JP2020527175A - Acc阻害剤としての新規な化合物およびそれらの使用 - Google Patents
Acc阻害剤としての新規な化合物およびそれらの使用 Download PDFInfo
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- JP2020527175A JP2020527175A JP2020524667A JP2020524667A JP2020527175A JP 2020527175 A JP2020527175 A JP 2020527175A JP 2020524667 A JP2020524667 A JP 2020524667A JP 2020524667 A JP2020524667 A JP 2020524667A JP 2020527175 A JP2020527175 A JP 2020527175A
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- compound according
- alkyl
- haloalkyl
- independently
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
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Abstract
Description
本願は、2017年7月17日出願の特許文献1に対する優先権を主張するものであり、その内容は全て本明細書の一部として援用される。
一態様において、本発明は、式(I)の化合物またはその鏡像異性体の薬学上許容される塩を提供し、
m、n、およびkのそれぞれは独立に、0、1、または2であり;
R1は、H、ハロ、アルキル、ハロアルキル、CN、アミド、アリール、またはヘテロアリールであり、
R2は、H、アルキル、ハロアルキル、CN、ヒドロキシル、またはアルコキシであり;
R3は、H、アルキル、アリール、ヘテロアリール、シクロアルキル、またはヘテロシクロアルキルであり、かつ、ハロ、アルキル、またはハロアルキルで場合により置換されていてもよく;
R4は、H、アルキル、ハロアルキル、CN、ヒドロキシル、またはアルコキシであり;
R5は、ORまたはN(R)2であり;
R6は、アリールまたはヘテロアリールであり、かつ、ハロ、アルキル、ハロアルキル、CN、ヒドロキシル、またはアルコキシで場合により置換されていてもよく;
R7およびR8のそれぞれは独立に、H、アルキル、ハロアルキル、アルコキシ、またはハロアルコキシであり;または代わりに、R7およびR8は、それらが結合している炭素原子と一緒になって、それぞれ独立にOまたはNR’である1もしくは2個の環ヘテロ基を場合により含有してよい3〜6員のシクロアルキルを形成し;
R9、R10、R11、およびR12のそれぞれは独立に、H、アルキル、ハロアルキル、アルコキシ、またはハロアルコキシであり;または代わりに、R9およびR8は、それらが結合している炭素原子と一緒になって、それぞれ独立にOまたはNR’である1もしくは2個の環ヘテロ基を場合により含有してよい3〜7員のシクロアルキルを形成し;またはさらにその代わりに、R7およびR10は一緒になって(それらが結合している炭素原子を含まない)、C1-3アルキレン基を形成し、かつ、R8およびR9は一緒になって(それらが結合している炭素原子を含まない)、別のC1-3アルキレン基を形成し;
Xは、C(R)2、S、O、またはNR’であり;
Yは、S、O、またはNR’であり;
各Rは独立に、H、アルキル、ハロ、またはハロアルキルであり;かつ
R’のそれぞれは独立に、H、ハロ、アルキル、ハロアルキル、CN、またはヒドロキシルである。
定義
本発明の化合物は、上記で一般に記載される化合物を含み、また本明細書に開示されるクラス、サブクラス、および種により、さらに例示される。本明細書で使用される場合、特に断りのない限り下記定義が適用されるものとする。本発明の目的上、化学元素は非特許文献2に従って特定される。加えて、有機化学の一般原理は非特許文献3および非特許文献4に記載されており、これらの全内容は本明細書の一部として援用される。
は;複素環式環の置換可能な窒素、例えばN(3,4−ジヒドロ−2H−ピロリルの場合)、NH(ピロリジニルの場合)またはNR+(N−置換ピロリジニルの場合)を含む)のうち1以上を意味する。
実施例1. シクロプロパンカルボン酸メチル−1−(6−ブロモ−5−メチル−2,4−ジオキソ−1H−チエノ[2,3−d]ピリミジン−3−イル)
この標題化合物は、下記の反応スキームに従って製造した。
