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Benzoate of 3-(3-aminopiperidine-1-yl)-5-oxo-1,2,4-triazine derivative, and preparation method and pharmaceutical composition thereof

A technology of triazine derivatives and aminopiperidine, applied in the field of medicine, can solve the problems of easy oxidation, instability, poor stability and the like, and achieve the effects of good stability, guaranteed quality and good bioavailability

Inactive Publication Date: 2015-07-29
SHENZHEN SALUBRIS PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] However, during the study of Compound A, it was found to be unstable and easily oxidized
Therefore, there is an urgent need to develop a new form of compound A to solve the problem of its poor stability and prepare a more ideal drug for the treatment of type II diabetes

Method used

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  • Benzoate of 3-(3-aminopiperidine-1-yl)-5-oxo-1,2,4-triazine derivative, and preparation method and pharmaceutical composition thereof
  • Benzoate of 3-(3-aminopiperidine-1-yl)-5-oxo-1,2,4-triazine derivative, and preparation method and pharmaceutical composition thereof
  • Benzoate of 3-(3-aminopiperidine-1-yl)-5-oxo-1,2,4-triazine derivative, and preparation method and pharmaceutical composition thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 Preparation of 1-bromo-4-fluoro-2-(methyl isothiocyanate)benzene (2)

[0039] To 1-bromo-2-(bromomethyl)-4-fluorobenzene (1,5.36g, 20.0mmol) in DMF (20ml), add sodium iodide (1.20g, 8.00mmol) and potassium thiocyanate (3.88g, 40.0mmol). The mixture was heated to 80° C. for 12 h under a nitrogen atmosphere, cooled to room temperature, 100 ml of water was added thereto, and extracted with ethyl acetate (50 mL×2), the combined organic layers were washed with saturated brine, and dried over anhydrous magnesium sulfate. The crude product was concentrated by suction filtration, and the residue was purified by silica gel column chromatography (eluent: petroleum ether) to obtain 1-bromo-4-fluoro-2-(methylisothiocyanate)benzene (2).

Embodiment 2

[0040] Example 2 Preparation of N-(2-bromo-5-fluorobenzyl)hydrazine thioformamide (3)

[0041] Hydrazine hydrate (80%, 2.22g, 35.5mmol) in 1,4-dioxane solution (20ml) was cooled to 0°C, and 1-bromo-4-fluoro-2-(methylisothiocyanate A solution of benzene (2,3.16g, 12.8mmol) in 1,4-dioxane (5ml). The mixture was stirred at room temperature for 2 hours, 100ml of ice water was added to it, and a solid precipitated out, filtered with suction, washed with water, and dried overnight with phosphorus pentoxide to obtain N-(2-bromo-5-fluorobenzyl)hydrazinothiomethyl Amide (3). MS: m / z, 278 (100%, M+1), 280 (100%), 300 (10%, M+23), 302 (10%).

Embodiment 3

[0042] Example 3 Preparation of methyl 2-(2-(2-bromo-5-fluorobenzylaminothiocarboxamide)hydrazino)propionate (4)

[0043] To a solution of pyruvic acid (352mg, 4.00mmol) in methanol (15mL) was added successively N-(2-bromo-5-fluorobenzyl)hydrazinothiocarboxamide (3, 1.112g, 4.00mmol), and concentrated Add 5 drops of sulfuric acid, heat the mixture to reflux for 7 hours, evaporate most of the solvent, extract the residue with ethyl acetate (150ml), wash the organic layer with water, saturated sodium bicarbonate solution, saturated brine, and anhydrous magnesium sulfate Dry and concentrate by suction to obtain methyl 2-(2-(2-bromo-5-fluorobenzylaminothiocarboxamide)hydrazino)propionate (4). MS: m / z, 362 (100%, M+1), 364 (100%), 384 (60%, M+23), 386 (60%).

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Abstract

A benzoate of a 3-(3-amino piperidine-1-yl)-5-oxo-1,2,4-triazine derivative, a preparation method for the benzoate, and a pharmaceutical composition thereof.

Description

technical field [0001] The invention belongs to the field of medical inventions, in particular to a derivative of 3-(3-aminopiperidin-1-yl)-5-oxo-1,2,4-triazine capable of inhibiting the activity of dipeptidyl peptidase-IV Benzoic acid salt of substance, its preparation method and pharmaceutical composition thereof. Background technique [0002] Diabetes affects millions of people worldwide and is considered one of the major threats to human mortality in the 21st century. Over time, uncontrolled diabetes can damage body systems, including the heart, blood vessels, eyes, kidneys and nerves. Worldwide, the socioeconomic burden of diabetes is high. [0003] There are two main types of diabetes, designated Type I and Type II, with Type II diabetes accounting for more than 90% of all diabetes worldwide. Type I diabetes is characterized by insulin deficiency, which is mainly caused by autoimmune-mediated destruction of pancreatic β cells, and type II diabetes is characterized b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04A61K31/53A61P3/10
CPCC07D401/04A61P3/10C07C63/08
Inventor 谭颂德谢福胜蔡泽绵植建琼陈淑君王为波李同双
Owner SHENZHEN SALUBRIS PHARMA CO LTD