JP5399248B2 - 3環系アミド化合物 - Google Patents
3環系アミド化合物 Download PDFInfo
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- JP5399248B2 JP5399248B2 JP2009528146A JP2009528146A JP5399248B2 JP 5399248 B2 JP5399248 B2 JP 5399248B2 JP 2009528146 A JP2009528146 A JP 2009528146A JP 2009528146 A JP2009528146 A JP 2009528146A JP 5399248 B2 JP5399248 B2 JP 5399248B2
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- methyl
- group
- reduced pressure
- under reduced
- hexahydro
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- PXCCPUPTKXBTBI-UHFFFAOYSA-N CC(CCC1)(CCCc2c3)c2c1cc3C(Nc1ccc(C(O)=O)c(F)c1)=O Chemical compound CC(CCC1)(CCCc2c3)c2c1cc3C(Nc1ccc(C(O)=O)c(F)c1)=O PXCCPUPTKXBTBI-UHFFFAOYSA-N 0.000 description 1
- LEGONRJFBCEPCL-UHFFFAOYSA-N CC(CCC1)(CCCc2c3)c2c1cc3C(O)=O Chemical compound CC(CCC1)(CCCc2c3)c2c1cc3C(O)=O LEGONRJFBCEPCL-UHFFFAOYSA-N 0.000 description 1
- IAFZRFBXIXUXAG-UHFFFAOYSA-N CC(CCC1)(CCCc2c3)c2c1cc3NC(c(cc1)ccc1C(OC)=O)=O Chemical compound CC(CCC1)(CCCc2c3)c2c1cc3NC(c(cc1)ccc1C(OC)=O)=O IAFZRFBXIXUXAG-UHFFFAOYSA-N 0.000 description 1
- NYGKHXIXMOGEGB-ZDUSSCGKSA-N CCOC(C[C@H]1c2ccccc2CCCC1)=O Chemical compound CCOC(C[C@H]1c2ccccc2CCCC1)=O NYGKHXIXMOGEGB-ZDUSSCGKSA-N 0.000 description 1
- SKWAFZSANAMTLP-UHFFFAOYSA-N OC(c(c(F)c1)ccc1NC(c1cc(CCCCC2CCCC3)c2c3c1)=O)=O Chemical compound OC(c(c(F)c1)ccc1NC(c1cc(CCCCC2CCCC3)c2c3c1)=O)=O SKWAFZSANAMTLP-UHFFFAOYSA-N 0.000 description 1
- KUFCFGLBJSLQCH-UHFFFAOYSA-N OC(c(ccc(NC(c1cc(CCCCC2CCCC3)c2c3c1)=O)c1)c1O)=O Chemical compound OC(c(ccc(NC(c1cc(CCCCC2CCCC3)c2c3c1)=O)c1)c1O)=O KUFCFGLBJSLQCH-UHFFFAOYSA-N 0.000 description 1
- OAOPNICFAVZYDG-UHFFFAOYSA-N OC(c(nc1)ccc1C(Nc1cc(CCCC2CCC3)c2c3c1)=O)=O Chemical compound OC(c(nc1)ccc1C(Nc1cc(CCCC2CCC3)c2c3c1)=O)=O OAOPNICFAVZYDG-UHFFFAOYSA-N 0.000 description 1
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Description
別の観点からは、本発明により、上記の一般式(I)で表される化合物、生理学的に許容されるその塩、又はそのエステルを含む医薬が提供される。この医薬はレチノイド作用剤として用いることができる。
(1)2,3,3a,4,5,6-ヘキサヒドロ-1H-フェナレン
1H-NMR(400MHz,CDCl3):δ1.26-1.40(2H,m),1.70-1.84(2H,m),1.85-2.00(4H,m),2.52-2.63(1H,m),2.78-2.82(4H,m),6.89(1H,d,J=7.5Hz),7.02(1H,t,J=7.5Hz)
1H-NMR(400MHz,CDCl3):δ1.26-1.40(2H,m),1.77-2.02(6H,m),2.55(3H,s),2.56-2.60(1H,m),2.82-2.87(4H,m),7.50(2H,s)
1H-NMR(400MHz,CDCl3):δ1.26-1.41(2H,m),1.73-1.86(2H,m),1.88-2.05(4H,m),2.54-2.65(1H,m),2.82-2.88(4H,m),7.64(2H,s)
1H-NMR(400MHz,CDCl3):δ1.22-1.34(2H,m),1.66-1.80(2H,m),1.81-1.93(4H,m),2.40-2.54(1H,m),2.69-2.74(4H,m),3.43(2H,br-s),6.29(2H,s)
1H-NMR(400MHz,CDCl3):δ1.24-1.38(2H,m),1.70-1.84(2H,m),1.86-1.99(4H,m),2.49-2.59(1H,m),2.80-2.83(4H,m),3.96(3H,s),7.19(2H,s),7.77(1H,br-s),7.90(2H,d,J=8.7Hz),8.12(2H,d,J=8.7Hz)
1H-NMR(400MHz,CD3OD):δ1.24-1.37(2H,m),1.73-1.87(2H,m),1.88-2.02(4H,m),2.50-2.60(1H,m),2.78-2.83(4H,m),7.20(2H,s),7.98(2H,d,J=8.7Hz),8.14(2H,d,J=8.7Hz)
1H-NMR(400MHz,DMSO-d6):δ1.21-1.30(2H,m),1.25-1.78(2H,m),1.81-1.94(4H,m),2.43-2.47(1H,m),2.73-2.76(4H,m),7.30(2H,s),8.01(2H,d,J=8.6Hz),8.05(2H,d,J=8.6 Hz),10.15(1H,s)
(1)4-[(5,6,6a,7,8,9-ヘキサヒドロ-4H-2-フェナレニル)カルボキサミド]安息香酸メチル
1H-NMR(400MHz,CDCl3):δ1.26-1.41(2H,m),1.74-1.87(2H,m),1.89-2.61(4H,m),2.54-2.64(1H,m),2.83-2.88(4H,m),3.91(3H,s),7.39(2H,s),7.74(2H,d,J=8.7Hz),7.95(1H,br-s),8.04(2H,d,J=8.7Hz)
1H-NMR(400MHz,CD3OD):δ1.28-1.41(2H,m),1.76-1.90(2H,m),1.91-2.07(4H,m),2.56-2.67(1H,m),2.88-2.90(4H,m),7.47(2H,s),7.83(2H,d,J=8.7Hz),8.01(2H,d,J=8.7Hz)
1H-NMR(400MHz,DMSO-d6):δ1.21-1.34(2H,m),1.73-1.99(6H,m),2.55-2.66(1H,m),2.80-2.85(4H,m),7.49(2H,s),7.90(4H,s),10.33(1H,s)
