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A sort of 18 F-labeled benzimidazole compound and its preparation method and application

A compound and synthesis method technology, applied in the field of medicine, can solve the problems of rare radiolabeling and imaging, and achieve the effects of good industrial application prospects, simple and easily controllable preparation process, and high specific activity of radioactivity.

Active Publication Date: 2020-06-02
SHANDONG UNIV QILU HOSPITAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are still few reports on the use of benzimidazole compounds for radiolabeling and imaging

Method used

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  • A sort of <sup>18</sup> F-labeled benzimidazole compound and its preparation method and application
  • A sort of <sup>18</sup> F-labeled benzimidazole compound and its preparation method and application
  • A sort of <sup>18</sup> F-labeled benzimidazole compound and its preparation method and application

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Experimental program
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preparation example Construction

[0056] In view of this, in a typical embodiment of the present invention, a kind of 18 The synthetic method of 2-[(1-methyl-1-methylamino) carbonamide-1-cyclohexyl-carbonyl-3-hydroxyl-pyrrole]-3-(4-fluoro-phenyl)-imidazole of F mark, The method comprises the following reaction steps:

[0057] (1)

[0058] (2)

[0059] (3)

[0060] (4)

[0061]

[0062] (5)

[0063]

[0064] (6)

[0065]

[0066] (7)

[0067]

[0068] In yet another specific embodiment of the present invention, the specific method of the step (1) is:

[0069] Dissolve 2-methyl-3-N,N-dimethylnitrobenzene in the mixed solution of methanol-water, add ammonium chloride, add Zn under ice bath, filter, concentrate the filtrate under reduced pressure, add ethyl acetate , dried to obtain intermediate 2;

[0070] In yet another specific embodiment of the present invention, the molar ratio of 2-methyl-3-N,N-dimethylnitrobenzene to ammonium chloride is 1:0.5-2; the volume ratio of methanol to wa...

Embodiment 1

[0093] Dissolve 2.6g of 2-methyl-3-N,N-dimethylnitrobenzene in a mixed solution of 50ml of methanol-water (volume ratio 1:1), add 0.2g of ammonium chloride, and add 1.5 g Zn, filtered, the filtrate was concentrated under reduced pressure, added ethyl acetate, washed with water, and dried over anhydrous sodium sulfate to obtain intermediate 2; ESI-MS (m / z): 227 (M + ); 1 H NMR (DMSO-d 6, , 400MHz) δ:8.79(s,4H,2×NH 2 ),6.39-7.41(m,7H,Ar-H) 13 , 2.65(s,6H,NCH 3 ×2) CNMR (CDCl 3 ,125MHz)δ,145.7,134.3,133.5,129.6,129.6,125.5,1 24.2,118.3,117.6,111.2,111.2,112.5,42.7,42.8; the reaction formula is as follows:

[0094]

Embodiment 2

[0096] Dissolve 3.5g of N-Cbz-protected proline derivatives and 2.5g of N-methylmorpholine in 30ml of dry dichloromethane, add 5ml of isobutyl chloroformate dropwise, stir, and dissolve 3.8g of intermediate 2 in 10ml In dichloromethane, add dropwise to the above system, react at low temperature, and rise to room temperature to obtain intermediate 3; ESI-MS (m / z): 474 (M + ); 1 H NMR (DMSO-d 6, , 400MHz) δ: 13.75(s, H, OH), 8.25(s, 2H, NH 2 ), 7.85(s,H,NH),6.12-7.68(m,12H,Ar-H) 13 ,2.11-3.41(d,4H,CH 2 ),5.56(S,2H,CH 2 ), 3.11-4. 25(t, 2H, CH), 2.65(s, 6H, NCH 3 ×2) 13 CNMR (CDCl 3 ,125MHz)δ, 169.5, 158.7, 141.4, 139.2, 128.5, 126., 7, 126.3, 125.9, 125.6, 124.5, 123.1, 122.9, 122.9, 122.6, 121.4, 120.9, 120.3, 114.6, 113.5, 123.9, 7 65.6, 55.3, 54.6, 41.6, 41.1; the reaction formula is as follows:

[0097]

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Abstract

The invention provides an 18F marked benzimidazole compound as well as a preparation method and application thereof. The benzimidazole compound is 2-[(1-methyl-1-methylamino)carbamide-1-cyclohexyl-carbonyl-3-hydroxyl-pyrrole]-3-(4-fluoro-phenyl)-imidazole. With high radiochemical yield and non-correction yield reaching up to 80% and high specific activity, the 18F marked benzimidazole compound issuitable for PET tumor imaging, and has a relatively high tumor uptake value and a value for the examination and diagnosis as well as radiotherapy of tumor. In the invention, the raw materials for preparing an 18F marked precursor compound are cheap and easily available, the preparation process is simple and easy to control, and the reaction conditions are mild; meanwhile, the synthesis efficiencyis effectively improved, and the 18F marked benzimidazole compound has a good prospect in industrialized application and a high value in practical application.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a 18F-labeled benzimidazole compound and a preparation method and application thereof. Background technique [0002] Positron emission tomography (PET) technology, as a cutting-edge technology for biomedical research and clinical diagnosis in the 21st century, is called "in vivo biochemical imaging" technology, which can noninvasively, quantitatively and dynamically observe the physiological and biochemical conditions in the human body from outside the body. Changes, insights into the activity of marker drugs in normal or sick people. In the last thirty years, with the research and development of PET technology, its advantages in tumor diagnosis have attracted more and more attention. PET can not only clearly display the functional tissue of living body, but also can be used to quantitatively detect the metabolic function of living tissue with the development of var...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/04C07B59/00A61K51/04A61P35/00A61K101/02
CPCA61K51/0453A61P35/00C07B59/002C07B2200/05C07D403/04
Inventor 刘剑峰李昕于红玲
Owner SHANDONG UNIV QILU HOSPITAL
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