New chiral and isomeric cyclopropyl ketoxime propanolamine derivatives with potent beta-adrenergic blocking properties.
The synthesis of R-(+) and S-(-) isomers of O-[3-tert-butylamino)-2-hydroxypropyl] cyclopropyl methyl ketone oxime (falintolol) is described. The syn and anti isomers of falintolol were obtained in two different ways from cyclopropyl methyl ketoxime or from falintolol. For comparison purposes, the enantiomers of the dicyclopropyl ketone oxime derivatives were also prepared. Structure-activity relationships are described.
Bouzoubaa
M
M
Leclerc
G
G
Rakhit
S
S
Andermann
G
G
D000319:Adrenergic beta-Antagonists / Q000494:pharmacology*; D000818:Animals; D016275:Atrial Function; D001681:Biological Assay; D006168:Guinea Pigs; D007536:Isomerism; D009119:Muscle Contraction / Q000187:drug effects; D009200:Myocardial Contraction / Q000187:drug effects; D011412:Propanolamines / Q000138:chemical synthesis / Q000494:pharmacology*; D011943:Receptors, Adrenergic, beta / Q000187:drug effects / Q000502:physiology; D013329:Structure-Activity Relationship; D014132:Trachea / Q000502:physiology
D000319:Adrenergic beta-Antagonists; D011412:Propanolamines; D011943:Receptors, Adrenergic, beta; C045888:falintolol