US4670385A
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US
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Compositions and elements containing triarylmethane leuco dyes and methods using same
Assignee: Clinical Diagnostic Systems Inc
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Filing: 1984-05-21
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Granted: 1987-06-02
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Expires: 2004-05-21
Abstract
Abstract A particular class of triarylmethane leuco dyes are useful in analytical compositions, elements and methods. These leuco dyes are triarylmethane compounds having an aromatic heterocyclic moiety attached to the central methane carbon and which, upon interaction with hydrogen peroxide, provide dyes having a maximum absorption at a wavelength equal to or greater than about 600 nm. Particularly useful leuco dyes have the structure: ##STR1## wherein R is a 5- to 15-membered aromatic heterocyclic moiety; and R' and R" are independently open chain or cyclic amines. These compounds are useful for providing detectable dyes in compositions and elements useful for detection of hydrogen peroxide or other analytes which react to produce hydrogen peroxide in aqueous liquids, e.g. biological fluids.
Inventors
- 👤 Bruce E. Babb
- 👤 Daniel S. Daniel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 14:52
CPC Classifications
C; C12; C12Q; C12Q1/00; C12Q1/26; C12Q1/28; C12Q2326/00; C12Q2326/40; Y; Y10; Y10S; Y10S435/00; Y10S435/805; Y10T; Y10T436/00; Y10T436/20; Y10T436/206664
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
90 words
A composition for the determination of hydrogen peroxide in an aqueous liquid, said composition comprising a substance having peroxidative activity and a triarylmethane leuco dye which provides a dye having a maximum absorption at a wavelength equal to or greater than about 600 nm upon interaction with hydrogen peroxide, said leuco dye having the structure: ##STR33## wherein R is a 5- to 15-membered aromatic heterocyclic moiety provided that said moiety does not have an --NH-- group in the ring; and R' and R" are independently open chain or cyclic amines.
Claim 2
Dependent Claim
90 words
A composition for the determination of hydrogen peroxide in an aqueous liquid, said composition comprising a substance having peroxidative activity and a triarylmethane leuco dye which provides a dye having a maximum absorption at a wavelength equal to or greater than about 600 nm upon interaction with hydrogen peroxide, said leuco dye having the structure: ##STR33## wherein R is a 5- to 15-membered aromatic heterocyclic moiety provided that said moiety does not have an --NH-- group in the ring; and R' and R" are independently open chain or cyclic amines.
Claim 3
Dependent Claim
13 words
The composition of claim 1 wherein said substance having peroxidative activity is peroxidase.
Claim 4
Dependent Claim
64 words
The composition of claim 1 wherein said leuco dye has the structure: ##STR34## wherein R 1 , R 2 , R 3 and R 4 are independently alkyl, alkaryl, aralkyl, aryl or a heterocyclic moiety, or R 1 and R 2 or R 3 and R 4 independently taken together with the respective nitrogen atom, represent the atoms necessary to complet a heterocyclic ring,
Claim 5
Dependent Claim
29 words
The composition of claim 3 wherein each of R 1 , R 2 , R 3 and R 4 is a lower alkyl of 1 to 6 carbon atoms.
Claim 6
Dependent Claim
12 words
The composition of claim 3 wherein R is a π-deficient heterocycliic moiety.
Claim 7
Dependent Claim
16 words
The composition of claim 3 wherein R 1 =R 3 and R 2 =R 4 .
Claim 8
Dependent Claim
20 words
The composition of claim 6 wherein R 1 , R 2 , R 3 and R 4 are the same.
Claim 9
Dependent Claim
17 words
The composition of claim 3 wherein said leuco dye is selected from the group consisting of: ##STR35##
Claim 10
Dependent Claim
14 words
The composition of claim 8 wherein said leuco dye is compound I or II.
