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Later work
editUS Patent 4148907 shows that replacing the -Cl with a -F or -CF3 leads to compounds that are over twice as potent but 50% less toxic. US Patent 4960788 (Zambon) are pyrollidone analogues, some of which are several hundred times more potent than morphine (compound 1 - (1S)-1-[(5S)-1-[(2-chlorophenyl)methyl]-2-oxo -5-pyrrolidinyl]-2-[(2R,2'R)-disec.butylamino]ethanol) ED50 0.011mg/kg to Morphine 3.5mg/kg. — Preceding unsigned comment added by 86.30.243.179 (talk) 15:32, 16 July 2011 (UTC)
Analogues
editThe papers that dealt with the Cl->F/CF3 used chiral amines so they are full agonists. — Preceding unsigned comment added by 81.99.74.135 (talk) 11:35, 13 March 2017 (UTC)
N Substitution
editI have tried but failed to find why the chiral (R,R)-Disec butyl N-substitution is so very specific. The Pyrrolidone derivative proves that the ring nitrogen doesn't have to be basic. Sadly, nobody has reported on the effects (if any) of adding a 5-methyl to the pyrrolidine ring. Obviously, even the potent analogue is never going be produced, even if it's still legal. The resolution of the active compound is far, far too complex BUT it's useful to students to see how compounds overlay in ChemOffice. — Preceding unsigned comment added by 81.99.74.135 (talk) 18:21, 10 April 2017 (UTC)