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US4287195A Expired / Lapsed US ⏱️ 0.0 years remaining

Heterocyclic derivatives of [4-(piperazin-1-yl-phenyloxymethyl)-1,3-dioxolan-2-ylmethyl]-1H-imidazoles and 1H-1,2,4-triazoles

Assignee: Janssen Pharmaceutica NV
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Filing: 1979-04-04
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Granted: 1981-09-01
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Expires: 1999-04-04
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Abstract

Abstract Novel heterocyclic derivatives of [4-(piperazin-1-yl-phenloxymethyl)-1,3-dioxolan-2-ylmethyl]-1H-imidazoles and 1H-1,2,4-triazoles, useful as antifungal and antibacterial agents.

Inventors

  • 👤 Jan Heeres
  • 👤 Robert Hendrickx

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 15:33
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/72; C07D213/74; C07D215/00; C07D215/02; C07D215/16; C07D215/38; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07D233/00; C07D233/54; C07D233/56; C07D233/66; C07D233/84; C07D249/00; C07D249/02; C07D249/08; C07D249/10; C07D249/14; C07D277/00; C07D277/02; C07D277/08; C07D277/12; C07D277/18; C07D277/20; C07D277/32; C07D277/38; C07D277/42; C07D295/00; C07D295/22; C07D295/28; C07D473/00; C07D473/02; C07D473/04; C07D473/06

