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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 difficult to realize industrialization requirements, unsuitable for industrialization, harsh reaction conditions, etc., achieve shortened production cycle, easy The effect of simple purification and preparation process

Inactive Publication Date: 2007-12-26
ZHEJIANG SUPOR PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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

[0039] 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

[0041] 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

[0043]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

This invention discloses a method for preparing sumatriptan succinate. The method comprises: (1) reacting 4-chlorobutyraldehyde and sodium pyrosulfite aqueous solution, filtering and drying to obtain sodium 4-chlorobutane-1,1-disulfonate; (2) heating and reacting 4-hydrazino-N-methyl phenylmethansulfonamide and 4-chlorobutane-1,1-disulfonate in the presence of inorganic acid or organic acid catalyst, neutralizing with an alkali solution, and extracting with an organic solvent to obtain 3-(2-chloroethyl)-N-methyl-1H-indole-5-methansulfonamide; (3) adding phase transfer catalyst into 3-(2-chloroethyl)-N-methyl-1H-indole-5-methansulfonamide, reacting with dimethylamine, extracting, decolorizing, refining to obtain sumatriptan product, dissolving in a solvent under heating, adding succinic acid, reacting, and precipitating the crystal to obtain white sumatriptan succinate. The method has such advantages as short process, easy 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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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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