Antipicornaviral compounds and compositions, their pharmaceutical uses, and materials for their synthesis
A compound and drug technology, applied in the field of compounds and analog peptides
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Embodiment 1
[0123] TMEDA (0.81 mL, 5.37 mmol) and dimethyl sulfide (0.49 mL, 6.67 mmol) were added to n-butyllithium (1.58 M in hexane, 3.4 mL, 5.37 mmol) at 0 °C under argon atmosphere ), the mixture was stirred for 5 hours while raising the temperature to 23°C, the reaction mixture was cooled to -40°C, and Cbz-L-Leu-L-Phe-L-(Tr-Gln)-N(CH 3 )OCH 3 (prepared as described in WIPO International Publication No. WO97 / 43305) (0.85 g, 1.03 mmol) in 9 mL of THF, the mixture was washed with 15 mL of 2N AcOH was quenched at -40 °C and extracted with excess EtOAc, the pH of the aqueous phase was measured with solid Na 2 CO 3 Adjusted to basic, extracted with EtOAc, combined the organic layers, and washed continuously with saturated NaHCO 3 and brine wash with MgSO 4 Drying, filtration and concentration in vacuo, column chromatography of the residue (45% EtOAc / Hexanes) provided the product as a white solid in 60% yield.
Embodiment 2
[0124] 1 H NMR (CDCl 3 )δ0.86(m, 6H), 1.31(m, 1H), 1.53(m, 2H), 1.75(m, 1H), 2.00(s, 3H), 2.27(m, 3H), 3.06(m, 2H ), 3.15(m, 2H), 3.93(m, 1H), 4.54(m, 1H), 4.70(m, 1H), 4.90(m, 2H), 6.50(m, 1H), 6.95(d, 1H, J=7.0), 7.14-7.41 (m, 27H).HRMSC 49 h 54 N 4 o 6 Calculated value of S (M+Cs). Measured value, (C 49 h 54 N 4 o 6 S·0.50H 2 O) Elemental Analysis C, H, N. Embodiment 2: Cbz-L-Leu-L-Phe-L-(Gln)-CH 2 SCH 3
[0125] Cbz-L-Leu-L-Phe-L-(Tr-Gln)-CH 2 SCH 3(0.30 g, 0.363 mmol) was added to 1:1 CH at 0 °C 2 Cl 2 and TFA and stirred for 45 min, the reaction mixture was concentrated in vacuo and extracted with excess EtOAc, the solution was washed with saturated NaHCO 3 and washed twice with brine, MgSO 4 dried, filtered and concentrated in vacuo, the residue was washed with Et 2 O Trituration yielded 0.15 g (71% yield) of the product as a white solid. 1 H NMR (DMSO-d 6 )δ0.80(d, 3H, J=6.6), 0.83(d, 3H, J=7.0), 1.33(m, 3H), 1.47(m, 1H), 1.72(m, 1H), 1.98(s, 3H...
Embodiment 3
[0125] Cbz-L-Leu-L-Phe-L-(Tr-Gln)-CH 2 SCH 3(0.30 g, 0.363 mmol) was added to 1:1 CH at 0 °C 2 Cl 2 and TFA and stirred for 45 min, the reaction mixture was concentrated in vacuo and extracted with excess EtOAc, the solution was washed with saturated NaHCO 3 and washed twice with brine, MgSO 4 dried, filtered and concentrated in vacuo, the residue was washed with Et 2 O Trituration yielded 0.15 g (71% yield) of the product as a white solid. 1 H NMR (DMSO-d 6 )δ0.80(d, 3H, J=6.6), 0.83(d, 3H, J=7.0), 1.33(m, 3H), 1.47(m, 1H), 1.72(m, 1H), 1.98(s, 3H), 2.05(m, 2H), 2.83(dd, 1H, J=14.0, 8.0), 3.05(dd, 1H, J=14.0, 4.4), 3.27(m, 2H), 3.98(m, 1H), 4.38(m, 1H), 4.52(m, 1H), 5.02(m, 2H), 6.78(s, 1H), 7.14-7.35(m, 11H), 7.42(d, 1H, J=7.7), 8.03( d, 1H, J=7.7), 8.42(d, 1H, J=7.4).HRMSC 30 h 40 N 4 o 6 Calculated value of S (M+H), 585.2747; measured value, 585.2720. (C 30 h 40 N 4 o 6 S) Elemental analysis C, H, N. Example 3: Cbz-L-Leu-L-Phe-L-(N-Ac-amino-Ala)-CH 2 O C(O...
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