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Method or preparing amisulpride acid

Amisulpride acid and amino technology, applied in the field of medicine and chemical industry, can solve the problems of strong acidity, high equipment requirements, unfavorable workshop material feeding, etc., and achieve the effects of low cost, low equipment requirements, and small residual solvent content

Active Publication Date: 2013-12-18
广安凯特制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] According to the current retrieval situation, the one-step preparation of amisulpride from 2-methoxy-4-amino-5-ethylthiobenzoic acid is all carried out in the acetic acid system, and the yield is only 55%-64%. Acetic acid has a strong irritating and sour taste, which is not conducive to feeding the workshop, and its acidity is strong, which requires relatively high equipment

Method used

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  • Method or preparing amisulpride acid
  • Method or preparing amisulpride acid

Examples

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Effect test

Embodiment 1

[0041] (1) Mix 140g of 4-aminosalicylic acid, 1640g of acetone, and 7g of tap water, add 129g of potassium hydroxide at 20-30°C, and then add 250g of dimethyl sulfate dropwise. After 2 hours of reaction at 200 rpm, the acetone was concentrated at 40-50°C, and 1400g of water was added for crystallization for 2 hours. After filtration, 149g of the product, methyl 2-methoxy-4-aminobenzoate, was obtained, with a yield of 90.0%.

[0042] (2) After mixing 44g of methyl 2-methoxy-4-aminobenzoate, 660g of methanol, and 59.5g of potassium thiocyanate, add 50g of bromine dropwise at 0-5°C, and react at 10-20°C after the addition is complete After 4 hours, 440 g of water was added for crystallization for 1 hour, and 53 g of methyl 4-amino-2-methoxy-5-cyanothiobenzoate were obtained by filtration, with a yield of 91.4%.

[0043] (3) Mix 130g of methyl 4-amino-2-methoxy-5-cyanothiobenzoate with 650g of ethanol and 156g of sodium sulfide, heat up to 50-60°C to dissolve, then add 71.5g of br...

Embodiment 2

[0046] (1) Mix 140g of 4-aminosalicylic acid, 1640g of acetone, and 7g of tap water, add 129g of potassium hydroxide at 20-30°C, and then add 250g of dimethyl sulfate dropwise. After 2 hours of reaction at 200 rpm, the acetone was concentrated at 40-50°C, and 1400g of water was added for crystallization for 2 hours. After filtration, 149g of the product, methyl 2-methoxy-4-aminobenzoate, was obtained, with a yield of 90.0%.

[0047] (2) After mixing 44g of methyl 2-methoxy-4-aminobenzoate, 660g of methanol, and 59.5g of potassium thiocyanate, add 50g of bromine dropwise at 0-5°C, and react at 10-20°C after the addition is complete After 4 hours, 440 g of water was added for crystallization for 1 hour, and 53 g of methyl 4-amino-2-methoxy-5-cyanothiobenzoate were obtained by filtration, with a yield of 91.4%.

[0048] (3) Mix 65g of methyl 2-methoxy-4-aminobenzoate with 325g of ethanol and 78g of sodium sulfide, heat up to 50-60°C to dissolve, then add 50g of diethyl sulfate dr...

Embodiment 3

[0051] (1) Mix 140g of 4-aminosalicylic acid, 1640g of acetone, and 7g of tap water, add 129g of potassium hydroxide at 20-30°C, and then add 250g of dimethyl sulfate dropwise. After 2 hours of reaction at 200 rpm, the acetone was concentrated at 40-50°C, and 1400g of water was added for crystallization for 2 hours. After filtration, 149g of the product, methyl 2-methoxy-4-aminobenzoate, was obtained, with a yield of 90.0%.

[0052] (2) After mixing 44g of methyl 2-methoxy-4-aminobenzoate, 660g of methanol, and 59.5g of potassium thiocyanate, add 50g of bromine dropwise at 0-5°C, and react at 10-20°C after the addition is complete After 4 hours, 440 g of water was added for crystallization for 1 hour, and 53 g of methyl 4-amino-2-methoxy-5-cyanothiobenzoate were obtained by filtration, with a yield of 91.4%.

[0053] (3) Mix 130g of methyl 2-methoxy-4-aminobenzoate with 650g of ethanol and 156g of sodium sulfide, heat up to 50-60°C to dissolve, then add 71.5g of bromoethane dr...

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Abstract

The invention discloses a method for preparing a key intermediate of amisulpride. 2- methoxyl-4-amino-5-diethyl sulfide benzoic acid is oxidized in an alkaline condition so as to obtain the amisulpride acid (key intermediate of amisulpride). Compared with the existing methods, the method can produce products with higher quality, the yield is improved remarkably, the operation is simpler, safer, and has environment-friendly effect, and the method is especially suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and specifically relates to a preparation method of amisulpride key intermediate (amisulpride acid). Background technique [0002] Amisulpride is a selective dopamine D2 and D3 receptor antagonist developed by Sanofi for the treatment of psychiatric disorders, especially with positive symptoms (eg delirium, hallucinations, cognitive impairment) and / or Acute or chronic schizophrenia with negative symptoms (such as slow response, apathy, and social withdrawal), as well as psychotic patients with predominantly negative symptoms, its chemical structure is as follows: [0003] [0004] The preparation of amisulpride is usually obtained by reacting amisulpride acid with a certain amount of 1-ethyl-2-aminomethylpyrrolidine (as shown below). Chinese Journal of Pharmaceutical Industry, 2011, 42(11): 801-803: [0005] [0006] Therefore, the key to the preparation of amisulpride lies i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/02C07C317/48
Inventor 王廷圣游洪全
Owner 广安凯特制药有限公司
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