US4101666A
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1-(2-Ar-4-R-1,3-dioxolan-2-ylmethyl)imidazoles
Assignee: Janssen Pharmaceutica NV
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Filing: 1976-10-15
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Granted: 1978-07-18
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Expires: 1996-10-15
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)
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 |