US4737466A
Expired / Lapsed
US
⏱️ 0.0 years remaining
N-acyldihydroresorufin derivatives, processes for their preparation, reagents containing them and the use thereof for determining hydrogen peroxide, peroxidate-acting compounds or peroxidase
Assignee: Roche Diagnostics GmbH
•
Filing: 1986-07-11
•
Granted: 1988-04-12
•
Expires: 2006-07-11
Abstract
Abstract The present invention provides N-acylidihydroresorufin derivatives of the general formula: <IMAGE> (I) wherein R1 is a lower alkyl, aryl or aralkyl radical, which can be substituted by carboxyl or sulphonic acid residues, R2, R3 and R4, which can be the same or different, are hydrogen or halogen atoms or lower alkyl or lower alkoxy radicals, Y is an -NR5R6 or -OR7 group, wherein R5 and R6 are, in each case, hydrogen atoms or lower alkyl radicals, which can be substituted by carboxyl or sulphonic acid residues, or together represent a hydrocarbon bridge optionally interrupted by hereto atoms and R7 is a lower alkyl radical which can be substituted by a lower alkoxy or poly-lower alkoxy radical.
Inventors
- 👤 Christian Klein
- 👤 Herbert von der Eltz
- 👤 Rupert Herrmann
- 👤 Martina Junius
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 13:25
CPC Classifications
C; C07; C07D; C07D265/00; C07D265/28; C07D265/34; C07D265/38; C12; C12Q; C12Q1/00; C12Q1/26; C12Q1/28; C12Q2326/00; Y; Y10; Y10S; Y10S436/00; Y10S436/904; Y10T; Y10T436/00; Y10T436/20; Y10T436/206664
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
103 words
An N-acyldihydroresorufin derivative of the formula: ##STR7## wherein R 1 is a C 1 -C 7 alkyl, C 6 -C 10 aryl or aralkyl wherein said aralkyl has 6 to 10 carbon atoms in the aryl moiety and 1-5 carbon atoms in the alkyl moiety and wherein said alkyl or said aryl as well as said aryl or alkyl moiety in the aralkyl are unsubstituted or substituted by carboxyl or sulphonic acid residues, R 2 , R 3 and R 4 , which can be the same or different, are hydrogen, halogen, C 1 -C 7 alkyl or C 1 -C 7 alkoxy,
Claim 2
Dependent Claim
103 words
An N-acyldihydroresorufin derivative of the formula: ##STR7## wherein R 1 is a C 1 -C 7 alkyl, C 6 -C 10 aryl or aralkyl wherein said aralkyl has 6 to 10 carbon atoms in the aryl moiety and 1-5 carbon atoms in the alkyl moiety and wherein said alkyl or said aryl as well as said aryl or alkyl moiety in the aralkyl are unsubstituted or substituted by carboxyl or sulphonic acid residues, R 2 , R 3 and R 4 , which can be the same or different, are hydrogen, halogen, C 1 -C 7 alkyl or C 1 -C 7 alkoxy,
Claim 3
Dependent Claim
137 words
Y is --NR 5 R 6 or --OR 7 wherein R 5 is hydrogen or a C 1 -C 7 alkyl, wherein said alkyl is unsubstituted or substituted by one or more carboxyl or sulphonic acid residues, and R 6 is hydrogen or a C 1 -C 7 alkyl wherein said alkyl is unsubstituted or substituted by one or more carboxyl or sulphonic acid residues or R 5 and R 6 together represent a C 2 -C 5 hydrocarbon bridge interrupted by 0 to 3 hetero atoms selected from the group consisting of oxygen, nitrogen and sulphur, and R 7 is C 1 -C 7 alkyl, or C 1 -C 7 alkyl substituted by a C 1 -C 7 alkoxy or poly-C 1 -C 7 alkoxy consisting of 2-5 alkoxy groups comprising 1 to 7 carbon atoms.
Claim 4
Dependent Claim
137 words
Y is --NR 5 R 6 or --OR 7 wherein R 5 is hydrogen or a C 1 -C 7 alkyl, wherein said alkyl is unsubstituted or substituted by one or more carboxyl or sulphonic acid residues, and R 6 is hydrogen or a C 1 -C 7 alkyl wherein said alkyl is unsubstituted or substituted by one or more carboxyl or sulphonic acid residues or R 5 and R 6 together represent a C 2 -C 5 hydrocarbon bridge interrupted by 0 to 3 hetero atoms selected from the group consisting of oxygen, nitrogen and sulphur, and R 7 is C 1 -C 7 alkyl, or C 1 -C 7 alkyl substituted by a C 1 -C 7 alkoxy or poly-C 1 -C 7 alkoxy consisting of 2-5 alkoxy groups comprising 1 to 7 carbon atoms.
Claim 5
Dependent Claim
36 words
The derivative of claim 1 wherein R 1 is selected from the group consisting of phenyl, naphthyl, phenyl carrying a C 1 -C 5 alkyl moiety and naphthyl carrying a C 1 -C 5 alkyl moiety.
