Novel compound, pharmaceutically acceptable salt or optical isomer thereof, method for preparing same, and pharmaceutical composition for prevention or treatment of viral diseases containing same as active ingredient
A technology of optical isomers, compounds, applied to novel compounds, pharmaceutically acceptable salts or optical isomers thereof, drugs for the preparation of them and drugs for preventing or treating viral diseases containing them as active ingredients In the field of composition, it can solve problems such as side effects, low treatment success rate, and unapproved antiviral drugs, and achieve low cytotoxicity
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Embodiment 1
[0190] N-(4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-benzo[d]indeno[1,2-b]furan-9b- Preparation of -2-(1H-indol-3-yl)-2-oxoacetamide
[0191] 2-(1H-indol-3-yl)-2-oxoacetic acid (352mg, 1.86mmol), EDCI (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide) (355mg, 1.86mmol) and HOBt (hydroxybenzotriazole) (251mg, 1.86mmol) were dissolved in dichloromethane (MC) (10ml), then added 9b-amino-4b-hydroxy-7-isopropyl- 4bH-Benzo[d]indeno[1,2-b]furan-10(9bH)-one (500 mg, 1.69 mmol) and the mixture was stirred at room temperature for one day. The reaction mixture was extracted with dichloromethane to collect the organic layer, which was dissolved in MgSO 4 Dry under low temperature and concentrate under reduced pressure. The concentrated compound was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1) to obtain N-(4b-hydroxy-7-isopropyl-10-oxo-9b,10-dihydro-4bH-benzo [d] Indeno[1,2-b]furan-9b-yl)-2-(1H-indol-3-yl)-2-oxoacetamide (199 mg, 25%).
[0192] 1 H-NM...
Embodiment 2
[0194] N-(4b-hydroxy-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno[1,2-b]benzofuran-9b-yl)- Preparation of 2-oxo-2-(thiophen-2-yl)acetamide
[0195] After dissolving 2-oxo-2-(thiophen-2-yl)acetic acid (107mg, 1.07mmol) in DMF (3ml), the temperature was lowered to 0°C, and the solution was stirred. After 10 minutes, triethylamine (TEA) (213mg, 1.07mmol) and HATU (407mg, 1.07mmol) were added, stirred for 10 minutes before the temperature dropped to 0°C, and 9b-amino-4b-hydroxy-7-isopropyl yl-4bH-indeno[1,2-b]benzofuran-10(9bH)-one (300 mg, 1.02 mmol). Then, the temperature was raised to normal temperature, and the solution was stirred overnight. After washing with water, Na 2 SO 4 Remove moisture. After filtration and concentration, it was purified by column chromatography (EA:Hex=3:7) to obtain the title compound (52mg, 28%).
[0196] 1 H-NMR (300MHz, DMS0-d6) δ1.12 (d, 6H, J = 6.0Hz), 4.13 (q, 1H, J = 6.0Hz), 4.72 (s, 1H), 6.88 (d, 1H, J =6.0Hz),7.32(d,2H,J=6.0Hz),7.63...
Embodiment 3
[0198] N-(4b-hydroxyl-7-isopropyl-10-oxo-9b, 10-dihydro-4bH-indeno[1,2-b]benzofuran-9b-yl)- Preparation of 3-(2-nitrophenyl)-2-oxopropionamide
[0199] 2-Nitrophenylpyruvate (390mg, 1.86mmol) was placed in DMF:DCM (1:2, 15ml), and EDCI (487mg, 2.54mmol) was added at 0°C. Then, after adding 1-hydroxybenzotriazole (343 mg, 2.54 mmol), the mixture was stirred at room temperature for 15-30 minutes. Then, after adding 9b-amino-4b-hydroxyl-7-isopropyl-4bH-indeno[1,2-b]benzofuran-10(9bH)-one (500mg, 1.69mmol), TEA was added ( 0.709ml, 5.09mmol). After stirring at 60°C for 2 days, water (100ml) was added. The separated organic layer was collected and ethyl acetate (70mlx3), washed with water (50ml) and brine (50ml), and the water was removed with sodium sulfate. After concentration, it was purified by silica gel column chromatography (25% ethyl acetate: hexane) to obtain 100 mg (24%) of the title compound.
[0200] 1 H-NMR (300MHz, CDC1 3 )δ1.18(dd, J=2.7Hz, J=6.9Hz, 6H, CH3),...
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