Preparation method of sparsenatan for stabilizing isotope labeling

A diphenylsulfonamide and isotope labeling technology, which is applied in the field of medicine, can solve the problems of no stable preparation methods of diphenylsulfonamide drugs, and achieve the effects of large application research value, reasonable process design and high yield

Active Publication Date: 2015-07-08
TLC NANJING PHARMA RANDD CO LTD
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Problems solved by technology

[0004] At present, there is no report on the preparation method of stable isotope-labeled diphenylsulfonamides drug standard

Method used

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  • Preparation method of sparsenatan for stabilizing isotope labeling
  • Preparation method of sparsenatan for stabilizing isotope labeling
  • Preparation method of sparsenatan for stabilizing isotope labeling

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Embodiment 1

[0030] Example 1 The preparation of a stable isotope-labeled diphenylsulfonamide drug (Sparsenatan) is as follows: figure 1 Shown is the reaction flow diagram of the present invention:

[0031] (1) Dissolve 3-methyl-4-bromobenzoic acid (0.093mol) in a mixed solvent of ethanol and toluene (1:1, 560ml), add a catalytic amount of concentrated sulfuric acid and then reflux for overnight reaction. After the reaction, use Sodium bicarbonate was neutralized and added to water to extract the organic phase obtained with dichloromethane. After drying and concentrating, it was dissolved in carbon tetrachloride (200ml) and N-bromosuccinimide (6.5g) was added for reflux reaction for three days. After cooling and filtration, the filtrate was concentrated and spin-dried to obtain 11g of bromide, which was dissolved in methanol (200ml), added sodium formate (8.87g) and refluxed for 6 hours, then concentrated and purified by column chromatography to obtain 8.5g of intermediate IV;

[0032] ...

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Abstract

The invention discloses a preparation method of sparsenatan for stabilizing isotope labeling. According to the method, 3-methyl-4-bromobenzoic acid is used as a raw material, iodoethane for deuterium labeling serves as a deuterium labeling initiator, and the sparsenatan is obtained through six-step reaction. Optimal preparation steps and reaction conditions are screened out through a large number of experiments, and the whole preparation method is reasonable in design and good in operability. The purity of the sparsenatan prepared by means of the method and used for stabilizing the isotope labeling can be higher than 99%, and the isotope abundance is higher than 99%. The sparsenatan prepared by means of the method and used for stabilizing the isotope labeling is a standard product for research on the metabolic mechanism of the sparsenatan, can be used for tracing the metabolic process of the sparsenatan in a living body and has great application and research value on clinic pharmacokinetic study.

Description

technical field [0001] The invention relates to a synthesis method of a stable isotope-labeled compound, in particular to a preparation method of a deuterium-labeled diphenylsulfonamide drug (Sparsenatan) standard product for treating hypertension and diabetic nephropathy, belonging to the technical field of medicine. Background technique [0002] Diphenylsulfonamide drugs, chemical name 4'-[2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)-methyl]- N-(3,4-Dimethyl-5-isoxazolyl)-2'-ethoxymethyl-[1,1'-biphenyl]-2-sulfonamide (Formula I), is produced by the United States A new drug recently developed by a company for the treatment of hypertension and diabetic nephropathy. [0003] Deuterium is a non-radioactive isotope of hydrogen, symbol D. The isotopic abundance of deuterium in nature is about 0.016%. Deuterium-labeled compounds are stable isotope-labeled compounds, which are compounds in which hydrogen atoms or part of hydrogen atoms in the compound are replaced with deute...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/12
CPCC07B2200/05C07D413/12
Inventor 马富宋化丰刘春徐一鸣
Owner TLC NANJING PHARMA RANDD CO LTD
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