N2下、0℃で、トリホスゲン(390.46mg、1.32mmol)に、DCM(6.00mL)中、化合物3(996.09mg、3.87mmol)の溶液を加えた。この混合物をTEA(1.57g、15.48mmol)に滴下し、0℃で2時間撹拌し、1−アミノシクロプロパンカルボン酸エチル(500.00mg、3.87mmol)を加えた。この混合物を0℃で一晩撹拌した。この混合反応物に水を加え、DCMで抽出し、有機層をブラインで洗浄し、Na2SO4で乾燥させ、濃縮した。粗物質をカラムクロマトグラフィー(P/E=8/1)により精製し、14(540.00mg、1.31mmol、収率33.83%)を得た。1H NMR(400MHz,CDCl3):δ4.34−4.26(m,4H),4.18−4.16(m,2H),2.74(s,3H),1.40−1.30(m,9H),1.23−1.21(m,4H)。
1,4−ジオキサン(8.00mL)中、化合物4(520.00mg、1.26mmol)の溶液に、NaH(45.36mg、1.89mmol)を加えた。この混合物を1時間加熱還流した。この混合反応物を飽和NH4Cl水溶液により急冷し、EAで抽出し、有機層を濃縮した。粗物質をカラムクロマトグラフィー(P/E=3/1)により精製し、15(210.00mg、573.16μmol、収率45.49%)を白色固体として得た。1H NMR(400MHz,CDCl3):δ4.37−4.31(m,2H),4.22−4.16(t,2H),2.81(s,3H),1.41−1.34(m,6H),1.25−1.16(m,4H)。
H2O/THF(200.00mL)中、化合物5(8.30g、22.65mmol)の溶液に、LiOH(3.80g、158.55mmol)を加えた。この混合反応物を一晩80℃に加熱した。この混合反応物を1M HClでPH2に酸性化し、EAで抽出し、有機層を乾燥させ、濃縮し、化合物16(6.70g、21.59mmol、収率95.34%)を白色固体として得た。1H NMR(400MHz,DMSO):δ13.00(s,2H),12.38(s,1H),2.70(s,3H),1.72−1.61(m,2H),1.35−1.26(m,2H)。
化合物6(200.00mg、644.58μmol)、K2CO3(1.61mmol)およびAgOAc(402.89mg、2.90mmol)の混合物をNMP(5.00mL)に溶解させた。この混合反応物を一晩110℃に加熱した。この反応物に水を加え、1.0M HClでpH2に酸性化した。この混合物(miture)をEAで抽出し、有機相を乾燥させ、濃縮した。残渣をカラムクロマトグラフィー(DCM/MeOH=10/1)により精製し、化合物17(100.00mg、375.56μmol、収率58.26%)を黄色固体として得た。1H NMR(400MHz,DMSO):δ12.70(s,1H),12.09(s,1H),6.69(s,1H),2.33(s,3H),1.69−1.61(m,2H),1.33−1.27(m,2H)。
化合物7(100.00mg、375.56μmol)とMeOH(19.16mg、1.13mmol)の混合物をDCM(3.00mL)に溶解させ、DMAP(4.59mg、37.56μmol)およびEDCI(143.84mg、751.12μmol)を加えた。この混合物を室温で3時間撹拌した。この混合反応物に水を加え、DCMで抽出し、有機層を乾燥させ、濃縮した。残渣をカラムクロマトグラフィー(P/E=2/1)により精製し、化合物18(70.00mg、249.73μmol、収率66.50%)を白色固体として得た。1H NMR(400MHz,CDCl3):δ10.62(s,1H),6.40(s,1H),3.71(s,3H),2.45(s,3H),2.05−1.94(m,2H),1.42(m,2H)。
−10℃で、DMF(10.00mL)中、化合物8(500.00mg、1.78mmol)の溶液に、NBS(316.80mg、1.78mmol)を加えた。この反応混合物を−10℃で2時間撹拌した。この反応混合物に飽和NH4Cl水溶液を加え、EAで抽出し、有機層をブラインで洗浄し、乾燥させ、濃縮し、粗物質をカラムクロマトグラフィー(P/E=2/1)により精製し、化合物19(500.00mg、1.39mmol、収率78.09%)を白色固体として得た。1H NMR(400MHz,DMSO):δ12.20(s,1H),3.59(s,3H),2.30(s,3H),1.74−1.68(m,2H),1.39−1.36(m,2H)。
標題化合物の混合物は、下記の反応スキームに従って製造した。
この標題化合物は、下記の反応スキームに従って製造した。
窒素雰囲気下、トルエン(10.00mL)中、化合物20(160.00mg、250.95μmol)の混合物に、Pd(PPh3)4(86.88mg、75.29μmol)を加えた。この混合物を一晩加熱還流した後、濃縮した。残渣を分取HPLCにより精製し、化合物22(36.00mg、94.11μmol、収率37.50%)を黄色固体として得た。1H NMR(400MHz,CDCl3):δ7.73(s,1H),7.60−7.50(m,1H),7.33−7.29(m,1H),7.26(s,1H),7.04−7.00(m,1H),6.90−6.88(m,1H),5.43−5.42(m,1H),3.90−3.86(m,3H),3.71−3.68(m,2H),3.43−3.41(m,1H),3.34−3.32(m,2H),2.90(s,3H),2.17(m,1H),2.13−1.94(m,2H),1.73−1.71(m,2H),1.52(m,1H),1.39−1.33(m,3H)。