Claim 11
Dependent Claim
104 words
A composition for the determination of an analyte in an aqueous liquid, said composition comprising: (1) an interactive composition which produces hydrogen peroxide upon interaction with said analyte, (2) a substance having peroxidative activity and (3) a triarylmethane leuco dye which provides a dye having a maximum absorption at a wavelength equal to or greater than about 600 nm upon interaction with hydrogen peroxide,said leuco dye having the structure: ##STR36## wherein R is a 5- to 15-membereed aromatic heterocyclic moiety provided that said moiety does not have an --NH-- group in the ring; and R' and R" are independently open chain or cyclic amines.
Claim 12
Dependent Claim
104 words
A composition for the determination of an analyte in an aqueous liquid, said composition comprising: (1) an interactive composition which produces hydrogen peroxide upon interaction with said analyte, (2) a substance having peroxidative activity and (3) a triarylmethane leuco dye which provides a dye having a maximum absorption at a wavelength equal to or greater than about 600 nm upon interaction with hydrogen peroxide,said leuco dye having the structure: ##STR36## wherein R is a 5- to 15-membereed aromatic heterocyclic moiety provided that said moiety does not have an --NH-- group in the ring; and R' and R" are independently open chain or cyclic amines.
Claim 13
Dependent Claim
64 words
The composition of claim 10 wherein said leuco dye has the structure: ##STR37## wherein R 1 , R 2 , R 3 and R 4 are independently alkyl, alkaryl, aralkyl, aryl or a heterocyclic moiety, or R 1 and R 2 or R 3 and R 4 independently taken together with the respective nitrogen atom, reperesent the atoms necessary to complete a heterocyclic ring.
Claim 14
Dependent Claim
94 words
A dry analytical element for the determination of hydrogen peroxide in an aqueous liquid, said element comprising: (1) a substance having peroxidative activity, and (2) a triarylmethane leuco dye which provides a dye having a maximum absorption at a wavelength equal to or greater than about 600 nm upon interaction with hydrogen peroxide, said leuco dye having the structure: ##STR38## wherein R is a 5- to 15-membered aromatic heterocyclic moiety provided that said moiety does not have an --NH-- group in the ring; and R' and R" are independently open chain or cyclic amines.
Claim 15
Dependent Claim
94 words
A dry analytical element for the determination of hydrogen peroxide in an aqueous liquid, said element comprising: (1) a substance having peroxidative activity, and (2) a triarylmethane leuco dye which provides a dye having a maximum absorption at a wavelength equal to or greater than about 600 nm upon interaction with hydrogen peroxide, said leuco dye having the structure: ##STR38## wherein R is a 5- to 15-membered aromatic heterocyclic moiety provided that said moiety does not have an --NH-- group in the ring; and R' and R" are independently open chain or cyclic amines.
Claim 16
Dependent Claim
64 words
The element of claim 12 wherein said leuco dye has the structure: ##STR39## wherein R 1 , R 2 , R 3 and R 4 are independently alkyl, alkaryl, aralkyl, aryl or a heterocyclic moiety, or R 1 and R 2 or R 3 and R 4 independently taken together with the respective nitrogen atom, represent the atoms necessary to complete a heterocyclic ring.
Claim 17
Dependent Claim
18 words
The element of claim 12 comprising an interactive composition which produces hydrogen peroxide upon interaction with an analyte.
Claim 18
Dependent Claim
156 words
A dry analytical element for the determination of an analyte in an aqueous liquid, said element comprising: a support having thereon a porous spreading zone and (1) an interactive composition which produces hydrogen peroxide upon interaction with said analyte, (2) a substance having peroxidative activity and (3) a triarylmethane leuco dye which provides a dye having a maximum absorption at a wavelength equal to or greater than about 600 nm upon interaction with hydrogen peroxide, said leuco dye having the structure: ##STR40## wherein R is a 5- to 15-membered aromatic heterocyclic moiety provided that said moiety does not have an --NH-- group in the ring; and R 1 , R 2 , R 3 and R 4 are independently alkyl, alkaryl, aralkyl, aryl or a heterocyclic moiety, or R 1 and R 2 or R 3 and R 4 independently taken together with the respective nitrogen atom reperesent the atoms necessary to complete a heterocyclic ring.
