JP2007531794A5 - - Google Patents

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JP2007531794A5
JP2007531794A5 JP2007507431A JP2007507431A JP2007531794A5 JP 2007531794 A5 JP2007531794 A5 JP 2007531794A5 JP 2007507431 A JP2007507431 A JP 2007507431A JP 2007507431 A JP2007507431 A JP 2007507431A JP 2007531794 A5 JP2007531794 A5 JP 2007531794A5
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  1. 構造式Iで表される化合物。
    Figure 2007531794
     （ここで、
    Xは、C(R6)またはNであり；
    R1、R2、R3およびR6は、それぞれ別異に、H、−NO2、−CN、−CF3、−SO2R8、−SR8、ハロゲン、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルコキシル、−OR7、−N(R7)2、−N(R7)C(O)R8、−C(O)R7または−CO2R8を表し；あるいは、R1およびR2、またはR2およびR3は、O、NおよびSより成る群から選択される0〜4個のヘテロ原子を有する4〜8員の環構造を形成し；
    R4は、空位、または、ぞれぞれ別異に、−(C(R9)2)nCH3・Yを表し；
    R5は、Hまたは−(C(R9)2)nCH3であり；
    R7は、それぞれ別異に、H、アルキル、アリールまたはアラルキルを表し；
    R8は、それぞれ別異に、アルキル、アリールまたはアラルキルを表し；
    R9は、それぞれ別異に、Hまたはアルキルを表し；
    nは、それぞれ別異に0〜15を表し；さらに、
    Yは、それぞれ別異に、ハロゲンまたはR8CO2 -を表す。）
  2. XはC(R6)であることを特徴とする請求項１記載の化合物。
  3. XはNであることを特徴とする請求項１記載の化合物。
  4. XはC(R6)であり；R1、R2、R3およびR6は、それぞれ別異に、H、−NO2、−CNであり；R4は空位であり；R5はHであることを特徴とする請求項１記載の化合物。
  5. XはC(R6)であり；R1、R2、R3およびR6はHであり；R4は空位であり；さらに、R5はHであることを特徴とする請求項１記載の化合物。
  6. XはNであり；R1、R2、R3およびR6はHであり；R4は空位であり；さらに、R5はHであることを特徴とする請求項１記載の化合物。
  7. 構造式IIで表される化合物。
    Figure 2007531794
     （ここで、
    R1 およびR3は、それぞれ別異に、H、−NO2、−CN、−CF3、−SO2R6、−SR6、ハロゲン、アルキル、アルケニル、アルキニル、アリール、アラルキル、−N(R5)C(O)R6、−C(O)R5または−CO2R6を表し；
    R2は、空位、または、それぞれ別異に−(C(R7)2)nCH3・Yを表し；
    R4は、Hまたは−(C(R7)2)nCH3を表し；
    R5は、それぞれ別異に、H、アルキル、アリールまたはアラルキルを表し；
    R6は、それぞれ別異に、アルキル、アリールまたはアラルキルを表し；
    R7は、それぞれ別異に、Hまたはアルキルを表し；
    nは、それぞれ別異に0〜15を表し；さらに、
    Yは、それぞれ別異に、ハロゲンまたはR6CO2 -を表す。）
  8. R1 およびR3は、それぞれ別異に、H、−NO2、−CNを表し；R2は空位であり；さらに、R4はHであることを特徴とする請求項７記載の化合物。
  9. R1 はHであり；R3は−NO2であり；R2は空位であり；さらに、R4はHであることを特徴とする請求項７記載の化合物。
  10. 構造式IIIで表される化合物。
    Figure 2007531794
     （ここで、
