Glaxo Inc.

Marcus F Brackeen

Paul L Feldman

Michael Ross Johnson

Harry J Leighton

Michael K James

Novel piperidinyl intermediates as set forth below wherein R, R.sup.1 and Ar are as set forth in the specification and W is either hydrogen or benzyloxycarbonyl. The intermediates are useful in the preparation of N-phenyl-N-(4-piperidinyl) amides having potent analgesic activity. ##STR1##

Intermediates for making analgesic N-phenyl-N-(3-OR.sup.1

N-Phenyl-N-(4-piperdinyl)amide derivatives are disclosed having the general formula (I): ##STR1## wherein X, Ar, R and R.sup.1 are defined, including isomeric forms thereof and acid addition salts thereof. The compounds exhibit analgesic activity. The invention embraces the compounds (I), pharmaceutical compositions of (I) and methods of providing analgesia with (I). Also included are certain novel intermediates for making (I).

Analgesic N-phenyl-N-(3-OR.sub.1 -3-ME-4-piperidinyl)amides

Analgesic n-phenyl-n-(3-or 1-3-me-4-piperidinyl)amides

A method of preparing certain substituted alkali metal 4-carboxy-piperidine salts (I) by alkaline hydrolysis of certain novel substituted 1,3,8-triazaspiro[4.5]decane-2, 4-diones (IV) which in turn are obtained from certain novel substituted chlorosulphonylamido piperidines (III).

Preparation of substituted alkali metal piperidine-4-carboxylates

N-Phenyl-N-(4-piperdinyl)amide derivatives are disclosed having the general formula (I): ##STR1## wherein X is a member selected from the group consisting of alkoxy-carbonyl-lower alkyl, lower alkyl-carbonyloxy-lower alkyl, alkenyloxy-carbonyl-lower alkyl, and (C.sub.1-2)alkoxy-(C.sub.1-2)-alkoxy-carbonyl-lower alkyl, and Ar, R, R.sup.1 and R.sup.2 are defined hereinafter, including isomeric forms thereof and acid addition salts thereof. The compounds exhibit analgesic activity having relatively short durations of analgesic action. The invention embraces the compounds (I), pharmaceutical compositions of (I) and methods of providing analgesia with (I). Also included are certain novel intermediates for making (I).

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Durham, NC, United States of America

Marcus F Brackeen