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F-triazole ring-polyethylene glycol-metronidazole compound and preparation method thereof

A polyethylene glycol and compound technology, applied in the field of metronidazole compounds and their preparation, can solve the problems of slow clearance rate of non-target tissues, low target/non-target ratio, long time interval between injection and imaging, etc.

Inactive Publication Date: 2013-05-01
BEIJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the low absolute uptake of tumor tissue in the body, high liver uptake, and slow clearance rate of non-target tissues, the time interval between injection and imaging is long (more than 90 minutes), and the target / non-target ratio is not high.

Method used

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  • F-triazole ring-polyethylene glycol-metronidazole compound and preparation method thereof
  • F-triazole ring-polyethylene glycol-metronidazole compound and preparation method thereof
  • F-triazole ring-polyethylene glycol-metronidazole compound and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1- Embodiment 6

[0105] Embodiment 1-embodiment 6 ( 19 Synthesis of F)

Embodiment 1

[0107] 1. Synthesis of the Intermediate Alkyne PETY1

[0108] 1) The structure of the compound PETY1

[0109]

[0110] 2) Synthesis method

[0111] a. Synthesis of compound PEGY1

[0112] Under the protection of inert gas, 3-bromo-1-propyne (5 mL, 45 mmol) and 1,2-ethanediol (5.57 g, 90 mmol) were successively added into a dry round bottom flask. After stirring and mixing, ground and crushed NaOH (2.16g, 54mmol) was added in an ice-water bath, stirred rapidly for 15 minutes, then heated to 45°C, and reacted for 3 hours until the alkyne reaction was complete. After the reaction was completed, it was filtered, and the solid was washed with ethyl acetate. The filtrate was washed with a small amount of water until neutral. The filtrate was collected, washed successively with water and saturated brine, and finally dried over sodium sulfate. After filtering again, the organic solvent was removed under reduced pressure, followed by column chromatography. The product componen...

Embodiment 2

[0151] 1. Synthesis of the Intermediate Alkyne PETY2

[0152] 1) The structure of compound PETY2

[0153]

[0154] 2) Synthesis method

[0155] a. Synthesis of compound PEGY2

[0156] Under the protection of an inert gas, 3-bromo-1-propyne (5 mL, 45 mmol) and ethylene glycol (7.2 g, 68 mmol) were successively added into a dry round bottom flask. After stirring and mixing, ground NaOH (2.16 g, 54 mmol) was added in an ice-water bath, stirred, and reacted for 15 minutes. Then react at room temperature for 3 hours until the alkyne reaction is complete. Filter and rinse the solid with ethyl acetate. The filtrate was washed with a small amount of water until neutral. The filtrate was collected, washed successively with water and saturated brine, and finally dried over sodium sulfate. After filtering again, the organic solvent was removed under reduced pressure, followed by column chromatography. The product fractions were collected, and the solvent was removed under reduc...

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Abstract

The invention relates to an F-1,2,3-triazole ring-polyethylene glycol-metronidazole compound which has the following structural general formula: L is ethyl or polyethylene glycol with the following structure: n is equal to 0, 1, 2 or 3; M is a triazole ring with the following structure: or, N is ethyl or polyethylene glycol with the following structure; n is equal to 0, 1, 2 or 3; and A is 19F or18F. Under a changeless condition that the invention keeps the metronidazole as a targeting base group, the polyethylene glycol is introduced to modify and change the molecular structure of a medicine, and the aims of improving medicine dynamics and pharmacodynamical properties and increasing the curative effect of the medicine are achieved. The triazole ring, a PEG base group, 2- metronidazole and 18 / 19F nuclide are connected by a click method, and a series of novel F-triazole ring-PEG-metronidazole derivatives are designed and synthesized. The nitro imidazole derivatives can quicken removing from normal tissues by lowering fat solubility so as to enhance a target / non-target ratio and is used for the development research of tumours, cardiac muscles or brain anoxia.

Description

technical field [0001] The invention relates to a metronidazole compound and a preparation method thereof, in particular to an F-triazole ring-polyethylene glycol-metronidazole compound and a preparation method thereof. Background technique [0002] PET imaging can noninvasively, dynamically and quantitatively study the chemical processes and physiological and biochemical processes in the human body, and study the metabolism of living substances, the distribution and function of receptors, the changes of gene regulation, etc. at the living level, which make the development of nuclear medicine Reaching the molecular level in the true sense, so the number of PET imaging equipment is increasing rapidly, and at the same time, the demand for positron drugs is increasing rapidly. There are many nuclides that emit positrons, and the main ones that can be applied to clinical nuclear medicine are 11 C. 13 N. 15 O. 18 F etc.; among them, 18 F has a relatively long half-life (109....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/12C07D403/06A61K51/04A61K101/02
Inventor 朱霖刘亚静杜风华
Owner BEIJING NORMAL UNIVERSITY
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