(1)2-フルオロ-4-[(5,6,6a,7,8,9-ヘキサヒドロ-4H-2-フェナレニル)カルボキサミド]安息香酸メチル
1H-NMR(400MHz,CDCl3):δ1.25-1.40(2H,m),1.73-1.87(2H,m),1.89-2.04(4H,m),2.53-2.62(1H,m),2.82-2.87(4H,m),3.92(3H,s),7.31(1H,dd,J=12.9,1.8Hz),7.37(2H,s),7.77(1H,dd,J=12.9,1.8Hz),7.94(1H,t,J=8.9Hz),7.99(1H,br-s)
1H-NMR(400MHz,CD3OD):δ1.27-1.40(2H,m),1.76-1.88(2H,m),1.89-1.95(2H,m),1.96-2.06(2H,m),2.55-2.65(1H,m),2.84-2.89(4H,m),7.46(2H,s),7.53(1H,dd,J=8.4,2.1Hz),7.80(1H,dd,J=13.5,2.1Hz),7.91(1H,t,J=8.4Hz)
1H-NMR(400MHz,DMSO-d6):δ1.21-1.34(2H,m),1.74-1.80(2H,m),1.83-1.89(2H,m),1.92-1.99(2H,m),2.53-2.62(1H,m),2.80-2.85(4H,m),7.49(2H,s),7.65(1H,dd,J=8.7,2.1Hz),7.81-7.91(2H,m),10.51(1H,s)
(1)2-クロロ-4-[(5,6,6a,7,8,9-ヘキサヒドロ-4H-2-フェナレニル)カルボキサミド]安息香酸メチル
1H-NMR(400MHz,CDCl3):δ1.27-1.41(2H,m),1.73-1.87(2H,m),1.89-2.04(4H,m),2.54-2.63(1H,m),2.83-2.88(4H,m),3.92(3H,s),7.38(2H,m),7.64(1H,dd,J=8.4,2.1Hz),7.84(1H,d,J=2.1Hz),7.91(1H,d,J=8.4Hz),7.91(1H,br-s)
1H-NMR(400MHz,CD3OD):δ1.27-1.41(2H,m),1.76-1.88(2H,m),1.89-1.96(2H,m),1.97-2.06(2H,m),2.56-2.67(1H,m),2.85-2.90(4H,m),7.46(2H,s),7.71(1H,dd,J=8.4,2.1Hz),7.90(1H,d,J=8.4Hz),8.02(1H,d,J=2.1Hz)
1H-NMR(400MHz,DMSO-d6):δ1.21-1.34(2H,m),1.73-1.80(2H,m),1.82-1.89(2H,m),1.92-1.99(2H,m),2.56-2.62(1H,m),2.80-2.85(4H,m),7.49(2H,s),7.80-7.87(2H,m),8.05(1H,d,J=2.1Hz),10.43(1H,s)
(1)2-ヒドロキシ4-[(5,6,6a,7,8,9-ヘキサヒドロ-4H-2-フェナレニル)カルボキサミド]安息香酸メチル
1H-NMR(400MHz,CDCl3):δ1.27-1.41(2H,m),1.73-1.87(2H,m),1.89-2.04(4H,m),2.53-2.63(1H,m),2.83-2.88(4H,m),3.94(3H,s),7.24(1H,dd,J=8.7,2.1Hz),7.30(1H,d,J=2.1Hz),7.37(2H,s),7.81(1H,d,J=8.7Hz),7.85(1H,br-s),10.87(1H,s)
1H-NMR(400MHz,CD3OD):δ1.27-1.40(2H,m),1.76-1.89(2H,m),1.90-1.96(2H,m),1.97-2.06(2H,m),2.55-2.66(1H,m),2.84-2.89(4H,m),7.22(1H,dd,J=8.7,2.1Hz),7.44(2H,s),7.47(1H,d,J=2.1Hz),7.81(1H,d,J=8.7Hz)
1H-NMR(400MHz,DMSO-d6):δ1.15-1.33(2H,m),1.68-1.80(2H,m),1.82-1.89(2H,m),1.91-1.99(2H,m),2.53-2.61(1H,m),2.79-2.85(4H,m),7.32(1H,dd,J=8.7,2.1Hz),7.47(2H,s),7.53(1H,d,J=2.1Hz),7.74(1H,d,J=8.7Hz),10.29(1H,s)
(1)2-メトキシ-4-[(5,6,6a,7,8,9-ヘキサヒドロ-4H-2-フェナレニル)カルボキサミド]安息香酸メチル
1H-NMR(400MHz,CDCl3):δ1.26-1.41(2H,m),1.73-1.87(2H,m),1.89-2.05(4H,m),2.54-2.63(1H,m),2.83-2.88(4H,m),3.88(3H,s),3.95(3H,s),6.96(1H,dd,J=8.7,2.1Hz),7.39(2H,s),7.83(1H,d,J=2.1Hz),7.85(1H,d,J=8.7Hz),7.99(1H,br-s)
1H-NMR(400MHz,CD3OD):δ1.26-1.41(2H,m),1.78-1.87(2H,m),1.88-1.96(2H,m),1.97-2.07(2H,m),2.55-2.67(1H,m),2.85-2.90(4H,m),3.94(3H,s),7.34(1H,dd,J=8.4,2.1Hz),7.47(2H,s),7.73(1H,d,J=2.1Hz),7.84(1H,d,J=8.4Hz)
1H-NMR(400MHz,DMSO-d6):δ1.21-1.34(2H,m),1.74-1.80(2H,m),1.84-1.89(2H,m),1.92-1.99(2H,m),2.52-2.56(1H,m),2.80-2.85(4H,m),3.78(3H,s),7.35(1H,d,J=8.1Hz),7.50(2H,s),7.56-7.62(2H,m),10.22(1H,s)
(1)6-[(5,6,6a,7,8,9-ヘキサヒドロ-4H-2-フェナレニル)カルバモイル]ニコチン酸メチル
1H-NMR(400MHz,CDCl3):δ1.26-1.39(2H,m),1.72-1.85(2H,m),1.88-1.99(4H,m),2.52-2.59(1H,m),2.81-2.86(4H,m),4.00(3H,s),7.35(2H,s),8.36(1H,d,J=8.4Hz),8.49(1H,dd,J=8.4,2.1Hz),9.18(1H,d,J=2.1Hz),9.85(1H,br-s)
1H-NMR(400MHz,CDCl3):δ1.26-1.40(2H,m),1.72-1.86(2H,m),1.88-2.00(4H,m),2.51-2.61(1H,m),2.82-2.87(4H,m),7.36(2H,s),8.42(1H,d,J=8.1Hz),8.58(1H,dd,J=8.1,2.1Hz),9.26(1H,d,J=2.1Hz),9.88(1H,s)
(1)6-[(5,6,6a,7,8,9-ヘキサヒドロ-4H-2-フェナレニル)カルボキサミド]ニコチン酸メチル
1H-NMR(400MHz,CDCl3):δ1.28-1.42(2H,m),1.74-1.88(2H,m),1.90-2.05(4H,m),2.55-2.64(1H,m),2.84-2.89(4H,m),3.94(3H,s),7.46(2H,s),8.35(1H,dd,J=8.7,2.2Hz),8.48(1H,d,J=8.7Hz),8.76(1H,br-s),8.93(1H,d,J=2.2Hz)
1H-NMR(400MHz,DMSO-d3):δ1.20-1.34(2H,m),1.68-1.80(2H,m),1.82-1.99(4H,m),2.55-2.62(1H,m),2.78-2.83(4H,m),7.58(2H,s),8.30(1H,s),8.31(1H,s),8.88(1H,d,J=1.8Hz),10.93(1H,s)
