Piperidine derivatives of 1-hydrocarbyl-4-alkenylene-isonipecotic acid esters

• Main Authors: DENSS ROLF, KUHNIS HANS HERBERT
• Format: Patent
• Language: English
• Published: 29.08.1967
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

Novel piperidine derivatives having the formula <FORM:1116326/C2/1> wherein R1 represents a C1- 8 alkyl or C2- 8 alkenyl radical, the cyclohexyl radical or a C7- 9 phenylalkyl radical, R2, R3, R4 and R5 each independently represent hydrogen or methyl radicals and R6-CO- represents the acetyl or propionyl radical and their salts with inorganic and organic acids are obtained (1) by reacting compounds of the formula <FORM:1116326/C2/2> wherein X represents hydrogen, a monovalent cation e.g. the -Mg-halogen ion or the normal equivalent of a polyvalent cation with reactive functional derivatives, e.g. anhydrides, of carboxylic acids R6-CO-OH or, when X is a hydrogen atom, with the free acids or the corresponding ketens; or (2), when R4 represents hydrogen, by hydrogenating the corresponding acetylenic piperidine derivatives in the presence of a suitable catalyst until the equimolar amount of hydrogen has been taken up, and if desired, converting the compounds into salts with inorganic or organic acids. The 4-piperidinol derivative used in (1) may be obtained by reacting a 4-piperidone with a metal-organic compound which contains an alkenyl radical -R5CH = CR4-CHR3- and, if desired, hydrolysing the product. Therapeutic compositions having antitussive and analgetic properties contain as the active ingredient the above piperidine derivatives or their pharmaceutically acceptable salts with inorganic or organic acids. The composition may be in a form suitable for oral, parenteral or rectal application.