H2O(2.00mL)、THF(2.00mL)およびMeOH(2.00mL)中、化合物22(200.00mg、343.86μmol)の溶液に、LiOH(41.18mg、1.72mmol)を加えた。この混合物を3時間70℃に加熱した。この混合反応物を1M HClでPH2に酸性化し、EAで抽出し、有機相を乾燥させ、濃縮した。残渣をカラムクロマトグラフィー(DCM/MeOH=20/1)により精製し、化合物16331−02(120.00mg、211.41μmol、収率61.48%)を黄色固体として得た。1H NMR(400MHz,CDCl3):δ7.71(s,1H),7.56−7.54(m,1H),7.32−7.26(m,1H),7.22(s,1H),7.03−7.01(m,1H),6.89−6.84(m,1H),5.43−5.42(m,1H),4.20(s,1H),3.90−3.86(m,3H),3.68−3.65(m,2H),3.40−3.38(m,1H),3.31−3.27(m,2H),2.88(s,3H),2.05−1.96(m,2H),1.69−1.65(m,2H),1.45−1.31(m,5H)。
H2O(1.00mL)、THF(1.00mL)およびMeOH(1.00mL)中、化合物20(40.00mg、67μmol)の溶液に、LiOH(11mg、0.27mmol)を加えた。この混合物を3時間70℃に加熱した。この混合反応物を1M HClでpH2に酸性化し、EAで抽出し、有機相を乾燥させ、濃縮した。残渣をカラムクロマトグラフィー(DCM/MeOH=20/1)により精製し、化合物16331−02(15.00mg)を黄色固体として得た。1H NMR(400MHz,DMSO):δ2.82(s,1H),7.45−7.43(m,1H),7.32−7.30(m,1H),7.03−6.98(m,2H),5.26−5.24(m,1H),3.81(s,2H),3.73(s,1H),3.5(m,1H),3.34(m,1H),3.31−3.25(m,2H),2.35(s,3H),1.73−1.58(m,4H),1.28−1.14(m,4H)。
この標題化合物は、下記の反応スキームに従って製造した。
N2下、0℃で、DCM(50mL)中、化合物3(8g、31.1mmol)の溶液に、トリホスゲン(5.5g、18.66mmol)を加えた。この混合物にTEA(12.5g、124.4mmol)を滴下し、0℃で2時間撹拌し、1−アミノシクロプロパンカルボン酸エチル(4g、31.1mmol)を加えた。この混合物を0℃で一晩撹拌した。この混合反応物に水を加え、DCMで抽出し、有機層をブラインで洗浄し、Na2SO4で乾燥させ、濃縮した。粗物質をカラムクロマトグラフィー(P/E=8/1)により精製し、24(8g、収率62%)を得た。
1,4−ジオキサン(24.00mL)中、化合物24(2.4g、5.6mmol)の溶液に、NaH(440mg、11.2mmol)を加えた。この混合物を1時間加熱還流した。この混合反応物を飽和NH4Cl水溶液により急冷し、EAで抽出し、有機層を濃縮した。粗物質をカラムクロマトグラフィー(P/E=3/1)により精製し、25(1.5g、収率68%)を白色固体として得た。
H2O/THF(100.00mL)中、化合物25(4.4g、11.58mmol)の溶液に、LiOH(2.9g、69.5mmol)を加えた。この混合反応物を一晩80℃に加熱した。この混合反応物を1M HClでPH2に酸性化し、EAで抽出し、有機層を乾燥させ、濃縮し、化合物26(2.5g、収率67%)を白色固体として得た。1H NMR(400MHz,DMSO):δ2.70(s,3H),2.51−2.43(m,2H),1.13−0.94(m,4H)。
NMP(20mL)中、化合物26(2.5g、7.71mmol)、K2CO3(2.4g、19.3mmol)およびAgOAc(3.8g、23.13mmol)の混合物。この混合反応物を一晩110℃に加熱した。この反応物に水を加え、1M HClでPH2に酸性化した。この混合物をEAで抽出し、有機相を乾燥させ、濃縮した。残渣をカラムクロマトグラフィー(DCM/MeOH=10/1)により精製し、化合物27(1.5g、収率71%)を黄色固体として得た。1H NMR(400MHz,DMSO):δ6.65(s,1H),2.50−2.43(s,2H),2.32(s,3H),1.12−1.08(m,2H),0.92(s,2H)。
