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US4200641A Expired / Lapsed US ⏱️ 0.0 years remaining

1-[(Heterocyclyl)-alkyl]-4-diarylmethoxy piperidine derivatives

Assignee: Janssen Pharmaceutica NV
•
Filing: 1978-02-06
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Granted: 1980-04-29
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Expires: 1998-02-06
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Abstract

Abstract Novel 1-[(heterocyclyl)alkyl]-4-diarylmethoxy piperidine derivatives are disclosed having the formula ##STR1## where n is 2-6, Ar 1 and Ar 2 are aryl and B is a substituted benzimidazolyl radical. These compounds are useful for their antianaphylactic and antihistaminic properties. Specific claimed compounds are 1-{3-[4-(diphenylmethoxy)-1-piperidinyl]-propyl}-1,3-dihydro-2H-benzimidazol-2-one, 1-{2-[4-(diphenylmethoxy)-1-piperidinyl]ethyl}1-, 3-dihydro-2H-benzimidazol-2-one, and 1-{4-[4-(diphenylmethoxy)-1-piperidinyl]butyl}-1,3-dihydro-2H-benzimidazol-2-one.

Inventors

  • 👤 Jan Vandenberk
  • 👤 Ludo E. J. Kennis
  • 👤 Marcel J. M. C. Van der Aa
  • 👤 Albert H. M. Th. Van Heertum

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 14:53
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/28; C07D213/30; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/44; C07D211/46; C07D213/26; C07D213/44; C07D213/46; C07D213/50; C07D235/00; C07D235/02; C07D235/04; C07D235/06; C07D235/08; C07D235/18; C07D235/24; C07D235/26; C07D235/28; C07D295/00; C07D295/04; C07D295/06; C07D295/073; C07D295/12; C07D295/125; C07D295/13

