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Deuterated compound as well as preparation method and application thereof

A technology for deuterated compounds and compounds, applied in the field of detection, can solve problems such as the inability to meet the requirements for quantitative detection of drug metabolites

Active Publication Date: 2022-03-01
SHENZHEN ASCENTAWITS PHARM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] With a small dose of drug, the external standard method or internal standard method corresponding to conventional liquid chromatography cannot meet the quantitative detection requirements of drug metabolites in biological samples under the condition of low dosage

Method used

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  • Deuterated compound as well as preparation method and application thereof
  • Deuterated compound as well as preparation method and application thereof
  • Deuterated compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0264] Example 1 Synthesis of AST-2660-D8-sodium salt

[0265]

[0266] Under nitrogen protection, deuterated 2-bromoethylamine hydrobromide (360mg, 1.72mmol), phosphorus oxychloride (132mg, 0.86mmol) was added to anhydrous dichloromethane (4mL) (deuterated 2 - hydrobromide of bromoethylamine, then add phosphorus oxychloride), cool to -78°C, add triethylamine (348mg, 3.44mmol) in dichloromethane solution (2mL) dropwise, and keep warm at -78°C After 30 minutes, the temperature was naturally raised to 0°C, and then kept at 0°C for 4 hours, and then the solid was quickly filtered off by suction, and the mother liquor was concentrated at low temperature and used directly in the next step.

[0267] The crude product obtained above was dissolved in water (30.8 mL), solid sodium hydroxide (275 mg, 6.88 mmol) was slowly added in portions, and the reaction was stirred at room temperature overnight. Then store at -20°C. 31 P-NMR characterization as figure 1 Shown: as the nuclear m...

Embodiment 2

[0282] Embodiment 2 detects the method for AST-2660-D8-sodium salt

[0283] In this embodiment, HMPA (hexamethylphosphoric triamide) is used as the internal standard of phosphorus spectrum to detect the content of AST-2660-D8-sodium salt prepared in Example 1.

[0284] Get HMPA (33.0mg, 0.1840mmol) and dissolve in water (2.2mL), the total mass is 2612mg, the concentration of HMPA is 7.050×10 -5 (mmol / mg, 31 The NMR shift of P-NMR is 29.890ppm)

[0285] The phosphorus spectrum was measured with HMPA aqueous solution as the internal standard, and the content of AST-2660-D8-sodium salt was determined.

[0286] 1. The first sample test

[0287] Get the AST-2660-D8-sodium salt aqueous solution prepared in Example 1, about 0.5mL (488mg) and the HMPA aqueous solution (317mg) that has been accurately weighed and prepared, and scan 64 times to measure the phosphorus spectrum (such as figure 2 Shown): The peak integral area ratio of the corresponding HMPA NMR peak of 29.874ppm and ...

Embodiment 5

[0291] The LC-MS / MS method of embodiment 5 and embodiment 7 is applicable to the low content detection of AST-2660-D8, AST-2660, and its corresponding LC liquid phase method (corresponding MS / MS detector is replaced by conventional differential detector, electrospray detector, evaporative light scattering detector) are also applicable to the constant (mg / ml) content detection of AST-2660 and AST-2660-D8.

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Abstract

The invention relates to a deuterated compound and a preparation method and application thereof.The structural formula of the deuterated compound I is shown in the formula (I), A is H or D, and at least one of the eight A is D; m is H or alkali metal, alkaline earth metal or ammonium. The invention provides an application of a deuterated compound I as an interior label in detecting the content of a metabolite II in a biological sample, and the metabolite II has a structural formula shown as a formula (II). Wherein A is H, and M is H or alkali metal, alkaline earth metal or ammonium. The content of the low-content metabolite II in the biological sample is quantitatively analyzed by using the deuterated compound I as an internal standard, the quantitative detection requirement under the low-concentration condition can be met, and the method is suitable for DMPK research in clinical tests.

Description

technical field [0001] The invention relates to the technical field of detection, in particular to a deuterated compound and a preparation method and application thereof. Background technique [0002] In human clinical trials, it is necessary to detect the content of drugs and drug metabolites in biological samples of subjects, such as blood, urine, tissues, etc., and conduct DMPK (DrugMetabolism and Pharmacokinetics, Chinese means drug metabolism and pharmacokinetics) research. In the process of new drug development, it is necessary to conduct DMPK research on drugs. [0003] Commonly used methods are liquid chromatography, with the help of high separation power of HPLC or UHPLC and ultraviolet absorption detector (UVD) diode array detector (PDAD), fluorescence detector (FLD), evaporative light scattering detector (ELSD), differential The detection performance of refractive index detectors, mass spectrometry detectors (MSDs) can detect almost all types of drugs and drug m...

Claims

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Application Information

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IPC IPC(8): C07F9/564C07B59/00G01N30/06
CPCC07F9/564C07B59/002G01N30/06C07B2200/05C07F9/65583C07B59/004G01N2030/045B01D15/166B01D15/426G01N30/16G01N30/7233G01N2030/027
Inventor 阮美珍蔡晓宏段建新唐纳德·T·荣李安蓉孟滕孙琳李兵
Owner SHENZHEN ASCENTAWITS PHARM TECH CO LTD
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