Tryptamine Prodrugs
The present invention provides a tryptamine prodrug compound. A compound represented by the formula (I) where each symbol is as described in the specification, or a salt or zwitterion thereof, is converted to an active which has 5HT2A receptor agonist activity, and is useful as an agent for the treatment of depression.
1 . A compound of Formula (I) (II), (III) or (IV) or a pharmaceutically acceptable salt or zwitterion thereof:
wherein:
(1) R1, R2, and R6 are each independently selected from hydrogen, linear or branched alkyl, or arylalkyl;
(2) R4 is
a. —X—CO2H, where X is a linear, cyclic or branched, saturated or unsaturated carbon chain, optionally substituted with —OH or —CO2H; or an aromatic ring, optionally substituted with alkyl or CO2H; or
b.
wherein R9 is X—CO2H, where X is as defined in (2)(a) above and R10 is hydrogen, linear or branched alkyl or arylalkyl, optionally substituted by —OH or —CO2H;
(3) R5 is hydrogen, linear or branched alkyl, arylalkyl, or O—R5′, where R5′ is hydrogen, linear or branched alkyl; and
(4) R7 and R8:
a. are each independently selected from hydrogen, linear or branched alkyl, or arylalkyl, or
b. together form a non-aromatic N-containing heterocycle, optionally substituted with alkyl.