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Radiolabelled compounds

A technology for radioactive labeling and compounds, applied in the direction of in vivo radioactive preparations, introduction of isotopes of heterocyclic compounds, introduction of isotopes into organic compounds, etc.

Pending Publication Date: 2022-06-21
F HOFFMANN LA ROCHE & CO AG +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Several PET tracers for selective imaging of MAGL have been reported, but most of them are based on covalent inhibitor structures

Method used

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Examples

Experimental program
Comparison scheme
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example

[0112] The present invention will be more fully understood by reference to the following examples. However, the claims should not be construed as limiting the scope of the embodiments.

[0113] The following abbreviations are used in this text:

[0114] AcOH=acetic acid, ACN=acetonitrile, BEMP=2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphine, Boc= tert-Butoxycarbonyl, CAS RN=Chemical Abstracts Registration Number, Cbz=benzyloxycarbonyl, Cs 2 CO 3 = cesium carbonate, CO = carbon monoxide, CuCl = cuprous(I) chloride, CuCN = cuprous(I) cyanide, CuI = cuprous(I) iodide, DMAP = 4-dimethylaminopyridine, DME = Dimethoxyethane, DMEDA=N,N'-dimethylethylenediamine, DMF=N,N-dimethylformamide, DIPEA=N,N-diisopropylethylamine, dppf=1, 1-Bis(diphenylphosphino)ferrocene, EDC.HCl=N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride, EI=electron bombardment, ESI = Electrospray ionization, EtOAc = ethyl acetate, EtOH = ethanol, h = hours, FA = formic acid,...

example 1

[0130] (4aR,8aS)-6-[3-[2-[2-Fluoro-6-(trifluoromethyl)phenyl]ethyl]azetidine-1-carbonyl]-4,4a,5, 7,8,8a-Hexahydropyrido[4,3-b][1,4]oxazin-3-one

[0131]

[0132] To (4aR,8aS)-3-oxohexahydro-2H-pyrido[4,3-b][1,4]oxazine-6(5H)-carboxylic acid 4-nitrophenyl ester (BB2) (42 mg , 131 μmol) and DIPEA (42.3 mg, 57.1 μL, 327 μmol) in ACN (0.5 mL) was added 3-(2-fluoro-4-(trifluoromethyl)phenethyl)azetidine 4 - Tosylate (60.3 mg, 144 μmol) and the yellow solution was stirred at RT overnight. To the reaction solution was added silica gel, and the mixture was evaporated. The compound was purified by silica gel chromatography using an MPLC system on a 4 g chromatography column and eluting with a gradient of n-heptane:EtOAc / ethanol 3 / 1 (70:30 to 10:90). Using ACN:H on preparative HPLC (Gemini NX column) 2 A secondary purification with O (containing 0.1% formic acid) (20:80 to 98:2) gave the title compound as a colorless foam (0.038 g, 68%). MS(ESI): m / z=430.2[M+H] + .

[0133] In...

example 3H

[0146] instance[ 3 H]1

[0147] [ 3 H](4aR,8aS)-6-[3-[2-[2-fluoro-6-(trifluoromethyl)phenyl]ethyl]azetidine-1-carbonyl]-4,4a, 5,7,8,8a-Hexahydropyrido[4,3-b][1,4]oxazin-3-one

[0148]

[0149]In a 4 mL tritiated flask, place (4aR, 8aS)-6-(3-((E)-2-fluoro-6-(trifluoromethyl)styryl)azetidine-1-carbonyl) Hexahydro-2H-pyrido[4,3-b][1,4]oxazin-3(4H)-one (2.0 mg, 4.68 μmol) and palladium on activated carbon (10%) (4.98 mg, 4.68 μmol) Mix in ethanol (1 mL). The flask was connected to an RC Tritec tritium manifold and degassed by three freeze-thaw cycles. Tritium gas was introduced and the suspension was vigorously stirred at 610 mbar for 4 h under a tritium gas atmosphere. The solution was cooled with liquid nitrogen and the excess tritium gas in the reaction vessel was reabsorbed in a uranium trap for spent tritium. The solvent was lyophilized and the labile tritium was removed by lyophilization using MeOH (3 x 0.5 mL). The remaining black residue was suspended in ethanol...

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Abstract

The present invention provides novel radiolabeled monoacylglycerol lipase (MAGL) inhibitors that are useful in medical imaging such as positron emission tomography (PET), single photon emission computed tomography (SPECT), and / or radioautography.

Description

technical field [0001] The present invention relates to radiolabeled organic compounds. More particularly, the present invention relates to radiolabeled monoacylglycerol lipase (MAGL) inhibitors useful in medical imaging such as positron emission tomography (PET), single photon emission computed tomography (SPECT) and / or or autoradiography. Background technique [0002] The radiolabeled compounds described herein have been found to be useful in molecular imaging of monoacylglycerol lipases (MAGL). Molecular imaging is based on the selectivity and Specific interactions, visualized by PET, NMR, NIR, or other means. As a nuclear medicine imaging modality, PET is well suited for generating three-dimensional images that provide information about the distribution of biological targets in a given organ or the metabolic activity of such organs or cells or the entry of drugs into such organs, binding to biological targets and and / or important information on the ability to alter b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/04C07B59/00A61K31/5365A61P25/16A61P25/28A61P35/00
CPCC07D498/04C07B59/002A61P25/16A61P25/28A61P35/00C07B2200/05A61B6/037A61K51/0463
Inventor 卢多维奇·科林马丁·埃德尔曼罗卡·戈比尤伟·格雷瑟托马斯·哈通何颖芳迈克尔·霍纳佰努瓦·霍恩斯普格卡斯滕·卡罗尔穆林静迪特尔·穆里菲奥·奥哈拉汉斯·里斯特马丁·里特尔
Owner F HOFFMANN LA ROCHE & CO AG
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