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Gabapentin synthesizing method

A synthesis method and gabapentin technology are applied in the field of anti-epileptic chemical drug synthesis, which can solve the problems of inconvenient industrialized production, long process route, complicated operation and the like, and achieve the effects of easy industrialized production, reasonable process design and low equipment investment.

Inactive Publication Date: 2014-03-26
湖北楚阳科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional process has the disadvantages of long process route, cumbersome operation, diversified raw materials, high cost and not easy for industrial production.

Method used

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  • Gabapentin synthesizing method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] A kind of synthetic method of gabapentin, its step is as follows:

[0028] (1) Add 1 mole (182.2g) 1,1-cyclohexyl diacetic anhydride (A) into the reaction kettle, then add 1822g solvent dichloromethane, stir to dissolve, add 2 moles (143g) to hydrate after complete dissolution Hydrazine (70%), stirred and controlled the temperature at 20°C, carried out the acylation reaction, kept the temperature for 15 hours, crystals were precipitated, and 205.5g of 1,1-cyclohexyldiacetic acid monohydrazide (B) wet product was obtained by suction filtration;

[0029] (2) Dissolve 205.5g of 1,1-cyclohexyldiacetic acid monohydrazide wet product (B) into 1928g of dichloromethane, then add 1.3 moles of sodium nitrite, add 2.7 moles of concentrated sulfuric acid (98%), stir and control the temperature 30°C, reacted for 6 hours, and obtained 198.6g of 1,1-cyclohexyldiacetic acid monoacyl azide (C) wet product by suction filtration;

[0030] (3) Dissolve 198.6g of 1,1-cyclohexyldiacetic aci...

Embodiment 2

[0032] A kind of synthetic method of gabapentin, its step is as follows:

[0033] (1) Add 1 mole (182.2g) 1,1-cyclohexyl diacetic anhydride (A) into the reaction kettle, then add 1000g solvent acetone, stir to dissolve, add 5 moles (357.5g) hydrazine hydrate after complete dissolution (70%), stirred and controlled the temperature at 55°C for acylation reaction, constant temperature reaction for 4 hours, cooled to room temperature, crystallized for 20 minutes, and suction filtered to obtain 195.5g of 1,1-cyclohexyldiacetic acid monohydrazide (B ) wet product;

[0034] (2) Dissolve 195.5g of 1,1-cyclohexyldiacetic acid monohydrazide (B) wet product into 977.5g of chloroform, then add 1.38 moles of sodium nitrite, add 6.9 moles of hydrochloric acid (36%), stir and control the temperature at 10°C , reacted for 10 hours, and obtained 180.5g of 1,1-cyclohexyldiacetic acid monoyl azide (C) wet product by suction filtration;

[0035] (3) Dissolve 180.5g of 1,1-cyclohexyldiacetic aci...

Embodiment 3

[0037] A kind of synthetic method of gabapentin, its step is as follows:

[0038] (1) Add 1 mole (182.2g) 1,1-cyclohexyl diacetic anhydride (A) into the reaction flask, then add 3644g solvent xylene, stir to dissolve, add 8 moles (572.1g) to hydrate after complete dissolution Hydrazine (70%), stirred and controlled the temperature at 100°C for acylation reaction, constant temperature reaction for 10 hours, cooled to room temperature, crystallized for 30 minutes, and suction filtered to obtain 208.6g of 1,1-cyclohexyldiacetic acid monohydrazide (B ) wet product;

[0039] (2) Dissolve 208.6g of 1,1-cyclohexyldiacetic acid monohydrazide (B) wet product into 3129g of toluene, then add 1.96 moles of sodium nitrite, and add a total of 5.88 moles of acetic acid and trichloroacetic acid mixture (including acetic acid The molar ratio with trichloroacetic acid is 1:1), stirring and controlling the temperature at 60°C, reacting for 20 hours, cooling and filtering with suction to obtain ...

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Abstract

The invention belongs to the technical field of anti-epileptic synthetic medicaments, particularly discloses a gabapentin synthesizing method. The gabapentin synthesizing method. includes steps: (1) obtaining 1,1-cyclohexanediacetic acid monohydrazide (B) by acylation reaction between hydrazine hydrate and 1,1-cyclohexane diacetic anhydride (A) which serves as a raw material; (2) obtaining azide compound (C) by reaction between 1,1-cyclohexanediacetic acid monohydrazide (B) and sodium nitrite by the aid of acid; and (3) heating the azide compound (C) in a solvent, and directly obtaining the object gabapentin. By the aid of the gabapentin synthesizing method, gabapentin with high purity can be directly obtained without utilization of virulent sodium azide as an azide reagent or an intermediate process of gabapentin hydrochloride, so that the gabapentin synthesizing method is simple in technique process, high in production yield and easy to realize industrialized production.

Description

technical field [0001] The invention relates to the technical field of synthesis of antiepileptic chemical drugs, in particular to a synthesis method of gabapentin. Background technique [0002] Gabapentin is an antiepileptic drug first developed by Warner-Lanbert in the United States, and it was first launched in the UK in 1993. Gabapentin is a novel antiepileptic drug. It is a derivative of γ-aminobutyric acid (GABA). Its pharmacological effects are different from those of existing antiepileptic drugs. Recent studies have shown that the effect of gabapentin is produced by changing the metabolism of GABA. It has the advantage of being well tolerated with minimal side effects. [0003] Most of the traditional techniques currently on the market are to first prepare the key intermediate gabapentin hydrochloride, then use gabapentin hydrochloride as raw material, dissolve gabapentin hydrochloride with alcohol solvent, add potassium bicarbonate and other inorganic salts to neut...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C227/04
Inventor 陈涛郭海涛李祯邓德忠邓德政王鹏
Owner 湖北楚阳科技股份有限公司