Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of synthetic method of rabeprazole metabolite of single configuration

A technology of rabeprazole and a synthesis method, which is applied in the field of drug metabolism to achieve the effects of reasonable process design, strong operability, and great application research value

Active Publication Date: 2018-05-04
TLC NANJING PHARMA RANDD CO LTD
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there is no report on the synthesis method of rabeprazole metabolites with a single configuration

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of synthetic method of rabeprazole metabolite of single configuration
  • A kind of synthetic method of rabeprazole metabolite of single configuration
  • A kind of synthetic method of rabeprazole metabolite of single configuration

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The preparation of the rabeprazole metabolite of the single configuration of embodiment 1 specifically comprises the following steps:

[0033] Such as figure 1 Shown is the reaction flow diagram of the present invention:

[0034] (1) Take rabeprazole sulfide (I) (20g) and suspend it in hydrobromic acid (300mL) with a volume concentration of 48%, heat to 100 degrees, react for 1 hour, cool the reaction solution to room temperature, and then Under the bath, slowly add water and ethyl acetate to the reaction solution, adjust the pH to 9-10 with 25% volume concentration of ammonia water, a large amount of white solid precipitates, filter to obtain desmethyl rabeprazole sulfide (II) Crude product 20g, obtain 11g desmethyl rabeprazole sulfide (II) intermediate after column chromatography purification;

[0035]

[0036] (2) Suspend the intermediate (II) (20g) in 200mL of dichloromethane, add imidazole (12.4g) and tert-butyldimethylsilyl chloride (12g) successively, after ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for synthesizing rabeprazole metabolites with a single configuration. The method takes rabeprazole sulfide as a starting material and synthesizes it through five-step reactions. The present invention screens out the optimal preparation steps and reaction conditions through a large number of experiments. The whole process design is reasonable and the operability is strong. The single-configuration rabeprazole metabolite prepared by the present invention has a chemical purity of more than 99%. And chiral purity >99.5%. The single-configuration rabeprazole metabolite prepared by the present invention provides a standard product for the research on the metabolic mechanism of rabeprazole drug, and can be used to explore the metabolic process of the drug in vivo, and has great potential in clinical pharmacokinetic research. Great applied research value.

Description

technical field [0001] The invention relates to a synthesis method of a compound, in particular to a method for synthesizing a single-configuration rabeprazole metabolite by a chemical method, and belongs to the field of drug metabolism. Background technique [0002] Rabeprazole drug, chemical name 2-[[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl]-1H-benzimidazole; Rabeprazole Prazole and its intermediates; 2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]-sulfoxyl}1H-benzimidazole is a novel Proton pump inhibitor, which is more effective than omeprazole, has no anticholinergic and anti-H2 histamine properties, but can attach to the surface of gastric parietal cells to inhibit the secretion of gastric acid by inhibiting H+ / K+-ATPase, mainly used for treatment Stomach trouble. [0003] Chiral resolution is essential for studying the pharmacokinetics of chiral drugs, because enantiomers and metabolites with optical activity often show different pharmacological activ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12C07B57/00
CPCY02P20/55
Inventor 张帅胡永铸刘春徐一鸣
Owner TLC NANJING PHARMA RANDD CO LTD