US 10,865,218 B2Granted

Fluoride fluorescence probe

AssigneeThe Procter & Gamble Company

InventorsYunming Shi, Ross Strand, Tao Yi, Peng Wei, FengFeng Xue

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Abstract

Methylene blue (MB) derivatives selectively detect F− by desilylation reaction to act as a fluorescent probe.

Claims3

Dependent claims

A compound selected from the group consisting of:

(i) 4-((tert-butyldiphenylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(ii) 4-((triisopropylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(iii)4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(iv) 4-((trimethylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(v) 4-((tri-tert-butylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(vi) 4-((triethylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(vii) 3,5-dimethyl-4-((trimethylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(viii) 4-((triphenylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(ix) 4-((methyldiphenylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(x) 4-((diisopropyl(phenyl)silyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(xi) 3-((tert-butyldimethylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(xii) 4-((tert-butyldiphenylsilyl)oxy)benzyl 3,7-bis(diethylamino)-10H-phenothiazine-10-carboxylate;
(xiii) 4-((tert-butyldiphenylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-2,8-dimethyl-10H-phenothiazine-10-carboxylate;
(xiv) 4-((tert-butyldiphenylsilyl)oxy)benzyl 3,7-bis(ethylamino)-2,8-dimethyl-10H-phenothiazine-10-carboxylate;
(xv) 4-((tert-butyldiphenylsilyl)oxy)benzyl 3,7-di(pyrrolidin-1-yl)-10H-phenothiazine-10-carboxylate;
(xvi) 4-((tert-butyldiphenylsilyl)oxy)benzyl 3,7-di(piperidin-1-yl)-10H-phenothiazine-10-carboxylate;
(xvii) 4-((tert-butyldiphenylsilyl)oxy)benzyl 3,7-dimorpholino-10H-phenothiazine-10-carboxylate;
(xviii) 4-((tert-butyldiphenylsilyl)oxy)benzyl 3,7-bis (phenylamino)-10H-phenothiazine-10-carboxylate;
(xix) 4-((tert-butyldiphenylsilyl)oxy)benzyl 1,2,3,4,8,9,10,11-octahydro-6H-dipyrido[3,2-b:2′,3′-i]phenothiazine-6-carboxylate;
(xx) 4-((tert-butyldiphenylsilyl)oxy)benzyl 5-methyl-1,2,3,4,10,11,12,13-octahydro-7H-dipyrido[2,3-c:3′,2′-h]phenothiazine-7-carboxylate;
(xxi) 4-((triisopropylsilyl)oxy)benzyl 3,7-bis(diethylamino)-10H-phenothiazine-10-carboxylate;
(xxii) 4-((triisopropylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-2,8-dimethyl-10H-phenothiazine-10-carboxylate;
(xxiii) 4-((triisopropylsilyl)oxy)benzyl 3,7-bis(ethylamino)-2,8-dimethyl-10H-phenothiazine-10-carboxylate;
(xxiv) 4-((triisopropylsilyl)oxy)benzyl 3,7-di(pyrrolidin-1-yl)-10H-phenothiazine-10-carboxylate;
(xxv) 4-((triisopropylsilyl)oxy)benzyl 3,7-di(piperidin-1-yl)-10H-phenothiazine-10-carboxylate;
(xxvi) 4-((triisopropylsilyl)oxy)benzyl 3,7-dimorpholino-10H-phenothiazine-10-carboxylate;
(xxvii) 4-((triisopropylsilyl)oxy)benzyl 3,7-bis(phenylamino)-10H-phenothiazine-10-carboxylate;
(xxviii) 4-((tert-butyldiisopropylsilyl)oxy)benzyl 1,2,3,4,8,9,10,11-octahydro-6H-dipyrido[3,2-b:2′,3′-i]phenothiazine-6-carboxylate;
(xxix) 4-((tert-butyldiisopropylsilyl)oxy)benzyl 5-methyl-1,2,3,4,10,11,12,13-octahydro-7H-dipyrido[2,3-c:3′,2′-h]phenothiazine-7-carboxylate;
(xxx) 4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-bis(diethylamino)-10H-phenothiazine-10-carboxylate;
(xxxi) 4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-2,8-dimethyl-10H-phenothiazine-10-carboxylate;
(xxxii) 4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-bis(ethylamino)-2,8-dimethyl-10H-phenothiazine-10-carboxylate;
(xxxiii) 4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-di(pyrrolidin-1-yl)-10H-phenothiazine-10-carboxylate;
(xxxiv) 4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-di(piperidin-1-yl)-10H-phenothiazine-10-carboxylate;
(xxxv) 4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-dimorpholino-10H-phenothiazine-10-carboxylate;
(xxxvi) 4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-dimorpholino-10H-phenothiazine-10-carboxylate;
(xxxvii) 4-((tert-butyldimethylsilyl)oxy)benzyl 1,2,3,4,8,9,10,11-octahydro-6H-dipyrido[3,2-b:2′,3′-i]phenothiazine-6-carboxylate;
(xxxviii) 4-((tert-butyldimethylsilyl)oxy)benzyl 5-methyl-1,2,3,4,10,11,12,13-octahydro-7H-dipyrido[2,3-c:3′,2′-h]phenothiazine-7-carboxylate;
(xxxix) 4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenoxazine-10-carboxylate;
(xl) 3-((tert-butyldimethylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
and
(xli) 4-((tert-butyldimethylsilyl)oxy)benzyl 2,8-bis(dimethylamino)-10-methylphenazine-5(10H)-carboxylate.

