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Water-soluble magnetic resonance imaging contrast agent containing nitroimidazole group and preparation method of contrast agent

A nitroimidazole-based, magnetic resonance imaging technology, applied in preparations for in vivo experiments, pharmaceutical formulations, etc., can solve the problems of unsatisfactory organ imaging, shorten the longitudinal relaxation time, improve sensitivity and specificity, Effect of increasing paramagnetic resonance signal intensity

Active Publication Date: 2015-03-25
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Synthesized more complex macrocyclic polyaminopolycarboxylic acid contrast agent Gd-DOTA (M.Magerstade et al, Magn.Reson.Med., 1986,3,808), Gd (HP-DO3A) (M.F.Tweedle et al, Drugs Future, 1992, 17, 187) has been used clinically, and has a good contrast enhancement effect on the central nervous system, but the contrast to some other organs in the body is not ideal

Method used

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  • Water-soluble magnetic resonance imaging contrast agent containing nitroimidazole group and preparation method of contrast agent
  • Water-soluble magnetic resonance imaging contrast agent containing nitroimidazole group and preparation method of contrast agent
  • Water-soluble magnetic resonance imaging contrast agent containing nitroimidazole group and preparation method of contrast agent

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Experimental program
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Effect test

Embodiment 1

[0053] EDTA-α,δ-bis[1-(2-nitro-1H-imidazole)]ethanol diester metal gadolinium(Ⅲ) chelate

[0054]

[0055] Step 1. Preparation of ethylenediaminetetraacetic acid cyclodianhydride (EDTAA)

[0056] 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 24 hours, 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 acid cyclobis Anhydride (EDTAA), 74% yield. 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).

[0057] Step 2. EDTA α,δ-bis[1-(2-nitro-1H-imidazole)]ethanol diester (L 1 )Synthesis

[0058] Add 1.63g (6mmol) ethylenediaminetetraacetic acid ...

Embodiment 2

[0065] Diethylenetriaminepentaacetic acid-α,η-bis[1-(2-nitro-1H-imidazole)]ethanol diester metal gadolinium(Ⅲ) chelate

[0066]

[0067] Step 1. Preparation of diethylenetriaminepentaacetic acid cyclodianhydride (DTPAA)

[0068] Weigh 7.86g (0.02mol) of diethylenetriaminepentaacetic acid into a 50mL three-neck flask, add 15.0mL of anhydrous pyridine, slowly add 8.0mL (0.08mol) of acetic anhydride dropwise under nitrogen protection, and stir and reflux at 60°C for 24h , cooled to room temperature, suction filtered, the resulting solid was washed with acetic anhydride until no amber, recrystallized from DMF-ether to obtain 6.68 g of white powder, yield 85%; m.p.189~191°C (literature value: 190°C); FT- IR (KBr, cm -1 ): 3430.7(n OH ), 1820.7 and 1773.5 (n 酸酐羰基 ); 1639.7(n COOH ),1108.4(n C-O-C ).Anal.calculated for C 14 h 19 N 3 o 8 : C 47.06, H 5.32, N 11.76; found C 46.85, H 5.52, N 11.58.

[0069] Step 2. Diethylenetriaminepentaacetic acid-α, η-bis[1-(2-nitro-1H-i...

Embodiment 3

[0077] EDTA-α,δ-bis[1-(2-methyl-5-nitro-1H-imidazole)]ethanol diester metal gadolinium(Ⅲ) chelate

[0078]

[0079] Step 1. Preparation of ethylenediaminetetraacetic acid cyclodianhydride (EDTAA)

[0080] 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 acid cyclobis Anhydride (EDTAA), 74% yield. 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).

[0081] Step 2. EDTA-α,δ-bis[1-(2-methyl-5-nitro-1H-imidazole)]ethanol diester (L 3 )Synthesis

[0082] Add 1.20g (4.8mmol) ethylenediaminete...

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Abstract

The invention relates to a water-soluble magnetic resonance imaging contrast agent containing a nitroimidazole group and a preparation method of the contrast agent, belonging to the technical fields of medicine and chemistry. The contrast agent is prepared by the following steps: carrying out an esterification reaction between an active derivative of polyaminopolycarboxylate and a compound containing the nitroimidazole group under the effect of microwave to obtain a novel organic ligand containing the nitroimidazole group; and chelating the ligand with paramagnetic metal ions to obtain a corresponding paramagnetic metal chelate contrast agent. The contrast agent disclosed by the invention is high in relaxation efficiency and good in water solubility, and especially has a kidney targeting property; and the contrast agent is applicable to the magnetic resonance imaging technology of various tissues or organs of human bodies or other mammals.

Description

technical field [0001] The invention discloses a kind of water-soluble magnetic resonance imaging contrast agent containing nitroimidazole groups and a preparation method thereof. Specifically, polyamine polycarboxylic acid chelating agents containing nitroimidazole groups react with paramagnetic metal ions to form metal chelates Objects as magnetic resonance imaging contrast agents and their preparation methods, the present invention belongs to the technical field of chemistry, and also belongs to the technical field of medicine. 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, for more than 40 years, MRI has achieved rapid development and wide application in the fields of medicine, biology, and material...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K49/10
Inventor 郝志峰余灿煌杨少兵何俊添黄淑贞谭桂珍黄建新余坚
Owner GUANGDONG UNIV OF TECH
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