Cathepsin inhibitors
A cathepsin, compound technology, applied in anti-inflammatory agents, drug combinations, non-central analgesics, etc., can solve problems such as inactivating proteins
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Embodiment 1
[0249] N 1 -(cyanomethyl)-N 2 -Synthesis of -(2,2,2-trifluoro-1-phenylethyl)-L-leucine amide
[0250]
[0251] To a solution of L-leucine methyl ester hydrochloride (975 mg, 5.37 mmol) in dichloromethane (30 mL) was added 2,2,2-trifluoroacetophenone (0.75 mL, 5.34 mmol) and diisopropyl Ethylamine (3.5 mL, 20 mmol). TiCl dissolved in 0.45mL dichloromethane solution was added dropwise 4 (0.55 mL, 5.0 mmol), and the mixture was stirred overnight. Then add additional TiCl 4 (0.4 mL, 3.6 mmol), and the mixture was stirred for 3 h. Join NaCNBH 3 (1050 mg, 16.7 mmol) in methanol (20 mL), and the mixture was stirred for 2 h. Poured into 1N NaOH and extracted with ethyl acetate (2x). The organic phase was washed with 1N NaOH and brine, followed by MgSO 4 Dry and evaporate. Purification by ISCO column chromatography (30% to 90% ethyl acetate / hexanes gradient) yielded methyl N-(2,2,2-trifluoro-1-phenethyl)-L-white ester.
[0252] To a room temperature solution of methyl N-(...
Embodiment 2
[0256] N 2 -[1-(-4-Bromophenyl)-2,2,2-trifluoroethyl]-N 1 Synthesis of -(cyanomethyl)-L-leucine amide
[0257]
[0258] Using the method of Example 1, N 2 ~[1-(4-bromophenyl)-2,2,2-trifluoroethyl]-N 1 -(cyanomethyl)-L-leucine amide.
[0259] MS (-ESI): 403.9, 405.9 [M-1] -
Embodiment 3
[0261] N 1 -(cyanomethyl)-N 2 -{[4'-((methylsulfonyl))-1,1'-biphenyl-4-yl][4-((methylsulfonyl))phenyl]methyl}-L-leucine amide Synthesis
[0262]
[0263] Step 1: N-{(4-bromophenyl)[4-((methylsulfonyl))phenyl]methylene}-L-leucine methyl ester
[0264] (4-bromophenyl)[4-((methylsulfonyl))phenyl]methanone (202mg, 0.59mmol), L-leucine methyl ester hydrochloride (328mg, 2.0mmol) and camphorsulfonic acid (52 mg, 0.22 mmol in toluene was refluxed for 18 h using a Dean-Stark trap. The solvent was removed in vacuo and the residue was purified by chromatography using EtOAc and hexanes as eluents to afford the title compound along with the starting material ( A mixture of 4-bromophenyl)[4-((methylsulfonyl))phenyl]methanone in a ratio of 1:1.
[0265] Step 2: N-{(4-bromophenyl)[4-((methylsulfonyl))phenyl]methyl}-L-leucine methyl ester
[0266] To N-{(4-bromophenyl)[4-((methylsulfonyl))phenyl]methylene}leucine methyl ester and (4-bromophenyl Base)[4-((methylsulfonyl))phenyl]methan...
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