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US4547514A Expired / Lapsed US ⏱️ 0.0 years remaining

Aryloxy-N-(aminoalkyl)-1-pyrrolidine and piperidine carboxamides and carbothioamides having antiarrhythmic activity

Assignee: AH Robins Co Inc
•
Filing: 1983-12-05
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Granted: 1985-10-15
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Expires: 2003-12-05
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Abstract

Abstract Pharmaceutical compositions comprised of aryloxy-N-(aminoalkyl)-1-pyrrolidine and piperidine carboxamides and carbothioamides are provided of the formula: ##STR1## wherein Ar is selected from the group consisting of 1-naphthyl, 2-naphthyl, 2,3-dihydro-1H-inden-4-yl, 2,3-dihydro-1H-inden-5-yl, phenyl, substituted phenyl wherein the substituents are selected from lower alkyl of from 1 to 8 carbon atoms, lower alkyloxy of from 1 to 8 carbon atoms, halogen and trifluoromethyl; m and n are 1 or 2 but are never 2 at the same time; p is 1, 2, 3 or 4; R is selected from hydrogen or lower alkyl of from 1 to 3 carbon atoms; R 1 and R 2 are selected from hydrogen, lower alkyl of from 1 to 8 carbon atoms, phenyl, phenyl lower alkyl of from 7 to 9 carbon atoms, and cycloalkyl of from 3 to 8 carbon atoms, and R 1 and R 2 taken together with the adjacent atom may form a heterocyclic residue selected from 4-morpholino, 1-pyrrolidino, 1-piperidino, 1-piperazino and 4-lower alkyl piperazin-1-yl; X is oxygen or sulfur; and the pharmaceutically acceptable acid addition salts thereof having antiarrhythmic activity.

Inventors

  • 👤 Pershottam P. Mathur
  • 👤 William L. Smith

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 03:53
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/40; A; A61; A61P; A61P9/00; A61P9/06; C07D207/00; C07D207/02; C07D207/04; C07D207/10; C07D207/12; C07D211/42; C07D211/44; C07D211/46

