Two series of cycloalkyl analogues of Antergan have been synthesized and analyzed. The compounds of the first series have the basic structure of N, N-dimethyl-N¹-phenyl-N¹ -(cycloalkylmethyl)-ethylenediamine in which the alkyl group was a propyl-, butyl-, pentyl-, hexyl-, or heptyl- ring structure. The second series of dicycloalkyl analogues has the general formula of N, N-dimethyl-N¹-cycloalkyl-N¹-(cycloalkylmethyl)-ethylenediamine in which both alkyl groups of propyl-, pentyl-, hexyl-, or heptyl- were the same ring size. Hydrochloride, picrate, and methyl iodide salts were prepared for these diamines, and for a number of the intermediates.
In both series, the general reaction sequence followed was to start with the appropriate cycloalkyl carboxylic acid and build up to a secondary amine via an acid chloride and amide. The desired amine was then condensed with β-dimethylaminoethylbromide hydrobromide to form the tertiary diamine analogue. Two compounds, the dicyclohexyl- and dicycloheptyl-analogues, were formed by condensing the cycloalkylcarbonyl chloride with a substituted secondary ethylenediamine, and then reducing the amide with lithium aluminum hydride.
Attempts to synthesize a sufficient quantity of the cyclo-octanecarboxanilide intermediate were unsuccessful. Difficulty was also encountered in preparing a stable and pure salt derivative for a number of the dicycloalkyl analogues.
Signature of Examiners / Pharmaceutical Sciences, Faculty of / Graduate
| Identifer | oai:union.ndltd.org:UBC/oai:circle.library.ubc.ca:2429/38000 |
| Date | January 1964 |
| Creators | Leung, Fred Ying Toy |
| Publisher | University of British Columbia |
| Source Sets | University of British Columbia |
| Language | English |
| Detected Language | English |
| Type | Text, Thesis/Dissertation |
| Rights | For non-commercial purposes only, such as research, private study and education. Additional conditions apply, see Terms of Use https://open.library.ubc.ca/terms_of_use. |
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