JP2015110624A - 治療薬として有用なレゾルシン酸ラクトンの合成 - Google Patents
治療薬として有用なレゾルシン酸ラクトンの合成 Download PDFInfo
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- JP2015110624A JP2015110624A JP2015016497A JP2015016497A JP2015110624A JP 2015110624 A JP2015110624 A JP 2015110624A JP 2015016497 A JP2015016497 A JP 2015016497A JP 2015016497 A JP2015016497 A JP 2015016497A JP 2015110624 A JP2015110624 A JP 2015110624A
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Abstract
Description
本出願は、2008年1月15日出願の米国暫定特許出願第61/011,163号の優先権を主張するものであり、該開示は、全体として参照することにより本明細書に組み込まれる。
本発明は、天然物のラジシコール、およびポコニンの新規の誘導体、類似体、および中間体、ならびにそれらの合成を対象にする。本発明はさらに、キナーゼ、および熱ショックタンパク質90(HSP90)として知られる酵素ファミリーの阻害剤としての、これらの化合物の使用を対象にする。
1950年代の半ばに、リン酸化を触媒するタンパク質キナーゼを用いて、または脱リン酸化ステップに関与するタンパク質ホスファターゼによって、リン酸化が酵素の機能を可逆的に変化させることができることが発見された。これらの反応は、多くの細胞過程、特に、シグナル変換経路を調整するのに重要な役割を果たす。1970年代の後半には、ラウス肉腫ウイルス(v−Src)の形質転換因子が、タンパク質キナーゼであることが発見され、また、発癌プロモーターホルボールエステルが、タンパク質キナーゼCの強力な活性剤であることが認められ、疾病とタンパク質の異常リン酸化との間の初めて知られる関連を明らかにした。その後、変換メカニズムの異常は、多数の発癌性過程を引き起こし、糖尿病、炎症性疾患、および循環器疾患に関与することが認められている(T.Hunter,Cell,100:113−127(2000)、P.Cohen,Nat.Rev.Drug Discov.,1:309(2002))。したがって、選択的キナーゼおよびホスファターゼ阻害剤は、重要な薬剤標的として出現し、キナーゼリン酸化活性の阻害は、化学療法の最も有望なストラテジーの1つである。
式I、I’、II、II’、III、III’、IV、およびVのポコニンマクロライドの新規の類似体、その互変異性体、またはその医薬的に許容される塩、溶媒和物、エステル、もしくはプロドラッグ、ならびにキナーゼ媒介もしくはHSP90媒介の疾患の治療のための、かかる化合物を備える医薬組成物を提供する。また、該化合物を用いて、キナーゼ媒介もしくはHSP90媒介の疾患の治療のための方法も示す。別の実施形態において、本発明は、キナーゼ媒介またはHSP90媒介疾患の治療における、または、患者のキナーゼ媒介またはHSP90媒介疾患の治療のための薬剤の製造における、式I、I’、II、II’、III、III’、IVおよびVの化合物の使用を提供する。本発明の化合物は、キナーゼ阻害剤およびHSP90の阻害剤として活性である。加えて、該化合物の調製のための改良されたプロセスを提供する。
XはO、S、またはNRであり、
Yは−OR、−O−(CH2)mCOOR、−O−(CH2)mCON(R)2、−N(R)2、−N(R)SORまたは−N(R)SO2Rであって、窒素原子に結合する基はZまたはE配置であり得、
R1およびR2は独立して、水素、ハロゲン、OR、N(R)2、SR、アジド、ニトロ、シアノ、脂肪族、アリール、アルキルアリール、アリールアルキル、ヘテロシクリル、ヘテロアリール、−S(O)R、−S(O)2R、−SO2N(R)2、−N(R)SO2R、−N(CO)R、−N(CO)N(R)2、−N(CO)OR、−O(CO)R、−(CO)R、−(CO)OR、−(CO)N(R)2、−O(CO)OR、または−O(CO)N(R)2であり、
R3、R4、R5、R6、R7、R8、R9およびR10は独立して、水素、ハロゲン、アジド、ニトロ、シアノ、脂肪族、アルキルアリール、アラルキル、アリール、ヘテロアルキル、アルキルヘテロアリール、ヘテロシクリル、ヘテロアリール、OR、N(R)2、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、−NR(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mC(O)(CH2)pN(R)2、−(CH2)mC(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−O(CH2)mN3、−(CH2)mN(R)2、−(CH2)mOR、−(CH2)mS(O)(CH2)pR、−(CH2)mS(O)2(CH2)pR、−(CH2)mSO2(CH2)pN(R)2、または−(CH2)mN(R)SO2(CH2)pRであり、
各Rは独立して、R11、水素、脂肪族、アミノ、アジド、シアノ、ニトロ、アルキルアミノ、ジアルキルアミノ、OH、アルコキシ、カルボニルアミノ、アミノカルボニル、アルコキシカルボニル、カルボニルオキシ、カルボキシ、アシル、アリール、カルカリール、ベンジルを含むアリールアルキル、ヘテロアルキル、ヘテロアリール、ヘテロシクリル、もしくは保護基であるか、または同一窒素上の2つのRは、前記窒素と一緒になって、5〜8員の複素環式環またはヘテロアリール環を形成し、基は2つ以上のR置換基を含む場合、Rは任意に置換され、各Rは同一であるか、または異なってもよく、
R11は以下の基であり、
nは0、1または2であり、
mおよびpは独立して、0、1、2、3、4または5であり、点線は単結合または二重結合のいずれかであることを示し、原子価要件は、追加の水素原子によって満たされ、
式I’において、nが1であり、XがOであり、炭素原子を担持するR9とR10との間に二重結合が存在する場合、R5、R6、R7、R8、R9またはR10のうちの少なくとも1つは水素でなく、
式I’において、nが1であり、XがOであり、炭素原子を担持するR9とR10との間の結合が単結合である場合、R5、R6、R7、またはR8のうちの少なくとも1つは水素ではない。
キナーゼおよびHSP90の阻害剤として有用であるレゾルシン酸ラクトンに基づいた新規化合物を提供する。また、化合物を含む組成物および該化合物の調製プロセスも提供する。キナーゼおよびHSP−90の阻害のための化合物の使用、ならびにキナーゼ媒介もしくはHSP90媒介の疾患を有する患者に、式I、I’、II、II’、III、III’、IV、またはVの化合物のキナーゼ阻害有効量またはHSP90阻害有効量を投与するステップを含む、キナーゼ媒介もしくはHSP90媒介の疾患の治療のための方法を提供する。
本発明の第1の実施形態において、式Iの化合物、その互変異性体、またはその医薬的に許容される塩、溶媒和物、エステル、もしくはプロドラッグを提供し、
XはO、SまたはNRであり、
Yは−OR、−O−(CH2)mCOOR、−O−(CH2)mCON(R)2、−N(R)2、−N(R)SORまたは−N(R)SO2Rであって、窒素原子に結合する基はZまたはE配置であり得、
R1およびR2は独立して、水素、ハロゲン、OR、N(R)2、SR、アジド、ニトロ、シアノ、脂肪族、アリール、アルキルアリール、アリールアルキル、ヘテロシクリル、ヘテロアリール、−S(O)R、−S(O)2R、−SO2N(R)2、−N(R)SO2R、−N(CO)R、−N(CO)N(R)2、−N(CO)OR、−O(CO)R、−(CO)R、−(CO)OR、−(CO)N(R)2、−O(CO)OR、または−O(CO)N(R)2であり、
R3、R4、R5、R6、R7、R8、R9およびR10は独立して、水素、ハロゲン、アジド、ニトロ、シアノ、脂肪族、アルキルアリール、アラルキル、アリール、ヘテロアルキル、アルキルヘテロアリール、ヘテロシクリル、ヘテロアリール、OR、N(R)2、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、−NR(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mC(O)(CH2)pN(R)2、−(CH2)mC(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−O(CH2)mN3、−(CH2)mN(R)2、−(CH2)mOR、−(CH2)mS(O)(CH2)pR、−(CH2)mS(O)2(CH2)pR、−(CH2)mSO2(CH2)pN(R)2、または−(CH2)mN(R)SO2(CH2)pRであり、
