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Preparation method of high-purity palonosetron hydrochloride

A palonosetron, high-purity technology, applied in the field of preparation of high-purity palonosetron hydrochloride, can solve the problems of low yield, unstable process, low purity of palonosetron hydrochloride, etc., and achieve saving The effect of cost, environmental protection, and convenience for solvent recovery

Inactive Publication Date: 2021-07-13
KUNMING YUANRUI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0020] The object of the present invention is to provide a kind of preparation method of high-purity palonosetron hydrochloride, the present invention solves the problems of low purity, low yield and unstable process of palonosetron hydrochloride in industrial production by optimizing the preparation process question

Method used

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  • Preparation method of high-purity palonosetron hydrochloride
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  • Preparation method of high-purity palonosetron hydrochloride

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preparation example Construction

[0048] The invention provides a kind of preparation method of high-purity palonosetron hydrochloride, comprising the following steps:

[0049] Step 1), the synthesis of (S)-1,2,3,4-tetrahydronaphthoic acid:

[0050] Add 1,2,3,4-tetrahydronaphthoic acid and quinine into 50% ethanol, stir at 30-60°C to dissolve the solution, TLC detects that the reaction is complete, lower the temperature to below 0°C and place overnight, crystallize, pump Filter, dry, then add ethanol to refine, crystallize below 0°C, filter with suction, dry, add hydrochloric acid and ethyl acetate, separate liquid, dry, filter, concentrate, add n-hexane to the residue for recrystallization to obtain (S) -1,2,3,4-tetrahydronaphthoic acid;

[0051] Step 2), the synthesis of (R)-N-((S)-3-quinyl)-1,2,3,4-tetrahydronaphthyl-1-carboxamide

[0052] Dissolve compound (S)-1,2,3,4-tetrahydronaphthoic acid in ethyl acetate, add oxalyl chloride under stirring, stir at room temperature, add DMF and stir at room temperat...

Embodiment 1

[0116] Step 1), the synthesis of (S)-1,2,3,4-tetrahydronaphthoic acid

[0117] Add 17.6g of 1,2,3,4-tetrahydronaphthoic acid and 32.4g of quinine into 170mL of 50V / V% ethanol, stir at 50°C for 30min to dissolve the solution, TLC detects that the reaction is complete, PE:EA= 1:2, cool down to below 0°C and place overnight, crystallize, filter with suction, dry, then add 100mL ethanol to refine, crystallize below 0°C, filter with suction, dry, add 60mL of 1mol / L hydrochloric acid and 120mL of ethyl acetate The ester was separated, dried, filtered, concentrated, and the residue was recrystallized by adding n-hexane to obtain 7.50 g of a white solid with a yield of 42.6%. The HPLC showed that the purity was 99.81%. , toluene).

[0118] Step 2), the synthesis of (R)-N-((S)-3-quinyl)-1,2,3,4-tetrahydronaphthyl-1-carboxamide

[0119] Dissolve 17.6g (S)-1,2,3,4-tetrahydronaphthoic acid in 50mL ethyl acetate, add 10mL oxalyl chloride under stirring, stir at room temperature for 30min...

Embodiment 2

[0128] Step 1), the synthesis of (S)-1,2,3,4-tetrahydronaphthoic acid

[0129] Add 15.6g of 1,2,3,4-tetrahydronaphthoic acid and 29.8g of quinine into 158mL of 50V / V% ethanol, stir at 50°C for 30min to dissolve the solution, TLC detects that the reaction is complete, PE:EA= 1:2, cool down to below 0°C and place overnight, crystallize, filter with suction, dry, then add 90mL of ethanol to refine, crystallize below 0°C, filter with suction, dry, add 55mL of 1mol / L hydrochloric acid and 100mL of ethyl acetate The ester was separated, dried, filtered, concentrated, and the residue was recrystallized by adding n-hexane to obtain (S)-1,2,3,4-tetrahydronaphthoic acid as a white solid 7.21g, the yield was 43.6%, and the purity was shown by HPLC It was 99.82%, [α]D=-61.0° (c=1.0333, toluene).

[0130] Step 2), the synthesis of (R)-N-((S)-3-quinyl)-1,2,3,4-tetrahydronaphthyl-1-carboxamide

[0131] Dissolve 15.6g (S)-1,2,3,4-tetrahydronaphthoic acid in 50mL ethyl acetate, add 8mL oxaly...

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Abstract

The invention relates to the technical field of medicine synthesis, and especially relates to a preparation method of high-purity palonosetron hydrochloride. The preparation method of high-purity palonosetron hydrochloride not only solves the long-standing problems of low yield and unstable process of palonosetron hydrochloride, but also adopts three types of solvents, namely ethyl acetate, for extraction in each step of synthesis, not only is environment-friendly, but also is convenient for solvent recovery and cost saving, and is suitable for industrial production.

Description

[0001] This application is a divisional application of a Chinese patent application submitted to the China Patent Office on January 26, 2018, with the application number 201810076240.8 and the title of the invention "a method for preparing high-purity palonosetron hydrochloride". References are incorporated in this application. technical field [0002] The invention relates to the technical field of pharmaceutical synthesis, in particular to a preparation method of high-purity palonosetron hydrochloride. Background technique [0003] Palonosetron hydrochloride, chemical name: 2-[1-azabicyclo(2.2.2)oct-3S-yl]-2,3,3aS,4,5,6-hexahydro-1H-benzo [de] Isoquinolin-1-one hydrochloride. On July 25, 2003, palonosetron hydrochloride developed by the Swiss HelSinn company was approved by the United States, and it was first listed in the United States two months later. It is a new type of highly selective and high affinity 5-HT3 receptor antagonist, clinically used for acute and delaye...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D453/02
CPCC07D453/02
Inventor 王高华徐春霞刘文祥牛树伟
Owner KUNMING YUANRUI PHARMA
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