Method for synthesizing tafluprost

A technology for tafluprost and compounds, which is applied in the field of synthesizing tafluprost, can solve the problems of low production efficiency, high cost, low purity, etc., and achieve the effect of precise control of reaction conditions and improvement of atom economy

Pending Publication Date: 2021-12-21
上海京河医药科技有限公司
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  • Abstract
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Problems solved by technology

[0005] Aiming at the deficiencies of the prior art, the invention provides a method for synth...

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  • Method for synthesizing tafluprost
  • Method for synthesizing tafluprost
  • Method for synthesizing tafluprost

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Embodiment

[0038] Such as Figure 1-6 As shown, the embodiment of the present invention provides a method for synthesizing tafluprost, comprising the following specific preparation steps:

[0039] S1. Preliminary reaction, the preliminary medicament is obtained through the oxidation reaction of the original compound, specifically, 9.0g, 1.2eq of NaOCl oxidant, 1.5g, 0.1eq of TEMPO catalyst and 11.7g of NaBr, 1.0eq are added to DCM100mL, stirred for 15 minutes, Cool down to -10-0°C, add 17.2g of the compound of formula 1 in DCM100mL solution dropwise to the above reaction mixture, keep stirring at -10-0°C for 3h, add DCM300mL to dilute, add 10% sodium thiosulfate aqueous solution Perform quenching, keep stirring at 0-10°C for 1 hour, separate the liquids, combine the organic phases, and dry the organic phases with anhydrous sodium sulfate to obtain a preliminary medicament;

[0040] S2. Secondary reaction, the secondary reaction compound is obtained through the Horner-Wadsworth-Emmons re...

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Abstract

The invention provides a method for synthesizing tafluprost, and relates to the technical field of tafluprost synthesis. The method for synthesizing the tafluprost comprises the following specific preparation steps: S1, primary reaction, S2, secondary reaction, S3, third reaction, S4, fourth reaction, S5, fifth reaction and S6, final reaction. The invention provides the method for synthesizing tafluprost. According to the method for synthesizing tafluprost, racemic Corey lactone diol is used as a raw material, the tafluprost is obtained through oxidation, condensation, fluorination, reduction, recondensation and esterification reaction, the total mass yield of six-step reaction of the preparation method can reach 22%, the process is stable, the prepared tafluprost product is colorless viscous oily liquid, and the purity of the tafluprost product is up to 99% or above.

Description

technical field [0001] The invention relates to the technical field of synthesizing tafluprost, in particular to a method for synthesizing tafluprost. Background technique [0002] Tafluprost is a new prostaglandin analog, mainly used for the treatment of open-angle glaucoma or ocular hypertension in patients with elevated intraocular pressure. The outflow of the sclera reduces intraocular pressure. The 15th hydroxyl group in the traditional prostaglandin analog structure is an essential functional group for prostaglandin receptor agonists to exert physiological activity. Tafluprost replaces this functional group with 2 F atoms, as An isopropyl ester that is rapidly hydrolyzed by corneal esterases to the free acid form, the active form of the compound, tafluprost has about the same affinity for the FP receptors of the iridociliary body as the carboxylic acid product of latanoprost 12 times stronger. [0003] The existing patent (CN103804195B) obtains a universal intermedia...

Claims

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Application Information

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IPC IPC(8): C07C69/736C07C67/307
CPCC07C67/307C07C67/00C07D307/935C07C69/736
Inventor 杨君
Owner 上海京河医药科技有限公司
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