JP5984837B2 - ピロロキノリニル−ピロリジン−2,5−ジオン組成物ならびにそれを調製および使用する方法 - Google Patents
ピロロキノリニル−ピロリジン−2,5−ジオン組成物ならびにそれを調製および使用する方法 Download PDFInfo
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- JP5984837B2 JP5984837B2 JP2013546445A JP2013546445A JP5984837B2 JP 5984837 B2 JP5984837 B2 JP 5984837B2 JP 2013546445 A JP2013546445 A JP 2013546445A JP 2013546445 A JP2013546445 A JP 2013546445A JP 5984837 B2 JP5984837 B2 JP 5984837B2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Saccharide Compounds (AREA)
Description
本特許出願は、2010年12月23日に出願された米国仮特許出願第61/426,749号の優先権および利益を主張する。この米国仮特許出願第61/426,749号の内容は、その全体が参考として本明細書に援用される。
がんは、米国において、心臓病に次ぐ二番目に主要な死因である(非特許文献1)。がんの診断および処置における最近の進歩にもかかわらず、がんが早期に見つかれば外科手術および放射線治療は治効があり得るが、転移性疾患に対する現行の薬物治療は、ほとんど待機的であり、長期間の治癒をほとんど与えない。市場に出ている新たな化学療法を用いてさえも、単剤療法において、または既存の剤との組み合わせにおいて、抵抗性腫瘍の処置における第一線の治療剤として、ならびに第二線および第三線の治療剤として有効な、新規薬物に対する必要性が継続している。
R1およびR2は、独立に、水素または−OR3であり、
R3は、独立に、水素またはグルクロニドであり、
X1、X2およびX3は、−CH2−、−CH(OH)−、および−C(O)−からなる群から選択され、X1、X2またはX3の1つのみは、−CH2−と異なってもよいが、
ただし、X1=X2=X3=−CH2−である場合、R1は、R2と異なる。
本発明の好ましい実施形態において、例えば以下の項目が提供される。
(項目1)
式Ia、Ib、IcもしくはIdの化合物
またはその薬学的に受容可能な塩もしくはエステルであって、式中、
R 1 およびR 2 は、独立に、水素または−OR 3 であり、
R 3 は、独立に、水素またはグルクロニドであり、
X 1 、X 2 およびX 3 は、−CH 2 −、−CH(OH)−、および−C(O)−からなる群から選択され、X 1 、X 2 またはX 3 の1つのみは、−CH 2 −と異なってもよいが、ただし、X 1 =X 2 =X 3 =−CH 2 −である場合、R 1 は、R 2 と異なる、
化合物またはその薬学的に受容可能な塩もしくはエステル。
(項目2)
X 1 =X 2 =X 3 =−CH 2 −である、項目1に記載の化合物。
(項目3)
X 1 、X 2 またはX 3 の少なくとも1つが、−CH(OH)−である、項目1に記載の化合物。
(項目4)
X 1 が、−CH(OH)−である、項目3に記載の化合物。
(項目5)
X 1 、X 2 またはX 3 の少なくとも1つが、−C(O)−である、項目1に記載の化合物。
(項目6)
X 1 が、−C(O)−である、項目5に記載の化合物。
(項目7)
X 3 が、−C(O)−である、項目5に記載の化合物。
(項目8)
R 1 が、Hであり、R 2 が、Hである、項目1に記載の化合物。
(項目9)
R 1 が、Hであり、R 2 が、−OR 3 である、項目1に記載の化合物。
(項目10)
R 3 が、Hである、項目9に記載の化合物。
(項目11)
R 3 が、