例9
1H-NMR(400MHz,CDCl3):δ1.24-1.38(2H,m),1.70-1.84(2H,m),1.86-1.99(4H,m),2.50-2.57(1H,m),2.79-2.82(4H,m),4.04(3H,s),7.17(2H,s),7.86(1H,br-s),8.22(1H,d,J=8.0Hz),8.32(1H,dd,J=8.0Hz,2.3Hz),9.15(1H,d,J=1.5Hz)
1H-NMR(400MHz,DMSO-d3):δ1.14-1.28(2H,m),1.63-1.76(2H,m),1.78-1.83(2H,m),1.84-1.92(2H,m),2.40-2.42(1H,m),2.71-2.74(4H,m),7.27(2H,s),8.13(1H,d,J=8.1Hz),8.40(1H,dd,J=8.1,2.1Hz),9.13(1H,d,J=2.1Hz),10.32(1H,s)
例10
1H-NMR(400MHz,CDCl3):δ1.23-1.41(2H,m),1.74-1.88(2H,m),1.89-2.04(4H,m),2.56-2.64(1H,m),2.81-2.91(4H,m),4.00(3H,s),7.42(2H,s),8.09(1H,br-s),8.17(1H,d,J=8.7Hz),8.57(1H,dd,J=8.7,2.7Hz),8.73(1H,d,J=2.7Hz)
1H-NMR(400MHz,DMSO-d3):δ1.19-1.32(2H,m),1.71-1.78(2H,m),1.82-1.87(2H,m),1.88-1.97(2H,m),2.53-2.60(1H,m),2.78-2.83(4H,m),7.50(2H,s),8.04(1H,d,J=8.4Hz),8.37(1H,dd,J=8.4,2.7Hz)9.01(1H,d,J=2.7Hz),10.55(1H,s)
(1)5-[(5,6,6a,7,8,9-ヘキサヒドロ-4H-2-フェナレニル)カルバモイル]チオフェン-2-カルボン酸メチル
1H-NMR(400MHz,CDCl3):δ1.24-1.38(2H,m),1.70-1.86(2H,m),1.88-1.99(4H,m),2.48-2.59(1H,m),2.78-2.83(4H,m),3.92(3H,s),7.14(2H,s),7.53(1H,d,J=3.9Hz),7.58(1H,br-s),7.76(1H,d,J=3.9Hz)
1H-NMR(400MHz,DMSO-d3):δ1.18-1.27(2H,m),1.66-1.76(2H,m),1.77-1.92(4H,m),2.44-2.45(1H,m),2.71-2.73(4H,m),7.22(2H,s),7.26(1H,d,J=4.2Hz),7.95(1H,d,J=4.2Hz),10.17(1H,s)
(1)5-[(5,6,6a,7,8,9-ヘキサヒドロ-4H-2-フェナレニル)カルボキサミド]チオフェン-2-カルボン酸メチル
1H-NMR(400MHz,CDCl3):δ1.34(2H,td,J=12.0,3.9Hz),1.72-1.85(2H,m),1.87-2.04(4H,m),2.52-2.63(1H,m),2.80-2.85(4H,m),3.87(3H,s),6.75(1H,d,J=4.2Hz),7.41(2H,s),7.64(1H,d,J=4.2Hz),8.94(1H,br-s)
1H-NMR(400MHz,DMSO-d3):δ1.20-1.32(2H,m),1.71-1.78(2H,m),1.79-1.87(2H,m),1.89-1.98(2H,m),2.53-2.61(1H,m),2.78-2.83(4H,m),6.90(1H,d,J=4.2Hz),7.52(2H,s),7.54(1H,d,J=4.2Hz)11.74(1H,s)
4-[(5,6,6a,7,8,9-ヘキサヒドロ-4H-2-フェナレニル)スルファモイル]安息香酸
1H-NMR(400MHz,DMSO-d3):δ1.06-1.18(2H,m),1.54-1.66(2H,m),1.70-1.74(2H,m),1.78-1.83(2H,m),2.32-2.43(1H,m),2.55-2.59(4H,m),6.58(2H,s),7.84(2H,d,J=8.1Hz),8.05(2H,d,J=8.1Hz),10.14(1H,s)
(1)(±)-3a-メチル-2,3,3a,4-テトラヒドロ-1H-フェナレン
1H-NMR(400MHz,CDCl3):δ1.16(3H,s),1.64(1H,td,J=13.1,3.4Hz),1.74(1H,dt,J=12.8,3.4Hz),1.79-1.89(1H,m),1.92-2.04(1H,m),2.10(1H,dd,J=17.1,6.3Hz),2.27(1H,dt,J=17.1,2.7Hz),2.77-2.83(2H,m)5.89-5.95(1H,m),6.45(1H,dd,J=9.6,3.0Hz),6.85(1H,d,J=7.5Hz),6.92(1H,d,J=7.5Hz),7.03(1H,t,J=7.5Hz)
1H-NMR(400MHz,CDCl3):δ1.17(3H,s),1.51(2H,td,J=13.1,5.1Hz),1.66(2H,dt,J=13.1,4.1Hz),1.74-1.86(2H,m),1.98-2.14(2H,m),2.79(2H,dt,J=17.1,8.6Hz),2.91(2H,ddd,J=17.1,8.1,3.5Hz),6.88(2H,dd,J=7.5,0.8Hz),7.00(1H,dd,J=8.1,6.6Hz)
1H-NMR(400MHz,CDCl3):δ1.17(3H,s),1.51(2H,td,J=13.0,4.8Hz),1.70(2H,dt,J=13.0,4.1Hz),1.78-1.89(2H,m),1.99-2.15(2H,m),2.55(3H,s),2.82(2H,dt,J=17.1,8.6Hz),2.97(2H,ddd,J=17.3,7.9,3.3Hz),7.48(2H,s)
1H-NMR(400MHz,CDCl3):δ1.17(3H,s),1.52(2H,td,J=13.1,5.1Hz),1.70(2H,dt,J=13.1,4.1Hz),1.78-1.89(2H,m),1.99-2.15(2H,m),2.84(2H,dt,J=17.3,8.6Hz),2.97(2H,ddd,J=17.3,8.1,3.6Hz),7.62(2H,s)
1H-NMR(400MHz,CDCl3):δ1.13(3H,s),1.46(2H,td,J=12.9,5.1Hz),1.62(2H,dt,J=12.9,4.1Hz),1.71-1.82(2H,m),1.94-2.10(2H,m),2.69(2H,dt,J=17.1,8.6Hz),2.81(2H,ddd,J=17.4,8.0,3.5Hz),3.40(2H,br-s),6.27(2H,s)
1H-NMR(400MHz,CDCl3):δ1.16(3H,s),1.50(2H,td,J=12.9,5.1Hz),1.68(2H,dt,J=12.9,4.1Hz),1.76-1.87(2H,m),1.98-2.15(2H,m),2.79(2H,dt,J=17.4,8.7Hz),2.92(2H,ddd,J=17.3,7.9,3.4Hz),3.96(3H,s),7.18(2H,s),7.69(1H,br-s),7.89(2H,d,J=8.4Hz),8.13(2H,d,J=8.4Hz)
1H-NMR(400MHz,CD3OD):δ1.17(3H,s),1.49(2H,td,J=12.9,4.1Hz),1.70(2H,dt,J=12.9,4.1Hz),1.76-1.87(2H,m),2.02-2.18(2H,m),2.78(2H,dt,J=17.3,8.6Hz),2.88(2H,ddd,J=17.1,7.8,3.3Hz),7.18(2H,s),7.97(2H,d,J=8.4Hz),8.12(2H,d,J=8.4Hz)
