Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

18F-labeled ethinyloestradiol and preparation method and application thereof

A technology of ethinyl estradiol and 18F, which is applied in the field of 18F-labeled ethinyl estradiol and its preparation, can solve the problems of serious adverse reactions and harsh reaction conditions, and achieve simplified labeling steps and purification time, fast reaction rate and good biological activity Effect

Active Publication Date: 2017-07-25
JIANGSU INST OF NUCLEAR MEDICINE
View PDF2 Cites 9 Cited by
  • 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

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
  • 18F-labeled ethinyloestradiol and preparation method and application thereof
  • 18F-labeled ethinyloestradiol and preparation method and application thereof
  • 18F-labeled ethinyloestradiol and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] Described in the present embodiment has formula (I) structure 18 F-labeled ethinyl estradiol, such as figure 1 shown, where R 1 Be ethylene, have 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 The resulting reaction solution was adjusted to a neutral pH value, and the above reaction solution was subjected to TLC detection, developed with dichloromethane:methanol=10:1 (v / v), the chromogen was simple iodine, Rf=0.5, and dichloromethane was used Methane extraction, the obtained organic phase was dried over anhydrous sodium sulfate, and spin-dried to obtain an oily liquid....

Embodiment 2

[0088] The structure shown in formula (I) described in the present embodiment 18 F-labeled ethinyl estradiol, such as figure 1 shown, where R 1 Be ethylene, have 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 The resulting reaction solution was adjusted to a neutral pH value, and the above reaction solution was subjected to TLC detection, developed with dichloromethane:methanol=10:1 (v / v), the chromogen was simple iodine, Rf=0.5, and dichloromethane was used Methane extraction, the obtained organic phase was dried over anhydrous sodium sulfate, and spin-dried to obtain an oily...

Embodiment 3

[0099] The structure shown in formula (I) described in the present embodiment 18 F-labeled ethinyl estradiol, such as figure 1 shown, where R 1 Be ethylene, have 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 The resulting reaction solution was adjusted to a neutral pH value, and the above reaction solution was subjected to TLC detection, developed with dichloromethane:methanol=10:1 (v / v), the chromogen was simple iodine, Rf=0.5, and dichloromethane was used Methane extraction, the obtained organic phase was dried over anhydrous sodium sulfate, and spin-dried to obtai...

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 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

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 Applications(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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com