3-aminopyrazolo heterocyclic derivatives, and use for colorimetric determinations

• US 5,234,818 A
• Filed: 12/21/1990
• Issued: 08/10/1993
• Est. Priority Date: 12/21/1989
• Status: Expired due to Fees

• Current Assignee: Boehringer Mannheim GmbH (Roche Holding AG)
• Original Assignee: Boehringer Mannheim GmbH (Roche Holding AG)
• Inventors: Zimmermann, Gerd, Siedel, Joachim, Frey, Gunter
• Primary Examiner(s): Wityshyn, Michael G.
• Assistant Examiner(s): Mohamed, Abdel A.
• Application Number:
  US07/631,797
• Time in Patent Office: 963 Days
• Field of Search: 435/28, 436/815, 436/904, 544/281, 546/121, 548/158, 548/154, 430/222
• US Class Current: 435/28
• CPC Class Codes: C07D 471/04 Ortho-condensed systems
• CPC Class Codes: C07D 487/04 Ortho-condensed systems
• CPC Class Codes: C07D 513/04 Ortho-condensed systems
• CPC Class Codes: C12Q 1/28 involving peroxidase
• CPC Class Codes: C12Q 2326/00 Chromogens for determinations of oxidoreductase enzymes
• CPC Class Codes: Y10S 436/815 Test for named compound or class of compounds
• CPC Class Codes: Y10S 436/904 Oxidation - reduction indicators

Abstract

The present invention is concerned with the use of certain 3-aminopyrazolo-heterocyclic compounds for the colorimetric determination of hydrogen peroxide, hydrogen peroxide-forming systems, peroxidase, peroxidate-active substances and electron-rich aromatic compounds. The present invention is also concerned with corresponding processes of determination and with agents appropriate therefor. Furthermore, the present invention is concerned with new 3-aminopyrazolo-heterocyclic compounds.

Claims

1. A method for colorimetric determination of hydrogen peroxide or hydrogen peroxide-forming systems, peroxidase or peroxidate-active substances by means of oxidative coupling of an electron-rich aromatic compound with a heterocyclic compound wherein the electron-rich aromatic compound enters into an oxidative coupling with p-phenylene diamine comprising a 3-amino pyrazolo heterocyclic derivative for color formation selected from the formulas consisting of II, III, IV, V, VI, VII, VIII, IX, X, XI, XII and XIII as follows:

##STR47## wherein --X--Y is --N═

CR² and wherein

R² is alkyl, alkenyl, alkoxy, alkylthio, aryl or aralkyl or wherein R² is unsubstituted or substituted by hydroxyl, dialkylphosphinyl, carboxyl, SO₃ H, PO₃ H₂, a salt of one of the acid residues or by amino, which amino is unsubstituted or substituted by one or two alkyls wherein said one or two alkyls are unsubstituted or substituted by hydroxyl, carboxyl or alkoxycarbonyl, and wherein when the amino is substituted by two alkyls these two alkyls are unjoined or are joined to form a ring which, apart from the first nitrogen atom of the amino group, are uninterrupted or interrupted by oxygen, sulphur or a second nitrogen atom, or the amino is unsubstituted or substituted by one or two from the group consisting of acyl, alkoxy, aralkoxycarbonyl, H₂ N--CO--, alkyl, aralkyl and arylcarbamoyl;

or R² is hydrogen, carboxyl, alkoxycarbonyl, carboxamido or halogen; and

wherein R³ is alkyl or aralkyl, and R⁴, R⁵, R⁶ and R⁷ each are hydrogen, alkyl, alkoxy, alkylthio, hydroxyl, aralkyl, aryl, carboxyl, carboxyamido, alkoxycarbonyl, cyano or amino, which amino is unsubstituted or substituted by one or two alkyls wherein said one or two alkyls are unsubstituted or substituted by one or two from the group consisting of hydroxyl, carboxyl, alkoxycarbonyl and halogen;

or two substituents on neighboring carbon atoms of a carbon chain form an alkylene radical which alkylene radical is unsubstituted or substituted or anellated with aryl, and tautomers and salts thereof.

2. The method of claim 1 wherein the 3-aminopyrozolo derivative is selected from the group of compounds consisting of formulas (II), (III), (IV), (VI), (VII), (IX), and tautomers and salts thereof.

3. The method of claim 1 wherein the electron-rich aromatic compound is a phenol or an aniline compound.

4. The method of claim 1 wherein the pyrazolo compound is 3-amino-2 methylpyrazolo [1,5-a]pyridine and salts thereof.

5. An reagent for colorimetric determination of hydrogen peroxide, hydrogen peroxide-forming systems, peroxidase or peroxidate-active substances by oxidative coupling, comprising an electron-rich aromatic compound and a heterocyclic compound, wherein the heterocyclic compound is a 3-aminopyrazolo derivative of claim 1.

6. The reagent of claim 5 wherein the electron-rich aromatic compound is a phenol or an aniline compound.

7. The reagent of claim 5 wherein a compound selected from the group of compounds which enter into an oxidative coupling with p-phenylenediamine is used as the electron-rich aromatic compound.

8. The reagent of claim 5 wherein the pyrazolo compound is 3-amino-2 methylpyrazolo [1,5-a]pyridine and salts thereof.

9. A method for the preparation of a reagent for the colorimetric determination of hydrogen peroxide, hydrogen peroxide-forming systems, peroxidase or peroxidate-active substances by oxidative coupling wherein the reagent comprises the 3-aminopyrazolo heterocyclic derivative of claim 1.

10. A process for the colorimetric determination of an election-rich aromatic compound by oxidative coupling thereof with a heterocyclic compound in the presence of an oxidation reagent wherein the heterocyclic compound is the 3-aminopyrazolo heterocyclic derivative of claim 1.

11. A reagent for the colorimetric determination of an electron-rich aromatic compound by oxidative coupling comprising a heterocyclic compound and an oxidation agent wherein the heterocyclic compound is a pyrazolo derivative of claim 1.

12. A method for the preparation of a reagent for colorimetric determination of an electron-rich aromatic compound by oxidative coupling wherein the reagent comprises a 3-aminopyrazolo heterocyclic derivative of claim 1.