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Marked cyclofenil derivative and referential compound and midbody thereof, and preparation method and application

A technology for compounds and derivatives, which is applied in the field of labeling drug derivatives and their reference compounds and intermediates, and can solve problems such as unsatisfactory imaging results

Inactive Publication Date: 2010-07-14
SHANGHAI INST OF APPLIED PHYSICS - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The technical problem to be solved by the present invention is to overcome the unsatisfactory defect of imaging results in the existing cyclofenyl labeling method, and provide a kind of labeling cyclofenyl derivatives and reference compounds and intermediates thereof, and preparation Methods and Applications

Method used

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  • Marked cyclofenil derivative and referential compound and midbody thereof, and preparation method and application
  • Marked cyclofenil derivative and referential compound and midbody thereof, and preparation method and application
  • Marked cyclofenil derivative and referential compound and midbody thereof, and preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0064] Synthesis of embodiment 1 bromocyclofenil (cyclofenil) compound (compound I, X=Br, m=3, n=2):

[0065]

[0066] Add compound V (n=2) (500mg, 1.79mmol) into the three-necked flask, anhydrous K 2 CO 3 (1.20g, 8.8mmol), evacuate and pass N 2 Replacement, back and forth three times. Inject 30ml of acetone into it, control the temperature at 46°C, and stir for 0.5h. Then 1,4-dibromobutane (400mg, 1.86mmol) was slowly added dropwise thereto, and reacted for 8h under the same temperature conditions. The resulting pink cloudy solution. Filter and wash with saturated NaCl, extract with dichloromethane (3×20 mL), dry over anhydrous sodium sulfate, filter, and spin to dry the solvent. With V (petroleum ether): V (ethyl acetate) = 10:1 as the eluent, 185.2 mg of light yellow viscous product I was rapidly obtained through the flash column, with a yield of 25%.

[0067] Its identification data are as follows:

[0068] IR(KBr) v: 3264.47, 2921.43, 2843.59, 1609.53, 1503.29, ...

Embodiment 2

[0070] The synthesis of embodiment 2Cyclofenil-dipicolylamine (compound II, m=3, n=2)

[0071]

[0072] Add compound I (X=Br, m=3, n=2) (145mg, 0.35mmol) in a three-necked flask, anhydrous K 2 CO 3 (150 mg, 1.09 mmol). Vacuum through N 2 Replacement, back and forth three times, inject 20ml of acetone into it, and react at 44°C for 0.5h. Then compound VI 2,2'-dipicolylamine (120mg, 0.603mmol) was added thereto, and reacted for 18h. Extract with dichloromethane (3×20 mL), dry over anhydrous sodium sulfate, filter, and spin to dry the solvent. Elute through a flash column with V (dichloromethane): V (methanol) = 50: 1 or separate on a plate with V (dichloromethane): V (methanol) = 10: 1. Obtained 82.1mg of colorless viscous liquid, yield 44%;

[0073] Its identification data are as follows:

[0074] IR(KBr) v: 2921.23, 2843.59, 2108.92, 1605.45, 1501.29, 1429.74, 1237.68, 1160.05, 833.14, 763.80, 575.71cm -1 ;

[0075] 1 H NMR (CDCl 3 , 400MHz) δ: 8.50(d, J=4.8Hz, 2...

Embodiment 3

[0077] Embodiment 3 Cyclofennel dippicolylamine Re(CO) 3 Synthesis of Complex (Compound III, m=3, n=2)

[0078] 1. Rhenium tricarbonyl ([N(Et) 4 ] 2 [Re(CO) 3 Br 3 ], tetraethyl bromide ammonium tricarbonyl rhenium complex) synthesis (referring to the above literature)

[0079] Under the condition of nitrogen protection, weigh 0.2527g (0.6mmol) tetraethylamine bromide (Swiss Fluka company product) and 0.2076g (0.5mmol) bromopentacarbonyl rhenium (Swiss Fluka company product), add solvent diethylamine Glycol dimethyl ether 50.0mL was first slowly heated to 80°C under the condition of magnetic stirring, and the solid was completely dissolved after 10 minutes of reaction, and then heated to 120°C for 8 hours of reaction. At this time, a light yellow solid was formed in the solution. Filter while hot, wash with cold diglyme and anhydrous diethyl ether several times, and dry in a desiccator. After drying, the yellow powder was washed with absolute ethanol, filtered, and vacuu...

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Abstract

The invention discloses a marked cyclofenil derivative as shown in formula IV, a referential compound and midbody thereof, a preparation method and an application, wherein m is equal to 0-9, n is equal to 0-6, 99mTc is 99m technetium, and CO is carbonyl group. The marked cyclofenil derivative in the invention has activity to resist breast cancer and has favorable visualization effect.

Description

technical field [0001] The present invention relates to a labeled drug derivative and its reference compound and intermediate, as well as its preparation method and application, in particular to a labeled cyclofenyl derivative, its reference compound and its intermediate, its preparation method and its application. Background technique [0002] Nuclear medicine can use the special physical properties of labeled nuclides in some radiopharmaceuticals to perform internal radiation therapy while imaging a variety of tumors and their lesions. This unique method of tumor diagnosis and treatment has been increasingly accepted in clinical practice. Pay attention to. At present, such radionuclides with both therapeutic and imaging functions mainly include 131 I. 153 Sm, 117m Sn, 186 Re, 188 Re et al. in, 188 Due to its excellent physical and chemical properties, Re has attracted much attention in the field of tumor diagnosis and treatment. [0003] 99m Tc has become the most...

Claims

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Application Information

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IPC IPC(8): C07F13/00C07D213/36C07C43/23A61K51/04A61K103/10
Inventor 沈玉梅朱华张元庆黄立梁孙艳红张春春许晓平许嘉
Owner SHANGHAI INST OF APPLIED PHYSICS - CHINESE ACAD OF SCI
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