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A kind of water-soluble magnetic resonance imaging contrast agent containing nitroimidazole group and preparation method thereof

A nitroimidazolyl, magnetic resonance imaging technology, which is applied to preparations and pharmaceutical formulations for in vivo experiments, can solve problems such as unsatisfactory organ imaging, shorten longitudinal relaxation time, improve paramagnetic resonance signal intensity, The effect of improving sensitivity and specificity

Active Publication Date: 2017-12-22
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 applied 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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  • A kind of water-soluble magnetic resonance imaging contrast agent containing nitroimidazole group and preparation method thereof
  • A kind of water-soluble magnetic resonance imaging contrast agent containing nitroimidazole group and preparation method thereof
  • A kind of water-soluble magnetic resonance imaging contrast agent containing nitroimidazole group and preparation method thereof

Examples

Experimental program
Comparison scheme
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 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).

[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) ethylenediam...

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Abstract

The invention relates to a novel water-soluble magnetic resonance imaging contrast agent containing nitroimidazole groups and a preparation method thereof, belonging to the technical fields of medicine and chemistry. The contrast agent of the present invention is a novel organic ligand containing nitroimidazole group prepared by the esterification reaction of the active derivative of polyamine polycarboxylic acid and the compound containing nitroimidazole group under the action of microwaves. Chelate with paramagnetic metal ions to obtain the corresponding paramagnetic metal chelate contrast agent. This type of contrast agent has high relaxation efficiency, good water solubility, especially kidney targeting, and can be used in magnetic resonance imaging techniques of various tissues or organs of the human body 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 Patents(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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