Pharmaceutical composition comprising a pyrazole-o-glucoside derivative
A technology of glycoside derivatives and glucopyranose, applied in the field of pharmaceutical compositions containing pyrazole-O-glucoside derivatives, can solve problems such as deterioration and blood sugar control deterioration, increase the number and size, delay or prevent β Effects of cell degeneration, improvement or restoration of pancreatic cell function
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[0219] According to a fourth preferred embodiment, aspects of the invention (especially pharmaceutical compositions, methods and uses) relate to
[0220] (16) 4-(2-fluoro-4-methoxy-benzyl)-1-isopropyl-5-methyl-3-β-D-glucopyranose-1-yloxy-1H-pyridine azole;
[0221] or its prodrug, wherein the hydroxyl group connected to the 6 carbon atoms of the β-D-glucopyranosyl group is substituted by a substituent selected from (C 1-3 -Alkyl)carbonyl, (C 1-6 -alkyl)oxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl and benzylcarbonyl, especially selected from acetyl, methoxycarbonyl and ethoxycarbonyl; eg compounds (47) and (72).
[0222] According to a fifth preferred embodiment, aspects of the invention (especially pharmaceutical compositions, methods and uses) relate to
[0223] (20) 4-(2-fluoro-4-ethoxy-benzyl)-1-isopropyl-5-methyl-3-β-D-glucopyranose-1-yloxy-1H-pyridine azole;
[0224] or its prodrug, wherein the hydroxyl group connected to the 6 carbon atoms of the β-D-glucopyran...
Embodiment I
[0379] 2-fluoro-4-hydroxy-benzaldehyde
[0380]
[0381] CH 2 Cl 2 (100mL) solution was added CH of boron tribromide 2 Cl 2 solution (1M, 160 mL, 160 mmol). After stirring the reaction solution at -68°C for 45 minutes, the cooling bath was removed, and the solution was further stirred at room temperature overnight. The reaction solution was poured into ice water and stirred for 30 minutes. The formed precipitate was separated with CH 2 Cl 2 Washed and dissolved in EtOAc. The resulting EtOAc phase was washed with water and washed with MgSO 4 dry. After evaporating the solvent, use a small amount of CH 2 Cl 2 The residue was washed and dried under vacuum to give the product as a beige solid.
[0382] Yield: 14.5g (86%)
[0383] ESI-MS: m / z=139[M-H] -
Embodiment II
[0385] 4-Benzyloxy-3-fluoro-benzaldehyde
[0386]
[0387] To a suspension of 4-hydroxy-3-fluoro-benzaldehyde (10.0 g, 70 mmol) and potassium carbonate (10.2 g, 74 mmol) in DMF (60 mL) was added benzyl bromide (8.7 mL, 74 mmol) dropwise. The mixture was stirred at ambient temperature for 48 hours and then quenched with ice water. The mixture was further diluted with water, and the precipitate was isolated by filtration. The precipitate was washed with water and dissolved in ethyl acetate. The organic solution was washed with brine, dried over sodium sulfate and the solvent was removed under vacuum.
[0388] Yield: 16.0g (99%)
[0389] ESI-MS: m / z=231[M+H] +
[0390] The following compounds can be obtained in a similar manner:
[0391] (1) 4-Benzyloxy-2-fluoro-benzaldehyde
[0392]
[0393] ESI-MS: m / z=253[M+Na] +
[0394] (2) 2-Chloro-4-methoxy-1-methyl-benzene
[0395]
[0396] The procedure above was followed except that methyl iodide was used instead of b...
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