DCM(3.00mL)中、化合物27(100.00mg、375.56μmol)およびMeOH(19.16mg、1.13mmol)の混合物に、DMAP(4.59mg、37.56μmol)およびEDCI(143.84mg、751.12μmol)を加えた。この混合物を室温で3時間撹拌した。この混合反応物に水を加え、DCMで抽出し、有機層を乾燥させ、濃縮した。残渣をカラムクロマトグラフィー(P/E=2/1)により精製し、化合物28(70.00mg、249.73μmol、収率66.50%)を白色固体として得た。1H NMR(400MHz,DMSO):δ6.66(s,1H),3.49(s,3H),2.54−2.41(s,2H),2.33(s,3H),1.11−1.08(m,2H),0.93−0.92(m,2H)。
−10℃で、DMF(10.00mL)中、化合物28(144mg、0.49mmol)の溶液に、NBS(87mg、0.49mmol)を加えた。この反応混合物を−10℃で2時間撹拌した。この反応混合物に飽和NH4Cl水溶液を加え、EAで抽出し、有機層をブラインで洗浄し、乾燥させ、濃縮し、粗物質をカラムクロマトグラフィー(P/E=2/1)により精製し、化合物29(0.11mg、収率61%)を白色固体として得た。1H NMR(400MHz,DMSO):δ3.49(s,3H),2.50(s,2H),2.30(s,3H),1.11−1.08(m,2H),0.93−0.92(m,2H)。
標題異性体化合物の混合物は、下記の反応スキームに従って製造した。
100mLの三頚丸底フラスコにN2下でTHF(8.00mL)、化合物9(330.00mg、818.27μmol)、化合物10(309.69mg、1.23mmol)およびPPh3(643.87mg、2.45mmol)を装填し、DIAD(237.52mg、1.80mmol)を加えた。この反応物を室温で一晩撹拌した。この反応混合物を濃縮し、残渣をカラムクロマトグラフィー(P/E=15/1)により精製し、化合物31(240.00mg、376.42μmol、収率46.0%)および30(120.00mg、188.21μmol、収率23.00%)を白色固体として得た。
窒素雰囲気下、トルエン(25.00mL)中、化合物30と31の混合物(500mg、825μmol)に、Pd(PPh3)4(275mg、250μmol)を加えた。この混合物を一晩加熱還流した後、濃縮した。残渣を分取HPLCにより精製し、化合物32および33(合わせて275mg、総収率56%)を黄色固体として得た。
H2O(4.00mL)、THF(4.00mL)およびMeOH(4.00mL)中、化合物32および33(275mg、462μmol)の溶液に、LiOH(97mg、2.12mmol)を加えた。この混合物を3時間70℃に加熱した。この混合反応物を1M HClでPH2に酸性化し、EAで抽出し、有機相を乾燥させ、濃縮した。残渣を分取HPLCにより精製し、16331−03(23mg、収率9.2%)および16331−03−ISO(30mg、収率11.2%)を黄色固体として得た。
標題化合物は、下記のスキームに基づいて合成した。
6N KOH(100mL)中、化合物34(30g、176mmol)の溶液を還流 温度で14時間撹拌し、この時、LCMSは、反応が完了していたことを示した。この溶液を4.0N HClでpH9に調整した。真空下で溶媒を除去した後、化合物35を白色固体として得(40g、粗、多くの塩を含有)、それ以上精製せずにそのまま次の工程に使用した。
メタノール(400mL)中、化合物35(40g、粗、多くの塩を含有)の溶液に、濃H2SO4(20mL)を加えた。この混合物を12時間、還流温度で撹拌し、この時、LCMSは、反応が完了していたことを示した。真空下で溶媒を除去した後、化合物36を白色固体として得(47g、粗、純度:35%)、それ以上精製せずにそのまま次の工程に使用した。
窒素の不活性雰囲気下でパージおよび維持した100mLの三頚丸底フラスコに、化合物B(2.87g、18.3mmol)およびDCM(30mL)を入れた。この後に0℃でジトリクロロメチル(1.84g、7.32mmol)を加えた。この後に0℃で撹拌しながら15分かけてTEA(6.28g、73.2mmol)を加えた。得られた溶液を0℃で2時間撹拌した。この溶液に化合物36(8g、純度:35%)を加え、得られた溶液を一晩室温で撹拌した。次に、この反応を50mLの水を加えることにより急冷し、2×50mLのDCMで抽出した。有機層を真空濃縮した。粗生成物をシリカゲルクロマトグラフィー(溶出剤としてPE/EtOAc=3/1)により精製し、1.4g(25%)の化合物937を黄色固体として得た。
窒素の不活性雰囲気下でパージおよび維持した50mLの三頚丸底フラスコに、化合物37(1.4g、3.78mmol)およびジオキサン(15mL)を入れた。この後に10℃で水素化ナトリウム(378mg、9.45mmol、油中60%)を加えた。得られた溶液を110℃で2時間撹拌した。この反応溶液を室温に冷却し、次いで、100mLのNH4Cl(飽和水溶液)を加えることにより急冷した。得られた溶液を100mL×3の酢酸エチルで抽出し、有機層を合わせ、真空濃縮して16gの粗生成物を得た。この粗生成物をシリカゲルクロマトグラフィー(溶出剤としてPE/EtOAc=3/2)により精製し、820mg(67%)の化合物9−Bを黄色固体として得た。
