Optimized medicine combination and application thereof for treating cancers and autoimmune diseases
A disease and compound technology, applied in the field of inhibition of Brutonine kinase activity, combined drug optimization and screening, can solve problems such as affecting drug efficacy and side effects, and achieve the effect of reducing drug inactivation
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Embodiment 1 and 2
[0103]
[0104] 1-[(R)-3-[4-amino-3-[2-fluoro-4-(2,3,5,6-trifluorophenoxy)phenyl]-1H-pyrazolo[3, 4-d]pyrimidin-1-yl]-1-piperidinyl]-2-propen-1-one
[0105]
[0106] 1-[(S)-3-[4-amino-3-[2-fluoro-4-(2,3,5,6-trifluorophenoxy)phenyl]-1H-pyrazolo[3, 4-d]pyrimidin-1-yl]-1-piperidinyl]-2-propen-1-one
[0107] Step A:
[0108]
[0109] 3-(4-Bromo-3-fluorophenoxy)-1,2,4,5-tetrafluorobenzene
[0110] Steps:
[0111] To a solution of compound 3-fluoro-4-bromophenol (47.0 g, 246.1 mmol, 1.0 eq.) in DMF (500 mL) was added potassium carbonate (68.0 g, 492.1 mmol, 2.0 eq.) and compounds 1, 2, 3, 4,5-Pentafluorobenzene (49.6 g, 295.3 mmol, 1.2 eq.). The reaction solution was stirred at 100°C for 12 hours, and the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate (300 mL), washed twice with water (100 mL) and once with saturated brine (100 mL). The organic phase was dried over anhydrous sodium sulfate, concentrated and spin-dried to o...
Embodiment 1
[0159] LC / MS (Method: UFLC): RT = 3.002 min; m / z = 531.1 [M+H] + ; The total run time is 7 minutes.
[0160] 1 H NMR (400MHz, CDCl 3 ) 8.36(s, 1H), 7.58(t, J=8.4Hz, 1H), 7.09-7.04(m, 1H), 6.94-6.88(m, 2H), 6.62-6.54(m, 1H), 6.32- 6.25(m, 1H), 5.73-5.63(m, 1H), 5.56-5.51(m, 1H), 4.90-4.85(m, 1.5H), 4.59-4.56(m, 0.5H), 4.21-4.17(m , 0.5H), 4.04-4.01(m, 0.5H), 3.76-3.71(m, 0.5H), 3.40-3.35(m, 0.5H), 3.22-3.15(m, 0.5H), 2.93-2.87(m , 0.5H), 2.39-2.27(m, 2H), 2.04-1.68(m, 2H).
Embodiment 2
[0162] LC / MS (Method: UFLC): RT = 3.006 min; m / z = 531.1 [M+H] + ; The total run time is 7 minutes.
[0163] 1 H NMR (400MHz, CD 3 OD) 8.24 (s, 1H), 7.62 (t, J=8.4Hz, 1H), 7.50-7.45 (m, 1H), 7.09-7.01 (m, 2H), 6.85-6.63 (m, 1H), 6.21 -6.09(m, 1H), 5.77-5.61(m, 1H), 4.63-4.59(m, 1H), 4.23-4.07(m, 1.5H), 3.90-3.85(m, 0.5H), 3.51-3.45( m, 0.5H), 3.34-3.17(m, 1.5H), 2.40-2.23(m, 2H), 2.08-2.05(m, 1H), 1.75-1.71(m, 1H).
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