    R1 およびR2は、それぞれ別異に、H、−NO2、−CN、−CF3、−SO2R6、−SR6、ハロゲン、アルキル、アルケニル、アルキニル、アリール、アラルキル、−N(R5)C(O)R6、−C(O)R5または−CO2R6を表し；
    R3は、空位、または、それぞれ別異に−(C(R7)2)nCH3・Yを表し；
    R4は、Hまたは−(C(R7)2)nCH3であり；
    R5は、それぞれ別異に、H、アルキル、アリールまたはアラルキルを表し；
    R6は、それぞれ別異に、アルキル、アリールまたはアラルキルを表し；
    R7は、それぞれ別異に、Hまたはアルキルを表し；
    nは、それぞれ別異に0〜15を表し；さらに、
    Yは、それぞれ別異に、ハロゲンまたはR6CO2 -を表す。）
  11. R1 およびR2は、それぞれ別異に、H、−NO2、−CNを表し；R3は空位であり；さらに、R4はHであることを特徴とする請求項１０記載の化合物。
  12. R1 はHであり；R2は−NO2であり；R3は空位であり；さらに、R4はHであることを特徴とする請求項１０記載の化合物。
  13. 構造式IVで表される化合物。
    Figure 2007531794
     （ここで、
    R1 は、H、−SR5、アルキル、アリール、−N(R4)2、−（C(R4)2)mCO2R5、−NO2、−CN、−CF3、−SO2R5、ハロゲン、アルケニル、アルキニル、アラルキル、−N(R4)C(O)R5、−C(O)R4または−CO2R5を表し；
    R2は、空位、または、それぞれ別異に−(C(R6)2)nCH3・Yを表し；
    R3は、Hまたは−(C(R6)2)nCH3であり；
    R4は、それぞれ別異に、H、アルキル、アリールまたはアラルキルを表し；
    R5は、それぞれ別異に、アルキル、アリールまたはアラルキルを表し；
    R6は、それぞれ別異に、Hまたはアルキルを表し；
    nは、それぞれ別異に0〜15を表し；
    ｍは、1、2、3、4、5、6、7または8であり；さらに、
    Yは、それぞれ別異に、ハロゲンまたはR5CO2 -を表す。）
  14. R1 は、−SR5、アルキル、アリール、−N(R4)2または−（C(R4)2)mCO2R5であることを特徴とする請求項１３記載の化合物。
  15. R2は空位であり；さらに、R3はHであることを特徴とする請求項１３記載の化合物。
  16. R1 は、−SR5、アルキル、アリール、−N(R4)2または−（C(R4)2)mCO2R5であり；R2は空位であり；R3はHであり；R4はHであり；R5は、アルキルまたはアラルキルであり；さらに、mは1であることを特徴とする請求項１３記載の化合物。
  17. 構造式Vで表される化合物。
    Figure 2007531794
     （ここで、
    R1 、R３およびR4は、それぞれ別異に、H、−NO2、−CN、−CF3、−SO2R7、−SR7、ハロゲン、アルキル、アルケニル、アルキニル、アリール、アラルキル、−N(R6)C(O)R5、−C(O)R6または−CO2R7を表し；
    R2は、空位、または、それぞれ別異に−(C(R8)2)nCH3・Yを表し；
    R5は、Hまたは−(C(R8)2)nCH3であり；
    R6は、それぞれ別異に、H、アルキル、アリールまたはアラルキルを表し；
    R7は、それぞれ別異に、アルキル、アリールまたはアラルキルを表し；
    R8は、それぞれ別異に、Hまたはアルキルを表し；
    nは、それぞれ別異に0〜15を表し；さらに、
    Yは、それぞれ別異に、ハロゲンまたはR7CO2 -を表す。）
  18. R2は空位であり；さらに、R5はHであることを特徴とする請求項１７記載の化合物。
  19. R1はHであり；R2は空位であり；R3およびR4は−CNであり；さらに、R5はHであることを特徴とする請求項１７記載の化合物。
  20. ホスファイト化合物の調製法であって、ホスホルアミダイト、アルコールおよび活性化剤を混合してホスファイト化合物を調製する工程を含み、該活性化剤は、以下の化合物群から選択されることを特徴とする調製方法。
    Figure 2007531794
     （ここで、
    Xは、C(R6)またはNであり；