各Rは独立して、R11、水素、脂肪族、アミノ、アジド、シアノ、ニトロ、アルキルアミノ、ジアルキルアミノ、OH、アルコキシ、カルボニルアミノ、アミノカルボニル、アルコキシカルボニル、カルボニルオキシ、カルボキシ、アシル、アリール、カルカリール、ベンジルを含むアリールアルキル、ヘテロアルキル、ヘテロアリール、ヘテロシクリル、もしくは保護基であるか、または同一窒素上の2つのRは、前記窒素と一緒になって、5〜8員の任意に置換された複素環式またはヘテロアリール環を形成し、Rは任意に置換され、各Rは同一であるか、または異なってもよく、
R11は以下の基であり、
nは0、1または2であり、
mおよびpは独立して、0、1、2、3、4または5であり、点線は単結合または二重結合のいずれかであることを示し、原子価要件は、追加の水素原子によって満たされる。
XはOまたはNRであり、
Yは−O−(CH2)mCOOR、または−O−(CH2)mCON(R)2であり、窒素原子に結合する基はZまたはE配置であり得、
R1およびR2は独立して、水素、ハロゲン、OR、N(R)2、または脂肪族であり、
R3およびR4は独立して、水素、脂肪族、OR、N(R)2、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mC(O)(CH2)pN(R)2、−(CH2)mC(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−(CH2)mN3、−(CH2)mN(R)2、−(CH2)mOR、−(CH2)mS(O)(CH2)pR、−(CH2)mS(O)2(CH2)pR、−(CH2)mSO2(CH2)pN(R)2、または−(CH2)mN(R)SO2(CH2)pRであり、
R5、R6、R9およびR10は独立して、水素、脂肪族、アルキルアリール、アラルキル、アリール、ヘテロアルキル、アルキルヘテロアリール、ヘテロシクリル、ヘテロアリール、OR、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、−NR(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mC(O)(CH2)pN(R)2、−(CH2)mC(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−O(CH2)mN3、−(CH2)mN(R)2、−(CH2)mOR、−(CH2)mS(O)(CH2)pR、−(CH2)mS(O)2(CH2)pR、−(CH2)mSO2(CH2)pN(R)2、または−(CH2)mN(R)SO2(CH2)pRであり、
R7およびR8は独立して、水素、ハロゲン、脂肪族、アルキルアリール、アラルキル、アリール、ヘテロアルキル、アルキルヘテロアリール、ヘテロシクリル、ヘテロアリール、OR、N(R)2、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、−NR(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mC(O)(CH2)pN(R)2、−(CH2)mC(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−O(CH2)mN3−(CH2)mN(R)2、−(CH2)mOR、−(CH2)mS(O)(CH2)pR、−(CH2)mS(O)2(CH2)pR、−(CH2)mSO2(CH2)pN(R)2、または−(CH2)mN(R)SO2(CH2)pRである化合物を提供する。
Yは−O−(CH2)mCOORまたは−O−(CH2)mCON(R)2であり、窒素原子に結合する基はZまたはE配置であり得、
R1およびR2は独立して、水素、ハロゲンであり、
R3およびR4は独立して、水素、脂肪族、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−(CH2)mN(R)2、または−(CH2)mORであり、
R5、R6、R9およびR10は独立して、水素、脂肪族、アラルキル、ヘテロアルキル、ヘテロシクリル、またはヘテロアリールであり、
R7およびR8は独立して、水素、脂肪族、アルキルアリール、アラルキル、アリール、ヘテロアルキル、アルキルヘテロアリール、ヘテロシクリル、ヘテロアリール、OR、N(R)2、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、または−NR(CH2)mOC(O)(CH2)pN(R)2である。
Yは−O−(CH2)mCOORまたは−O−(CH2)mCON(R)2であり、窒素原子に結合する基はZまたはE配置であり得、
R1およびR2は独立して、水素、ハロゲンであり、
R3およびR4は独立して、水素、脂肪族、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−(CH2)mN(R)2、または−(CH2)mORであり、
R5、R6、R9およびR10は独立して、水素、脂肪族、アラルキル、ヘテロアルキル、ヘテロシクリル、またはヘテロアリールであり、
R7およびR8は独立して、アルキルアリール、アラルキル、アリール、ヘテロアルキル、アルキルヘテロアリール、ヘテロシクリル、ヘテロアリール、OR、N(R)2、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、または−NR(CH2)mOC(O)(CH2)pN(R)2である。
XはOまたはNRであり、
Yは−O−(CH2)mCOORまたは−O−(CH2)mCON(R)2であり、窒素原子に結合する基はZまたはE配置であり得、
R1およびR2は独立して、水素、ハロゲン、OR、N(R)2または脂肪族であり、
R3またはR4は独立して、水素、脂肪族、OR、N(R)2、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mC(O)(CH2)pN(R)2、−(CH2)mC(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−O(CH2)mN3−(CH2)mN(R)2、−(CH2)mOR、−(CH2)mS(O)(CH2)pR、−(CH2)mS(O)2(CH2)pR、−(CH2)mSO2(CH2)pN(R)2、または−(CH2)mN(R)SO2(CH2)pRであり、
R5、R6、R9、およびR10は独立して、水素、脂肪族、アルキルアリール、アラルキル、アリール、ヘテロアルキル、アルキルヘテロアリール、ヘテロシクリル、ヘテロアリール、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mC(O)(CH2)pN(R)2、−(CH2)mC(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−O(CH2)mN3、−(CH2)mN(R)2、−(CH2)mOR、−(CH2)mS(O)(CH2)pR、−(CH2)mS(O)2(CH2)pR、−(CH2)mSO2(CH2)pN(R)2、または−(CH2)mN(R)SO2(CH2)pRであり、
R7またはR8は独立して、水素、ハロゲン、脂肪族、アルキルアリール、アラルキル、アリール、ヘテロアルキル、アルキルヘテロアリール、ヘテロシクリル、ヘテロアリール、OR、N(R)2、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、−NR(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mC(O)(CH2)pN(R)2、−(CH2)mC(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−(CH2)mN3、−(CH2)mN(R)2、−(CH2)mOR、−(CH2)mS(O)(CH2)pR、−(CH2)mS(O)2(CH2)pR、−(CH2)mSO2(CH2)pN(R)2、または−(CH2)mN(R)SO2(CH2)pRである化合物を提供する。
Yは−O−(CH2)mCOORまたは−O−(CH2)mCON(R)2であり、窒素原子に結合する基はZまたはE配置であり得、
R1およびR2は独立して、水素またはハロゲンであり、
R3またはR4は独立して、水素、脂肪族、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−(CH2)mN(R)2、または−(CH2)mORであり、
R5、R6、R9、およびR10は独立して、水素、脂肪族、アラルキル、ヘテロアルキル、ヘテロシクリル、またはヘテロアリールであり、
