- A one-pot synthesis of tetrazolones from acid chlorides: Understanding functional group compatibility, and application to the late-stage functionalization of marketed drugs
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A one-pot and scalable synthesis of tetrazolones (tetrazol-5-ones) from acid chlorides using azidotrimethylsilane is presented. The reaction tolerates many functional groups and can furnish aryl-, heteroaryl-, alkenyl-, or alkyl-substituted tetrazolone products in moderate to excellent yield (14-94%). No reduction in yield was observed when the reaction was undertaken on a larger-scale (20-36 g). The method could be used for the late-stage functionalization of pharmaceuticals, to provide tetrazolone congeners of the marketed drugs aspirin, indomethacin, probenecid, telmisartan, bexarotene, niacin (vitamin B3), and the active metabolite of the recently-launched immuno-modulatory agent, BG-12 (Tecfidera). The ability of a tetrazolone group to serve as a bioisostere of a carboxylic acid, and to improve drug pharmacokinetic profiles is also highlighted.
- Duncton, Matthew A. J.,Singh, Rajinder
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supporting information
p. 9338 - 9342
(2016/10/13)
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- Tetrazolones as a Carboxylic Acid Bioisosteres
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The present disclosure provides compounds that include a tetrazolone derivative of a carboxyl group of an active agent. This disclosure also relates to pharmaceutical compositions that include these compounds, methods of using these compounds in the treatment of various diseases and disorders, and processes for preparing these compounds.
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Paragraph 0329; 0330
(2016/08/17)
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- COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS
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Disclosed herein are compounds of formula (I) wherein Ring A and R1 are as defined in the specification. Pharmaceutical compositions comprising such compounds, and methods for treating conditions and disorders using such compounds and pharmaceutical compositions are also disclosed.
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Page/Page column 33
(2010/10/19)
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- NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS
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The present invention relates compounds of formula (I) wherein A and R1 are as defined in the specification, pharmaceutical compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and pharmaceutical compositions.
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Page/Page column 30
(2009/05/29)
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