Novel 4-amino-4-arylcyclohexanones and their ketals

Details Novel 4-amino-4-arylcyclohexanones and their ketals Novel 4-amino-4-arylcyclohexanones and their ketals

C - Chemistry, Metallurgy

07

D

260/351, 260/390

C07D 317/72 (2006.01) C07D 295/10 (2006.01) C07D 295/116 (2006.01) C07D 319/08 (2006.01) C07D 333/16 (2006.01) C07D 333/24 (2006.01)

Patent

CA 1093553

ABSTRACT OF THE DISCLOSURE A class of new 4-amino-4-arylcyclohexanones, their ketals, and acid addition salts have been synthesized and found to be useful for relieving pain in animals. Their analgesic activity appears to be of high order, and in addition some exhibit narcotic antagonist activity that is useful in modifying the cardiovascular, respiratory and behavioral depression caused by other analgesics. Several show mixed analgesic and narcotic antagonist activity. Preferred compounds of the class are 4-(m-hydroxyphenyl)-4- dimethylaminocyclohexanone ethylene ketal, and 4-(m-hydroxy- phenyl)-4-(n-butylmethylamino)cyclohexanone ethylene ketal as free bases and as their hydrochloride salts. Processes for synthesis and intermediates are described. Unit dosage forms and therapeutic treatments are disclosed. The compounds of the invention have the formula: Image Formula 1 wherein X is oxo, and Image wherein the substituents R1, R2, R3, R4 and R5 can be hydrogen or other substituents defined in the specification and n is zero or one.

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