(1999):非特許文献5)。これは、医薬品産業に関して特にあてはまる。
本発明は、少なくとも1種の有効な薬剤構成要素を有する、多構成要素結晶のような、新規多構成要素固相のデザインへの結晶工学の概念の適用に関する。本発明の多構成要素結晶の例は、アセトアミノフェン/4,4'-ビピリジン/水、フェニトイン/ピリドン、アスピリン/4,4'-ビピリジン、イブプロフェン/4,4'-ビピリジン、フルルビプロフェン/4,4'-ビピリジン、フルルビプロフェン/trans-1,2-ビス(4-ピリジル)エチレン、カルバマゼピン/p-フタルアルデヒド、カルバマゼピン/ニコチンアミド(GRAS)、カルバマゼピン/サッカリン(GRAS)、カルバマゼピン/2,6-ピリジンジカルボン酸、カルバマゼピン/5-ニトロイソフタル酸、カルバマゼピン/酢酸、カルバマゼピン/1,3,5,7-アダマンタンテトラカルボン酸、カルバマゼピン/ベンゾキノン、カルバマゼピン/酪酸、カルバマゼピン/ジメチルスルホキシド(DMSO)、カルバマゼピン/ホルムアミド、カルバマゼピン/ギ酸、およびカルバマゼピン/トリメシン酸を含むが、これらに限定されるものではなく、これらは様々な技術により特徴決定され、および水素結合相互作用の直接の結果として、親薬剤成分とは異なる物理特性を示す。これらの結晶集合体は、例えば、改善された薬物溶解度、溶解速度、安定性およびバイオアベイラビリティをもたらすことができる。
アセトアミノフェン50mg(0.3307mmol)および4,4'-ビピリジン52mg(0.3329mmol)を、温水に溶解し、静置した。緩徐な蒸発は、図4Bに示されたような、1:1:1アセトアミノフェン/4,4'-ビピリジン/水共結晶の無色の針状物を生じた。
フェニトイン28mg(0.1109mmol)および4-ヒドロキシピリドン11mg(0.1156mmol)を、アセトン2mLおよびエタノール1mLに、加熱および攪拌しながら溶解した。緩徐な蒸発は、図5Bに示されたような、1:1フェニトイン/ピリドン共結晶の無色の針状物を生じた。
アスピリン50mg(0.2775mmol)および4,4'-ビピリジン22mg(0.1388mmol)を、ヘキサン4mLに溶解した。この溶液に、エーテル8mLを添加し、1時間静置し、図6Dに示されたような、2:1アスピリン/4,4'-ビピリジン共結晶の無色の針状物を得た。あるいは、アスピリン/4,4'-ビピリジン(化学量論2:1)を、これらの固形成分を、乳棒および乳鉢中で摩砕することにより作成することができる。
ラセミ体イブプロフェン50mg(0.242mmol)および4,4'-ビピリジン18mg(0.0960mmol)を、アセトン5mLに溶解した。この溶媒の緩徐な蒸発は、図7Dに示されたような、2:1イブプロフェン/4,4'-ビピリジン共結晶の無色の針状物を生じた。
フルルビプロフェン50mg(0.2046mmol)および4,4'-ビピリジン15mg(0.0960mmol)を、アセトン3mLに溶解した。この溶媒の緩徐な蒸発は、図8Dに示されたような、2:1フルルビプロフェン/4,4'-ビピリジン共結晶の無色の針状物を生じた。
フルルビプロフェン25mg(0.1023mmol)およびtrans-1,2-ビス(4-ピリジル)エチレン10mg(0.0548mmol)を、アセトン3mLに溶解した。この溶媒の緩徐な蒸発は、図9Bに示されたような、2:1フルルビプロフェン/1,2-ビス(4-ピリジル)エチレン共結晶を生じた。
カルバマゼピン25mg(0.1058mmol)およびp-フタルアルデヒド7mg(0.0521mmol)を、メタノールおよそ3mLに溶解した。この溶媒の緩徐な蒸発は、図10Bに示されたような、1:1カルバマゼピン/p-フタルアルデヒド共結晶の無色の針状物を生じた。
カルバマゼピン25mg(0.1058mmol)およびニコチンアミド12mg(0.0982mmol)を、4mLのDMSO、メタノールまたはエタノールに溶解した。溶媒の緩徐な蒸発は、図11に示されたような、1:1カルバマゼピン/ニコチンアミド共結晶の無色の針状物を生じた。
カルバマゼピン25mg(0.1058mmol)およびサッカリン19mg(0.1037mmol)を、エタノールおよそ4mLに溶解した。この溶媒の緩徐な蒸発は、図12に示されたような、1:1カルバマゼピン/サッカリン共結晶を無色の針状物として生じた。溶解度測定は、このカルバマゼピン多構成要素結晶が、これまでわかっているカルバマゼピン型に勝る改善された溶解度を有することを示している(例えば、増大した分子溶解度およびより長期の水溶液中の溶解性)。
