Paramagnetic metal-phthalocyanine complex compounds and contrast agent using the same

A compound and contrast agent technology, applied in computer X-ray diagnosis, diagnostic X-ray imaging, and contrast agent, can solve the problem of side effects of patients

Inactive Publication Date: 2004-04-07
DAI HAN PHARM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The use of contrast agents with such a high osmolarity is known to cause side effects in patients

Method used

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  • Paramagnetic metal-phthalocyanine complex compounds and contrast agent using the same
  • Paramagnetic metal-phthalocyanine complex compounds and contrast agent using the same
  • Paramagnetic metal-phthalocyanine complex compounds and contrast agent using the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Example 1: Synthesis of eight (1,4,7,10-tetraoxaundecyl) Gd-phthalocyanine

[0056] Dissolve 0.972g (2.15mmol) of 1,2-bis(1,4,7,10-tetraoxaundecyl)-4,5-dicyanobenzene in 10ml DMF, and add 0.779g (2.15 mmol) of gadolinium(III) oxide. Then, a reaction was performed at 150° C. for 12 hours with stirring. After the reaction, the solution was filtered and the solvent was evaporated to obtain the final product. The product thus obtained was purified by column chromatography, whereby 0.74 g of octa(1,4,7,10-tetraoxaundecyl)Gd-phthalocyanine was obtained (yield 69.7%). Use 1:5 methanol and CH for purification 2 CH 2 The mixed solvent was used as the elution solvent.

[0057] The resulting substance 1 H NMR spectrum and UV spectrum as attached figure 1 and 2 shown.

Embodiment 2

[0058] Example 2: Synthesis of eight (1,4,7,10-tetraoxaundecyl) Mn-phthalocyanine

[0059] Dissolve 1.15g (2.55mmol) of 1,2-bis(1,4,7,10-tetraoxaundecyl)-4,5-dicyanobenzene in 10ml DMF, and add 0.44g (2.55 mmol) of Mn(OAc) 2 . Then, it was reacted at 150° C. for 4 days with stirring. After the reaction, the solution was filtered and the solvent was evaporated to obtain the final product. The product thus obtained was purified by column chromatography, whereby 0.303 g of octa(1,4,7,10-tetraoxaundecyl)Mn-phthalocyanine was obtained (yield 25.5%). Use 1:5 methanol and CH for purification 2 CH 2 The mixed solvent was used as the elution solvent.

[0060] The resulting substance 1 H NMR spectrum and UV spectrum as attached image 3 and 4 shown.

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Abstract

The present invention provides a novel paramagnetic metal-phthalocyanine complexes and pharmaceutically acceptable salts thereof, which are useful as contrast agents for MRI (Magnetic Resonance Imaging), diagnostic X-ray imaging and computed tomography (CT). The present invention also provides contrast agents for imaging, comprising the new paramagnetic metal-phthalocyanine complexes. The new contrast agents of the present invention show high imaging enhancement effects at lower concentration and are safer than the previously reported contrast agents.

Description

field of invention [0001] The present invention relates to contrast agents for use in Magnetic Resonance Imaging (MRI), Diagnostic X-ray Imaging, Computed Tomography (CT), etc., or more particularly, to novel paramagnetic metal-phthalocyanine complexes The compound, its pharmaceutically acceptable salt and the imaging contrast agent containing the compound can further sharpen the image of the patient's organ or cell tissue obtained by MRI etc. after being administered to the patient. Background of the invention [0002] Contrast agents are primarily used to obtain images of tissue (ie, blood vessels, masses, etc.) and surrounding organ tissue. They are used to examine the location, size and condition of tissue by further clarifying the brightness contrast of the mass and surrounding tissue, which have similar substituents. Magnetic resonance imaging (MRI) has proven to be excellent and stable for distinguishing mass tissue from surrounding tissue. [0003] Many methods for...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K49/00A61K49/04A61K49/08A61K49/10C07D487/22C07F5/00C07F13/00C09B47/067
CPCA61K49/04C07F5/003C07D487/22C09B47/0673C07F13/005A61K49/106A61K49/085
Inventor 李承泳具教妊
Owner DAI HAN PHARM
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