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Generated: August 22, 2017

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Title: N-phenyl-N-(4-piperidinyl)amides
Abstract:Novel compounds of the series of N-phenyl-N-(4-piperidinyl)amides having a (4,5-dihydro-4-R-5-oxo-1H-tetrazol-1-yl)alkyl or (4,5-dihydro-4-R-5-thioxo-1H-tetrazol-1-yl)alkyl substituent group in the 1-position of the piperidine nucleus, said compounds being useful as analgesic agents.
Inventor(s): Janssens; Frans (Putte, BE)
Assignee: Janssen Pharmaceutica, N.V. (BE)
Application Number:05/954,709
Patent Claims: 1. A chemical compound selected from the group consisting of a N-phenyl-N-(4-piperidinyl)amide derivative having the formula: ##STR23## and the pharmaceutically acceptable acid addition salts thereof, wherein:

R is a member selected from the group consisting of hydrogen, lower alkyl, cycloalkyl, having 3 to 6 ring carbon atoms lower alkenyl, lower alkynyl, (lower alkyl)oxy(lower alkyl), aryl and aryl(lower alkyl);

R.sup.1 is a member selected from the group consisting of hydrogen, lower alkyl and aryl;

R.sup.2 is a member selected from the group consisting of hydrogen and lower alkyl;

R.sup.3 is a member selected from the group consisting of lower alkyloxycarbonyl, lower alkyloxymethyl and lower alkylcarbonyl;

R.sup.4 is a member selected from the group consisting of lower alkyl, cycloalkyl, having 3 to 6 ring carbon atoms lower alkenyl, lower alkyloxy and arylmethyl;

R.sup.5 is a member selected from the group consisting of hydrogen and lower alkyl;

R.sup.6 is a member selected from the group consisting of hydrogen, halo, lower alkyl, lower alkyloxy and trifluoromethyl;

Z is a member selected from the group consisting of O and S; and

n is the integer 0 or 1;

wherein said aryl as used in the foregoing definitions is selected from the group consisting of phenyl, substituted phenyl, thienyl and pyridinyl, said substituted phenyl having from 1 to 2 substituents independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, and trifluoromthyl.

2. A chemical compound selected from the group consisting of N-{1-[2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl]-4-(methoxymethy l)-4-piperidinyl}-N-phenylpropanamide and the pharmaceutically acceptable acid addition salts thereof.

3. A chemical compound selected from the group consisting of methyl 1-[2-(4,5-dihydro-4-methyl-5-oxo-1H-tetrazol-1-yl)ethyl]-4-[(1-oxopropyl)p henylamino]-4-piperidinecarboxylate and the pharmaceutically acceptable acid addition salts thereof.

4. A chemical compound selected from the group consisting of methyl 1-[2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl]-4-[(1-oxopropyl)me thylamino]-4-piperidinecarboxylate and the pharmaceutically acceptable acid addition salts thereof.

5. A chemical compound selected from the group consisting of methyl 1-[2-(4,5-dihydro-5-oxo-4-propyl-1H-tetrazol-1-yl)ethyl]-4-[(1-oxopropyl)p henylamino]-4-piperidinecarboxylate and the pharmaceutically acceptable acid addition salts thereof.

6. A chemical compound selected from the group consisting of N-{1-[2-(4,5-dihydro-4-methyl-5-oxo-1H-tetrazol-1-yl)ethyl]-4-(methoxymeth yl)-4-piperidinyl}-N-phenylpropanamide and the pharmaceutically acceptable acid addition salts thereof.

7. A chemical compound selected from the group consisting of N-{1-[2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)-1-methylethyl]-4-(met hoxymethyl)-4-piperidinyl}-N-phenylpropanamide and the pharmaceutically acceptable acid addition salts thereof.

8. A pharmaceutical composition comprising an inert carrier material and as an active ingredient an effective analgesic amount of a compound selected from the group consisting of a N-phenyl-N-(4-piperidinyl)amide derivative having the formula: ##STR24## and the pharmaceutically acceptable acid addition salts thereof, wherein: R is a member selected from the group consisting of hydrogen, lower alkyl, cycloalkyl, having 3 to 6 ring carbon atoms lower alkenyl, lower alkynyl, (lower alkyl)oxy(lower alkyl), aryl and aryl(lower alkyl);

R.sup.1 is a member selected from the group consisting of hydrogen, lower alkyl and aryl;

R.sup.2 is a member selected from the group consisting of hydrogen and lower alkyl;

R.sup.3 is a member selected from the group consisting of lower alkyloxycarbonyl, lower alkyloxymethyl and lower alkylcarbonyl;

R.sup.4 is a member selected from the group consisting of lower alkyl, cycloalkyl, having 3 to 6 ring carbon atoms lower alkenyl, lower alkyloxy and arylmethyl;

R.sup.5 is a member selected from the group consisting of hydrogen and lower alkyl;

R.sup.6 is a member selected from the group consisting of hydrogen, halo, lower alkyl, lower alkyloxy and trifluoromethyl;

Z is a member selected from the group consisting of O and S; and

n is the integer 0 or 1;

wherein said aryl as used in the foregoing definitions is selected from the group consisting of phenyl, substituted phenyl, thienyl and pyridinyl, said substituted phenyl having from 1 to 2 substituents independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, and trifluoromethyl.

9. A pharmaceutical composition comprising an inert carrier material and as an active ingredient an effective analgesic amount of a compound selected from the group consisting of N-{1-[2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl]-4-(methoxymethy l)-4-piperidinyl}-N-phenylpropanamide and the pharmaceutically acceptable acid addition salts thereof.

10. A pharmaceutical composition comprising an inert carrier material and as an active ingredient an effective analgesic amount of a compound selected from the group consisting of methyl 1-[2-(4,5-dihydro-4-methyl-5-oxo-1H-tetrazol-1-yl)ethyl]-4-[(1-oxopropyl)p henylamino]-4-piperidinecarboxylate and the pharmaceutically acceptable acid addition salts thereof.

11. A pharmaceutical composition comprising an inert carrier material and as an active ingredient an effective analgesic amount of a compound selected from the group consisting of methyl 1-[2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)ethyl]-4-[(1-oxopropyl)ph enylamino]-4-piperidinecarboxylate and the pharmaceutically acceptable acid addition salts thereof.

12. A pharmaceutical composition comprising an inert carrier material and as an active ingredient an effective analgesic amount of a compound selected from the group consisting of methyl 1-[2-(4,5-dihydro-5-oxo-4-propyl-1H-tetrazol-1-yl)ethyl]-4-[(1-oxopropyl)p henylamino]-4-piperidinecarboxylate and the pharmaceutically acceptable acid addition salts thereof.

13. A pharmaceutical composition comprising an inert carrier material and as an active ingredient an effective analgesic amount of a compound selected from the group consisting of N-{1-[2-(4,5-dihydro-4-methyl-5-oxo-1H-tetrazol-1-yl)ethyl]-4-(methoxymeth yl)-4-piperidinyl}-N-phenylpropanamide and the pharmaceutically acceptable acid addition salts thereof.

14. A pharmaceutical composition comprising an inert carrier material and as an active ingredient an effective analgesic amount of a compound selected from the group consisting of N-{1-[2-(4-ethyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)-methylethyl]-4-(metho xymethyl)-4-piperidinyl}-N-phenylpropanamide and the pharmaceutically acceptable acid addition salts thereof.
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