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Refining method of deuterium tryptophan hydroxylase inhibitor compound

A technology of tryptophan hydroxylase and refining method, which is applied in the field of refining deuterated tryptophan hydroxylase inhibitor compounds, and can solve the problem of high compound content

Inactive Publication Date: 2018-11-13
湖南华腾制药有限公司
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Problems solved by technology

[0012] The invention provides a method for refining deuterated tryptophan hydroxylase inhibitor compounds, the purpose of which is to solve the problem that the content of the main impurity compound of formula (II) in the product is too high

Method used

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  • Refining method of deuterium tryptophan hydroxylase inhibitor compound
  • Refining method of deuterium tryptophan hydroxylase inhibitor compound
  • Refining method of deuterium tryptophan hydroxylase inhibitor compound

Examples

Experimental program
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Embodiment 1

[0024] Refining of formula (I) compound:

[0025]

[0026] Add 2g of deuterated Xermelo (compound of formula I) to 24g of butyl acetate, then add 0.2g of activated carbon, heat to 60°C, stir for 4h, cool to room temperature, filter, and concentrate the filtrate under reduced pressure, then add the concentrated residue to iso Propanol, ammonia water and acetonitrile (isopropanol: ammonia water: acetonitrile = 10:3:1, mass ratio) mixed solvent (total mass is 28g), heated to reflux, stirred for 5h, cooled to room temperature, filtered, filter cake Then wash with cold isopropanol and dry to obtain the pure product of formula (I). The content of the compound of the formula (I) is 99.73%, the content of the compound of the formula (II) is 0.02%, and other simple impurities are all less than 0.1%.

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Abstract

The invention provides a refining method of a deuterium tryptophan hydroxylase inhibitor compound. In the method, active carbon is used in an organic solvent to adsorb and remove impurities, and thenrecrystalization is performed. A solvent for the recrystalization is an isopropanol-ammonia water-acetonitrile mixed solvent system. According to the refining method, the HPLC purity of the deuteriumtryptophan hydroxylase inhibitor compound to be refined is 99.5 percent or more; furthermore, the refining method is easy to operate and short in period, and the single impurity content is controllable.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, in particular to a method for refining deuterated tryptophan hydroxylase inhibitor compounds. Background technique [0002] Xermelo is a tryptophan hydroxylase inhibitor developed by Lexicon Pharmaceuticals and approved by the FDA in February 2017 for the treatment of carcinoid syndrome diarrhea. The chemical structural formula is as follows: [0003] [0004] Its most common adverse reactions (≥5%) were nausea, headache, increased GGT, depression, flatulence, decreased appetite, peripheral edema, and pyrexia. Therefore, in order to increase the half-life, reduce the dosage of medicine, and reduce drug toxicity, by optimizing the structure of this medicine, obtain the compound shown in formula (I): [0005] [0006] Animal experiments show that the compound of formula (I) has better pharmacokinetic properties than Xermelo. However, the compound of formula (I) is difficult to purify, an...

Claims

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Application Information

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IPC IPC(8): C07D403/12
CPCC07D403/12
Inventor 邓泽平许慧
Owner 湖南华腾制药有限公司
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