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Method for preparing Sumatriptan Succinate

A technology for sumatriptan succinate and hydrochloride, which is applied in the field of preparation of sumatriptan succinate, can solve problems such as difficulty in realizing industrialization requirements, harsh reaction conditions, and unsuitability for industrialization, and achieve shortened production cycle and preparation The effect of simple process and easy purification

Inactive Publication Date: 2009-10-28
ZHEJIANG SUPOR PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Method ④ The synthesis route is long, the total cost is high, and it is not suitable for industrialization
Method 5. uses expensive 5-bromoindole as the starting raw material, and repeatedly uses strong bases such as sodium hydride, lithium tetrahydrogen aluminum, metal sodium, and dangerous raw materials in the route. The reaction conditions are harsh, and the route is long, and it is difficult to Realize the needs of industrialization

Method used

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  • Method for preparing Sumatriptan Succinate
  • Method for preparing Sumatriptan Succinate
  • Method for preparing Sumatriptan Succinate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Add 106.8g (1.0mol) of 4-chlorobutyraldehyde (GC content 99.7%, commercially available) into a 500ml three-necked flask, stir and cool, and start to drop 209.1g (1.1mol) of sodium metabisulfite and 315ml of water at 20°C The prepared solution. After the dropwise addition, stir at room temperature for 0.5 hour, filter, and dry to obtain 289.2 g (content 98.6%) of white solid 4-chlorobutane-1, 1-sodium disulfonate with the structure shown in general formula IX, yield 96.1% .

Embodiment 2

[0042] 106.8g (1.0mol) 4-chlorobutyraldehyde (GC content 99.7%, commercially available) was joined in the there-necked flask of 500ml, stirred, and began to dropwise add 190.1g (1.0mol) of sodium metabisulfite and 290ml of water at room temperature. solution. After the dropwise addition, stir at room temperature for 0.75 hours, filter, and dry to obtain 288.9 g (content 98.4%) of white solid 4-chlorobutane-1,1-sodium disulfonate with the structure shown in general formula IX, yield 95.8% .

Embodiment 3

[0044]62.8g (208.6mmol) of 4-chlorobutane-1,1-disulfonic acid prepared in 50.0g (198.7mmol) of 4-hydrazine-N-methylbenzenesulfonamide hydrochloride and embodiment 1 Sodium was added to a 1L three-necked flask, and then 550ml of 5% sulfuric acid was added. Heat to 65±2°C and hold for 2 hours. After the incubation is completed, adjust the pH of the reaction solution to neutral with 25% aqueous sodium hydroxide solution. Extracted 3 times with ethyl acetate, combined the organic phases and washed 3 times with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, distilled and recovered ethyl acetate, and the residue was about 35.0g oil, which was 3-(2-chloro The crude product of ethyl)-N-methyl-1H-indole-5-methanesulfonamide (structure shown in general formula X) has a content of 93.4% (HPLC), and a yield of 57.6%.

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Abstract

A preparation method of sumatriptan succinate belongs to the technical field of chemical pharmacy, and is mainly carried out by the following steps: 1. After reacting 4-chlorobutyraldehyde and sodium metabisulfite aqueous solution, filter and dry to obtain 4-chlorobutane-1 , 1-sodium disulfonate; ②4-hydrazino-N-methylbenzenesulfonamide hydrochloride and 4-chlorobutane-1,1-sodium disulfonate are heated in the presence of inorganic acid or organic acid catalyst After the reaction, adjust the reaction solution to neutrality with an alkali solution, and extract with an organic solvent to obtain 3-(2-chloroethyl)-N-methyl-1H-indole-5-methanesulfonamide; ③3-(2- Chloroethyl)-N-methyl-1H-indole-5-methanesulfonamide addition phase transfer catalyst, react with dimethylamine, after the reaction is completed, extract, decolorize and refine to obtain sumatriptan refined product, and then heat with solvent Dissolve, add succinic acid to form a salt, and then crystallize to obtain the white final product sumatriptan succinate. The invention has short process route, simple operation, high yield, low cost and stable product quality.

Description

technical field [0001] The utility model relates to a preparation method of sumatriptan succinate, which belongs to the technical field of chemical pharmacy. Background technique [0002] The chemical name of sumatriptan succinate is 3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide succinate, which has the general formula I The structure is obtained by salting sumatriptan (structure shown in general formula II) and succinic acid. Sumatriptan succinate, the first triptan drug for the acute treatment of migraine, selectively constricts overdilated blood vessels in the brain, resulting in rapid relief of severe headache attacks. [0003] [0004] General formula I General formula II [0005] The preparation method of sumatriptan succinate reported in the existing literature mainly contains the following several kinds: ①Patent WO2004099141 reports that by Grignard reaction of N,N-dimethyl-3-chloropropylamine and triethyl orthoformate, 4 -(N, N-dimethylami...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/14
Inventor 陶伟峰石岳崚樊友斌吕建国邓莉平
Owner ZHEJIANG SUPOR PHARM CO LTD
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