R7またはR8は独立して、水素、脂肪族、アルキルアリール、アラルキル、アリール、ヘテロアルキル、アルキルヘテロアリール、ヘテロシクリル、ヘテロアリール、OR、N(R)2、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、または−NR(CH2)mOC(O)(CH2)pN(R)2である。
Yは−O−(CH2)mCOORまたは−O−(CH2)mCON(R)2であり、窒素原子に結合する基はZまたはE配置であり得、
R1およびR2は独立して、水素またはハロゲンであり、
R3またはR4は独立して、水素、脂肪族、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−(CH2)mN(R)2、または−(CH2)mORであり、
R5、R6、R9、およびR10は独立して、水素、脂肪族、アラルキル、ヘテロアルキル、ヘテロシクリル、またはヘテロアリールであり、
R7またはR8は独立して、アルキルアリール、アラルキル、アリール、ヘテロアルキル、アルキルヘテロアリール、ヘテロシクリル、ヘテロアリール、−OR、−N(R)2、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、または−NR(CH2)mOC(O)(CH2)pN(R)2である。
Yは−O−(CH2)mCOORまたは−O−(CH2)mCON(R)2であり、窒素原子に結合する基はZまたはE配置であり得、
R1およびR2は独立して、水素またはハロゲンであり、
R3またはR4は独立して、水素、脂肪族、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−(CH2)mN(R)2、または−(CH2)mORであり、
R5、R6、R9、およびR10は独立して、水素、脂肪族、アラルキル、ヘテロアルキル、ヘテロシクリル、またはヘテロアリールであり、
R7またはR8は独立して、アルキルアリール、アラルキル、アリール、ヘテロアルキル、アルキルヘテロアリール、ヘテロシクリル、ヘテロアリール、−OR、−N(R)2、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、または−NR(CH2)mOC(O)(CH2)pN(R)2である。
XはOまたはNRであり、
Yは−O−(CH2)mCOORまたは−O−(CH2)mCON(R)2であり、窒素原子に結合する基はZまたはE配置であり得、
R1およびR2は独立して、水素、ハロゲン、OR、N(R)2または脂肪族であり、
R3およびR4は独立して、水素、脂肪族、OR、N(R)2、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mC(O)(CH2)pN(R)2、−(CH2)mC(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−O(CH2)mN3、−(CH2)mN(R)2、−(CH2)mOR、−(CH2)mS(O)(CH2)pR、−(CH2)mS(O)2(CH2)pR、−(CH2)mSO2(CH2)pN(R)2、または−(CH2)mN(R)SO2(CH2)pRであり、
R5およびR6は独立して、水素、脂肪族、アルキルアリール、アラルキル、アリール、ヘテロアルキル、アルキルヘテロアリール、ヘテロシクリル、ヘテロアリール、OR、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、−NR(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mC(O)(CH2)pN(R)2、−(CH2)mC(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−O(CH2)mN3、−(CH2)mN(R)2、−(CH2)mOR、−(CH2)mS(O)(CH2)pR、−(CH2)mS(O)2(CH2)pR、−(CH2)mSO2(CH2)pN(R)2、または−(CH2)mN(R)SO2(CH2)pRであり、
R7、R8、R9、およびR10は独立して、水素、ハロゲン、脂肪族、アルキルアリール、アラルキル、アリール、ヘテロアルキル、アルキルヘテロアリール、ヘテロシクリル、ヘテロアリール、OR、N(R)2、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、−NR(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mC(O)(CH2)pN(R)2、−(CH2)mC(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−O(CH2)mN3、−(CH2)mN(R)2、−(CH2)mOR、−(CH2)mS(O)(CH2)pR、−(CH2)mS(O)2(CH2)pR、−(CH2)mSO2(CH2)pN(R)2、または−(CH2)mN(R)SO2(CH2)pRであり、R、m、およびpは上記式Iに対して定義されたとおりである化合物を提供する。
Yは−O−(CH2)mCOORまたは−O−(CH2)mCON(R)2であり、窒素原子に結合する基はZまたはE配置であり得、
R1およびR2は独立して、水素、ハロゲンであり、
R3およびR4は独立して、水素、脂肪族、OR、N(R)2、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mN(R)C(O)(CH2)pOR,−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR,−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−(CH2)mN(R)2、または−(CH2)mORであり、
R5およびR6は独立して、水素、脂肪族、アラルキル、ヘテロアルキル、ヘテロシクリル、またはヘテロアリールであり、
R7、R8、R9、およびR10は独立して、水素、脂肪族、アルキルアリール、アラルキル、アリール、ヘテロアルキル、アルキルヘテロアリール、ヘテロシクリル、ヘテロアリール、OR、N(R)2、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、または−NR(CH2)mOC(O)(CH2)pN(R)2である。
Yは−O−(CH2)mCOORまたは−O−(CH2)mCON(R)2であり、窒素原子に結合する基はZまたはE配置であり得、
R1およびR2は独立して、水素、ハロゲンであり、
R3およびR4は独立して、水素、脂肪族、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−(CH2)mN(R)2、または−(CH2)mORであり、
R5およびR6は独立して、水素、脂肪族、アラルキル、ヘテロアルキル、ヘテロシクリル、またはヘテロアリールであり、
R7、R8は独立して、アルキルアリール、アラルキル、アリール、ヘテロアルキル、アルキルヘテロアリール、ヘテロシクリル、ヘテロアリール、OR、N(R)2、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、または−NR(CH2)mOC(O)(CH2)pN(R)2であり、
R9およびR10は独立して、水素、脂肪族、アルキルアリール、アラルキル、アリール、ヘテロアルキル、アルキルヘテロアリール、ヘテロシクリル、ヘテロアリール、OR、N(R)2、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、または−NR(CH2)mOC(O)(CH2)pN(R)2である。
Yは−O−(CH2)mCOORまたは−O−(CH2)mCON(R)2であり、窒素原子に結合する基はZまたはE配置であり得、
R1およびR2は独立して、水素、ハロゲンであり、
R3およびR4は独立して、水素、脂肪族、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−(CH2)mN(R)2、または−(CH2)mORであり、
R5およびR6は独立して、水素、脂肪族、アラルキル、ヘテロアルキル、ヘテロシクリル、またはヘテロアリールであり、
R7、R8は独立して、OR、N(R)2、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、または−NR(CH2)mOC(O)(CH2)pN(R)2であり、
R9およびR10は独立して、水素、脂肪族、アルキルアリール、アラルキル、アリール、ヘテロアルキル、アルキルヘテロアリール、ヘテロシクリル、ヘテロアリール、OR、N(R)2、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、または−NR(CH2)mOC(O)(CH2)pN(R)2である。
式IVの別の実施形態において、R1およびR2は水素である。
