JP5176240B2 - ヒストン脱アセチル化酵素(hdac)阻害剤としてのチオフェン及びチアゾール置換トリフルオロエタノン誘導体 - Google Patents
ヒストン脱アセチル化酵素(hdac)阻害剤としてのチオフェン及びチアゾール置換トリフルオロエタノン誘導体 Download PDFInfo
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- JP5176240B2 JP5176240B2 JP2008529700A JP2008529700A JP5176240B2 JP 5176240 B2 JP5176240 B2 JP 5176240B2 JP 2008529700 A JP2008529700 A JP 2008529700A JP 2008529700 A JP2008529700 A JP 2008529700A JP 5176240 B2 JP5176240 B2 JP 5176240B2
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- alkyl
- ring
- trifluoroacetyl
- membered
- independently
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Description
(X=O)結合基及びトリフルオロアセチル基の各々は、独立して、任意の炭素環原子上に置換されており;
Aは、CH又はNであり;
Dは、CHであり;
Xは、C又はS=Oであり;
R1は、水素、C1−6アルキル、C2−10アルケニル、C2−10アルキニル、C3−10シクロアルキル、C6−10アリール、独立してN、O、及びSから選択される、1、2、3、又は4個のヘテロ原子を含有し、その多くとも1個のヘテロ原子がO又はSである5員のヘテロ芳香環、1、2、又は3個の窒素原子を含有する6員のヘテロ芳香環、又は、独立してN、O、及びSから選択される、1、2、3、又は4個のヘテロ原子を含有する7〜10員の、飽和、部分飽和、又は不飽和のヘテロ環であって;任意の該環は、独立してハロゲン、シアノ、C1−6アルキル、C1−6アルコキシ、メルカプトC1−6アルキル、ハロC1−6アルキル、ハロC1−6アルコキシ、アミノ、C1−6アルキルアミノ、及びジ(C1−6アルキル)アミノから選択される、1以上の基で置換されてもよく;或いは、
R1は、−(CH2)b−N−(CR2R3)aWと一緒になって、1個のN原子を含有する4員の飽和ヘテロ環か、又は、1、2、又は3個のN原子と、ゼロ又は1個のO原子とを含有する5、6、又は7員の飽和ヘテロ環を形成し;該環は、C3−10シクロアルキル環か、独立してN、O、及びSから選択される1、2、又は3個のヘテロ原子を含有する5、6、又は7員の飽和又は部分飽和ヘテロ環か、フェニル環か、独立してN、O、及びSから選択される1、2、又は3個のヘテロ原子を含有し、その多くとも1個のヘテロ原子がO又はSである5員のヘテロ芳香環か、又は1、2、又は3個の窒素原子を含有する6員のヘテロ芳香環に縮合されてもよく;1つの炭素環原子において、独立してN、O、又はSから選択されるゼロ、1、又は2個のヘテロ原子を含有する5又は6員のスピロ環によって置換されてもよく、該環はフェニル環に縮合されてもよく;或いは、1又は2個のC1−4アルキル基により架橋されてもよく;任意の該環は、独立してL−R4から選択される1以上の基によって置換されてもよく;
各Lは、独立して直接結合か、(CH2)d、又はC=Oであり;
R2及びR3は、独立して、水素、C1−6アルキル、C2−6アルケニル、C2−6アルキニル、ハロC1−6アルキル、C6−10アリール、独立してN、O、及びSから独立して選択される1、2、3、又は4個のヘテロ原子を含有し、その多くとも1個のヘテロ原子がO又はSである5員のヘテロ芳香環;1、2、又は3個の窒素原子を含有する6員のヘテロ芳香環;又は、独立してN、O、及びSから選択される1、2、又は3個のヘテロ原子を含有する7〜10員の、不飽和又は部分飽和ヘテロ環であるか;或いは
R2及びR3は、それらが結合している炭素原子と一緒になって、C3−7シクロアルキル基、>C=O、又は>C=CHを形成し;
Wは、ハロゲン、C1−6アルキル、アミノ、C1−6アルキルアミノ、ジ(C1−6アルキル)アミノ、C1−6アルコキシ、S(O)r(CH2)cR5であるか;又は、環であって:C3−5シクロアルキル基か;独立してN、O、及びSから選択される1、2、又は3個のヘテロ原子を含有する5又は6員の、飽和又は部分飽和ヘテロ環;6〜13員の、飽和、部分飽和、又は不飽和の炭化水素環;独立してN、O、及びSから選択される1、2、3、又は4個のヘテロ原子を含有し、その多くとも1個のヘテロ原子がO又はSである5員のヘテロ芳香環;1、2、又は3個の窒素原子を含有する6員のヘテロ芳香環;又は、独立してN、O、及びSから選択される1、2、3、又は4個のヘテロ原子を含有する7〜15員の、飽和、部分飽和、又は不飽和のヘテロ環であって;任意の該アルキル基又は環は、独立してR6から選択される1以上の基によって置換されてもよく;
各R4は、独立して、ハロゲン;シアノ;ヒドロキシ;オキソ;C1−6アルキル;ハロC1−6アルキル;C1−6アルコキシ;メルカプトC1−6アルキル;ハロC1−6アルコキシ;C1−6アルキルカルボニル;C1−6アルコキシカルボニル;ニトロ;N(Ra)2;N(Ra)CON(Ra)2;N(Ra)CO(C1−6アルキル);N(Ra)CO2(C1−6アルキル);S(O)r(CH2)cR5であるか;又は、環であって:C3−10シクロアルキル;C6−10アリール;C6−10アリールC1−6アルキル;C6−10アリールオキシC1−6アルキル;C6−10アリールカルボニル;独立してN、O、及びSから選択される1、2、又は3個のヘテロ原子を含有する、5又は6員の、飽和又は部分飽和ヘテロ環;独立してN、O、及びSから選択される1、2、3、又は4個のヘテロ原子を含有し、その多くとも1個のヘテロ原子がO又はSである5員のヘテロ芳香環;1、2、又は3個の窒素原子を含有する6員のヘテロ芳香環;又は、独立してN、O、及びSから選択される1、2、又は3個のヘテロ原子を含有する7〜10員の、不飽和又は部分飽和ヘテロ環であって;任意の該アルキル基又は環は、独立してシアノ、オキソ、ヒドロキシ、ハロゲン、C1−6アルキル、C1−6アルコキシ、メルカプトC1−6アルキル、ハロC1−6アルキル、ハロC1−6アルコキシ、アミノ、C1−6アルキルアミノ、ジ(C1−6アルキル)アミノ、1、2、又は3個の窒素原子を含有する6員のヘテロ芳香環、及び、C6−10アリールから選択される1以上の基によって置換されてもよく、任意の該環は、独立してハロゲン、C1−6アルキル、C1−6アルコキシ、及びハロC1−6アルキルから選択される1以上の基によって置換されてもよく;
R5は、C1−6アルキル、アミノ、C1−6アルキルアミノ、ジ(C1−6アルキル)アミノ、C2−10アルケニル、C2−10アルキニル、C3−10シクロアルキル、C6−10アリール、C6−10アリールオキシ、独立してN、O、及びSから選択される1、2、3、又は4個のヘテロ原子を含有し、その多くとも1個のヘテロ原子がO又はSである5員のヘテロ芳香環、1、2、又は3個の窒素原子を含有する6員のヘテロ芳香環、又は、独立してN、O、及びSから選択される1、2、3、又は4個のヘテロ原子を含有する7〜10員の、飽和、部分飽和、又は不飽和のヘテロ環であって;任意の該アルキル又はアルケニル基、又は環は、独立してハロゲン、シアノ、オキソ、ヒドロキシ、C1−6アルキル、C1−6アルコキシ、ハロC1−6アルキル、ハロC1−6アルコキシ、N(Ra)2、−C1−6アルキルN(Ra)2、C1−6アルキルカルボニル、C1−6アルコキシカルボニル、C6−10アリール、及びC6−10アリールオキシ環から選択される1以上の基によって置換されてもよく、該環は、独立してハロゲン、C1−6アルキル、ハロC1−6アルキルから選択される1、2、又は3個の基によって置換されてもよく;
各R6は、独立してハロゲン、シアノ、オキソ、ヒドロキシ、C1−6アルキル、C1−6アルコキシ、メルカプトC1−6アルキル、ハロC1−6アルキル、ハロC1−6アルコキシ、C1−6アルコキシC1−6アルキル、C1−6アルキルカルボニル;C1−6アルコキシカルボニル;ニトロ;N(Ra)2;CON(Ra)2;N(Ra)CON(Ra)2;N(Ra)CO(C1−6アルキル);N(Ra)CO2(C1−6アルキル);S(O)r(CH2)cR5、O(C1−10アルキル)N(Ra)COR7であるか;又は、環であって:C3−7シクロアルキル、C6−10アリール、C6−10アリールC1−6アルキル、C6−10アリールオキシC1−6アルキル、C6−10アリールオキシ、C6−10アリールカルボニル、独立してN、O、及びSから選択される1、2、又は3個のヘテロ原子を含有する5又は6員の、飽和又は部分飽和ヘテロ環、又は、独立してN、O、及びSから選択される1、2、3、又は4個のヘテロ原子を含有し、その多くとも1個のヘテロ原子がO又はSである5員のヘテロ芳香環であって;任意の該環は、独立してハロゲン、C1−6アルキル、及びC1−6アルコキシから選択される1以上の基によって置換されてもよく;
R7は、ハロゲンによって置換されてもよい、C1−6アルコキシ又はC1−6アルキルか、又は、独立してN、O、及びSから選択される1、2、3、又は4個のヘテロ原子を含有する7〜10員の、飽和又は部分飽和ヘテロ環であって、該環は、独立してハロゲン、ヒドロキシ、オキソ、C1−6アルキル、及びC1−6アルコキシから選択される1以上の基によって置換されてもよく;
各Raは、独立して水素、C1−6アルキル、C1−6アルキルカルボニル、C1−6アルコキシカルボニル、C6−10アリール、又はC6−10アリールカルボニルであり;
aは、ゼロ、1、2、3、4、5、又は6であり;
bは、ゼロ、1、2、3、又は4であり;
cは、ゼロ、1、2、3、又は4であり;
各dは、独立して1、2、3、又は4であり;
rは、ゼロ、1、又は2である]
の化合物か、又は医薬的に許容され得るその塩を提供する。
Aは、CH又はNであり;
Dは、CHであり;
AがNであるとき、トリフルオロアセチル基は、D上に置換され;
AがCHであるとき、トリフルオロアセチル基は、A又はDのいずれかの上に置換され;
XはCであるか、又はS=Oであり;
R1は、水素、C1−6アルキル、C2−10アルケニル、C2−10アルキニル、C6−10アリール、独立してN、O、及びSから選択される1、2、3、又は4個のヘテロ原子を含有し、その多くとも1個のヘテロ原子がO又はSである5員のヘテロ芳香環、1、2、又は3個の窒素原子を含有する6員のヘテロ芳香環、又は、独立してN、O、及びSから選択される1、2、3、又は4個のヘテロ原子を含有する7〜10員の、飽和、部分飽和、又は不飽和のヘテロ環であって;任意の該環は、独立してハロゲン、シアノ、C1−6アルキル、C1−6アルコキシ、メルカプトC1−6アルキル、ハロC1−6アルキル、ハロC1−6アルコキシ、アミノ、C1−6アルキルアミノ、及びジ(C1−6アルキル)アミノから選択される1以上の基で置換されてもよく;或いは、
R1は、−(CH2)b−N−(CR2R3)aWと一緒になって、1個のN原子を含有する4員の飽和ヘテロ環か;1、2、又は3個のN原子と、ゼロ又は1個のO原子とを含有する5、6、又は7員の飽和ヘテロ環を形成しており;該環は、フェニル環か、独立してN、O、及びSから選択される1、2、又は3個のヘテロ原子を含有し、その多くとも1個のヘテロ原子がO又はSである5員のヘテロ芳香環か、又は1、2、又は3個の窒素原子を含有する6員のヘテロ芳香環に縮合されてもよく;1つの炭素環原子においては、独立してN、O、又はSから選択されるゼロ、1、又は2個のヘテロ原子を含有する5又は6員のスピロ環によって置換されてもよく、該環はフェニル環に縮合されてもよく;又は、C1−4アルキル基によって架橋されてもよく;任意の該環は、独立してR4から選択される1以上の基によって置換されてもよく;
R2及びR3は、独立して、水素、C1−6アルキル、C2−6アルケニル、C2−6アルキニル、C6−10アリール、独立してN、O、及びSから独立して選択される1、2、3、又は4個のヘテロ原子を含有し、その多くとも1個のヘテロ原子がO又はSである5員のヘテロ芳香環;1、2、又は3個の窒素原子を含有する6員のヘテロ芳香環;又は、独立してN、O、及びSから選択される1、2、又は3個のヘテロ原子を含有する7〜10員の、不飽和又は部分飽和ヘテロ環であり;或いは
R2及びR3は、それらが結合している炭素原子と一緒になってC3−7シクロアルキル基を形成し;
Wは、C1−6アルキル、アミノ、C1−6アルキルアミノ、ジ(C1−6アルキル)アミノ、C1−6アルコキシ、S(O)r(CH2)cR5であるか;又は、環であって:C3−5シクロアルキル基か;独立してN、O、及びSから選択される1、2、又は3個のヘテロ原子を含有する5又は6員の、飽和又は部分飽和ヘテロ環;6〜13員の、飽和、部分飽和、又は不飽和の炭化水素環;独立してN、O、及びSから選択される1、2、3、又は4個のヘテロ原子を含有し、その多くとも1個のヘテロ原子がO又はSである5員のヘテロ芳香環;1、2、又は3個の窒素原子を含有する6員のヘテロ芳香環;又は、独立してN、O、及びSから選択される1、2、3、又は4個のヘテロ原子を含有する7〜10員の、飽和、部分飽和、又は不飽和のヘテロ環であって;任意の該環は、独立してR6から選択される1以上の基によって置換されてもよく;
各R4は、ハロゲン;シアノ;C1−6アルキル;ハロC1−6アルキル;C1−6アルコキシ;メルカプトC1−6アルキル;ハロC1−6アルコキシ;C1−6アルキルカルボニル;C1−6アルコキシカルボニル;ニトロ;N(Ra)2;CON(Ra)2;N(Ra)CON(Ra)2;N(Ra)CO(C1−6アルキル);N(Ra)CO2(C1−6アルキル);S(O)r(CH2)cR5であるか;又は、環であって:C6−10アリール;C6−10アリールC1−6アルキル;C6−10アリールオキシC1−6アルキル;C6−10アリールカルボニル;独立してN、O、及びSから選択される1、2、3、又は4個のヘテロ原子を含有し、その多くとも1個のヘテロ原子がO又はSである5員のヘテロ芳香環;1、2、又は3個の窒素原子を含有する6員のヘテロ芳香環;又は、独立してN、O、及びSから選択される1、2、又は3個のヘテロ原子を含有する7〜10員の、不飽和又は部分飽和ヘテロ環であって;任意の該環は、独立してハロゲン、C1−6アルキル、C1−6アルコキシ、メルカプトC1−6アルキル、ハロC1−6アルキル、ハロC1−6アルコキシ、アミノ、C1−6アルキルアミノ、ジ(C1−6アルキル)アミノ、1、2、又は3個の窒素原子を含有する6員のヘテロ芳香環、及び、独立してハロゲン、C1−6アルキル、ハロC1−6アルキルから選択される1以上の基によって置換されてもよいC6−10アリールから選択される、1以上の基によって置換されてもよく;
R5は、C1−6アルキル、アミノ、C1−6アルキルアミノ、ジ(C1−6アルキル)アミノ、C2−10アルケニル、C2−10アルキニル、C6−10アリール、独立してN、O、及びSから選択される1、2、3、又は4個のヘテロ原子を含有し、その多くとも1個のヘテロ原子がO又はSである5員のヘテロ芳香環、1、2、又は3個の窒素原子を含有する6員のヘテロ芳香環、又は、独立してN、O、及びSから選択される1、2、3、又は4個のヘテロ原子を含有する7〜10員の、飽和、部分飽和、又は不飽和のヘテロ環であって;任意の環は、独立してハロゲン、シアノ、C1−6アルキル、C1−6アルコキシ、ハロC1−6アルキル、ハロC1−6アルコキシ、アミノ、C1−6アルキルアミノ、ジ(C1−6アルキル)アミノから選択される1以上の基によって置換されてもよく;
