Method for preparing fingolimod hydrochloride

A technology of fingolimod hydrochloride and preparation process, which is applied in the field of pharmaceutical synthesis, can solve the problems of long reaction time, low yield, unsuitability for large-scale production, etc. High efficiency and easy post-reaction treatment

Active Publication Date: 2014-07-16
安徽安腾药业有限责任公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] At the same time, Chinese patents CN1310869C and CN1212308C have also improved on the basis of this method, but the construction reaction time of hydroxyl and nitro in this type of method is long and the yield is low, so it is not suitable for large-scale production

Method used

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  • Method for preparing fingolimod hydrochloride
  • Method for preparing fingolimod hydrochloride
  • Method for preparing fingolimod hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Preparation of compound (III). Add 200g of raw material compound (II), 800ml of absolute ethanol, 160g of sodium ethoxide into a 2L flask, install a thermometer and a reflux condensing device, stir and heat to 50-55°C, stir and react for 5 hours, TLC detects that the reaction is complete, cool, Pour the reaction solution into 1L saturated sodium chloride solution, add 800ml ethyl acetate, separate the layers, and evaporate the organic phase to dryness under reduced pressure to obtain 160g of crude product compound (III) as light yellow oil, which was directly carried out without further purification One step reaction.

Embodiment 2

[0042] Preparation of compound (III). Add 100g of raw material compound (II), 600ml of anhydrous methanol, and 130g of sodium methoxide into a 2L flask, install a thermometer and a reflux condenser, stir and heat to 60-65°C, stir and react for 8 hours, TLC detects that the reaction is complete, cool, Pour the reaction solution into 500mL saturated sodium chloride solution, add 400ml ethyl acetate, separate the layers, and evaporate the organic phase to dryness under reduced pressure to obtain 76g of the crude product as light yellow oil compound (III). The crude product was directly carried out without further purification. One step reaction.

Embodiment 3

[0044] Preparation of compound (IV). Add 160g of crude compound (III) and 900ml of dichloromethane to a 2L flask, install a thermometer and a reflux condensing device, add 220g of thionyl chloride in batches, after the addition is complete, stir and heat to 80-85°C, and stir for 2 hours. TLC detected that the reaction was complete, cooled, poured the reaction solution into 2L saturated ammonium chloride solution, stirred and separated the liquids, and evaporated the organic phase to dryness under reduced pressure to obtain 190 g of crude yellow oil compound (IV), which was directly processed without further purification Next reaction.

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Abstract

The invention discloses a method for preparing fingolimod hydrochloride. The fingolimod hydrochloride is prepared by taking a compound (II) as starting material through six reaction steps such as hydrolysis, chlorination, reaction and salification. Compared with a traditional method, the method disclosed by the invention has the advantages that the required raw material is convenient and easily obtained, the operation is simple, the conditions are mild and easily controlled, the posttreatment is convenient, the environmental friendliness is realized and the yield in high; the method disclosed by the invention is suitable for industrial mass production.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and in particular relates to a method for preparing fingolimod hydrochloride. Background technique [0002] The structural formula of Fingolimod hydrochloride (Fingolimod, FTY720) is as formula (I), [0003] [0004] Its trade name is Gilenya, and its chemical name is 2-amino-2-[2-(4-n-octylphenyl)ethyl]-1,3-propanediol. On September 22, 2010, the US FDA approved the use of fingolimod as a first-line drug for relapsing multiple sclerosis, becoming the first oral drug approved for this disease. At present, the drug has been approved for marketing in the United States, Europe, Australia and other countries. [0005] Currently known preparation methods for compounds of formula (I) mainly include: [0006] Method 1: U.S. Patent No. 5,609,226 uses 2-(4-n-octylbenzene) iodoethane as the key intermediate. The specific synthetic route is as follows: [0007] [0008] This method has a lo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C215/28C07C213/08
Inventor 汪迅李新涓子李勇刚王卓史玉军高艳吕兴红王治越
Owner 安徽安腾药业有限责任公司
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