Chemical synthesis method of bosentan metabolite

A technology for chemical synthesis and metabolites, which is applied in the field of chemical synthesis of bosentan metabolites, and can solve problems such as reports on preparation methods of bosentan metabolites

Active Publication Date: 2021-07-06
四川摩尔生物制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In the prior art, there is no report on the preparation method of bosentan metabolites

Method used

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  • Chemical synthesis method of bosentan metabolite
  • Chemical synthesis method of bosentan metabolite
  • Chemical synthesis method of bosentan metabolite

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] A chemical synthesis method of bosentan metabolites, comprising the following steps:

[0028] The first step: the reaction process is shown in formula (1-1)

[0029]

[0030] Add 0.6 g of ammonium chloride to 22 g of chlorosulfonic acid at room temperature, stir for 5 minutes, then slowly drop in 25 g of methyl 2,2-dimethylphenylacetate, raise the temperature to 75°C after the dropping, and keep it warm for 0.5 hours; then Cool down to room temperature and pour into ice water, extract with 200ml ethyl acetate, then wash with saturated brine, mix and stir the washed material with 250ml ice water, then add 50ml ammonia water, stir naturally for 2h, TLC shows that the basic reaction is complete, After standing still, the organic layer was separated, washed with water, dried, evaporated to dryness, and purified by column to obtain 18 g of brown oil M1.

[0031] The second step: the reaction process is shown in formula (1-2)

[0032]

[0033] Dissolve 18g of M1 in 20...

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PUM

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Abstract

The invention discloses a chemical synthesis method of bosentan metabolite. According to the method disclosed by the invention, the bosentan metabolite is obtained from 2, 2-dimethyl methyl phenylacetate through six-step reaction. The whole preparation method is high in operability, high in preparation efficiency and low in production cost, and industrial mass production can be achieved. The bosentan metabolite prepared by the invention is higher in bioavailability, can directly play a role in resisting hypertension, and is lower in adverse reaction.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and in particular relates to a chemical synthesis method of bosentan metabolites. Background technique [0002] Bosentan is an endothelin receptor antagonist belonging to a class of highly substituted pyrimidine derivatives with affinity for ETA and ETB receptors. Bosentan reduces pulmonary and systemic vascular resistance, thereby increasing cardiac output without increasing heart rate. The neurohormone endothelin is a potent vasoconstrictor that promotes fibrosis, cell proliferation, and tissue remodeling. Bosentan tablets are indicated for the treatment of pulmonary arterial hypertension in patients with WHO stage III and IV primary pulmonary hypertension, or pulmonary hypertension caused by scleroderma. Bosentan is metabolized in the liver by the cytochrome P450 isoenzymes CYP3A4 and CYP2C9. There are three bosentan metabolites in human plasma. Only one metabolite Ro48-5033 (hydrox...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/52
CPCC07D239/52
Inventor 田单杨开勇
Owner 四川摩尔生物制药有限公司
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