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Home TV Signal Intermediates-for-making-analgesic-N-phenyl-N-3-OR-sup-1-3-Me-4-piperidinyl-amides

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 Intermediates for making analgesic N-phenyl-N-(3-OR.sup.1 -3-Me-4-piperidinyl)amides

Details
Inventors: Feldman, Paul L.; Brackeen, Marcus F.;
Assignee: Glaxo Inc. (Research Triangle Park, NC)
Primary Examiner: Chang; Celia
Assistant Examiner:
Attorney, Agent or Firm: Harrington; R. Cole, Conte; Salvatore R.

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##

DETAILED DESCRIPTION OF THE INVENTION The invention relates to novel chemical compounds and pharmaceutical compositions and method of use thereof.
More particularly, the subject chemical compounds are N-aryl-N-(3-OR.
sup.
1 -3-Me-4-piperidinyl)amides represented by the formula: ##STR2## wherein: X is a member selected from Group I consisting of: alkoxy-carbonyl-lower alkyl (preferred), lower alkyl-carbonyloxy-lower alkyl, alkenyloxy-carbonyl-lower alkyl, and (C.
sub.
1-2)alkoxy-(C.
sub.
1-2)alkoxy-carbonyl-lower alkyl; and from Group II consisting of: lower alkyl, lower alkenyl, lower alkynyl, thienyl lower alkyl, aryl lower alkyl and (4,5-dihydro-5-oxo-1H-tetrazol-1-yl) lower alkyl which can be substituted in the 4-position with lower alkyl, cyclo(C.
sub.
5-6) lower alkyl or aryl lower alkyl; Ar is aryl; R is a member selected from the group consisting of lower alkyl, preferably ethyl, and lower alkoxy-lower alkyl, preferably methoxymethyl; and R.
sup.
1 is a member selected from the group consisting hydrogen and straight chained lower alkyl.
and the optically active and cis-trans isomers thereof, and the acid addition salts, preferably the pharmaceutically acceptable acid addition salts, of said compounds and isomers.
An additional aspect of the subject invention relates to certain novel intermediates which are useful in the synthesis of certain formula (I) compounds.
Said intermediates are represented by formula (A) wherein Z is a benzyloxy-carbonyl substituent on the ring nitrogen, replacing the aforementioned X-substituent in formula (I): ##STR3## As used in the foregoing definitions the term "lower" is meant to modify the so-indicated group by 1 to 4 carbons; the unmodified terms "alkoxy" and "alkenyl" are each meant to denote straight and branch chained hydrocarbons of from 1 to about 10 carbons and include the respective "lower" group of 1 to 4 carbons; the term "halo" is generic to halogens of atomic weight less than 127, i.
e.
fluoro (preferred), chloro, bromo, and iodo; and the term "aryl" denotes phenyl (preferred) and mono-, di- and tri-substituted phenyl, preferably monosubstituted in the 2-position, wherein each substituent is independently selected from the group consisting of halo, lower alkyl, lower alkoxy and trifluoromethyl



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