Optically pure thioacetic compound

A pure compound, thioacetic acid technology, applied in the field of pharmacy, can solve the problem of no chiral enantiomer reporting

Active Publication Date: 2016-10-05
CHINA RESOURCES SAIKE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Because it does not contain chiral atoms, it was studied as an achiral molecule

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0046] Racemic Lesinurad (2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid) The synthesis can refer to the synthesis of documents WO2009070740A2, CN103524440A and WO2014008295A1, and the synthesis route is as follows:

[0047]

Embodiment 2

[0048] Example 2: Optically pure single enantiomer 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio) Preparation of acetic acid

[0049] 1. Preparative chromatographic conditions are as follows:

[0050] Instrument: SFC350

[0051] Chromatographic column: CHIRALPAK AS-3 50*250mm, 50um.

[0052] Mobile phase: mobile phase A: 0.1% acetic acid methanol solution, mobile phase B: liquid carbon dioxide;

[0053] Mobile phase gradient program: mobile phase A 50%, mobile phase B 50%,

[0054] Detection wavelength: 220nm;

[0055] Column temperature: 34;

[0056] Injection volume: 4mL;

[0057] Flow rate: 160mL / min;

[0058] The corresponding component peaks were collected, and the collection time of the front peak was from 3.761 minutes to 5.074 minutes, which was identified as L-(-)-2-(5-bromo-4-(4-cyclopropylnaphthalene-1-yl)-4H-1 ,2,4-triazol-3-ylthio)acetic acid (the specific rotation is [α] 20 D =—9.5゜~—12.5゜, C=1, CH 3 OH); after peak collection t...

Embodiment 3

[0070] Example 3: Preparation of optically pure 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid sodium salt

[0071] Aqueous sodium hydroxide solution (1M, 2.0 mL, 2.0 mmol) was added dropwise to (-) or (+)-2-(5-bromo-4-(4-cyclopropylnaphthalene) at 10 °C over 5 minutes In a solution of -1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid (810 mg, 2.0 mmol) in ethanol (10 mL). The mixture was stirred for a further 10 minutes at 10°C. The volatile solvent was removed under vacuum at 30°C, the residue was dissolved in 15 mL of redistilled water, and freeze-dried to obtain solid (-) or (+)-2-(5-bromo-4-(4-cyclopropylnaphthalene-1- yl)-4H-1,2,4-triazol-3-ylthio)sodium acetate (850mg), Ms (Elpos): m / z=404.28[M+H] + .

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Abstract

The invention belongs to the field of pharmacy and relates to an optically pure thioacetic compound and application thereof to medicine. The optically pure thioacetic compound comprises levorotatory 2-(5-bromo-4-(4-cyclopropyl-naphthalene-1-base)-4H-1,2,4-triazole-3-based sulfenyl) acetic acid and dextral 2-(5-bromo-4-(4-cyclopropyl-naphthalene-1-base)-4H-1,2,4-triazole-3-based sulfenyl) acetic acid.

Description

Technical field: [0001] The invention belongs to the field of pharmacy, and relates to an optically pure thioacetic acid compound and the application of the compound in medicine. Background technique: [0002] The fundamental difference between chiral drugs and ordinary drugs is that the molecular structure contains at least one chiral center. Since various enzymes in the human body have chiral recognition and selectivity, only drugs with matching three-dimensional structures are selected. Therefore, only some of these drugs work in the human body, and the other part does not work or has little effect. , and even bring serious toxic side effects, such as the tragedy of "reactant" in the last century is a typical case. [0003] Chiral drugs have become the direction of new drug research and development due to their high curative effect, low toxicity and small dosage. As of 2000, among the total of 1850 drugs, 525 are natural and semi-synthetic drugs, and 517 are chiral drug...

Claims

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Application Information

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IPC IPC(8): C07D249/12A61P19/06A61P29/00A61P19/02A61P13/12A61P13/04
Inventor 杨琰杨广兴吕会超孙翔宇王文峰
Owner CHINA RESOURCES SAIKE PHARMA
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