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1. WO1996002513 - OPTICALLY ACTIVE ISOMERS OF DIHYDREXIDINE AND ITS SUBSTITUTED ANALOGS

Publication Number WO/1996/002513
Publication Date 01.02.1996
International Application No. PCT/US1995/008598
International Filing Date 10.07.1995
Chapter 2 Demand Filed 08.02.1996
IPC
C07D 221/18 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
221Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/-C07D219/187
02condensed with carbocyclic rings or ring systems
04Ortho- or peri-condensed ring systems
18Ring systems of four or more rings
CPC
C07D 221/18
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
221Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
02condensed with carbocyclic rings or ring systems
04Ortho- or peri-condensed ring systems
18Ring systems of four or more rings
Y02P 20/55
YSECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
20Technologies relating to chemical industry
50Improvements relating to the production of products other than chlorine, adipic acid, caprolactam, or chlorodifluoromethane, e.g. bulk or fine chemicals or pharmaceuticals
55Synthetic design, e.g. reducing the use of auxiliary or protecting groups
Applicants
  • PURDUE RESEARCH FOUNDATION [US/US]; Room 100 1022 Hovde Hall West LaFayette, IN 47907, US
  • UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL [US/US]; CB 4100 Bynum Hall Chapel Hill, NC 27599-4100, US
Inventors
  • NICHOLS, David, E.; US
  • MAILMAN, Richard, B.; US
Agents
  • VILLACORTA, Gilberto, M. ; Lowe, Price, LeBlanc & Becker Suite 300 99 Canal Center Plaza Alexandria, VA 22314, US
Priority Data
08/275,34215.07.1994US
Publication Language English (EN)
Filing Language English (EN)
Designated States
Title
(EN) OPTICALLY ACTIVE ISOMERS OF DIHYDREXIDINE AND ITS SUBSTITUTED ANALOGS
(FR) ISOMERES OPTIQUEMENT ACTIFS DE LA DIHYDREXIDINE ET DE SES ANALOGUES SUBSTITUES
Abstract
(EN)
Optically active hexahydrobenzo[$i(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 $i(trans)-hexahydrobenzo[a]phenanthridines into their component enantiomers is also disclosed. Pharmacological evidence reveals that only one of the enantiomers of a preferred phenanthridine, dihydrexidine, the (6a$i(R), 12b$i(S))-(+)-isomer, is active in binding to both D1-like and D2-like dopamine receptors. Various other compounds, compositions, and methods of using the optically active stereoisomers are likewise disclosed.
(FR)
L'invention concerne des hexahydrobenzo[$i(a)]phénanthridines optiquement actives de la formule (I). Dans cette formule, R est un hydrogène ou un C1-C4 alkyle; R1 est un hydrogène ou un groupe protecteur du phénol, X est un fluoro, un chloro, un bromo, un iodo ou un groupe de la formule OR5; R2, R3 et R4 sont choisis d'une manière indépendante dans le groupe constitué par l'hydrogène, C1-C4 alkyle, phényle, fluoro, chloro, bromo, iodo ou un groupe -OR1. On décrit également un procédé pour fractionner le mélange racémique de $i(trans)-hexahydrobenzo[$i(a)]phénanthridines en composants énantiomères. Les études pharmacologiques montrent qu'un seul des enantiomères d'une phénanthridine préférée, la dihydrexidine, en l'occurrence l'isomère (6a$i(R), 12b$i(S))-(+) se fixe activement simultanément aux récepteurs de la dopamine du type D1 et du type D2. On décrit également différents autres composés, ainsi que des compositions et des procédés d'utilisation des stéréoisomères optiquement actifs.
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