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US4101666A Expired / Lapsed US ⏱️ 0.0 years remaining

1-(2-Ar-4-R-1,3-dioxolan-2-ylmethyl)imidazoles

Assignee: Janssen Pharmaceutica NV
•
Filing: 1976-10-15
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Granted: 1978-07-18
•
Expires: 1996-10-15
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Abstract

Abstract 1-(2-Ar-4-R-1,3-dioxolan-2-ylmethyl)imidazoles, useful as antifungal and antibacterial agents.

Inventors

  • 👤 Jan Heeres

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-31 19:27
CPC Classifications
C; C07; C07D; C07D303/00; C07D303/02; C07D303/04; C07D303/08; C07D303/12; C07D317/00; C07D317/08; C07D317/10; C07D317/14; C07D317/16; C07D317/18; C07D317/22

Claims Analysis

Total Claims: 24
Claim 1
Independent Claim 197 words
A chemical compound selected from the group consisting of an imidazole derivative having the formula: ##STR19## and the therapeutically acceptable acid addition salts and stereochemical optical isomeric forms thereof, wherein: Ar is a member selected from the group consisting of phenyl, substituted phenyl, thienyl, halothienyl and naphthalenyl, and wherein said substituted phenyl is phenyl having from 1 to 3 substituents independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, nitro and cyano; and R is a member selected from the group consisting of alkyloxymethyl wherein the alkylgroup has from 1 to 10 carbon atoms, alkenyl, alkenyloxymethyl, wherein said alkenyl has from 2 to 10 carbon atoms, hydroxymethyl, 2-propynyloxymethyl, halomethyl, arylmethyl and arylmethoxymethyl, wherein said aryl is a member selected from the group consisting of phenyl, substituted phenyl, naphthalenyl and mono- and di-halonaphthalenyl, and wherein said substituted phenyl is phenyl having from 1 to 3 substituents independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, cyano, nitro, phenyl, phenylmethyl, benzoyl, halobenzoyl, lower alkylcarbonyl, lower alkyloxycarbonyl and trifluoromethyl, provided that when more than 1 substituents are present only 1 thereof may be selected from the group consisting of phenyl, phenylmethyl, benzoyl and halobenzoyl.
Claim 2
Dependent Claim 197 words
A chemical compound selected from the group consisting of an imidazole derivative having the formula: ##STR19## and the therapeutically acceptable acid addition salts and stereochemical optical isomeric forms thereof, wherein: Ar is a member selected from the group consisting of phenyl, substituted phenyl, thienyl, halothienyl and naphthalenyl, and wherein said substituted phenyl is phenyl having from 1 to 3 substituents independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, nitro and cyano; and R is a member selected from the group consisting of alkyloxymethyl wherein the alkylgroup has from 1 to 10 carbon atoms, alkenyl, alkenyloxymethyl, wherein said alkenyl has from 2 to 10 carbon atoms, hydroxymethyl, 2-propynyloxymethyl, halomethyl, arylmethyl and arylmethoxymethyl, wherein said aryl is a member selected from the group consisting of phenyl, substituted phenyl, naphthalenyl and mono- and di-halonaphthalenyl, and wherein said substituted phenyl is phenyl having from 1 to 3 substituents independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, cyano, nitro, phenyl, phenylmethyl, benzoyl, halobenzoyl, lower alkylcarbonyl, lower alkyloxycarbonyl and trifluoromethyl, provided that when more than 1 substituents are present only 1 thereof may be selected from the group consisting of phenyl, phenylmethyl, benzoyl and halobenzoyl.
Claim 3
Dependent Claim 151 words
A chemical compound selected from the group consisting of an imidazole derivative having the formula: ##STR20## and the therapeutically acceptable acid addition salts and stereochemical optical isomeric forms thereof, wherein: R is a member selected from the group consisting of alkyloxymethyl wherein the alkylgroup has from 1 to 10 carbon atoms, alkenyl, alkenyloxymethyl, wherein said alkenyl has from 2 to 10 carbon atoms, hydroxymethyl, 2-propynyloxymethyl, halomethyl, arylmethyl and arylmethoxymethyl, wherein said aryl is a member selected from the group consisting of phenyl, substituted phenyl, naphthalenyl wnd mono- and di-halonaphthalenyl, and wherein said substituted phenyl is phenyl having from 1 to 3 substituents independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, cyano, nitro, phenyl, phenylmethyl, benzoyl, halobenzoyl, lower alkylcarbonyl, lower alkyloxycarbonyl and trifluoromethyl, provided that when more than 1 substituents are present only 1 thereof may be selected from the group consisting of phenyl, phenylmethyl, benzoyl and halobenzoyl.
Claim 4
Dependent Claim 151 words
