US4468467A
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US
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Diazonium salt for bilirubin assay
Assignee: Clinical Diagnostic Systems Inc
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Filing: 1982-02-01
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Granted: 1984-08-28
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Expires: 2002-02-01
Abstract
Abstract Diazonium salts which are useful in an assay for bilirubin are disclosed. The novel salts have the structural formula: ##STR1## wherein X - is a stabilizing anion, Y is CO-- or SO 2 --; and R 1 and R 2 are independently selected from hydrogen, alkyl, aryl, carboxyalkyl and hydroxyalkyl providing R 1 and R 2 are not both hydrogen; R 3 and R 4 are independently selected from groups such that the sum of the Hammett sigma values for R 3 and R 4 does not exceed +0.4 or R 3 and R 4 represent the carbon atoms necessary to complete a fused carbocyclic ring structure. Reagent compositions, analytical elements and methods which use the described diazonium salt are also disclosed.
Inventors
- 👤 Bruce E. Babb
- 👤 Glen M. Dappen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 09:06
CPC Classifications
G; G01; G01N; G01N33/00; G01N33/48; G01N33/50; G01N33/72; G01N33/728; Y; Y10; Y10S; Y10S436/00; Y10S436/903; Y10T; Y10T436/00; Y10T436/14; Y10T436/145555; Y10T436/146666
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
93 words
A compound of the formula: ##STR6## wherein X - is a stabilizing anion, Y is CO-- or SO 2 --; and R 1 and R 2 are independently selected from hydrogen, alkyl, aryl, carboxyalkyl and hydroxyalkyl providing R 1 and R 2 are not both hydrogen; R 3 and R 4 are independently selected from groups such that the sum of the Hammett sigma values for R 3 and R 4 does not exceed +0.4 or R 3 and R 4 represent the carbon atoms necessary to complete a fused carbocyclic ring structure.
Claim 2
Dependent Claim
93 words
A compound of the formula: ##STR6## wherein X - is a stabilizing anion, Y is CO-- or SO 2 --; and R 1 and R 2 are independently selected from hydrogen, alkyl, aryl, carboxyalkyl and hydroxyalkyl providing R 1 and R 2 are not both hydrogen; R 3 and R 4 are independently selected from groups such that the sum of the Hammett sigma values for R 3 and R 4 does not exceed +0.4 or R 3 and R 4 represent the carbon atoms necessary to complete a fused carbocyclic ring structure.
Claim 3
Dependent Claim
119 words
A reagent composition comprising an acid and a diazonium salt or reagents capable of producing a diazonium salt when contacted with water wherein said diazonium salt is represented by the formula: ##STR7## wherein X - is a stabilizing anion, Y is CO-- or SO 2 --; and R 1 and R 2 are independently selected from hydrogen, alkyl, aryl, carboxyalkyl and hydroxyalkyl providing R 1 and R 2 are not both hydrogen; R 3 and R 4 are independently selected from groups such that the sum of the Hammett sigma values for R 3 and R 4 does not exceed +0.4 or R 3 and R 4 represent the carbon atoms necessary to complete a fused carboxylic ring structure.
Claim 4
Dependent Claim
119 words
A reagent composition comprising an acid and a diazonium salt or reagents capable of producing a diazonium salt when contacted with water wherein said diazonium salt is represented by the formula: ##STR7## wherein X - is a stabilizing anion, Y is CO-- or SO 2 --; and R 1 and R 2 are independently selected from hydrogen, alkyl, aryl, carboxyalkyl and hydroxyalkyl providing R 1 and R 2 are not both hydrogen; R 3 and R 4 are independently selected from groups such that the sum of the Hammett sigma values for R 3 and R 4 does not exceed +0.4 or R 3 and R 4 represent the carbon atoms necessary to complete a fused carboxylic ring structure.
Claim 5
Dependent Claim
12 words
The reagent composition according to claim 2 comprising a diazobilirubin accelerating agent.