各R6は、ハロゲン、シアノ、C1−6アルキル、C1−6アルコキシ、メルカプトC1−6アルキル、ハロC1−6アルキル、ハロC1−6アルコキシ、C1−6アルコキシC1−6アルキル、C1−6アルキルカルボニル;C1−6アルコキシカルボニル;ニトロ;N(Ra)2;CON(Ra)2;N(Ra)CON(Ra)2;N(Ra)CO(C1−6アルキル);N(Ra)CO2(C1−6アルキル);S(O)r(CH2)cR5、O(C1−10アルキル)N(Ra)COR7であるか;又は、環であって:C3−7シクロアルキル;、C6−10アリール、C6−10アリールC1−6アルキル、C6−10アリールオキシC1−6アルキル、C6−10アリールオキシ、C6−10アリールカルボニル、独立してN、O、及びSから選択される1、2、又は3個のヘテロ原子を含有する5又は6員の、飽和又は部分飽和ヘテロ環、又は、独立してN、O、及びSから選択される1、2、3、又は4個のヘテロ原子を含有し、その多くとも1個のヘテロ原子がO又はSである5員のヘテロ芳香環であって;任意の該環は、独立してハロゲン、C1−6アルキル、及びC1−6アルコキシから選択される1以上の基によって置換されてもよく;
R7は、ハロゲンによって置換されてもよい、C1−6アルコキシ又はC1−6アルキルか、又は、独立してN、O、及びSから選択される1、2、3、又は4個のヘテロ原子を含有する7〜10員の、飽和又は部分飽和ヘテロ環であって、該環は、独立してハロゲン、ヒドロキシ、オキソ、C1−6アルキル、及びC1−6アルコキシから選択される1以上の基によって置換されてもよく;
各Raは、独立して水素、又はC1−6アルキルであり;
aは、ゼロ、1、2、3、4、5、又は6であり;
bは、ゼロ、1、2、3、又は4であり;
cは、ゼロ、1、2、3、又は4であり;
rは、ゼロ、1、又は2であり、
又は、医薬的に許容され得るその塩である。
1つの実施態様においては、Lは、直接結合、CH2、CH2CH2、又はC=Oである。
好ましくは、R1は、−(CH2)b−N−(CR2R3)aWと一緒になって、1、2、又は3個のN原子と、ゼロ又は1個のO原子とを含有する5又は6員の飽和ヘテロ環を形成しており;該環は、フェニル又はイミダゾール環に縮合されてもよく;1つの炭素環原子において、独立してN、O、及びSから選択されるゼロ、1、又は2個のヘテロ原子を含有する5又は6員のスピロ環によって置換されてもよく、該環はフェニル環に縮合されてもよく;任意の該環は、独立してR4から選択される1以上の基によって置換されてもよい。
さらに具体的な基は、3−メチル−4−(4−メチルフェニル)ピペラジン−1−イル、4−アセチルピペラジン−1−イル、4−(メトキシカルボニル)ピペリジン−1−イル、4−[(4−クロロフェニル)(フェニル)メチル]ピペラジン−1−イル、4−テトラヒドロフラン−2−イルカルボニル)ピペラジン−1−イル、4−(2−エトキシ−2オキソエチル)ピペラジン−1−イル、4−(3−メトキシフェニル)ピペラジン−1−イル、4−シアノ−4−フェニルピペリジン−1−イル、4−エチルカルボニル−4−フェニルピペリジン−1−イル、4−[2−(メチルスルホニル)エチル]ピペラジン−1−イル、4−[3,5−ジクロロピリジン−4−イル]ピペラジン−1−イル、4−(1H−1,2,3−ベンゾトリアゾール−1−イル)ピペリジン−1−イル、4−[(3−メチルピリジン−2−イル)メチル]ピペラジン−1−イル、3−フェニルピペリジン−1−イル、4−(1,2,3,4−テトラヒドロナフタレン−2−イル)ピペラジン−1−イル、3−オキソピペラジン−1−イル、4−(1−アダマンチル)ピペラジン−1−イル、3,4−ジメチルピペラジン−1−イル、4−(モルホリン−4−イルカルボニル)ピペリジン−1−イル、4−(ピロリジン−1−イルカルボニル)ピペリジン−1−イル、4−(3−クロロベンジル)ピペリジン−1−イル、4−(5−フルオロ−1H−ベンゾイミダゾール−2−イルピペリジン−1−イル、3−(1−メチル−1H−イミダゾール−2−イルカルボニル)ピペリジン−1−イル、3−(6−メチル−1H−ベンゾイミダゾール−2−イル)ピペリジン−1−イル、4−(4−フルオロベンジル)−3−オキソピペラジン−1−イル、4−(1H−1,2,4−トリアゾール−3−イルカルボニル)ピペラジン−1−イル、4−(3,4−ジクロロフェニル)ピペラジン−1−イル、(3R,4aS,8aS)−3−(tertブチルアミノカルボニル)デカヒドロイソキノリン−2−イル、(1R,4R)−5−ベンジル−5−アザ−2−アゾニアビシクロ[2.2.1]ヘプタ−2−イル、4−(5−クロロ−2−メトキシフェニル)ピペラジン−1−イル、4−(4−シアノフェニル)ピペラジン−1−イル、4−ブロモピペリジン−1−イル、(4aR,8aR)−4−(オキソ)オクタヒドロキノリン−1−イル、4−(2−オキソ−1,3−ジヒドロ−2H−ベンゾイミダゾール−1−イル)ピペリジン−1−イル、4−(2−クロロフェニル)ピペラジン−1−イル、4−(2−エトキシフェニル)ピペラジン−1−イル、4−(4−メトキシフェニル)ピペラジン−1−イル、4−(2−メチルフェニル)ピペラジン−1−イル、4−(ブタン−1−オン)−4−フェニルピペリジン−1−イル、(1S,4S)−5−(3−クロロフェニル)−2,5−ジアザビシクロ[2.2.1]ヘプタ−2−イル、(1S,4S)−5−(2−クロロフェニル)−2,5−ジアザビシクロ[2.2.1]ヘプタ−2−イル、4−(2−メトキシベンジル)ピペラジン−1−イル、4−(3−メトキシベンジル)ピペラジン−1−イル、4−(キナゾリン−4−イル)ピペラジン−1−イル、4−(ピリジン−3−イル)ピペラジン−1−イル、4−シクロヘキシル−3−オキソピペラジン−1−イル、4−[(2−メチル−1,3−チアゾール−4−イル)メチル]ピペラジン−1−イル、4−シクロプロピルピペラジン−1−イル、(2S)−4−メチル−2−フェニルピペラジン−1−イル、2−(トリフルオロメチル)−5,6,7,8−テトラヒドロイミダゾ[1,2−a]ピラジン−7−イル、4−(4−メチル−1,2,5−オキサジアゾール−3−イル)ピペラジン−1−イル、4−(ピリジン−3−イルメチル)ピペラジン−1−イル、4−(ピリジン−4−イルメチル)ピペラジン−1−イル、4−メチル−3−フェニルピペラジン−1−イル、4−[(4,6−ジメトキシピリミジン−2−イル)メチル]ピペラジン−1−イル、4−[(4,6−ジメトキシピリミジン−2−イル)(フェニル)メチル]ピペラジン−1−イル、(1S,4S)−5−メチル−5−アザ−2−アゾニアビシクロ[2.2.1]ヘプタ−2−イル、(1S,4S)−5−(4−フルオロフェニル)−2,5−ジアザビシクロ[2.2.1]ヘプタ−2−イル、4−(1H−インドール−6−イルカルボニル)ピペラジン−1−イル、4−(2,3−ジヒドロ−1H−インデン−2−イル)ピペラジン−1−イル、4−(1,2−ベンゾイソチアゾール−3−イル)ピペラジン−1−イル、(1S,4S)−5−(4−クロロフェニル)−5−アザ−2−アゾニアビシクロ[2.2.1]ヘプタ−2−イル、4−[(3,5−ビス(トリフルオロメチル)フェニル]ピペラジン−1−イル、4−(イソキノリン−1−イル)ピペラジン−1−イル、4−(2,3−ジヒドロ−1,4−ベンゾジオキシン−5−イル)ピペラジン−1−イル、4−(2,5−ジメトキシフェニル)ピペラジン−1−イル、(1S,4S)−5−(2−メトキシベンジル)−5−アザ−2−アゾニアビシクロ[2.2.1]ヘプタ−2−イル、(1S,4S)−5−(4−メトキシベンジル)−5−アザ−2−アゾニアビシクロ[2.2.1]ヘプタ−2−イル、(1S,4S)−5−(4−クロロベンジル)−5−アザ−2−アゾニアビシクロ[2.2.1]ヘプタ−2−イル、オクタヒドロピロロ[1,2−a]ピラジン−2−イル、オクタヒドロ−2H−ピリド[1,2−a]ピラジン−2−イル、デカヒドロピラジノ[1,2−a]アゼピン−2−イル、2−ベンジル−4−フェニルピペラジン−1−イル、4−(4−メトキシピリジン−2−イル)ピペラジン−1−イル、5,6,7,8−テトラヒドロ[1,2,4]トリアゾロ[4,3−a]ピラジン−7−イル、4−(1,3−ベンゾジオキソール−5−イル)ピペラジン−1−イル、(1S,4S)−5−(4−メトキシフェニル)−5−アザ−2−アゾニアビシクロ[2.2.1]ヘプタ−2−イル、及び10−アザ−9−アゾニアトリシクロ[4.2.1.12,5]デカン−10−イルである。
トリフルオロアセチル基は、任意の炭素環原子上に置換されており;かつ
a、b、A、D、R1、R2、R3、W、及びXは、前文に定義されたとおりである]
の化合物か、又は医薬的に許容され得るその塩も提供する。
Aは、CH又はNであり;
Dは、CHであり;
AがNであるとき、トリフルオロアセチル基は、D上に置換されており;
AがCHであるとき、トリフルオロアセチル基は、A又はD上に置換されている。
a、b、R1、R2、R3、W、及びXは、前文に定義されたとおりである]
の化合物か、又は医薬的に許容され得るその塩も提供する。
a、b、R1、R2、R3、W、及びXは、前文に定義されたとおりである]
の化合物か、又は医薬的に許容され得るその塩を提供する。
a、b、R1、R2、R3、W、及びXは、前文に定義されたとおりである]
の化合物か、又は医薬的に許容され得るその塩を提供する。
a、b、R1、R2、R3、W、及びXは、前文に定義されたとおりである]
の化合物か、又は医薬的に許容され得るその塩を提供する。
トリフルオロアセチル基は、任意の炭素環原子上に置換されており;
R8は水素、C1−4アルキル、C6−10アリール、C6−10アリールC1−4アルキル、又はC3−7シクロアルキルであり;かつ
a、A、D,X、R2、R3、及びWは、前文に定義されたとおりである]
の化合物か、又は医薬的に許容され得るその塩を提供する。
Aは、CH又はNであり;
Dは、CHであり;
AがNであるとき、トリフルオロアセチル基は、D上に置換されており;
AがCHであるとき、トリフルオロアセチル基は、A又はD上に置換されており;
R8は、水素、C1−4アルキル、C6−10アリール、又はC6−10アリールC1−4アルキルである。
好ましくは、R8は、水素、メチル、又はベンジルである。さらに好ましいR8基は、シクロプロピルである。
(X=O)結合基及びトリフルオロアセチル基の各々は、独立して、任意の炭素環原子上に置換されており;
eは、0、1、2、又は3であり;
Hetは、1個のN原子を含有する4員の飽和ヘテロ環か、1、2、又は3個のN原子と、ゼロ又は1個のO原子とを含有する5、6、又は7員の飽和ヘテロ環であって;該環は、C3−10シクロアルキル環か、独立してN、O、及びSから選ばれる1、2、又は3個のヘテロ原子を含有する5、6、又は7員の、飽和又は部分飽和ヘテロ環か、フェニル環か、独立してN、O、及びSから選択される1,2、又は3個のヘテロ原子を含有し、その多くとも1個のヘテロ原子がO又はSである5員のヘテロ芳香環か、又は、1,2、又は3個の窒素原子を含有する6員のヘテロ芳香環に縮合されてもよく;1つの炭素環原子において、独立してN、O、及びSから選択されるゼロ,1、又は2個のヘテロ原子を含有する5又は6員のスピロ環によって置換されてもよく、該環は、フェニル環に縮合されてもよく;或いは、1又は2個のC1−4アルキル基によって架橋されてもよく;かつ
A、D、L、X、及びR4は、前文に定義されたとおりである]
の化合物か、又は医薬的に許容され得るその塩を提供する。
nは、ゼロ、1、又は2であり;
mは、ゼロ、1、又は2であり;
nがゼロであるとき、YはCH2であり;
nが1又は2であるとき、YはCH2、O、又はNHであり;
YがCH2であるとき、Yと隣接する炭素環原子とによって形成される結合は、フェニル環に縮合されてもよく;又は、Yは、N、O、及びSから選択される1つのヘテロ原子を含有する5又は6員のスピロ環によって置換されてもよく、該環は、フェニル環に縮合されてもよく;
YがNHであるとき、Yと隣接する炭素環原子とによって形成される結合は、イミダゾール環に縮合されてもよく;かつ
A、D、X、及びR4は、前文に定義されたとおりである]
の化合物か、又は医薬的に許容され得るその塩を提供する。
N−(4−メトキシベンジル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−メチル−N−(キノリン−7−イルメチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−エチル−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(2−フェニルエチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−ベンジル−N−メチル−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[2−(ジメチルアミノ)エチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(1S)−1−フェニルエチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(1R)−1−フェニルエチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
2−チオフェンカルボキサミド、N−(フェニルメチル)−5−(トリフルオロアセチル);
N−(4−クロロベンジル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(4−メチルベンジル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(1−ナフチルメチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(ピリジン−3−イルメチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−フェニル−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(ビフェニル−3−イルメチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(シクロヘキシルメチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−メチル−N−(1−ナフチルメチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
1−[5−(1,3−ジヒドロ−2H−イソインドール−2−イルカルボニル)−2−チエニル]−2,2,2−トリフルオロエタノン;
