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US4223036A Expired / Lapsed US ⏱️ 0.0 years remaining

1-(1,3-Dioxolan-2-ylmethyl)-1H-1,2,4-triazoles

Assignee: Janssen Pharmaceutica NV
•
Filing: 1979-01-08
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Granted: 1980-09-16
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Expires: 1999-01-08
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Abstract

Abstract Novel 1-(1,3-dioxolan-2-ylmethyl)-1H-imidazoles and 1H-1,2,4-triazoles useful as antifungal and antibacterial agents.

Inventors

  • 👤 Jan Heeres
  • 👤 Leo J. J. Backx
  • 👤 Joseph H. Mostmans

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-31 17:28
CPC Classifications
C; C07; C07D; C07D405/00; C07D405/02; C07D405/06; A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/41; A61K31/415; A61K31/435; A61K31/44; A61K31/445; A61K31/495; A61K31/535; A61P; A61P31/00; A61P31/04; A61P31/10; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08; C07D295/00; C07D295/02; C07D295/027; C07D295/03; C07D295/04; C07D295/08; C07D295/096; C07D295/16; C07D295/18; C07D295/182; C07D295/185; C07D295/22; C07D295/26

Claims Analysis

Total Claims: 6
Claim 1
Independent Claim 259 words
A chemical compound selected from the group consisting of an azole derivative having the formula: ##STR57## and the pharmaceutically acceptable acid addition salts and stereochemical optical isomeric forms thereof, wherein: Q is N; Ar is a member selected from the group consisting of phenyl and substituted phenyl, said substituted phenyl being phenyl having from 1 to 3 substituents independently selected from the group consisting of halo, lower alkyl and lower alkyloxy; the radical A is a member selected from the group consisting of: (a) an isothiocyanato group --N═C═S; (b) an amino radical of the formula ##STR58## wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen and lower alkyl; (c) a radical of the formula ##STR59## wherein X is selected from the group consisting of O and S, Y is selected from the group consisting of O and NH, m is the integer 0 or 1, and R 3 is selected from the group consisting of hydrogen, lower alkyl, mono- and dihalo(lower alkyl), phenyl and substituted phenyl, said substituted phenyl having from 1 to 2 substituents independently selected from the group consisting of halo, lower alkyl and lower alkyloxy, provided that: (i) when said X is S, then said Y is NH and said m is 1, and (ii) when said Y is O and said m is 1, then said R 3 is other than hydrogen; and R is a member selected from the group consisting of hydrogen and nitro, provided that when said R is nitro, then said A is amino.
Claim 2
Dependent Claim 259 words
A chemical compound selected from the group consisting of an azole derivative having the formula: ##STR57## and the pharmaceutically acceptable acid addition salts and stereochemical optical isomeric forms thereof, wherein: Q is N; Ar is a member selected from the group consisting of phenyl and substituted phenyl, said substituted phenyl being phenyl having from 1 to 3 substituents independently selected from the group consisting of halo, lower alkyl and lower alkyloxy; the radical A is a member selected from the group consisting of: (a) an isothiocyanato group --N═C═S; (b) an amino radical of the formula ##STR58## wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen and lower alkyl; (c) a radical of the formula ##STR59## wherein X is selected from the group consisting of O and S, Y is selected from the group consisting of O and NH, m is the integer 0 or 1, and R 3 is selected from the group consisting of hydrogen, lower alkyl, mono- and dihalo(lower alkyl), phenyl and substituted phenyl, said substituted phenyl having from 1 to 2 substituents independently selected from the group consisting of halo, lower alkyl and lower alkyloxy, provided that: (i) when said X is S, then said Y is NH and said m is 1, and (ii) when said Y is O and said m is 1, then said R 3 is other than hydrogen; and R is a member selected from the group consisting of hydrogen and nitro, provided that when said R is nitro, then said A is amino.
Claim 3
Dependent Claim 287 words
A composition for combatting a microorganism selected from the group consisting of fungus and bacterium comprising an inert carrier material and as an active ingredient an effective amount of a compound selected from the group consisting of an azole derivative having the formula: ##STR60## and the pharmaceutically acceptable acid addition salts and stereochemical optical isomeric forms thereof, wherein: Q is N; Ar is a member selected from the group consisting of phenyl and substituted phenyl, said substituted phenyl being phenyl having from 1 to 3 substituents independently selected from the group consisting of halo, lower alkyl and lower alkyloxy; the radical A is a member selected from the group consisting of (a) an isothiocyanato group --N═C═S; (b) an amino radical of the formula ##STR61## wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen and lower alkyl; (c) a radical of the formula ##STR62## wherein X is selected from the group consisting of O and S, Y is selected from the group consisting of O and NH, m is the integer 0 or 1, and R 3 is selected from the group consisting of hydrogen, lower alkyl, mono- and dihalo(lower alkyl), phenyl and substituted phenyl, said substituted phenyl having from 1 to 2 substituents independently selected from the group consisting of halo, lower alkyl and lower alkyloxy, provided that: (i) when said X is S, then said Y is NH and said m is 1, and (ii) when said Y is O and said m is 1, then said R 3 is other than hydrogen; and R is a member selected from the group consisting of hydrogen and nitro, provided that when said R is nitro, then said A is amino.
Claim 4
Dependent Claim 287 words
A composition for combatting a microorganism selected from the group consisting of fungus and bacterium comprising an inert carrier material and as an active ingredient an effective amount of a compound selected from the group consisting of an azole derivative having the formula: ##STR60## and the pharmaceutically acceptable acid addition salts and stereochemical optical isomeric forms thereof, wherein: Q is N; Ar is a member selected from the group consisting of phenyl and substituted phenyl, said substituted phenyl being phenyl having from 1 to 3 substituents independently selected from the group consisting of halo, lower alkyl and lower alkyloxy; the radical A is a member selected from the group consisting of (a) an isothiocyanato group --N═C═S; (b) an amino radical of the formula ##STR61## wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen and lower alkyl; (c) a radical of the formula ##STR62## wherein X is selected from the group consisting of O and S, Y is selected from the group consisting of O and NH, m is the integer 0 or 1, and R 3 is selected from the group consisting of hydrogen, lower alkyl, mono- and dihalo(lower alkyl), phenyl and substituted phenyl, said substituted phenyl having from 1 to 2 substituents independently selected from the group consisting of halo, lower alkyl and lower alkyloxy, provided that: (i) when said X is S, then said Y is NH and said m is 1, and (ii) when said Y is O and said m is 1, then said R 3 is other than hydrogen; and R is a member selected from the group consisting of hydrogen and nitro, provided that when said R is nitro, then said A is amino.
Claim 5
Dependent Claim 23 words
A chemical compound selected from the group consisting of N-{4-[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-ylmethoxy]phenyl}acetamide and the pharmaceutically acceptable acid addition salts and stereochemical optical isomeric forms thereof.
Claim 6
Dependent Claim 23 words
A chemical compound selected from the group consisting of N-{4-[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-ylmethoxy]phenyl}acetamide and the pharmaceutically acceptable acid addition salts and stereochemical optical isomeric forms thereof.

References Cited (Backward Citations)

US4160841A Cited
US4160838A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-09-16 1984-03-17 1984-09-16 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-09-16 1988-03-17 1988-09-16 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-09-16 1992-03-17 1992-09-16 $7700.00 Window Closed / Lapsed

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