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Deuterium-labeled metenolone stable isotope labeled compound

A technology of isotope labeling and primobolone, which is applied in the direction of isotope introduction into organic compounds, steroids, steroid isotope introduction, etc., can solve the problems of unsatisfactory internal standard reagents, danger, and little difference, etc., and achieve process design Reasonable, reproducible, and easy-to-operate results

Inactive Publication Date: 2021-07-02
阿尔塔(天津)标准物质研究院有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are relatively few reports about its isotope-labeled compounds, among which Primothenolone Acetate- 14 C 1 Synthesis of the expensive diazomethane- 14 C 1 , is not only costly and dangerous, but also the relative molecular mass is not much different from the natural abundance primobolone, which cannot meet the requirements of internal standard reagents

Method used

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  • Deuterium-labeled metenolone stable isotope labeled compound
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  • Deuterium-labeled metenolone stable isotope labeled compound

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Experimental program
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Effect test

Embodiment 1

[0031] The starting compound I (1.0 g) was dissolved in 13 mL of deuterated methanol (CH 3 OD), under nitrogen protection, sodium methoxide (0.5g, 3eq) was added at room temperature, and the reaction was carried out at this temperature for about 48 hours. The reaction mixture was quenched with 30% deuterium hydrochloric acid (DCl), monitored the system to pH = 6, extracted 2-3 times with dichloromethane, combined the organic phases, dried, filtered, and concentrated under reduced pressure to obtain the product, and repeated the above process 3 times , and then through normal phase purification to obtain the target compound (0.92g), the yield was 90%, the HPLC detection, the chemical purity was 99.3%, the MS detection, the isotope abundance was 94.7%.

Embodiment 2

[0033] The raw material compound I (1.5g) was dissolved in 10mL of tetrahydrofuran and 10mL of heavy water (D 2 O) under nitrogen protection, potassium carbonate (2.1g, 3eq) was added at room temperature, after the addition was complete, the reaction was carried out at this temperature for about 48 hours. The reaction mixture was quenched with 30% deuterium hydrochloric acid to pH = 6, extracted 2-3 times with ethyl acetate, the organic phases were combined, dried, filtered, and concentrated under reduced pressure to obtain a crude product. Repeat the above process 3 times, and then The target compound (1.4 g) was obtained by normal phase purification, with a yield of 92%, a chemical purity of 99.6% detected by HPLC, and an isotopic abundance of 93.0% detected by MS.

Embodiment 3

[0035] The raw material compound I (1.2g) was dissolved in 10mL of tetrahydrofuran and 10mL of heavy water (D 2 O) under nitrogen protection, sodium hydroxide (1.6g, 10eq) was added at room temperature, and after the addition was completed, the reaction was carried out at this temperature for about 48 hours. The reaction mixture was quenched with 30% deuterated hydrochloric acid to pH = 6, extracted 2-3 times with acetic acid, the organic phases were combined, dried, filtered, and concentrated under reduced pressure to obtain a crude product. Repeat the above process 3 times for normal phase purification The target compound (1.1 g) was obtained with a yield of 91.0%, a purity of 99.1% detected by HPLC, and an isotopic abundance of 92.5% detected by MS.

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Abstract

The invention provides a deuterium-labeled metenolone stable isotope labeled compound. The structural formula of the deuterium-labeled metenolone stable isotope labeled compound is shown as a formula II, and the deuterium-labeled metenolone stable isotope labeled compound is obtained by taking a compound I as a raw material and carrying out H-D exchange reaction in a deuterium-labeled solvent, namely a deuterium source, in the presence of alkali at a proper temperature. According to the deuterium-labeled metenolone stable isotope labeled compound disclosed by the invention, deuterium replacement is carried out on 1-position methyl-H, 2-position olefinic bond H at carbonyl alpha position and 4-position methylene H in a natural abundance metenolone structure, the deuterium-labeled metenolone stable isotope labeled compound is 6 mass numbers different from that of metenolone, and the mass spectrum response data is obviously different, the physical property requirements of the internal standard substance required by isotope dilution mass spectrometry are completely met, the preparation method is reasonable in process design, controllable in experimental process and simple and convenient to operate, the prepared target product is high in purity, the yield reaches about 90.0%, the isotope abundance of the final product reaches about 93.5%-95.0%, the reproducibility is good, and a standard sample can be provided for the food safety detection industry.

Description

technical field [0001] The invention belongs to the field of drug synthesis, in particular to a deuterium-labeled primothenolone stable isotope-labeled compound. Background technique [0002] Methenolone, Chinese name 17β-hydroxy-1-methyl-5α-androst-1-en-3-one, is a mild anabolic steroid with very low androgen production. It can be used to allow the human body to maintain muscle fullness and anabolic capacity under the condition of low-carb water, and it can also improve human immunity. Since it has little side effects on the human liver and rarely causes symptoms of high blood pressure, it is considered "the safest of all steroids". Has great therapeutic value. In clinical practice, it will be used as protein anabolic agent, taking it or taking it by mistake will have a great impact on the performance of athletes. [0003] World Anti-Doping Agency (World Anti-Doping Agency, WADA) has included primobolone, metbolone, nandrolone, mesterolone, dehydromethyltestosterone, and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B59/00C07J1/00
CPCC07B59/007C07J1/0022C07B2200/05
Inventor 张磊秦爽韩世磊
Owner 阿尔塔(天津)标准物质研究院有限公司
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