カルバマゼピン36mg(0.1524mmol)および2,6-ピリジンジカルボン酸26mg(0.1556mmol)を、エタノールおよそ2mLに溶解した。この溶媒の緩徐な蒸発は、図14Bに示されたような、1:1カルバマゼピン/2,6-ピリジンジカルボン酸共結晶を透明な針状物として生じた。
カルバマゼピン40mg(0.1693mmol)および5-ニトロイソフタル酸30mg(0.1421mmol)を、メタノールまたはエタノールおよそ3mLに溶解した。この溶媒の緩徐な蒸発は、図15Bに示されたような、1:1カルバマゼピン/5-ニトロイソフタル酸共結晶を黄色の針状物として生じた。
カルバマゼピン25mg(0.1058mmol)を、酢酸およそ2mLに溶解した。この溶媒の緩徐な蒸発は、図16Bに示されたような、1:1カルバマゼピン/酢酸共結晶を、黄色の針状物として生じた。
カルバマゼピン15mg(0.1524mmol)および1,3,5,7-アダマンタンテトラカルボン酸20mg(0.1556mmol)を、メタノールおよそ1mLまたはエタノール1mLに溶解した。この溶媒の緩徐な蒸発は、図17Bに示されたような、2:1カルバマゼピン/1,3,5,7-アダマンタンテトラカルボン酸共結晶を、透明な平面として生じた。
カルバマゼピン25mg(0.1058mmol)およびベンゾキノン11mg(0.1018mmol)を、メタノールまたはTHFの2mLに溶解した。この溶媒の緩徐な蒸発は、図18Bに示されたような、1:1カルバマゼピン/ベンゾキノン共結晶の黄色の結晶の平均収量を生じた。
カルバマゼピン10mg(0.0423mmol)は、酪酸およそ1mLに溶解した。この溶媒の緩徐な蒸発は、図19Bに示されたような、1:1カルバマゼピン/酪酸共結晶の黄色/褐色結晶の平均収量を生じた。
熱重量分析:(TA機器2950高解像度TGA)。開始温度54℃で減量16%、開始温度134℃で減量16%、開始温度174℃で減量49%、その後完全に分解。
カルバマゼピン25mg(0.1058mmol)を、DMSOおよそ1.5mLに溶解した。この溶媒の緩徐な蒸発は、図20Bに示されたような、1:1カルバマゼピン/DMSO共結晶の無色の平板を生じた。
カルバマゼピン10mg(0.0423mmol)を、およそ1mLホルムアミド/1mL THFまたは1mLホルムアミド/1mLメタノールの混合液に溶解した。この溶媒混合物の緩徐な蒸発は、図21Bに示されたような、1:1カルバマゼピン/ホルムアミド共結晶の透明な針状物の平均収量を生じた。
カルバマゼピン40mg(0.1693mmol)を、ギ酸およそ2mLに溶解した。この溶媒混合物の緩徐な蒸発は、図22Bに示されたような、1:1カルバマゼピン/ギ酸共結晶の乳白色の星状物を生じた。
カルバマゼピン36mg(0.1524mmol)およびトリメシン酸31mg(0.1475mmol)を、およそメタノール2mLおよびジクロロメタン2mLの溶媒混合物に溶解した。この溶媒混合物の緩徐な蒸発は、図23Bに示されたような、1:1カルバマゼピン/トリメシン酸共結晶の白色の星状物を生じた。
Claims (36)
- 2種以上の独立した分子実体間の分子間相互作用により維持される固相を含む多構成要素相組成物であって、該2種以上の独立した分子実体のうち少なくとも1種が薬剤分子である、多構成要素相組成物。
- 個別の超分子実体である、請求項1記載の多構成要素相組成物。
- 高分子構造である、請求項1記載の多構成要素相組成物。
- 薬剤分子がその純相中にある場合、該薬剤分子が、超分子ホモシントンにより維持される、請求項1記載の多構成要素相組成物。
- 薬剤分子がその純相にある場合の該薬剤のものと異なった少なくとも1種の物理特性または化学特性を有する、請求項1記載の多構成要素相組成物。
- 薬剤分子がその純相にある場合の該薬剤分子のものと同じである少なくとも1種の物理特性または化学特性を有する、請求項1記載の多構成要素相組成物。
- 少なくとも1種の物理特性または化学特性が、化学安定性、熱力学的安定性、溶解度、溶解、バイオアベイラビリティ、結晶形態、および吸湿性からなる群より選択される、請求項5記載の多構成要素相組成物。
- 少なくとも1種の物理特性または化学特性が、化学安定性、熱力学的安定性、溶解度、溶解、バイオアベイラビリティ、結晶形態、および吸湿性からなる群より選択される、請求項6記載の多構成要素相組成物。