    R1、R2、R3およびR6は、それぞれ別異に、H、−NO2、−CN、−CF3、−SO2R8、−SR8、ハロゲン、アルキル、アルケニル、アルキニル、アリール、アラルキル、アルコキシル、−OR7、−N(R7)2、−N(R7)C(O)R8、−C(O)R7または−CO2R8を表し；あるいは、R1およびR6、R1およびR2、または、R2およびR3は、O、NおよびSより成る群から選択される0〜4個のヘテロ原子を有する4〜8員の環構造を形成し；
    R4は、空位、または、ぞれぞれ別異に、−(C(R9)2)nCH3・Yを表し；
    R5は、Hまたは−(C(R9)2)nCH3であり；
    R7は、それぞれ別異に、H、アルキル、アリールまたはアラルキルを表し；
    R8は、それぞれ別異に、アルキル、アリールまたはアラルキルを表し；
    R9は、それぞれ別異に、Hまたはアルキルを表し；
    nは、それぞれ別異に0〜15を表し；さらに、
    Yは、それぞれ別異に、ハロゲンまたはR8CO2 -を表す）；
    Figure 2007531794
     （ここで、
    R1 およびR3は、それぞれ別異に、H、−NO2、−CN、−CF3、−SO2R6、−SR6、ハロゲン、アルキル、アルケニル、アルキニル、アリール、アラルキル、−N(R5)C(O)R6、−C(O)R5または−CO2R6を表し；
    R2は、空位、または、それぞれ別異に−(C(R7)2)nCH3・Yを表し；
    R4は、Hまたは−(C(R7)2)nCH3であり；
    R5は、それぞれ別異に、H、アルキル、アリールまたはアラルキルを表し；
    R6は、それぞれ別異に、アルキル、アリールまたはアラルキルを表し；
    R7は、それぞれ別異に、Hまたはアルキルを表し；
    nは、それぞれ別異に0〜15を表し；さらに、
    Yは、それぞれ別異に、ハロゲンまたはR6CO2 -を表す）；
    Figure 2007531794
     （ここで、
    R1 およびR2は、それぞれ別異に、H、−NO2、−CN、−CF3、−SO2R6、−SR6、ハロゲン、アルキル、アルケニル、アルキニル、アリール、アラルキル、−N(R5)C(O)R6、−C(O)R5または−CO2R6を表し；
    R3は、空位、または、それぞれ別異に−(C(R7)2)nCH3・Yを表し；
    R4は、Hまたは−(C(R7)2)nCH3であり；
    R5は、それぞれ別異に、H、アルキル、アリールまたはアラルキルを表し；
    R6は、それぞれ別異に、アルキル、アリールまたはアラルキルを表し；
    R7は、それぞれ別異に、Hまたはアルキルを表し；
    nは、それぞれ別異に0〜15を表し；さらに、
    Yは、それぞれ別異に、ハロゲンまたはR6CO2 -を表す）；
    Figure 2007531794
     （ここで、
    R1 は、H、−SR5、アルキル、アリール、−N(R4)2、−（C(R4)2)mCO2R5、−NO2、−CN、−CF3、−SO2R5、ハロゲン、アルケニル、アルキニル、アラルキル、−N(R4)C(O)R5、−C(O)R4または−CO2R5を表し；
    R2は、空位、または、それぞれ別異に−(C(R6)2)nCH3・Yを表し；
    R3は、Hまたは−(C(R6)2)nCH3であり；
    R4は、それぞれ別異に、H、アルキル、アリールまたはアラルキルを表し；
    R5は、それぞれ別異に、アルキル、アリールまたはアラルキルを表し；
    R6は、それぞれ別異に、Hまたはアルキルを表し；
    nは、それぞれ別異に0〜15を表し；
    ｍは、1、2、3、4、5、6、7または8であり；さらに、
    Yは、それぞれ別異に、ハロゲンまたはR5CO2 -を表す）；および、
    Figure 2007531794
     ここで、
    R1 、R３およびR4は、それぞれ別異に、H、−NO2、−CN、−CF3、−SO2R7、−SR7、ハロゲン、アルキル、アルケニル、アルキニル、アリール、アラルキル、−N(R6)C(O)R5、−C(O)R6または−CO2R7を表し；
    R2は、空位、または、それぞれ別異に−(C(R8)2)nCH3・Yを表し；
    R5は、Hまたは−(C(R8)2)nCH3であり；
