Diarylmethyl Piperazine Derivatives, Preparations Thereof and Uses Thereof
AssigneeAstraZeneca AB
InventorsWilliam Brown, Andrew Griffin, Thomas Hudzik, Carla Maciag, Gennady Smagin, Christopher Walpole
Life of this patent
Estimating the term…
Abstract
Compounds of general formula: as well as salts, enantiomers thereof and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain, depression and anxiety.
Claims19
A compound of formula I, pharmaceutically acceptable salts thereof, solvates thereof, prodrugs thereof, diastereomers thereof, one or more enantiomers thereof, and mixtures thereof:
7-8. (canceled)
A process for preparing a compound of formula I, comprising:
- reacting N,N-diethyl-4-[(3-nitrophenyl)(1-piperazinyl)methyl]benzamide with R—CH2X or R—CHO to form an intermediate compound;
- reducing said intermediate compound with a suitable reducing agent, wherein
- R is selected from 2-fluorophenyl, 3-fluorophenyl and 4-fluorophenyl;
- and
- X is selected from Cl, I, Br, —OTs (tosyl) and —OMs (mesylate).
A compound selected from enantiomerically pure 4-{(S)-(3-aminophenyl)[4-(4-fluorobenzyl)piperazin-1-yl]methyl}-N,N-diethylbenzamide;
- enantiomerically pure 4-{(R)-(3-aminophenyl)[4-(4-fluorobenzyl)piperazin-1-yl]methyl}-N,N-diethylbenzamide;
- enantiomerically pure 4-[(R)-(3-aminophenyl)[4-[(2-fluorophenyl)methyl]-1-piperazinyl]methyl]N,N-diethyl-benzamide;
- enantiomerically pure 4-[(R)-(3-aminophenyl)[4-[(3-fluorophenyl)methyl]-1-piperazinyl]methyl]N,N-diethyl-benzamide and pharmaceutically acceptable salts thereof.
Dependencies are inferred from the claim text.