US4954630A
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Resorufin derivatives
Assignee: Roche Diagnostics GmbH
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Filing: 1986-07-24
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Granted: 1990-09-04
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Expires: 2006-07-24
Abstract
Abstract The present invention provides resorufin derivatives of the general formulae: <IMAGE> wherein R1, R2, R3, R4 and R5, which can be the same or different, are hydrogen, halogen, carboxyl, carboxamido, lower alkoxycarbonyl, cyano or nitro groups or lower alkyl or lower alkoxy radicals, which can be substituted by carboxyl, carboxamido, lower alkoxycarbonyl, cyano or nitro groups, and wherein R4 and R5 can together also represent an anellated aromatic residue, Z is a bridge member, A is the residue of a ligand and n is a whole number of from 1 to 200. The present invention also provides processes for the preparation of these resorufin derivatives, as well as intermediates for the preparation thereof.
Inventors
- 👤 Christian Klein
- 👤 Hans-Georg Batz
- 👤 Rupert Herrmann
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 06:20
CPC Classifications
G; G01; G01N; G01N33/00; G01N33/48; G01N33/50; G01N33/53; G01N33/531; G01N33/532; G01N33/533; C; C07; C07D; C07D265/00; C07D265/28; C07D265/34; C07D265/38; Y; Y10; Y10S; Y10S436/00; Y10S436/80; Y10S530/00; Y10S530/802
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
123 words
A resorufin derivative of the formula: ##STR13## wherein R 1 , R 2 , R 3 , R 4 and R 5 , which can be the same or different, are hydrogen, halogen, carboxyl, carboxamido, C 1 -C 5 alkoxy-carbonyl, cyano, nitro, C 1 -C 5 alkyl, C 1 -C 5 alkoxy; or C 1 -C 5 alkyl or C 1 -C 5 alkoxy substituted by carboxyl, carboxamido, C 1 -C 5 alkoxy-carbonyl, cyano or nitro; or R 1 , R 2 and R 3 are as defined above and R 4 and R 5 together represent an anellated aromatic residue, Z is bridge member, A is the residue of a ligand and n is a whole number of from 1 to 200.
Claim 2
Dependent Claim
123 words
A resorufin derivative of the formula: ##STR13## wherein R 1 , R 2 , R 3 , R 4 and R 5 , which can be the same or different, are hydrogen, halogen, carboxyl, carboxamido, C 1 -C 5 alkoxy-carbonyl, cyano, nitro, C 1 -C 5 alkyl, C 1 -C 5 alkoxy; or C 1 -C 5 alkyl or C 1 -C 5 alkoxy substituted by carboxyl, carboxamido, C 1 -C 5 alkoxy-carbonyl, cyano or nitro; or R 1 , R 2 and R 3 are as defined above and R 4 and R 5 together represent an anellated aromatic residue, Z is bridge member, A is the residue of a ligand and n is a whole number of from 1 to 200.
Claim 3
Dependent Claim
21 words
The resorufin derivatives of claim 1 wherein Z is ##STR14## and m is zero or an integer from 1 to 3.
Claim 4
Dependent Claim
65 words
The resorufin derivative of claim 1 wherein R 4 and R 5 are individually selected from the group consisting of hydrogen, halogen, carboxyl, carboxamido, C 1 -C 5 alkoxy-carbonyl, cyano, nitro, C 1 -C 5 alkyl, C 1 -C 5 alkoxy; or C 1 -C 5 alkyl or C 1 -C 5 alkoxy substituted by carboxyl, carboxamido, C 1 -C 5 alkoxy-carbonyl, cyano or nitro.
Claim 5
Dependent Claim
32 words
The resorufin derivative of claim 1 wherein R 4 and R 5 together represent benzene, naphthalene; or benzene or naphthalene substituted by SO 3 H, COOH or C 1 -C 5 alkoxy.
Claim 6
Dependent Claim
24 words
The derivative of claim 1 designated 8-ethylresorufin-4-carboxylic acid (1-diphenylhydantoinylmethylcarbonyl) piperazide, high mannose glycopeptide labeled with N-(4-resorufinylcarbonyl)sarcosine, resorufin-4-carboxylic acid (L-thyroxyl) piperazide or resorufin-4-carboxylic acid (7-theophylline-ethylcarbonyl)piperazide.
Claim 7
Dependent Claim
117 words
In a ligand having a single colorimetric or fluorescent tag, the improvement wherein the tag is a resorufin derivative of the formula: ##STR15## wherein R 1 , R 2 , R 3 , R 4 and R 5 , which can be the same or different, are hydrogen, halogen, carboxyl, carboxamido, C 1 -C 5 alkoxy-carbonyl, cyano, nitro, C 1 -C 5 alkyl, C 1 -C 5 alkoxy; or C 1 -C 5 alkyl or C 1 -C 5 alkoxy substituted by carboxyl, carboxamido, C 1 -C 5 alkoxy-carbonyl, cyano, or nitro; or R 1 , R 2 and R 3 are as defined above and R 4 and R 5 together represent an anellated aromatic residue.
Claim 8
Dependent Claim
117 words
In a ligand having a single colorimetric or fluorescent tag, the improvement wherein the tag is a resorufin derivative of the formula: ##STR15## wherein R 1 , R 2 , R 3 , R 4 and R 5 , which can be the same or different, are hydrogen, halogen, carboxyl, carboxamido, C 1 -C 5 alkoxy-carbonyl, cyano, nitro, C 1 -C 5 alkyl, C 1 -C 5 alkoxy; or C 1 -C 5 alkyl or C 1 -C 5 alkoxy substituted by carboxyl, carboxamido, C 1 -C 5 alkoxy-carbonyl, cyano, or nitro; or R 1 , R 2 and R 3 are as defined above and R 4 and R 5 together represent an anellated aromatic residue.
Claim 9
Dependent Claim
64 words
The ligand of claim 6 wherein R 4 and R 5 are individually selected from the group consisting of hydrogen, halogen, carboxyl, carboxamido, C 1 -C 5 alkoxy-carbonyl, cyano, nitro, C 1 -C 5 alkyl, C 1 -C 5 alkoxy; or C 1 -C 5 alkyl or C 1 -C 5 alkoxy substituted by carboxyl, carboxamido, C 1 -C 5 alkoxy-carbonyl, cyano or nitro.
Claim 10
Dependent Claim
31 words
The ligand of claim 6 wherein R 4 and R 5 together represent benzene, naphthalene; or benzene or naphthalene substituted by SO 3 H, COOH or C 1 -C 5 alkoxy.
Claim 11
Dependent Claim
17 words
The resorufin derive of claim 1 wherein the residue A is hapten, antigen, antibody, substrate or carrier.
References Cited (Backward Citations)
US4714763A
Cited
US4737466A
Cited
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