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Paroxetine hydrochloride compound and synthetic method thereof

A technology of paroxetine hydrochloride and paroxetine methyl, which is applied in the field of medicine, can solve problems such as unfavorable removal of organic solvents, poor stability of chloroformic acid-α-chloroethyl ester, complicated operation, etc., and achieve mild production conditions and good stability , the effect of high total yield

Active Publication Date: 2012-10-10
ZHEJIANG JIANFENG PHARM CO LTD
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AI Technical Summary

Problems solved by technology

In the original process, chloroformic acid-α-chloroethyl was used as a demethylation reagent. In the synthesis of this reagent, freshly distilled thionyl chloride was used. The operation was complicated, and the synthesized chloroformic acid-α-chloroethyl had poor stability, and the yield was about 67%
[0006] Chinese invention patent application (application number: 200810104136.1 application date: 2008-04-16) discloses a preparation method of paroxetine hydrochloride and its intermediates. Using a compound of structural formula (II) to prepare a compound of structural formula (I), and then preparing paroxetine, this method involves a variety of organic solvents, which is not conducive to the removal of organic solvents;

Method used

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  • Paroxetine hydrochloride compound and synthetic method thereof
  • Paroxetine hydrochloride compound and synthetic method thereof
  • Paroxetine hydrochloride compound and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthetic process and refining method of paroxetine hydrochloride

[0031] 1) Preparation of crude paroxetine hydrochloride:

[0032] Such as figure 2 As shown, add 20 kg of N-methylparoxetine into 290 kg of toluene, stir, add ethyl chloroformate toluene mixture dropwise at room temperature, after the addition, stir for 30 minutes, heat up to 60-70 ° C, keep stirring for 4- After 6 hours (TLC detected that the reaction was complete, petroleum ether: ethyl acetate = 3:1), the organic layer was washed with water and aqueous sodium bicarbonate solution respectively, the water layer was separated, and the toluene was concentrated under reduced pressure to obtain a viscous substance.

[0033] N-methylparoxetine, source: Linhai Jinqiao Chemical Factory

[0034]

[0035] Add 700kg of ethanol to the residue, add 70.0Kg of potassium hydroxide, and heat up and reflux for 20-25 hours (about 80°C) (TLC test shows that the reaction is complete, if the reaction is too slow, add...

Embodiment 1 3

[0043] The stability situation of embodiment 1 three batches of samples is as follows:

[0044] Stability inspection items: selected according to the key inspection items stipulated in the above guiding principles and the properties of this variety, mainly including appearance, pH, moisture, related substances, and content.

[0045] Inspection basis: According to the 2010 edition of the Pharmacopoeia standard of paroxetine hydrochloride

[0046] Sample: three batches of 100401, 100402, and 100403 produced in Example 1.

[0047] accelerated test

[0048] Test method: Take this product to simulate the packaging of the marketed drug, and place it at 40 ° C ± 2 o C Place it under the condition of relative humidity RH75%±5% for 6 months. Samples were taken at 0, 1, 2, 3 and 6 months, and the indicators measured were compared with the samples at 0. The test results are shown in Table 1.

[0049] The accelerated test was carried out for 6 months, and the test results showed tha...

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Abstract

The invention relates to the field of medicine and particularly relates to a paroxetine hydrochloride compound and a synthetic method thereof. The paroxetine hydrochloride compound has the following structural formula. According to the paroxetine hydrochloride compound, ethyl chloroformate for industrial production is used as a demethylation reagent, the reagent is stable, the production condition of demethylation is moderate, the total yield is high and about 75%, and the paroxetine hydrochloride compound accords with the requirement of a 2010 edition of a pharmacopeia and applicable to industrial production.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a paroxetine hydrochloride compound and a synthesis method thereof. Background technique [0002] Paroxetine hydrochloride, chemical name: (-)-(3S,4R)-4-(fluorophenyl)-3-{[3,4-(methylenedioxy)phenoxy]methyl}-piperidine Hydrochloride hemihydrate. Its structural formula is as follows: [0003] ; [0004] It is suitable for the treatment of various depressions. Includes depression with anxiety and reactive depression, panic disorder with or without agoraphobia, and obsessive-compulsive disorder. [0005] In the existing paroxetine hydrochloride process, p-fluorobenzaldehyde is used as the starting raw material, and methyl paroxetine hydrochloride is generated through five-step reactions, and then paroxetine hydrochloride is generated through demethylation reaction, and the specific route is as follows figure 1 . Using p-fluorobenzaldehyde as the starting material, it undergoes a five...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12
Inventor 蒋晓萌黄金龙施存元张孝君蔡月苹
Owner ZHEJIANG JIANFENG PHARM CO LTD
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