    R6は、それぞれ別異に、H、アルキル、アリールまたはアラルキルを表し；
    R7は、それぞれ別異に、アルキル、アリールまたはアラルキルを表し；
    R8は、それぞれ別異に、Hまたはアルキルを表し；
    nは、それぞれ別異に0〜15を表し；さらに、
    Yは、それぞれ別異に、ハロゲンまたはR7CO2 -を表す。）
  21. 前記ホスホルアミダイトは、3'−ヌクレオシドホスホルアミダイト、3'−ヌクレオチドホスホルアミダイトまたは3'−オリゴヌクレオチドホスホルアミダイトであることを特徴とする請求項２０記載の方法。
  22. 前記ホスホルアミダイトは、下記の構造式Aで表されることを特徴とする請求項２０記載の方法。
    Figure 2007531794
     （ここで、
    R1は、アルキル、アリール、アラルキルまたは−Si(R5)5であり；このとき、該アルキル、アリールおよびアラルキル基は、−CN、−NO2、−CF3、ハロゲン、−O2CR5または−OSO2R5で必要に応じて置換されており；
    R2は、必要に応じて置換されたアルキル、シクロアルキル、ヘテロシクロアルキル、アリール、アラルキルまたはアルケニルであり；
    R3およびR4は、それぞれ別異に、アルキル、シクロアルキル、ヘテロシクロアルキル、アリールまたはアラルキルを表し；あるいは、R3およびR4は、共に3〜8員の環構造を形成し；さらに、
    R5は、アルキル、シクロアルキル、ヘテロシクロアルキル、アリールまたはアラルキルである。）
  23. R1は−CH2CH2CNであることを特徴とする請求項２２記載の方法。
  24. R2は、必要に応じて置換されたヘテロシクロアルキルであることを特徴とする請求項２２記載の方法。
  25. R2は、必要に応じて置換されたリボースであることを特徴とする請求項２２記載の方法。
  26. R2は、必要に応じて置換されたデオキシリボースであることを特徴とする請求項２２記載の方法。
  27. R2は、ヌクレオシドまたはヌクレオチドであることを特徴とする請求項２２記載の方法。
  28. R3およびR4は、アルキルであることを特徴とする請求項２２記載の方法。
  29. 前記アルコールは、必要に応じて置換されたリボースであることを特徴とする請求項２０記載の方法。
  30. 前記アルコールは、必要に応じて置換されたデオキシリボースであることを特徴とする請求項２０記載の方法。
  31. 前記アルコールは、ヌクレオシド、ヌクレオチドまたはオリゴヌクレオチドであることを特徴とする請求項２０記載の方法。
  32. 前記アルコールは、R5−OHで表され、ここで、R5は、必要に応じて置換されたアルキル、シクロアルキル、ヘテロシクロアルキル、アリール、アラルキル、アルケニルまたは−(C(R6)2)pヘテロシクロアルキルであり；R6は、Hまたはアルキルであり；さらに、pは、1、2、3、4、5、6、7、または8であることを特徴とする請求項２０記載の方法。
  33. R5は、−(C(R6)2)pヘテロシクロアルキルであることを特徴とする請求項３２記載の方法。
  34. 前記ホスホルアミダイト、前記アルコールおよび前記活性化剤の混合物に、プロトンシャトル化合物を混合する工程をさらに含み、該プロトンシャトル化合物のpKaは、前記活性化剤のpKaより高く、かつ前記ホスホルアミダイトのpKaより低いことを特徴とする請求項２０記載の方法。
  35. 前記プロトンシャトル化合物は、一級、二級または三級アミンであることを特徴とする請求項３４記載の方法。
  36. 前記プロトンシャトル化合物はN(R7)(R8)R9で表され、ここで、R7、R8およびR9は、それぞれ別異に、H、アルキル、シクロアルキル、アリール、アラルキル、アルケニルを表し；あるいは、R7およびR8は、共に3〜8員の環構造を形成し；さらに、R9は、H、アルキル、シクロアルキル、アリールまたはアラルキルであることを特徴とする請求項３４記載の方法。
JP2007507431A 2004-04-05 2005-04-05 オリゴヌクレオチドの合成および精製に使用する方法および反応試薬 Pending JP2007531794A (ja)

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