Technetium-99m-labeled higher fatty acid derivative

A higher fatty acid, -99m technology, applied in the field of higher fatty acid derivatives, can solve the problems of poor myocardial uptake, high fat solubility of drugs, affecting myocardial imaging, etc., and achieve the effect of prolonging myocardial retention, reducing blood background, and improving myocardial uptake

Inactive Publication Date: 2014-05-07
BEIJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

18F-FDG is too expensive
However, no high-grade fatty acid myocardial metabolism imaging agent labeled with technetium-99m with excellent nuclide properties and low price has been successfully put into the market. imaging

Method used

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  • Technetium-99m-labeled higher fatty acid derivative
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  • Technetium-99m-labeled higher fatty acid derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: preparation of

[0031] ①Add 30mL of SOCl2 dropwise to 4.06g of dodecanedioic acid (Compound I) in an ice bath, continue to stir for half an hour, and reflux and stir for 12h under an oil bath at 90°C to remove excess SOCl 2 , to obtain a transparent oily product, which is compound II, which is not further purified and is reserved for the next step;

[0032]

[0033] ②Add 5 mL of dry methanol to the compound II obtained in ①, and stir at 60°C for 2 h to obtain a mixture whose main product is compound III, which is left for the next step without further treatment.

[0034]

[0035] ③Add 20mL of SOCl to 3g of thienylpropionic acid 2 , and stirred for 2h, 2.9g of thienylpropionyl chloride was obtained with a yield of 96%.

[0036]

[0037] 4. under ice-bath conditions, the thiophene propionyl chloride that step 3. gained is joined in the dichloromethane that is dissolved with 2.58g ferrocene, stirs 4 hours under room temperature, obtains the mixed s...

Embodiment 2

[0043] Example 2: preparation of

[0044] ① Dissolve 30mL of SOCl in an ice bath 2 Add dropwise to 4.06 g of compound I, continue to stir for 30 min, and then reflux and stir for 12 h under the condition of an oil bath at 90 ° C to remove excess SOCl 2 , to obtain a transparent oily product, that is, compound II, which was reserved for the next step without further purification.

[0045]

[0046] ② Add 5 mL of dry methanol to ①, stir at 60°C for 2 h to obtain a mixed solution of compound III, which will be used for the next step without further treatment.

[0047]

[0048] ③Add 20mL of SOCl to 3g of thienylpropionic acid 2 , and stirred for 2 hours to obtain thienylpropionyl chloride, which was not treated and was reserved for the next step.

[0049]

[0050] 4. under ice-bath conditions, the thiophene propionyl chloride that step 3. gained is joined in the dichloromethane that is dissolved with 2.58g ferrocene, stirs 4 hours under room temperature, obtains the m...

Embodiment 3

[0056] Example 3: preparation of

[0057] ① Dissolve ethyl 5-bromopentanoate (3.8mL, 24.0mmol) and thiourea (2.7g, 34mmol) in 50mL of ethanol, reflux for 20h, remove the solvent under reduced pressure, add 7.5M NaOH aqueous solution (aq) (50mL , 360mmol), the mixture was stirred at 90°C under nitrogen protection for 16h; in ice bath, 2M H 2 SO 4 aq, adjust the pH to 1, the product with CH 2 Cl 2 Extracted twice with anhydrous MgSO 4 After drying, filtering, and removing the solvent, the product was directly used in the next reaction without further treatment.

[0058]

[0059] ② Dissolve ethyl 5-bromopentanoate (3.8mL, 24.0mmol) in 16.7M (8mL) NaOH, add it dropwise to the NaOH solution of compound III under ice-bath conditions, and then Under the condition of stirring for 24h; the reactant was adjusted to pH 1 with concentrated HCl, and CH 2 Cl 2 After extracting 5 times, the organic layers were combined, dried with anhydrous NaSO4, filtered, and the solvent was re...

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PUM

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Abstract

The invention relates to a technetium-99m-labeled higher fatty acid derivative and in particular relates to a technetium-99m-labeled long-chain fatty acid metabolism product. According to the long-chain fatty acid metabolism product, sulfonyl and a thiophene ring are introduced into long-chain fatty acids, so that the molecular lipid solubility is reduced, the myocardial uptake of the medicament is increased, and the retention time of the medicament in the myocardium is prolonged. The experiment proves that according to the designed higher fatty acid compounds, the myocardial uptake is improved, and the retention time of the medicament is prolonged.

Description

technical field [0001] The invention relates to a fatty acid compound in the fields of organic chemistry and medicinal chemistry, in particular to a technetium-99m labeled higher fatty acid derivative. Background technique [0002] Cardiovascular and cerebrovascular disease is a common disease that seriously threatens human health. At present, there are more than 270 million people with cardiovascular and cerebrovascular diseases in my country, and nearly 3 million people die from cardiovascular and cerebrovascular diseases in China every year, accounting for 51% of the total death causes in my country every year. %. However, it only takes a few minutes to go from asymptomatic arteriosclerosis to symptomatic arteriosclerosis. If the early diagnosis of the disease can be realized, the mortality rate of the disease can be greatly reduced, and it will have a positive impact on the overall situation of building a well-off society in our country. At present, PET / SPECT-based radi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/00A61K51/04A61K103/10
CPCC07F13/00A61K51/0402
Inventor 张华北薛甜李香
Owner BEIJING NORMAL UNIVERSITY
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