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US 11,896,670 B2Granted
Synthesis routes to access MDMA prodrugs by using controlled and non-controlled intermediates
AssigneeMind Medicine, Inc.
InventorsDaniel Trachsel, Matthias Emanuel Liechti, Felix Lustenberger
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Abstract
A method of synthesizing a pharmacological compound substance by attaching a psychoactive base substance to an amino acid and creating a prodrug with modified pharmacological behavior. A prodrug made by the method. A pharmaceutical composition comprising a prodrug of a psychoactive base substance attached to an amino acid and a pharmaceutically acceptable salt.
Claims2
A method of synthesizing a pharmacological compound substance including the steps of:
- performing an aldol condensation on 3,4-dibenzyloxybenzaldehyde to obtain 1-(3,4-Dibenzyloxyphenyl)-2-nitropropene;
- dissolving 1-(3,4-Dibenzyloxyphenyl)-2-nitropropene in an inert solvent, adding the solution to a suspension of alane, and obtaining 3,4-Dibenzyloxyamphetamine hydrochloride;
- reacting 3,4-Dibenzyloxyamphetamine hydrochloride with an activated lysine derivative to obtain Boc-L-Lys(Boc)-3,4-dibenzyloxyamphetamine;
- dissolving Boc-L-Lys(Boc)-3,4-dibenzyloxyamphetamine in a solvent and performing a hydrogenolytic removal of O-benzyl groups to obtain Boc-L-Lys(Boc)-3,4-dihydroxyamphetamine;
- O,O′—methylating Boc-L-Lys(Boc)-3,4-dihydroxyamphetamine to obtain Boc-L-Lys(Boc)-3,4-methylenedioxyamphetamine;
- and
- performing a step chosen from the group consisting of
- (A) deprotecting Boc-L-Lys(Boc)-3,4-methylenedioxyamphetamine to obtain L-Lys-(R,S)-MDA, and
- (B) alkylating an amide nitrogen of Boc-L-Lys(Boc)-3,4-methylenedioxyamphetamine to obtain Boc-L-Lys(Boc)-3,4-methylenedioxymethamphetamine, and deprotecting Boc-L-Lys(Boc)-3,4-methylenedioxymethamphetamine to obtain L-Lys-(R,S)-MDMA.
6 more elements
A method of synthesizing a pharmacological compound substance including the steps of:
- reducing 1-(3,4-Dibenzyloxyphenyl)-2-nitropropene to a ketone 3,4-Dibenzyloxyphenylacetone;
- applying reductive amination conditions to 3,4-Dibenzyloxyphenylacetone to obtain 3,4-Dibenzyloxymethamphetamine hydrochloride;
- reacting 3,4-Dibenzyloxymethamphetamine hydrochloride with an activated lysine derivative to obtain Boc-L-Lys(Boc)-3,4-dibenzyloxymethamphetamine;
- performing a hydrogenolytic removal of O-benzyl groups on Boc-L-Lys(Boc)-3,4-dibenzyloxymethamphetamine to obtain Boc-L-Lys(Boc)-3,4-dihydroxymethamphetamine;
- O,O′—methylating Boc-L-Lys(Boc)-3,4-dihydroxymethamphetamine to obtain Boc-L-Lys(Boc)-3,4-methylenedioxymethamphetamine;
- and
- deprotecting Boc-L-Lys(Boc)-3,4-methylenedioxymethamphetamine to obtain L-Lys-(R,S)-MDMA.
4 more elements
Dependencies are inferred from the claim text.