Verfahren zur Herstellung neuer 1-Cycloalkenylpiperidine

• Main Authors: LANGBEIN,ADOLF,DR, SCHROEDER,HANS-DETLEF,DR, MERZ,HERBERT,DR, ZEILE,KARL
• Format: Patent
• Language: German
• Published: 31.05.1969
• Edition: 1
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

Novel 1-cycloalkenyl-piperidines of the general formula <FORM:1078890/C2/1> wherein R1 represents a hydrogen, chlorine or bromine atom, R2 represents a hydrogen atom or an a - or b -methyl group, R3 represents a m- or p-hydroxy or a m- or p-methoxy group, R4 represents a methyl, ethyl, propyl, methoxy, ethoxy or propoxy group and n represents an integer from 1 to 4, and non-toxic acid addition salts thereof are prepared by reacting together a secondary piperidine and an alkylating agent of the corresponding formulae <FORM:1078890/C2/2> AND <FORM:1078890/C2/3> wherein Z represents a halogen atom, preferably bromine, or an O-tosyl group, and optionally converting to a non-toxic acid addition salt. Where a secondary piperidine in which R3 represents a m- or p-hydroxy group is used, the compound of the first general formula thus obtained can optionally be methylated to form a further compound of the first general formula wherein R3 represents a m- or p-methoxy group. Similarly, compounds of the first general formula in which R3 represents a m- or p-methoxy group can be demethylated to form corresponding compounds in which R3 represents a m- or p-hydroxy group.ALSO:Pharmaceutical compositions contain novel 1-cycloalkenyl-piperidines of the general formula <FORM:1078890/A5-A6/1> wherein R1 represents a hydrogen, chlorine or bromine atom, R2 represents a hydrogen atom or an a - or b -methyl group, R3 represents a m- or p-hydroxy or a m- or p-methoxy group R4 represents a methyl, ethyl, propyl, methoxy, ethoxy or propoxy group and n represents an integer from 1 to 4, and non-toxic acid addition salts thereof, which have a marked analgesic activity can be used as non-habit forming analgesics. The compositions may be used in conjunction with a habit-forming analgesic, such as morphine, pethidine or ketobemidone and/or a pharmaceutical carrier, and may be presented in a form suitable for oral, rectal or parenteral administration.