Bicyclic fused pyrazole derivatives for the treatment of rsv
A compound, bicyclic heteroaryl technology, applied in the field of small molecule therapeutics, can solve unmet problems, high cost, preventing large-scale implementation, etc.
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Embodiment 1
[0194] Process for the preparation of series A compounds
[0195] In all experimental data reported below, the following abbreviations are used:
[0196] rt: room temperature
[0197] UV: Ultraviolet
[0198] HPLC: High Pressure Liquid Chromatography
[0199] Rt: retention time
[0200] LCMS: Liquid Chromatography Mass Spectrometry
[0201] NMR: Nuclear Magnetic Resonance Spectroscopy
[0202] CC: Column chromatography
[0203] TLC: Thin Layer Chromatography
[0204] sat: saturated
[0205] aq: water-based
[0206] DCM: dichloromethane
[0207] DCE: Dichloroethane
[0208] DMF: Dimethylformamide
[0209] DIPEA: Diisopropylethylamine
[0210] EtOAc: ethyl acetate
[0211] TEA: Triethylamine
[0212] THF: Tetrahydrofuran
[0213] TFA: trifluoroacetic acid
[0214] t-BuOK: Potassium tert-butoxide
[0215] n-BuOH: n-butanol
[0216] EtOH: Ethanol
[0217] HOAc: acetic acid
[0218] o / n: overnight
[0219] MW: microwave
[0220] h: hours
[0221] min: minutes...
Embodiment 1A
[0224] Example 1A: Conventional Synthesis Method A1
[0225]
[0226] Exemplary experimental procedure for conventional method A1
[0227] 1.4-(3-(Cyclopentyloxy)-4-methoxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-b]pyridine-6(7H )-keto (AVG-065) was synthesized as follows:
[0228]
[0229] Compound M2 (200 mg, 1.3 mmol), 2,2-dimethyl-1,3-dioxane-4,6-dione (272 mg, 1.9 mmol) and 3-(cyclopentyloxy)-4- A mixture of methoxybenzaldehyde (415 mg, 1.9 mmol) in EtOH (10 mL) was refluxed for 16 h. After cooling to room temperature, the mixture was concentrated in vacuo. The residue was diluted with water and extracted with EtOAc (30 mL x 2). The organic layer was washed with water and brine, filtered through Na 2 SO 4 Drying, filtration and concentration gave crude product, which was purified by preparative TLC to give compound AVG-065 (50 mg, 10% yield) as a white solid.
[0230]Agilent LCMS1200-6110, column: Waters X-Bridge C18 (50mm*4.6mm*3.5μm); column temperature...
Embodiment 1B
[0239] Example 1B: Conventional Synthesis Method A2
[0240]
[0241] Exemplary experimental procedure for conventional method A2
[0242] 1. Synthesis of 3-(2-(2,4-dimethoxybenzylidene)hydrazino)propionitrile (F2-2)
[0243]
[0244] Hydrazine hydrate (80%, 5.0 g, 124 mmol) was added to a stirred solution of acrylonitrile (6.0 g, 113 mmol) in THF (50 mL) cooled to 0°C over a period of about 20 min, then the reaction mixture was stirred at room temperature 2h. 2,4-Dimethoxybenzaldehyde (19.7 g, 119 mmol) was added to the reaction mixture over a period of about 15 min, and the reaction mixture was stirred at room temperature for 4 h. Crude oil was then obtained by concentration, which was used directly in the next step.
[0245] Agilent LCMS1200-6110, column: Waters X-Bridge C18 (50mm*4.6mm*3.5μm); column temperature: 40°C; flow rate: 2.0mL / min; mobile phase: from 95% [water+0.05% in 1.6min] TFA] and 5% [CH 3 CN+0.05%TFA] to 0%[Water+0.05%TFA] and 100%[CH 3 CN+0.05%...
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