US4558130A
Expired / Lapsed
US
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Fluorogenic dihydroquinolone and dihydrocoumarin indicators for hydrogen peroxide
Assignee: Bayer Corp
•
Filing: 1984-03-27
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Granted: 1985-12-10
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Expires: 2004-03-27
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 ═O 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 05:07
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: 15
Claim 1
Independent Claim
63 words
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.
Claim 2
Dependent Claim
63 words
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.
Claim 3
Dependent Claim
23 words
The compound of claim 1 wherein R 2 is --NR 3 R 4 and R 3 and R 4 are both lower alkyl.
Claim 4
Dependent Claim
14 words
The compound of claim 2 wherein R 3 and R 4 are both methyl.
Claim 5
Dependent Claim
11 words
The compound of claim 2 wherein Y is ═N--R 5 .
Claim 6
Dependent Claim
26 words
The compound 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 7
Dependent Claim
56 words
A compound of the formula: ##STR15## 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 8
Dependent Claim
56 words
A compound of the formula: ##STR15## 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 9
Dependent Claim
14 words
The compound of claim 6 wherein R 3 and R 4 are both methyl.
Claim 10
Dependent Claim
20 words
The compound of claim 7 wherein R 1 is --COOR 6 , --CONHR 6 or --CON(R 6 ) 2 .
Claim 11
Dependent Claim
12 words
The compound of claim 8 wherein R 5 is hydrogen or methyl.
Claim 12
Dependent Claim
48 words
A compound of the formula: ##STR16## 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; and Y is ═O or ═N--R 5 where R 5 is hydrogen or lower alkyl.
Claim 13
Dependent Claim
48 words
A compound of the formula: ##STR16## 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; and Y is ═O or ═N--R 5 where R 5 is hydrogen or lower alkyl.
Claim 14
Dependent Claim
9 words
The compound of claim 10 wherein Y is ═O.
Claim 15
Dependent Claim
19 words
The compound of claim 11 wherein R 1 is --COOR 6 where R 6 is hydrogen or lower alkyl.
References Cited (Backward Citations)
US4065456A
Cited
US4105665A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-12-09 | 1989-06-10 | 1989-12-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-12-09 | 1993-06-10 | 1993-12-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-12-09 | 1997-06-10 | 1997-12-10 | $7700.00 | Window Closed / Lapsed |