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Imidazole derivatives as redox indicators

Assignee: Roche Diagnostics GmbH
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Filing: 1985-03-29
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Granted: 1987-05-12
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Expires: 2005-03-29
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Abstract

Abstract The present invention provides imidazole derivatives of the general formula: ##STR1## wherein R, R 1 and R 2 are defined hereinbelow. The present invention is also concerned with processes for the preparation of these imidazole derivatives and with the use thereof as redox indicators.

Inventors

  • 👤 Ulfert Deneke
  • 👤 Werner Guthlein
  • 👤 Manfred Kuhr
  • 👤 Hartmut Merdes
  • 👤 Hans-Rudiger Murawski
  • 👤 Hans Wielinger

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 21:11
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/64; C07D403/00; C07D403/02; C07D403/04; C07D405/00; C07D405/02; C07D405/04; C07D455/00; C07D455/03; C07D455/04; C12; C12Q; C12Q1/00; C12Q1/26; C12Q1/28; C12Q2326/00; Y; Y10; Y10T; Y10T436/00; Y10T436/20; Y10T436/206664

Claims Analysis

Total Claims: 16
Claim 1
Independent Claim 196 words
An imidazole derivative of the formula ##STR8## wherein R is a hydrogen atom, a tetrahydrofuranyl, cycloloweralkyl or loweralkyl radical, which can be substituted by hydroxyl, loweralkoxy, a sulphuric acid, phosphonic acid or carboxylic acid residue, as well as by a phenyl radical, and R 1 and R 2 , which are different, are julolidine radicals attached at C9, tetrahydroquinoline radicals attached at C6, which optionally carry on the nitrogen atom a loweralkyl radical which, in turn, can be substituted by a sulphuric acid, phosphonic acid or carboxylic acid residue, or radicals of the formula: ##STR9## in which R 4 is a hydroxyl or amino group or a mono- or diloweralkoxylated amino group, in which the loweralkyl radicals can carry a sulphuric acid, phosphonic acid or carboxylic acid residue, and R 3 and R 5 , which can be the same or different, are hydrogen atoms or loweralkyl or loweralkoxy radicals which are optionally substituted by a carboxyl group, with the proviso that R 1 and R 2 cannot simultaneously be julolidine or tetrahydroquinoline and at least one R 4 of the substituents R 1 and R 2 must be a hydroxyl group; or a salt thereof.
Claim 2
Dependent Claim 196 words
An imidazole derivative of the formula ##STR8## wherein R is a hydrogen atom, a tetrahydrofuranyl, cycloloweralkyl or loweralkyl radical, which can be substituted by hydroxyl, loweralkoxy, a sulphuric acid, phosphonic acid or carboxylic acid residue, as well as by a phenyl radical, and R 1 and R 2 , which are different, are julolidine radicals attached at C9, tetrahydroquinoline radicals attached at C6, which optionally carry on the nitrogen atom a loweralkyl radical which, in turn, can be substituted by a sulphuric acid, phosphonic acid or carboxylic acid residue, or radicals of the formula: ##STR9## in which R 4 is a hydroxyl or amino group or a mono- or diloweralkoxylated amino group, in which the loweralkyl radicals can carry a sulphuric acid, phosphonic acid or carboxylic acid residue, and R 3 and R 5 , which can be the same or different, are hydrogen atoms or loweralkyl or loweralkoxy radicals which are optionally substituted by a carboxyl group, with the proviso that R 1 and R 2 cannot simultaneously be julolidine or tetrahydroquinoline and at least one R 4 of the substituents R 1 and R 2 must be a hydroxyl group; or a salt thereof.
Claim 3
Dependent Claim 34 words
A compound of claim 1, where R 1 is julolidine or tetrahydroquinoline, wherein the nitrogen atom of said tetrahydroquinoline carries loweralkyl radical which may be substituted by a sulfuric, phosphonic or carboxylic acid residue.
Claim 4
Dependent Claim 38 words
A compound of claim 1, wherein R 2 is a julolidine or tetrahydroquinoline radical, optionally carrying on the nitrogen atom of said radical loweralkyl radical said loweralkyl radical optionally substituted by a sulfuric, phosphonic or carboxylic acid residue.
Claim 5
Dependent Claim 48 words
A compound of claim 1, wherein R 1 is the radical ##STR10## where R 4 is a hydroxyl, amino, or a mono or diloweralkylated amino group, and R 3 and R 5 may be hydrogen or loweralkyl or loweralkoxy groups, each of said groups optionally substituted by carboxyl.
Claim 6
Dependent Claim 31 words
A compound of claim 4, wherein R 4 is a mono or diloweralkylated amino group, further substituted by a sulfuric acid, phosphonic acid, or carboxylic acid residue on said loweralkyl groups.
Claim 7
Dependent Claim 12 words
A compound of claim 4, wherein R 4 is an hydroxy group.
Claim 8
Dependent Claim 14 words
A compound of claim 1, wherein R is hydrogen, tetrahydrofuranyl, cycloloweralkyl, or loweralkyl group.
Claim 9
Dependent Claim 32 words
A compound of claim 7, wherein R is loweralkyl group further substituted by a hydroxyl or loweralkoxy group, or a sulfuric acid, phosphonic acid, or carboxylic acid residue, or a phenyl group.
Claim 10
Dependent Claim 1 words
2-(3,5-Dimethoxy-4-hydroxyphenyl)-4-(5)-(4-dimethyl-aminophenyl)-5-(4)-methyl-(1H)-imidazole.
Claim 11
Dependent Claim 1 words
2-(3,5-Dimethoxy-4-hydroxyphenyl)-4-(5)-(4-dimethyl-aminophenyl)-5-(4)-methyl-(1H)-imidazole.
Claim 12
Dependent Claim 1 words
2-[3,5-Di-(tert-butyl)-4-hydroxyphenyl]-4-(5)-(4-dimethylaminophenyl)-5-(4)-methyl-(1H)-imidazole.
Claim 13
Dependent Claim 1 words
2-[3,5-Di-(tert-butyl)-4-hydroxyphenyl]-4-(5)-(4-dimethylaminophenyl)-5-(4)-methyl-(1H)-imidazole.
Claim 14
Dependent Claim 20 words
Reagent for the detection of hydrogen peroxide or a peroxidate-active substance, comprising a compound of claim 1 and a peroxidase.
Claim 15
Dependent Claim 21 words
Reagent according to claim 11, wherein said reagent is in the form of tablets, lyophilisates, impregnated reagent carriers or reagent films.
Claim 16
Dependent Claim 56 words
A method of detecting hydrogen peroxide or of a peroxide active substance which comprises adding to a sample containingg hydrogen peroxide or a peroxidate active substance a sufficient amount of a compound of claim 1 and a peroxidase to detect hydrogen peroxide or peroxidate active substances and detecting said hydrogen peroxide or peroxidate active substance thereby.

References Cited (Backward Citations)

US4535165A Cited
US4472406A Cited
US4567177A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1990-05-11 1990-11-10 1991-05-12 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1994-05-11 1994-11-10 1995-05-12 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1998-05-11 1998-11-10 1999-05-12 $7700.00 Window Closed / Lapsed

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