A sort of 18 F-labeled ethinyl estradiol and its preparation method and application

A technology of ethinyl estradiol and 18F, which is applied in the field of 18F-labeled ethinyl estradiol and its preparation, can solve problems such as harsh reaction conditions and serious adverse reactions, achieve fast reaction rate, simplify labeling steps and purification time, and solve reaction time long effect

Active Publication Date: 2020-02-07
JIANGSU INST OF NUCLEAR MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is to overcome the 18 F-labeled ethinyl estradiol synthesis and labeling reaction conditions are harsh and there are serious adverse reactions in the course of medication, thus providing a safe curative effect, easy to synthesize and label, and can use PET technology to clearly determine the activity of estrogen receptors 18 F-labeled ethinyl estradiol

Method used

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  • A sort of <sup>18</sup> F-labeled ethinyl estradiol and its preparation method and application
  • A sort of <sup>18</sup> F-labeled ethinyl estradiol and its preparation method and application
  • A sort of <sup>18</sup> F-labeled ethinyl estradiol and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0076] The compound described in this embodiment has the structure of formula (I) 18 F-labeled ethinyl estradiol, such as figure 1 shown, where R 1 Is ethylene, has formula (I-a) structure:

[0077]

[0078] The synthetic route of compound (I-a) is:

[0079]

[0080] The synthetic steps of the compound shown in above-mentioned formula I-a comprise:

[0081] Q1, mix 2.33g (10mmol) of compound 2-(dimethylamino) bromoethane hydrobromide shown in formula X-1 with 2.60g (40mmol) of sodium azide, add water 50ml to dissolve, nitrogen protection, 90 React at ℃ for 16h, add Na at the end of the reaction 2 CO 3 Adjust the pH value of the obtained reaction solution to neutral, carry out TLC detection on the above reaction solution, develop with dichloromethane:methanol=10:1 (v / v), the chromogenic agent is iodine simple substance, Rf=0.5, using dichloromethane Methane extraction, the obtained organic phase was dried over anhydrous sodium sulfate, and spin-dried to obtain an oi...

Embodiment 2

[0088] The structure shown in the formula (I) described in this embodiment 18 F-labeled ethinyl estradiol, such as figure 1 shown, where R 1 Is ethylene, has formula (I-a) structure:

[0089]

[0090] The synthetic route of compound (I-a) is:

[0091]

[0092] The synthetic steps of the compound shown in above-mentioned formula I-a comprise:

[0093] Q1, mix 4.66g (20mmol) of compound 2-(dimethylamino)bromoethane hydrobromide shown in formula X-1 with 4.9g (76mmol) of sodium azide, add water 100ml to dissolve, nitrogen protection, 93 React at ℃ for 15h, add Na at the end of the reaction 2 CO 3 Adjust the pH value of the obtained reaction solution to neutral, carry out TLC detection on the above reaction solution, develop with dichloromethane:methanol=10:1 (v / v), the chromogen is simple iodine, Rf=0.5, using dichloromethane Methane extraction, the obtained organic phase was dried over anhydrous sodium sulfate, and spin-dried to obtain an oily liquid, which was the c...

Embodiment 3

[0099] The structure shown in the formula (I) described in this embodiment 18 F-labeled ethinyl estradiol, such as figure 1 shown, where R 1 Is ethylene, has formula (I-a) structure:

[0100]

[0101] The synthetic route of compound (I-a) is:

[0102]

[0103] The synthetic steps of the compound shown in above-mentioned formula I-a comprise:

[0104] Q1. Mix 3493.5mg (15mmol) of compound 2-(dimethylamino)bromoethane hydrobromide shown in formula X-1 with 4095.6mg (63mmol) of sodium azide, add 75ml of water to dissolve, nitrogen protection, 87 React at ℃ for 17h, add Na at the end of the reaction 2 CO 3 Adjust the pH value of the obtained reaction solution to neutral, carry out TLC detection on the above reaction solution, develop with dichloromethane:methanol=10:1 (v / v), the chromogen is simple iodine, Rf=0.5, using dichloromethane Methane extraction, the obtained organic phase was dried over anhydrous sodium sulfate, and spin-dried to obtain an oily liquid, which ...

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Abstract

The present invention relates to the field of medicinal chemistry, and in particular relates to 18F-labeled ethinyloestradiol and a preparation method and application thereof, a modifying group is introduced into ethinylestradiol, and the ethinylestradiol is labeled by 18F, and the 18F-labeled ethinyloestradiol has good bioactivity, excellent pharmacokinetic properties and good stability in vitro, can be better targeting to breast cancer ER + cells, and can be used as a PET tracer for early diagnosis or therapeutic effect evaluation of high metastatic breast cancer ER + cells. The invention also provides the preparation method of the 18F labeled ethinylestradiol, a labeling group is introduced into the ethinylestradiol as a raw material by Click reaction, and heated for being exchanged with 18F<-> under relatively mild conditions, a labeling step and purification time are simplified, the radiochemical yield of the 18F-labeled ethinyloestradiol is high, and commercial application and clinical promotion of radiolabeled compounds are facilitated.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a 18 F-labeled ethinyl estradiol and its preparation method and application. Background technique [0002] Breast cancer is a common cancer that women are prone to, and it is prone to metastasis. The incidence rate is increasing year by year and it is getting younger, which seriously affects women's health. Clinical studies have found that estrogen receptor-positive breast cancer has a lower invasive behavior and is more sensitive to endocrine therapy. However, after a stage of endocrine therapy, the estrogen receptor activity of the lesion may change and affect the subsequent efficacy. Immunopathological examination can only obtain the distribution of estrogen receptors in surgical lesions, but the receptors in primary lesions cannot fully represent metastatic lesions, especially the activity of estrogen receptors in treatment lesions. Therefore, it is the key to timely adj...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J43/00A61K51/04A61K31/58A61P35/04A61P35/00A61P15/14A61K101/02
CPCA61K51/0453C07B2200/05C07J43/003
Inventor 林建国邱玲刘桂青李珂吕高超刘清竹
Owner JIANGSU INST OF NUCLEAR MEDICINE
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