N−(2−メトキシベンジル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(3−メトキシベンジル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(2−クロロベンジル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(3−クロロベンジル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(4−フルオロベンジル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(4−トリフルオロメチルベンジル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(4−トリフルオロメトキシベンジル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[4−(メチルスルホニル)ベンジル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(ビフェニル−4−イルメチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[4−(1,2,3−チアジアゾール−4−イル)ベンジル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(2,2−ジフェニルエチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(ジフェニルメチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N,N−ジベンジル−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[2−(4−メトキシフェニル)エチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(4−フェニル−1,3−チアゾール−2−イル)メチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(1R)−2,3−ジヒドロ−1H−インデン−1−イル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[2−(2−ナフチル)エチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[2−(3,4−ジヒドロキノリン−1(2H)−イル)エチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(1,2,3,4−テトラヒドロナフタレン−1−イルメチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(1−フェニルピペリジン−4−イル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[4−(1H−イミダゾール−4−イル)ベンジル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(2,4−ジクロロベンジル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[2−(4−フェニル−1,3−チアゾール−2−イル)エチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−メチル−N−(キノリン−6−イルメチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(キノリン−5−イルメチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−メチル−N−(1,3−チアゾール−2−イルメチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[2−(2−メチル−1−フェニル−1H−インドール−3−イル)エチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−メチル−N−[(1−メチル−1H−イミダゾール−2−イル)メチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
2,2,2−トリフルオロ−1−(5−{[4−(3−ピリジン−3−イル−1,2,4−オキサジアゾール−5−イル)ピペリジン−1−イル]カルボニル}−2−チエニル)エタノン;
2,2,2−トリフルオロ−1−(5−{[4−(5−フェニル−1,3,4−オキサジアゾール−2−イル)ピペリジン−1−イル]カルボニル}−2−チエニル)エタノン;
1−(5−{[4−(1,3−ベンゾオキサゾール−2−イル)ピペラジン−1−イル]カルボニル}−2−チエニル)−2,2,2−トリフルオロエタノン;
1−(5−{[4−(1,3−ベンゾチアゾール−2−イル)ピペラジン−1−イル]カルボニル}−2−チエニル)−2,2,2−トリフルオロエタノン;
N−(4−シクロヘキシル−1,3−チアゾール−2−イル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(2−メチルイミダゾ[1,2−a]ピリジン−3−イル)メチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[4−(2−クロロフェニル)−1,3−チアゾール−2−イル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(2−シクロヘキシルエチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(1,3−オキサゾール−2−イルメチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[2−(1−ナフチル)エチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
tert−ブチル (6−{4−[({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]フェノキシ}ヘキシル)カルバメート;
N−[(5−フェニルイソオキサゾール−3−イル)メチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(4−フェノキシフェニル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(3−フリルメチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(4−フェニルシクロヘキシル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(1,3−ベンゾチアゾール−2−イルメチル)−N−メチル−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[4−(アミノスルホニル)ベンジル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(2,6−ジフルオロベンジル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(ビフェニル−2−イルメチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
1−[5−(2,3−ジヒドロ−1H−インドール−1−イルカルボニル)−2−チエニル]−2,2,2−トリフルオロエタノン;
1−{5−[(4−ベンゾイルピペリジン−1−イル)カルボニル]−2−チエニル}−2,2,2−トリフルオロエタノン;
2,2,2−トリフルオロ−1−[5−(1’H,3H−スピロ[2−ベンゾフラン−1,4’−ピペリジン]−1’−イルカルボニル)−2−チエニル]エタノン;
N−メチル−N−(キノキサリン−6−イルメチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−{[5−(メトキシメチル)−1H−ピラゾール−3−イル]メチル}−N−メチル−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(5−フェニル−4H−1,2,4−トリアゾール−3−イル)メチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(イソオキサゾール−4−イルメチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(2,1,3−ベンゾチアジアゾール−5−イルメチル)−N−メチル−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−ピリジン−3−イル−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[4−(4−メトキシフェニル)−2−チエニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−2−ナフチル−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[3−(1H−ピロール−1−イル)フェニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
2,2,2−トリフルオロ−1−(5−{[2−(フェノキシメチル)モルホリン−4−イル]カルボニル}−2−チエニル)エタノン;
1−(5−{[4−(6,7−ジメトキシ−3,4−ジヒドロイソキノリン−2(1H)−イル)ピペリジン−1−イル]カルボニル}−2−チエニル)−2,2,2−トリフルオロエタノン;
N−(4−フェノキシベンジル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
2,2,2−トリフルオロ−1−{5−[(4−イソキノリン−3−イルピペラジン−1−イル)カルボニル]−2−チエニル}エタノン;
N−メチル−N−[(3−フェニルイソオキサゾール−5−イル)メチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(4−モルホリン−4−イルフェニル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−1,3−ベンゾチアゾール−2−イル−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(5−クロロ−1,3−ベンゾオキサゾール−2−イル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−9H−フルオレン−2−イル−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
1−(5−{[4−(1,2−ベンゾイソチアゾール−3−イル)ピペリジン−1−イル]カルボニル}−2−チエニル)−2,2,2−トリフルオロエタノン;
N−シクロペンチル−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
2,2,2−トリフルオロ−1−[5−({4−[2−(4−メチルフェニル)エチル]ピペリジン−1−イル}カルボニル)−2−チエニル]エタノン;
N−[(1−ピペリジン−1−イルシクロヘキシル)メチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(1−メチル−1H−ピラゾール−4−イル)メチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(1−モルホリン−4−イルシクロヘキシル)メチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
1−[5−({3−[4−(ジメチルアミノ)フェニル]ピロリジン−1−イル}カルボニル)−2−チエニル]−2,2,2−トリフルオロエタノン;
N−[(1R)−1−(1−ナフチル)エチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[2−(2,4−ジクロロフェニル)エチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(シクロプロピルメチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(1R)−1−シクロヘキシルエチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(テトラヒドロフラン−2−イルメチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(3−モルホリン−4−イルプロピル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(2−メトキシエチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(1−アダマンチルメチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
1−{5−[(4−ベンジルピペリジン−1−イル)カルボニル]−2−チエニル}−2,2,2−トリフルオロエタノン;
2,2,2−トリフルオロ−1−{5−[(4−ピリジン−2−イルピペラジン−1−イル)カルボニル]−2−チエニル}エタノン;
N−メチル−N−[(1−フェニル−1H−ピラゾール−4−イル)メチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
2,2,2−トリフルオロ−1−{5−[(4−{3−[4−(トリフルオロメチル)フェニル]−1,2,4−オキサジアゾール−5−イル}ピペリジン−1−イル)カルボニル]−2−チエニル}エタノン;
2,2,2−トリフルオロ−1−[5−({4−[5−(トリフルオロメチル)−1,3,4−チアジアゾール−2−イル]ピペラジン−1−イル}カルボニル)−2−チエニル]エタノン;
N−[1−(1−ナフチル)エチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(2,3−ジヒドロ−1,4−ベンゾジオキシン−2−イルメチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(6,7,8,9−テトラヒドロ−5H−ベンゾ[7]アヌレン−5−イルメチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−{[2−(2−チエニル)−1,3−チアゾール−4−イル]メチル}−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
1−{5−[(4,4−ジフルオロピペリジン−1−イル)カルボニル]−2−チエニル}−2,2,2−トリフルオロエタノン;
N−[2−(1H−1,2,3−ベンゾトリアゾール−1−イル)エチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[2−(4−フェノキシフェニル)エチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(2,4−ジメトキシベンジル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(2,6−ジメトキシベンジル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(1R)−1−(4−メトキシフェニル)エチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(1,3−ベンゾジオキソール−5−イルメチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(4−メトキシベンジル)−N−メチル−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
2,2,2−トリフルオロ−1−{5−[(3−フェニル−5,6−ジヒドロイミダゾ[1,2−a]ピラジン−7(8H)−イル)カルボニル]−2−チエニル}エタノン;
N−(ベンジルスルホニル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(ジメチルアミノ)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(4−{[6−({5−[(3aR,4R,6aS)−2−オキソヘキサヒドロ−1H−チエノ[3,4−d]イミダソール−4−イル]ペンタノイル}アミノ)ヘキシル]オキシ}ベンジル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(4−メトキシベンジル)−4−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−ベンジル−N−メチル−4−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(シクロヘキシルメチル)−4−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−ベンジル−N−メチル−5−(トリフルオロアセチル)チオフェン−2−スルホンアミド;
