Cathepsin cysteine protease inhibitors
A compound, alkyl technology, applied in the field of cathepsin cysteine protease inhibitors, can solve problems such as inactivity
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Embodiment 1
[0218] N 1 -(2-oxotetrahydrofuran-3-yl)-N 2 -{(1S)-2,2,2-Trifluoro-1-[4'-(methylsulfonyl)biphenyl-4-yl]ethyl}-L-leucinamide
[0219]
[0220] Under stirring at room temperature within 30 minutes, to N-{(1S)-2,2,2-trifluoro-1-[4'-(methylsulfonyl)biphenyl-4-yl]ethyl}-L - Leucine (30 mg, 68 μmol), benzotriazol-1-yl-oxotripyrrophosphine hexafluorophosphate (40 mg, 77 μmol) and α-amino-γ-butyrolactone (26 mg, 140 μmol) in DMF (0.20ml) was added triethylamine (30μl, 220μmol). The mixture was partitioned between ethyl acetate and water and the layers were separated. The organic phase was washed with brine, dried (sodium sulfate) and concentrated, and purified by flash chromatography on silica gel eluting with ethyl acetate to afford the title compound as a colorless solid. MS(+ESI):527.2(M+1) + .
[0221] h 1 NMR (acetone-d 6 , 500MHz) δ8.06 (4H, d), 8.00-7.95 (4H, m), 7.90 (1H, m), 7.83 (1H, overlapping m), 7.80 (4H, d), 7.67 (4H, t), 4.58(2H,m), 4.45(2H,m), 4.37(2H,m),...
Embodiment 2
[0223] N 1 -[2-Oxo-1-(phenylsulfonyl)pyrrolidin-3-yl]-N2 -{(1S)-2,2,2-Trifluoro-1-[4'-(methylsulfonyl)biphenyl-4-yl]ethyl}-L-leucinamide
[0224]
[0225] Under stirring at room temperature within 2.5 hours, to N-{(1S)-2,2,2-trifluoro-1-[4'-(methylsulfonyl)biphenyl-4-yl]ethyl}-L -Leucine (40 mg, 90 μmol), benzotriazol-1-yl-oxotripyrrophosphine hexafluorophosphate (55 mg, 110 μmol) and (54 mg, 220 μmol) in DMF (0.2ml) were added tris Ethylamine (30 μl, 220 μmol). The mixture was partitioned between ethyl acetate and water and the layers were separated. The organic phase was washed with brine, dried (sodium sulfate) and concentrated, and purified by flash chromatography on silica gel eluting with 3 / 2 ethyl acetate / hexanes to give the title compound as a colorless thick syrup. MS(+ESI):666.3(M+1) + .
[0226] h 1 NMR (acetone-d 6 , 500MHz) δ8.07-7.97 (8H, d), 7.96-7.92 (4H, m), 7.86-7.70 (8H, m), 7.65-7.57 (8H, m), 4.54 (2H, m), 4.40 ( 2H, m), 3.93 (2H, m), 3.80 (2H, ...
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