JP2005512959A - ラパマイシン類似体を含む医療装置 - Google Patents
ラパマイシン類似体を含む医療装置 Download PDFInfo
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Abstract
Description
(用語の定義)
ここで使用する、「プロドラッグ」の語は、例えば血液中で加水分解によって、インビボで上記式の親化合物に速やかに変換される化合物を指す。いずれも参照してここに組み込まれる、T.HiguchiとV.Stella、「Pro−drugs as Novel Delivery systems」、the A.C.S.Symposium Series、第14巻、及びEdward B.Roche編集、「Bioreversible Carriers in Drug Design」American Pharmaceutical Association and Pergamon Press,1987において詳細な考察が為されている。
本発明の1つの実施形態では、式:
本発明の化合物及び方法は、本発明の化合物を製造することができる方法を例示した下記の合成スキームと関連付けてより良く理解される。
下記の実施例を参照することにより、上記がより良く理解される。下記の実施例は本発明の化合物を製造しうる方法を例示するものであって、付属の特許請求の範囲において定義される本発明の範囲を限定することを意図しない。
(実施例1A)
窒素ガス体下に−78℃でジクロロメタン(0.6mL)中のラパマイシン(100mg、0.11mmol)の溶液を2,6−ルチジン(53μL、0.46mmol、4.3当量)及び無水トリフルオロメタンスルホン酸(37μL、0.22mmol)で連続的に処理し、その後15分間攪拌して、室温に温め、シリカゲル(6mL)のパッドを通してジエチルエーテルで溶出した。トリフレートを含む分画をプールし、濃縮して、表題化合物を琥珀色の泡として得た。
42−Epi−(テトラゾリル)−ラパマイシン(弱い極性の異性体)
酢酸イソプロピル(0.3mL)中の実施例1Aの溶液をジイソプロピルエチルアミン(87mL、0.5mmol)及び1H−テトラゾール(35mg、0.5mmol)で連続的に処理し、その後18時間攪拌した。この混合物を水(10mL)とエーテル(10mL)に分配した。その有機層をブライン(10mL)で洗い、乾燥した(Na2SO4)。有機物を濃縮して粘性の黄色固体を得、それを、ヘキサン(10mL)、ヘキサン:エーテル(4:1(10mL)、3:1(10mL)、2:1(10mL)、1:1(10mL))、エーテル(30mL)、ヘキサン:アセトン(1:1(30mL))で溶出するシリカゲル(3.5g、70−230mL)でのクロマトグラフィーによって精製した。異性体の1つはエーテル分画中で収集した。
(実施例2A)
42−Epi−(テトラゾリル)−ラパマイシン(より強い極性の異性体)
実施例1Bにおけるヘキサン:アセトン(1:1)移動相を用いたクロマトグラフィーカラムから、よりゆっくりと移動するバンドを収集して、表題化合物を得た。
本発明の化合物の免疫抑制活性を、ラパマイシン及び2つのラパマイシン類似体;40−epi−N−[2’−ピリドン]−ラパマイシン及び40−epi−N−[4’−ピリドン]−ラパマイシン(いずれも米国特許第5,527,907号に開示されている)と比較した。Transplantatin Proceedings,XIX(5):36−39、Suppl.6(1987)の中でKino,T.らによって述べられているヒト混合リンパ球反応(MLR)アッセイを用いて活性を測定した。アッセイの結果は、表1に示すように、本発明の化合物がナノモル濃度で有効な免疫モジュレーターであることを明らかにしている。
実施例で規定するものを含むがこれらに限定されない、本発明の化合物は、哺乳類(特にヒト)において免疫調節活性を有する。免疫抑制剤として、本発明の化合物は、心臓、腎臓、肝臓、骨髄、皮膚、角膜、肺、膵臓、小腸、四肢、筋肉、神経、十二指腸、小腸、膵島細胞等のような器官又は組織の移植による拒否反応;骨髄移植によって引き起こされる対宿主性移植片病;慢性関節リウマチ、全身性エリテマトーデス、橋本甲状腺炎、多発性硬化症、重症筋無力症、I型糖尿病、ブドウ膜炎、アレルギー性脳脊髄炎、糸球体腎炎等のような自己免疫疾患などの、免疫を介した疾患の治療及び予防のために有用である。さらなる使用は、乾癬、アトピー性皮膚炎、接触皮膚炎及びさらなる湿疹性皮膚炎、脂漏性皮膚炎、扁平苔癬、天疱瘡、水疱性類天疱瘡、表皮水疱症、じんま疹、血管性水腫、脈管炎、紅斑、皮膚好酸球増加症、エリテマトーデス、座瘡及び円形脱毛症などの、炎症性及び過増殖性皮膚疾患及び免疫を介した疾病の皮膚症状発現;角結膜炎、春季結膜炎、ベーチェット病に関連するブドウ膜炎、角膜炎、ヘルペス性角膜炎、円錐角膜、角膜上皮性ジストロフィー、角膜白斑、及び眼天疱瘡などの様々な眼疾患(自己免疫及びその他)の治療及び予防を含む。さらに、喘息(例えば気管支喘息、アレルギー性喘息、内因性喘息、外因性喘息及び塵埃喘息)、特に慢性又は難治性喘息(例えば遅発型喘息及び気道過敏症)、気管支炎、アレルギー性鼻炎等のような状態を含む、可逆性閉塞性気道疾患は、本発明の化合物の標的となる。胃潰瘍、虚血性疾患によって引き起こされる血管損傷及び血栓症などの粘膜及び血管の炎症。さらに、内膜平滑筋細胞過形成、特に生物又は機械を介した血管損傷後の再狭窄及び血管閉塞は、本発明の化合物によって治療又は予防することができる。ここで述べる化合物又は薬剤は、ポリマー化合物で被覆したステントに適用することができる。