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Novel amino adamantane compounds and 3-amino adamantane 1-carboxylic acids

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13.12.2006

All previously known synthesis procedures for the production of adamantane derivatives require drastic reaction conditions like, for example, the use of concentrated acids and high temperatures. Thus, the range of functional groups that can be introduced is starkly restricted. Above all, from the group of pharmacologically relevant 3-amino adamantane 1-carboxylic acids, only a few individual compounds of this chemical class are currently accessible. In contrast, the novel synthesis procedure enables the production of adamantane derivatives under mild reaction conditions and at lower temperatures. The syntheses are chemo- and regioselective, so that a multitude of functional groups can be selectively introduced. The production method of amino adamantane derivatives, based on the present invention, allows for the direct introduction of amido groups without prior halogenation and therewith offers an alternative to conventional methods. Further methods, based on the present invention, allow for the direct production of 5,7-substituted 3-amino adamantane 1-carboxylic acids, as well as their linkage to oligomers. Therapeutic uses of the novel compounds: antiviral agents, GABA modulation, components of peptide catalysts, artificial ion channels.

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