Novel SGLT2 inhibitor compounds and pharmaceutical composition thereof
A compound and drug technology, applied in the field of sodium-glucose cotransporter SGLT2 inhibitors, can solve hypoglycemia and other problems
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0083] (3R,4S,5S,6R)-2-{3-[(5-(4-Fluorophenyl)selenophen-2-yl)methyl]-4-methylphenyl}-6-hydroxymethyl -2-Methoxytetrahydro-2H-pyran-3,4,5-triol (7) and (2S,3R,4R,5S,6R)-2-{3-{[5-(4- Fluorophenyl)selenophen-2-yl]methyl}-4-methylphenyl}-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (10) synthesis
[0084]
[0085] Step A: D-gluconolactone (5.0g, 28.1mmol) and N-methylmorpholine (23.3g, 222mmol) were dissolved in THF (50mL), and trimethylchlorosilane (18.3 g, 168 mmol). Stirring was continued at this temperature for 1 hour after the addition was complete, and then the mixture was naturally warmed to room temperature and stirred overnight. Toluene (200 mL) was added, and ice water (200 mL) was added dropwise under an ice-water bath to control the inner temperature not to exceed 10°C. Separate the layers, collect the organic layer, and extract the aqueous layer with toluene (50 mL). The combined organic layers were washed successively with saturated aqueous sodium dihydr...
Embodiment 2
[0100] (2S,3R,4R,5S,6R)-2-{3-{[5-(3,4-Difluorophenyl)selenophen-2-yl]methyl}-4-methylphenyl}- Synthesis of 6-(Hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (11)
[0101]
[0102] For the preparation method, refer to Example 1, wherein 4-fluorophenylboronic acid in step C of Example 1 is replaced with 3,4-difluorophenylboronic acid.
[0103] 1 H NMR (CD 3 OD, 500MHz) δ7.40-7.36(m, 1H), 7.31(s, 1H), 7.28(d, J=4.0Hz, 1H), 7.25-7.23(m, 2H), 7.22-7.14(m, 2H ), 6.90(d, J=3.5Hz, 1H), 4.20-4.19(m, 2H), 4.12-4.10(m, 1H), 3.89-3.87(m, 1H), 3.71-3.68(m, 1H), 3.47-3.36 (m, 4H), 2.29 (s, 3H). MS (EI, m / z): 533.1 [M+Na] + .
Embodiment 3
[0105] (2S,3R,4R,5S,6R)-2-{3-{[5-(4-Chlorophenyl)selenophen-2-yl]methyl}-4-methylphenyl}-6-( Synthesis of Hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (12)
[0106]
[0107] For the preparation method, refer to Example 1, wherein 4-fluorophenylboronic acid in step C of Example 1 is replaced with 4-chlorophenylboronic acid.
[0108] 1 H NMR (CD 3 OD, 500MHz) δ7.46-7.44(m, 2H), 7.31-7.29(m, 4H), 7.25-7.24(m, 1H), 7.16-7.14(m, 1H), 6.90-6.89(m, 1H) , 4.23-4.19(m, 2H), 4.16-4.08(m, 1H), 3.89-3.87(m, 1H), 3.71-3.68(m, 1H), 3.48-3.36(m, 4H), 2.30(s, 3H). MS (EI, m / z): 531.0 [M+Na] + .
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More 
PatSnap Eureka turns technology decisions into work you can execute. Powered by our Innovation Knowledge Graph, it runs expert workflows across engineering, life sciences, materials and intellectual property. Get your review-ready output in minutes.