39 more elements

Dependencies are inferred from the claim text.

Facts

Application: 16/005,817Filed 12 Jun 2018
Priority: WO PCT/CN2017/08947122 Jun 2017
Published: US 2018/0370996 A127 Dec 2018
Granted: 15 Dec 2020
Term ends: Not estimatedThe source records don’t support an estimate.

Classification6 codes

C07F 7/1804
Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages: compounds having Si-O-C linkages
G01N 21/643
Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects,…:…
G01N 31/22
Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted…
G01N 2021/6439
Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects,…:…

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US 2018/0370996 A1Pre-grant publication · published 27 Dec 2018
US 10,865,218 B2This patent

From the US filing history. Foreign family members aren’t listed.

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A compound selected from the group consisting of:

(i) 4-((tert-butyldiphenylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(ii) 4-((triisopropylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(iii)4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(iv) 4-((trimethylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(v) 4-((tri-tert-butylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(vi) 4-((triethylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(vii) 3,5-dimethyl-4-((trimethylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(viii) 4-((triphenylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(ix) 4-((methyldiphenylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(x) 4-((diisopropyl(phenyl)silyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(xi) 3-((tert-butyldimethylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
(xii) 4-((tert-butyldiphenylsilyl)oxy)benzyl 3,7-bis(diethylamino)-10H-phenothiazine-10-carboxylate;
(xiii) 4-((tert-butyldiphenylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-2,8-dimethyl-10H-phenothiazine-10-carboxylate;
(xiv) 4-((tert-butyldiphenylsilyl)oxy)benzyl 3,7-bis(ethylamino)-2,8-dimethyl-10H-phenothiazine-10-carboxylate;
(xv) 4-((tert-butyldiphenylsilyl)oxy)benzyl 3,7-di(pyrrolidin-1-yl)-10H-phenothiazine-10-carboxylate;
(xvi) 4-((tert-butyldiphenylsilyl)oxy)benzyl 3,7-di(piperidin-1-yl)-10H-phenothiazine-10-carboxylate;
(xvii) 4-((tert-butyldiphenylsilyl)oxy)benzyl 3,7-dimorpholino-10H-phenothiazine-10-carboxylate;
(xviii) 4-((tert-butyldiphenylsilyl)oxy)benzyl 3,7-bis (phenylamino)-10H-phenothiazine-10-carboxylate;
(xix) 4-((tert-butyldiphenylsilyl)oxy)benzyl 1,2,3,4,8,9,10,11-octahydro-6H-dipyrido[3,2-b:2′,3′-i]phenothiazine-6-carboxylate;
(xx) 4-((tert-butyldiphenylsilyl)oxy)benzyl 5-methyl-1,2,3,4,10,11,12,13-octahydro-7H-dipyrido[2,3-c:3′,2′-h]phenothiazine-7-carboxylate;
(xxi) 4-((triisopropylsilyl)oxy)benzyl 3,7-bis(diethylamino)-10H-phenothiazine-10-carboxylate;
