US3991202A
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Imidazolium salts
Assignee: Janssen Pharmaceutica NV
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Filing: 1974-11-19
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Granted: 1976-11-09
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Expires: 1994-11-19
Abstract
Abstract Novel quaternary imidazolium salts substituted on one nitrogen of the imidazolium cation with a ##EQU1## group in which each A is an aryl radical and B is an aliphatic, aryl-substituted aliphatic or aromatic radical, said salts being useful as antimicrobial agents.
Inventors
- 👤 Paul Adriaan Jan Janssen
- 👤 Jan Heeres
- 👤 Hubert Karel Frans Hermans
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 21:48
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/77; C07D307/78; C07D307/79; A; A61; A61P; A61P31/00; A61P31/04; C07C; C07C37/00; C07C37/01; C07C37/055; C07C45/00; C07C45/27; C07C45/29; C07C45/292; C07C49/00; C07C49/20; C07C49/255; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
536 words
A quaternary imidazolium salt represented by the structure ##SPC18## and hydrates thereof, wherein A is a member selected from the group consisting of phenyl, mono-, di- and trihalophenyl, lower alkylphenyl, lower alkoxyphenyl, thienyl and halothienyl; B is a member selected from the group consisting of benzyl, mono-, di- and trihalobenzyl, mono- and di-lower alkylbenzyl, lower alkoxybenzyl, cyanobenzyl, phenethyl, mono-, di- and tri-halophenethyl, mono- and di-lower alkylphenethyl, lower alkoxyphenethyl, cyanophenethyl, mono- and di-nitrophenyl, mono- and di-aminophenyl, lower alkyl, lower alkenyl and lower alkynyl; D is selected from the group consisting of: a. an alkyl radical containing from 1 to 12 carbon atoms inclusive; b. a carbamoyl-alkyl radical represented by the formula ##SPC19## wherein R is selected from the group consisting of hydrogen and loweralkyl; each R 1 is independently selected from the group consisting of hydrogen, lower alkyl, halo, nitro, trifluoromethyl, lower alkoxy and phenoxy; a and m are integers of from 1 to 1 inclusive; and n is an integer of from 0 to 2 inclusive; c. an aroylalkyl radical represented by the formula ##EQU2## wherein Ar is selected from the group consisting of thienyl, halothienyl, phenyl, mono- and di-substituted phenyl and wherein each substituent in said substituted phenyl is selected independently from the group consisting of halo, lower alkyl and lower alkoxy; and p is an integer of from 1 to 4 inclusive; d. an aralkyl radical represented by the formula ##SPC20## wherein R 2 is selected from the group consisting of hydrogen, halo, lower alkyl, lower alkoxy, nitro and sulfamoyl; R 3 is selected from the group consisting of hydrogen, halo, lower alkyl, lower alkoxy and cyano; and p is an integer of from 1 to 4 inclusive; e. a diarylmethyl radical represented by the formula ##EQU3## wherein each Ar 1 is selected independently from the group consisting of phenyl and halophenyl; f. an arylaminoethyl radical represented by the formula ##SPC21## wherein each R 4 is independently selected from the group consisting of hydrogen, halo and lower alkyl; and a is an integer of from 1 to 2 inclusive; g. an arylether-alkyl radical represented by the formula -(CH.sub.2).sub.q --Q--Ar.sup.2 wherein Q is selected from the group consisting of oxygen and sulfur; Ar 2 is selected from the group consisting of phenyl, mono- and di-substituted phenyl and naphthyl, and wherein each substituent in said substituted phenyl is selected independently from the group consisting of halo, lower alkyl, lower alkoxy and allyl; and q is an integer of from 2 to 3 inclusive; h. a dihydrobenzofuranylmethyl radical represented by the formula ##SPC22## wherein R 5 is selected from the group consisting of hydrogen and halo; i. an aryl hydroxyethyl radical represented by the formula ##SPC23## wherein R 6 is selected from the group consisting of hydrogen, halo and lower alkoxy, and a is a integer of from 1 to 2 inclusive; k. a phenoxy-2-oxopropyl radical represented by the formula ##EQU4## wherein Ar 3 is selected from the group consisting of phenyl, halophenyl and dihalophenyl; and W is a pharmaceutically acceptable anion selected from the group consisting of chloride, bromide, iodide, methanesulfonate, p-toluenesulfonate, nitrate, sulfate, phosphate, acetate, propionate, glycolate, lactate, pyruvate, malonate, succinate, maleate, fumarate, malate, tartrate, citrate, benzoate, cinnamate, mandelate, ethanesulfonate, benzenesulfonate, cyclohexanesulfamate, salicylate and p-aminosalicylate.
