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Method for synthesizing medicine for treating epilepsy by using L-2-aminobutanamide hydrochloride

A technology of aminobutyramide and hydrochloride, applied in organic chemistry methods, preparation of carboxylic acid amide optical isomers, organic chemistry, etc., can solve the problems of great health hazards for operators, restrictions on industrial promotion, and high processing costs, and achieve Environmentally friendly, high chemical purity, and low impurity content

Pending Publication Date: 2021-11-02
CANGZHOU SENARY CHEM SCI TEC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, sodium cyanide, a highly toxic substance, is used. Improper operation of sodium cyanide in the feeding and weighing stage will cause poisoning or even death, which is very harmful to the health of operators.
In addition, the reaction produces a large amount of wastewater containing ammonium chloride and excess sodium cyanide, and the treatment cost is high. These safety hazards limit the industrial promotion of these processes

Method used

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  • Method for synthesizing medicine for treating epilepsy by using L-2-aminobutanamide hydrochloride
  • Method for synthesizing medicine for treating epilepsy by using L-2-aminobutanamide hydrochloride
  • Method for synthesizing medicine for treating epilepsy by using L-2-aminobutanamide hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] The method for synthesizing epilepsy medicine with L-2-aminobutyramide hydrochloride, its synthetic steps are as follows:

[0051] One) the resolution of L-2-aminobutanamide hydrochloride

[0052] Take 10.2g (0.1mol) of 2-aminobutanamide and put it into a 100mL three-necked bottle, add 60mL of ethanol, stir and disperse, add 4.5g (0.05mol) of inducer glyceraldehyde and 15.0g (0.1mol) of resolving agent L-tartaric acid , heated to 70°C, maintained at 70°C for asymmetric resolution, stirred for 6 hours, filtered, and washed with a small amount of ethanol to obtain L-2-aminobutyramide L-tartrate double salt (directly proceed to the next step without drying).

[0053] Take the obtained L-2-aminobutyramide L-tartrate double salt and add it to 11.6mL of 30wt% concentrated hydrochloric acid (the molar ratio of 2-aminobutanamide to hydrochloric acid is 1:1.1), and stir at room temperature for separation reaction for 1.5h to The solution was completely clear, and then slowly ad...

Embodiment 2

[0059] The method for synthesizing epilepsy medicine with L-2-aminobutyramide hydrochloride, its synthetic steps are as follows:

[0060] One) the resolution of L-2-aminobutanamide hydrochloride

[0061] Take 10.2g (0.1mol) of 2-aminobutyramide into a 100mL three-necked flask, add 51mL of n-propanol, stir to disperse, add 2.7g (0.03mol) of inducer glyceraldehyde and 16.5g (0.11mol) of resolving agent L - Tartaric acid, heated to 80°C, maintained at 80°C for asymmetric resolution, stirred for 5 hours, filtered, washed with a small amount of ethanol to obtain L-2-aminobutyramide L-tartrate double salt (directly proceed to the next step without drying ).

[0062] Take the obtained L-2-aminobutyramide L-tartrate double salt and add it to 11.8mL of concentrated hydrochloric acid (2-aminobutanamide:hydrochloric acid molar ratio 1:1.2) with a concentration of 32wt%, and stir at room temperature for separation reaction for 1.5h to The solution was completely clarified, and then slow...

Embodiment 3

[0066] The method for synthesizing epilepsy medicine with L-2-aminobutyramide hydrochloride, its synthetic steps are as follows:

[0067] One) the resolution of L-2-aminobutanamide hydrochloride

[0068] Take 10.2g (0.1mol) of 2-aminobutanamide and put it into a 250mL three-necked flask, add 80mL of isopropanol, stir to disperse, add 3.6g (0.04mol) of inducer glyceraldehyde and 18.0g (0.12mol) of resolving agent L - Tartaric acid, heated to 65°C, maintained at 65°C for asymmetric resolution, stirred for 8 hours, filtered, washed with a small amount of ethanol to obtain L-2-aminobutyramide L-tartrate double salt (directly proceed to the next step without drying ).

[0069] Add the obtained L-2-aminobutyramide L-tartrate double salt to 11.9 mL of concentrated hydrochloric acid (2-aminobutanamide to hydrochloric acid molar ratio 1:1.25) with a concentration of 33 wt%, and stir at room temperature for separation reaction for 2 hours to the solution Completely clarified, then slo...

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Abstract

The invention discloses a method for synthesizing a medicine for treating epilepsy by using L-2-aminobutanamide hydrochloride, and relates to the technical field of medicine synthesis, and the method comprises the following steps: under the protection of nitrogen, adding L-2-aminobutanamide hydrochloride and 4-chlorobutyrate into isopropyl alcohol, and reacting under the action of an alkaline substance and a catalyst, heating and refluxing to carry out nucleophilic substitution reaction and ring-closure reaction to prepare the levetiracetam. According to the method, the levetiracetam is synthesized by adopting a milder alkaline substance and a one-pot method, the operation is simple, the levetiracetam can be prepared without post-treatment, the levetiracetam obtained by the method is low in impurity content and high in chemical purity, the yield can reach 83.43% or above, and the purity reaches 99.6%.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a method for synthesizing drugs for treating epilepsy with L-2-aminobutyramide hydrochloride. Background technique [0002] Epilepsy is a chronic recurrent short-term brain dysfunction syndrome caused by a variety of etiologies. The long-term recurrent seizures of the disease seriously affect the patient's quality of life and social work ability, and cause great harm to individuals and society. [0003] Levetiracetam, chemical name (S)-α-ethyl-2-oxo-1-pyrrolidineacetamide, is a new type of antiepileptic drug developed by UCB Company in Belgium. Etiracetam has the characteristics of high therapeutic index, high safety index, can be used for monotherapy, does not interact with other antiepileptic drugs, has mild side effects, good tolerance, and excellent pharmacokinetic indexes. The only antiepileptic drug with unique properties to prevent epilepsy. The chemical structura...

Claims

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Application Information

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IPC IPC(8): C07D207/27C07C231/20C07C237/06
CPCC07D207/27C07C231/20C07B2200/07C07C237/06
Inventor 漆定超张宝成张少平刘劲松于树岭
Owner CANGZHOU SENARY CHEM SCI TEC
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