N−(シクロヘキシルメチル)−5−(トリフルオロアセチル)チオフェン−2−スルホンアミド;
N−ベンジル−N−メチル−2−(トリフルオロアセチル)−1,3−チアゾール−5−カルボキサミド;
N−(シクロヘキシルメチル)−2−(トリフルオロアセチル)−1,3−チアゾール−5−カルボキサミド;
及び医薬的に許容され得るそれらの遊離塩基、塩、及び立体異性体である。
N,N−ジメチル−2−({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)エタンアミニウム・トリフルオロアセテート;
3−[({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]ピリジニウム・トリフルオロアセテート;
1−[2−({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)エチル]−1,2,3,4−テトラヒドロキノリニウム・トリフルオロアセテート;
1−フェニル−4−({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)ピペリジニウム・トリフルオロアセテート;
4−{4−[({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]フェニル}−1H−イミダゾール−1−イウム・トリフルオロアセテート;
5−[({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]−7,8−ジヒドロキノリニウム・トリフルオアセテート;
3−({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)ピリジニウム・トリフルオロアセテート;
6,7−ジメトキシ−2−(1−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペリジン−4−イル)−1,2,3,4−テトラヒドロイソキノリニウム・トリフルオロアセテート;
1−イソキノリン−3−イル−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
4−[4−({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)フェニル]モルホリン−4−イウム・トリフルオロアセテート;
1−{1−[({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]シクロヘキシル}ピペリジニウム・トリフルオロアセテート;
1−ピリジン−2−イル−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
2−(2−チエニル−4−[({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]−1,3−チアゾール−3−イウム・トリフルオロアセテート;
3−フェニル−7−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}−5,6,7,8−テトラヒドロイミダゾ[1,2−A]ピラジン−4−イウム・トリフルオロアセテート;
N−メチル(フェニル)−N−{[5−(トリフルオロアセチル)−2−チエニル]メチル}メタンアミニウム・トリフルオロアセテート;
(1R)−1−フェニル−N−{[5−(トリフルオロアセチル)−2−チエニル]メチル}エタンアミニウム・トリフルオロアセテート;及び
シクロヘキシル−N−{[5−(トリフルオロアセチル)−2−チエニル]メチル}メタンアミニウム・トリフルオロアセテートである。
2−フェニル−5−[1−({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)エチル]−1,3−チアゾール−3−イウム・トリフルオロアセテート;
N−{[4−(アセチルアミノ)フェニル]スルホニル}−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−メチル−N−(キノキサリン−6−イルメチル)−5−(トリフルオロアセチル)−1,3−チアゾール−2−カルボキサミド;
2−メチル−1−(4−メチルフェニル)−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
1−{5−[(4−アセチルピペラジン−1−イル)カルボニル]2−チエニル}−2,2,2−トリフルオロエタノン;
メチル 1−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペリジン−4−カルボキシレート;
1−[(4−クロロフェニル)(フェニル)メチル]−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
2,2,2−トリフルオロ−1−(5−{[4−(テトラヒドロフラン−2−イルカルボニル)ピペラジン−1−イル]カルボニル}−2−チエニル)エタノン;
1−(2−エトキシ−2−オキソエチル)−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
1−(3−メトキシフェニル)−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
4−フェニル−1−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペリジン−4−カルボニトリル;
1−(4−フェニル−1−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペリジン−4−イル)プロパン−1−オン;
1−メチル−4−[2−(メチル{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)−2−フェニルエチル]ピペラジンジイウム・ビス(トリフルオロアセテート);
1−[2−(メチルスルホニル)エチル]−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
1−(3,5−ジクロロピリジニウム−4−イル)−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・ビス(トリフルオロアセテート);
1−(5−{[4−(1H−1,2,3−ベンゾトリアゾール−1−イル)ピペリジン−1−イル]カルボニル}−2−チエニル)−2,2,2−トリフルオロエタノン;
1−[(3−メチルピリジニウム−2−イル)メチル]−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・ビス(トリフルオロアセテート);
2,2,2−トリフルオロ−1−{5−[(3−フェニルピペリジン−1−イル)カルボニル]−2−チエニル}エタノン;
1−(1,2,3,4−テトラヒドロナフタレン−2−イル)−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−2−オン;
1−(1−アダマンチル)−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
1,2−ジメチル−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
2,2,2−トリフルオロ−1−(5−{[4−(モルホリン−4−イルカルボニル)ピペリジン−1−イル]カルボニル}−2−チエニル)エタノン;
2,2,2−トリフルオロ−1−(5−{[4−(ピロリジン−4−イルカルボニル)ピペリジン−1−イル]カルボニル}−2−チエニル)エタノン;
1−(3−クロロベンジル)−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
5−フルオロ−2−(1−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペリジン−4−イル)−1H−ベンゾイミダゾール−3−イウム・トリフルオロアセテート;
1−メチル−2−[(1−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペリジン−3−イル)−1H−イミダゾール−3−イウム・トリフルオロアセテート;
6−メチル−2−(1−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペリジン−3−イル)−1H−ベンゾイミダゾール3−イウム・トリフルオロアセテート;
1−(4−フルオロベンジル)−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−2−オン;
2,2,2−トリフルオロ−1−(5−{[4−(1H−1,2,4−トリアゾール−3−イルカルボニル)ピペラジン−1−イル]カルボニル}−2−チエニル)エタノン;
1−(3,4−ジクロロフェニル)−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
(3R,4aS,8aS)−N−(tert−ブチル)−2−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}デカヒドロイソキノリン−3−カルボキサミド;
(1R,4R)−2−ベンジル−5−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}−5−アザ−2−アゾニアビシクロ[2.2.1]ヘプタン・トリフルオロアセテート;
1−(5−クロロ−2−メトキシフェニル)−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
4−(4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イル)ベンゾニトリル;
1−{5−[(4−ブロモピペリジン−1−イル)カルボニル]−2−チエニル}−2,2,2−トリフルオロエタノン;
(4aR,8aR)−1−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}オクタヒドロキノリン−4(1H)−オン;
1−(1−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペリジン−4−イル)−1,3−ジヒドロ−2H−ベンゾイミダゾール−2−オン;
1−(2−クロロフェニル)−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
1−(2−エトキシフェニル)−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
1−(4−メトキシフェニル)−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
1−(2−メチルフェニル)−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
1−(4−フェニル−1−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペリジン−4−イル)ブタン−1−オン;
N−(テトラヒドロフラン−3−イルメチル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N,N−ジメチル−2−({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)プロパン−1−アミニウム・トリフルオロアセテート;
tert−ブチル 3−[({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]−1H−インドール−1−カルボキシレート;
N−[3−オキソ−3−(トリチルアミノ)プロピル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[2−オキソ−2−(トリチルアミノ)エチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[5−オキソ−5−(トリチルアミノ)ペンチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
4−フェニル−2−[({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]モルホリン−4−イウム・トリフルオロアセテート;
1−フェニル−9−({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)−3,6−ジアゾニアトリシクロ[4.3.1.13,8]ウンデカン・ビス(トリフルオロアセテート);
4−ベンジル−2−[({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]モルホリン−4−イウム・トリフルオロアセテート;
4−[1−({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)エチル]ピリジニウム・トリフルオロアセテート;
3−[1−({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)エチル]ピリジニウム・トリフルオロアセテート;
11−オキソ−10−[2−({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)エチル]−10,11−ジヒドロ−5H−ジベンゾ[b,e][1,4]ジアゼピン−5−イウム・トリフルオロアセテート;
N−[2−(1,4−ジオキソ−3,4−ジヒドロフタラジン−2(1H)−イル)エチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
2−[1−({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)エチル]ピリジニウム・トリフルオロアセテート;
3−[({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]ピラゾロ[1,5−a]ピリジン−1−イウム・トリフルオロアセテート;
2−[2,2,2−トリフルオロ−1−({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)エチル]ピリジニウム・トリフルオロアセテート;
3−[({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]キノリニウム・トリフルオロアセテート;
N−(2−フルオロプロプ−2−エン−1−イル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
7−[({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]ピラゾロ[1,5−a]ピリジン−1−イウム・トリフルオロアセテート;
1−(5−{[(1S,4S)−5−(3−クロロフェニル)−2,5−ジアザビシクロ[2.2.1]ヘプタ−2−イル]カルボニル}−2−チエニル)−2,2,2−トリフルオロエタノン;
1−(5−{[(1S,4S)−5−(2−クロロフェニル)−2,5−ジアザビシクロ[2.2.1]ヘプタ−2−イル]カルボニル}−2−チエニル)−2,2,2−トリフルオロエタノン;
1−(2−メトキシベンジル)−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
1−(3−メトキシベンジル)−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
4−(4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イル)キナゾリン−3−イウム・トリフルオロアセテート;
3−(4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イル)ピリジニウム・トリフルオロアセテート;
