Abstract:
DEXTRO-ROTATORY AND LEVO-ROTATORY ISOMERS OF N-ACYL-N(2''-PYRIDYL)-1-PIPERIDINO-2-AMINOPROPANES OF THE FORMULA:
2-(PIPERIDINO-CH2-CH(-CH3)-N(-CO-R)-)PYRIDINE
WHEREIN R IS METHYL OR ETHYL OR A PHARMACEUTICALLY ACCEPTABLE NON-TOXIC ACID SALT THEREOF EXHIBIT PHARMACEUTICAL PROPERTIES WHICH DIFFER QUALITATIVELY FROM THE RACEMATE. THE L-ISOMER EXHIBITS APPROXIMATELY THE SAME ANALGESIC ACTIVITY AS THE RACEMATE BUT ALSO EXHIBITS A STRONG SEDATIVE EFFECT. THE D-ISOMER EXHIBITS APPROXIMATELY THE SAME ANALGESIC ACTIVITY AS THE RACEMATE BUT EXHIBITS ALSO A CENTRAL NERVOUS SYSTEM STIMULANT EFFECT.
WHEREIN R is cyclopropylmethyl or cyclobutylmethyl; R'' and R'''' are the same or different, and are straight or branched chain hydrocarbons of 1 to 5 carbon atoms; X is OH, OR'''''' or
WHEREIN R'''''' is a straight or branched chain, saturated or unsaturated hydrocarbon of 1 to 11 carbon atoms; R4 and R5 are the same or different, and are hydrogen, straight or branched chain, saturated hydrocarbon of 1 to 4 carbon atoms, or R4 and R5 together with the nitrogen atom form a 5or 6-membered heterocyclic ring which may have oxygen as a second heteroatom; and A is a bivalent, straight or branched chain, saturated or unsaturated hydrocarbon of 1 to 10 carbon atoms or said hydrocarbon substituted by 1 or more phenyl moieties, or 1 or more phenyl moieties substituted by alkyl, alkoxy, halogen, nitro or acylamino, and PHARMACEUTICALLY ACCEPTABLE NON-TOXIC SALTS THEREOF ARE USEFUL AS ANALGESICS.