99mtc marked 2-methoxyphenyl piperazine derivative complexes as well as preparation method and uses thereof

A technology of methoxyphenyl and 99mtc, which is applied in the field of radioactive complexes, can solve the problems of low brain uptake, strong fat-solubility, and poor specificity of complexes, and achieve simple preparation methods, excellent biological properties, and low cost of preparation and use low effect

Inactive Publication Date: 2008-05-21
BEIJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

More importantly, such 99m Although the Tc-labeled complex showed high receptor affinity in vitro, the in vivo experimental results were unsatisfactory, mainly due to low brain uptake and poor specificity. The possible reasons were that the complex was too fat-soluble and the molecular weight was too large.

Method used

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  • 99mtc marked 2-methoxyphenyl piperazine derivative complexes as well as preparation method and uses thereof
  • 99mtc marked 2-methoxyphenyl piperazine derivative complexes as well as preparation method and uses thereof
  • 99mtc marked 2-methoxyphenyl piperazine derivative complexes as well as preparation method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] One of the ligands prepared according to the following steps is the compound HYNIC-MPP3 with n taking 3 shown in formula (A), and the other ligands are HEDTA 99m Tc-labeled 2-methoxyphenylpiperazine complexes:

[0059] 1) Synthesis of HYNIC-MPP3 ligand

[0060] 1.1) Potassium phthalimide (4.003g, 0.022mol) and 1,3-dibromopropane (11.151g, 0.055mol) were added to a 50mL three-necked flask, heated to reflux in 30mL of acetonitrile for 5 hours , The solution was a white cloudy liquid during the reaction. After the reaction, filter and concentrate the filtrate to obtain a light yellow-green liquid, add 8 mL of methanol, and precipitate about 2.010 g of crystals at -18° C., with a yield of 24%.

[0061] 1.2) Take the crystallization 1.021g (4mmol) obtained in step 1.1), add 0.912g (4mmol) of 2-methoxyl-phenylpiperazine hydrochloride and K in a 50mL three-necked flask 2 CO 3 1.108 g (4 mmol). After refluxing in acetonitrile for a while, the solution turned milky yellow. ...

Embodiment 2

[0076] One of the ligands prepared according to the following steps is the compound HYNIC-MPP3 with n taking 3 shown in formula (A), and the other ligands are tricine 99m Tc-labeled 2-methoxyphenylpiperazine complexes:

[0077] 1) Synthesis of HYNIC-MPP3 ligand

[0078] The ligand HYNIC-MPP3 was synthesized according to the method described in step 1) of Example 1.

[0079] 2) Synthesis of complexes

[0080] 2.1) Prepare the solution according to the method of step 2.1) in Example 1, except that HEDTA as other ligands is replaced with tricine;

[0081] 2.2) Use the reactant solution prepared in step 2.1) of this example to synthesize the complex according to the method in step 2.2) in Example 1, except that the reaction condition after adjusting the pH value of the solution is to react at 60°C for 10 minutes, and the obtained complex Material use 99m Expressed by Tc-tricine / HYNIC-MPP3.

Embodiment 3

[0083] One of the ligands prepared according to the following method is the compound HYNIC-MPP4 with n taking 4 shown in formula (A), and the other ligands are HEDTA 99m Tc-labeled 2-methoxyphenylpiperazine complexes:

[0084] 1) Synthesis of HYNIC-MPP4 ligand

[0085] The ligand was synthesized according to the method described in step 1) of Example 1, except that the 1,3-dibromopropane used therein was replaced by the same mole number of 1,3-dibromobutane.

[0086] 2) Synthesis of complexes

[0087] 2.1) Prepare the solution according to the method of step 2.1) in Example 1, except that the ligand HYNIC-MPP3 used is replaced by the HYNIC-MPP4 ligand prepared in step 1) of this example;

[0088] 2.2) Use the various reactant solutions prepared in step 2.1) of this example to synthesize the complex according to the method in step 2.2) in Example 1, except that the reaction condition after adjusting the pH value of the solution is to react at 40°C for 50 minutes to obtain co...

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Abstract

The invention relates to a 2-methoxy benzene group piperazine derivative complex marked by radioactive <99m>Tc. The 2-methoxy benzene group piperazine derivative complex considers the <99m>Tc as a central core; one ligand is 2-methoxy benzene group piperazine derivative compound, the structure of which is shown in a formula (A), wherein, n is an integer of 1 to 6; carbon chain length is shown as C1 to C6; the other ligand is one kind of nitrilotriacetic acid, tris (hydroxymethyl) methyl glycine, di (hydroxymethyl) methyl glycine or hydroxyethylethylenediaminetriacetic acid. The complex can be used as 5-HT1A brain receptor imaging agent and has the advantages of simple preparation, low price, high target / non-target ratio etc. The invention also relates to a preparation method of the complex and an application of the complex as the 5-HT1A brain receptor imaging agent.

Description

technical field [0001] The present invention relates to a 99m Tc-labeled radioactive complexes, especially 99m Tc-labeled 2-methoxyphenylpiperazine complex, its preparation method and as 5-HT 1A Application of brain receptor imaging agents. Background technique [0002] Functional imaging of central nervous system (CNS) receptors has become an important field in radiopharmaceutical research. Changes in neuroreceptor density and function are strongly associated with neurological and psychiatric disorders (Gross C, Zhuang X, Stark K, et al.Serotoninl A receptor acts during development to establish normal Lanxiety-like behavior in the adult[J].Nature , 2002, 416(6879): 396). In particular, the subtype 5-HT of the central neurotransmitter 5-hydroxytryptamine (5-HT) receptor 1A It is related to insomnia, anxiety disorder, depression, schizophrenia and senile dementia (Alzheimer's disease). 5-HT 1A The receptor is a G-protein-coupled receptor with discontinuous distribution...

Claims

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Application Information

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IPC IPC(8): C07F13/00A61K51/04A61K103/10
Inventor 张现忠范卫卫林艳庞燕唐志刚张俊波王学斌陆洁
Owner BEIJING NORMAL UNIVERSITY
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