Fluorine-18-labeled spiropiperidine sigma-1 receptor compound and its preparation method and use

A technology for spirocyclic piperidine and compound, which is applied in the field of spirocyclic piperidine sigma-1 receptor compounds and preparation, and can solve the problems of low selectivity, short carbon-11 half-life, and unfavorable clinical promotion and use.

Inactive Publication Date: 2012-09-12
BEIJING NORMAL UNIVERSITY
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  • Abstract
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Problems solved by technology

[ 18 F] When FPS is applied to human brain imaging, it can reach its peak value only 4 hours after injection, which is not conducive to clinical promotion and use
[ 11 C] SA4503 is a σ that has entered clinical trials 1 Receptor imaging agent, but its selectivity is not

Method used

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  • Fluorine-18-labeled spiropiperidine sigma-1 receptor compound and its preparation method and use
  • Fluorine-18-labeled spiropiperidine sigma-1 receptor compound and its preparation method and use
  • Fluorine-18-labeled spiropiperidine sigma-1 receptor compound and its preparation method and use

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Embodiment Construction

[0069] Describe the present invention in detail below by embodiment,

[0070] A fluorine-18 labeled spirocyclic piperidine sigma-1 receptor compound, the general structural formula of which is:

[0071]

[0072] Where: R=OCH 3 , OCH 2 CH 2 F. (OCH 2 CH 2 ) 2 F or (OCH 2 CH 2 ) 3 F;

[0073] Fluorine-18 labeled spirocyclic piperidines σ 1 The preparation method of receptor compound comprises: receptor ligand Spiro-OCH 3 (R=OCH 3 ), synthesis of receptor ligand Spiro-PEG1-F, synthesis of compound intermediate Spiro-OH, synthesis of receptor ligand Spiro-PEG2-F, Spiro-PEG3-F, labeling precursor Spiro-PEGn (n= 1) Preparation of -OTs, labeling precursor Spiro-PEGn(n=3)-OTs and fluorine-18-labeled spirocyclic piperidine compounds, the process steps are as follows:

[0074] a. Receptor ligand Spiro-OCH 3 (R=OCH 3 )Synthesis:

[0075] Dissolve 500mg Spiro-piperidine in 20mL acetonitrile, add 2g K 2 CO 3 , 200mg KI, then add 580mg 4-methoxybenzyl bromide, react at ...

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Abstract

The invention discloses a fluorine-18-labeled spiropiperidine sigma-1 receptor compound and its preparation method and use. The preparation method comprises synthesis of a receptor ligand Spiro-OCH3(R=OCH3), synthesis of a receptor ligand Spiro-PEG1-F, synthesis of a compound intermediate Spiro-OH, synthesis of a receptor ligand Spiro-PEG2-F, synthesis of a receptor ligand Spiro-PEG3-F, synthesis of a labelled precursor Spiro-PEGn(n=1)-OTs, synthesis of a labeled precursor Spiro-PEGn(n=3)-OTs and preparation of the fluorine-18-labelled spiropiperidine sigma-1 receptor compound. The fluorine-18-labelled spiropiperidine sigma-1 receptor compound has high affinity and selectivity to a sigma-1 receptor. Through fluorine-18 labeling, the fluorine-18-labelled spiropiperidine sigma-1 receptor compound has a high labeling rate, high radiochemical purity and excellent biological properties and can be widely used for preparation of a positron imaging agent.

Description

Technical field [0001] The invention relates to the technical fields of fluorine-18 labeled radiopharmaceutical chemistry and clinical nuclear medicine, in particular to a fluorine-18 labeled spirocyclic piperidine sigma-1 receptor compound, its preparation method and application. Background technique [0002] In the field of radiopharmaceutical chemistry and clinical nuclear medicine technology, Sigma (σ) receptor is a new type of receptor different from opioid receptors, divided into σ 1 and σ 2 Two subtypes. σ 1 Also known as the sigma-1 receptor, σ 1 The receptors are highly expressed in the brain and peripheral organs such as heart, spleen, kidney, liver, ovary, testis, placenta, etc. Located in the cytoplasm, endoplasmic reticulum, and mitochondrial membranes. In the central nervous system (CNS), σ 1 Receptor expression was highest in various brain nuclei, such as the red nucleus, periaqueductal gray matter, and substantia nigra in the midbrain region, and the ha...

Claims

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Application Information

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IPC IPC(8): C07D491/107A61K51/04A61K101/02
Inventor 贾红梅李艳
Owner BEIJING NORMAL UNIVERSITY
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