EP 0773933 A1 19970521 - OPTICALLY ACTIVE ISOMERS OF DIHYDREXIDINE AND ITS SUBSTITUTED ANALOGS
Title (en)
OPTICALLY ACTIVE ISOMERS OF DIHYDREXIDINE AND ITS SUBSTITUTED ANALOGS
Title (de)
OPTISCH AKTIVE ISOMERE DES DIHYDREXIDIN UND SUBSTITUIERTE ANALOGE DAVON
Title (fr)
ISOMERES OPTIQUEMENT ACTIFS DE LA DIHYDREXIDINE ET DE SES ANALOGUES SUBSTITUES
Publication
Application
Priority
- US 9508598 W 19950710
- US 27534294 A 19940715
Abstract (en)
[origin: WO9602513A1] Optically active hexahydrobenzo[a]phenanthridines of formula (I) wherein R is hydrogen or C1-C4 alkyl; R1 is hydrogen or a phenol protecting group, X is fluoro, chloro, bromo, iodo or a group of the formula OR5, and R2, R3, and R4 are independently selected from the group consisting of hydrogen, C1-C4alkyl, phenyl, fluoro, chloro, bromo, iodo, or a group -OR1 are disclosed. The method of resolving the racemic trans-hexahydrobenzo[a]phenanthridines into their component enantiomers is also disclosed. Pharmacological evidence reveals that only one of the enantiomers of a preferred phenanthridine, dihydrexidine, the (6aR, 12bS)-(+)-isomer, is active in binding to both D1-like and D2-like dopamine receptors. Various other compounds, compositions, and methods of using the optically active stereoisomers are likewise disclosed.
IPC 1-7
IPC 8 full level
A61K 31/47 (2006.01); A61K 31/473 (2006.01); A61P 25/00 (2006.01); C07D 221/18 (2006.01)
CPC (source: EP)
A61P 25/00 (2017.12); C07D 221/18 (2013.01); Y02P 20/55 (2015.11)
Citation (search report)
See references of WO 9602513A1
Designated contracting state (EPC)
AT BE CH DE DK ES FR GB GR IE IT LI LU MC NL PT SE
DOCDB simple family (publication)
WO 9602513 A1 19960201; AU 2966795 A 19960216; CA 2195239 A1 19960201; EP 0773933 A1 19970521; IL 114608 A0 19951127; JP H10502923 A 19980317; ZA 955931 B 19960126
DOCDB simple family (application)
US 9508598 W 19950710; AU 2966795 A 19950710; CA 2195239 A 19950710; EP 95925584 A 19950710; IL 11460895 A 19950714; JP 50508596 A 19950710; ZA 955931 A 19950717