1−シクロヘキシル−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−2−オン;
1−[(2−メチル−1,3−チアゾール−4−イル)メチル]−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
1−シクロプロピル−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
(3S)−1−メチル−3−フェニル−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
7−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}−2−(トリフルオロメチル)−5,6,7,8−テトラヒドロイミダゾ[1,2−a]ピラジン−1−
−イウム・トリフルオロアセテート;
2,2,2−トリフルオロ−1−(5−{[4−(4−メチル−1,2,5−オキサジアゾール−3−イル)ピペラジン−1−イル]カルボニル}−2−チエニル)エタノン;
1−(ピリジン−3−イルメチル)−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
1−(ピリジン−4−イルメチル)−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
1−メチル−2−フェニル−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
1−[(4,6−ジメトキシピリミジン−2−イル)メチル]−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
1−[(4,6−ジメトキシピリミジン−2−イル)(フェニル)メチル]−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
(1S,4S)−2−メチル−5−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}−5−アザ−2−アゾニアビシクロ[2.2.1]ヘプタン・トリフルオロアセテート;
2,2,2−トリフルオロ−1−(5−{[(1S,4S)−5−(4−フルオロフェニル)−2,5−ジアザビシクロ[2.2.1]ヘプタ−2−イル]カルボニル}−2−チエニル)エタノン;
2,2,2−トリフルオロ−1−(5−{[4−(1H−インドール−6−イルカルボニル)ピペラジン−1−イル]カルボニル}−2−チエニル)エタノン;
1−(2,3−ジヒドロ−1H−インデン−2−イル)−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
1−(1,2−ベンゾイソチアゾール−3−イル)−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
(1S,4S)−2−(4−クロロフェニル)−5−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}−5−アザ−2−アゾニアビシクロ[2.2.1]ヘプタン・トリフルオロアセテート;
1−[5−({4−[3,5−ビス(トリフルオロメチル)フェニル]ピペラジン−1−イル}カルボニル)−2−チエニル]−2,2,2−トリフルオロエタノン;
1−(4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イル)イソキノリニウム・トリフルオロアセテート;
1−(5−{[4−(2,3−ジヒドロ−1,4−ベンゾジオキシン−5−イル)ピペラジン−1−イル]カルボニル}−2−チエニル)−2,2,2−トリフルオロエタノン;
1−(2,5−ジメトキシフェニル)−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
(1S,4S)−2−(2−メトキシベンジル)−5−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}−5−アザ−2−アゾニアビシクロ[2.2.1]ヘプタン・トリフルオロアセテート;
(1S,4S)−2−(4−メトキシベンジル)−5−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}−5−アザ−2−アゾニアビシクロ[2.2.1]ヘプタン・トリフルオロアセテート;
(1S,4S)−2−(4−クロロベンジル)−5−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}−5−アザ−2−アゾニアビシクロ[2.2.1]ヘプタン・トリフルオロアセテート;
2−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}オクタヒドロピロロ[1,2−a]ピラジン−5−イウム・トリフルオロアセテート;
2−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}オクタヒドロ−2H−ピリド[1,2−a]ピラジン−5−イウム・トリフルオロアセテート;
2−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}デカヒドロピラジノ[1,2−a]アゼピン−5−イウム・トリフルオロアセテート;
3−ベンジル−1−フェニル−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
4−メトキシ−2−(4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イル)ピリジニウム・トリフルオロアセテート;
7−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}−5,6,7,8−テトラヒドロ[1,2,4]トリアゾロ[4,3−a]ピラジン−2−イウム・トリフルオロアセテート;
1−(1,3−ベンゾジオキソール−5−イル)−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート;
(1S,4S)−2−(4−メトキシフェニル)−5−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}−5−アザ−2−アゾニアビシクロ[2.2.1]ヘプタン・トリフルオロアセテート;
10−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}−10−アザ−9−アゾニアトリシクロ[4.2.1.12,5]デカン・トリフルオロアセテート;
4−メチル−2−[(メチル{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]−1H−イミダゾール−3−イウム・トリフルオロアセテート;
5−[(メチル{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]−3−フェニル−1,2,4−オキサジアゾール−4−イウム・トリフルオロアセテート;
4−[(シクロプロピル{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]−1,3,5−トリメチル−1H−ピラゾール−2−イウム・トリフルオロアセテート;
4−[(メチル{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]−2−(2−チエニル)−1,3−チアゾール−3−イウム・トリフルオロアセテート;
2−メチル−3−[(メチル{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]イミダゾ[1,2−a]ピリジン−1−イウム・トリフルオロアセテート;
2−[1−(メチル{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)エチル]−1,3−チアゾール−3−イウム・トリフルオロアセテート;
N−メチル−N−[(4−メチル−1,2,5−オキサジアゾール−3−イル)メチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
3−[1−(メチル{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)エチル]イソオキサゾール−2−イウム・トリフルオロアセテート;
3−[1−(メチル{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)エチル]−5−フェニル−1H−ピラゾール−2−イウム・トリフルオロアセテート;
3−[(メチル{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]−5−フェニル−1H−ピラゾール−2−イウム・トリフルオロアセテート;
4−[(メチル{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]−2−フェニル−1,3−チアゾール−3−イウム・トリフルオロアセテート;
2−[(メチル{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]−4−フェニル−1,3−チアゾール−3−イウム・トリフルオロアセテート;
5−シクロプロピル−3−[(メチル{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]−1,2,4−オキサジアゾール−4−イウム・トリフルオロアセテート;
5−[(シクロプロピル{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]−1,3−チアゾール−3−イウム・トリフルオロアセテート;
3−[(メチル{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]−5−フェニルイソオキサゾール−2−イウム・トリフルオロアセテート;
N−[1−(2−フリル)エチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
4−[1−({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)エチル]−1,3−チアゾール−3−イウム・トリフルオロアセテート;
5−[1−({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)エチル]−1H−1,2,4−トリアゾール−4−イウム・トリフルオロアセテート;
5−[1−({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)エチル]イソオキサゾール−2−イウム・トリフルオロアセテート;
N−[1−(2−チエニル)エチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
2−メチル−4−[1−({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ]エチル]−1,3−チアゾール−3−イウム・トリフルオロアセテート;
3−メチル−5−[1−({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ]エチル]−4H−1,2,4−トリアゾール−1−イウム・トリフルオロアセテート;
2−[1−(メチル{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)エチル]ピリジニウム・トリフルオロアセテート;
4−[1−(メチル{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)エチル]ピリジニウム・トリフルオロアセテート;
3−[1−(メチル{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)エチル]ピリジニウム・トリフルオロアセテート;
tert−ブチル 3−[1−({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)エチル]−1H−インドール−1−カルボキシレート;
N−[1−(4−ヒドロキシフェニル)エチル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−{[5−(ジメチルアミノ)−1−ナフチル]スルホニル}−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−{[5−(アセチルアミノ)−1,3,4−チアジアゾール−2−イル]スルホニル}−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(2−フルオロフェニル)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(6−エトキシ−1,3−ベンゾチアゾール−2−イル)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(2−フェニルエチル)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(4−クロロベンジル)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−{[2−(1−ナフチル)エチル]スルホニル}−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(5−メチルピリジン−2−イル)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
メチル 2−{[({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)スルホニル]メチル}ベンゾエート;
N−(1−ベンゾチエン−3−イルスルホニル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(2−メチルフェニル)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(4−フェノキシフェニル)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(4,4−ジフェニルブチル)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(3,3−ジフェニルプロピル)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(2−クロロベンジル)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(2,2−ジフェニルエチル)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(ビフェニル−4−イルメチル)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(1,2−ベンゾイソオキサゾール−3−イルメチル)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−({[4−(4−クロロフェニル)−1,3−チアゾール−2−イル]メチル}スルホニル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(4−シアノベンジル)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(ピリジン−4−イルメチル)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(2,4−ジクロロベンジル)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(2−シクロヘキシルエチル)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−{[(E)−2−フェニルビニル]スルホニル}−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(3,4−ジクロロベンジル)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
