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US4794079A
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Determination of hydrogen peroxide using fluorogenic dihydroquinolone and dihydrocoumarin indicators
Assignee: Bayer Corp
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Filing: 1985-09-30
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Granted: 1988-12-27
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Expires: 2005-09-30
Abstract
Abstract Fluorogenic indicator compounds responsive to the presence of hydrogen peroxide and methods and test compositions for determining hydrogen peroxide in a test sample. Preferred indicator compounds are 3,4-dihydrocoumarin derivatives and 3,4-dihydro-2-quinolone derivatives, especially those having a dialkylamino group at the 7-position. Such particularly preferred compounds are of the formula: ##STR1## wherein R 1 is hydrogen, cyano, or --COOR 6 , --CONHR 6 or --CON(R 6 ) 2 where R 6 is hydrogen, alkyl, alkenyl, or aryl; R 3 and R 4 are lower alkyl; and Y is ═0 or ═N--R 5 where R 5 is hydrogen or lower alkyl. The indicator compounds yield highly fluorescent products upon oxidation by hydrogen peroxide in the presence of a peroxidatively active substance and are useful in analytical systems which generate hydrogen peroxide in response to an analyte under determination in a test sample.
Inventors
- 👤 Robert T. Buckler
- 👤 Robert P. Hatch
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 11:17
CPC Classifications
C; C07; C07D; C07D407/00; C07D407/02; C07D407/12; C07D215/00; C07D215/02; C07D215/16; C07D215/38; C07D215/48; C07D215/54; C07D491/00; C07D491/02; C07D491/06; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/553; C07F9/576; C07F9/60; C12; C12Q; C12Q1/00; C12Q1/26; C12Q1/28; C12Q2326/00
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
104 words
A method for determining hydrogen peroxide comprising the steps of (a) contacting a test sample in the presence of a peroxidatively active substance with a compound of the formula: ##STR14## wherein R 1 is hydrogen, alkyl, alkenyl, aryl, or an electron withdrawing group; R 2 is hydroxyl or --NR 3 R 4 where R 3 and R 4 , which can be the same or different, are hydrogen, alkyl, alkenyl, or aryl; and Y is ═O or ═N--R 5 where R 5 is hydrogen or lower alkyl; and (b) measuring the fluorescence of a product resulting from oxidation of said compound by hydrogen peroxide.
Claim 2
Independent Claim
104 words
A method for determining hydrogen peroxide comprising the steps of (a) contacting a test sample in the presence of a peroxidatively active substance with a compound of the formula: ##STR14## wherein R 1 is hydrogen, alkyl, alkenyl, aryl, or an electron withdrawing group; R 2 is hydroxyl or --NR 3 R 4 where R 3 and R 4 , which can be the same or different, are hydrogen, alkyl, alkenyl, or aryl; and Y is ═O or ═N--R 5 where R 5 is hydrogen or lower alkyl; and (b) measuring the fluorescence of a product resulting from oxidation of said compound by hydrogen peroxide.
Claim 3
Dependent Claim
12 words
The method of claim 1 wherein the peroxidatively active substance is peroxidase.
Claim 4
Dependent Claim
23 words
The method of claim 1 wherein R 2 is --NR 3 R 4 and R 3 and R 4 are both lower alkyl.
Claim 5
Dependent Claim
22 words
The method of claim 3 wherein R 2 is --NR 3 R 4 and R 3 and R 4 are both methyl.
Claim 6
Dependent Claim
11 words
The method of claim 3 wherein Y is ═N--R 5 .
Claim 7
Dependent Claim
26 words
The method of claim 1 wherein R 1 is hydrogen, alkyl, alkenyl, aryl, cyano, carboxyl, carboalkoxy, carboaryloxy, carboxamide, sulfonyl, sulfoxy, sulfonium, phosphonyl, phosphonium, halo, or nitro.
Claim 8
Dependent Claim
63 words
The method of claim 1 wherein the compound is of the formula: ##STR15## wherein R 1 is hydrogen, cyano, or --COOR 6 , --CONHR 6 or --CON(R 6 ) 2 wherein R 6 is hydrogen, alkyl, alkenyl, or aryl; R 3 and R 4 , which can be the same or different, are lower alkyl; and R 5 is hydrogen or lower alkyl.
Claim 9
Dependent Claim
14 words
The method of claim 7 wherein R 3 and R 4 are both methyl.
Claim 10
Dependent Claim
21 words
The method of claim 8 wherein R 1 is 13 COOR 6 , --CONHR 6 or --CON(R 6 ) 2 .
Claim 11
Dependent Claim
12 words
The method of claim 9 wherein R 5 is hydrogen or methyl.
Claim 12
Dependent Claim
82 words
A test composition for determining hydrogen peroxide in a test sample comprising (a) a compound of the formula: ##STR16## wherein R 1 is hydrogen, alkyl, alkenyl, aryl, or an electron withdrawing group; R 2 is hydroxyl or --NR 3 R 4 where R 3 and R 4 , which can be the same or different, are hydrogen, alkyl, alkenyl, or aryl; and Y is ═O or ═N--R 5 where R 5 is hydrogen or lower alkyl; and (b) a peroxidatively active substance.
Claim 13
Dependent Claim
82 words
A test composition for determining hydrogen peroxide in a test sample comprising (a) a compound of the formula: ##STR16## wherein R 1 is hydrogen, alkyl, alkenyl, aryl, or an electron withdrawing group; R 2 is hydroxyl or --NR 3 R 4 where R 3 and R 4 , which can be the same or different, are hydrogen, alkyl, alkenyl, or aryl; and Y is ═O or ═N--R 5 where R 5 is hydrogen or lower alkyl; and (b) a peroxidatively active substance.
Claim 14
Dependent Claim
13 words
The test composition of claim 11 wherein the peroxidatively active substance is peroxidase.
Claim 15
Dependent Claim
24 words
The test composition of claim 11 wherein R 2 is --NR 3 R 4 and R 3 and R 4 are both lower alkyl.
Claim 16
Dependent Claim
15 words
The test composition of claim 13 wherein R 3 and R 4 are both methyl.
Claim 17
Dependent Claim
12 words
The test composition of claim 13 wherein Y is ═N--R 5 .
Claim 18
Dependent Claim
27 words
The test composition of claim 11 wherein R 1 is hydrogen, alkyl, alkenyl, aryl, cyano, carboxyl, carboalkoxy, carboaryloxy, carboxamide, sulfonyl, sulfoxy, sulfonium, phosphonyl, phosphonium, halo, or nitro.
Claim 19
Dependent Claim
64 words
The test composition of claim 11 wherein the compound is of the formula: ##STR17## wherein R 1 is hydrogen, cyano, or --COOR 6 , --CONHR 6 or --CON(R 6 ) 2 where R 6 is hydrogen, alkyl, alkenyl, or aryl; R 3 and R 4 , which can be the same or different, are lower alkyl; and R 5 is hydrogen or lower alkyl.
Claim 20
Dependent Claim
15 words
The test composition of claim 17 wherein R 3 and R 4 are both methyl.
Claim 21
Dependent Claim
21 words
The test composition of claim 18 wherein R 1 is --COOR 6 , --CONHR 6 or --CON(R 6 ) 2 .
Claim 22
Dependent Claim
13 words
The test composition of claim 19 wherein R 5 is hydrogen or methyl.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-12-27 | 1992-06-27 | 1992-12-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-12-27 | 1996-06-27 | 1996-12-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-12-27 | 2000-06-27 | 2000-12-27 | $7700.00 | Window Closed / Lapsed |