Claims Analysis

Total Claims: 22
Claim 1
Independent Claim 185 words
A method for the treatment of cardiac arrhythmia in a patient consisting essentially of administering a cardiac arrhythmia inhibiting quantity of a compound of the formula: ##STR18## wherein Ar is selected from the group consisting of 1-naphthyl, 2-naphahyl, 2,3-dihydro-1H-inden-4-yl, 2,3-dihydro-1H-inden-5-yl, phenyl, substituted phenyl wherein the substituents are selected from lower alkyl of from 1 to 8 carbon atoms, lower alkyloxy of from 1 to 8 carbon atoms, halogen and trifluoromethyl; m and n are 1 or 2 but are never 2 at the same time; p is 1, 2, 3 or 4; R is selected from hydrogen or lower alkyl of from 1 to 3 carbon atoms; R 1 and R 2 are selected from hydrogen, lower alkyl of from 1 to 8 carbon atoms, phenyl, phenyl lower alkyl of from 7 to 9 carbon atoms, and cycloalkyl of from 3 to 8 carbon atoms, and R 1 and R 2 taken together with the adjacent atom may form a heterocyclic residue selected from 4-morpholino, 1-pyrrolidino, 1-piperidino, 1-piperazino and 4-lower alkyl piperazin-1-yl; X is oxygen or sulfur; and the pharmaceutically acceptable acid addition salts thereof.
Claim 2
Independent Claim 185 words
A method for the treatment of cardiac arrhythmia in a patient consisting essentially of administering a cardiac arrhythmia inhibiting quantity of a compound of the formula: ##STR18## wherein Ar is selected from the group consisting of 1-naphthyl, 2-naphahyl, 2,3-dihydro-1H-inden-4-yl, 2,3-dihydro-1H-inden-5-yl, phenyl, substituted phenyl wherein the substituents are selected from lower alkyl of from 1 to 8 carbon atoms, lower alkyloxy of from 1 to 8 carbon atoms, halogen and trifluoromethyl; m and n are 1 or 2 but are never 2 at the same time; p is 1, 2, 3 or 4; R is selected from hydrogen or lower alkyl of from 1 to 3 carbon atoms; R 1 and R 2 are selected from hydrogen, lower alkyl of from 1 to 8 carbon atoms, phenyl, phenyl lower alkyl of from 7 to 9 carbon atoms, and cycloalkyl of from 3 to 8 carbon atoms, and R 1 and R 2 taken together with the adjacent atom may form a heterocyclic residue selected from 4-morpholino, 1-pyrrolidino, 1-piperidino, 1-piperazino and 4-lower alkyl piperazin-1-yl; X is oxygen or sulfur; and the pharmaceutically acceptable acid addition salts thereof.
Claim 3
Dependent Claim 9 words
The method of claim 1 wherein Ar is phenyl.
Claim 4
Dependent Claim 10 words
The method of claim 1 wherein Ar is substituted phenyl.
Claim 5
Dependent Claim 10 words
The method of claim 3 wherein Ar is halo-substituted phenyl.
Claim 6
Dependent Claim 9 words
The method of claim 1 wherein X is oxygen.
Claim 7
Dependent Claim 9 words
The method of claim 1 wherein R is hydrogen.
Claim 8
Dependent Claim 15 words
The method of claim 1 wherein R 1 and R 2 are each lower alkyl.
Claim 9
Dependent Claim 14 words
The method of claim 1 wherein R 1 and R 2 are each methyl.
Claim 10
Dependent Claim 19 words
The method of claim 1 wherein said compound is 3-(3-chlorophenoxy)-N-[2-(dimethylamino)ethyl]-1-pyrrolidine carboxamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 11
Dependent Claim 19 words
The method of claim 1 wherein said compound is 3-(3,5-dichlorophenoxy)-N-[2-(dimethylamino)ethyl]-1-pyrrolidine carboxamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 12
Dependent Claim 19 words
The method of claim 1 wherein said compound is 3-(2,6-dichlorophenoxy)-N-[3-(dimethylamino)propyl]-1-pyrrolidine carboxamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 13
Dependent Claim 19 words
The method of claim 1 wherein said compound is 3-(2,3-dichlorophenoxy)-N-(2-dimethylaminoethyl)-1-pyrrolidine carboxamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 14
Dependent Claim 19 words
The method of claim 1 wherein said compound is 3-(2,3-dichlorophenoxy)-N-[3-(dimethylamino)propyl]-1-pyrrolidine carboxamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 15
Dependent Claim 19 words
The method of claim 1 wherein said compound is 3-(3-chlorophenoxy)-N-[3-(dimethylamino)propyl]-1-pyrrolidine carboxamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 16
Dependent Claim 19 words
The method of claim 1 wherein said compound is 3-(3-dichlorophenoxy)-N-[2-(dimethylamino)propyl]-1-pyrrolidine carboxamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 17
Dependent Claim 19 words
The method of claim 1 wherein said compound is 3-(3,5-dichlorophenoxy)-N-[3-(dimethylamino)propyl]-1-pyrrolidine carboxamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 18
Dependent Claim 19 words
The method of claim 1 wherein said compound is N-[2-(dimethylamino)ethyl]-3-phenoxy-1-pyrrolidine carboxamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 19
Dependent Claim 19 words
The method of claim 1 wherein said compound is 3-(3-chlorophenoxy)-N-[2-(dimethylamino)ethyl]-N-methyl-1-pyrrolidine carboxamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 20
Dependent Claim 19 words
The method of claim 1 wherein said compound is 3-(3,4-dichlorophenoxy)-N-[2-(dimethylamino)ethyl]-1-pyrrolidine carboxamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 21
Dependent Claim 19 words
The method of claim 1 wherein said compound is 3-(3,4-dichlorophenoxy)-N-[2-(dimethylamino)ethyl]-1-piperidine carboxamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 22
Dependent Claim 19 words
The method of claim 1 wherein said compound is 4-(3,4-dichlorophenoxy)-N-[2-(dimethylamino)ethyl]-N-methyl-1-piperidine carboxamide or a pharmaceutically acceptable acid addition salt thereof.

References Cited (Backward Citations)

US3577415A Cited
US4075340A Cited
US4036957A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1988-10-14 1989-04-15 1989-10-15 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-10-14 1993-04-15 1993-10-15 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-10-14 1997-04-15 1997-10-15 $7700.00 Window Closed / Lapsed

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