式IVのさらに別の実施形態において、R3またはR4は独立して、アルキルまたは水素である。
XはOまたはNRであり、
Yは−O−(CH2)mCOORまたは−O−(CH2)mCON(R)2であり、窒素原子に結合する基はZまたはE配置であり得、
R1およびR2は独立して、水素、ハロゲン、OR、N(R)2または脂肪族であり、
R3は水素、脂肪族、OR、N(R)2、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mC(O)(CH2)pN(R)2、−(CH2)mC(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−O(CH2)mN3、−(CH2)mN(R)2、−(CH2)mOR、−(CH2)mS(O)(CH2)pR、−(CH2)mS(O)2(CH2)pR、−(CH2)mSO2(CH2)pN(R)2、または−(CH2)mN(R)SO2(CH2)pRであり、
R5、R6、R9およびR10は独立して、水素、脂肪族、アルキルアリール、アラルキル、アリール、ヘテロアルキル、アルキルヘテロアリール、ヘテロシクリル、ヘテロアリール、OR、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、−NR(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mC(O)(CH2)pN(R)2、−(CH2)mC(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−O(CH2)mN3、−(CH2)mN(R)2、−(CH2)mOR、−(CH2)mS(O)(CH2)pR、−(CH2)mS(O)2(CH2)pR、−(CH2)mSO2(CH2)pN(R)2、または−(CH2)mN(R)SO2(CH2)pRであり、
R7およびR8は独立して、水素、ハロゲン、脂肪族、アルキルアリール、アラルキル、アリール、ヘテロアルキル、アルキルヘテロアリール、ヘテロシクリル、ヘテロアリール、OR、N(R)2、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、−NR(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mC(O)(CH2)pN(R)2、−(CH2)mC(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−O(CH2)mN3、−(CH2)mN(R)2、−(CH2)mOR、−(CH2)mS(O)(CH2)pR、−(CH2)mS(O)2(CH2)pR、−(CH2)mSO2(CH2)pN(R)2、または−(CH2)mN(R)SO2(CH2)pRである。
Yは−O−(CH2)mCOORまたは−O−(CH2)mCON(R)2であり、窒素原子に結合する基はZまたはE配置であり得、
R1およびR2は独立して、水素、ハロゲンであり、
R3は水素、脂肪族、OR、N(R)2、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−(CH2)mN(R)2、または−(CH2)mORであり、
R5、R6、R9およびR10は独立して、水素、脂肪族、アラルキル、ヘテロアルキル、ヘテロシクリル、またはヘテロアリールであり、
R7およびR8は独立して、水素、脂肪族、アルキルアリール、アラルキル、アリール、ヘテロアルキル、アルキルヘテロアリール、ヘテロシクリル、ヘテロアリール、OR、N(R)2、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、または−NR(CH2)mOC(O)(CH2)pN(R)2である化合物を提供する。
Yは−O−(CH2)mCOORまたは−O−(CH2)mCON(R)2であり、窒素原子に結合する基はZまたはE配置であり得、
R1およびR2は独立して、水素、ハロゲンであり、
R3は水素、脂肪族、OR、N(R)2、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−(CH2)mN(R)2、または−(CH2)mORであり、
R5、R6、R9およびR10は独立して、水素、脂肪族、アラルキル、ヘテロアルキル、ヘテロシクリル、またはヘテロアリールであり、
R7およびR8は独立して、OR、N(R)2、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、または−NR(CH2)mOC(O)(CH2)pN(R)2である。
XはOまたはNRであり、
Yは−O−(CH2)mCOORまたは−O−(CH2)mCON(R)2であり、窒素原子に結合する基はZまたはE配置であり得、
R1およびR2は独立して、水素、ハロゲン、OR、N(R)2または脂肪族であり、
R3、R4、およびR4aは独立して、水素、脂肪族、OR、N(R)2、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mC(O)(CH2)pN(R)2、−(CH2)mC(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−O(CH2)mN3、−(CH2)mN(R)2、−(CH2)mOR、−(CH2)mS(O)(CH2)pR、−(CH2)mS(O)2(CH2)pR、−(CH2)mSO2(CH2)pN(R)2、または−(CH2)mN(R)SO2(CH2)pR、であり、
R5、R6、R9およびR10は独立して、水素、脂肪族、アルキルアリール、アラルキル、アリール、ヘテロアルキル、アルキルヘテロアリール、ヘテロシクリル、ヘテロアリール、OR、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、−NR(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mC(O)(CH2)pN(R)2、−(CH2)mC(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−O(CH2)mN3、−(CH2)mN(R)2、−(CH2)mOR、−(CH2)mS(O)(CH2)pR、−(CH2)mS(O)2(CH2)pR、−(CH2)mSO2(CH2)pN(R)2、または−(CH2)mN(R)SO2(CH2)pRであり、
R7およびR8は独立して、水素、ハロゲン、脂肪族、アルキルアリール、アラルキル、アリール、ヘテロアルキル、アルキルヘテロアリール、ヘテロシクリル、ヘテロアリール、OR、N(R)2、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、−NR(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mC(O)(CH2)pN(R)2、−(CH2)mC(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−O(CH2)mN3、−(CH2)mN(R)2、−(CH2)mOR、−(CH2)mS(O)(CH2)pR、−(CH2)mS(O)2(CH2)pR、−(CH2)mSO2(CH2)pN(R)2、または−(CH2)mN(R)SO2(CH2)pRである化合物を提供する。
Yは−O−(CH2)mCOORまたは−O−(CH2)mCON(R)2であり、窒素原子に結合する基はZまたはE配置であり得、
R1およびR2は独立して、水素、ハロゲンであり、
R3、R4、およびR4aは独立して、水素、脂肪族、OR、N(R)2、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−(CH2)mN(R)2、または−(CH2)mORであり、
R5、R6、R9およびR10は独立して、水素、脂肪族、アラルキル、ヘテロアルキル、ヘテロシクリル、またはヘテロアリールであり、
R7およびR8は独立して、水素、脂肪族、アルキルアリール、アラルキル、アリール、ヘテロアルキル、アルキルヘテロアリール、ヘテロシクリル、ヘテロアリール、OR、N(R)2、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、または−NR(CH2)mOC(O)(CH2)pN(R)2である。
Yは−O−(CH2)mCOORまたは−O−(CH2)mCON(R)2であり、窒素原子に結合する基はZまたはE配置であり得、
R1およびR2は独立して、水素、ハロゲンであり、
R3、R4、およびR4aは独立して、水素、脂肪族、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−(CH2)mN(R)2、または−(CH2)mORであり、
R5、R6、R9およびR10は独立して、水素、脂肪族、アラルキル、ヘテロアルキル、ヘテロシクリル、またはヘテロアリールであり、
