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The synthesis of (S)-di-n-propyl-(8-isoxazol-5-yl-1,2,3,4-tetrahydronaphthalen-2-yl)amine hydrochloride and its C-14-labeled isotopomer

✍ Scribed by William J. Wheeler; Douglas D. O'Bannon; Steven Swanson; Todd A. Gillespie; David L. Varie

Publisher
John Wiley and Sons
Year
2005
Tongue
French
Weight
163 KB
Volume
48
Category
Article
ISSN
0022-2135

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✦ Synopsis

The partial ergoline LY228729 (1) which was a potent 5HT 1A agonist has been studied clinically. Somewhat later, a related analog, (S)-di-n-propyl-(8-isoxazol-5-yl-1,2,3,4-tetrahydronaphthalen-2-yl)amine (2a) which in addition to potent 5HT 1A agonist activity was a muscarinic antagonist, was chosen for clinical development for use in the treatment of irritable bowel syndrome. In the course of pre-clinical evaluation of 2a, radiolabeled material was required for ADME studies. In this paper, we have discussed the preparation of 2a and 2b (the C-14-labeled isotopomer of 2a).

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