5−(トリフルオロアセチル)−N−{[2−(トリフルオロメチル)ベンジル]スルホニル}チオフェン−2−カルボキサミド;
5−(トリフルオロアセチル)−N−{[4−(トリフルオロメトキシ)フェニル]スルホニル}チオフェン−2−カルボキサミド;
N−[(5−ブロモ−2−チエニル)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(2−ナフチルスルホニル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(3−フェニルプロピル)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(3,4−ジクロロフェニル)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−({5−[(ベンゾイルアミノ)メチル]−2−チエニル}スルホニル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(2,4−ジメトキシフェニル)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(ビフェニル−4−イルスルホニル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(2,5−ジクロロ−3−チエニル)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−{[3−(4−メトキシフェノキシ)プロピル]スルホニル}−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(1−ナフチルスルホニル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−[(3−クロロベンジル)スルホニル]−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
N−(2,3−ジヒドロ−1,4−ベンゾジオキシン−6−イルスルホニル)−5−(トリフルオロアセチル)チオフェン−2−カルボキサミド;
1−[2−(2,3−ジヒドロ−1H−インドール−1−イルカルボニル)−1,3−チアゾール−5−イル]−2,2,2−トリフルオロエタノン;
及び医薬的に許容され得るそれらの遊離塩基、塩、及び立体異性体である。
DMF:ジメチルホルムアミド;DMSO:ジメチルスルホキシド;MeOH:メタノール;EtOAc:酢酸エチル;PE:石油エーテル;THF:テトラヒドロフラン;DCM:ジクロロメタン;CHCl3:クロロホルム;CD3CD:アセトニトリル−d3;CDCl3:クロロホルム−d;HCl:塩化水素;min:分;h:時間;eq.:当量;M:モル濃度の;RT:室温;O/N:一晩;RP−HPLC:逆相高圧液体クロマトグラフィー;BuLi:ブチルリチウム;LDA:リチウムジイソプロピルアミド;EDCl:1−(3−ジメチルアミノプロピル−3−エチルカルボジイミド・ヒドロクロリド;HOBt:1−ヒドロキシベンゾトリアゾール;TMSCF3:トリメチル(トリフルオロメチル)シラン;及びLiOH:水酸化リチウムである。BSA(牛血清アルブミン);DTT(ジチオスレイトール);EDTA(エチレンジアミン四酢酸);em(エミッション);ex(exitation);Hepes((N−(2−ヒドロキシエチル)ピペラジン)−N’−(2−エタンスルホン酸));ILB(等張溶解緩衝液);IPTG(イソプロピル−ベータ−D−チオガラクトピラノシド);NP40(ノニデットP40);PBS(リン酸緩衝食塩水);PMSF(フッ化フェニルメチルスルホニル);SEC(サイズ排除クロマトグラフィー);TBS(トリス緩衝食塩水);Tris−HCl(トリス ヒドロキシメチルアミノエタン);TSA(トリコスタチンA);BEMP(2−tert−ブチルイミノ−2−ジエチルアミノ−1,3−ジメチル−ペルヒドロ−1,3,2−ジアザホスホリン);BOP(ベンゾトリアゾール−1−イルオキシトリス(ジメチルアミノ)−ホスホニウム・ヘキサフルオロホスフェート);DIPEA(N,N’−ジイソプロピルエチルアミン);及びHBTU:O−ベンゾトリアゾール−1−イル−N,N,N’,N’−テトラメチルウロニウム・ヘキサフルオロホスフェート。
と反応させることによって調製され得る。反応は一般に、EDCl及びHOBtのようなカップリング剤の存在下に、DMFのような溶媒中で、ほぼ室温において行われる。他の好ましいカップリング剤は、DIPEA及びHBTUである。L1がヒドロキシであるとき、それは、BuLiのような塩基の存在下に、最初に脱プロトン化されてよい。反応は、別法として、PS−カルボジイミドのようなポリマー担持試薬、及びMP−カルボネート又はPS−イソシアネートのようなポリマー担持スカベンジャーを用いて、DCMのような溶媒中で、ほぼ室温において行われ得る。
の化合物を、LiOHのような塩基を用いて、一般にMeOH及び水のような溶媒中で、ほぼ室温において反応させることによって調製され得る。
と、一般にLDA又はBuLiのような塩基の存在下に、THFのような溶媒中で、約−78℃の温度において反応させることによって調製可能である。
の化合物と、一般にLDA又はBuLiのような塩基の存在下に、THFのような溶媒中で、約−78℃の温度において反応させることによって調製可能である。
の化合物と、一般にトリエチルアミンのような塩基の存在下に、クロロホルムのような溶媒中で、ほぼ室温において反応させることによって調製可能である。
の化合物の酸化によって調製可能である。例えば、酸化は、デス・マーチン・ペルヨージナン(Dess−Martin periodinane)の存在下に、DCMのような溶媒中で、ほぼ室温において行われる。
の化合物を、式IIIの試薬と、一般に、EDCl及びHOBt、又はHBTUのようなカップリング剤と、DIPEAのような塩基とを用いるといった、標準的なカップリングの方法論を用いて、DMFのような溶媒中で、ほぼ室温において反応させることによって調製可能である。
の化合物から、ハロゲン−リチウム交換により、BuLiのような有機金属試薬を用いて調製可能である。反応は一般に、THFのような溶媒中で、約−78℃の温度において行われ、中間の有機金属試薬を形成する。次いでカルボニル基が、形成された有機金属中間体を二酸化炭素でクエンチすることにより付加される。
のアルデヒドへの、トリフルオロメチル基の付加によって調製可能である。トリフルオロメチル基は、例えば、TMSCF3を用いて、フッ化セシウムのような触媒フッ化物供給源の存在下に、DMFのような溶媒中で、ほぼ室温において導入される。
2−トリフルオロアセチルチオフェン−5−カルボキサミドは、アミン又はスルホンアミドの、2−トリフルオロアセチルチオフェン−5−カルボン酸とのアミドカップリングによって調製された。好適なカップリング法は、「テトラへドロン・レターズ(Tetrahedron Lett.)」、1974年、p.2695において溶液相化学に関して、又は「テトラへドロン・レターズ」、1993年、p.7685においてポリマー結合試薬及びスカベンジャーの使用に関して記述されたような、当該技術分野における方法である。2−トリフルオロアセチルチオフェン−5−カルボン酸は、アルキルエステルの、LiOHを用いたエステル加水分解によって合成された。
2−置換チオフェンの、BuLi又はLDAを用いた、−78℃における、「ジャーナル・オブ・メディシナル・ケミストリー(J.Med.Chem.)」、2001年、第44巻、p.3203に記述されたような、リチオ化と、それに続く、N−メチル−N−メトキシトリフルオロアセトアミドの付加は、5−置換−2−トリフルオロアセチルチオフェンをもたらした。
1,3−チアゾール−5−カルボン酸の、BuLiのような塩基を用いた、「テトラへドロン・レターズ」、1978年、p.5に記述されたような二重脱プロトン化と、それに続くN−メチル−N−メトキシトリフルオロアセトアミドを用いた反応は、2−トリフルオロアセチル−1,3−チアゾール−5−カルボン酸をもたらした。2−トリフルオロアセチル−1,3−チアゾール−5−カルボキサミドは、第一級アミン及び第二級アミンとのアミドカップリングにより、スキーム1に記述されたように合成された。
4−ブロモ−1,3−チアゾール−2−カルボン酸の、BuLiのような塩基を用いた、「ザ・ジャーナル・オブ・オーガニック・ケミストリー(J.Org.Chem.)」、1988年、第53巻、p.417に記述されたような処理は、ブロモ−リチウム交換をもたらし、続くN−メチル−N−メトキシトリフルオロアセトアミドとの反応は、4−トリフルオロアセチル−1,3−チアゾール−2−カルボン酸をもたらした。4−トリフルオロアセチル−1,3−チアゾール−2−カルボキサミドは、第一級アミン及び第二級アミンを用いたアミドカップリングにより、スキーム1に記述されたように合成された。
2−ブロモ−5−ホルミルチアゾールの、CF3TMSを用いた、F−供給源、例えばCsF又はnBu4NFの存在下での反応は、「ザ・ジャーナル・オブ・オーガニック・ケミストリー」、1999年、第64巻、p.2873に記述されたように、トリフルオロエチルアルコールを与えた。この中間体の、2当量のBuLiのような塩基を用いた、「ザ・ジャーナル・オブ・オーガニック・ケミストリー」、1988年、第53巻、p.417に記述されたような処理は、アルコール脱プロトン化及び、ブロモ−リチウム交換をもたらし、次に続く無水炭素との反応は、カルボキシレート中間体をもたらし、それが、対応する第一級及び第二級体と、スキーム1に記述された合成方法を用いて結合された。最後に、「ザ・ジャーナル・オブ・オーガニック・ケミストリー」、1983年、第48巻、p.4155に記述されたような、アルコールの、デス・マーチン・ペルヨージナン又はMnO2を用いた、酸化が、5−トリフルオロアセチル−1,3−チアゾールカルボキサミドをもたらした。
野生型触媒ドメイン、HisタグHDAC4は、大腸菌株BL21StarTM(DE3)において発現された。細胞は37℃において、1g/lの(15NH4)2SO4及び5g/lのグルコース、及び100μMのZnCl2を補足された最少培地中で、600nmにおける光学密度0.8まで増殖され、IPTGを用いて23℃で16時間誘導された。23℃では、80%を超えるタンパク質が可溶性であった。
HEK293細胞、6x106細胞/10cmディッシュは、15μgのプラスミドDNAにより、製造業者の助言に従ってリポフェクタミン試薬(インビトロジェン(Invitrogen))を用いてトランスフェクトされた。24時間後、予冷された1xPBS中に細胞を掻取り、1500xgにおいて4℃で5分間遠心分離、1xPBSで2回洗浄、細胞を計数、遠心分離により細胞ペレットを回収し、−80℃で凍結する。
使用試薬
TSAストック:TSAは、100%DMSO中の10mM溶液として提供される。
アッセイ緩衝液:25mMトリス/HCl pH8、137mM NaCl、2.7mM KCl、1mM MgCl2、0.1mg/ml BSA
希釈基質溶液:tert−ブチル {(1S)−1−{[(4−メチル−2−オキソ−2H−クロメン−7−イル)アミノ]カルボニル}−5−[(トリフルオロアセチル)アミノ]フェニル}カルバメートは、各使用に先立ち、1mMトリス pH7.4を用いて200μMに希釈される。アッセイにおける最終濃度は、20μMである。
希釈展開剤溶液:市販の20倍の展開剤濃縮物(KI−105、バイオモル・リサーチ・ラボラトリーズ(BioMol Research Laboratories)は、1mMトリス pH7.4中に、1:167に希釈される。この溶液への2μM[終濃度]のTSAは、反応を停止するその能力を高める。
酵素ワーキング溶液:酵素は、各使用に先立ち、新鮮な酵素のアリコートから、1.25倍のアッセイ緩衝液中に希釈される。アッセイにおける最終濃度は、0.2nMである。
反応は、96−穴マイクロプレートにおいて、50μl/ウエルの終体積において行われる。5μlのDMSO/化合物溶液を添加し、アッセイ緩衝液中の40μlのHDAC4酵素を添加し、室温において10分間インキュベートする。5μlの、200μMの基質溶液の添加によって反応を開始し、37℃において1時間インキュベートする。50μlの、展開剤/4μMのTSA溶液の添加によって反応を停止し、室温で30分間インキュベートする。ex.360nM、及びem.460nMにおいて、蛍光を測定する。
使用試薬:
TSAストック:TSAは、100%DMSO中の10mMストック溶液として提供される。
アッセイ緩衝液:20mMヘペス pH7.5、137mM NaCl、2.7mM KCl、1mM MgCl2、0.1mg/ml BSA
希釈基質溶液:50mMのFluor−de−LysTM基質(KI−104、バイオモル・リサーチ・ラボラトリーズ)は、各使用に先立ち、HDACアッセイ緩衝液を用いて150μMに希釈される。アッセイにおける最終濃度は、30μMである。
希釈展開剤溶液:市販の20倍の展開剤濃縮物(KI−105、バイオモル・リサーチ・ラボラトリーズ)は、HDACアッセイ緩衝液中に、1:167に希釈される。この溶液への2μM[終濃度]のTSAは、反応を停止するその能力を高める。
HDAC6ワーキング溶液:HDAC6酵素は、各使用に先立ち、新鮮な酵素のアリコートから、アッセイ緩衝液中に希釈される。アッセイにおける最終濃度は、1〜2nMである。
反応は、96−穴マイクロプレートにおいて、50μl/ウエルの終体積において行われる。5μlのDMSO/化合物溶液を、続いてアッセイ緩衝液中の35μlのHDAC6酵素(又はネガティブコントロール中の35μmアッセイ緩衝液)を添加し、室温において10分間インキュベートする。10μlの、150μMの基質溶液の添加によって反応を開始し、37℃において1時間インキュベートする。50μl展開剤/4μM TSA溶液の添加によって反応を停止し、室温で30分間インキュベートする。ex.360nM、及びem.460nMにおいて、蛍光を測定する。
工程1:5−(トリフルオロアセチル)チオフェン−2−カルボン酸
MeOH/水(1:1)中の、エチル 5−(トリフルオロアセチル)チオフェン−2−カルボキシレート(リエケ・メタル(Rieke Metals)から)の溶液(0.1M)は、LiOH(2.0当量)で処理された。反応混合物は、室温で64時間攪拌された。反応混合物に対し、6N HClがpH2まで滴下添加され、次いで、真空下にMeOHを蒸発させた。水性相はEtOAcで数回抽出された。合された有機層は食塩水で洗浄され、乾燥され、濃縮されて、標題化合物を固体として与えた(95%)。
1H−NMR(300MHz,DMSO−d6,300K)δ13.38(bs,1H),8.11(bs,1H),7.85(d,J=4.2Hz,1H);MS(ES+)C7H3F3O3S要求値:224,実測値:225(M+H)+.
工程1からの生成物は、DMF中のHOBt(1.5当量)及びEDCI(1.5当量)の溶液(0.5M)へ添加され、攪拌は1時間続けられた。次に、(4−メトキシベンジル)アミン(1.5当量)が添加され、反応混合物は室温で16時間攪拌された。粗生成物は、RP−HPLCにより精製され、標題化合物を固体として与えた(7%)。
1H−NMR(400MHz,DMSO−d6,300K)δ9.45(t,J=5.8Hz,1H),8.11(bs,1H),7.96(d,J=4.3Hz,1H),7.25(d,J=8.8Hz,2H),6.90(d,J=8.6Hz,2H),4.41(d,J=5.8Hz,2H),3.73(s,3H);MS(ES+)C15H12F3NO3S要求値:343,実測値:344(M+H)+.