1H-NMR(400MHz,DMSO-d6):δ1.11(3H,s),1.42(2H,td,J=12.8,4.9Hz),1.64(2H,dt,J=12.8,4.0Hz),1.71-1.80(2H,m),1.93-2.09(2H,m),2.72(2H,dt,J=17.4,8.7Hz),2.85(2H,ddd,J=17.1,7.8,3.0Hz),7.28(2H,s),8.01(2H,d,J=8.4Hz),8.05(2H,d,J=8.4 Hz),10.13(1H,s)
(1)4-[(6a-メチル-5,6,6a,7,8,9-ヘキサヒドロ-4H-2-フェナレニル)カルボキサミド]安息香酸メチル
1H-NMR(400MHz,CDCl3):δ1.17(3H,s),1.52(2H,td,J=12.9,4.8Hz),1.71(2H,dt,J=12.9,4.2Hz),1.78-1.90(2H,m),1.99-2.16(2H,m),2.87(2H,dt,J=17.4,8.7Hz),2.98(2H,ddd,J=17.4,7.8,3.3Hz),3.91(3H,s),7.38(2H,s),7.73(2H,d,J=8.9Hz),7.94(1H,br-s),8.04(2H,d,J=8.9Hz)
1H-NMR(400MHz,CD3OD):δ1.20(3H,s),1.53(2H,td,J=13.0,5.0Hz),1.74(2H,dt,J=13.0,4.1Hz),1.80-1.91(2H,m),2.04-2.21(2H,m),2.86(2H,dt,J=17.3,8.6Hz),3.00(2H,ddd,J=17.4,7.8,3.3Hz),7.45(2H,s),7.82(2H,d,J=9.0Hz),8.00(2H,d,J=9.0Hz)
1H-NMR(400MHz,DMSO-d6):δ1.14(3H,s),1.45(2H,td,J=12.8,4.8Hz),1.69(2H,dt,J=12.8,3.8Hz),1.74-1.83(2H,m),1.95-2.11(2H,m),2.81(2H,dt,J=17.4,8.7Hz),2.96(2H,ddd,J=17.0,7.8,2.9Hz),7.45(2H,s),7.87(2H,d,J=8.9Hz),7.92(2H,d,J=8.9Hz),10.34(1H,s)
(1)2-フルオロ-4-[(6a-メチル-5,6,6a,7,8,9-ヘキサヒドロ-4H-2-フェナレニル)カルボキサミド]安息香酸メチル
1H-NMR(400MHz,CDCl3):δ1.17(3H,s),1.51(2H,td,J=12.9,5.1Hz),1.72(2H,dt,J=12.9,4.1Hz),1.80-1.91(2H,m),2.01-2.17(2H,m),2.85(2H,dt,J=17.3,8.6Hz),2.99(2H,ddd,J=17.6,7.8,3.5Hz),3.92(3H,s),7.30(1H,dd,J=8.4,2.1Hz),7.36(2H,s),7.77(1H,dd,J=13.1,2.1Hz),7.91(1H,br-s),7.95(1H,t,J=8.4Hz)
1H-NMR(400MHz,CD3OD):δ1.19(3H,s),1.52(2H,td,J=12.9,5.1Hz),1.73(2H,dt,J=12.9,4.1Hz),1.79-1.91(2H,m),2.01-2.20(2H,m),2.86(2H,dt,J=17.3,8.7Hz),3.00(2H,ddd,J=17.4,8.0,3.5Hz),7.45(2H,s),7.53(1H,dd,J=8.7,2.1Hz),7.80(1H,dd,J=13.7,2.1Hz),7.91(1H,t,J=8.7Hz)
1H-NMR(400MHz,DMSO-d6):δ1.14(3H,s),1.45(2H,td,J=12.9,5.1Hz),1.67(2H,dt,J=12.9,3.9Hz),1.74-1.85(2H,m),1.95-2.11(2H,m),2.82(2H,dt,J=17.3,8.7Hz),2.96(2H,ddd,J=17.3,7.8,3.3Hz),7.45(2H,s),7.63(1H,d,J=8.7Hz),7.79-7.91(2H,m),10.50(1H,s)
(1)2-クロロ-4-[(6a-メチル-5,6,6a,7,8,9-ヘキサヒドロ-4H-2-フェナレニル)カルボキサミド]安息香酸メチル
1H-NMR(400MHz,CDCl3):δ1.16(3H,s),1.51(2H,td,J=12.9,4.8Hz),1.71(2H,dt,J=12.9,4.1Hz),1.78-1.89(2H,m),1.99-2.15(2H,m),2.82(2H,dt,J=17.1,8.6Hz),2.96(2H,ddd,J=17.3,7.8,3.2Hz),3.91(3H,s),7.36(2H,s),7.64(1H,dd,J=8.7,2.1Hz),7.84(1H,d,J=2.1Hz),7.89(1H,d,J=8.7Hz),7.98(1H,br-s)
1H-NMR(400MHz,CD3OD):δ1.19(3H,s),1.52(2H,td,J=12.9,5.1Hz),1.73(2H,dt,J=12.9,4.1Hz),1.79-1.90(2H,m),2.03-2.20(2H,m),2.85(2H,dt,J=17.1,8.6Hz),3.00(2H,ddd,J=17.3,7.7,3.3Hz),7.44(2H,s),7.71(1H,dd,J=8.7,1.8Hz),7.90(1H,d,J=8.7Hz),8.02(1H,d,J=1.8Hz)
1H-NMR(400MHz,DMSO-d6):δ1.13(3H,s),1.45(2H,td,J=12.9,5.1Hz),1.68(2H,dt,J=12.9,3.9Hz),1.75-1.83(2H,m),1.95-2.10(2H,m),2.81(2H,dt,J=17.3,8.7Hz),2.96(2H,ddd,J=17.1,7.6,3.0Hz),7.46(2H,s),7.81(1H,dd,J=8.7,1.8Hz),7.87(1H,d,J=8.7Hz),8.04(1H,d,J=1.8Hz),10.43(1H,s)
(1)2-ヒドロキシ-4-[(6a-メチル-5,6,6a,7,8,9-ヘキサヒドロ-4H-2-フェナレニル)カルボキサミド]安息香酸メチル
1H-NMR(400MHz,CDCl3):δ1.16(3H,s),1.51(2H,td,J=12.9,4.8Hz),1.71(2H,dt,J=12.9,3.9Hz),1.78-1.89(2H,m),1.99-2.15(2H,m),2.83(2H,dt,J=17.1,8.6Hz),2.97(2H,ddd,J=17.7,7.8,3.3Hz),3.94(3H,s),7.24(1H,dd,J=8.7,2.1Hz),7.32(1H,d,J=2.1Hz),7.35(2H,s),7.81(1H,d,J=8.7Hz),7.88(1H,br-s),10.87(1H,s)
1H-NMR(400MHz,CD3OD):δ1.19(3H,s),1.52(2H,td,J=12.9,5.1Hz),1.73(2H,dt,J=12.9,4.1Hz),1.79-1.90(2H,m),2.04-2.20(2H,m),2.86(2H,dt,J=17.1,8.6Hz),3.00(2H,ddd,J=17.4,7.9,2.9Hz),7.21(1H,dd,J=8.7,1.8Hz),7.43(2H,s),7.46(1H,d,J=1.8Hz),7.81(1H,d,J=8.7Hz)
1H-NMR(400MHz,DMSO-d6):δ1.13(3H,s),1.45(2H,td,J=12.9,5.1Hz),1.68(2H,dt,J=12.9,3.9Hz),1.74-1.84(2H,m),1.95-2.11(2H,m),2.81(2H,dt,J=17.3,8.4Hz),2.96(2H,ddd,J=17.4,7.8,3.0Hz),7.31(1H,dd,J=8.7,1.8Hz),7.43(2H,s),7.51(1H,d,J=1.8Hz),7.74(1H,d,J=8.7Hz),10.29(1H,s)
