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Etazocine hydrobromide bulk drug impurity and preparation method thereof

A technology of etazocine hydrobromide and raw materials, applied in the field of medicinal chemistry, to achieve the effect of high purification difficulty

Inactive Publication Date: 2020-11-20
深圳万乐药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is no relevant report about the impurity of etazocine hydrobromide crude drug at present, in order to obtain high-quality etazocine hydrobromide crude drug and further prepare safe and effective etazocine hydrobromide preparations, it is necessary to Confirm the structure of the impurity produced in the synthesis process of etazocine hydrobromide raw material drug and prepare the impurity compound with high purity for the quality control process of etazocine hydrobromide raw material drug and preparation

Method used

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  • Etazocine hydrobromide bulk drug impurity and preparation method thereof
  • Etazocine hydrobromide bulk drug impurity and preparation method thereof
  • Etazocine hydrobromide bulk drug impurity and preparation method thereof

Examples

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Effect test

Embodiment 1

[0028] The preparation of embodiment 1 impurity a compound

[0029] Add 26g of compound II and 190.2g of 48% hydrobromic acid to a 250ml glass reaction bottle successively, and react at 100-120°C under the protection of nitrogen. Concentrate to dryness under pressure. The concentrate was dissolved by adding an appropriate amount of absolute ethanol, and then concentrated to dryness under reduced pressure. This step was repeated three times to obtain 38.2 g of a black oily crude compound I.

[0030] Add 80 g of absolute ethanol to the crude compound I above to dissolve until clear, add dropwise 350 ml of isopropyl ether and stir, the precipitated solid will turn into oil at the bottom, slowly pour out the supernatant, and concentrate the remaining solvent under reduced pressure. Add 80 g of absolute ethanol to the concentrate, add dropwise 400 ml of isopropyl ether, stir and crystallize, and suction filter to dryness.

[0031] The solid was transferred to a vacuum oven at 40-...

Embodiment 2

[0040] The preparation of embodiment 2 impurity a compound

[0041] Add 26g of compound II and 193.7g of 40% hydrobromic acid to a 250ml glass reaction bottle successively, and react at 100-120°C under the protection of nitrogen. Concentrate to dryness under pressure. The concentrate was dissolved by adding an appropriate amount of absolute ethanol, and then concentrated to dryness under reduced pressure. This step was repeated three times to obtain 37.8 g of a black oily crude compound I.

[0042]Add 80 g of absolute ethanol to the crude compound I above to dissolve until clear, add dropwise 350 ml of isopropyl ether and stir, the precipitated solid will turn into oil at the bottom, slowly pour out the supernatant, and concentrate the remaining solvent under reduced pressure. Add 80 g of absolute ethanol to the concentrate, add dropwise 350 ml of isopropyl ether, stir and crystallize, and suction filter to dryness.

[0043] The solid was transferred to a vacuum oven at 40-5...

Embodiment 3

[0044] The preparation of embodiment 3 etazocine hydrobromide crude drug

[0045] According to the process disclosed in patent CN 104356065A, etazocine hydrobromide was prepared, and the product was detected by HPLC under the same chromatographic conditions as in Example 1. figure 2 , wherein, the appearance of each chromatographic peak comprising etazocine hydrobromide and its contained impurity a is as follows:

[0046] name Peak time (min) Peak area content(%) Peak height N / A 17.608 12767 0.15 1348 Impurity a 19.266 50060 0.58 6512 Etazocine Hydrobromide 21.623 8592118 98.88 682547 N / A 31.120 34110 0.39 1804

[0047] Compared with the HPLC chromatogram of compound I prepared in Example 1, it can be seen that the peak time of compound I and impurity a is the same, so that impurity a can be determined to be the structure of compound I.

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Abstract

The invention provides an impurity a generated in the synthesis of the etazocine hydrobromide bulk drug and the preparation method thereof. The purity of the impurity a compound prepared by the preparation method provided by the invention reaches 95% or above, and the impurity a compound is suitable for being used as a reference substance in the quality control process of the etazocine hydrobromide bulk drug or preparation.

Description

technical field [0001] The present invention relates to but not limited to the field of medicinal chemistry, in particular to an impurity of etazocine hydrobromide and a preparation method thereof. Background technique [0002] Eptazocine hydrobromide was originally developed by Nihon lyakuhin Kogyo Co., Ltd. and was launched in Japan in 1987. It is mainly used for the treatment of postoperative pain and cancer pain. Eptazocine hydrobromide Xin is a partial agonist of opioid receptors, acts on K receptors, uses selective antagonists to block postsynaptic receptors, and blocks chemical messengers that transmit pain information. In terms of analgesia, the analgesic efficacy of ethazocine is 1-2 times that of pentazocine. The structural formula of etazocine hydrobromide is as follows: [0003] [0004] Patent EP0384917A1 discloses the synthetic method of etazocine hydrobromide, the method uses compound 1-1,4-dimethyl-10-methoxy-2,3,4,5-tetrahydro-1,6- Endomethylene-1H-4-b...

Claims

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Application Information

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IPC IPC(8): C07D223/14
CPCC07B2200/13C07D223/14
Inventor 陈齐阳吴子强刘东华罗唐于玉根
Owner 深圳万乐药业有限公司
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