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 252 words
A chemical compound selected from the group consisting of an azole derivative having the formula: ##STR36## and the pharmaceutically acceptable acid addition salts and stereochemically isomeric forms thereof, wherein: Q is a member selected from the group consisting of CH and N; Ar is a member selected from the group consisting of phenyl, thienyl, halothienyl and substituted phenyl, said substituted phenyl having from 1 to 3 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy and trifluoromethyl; and the radical Y is an optionally substituted mono- or binuclear nitrogen-containing heteroaromatic radical selected from the group consisting of: a radical of formula ##STR37## wherein R 1 is selected from the group consisting of hydrogen, lower alkylthio, aryl lower alkylthio and arylthio and R 2 and R 3 are each independently selected from the group consisting of hydrogen, lower alkyl, aryl and aryl lower alkyl; a radical of formula ##STR38## wherein each of R 4 and R 5 are independently selected from the group consisting of hydrogen, lower alkyl, aryl and aryllower alkyl; a radical of formula ##STR39## wherein L is a member selected from the group consisting of S and N-R 18 , said R 18 being selected from the group consisting of hydrogen, lower alkyl and aryllower alkyl, and R 16 and R 17 are each independently selected from the group consisting of hydrogen, lower alkyl, nitro and aryllower alkyl, or R 16 and R 17 , when taken together, represent a radical of the formula --CH═CH--CH═CH--.
Claim 2
Dependent Claim 252 words
A chemical compound selected from the group consisting of an azole derivative having the formula: ##STR36## and the pharmaceutically acceptable acid addition salts and stereochemically isomeric forms thereof, wherein: Q is a member selected from the group consisting of CH and N; Ar is a member selected from the group consisting of phenyl, thienyl, halothienyl and substituted phenyl, said substituted phenyl having from 1 to 3 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy and trifluoromethyl; and the radical Y is an optionally substituted mono- or binuclear nitrogen-containing heteroaromatic radical selected from the group consisting of: a radical of formula ##STR37## wherein R 1 is selected from the group consisting of hydrogen, lower alkylthio, aryl lower alkylthio and arylthio and R 2 and R 3 are each independently selected from the group consisting of hydrogen, lower alkyl, aryl and aryl lower alkyl; a radical of formula ##STR38## wherein each of R 4 and R 5 are independently selected from the group consisting of hydrogen, lower alkyl, aryl and aryllower alkyl; a radical of formula ##STR39## wherein L is a member selected from the group consisting of S and N-R 18 , said R 18 being selected from the group consisting of hydrogen, lower alkyl and aryllower alkyl, and R 16 and R 17 are each independently selected from the group consisting of hydrogen, lower alkyl, nitro and aryllower alkyl, or R 16 and R 17 , when taken together, represent a radical of the formula --CH═CH--CH═CH--.
Claim 3
Dependent Claim 18 words
A chemical compound selected from the group consisting of cis-8-[4-{4-[2-(2,4-dichlorophenyl)-2-(1H-imidazol--ylmethyl)-1,3-dioxolan-4-ylmethoxy]phenyl}-1-piperazinyl]-7-ethyl-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione and the pharmaceutically acceptable acid addition salts thereof.
Claim 4
Dependent Claim 18 words
A chemical compound selected from the group consisting of cis-8-[4-{4-[2-(2,4-dichlorophenyl)-2-(1H-imidazol--ylmethyl)-1,3-dioxolan-4-ylmethoxy]phenyl}-1-piperazinyl]-7-ethyl-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione and the pharmaceutically acceptable acid addition salts thereof.
Claim 5
Dependent Claim 18 words
A chemical compound selected from the group consisting of cis-1-{4-[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-ylmethoxy]phenyl}-4-(2-thiazolyl)piperazine and the pharmaceutically acceptable acid addition salts thereof.
Claim 6
Dependent Claim 18 words
A chemical compound selected from the group consisting of cis-1-{4-[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-ylmethoxy]phenyl}-4-(2-thiazolyl)piperazine and the pharmaceutically acceptable acid addition salts thereof.
Claim 7
Dependent Claim 19 words
A chemical compound selected from the group consisting of cis-1-{4-[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-ylmethoxy]-phenyl}-4-(1H-imidazol-1-yl)piperazine hemihydrate and the pharmaceutically acceptable acid addition salts thereof.
Claim 8
Dependent Claim 19 words
A chemical compound selected from the group consisting of cis-1-{4-[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-ylmethoxy]-phenyl}-4-(1H-imidazol-1-yl)piperazine hemihydrate and the pharmaceutically acceptable acid addition salts thereof.
Claim 9
Dependent Claim 283 words
A composition for combatting the growth of a microorganism selected from the group consisting of fungus and bacterium comprising an inert carrier material and as an active ingredient an effective antifungal or antibacterial amount of a compound selected from the group consisting of an azole derivative having the formula: ##STR40## and the pharmaceutically acceptable addition salts and stereochemically isomeric forms thereof, wherein: Q is a member selected from the group consisting of CH and N; Ar is a member selected from the group consisting of phenyl, thienyl, halothienyl and substituted phenyl, said substituted phenyl having from 1 to 3 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy and trifluoromethyl; and the radical Y is an optionally substituted mono- or binuclear nitrogen-containing heteroaromatic radical selected from the group consisting of: a radical of formula ##STR41## wherein R 1 is selected from the group consisting of hydrogen, lower alkylthio, aryllower alkylthio and arylthio and R 2 and R 3 are each independently selected from the group consisting of hydrogen, lower alkyl, aryl and aryllower alkyl; a radical of formula ##STR42## wherein each of R 4 and R 5 are independently selected from the group consisting of hydrogen, lower alkyl, aryl and aryllower alkyl; a radical of formula ##STR43## wherein L is a member selected from the group consisting of S and N-R 18 , said R 18 being selected from the group consisting of hydrogen, lower alkyl and aryllower alkyl, and R 16 and R 17 are each independently selected from the group consisting of hydrogen, lower alkyl, nitro and aryllower alkyl, or R 16 and R 17 , when taken together, represent a radical of the formula --CH═CH--CH═CH--.
Claim 10
Dependent Claim 283 words
A composition for combatting the growth of a microorganism selected from the group consisting of fungus and bacterium comprising an inert carrier material and as an active ingredient an effective antifungal or antibacterial amount of a compound selected from the group consisting of an azole derivative having the formula: ##STR40## and the pharmaceutically acceptable addition salts and stereochemically isomeric forms thereof, wherein: Q is a member selected from the group consisting of CH and N; Ar is a member selected from the group consisting of phenyl, thienyl, halothienyl and substituted phenyl, said substituted phenyl having from 1 to 3 substituents each independently selected from the group consisting of halo, lower alkyl, lower alkyloxy and trifluoromethyl; and the radical Y is an optionally substituted mono- or binuclear nitrogen-containing heteroaromatic radical selected from the group consisting of: a radical of formula ##STR41## wherein R 1 is selected from the group consisting of hydrogen, lower alkylthio, aryllower alkylthio and arylthio and R 2 and R 3 are each independently selected from the group consisting of hydrogen, lower alkyl, aryl and aryllower alkyl; a radical of formula ##STR42## wherein each of R 4 and R 5 are independently selected from the group consisting of hydrogen, lower alkyl, aryl and aryllower alkyl; a radical of formula ##STR43## wherein L is a member selected from the group consisting of S and N-R 18 , said R 18 being selected from the group consisting of hydrogen, lower alkyl and aryllower alkyl, and R 16 and R 17 are each independently selected from the group consisting of hydrogen, lower alkyl, nitro and aryllower alkyl, or R 16 and R 17 , when taken together, represent a radical of the formula --CH═CH--CH═CH--.

References Cited (Backward Citations)

US4160841A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-08-31 1985-03-02 1985-09-01 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-08-31 1989-03-02 1989-09-01 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-08-31 1993-03-02 1993-09-01 $7700.00 Window Closed / Lapsed

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