ステントのポリマー被覆物への化合物又は薬剤の組み込みは、ポリマー被覆したステントを、化合物又は薬剤を含む溶液中に十分な時間(例えば5分間など)浸し、その後被覆ステントを乾燥することにより、好ましくは十分な時間(例えば30分間など)空気乾燥することにより、実施できる。その後、バルーンカテーテルからの展開によって化合物又は薬剤を含むポリマー被覆ステントを冠状動脈血管に送達することができる。ステントに加えて、本発明の薬剤を血管系に導入するために使用できる他の装置は、移植片、カテーテル及びバルーンを含むが、これらに限定されない。さらに、本発明の薬剤の代わりに使用できる他の化合物又は薬剤は、A−94507及びSDZ RADを含むが、これらに限定されない。本発明において使用するとき、該被覆物は、治療物質、すなわち薬剤が実質的にそれに可溶であるいかなるポリマー材料も含みうる。被覆物の目的は、治療物質のための制御放出賦形剤として働くこと又は病変部位において送達される治療物質の貯蔵所となることである。被覆物はポリマーであり得、さらに親水性、疎水性、生分解性又は非生分解性でありうる。ポリマー被覆物のための材料は、ポリカルボン酸、セルロース系ポリマー、ゼラチン、ポリビニルピロリドン、無水マレイン酸ポリマー、ポリアミド、ポリビニルアルコール、ポリエチレンオキシド、グリコサミノグリカン、多糖類、ポリエステル、ポリウレタン、シリコーン、ポリオルトエステル、ポリ無水物、ポリカーボネート、ポリプロピレン、ポリ乳酸、ポリグリコール酸、ポリカプロラクトン、ポリヒドロキシブチレートバレレート、ポリアクリルアミド、ポリエーテル、及び前記の混合物及びコポリマーから成る群より選択されうる。ポリウレタン分散(BAYHYDROL等)及びアクリル酸ラテックス分散などのポリマー分散から調製される被覆物も、本発明の治療物質に関して使用できる。
本発明の医薬組成物は、経口的、直腸的、非経口的、槽内、膣内、腹腔内、局所外用的(粉末、軟膏、ドロップ又は経皮パッチなどによって)、口腔粘膜経路で、経口又は経鼻スプレーとして、又は血管系内に設置されたステントにおけるように局所的に投与しうる、本発明の化合物及び医薬適合性の担体又は賦形剤を含有する。「医薬適合性の担体」の語句は、非毒性の固体、半固体又は液体充填剤、希釈剤、被包材料又は何らかの種類の製剤補助物質を意味する。ここで使用する、「非経口」の語は、静脈内、動脈内、筋肉内、腹腔内、胸骨内、皮下及び関節内注射、注入及び、例えば血管系におけるような、設置を含む投与様式を指す。
0 内弾性板は無傷;内皮は典型的に露出、中膜は圧迫されているが、裂傷してはいない。
1 内弾性板裂傷;中膜は典型的には圧迫されているが、裂傷してはいない。
2 内弾性板裂傷;中膜は可視的に裂傷;外弾性板は無傷であるが、圧迫されている。
3 外弾性板裂傷;典型的には外弾性板を超えて広がる中膜の大きな裂傷;時としてコイルワイヤが外膜に存在する。
対照(平均±SD) 4.46±1.20 3.96±1.16
試験(平均±SD) 4.26±1.26 3.41±0.96
注入量=100μl
取得時間=40分間
流量=1.0ml/分
カラム温度=40℃
波長=278nm
移動相=65%アセトニトリル/35%H2O
カラム=YMC ODS−A S5μm、4.6×250mm Part No.A12052546WT
上記実験からの結果は下記の放出データを示した。
Claims (20)
- 前記支持構造が、冠状動脈ステント、末梢血管ステント、カテーテル、動静脈移植片、バイパス移植片及び血管系において使用される薬剤送達バルーンから成る群より選択される、請求項1に記載の医療装置。
- 前記支持構造が、前記治療物質を含有する被覆物をさらに含む、請求項1に記載の医療装置。
- 前記被覆物がポリマーである、請求項3に記載の医療装置。
- 前記ポリマー被覆物が生体安定である、請求項4に記載の医療装置。
- 前記ポリマー被覆物が生分解性である、請求項4に記載の医療装置。
- 前記支持構造が、冠状動脈ステント、末梢血管ステント、カテーテル、動静脈移植片、バイパス移植片及び血管系において使用される薬剤送達バルーンから成る群より選択される、請求項9に記載の医療装置。
- 前記支持構造が、前記治療物質を含有する被覆物をさらに含む、請求項9に記載の医療装置。
- 前記被覆物がポリマーである、請求項11に記載の医療装置。
- 前記ポリマー被覆物が生体安定である、請求項12に記載の医療装置。
- 前記ポリマー被覆物が生分解性である、請求項12に記載の医療装置。
- 前記支持構造が、冠状動脈ステント、末梢血管ステント、カテーテル、動静脈移植片、バイパス移植片及び血管系において使用される薬剤送達バルーンから成る群より選択される、請求項15に記載の医療装置。
- 前記支持構造が、前記治療物質を含有する被覆物をさらに含む、請求項15に記載の医療装置。
- 前記被覆物がポリマーである、請求項17に記載の医療装置。
- 前記ポリマー被覆物が生体安定である、請求項18に記載の医療装置。
- 前記ポリマー被覆物が生分解性である、請求項18に記載の医療装置。
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US09/950,307 US6890546B2 (en) | 1998-09-24 | 2001-09-10 | Medical devices containing rapamycin analogs |
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PCT/US2002/028798 WO2003022324A1 (en) | 2001-09-10 | 2002-09-10 | Medical devices containing rapamycin analogs |
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