A chemical compound selected from the group consisting of an imidazole derivative having the formula: ##STR20## and the therapeutically acceptable acid addition salts and stereochemical optical isomeric forms thereof, wherein: R is a member selected from the group consisting of alkyloxymethyl wherein the alkylgroup has from 1 to 10 carbon atoms, alkenyl, alkenyloxymethyl, wherein said alkenyl has from 2 to 10 carbon atoms, hydroxymethyl, 2-propynyloxymethyl, halomethyl, arylmethyl and arylmethoxymethyl, wherein said aryl is a member selected from the group consisting of phenyl, substituted phenyl, naphthalenyl wnd mono- and di-halonaphthalenyl, and wherein said substituted phenyl is phenyl having from 1 to 3 substituents independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, cyano, nitro, phenyl, phenylmethyl, benzoyl, halobenzoyl, lower alkylcarbonyl, lower alkyloxycarbonyl and trifluoromethyl, provided that when more than 1 substituents are present only 1 thereof may be selected from the group consisting of phenyl, phenylmethyl, benzoyl and halobenzoyl.
Claim 5
Dependent Claim 18 words
A chemical compound selected from the group consisting of 1-[2-(2,4-dichlorophenyl)-4-(2-propenyloxymethyl)-1,3-dioxolan-2-ylmethyl]-1H-imidazole and the therapeutically acceptable acid addition salts thereof.
Claim 6
Dependent Claim 18 words
A chemical compound selected from the group consisting of 1-[2-(2,4-dichlorophenyl)-4-(2-propenyloxymethyl)-1,3-dioxolan-2-ylmethyl]-1H-imidazole and the therapeutically acceptable acid addition salts thereof.
Claim 7
Dependent Claim 18 words
A chemical compound selected from the group consisting of cis-1-[2-(2,4-dichlorophenyl)-4-(2-propenyloxymethyl)-1,3-dioxolan-2-ylmethyl]-1H-imidazole and the therapeutically acceptable acid addition salts thereof.
Claim 8
Dependent Claim 18 words
A chemical compound selected from the group consisting of cis-1-[2-(2,4-dichlorophenyl)-4-(2-propenyloxymethyl)-1,3-dioxolan-2-ylmethyl]-1H-imidazole and the therapeutically acceptable acid addition salts thereof.
Claim 9
Dependent Claim 18 words
A chemical compound selected from the group consisting of 1-{2-(2,4-dichlorophenyl)-4-[(2-propynyloxy)methyl]-1,3-dioxolan-2-ylmethyl}-1H-imidazole and the therapeutically acceptable acid addition salts thereof.
Claim 10
Dependent Claim 18 words
A chemical compound selected from the group consisting of 1-{2-(2,4-dichlorophenyl)-4-[(2-propynyloxy)methyl]-1,3-dioxolan-2-ylmethyl}-1H-imidazole and the therapeutically acceptable acid addition salts thereof.
Claim 11
Dependent Claim 18 words
A chemical compound selected from the group consisting of cis-1-{2-(2,4-dichlorophenyl)-4-[(2-propynyloxy)methyl]-1,3-dioxolan-2-ylmethyl}-1H-imidazole and the therapeutically acceptable acid addition salts thereof.
Claim 12
Dependent Claim 18 words
A chemical compound selected from the group consisting of cis-1-{2-(2,4-dichlorophenyl)-4-[(2-propynyloxy)methyl]-1,3-dioxolan-2-ylmethyl}-1H-imidazole and the therapeutically acceptable acid addition salts thereof.
Claim 13
Dependent Claim 231 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 amidazole derivative having the formula ##STR21## and the therapeutically active acid addition salts and stereochemical optical isomeric forms thereof, wherein: Ar is a member selected from the group consisting of phenyl, substituted phenyl, thienyl, halothienyl and naphthalenyl, and wherein said substituted phenyl is phenyl having from 1 to 3 substituents independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, nitro and cyano; and R is a member selected from the group consisting of alkyloxymethyl wherein the alkylgroup has from 1 to 10 carbon atoms, alkenyl, alkenyloxymethyl, wherein said alkenyl has from 2 to 10 carbon atoms, hydroxymethyl, 2-propynyloxymethyl, halomethyl, arylmethyl and arylmethoxymethyl, wherein said aryl is a member selected from the group consisting of phenyl, substituted phenyl, naphthalenyl and mono- and di-halonaphthalenyl, and wherein said substituted phenyl is phenyl having from 1 to 3 substituents independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, cyano, nitro, phenyl, phenylmethyl, benzoyl, halobenzoyl, lower alkylcarbonyl, lower alkyloxycarbonyl and trifluoromethyl, provided that when more than 1 substituents are present only 1 thereof may be selected from the group consisting of phenyl, phenylmethyl, benzoyl and halobenzoyl.
Claim 14
Dependent Claim 231 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 amidazole derivative having the formula ##STR21## and the therapeutically active acid addition salts and stereochemical optical isomeric forms thereof, wherein: Ar is a member selected from the group consisting of phenyl, substituted phenyl, thienyl, halothienyl and naphthalenyl, and wherein said substituted phenyl is phenyl having from 1 to 3 substituents independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, nitro and cyano; and R is a member selected from the group consisting of alkyloxymethyl wherein the alkylgroup has from 1 to 10 carbon atoms, alkenyl, alkenyloxymethyl, wherein said alkenyl has from 2 to 10 carbon atoms, hydroxymethyl, 2-propynyloxymethyl, halomethyl, arylmethyl and arylmethoxymethyl, wherein said aryl is a member selected from the group consisting of phenyl, substituted phenyl, naphthalenyl and mono- and di-halonaphthalenyl, and wherein said substituted phenyl is phenyl having from 1 to 3 substituents independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, cyano, nitro, phenyl, phenylmethyl, benzoyl, halobenzoyl, lower alkylcarbonyl, lower alkyloxycarbonyl and trifluoromethyl, provided that when more than 1 substituents are present only 1 thereof may be selected from the group consisting of phenyl, phenylmethyl, benzoyl and halobenzoyl.
