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US 2014/0212903 A1Published application
Azo mediators and methods of use thereof
AssigneeRoche Diagnostics Operations, Inc.
InventorsStacy H. Duvall, Peter Gebauer, Dieter Heindl, Carina Horn, Peter Kratzsch, Michael Marquant, Thomas Meier
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Abstract
Azo compounds are disclosed that do not form azoxy dimers and that do not have any reactive nitroso groups. Also disclosed are use of the azo compounds as mediators in optical and electrochemical diagnostic methods, as well as detection reagents, kits and test elements that include such azo compounds and that can be used in the diagnostic methods.
Claims20
An azo compound of the general formula (I):
- wherein R1 denotes a residue selected from the group consisting of OR7 and NR7R8;
- wherein R2, R3, R4 and R5 independently of one another denote a residue selected from the group consisting of H, alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heterocycloalkyl, heteroaryl, CN, COO−, halogen, O(alkyl), O(aryl), NH(alkyl), N(alkyl)2, N(alkyl)3+, NH(aryl), N(aryl)2, NO2 and SO3−, and wherein the alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heterocycloalkyl, heteroaryl, O(alkyl), O(aryl), NH(alkyl), N(alkyl)2, N(alkyl)3+, NH(aryl) or N(aryl)2 can contain one or more substituents selected from the group consisting of COO−, N(alkyl)3+, NH—C(═NH2)—NH2+, OH, O—(CH2CH2)n—OH, O—(CH2CH2)n—O(alkyl), OPO32−, PO32− and SO3−;
- wherein R6 denotes a residue selected from the group consisting of C(═X)NR9R10, C(═X)NHOH and C(═X)R9;
- wherein R7 denotes a residue selected from the group consisting of alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heterocycloalkyl and heteroaryl, and wherein the alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heterocycloalkyl or heteroaryl contains one or more substituents selected from the group consisting of COO−, N(alkyl)3+, NH—C(═NH2)—NH2+, OH, O—(CH2CH2)n—OH, O—(CH2CH2)n—O(alkyl), OPO32−, PO32− and SO3−;
- wherein R8 denotes a residue selected from the group consisting of alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heterocycloalkyl and heteroaryl, and wherein the alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heterocycloalkyl or heteroaryl can contain one or more substituents selected from the group consisting of COO−, N(alkyl)3+, NH—C(═NH2)—NH2+, OH, O—(CH2CH2)n—OH, O—(CH2CH2)n—O(alkyl), OPO32−, PO32− and SO3−;
- alternatively wherein R7 and R8 together with the N atom to which they are bound form a 5-membered to 7-membered heterocycle, and wherein the heterocycle can contain a further heteroatom selected from the group consisting of N, O and S and one or more substituents selected from the group consisting of COO−, N(alkyl)3+, NH—C(═NH2)—NH2+, OH, O—(CH2CH2)n—OH, O—(CH2CH2)n—O(alkyl), OPO32−, PO32− and SO3−;
- wherein R9 and R10 independently of one another denote a residue selected from the group consisting of alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heterocycloalkyl and heteroaryl, and wherein the alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heterocycloalkyl or heteroaryl can contain one or more substituents selected from the group consisting of CN, COO−, halogen, NH2, NH(alkyl), N(alkyl)2, N(alkyl)3+, NH(aryl), N(aryl)2, NH—C(═NH2)—NH2+, NO2, OH, O(alkyl), O—(CH2CH2)n—OH, O—(CH2CH2)n—O(alkyl), O(aralkyl), O(aryl), OPO32−, PO32− and SO3−;
- alternatively wherein R9 and R10 together with the N atom to which they are bound form a 5-membered to 7-membered heterocycle, and wherein the heterocycle can contain a further heteroatom selected from the group consisting of N, O and S and/or one or more substituents selected from the group consisting of CN, COO−, halogen, NH2, NH(alkyl), N(alkyl)2, N(alkyl)3+, NH(aryl), N(aryl)2, NH—C(═NH2)—NH2+, NO2, OH, O(alkyl), O—(CH2CH2)n—OH, O—(CH2CH2)n—O(alkyl), O(aralkyl), O(aryl), OPO32−, PO32− and SO3−;
- wherein X denotes a heteroatom selected from the group consisting of O and S, and n denotes an integer from 1 to 6, provided that at least two residues selected from the group consisting of R2, R3, R4 and R5 denote H, and wherein and the azo compound of the general formula (I) is not 2-(ethyl-{3-methyl-4-[(piperidin-1-ylcarbonyl)diazenyl]phenyl}-amino]ethanol.
