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

18F-labeled fluoropropionyl ornithine as well as preparation method and application thereof

A technology for fluoropropionylation of ornithine and ornithine, which is applied in the preparation of carboxylic acid amides, chemical instruments and methods, and the preparation of organic compounds, etc., can solve the problems of false negatives and achieve good stability

Pending Publication Date: 2020-07-03
SHANXI MEDICAL UNIV
View PDF9 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[ 18 F] Fluorodeoxyglucose ([ 18 F]FDG) is the most clinically used tumor metabolism PET imaging agent, but due to its universality of metabolism, there is also a high uptake in non-tumor tissues, such as the brain, inflammation, tumor-like lesions, etc. The diagnosis of tumors that cause obvious abnormalities in glucose metabolism, such as mucinous adenocarcinoma, bronchoalveolar carcinoma, and prostate cancer, is prone to false negative results

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 fluoropropionyl ornithine as well as preparation method and application thereof
  • 18F-labeled fluoropropionyl ornithine as well as preparation method and application thereof
  • 18F-labeled fluoropropionyl ornithine as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0031] The present invention provides the described above-mentioned technical solution 18 The preparation method of F-labeled fluoropropionylated ornithine comprises the following steps:

[0032] (1) put N 5 -(2-Bromopropionyl)-N 2 -Boc-Ornithine tert-butyl ester, solvent and [ 18 F]F - The source is mixed, and the nucleophilic reaction is carried out to obtain N 5 -(2- 18 F-fluoropropionyl)-N 2 -Boc-tert-butyl ornithine; The [ 18 F]F - source contains [ 18 F]F - and catalysts;

[0033] (2) the N 5 -(2- 18 F-fluoropropionyl)-N 2 -Boc-ornithine tert-butyl ester is mixed with hydrochloric acid for hydrolysis reaction to obtain 18 F-labeled fluoropropionylated ornithine.

[0034] In the present invention, unless otherwise specified, the raw materials and reagents used are commercially available products well known to those skilled in the art.

[0035] The present invention will N 5 -(2-Bromopropionyl)-N 2 -Boc-Ornithine tert-butyl ester, solvent and [ 18 F]F -...

Embodiment 1

[0058] Preparation of N 5 -(2-[ 18 F]-fluoropropionyl) ornithine, wherein the reaction formulas of acylation reaction, nucleophilic reaction and hydrolysis reaction are shown in formula a, formula b and formula c respectively:

[0059]

[0060] Will N 2 -Boc-L-ornithine tert-butyl ester (1g, 3.473mmol), triethylamine (6.946mmol) and anhydrous dichloromethane (20mL) were mixed, stirred evenly under the condition of ice-water bath (0°C), and slowly Add 2-bromopropionyl bromide (0.25mL, 2.315mmol) dropwise to the reaction system, stir thoroughly for 30min, then return to room temperature (23°C), continue stirring for 20h for acylation reaction, TLC detects that the reaction is complete, then filter, and add to the obtained Add 50mL water to the filtrate, use ethyl acetate (3×50mL) to extract, combine the organic phase, anhydrous Na 2 SO 4 After drying, the solvent was evaporated to obtain 0.51 g of yellow powdery solid, namely N 5 -(2-Bromopropionyl)-N 2 -Boc-ornithine t...

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 invention provides 18F-labeled fluoropropionyl ornithine as well as a preparation method and application thereof, and belongs to the technical field of radiopharmaceutical chemistry. The provided18F labeled fluoropropionyl ornithine is N5-(2-[18F]-fluoropropionyl) ornithine. The 18F labeled fluoropropionyl ornithine is good in stability, high in uptake in tumor tissues, high in tumor / normal tissue ratio and capable of being used as a PET-CT tumor imaging agent. Furthermore, the invention provides a preparation method of the 18F-labeled fluoropropionyl ornithine, and the provided preparation method has the advantages that the used raw materials are easy to obtain, the process is simple, the operation is easy, and the automatic preparation of 18F-labeled fluoropropionyl ornithine is convenient to realize.

Description

technical field [0001] The invention relates to the technical field of radiopharmaceutical chemistry, in particular to a 18 F-labeled fluoropropionylated ornithine, its preparation method and application. Background technique [0002] As an important representative of functional imaging, positron emission tomography (PET) technology is becoming more and more mature in the application of tumor diagnosis, staging and restaging, curative effect monitoring and evaluation, and radiotherapy target delineation, and gradually develops into predictability and specificity. . [ 18 F] Fluorodeoxyglucose ([ 18 F]FDG) is the most clinically used tumor metabolism PET imaging agent, but due to its universality of metabolism, there is also a high uptake in non-tumor tissues, such as brain, inflammation, tumor-like lesions, etc. The diagnosis of tumors that cause obvious abnormalities in glucose metabolism, such as mucinous adenocarcinoma, bronchoalveolar carcinoma, and prostate cancer, i...

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): C07C233/47C07C231/12A61P35/00A61K51/04
CPCC07C233/47A61P35/00A61K51/0406
Inventor 王红亮武志芳李思进赵琦南董伟璇刘海燕李建国
Owner SHANXI MEDICAL UNIV
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