Oxatomide
Template:Short description Template:Cs1 config Template:Drugbox Oxatomide, sold under the brand name Tinset among others, is a antihistamine of the diphenylmethylpiperazine family which is marketed in Europe, Japan, and a number of other countries.[1][2][3][4] It was discovered at Janssen Pharmaceutica in 1975.[5] Oxatomide lacks any anticholinergic effects.[2] In addition to its H1 receptor antagonism, it also possesses antiserotonergic activity similarly to hydroxyzine.[2] Oxatomide was also found to have antiviral activity against Venezuelan equine encephalitis virus (VEEV).[6]
It was patented in 1976 and came into medical use in 1981.[7]
Chemistry
Synthesis
Reaction of 2-Benzimidazolinone with isopropenyl acetate leads to the singly protected imidazolone derivative (2). Alkylation of this with 3-chloro-1-bromopropane affords the functionalized derivative (3). Alkylation of the monobenzhydryl derivative of piperazine (4) with 3 gives oxatomide (5), after hydrolytic removal of the protecting group.
References
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- ↑ <templatestyles src="Citation/styles.css"/>Template:Citation/make link, Vandenberk J, Kennis LE, Van der Aa MJ, Van Heertum AH, "Piperazin- und Piperidinderivate, Verfahren zu ihrer Herstellung und Arzneipräparate [Piperazine and piperide derivatives, procedures for their manufacturing and medicinal preparations]", published Script error: No such module "auto date formatter"., assigned to Janssen PharmaceuticaScript error: No such module "Check for unknown parameters".
- ↑ <templatestyles src="Citation/styles.css"/>Template:Citation/make link, Vandenberk J, Kennis LE, Van der Aa MJ, Van Heertum AH, issued Script error: No such module "auto date formatter"., assigned to Janssen Pharmaceutica NV.Script error: No such module "Check for unknown parameters".
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