US 12,275,708 B2
Hydrophilic high quantum yield acridinium esters with improved stability and fast light emission
Anand Natrajan, Manchester, NH (US); David Sharpe, Foxborough, MA (US); Qingping Jiang, East Walpole, MA (US); and David Wen, Northborough, MA (US)
Assigned to Siemens Healthcare Diagnostics Inc., Tarrytown, NY (US)
Filed by Siemens Healthcare Diagnostics Inc., Tarrytown, NY (US)
Filed on Feb. 15, 2024, as Appl. No. 18/442,393.
Application 17/658,438 is a division of application No. 16/801,354, filed on Feb. 26, 2020, granted, now 11,332,445, issued on May 17, 2022.
Application 17/658,438 is a division of application No. 14/901,009, abandoned, previously published as PCT/US2014/045505, filed on Jul. 4, 2014.
Application 16/801,354 is a division of application No. 14/901,009, abandoned, previously published as PCT/US2014/045505, filed on Jul. 4, 2014.
Application 18/442,393 is a continuation of application No. 17/658,438, filed on Apr. 7, 2022, granted, now 11,932,603.
Claims priority of provisional application 61/843,528, filed on Jul. 8, 2013.
Prior Publication US 2024/0254088 A1, Aug. 1, 2024
Int. Cl. C07D 219/06 (2006.01); C09K 11/07 (2006.01); F21K 2/06 (2006.01); G01N 21/76 (2006.01); G01N 33/543 (2006.01); G01N 33/58 (2006.01)
CPC C07D 219/06 (2013.01) [C09K 11/07 (2013.01); F21K 2/06 (2013.01); G01N 21/76 (2013.01); G01N 33/543 (2013.01); G01N 33/582 (2013.01)] 9 Claims
OG exemplary drawing
 
1. An acridinium compound having the structure:

OG Complex Work Unit Chemistry
wherein,
R1 is a methyl or sulfopropyl group;
R2a is alkylene or arylene,
R3a is alkyl or aryl,
G is, at both occurrences, a branched group selected from:

OG Complex Work Unit Chemistry
and
R12 is selected from the group consisting of
(1) —OH;
(2) —O—N-succinimidyl;
(3) —NH—(CH2)5—C(O)—O—N-succinimidyl;
(4) —NH—(CH2)5—COOH;
(5) —NH—(C2H4O)p—C2H4NH—C(O)—(CH2)3—C(O)—O—N—R″ wherein p=1 to 5; and
where R″ is hydrogen or —N-succinimidyl; and
(6) —NH—(C2H4O)q—C2H4NH2, wherein q=1 to 5.