US4714763A
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Novel oxazine-ureas and thiazine urea chromophors as fluorescent labels
Assignee: Viomedics Inc
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Filing: 1985-07-11
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Granted: 1987-12-22
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Expires: 2005-07-11
Abstract
Abstract Novel urea derivatives of oxazine and thiazine chromophors have the structural formula I or II. ##STR1## wherein M is oxygen or sulfur, R 1 and R 2 are aliphatic alkyl groups or hydrogen; R 3 is hydrogen or alkyl group; R 4 is hydrogen, alkyl or amine group; R 5 is hydrogen, amine or alkyl group; X.sup.⊖ is an anion consisting of an organic (e.g. CH 3 COO.sup.⊖, CH 3 CH 2 COO.sup.⊖ and the like) or inorganic specie (e.g. Cl.sup.⊖, Br.sup.⊖, I.sup.⊖, ClO 4 .sup.⊖, SO 4 ", and the like); n is 0 to 20; Z is N═C═O, N═C═S, carboxylic, primary or secondary amine, and when n=0, Z may be ##STR2## wherein Q is hydroxyl, amino, carboxylic, sulfydryl, isocyanato, or isothiocyanato. The functional oxazine-urea and thiazine-urea derivatives react with compounds of interest to form adducts resulting in the fluorescent labeling of the compound.
Inventors
- 👤 Spyros Theodoropulos
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 15:24
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; C07D279/00; C07D279/10; C07D279/14; C07D279/36; C07J; C07J43/00; C07J43/003; C09; C09B; C09B19/00; C09B21/00
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
125 words
Urea derivatives of oxazine and thiazine chromophors selected from the group consisting of: ##STR21## wherein n is 0 to 20; M is oxygen or sulfur; R 1 is hydrogen or alkyl group from 1 to 10 carbon atoms; R 2 is hydrogen or alkyl group from 1 to 10 carbon atoms; R 3 is hydrogen or alkyl group from 1 to 10 carbon atoms; R 4 is hydrogen, alkyl group from 1 to 10 carbon atoms, halogen or amino group; R 5 is hydrogen, alkyl group from 1 to 10 carbon atoms, halogen or amino group; X.sup.⊖ is an organic or an inorganic anion and Z is N═C═O, N═C═S, carboxylic, or amino, and when n=0, Z may be ##STR22## wherein Q is isocyanato or isothiocyanato.
Claim 2
Dependent Claim
125 words
Urea derivatives of oxazine and thiazine chromophors selected from the group consisting of: ##STR21## wherein n is 0 to 20; M is oxygen or sulfur; R 1 is hydrogen or alkyl group from 1 to 10 carbon atoms; R 2 is hydrogen or alkyl group from 1 to 10 carbon atoms; R 3 is hydrogen or alkyl group from 1 to 10 carbon atoms; R 4 is hydrogen, alkyl group from 1 to 10 carbon atoms, halogen or amino group; R 5 is hydrogen, alkyl group from 1 to 10 carbon atoms, halogen or amino group; X.sup.⊖ is an organic or an inorganic anion and Z is N═C═O, N═C═S, carboxylic, or amino, and when n=0, Z may be ##STR22## wherein Q is isocyanato or isothiocyanato.
Claim 3
Dependent Claim
150 words
Urea derivatives of oxazine and thiazine chromophors having the structural formula ##STR23## wherein n is 0 to 20; M is oxygen or sulfur; R 1 is hydrogen or alkyl group from 1 to 10 carbon atoms; R 2 is hydrogen or alkyl group from 1 to 10 carbon atoms; R 3 is hydrogen or alkyl group from 1 to 10 carbon atoms; R 4 is hydrogen, alkyl group from 1 to 10 carbon atoms, halogen or amino group; R 5 is hydrogen, alkyl group from 1 to 10 carbon atoms, halogen or amino group; X.sup.⊖ is an anion consisting of an organic specie CH 3 COO.sup.⊖, CH 3 CH 2 COO.sup.⊖, or CF 3 COO.sup.⊖, or an inorganic specie Cl.sup.⊖, Br.sup.⊖, I.sup.⊖, ClO 4 .sup.⊖ or SO 4 -2 , Z is N═C═O, N═C═S, carboxylic, or amino, and when n=0, Z may be ##STR24## wherein Q is isocyanato or isothiocyanato.
