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Radioactive arginine derivative for diagnosis and treatment and preparation method thereof

A mixture and compound technology, which is applied in the field of preparation of arginine derivatives, can solve the problems of harsh arginine labeling conditions and no new imaging agents for arginine derivatives reported.

Active Publication Date: 2019-04-09
CAPITAL UNIVERSITY OF MEDICAL SCIENCES +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the harsh conditions for the design, synthesis and labeling of arginine, there are currently no reported imaging agents for new arginine derivatives that retain the properties of arginine

Method used

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  • Radioactive arginine derivative for diagnosis and treatment and preparation method thereof
  • Radioactive arginine derivative for diagnosis and treatment and preparation method thereof
  • Radioactive arginine derivative for diagnosis and treatment and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0792] (2S,4S)-2-Amino-7-fluoro-4-(guanidinomethyl)heptanoic acid

[0793]

[0794] The synthetic route is as follows:

[0795]

[0796] (2S, 4S)-5-(tert-butoxy)-4-((tert-butoxycarbonyl)amino)-5-oxo-2-(3-((tetrahydro-2H-pyran-2- base)oxy)propyl)pentanoic acid

[0797]

[0798] 1-benzyl 5-(tert-butyl)(2S,4S)-4-((tert-butoxycarbonyl)amino)-2-(3-((tetrahydro-2H-pyran-2-yl) A mixture of oxy)propyl)glutarate (1.5 g, 2.8 mmol) and 10% Pd / C (0.2 g) in anhydrous EtOH (20 mL) was dissolved in H 2 Stirring was continued for 3 hours. The mixture was then filtered and the filtrate was concentrated in vacuo to give 8 as a white solid (1.24 g, 100%). 1 HNMR (400MHz, CDCl3) δ: 5.09(s, 1H), 4.58(d, J=4.0Hz, 1H), 4.23(d, J=5.6Hz, 1H), 4.0(s, 1H), 3.86(d, J=6.0Hz, 2H), 2.59-2.44(m, 1H), 1.91-1.79(m, 2H), 1.71-1.69(m, 6H), 1.55-1.53(m, 4H), 1.47(s, 9H) ,1.45(s,9H).13C NMR(100MHz,CDCl3)δ:172.14,159.40,155.60,129.16,128.28,114.36,84.88,83.24,82.80,81.85,79.28,55.31,52.15,560.95,445....

example 2

[0822] (2S,4S)-2-Amino-4-(4-(2-fluoroethoxy)benzyl)-5-guanidinopentanoic acid

[0823]

[0824] The synthetic route is as follows:

[0825]

[0826] (2S,4S)-4-(4-(Benzyloxy)benzyl)-2-((tert-butoxycarbonyl)amino)-5-hydroxypentanoic acid tert-butyl ester

[0827]

[0828]The acid (1 g, 2.12 mmol) was dissolved in 5 mL THF in a 50 mL round bottom flask, and the solution was cooled to 0 °C. To this solution was added dropwise Et 3 N (0.22 mL, 2.12 mmol) and ethyl chloroformate (0.26 mL, 2.2 mmol). After stirring at 0°C for 30 minutes, the reaction mixture was filtered off. In a 100 mL round bottom flask cooled with an ice bath, add NaBH 4 (0.17g, 4.24mmol) with 2mLH 2 The above filtrate was slowly added to the mixture of O. The mixture was stirred at room temperature for another 1 hour, then acidified to pH=7 with 1M HCl while cooling in an ice bath. The organic phase was collected, and the aqueous phase was extracted with EtOAc (20 mL×3). The combined organic pha...

example 3

[0849] (2S,4S)-2-Amino-4-(4-(3-fluoro-2-hydroxypropoxy)benzyl)-5-guanidinovaleric acid

[0850]

[0851] The synthetic route is:

[0852]

[0853] tert-butyl(2S,4S)-5-((E)-1,2-bis(tert-butoxycarbonyl)-3-(4-methoxybenzyl)guanidino)-2-((tert-butyl Oxycarbonyl)amino)-4-(4-(2-((tetrahydro-2H-pyran-2-yl)oxy)-3-(tosyloxy)propoxy)benzyl)pentyl ethyl acetate

[0854]

[0855] The compound (tert-butyl (2S, 4S)-5-((E)-1,2-bis(tert-butoxycarbonyl)-3-(4-methoxybenzyl)guanidino)-2-( (tert-butoxycarbonyl)amino)-4-(4-hydroxybenzyl)ethyl pentanoate (0.5g, 0.73mmol) and K 2 CO 3 (0.2g, 1.4mmol) was dissolved in 15mL DMF, stirred at room temperature, and then 2-((tetrahydro-2H-pyran-2-yl)oxy)propane-1,3-diylbis(4 -toluenesulfonate) (0.67g, 1.4mmol) was added and reacted overnight at room temperature. After adding ethyl acetate (50ml), washing with saturated NaCl, drying over anhydrous sodium sulfate, and removing the organic solvent, the product was obtained by column chromatogra...

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Abstract

The invention discloses a radioactive arginine derivative for diagnosis and treatment and a preparation method thereof and belongs to the field of preparation of arginine derivatives. The invention relates to a novel radioactive arginine derivative suitable for being labeled by 18F, 123I, 124I, 125I or 131I, a corresponding arginine derivative labeled by the 18F, the 123I, the 124I, the 125I or the 131I, 19F or 127I analogues thereof and application of the derivatives to reference standards, a method for preparing a compound, a composition containing the compound, a kit containing the compoundor the composition, and application of the compound, the composition or the kit to positron emission tomography (PET), or diagnostic imaging through single photon emission computed tomography (SPECT)or tumor treatment through the 131I.

Description

technical field [0001] The invention relates to the field of preparation of arginine derivatives, and specifically provides a radioactive arginine derivative for diagnosis and treatment and a preparation method thereof. suitable for use 18 F-labeled novel arginine derivatives and their corresponding 18 Labeled precursors and intermediates of F, their 19 F Fluorinated intermediates and cold compounds and their use as reference standards, preparation 18 Method and preparation of F-labeled compounds 19 F. Methods of Fluorinated Analogs, Compositions Comprising Such Compounds, Kits Comprising Such Compounds or Analogs, and 18 F-labeled compounds are useful for uses such as tumor positron emission tomography positron emission tomography (PET) and single photon emission computed tomography (SPECT), or therapy. Background technique [0002] Positron emission tomography (PET) and single photon emission computed tomography (SPECT), as one of the most advanced modern molecular im...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C277/08C07C279/14C07C309/73C07D309/12C07F7/22A61K51/04A61P35/00
CPCA61K51/0406A61P35/00C07B2200/05C07B2200/07C07C279/14C07C309/73C07D309/12Y02P20/55
Inventor 吴泽辉吴仁博黄勇刘松
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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