(1)2-メトキシ-4-[(6a-メチル-5,6,6a,7,8,9-ヘキサヒドロ-4H-2-フェナレニル)カルボキサミド]安息香酸メチル
1H-NMR(400MHz,CDCl3):δ1.17(3H,s),1.51(2H,td,J=12.9,5.1Hz),1.71(2H,dt,J=12.9,3.9Hz),1.78-1.89(2H,m),1.99-2.15(2H,m),2.82(2H,dt,J=17.1,8.6Hz),2.96(2H,ddd,J=17.1,7.8,3.0Hz),3.87(3H,s),3.93(3H,s),6.97(1H,dd,J=8.4,1.8Hz),7.38(2H,s),7.82(1H,d,J=1.8Hz),7.85(1H,d,J=8.4Hz),8.05(1H,br-s)
1H-NMR(400MHz,CD3OD):δ1.23(3H,s),1.53(2H,td,J=12.9,4.9Hz),1.74(2H,dt,J=13.1,4.0Hz),1.80-1.91(2H,m),2.05-2.21(2H,m),2.87(2H,dt,J=17.1,8.6Hz),3.01(2H,ddd,J=17.4,7.9,3.5Hz),3.94(3H,s),7.34(1H,dd,J=8.7,2.1Hz),7.46(2H,s),7.73(1H,d,J=2.1Hz),7.84(1H,d,J=8.7Hz)
1H-NMR(400MHz,DMSO-d6):δ1.14(3H,s),1.46(2H,td,J=12.9,5.4Hz),1.69(2H,dt,J=12.5,3.8Hz),1.75-1.85(2H,m),1.95-2.01(2H,m),2.82(2H,dt,J=17.4,8.7Hz),2.96(2H,ddd,J=17.3,7.7,3.3Hz),3.77(3H,s),7.41(1H,dd,J=8.6,2.1Hz),7.46(2H,s),7.55-57(2H,m),10.19(1H,s)
(1)6-[(6a-メチル-5,6,6a,7,8,9-ヘキサヒドロ-4H-2-フェナレニル)カルバモイル]ニコチン酸メチル
1H-NMR(400MHz,CDCl3):δ1.17(3H,s),1.51(2H,td,J=12.9,4.8Hz),1.68(2H,dt,J=12.9,4.1Hz),1.76-1.88(2H,m),1.99-2.15(2H,m),2.82(2H,dt,J=17.3,8.7Hz),2.95(2H,ddd,J=17.4,8.1,3.3Hz),4.00(3H,s),7.33(2H,s),8.35(1H,d,J=8.1Hz),8.49(1H,dd,J=8.1,2.1Hz),9.18(1H,d,J=2.1Hz),9.83(1H,br-s)
1H-NMR(400MHz,CDCl3):δ1.17(3H,s),1.51(2H,td,J=12.9,5.1Hz),1.69(2H,dt,J=12.9,3.9Hz),1.77-1.88(2H,m),2.00-2.16(2H,m),2.83(2H,dt,J=17.4,8.7Hz),2.96(2H,ddd,J=17.3,8.1,3.2Hz),7.31(2H,s),8.42(1H,d,J=8.1Hz),8.57(1H,dd,J=8.1,1.8Hz),9.26(1H,d,J=1.8Hz),9.87(1H,s)
(1)6-[(6a-メチル-5,6,6a,7,8,9-ヘキサヒドロ-4H-2-フェナレニル)カルボキサミド]ニコチン酸メチル
1H-NMR(400MHz,CDCl3):δ1.18(3H,s),1.52(2H,td,J=13.1,5.1Hz),1.71(2H,dt,J=12.9,4.1Hz),1.79-1.90(2H,m),2.00-2.17(2H,m),2.84(2H,dt,J=17.1,8.6Hz),2.98(2H,ddd,J=17.4,7.8,3.3Hz),3.94(3H,s),7.44(2H,s),8.34(1H,dd,J=8.7,2.1Hz),8.47(1H,d,J=8.7Hz),8.73(1H,br-s),8.92(1H,d,J=2.1Hz)
1H-NMR(400MHz,DMSO-d6):δ1.14(3H,s),1.48(2H,td,J=12.9,5.1Hz),1.68(2H,dt,J=12.9,4.4Hz),1.75-1.84(2H,m),1.94-2.11(2H,m),2.80(2H,dt,J=17.3,8.6Hz),2.95(2H,ddd,J=17.4,7.7,3.2Hz),7.57(2H,s),8.29-8.32(2H,m),8.87(1H,s),10.88(1H,s)
(1)5-[(6a-メチル-5,6,6a,7,8,9-ヘキサヒドロ-4H-フェナレニル)カルバモイル]ピリジン-2-カルボン酸メチル
1H-NMR(400MHz,CDCl3):δ1.14(3H,s),1.47(2H,td,J=12.9,5.1Hz),1.66(2H,dt,J=12.9,4.2Hz),1.73-1.84(2H,m),1.96-2.12(2H,m),2.73(2H,dt,J=17.1,8.4Hz),2.86(2H,ddd,J=17.1,7.8,3.3Hz),4.02(3H,s),7.14(2H,s),8.16(1H,d,J=7.8Hz),8.25(1H,br-s),8.30(1H,dd,J=7.8,2.1Hz),9.13(1H,d,J=2.1Hz)
1H-NMR(400MHz,DMSO-d6):δ1.09(3H,s),1.39(2H,td,J=12.9,5.1Hz),1.62(2H,dt,J=12.6,3.6Hz),1.68-1.78(2H,m),1.91-2.06(2H,m),2.70(2H,dt,J=17.1,8.7Hz),2.79-2.88(2H,m),7.25(2H,s),8.13(1H,d,J=8.1Hz),8.40(1H,dd,J=8.1,2.1Hz),9.12(1H,d,J=2.1Hz),10.30(1H,s)
(1)5-[(6a-メチル-5,6,6a,7,8,9-ヘキサヒドロ-4H-2-フェナレニル)カルボキサミド]ピリジン-2-カルボン酸メチル
1H-NMR(400MHz,CDCl3):δ1.17(3H,s),1.51(2H,td,J=12.9,5.1Hz),1.68-1.75(2H,m),1.79-1.90(2H,m),2.00-2.14(2H,m),2.84(2H,dt,J=17.4,8.4Hz),2.97(2H,ddd,J=17.4,7.8,3.3Hz),4.00(3H,s),7.40(2H,s),8.14(1H,br-s),8.16(1H,d,J=8.7Hz),8.56(1H,dd,J=8.7,2.4Hz),8.72(1H,d,J=2.4Hz)
1H-NMR(400MHz,DMSO-d6):δ1.11(3H,s),1.43(2H,td,J=12.9,4.8Hz),1.66(2H,dt,J=12.9,3.6Hz),1.71-1.81(2H,m),1.93-2.09(2H,m),2.80(2H,dt,J=17.4,8.7Hz),2.94(2H,ddd,J=17.4,8.1,3.3Hz),7.47(2H,s),8.04(1H,d,J=8.7Hz),8.36(1H,dd,J=8.7,2.4Hz),9.00(1H,d,J=2.4Hz),10.54(1H,s)
(1)5-[(6a-メチル-5,6,6a,7,8,9-ヘキサヒドロ-4H-2-フェナレニル)カルバモイル]チオフェン-2-カルボン酸メチル
1H-NMR(400MHz,CDCl3):δ1.15(3H,s),1.49(2H,td,J=12.9,5.4Hz),1.67(2H,dt,J=12.9,3.9Hz),1.75-1.86(2H,m),1.98-2.14(2H,m),2.78(2H,dt,J=17.3,8.7Hz),2.91(2H,ddd,J=17.3,7.8,3.3Hz),3.92(3H,s),7.13(2H,s),7.52(1H,d,J=3.9Hz),7.56(1H,br-s),7.76(1H,d,J=3.9Hz)
