O-galactoside derivative with nitrobenzene thiazolyl and preparation method and application thereof
A compound and general formula technology, applied in the field of type 2 sodium-dependent glucose transporter inhibitors, can solve problems such as side effects and difficulty in controlling blood sugar in patients
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Embodiment 1
[0030]
[0031] 2.34 g (10 mmol) of II-1 and 3.48 g (10 mmol) of compound III were refluxed overnight in 20 mL of dry THF under nitrogen protection. TLC showed the reaction was complete. The reaction compound was poured into 100 mL of ice water, stirred, extracted with 50 mL×3 dichloromethane, combined and extracted organic phases, washed with saturated brine, dried over anhydrous sodium sulfate, and evaporated to dryness on a rotary evaporator to obtain a column of residue Purified by chromatography to obtain product IV-1, a white solid, ESI-MS, m / z=305 ([M+H] + ).
[0032] 2.43g (8mmol) of compound IV-1 was dissolved in 20mL of 95% ethanol, and 0.5g of Raney nickel was added, followed by catalytic hydrogenation at room temperature of 0.2MPa. After 12 hours the reaction was complete. The reaction mixture was suction filtered to remove the catalyst, the filtrate was evaporated to dryness on a rotary evaporator, and the residue obtained was V-1, a white solid, ESI-MS, m / z...
Embodiment 2-3
[0037] With reference to the operating steps of Example 1, the compounds listed in the following table have been prepared:
[0038]
[0039]
Embodiment 4
[0040] The preparation of embodiment 4 reference compound D1
[0041] In order to fully illustrate the beneficial effects of the compounds of the present invention, the applicant has recorded the findings during the experiment
[0042] Compound D1 (undisclosed) of the following formula is used as a pharmacodynamic reference compound.
[0043]
[0044] The synthesis method is as follows:
[0045]
[0046] 1.89 g (10 mmol) of II-4 and 3.48 g (10 mmol) of compound III were refluxed overnight in 20 mL of dry THF under nitrogen protection. TLC showed the reaction was complete. The reaction compound was poured into 100 mL of ice water, stirred, extracted with 50 mL×3 dichloromethane, combined and extracted organic phases, washed with saturated brine, dried over anhydrous sodium sulfate, and evaporated to dryness on a rotary evaporator to obtain a column of residue Purified by chromatography to obtain product IV-4, a white solid, ESI-MS, m / z=260 ([M+H] + ).
[0047] 2.07g ...
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