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Glucoside derivatives and pharmaceutical compositions thereof

A kind of drug and compound technology, applied in the field of a class of glucoside derivatives and pharmaceutical compositions thereof

Inactive Publication Date: 2015-08-05
JIANGSU ATOM BIOSCI & PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, SGLT1 inhibitors can also lower blood sugar, but because SGLT1 is distributed in many important organs such as the heart and brain, inhibiting SGLT1 may cause a variety of adverse reactions, and inhibiting SGLT1 in the intestine will affect the absorption of carbohydrates and cause diarrhea other gastrointestinal reactions

Method used

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  • Glucoside derivatives and pharmaceutical compositions thereof
  • Glucoside derivatives and pharmaceutical compositions thereof
  • Glucoside derivatives and pharmaceutical compositions thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] (2S,3R,4R,5S,6R)-2-{3-{Deutero[5-(4-fluorophenyl)selenophen-2-yl]methyl}-4-methylphenyl}-6 Synthesis of -(Hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (10)

[0070]

[0071] 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 dihydrogen phosphate (70 mL×2), water (50 mL), saturated brine (50 mL), and dried over anhydrous sodium sulfate. The solvent was distilled off...

Embodiment 2

[0082] (2S,3R,4R,5S,6R)-2-{3-{Dideutero[5-(4-fluorophenyl)selenophen-2-yl]methyl}-4-methylphenyl}- Synthesis of 6-(Hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (15)

[0083]

[0084]Step A: Dissolve compound 4 (300mg, 0.639mmol) in anhydrous THF (10mL), add sodium borodeuteride (80mg, 1.91mmol), then add boron trifluoride diethyl ether (364mg, 2.56mmol) dropwise in an ice-water bath ). Stirring was continued at this temperature for 20 minutes after the addition was complete, then the temperature was raised to room temperature and stirred for 1 hour, and then the temperature was raised to reflux and stirred overnight. Saturated brine (20 mL) was added, extracted with dichloromethane (15 mL×3), the combined organic layers were washed successively with saturated aqueous sodium bicarbonate (15 mL) and saturated brine (10 mL), and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the product was purified by column chromatography (200-...

Embodiment 3

[0087] (2S,3R,4R,5S,6R)-2-{3-{Deuterated[5-(4-fluorophenyl)selenophen-2-yl]methyl}-4-chlorophenyl}-6- Synthesis of (Hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (16)

[0088]

[0089] For the preparation method of compound 16, refer to Example 1, wherein 2-methyl-5-iodobenzoic acid in step D of Example 1 is replaced by 2-chloro-5-iodobenzoic acid. 1 H NMR (CD 3 OD, 300MHz) δ7.51-7.46(m, 3H), 7.39-7.36(m, 1H), 7.33-7.30(m, 1H), 7.24-7.23(m, 1H), 7.07-7.02(m, 2H) , 6.98-6.97(m, 1H), 4.31-4.27(m, 1H), 4.14-4.11(m, 1H), 3.89-3.85(m, 1H), 3.72-3.67(m, 1H), 3.43-3.39( m, 4H). MS (EI, m / z): 536.1 [M+Na] + .

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Abstract

The invention provides glucoside derivatives and pharmaceutical compositions thereof. The invention discloses chemical compounds as shown in general formula (I), pharmaceutically-acceptable salts thereof, easily-hydrolytic lipid prodrug thereof or isomers thereof, and the pharmaceutical compositions containing the chemical compounds which is used as sodium-glucose cotransporter 2 inhibitor used for treating or suspending relative diseases like diabetes mellitus, diabetic retinopathy, diabetic neuropathy, diabetic nephropathy and insulin resistance.

Description

technical field [0001] The present invention relates to a class of glucoside derivatives represented by general formula (I) or pharmaceutically acceptable salts or stereoisomers thereof, pharmaceutical compositions containing the derivatives thereof, and their use as therapeutic agents, especially Use as an inhibitor of sodium-glucose cotransporter 2 (SGLT2). Background technique [0002] With the improvement of people's living standards and changes in lifestyles, the number of diabetic patients has increased dramatically worldwide, and diabetes has become one of the main problems that endanger public health. According to figures released by the World Health Organization (WHO) in 2013, approximately 382 million adults worldwide suffer from diabetes. By 2035, the number of patients is expected to rise to 592 million. [0003] Early diabetes drugs include biguanides (such as metformin), sulfonylureas (such as glimepiride), glucosidase inhibitors (such as acarbose), oxazolidi...

Claims

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Application Information

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IPC IPC(8): C07D421/10A61K31/351A61P3/10A61P27/02A61P25/00A61P13/12A61P5/50A61P3/06A61P3/04A61P3/00A61P9/10A61P9/12
CPCA61K31/351C07D421/10
Inventor 史东方傅长金刘伟方飞曹成跑张长亮承曦
Owner JIANGSU ATOM BIOSCI & PHARMA CO LTD
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