実施例1、工程1からの生成物は、DCM中のPS−カルボジイミド(7.0mL/g樹脂、4.0当量)の懸濁液へ添加された。反応混合物は室温で30分間攪拌され、次に、N−メチル−1−キノリン−7−イルメタンアミン(1.5当量)が添加され、攪拌は室温で一晩継続された。次に、MP−カルボネート(4.0当量)及びPS−イソシアネート(4.0当量)が添加され、混合物は室温で一晩攪拌され、次いで濾過され、溶媒を蒸発させて、標題化合物を固体として与えた(30%)。
LC−MS(ES+)C18H13F3N2O2S要求値:378,実測値:379(M+H)+。保持時間:2.93分。
工程1:4−(トリフルオロアセチル)チオフェン−2−カルボン酸
無水THF中、−78℃の、4−ブロモチオフェン−2−カルボン酸(メイブリッジ(Maybridge)から)の溶液(0.2M)に対し、BuLi(ヘキサン中の1.6N溶液、3.0当量)が滴下添加され、得られた溶液は、−78℃において15分間攪拌された。無水THF中の、N−メチル−N−メトキシトリフルオロアセトアミド(1.5当量)の溶液(1M)が、−78℃において滴下添加された。反応混合物は−78℃で1時間攪拌され、次いで、一晩で室温に達するようにした。反応混合物は、NH4Cl溶液の添加によってクエンチされ、EtOAcで抽出された。合された有機層は食塩水で洗浄され、乾燥され、濃縮されて、標題化合物を油として与えた。
LC−MS(ES+)C7H3F3O3S要求値:224,実測値:225(M+H)+。保持時間:2.80分。
工程1からの生成物は、DMF中に溶解され、得られた溶液(0.5M)は、HOBt(1.5当量)及びEDCl(1.5当量)で処理された。反応混合物は室温で20分間攪拌された。次に、(4−メトキシベンジル)アミン(1.5当量)が添加され、攪拌は室温で一晩継続された。粗溶液は、RP−HPLCにより精製され、標題化合物を固体として与えた(2工程で23%)。
1H−NMR(400MHz,DMSO−d6,300K)δ9.33(t,J=5.6Hz,1H),8.93(s,1H),8.38(s,1H),7.25(d,J=8.4Hz,2H),6.90(d,J=8.4Hz,2H),4.39(d,J=6.0Hz,2H),3.73(s,3H)。MS(ES+)C15H12F3NO3S要求値:343,実測値:344(M+H)+。
CHCl3中の、チオフェン−2−スルホニルクロライド(ランカスター(Lancaster)から)の攪拌された溶液(0.05M)に対し、Et3N(4.0当量)が添加され、続いてN−ベンジルメチルアミン(2.0当量)が0℃において添加された。反応混合物は室温で一晩攪拌され、次いでNH4Cl溶液の添加によってクエンチされた。有機層は分離され、1N HCl、及び食塩水で洗浄され、乾燥された。溶媒の蒸発は、残渣を与え((LC−MS(ES+)C12H13NO2S2要求値:267,実測値:268(M+H)+。保持時間:5.49分)、それは無水THF中に溶解された。得られた溶液(0.2M)は、無水THF中の、LDA(THF/ヘプタン/エチルベンゼン中の2N溶液、1.5当量)の攪拌された溶液(0.1M)に対し、−78℃において滴下添加され、−78℃において45分間攪拌された。無水THF中の、N−メチル−N−メトキシトリフルオロアセトアミド(1.2当量)の溶液(1M)が添加され、反応は0℃まで温められ、この温度に1時間維持された。反応混合物は、NH4Cl溶液の添加によりクエンチされ、次いでDCMで抽出された。合された有機層は1N HCl、食塩水で洗浄され、乾燥された。溶媒の蒸発は、粗生成物を与え、それはRP−HPLCにより精製されて、標題化合物を固体として与えた(52%)。
1H−NMR(600MHz,DMSO−d6,300K)δ8.19(bs,1H),7.92(d,J=4.2Hz,1H),7.40−7.30(m,5H),4.28(s,2H),2.70(s,3H);MS(ES+)C14H14F3NO3S2要求値:363,検出値:364(M+H)+.
無水THF中の、1,3−チアゾール−5−カルボン酸(コンビブロックス(Combi−blocks)から)の溶液(0.2M)に対し、−78℃において、BuLiの溶液(ヘキサン中1.6M溶液、2.2当量)が滴下添加され、−78℃において45分間攪拌された。反応溶液に対し、−78℃において、無水THF中の、N−メチル−N−メトキシトリフルオロアセトアミドの溶液(1M,1.5当量)が添加され、−60℃において1時間攪拌された。反応混合物は、NH4Cl溶液の添加によってクエンチされ、次いでDCMで抽出された。合された有機層は食塩水で洗浄され、乾燥された。溶媒の蒸発は、残渣(LC−MS(ES+)C6H2F3NO3S要求値:225,実測値:226(M+H)+。保持時間:2.26分)を与え、DMF中に溶解された。得られた溶液(0.5M)に対し、HOBt(1.5当量)及びEDCl(1.5当量)が添加され、攪拌は1時間続けられた。N−ベンジルメチルアミド(1.5当量)が添加され、反応混合物は室温で一晩攪拌された、粗生成物は、RP−HPLCにより精製され、標題化合物を固体として与えた(3%)。
1H−NMR(400MHz,DMSO−d6,300K)δ8.43(bs,1H),7.40−7.20(m,5H),4.70(s,2H),3.15(bs,3H);MS(ES+)C14H11F3N2O2S要求値:328,実測値:329(M+H)+.
実施例130 N,N−ジメチル−2−({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)エタンアミニウム・トリフルオロアセテート
実施例131 3−[({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]ピリジニウム・トリフルオロアセテート
実施例132 1−[2−({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)エチル]−1,2,3,4−テトラヒドロキノリニウム・トリフルオロアセテート
実施例133 1−フェニル−4−({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)ピペリジニウム・トリフルオロアセテート
実施例134 4−{4−[({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]フェニル}−1H−イミダゾール−1−イウム・トリフルオロアセテート
実施例135 5−[({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]−7,8−ジヒドロキノリニウム・トリフルオロアセテート
実施例136 3−({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)ピリジニウム・トリフルオロアセテート
実施例137 6,7−ジメトキシ−2−(1−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペリジン−4−イル)−1,2,3,4−テトラヒドロイソキノリニウム・トリフルオロアセテート
実施例138 1−イソキノリン−3−イル−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート
実施例139 4−[4−({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)フェニル]モルホリン−4−イウム・トリフルオロアセテート
実施例140 1−{1−[({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]シクロヘキシル}ピペリジニウム・トリフルオロアセテート
実施例141 1−ピリジン−2−イル−4−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}ピペラジン−1−イウム・トリフルオロアセテート
実施例142 2−(2−チエニル−4−[({[5−(トリフルオロアセチル)−2−チエニル]カルボニル}アミノ)メチル]−1,3−チアゾール−3−イウム・トリフルオロアセテート
実施例143 3−フェニル−7−{[5−(トリフルオロアセチル)−2−チエニル]カルボニル}−5,6,7,8−テトラヒドロイミダゾ[1,2−A]ピラジン−4−イウム・トリフルオロアセテート
実施例144 N−メチル(フェニル)−N−{[5−(トリフルオロアセチル)−2−チエニル]メチル}メタンアミニウム・トリフルオロアセテート
実施例145 (1R)−1−フェニル−N−{[5−(トリフルオロアセチル)−2−チエニル]メチル}エタンアミニウム・トリフルオロアセテート
実施例146 シクロヘキシル−N−{[5−(トリフルオロアセチル)−2−チエニル]メチル}メタンアミニウム・トリフルオロアセテート
DCM/DMF(9:1)中の、実施例1、工程1からの生成物の溶液(0.11M)、HOBt(1.5当量)及びDIPEA(1当量)は、DCM中のPS−カルボジイミド(2.5当量)の懸濁液へ添加された。反応混合物は室温で1時間攪拌され、次いで、DMF中の、1−(2−フェニル−1,3−チアゾール−5−イル)エタンアミンの溶液(0.4M、1.5当量)及びDIPEA(3当量)が添加され、攪拌は室温で24時間続けられた。次に、反応混合物は濾過され、溶媒を蒸発させて粗生成物を得、RP−HPLCにより精製されて、標題化合物を与えた(56%)。
LC−MS(ES+)C18H13F3N2O2S2要求値:410,実測値:411(M+H)+。保持時間:4.1分(LC−MS条件2)。
工程1:N−[4−(アミノスルホニル)フェニル]アセトアミド
無水DCM中の、4−(アセチルアミノ)−ベンゼンスルホニルクロライドの攪拌された溶液(0.1M)を通して、NH3(g)が室温で10分間バブルされた。水の添加後、反応混合物は5分間攪拌された。反応混合物は、Isolute(登録商標)HM−Nカートリッジを通され、次いでEtOAcで数回洗浄された。有機溶液の蒸発は、標題化合物を固体として与えた(99%)。
UPLC−MS(ES+)C8H10N2O3S要求値:214,実測値:215(M+H)+。保持時間:0.53 min.
DCM中の、実施例1、工程1からの生成物の溶液(0.1M)は、BOP(1.3当量)で処理された。反応混合物は室温で5分間攪拌された。次いで、N−[4−(アミノスルホニル)フェニル]アセトアミド(工程1から)(1.3当量)及びBEMP(3当量)が添加され、反応混合物は室温で一晩攪拌され、次いで溶媒の蒸発は粗生成物を与え、RP−HPLCにより精製されて、標題化合物を固体として与えた(63%)。
1H−NMR(300MHz,DMSO−d6,300K)δ10.38(bs,1H.),8.10(bs,1H),7.95(d,J=4Hz,1H),7.91(dd,J=6.0,2.0Hz,2H),7.79(dd,J=6.0,2.0Hz,2H),7.21(d,J=4Hz,1H),2.09(s,3H);MS(ES+)C15H11F3N2O5S2要求値:420,実測値:421(M+H)+.
工程1:1−(2−ブロモ−1,3−チアゾール−5−イル)−2,2,2−トリフルオロエタノール
DME中の、2−ブロモ−5−ホルミルチアゾールの溶液(0.52M)及びCsF(0.2当量)は、TMSCF3(2.0当量)で処理され、得られた溶液は、室温で2時間攪拌された。次いで、反応混合物は水でクエンチされ、室温で15分間攪拌された。水性溶液は、EtOAcで数回抽出され、合された有機層は乾燥され、濃縮され、残渣を与え、シリカゲル上でのフラッシュクロマトグラフィー(石油エーテル/EtOAc20:1〜3:1)により精製されて、標題化合物を黄色の固体として与えた(48%)。
1H NMR(300MHz,CDCl3,300K)δ4.04(d,J=5.9Hz,1H),5.32(m,1H),7.59(s,1H);MS(ES+)C5H3BrF3NOS要求値:261,263,実測値:262,264(M+H)+.
