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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

Inactive Publication Date: 2015-06-03
JIANGSU ATOM BIOSCI & PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main side effect of sulfonylureas is hypoglycemia

Method used

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  • Novel SGLT2 inhibitor compounds and pharmaceutical composition thereof
  • Novel SGLT2 inhibitor compounds and pharmaceutical composition thereof
  • Novel SGLT2 inhibitor compounds and pharmaceutical composition thereof

Examples

Experimental program
Comparison scheme
Effect test

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] + .

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PUM

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Abstract

The invention discloses novel SGLT2 inhibitor compounds shown in a formula (I), pharmaceutically acceptable salts, easily hydrolyzed pre-drug esters or isomers and a pharmaceutical composition which contains the compounds as an inhibitor of a sodium-glucose co-transporter (SGLT). The pharmaceutical composition is used for treating or delaying related diseases such as diabetes, diabetic retinopathy, diabetic neuropathy, diabetic nephropathy, insulin resistance, hyperglycemia, hyperinsulinemia, rise of fatty acid or glycerinum, hyperlipemia, obesity, hypertriglyceridemia, X syndrome, diabetic complications, atherosclerosis, hypertension and the like. The formula is shown in the description.

Description

technical field [0001] The present invention relates to a compound represented by general formula (I) and general formula (II), its pharmaceutically acceptable salt, its easily hydrolyzed prodrug ester or its isomer, and a pharmaceutical composition containing the compound , and its use as a therapeutic agent, in particular as an inhibitor of the sodium-glucose cotransporter SGLT2. Background technique [0002] Diabetes is a metabolic disorder syndrome characterized by hyperglycemia caused by defects in insulin secretion and / or insufficient insulin action. Long-term hyperglycemia can damage many organs, leading to dysfunction and serious complications, such as diabetic retinopathy, diabetic nephropathy, and diabetic neuropathy. Diabetes can be divided into two types: insulin-dependent type 1 and non-insulin-dependent type 2, of which type 2 diabetes is the most common, accounting for more than 90% of diabetic patients. Diabetes has become the most prevalent disease in the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D421/10C07H15/26C07H1/00A61K31/351A61K31/7042A61P3/10A61P27/02A61P25/00A61P13/12A61P5/50A61P3/06A61P3/04A61P3/00A61P9/10A61P9/12
CPCC07D421/10A61P3/00A61P3/04A61P3/06A61P3/10A61P5/50A61P9/10A61P9/12A61P13/12A61P25/00A61P27/02
Inventor 史东方傅长金蒋强华刘伟张长亮
Owner JIANGSU ATOM BIOSCI & PHARMA CO LTD
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