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Method for preparing adamantine disulfide tetroxide derivative

A technology of dimethyladamantaneaminoacetamide and dimethyladamantaneaminoacetamide, which is applied in the field of synthesis of radiopharmaceutical-labeled precursor compounds, and can solve problems such as no relevant reports

Inactive Publication Date: 2008-04-09
JIANGSU INST OF NUCLEAR MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There is no registration number on CA, and there are no related reports at home and abroad

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  • Method for preparing adamantine disulfide tetroxide derivative
  • Method for preparing adamantine disulfide tetroxide derivative
  • Method for preparing adamantine disulfide tetroxide derivative

Examples

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Embodiment 1

[0024] Example 1 N-[2-((2-(S-(4-methoxybenzyl)mercapto)ethyl)amino)acetyl]-S-(4-methoxybenzyl)-2-amino Synthesis of ethanethiol (compound II):

[0025] 4-Methoxybenzyl-(2-chloroacetamidoethyl)sulfide (5.47g, 20mmol), 2-(4-methoxybenzylthio)ethylamine (3.94g, 20mmol) and Potassium carbonate (20mmol), dry triethylamine 4.2mL, anhydrous acetonitrile 100mL, potassium iodide (15mmol), reflux for 22 hours, and the reaction was complete as detected by thin layer chromatography. Acetonitrile was removed by rotary evaporation, water and dichloromethane in equal volume ratio were added to separate layers, the organic phase was washed with water, dried over anhydrous sodium sulfate, and rotary evaporated to dryness to obtain 6.93 g of crude white solid, which was purified by column chromatography to obtain compound II as a white solid.

Embodiment 2

[0026] Embodiment 2 Bromoacetyl-3, the synthesis of 5-dimethylamantadine (compound III):

[0027] Under N2 protection, control the temperature at -45°C, dissolve (10.54g, 58.9mmol) amantadine in 75mL of dry dichloromethane, add dropwise to a solution of chloroacetyl chloride (58.7mmol) in 75mL of dichloromethane, dropwise, dropwise Add 10 mL of triethylamine, continue to stir for 1 hour, rise to room temperature and stir for 1 hour, add 150 mL of water to separate layers, wash the organic layer with water until neutral, dry with anhydrous sodium sulfate, and rotary evaporate to dryness to obtain 13.4 g of crude light yellow solid, which was used Recrystallization from ethyl acetate:n-hexane (1:6) gave pale yellow granular crystals (compound III).

Embodiment 3

[0028] Example 3 N-[2-(S-(4-methoxybenzyl)thio)ethyl]N-[(N-(2-(S-(4-methoxybenzyl)thio) Ethyl)amino)formylmethyl]-3,5-dimethyladamantanylaminoacetamide (compound IV) synthesis:

[0029]Compound II (1.6g, 3.6mmol), compound III (0.98g, 3.6mmol), potassium carbonate (5g, 36mmol), potassium iodide (0.6g, 3.6mmol), anhydrous acetonitrile 100mL, reflux reaction for 12 hours, thin layer Chromatographic detection of complete reaction, spin-dried anhydrous acetonitrile, added 100mL water and 100mL dichloromethane for layering, washed the organic layer with water until neutral, dried over anhydrous sodium sulfate, and spin-dried to obtain 2.2 g of a dark red oily crude product, dissolved in ethyl acetate : n-Hexane (1:5) as the eluent column chromatography to obtain translucent oil (compound IV).

[0030] HPLC: 97%.

[0031] Mass Spectrum MS: MS (m / z): 654(m+1), 676(m+Na), 692(m+K), 708(m+NaS) 2 methyl groups on 1H-NMR adamantane -0.832ppm (6H singlet), 1.10-1.18ppm (2H multiplet); ...

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Abstract

The invention relates to a preparative method of derivative of memantine hydrochloride alkyl 2-sulfer 2-nitrogen, and belongs to the technical field of synthesis of marking precursor compound for radiopharmaceutical. The invention provides a preparative method of N-[-(N-2-thiolethy)) amino acetyl]-(2- thiolethy)-3, 5-NCAM to prepare the radiopharmaceutical of 99m<Tc-NCAM marked by technetium which is used for image display of brain receptor. Being approved by experiment, the NCAM meets the requirements of permeability about blood brain barrier(BBB) in the aspects such as electroneutrality, molecule size and lipid solubility(LogP). After being mixed with other adjuvant drug and frozen, the NACM is easy to product a medicine box with good stability and a marking rate of above 95 percent. The prepared 99m<Tc-NCAM is tested by an animal distribution in mouse and radiation self-developing test, and the result is that the 99m<Tc-NCAM concentrates on the striaturn and hippocampus of the mouse. With high safety in animal test, the invention is a potential developer of the brain receptor.

Description

technical field [0001] The invention relates to a preparation of N-[2-(N-(2-mercaptoethyl))aminoacetyl]-N-(2-mercaptoethyl)-3,5-dimethyladamantylaminoacetamide The method belongs to the technical field of radiopharmaceutical labeling precursor compound synthesis. Background technique [0002] N-[2-(N-(2-mercaptoethyl))aminoacetyl]-N-(2-mercaptoethyl)-3,5-dimethyladamantanylaminoacetamide (abbreviated as NCAM), which Molecular formula is C 20 h 35 N 3 o 2 S 2 , can conveniently form a stable complex with the isotope technetium 99m Tc-NCAM. [0003] Brain receptor imaging is a new field of neuronuclear medicine in the 21st century. In recent years, the relationship between receptor function and nervous system diseases has been explored from the level of molecular medicine, and used for diagnosis and treatment. It is the frontier of medical science research in the world. Human brain receptor imaging using radionuclides is a new technology for molecular nuclear medicine ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/41C07C319/02A61K51/04A61K103/10
Inventor 张建康周杏琴徐希杰钦晓峰邹美芬曹国宪罗世能
Owner JIANGSU INST OF NUCLEAR MEDICINE
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