A kind of method for preparing clorprenaline optical isomers based on chiral liquid chromatography

A technology of optical isomers and clorprenaline, which is applied in organic chemistry methods, chemical instruments and methods, preparation of amino hydroxyl compounds, etc., can solve difficult and unseen problems, and reduce preparation costs and preparation costs Low and fast preparation effect

Active Publication Date: 2018-11-27
大连润生康泰医学检验实验室有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, for different separation objects, it is necessary to determine a large number of parameters such as sample volume, column temperature, eluent, flow rate, etc., which is extremely difficult. Research and Patent Literature Reports of Clorprenaline

Method used

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  • A kind of method for preparing clorprenaline optical isomers based on chiral liquid chromatography
  • A kind of method for preparing clorprenaline optical isomers based on chiral liquid chromatography
  • A kind of method for preparing clorprenaline optical isomers based on chiral liquid chromatography

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1 racemic clorprenaline hydrochloride is raw material

[0030] 1. Sample preparation

[0031] Dissolve 0.1 g of racemic chlorprenaline hydrochloride (Mirrell Chemical Reagent Co., Ltd., Shanghai) in 10 mL of water:methanol=90:10 (volume ratio) mixed solvent, then add 50 μL of triethylamine, swirl for 30 s, pH=8~9.

[0032] 2. Sample separation

[0033] Pre-HPLC adopts dionex ultimate 3000 liquid chromatography system, equipped with WPS-3000SL autosampler and AFC-3000 automatic fraction collection system.

[0034] Chromatographic column: Daicel CHIRALFLASH IF medium pressure preparative column (100mm*30mm*20μm).

[0035] Chromatographic conditions:

[0036] ①The total injection volume is 10mL, set the single injection volume of the autosampler to 2mL, and repeat 5 times;

[0037] 2. eluent is water: the mixed solvent of methanol=90:10 (volume ratio), flow velocity is 12mL / min, isocratic elution;

[0038] ③The temperature of the column thermostat (column ...

Embodiment 2

[0057] Embodiment 2 Racemic chlorprenaline is a raw material (seeing for optical purity detection figure 1 )

[0058] Except following conditions, other conditions are identical with embodiment 1:

[0059] 1. 0.1g racemic chlorprenaline (Mai Ruier Chemical Reagent Co., Ltd., Shanghai) was dissolved in 10mL of water: the mixed solvent of methanol=80:20 (volume ratio) (the pH of the obtained injection sample=8~9, no need to adjust );

[0060] ②Single injection volume is 2mL (Pre-HPLC results see Figure 2a ). Or the concentration is 40mg / mL (pH=8~9), and the single injection volume is 10mL (Pre-HPLC results see Figure 2b ). The eluent is a mixed solvent of water:ethanol=80:20 (volume ratio), and the flow rate is 12mL / min, isocratic elution.

[0061] ③ The first freeze-drying temperature is -10°C, and the drying time is 48 hours;

[0062] The total recovery rate is 91%, the ordinary purity is greater than 99%, the optical purity of (R)-chlorprenaline is greater than 97%, ...

Embodiment 3

[0063] Embodiment 3 takes the clorprenaline sulfate with low optical purity as raw material

[0064] The raw material sample was analyzed for the purity of the sample in Example 1, and the result was: the ordinary purity was greater than 94%, and the optical purity was 74%.

[0065] Except following conditions, other conditions are identical with embodiment 1:

[0066] ① 0.1 g of the above-mentioned cloprenaline sulfate (Xi'an Pusen Instrument Co., Ltd., Xi'an) was dissolved in a mixed solvent of 15 mL of water:isopropanol=85:15 (volume ratio).

[0067] ② The eluent is a mixed solvent of water:ethanol=85:15 (volume ratio), the flow rate is 15mL / min, isocratic elution.

[0068] ③ The first freeze-drying temperature is -15°C, and the drying time is 24 hours;

[0069] Total recovery rate is 90%, common purity is all greater than 99%, (R)-chlorprenaline optical purity is greater than 98% ( Figure 3a ), (S)-chlorprenaline optical purity is greater than 97% ( Figure 3b ).

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Abstract

The invention provides a method for preparing clorprenaline optical isomers based on chiral liquid chromatography, comprising the specific steps: 1), preparing a sample; 2) determining chiral chromatographic separation conditions, and preparing under medium pressure; 3), collecting optical isomers respectively, and lyophilizing; 4), measuring purity of the optical isomers. Chiral liquid chromatography is selected to prepare clorprenaline optical isomers for the purpose of solving the problem that synthesis of optically pure clorprenaline in actual scientific research and production is high in difficulty and high in preparation cost, preparation of optical isomers is available for both clorprenaline and its salts, the method has the advantages of good operation simplicity, high preparation efficiency, low cost, high optical purity and the like, the method is applicable particularly to the preparation of high-performance low-toxicity optically pure clorprenaline required by medical industry, corresponding quality control standards may be established for preparation, the method is more widely applicable, and a new concept and method is provided for the research and development, production and quality control for optically pure clorprenaline.

Description

technical field [0001] The invention relates to a method for preparing (R)-chlorprenaline and (S)-chlorprenaline optical isomers based on chiral liquid-phase preparative chromatographic technology. Background technique [0002] The chemical name of clorprenaline is α-[[(1-methylethyl)amino]methyl]-2-chloro-benzyl alcohol, which is a class of β-adrenoceptor agonist drugs, and its clinical application is generally its hydrochloride Salt is suitable for bronchial asthma, asthmatic bronchitis, chronic bronchitis, and emphysema, which can relieve asthma and improve lung function. [0003] Recent studies have shown that clorprenaline can increase the antihypertensive effect of angiotensin-converting enzyme I inhibitors, such as captopril and benazepril, and reduce the toxicity of long-term medication. The effect may be that (R)-cloprenaline reduces the content of renin in plasma, which reduces the amount of angiotensinogen converted into angiotensin I, thereby reducing the conten...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C213/10C07C215/30
CPCC07B2200/07C07C213/10C07C215/30
Inventor 龚频常相娜杨文娟王兰陈福欣
Owner 大连润生康泰医学检验实验室有限公司
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