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US4167574A Expired / Lapsed US ⏱️ 0.0 years remaining

N-phenyl-N-(4-piperidinyl)amides

Assignee: Janssen Pharmaceutica NV
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Filing: 1978-10-25
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Granted: 1979-09-11
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Expires: 1998-10-25
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Abstract

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.

Inventors

  • 👤 Frans Janssens

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-30 09:50
CPC Classifications
C; C07; C07D; C07D257/00; C07D257/02; C07D257/04; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/56; C07D211/58

Claims Analysis

Total Claims: 28
Claim 1
Independent Claim 233 words
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 1 is a member selected from the group consisting of hydrogen, lower alkyl and aryl; R 2 is a member selected from the group consisting of hydrogen and lower alkyl; R 3 is a member selected from the group consisting of lower alkyloxycarbonyl, lower alkyloxymethyl and lower alkylcarbonyl; R 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 5 is a member selected from the group consisting of hydrogen and lower alkyl; R 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.
Claim 2
Dependent Claim 233 words
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 1 is a member selected from the group consisting of hydrogen, lower alkyl and aryl; R 2 is a member selected from the group consisting of hydrogen and lower alkyl; R 3 is a member selected from the group consisting of lower alkyloxycarbonyl, lower alkyloxymethyl and lower alkylcarbonyl; R 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 5 is a member selected from the group consisting of hydrogen and lower alkyl; R 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.
Claim 3
Dependent Claim 18 words
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-(methoxymethyl)-4-piperidinyl}-N-phenylpropanamide and the pharmaceutically acceptable acid addition salts thereof.
Claim 4
Dependent Claim 18 words
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-(methoxymethyl)-4-piperidinyl}-N-phenylpropanamide and the pharmaceutically acceptable acid addition salts thereof.
Claim 5
Dependent Claim 19 words
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)phenylamino]-4-piperidinecarboxylate and the pharmaceutically acceptable acid addition salts thereof.
Claim 6
Dependent Claim 19 words
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)phenylamino]-4-piperidinecarboxylate and the pharmaceutically acceptable acid addition salts thereof.
Claim 7
Dependent Claim 19 words
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)methylamino]-4-piperidinecarboxylate and the pharmaceutically acceptable acid addition salts thereof.
Claim 8
Dependent Claim 19 words
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)methylamino]-4-piperidinecarboxylate and the pharmaceutically acceptable acid addition salts thereof.
Claim 9
Dependent Claim 19 words
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)phenylamino]-4-piperidinecarboxylate and the pharmaceutically acceptable acid addition salts thereof.
Claim 10
Dependent Claim 19 words
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)phenylamino]-4-piperidinecarboxylate and the pharmaceutically acceptable acid addition salts thereof.
Claim 11
Dependent Claim 18 words
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-(methoxymethyl)-4-piperidinyl}-N-phenylpropanamide and the pharmaceutically acceptable acid addition salts thereof.
Claim 12
Dependent Claim 18 words
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-(methoxymethyl)-4-piperidinyl}-N-phenylpropanamide and the pharmaceutically acceptable acid addition salts thereof.
Claim 13
Dependent Claim 18 words
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-(methoxymethyl)-4-piperidinyl}-N-phenylpropanamide and the pharmaceutically acceptable acid addition salts thereof.
Claim 14
Dependent Claim 18 words
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-(methoxymethyl)-4-piperidinyl}-N-phenylpropanamide and the pharmaceutically acceptable acid addition salts thereof.
Claim 15
Dependent Claim 250 words
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 1 is a member selected from the group consisting of hydrogen, lower alkyl and aryl; R 2 is a member selected from the group consisting of hydrogen and lower alkyl; R 3 is a member selected from the group consisting of lower alkyloxycarbonyl, lower alkyloxymethyl and lower alkylcarbonyl; R 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 5 is a member selected from the group consisting of hydrogen and lower alkyl; R 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.
Claim 16
Dependent Claim 250 words
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 1 is a member selected from the group consisting of hydrogen, lower alkyl and aryl; R 2 is a member selected from the group consisting of hydrogen and lower alkyl; R 3 is a member selected from the group consisting of lower alkyloxycarbonyl, lower alkyloxymethyl and lower alkylcarbonyl; R 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 5 is a member selected from the group consisting of hydrogen and lower alkyl; R 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.
Claim 17
Dependent Claim 35 words
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-(methoxymethyl)-4-piperidinyl}-N-phenylpropanamide and the pharmaceutically acceptable acid addition salts thereof.
Claim 18
Dependent Claim 35 words
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-(methoxymethyl)-4-piperidinyl}-N-phenylpropanamide and the pharmaceutically acceptable acid addition salts thereof.
Claim 19
Dependent Claim 36 words
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)phenylamino]-4-piperidinecarboxylate and the pharmaceutically acceptable acid addition salts thereof.
Claim 20
Dependent Claim 36 words
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)phenylamino]-4-piperidinecarboxylate and the pharmaceutically acceptable acid addition salts thereof.
Claim 21
Dependent Claim 36 words
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)phenylamino]-4-piperidinecarboxylate and the pharmaceutically acceptable acid addition salts thereof.
Claim 22
Dependent Claim 36 words
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)phenylamino]-4-piperidinecarboxylate and the pharmaceutically acceptable acid addition salts thereof.
Claim 23
Dependent Claim 36 words
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)phenylamino]-4-piperidinecarboxylate and the pharmaceutically acceptable acid addition salts thereof.
Claim 24
Dependent Claim 36 words
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)phenylamino]-4-piperidinecarboxylate and the pharmaceutically acceptable acid addition salts thereof.
Claim 25
Dependent Claim 35 words
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-(methoxymethyl)-4-piperidinyl}-N-phenylpropanamide and the pharmaceutically acceptable acid addition salts thereof.
Claim 26
Dependent Claim 35 words
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-(methoxymethyl)-4-piperidinyl}-N-phenylpropanamide and the pharmaceutically acceptable acid addition salts thereof.
Claim 27
Dependent Claim 35 words
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-(methoxymethyl)-4-piperidinyl}-N-phenylpropanamide and the pharmaceutically acceptable acid addition salts thereof.
Claim 28
Dependent Claim 35 words
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-(methoxymethyl)-4-piperidinyl}-N-phenylpropanamide and the pharmaceutically acceptable acid addition salts thereof.

References Cited (Backward Citations)

US3998834A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-09-10 1983-03-12 1983-09-11 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-09-10 1987-03-12 1987-09-11 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-09-10 1991-03-12 1991-09-11 $7700.00 Window Closed / Lapsed

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