THF中の、工程1からの生成物の−78℃の溶液(0.25M)に対し、BuLi(2.2当量)が滴下添加され、得られた溶液は、−78℃で30分間攪拌された。次に、反応混合物を通して、CO2(g)が10分間バブルされ、反応混合物は−78℃で1時間攪拌された。溶媒の蒸発は、標題化合物を白色の固体として与えた。
LC−MS(ES+)C6H4F3NO3S要求値:227,実測値:228(M+H)+。保持時間:1.80分(LC−MS条件2)。
工程2からの生成物は、DMF中に溶解され、得られた溶液は、N−メチル(キノキサリン−6−イル)メタンアミニウムクロライド(3.0当量)、DIPEA(4.0当量)、及びHBTU(3.0当量)で処理された。反応混合物は室温で12時間攪拌された。EtOAcによる希釈の後、有機相はNaHCO3水溶液(飽和溶液)、1N HCl、食塩水で洗浄され、乾燥され、濃縮されて、標題化合物を固体として与えた。
LC−MS(ES+)C16H13F3N4O2S要求値:382,実測値:383(M+H)+。保持時間:2.89分(LC−MS条件2)。
DCM中の、工程3からの生成物の、室温における溶液(0.1M)は、デス・マーチン・ペルヨージナン(1.5当量)で処理された。反応混合物は室温で2時間攪拌され、次いで、7倍過剰のNa2S2O3を含有するNaHCO3溶液(飽和溶液)へ注ぎいれることによってクエンチされた。30分間の攪拌の後、層は分離され、有機相は食塩水で洗浄され、乾燥された。溶媒の蒸発は、粗生成物を与え、RP−HPLC(条件2)で精製されて、標題化合物を固体として与えた(3工程で21%)。
1H NMR(300MHz,DMSO−d6,300K)δ3.03及び3.51(s,3H),4.97及び5.58(s,2H),7.81(m,1H),7.93(s,1H),8.00(m,1H),8.09(d,J=8.8Hz,1H),8.93(s,2H)。LC−MS(ES+)C16H11F3N4O2S要求値:380,実測値:381(M+H)+。保持時間:2.69分(LC−MS条件2)。
表8に示された化合物の活性は、前文に記述されたアッセイに従って試験され、HDAC1活性は、WO 2006/061638の第104〜106頁に記述されたアッセイにおいて試験された。亜鉛結合基(ZBG)としてトリフルオロアセチル基を有する実施例8のみが、クラスI(HDAC1)を超えて、クラスIIHDAC(HDAC4及び6)に対する選択性を示した。
Claims (10)
- 式I:
(X=O)結合基及びトリフルオロアセチル基の各々は、独立して、任意の炭素環原子上に置換されており;
Aは、CH又はNであり;
Dは、CHであり;
Xは、C又はS=Oであり;
R1は、水素、C1−6アルキル、C2−10アルケニル、C2−10アルキニル、C3−10シクロアルキル、C6−10アリール、独立してN、O、及びSから選択される、1、2、3、又は4個のヘテロ原子を含有し、その多くとも1個のヘテロ原子がO又はSである5員のヘテロ芳香環、1、2、又は3個の窒素原子を含有する6員のヘテロ芳香環、又は、独立してN、O、及びSから選択される、1、2、3、又は4個のヘテロ原子を含有する7〜10員の、飽和、部分飽和、又は不飽和のヘテロ環であって;任意の該環は、独立してハロゲン、シアノ、C1−6アルキル、C1−6アルコキシ、メルカプトC1−6アルキル、ハロC1−6アルキル、ハロC1−6アルコキシ、アミノ、C1−6アルキルアミノ、及びジ(C1−6アルキル)アミノから選択される、1以上の基で置換されてもよく;或いは、
R1は、−(CH2)b−N−(CR2R3)aWと一緒になって、1個のN原子を含有する4員の飽和ヘテロ環か、又は、1、2、又は3個のN原子と、ゼロ又は1個のO原子とを含有する5、6、又は7員の飽和ヘテロ環を形成し;該環は、C3−10シクロアルキル環か、独立してN、O、及びSから選択される1、2、又は3個のヘテロ原子を含有する5、6、又は7員の飽和又は部分飽和ヘテロ環か、フェニル環か、独立してN、O、及びSから選択される1、2、又は3個のヘテロ原子を含有し、その多くとも1個のヘテロ原子がO又はSである5員のヘテロ芳香環か、又は1、2、又は3個の窒素原子を含有する6員のヘテロ芳香環に縮合されてもよく;1つの炭素環原子において、独立してN、O、又はSから選択されるゼロ、1、又は2個のヘテロ原子を含有する5又は6員のスピロ環によって置換されてもよく、該環はフェニル環に縮合されてもよく;或いは、1又は2個のC1−4アルキル基により架橋されてもよく;任意の該環は、独立してL−R4から選択される1以上の基によって置換されてもよく;
各Lは、独立して直接結合か、(CH2)d、又はC=Oであり;
R2及びR3は、独立して、水素、C1−6アルキル、C2−6アルケニル、C2−6アルキニル、ハロC1−6アルキル、C6−10アリール、独立してN、O、及びSから独立して選択される1、2、3、又は4個のヘテロ原子を含有し、その多くとも1個のヘテロ原子がO又はSである5員のヘテロ芳香環;1、2、又は3個の窒素原子を含有する6員のヘテロ芳香環;又は、独立してN、O、及びSから選択される1、2、又は3個のヘテロ原子を含有する7〜10員の、不飽和又は部分飽和ヘテロ環であるか;或いは
R2及びR3は、それらが結合している炭素原子と一緒になって、C3−7シクロアルキル基、>C=O、又は>C=CHを形成し;
Wは、ハロゲン、C1−6アルキル、アミノ、C1−6アルキルアミノ、ジ(C1−6アルキル)アミノ、C1−6アルコキシ、S(O)r(CH2)cR5であるか;又は、環であって:C3−5シクロアルキル基か;独立してN、O、及びSから選択される1、2、又は3個のヘテロ原子を含有する5又は6員の、飽和又は部分飽和ヘテロ環;6〜13員の、飽和、部分飽和、又は不飽和の炭化水素環;独立してN、O、及びSから選択される1、2、3、又は4個のヘテロ原子を含有し、その多くとも1個のヘテロ原子がO又はSである5員のヘテロ芳香環;1、2、又は3個の窒素原子を含有する6員のヘテロ芳香環;又は、独立してN、O、及びSから選択される1、2、3、又は4個のヘテロ原子を含有する7〜15員の、飽和、部分飽和、又は不飽和のヘテロ環であって;任意の該アルキル基又は環は、独立してR6から選択される1以上の基によって置換されてもよく;
各R4は、独立して、ハロゲン;シアノ;ヒドロキシ;オキソ;C1−6アルキル;ハロC1−6アルキル;C1−6アルコキシ;メルカプトC1−6アルキル;ハロC1−6アルコキシ;C1−6アルキルカルボニル;C1−6アルコキシカルボニル;ニトロ;N(Ra)2;N(Ra)CON(Ra)2;N(Ra)CO(C1−6アルキル);N(Ra)CO2(C1−6アルキル);S(O)r(CH2)cR5であるか;又は、環であって:C3−10シクロアルキル;C6−10アリール;C6−10アリールC1−6アルキル;C6−10アリールオキシC1−6アルキル;C6−10アリールカルボニル;独立してN、O、及びSから選択される1、2、又は3個のヘテロ原子を含有する、5又は6員の、飽和又は部分飽和ヘテロ環;独立してN、O、及びSから選択される1、2、3、又は4個のヘテロ原子を含有し、その多くとも1個のヘテロ原子がO又はSである5員のヘテロ芳香環;1、2、又は3個の窒素原子を含有する6員のヘテロ芳香環;又は、独立してN、O、及びSから選択される1、2、又は3個のヘテロ原子を含有する7〜10員の、不飽和又は部分飽和ヘテロ環であって;任意の該アルキル基又は環は、独立してシアノ、オキソ、ヒドロキシ、ハロゲン、C1−6アルキル、C1−6アルコキシ、メルカプトC1−6アルキル、ハロC1−6アルキル、ハロC1−6アルコキシ、アミノ、C1−6アルキルアミノ、ジ(C1−6アルキル)アミノ、1、2、又は3個の窒素原子を含有する6員のヘテロ芳香環、及び、C6−10アリールから選択される1以上の基によって置換されてもよく、任意の該環は、独立してハロゲン、C1−6アルキル、C1−6アルコキシ、及びハロC1−6アルキルから選択される1以上の基によって置換されてもよく;
R5は、C1−6アルキル、アミノ、C1−6アルキルアミノ、ジ(C1−6アルキル)アミノ、C2−10アルケニル、C2−10アルキニル、C3−10シクロアルキル、C6−10アリール、C6−10アリールオキシ、独立してN、O、及びSから選択される1、2、3、又は4個のヘテロ原子を含有し、その多くとも1個のヘテロ原子がO又はSである5員のヘテロ芳香環、1、2、又は3個の窒素原子を含有する6員のヘテロ芳香環、又は、独立してN、O、及びSから選択される1、2、3、又は4個のヘテロ原子を含有する7〜10員の、飽和、部分飽和、又は不飽和のヘテロ環であって;任意の該アルキル又はアルケニル基、又は環は、独立してハロゲン、シアノ、オキソ、ヒドロキシ、C1−6アルキル、C1−6アルコキシ、ハロC1−6アルキル、ハロC1−6アルコキシ、N(Ra)2、−C1−6アルキルN(Ra)2、C1−6アルキルカルボニル、C1−6アルコキシカルボニル、C6−10アリール、及びC6−10アリールオキシ環から選択される1以上の基によって置換されてもよく、該環は、独立してハロゲン、C1−6アルキル、ハロC1−6アルキルから選択される1、2、又は3個の基によって置換されてもよく;
各R6は、独立してハロゲン、シアノ、オキソ、ヒドロキシ、C1−6アルキル、C1−6アルコキシ、メルカプトC1−6アルキル、ハロC1−6アルキル、ハロC1−6アルコキシ、C1−6アルコキシC1−6アルキル、C1−6アルキルカルボニル;C1−6アルコキシカルボニル;ニトロ;N(Ra)2;CON(Ra)2;N(Ra)CON(Ra)2;N(Ra)CO(C1−6アルキル);N(Ra)CO2(C1−6アルキル);S(O)r(CH2)cR5、O(C1−10アルキル)N(Ra)COR7であるか;又は、環であって:C3−7シクロアルキル、C6−10アリール、C6−10アリールC1−6アルキル、C6−10アリールオキシC1−6アルキル、C6−10アリールオキシ、C6−10アリールカルボニル、独立してN、O、及びSから選択される1、2、又は3個のヘテロ原子を含有する5又は6員の、飽和又は部分飽和ヘテロ環、又は、独立してN、O、及びSから選択される1、2、3、又は4個のヘテロ原子を含有し、その多くとも1個のヘテロ原子がO又はSである5員のヘテロ芳香環であって;任意の該環は、独立してハロゲン、C1−6アルキル、及びC1−6アルコキシから選択される1以上の基によって置換されてもよく;
R7は、ハロゲンによって置換されてもよい、C1−6アルコキシ又はC1−6アルキルか、又は、独立してN、O、及びSから選択される1、2、3、又は4個のヘテロ原子を含有する7〜10員の、飽和又は部分飽和ヘテロ環であって、該環は、独立してハロゲン、ヒドロキシ、オキソ、C1−6アルキル、及びC1−6アルコキシから選択される1以上の基によって置換されてもよく;
各Raは、独立して水素、C1−6アルキル、C1−6アルキルカルボニル、C1−6アルコキシカルボニル、C6−10アリール、又はC6−10アリールカルボニルであり;
aは、ゼロ、1、2、3、4、5、又は6であり;
bは、ゼロ、1、2、3、又は4であり;
cは、ゼロ、1、2、3、又は4であり;
各dは、独立して1、2、3、又は4であり;
rは、ゼロ、1、又は2である]
で示される化合物、又は医薬的に許容され得るその塩。 - 式IG:
(X=O)結合基及びトリフルオロアセチル基の各々は、独立して、任意の炭素環原子上に置換されており;
eは、0、1、2、又は3であり;
Hetは、1個のN原子を含有する4員の飽和ヘテロ環か、1、2、又は3個のN原子と、ゼロ又は1個のO原子とを含有する5、6、又は7員の飽和ヘテロ環であって;該環は、C3−10シクロアルキル環か、独立してN、O、及びSから選ばれる1、2、又は3個のヘテロ原子を含有する5、6、又は7員の、飽和又は部分飽和ヘテロ環か、フェニル環か、独立してN、O、及びSから選択される1,2、又は3個のヘテロ原子を含有し、その多くとも1個のヘテロ原子がO又はSである5員のヘテロ芳香環か、又は、1,2、又は3個の窒素原子を含有する6員のヘテロ芳香環に縮合されてもよく;1つの炭素環原子において、独立してN、O、及びSから選択されるゼロ,1、又は2個のヘテロ原子を含有する5又は6員のスピロ環によって置換されてもよく、該環は、フェニル環に縮合されてもよく;或いは、1又は2個のC1−4アルキル基によって架橋されてもよく;かつ
A、D、L、X、及びR4は、請求項1に定義されたとおりである]
の請求項1の化合物、又は医薬的に許容され得るその塩。 - AがCHである、請求項1、2、4、及び5の任意の1項の化合物。
- 任意の先行する請求項の化合物又は医薬的に許容され得るその塩と、医薬的に許容され得る担体とを含んでなる医薬組成物。
- 治療における使用のための、請求項1〜6の任意の1項の化合物、又は医薬的に許容され得るその塩。
- 請求項1〜6の任意の1項の化合物、又は医薬的に許容され得るその塩を有効成分とする、HDAC活性の調整剤。
- 癌、神経変性疾患、統合失調症、脳卒中、再狭窄、及び精神遅滞から選択される疾患の、治療又は予防のための医薬品を製造するための、請求項1〜6の任意の1項の化合物、又は医薬的に許容され得るその塩の使用。
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JP2009507065A (ja) | 2009-02-19 |
EP1926721A2 (en) | 2008-06-04 |
EP1926721B1 (en) | 2016-05-04 |
CA2621448A1 (en) | 2007-03-15 |
WO2007029037A3 (en) | 2007-05-18 |
US20090136979A1 (en) | 2009-05-28 |
AU2006288866B2 (en) | 2012-03-08 |
WO2007029037A2 (en) | 2007-03-15 |
CA2621443A1 (en) | 2007-03-15 |
US20090156591A1 (en) | 2009-06-18 |
WO2007029035A2 (en) | 2007-03-15 |
AU2006288866A1 (en) | 2007-03-15 |
GB0518237D0 (en) | 2005-10-19 |
US7977374B2 (en) | 2011-07-12 |
EP1926826A2 (en) | 2008-06-04 |
WO2007029035A3 (en) | 2007-05-18 |
CA2621443C (en) | 2014-04-08 |
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