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C-triaryl glucoside compound, preparation method and application of C-triaryl glucoside compound

A technology of glucoside and compound, which is applied in the field of medicine, can solve problems such as poor tolerance, weight gain, and hypoglycemia, and achieve the effects of lowering blood sugar, promoting urine sugar discharge, and low toxicity

Active Publication Date: 2018-01-09
GUANGZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these antidiabetic drugs have their own limitations
For example, biguanide compounds can easily cause lactic acidosis, sulfonylureas can cause hypoglycemia, and DPP-IV inhibitors can easily cause weight gain and poor tolerance, etc.

Method used

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  • C-triaryl glucoside compound, preparation method and application of C-triaryl glucoside compound
  • C-triaryl glucoside compound, preparation method and application of C-triaryl glucoside compound
  • C-triaryl glucoside compound, preparation method and application of C-triaryl glucoside compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Embodiment 1. Synthesis of compound 1

[0069]

[0070] Synthesis of compound 1-1:

[0071] Add 70.6g of 2-chloro-5-bromobenzoic acid and 500mL of tetrahydrofuran into a round bottom flask, slowly add 200mL of 2M borane dimethyl sulfide complex dropwise at 0°C; Slowly add methanol dropwise until no bubbles emerge; spin the reaction solution; then add 300mL water and 300mL ethyl acetate, extract and separate layers; wash the organic phase once with saturated brine and dry it with anhydrous sodium sulfate; The crude compound 1-1 was obtained, which was directly carried out to the next reaction without purification.

[0072] Synthesis of compound 1-2:

[0073] Add 60g PCC and 60g silica gel powder in a round bottom flask; add 500mL dichloromethane after mixing; cool to 0°C, add dropwise a dichloromethane solution (300mL) containing 45g compound 1-1 under stirring; maintain 0°C, The reaction was monitored by TLC; after the reaction was complete, the reaction solution ...

Embodiment 2

[0087] Embodiment 2. Synthesis of compound 2

[0088]

[0089] The synthetic method refers to Example 1, and the total yield is 32%.

[0090] 1 H NMR (400MHz, CDCl 3 )δ:7.24(s,1H),7.19-7.12(m,4H),6.99-6.98(m,6H),5.29(br,1H),5.07(br,1H),3.96-3.93(m,3H) ,3.77(s,2H),3.67(s,2H),3.57(s,1H),3.47(s,1H),3.35-3.33(m,2H),3.22-3.20(m,1H),2.97(br ,1H),2.87-2.81(q,J=7.2Hz,2H),1.26-1.22(t,J=7.2Hz,3H); MS m / z(ESI)537.1[M+Na] + .

Embodiment 3

[0091] Embodiment 3. Synthesis of compound 3

[0092]

[0093] The synthetic method refers to Example 1, and the total yield is 30%.

[0094] 1 H NMR (400MHz, CDCl 3 )δ:7.28(s,1H),7.18-7.08(m,4H),7.04-7.01(m,6H),5.25(br,1H),4.99(br,3H),4.02-3.91(m,4H) ,3.81(s,2H),3.69(S,2H),3.62-3.58(m,1H),3.51-3.47(m,1H),3.39-3.37(m,1H),3.23-3.21(m,1H) ,3.12(br,1H),2.85-2.80(m,1H),1.21-1.20(d,J=6.8Hz,6H); MS m / z(ESI)519.2[M+Na] + .

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PUM

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Abstract

The invention discloses a C-triaryl glucoside compound with the structure shown in the formula I as shown in the description, or an optical isomer thereof, or pharmaceutically acceptable salt, co-crystallization composite, hydrate, solvate or prodrug molecule thereof. The compound disclosed by the invention has a very good selective inhibition effect on SGLT-2, has an obvious promotion effect on releasing of animal urine sugar, can effectively reduce blood glucose and meanwhile cannot result in the risks of weight increase, hypoglycemia and the like. The compound disclosed by the invention haslittle influence on the activity of SGLT-1 while effectively inhibiting the activity of SGLT-2, can be expected that the toxicity is low when being developed into drugs, and has obvious medication advantage.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a C-triaryl glucoside compound and its preparation method and application. Background technique [0002] Diabetes caused by absolute or relative insufficiency of insulin raises blood sugar and causes serious complications, which can eventually lead to disability or death of the patient. Clinically, diabetes is divided into type I and type II. Type Ⅱ diabetes is hyperglycemia caused by relatively insufficient insulin secretion or unsound insulin action, and its incidence rate accounts for more than 90% of all diabetic patients. Currently common drugs for the treatment of type 2 diabetes include insulin sensitizers (such as biguanides, thiazolidinediones, etc.), insulin secretagogues (such as sulfonylureas and non-sulfonyl drugs), and DPP-IV, which has been on the market in recent years. Inhibitors etc. However, these antidiabetic drugs have their own limitations. For example,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/10C07D409/10A61K31/351A61K31/381A61P3/10A61P3/04
Inventor 胡文辉余细勇赵昕吴波
Owner GUANGZHOU MEDICAL UNIV
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