- 薬剤分子が、アスピリン、アセトアミノフェン、プロフェン、フェニトイン、およびカルバマゼピンからなる群より選択される、請求項1記載の多構成要素相組成物。
- 2種以上の独立した分子実体が、アセトアミノフェン、4,4'-ビピリジン、および水;フェニトインおよびピリジン;アスピリンおよび4,4'-ビピリジン;イブプロフェンおよび4,4'-ビピリジン;フルルビプロフェンおよび4,4'-ビピリジン;フルルビプロフェン、trans-1,2-ビス(4-ピリジル)エチレン;カルバマゼピン、p-フタルアルデヒド;カルバマゼピンおよびニコチンアミド;カルバマゼピンおよびサッカリン;カルバマゼピンおよび2,6-ピリジンジカルボン酸;カルバマゼピンおよび5-ニトロイソフタル酸;カルバマゼピンおよび酢酸;カルバマゼピンおよび1,3,5,7-アダマンタンテトラカルボン酸;カルバマゼピンおよびベンゾキノン;カルバマゼピンおよび酪酸;カルバマゼピンおよびジメチルスルホキシド;カルバマゼピンおよびホルムアミド;カルバマゼピンおよびギ酸;ならびに、カルバマゼピンおよびトリメシン酸からなる群より選択される、請求項1記載の多構成要素相組成物。
- 分子間相互作用が、水素結合(弱および/または強)、双極子相互作用(誘導性および/または非誘導性)、スタッキング相互作用、疎水性相互作用、およびその他の分子間静電気的相互作用からなる群より選択される、請求項1記載の多構成要素相組成物。
- 分子間相互作用が、2種以上の独立した分子実体上の相補的化学官能基間である、請求項1記載の多構成要素相組成物。
- 相補的化学官能基が、酸、アミド、脂肪族窒素基部、不飽和芳香族窒素基部、アミン、アルコール、ハロゲン、スルホン、ニトロ基、S-複素環、N-複素環、O-複素環、エーテル、チオエーテル、チオール、エステル、チオエステル、チオケトン、エポキシド、アセトネート、ニトリル、オキシム、および有機ハロゲン化物からなる群より選択される、少なくとも1種の化学官能基を含む、請求項12記載の多構成要素相組成物。
- 2種以上の独立した分子実体上の相補的化学官能基が同じである、請求項12記載の多構成要素相組成物。
- 相補的化学官能基が酸である、請求項14記載の多構成要素相組成物。
- 相補的化学官能基がアミドである、請求項14記載の多構成要素相組成物。
- 2種以上の独立した分子実体上の相補的化学官能基が同じでない、請求項12記載の多構成要素相組成物。
- 2種以上の独立した分子実体上の相補的化学官能基が、酸およびアミド;ピリジンおよびアミド;ならびに、アルコールおよびアミンからなる群より選択される、請求項17記載の多構成要素相組成物。
- 2種以上の独立した分子実体が薬剤分子である、請求項1記載の多構成要素相組成物。
- アスピリンと少なくとも1種の独立した分子実体の間の分子間相互作用により維持された固相を含む、多構成要素相組成物。
- アセトアミノフェンと少なくとも1種の独立した分子実体の間の分子間相互作用により維持された固相を含む、多構成要素相組成物。
- プロフェンと少なくとも1種の独立した分子実体の間の分子間相互作用により維持された固相を含む、多構成要素相組成物。
- フェニトインと少なくとも1種の独立した分子実体の間の分子間相互作用により維持された固相を含む、多構成要素相組成物。
- カルバマゼピンと少なくとも1種の独立した分子実体の間の分子間相互作用により維持された固相を含む、多構成要素相組成物。
- 所望の超分子シントンを形成するために相補的化学官能基を同定する方法であって、以下の段階を含む方法:
(a)有効薬剤成分の構造を評価する段階;
(b)有効薬剤成分が、それ自身との超分子シントンを形成できる化学官能基を含むかどうかを判定する段階;
(c)超分子シントンを形成することが公知である複数の化学官能基から、更なる超分子シントンを形成して有効薬剤成分により形成された超分子シントンとすると考えられる少なくとも1種の官能基を同定する段階であって、同定された化学官能基は、有効薬剤成分により形成された超分子シントンにより形成された超分子シントン内の非共有結合を破壊することができず、かつ、選択された化学官能基が、有効薬剤成分により形成された超分子シントンと非共有結合を形成できる段階;ならびに
(d)有効薬剤成分と相補的である化学官能基を有する共結晶形成体を同定する段階。 - 多構成要素固相組成物を調製する段階を更に含む請求項25記載の方法であって、多構成要素固相組成物が、有効薬剤成分および少なくとも1種の同定された共結晶形成体を含む方法。