Claim 19
Dependent Claim
156 words
A dry analytical element for the determination of an analyte in an aqueous liquid, said element comprising: a support having thereon a porous spreading zone and (1) an interactive composition which produces hydrogen peroxide upon interaction with said analyte, (2) a substance having peroxidative activity and (3) a triarylmethane leuco dye which provides a dye having a maximum absorption at a wavelength equal to or greater than about 600 nm upon interaction with hydrogen peroxide, said leuco dye having the structure: ##STR40## wherein R is a 5- to 15-membered aromatic heterocyclic moiety provided that said moiety does not have an --NH-- group in the ring; and R 1 , R 2 , R 3 and R 4 are independently alkyl, alkaryl, aralkyl, aryl or a heterocyclic moiety, or R 1 and R 2 or R 3 and R 4 independently taken together with the respective nitrogen atom reperesent the atoms necessary to complete a heterocyclic ring.
Claim 20
Dependent Claim
16 words
The element of claim 15 wherein R 1 =R 3 and R 2 =R 4 .
Claim 21
Dependent Claim
13 words
The element of claim 15 wherein said substance having peroxidative activity is peroxidase.
Claim 22
Dependent Claim
20 words
The element of claim 15 wherein R 1 , R 2 , R 3 and R 4 are the same.
Claim 23
Dependent Claim
29 words
The element of claim 18 wherein each of R 1 , R 2 , R 3 and R 4 is a lower alkyl of 1 to 6 carbon atoms.
Claim 24
Dependent Claim
17 words
The element of claim 15 wherein said leuco dye is selected from the group consisting of: ##STR41##
Claim 25
Dependent Claim
14 words
The element of claim 20 wherein said leuco dye is compound I or II.
Claim 26
Independent Claim
127 words
A method for determing hydrogen peroxide or an analyte which reacts to produce hydrogen peroxide in an aqueous liquid, said method comprising the steps of: A. physically contacting a sample of said liquid with a composition comprising a substance having peroxidative activity and tariarylmethane leuco dye which provides a dye having a maximum absorption at a wavelength equal to or greater than about 600 nm upon interaction with hydrogen peroxide, said leuco dye having the sructure: ##STR42## wherein R is a 5- to 15-membered aromatic heterocyclic moiety provided that said moiety does not have an --NH-- group in the ring; and R' and R" are independently open chain or cyclic amines; and B. detecting said dye at a wavelength equal to or greater than about 600 nm.
Claim 27
Independent Claim
127 words
A method for determing hydrogen peroxide or an analyte which reacts to produce hydrogen peroxide in an aqueous liquid, said method comprising the steps of: A. physically contacting a sample of said liquid with a composition comprising a substance having peroxidative activity and tariarylmethane leuco dye which provides a dye having a maximum absorption at a wavelength equal to or greater than about 600 nm upon interaction with hydrogen peroxide, said leuco dye having the sructure: ##STR42## wherein R is a 5- to 15-membered aromatic heterocyclic moiety provided that said moiety does not have an --NH-- group in the ring; and R' and R" are independently open chain or cyclic amines; and B. detecting said dye at a wavelength equal to or greater than about 600 nm.
Claim 28
Dependent Claim
64 words
The method of claim 22 wherein said leuco dye has the structure: ##STR43## wherein R 1 , R 2 , R 3 and R 4 are independently alkyl, alkaryl, aralkyl, aryl or a heterocyclic moiety, or R 1 and R 2 or R 3 and R 4 independently taken together with the respective nitrogen atom, represent the atoms necessary to complete a heterocyclic ring.
Claim 29
Dependent Claim
15 words
The method of claim 22 wherein said leuco dye is in a dry analytical element.
Claim 30
Dependent Claim
27 words
The method of claim 22 wherein said contacting step a occurs in the presence of an interactive composition which reacts with said analyte to provide hydrogen peroxide.
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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) | 1990-06-01 | 1990-12-01 | 1991-06-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-06-01 | 1994-12-01 | 1995-06-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-06-01 | 1998-12-01 | 1999-06-02 | $7700.00 | Window Closed / Lapsed |