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US5587472A Expired / Lapsed US ⏱️ 0.0 years remaining

Coumarin-labeled nucleoside 5'-triphosphates

Assignee: Siemens Healthcare Diagnostics GmbH Germany
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Filing: 1995-06-02
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Granted: 1996-12-24
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Expires: 2015-06-02
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Abstract

Abstract A fluorescent label compound having the formula A-B1-B2-B3-C wherein A represents the residue of a natural or synthetic nucleotide or nucleoside or a derivative thereof; B1 represents a divalent spacer radical or a single bond; B2 represents a divalent spacer radical; B3 represents a divalent spacer radical or a single bond; and C represents a coumarin radical having the formula <IMAGE> in which R1 represents hydrogen or cyano; R2 represents phenyl or thiazolyl bonded in the 2-, 4- or 5-position, wherein the phenyl is unsubstituted or substituted by nitro, cyano, amino, -NH-C1-4-alkyl, -(CH2)1-4-NH2, -(CH2)1-4-NH-(CH2)1-3-CH3, carboxy, C1-4-alkoxycarbonyl, C1-4-alkoxycarbonyloxy, hydroxy, C1-4-alkylaminocarbonyl, or C1-4-alkylcarbonylamino and either further unsubstituted or substituted by C1-4-alkyl, fluorine, chlorine or bromine, and where the thiazolyl is unsubstituted or monosubstituted or disubstituted by chlorine, cyano, carboxyl, or C1-4-alkoxycarbonyl, or the thiazolyl is fused in the 4- and 5-position with a benzene ring which is either unsubstituted or substituted by carboxyl, amino, or hydroxyl; R3 represents hydrogen, C1-4-alkyl, C1-4-alkoxycarbonyl-C1-4-alkyl, or phenylsulphonyl, where the C1-4-alkyl is unsubstituted or substituted by hydroxyl, amino, carboxyl, or C1-4-alkoxycarbonyl, and where the phenylsulphonyl is unsubstituted or monosubstituted or disubstituted by chlorine, bromine, or C1-4-alkyl; or where one of the radicals R2 or R3 denotes or is substituted by a primary or secondary amino group, hydroxyl, carboxyl, or C1-4-alkoxycarbonyl, or can be converted into such a group by hydrolysis or hydrogenation.

Inventors

  • 👤 Nanibhushan Dattagupta
  • 👤 Jurgen Kocher

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-30 15:35
CPC Classifications
C; C07; C07H; C07H21/00

Claims Analysis

Total Claims: 6
Claim 1
Independent Claim 70 words
A fluorescent label compound having the formula: A--B.sup.1 --B.sup.2 --B.sup.3 --C wherein A represents a radical selected from the group consisting of dATP-8-yl and dUTP-5-yl; B 1 --B 2 --B 3 collectively represent a spacer moiety selected from the group consisting of: --CH═CH--CH.sub.2 --NH--CO--(CH.sub.2).sub.5 --NH--CO--(CH.sub.2).sub.3 --a and --NH--(CH.sub.2).sub.6 --NH--CO--(CH.sub.2).sub.5 --NH--CO--(CH.sub.2).sub.3 --a wherein "a" represents the point of attachment to A; and C represents a coumarin radical having the formula: ##STR26##
Claim 2
Dependent Claim 70 words
A fluorescent label compound having the formula: A--B.sup.1 --B.sup.2 --B.sup.3 --C wherein A represents a radical selected from the group consisting of dATP-8-yl and dUTP-5-yl; B 1 --B 2 --B 3 collectively represent a spacer moiety selected from the group consisting of: --CH═CH--CH.sub.2 --NH--CO--(CH.sub.2).sub.5 --NH--CO--(CH.sub.2).sub.3 --a and --NH--(CH.sub.2).sub.6 --NH--CO--(CH.sub.2).sub.5 --NH--CO--(CH.sub.2).sub.3 --a wherein "a" represents the point of attachment to A; and C represents a coumarin radical having the formula: ##STR26##
Claim 3
Dependent Claim 11 words
The fluorescent compound according to claim 1 having the formula ##STR27##
Claim 4
Dependent Claim 12 words
The fluorescent label compound according to claim 1 having the formula ##STR28##
Claim 5
Dependent Claim 52 words
In a test for the presence of a particular nucleic acid sequence in a sample, wherein the sample is subjected to a labeled probe under hybridizing conditions and the sample is thereafter assayed for hybridization product, the improvement wherein the probe is labeled with a fluorescent label compound according to claim 1.
Claim 6
Dependent Claim 29 words
A diagnostic kit for use in detecting the presence of a particular nucleic acid sequence in a sample, said kit comprising a fluorescent label compound according to claim 1.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1999-12-24 2000-06-24 2000-12-24 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2003-12-24 2004-06-24 2004-12-24 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2007-12-24 2008-06-24 2008-12-24 $7700.00 Window Closed / Lapsed

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