Claim 6
Dependent Claim
10 words
The derivative of claim 1 wherein R 1 is benzyl.
Claim 7
Dependent Claim
29 words
The derivative of claim 1 wherein said N-acyldihydroresorufin derivative is selected from the group consisting of N-acetyldihydroresorufin-4-carboxylic acid morpholide, N-acetyl-8-bromodihydroresorufin-4-carboxylic acid morpholide, N-acetyldihydroresorufin-4-carboxylic acid carboxymethylamide and N-acetyl-8-chlorodihydroresorufin-4-carboxylic acid carboxymethylamide.
Claim 8
Dependent Claim
40 words
The derivative of claim 1 wherein one or more of the substituents R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are C 1 -C 7 alkyl or alkoxy.
Claim 9
Dependent Claim
17 words
The derivative of claim 5 wherein alkyl is methyl or ethyl and alkoxy is methoxy or ethoxy.
Claim 10
Dependent Claim
43 words
The derivative of claim 1 wherein Y is --NR 5 R 6 and R 5 and R 6 together represent a C 2 -C 5 hydrocarbon bridge interrupted by up to 3 heteroatoms selected from the group consisting of oxygen, nitrogen and sulphur.
Claim 11
Dependent Claim
16 words
The derivative of claim 7 wherein the --NR 5 R 6 moiety represents the morpholine radical.
Claim 12
Dependent Claim
71 words
A process for the determination of hydrogen peroxide, peroxidate-acting compounds or substances which produce hydrogen peroxide or peroxidate-acting compounds with oxygen in the presence of appropriate oxidases, comprising mixing one or more of an N-acyldihydroresorufin derivative according to claim 1, peroxidase and a buffer, with a sample containing a substance to be determined and measuring the change in absorption or emitted fluorescence as a measure of the substance to be determined.
Claim 13
Dependent Claim
74 words
A process for the determination of peroxidase, of compounds with peroxidase activity or of enzyme activities in systems producing hydrogen peroxide or peroxidate-acting compounds, comprising mixing one or more of an N-acyldihydroresorufin derivative according to claim 1, hydrogen peroxide or a peroxidate-acting compound, and a buffer with the sample which contains a substance to be determined and measuring the change in absorption or emitted fluorescence as a measure of the substance to be determined.
Claim 14
Dependent Claim
69 words
In a reagent for the detection of hydrogen peroxide, peroxidate-acting substances or substances which provide hydrogen peroxide or peroxidate-acting compounds with oxygen in the presence of appropriate oxidases, and wherein said reagent contains peroxidase as well as further necessary enzymes, one or more chromogenic or fluorogenic substrates and an appropriate buffer, the improvement wherein an N-acyldihydroresorufin derivative according to claim 1 is used as a chromogenic or fluorogenic substrate.
Claim 15
Dependent Claim
19 words
The reagent of claim 11 further comprising one or more wetting agents, stabilizers, galenical additives, organic acids structure formers.
Claim 16
Dependent Claim
30 words
The reagent of claim 11 wherein said reagent is in the form of a solution tablet, lyophilisate or, powder mixture or said reagent is applied to an appropriate carrier material.
Claim 17
Dependent Claim
28 words
The reagent of claim 11 wherein said derivative is selected from the group consisting of N-acetyldihydroresorufin-4-carboxylic acid morpholide, N-acetyl-8-bromodihydroresorufin-4-carboxylic acid morpholide, N-acetyldihydroresorufin-4-caboxylic acid carboxymethylamide and N-acetyl-8-chlorodihydroresorufin-4-carboxylic acid carboxymethylamide.
Claim 18
Dependent Claim
71 words
In a reagent for the determination of peroxidase, of compounds with peroxidase activity or of enzyme activities in systems producing hydrogen peroxide or peroxidate-acting compounds, wherein said reagent contains hydrogen peroxidase or peroxidate-acting substances, one or more chromogenic or fluorogenic substrates, necessary substrates and adjuvant enzymes, an appropriate buffer, further reagents and adjuvants, the improvement wherein an N-acyldihydroresorufin derivative according to claim 1 is used as a chromogenic or fluorogenic substrate.
Claim 19
Dependent Claim
29 words
The reagent of claim 15 wherein said derivative is selected from the group consisting of N-acetyldihydroresorufin-4-carboxylic acid morpholide, N-acetyl-8-bromodihydroresorufin-4-carboxylic acid morpholide, N-acetyldihydroresorufin-4-carboxylic acid carboxymethylamide and N-acetyl-8-chlorodihydroresorufin-4-carboxylic acid carboxy methylamide.
References Cited (Backward Citations)
US4567139A
Cited
US4556640A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-04-12 | 1991-10-12 | 1992-04-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-04-12 | 1995-10-12 | 1996-04-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-04-12 | 1999-10-12 | 2000-04-12 | $7700.00 | Window Closed / Lapsed |