- 少なくとも1種の共結晶形成体が、異なる有効薬剤成分、GRAS化合物、食品添加剤、毒性の低い有機物、および金属有機錯体からなる群より選択される、請求項26記載の方法。
- 多構成要素固相組成物が、溶液からの結晶化、溶融物の冷却、昇華、および摩砕からなる群より選択される1種または複数の方法により形成される、請求項26記載の方法。
- 所望の超分子シントンを形成するために、相補的化学官能基を同定する方法であって、以下の段階を含む方法:
(a)有効薬剤成分の構造を評価する段階;
(b)有効薬剤成分が、それ自身との超分子シントンを形成できる化学官能基を含むかどうかを判定する段階;
(c)超分子シントンを形成することが公知である複数の化学官能基から、有効薬剤成分により超分子シントンを形成すると考えられる少なくとも1種の官能基を同定する段階であって、同定された化学官能基は、有効薬剤成分により形成された超分子シントン内の非共有結合を破壊することができ、かつ、選択された化学官能基が、有効薬剤成分上に相補的化学官能基との非共有結合を形成できる段階;ならびに
(d)有効薬剤成分と相補的である化学官能基を有する共結晶形成体を同定する段階。 - 多構成要素固相組成物を調製する段階を更に含む請求項29記載の方法であって、多構成要素固相組成物が、有効薬剤成分および少なくとも1種の同定された共結晶形成体を含む方法。
- 少なくとも1種の共結晶形成体が、異なる有効薬剤成分、GRAS化合物、食品添加剤、毒性の低い有機物、および金属有機錯体からなる群より選択される、請求項30記載の方法。
- 多構成要素固相組成物が、溶液からの結晶化、溶融物の冷却、昇華、および摩砕からなる群より選択された1種または複数の方法により形成される、請求項30記載の方法。
- 所望の超分子シントンを形成するために、相補的化学官能基を同定する方法であって、以下の段階を含む方法:
(a)有効薬剤成分の構造を評価する段階;
(b)有効薬剤成分が、別の分子との超分子シントンを形成できる化学官能基を含むかどうかを判定する段階;
(c)超分子シントンを形成することが公知である複数の化学官能基から、有効薬剤成分により超分子シントンを形成すると考えられる少なくとも1種の官能基を同定する段階であって、選択された化学官能基が、有効薬剤成分上に相補的化学官能基との非共有結合を形成できる段階;ならびに
(d)有効薬剤成分と相補的である化学官能基を有する共結晶形成体を同定する段階。 - 多構成要素固相組成物を調製する段階を更に含む請求項33記載の方法であって、多構成要素固相組成物が、有効薬剤成分および少なくとも1種の同定された共結晶形成体を含む方法。
- 少なくとも1種の共結晶形成体が、異なる有効薬剤成分、GRAS化合物、食品添加剤、毒性の低い有機物、および金属有機錯体からなる群より選択される、請求項34記載の方法。
- 多構成要素固相組成物が、溶液からの結晶化、溶融物の冷却、昇華、および摩砕からなる群より選択される1種または複数の方法により形成される、請求項34記載の方法。
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US10633344B2 (en) | 2020-04-28 |
US20030224006A1 (en) | 2003-12-04 |
CA2477923A1 (en) | 2003-09-12 |
JP2005519112A (ja) | 2005-06-30 |
CA2477923C (en) | 2021-02-23 |
WO2003074474A3 (en) | 2003-12-18 |
JP4906233B2 (ja) | 2012-03-28 |
IL163846A (en) | 2015-07-30 |
AU2003213719A1 (en) | 2003-09-16 |
IL163846A0 (en) | 2005-12-18 |
US20140162989A1 (en) | 2014-06-12 |
EP1494998A2 (en) | 2005-01-12 |
JP2010180239A (ja) | 2010-08-19 |
US20170362182A1 (en) | 2017-12-21 |
WO2003074474A2 (en) | 2003-09-12 |
AU2003213719A8 (en) | 2003-09-16 |
US20190169130A1 (en) | 2019-06-06 |
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