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Radionuclide-labeled compound and imaging agent containing same

A technology of radionuclides and compounds, applied in the directions of in vivo radioactive preparations, radioactive carriers, isotope introduction of heterocyclic compounds, etc., can solve the problems of inability to image amyloid and tau protein at the same time and high affinity

Active Publication Date: 2020-08-18
上海富吉医疗科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004]In the past, a large number of radiopharmaceuticals that image amyloid or tau have been developed, but these radiopharmaceuticals only interact with either amyloid or tau Because of its high affinity (Patent Documents 1 to 4), both amyloid and tau accumulated in the brain cannot be imaged at the same time

Method used

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  • Radionuclide-labeled compound and imaging agent containing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] Example 1: Synthesis of DRK092N Labeled Precursor (Compound 10)

[0083] Compound 10 was synthesized according to the scheme shown below.

[0084]

Embodiment 1-1

[0085] Embodiment 1-1: Synthesis of Compound 2

[0086] Under an argon atmosphere, 848 mL of a diethyl ether solution of 50.9 g of Compound 1 was cooled, and 131 mL of a 1.64 mol / L n-BuLi hexane solution was added dropwise over 30 minutes at -62°C or lower. After stirring at this temperature for 30 minutes, 21.5 g of dehydrated N,N-dimethylacetamide was added dropwise over 10 minutes. Aqueous ammonium chloride solution was added and stirred at room temperature for 2 days. It extracted with ethyl acetate, dried the organic layer with anhydrous magnesium sulfate, and concentrated under reduced pressure. Compound 2 was used directly in the following reaction without further purification.

Embodiment 1-2

[0087] Embodiment 1-2: the synthesis of compound 3

[0088]40.0 g of 1,2-ethanediol and 12.3 g of p-toluenesulfonic acid monohydrate were added to 830 mL of a toluene solution of compound 2, and the generated water was removed, followed by reflux for 20 hours. After cooling, an aqueous solution of sodium carbonate was added, and a small amount of ethyl acetate was added for extraction. The obtained organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.

[0089] The concentrated residue was purified by silica gel column chromatography (mobile phase: heptane / ethyl acetate=9 / 1 to 7 / 3) to obtain 24.3 g of Compound 3 (yield 46%).

[0090] 1 H-NMR (CDCl 3 )δ: 8.48 (1H, s), 7.63 (1H, dd, J = 8.2, 4.1Hz), 7.45 (1H, dd, J = 8.2, 4.1Hz), 4.08-4.05 (2H, m), 3.81-3.75 (2H, m), 1.67 (3H, s).

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Abstract

Provided are a radionuclide-labeled compound having both tau protein affinity and amyloid protein affinity; an imaging agent that contains the radionuclide-labeled compound and that is used for imaging tau proteins and / or amyloid proteins; and a radioactive medicine that contains the radionuclide-labeled compound and that is used for diagnostic imaging of diseases caused by the aggregation of tauproteins and / or amyloid proteins. Radionuclide-labeled compounds represented by general formula (1) or salts thereof. (In the formula, X represents a radioactive iodine atom, 18F or 11CH3; pyridine and oxazole are bound by a carbon atom; and pyridine is bound to imidazopyridine by a carbon atom.)

Description

technical field [0001] The present invention relates to radionuclide labeled compounds and imaging agents containing the compounds. Background technique [0002] In Japan, where the aging population is getting worse, the number of people with dementia is gradually increasing, becoming a serious social problem. According to statistics published in 2013 by the Research Group of the Japanese Ministry of Labor and Welfare, 15% of people over the age of 65 suffer from dementia, and it is estimated that there are 4.62 million people with dementia. , MCI) patients have 4 million people. Regarding the details of dementia patients in this statistics, it is reported that Alzheimer's Disease (AD) is as high as 67.6%, vascular dementia as high as 19.5%, Lewy's dementia as follows: Dementia with Lewy body (DLB) is as high as 4.3% (Non-Patent Document 1). In addition, among other statistics, it has been reported that patients with frontotemporal lobar degeneration (FTLD) account for ab...

Claims

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Application Information

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IPC IPC(8): C07D401/14C07D413/14C07D471/04A61K31/435A61K31/4353A61P25/28
CPCA61K51/04C07D471/04C07B59/002A61K51/0455A61K51/0453A61K2123/00
Inventor 季斌樋口真人须原哲也陈忠正藤本央介
Owner 上海富吉医疗科技有限公司
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