1H-NMR(400MHz,DMSO-d6):δ1.08(3H,s),1.38(2H,td,J=12.9,5.1Hz),1.61(2H,dt,J=12.6,3.9Hz),1.68-1.79(2H,m),1.88-2.04(2H,m),2.68(2H,dt,J=17.4,8.7Hz),2.82(2H,ddd,J=17.7,8.1,3.3Hz),7.20(2H,s),7.72(1H,d,J=3.9Hz),7.94(1H,d,J=3.9Hz),10.16(1H,s)
(1)5-[(6a-メチル-5,6,6a,7,8,9-ヘキサヒドロ-4H-2-フェナレニル)カルボキサミド]チオフェン-2-カルボン酸メチル
1H-NMR(400MHz,CDCl3):δ1.15(3H,s),1.49(2H,td,J=12.9,5.1Hz),1.69(2H,dt,J=12.9,3.9Hz),1.76-1.87(2H,m),1.97-2.12(2H,m),2.73-2.84(2H,m),2.88-2.96(2H,m),3.86(3H,s),6.76(1H,d,J=4.2Hz),7.39(2H,s),7.63(1H,d,J=4.2Hz),9.09(1H,br-s)
1H-NMR(400MHz,DMSO-d6):δ1.11(3H,s),1.42(2H,td,J=12.9,4.5Hz),1.62-1.69(2H,m),1.72-1.80(2H,m),1.92-2.08(2H,m),2.79(2H,dt,J=17.3,8.7Hz),2.94(2H,ddd,J=17.7,8.1,3.3Hz),6.91(1H,d,J=4.2Hz),7.48(2H,s),7.61(1H,d,J=4.2Hz),11.80(1H,s)
4-[(6a-メチル-5,6,6a,7,8,9-ヘキサヒドロ-4H-2-フェナレニル)スルファモイル]安息香酸
1H-NMR(400MHz,DMSO-d3):δ0.99(3H,s),1.29(2H,td,J=12.9,4.5Hz),1.50-1.57(2H,m),1.61-1.69(2H,m),1.81-1.95(2H,m),2.50-2.61(1H,m),2.64-2.74(4H,m),6.56(2H,s),7.85(2H,d,J=8.1Hz),8.05(2H,d,J=8.1Hz),10.14(1H,s)
(1)(6,7,8,9-テトラヒドロ-5-ベンゾシクロヘプテニリデン)酢酸エチル
1H-NMR(400MHz,CDCl3):δ1.22(3H,t,J=7.2Hz),1.47-1.64(2H,m),1.72-1.95(4H,m),2.65-2.79(2H,m),2.82-2.95(2H,m),3.43-3.52(1H,m),4.12(2H,q,J=7.2Hz),7.07-7.15(4H,m)
1H-NMR(400MHz,CDCl3):δ1.48-1.65(2H,m),1.73-1.90(4H,m),2.75-2.98(4H,m),3.53-3.61(1H,m),7.05-7.16(4H,m),9.80(1H,t,J=2.1Hz)
1H-NMR(400MHz,CDCl3):δ1.25(3H,t,J=7.2Hz),1.58-1.89(10H,m),2.32(2H,t,J=7.2Hz),2.83(3H,dd,J=11.4,4.8Hz),4.12(2H,q,J=7.2Hz),7.06-7.09(2H,m),7.10-7.12(2H,m)
1H-NMR(400MHz,CDCl3):δ1.51-1.92(10H,m),2.38(2H,t,J=7.2Hz),2.80-2.85(3H,m),7.07-7.12(4H,m)
1H-NMR(400MHz,CDCl3):δ1.45-1.54(1H,m),1.61-1.75(2H,m),1.92-1.99(7H,m),2.56-2.62(1H,m),2.81-2.97(3H,m),3.40-3.48(1H,m)7.13(1H,t,J=7.5Hz),7.20(1H,dd,J=7.5,1.5Hz),7.37(1H,dd,J=7.5,1.5Hz)
1H-NMR(400MHz,CDCl3):δ1.47-1.66(6H,m),1.78-1.96(6H,m),2.81-2.86(4H,m),3.20-3.29(1H,m)6.90-6.99(3H,m)
1H-NMR(400MHz,CDCl3):δ1.47-1.70(6H,m),1.78-1.98(6H,m),2.56(3H,s),2.90(4H,t,J=5.4Hz),3.24-3.31(1H,m),7.52(2H,s)
1H-NMR(400MHz,CDCl3):δ1.48-1.71(6H,m),1.78-1.96(6H,m),2.91(4H,t,J=5.4Hz),3.26-3.33(1H,m),7.67(2H,s)
1H-NMR(400MHz,CDCl3):δ1.44-1.64(6H,m),1.76-1.92(6H,m),2.70-2.76(4H,m),3.09-3.16(1H,m),3.43(2H,br-s),6.31(2H,s)
1H-NMR(400MHz,CDCl3):δ1.51-1.69(6H,m),1.79-1.95(6H,m),2.84(4H,t,J=5.4Hz),3.18-3.25(1H,m),3.96(3H,s),7.23(2H,s),7.69(1H,br-s),7.90(2H,d,J=8.7Hz),8.14(2H,d,J=8.7Hz)
1H-NMR(400MHz,DMSO-d6):δ1.34-1.59(6H,m),1.69-1.88(6H,m),2.71-2.80(4H,m),3.10-3.21(1H,m),7.27(2H,s),7.95(2H,d,J=8.1Hz),8.05(2H,d,J=8.1 Hz),10.17(1H,s)
(1)4-[(5,6,7,7a,8,9,10,11-オクタヒドロ-4H-2-ベンゾ[ef]ヘプタレニル)カルボキサミド]安息香酸メチル
1H-NMR(400MHz,CDCl3):δ1.51-1.71(6H,m),1.79-1.97(6H,m),2.92(4H,t,J=5.4Hz),3.26-3.33(1H,m),3.91(3H,s),7.42(2H,s),7.74(2H,d,J=8.7Hz),7.94(1H,br-s),8.05(2H,d,J=8.7Hz)
1H-NMR(400MHz,DMSO-d6):δ1.37-1.60(6H,s),1.70-1.90(6H,m),2.84-2.87(4H,m),3.20-3.31(1H,m),7.48(2H,s),7.83(2H,d,J=8.7Hz),7.89(2H,d,J=8.7Hz),10.32(1H,s)
2-フルオロ-4-[(5,6,7,7a,8,9,10,11-オクタヒドロ-4H-2-ベンゾ[ef]ヘプタレニル)カルボキサミド]安息香酸
1H-NMR(400MHz,CDCl3):δ1.51-1.71(6H,m),1.79-1.95(6H,m),2.91(4H,t,J=5.7 Hz),3.26-3.32 (1H,m),3.92(3H,s),7.31(1H,dd,J=8.4,2.1 Hz),7.41(2H,s),7.77(1H,dd,J=12.9,2.1 Hz),7.94(1H,br-s),7.95(1H,t,J=8.4 Hz)
1H-NMR(400MHz,DMSO-d6):δ1.43-1.56(6H,m),1.74-1.91(6H,m),2.88(4H,t,J=5.7Hz),3.11-3.19(1H,m),7.50(2H,s),7.62(1H,dd,J=8.7,2.1Hz),7.78-7.89(2H,m),10.47(1H,s)
2-クロロ-4-[(5,6,7,7a,8,9,10,11-オクタヒドロ-4H-2-ベンゾ[ef]ヘプタレニル)カルボキサミド]安息香酸
