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

Synthesis of oligomerized fragrant amide-containing paramagnetic metallo-chelates contrast medium

A paramagnetic metal and synthesis method technology, applied in the fields of chemistry and medicine, can solve the problems of poor imaging effect, short residence time and high osmotic pressure of hepatic and biliary tract systems, achieve good stability and relaxation rate, and improve early diagnosis Level, enhance the effect of relaxation

Inactive Publication Date: 2011-04-13
GUANGDONG UNIV OF TECH
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These contrast agents are suitable for imaging the brain, kidneys, and blood systems, but are less effective for imaging systems such as the hepatobiliary tract
Moreover, these small molecule complexes have disadvantages such as high osmotic pressure and short residence time in the body, resulting in disadvantages such as large dosage and multiple injections.

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
  • Synthesis of oligomerized fragrant amide-containing paramagnetic metallo-chelates contrast medium
  • Synthesis of oligomerized fragrant amide-containing paramagnetic metallo-chelates contrast medium
  • Synthesis of oligomerized fragrant amide-containing paramagnetic metallo-chelates contrast medium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Oligoethylenediamine-N,N'-bis(acetanilide)-gadolinium(III) diacetate chelate

[0043] The preparation of step 1.ethylenediaminetetraacetic dianhydride (EDTAA):

[0044] Weigh 5.80g (0.02mol) of ethylenediaminetetraacetic acid (EDTA) into a 50mL round bottom flask, add 8mL (0.08mol) of acetic anhydride and 10mL (0.12mol) of pyridine, and install a straight condenser with a drying tube above the flask Stir and reflux at 65°C for 24h, cool to room temperature, filter with suction, wash with acetic anhydride, cold DMF and ether, recrystallize with DMF-ether, and dry in vacuo to obtain a white powder called ethylenediaminetetraacetic dianhydride (EDTAA), yield 74%. m.p. is 189-191°C; elemental analysis measured value (%, calculated value): C 46.51 (46.87), H 4.98 (4.69), N 10.27 (10.94).

[0045] Step 2. Preparation of oligoethylenediamine-N, N'-bis(acetanilide)-diacetic acid:

[0046] 10.81g (0.1mol) p-phenylenediamine, 25.63g (0.1mol) ethylenediaminetetraacetic dianhydr...

Embodiment 2

[0050] Oligomeric diethylenetriamine-N,N'-bis(acetanilide)-triacetate gadolinium(III) chelate

[0051] The preparation of step 1. diethylenetriaminepentaacetic dianhydride (DTPAA):

[0052] Weigh 7.80g (0.02mol) of diethylenetriaminepentaacetic acid (DTPA) into a 50mL round bottom flask, add 8mL (0.08mol) of acetic anhydride and 10mL (0.12mol) of pyridine, and install a straight drying tube on the top of the flask Condenser, stirred and refluxed at 65°C for 24 hours, cooled to room temperature, filtered with suction, washed with acetic anhydride, cold DMF and ether, recrystallized with DMF-ether, and dried in vacuo to obtain white powder as diethylenetriaminepentaacetic acid Dianhydride (DTPAA), yield 78%. m.p. is 182-184°C; elemental analysis measured value (%, calculated value): C 47.51 (47.06), H 5.47 (5.32), N 12.03 (11.76).

[0053] Step 2. Oligomeric diethylenetriamine-N,N'-bis(acetanilide)-triacetic acid:

[0054] Put 10.81g (0.1mol) p-phenylenediamine, 35.73g (0.1mo...

Embodiment 3

[0058] Oligoethylenediamine-N,N'-bis(acetylbenzidine)-gadolinium(III) diacetate chelate

[0059] The preparation of step 1.ethylenediaminetetraacetic dianhydride (EDTAA):

[0060] With embodiment 1.

[0061] Step 2. The preparation of oligoethylenediamine-N, N'-bis(acetylbenzidine)-diacetic acid:

[0062] Put 18.40g (0.1mol) p-diaminobiphenyl into the three-necked flask, 25.63g (0.1mol) ethylenediaminetetraacetic dianhydride (EDTAA), then add 25mL N-methylpyrrolidone (NMP), 15mL pyridine, and nitrogen , after stirring and reacting at 30° C. for 5 h, the mixed solution was dropped into rapidly stirred distilled water to precipitate a precipitate, which was filtered to obtain a solid. Then the solid was dissolved with an appropriate amount of N-methylpyrrolidone (NMP), filtered, and the filtrate was dropped into rapidly stirred distilled water. This was repeated three times and dried in vacuo to obtain a white powder of oligoethylenediamine-N, N'-bis( Acetylbenzidine)-diaceti...

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 discloses a method for synthesizing an oligomer aryl-containing amide paramagnetic metal chelate contrast agent, which comprises the following steps: performing acylation polymerization on polyamine polycarboxylic acid dianhydride and aryl-containing diamine to obtain an aryl-containing amide oligomer ligand with adjustable polymerization degree, number average molecular weight and flexibility, and further coordinating the compounds with paramagnetic metal ions to form a chelate contrast agent. The contrast agent can be applied to magnetic resonance imaging technology of varioustissues or organs of a human body or other mammalians. The method has the advantages of simpler synthetic route, easy obtaining of raw material, lower price, higher yield, mild reaction condition, and suitability for mass preparation and industrial production.

Description

technical field [0001] The invention belongs to the technical fields of medicine and chemistry. The invention relates to a method for synthesizing oligomeric aramid-containing paramagnetic metal chelates, and these chelates can be used as contrast agents for magnetic resonance imaging. Background technique [0002] Cancer is one of the three major diseases that seriously threaten human health today. In modern clinical medicine, the timely and accurate detection and diagnosis of tumors is very important for the treatment of cancer. Since Lauterbur first realized Magnetic Resonance Imaging (MRI) in 1973, MRI has been rapidly developed and widely used in the fields of medicine, biology, and material science for more than 30 years. What is particularly noteworthy is that in the field of diagnosis, MRI is the latest imaging diagnostic technology after CT scanners. It has the advantages of high resolution, arbitrary imaging, and no radiation damage. Medical non-destructive imag...

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 Patents(China)
IPC IPC(8): A61K49/12
Inventor 郝志峰黄卓亮余坚彭婉芬梁彩婵李永峰余林
Owner GUANGDONG UNIV OF TECH
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