High-purity dapoxetine preparation method suitable for industrialization

A technology for dapoxetine hydrochloride and compounds, which is applied in the preparation of organic compounds, chemical instruments and methods, preparation of aminohydroxy compounds, etc., can solve the problems of high cost, harsh reaction conditions, complicated routes, etc., and achieves low cost and conversion. The effect of high rate and high reaction selectivity

Active Publication Date: 2015-05-20
REGENEX PHARMA LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0021] Aiming at the disadvantages of the prior art, such as harsh reaction conditions, the need to use highly toxic chemicals, cumbersome routes, and high cost, the present invention further studies the preparation proce

Method used

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  • High-purity dapoxetine preparation method suitable for industrialization
  • High-purity dapoxetine preparation method suitable for industrialization
  • High-purity dapoxetine preparation method suitable for industrialization

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Compound 1 (1.0g) was dissolved in 10ml of dichloromethane, under the protection of nitrogen, the temperature was controlled at -5~5°C, triphenylphosphine (1.7g) was added, and N-bromosuccinimide (1.1g ), reacted for 4h, and monitored the reaction by HPLC until compound 3 was completely reacted to generate compound 2.

Embodiment 2

[0049] 10eq of dimethylamine (1.7g) was added to the reaction system of Example 1, and the reaction temperature was 5°C. The reaction was monitored for completion by HPLC. They were washed with alkaline water, water and saturated brine respectively, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain compound 3 (0.84 g), with a yield of 87.9%.

Embodiment 3

[0051] Compound 3 (0.76g) was dissolved in ethyl acetate, and hydrogen chloride gas was passed through until no precipitation occurred, and filtered, and the resulting solid was recrystallized from isopropanol to obtain compound 4 (0.78g), namely dapoxetine hydrochloride, with a yield of 91.8 %, purity 99.9%, chiral purity 99.9%.

[0052] Route B:

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Abstract

The invention relates to a high-purity dapoxetine preparation method suitable for industrialization. In the preparation, S-3-(1-naphthoxy)-1-phenyl-1-propanol is taken as the raw material and is subjected to bromination, coupling, and salt-forming reactions so as to obtain dapoxetine; or racemic 3-(1-naphthoxy)-1-phenyl-1-propanol is taken as the raw material and is subjected to bromination, coupling, resolution, and salt-forming reactions so as to obtain dapoxetine. The provided preparation method overcomes the shortages of long reaction route, tedious technology, and high cost in the prior art, and has the advantages of mild reaction conditions, no requirement of high pressure and toxic reagent, short route, high conversion rate, and low cost. The prepared drug raw materials have better quality, and the preparation method is very practical in industry.

Description

technical field [0001] The invention relates to a preparation method of dapoxetine hydrochloride. Background technique [0002] Dapoxetine hydrochloride (S-dapoxetine hydrochloride), a selective serotonin (5-HT) reuptake inhibitor (SSR I), has been widely used in the treatment of depression and related affective disorders. Later studies have shown that the 5-HT receptors of premature ejaculation patients are highly sensitive. Dapoxetine has been shown to be effective in the treatment of premature ejaculation due to its ability to inhibit 5-HT reabsorption. In 2009, Dapoxetine Hydrochloride developed by Eli Lilly and Company for the treatment of male premature ejaculation (PE) was launched in Europe under the trade name Priligy. Prescription for oral administration approved for the treatment of PE. [0003] At present about the synthetic method of dapoxetine hydrochloride, mainly contain three kinds: [0004] The first route (see patent ZL200610024697.1), the reaction rou...

Claims

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Application Information

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IPC IPC(8): C07C217/48C07C213/08C07C213/02
Inventor 陈与华李智敏李斌彭贵子左联
Owner REGENEX PHARMA LTD
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