1H-NMR(400MHz,CDCl3):δ1.51-1.71(6H,m),1.79-1.98(6H,m),2.91(4H,t,J=5.7 Hz),3.25-3.32 (1H,m),3.92(3H,s),7.41(2H,s),7.65(1H,dd,J=8.7,2.1 Hz),7.84(1H,d,J=2.1 Hz), 7.91(1H,d,J=8.7 Hz),7.93(1H,br-s)
1H-NMR(400MHz,DMSO-d6):δ1.43-1.59(6H,m),1.72-1.90(6H,m),2.87(4H,t,J=5.4Hz),3.12-3.18(1H,m),7.50(2H,s),7.79(1H,dd,J=8.4,1.8Hz),7.84(1H,d,J=8.4Hz),8.02(1H,d,J=1.8Hz),10.38(1H,s)
2-ヒドロキシ-4-[(5,6,7,7a,8,9,10,11-オクタヒドロ-4H-2-ベンゾ[ef]ヘプタレニル)カルボキサミド]安息香酸
1H-NMR(400MHz,CDCl3):δ1.48-1.70(6H,m),1.78-1.96(6H,m),2.90(4H,t,J=5.7Hz),3.24-3.31(1H,m),3.94(3H,s),7.24(1H,dd,J=8.7,2.1Hz),7.30(1H,d,J=2.1Hz),7.40(2H,s),7.81(1H,d,J=8.7Hz),7.89(1H,br-s),10.86(1H,s)
1H-NMR(400MHz,DMSO-d6):δ1.43-1.59(6H,m),1.71-1.91(6H,m),2.87(4H,t,J=5.4Hz),3.06-3.13(1H,m),7.29(1H,dd,J=8.7,1.8Hz),7.48(2H,s),7.49(1H,d,J=1.8Hz),7.72(1H,d,J=8.7Hz),10.25(1H,s)
2-メトキシ-4-[(5,6,7,7a,8,9,10,11-オクタヒドロ-4H-2-ベンゾ[ef]ヘプタレニル)カルボキサミド]安息香酸
1H-NMR(400MHz,CDCl3):δ1.51-1.70(6H,m),1.79-1.97(6H,m),2.94(4H,t,J=5.7Hz),3.25-3.32(1H,m),3.88(3H,s),3.95(3H,s),6.96(1H,dd,J=8.7,2.1Hz),7.42(2H,s),7.82(1H,d,J=2.1Hz),7.85(1H,d,J=8.7Hz),7.96(1H,br-s)
1H-NMR(400MHz,DMSO-d6):δ1.43-1.56(6H,m),1.72-1.91(6H,m),2.88(4H,t,J=5.4Hz),3.06-3.15(1H,m),3.78(3H,s),7.43(1H,d,J=8.7Hz),7.50(2H,s),7.56-7.63(2H,m),10.21(1H,s)
6-[(5,6,7,7a,8,9,10,11-オクタヒドロ-4H-2-ベンゾ[ef]ヘプタレニル)カルバモイル]ニコチン酸
1H-NMR(400MHz,CDCl3):δ1.51-1.69(6H,m),1.79-1.94(6H,m),2.87(4H,t,J=5.4Hz),3.19-3.26(1H,m),4.00(3H,s),7.38(2H,s),8.36(1H,d,J=8.1Hz),8.49(1H,dd,J=8.1,1.8Hz),9.18(1H,d,J=1.8Hz),9.86(1H,br-s)
1H-NMR(400MHz,DMSO-d6):δ1.53-1.66(6H,m),1.79-1.91(6H,m),2.84-2.88(4H,m),3.19-3.26(1H,m),7.38(2H,s),8.39(1H,d,J=8.1Hz),8.54(1H,d,J=8.1),9.24(1H,s),9.86(1H,s)
6-[(5,6,7,7a,8,9,10,11-オクタヒドロ-4H-2-ベンゾ[ef]ヘプタレニル)カルボキサミド]ニコチン酸
1H-NMR(400MHz,CDCl3):δ1.50-1.71(6H,m),1.79-1.99(6H,m),2.92(4H,t,J=5.4Hz),3.26-3.33(1H,m),3.94(3H,s),7.49(2H,s),8.34(1H,dd,J=9.0,2.1Hz),8.47(1H,d,J=9.0Hz),8.74 (1H,br-s),8.93(1H,d,J=2.1Hz)
1H-NMR(400MHz,DMSO-d6):δ1.44-1.62(6H,m),1.73-1.93(6H,m),2.87-2.91(4H,m),3.25-3.68(1H,m),7.63(2H,s),8.28-8.91(2H,m),8.86(1H,s),10.87(2H,s)
2,6-ジフルオロ-4-[(5,6,7,7a,8,9,10,11-オクタヒドロ-4H-2-ベンゾ[ef]ヘプタレニル)カルボキサミド]安息香酸
1H-NMR(400MHz,CDCl3):δ1.39(3H,t,J=7.2Hz),1.50-1.70(6H,m),1.79-1.97(6H,m),2.90(4H,t,J=5.7 Hz),3.22-3.32(1H,m),4.40(2H,q,J=7.2Hz),7.36(2H,d,J=9.9Hz),7.39(2H,s),7.98(1H,br-s)
1H-NMR(400MHz,DMSO-d6):δ1.45-1.62(6H,m),1.73-1.94(6H,m),2.90(4H,t,J=6.0Hz),3.26-3.34(1H,m),7.51(2H,s),7.61(2H,d,J=10.8Hz),10.56(1H,s)
ヒト急性前骨髄球性白血病細胞株HL-60を5% FBS含有RPMI培地を用いてCO2インキュベーター内(5% CO2、37℃)で培養した。上記実施例で製造した本発明の化合物(いずれもカルボン酸化合物)のHL-60細胞に対する分化誘導作用を前骨髄球から顆粒球への分化度を指標としたニトロブルーテトラゾリウム(NBT)還元能により評価した。対数増殖期に入りコンフルエント程度に達した細胞を1000 rpmで5分間遠心し、培養上清を除去した。細胞ペレットを新たな5% FBS含有RPMI培地で8.0×104 cells/mlに調製し、次いでDMSOで溶解した被験化合物を目的濃度になるように添加し、4日間培養後に実験に供した。各サンプルについていずれもDMSO濃度が同じになるよう調製した。
Claims (3)
- 下記の一般式(I):
- R1が水素原子又はメチル基であり、A及びBが共に-(CH2)3-であるか、又は共に-(CH2)4-であり、Xが-NH-CO-又は-CO-NH-であり、Arがフェニレン基、モノフルオロフェニレン基、モノクロロフェニレン基、モノヒドロキシフェニレン基、モノアルコキシフェニレン基、ピリジンジイル基、又はチオフェンジイル基である請求項1に記載の一般式(I)で表される化合物又はその塩。
- 請求項1又は2に記載の化合物又は生理学的に許容されるその塩を有効成分として含むレチノイド作用剤。
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JP2009528146A JP5399248B2 (ja) | 2007-08-15 | 2008-08-14 | 3環系アミド化合物 |
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JP2009528146A JP5399248B2 (ja) | 2007-08-15 | 2008-08-14 | 3環系アミド化合物 |
PCT/JP2008/064576 WO2009022721A1 (ja) | 2007-08-15 | 2008-08-14 | 3環系アミド化合物 |
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JPWO2009022721A1 JPWO2009022721A1 (ja) | 2010-11-18 |