250mLの三頚丸底フラスコに、化合物37−B(820mg、2.53mmol)、CH3COONa(456mg、5.06mmol)および酢酸(8mL)を入れた。この後に撹拌しながらBr2(364mg、2.23mmol)を滴下した。得られた溶液を室温で0.5時間撹拌し、真空濃縮した。この混合物をEA(50mL)で溶解させ、20mLのNa2CO3(飽和水溶液)で洗浄した。EA相をブラインで洗浄し、Na2SO4で乾燥させ、濃縮し、1.3gの粗生成物を得た。生成物をシリカゲルクロマトグラフィー(溶出剤としてPE/EtOAc=3/2)で精製し、810mg(79%)の化合物10を黄色固体として得た。
化合物38は、DIADおよびPPh3の存在下で化合物7と反応して化合物39を生じる。
化合物39は、メタノール、THFおよび水の混合溶媒中でLiOHと反応して標題化合物34155を生じる。
本発明の下記のさらなる化合物は、上記のものと同様の方法において、当技術分野で周知の方法での酸とアミド間の変換を用いて製造した。
実施例25:(MS:599.66;1H−NMR:2.862,3.876,7.298)
実施例26(MS:581.64;1H−NMR:2.877,3.909,7.301,7.741)
実施例27(MS:570.7;1H−NMR:2.329,3.390,3.729,4.527,7.278)
実施例28(MS:567.61;1H−NMR:1.428,2.868,3.330,3.853,3.919,4.867,7.303,8.005)
実施例29(MS:579.46;1H−NMR:2.434,3.330,3.823,3.892,4.869)
実施例30(MS:607.51;1H−NMR:2.211,2,417,3.850,7.270)
実施例31(MS:593.09;1H−NMR:2.242,3.203,3.733,4.764)
実施例32(MS:579.46;1H−NMR:2.302,3.197,3.693,3.757,4.757)
実施例33(MS:567.61;1H−NMR:2.865,3.321,3.852,3.917,4.883,7.301,8.004)
実施例34(MS:543.63;1H−NMR:1,533,2.593,3.329,3.880,4.329,4.882,7.015)
実施例35(MS:543.63)
実施例36(MS:595.66;1H−NMR:2.844,3.863,7.261,7.720)
実施例37(MS:581.18;1H−NMR:2.832,3.325,3.894,4.865,7.300,8.000)
実施例38(MS:569.63;1H−NMR:1.250,1.838,1.873,2.854,3.865,7.266)
実施例39(MS:547.56;1H−NMR:1.265,1.395,1.613,1,899,3.299,3.820,3.927,4.850,7.057,7.356,8.050,8.774)
実施例40(MS:535.01;1H−NMR:2.426,3.323,4.856)
実施例41(MS:644.16;1H−NMR:2.872,3.241,3.326,4.884)
実施例42(MS:568.64;1H−NMR:1.899,1.912,2.861,3.876,7.272,7.740)
実施例43(MS:594.68;1H−NMR:1.827,2.874,3.833,7.305,7.760)
実施例44(MS:608.23;1H−NMR:1.773,2.122,2.867,3.884,7.319,7.745)
実施例45(MS:566.63;1H−NMR:2.391,3.323,3.810,3.883,4.884,7.791)
実施例46(MS:566.63;1H−NMR:1.665,2.741,3.210,3.701,3.790,4.750,7.183)
実施例47(MS:580.65;1H−NMR:1.771,2.580,2.731,3.209,3.694,3.789,4.762,7.192)
実施例48(MS:606.52;1H−NMR:1.195,1.679,2.335,3.765,7.193)
実施例49(MS:567.61;1H−NMR:2.633,3.323,4.971,7.973)
実施例50(MS:620.56;1H−NMR:1.701,2.319,2.736,2.816,7.184)
実施例51(MS:592.5;1H−NMR:2.394,3.322,3.960,5.010)
実施例52(MS:606.53;1H−NMR:2.391,2.715,3.322,3.850,4.980)
実施例53(MS:594.68;1H−NMR:2.731,2.834,3.398,4.802)
実施例54(MS:580.65;1H−NMR:2.830,3.323,3.871,4.953,7.297,8.003)
実施例55(MS:595.67;1H−NMR:2.586,3.787,7.166,7.765)
実施例56(MS:567.61;1H−NMR:2.283,3.720,4.850,6.861,8.122,8.753)