R7およびR8は独立して、OR、N(R)2、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH2)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、または−NR(CH2)mOC(O)(CH2)pN(R)2である。
「医薬的に許容される塩」および「プロドラッグ」という用語は、患者への投与後、本明細書の化合物を提供する、化合物の任意の医薬的に許容される型(塩、エステル、リン酸エステル、エステルまたは関連した基の塩等)を記載するために本明細書を通じて使用される。化合物が、安定した非毒性酸または塩基性塩を形成するのに十分に塩基性または酸性である場合、塩として化合物の投与は適切であり得る。医薬的に許容される塩または複合体という用語は、本発明の化合物の所望の生物活性を維持し、最小限の望ましくない毒性効果を示す、塩または複合体を意味する。
キラル中心を有する本発明の化合物は、光学的活性体およびラセミ体で存在し、単離され得る。本発明は、本発明の化合物の、任意のラセミ体、光学活性体、ジアステレオ異性体、多型体、もしくは立体異性体、またはその混合物を包含し、本明細書の有用な特性を所有する。
i) 複数の結晶の物理的分離−−個々の鏡像体の巨視的結晶を手作業で分離させる方法。本方法は、分離鏡像体の結晶が存在する、すなわち、材料が集合体であり、該結晶が、視覚的に異なる場合、使用され得る。
本明細書における用語が範囲(すなわち、C1−4アルキル)として特定される場合には、該範囲は独立して、それぞれの元素の範囲を意味する。限定されない例として、C1−4アルキルは独立して、C1、C2、C3、またはC4アルキルを意味する。同様に、1つ以上の置換基が群「から独立して選択される」と称する場合には、それぞれの置換基がその群から成るいずれの要素でもあり得、これらの群から成るいずれの組み合わせも該群から分離され得ることを意味する。例えば、R1およびR2は独立して、X、Y、およびZから選択される場合、これには、R1はXでありR2はXであること、R1はXでありR2はYであること、R1はXでありR2はZであること、R1はYでありR2はXであること、R1はYでありR2はYであること、R1はYでありR2はZであること、R1はZでありR2はXであること、R1はZでありR2はYであること、および、R1はZでありR2はZであるという、群を単独に含む。
本明細書の化合物は、特に、キナーゼによって媒介される、またはHSP90によって媒介される、疾病の治療または予防に有用である。一実施形態において、本明細書の化合物は、癌転移を含む、増殖性疾患の治療または予防に有用である。別の実施形態において、本明細書の化合物は、キナーゼまたはHSP90に関連する炎症性または自己免疫疾患の治療または予防に有用である。
呼吸器疾患に罹患している哺乳類、特にヒトは、任意に医薬的に許容される担体または希釈剤中で、有効量の本明細書の化合物、またはその医薬的に許容される塩、エステル、もしくはプロドラッグを含む組成物の吸入、全身、経口、局所、または経皮投与により治療され得る。
化合物はまた、所望の作用を低下させない他の活性材料、または所望の作用を補う材料とともに混合され得る。活性化合物は、キナーゼまたはHSP90により媒介される疾患の治療に使用される他の薬剤とともに、すなわち、組み合わせて、またはそれと交互に、投与され得る。
代表的なステロイドは、リン酸ベタメタゾンナトリウムおよび酢酸ベタメタゾンを含む。Physicians’Desk Reference,50th Edition,1996。
本発明のレゾルシン酸ラクトンの合成を対象とするモジュラー合成プロセスを以下に示す。開発された合成は、樹脂介在または固体相合成を利用して、中間体および最終生成物の分離を最小化および促進し得る。
本明細書において、以下の省略形を使用する。
Ac アセチル(CH3C=O)
BBN ボラビジクロノナン
Bn ベンジル
Bz ベンゾイル
Cy3 シアニン染料標識試薬
δ 化学シフト(NMR)
DCC ジシクロヘキシルカルボジイミド
DEAD アゾジカルボン酸ジエチル
DIAD アゾジカルボン酸ジイソプロピル
d.e. ジアステレオ異性体過剰率
DIBALまたはDibal−H 水素化ジイソブチルアルミニウム
DIC N,N’−ジイソプロピルカルボジイミド
DMAP 4−ジメチルアミノピリジン
DMF ジメチルホルムアミド
DMSO ジメチルスルホキシド
EC50 生体内で50%の最大有効濃度を得るために必要とされる血漿濃度
e.e. 鏡像体過剰率
EOM エトキシメチル(CH3CH2OCH2−)
FDA 食品医薬品局
Grubbs’II 第2世代グラブス触媒:(ルテニウム[1,3−ビス(2,4,6−トリメチルフェニル)−2−イミダゾリニリデン]ジクロロ(フェニルメチレン)(トリシクロヘキシルホスファン)
HPLC 高速クロマトグラフィ
HRMS 高分解能質量分析
HSP90 熱ショックタンパク質90
ヒューニッヒ塩基 ジイソプロピルエチルアミン
IC50 体外で50%阻害に必要とされる薬物濃度
Ipc2 ビス−イソピノカンホリル
J 結合定数
LDA リチウムジイソプロピルアミド
μM マイクロモル濃度(μmol.l−1)
M.S. マススペクトル
NMR 核磁気共鳴
PG 保護基
PS− ポリマー担持
PS−DCC ポリマー担持ジシクロヘキシルカルボジイミド
PS−TBD (1,5,7)−トリアザ−ビシクロ[4.4.0]ドデカ−5−エン−7−メチルポリスチレン
PyrまたはPy ピリジン
rac ラセミ化合物
RAL レゾルシン酸ラクトン
RCM 閉環メタセシス
Rf 保持因子
RT 室温
SEM 2−トリメチルシリルエトキシメトキシ
TBAF フッ化テトラ−n−ブチルアンモニウム
TBAI ヨウ化テトラ−n−ブチルアンモニウム
TBDPS t−ブチルジフェニルシリル
TBS t−ブチルジメチルシリル
TFA トリフルオロ酢酸
TFAA トリフルオロ酢酸無水物
THF テトラヒドロフラン
THP テトラヒドロピラン
TLC 薄膜クロマトグラフィ
TMS トリメチルシリル
TMSCl トリメチルシリルクロリド
TNTU 2−(エンド−5−ノルボルネン−2.3−ジカルボキシルイミド)−,1,3,3−テトラメチルウロニウムテトラフルオロホウ酸
Ts トシル(p−CH3C6H4SO2)
p−TSOH パラ−トルエンスルホン酸
以下に例証されるスキームは、本発明の化合物、および該化合物の調製に使用される中間体の合成の非限定的な例である。スキームにおいて描写される反応は、代替試薬および条件を使用して、所望の形質転換を達成し得ることが、当業者には明らかとなるであろう。例えば、様々な保護基を化合物の合成に使用してもよく、スキームにおいて描写される特定の基は、非限定的な例である。例えば、示される保護基の代わりに、Greene et al.,Protective Groups in Organic Synthesis, John Wiley & Sons,3rd Ed.,1999において教示される、ヒドロキシおよびカルボキシル基の任意の適切な保護基を使用してもよい。さらに、示される形質転換のための当該技術分野で既知の代替試薬を使用してもよく、例えば、芳香族カルボン酸のエステル化、または閉環反応を含む。
多様なホモアリルアルコールが商業的に入手可能であり、合成に使用してもよい。他のホモアリルアルコールを担持する様々な置換基は、当該技術分野で既知の方法によって調製され得る。以下のスキーム3は、商業的に入手可能でない様々なホモアリルアルコールの合成を説明する。一実施形態において、ホモアリルアルコール3−3は、ラセミアルコールの酵素的分割(H.E.Master et al.,Tet.Lett.,37:9253(1996)、S.Singh et al.,Tet.Asymm.,13:2679(2002))、あるいは対応するアルデヒドのBrownアリル化(H.C.Brown and P.K.Jadhav J.Am.Chem.Soc.,105:2092(1983))のいずれかにより最も高い鏡像体形成において得られた。フェニル(3−3a)、ピリジニル(3−3b)、およびフリル(3−3c)アルコールは、酵素的分割により調製された(スキーム3)。ラセミアルコール3−2a−cは、対応するアルデヒド3−1a−cにおける市販の臭化アリルマグネシウムのグリニャール付加後、得られた。
a)アリルMgBr(1.5当量)、THF、0.5時間、0℃、71%(3−2a)、41%(3−2b)、74%(3−2c)、b)R 2 =Ph:酢酸ビニル(32.5当量)、アマノリパーゼPS−CII(50mg/mmolの3−2)、23℃、30時間(1H NMRにより観察)、R 2 =Pyr、Fur:酢酸ビニル(10.0当量)、アマノリパーゼPS−CII(50mg/mmolの3−2)、THF、23℃、5−30時間(1H NMRにより観察)、c)K2CO3(0.8当量)、MeOH、23℃、98%((R)−3−2a)、92%((R)−3−2b)、84%((R)−3−2c)。