Claim 6
Dependent Claim
128 words
A dry analytical element comprising a carrier matrix having therein a reagent composition comprising an acid and a diazonium salt or reagents capable of producing a diazonium salt when contacted with water wherein said diazonium salt has the structural formula: ##STR8## wherein X - is a stabilizing anion, Y is CO-- or SO 2 --; and R 1 and R 2 are independently selected from hydrogen, alkyl, aryl, carboxyalkyl and hydroxyalkyl providing R 1 and R 2 are not both hydrogen; R 3 and R 4 are independently selected from groups such that the sum of the Hammett sigma values for R 3 and R 4 does not exceed +0.4 or R 3 and R 4 represent the carbon atoms necessary to complete a fused carbocyclic ring structure.
Claim 7
Dependent Claim
128 words
A dry analytical element comprising a carrier matrix having therein a reagent composition comprising an acid and a diazonium salt or reagents capable of producing a diazonium salt when contacted with water wherein said diazonium salt has the structural formula: ##STR8## wherein X - is a stabilizing anion, Y is CO-- or SO 2 --; and R 1 and R 2 are independently selected from hydrogen, alkyl, aryl, carboxyalkyl and hydroxyalkyl providing R 1 and R 2 are not both hydrogen; R 3 and R 4 are independently selected from groups such that the sum of the Hammett sigma values for R 3 and R 4 does not exceed +0.4 or R 3 and R 4 represent the carbon atoms necessary to complete a fused carbocyclic ring structure.
Claim 8
Dependent Claim
12 words
The dry analytical element according to claim 4 comprising a diazobilirubin promoter.
Claim 9
Dependent Claim
136 words
A dry analytical element comprising a support having thereon a nonfibrous isotropically porous spreading layer having therein a reagent composition comprising an acid and a diazonium salt or reagents capable of producing a diazonium salt when contacted with water wherein said diazonium salt is represented by the formula: ##STR9## wherein X - is a stabilizing anion, Y is CO-- or SO 2 --; and R 1 and R 2 are independently selected from hydrogen, alkyl, aryl, carboxyalkyl and hydroxyalkyl providing R 1 and R 2 are not both hydrogen; R 3 and R 4 are independently selected from groups such that the sum of the Hammett sigma values of R 3 and R 4 does not exceed +0.4 or R 3 and R 4 represent the carbon atoms necessary to complete a fused carbocyclic ring structure.
Claim 10
Dependent Claim
136 words
A dry analytical element comprising a support having thereon a nonfibrous isotropically porous spreading layer having therein a reagent composition comprising an acid and a diazonium salt or reagents capable of producing a diazonium salt when contacted with water wherein said diazonium salt is represented by the formula: ##STR9## wherein X - is a stabilizing anion, Y is CO-- or SO 2 --; and R 1 and R 2 are independently selected from hydrogen, alkyl, aryl, carboxyalkyl and hydroxyalkyl providing R 1 and R 2 are not both hydrogen; R 3 and R 4 are independently selected from groups such that the sum of the Hammett sigma values of R 3 and R 4 does not exceed +0.4 or R 3 and R 4 represent the carbon atoms necessary to complete a fused carbocyclic ring structure.
Claim 11
Dependent Claim
12 words
The dry analytical element according to claim 6 comprising a diazobilirubin promoter.
Claim 12
Dependent Claim
16 words
The dry analytical element according to claim 6 wherein said spreading layer is translucent when wet.
Claim 13
Dependent Claim
167 words
A dry analytical element comprising a support having thereon, in order: (1) a layer comprising a hydrophilic binder and a buffer capable of buffering the layer to a pH of about 3.0-7.0, (2) a nonfibrous isotropically porous spreading layer which is translucent when wet having therein (a) an acid, (b) a diazobilirubin promoter and, (c) a diazonium salt or reagents capable of producing a diazonium salt when contacted with water wherein said diazonium salt is represented by the formula: ##STR10## wherein X - is a stabilizing anion, Y is CO-- or SO 2 --; and R 1 and R 2 are independently selected from hydrogen, alkyl, aryl, carboxyalkyl and hydroxyalkyl providing R 1 and R 2 are not both hydrogen; R 3 and R 4 are independently selected from groups such that the sum of the Hammett sigma values for R 3 and R 4 does not exceed +0.4 or R 3 and R 4 represent the carbon atoms necessary to complete a fused carbocyclic ring structure.
