Methods and compositions for preparing and purifying noribogaine

a technology of alkaloids and compositions, applied in the field of methods and compositions for purifying the nonaddictive alkaloids of noribogaine, can solve the problems that the one-step method for preparing noribogaine from ibogaine via demethylation does not provide the requisite assurance that ibogaine will be consistently removed, and achieve the effect of reducing the probability of contamination by ibogain

Active Publication Date: 2014-07-03
DEMERX
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  • Abstract
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  • Application Information

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Problems solved by technology

As above, a one-step method for preparation of noribogaine from ibogaine via demethylation does not provide the requisite assurance that ibogaine will consistently be removed as a potential contaminant.

Method used

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  • Methods and compositions for preparing and purifying noribogaine
  • Methods and compositions for preparing and purifying noribogaine
  • Methods and compositions for preparing and purifying noribogaine

Examples

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example 1

Synthesis and Purification of Noribogaine from Ibogaine

[0055]Example 1 illustrates one method for the synthesis and purification of noribogaine from ibogaine which method follows Scheme 4 below:

[0056]Specifically, in Scheme 4, ibogaine is contacted with a stoichiometric excess of benzyl chloroformate in an inert solvent such as methylene chloride. The reaction mixture further contains at least a stoichiometric equivalent of diisopropylethylamine relative to ibogaine so as to scavenge the acid generated during the reaction. The reaction is maintained at room temperature under an inert atmosphere until the reaction is substantially complete as evidenced by, for example, thin layer chromatograpy. At which time, an O-demethylation reagent (e.g. boron tribromide, aluminum trichloride, or lithium diphenylphosphine), or preferably a stoichiometric excess thereof, is added to the reaction mixture which is then maintained under conditions (e.g. room temperature) wherein the methoxy group of ...

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Abstract

Disclosed are methods and compositions for purifying the non-addictive alkaloid noribogaine.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application claims priority under 35 U.S.C. §119(e) to U.S. Provisional Patent Application Ser. No. 61 / 333,476, filed on May 11, 2010, and to U.S. Provisional Patent Application Ser. No. 61 / 419,772, filed on Dec. 3, 2010, both of which applications are incorporated by reference herein in their entirety.FIELD OF THE INVENTION[0002]This invention relates generally to methods and compositions for purifying the non-addictive alkaloid noribogaine.STATE OF THE ART[0003]Noribogaine is a well known derivative of ibogaine and is sometimes referred to as 12-hydroxyibogaine. It is a metabolite of ibogaine. U.S. Pat. No. 2,813,873 claims noribogaine albeit as “12-O-demethylibogaine” while providing an incorrect structural formula for ibogaine. The structure of noribogaine has now been thoroughly evaluated and is found to combine the features of tyrptamine, tetrahydrohavaine and indolazepines. Noribogaine can be depicted by the following formula:...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07D487/18B01J41/14
CPCC07D471/22
Inventor MASH, DEBORAH C.GLESS, JR., RICHARD D.
Owner DEMERX
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