6 more elements
A detection reagent for determining an analyte presence or concentration, the detection reagent comprising:
- (a) a flavine-, nicotinamide- or pyrroloquinoline quinone-dependent oxidoreductase;
- (b) a reducible flavine, nicotinamide or pyrroloquinoline quinone coenzyme;
- (c) an azo compound of the general formula (I):
- wherein R1 denotes a residue selected from the group consisting of OH, OR7, SR7, NHR7 and NR7R8;
- wherein R2, R3, R4 and R5 independently of one another denote a residue selected from the group consisting of H, alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heterocycloalkyl, heteroaryl, CN, COO−, halogen, O(alkyl), O(aryl), NH(alkyl), N(alkyl)2, N(alkyl)3+, NH(aryl), N(aryl)2, NO2 and SO3−, and wherein the alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heterocycloalkyl, heteroaryl, O(alkyl), O(aryl), NH(alkyl), N(alkyl)2, N(alkyl)3+, NH(aryl) or N(aryl)2 can contain one or more substituents selected from the group consisting of CN, COO−, halogen, NH2, NH(alkyl), N(alkyl)2, N(alkyl)3+, NH(aryl), N(aryl)2, NH—C(═NH2)—NH2+, NO2, OH, O—(CH2CH2)n—OH, O—(CH2CH2)n—O(alkyl), O(alkyl), O(aralkyl), O(aryl), OPO32−, PO32− and SO3−;
- wherein R6 denotes a residue selected from the group consisting of CN, C(═X)NH2, C(═X)NHR9, C(═X)NR9R10, C(═X)NHOH and C(═X)R9;
- wherein R7 and R8 independently of one another denote a residue selected from the group consisting of alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heterocycloalkyl and heteroaryl, and wherein the alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heterocycloalkyl or heteroaryl can contain one or more substituents selected from the group consisting of CN, COO−, halogen, NH2, NH(alkyl), N(alkyl)2, N(alkyl)3+, NH(aryl), N(aryl)2, NH—C(═NH2)—NH2+, NO2, OH, O—(CH2CH2)n—OH, O—(CH2CH2)n—O(alkyl), O(alkyl), O(aralkyl), O(aryl), OPO32−, PO32− and SO3−;
- alternatively wherein R7 and R8 together with the N atom to which they are bound form a 5-membered to 7-membered heterocycle, and wherein the heterocycle can contain a further heteroatom selected from the group consisting of N, O and S and/or one or more substituents selected from the group consisting of CN, COO−, halogen, NH2, NH(alkyl), N(alkyl)2, N(alkyl)3+, NH(aryl), N(aryl)2, NH—C(═NH2)—NH2+, NO2, OH, O—(CH2CH2)n—OH, O—(CH2CH2)n—O(alkyl), O(alkyl), O(aralkyl), O(aryl), OPO32−, PO32− and SO3−;
- wherein R9 and R10 independently of one another denote a residue selected from the group consisting of alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heterocycloalkyl and heteroaryl, and wherein the alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heterocycloalkyl or heteroaryl can contain one or more substituents selected from the group consisting of CN, COO−, halogen, NH2, NH(alkyl), N(alkyl)2, N(alkyl)3+, NH(aryl), N(aryl)2, NH—C(═NH2)—NH2+, NO2, OH, O—(CH2CH2)n—OH, O—(CH2CH2)n—O(alkyl), O(alkyl), O(aralkyl), O(aryl), OPO32−, PO32− and SO3−;
- alternatively wherein R9 and R10 together with the N atom to which they are bound form a 5-membered to 7-membered heterocycle, and wherein the heterocycle can contain a further heteroatom selected from the group consisting of N, O and S and/or one or more substituents selected from the group consisting of CN, COO−, halogen, NH2, NH(alkyl), N(alkyl)2, N(alkyl)3+, NH(aryl), N(aryl)2, NH—C(═NH2)—NH2+, NO2, OH, O—(CH2CH2)n—OH, O—(CH2CH2)n—O(alkyl), O(alkyl), O(aralkyl), O(aryl), OPO32−, PO32− and SO3−;
- wherein X denotes a heteroatom selected from the group consisting of O and S, and wherein n denotes an integer from 1 to 6;
- and
- (d) optionally a reducible optical indicator.
10 more elements
Dependencies are inferred from the claim text.