Chemistry:Tolazamide
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Tolazamide is an oral blood glucose lowering drug used for people with Type 2 diabetes. It is part of the sulfonylurea family (ATC A10BB).
Synthesis
The reaction between p-toluenesulfonamide (1) and ethyl chloroformate (2) in the presence of base gives tosylurethane [5577-13-9] (3). Heating that intermediate with azepane (4) leads to the displacement of the ethoxy group and the formation of tolazemide (5).[1][2][3][4][5]
Azepane proper would lead to [13078-23-4].
References
- ↑ Synthesis of essential drugs. Elsevier. 2006. ISBN 9780444521668.
- ↑ "Antidiabetic Agents. N4-Arylsulfonylsemicarbazides". Journal of Medicinal and Pharmaceutical Chemistry 91 (4): 815–22. July 1962. doi:10.1021/jm01239a016. PMID 14056414.
- ↑ John B Wright, U.S. Patent 3,063,903 (1962 to Upjohn Co).
- ↑ Wright John Brenton, GB patent 887886 (1962 to Upjohn).
- ↑ DE1196200 idem Korger Gerhard, Weber Helmut, Aumuller Walter, U.S. Patent 3,248,384 (1966 to Hoechst Ag).
External links
- "Tolazamide". Medline Plus. U.S. National Library of Medicine. https://medlineplus.gov/druginfo/meds/a682482.html.
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