Claim 2
Dependent Claim
536 words
A quaternary imidazolium salt represented by the structure ##SPC18## and hydrates thereof, wherein A is a member selected from the group consisting of phenyl, mono-, di- and trihalophenyl, lower alkylphenyl, lower alkoxyphenyl, thienyl and halothienyl; B is a member selected from the group consisting of benzyl, mono-, di- and trihalobenzyl, mono- and di-lower alkylbenzyl, lower alkoxybenzyl, cyanobenzyl, phenethyl, mono-, di- and tri-halophenethyl, mono- and di-lower alkylphenethyl, lower alkoxyphenethyl, cyanophenethyl, mono- and di-nitrophenyl, mono- and di-aminophenyl, lower alkyl, lower alkenyl and lower alkynyl; D is selected from the group consisting of: a. an alkyl radical containing from 1 to 12 carbon atoms inclusive; b. a carbamoyl-alkyl radical represented by the formula ##SPC19## wherein R is selected from the group consisting of hydrogen and loweralkyl; each R 1 is independently selected from the group consisting of hydrogen, lower alkyl, halo, nitro, trifluoromethyl, lower alkoxy and phenoxy; a and m are integers of from 1 to 1 inclusive; and n is an integer of from 0 to 2 inclusive; c. an aroylalkyl radical represented by the formula ##EQU2## wherein Ar is selected from the group consisting of thienyl, halothienyl, phenyl, mono- and di-substituted phenyl and wherein each substituent in said substituted phenyl is selected independently from the group consisting of halo, lower alkyl and lower alkoxy; and p is an integer of from 1 to 4 inclusive; d. an aralkyl radical represented by the formula ##SPC20## wherein R 2 is selected from the group consisting of hydrogen, halo, lower alkyl, lower alkoxy, nitro and sulfamoyl; R 3 is selected from the group consisting of hydrogen, halo, lower alkyl, lower alkoxy and cyano; and p is an integer of from 1 to 4 inclusive; e. a diarylmethyl radical represented by the formula ##EQU3## wherein each Ar 1 is selected independently from the group consisting of phenyl and halophenyl; f. an arylaminoethyl radical represented by the formula ##SPC21## wherein each R 4 is independently selected from the group consisting of hydrogen, halo and lower alkyl; and a is an integer of from 1 to 2 inclusive; g. an arylether-alkyl radical represented by the formula -(CH.sub.2).sub.q --Q--Ar.sup.2 wherein Q is selected from the group consisting of oxygen and sulfur; Ar 2 is selected from the group consisting of phenyl, mono- and di-substituted phenyl and naphthyl, and wherein each substituent in said substituted phenyl is selected independently from the group consisting of halo, lower alkyl, lower alkoxy and allyl; and q is an integer of from 2 to 3 inclusive; h. a dihydrobenzofuranylmethyl radical represented by the formula ##SPC22## wherein R 5 is selected from the group consisting of hydrogen and halo; i. an aryl hydroxyethyl radical represented by the formula ##SPC23## wherein R 6 is selected from the group consisting of hydrogen, halo and lower alkoxy, and a is a integer of from 1 to 2 inclusive; k. a phenoxy-2-oxopropyl radical represented by the formula ##EQU4## wherein Ar 3 is selected from the group consisting of phenyl, halophenyl and dihalophenyl; and W is a pharmaceutically acceptable anion selected from the group consisting of chloride, bromide, iodide, methanesulfonate, p-toluenesulfonate, nitrate, sulfate, phosphate, acetate, propionate, glycolate, lactate, pyruvate, malonate, succinate, maleate, fumarate, malate, tartrate, citrate, benzoate, cinnamate, mandelate, ethanesulfonate, benzenesulfonate, cyclohexanesulfamate, salicylate and p-aminosalicylate.
Claim 3
Dependent Claim
2 words
1-[2,4-Dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-phenethylimidazolium chloride.
Claim 4
Dependent Claim
2 words
1-[2,4-Dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-phenethylimidazolium chloride.
Claim 5
Dependent Claim
2 words
1-[2,4-Dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-(p-fluorobenzoylmethyl)imidazolium chloride.
Claim 6
Dependent Claim
2 words
1-[2,4-Dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-(p-fluorobenzoylmethyl)imidazolium chloride.
Claim 7
Dependent Claim
30 words
A composition for combating bacterial and fungal microorganisms comprising an inert carrier material and as an active ingredient an effective antimicrobial amount of a quaternary imidazolium salt of claim 1.
Claim 8
Dependent Claim
13 words
A composition according to claim 4 wherein the imidazolium salt is 1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-phenethylimidazolium chloride.
Claim 9
Dependent Claim
13 words
A composition according to claim 4 wherein the imidazolium salt is 1-[2,4-dichloro-β-(2,4-dichlorobenzyloxy)phenethyl]-3-(p-fluorobenzoylmethyl)imidazolium chloride.
Claim 10
Dependent Claim
26 words
A method of combating bacterial and fungal microorganisms which comprises contacting said microorganisms with an antimicrobial effective amount of a quaternary imidazolium salt of claim 1.
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) | 1979-11-09 | 1980-05-10 | 1980-11-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-11-09 | 1984-05-10 | 1984-11-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-11-09 | 1988-05-10 | 1988-11-09 | $7700.00 | Window Closed / Lapsed |