Claim 4
Dependent Claim
150 words
Urea derivatives of oxazine and thiazine chromophors having the structural formula ##STR23## wherein n is 0 to 20; M is oxygen or sulfur; R 1 is hydrogen or alkyl group from 1 to 10 carbon atoms; R 2 is hydrogen or alkyl group from 1 to 10 carbon atoms; R 3 is hydrogen or alkyl group from 1 to 10 carbon atoms; R 4 is hydrogen, alkyl group from 1 to 10 carbon atoms, halogen or amino group; R 5 is hydrogen, alkyl group from 1 to 10 carbon atoms, halogen or amino group; X.sup.⊖ is an anion consisting of an organic specie CH 3 COO.sup.⊖, CH 3 CH 2 COO.sup.⊖, or CF 3 COO.sup.⊖, or an inorganic specie Cl.sup.⊖, Br.sup.⊖, I.sup.⊖, ClO 4 .sup.⊖ or SO 4 -2 , Z is N═C═O, N═C═S, carboxylic, or amino, and when n=0, Z may be ##STR24## wherein Q is isocyanato or isothiocyanato.
Claim 5
Dependent Claim
132 words
Urea derivatives of oxazine and thiazine chormophors having the structural formula ##STR25## wherein n is 0 to 20; M is oxygen or sulfur; R 1 is hydrogen or alkyl group from 1 to 10 carbon atoms; R 2 is hydrogen or alkyl group from 1 to 10 carbon atoms; R 3 is hydrogen or alkyl group from 1 to 10 carbon atoms; R 4 is hydrogen, alkyl group from 1 to 10 carbon atoms, halogen or amino group; Z is N═C═O, N═C═S, carboxylic, or amino and when n=0, Z may be ##STR26## wherein Q is isocyanato or isothiocyanato, X.sup.⊖ is an anion consisting of an organic specie CH 3 COO.sup.⊖, CH 3 CH 2 COO.sup.⊖, CF 3 COO.sup.⊖ or an inorganic specie Cl.sup.⊖, Br.sup.⊖, I.sup.⊖, ClO 4 .sup.⊖, SO 4 -2 .
Claim 6
Dependent Claim
132 words
Urea derivatives of oxazine and thiazine chormophors having the structural formula ##STR25## wherein n is 0 to 20; M is oxygen or sulfur; R 1 is hydrogen or alkyl group from 1 to 10 carbon atoms; R 2 is hydrogen or alkyl group from 1 to 10 carbon atoms; R 3 is hydrogen or alkyl group from 1 to 10 carbon atoms; R 4 is hydrogen, alkyl group from 1 to 10 carbon atoms, halogen or amino group; Z is N═C═O, N═C═S, carboxylic, or amino and when n=0, Z may be ##STR26## wherein Q is isocyanato or isothiocyanato, X.sup.⊖ is an anion consisting of an organic specie CH 3 COO.sup.⊖, CH 3 CH 2 COO.sup.⊖, CF 3 COO.sup.⊖ or an inorganic specie Cl.sup.⊖, Br.sup.⊖, I.sup.⊖, ClO 4 .sup.⊖, SO 4 -2 .
Claim 7
Dependent Claim
14 words
The urea derivative of claim 3 which is isothiocyanato pentyl Nile Blue A urea.
Claim 8
Dependent Claim
13 words
The urea derivative of claim 3 which is isocyanatohexyl Nile Blue A urea.
Claim 9
Dependent Claim
11 words
The urea derivative of claim 3 which is N-(2-thiolactone)-cresyl violet urea.
Claim 10
Dependent Claim
14 words
The urea derivative of claim 2 which is isothiocyanato pentyl toluidine blue O urea.
Claim 11
Dependent Claim
14 words
The urea derivative of claim 2 which is isothiocyanato pentyl Brilliant cresyl blue urea.
References Cited (Backward Citations)
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