Claim 14
Dependent Claim
167 words
A dry analytical element comprising a support having thereon, in order: (1) a layer comprising a hydrophilic binder and a buffer capable of buffering the layer to a pH of about 3.0-7.0, (2) a nonfibrous isotropically porous spreading layer which is translucent when wet having therein (a) an acid, (b) a diazobilirubin promoter and, (c) a diazonium salt or reagents capable of producing a diazonium salt when contacted with water wherein said diazonium salt is represented by the formula: ##STR10## wherein X - is a stabilizing anion, Y is CO-- or SO 2 --; and R 1 and R 2 are independently selected from hydrogen, alkyl, aryl, carboxyalkyl and hydroxyalkyl providing R 1 and R 2 are not both hydrogen; R 3 and R 4 are independently selected from groups such that the sum of the Hammett sigma values for R 3 and R 4 does not exceed +0.4 or R 3 and R 4 represent the carbon atoms necessary to complete a fused carbocyclic ring structure.
Claim 15
Dependent Claim
15 words
The dry analytical element according to claim 9 wherein layer (1) comprises a cationic mordant.
Claim 16
Dependent Claim
137 words
In a method for the quantitation of bilirubin in a sample said method comprising the steps of (1) contacting said sample with a reagent composition comprising an acid and a diazonium salt and (2) measuring the amount of azobilirubin formed the improvement wherein said diazonium salt has the formula: ##STR11## wherein X - is a stabilizing anion, Y is CO-- or SO 2 --; and R 1 and R 2 are independently selected from hydrogen, alkyl, aryl, carboxyalkyl and hydroxyalkyl providing R 1 and R 2 are not both hydrogen; R 3 and R 4 are independently selected from groups such that the sum of the Hammett sigma values for R 3 and R 4 does not exceed +0.4 or R 3 and R 4 represent the carbon atoms necessary to complete a fused carbocyclic ring structure.
Claim 17
Dependent Claim
137 words
In a method for the quantitation of bilirubin in a sample said method comprising the steps of (1) contacting said sample with a reagent composition comprising an acid and a diazonium salt and (2) measuring the amount of azobilirubin formed the improvement wherein said diazonium salt has the formula: ##STR11## wherein X - is a stabilizing anion, Y is CO-- or SO 2 --; and R 1 and R 2 are independently selected from hydrogen, alkyl, aryl, carboxyalkyl and hydroxyalkyl providing R 1 and R 2 are not both hydrogen; R 3 and R 4 are independently selected from groups such that the sum of the Hammett sigma values for R 3 and R 4 does not exceed +0.4 or R 3 and R 4 represent the carbon atoms necessary to complete a fused carbocyclic ring structure.
Claim 18
Dependent Claim
18 words
The invention according to claim 1, 2, 4, 6, 9 or 11 wherein Y is SO 2 --.
Claim 19
Dependent Claim
28 words
The invention according to claim 1, 2, 4, 6, 9 or 11 wherein X - is the anion of a Lewis acid coordinatively saturated by a hydrogen halide.
Claim 20
Dependent Claim
17 words
The invention according to claim 1, 2, 4, 6, 9 or 11 wherein said anion is hexafluorophosphate.
Claim 21
Dependent Claim
22 words
The invention according to claim 1, 2, 4, 6, 9 or 11 wherein R 1 is hydrogen and R 2 is carboxymethyl.
Claim 22
Dependent Claim
18 words
The invention according to claim 2, 4, 6, 9 or 11 wherein said diazonium salt is 4-(N-carboxymethylsulfamyl)benzenediazonium hexafluorophosphate.
Claim 23
Dependent Claim
2 words
4-(N-carboxymethylsulfamyl)benzenediazonium hexafluorophosphate.
Claim 24
Dependent Claim
2 words
4-(N-carboxymethylsulfamyl)benzenediazonium hexafluorophosphate.
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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) | 1987-08-28 | 1988-02-27 | 1988-08-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-08-28 | 1992-02-27 | 1992-08-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-08-28 | 1996-02-27 | 1996-08-28 | $7700.00 | Window Closed / Lapsed |