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Process method for preparing vinorelbine

A technology of vinorelbine and dehydrated vinblastine, which is applied in the field of chemical pharmaceuticals, can solve the problems of low yield, high cost, and increased production cost, and achieve the effect of reducing production cost and cheap price

Inactive Publication Date: 2010-07-21
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

[0003] The chemical structure of vinorelbine is complicated, the synthesis is difficult, and the separation is also difficult, so that the synthetic yield is low and the cost is high
Published patents, such as the patent applications CN101037446A, CN101284842A, and CN1552715A, all adopt silver boron tetrafluoride as the ring shrinkage reagent, but silver boron tetrafluoride is a relatively expensive chemical reagent, which increases production costs

Method used

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  • Process method for preparing vinorelbine
  • Process method for preparing vinorelbine

Examples

Experimental program
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Effect test

Embodiment 1

[0013] (1) Preparation of Vinorelbine Crude Product (III) from Dehydrated Vinblastine Hydrochloride (I)

[0014] In a dry round bottom flask, add 20 g of dehydrated vinblastine hydrochloride (prepared in laboratory, HPLC purity 92.5%), under the protection of light and nitrogen, add 1000 ml of dry dichloromethane, stir to dissolve, add 20 ml of pyridine, and use dry ice Cool the acetone bath to below -50°C, add dropwise a mixed solution of 6g of bromosuccinimide, 13ml of trifluoroacetic acid and 1000ml of dry dichloromethane, and keep stirring below -50°C for 2 hours after the dropwise addition. After the reaction, add a mixed solution of 12g silver nitrate, 12g ammonium acetate, 1000ml deionized water and 800ml tetrahydrofuran, stir rapidly, gradually heat up to 20-30°C, maintain this temperature, and stir for 16 hours. After the reaction was completed, 10% sodium carbonate aqueous solution was added dropwise with stirring to make the water phase pH 8-9, and the phases were s...

Embodiment 2

[0018] (1) Preparation of Vinorelbine Crude Product (III) from Dehydrated Vinblastine Hydrochloride (I)

[0019] In a dry round bottom flask, add 20 g of dehydrated vinblastine hydrochloride (prepared in laboratory, HPLC purity 92.5%), under the protection of light and nitrogen, add 1000 ml of dry dichloromethane, stir to dissolve, add 2,6-dichloromethane Take 20ml of picoline, cool down to below -50°C with a dry ice acetone bath, add dropwise a mixed solution of 5.5g of bromosuccinimide, 15ml of trifluoroacetic acid and 1000ml of dry dichloromethane, and keep at -50°C after the dropwise addition The reaction was then stirred for 1.5 hours. After the reaction is over, add a mixed solution of 12g silver nitrate, 12g ammonium acetate, 1000ml deionized water and 800ml tetrahydrofuran, stir rapidly, gradually heat up to 20-30°C, maintain this temperature, and stir for 24 hours. After the reaction was completed, 10% sodium carbonate aqueous solution was added dropwise with stirrin...

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Abstract

The invention discloses a process method for preparing vinorelbine, which comprises the following steps: taking dehydration vinblastine or salt thereof as a starting material, obtaining rough vinorelbine after bromoforming and a ring contraction reaction, and obtaining vinorelbine through column chromatography. The method adopts silver nitrate to replace silver boron tetrafluoride to be served as a reduction cyclization reagent, and thereby not influencing the yield of the reaction and the purity of crude products, and further reducing the production cost.

Description

technical field [0001] The invention relates to the field of chemical pharmacy, in particular to a process for preparing the antineoplastic drug vinorelbine Background technique [0002] Vinorelbine (trade name: Navelbing) is a new type of semi-synthetic vinblastine anticancer drug, chemical name 3',4'-didehydro-4'-deoxy-8'-de Vinblastine, developed by the French company PieerFabre and first listed in France in 1989, it mainly inhibits the polymerization of centromere tubulin to stop cell division in the middle stage of mitosis, and is a cell cycle-specific antineoplastic drug . The change in its structure makes it have strong and specific anti-mitotic properties, and it shows lower neurotoxicity and stronger anti-tumor activity than other vinblastine anti-tumor drugs. [0003] The chemical structure of vinorelbine is complicated, the synthesis is difficult, and the separation is also difficult, so that the synthesis yield is low and the cost is high. Published patents, s...

Claims

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Application Information

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IPC IPC(8): C07D519/04
Inventor 钱建彬刘飞键吴祖望陈轶之张广明
Owner 深圳万乐药业有限公司
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