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Gabapentin impurity compound and preparation method thereof

A technology of gabapentin and compounds, which is applied in the field of gabapentin impurity compounds and its preparation, and can solve problems such as product quality impact

Pending Publication Date: 2022-07-01
SHANGHAI AOBO PHARMTECH INC LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few reports on its related process impurities and degradation impurities, but the present invention is aimed at the impurities that are produced during the synthesis process, storage and use of gabapentin, and will affect product quality, and have important significance for controlling product quality.

Method used

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  • Gabapentin impurity compound and preparation method thereof
  • Gabapentin impurity compound and preparation method thereof
  • Gabapentin impurity compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Example 1: 20.0 g of 2-oxaspiro[4.5]decane-1,3-dione (compound 1) was combined with 24.4 g of 2-(1-(aminomethyl)cyclohexyl)acetic acid (compound 1) 2) Add 300 mL of toluene, add 15.1 g of sodium carbonate and 10 g of sodium sulfate, and heat to 80° C. to react for 24 hours. After the reaction is completed, the system is cooled to room temperature 15~30°C, filtered to obtain a filtrate, the filtrate is decompressed to obtain a crude product, and 2-(1-((1,3-dioxa-2-aza is obtained through column chromatography. Spiro[4.5]decan-2-yl)methyl)cyclohexyl)acetic acid 25.2 g, yield 66.0%.

Embodiment 2

[0016] Example 2: Combine 20.0 g of 2-oxaspiro[4.5]decane-1,3-dione (compound 1) with 28.4 g of 2-(1-(aminomethyl)cyclohexyl)acetic acid (compound 2) Add 300 mL of 1,4-dioxane, add 19.6 g of potassium carbonate and 10 g of magnesium sulfate, and heat to 90° C. to react for 24 hours. After the reaction is completed, the system is cooled to room temperature 15~30°C, filtered to obtain a filtrate, the filtrate is decompressed to obtain a crude product, and 2-(1-((1,3-dioxa-2-aza is obtained through column chromatography. Spiro[4.5]decan-2-yl)methyl)cyclohexyl)acetic acid 27.1 g, yield 71.0%.

Embodiment 3

[0017] Example 3: Combine 20.0 g of 2-oxaspiro[4.5]decane-1,3-dione (compound 1) with 40.7 g of 2-(1-(aminomethyl)cyclohexyl)acetic acid (compound 2) Add 300 mL of dimethyl sulfoxide, add 14.3 g of triethylamine and 10 g of calcium chloride, and heat to 100° C. to react for 24 hours. After the reaction is completed, the system is cooled to room temperature 15~30°C, filtered to obtain a filtrate, the filtrate is decompressed to obtain a crude product, and 2-(1-((1,3-dioxa-2-aza is obtained through column chromatography. Spiro[4.5]decan-2-yl)methyl)cyclohexyl)acetic acid 21 g, yield 55.0%.

[0018] 1 H-NMR (d 6 -CDCl3)δ(ppm): 3.59(2H,s), 2.61(2H,s), 2.36(2H,s), 1.78-1.83(4H,m), 1.56-1.61(4H,m), 1.30-1.52 (13H, m).

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Abstract

The invention discloses an impurity compound of gabapentin and a preparation method of the impurity compound. The impurity is a compound shown in a formula I, the method is simple and easy to operate, mild in condition, high in yield, low in energy consumption and pollution and suitable for laboratory-level standard substance preparation.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, in particular to a gabapentin impurity compound and a preparation method thereof. [0002] technical background [0003] Gabapentin (Gabapentin), shown in chemical structure 3, chemical name is 2-(1-(aminomethyl)cyclohexyl)acetic acid [0004] [0005] Gabapentin is similar in structure to γ-aminobutyric acid (GABA), and its mechanism of action is not yet clear. At present, it is believed that its main mechanism of action has the following aspects: antagonism of N-methyl-D-aspartate (NMDA) receptors; It can produce GABA-like inhibitory effects, increase GABA synthesis and reduce GABA degradation; inhibit calcium ion channels in postsynaptic membranes, block abnormal discharge of diseased nerves; adjust abnormal sensory information by affecting peripheral nerves or most of the central nervous system. processing in the spinal cord. Indications: epilepsy, adjuvant therapy for partial...

Claims

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Application Information

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IPC IPC(8): C07D209/54
CPCC07D209/54
Inventor 王铨顾正杰张继承黄鲁宁陈茜陶安平安建国顾虹
Owner SHANGHAI AOBO PHARMTECH INC LTD
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