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Novel organic phosphine compound and preparation method and application thereof

A compound and organic phosphine technology, applied in a new type of organic phosphine compound and its preparation and application fields, can solve the problems of clinical application limitations, short half-life of imaging agents, etc., and achieve high initial uptake value and high ratio of target to non-target , good stability

Inactive Publication Date: 2013-01-30
BEIJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the half-life of the above-mentioned imaging agents is short, and the clinical application is still greatly limited.

Method used

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  • Novel organic phosphine compound and preparation method and application thereof
  • Novel organic phosphine compound and preparation method and application thereof
  • Novel organic phosphine compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Example 1. [ 19 F] Preparation of FMBTP

[0061] (1)[ 19 F] Synthesis of BMFMB:

[0062] Under anhydrous and oxygen-free conditions, add 6 mL of tetrabutylammonium fluoride solution in THF to a 100 mL three-necked flask, and blow dry with nitrogen at 110°C. Add 2 mL of anhydrous acetonitrile and blow dry with nitrogen, repeat three times. Add 30 mL of anhydrous acetonitrile, then add 1.32 g of 1,4-bis(bromomethyl)benzene, reflux overnight at 100°C, cool the reaction solution to room temperature, remove the solvent by rotary evaporation, and purify the crude product through a 200-300 mesh silica gel column , developing agent is sherwood oil, finally obtains pale yellow solid 1-(bromomethyl)-4-(fluoromethyl)benzene ([ 19 F] BMFMB). NMR spectrum: ( 1 HNMR, CDCl 3 )δ:4.496(s,2H,BrCH 2 ),5.372(d,2H,CH 2 F),7.351(d,2H),7.422(d,2H);( 19 FNMR, CDCl 3 )δ: -208.48.

[0063] (2)[ 19 F] Synthesis of FMBTP

[0064] Under anhydrous and anaerobic conditions, the [ 19 F]...

Embodiment 2

[0066] Example 2. [ 18 F] Preparation of FMBTP

[0067] it's here[ 18 F] There are two methods for the preparation of FMBTP, one is a two-step method, and the other is a one-pot method. The two preparation methods will be described below:

[0068] 1. Two-step preparation[ 18 F] FMBTP

[0069] (1)[ 18 F] Synthesis of BMFMB:

[0070] 1.3mL containing 1.5mg K 2 CO 3 and 2 mg K 2.2.2. of[ 18 F]F - The solution was added to a 10 mL reaction flask, blown dry with nitrogen at 110°C, added 0.7 mL of anhydrous acetonitrile and evaporated to dryness, and repeated three times. Add 0.5 mL of anhydrous acetonitrile solution of 3 mg of 1,4-bis(bromomethyl)benzene into the above reaction flask, and react under airtight conditions at 100°C for 6 min to obtain [ 18 F] BMFMB. After the reaction, cool to room temperature, pass through a 0.22 μm membrane filter, dilute to 1 mL with acetonitrile, mix well and inject into a C-18 reverse-phase semi-preparative column (10×250 mm, Venusil MP...

Embodiment 3

[0081] Example 3. [ 19 F] Preparation of mFMBTP

[0082] (1)[ 19 F] Synthesis of mBMFMB:

[0083] Under anhydrous and oxygen-free conditions, add KF.2H to a 100mL three-neck flask 2 O 0.224g, add anhydrous acetonitrile 10mL, blow dry with nitrogen at 110°C, repeat three times. Add 20mL of anhydrous acetonitrile, 18-Crown-60.644g, then add 0.528g of 1,3-bis(bromomethyl)benzene, reflux overnight at 100°C, cool the reaction solution to room temperature, remove the solvent by rotary evaporation, and the crude product is 200-300 purpose silica gel column purification, developer is sherwood oil, finally obtains colorless liquid 1-(bromomethyl)-3-(fluoromethyl)benzene ([ 19 F] mBMFMB). NMR spectrum: ( 1 HNMR, CDCl 3 )δ:4.506(s,2H,BrCH 2 ),5.324(d,2H,CH 2 F), 7.306(d,2H), 7.391(d,2H).

[0084] (2)[ 19 F] Synthesis of mFMBTP

[0085] Under anhydrous and anaerobic conditions, the [ 19 F] mBMFMB and triphenylphosphine 0.24g were added to 25mL of anhydrous acetonitrile, react...

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Abstract

The invention provides a novel organic phosphine compound. According to the organic phosphine compound, a structural formula is shown as a formula (1), wherein fluoro methyl is positioned at para-positions or meta-positions of benzene rings, F is 19F or 18F. The organic phosphine compound has high stability, high cardiac initial intake value, high target-to-nontarget ratio and the like, and particularly, a radioactive fluorine-18 marked organic phosphine cation compound has the advantages of high chemical stability and biological properties, high radiochemical purity, high cardiac initial intake value, simplicity of preparation, low using cost and the like, and can be used as a novel fluorine-18 marked polyethylene glycol terephthalate (PET) myocardial perfusion photographic developer to be applied to the technical fields of radiopharmaceutical chemistry and clinical nuclear medicine.

Description

technical field [0001] The invention relates to a novel organic phosphine compound and its preparation method and application. Background technique [0002] Coronary heart disease is one of the most serious diseases threatening human health. In my country, the morbidity and mortality of coronary heart disease are on the rise. In 2007, the data released by the Ministry of Health showed that about 3 million people died of cardiovascular disease in my country every year, which has become the first cause of death among urban and rural people in my country, accounting for nearly 40% of the causes of death in my country. [0003] The use of myocardial perfusion imaging in non-invasive heart disease examinations began in the 1970s, and its great diagnostic value has been widely accepted around the world. It has become one of the most important imaging methods for the diagnosis, efficacy evaluation and prognosis of coronary heart disease. one. Myocardial perfusion single photon e...

Claims

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Application Information

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IPC IPC(8): C07F9/54A61K51/04A61K101/02
Inventor 张现忠赵祚全张明如刘畅郭志德
Owner BEIJING NORMAL UNIVERSITY
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