a)(−)−α−ピネン(2.4当量)、BH3・Me2S(1.0当量)、THF、23℃で1時間、その後、4℃で12時間、76%、b)MeOH(1.2当量)、Et2O、0℃、2時間、94%、c)アリルMgBr(0.95当量)、Et2O、0→23℃、1時間、92%、d)4−3d−f(1.05当量)、Et2O、−100℃、0.5時間、3N NaOH、H2O235%、還流、3時間、77〜93%。アルコールの鏡像体過剰率は、3,5−ジニトロ塩化ベンゾイルを用いたアシル化後、キラルHPLC分析により測定された。
様々なワインレブアミドを使用して、本発明の化合物を調製してもよい。ワインレブアミドは、当該技術分野においてよく知られ、ワインレブアミドの調製のための多くのワインレブアミドまたは試薬は、商業的に入手可能である。さらに、ワインレブアミドの調製のための方法が知られている。例えば、多様なワインレブアミドは、所望の官能性を有するアルデヒドを、ワインレブアミドイリド(化合物5−4、スキーム5)またはリン酸ワインレブアミド(化合物6−6、スキーム6)と反応させることによって調製し、所望のα、β−不飽和ワインレブアミドを形成してもよい。一実施形態において、保護ヒドロキシ基を含むワインレブアミドは、以下のスキーム5に従って調製される。
トランス−3−ヘキセン二酸ジメチルエステル5−1を、水素化アルミニウムリチウムを用いて、対応するジオールに還元した。ジオールは、tert−ブチルジフェニルシリルエーテル5−2としてモノ保護され、遊離アルコールは、ニトリルを介して、3ステップでアルデヒド5−3に変換した。次いで、アルデヒド5−3を、ワインレブアミドイリド5−4で処理し、ジエンワインレブアミド5−5を産生した。様々な他のワインレブアミドは、化合物5−4および所望の官能性を有するアルデヒドを使用して調製してもよい。
LDA等の巨大基による酢酸t−ブチル6−1の処理、および生じるエノレートとビニルアルデヒドとの反応は、アルコール6−2をもたらす。アミノリパーゼPS−C IIでの処理によってラセミアルコールを溶解し、キラル酢酸6−3およびキラルアルコール6−4を産生する。ヒドロキシ基は、例えば、t−ブチルジメチルシリルエーテル6−5として適切に保護され、対応するアルデヒドは、DIBAL−Hとの反応によって産生される。ワインレブホスホン酸6−6との反応は、所望のワインレブアミド6−7をもたらす。
本発明の別の実施形態において、化合物459/460等のアジド基と置換される本発明の化合物をさらに合成して、アジド基の還元により、アミノ置換大員環を提供してもよい。スキーム8は、アミノ置換化合物の調製、およびあるアミド含有誘導体の合成のための化合物の使用を説明する。アミノ置換大員環の調製が、求核アミノ基との反応によって、多様な官能基を有する大員環の置換のための手段を提供することは、当業者には明らかとなるであろう。
HCC1954およびSK−BR−3腫瘍細胞における細胞毒性について、大員環のライブラリを試験した。SK−BR3におけるErbB2等の周知のHSP90クライアントタンパク質の分解を誘導する能力について、有意な細胞毒性を示す化合物をさらに試験した。したがって、化合物での処理から18時間後に、全体細胞タンパク質溶解物を得て、タンパク質濃度を標準化し、ErbB2の濃度をウェスタンブロットによって定量化した(C.Chavany et al J.Biol.Chem.271:4974−4977(1996))。ライブラリからのいくつかの化合物は、ErbB2濃度を低減する際に、ラジシコールおよび17−AAGよりも有効であった。例えば、化合物13a、13bおよび13cは、E−オキシム異性体の形態で、ラジシコールおよび17−AAGの双方よりも有意に有効であった。
上述されるとおり、本発明の化合物を調製するために使用される多くのワインレブアミドは、当該技術分野で既知の方法によって調製される。特性化データは、本発明の化合物を調製するために使用される、選択したワインレブアミドに対して、以下に示される。
保護されたヒドロキシ基を含有するワインレブアミドは、スキーム6に描写され、以下で説明される手順に従って調製され、ラセミアルコール6−2の調製から開始する。
本発明において、適切に保護された様々な芳香族基が使用される。大員環の調製のための適切なレゾルシン酸ラクトンを調製するための方法は、当該技術分野において既知である。例えば、その全体を参照することにより本明細書に組み込まれる、国際公開第WO2008/021213号は、本発明の化合物を調製するために使用することができる、多様なレゾルシン酸の誘導体の合成方法を説明する。本発明において使用される芳香族化合物に対して選択した特性化データを以下に提供する。
レゾルシン酸芳香酸誘導体およびワインレブアミドに由来するアルキル化中間体の調製をスキーム2で説明する。様々な異なるアルキル化中間体を、芳香環および大員環上の様々な置換とともに使用して、本発明の化合物を調製してもよい。これらの化合物は、該スキームにおいて描写されるプロセスに従って、所望の芳香族成分およびワインレブアミドから調製されてもよい。本発明の化合物の調製において使用される、選択したアルキル化中間体の特性化データを以下に提供する。
本発明の化合物の合成のための一般的な手順
カルボン酸1−1から開始する、以下に説明される大員環の一般的な合成をスキーム1で説明する。CH2Cl2中の3.0当量のポリスチレンベースのクロロトリチル樹脂(1.1mmol/g)の懸濁液に、室温で、6.0当量のヒューニッヒ基および1.0当量の対応する酸1−1を添加した(スキーム1)。混合液を24時間攪拌した後、異なる樹脂を酢酸でさらに24時間被覆した。この後、樹脂をCH2Cl2、DMF、CH2Cl2およびEt2Oで洗浄し、次いで、乾燥してTHF中で再懸濁した。これらの懸濁液に、4.0当量のTBAF(1M)を添加し、混合液を4時間攪拌した。次いで、樹脂を濾過し、THF、CH2Cl2、CH2Cl2中の1%AcOH、CH2Cl2、Et2Oを数回使用して、完全に洗浄した。脱保護の完了およびテトラブチルアンモニウム塩の完全除去は、CH2Cl21/4中のHFIPの溶液を使用して、各樹脂のごくわずかな部分を30分間開裂した後、LC−MSによって評価した(LC−MSは、Supelco C8(5cmx4.6mm、5μm粒子)カラムを有するAgilent1100HPLCを使用し、95%H2O(0.5% HCO2H)〜100%MeCNの線形溶出勾配を使用して、0.5mL/分の流量で8分間記録した)。異なるアルコールを用いるさらなる多様化のために、樹脂を分割した。ミツノブ反応は、5.0当量の対応するアルコールR2OH、2.0当量のPh3P、および2.0当量のDIADを使用して、乾燥トルエン中で実行し、懸濁液を一晩攪拌した。エステル化反応の生産性は、前述されるとおり、小部分の開裂後、LC−MSによって評価し、完了まで進行しなかったプールは、同一条件に再び供した。樹脂を洗浄および乾燥した後、それらをトルエン中で懸濁し、メタセシス反応に提供した。Grubbの第2代触媒を各懸濁液(3x0.06当量)に添加し、反応液をCEMマイクロ波反応器中で、3x45分間120℃で加熱した(各サイクルにおいて、新たな触媒を添加した)。次いで、樹脂をCH2Cl2、DMF、CH2Cl2、およびEt2Oで数回洗浄した。次いで、CH2Cl21/4中のHFIP溶液を使用して、化合物を樹脂から3時間開裂し(樹脂を開裂条件に再び供することによって、最小量の化合物を生じ、元の開裂が完了まで進行したことを示唆する)、対応する生成物をPTLCにより精製し、5ステップ後、20〜30%の収率で単離した。
オキシムの形状は、x線回折によって判定した。図3は、13aの結晶構造のワイヤフレーム表示を示す。
オキシムの形状は、x線回折によって判定した。図4は、13bの結晶構造のワイヤフレーム表示を示す。
オキシムの形状は、13cのZ異性体のx線回折に基づいて推定した。図5は、13cのZ異性体のワイヤフレーム表示を示す。
6.4Hz,1H),5.31−5.29(m,2H),4.57(s,2H),4.16(t,J=4.8Hz,2H),3.70(s,2H),3.35−3.30(m,4H),2.31(m,2H),2.08−2.05(m,4H),1.56−1.51(m,2H),1.45−1.35(m,4H),1OHは目に見えない。13C NMR(DMSO−d6,100MHz,25℃)δ167.9,166.3,155.4,155.2,153.4,140.6,134.3,131.4,119.4,113.9,112.4,102.1,71.9,65.2,45.4,42.1,34.7,31.8,31.7,30.9,26.0,25.9,25.2,24.0;C24H29ClN2O6HのHRMS(MALDI−TOF)m/z[M+Na]+算出値:499.1612;実測値:499.1624.