であり、「 * 」でマークされている環の位置における炭素原子が、−OR 3 の酸素に結合している、項目9に記載の化合物。
(項目12)
からなる群から選択される、項目1に記載の化合物またはその薬学的に受容可能な塩もしくはエステル。
(項目13)
治療有効量の項目1に記載の化合物、またはその塩、溶媒和物、水和物もしくはプロドラッグと、薬学的に受容可能なキャリアまたは賦形剤とを含む薬学的組成物。
(項目14)
細胞増殖性障害を処置する方法であって、該障害が処置されるように、それを必要とする被験体に、薬学的に受容可能なキャリアと組み合わせて、治療有効量の項目1に記載の化合物またはその塩、溶媒和物、水和物もしくはプロドラッグを投与することによって処置する方法。
(項目15)
前記それを必要とする被験体に、第2の抗増殖剤を投与することをさらに含む、項目14に記載の方法。
本発明は、新規のピロロキノリニル−ピロリジン−2,5−ジオン化合物、上記化合物を作製するための合成法、これらを含有する薬学的組成物、および化合物の様々な使用を提供する。
本発明は、部分的に、式Ia、Ib、IcまたはIdの化合物、および式Ia、Ib、IcもしくはIdの化合物、
R1およびR2は、独立に、水素または−OR3であり、
R3は、独立に、水素またはグルクロニドであり、
X1、X2およびX3は、−CH2−、−CH(OH)−、および−C(O)−からなる群から選択され、X1、X2またはX3の1つのみは、−CH2−と異なってもよいが、
ただし、X1=X2=X3=−CH2−である場合、R1は、R2と異なる。
本発明は、式Ia、Ib、Ic、またはIdの化合物の合成のための方法を提供する。本発明はまた、以下のスキームおよび実施例に従う、本発明の種々の開示化合物の合成のための詳細な方法を提供する。
室温と溶媒の沸点との間の温度、典型的には還流温度での、適切な溶媒(例えば、四塩化炭素)中での、臭素の源としてN−ブロモスクシンアミド、およびラジカル開始剤としてアゾビスイソブチロニトリルを使用したVIIのラジカル開始ベンジル位臭素化によって、ブロミドXIが得られる。ブロミドは、0℃と100℃の間の温度、典型的には0℃で、極性非プロトン性溶媒(例えば、ジメチルホルムアミド)中の試薬(例えば、酢酸銀)を使用した置換反応によってアセテート中間体XIIに変換される。次いで、この中間体を、上記と同様の手順において使用する。三環式ケトエステルXIIと適切に置換されたインドール−3−アセトアミドVIとのカップリングによって、中間体XIIIが得られる。ここで使用される条件下で、アセテート基が除去され、アルコールを遊離する。上記のようにマグネシウム金属による二重結合の還元によって、トランス相対立体配置を有するラセミ中間体XIVが得られる。
本発明は、細胞増殖性障害の処置を必要とする被験体において、細胞増殖性障害を処置する方法を提供し、この方法は、このような処置を必要とする被験体に、治療有効量の本発明の化合物、またはその薬学的に受容可能な塩、プロドラッグ、代謝産物、多型もしくは溶媒和物を投与することによって処置する方法である。この細胞増殖性障害は、がんまたは前がん状態であり得る。本発明は、細胞増殖性障害の処置に有用な医薬の調製のための、本発明の化合物、またはその薬学的に受容可能な塩、プロドラッグ、代謝産物、多型もしくは溶媒和物の使用をさらに提供する。
本発明はまた、式Ia、Ib、Ic、またはIdの化合物を、少なくとも1種の薬学的に受容可能な賦形剤またはキャリアと組み合わせて含有する、薬学的組成物を提供する。
(実施例1)
(rac)−3−(5,6−ジヒドロ−4H−ピロロ[3,2,1−ij]キノリン−1−イル)−4−(6−ヒドロキシ−1H−インドール−3−イル)ピロリジン−2,5−ジオン(1)の調製
