Identification | Back Directory | [Name]
BIA10-2474 | [CAS]
1233855-46-3 | [Synonyms]
CS-2451 BIA10-2474 BIA10-2474; BIA-10-2474 1H-Imidazole-1-carboxamide,N-cyclohexyl-N-methyl-4-(1-oxido-3-pyridinyl)- | [Molecular Formula]
C16H20N4O2 | [MDL Number]
MFCD30532661 | [MOL File]
1233855-46-3.mol | [Molecular Weight]
300.36 |
Chemical Properties | Back Directory | [storage temp. ]
Store at -20°C | [solubility ]
DMSO:2.2(Max Conc. mg/mL);7.32(Max Conc. mM) | [form ]
A crystalline solid | [color ]
White to off-white |
Hazard Information | Back Directory | [Uses]
N-Cyclohexyl-N-methyl-4-(1-oxido-3-pyridinyl)-1H-imidazole-1-carboxamide is a potential fatty acid amide hydrolase (FAAH) inhibitor used for treating and preventing diseases. | [Synthesis]
In a further step of this synthesis, N-cyclohexyl-N-methyl-4-(pyridin-3-yl)-1H-imidazole-1-carboxamide (90 g, 317 mmol) was dissolved in dichloromethane (1350 ml) in a 2L reactor followed by addition of peracetic acid (84 ml, 475 mmol). The reaction mixture was stirred at 25 °C and the progress of the reaction was monitored by HPLC until N-cyclohexyl-N-methyl-4-(pyridin-3-yl)-1H-imidazole-1-carboxamide was completely consumed. After completion of the reaction, an aqueous solution (270 ml) of sodium metabisulfite (60.2 g, 317 mmol) was slowly added, keeping the reaction temperature below 30 °C. After performing phase separation, the organic phase was washed with water. After phase separation again, the organic phase was concentrated to 1/5 of the original volume at atmospheric pressure.Subsequently, the solvent was replaced with isopropanol (1350 ml) and the suspension was cooled down to 0 °C over a period of 4 hours and stirring was continued at this temperature for 1 hour. The resulting white crystalline solid was collected by filtration and washed sequentially with water (270 ml) and isopropanol (270 ml) to give 84.8 g (89% yield) of the target product. | [in vivo]
In January 2016, severe adverse events (SAE) occurs in the Phase I clinical trial using the drug BIA 10-2474 including one death. The possibilities for failure of trials such as off-target effect, dose calculation, unexpected immune response, species variation, and cumulative dose toxicity would be sought[2]. | [storage]
Store at -20°C | [References]
[1] Patent: WO2012/15324, 2012, A1. Location in patent: Page/Page column 58-59 [2] Patent: US2012/65191, 2012, A1. Location in patent: Page/Page column 32 [3] Patent: WO2014/17938, 2014, A2. Location in patent: Page/Page column 67; 68 |
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Company Name: |
BOC Sciences
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Tel: |
1-631-485-4226; 16314854226 |
Website: |
https://www.bocsci.com |
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