オキシムの形状は、構造13aから推定した。
オキシムの形状は、構造13bから推定した。
オキシムの形状は、14aとの比較により割り当てた。
5.88(m,3H),5.58−5.67(m,1H),5.50(d,J=15.6Hz,1H),4.99−5.15(m,6H),4.84−4.91(m,2H),4.80(s,2H),4.50(s,2H),4.30−4.36(dtx2,J=12.3,6.48Hz,4H),4.23(s,2H),4.19(s,2H),3.23−3.58(m,8H),2.38−2.48(m,4H),2.31−2.37(m,2H),2.21−2.26(m,2H),2.00−2.04(m,4H),1.44−1.66(m,12H);C26H33ClN2O6Naに対するHRMS(MALDI−TOF)m/z[M+Na]+のHRMS(MALDI−TOF)m/z[M+Na]+算出値:527.1925;実測値:527.1906.
0.94(d,J=5.6Hz,3H).C25H32NaN2O6のHRMS(MALDI−TOF)m/z[M+Na]+算出値:479.2158;実測値:479.2182
大員環上にヒドロキシ置換基を含有する、本発明の化合物の調製は、保護されたヒドロキシ基で置換したワインレブアミドから調製するか、または上記スキームに9おいて描写されるように、最終大員環の酸化によって調製してもよい。ヒドロキシ置換基を含有する大員環は、ヒドロキシ基に反応性のある試薬によって誘導体化され、大員環状環上の様々な基で置換された大員環を産生し得る。ワインレブアミド前駆体上の直交保護基の使用は、大員環ヒドロキシ基の選択的単体分離および反応を可能にする。
THF(0.6mL)中の遊離アルコール(50mg、0.085mmol)の溶液に、0℃の窒素雰囲気下、NaH(20mg、0.5mmol、5.8当量)を添加し、反応液をさらに30分間攪拌し続けた。次に、Bu4NI(10mg、0.027mmol,0.3当量)および塩化物(79mg、0.51mmol、6.0当量)を同一温度で連続的に添加した。反応液を徐々に加温し、60℃まで一晩加熱した。混合液を飽和NH4Clおよび酢酸エチルから抽出し、有機相を合わせて、塩水で洗浄し、無水Na2SO4上で乾燥して濃縮した。フラッシュクロマトグラフィ(PE/EA、1/2、EA、次いでEA/MeOH,20:1)により、所望の化合物(36mg)を得た。MeOH(5mL)中の以前に得られた化合物(36mg、0.05mmol)の溶液を、スルホン酸樹脂(83mg、3mmol/g、5.0当量)で、40℃で処理した。2時間攪拌した後、反応液をCH2Cl2(5mL)で希釈し、濾過して、MeOHおよびCH2Cl2で洗い流した。濾液を濃縮し、逆相カラムにかけ(CH3CN/H2O、10%、20%、30%)、所望の化合物(19mg)を得た。C31H41N3O9のHRMS(MALDI−TOF)m/z[M+H]+算出値:600.2921;実測値:600.2919。
ヒドロキシ置換大員環の調製のためのヒドロキシ置換ワインレブアミドの使用に加えて、スキーム9に描写され、以下に説明されるように、化合物の軽度のアリル酸化によって、大員環にヒドロキシ基を導入してもよい。
大員環を含有するアジドを修正して、上記の実施例6に類似する、アミノ−置換化合物およびその誘導体を産生してもよい。
本発明の化合物を、HCC1954およびSK−BR−3腫瘍細胞中の細胞毒性について試験した。有意な細胞毒性を示した化合物は、SK−BR3中のErbB2等の、周知のHSP90クライアントタンパク質の分解を誘導する能力についてさらに試験した。そのようにして、該化合物での処理から18時間後、全体細胞タンパク質の溶解物を得て、タンパク質濃度を標準化し、ErbB2の濃度をウェスタンブロットによって定量化した(C.Chavany et al J.Biol.Chem.271:4974−4977(1996))。ライブラリからのいくつかの化合物は、ErbB2の濃度を低減する際に、ラジシコールおよび17−AAGよりも有効であった。例えば、化合物13a、13bおよび13cは、E−オキシム異性体の形態で、ラジシコールおよび17−AAGの双方よりも有意に有効であった。
Claims (36)
- 式IもしくはI’の化合物、またはその互変異性体、その医薬的に許容される塩、溶媒和物、エステル、もしくはプロドラッグ
XはO、SまたはNRであり、
Yは−OR、−O−(CH2)mCOOR、−O−(CH2)mCON(R)2、−N(R)2、−N(R)SORまたは−N(R)SO2Rであって、窒素原子に結合する基はZまたはE配置であり得、
R1およびR2は独立して、水素、ハロゲン、OR、N(R)2、SR、アジド、ニトロ、シアノ、脂肪族、アリール、アルキルアリール、アリールアルキル、ヘテロシクリル、ヘテロアリール、−S(O)R、−S(O)2R、−SO2N(R)2、−N(R)SO2R、−N(CO)R、−N(CO)N(R)2、−N(CO)OR、−O(CO)R、−(CO)R、−(CO)OR、−(CO)N(R)2、−O(CO)OR、または−O(CO)N(R)2であり、
R3、R4、R5、R6、R7、R8、R9およびR10は独立して、水素、ハロゲン、アジド、ニトロ、シアノ、脂肪族、アルキルアリール、アラルキル、アリール、ヘテロアルキル、アルキルヘテロアリール、ヘテロシクリル、ヘテロアリール、OR、N(R)2、SR、−O(CH2)mN(R)C(O)(CH2)pR、−O(CH2)mOC(O)(CH2)pR、−O(CH2)mC(O)(CH2)pN(R)2、−O(CH2)mC(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pOR、−O(CH2)mN(R)C(O)(CH2)pN(R)2、−O(CH2)mOC(O)(CH2)pOR、−O(CH2)mOC(O)(CH2)pN(R)2、−NR(CH2)mN(R)C(O)(CH)pR、−NR(CH2)mOC(O)(CH2)pR、−NR(CH2)mC(O)(CH2)pN(R)2、−NR(CH2)mC(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pOR、−NR(CH2)mN(R)C(O)(CH2)pN(R)2、−NR(CH2)mOC(O)(CH2)pOR、−NR(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN(R)C(O)(CH2)pR、−(CH2)mOC(O)(CH2)pR、−(CH2)mC(O)(CH2)pN(R)2、−(CH2)mC(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pOR、−(CH2)mN(R)C(O)(CH2)pN(R)2、−(CH2)mOC(O)(CH2)pOR、−(CH2)mOC(O)(CH2)pN(R)2、−(CH2)mN3、−O(CH2)mN3 −(CH2)mN(R)2、−(CH2)mOR、−(CH2)mS(O)(CH2)pR、−(CH2)mS(O)2(CH2)pR、−(CH2)mSO2(CH2)pN(R)2、または−(CH2)mN(R)SO2(CH2)pRであり、および
各Rは独立して、R11、水素、脂肪族、アミノ、アジド、シアノ、ニトロ、アルキルアミノ、ジアルキルアミノ、OH、アルコキシ、カルボニルアミノ、アミノカルボニル、アルコキシカルボニル、カルボニルオキシ、カルボキシ、アシル、アリール、カルカリール、ベンジルを含むアリールアルキル、ヘテロアルキル、ヘテロアリール、ヘテロシクリル、もしくは保護基であるか、または同一窒素上の2つのRは、前記窒素と一緒になって、5〜8員の複素環式またはヘテロアリール環を形成し、基は2つ以上のR置換基を含む場合、Rは任意に置換され、各Rは同一であるか、または異なってもよく、
R11は以下の基であり、
nは0、1または2であり、
mおよびpは独立して、0、1、2、3、4または5であり、ならびに点線は単結合または二重結合のいずれかであることを示し、原子価要件は、追加の水素原子によって満たされ、