1の混合物(350mg)を、IPA:ヘキサン(20:80)を移動相として使用して逆相キラルHPLC(Chiralpak AD−H)によって分離し、4(138mg)を紫色の固体として(保持時間=7.85分)、1H NMR (DMSO) 400 MHz δ: 11.50 (bs, 1H), 10.62 (s, 1H), 8.93 (s, 1H), 7.32 (s, 1H), 7.13−7.17 (m, 3H), 6.84−6.89 (m, 2H), 6.71 (d, 1H, J = 1.9Hz), 6.51 (dd, 1H, J = 1.9Hz, 2.3Hz), 4.46 (d, 1H, J = 6.6Hz), 4.37 (d, 1H, J = 6.6Hz), 4.08−4.10 (m, 2H), 2.88−2.91 (m, 2H), 2.08−2.11 (m, 2H).MS[M+H]386;Mp:170〜172℃;および5(157mg)を紫色の固体(保持時間=11.30分)として得た。1H NMR (DMSO) 400 MHz δ: 11.50 (bs, 1H), 10.62 (s, 1H), 8.9s (s, 1H), 7.32 (s, 1H), 7.13−7.17 (m, 3H), 6.84−6.89 (m, 2H), 6.71 (d, 1H, J = 1.9Hz), 6.51 (dd, 1H, J = 1.9Hz, 2.3Hz), 4.46 (d, 1H, J = 6.6Hz), 4.37 (d, 1H, J = 6.6Hz), 4.08−4.10 (m, 2H), 2.88−2.91 (m, 2H), 2.08−2.11 (m, 2H).MS[M+H]386;Mp:173〜175℃。
(2S,3S,4S,5R)−6−((3−((rac)−trans−4−(5,6−ジヒドロ−4H−ピロロ[3,2,1−ij]キノリン−1−イル)−2,5−ジオキソピロリジン−3−イル)−1H−インドール−6−イル)オキシ)−3,4,5−トリヒドロキシテトラヒドロ−2H−ピラン−2−カルボン酸の調製
4および5を得るための(rac)−trans−3−[6−(ベンジルオキシ)−1H−インドール−3−イル]−4−(5,6−ジヒドロ−4H−ピロロ[3,2,1−ij]キノリン−1−イル)ピロリジン−2,5−ジオンのエナンチオマーのキラル分離
(rac)−trans−3−[6−(ベンジルオキシ)−1H−インドール−3−イル]−4−(5,6−ジヒドロ−4H−ピロロ[3,2,1−ij]キノリン−1−イル)ピロリジン−2,5−ジオンの混合物(350mg)を、イソプロパノール:ヘキサン(20:80)を移動相として使用して逆相キラルHPLC(Chiralpak AD−H)によって分離し、第1のエナンチオマー(保持時間=7.85分)(138mg)を紫色の固体として(Mp:170〜172℃)、1H NMR (DMSO−d6) 400 MHz δ: 11.50 (bs, 1H), 10.62 (s, 1H), 8.93 (s, 1H), 7.32 (s, 1H), 7.13−7.17 (m, 3H), 6.84−6.89 (m, 2H), 6.71 (d, J = 1.9Hz, 1H), 6.51 (dd, Ja = 2.3Hz, Jb =1.9Hz, 1H), 4.46 (d, J = 6.6Hz, 1H), 4.37 (d, J = 6.6Hz, 1H), 4.08−4.10 (m, 2H), 2.88−2.91 (m, 2H), 2.08−2.11 (m, 2H);LCMS[M+H]:386、および第2のエナンチオマー(保持時間=11.30分)(157mg)を紫色の固体として(Mp:173〜175℃)得た。1H NMR (DMSO−d6) 400 MHz δ: 11.50 (bs, 1H), 10.62 (s, 1H), 8.9s (s, 1H), 7.32 (s, 1H), 7.13−7.17 (m, 3H), 6.84−6.89 (m, 2H), 6.71 (d, J = 1.9Hz, 1H), 6.51 (dd, Ja = 2.3Hz, Jb =1.9Hz, 1H), 4.46 (d, J = 6.6Hz, 1H), 4.37 (d, J = 6.6Hz, 1H), 4.08−4.10 (m, 2H), 2.88−2.91 (m, 2H), 2.08−2.11 (m, 2H);LCMS[M+H]:386。