(xxii) 4-((triisopropylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-2,8-dimethyl-10H-phenothiazine-10-carboxylate;
(xxiii) 4-((triisopropylsilyl)oxy)benzyl 3,7-bis(ethylamino)-2,8-dimethyl-10H-phenothiazine-10-carboxylate;
(xxiv) 4-((triisopropylsilyl)oxy)benzyl 3,7-di(pyrrolidin-1-yl)-10H-phenothiazine-10-carboxylate;
(xxv) 4-((triisopropylsilyl)oxy)benzyl 3,7-di(piperidin-1-yl)-10H-phenothiazine-10-carboxylate;
(xxvi) 4-((triisopropylsilyl)oxy)benzyl 3,7-dimorpholino-10H-phenothiazine-10-carboxylate;
(xxvii) 4-((triisopropylsilyl)oxy)benzyl 3,7-bis(phenylamino)-10H-phenothiazine-10-carboxylate;
(xxviii) 4-((tert-butyldiisopropylsilyl)oxy)benzyl 1,2,3,4,8,9,10,11-octahydro-6H-dipyrido[3,2-b:2′,3′-i]phenothiazine-6-carboxylate;
(xxix) 4-((tert-butyldiisopropylsilyl)oxy)benzyl 5-methyl-1,2,3,4,10,11,12,13-octahydro-7H-dipyrido[2,3-c:3′,2′-h]phenothiazine-7-carboxylate;
(xxx) 4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-bis(diethylamino)-10H-phenothiazine-10-carboxylate;
(xxxi) 4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-2,8-dimethyl-10H-phenothiazine-10-carboxylate;
(xxxii) 4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-bis(ethylamino)-2,8-dimethyl-10H-phenothiazine-10-carboxylate;
(xxxiii) 4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-di(pyrrolidin-1-yl)-10H-phenothiazine-10-carboxylate;
(xxxiv) 4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-di(piperidin-1-yl)-10H-phenothiazine-10-carboxylate;
(xxxv) 4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-dimorpholino-10H-phenothiazine-10-carboxylate;
(xxxvi) 4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-dimorpholino-10H-phenothiazine-10-carboxylate;
(xxxvii) 4-((tert-butyldimethylsilyl)oxy)benzyl 1,2,3,4,8,9,10,11-octahydro-6H-dipyrido[3,2-b:2′,3′-i]phenothiazine-6-carboxylate;
(xxxviii) 4-((tert-butyldimethylsilyl)oxy)benzyl 5-methyl-1,2,3,4,10,11,12,13-octahydro-7H-dipyrido[2,3-c:3′,2′-h]phenothiazine-7-carboxylate;
(xxxix) 4-((tert-butyldimethylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenoxazine-10-carboxylate;
(xl) 3-((tert-butyldimethylsilyl)oxy)benzyl 3,7-bis(dimethylamino)-10H-phenothiazine-10-carboxylate;
and
(xli) 4-((tert-butyldimethylsilyl)oxy)benzyl 2,8-bis(dimethylamino)-10-methylphenazine-5(10H)-carboxylate.

39 more elements

Facts

Application

16/005,817Filed 12 Jun 2018

Priority

WO PCT/CN2017/08947122 Jun 2017

Published

US 2018/0370996 A127 Dec 2018

Granted

15 Dec 2020

Term ends

Not estimatedThe source records don’t support an estimate.

Classification6 codes

C07F 7/1804
Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages: compounds having Si-O-C linkages
G01N 21/643
Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects,…:…
G01N 31/22
Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted…
G01N 2021/6439
Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects,…:…