An improved synthesis of enantiomerically pure RWJ 69442, a development candidate for the treatment of benign prostatic hyperplasia

Citation
Gh. Kuo et al., An improved synthesis of enantiomerically pure RWJ 69442, a development candidate for the treatment of benign prostatic hyperplasia, J HETERO CH, 38(4), 2001, pp. 1003-1006
Citations number
12
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022-152X → ACNP
Volume
38
Issue
4
Year of publication
2001
Pages
1003 - 1006
Database
ISI
SICI code
0022-152X(200107/08)38:4<1003:AISOEP>2.0.ZU;2-A
Abstract
This report describes an improved synthesis of enantiomerically pure (S)-2- [4-(Dimethylamino)phenyl]-2,3-dihydro-N-[2-hydroxy-3-[4-[2-(1-methylethoxy) -phenyl]-1-piperazinyl]propyl]-1,3-dioxo-1H-isoindole-5-carboxamide (RWJ 69 442), a potent and selective alpha (1a)-adrenergic receptor antagonist for the treatment of benign prostatic hyperplasia. The synthesis highlights les s hazardous reagents, easier purification and higher enantiomeric purity. T he N-benzyl-N-t-butoxycarbonyl amine 6 could serve as an enantiomerically p ure chiral building block for asymmetric synthesis.