(rac)−trans−3−(6−ヒドロキシ−5,6−ジヒドロ−4H−ピロロ[3,2,1−ij]キノリン−1−イル)−4−(1H−インドール−3−イル)ピロリジン−2,5−ジオン(3)の調製
(3R,4R)−3−((S)−6−ヒドロキシ−5,6−ジヒドロ−4H−ピロロ[3,2,1−ij]キノリン−1−イル)−4−(1H−インドール−3−イル)ピロリジン−2,5−ジオン(10)および(3R,4R)−3−((R)−6−ヒドロキシ−5,6−ジヒドロ−4H−ピロロ[3,2,1−ij]キノリン−1−イル)−4−(1H−インドール−3−イル)ピロリジン−2,5−ジオン(11)のキラル分離
(3R,4R)−3−(1H−インドール−3−イル)−4−(6−オキソ−5,6−ジヒドロ−4H−ピロロ[3,2,1−ij]キノリン−1−イル)ピロリジン−2,5−ジオン(14)および(3S,4S)−3−(1H−インドール−3−イル)−4−(6−オキソ−5,6−ジヒドロ−4H−ピロロ[3,2,1−ij]キノリン−1−イル)ピロリジン−2,5−ジオン(8)の混合物の調製
(3R,4R)−3−(1H−インドール−3−イル)−4−(6−オキソ−5,6−ジヒドロ−4H−ピロロ[3,2,1−ij]キノリン−1−イル)ピロリジン−2,5−ジオン(14)および(3S,4S)−3−(1H−インドール−3−イル)−4−(6−オキソ−5,6−ジヒドロ−4H−ピロロ[3,2,1−ij]キノリン−1−イル)ピロリジン−2,5−ジオン(15)を得るための(8)のキラル分離
(3R,4R)−3−(1H−インドール−3−イル)−4−(4−オキソ−5,6−ジヒドロ−4H−ピロロ[3,2,1−ij]キノリン−1−イル)ピロリジン−2,5−ジオンおよび(3S,4S)−3−(1H−インドール−3−イル)−4−(4−オキソ−5,6−ジヒドロ−4H−ピロロ[3,2,1−ij]キノリン−1−イル)ピロリジン−2,5−ジオンの混合物(9)の合成
(3R,4R)−3−(1H−インドール−3−イル)−4−(4−オキソ−5,6−ジヒドロ−4H−ピロロ[3,2,1−ij]キノリン−1−イル)ピロリジン−2,5−ジオン(16)および(3S,4S)−3−(1H−インドール−3−イル)−4−(4−オキソ−5,6−ジヒドロ−4H−ピロロ[3,2,1−ij]キノリン−1−イル)ピロリジン−2,5−ジオン(17)の混合物のキラル分離
c−Met自己リン酸化阻害アッセイを、Journal of Biological Chemistry、286巻(23号)、20666〜20676頁(2010年6月10日)によって行った。
細胞増殖分析
細胞生存を、MTSアッセイによって決定した。手短に言えば、細胞を96ウェルプレート中にウェル毎に2,000〜10,000個の細胞で蒔き、完全増殖培地中で24時間培養し、次いで様々な薬物および薬物の組合せで72時間処理した。MTSを加え、4時間インキュベートし、その後570nmでマイクロプレートリーダーを使用して細胞生存率を評価した。データを未処理対照で正規化し、分析した。表2は、本発明の化合物の生物活性を示す。
Claims (15)
- X1=X2=X3=−CH2−である、請求項1に記載の化合物。
- X1、X2またはX3の少なくとも1つが、−CH(OH)−である、請求項1に記載の化合物。
- X1が、−CH(OH)−である、請求項3に記載の化合物。
- X1、X2またはX3の少なくとも1つが、−C(O)−である、請求項1に記載の化合物。
- X1が、−C(O)−である、請求項5に記載の化合物。
- X3が、−C(O)−である、請求項5に記載の化合物。
- R1が、Hであり、R2が、Hである、請求項1に記載の化合物。
- R1が、Hであり、R2が、−OR3である、請求項1に記載の化合物。
- R3が、Hである、請求項9に記載の化合物。
- 第2の抗増殖剤と組み合わせて投与されることを特徴とする、請求項14に記載の組成物。
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