Pharmaceutical composition comprising 7-azaidolin-2-one derivative or pharmaceutically acceptable salt thereof as an active ingredient
A technology of medicinal salts and compounds, which is applied in the field of pharmaceutical compositions for the prevention or treatment of cancer diseases, can solve problems such as improving the viability of cancer patients, and achieve the effect of inhibiting cancer growth and cancer metastasis
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Embodiment 1
[0161] 5-(hydroxymethyl)-2, the preparation of 4-lutidine-3-alcohol hydrochloride (2)
[0162] After zinc (Zn) powder (12.7 g, 0.195 mol) was added in small portions to a solution of pyridoxine hydrochloride (1, 10.0 g, 48.6 mmol) in acetic acid (40 mL), the mixture was refluxed for 24 hours. After cooling the reaction mixture to room temperature, the reaction mixture was filtered under reduced pressure and washed with acetonitrile (CH 3 CN, 50 mL), and excess hydrochloric acid-methanol solution (150 mL) was added to the filtrate. After stirring under ice cooling for 2 hours, the resulting suspension was filtered under reduced pressure to obtain the desired compound 2 (8.7 g, 94%) as a white solid.
[0163] 1 H-NMR ((CD3)2SO) δ10.62 (br s, 1H), 8.08 (s, 1H), 5.70 (br s, 1H), 4.60 (s, 2H), 2.61 (s, 3H), 2.32 ( s, 3H).
Embodiment 2
[0164] Preparation of (5-(benzyloxy)-4,6-dimethylpyridin-3-yl)methanol (3)
[0165] Potassium carbonate (107 g, 0.776 mol) and benzyl chloride (26.2 mL, 0.228 mol) were added to a solution of compound 2 (8.6 g, 45.7 mmol) in DMF (N,N-dimethylformamide, 450 mL) Afterwards, the mixture was stirred at room temperature for 24 hours. After the reaction solution was concentrated under reduced pressure, the reaction solution was diluted with ethyl acetate (EtOAc, 1 L) and washed with water (3×100 mL). The ethyl acetate solution was washed with saturated brine, and anhydrous magnesium sulfate (MgSO 4 ) was dried and filtered, and concentrated under reduced pressure. The residue was subjected to column chromatography (CH 2 Cl 2 :MeOH=20:1) to obtain the desired compound 3 (8.2 g, 74%) as a brown solid.
[0166] 1 H-NMR (CDCl3) δ8.07(s, 1H), 7.38-7.47(m, 5H), 4.80(s, 2H), 4.65(s, 2H), 2.48(s, 3H), 2.32(s, 3H) ).
Embodiment 3
[0167] The preparation of 3-benzyloxy-5-chloromethyl-2,4-lutidine hydrochloride (4)
[0168] DMF (0.09 mL, 23.43 mmol) and thionyl chloride (1.7 mL, 23.43 mmol) were added to a solution of compound 3 (2.85 g, 11.71 mmol) in 1,2-dichloroethane (35 mL), and The mixture was stirred at 80°C for 1 hour. After cooling the reaction solution to room temperature, diethyl ether (150 mL) was added to the reaction solution, followed by stirring under ice-cooling for 1 hour. After the precipitated solid was filtered under reduced pressure, the filtered solid was washed with diethyl ether and dried to obtain the desired compound 4 (3 g, 86%) as a brown solid.
[0169] 1 H-NMR (CDCl3) δ8.19(s, 1H), 7.34-7.44(m, 5H), 4.81(s, 2H), 4.56(s, 2H), 2.50(s, 3H), 2.32(s, 3H) ).
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