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 274 words
A chemical compound selected from the group consisting of a compound having the formula ##STR61## and the pharmaceutically acceptable acid addition salts thereof, wherein: Ar 1 and Ar 2 are each independently selected from the group consisting of phenyl, substituted phenyl and pyridinyl, wherein said substituted phenyl is phenyl having from 1 to 2 substituents independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, trifluoromethyl and nitro; m is the ingeger 1; A is >CH-- n is an integer of from 2 to 6 inclusive, provided that when C n H 2n represents a branched alkylene chain, then at least 2 carbon atoms are present in the linear portion of the chain linking B with the piperidine nitrogen atom; and B is a member selected from the group consisting of: (a) a radical having the formula ##STR62## wherein: R 1 and R 2 are each independently selected from the group consisting of hydrogen, halo, lower alkyl and trifluoromethyl; and Y is a member selected from the group consisting of oxygen, sulfur and a substituted nitrogen of the formula >N--L wherein said L is a member selected from the group consisting of hydrogen, lower alkyl, lower alkylcarbonyl, lower alkyloxycarbonyl-lower alkyl, carboxy-lower alkyl, phenyl, phenylmethyl, lower alkylaminocarbonyl, hydroxymethyl, and lower alkenyl; and (b) a radical having the formula ##STR63## wherein: R 1 and R 2 are each independently selected from the group consisting of hydrogen, halo, lower alkyl and trifluoromethyl; and M is a member selected from the group consisting of hydrogen, lower alkyl, phenyl, phenylmethyl, mercapto, lower alkylthio, amino, lower alkylcarbonylamino, lower alkyloxycarbonylamino, and cycloalkyl having from 3 to 6 carbon atoms.
Claim 2
Dependent Claim 274 words
A chemical compound selected from the group consisting of a compound having the formula ##STR61## and the pharmaceutically acceptable acid addition salts thereof, wherein: Ar 1 and Ar 2 are each independently selected from the group consisting of phenyl, substituted phenyl and pyridinyl, wherein said substituted phenyl is phenyl having from 1 to 2 substituents independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, trifluoromethyl and nitro; m is the ingeger 1; A is >CH-- n is an integer of from 2 to 6 inclusive, provided that when C n H 2n represents a branched alkylene chain, then at least 2 carbon atoms are present in the linear portion of the chain linking B with the piperidine nitrogen atom; and B is a member selected from the group consisting of: (a) a radical having the formula ##STR62## wherein: R 1 and R 2 are each independently selected from the group consisting of hydrogen, halo, lower alkyl and trifluoromethyl; and Y is a member selected from the group consisting of oxygen, sulfur and a substituted nitrogen of the formula >N--L wherein said L is a member selected from the group consisting of hydrogen, lower alkyl, lower alkylcarbonyl, lower alkyloxycarbonyl-lower alkyl, carboxy-lower alkyl, phenyl, phenylmethyl, lower alkylaminocarbonyl, hydroxymethyl, and lower alkenyl; and (b) a radical having the formula ##STR63## wherein: R 1 and R 2 are each independently selected from the group consisting of hydrogen, halo, lower alkyl and trifluoromethyl; and M is a member selected from the group consisting of hydrogen, lower alkyl, phenyl, phenylmethyl, mercapto, lower alkylthio, amino, lower alkylcarbonylamino, lower alkyloxycarbonylamino, and cycloalkyl having from 3 to 6 carbon atoms.
Claim 3
Dependent Claim 18 words
A chemical compound selected from the group consisting of 1-{3-[4-(diphenylmethoxy)-1-piperidinyl]-propyl}-1,3-dihydro-2H-benzimidazol-2-one and the pharmaceutically acceptable acid addition salts thereof.
Claim 4
Dependent Claim 18 words
A chemical compound selected from the group consisting of 1-{3-[4-(diphenylmethoxy)-1-piperidinyl]-propyl}-1,3-dihydro-2H-benzimidazol-2-one and the pharmaceutically acceptable acid addition salts thereof.
Claim 5
Dependent Claim 18 words
A chemical compound selected from the group consisting of 1-{2-[4-(diphenylmethoxy)-1-piperidinyl]ethyl}-1,3-dihydro-2H-benzimidazol-2-one and the pharmaceutically acceptable acid addition salts thereof.
Claim 6
Dependent Claim 18 words
A chemical compound selected from the group consisting of 1-{2-[4-(diphenylmethoxy)-1-piperidinyl]ethyl}-1,3-dihydro-2H-benzimidazol-2-one and the pharmaceutically acceptable acid addition salts thereof.
Claim 7
Dependent Claim 18 words
A chemical compound selected from the group consisting of 1-{4-[4-(diphenylmethoxy)-1-piperidinyl]butyl}-1,3-dihydro-2H-benzimidazol-2-one and the pharmaceutically acceptable acid addition salts thereof.
Claim 8
Dependent Claim 18 words
A chemical compound selected from the group consisting of 1-{4-[4-(diphenylmethoxy)-1-piperidinyl]butyl}-1,3-dihydro-2H-benzimidazol-2-one and the pharmaceutically acceptable acid addition salts thereof.
Claim 9
Dependent Claim 294 words
A pharmaceutical composition comprising an inert carrier material and as an active ingredient an effective antihistaminic or anti-anaphylactic amount of a chemical compound selected from the group consisting of a compound having the formula ##STR64## and the pharmaceutically acceptable acid addition salts thereof, wherein: Ar 1 and Ar 2 are each independently selected from the group consisting of phenyl, substituted phenyl and pyridinyl, wherein said substituted phenyl is phenyl having from 1 to 2 substituents independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, trifluoromethyl and nitro; m is the integer 1; A is >CH-- n is an integer of from 2 to 6 inclusive, provided that when C n H 2n represents a branched alkylene chain, then at least 2 carbon atoms are present in the linear portion of the chain linking B with the piperidine nitrogen atom; and B is a member selected from the group consisting of: (a) a radical having the formula ##STR65## wherein: R 1 and R 2 are each independently selected from the group consisting of hydrogen, halo, lower alkyl and trifluoromethyl; and Y is a member selected from the group consisting of oxygen, sulfur and a substituted nitrogen of the formula >N--L wherein said L is a member selected from the group consisting of hydrogen, lower alkyl, lower alkylcarbonyl, lower alkyloxycarbonyl-lower alkyl, carboxy-lower alkyl, phenyl, phenylmethyl, lower alkylaminocarbonyl, hydroxymethyl, and lower alkenyl; and (b) a radical having the formula ##STR66## wherein: R 1 and R 2 are each independently selected from the group consisting of hydrogen, halo, lower alkyl, and trifluoromethyl; and M is a member selected from the group consisting of hydrogen, lower alkyl, phenyl, phenylmethyl, mercapto, lower alkylthio, amino, lower alkylcarbonylamino, lower alkyloxycarbonylamino, and cycloalkyl having from 3 to 6 carbon atoms.
Claim 10
Dependent Claim 294 words
A pharmaceutical composition comprising an inert carrier material and as an active ingredient an effective antihistaminic or anti-anaphylactic amount of a chemical compound selected from the group consisting of a compound having the formula ##STR64## and the pharmaceutically acceptable acid addition salts thereof, wherein: Ar 1 and Ar 2 are each independently selected from the group consisting of phenyl, substituted phenyl and pyridinyl, wherein said substituted phenyl is phenyl having from 1 to 2 substituents independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, trifluoromethyl and nitro; m is the integer 1; A is >CH-- n is an integer of from 2 to 6 inclusive, provided that when C n H 2n represents a branched alkylene chain, then at least 2 carbon atoms are present in the linear portion of the chain linking B with the piperidine nitrogen atom; and B is a member selected from the group consisting of: (a) a radical having the formula ##STR65## wherein: R 1 and R 2 are each independently selected from the group consisting of hydrogen, halo, lower alkyl and trifluoromethyl; and Y is a member selected from the group consisting of oxygen, sulfur and a substituted nitrogen of the formula >N--L wherein said L is a member selected from the group consisting of hydrogen, lower alkyl, lower alkylcarbonyl, lower alkyloxycarbonyl-lower alkyl, carboxy-lower alkyl, phenyl, phenylmethyl, lower alkylaminocarbonyl, hydroxymethyl, and lower alkenyl; and (b) a radical having the formula ##STR66## wherein: R 1 and R 2 are each independently selected from the group consisting of hydrogen, halo, lower alkyl, and trifluoromethyl; and M is a member selected from the group consisting of hydrogen, lower alkyl, phenyl, phenylmethyl, mercapto, lower alkylthio, amino, lower alkylcarbonylamino, lower alkyloxycarbonylamino, and cycloalkyl having from 3 to 6 carbon atoms.

References Cited (Backward Citations)

US4021564A Cited
US4031226A Cited
US4035369A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-04-29 1983-10-29 1984-04-29 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-04-29 1987-10-29 1988-04-29 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-04-29 1991-10-29 1992-04-29 $7700.00 Window Closed / Lapsed

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