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Preparation method of high-purity Tafluprost and analogs thereof and intermediate compound

A technology of tafluprost and compounds, applied in the field of medicine, can solve problems such as not being suitable for industrial production

Inactive Publication Date: 2017-10-03
SUZHOU LANXITE BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the difficulty of simple removal of trans-VI, preparative HPLC purification is required, which makes this process unsuitable for industrial production

Method used

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  • Preparation method of high-purity Tafluprost and analogs thereof and intermediate compound
  • Preparation method of high-purity Tafluprost and analogs thereof and intermediate compound
  • Preparation method of high-purity Tafluprost and analogs thereof and intermediate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: 5-(triphenylphosphine) ethyl n-pentanoate bromide

[0029] Ethyl 5-bromo-n-valerate (4.16g) and triphenylphosphine (5.24g, 1eq) were dissolved in 100mL of anhydrous toluene and refluxed for 2 days under N2 protection. Cool down to room temperature, filter the precipitated white solid, and rinse with cold n-hexane. The resulting solid was dried in vacuo to obtain 8.46 g of the title compound (90% yield)

Embodiment 2

[0030] Embodiment 2: 5-(triphenylphosphine) isopropyl bromide n-pentanoate

[0031] Isopropyl 5-bromo-n-valerate (4.44 g) and triphenylphosphine (5.24 g, 1 eq) were dissolved in 100 mL of anhydrous toluene and refluxed for 2 days under N2 protection. Cool down to room temperature, filter the precipitated white solid, and rinse with cold n-hexane. The resulting solid was dried in vacuo to obtain 9.0 g of the title compound (93% yield)

[0032] HNMR: 7.23~7.56(15H), 3.89(1H), 2.32~2.87(4H), 1.45~1.75(4H), 1.32(6H)

Embodiment 3

[0033] Example 3: 5-(triphenylphosphine) tert-butyl n-pentanoate bromide

[0034] tert-butyl 5-bromo-n-valerate (4.72g) and triphenylphosphine (5.24g, 1eq) were dissolved in 100mL of anhydrous toluene and refluxed for 2 days under N2 protection. Cool down to room temperature, filter the precipitated white solid, and rinse with cold n-hexane. The resulting solid was dried in vacuo to obtain 7.1 g of the title compound (yield 71%)

[0035] HNMR: 7.23~7.56(15H), 2.32~2.87(4H), 1.45~1.75(4H), 1.25(9H)

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Abstract

The invention belongs to the technical field of medicine, and relates to a preparation method of Tafluprost and analogs thereof and a related intermediate compound. The preparation method is characterized in that (4-carboxybutyl)triphenylphosphonium bromide having a structure shown below is used as a witting reaction reagent, wherein R is alkyl or aryl. The method is simple, feasible and convenient for industrial production; and the Tafluprost and analogs thereof which are basically free of omega chain trans-isomers can be prepared.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a preparation method of high-purity tafluprost and similar compounds thereof and related intermediate compounds. Background technique [0002] Glaucoma is a common eye disease and has become the second most common eye disease. Topical drugs for the treatment of glaucoma include: β-adrenergic antagonists, the main varieties are betaxolol, timolol, etc.; α-adrenoceptor agonists, the main varieties are clonidine and aclonidine; Drug derivatives, including tafluprost, latanoprost, bimatoprost, etc. Prostaglandin derivatives reduce intraocular pressure mainly by increasing the outflow of aqueous humor through the uveoscleral pathway, and the effect of reducing intraocular pressure with these drugs alone is better than that of other drugs. In addition, because the mechanism of action of prostaglandin derivative anti-glaucoma drugs is different from that of other anti-glaucoma drugs, i...

Claims

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Application Information

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IPC IPC(8): C07C405/00C07F9/54
CPCC07C405/00C07F9/5442
Inventor 张健王润卿俞蒋辉
Owner SUZHOU LANXITE BIOTECH
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