実施例57(MS:592.5;1H−NMR:1.215,2,440,2.674,3.391,4.900)
実施例58(MS:578.48;1H−NMR:2.413,3.324,3.855,4.900)
実施例59(MS:593.49;1H−NMR:1.233,2.299,3.206,4.756)
実施例60(MS:592.5;1H−NMR:1.211,2.299,2.482,2.724,3.209,3.682,3.720,4.750)
実施例61(MS:581.64;1H−NMR:2.825,3.332,3.873,4.850,5.419,7.016,7.294,7.968)
実施例62(MS:606.53;1H−NMR:2.397,2,681,3.343,3.776,3.821,4.850)
実施例63(MS:594.68;1H−NMR:1.285,2.692,2.838,3.302,3,791,3.862,4.850,7.295,7.974)
実施例64(MS:580.65;1H−NMR:2.861,3.359,4.850)
実施例65(MS:638.73;1H−NMR:2.848,3.306,3.797,3.860,4.850,7.210,7.971)
実施例66(1H−NMR:0.977,1.484,1.752,1.772,2.829,3.321,3.874,4.850,7.294,7.994)
実施例67(MS:625.73;1H−NMR:2.272,3.201,3.674,3.746,4.752)
実施例68(MS:581.64;1H−NMR:1.439,1.752,2.392,3.329,3.840,4.853)
実施例69(MS:581.64;1H−NMR:2.882,3.360,3.844,4.850,7.286,7.989)
実施例70(MS:608.08)
実施例71(MS:622.1)
実施例72(MS:597.64)
実施例73(MS:611.66)
実施例74(MS:611.66)
実施例75(MS:568.60)
実施例76(MS:567.61)
実施例77(MS:581.64)
実施例78(MS:594.21)
実施例79(MS:595.21)
実施例80(MS:567.12)
実施例81(MS:623.51)
ACC1またはACC2のいずれかに対する本発明の化合物の阻害作用を決定するために使用可能なin vitro ACC阻害アッセイのための例示的手順を以下に示す。Promega社からのADP−Glo(商標)キナーゼアッセイキットを使用した。ADP−Glo(商標)キナーゼアッセイは、酵素反応中に生産されるADPの量を定量することによって酵素活性を測定する、発光ADP検出アッセイである。アッセイは二工程で行われ、まず、酵素反応の後、等量のADP−Glo(商標)試薬を添加して反応を終了させ、残存するATPを枯渇させる。第二に、キナーゼ検出試薬を添加してADPをATPに同時に転換し、新たに合成されたATPを、ルシフェラーゼ/ルシフェリン反応を使用して測定可能にする。ATPからADPへの転換曲線を使用することにより、発光をADP濃度に相関させることができる。詳細な手順は以下の通りである。50μLの供試化合物(DMSO中の600μM)を、384ウェル希釈プレートに加える。11のウェルについて、各列毎にDMSOで化合物の1:3連続希釈を行う。0.5μLのACC2検量線用溶液を、384ウェル白色Optiplateアッセイプレートに加える。工程2からの各カラム中の0.5μLの希釈化合物溶液を、各列が2反復を含むようにアッセイプレートに加える。最後の2列については、0.5μLの陰性対照(DMSO)を1つの列に、0.5μLの陽性対照(化合物I−97)を他方の列に加える。これらのプレートを室温で15分間インキュベートする。5μLの基質検量線用溶液を各ウェルに加えて反応を開始させる。最終的なACC2反応濃縮物は下記からなる:5nM ACC2、20μM ATP、20μMアセチルCoA、12mM NaHCO3、0.01%Brij35、2 mM DTT、5%DMSO、試験化合物濃度:30μM、10μM、3.33μM、1.11μM、0.37μM、0.123μM、0.0411μM、0.0137μM、0.00457μM、0.00152μM、および0.00051μM。プレートを室温で60分間インキュベートした。10μLのADP glo試薬を加えた。プレートを室温で40分間インキュベートした。20μLのキナーゼ検出試薬を加えた。プレートを室温で40分間インキュベートした後、Perkin Elmer EnVision 2104プレートリーダーにて発光を相対光単位(RLU)として読み取った。
別の実施形態によれば、本発明は、本発明の化合物またはその薬学上許容される塩、エステル、もしくはエステルの塩と、薬学上許容される担体、補助剤、もしくはビヒクルとを含む組成物を提供する。本発明の組成物中の化合物の量は、生物学的サンプル中または患者においてACCを測定可能に阻害するために有効な量である。特定の実施形態において、本発明の組成物中の化合物の量は、生物学的サンプル中または患者においてACCを測定可能に阻害するために有効な量である。特定の実施形態において、本発明の組成物は、そのような組成物を必要としている患者への投与用に調剤される。いくつかの実施形態では、本発明の組成物は、患者への経口投与用に調剤される。
