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A kind of sglts inhibitor and application thereof

A compound, selected technology, applied in the application field of medicine, can solve the problems of edema, hypoglycemia symptoms, heart failure weight, etc.

Active Publication Date: 2021-08-10
SHANDONG DANHONG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These drugs have good therapeutic effects, but there are still safety problems in long-term treatment. For example, biguanides can easily cause lactic acidosis; sulfonylureas can cause hypoglycemia symptoms; insulin resistance improvers can cause edema, heart failure and Weight gain; alpha-glucosidase inhibitors can cause symptoms such as abdominal pain, bloating, and diarrhea

Method used

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  • A kind of sglts inhibitor and application thereof
  • A kind of sglts inhibitor and application thereof
  • A kind of sglts inhibitor and application thereof

Examples

Experimental program
Comparison scheme
Effect test

reference example 1

[0098] Reference Example 1: Fragment A-1

[0099]

[0100] synthetic route:

[0101]

[0102] Step 1: Synthesis of Compound A-1-3.

[0103] Add compound A-1-1 (20g, 84.78mmol, 10.87mL, 1eq) and tetrahydrofuran (125mL) to the pre-dried three-necked flask (500mL) in sequence, replace the nitrogen, drop the temperature to -78°C, and slowly add n-butyl Lithium (2.5M, 37.64 mL, 1.11 eq), stirred for 0.5 h. Finally, compound A-1-2 (12.5g, 93.26mmol, 1.1eq) was added, and the temperature was slowly raised to 0°C and stirred for 0.5 hours. After the reaction was completed, it was slowly quenched with saturated aqueous ammonium chloride (200 mL) at 0 to 10 degrees Celsius, extracted with ethyl acetate (200 mL x 2), combined the organic phases, washed with saturated sodium chloride (100 mL), and then washed with anhydrous After drying over sodium sulfate, the desiccant was filtered off, and the solvent was removed under reduced pressure to obtain the crude compound A-1-3, which...

reference example 9

[0111] Reference Example 9: Fragment B-1

[0112]

[0113] synthetic route:

[0114]

[0115] Step 1: Synthesis of Compound B-1-2

[0116] Add compound B-1-1 (30g, 127.41mmol, 1eq) and tetrahydrofuran (6mL) to a 3L three-necked flask, add borane tetrahydrofuran complex (1M, 382.23mL, 3eq) while bubbling nitrogen, at 25°C The mixture was reacted for 16 hours. After the reaction was completed, methanol (150 mL) was added dropwise to the reaction solution at 25° C. while blowing nitrogen gas to quench the reaction solution. Then, the mixture was concentrated to dryness at 45° C. by water pump to obtain compound B-1-2. 1 H NMR (400MHz, CHLOROFORM-d) δ = 7.68 (d, J = 2.4Hz, 1H), 7.37 (dd, J = 2.2, 8.6Hz, 1H), 7.22 (d, J = 8.4Hz, 1H), 4.77 (d,J=5.3Hz,2H).

[0117] Step 2: Synthesis of Compound B-1-3

[0118] Add compound B-1-2 (27g, 121.91mmol, 1eq) and dimethylformamide (150mL) into the three-necked flask, and add sodium hydrogen (9.75g, 243.82mmol, 60% purity, 2eq ), a...

reference example 10

[0131] Reference Example 10: Fragment B-2

[0132]

[0133] synthetic route:

[0134]

[0135] Step 1: Synthesis of Compound B-2-2

[0136] Lithium aluminum hydride (11g, 289.82mmol, 1.25eq) was dissolved in tetrahydrofuran (200mL) at 0°C, replaced with nitrogen three times, and then filled with nitrogen for protection. Compound B-2-1 (50g, 232.51mmol, 1eq) was dissolved in tetrahydrofuran (200mL) and slowly added to the reaction solution at 0°C. Bubbles were generated, and the reaction was heated to 25°C for 2 hours. At 0°C, water (11 mL) was slowly added dropwise first, then 15% aqueous sodium hydroxide solution (11 mL) was added dropwise, and finally water (33 mL) was added. Filter and wash the filter residue twice with ethyl acetate. Suspend the filtrate to dryness. Crude compound B-2-2 was obtained. Step 2: Synthesis of Compound B-2-3

[0137] Compound B-2-2 (47.9g, 238.24mmol, 1eq) was dissolved in dimethylformamide (120mL), and sodium hydrogen (14.29g, 357....

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Abstract

Compounds as dual SGLT1 / SGLT2 inhibitors, and use in the preparation of medicaments as dual SGLT1 / SGLT2 inhibitors. The compound is a compound represented by formula (I), an isomer thereof or a pharmaceutically acceptable salt thereof.

Description

[0001] This application claims the following priority: [0002] CN201810012284.4, application date 2018.01.05. technical field [0003] The present invention relates to a class of compounds as SGLT1 / SGLT2 dual inhibitors and the application in preparation of drugs as SGLT1 / SGLT2 dual inhibitors. It specifically relates to the compound represented by formula (I), its isomer or its pharmaceutically acceptable salt. Background technique [0004] Diabetes is a metabolic disease characterized by high blood sugar. Hyperglycemia is caused by defective insulin secretion or impaired biological action, or both. In diabetes, long-term abnormal blood glucose levels can lead to serious complications, including cardiovascular disease, chronic renal failure, retinal damage, nerve damage, microvascular damage, and obesity. In the treatment of diabetes, in the early stage, diet control and exercise therapy are the preferred blood sugar control programs. When these methods are difficult t...

Claims

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Application Information

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IPC IPC(8): C07D407/10C07D309/10C07D309/22C07D409/10C07D409/14A61K31/351A61K31/381A61P3/10
CPCA61P3/10C07H15/14C07D309/10A61K31/351A61K31/357A61K31/381C07D309/22C07D407/10C07D409/10C07D409/14
Inventor 吴成德毛庆华李翼于涛陈曙辉
Owner SHANDONG DANHONG PHARMA
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