JP5399248B2 true JP5399248B2 (ja) | 2014-01-29 |
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US (1) | US8232300B2 (ja) |
EP (1) | EP2189443B1 (ja) |
JP (1) | JP5399248B2 (ja) |
CN (1) | CN101855199A (ja) |
AU (1) | AU2008287818A1 (ja) |
CA (1) | CA2695977A1 (ja) |
EA (1) | EA201070273A1 (ja) |
NZ (1) | NZ583876A (ja) |
TW (1) | TW200920351A (ja) |
WO (1) | WO2009022721A1 (ja) |
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ES2861268T3 (es) | 2011-09-20 | 2021-10-06 | Basf Se | Moduladores de bajo peso molecular del receptor de mentol frío TRPM8 y su uso |
CN107304172B (zh) * | 2016-04-20 | 2020-04-03 | 沈阳药科大学 | 八氢蒽类化合物及其制备方法和用途 |
Citations (1)
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JPH0344348A (ja) * | 1989-06-30 | 1991-02-26 | Firmenich Sa | 新規芳香族化合物、その製法、該化合物を含有する賦香組成物または香料添加製品、ならびに芳香特性を改良、強調または変更する方法および該化合物の中間体 |
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JPS6122047A (ja) | 1984-07-07 | 1986-01-30 | Koichi Shiyudo | 安息香酸誘導体 |
JPS6176440A (ja) | 1984-09-19 | 1986-04-18 | Koichi Shiyudo | 安息香酸誘導体 |
US5442124A (en) | 1989-06-30 | 1995-08-15 | Firmenich Sa | Process for the preparation of novel aromatic compounds |
US5185318A (en) | 1989-06-30 | 1993-02-09 | Firmenich S.A. | Aromatic compounds, a process for preparation thereof and use of same as perfuming ingredients |
US5420145A (en) * | 1993-03-22 | 1995-05-30 | Koichi Shudo | Carboxylic acid derivative |
US5977125A (en) * | 1994-10-31 | 1999-11-02 | Eisai Co., Ltd. | Mono-or polyenic carboxylic acid derivatives |
JP3964478B2 (ja) | 1995-06-30 | 2007-08-22 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ヘテロ環含有カルボン酸誘導体及びそれを含有する医薬 |
JP3044348B1 (ja) | 1998-12-28 | 2000-05-22 | 株式会社大阪冷研 | プリフォ―ム口首部の内径規制用コア |
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- 2008-08-14 EA EA201070273A patent/EA201070273A1/ru unknown
- 2008-08-14 EP EP08792457.7A patent/EP2189443B1/en not_active Not-in-force
- 2008-08-14 TW TW097130990A patent/TW200920351A/zh unknown
- 2008-08-14 US US12/673,207 patent/US8232300B2/en not_active Expired - Fee Related
- 2008-08-14 CN CN200880111357A patent/CN101855199A/zh active Pending
- 2008-08-14 AU AU2008287818A patent/AU2008287818A1/en not_active Abandoned
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JPH0344348A (ja) * | 1989-06-30 | 1991-02-26 | Firmenich Sa | 新規芳香族化合物、その製法、該化合物を含有する賦香組成物または香料添加製品、ならびに芳香特性を改良、強調または変更する方法および該化合物の中間体 |
Non-Patent Citations (3)
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JPN6008046075; LARS Eklund et al.: 'Synthetic studies towards pseudopterosin A' Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry No.4, 1996, P.303-305 * |
JPN7008006927; Edward PIERS et al.: 'Synthesis of functionalized hexahydro-, octahydro-, and decahydro-1H-phenalenes via Diels-Alder reac' Canadian Journal of Chemistry Vol.71, No.9, 1993, P.1463-1483 * |
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Also Published As
Publication number | Publication date |
---|---|
WO2009022721A1 (ja) | 2009-02-19 |
US8232300B2 (en) | 2012-07-31 |
CA2695977A1 (en) | 2009-02-19 |
EP2189443A1 (en) | 2010-05-26 |
EP2189443B1 (en) | 2013-10-23 |
EA201070273A1 (ru) | 2010-10-29 |
TW200920351A (en) | 2009-05-16 |
CN101855199A (zh) | 2010-10-06 |
AU2008287818A1 (en) | 2009-02-19 |
JPWO2009022721A1 (ja) | 2010-11-18 |
EP2189443A4 (en) | 2010-08-04 |
US20110213157A1 (en) | 2011-09-01 |
NZ583876A (en) | 2011-11-25 |
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