- 3-alkyl-3-phenyl-piperidines
-
PCT No. PCT/US97/15443 Sec. 371 Date Jan. 22, 1998 Sec. 102(e) Date Jan. 22, 1998 PCT Filed Sep. 2, 1997 PCT Pub. No. WO98/11090 PCT Pub. Date Mar. 19, 1998The small nonpeptides of the instant invention are tachykinin antagonists of formula or a pharmaceutically acceptable salt thereof wherein: R1 is straight or branched alkyl of from 5 to 15 carbon atoms, aryl, or heteroaryl; R2 is hydrogen, hydroxy, amino, or thiol; R3 is aryl, arylsulfonylmethyl, or saturated or unsaturated heterocycle; R4 is from 1 to 4 groups each independently selected from halogen, alkyl, hydroxy, and alkoxy; n is an integer of from 2 to 6; and the carbon atom of (CH2)n group can be replaced by oxygen, nitrogen, or sulphur. The compounds are highly selective and functional NK3 antagonists expected to be useful in the treatment of pain, depression, anxiety, panic, schizophrenia, neuralgia, addiction disorders, inflammatory diseases, gastrointestinal disorders, vascular disorders, and neuropathological disorders.
- -
-
-
- A practical and scalable synthesis of SR 142801, a tachykinin NK3 antagonist
-
A practical and scalable total synthesis of tachykinin NK3 receptor antagonist SR 142801, (R)-N-[1-[3-[1-benzoyl-3-(3,4-dichlorophenyl)-3-piperidinyl]propyl]-4-phenyl-4 -piperidinyl]-N-methyl acetamide 1 is described. The absolute configuration of the key intermediate 7 was determined by single crystal X-ray crystallography, on the basis of which, the absolute configuration of SR 142801 should be (R)-(+), instead of the recently reported (S)-(+).
- Chen, Huai G.,Chung,Goel,Johnson,Kesten,Knobelsdorf,Lee,Rubin
-
p. 555 - 560
(2007/10/03)
-
- A reliable and efficient synthesis of SR 142801
-
A convenient synthesis of the potent human NK-3 receptor antagonist SR 142801, (S)-(+)-N-{{3-[1-benzoyl-3-(3,4-dichlorophenyl)piperidin-3-yl]prop-1 -yl}-4-phenylpiperidin-4-yl}-N-methylacetamide [(S)-(+)-(15)], is described. Improvements over the previously reported procedure are the preparation of the intermediate 5 via the novel imide 3 and subsequent reaction with the nucleophile 14, which reacts, regioselectively, at the endocyclic nitrogen.
- Giardina,Grugni, Mario,Rigolio, Roberto,Vassallo, Marco,Erhard, Karl,Farina, Carlo
-
p. 2307 - 2310
(2007/10/03)
-