アセチルCoAカルボキシラーゼ(ACC)は、アセチルCoAのATP依存的カルボキシル化を触媒してマロニルCoAを生成する。この反応は、ビオチンカルボキシラーゼ(BC)反応およびカルボキシルトランスフェラーゼ(CT)反応の二つに分かれた反応で進行し、脂肪酸(FA)生合成において最初に行われる工程であり、この経路の律速反応である。FA生合成における基質としての役割に加えて、ACC触媒反応の産物であるマロニルCoAは、カルニチンパルミトイルトランスフェラーゼI(CPT−I)(ミトコンドリアFA酸化において最初に行われる工程を触媒する酵素)のアロステリック阻害によるミトコンドリアFA取込みを制御する際にも、重要な調節の役割を果たす。従って、マロニルCoAは、動物における、例えば運動中の、食餌の変化および変化した栄養要求に応答したFAの産生および利用の制御に重要な代謝シグナルであるため、肝臓および骨格筋における炭水化物の利用と脂肪の利用との間の切り替えの制御に重要な役割を果たす[非特許文献1]。
Claims (39)
- 式(I):
[式中、
m、n、およびkのそれぞれは独立に、0、1、または2であり;
R1は、H、ハロ、アルキル、ハロアルキル、CN、アミド、アリール、またはヘテロアリールであり、
R2は、H、アルキル、ハロアルキル、CN、ヒドロキシル、またはアルコキシであり;
R3は、H、アルキル、アリール、ヘテロアリール、シクロアルキル、またはヘテロシクロアルキルであり、かつ、ハロ、アルキル、またはハロアルキルで場合により置換されていてもよく;
R4は、H、アルキル、ハロアルキル、CN、ヒドロキシル、またはアルコキシであり;
R5は、ORまたはN(R)2であり;
R6は、アリールまたはヘテロアリールであり、かつ、ハロ、アルキル、ハロアルキル、CN、ヒドロキシル、またはアルコキシで場合により置換されていてもよく;
R7およびR8のそれぞれは独立に、H、アルキル、ハロアルキル、アルコキシ、またはハロアルコキシであり;または代わりに、R7およびR8は、それらが結合している炭素原子と一緒になって、それぞれ独立にOまたはNR’である1もしくは2個の環ヘテロ基を場合により含有してよい3〜6員のシクロアルキルを形成し;
R9、R10、R11、およびR12のそれぞれは独立に、H、アルキル、ハロアルキル、アルコキシ、またはハロアルコキシであり;または代わりに、R9およびR8は、それらが結合している炭素原子と一緒になって、それぞれ独立にOまたはNR’である1もしくは2個の環ヘテロ基を場合により含有してよい3〜7員のシクロアルキルを形成し;またはさらにその代わりに、R7およびR10は一緒になって(それらが結合している炭素原子を含まない)、C1-3アルキレン基を形成し、かつ、R8およびR9は一緒になって(それらが結合している炭素原子を含まない)、別のC1-3アルキレン基を形成し;
Xは、C(R)2、S、O、またはNR’であり;
Yは、S、O、またはNR’であり;
各Rは独立に、H、アルキル、ハロ、またはハロアルキルであり;かつ
R’のそれぞれは独立に、H、ハロ、アルキル、ハロアルキル、CN、またはヒドロキシルである]
で表される
ことを特徴とする化合物またはその鏡像異性体の薬学上許容される塩。 - kが0である
請求項1に記載の化合物。 - XがSまたはOである
請求項1または2に記載の化合物。 - XがSである
請求項1ないし3のいずれかに記載の化合物。 - kが1である
請求項1に記載の化合物。 - XがCH2、S、O、またはNHである
請求項1または5に記載の化合物。 - XがCH2である
請求項1、5、6のいずれかに記載の化合物。 - YがS、OまたはNHである
請求項1ないし7のいずれかに記載の化合物。 - YがOである
請求項1ないし8のいずれかに記載の化合物。 - R1がハロ、ハロアルキル、CN、またはヘテロアリールである
請求項1ないし9のいずれかに記載の化合物。 - R1がBr、F、CF3、CN、オキサゾリル、オキサゾリル、またはオキサジアゾリルである
請求項1ないし10のいずれかに記載の化合物。 - R1がBr、F、CF3、CN、2−オキサゾリル、4−オキサゾリル、または4−オキサジアゾリル、または5−オキサジアゾリルである
請求項1ないし11のいずれかに記載の化合物。 - R2およびR4のそれぞれが独立にHまたはアルキルである
請求項1ないし12のいずれかに記載の化合物。 - R3がシクロアルキルまたはヘテロシクロアルキルであり、かつ、ハロ、アルキル、またはハロアルキルで場合により置換されていてもよい
請求項1ないし13のいずれかに記載の化合物。 - R3が、ハロ、アルキル、またはハロアルキルで場合により置換されていてもよいヘテロシクロアルキルである