式I’において、nが1であり、およびXがOであり、および炭素原子を担持するR9とR10との間に二重結合が存在する場合、R5、R6、R7、R8、R9またはR10のうちの少なくとも1つは水素でなく、ならびに
式I’において、nが1であり、およびXがOであり、および炭素原子を担持するR9とR10との間の結合が単結合である場合、R5、R6、R7、またはR8のうちの少なくとも1つは水素ではない。)。 - XはOまたはNRである、請求項1の化合物。
- XはOまたはNRであり、Yは−OR、−O−(CH2)mCOOR、または−O−(CH2)mCON(R)2である、請求項1の化合物。
- R1およびR2は独立して、水素またはハロゲンである、請求項1の化合物。
- R1およびR2は、水素またはハロゲンである、請求項5の化合物。
- R3およびR4は、アルキルまたは水素である、請求項5の化合物。
- R9およびR10は独立して、水素または脂肪族である、請求項5の化合物。
- XはOであり、Yは−O−(CH2)mCOORまたは−O−(CH2)mCON(R)2であり、窒素原子に結合する基はZまたはE配置であり得、R1、R2は独立して、水素またはハロゲンであり、ならびにR9およびR10は独立して、水素または脂肪族である、請求項5の化合物。
- XはOまたはNRである、請求項10の化合物。
- Yは−O−(CH2)mCOORまたは−O−(CH2)mCON(R)2であり、窒素原子に結合する基はZまたはE配置であり得る、請求項10の化合物。
- XはOであり、Yは−O−(CH2)mCOORまたは−O−(CH2)mCON(R)2であり、窒素原子に結合する基はZまたはE配置であり得、R1およびR2は独立して、水素またはハロゲンであり、ならびにR9およびR10は水素である、請求項10の化合物。
- 化合物が、式Vを有し、
- 医薬的に許容される担体と組み合わせて、HSP90阻害有効量の請求項1の化合物を含む、医薬組成物。
- 医薬的に許容される担体と組み合わせて、キナーゼ阻害有効量の請求項1の化合物を含む、医薬組成物。
- 組成物は、平均粒径が約2ミクロン未満である粒子を含む、請求項17の組成物。
- 組成物は、平均粒径が約2ミクロン未満である粒子を含む、請求項18の組成物。
- 担体は、経口、非経口、吸入、局所、または皮内投与に適切である、請求項17の組成物。
- 担体は、経口、非経口、吸入、局所、または皮内投与に適切である、請求項18の組成物。
- 別の活性薬剤および医薬的に許容される担体と組み合わせて、または交互に、HSP90阻害有効量の請求項1の化合物を含む、医薬組成物。
- 別の活性薬剤および医薬的に許容される担体と組み合わせて、または交互に、キナーゼ阻害有効量の請求項1の化合物を含む、医薬組成物。
- 疾患を有する患者を治療する方法であって、前記疾患を有する前記患者に、有効量の請求項1の化合物を投与するステップを含み、前記疾患は、自己免疫疾患、炎症性疾患、神経疾患または神経変性疾患、癌、心血管疾患、アレルギー、喘息、もしくはホルモン関連疾患である、方法。
- 患者はヒトである、請求項25の方法。
- 疾患は癌である、請求項25の方法。
- 癌は、固形腫瘍、血液感染性腫瘍、乳癌、卵巣癌、頸癌、前立腺癌、精巣癌、尿生殖器癌、食道癌、喉頭癌、膠芽細胞腫、胃癌、皮膚癌、角化棘細胞腫、肺癌、扁平上皮癌、大細胞癌、小細胞癌、肺腺癌、骨肉腫、結腸癌、腺腫、膵臓癌、腺癌、甲状腺癌、濾胞腺癌、未分化癌、乳頭癌、精上皮腫、黒色腫、肉腫、膀胱癌、肝臓癌および胆道癌、腎臓癌、骨髄疾患、リンパ疾患、ホジキン病、ヘアリー細胞白血病、頬側口腔(buccal cavity)癌、咽頭癌、口唇癌、舌癌、口腔(mouth)癌、咽頭癌、小腸癌、結腸直腸癌、大腸癌、直腸癌、脳および中枢神経系の癌または白血病である、請求項27の方法。
- 疾患は炎症性疾患である、請求項25の方法。
- 炎症性疾患は、内皮細胞の過剰もしくは異常刺激、アテローム性動脈硬化、血管機能不全、異常な創傷治癒、炎症性および免疫性疾患、ベチェット病、痛風もしくは痛風性関節炎、関節リウマチを伴う異常な血管形成、皮膚病、乾癬、糖尿病性網膜症、未熟児網膜症、水晶体後部線維増殖症、黄斑変性、角膜移植拒絶反応、血管新生緑内障、またはオスラーウェーバー症候群である、請求項29の方法。
- 自己免疫性疾患、炎症性疾患、神経性または神経変性疾患、癌、心血管疾患、アレルギー、喘息、またはホルモン関連疾患の治療のための薬剤の製造における、請求項1の化合物の使用。
- 患者はヒトである、請求項31の使用。
- 疾患は癌である、請求項31の使用。
- 癌は、固形腫瘍、血液感染性腫瘍、乳癌、卵巣癌、子宮癌、前立腺癌、精巣癌、尿生殖路癌、食道癌、咽頭癌、膠芽細胞腫、胃癌、皮膚癌、角化棘細胞腫、肺癌、扁平上皮癌、大細胞癌、小細胞癌、肺腺癌、骨肉腫、結腸癌、腺腫、膵臓癌、腺癌、甲状腺癌、濾胞癌、未分化癌、乳頭癌、精上皮腫、黒色腫、肉腫、膀胱癌、肝臓癌および胆道癌、腎臓癌、骨髄疾患、リンパ疾患、ホジキン病、ヘアリー細胞白血病、頬側口腔癌、咽頭癌、口唇癌、舌癌、口腔癌、咽頭癌、小腸癌、結腸直腸癌、大腸癌、直腸癌、脳および中枢神経系の癌、または白血病である、請求項33の使用。
- 疾患は炎症性疾患である、請求項31の使用。
- 炎症性疾患は、内皮細胞の過剰または異常刺激、アテローム性動脈硬化症、血管機能不全、異常な創傷治癒、炎症性および免疫性疾患、ベーチェット病、通風または痛風性関節炎、関節リウマチを併う異常な血管形成、皮膚病、乾癬、糖尿病性網膜症、未熟児網膜症、後水晶体繊維増殖症、黄斑変性、角膜移植拒絶反応、血管新生緑内障またはオスラーウェーバー症候群である、請求項35の使用。
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KR20140021520A (ko) * | 2010-10-22 | 2014-02-20 | 위니베르시떼 드 스트라스부르 | Hsp90 관련 질환의 치료에 유용한 포코옥심 컨쥬게이트 |
US9757529B2 (en) | 2012-12-20 | 2017-09-12 | Otitopic Inc. | Dry powder inhaler and methods of use |
US9757395B2 (en) | 2012-12-20 | 2017-09-12 | Otitopic Inc. | Dry powder inhaler and methods of use |
WO2014178891A1 (en) | 2013-04-30 | 2014-11-06 | Otitopic Inc. | Dry powder formulations and methods of use |
KR20230040375A (ko) | 2017-09-22 | 2023-03-22 | 오티토픽 인코퍼레이티드 | 스테아르산마그네슘을 갖는 건조 분말 조성물 |
US10786456B2 (en) | 2017-09-22 | 2020-09-29 | Otitopic Inc. | Inhaled aspirin and magnesium to treat inflammation |
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US20110217335A1 (en) | 2011-09-08 |
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CN101990399B (zh) | 2016-05-04 |
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US20190359585A1 (en) | 2019-11-28 |
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