Claim 15
Dependent Claim 185 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 imidazole derivative having the formula ##STR22## and the therapeutically active acid addition salts and stereochemical optical isomeric forms thereof, wherein: R is a member selected from the group consisting of alkyloxymethyl wherein the alkylgroup has from 1 to 10 carbon atoms, alkenyl, alkenyloxymethyl, wherein said alkenyl has from 2 to 10 carbon atoms, hydroxymethyl, 2-propynyloxymethyl, halomethyl, arylmethyl and arylmethoxymethyl, wherein said aryl is a member selected from the group consisting of phenyl, substituted phenyl, naphthalenyl and mono- and di-halonaphthalenyl, and wherein said substituted phenyl is phenyl having from 1 to 3 substituents independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, cyano, nitro, phenyl, phenylmethyl, benzoyl, halobenzoyl, lower alkylcarbonyl, lower alkyloxycarbonyl and trifluoromethyl, provided that when more than 1 substituents are present only 1 thereof may be selected from the group consisting of phenyl, phenylmethyl, benzoyl and halobenzoyl.
Claim 16
Dependent Claim 185 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 imidazole derivative having the formula ##STR22## and the therapeutically active acid addition salts and stereochemical optical isomeric forms thereof, wherein: R is a member selected from the group consisting of alkyloxymethyl wherein the alkylgroup has from 1 to 10 carbon atoms, alkenyl, alkenyloxymethyl, wherein said alkenyl has from 2 to 10 carbon atoms, hydroxymethyl, 2-propynyloxymethyl, halomethyl, arylmethyl and arylmethoxymethyl, wherein said aryl is a member selected from the group consisting of phenyl, substituted phenyl, naphthalenyl and mono- and di-halonaphthalenyl, and wherein said substituted phenyl is phenyl having from 1 to 3 substituents independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, cyano, nitro, phenyl, phenylmethyl, benzoyl, halobenzoyl, lower alkylcarbonyl, lower alkyloxycarbonyl and trifluoromethyl, provided that when more than 1 substituents are present only 1 thereof may be selected from the group consisting of phenyl, phenylmethyl, benzoyl and halobenzoyl.
Claim 17
Dependent Claim 52 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 1-[2-(2,4-dichlorophenyl)-4-(2-propenyloxymethyl)-1,3-dioxolan-2-ylmethyl]-1H-imidazole and the therapeutically acceptable acid addition salts thereof.
Claim 18
Dependent Claim 52 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 1-[2-(2,4-dichlorophenyl)-4-(2-propenyloxymethyl)-1,3-dioxolan-2-ylmethyl]-1H-imidazole and the therapeutically acceptable acid addition salts thereof.
Claim 19
Dependent Claim 52 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 cis-1-[2-(2,4-dichlorophenyl)-4-(2-propenyloxymethyl)-1,3-dioxolan-2-ylmethyl]-1H-imidazole and the therapeutically acceptable acid addition salts thereof.
Claim 20
Dependent Claim 52 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 cis-1-[2-(2,4-dichlorophenyl)-4-(2-propenyloxymethyl)-1,3-dioxolan-2-ylmethyl]-1H-imidazole and the therapeutically acceptable acid addition salts thereof.
Claim 21
Dependent Claim 52 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 1-{2-(2,4-dichlorophenyl)-4-[(2-propynyloxy)methyl]-1,3-dioxolan-2-ylmethyl}-1H-imidazole and the therapeutically acceptable acid addition salts thereof.
Claim 22
Dependent Claim 52 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 1-{2-(2,4-dichlorophenyl)-4-[(2-propynyloxy)methyl]-1,3-dioxolan-2-ylmethyl}-1H-imidazole and the therapeutically acceptable acid addition salts thereof.
Claim 23
Dependent Claim 52 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 cis-1-{2-(2,4-dichlorophenyl)-4-[(2-propynyloxy)methyl]-1,3-dioxolan-2-ylmethyl}-1H-imidazole and the therapeutically acceptable acid addition salts thereof.
Claim 24
Dependent Claim 52 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 cis-1-{2-(2,4-dichlorophenyl)-4-[(2-propynyloxy)methyl]-1,3-dioxolan-2-ylmethyl}-1H-imidazole and the therapeutically acceptable acid addition salts thereof.

References Cited (Backward Citations)

US3575999A Cited
US3717655A Cited
US3936470A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-07-17 1982-01-16 1982-07-18 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-07-17 1986-01-16 1986-07-18 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-07-17 1990-01-16 1990-07-18 $7700.00 Window Closed / Lapsed

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