請求項1ないし14のいずれかに記載の化合物。 - R3がテトラヒドロ−2H−ピラニル、テトラヒドロフラニル、テトラヒドロ−2H−チオピラニル、またはテトラヒドロチオフェニルであり、かつ、ハロ、アルキル、またはハロアルキルで場合により置換されていてもよい
請求項1ないし15のいずれかに記載の化合物。 - R3が4−(テトラヒドロ−2H−ピラニル)または3−(テトラヒドロフラニル)である
請求項1ないし16のいずれかに記載の化合物。 - R5がORまたはN(R)2であり、ここで、各Rは独立にHまたはアルキルである
請求項1ないし17のいずれかに記載の化合物。 - RがHである
請求項1ないし18のいずれかに記載の化合物。 - R6がフェニル、ピリジニル、ピロリル、またはチオフェニルであり、かつ、ハロ、アルキル、ハロアルキル、CN、ヒドロキシル、またはアルコキシで場合により置換されていてもよい
請求項1ないし19のいずれかに記載の化合物。 - R6が、ハロ、アルキル、ハロアルキル、またはアルコキシで置換されたフェニルである
請求項1ないし20のいずれかに記載の化合物。 - mが0であり、かつ、nが1である
請求項1ないし21のいずれかに記載の化合物。 - R7およびR8のそれぞれが独立に、H、アルキル、ハロアルキル、アルコキシ、またはハロアルコキシであり、かつ、R9およびR10のそれぞれが独立に、H、アルキル、ハロアルキル、アルコキシ、またはハロアルコキシである
請求項1ないし22のいずれかに記載の化合物。 - R7およびR8が、それらが結合している炭素原子と一緒になって、独立にOまたはNR’である1もしくは2個の環ヘテロ基を場合により含有してよい3〜6員のシクロアルキルを形成し、かつ、R9およびR10のそれぞれが独立に、H、アルキル、ハロアルキル、アルコキシ、またはハロアルコキシである
請求項1ないし22のいずれかに記載の化合物。 - R7およびR8が、それらが結合している炭素原子と一緒になって、1個のOの環ヘテロ基を場合により含有してよい3〜6員のシクロアルキルを形成する
請求項24に記載の化合物。 - R7およびR10のそれぞれが独立に、H、アルキル、ハロアルキル、アルコキシ、またはハロアルコキシであり、かつ、R8およびR9は、それらが結合している炭素原子と一緒になって、それぞれ独立にOまたはNR’である1もしくは2個の環ヘテロ基を場合により含有してよい3〜7員のシクロアルキルを形成する
請求項1ないし22のいずれかに記載の化合物。 - R7およびR10のそれぞれが独立に、H、アルキル、またはハロアルキルであり、かつ、R8およびR9は、それらが結合している炭素原子と一緒になって、3〜7員のシクロアルキルを形成する
請求項27に記載の化合物。 - R7およびR10が一緒になって(それらが結合している炭素原子を含まない)、C1-3アルキレン基を形成し、かつ、R8およびR9が一緒になって(それらが結合している炭素原子を含まない)、別のC1-3アルキレン基を形成する、請求項1〜22のいずれか一項に記載の化合物。
- R7およびR10が一緒になって(それらが結合している炭素原子を含まない)、メチレンまたはエチレン基を形成し、かつ、R8およびR9が一緒になって(それらが結合している炭素原子を含まない)、メチレンまたはエチレン基を形成する
請求項29に記載の化合物。 - 各Rおよび各R’が独立にH、ハロ、アルキル、またはハロアルキルである
請求項1ないし30のいずれかに記載の化合物。 - 治療上有効な量の請求項1ないし32のいずれかに記載の化合物と薬学上許容される担体とを含む医薬組成物。
- 必要とする対象においてACCを阻害する方法であって、
前記対象に請求項1ないし32のいずれかに記載の化合物または請求項33に記載の組成物を投与することを含む
ことを特徴とする方法。 - 必要とする対象において非アルコール性脂肪肝疾患、代謝性疾患または癌を治療する方法であって、前記対象に治療上有効な量の請求項1ないし32のいずれかに記載の化合物または請求項33に記載の組成物を投与することを含む
ことを特徴とする方法。 - 非アルコール性脂肪肝疾患が非アルコール性脂肪性肝炎、肝脂肪変性、大滴性脂肪変性、進行性線維症、または硬変である
請求項35に記載の方法。 - 前記代謝障害が肥満症、異脂肪血症または高脂血症である
請求項36に記載の方法。 - 前記肥満症がプラダー・ウィリー症候群、バルデー・ビードル症候群、コーエン症候群、もしくはMOMO症候群の症状であるか、または前記肥満症は、インスリン、スルホニル尿素、チアゾリジンジオン、抗精神病薬、抗鬱薬、ステロイド、抗痙攣薬(フェニロインおよびバルプロ酸塩を含む)、ピゾチフェン、およびホルモン避妊薬から選択する群から選択される薬剤の投与の副作用である
請求項37に記載の方法。 - 前記癌が肝臓癌、黒色腫、脂肪肉腫、肺癌、乳癌、前立腺癌、白血病、腎臓癌、食道癌、脳癌、リンパ腫または結腸癌である
請求項35に記載の方法。
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