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Preparation method of compound serving as farnesoid X receptor (FXR)

A compound and solid technology, applied in the field of compound preparation, can solve the problems of low process efficiency, difficult separation and purification, low total yield, etc., and achieve the effects of flexible compound structure, easy purification and economical raw material cost.

Active Publication Date: 2017-04-26
BIRDO (SHANGHAI) PHARMATECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, this reaction route is a vertical reaction route, that is, compounds are synthesized step by step, and the overall yield is relatively low, and the final product after step 4 contains unreacted raw materials, and the unreacted raw materials are similar to the product structure and very little difference in properties, difficult to separate and purify
Therefore, the efficiency of the process is low

Method used

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  • Preparation method of compound serving as farnesoid X receptor (FXR)
  • Preparation method of compound serving as farnesoid X receptor (FXR)
  • Preparation method of compound serving as farnesoid X receptor (FXR)

Examples

Experimental program
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Embodiment 1

[0028]

[0029] Step 1: Preparation of compound B

[0030] Compound A (18.2g) Vinyl borate pinacol ester (13.3g) and triethylamine (TEA) (23.5mL) in anhydrous toluene (200mL), under the protection of nitrogen, add the catalyst PdCl 2 (Dppf) (0.5g). The reaction was raised to 80°C for 2 hours. The reaction was cooled to room temperature and filtered. The filtrate was washed with saturated sodium chloride solution (brine), dried and filtered to obtain a crude product. Purified by column chromatography to obtain 9.2 g of compound B as a yellow solid with a yield of 37%.

[0031] Step 2: Preparation of Compound C

[0032] Diazomethane (CH 2 N 2 ) preparation:

[0033] Add KOH (27g, 0.5mol), water (50mL), and ethylene glycol monomethyl ether (150mL) into a 1L three-necked flask. The system is equipped with an atmospheric distillation device, and the temperature is raised to 70°C. Diethyl ether solution (500 mL) of nitro-p-toluenesulfonamide (103 g, 0.5 mol) was added...

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Abstract

The invention discloses a preparation method of a compound shown in the chemical formula 1. According to the preparation method, parallel routes are adopted, so that the relative total yield is higher; besides, unreacted reactants and a reaction product have a large structural difference and a large polar phase, so that purification is easier, and the raw material cost is lower. The chemical formula 1 is defined in the description.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a method for preparing a compound as a farnesoid X receptor (FXR). Background technique [0002] The farnesoid X receptor (FXR) is a nuclear hormone receptor (also often referred to as NR1H4 when referring to human receptors) that belongs to the orphan nuclear receptor family. Both bile acids and farnesoids are ligands for FXR. FXR plays an important role in regulating cholesterol compounds, and its mechanism of action is related to the regulation of many genes. Guggul sterol (GS), a natural product found in Indian gum tree, is an FXR antagonist with good lipid-lowering effect. Studying the relationship between natural products and nuclear receptors such as FXR will find more lipid-lowering compounds similar to GS. For example, the compound represented by the following chemical formula 1 is a very concerned NR1H4 compound (CAS: 1268246-14-5). [0003] chemical formula 1 ...

Claims

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Application Information

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IPC IPC(8): C07D261/08
CPCC07D261/08
Inventor 王雷陈达王晓磊曹如圻
Owner BIRDO (SHANGHAI) PHARMATECH CO LTD
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