Imidazole derivatives as redox indicators

• US 4,665,023 A
• Filed: 03/29/1985
• Issued: 05/12/1987
• Est. Priority Date: 03/31/1984
• Status: Expired due to Term

• Current Assignee: Boehringer Mannheim GmbH Sandhofer Strabe
• Original Assignee: Boehringer Mannheim GmbH (Roche Holding AG)
• Inventors: Merdes, Hartmut, Deneke, Ulfert, Wielinger, Hans, Guthlein, Werner, Kuhr, Manfred, Murawski, Hans-Rudiger
• Primary Examiner(s): Schwartz, Richard A.
• Application Number:
  US06/717,511
• Time in Patent Office: 774 Days
• Field of Search: 548/346, 548/336, 548/342, 548/343, 548/119, 546/94, 546/165, 435/28, 436/135
• US Class Current: 435/28
• CPC Class Codes: C07D 233/64 with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
• CPC Class Codes: C07D 403/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 405/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 455/04 containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
• CPC Class Codes: C12Q 1/28 involving peroxidase
• CPC Class Codes: C12Q 2326/00 Chromogens for determinations of oxidoreductase enzymes
• CPC Class Codes: Y10T 436/206664 Ozone or peroxide

Abstract

The present invention provides imidazole derivatives of the general formula: ##STR1## wherein R, R₁ and R₂ 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.

Claims

1. 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 R₁ and R₂, 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 R₄ 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 R₃ and R₅, 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 R₁ and R₂ cannot simultaneously be julolidine or tetrahydroquinoline and at least one R₄ of the substituents R₁ and R₂ must be a hydroxyl group;

or a salt thereof.

2. A compound of claim 1, where R₁ 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.

3. A compound of claim 1, wherein R₂ 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.

4. A compound of claim 1, wherein R₁ is the radical ##STR10## where R₄ is a hydroxyl, amino, or a mono or diloweralkylated amino group, and R₃ and R₅ may be hydrogen or loweralkyl or loweralkoxy groups, each of said groups optionally substituted by carboxyl.

5. A compound of claim 4, wherein R₄ is a mono or diloweralkylated amino group, further substituted by a sulfuric acid, phosphonic acid, or carboxylic acid residue on said loweralkyl groups.

6. A compound of claim 4, wherein R₄ is an hydroxy group.

7. A compound of claim 1, wherein R is hydrogen, tetrahydrofuranyl, cycloloweralkyl, or loweralkyl group.

8. 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.

11. Reagent for the detection of hydrogen peroxide or a peroxidate-active substance, comprising a compound of claim 1 and a peroxidase.

12. Reagent according to claim 11, wherein said reagent is in the form of tablets, lyophilisates, impregnated reagent carriers or reagent films.

13. 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.

9. 2-(3,5-Dimethoxy-4-hydroxyphenyl)-4-(5)-(4-dimethyl-aminophenyl)-5-(4)-methyl-(1H)-imidazole.

10. 2-[3,5-Di-(tert-butyl)-4-hydroxyphenyl]-4-(5)-(4-dimethylaminophenyl)-5-(4)-methyl-(1H)-imidazole.