US 11,981,820 B2
Ultra bright dimeric or polymeric dyes
Tracy Matray, Snohomish, WA (US); Sharat Singh, Rancho Santa Fe, CA (US); and Michael VanBrunt, Covington, WA (US)
Assigned to SONY GROUP CORPORATION, Tokyo (JP)
Filed by Sony Group Corporation, Tokyo (JP)
Filed on Aug. 27, 2021, as Appl. No. 17/458,938.
Application 17/458,938 is a division of application No. 15/543,885, granted, now 11,142,647, previously published as PCT/US2017/025530, filed on Mar. 31, 2017.
Claims priority of provisional application 62/317,192, filed on Apr. 1, 2016.
Prior Publication US 2021/0395530 A1, Dec. 23, 2021
Int. Cl. C09B 69/10 (2006.01); C07C 215/68 (2006.01); C07F 9/09 (2006.01); C07F 9/24 (2006.01); G01N 33/58 (2006.01)
CPC C09B 69/102 (2013.01) [C07C 215/68 (2013.01); C07F 9/091 (2013.01); C07F 9/2408 (2013.01); C09B 69/103 (2013.01); C09B 69/109 (2013.01); G01N 33/582 (2013.01)] 17 Claims
 
1. A compound having the following structure (II):

OG Complex Work Unit Chemistry
or a stereoisomer, salt or tautomer thereof, wherein:
G is, at each occurrence, independently a moiety comprising an aldehyde, oxime, hydrazone, alkyne, amine, azide, acylazide, acylhalide, nitrile, nitrone, sulfhydryl, disulfide, sulfonyl halide, isothiocyanate, activated ester, ketone, α, β-unsaturated carbonyl, alkene, maleimide, α-haloimide, epoxide, aziridine, tetrazine, tetrazole, phosphine, biotin, or thiirane functional group, wherein the activated ester is an N-succinimide ester, imidoester or polyflourophenyl ester;
L1a, L2 and L3 are, at each occurrence, independently an optional alkylene, alkenylene, alkynylene, heteroalkylene, heteroalkenylene, heteroalkynylene or heteroatomic linker;
L4 is, at each occurrence, independently an alkylene, alkenylene, alkynylene, heteroalkylene, heteroalkenylene or heteroalkynylene linker;
R1 is, at each occurrence, independently H, alkyl or alkoxy;
R2 and R3 are each independently H, OH, SH, alkyl, alkoxy, alkylether, —OP(═Ra)(Rb)Rc, Q, a linker comprising a covalent bond to Q, a linker comprising a covalent bond to an analyte molecule, a linker comprising a covalent bond to a solid support or a linker comprising a covalent bond to a further compound of structure (II), wherein: Ra is O or S; Rb is OH, SH, O, S, ORd or SRd; Rc is OH, SH, O, S, ORd, SRd, alkyl, alkoxy, alkylether, alkoxyalkylether, phosphate, thiophosphate, phosphoalkyl, thiophosphoalkyl, phosphoalkylether or thiophosphoalkylether; and Rd is a counter ion;
R4 is, at each occurrence, independently OH, SH, O, S, ORd or SRd;
R5 is, at each occurrence, independently oxo, thioxo or absent;
Q is, at each occurrence, independently a moiety comprising a sulfhydryl, disulfide, activated ester, isothiocyanate, azide, alkyne, alkene, diene, dienophile, acid halide, sulfonyl halide, phosphine, a-haloamide, biotin, amino or maleimide functional group, wherein the activated ester is an N-succinimide ester, imidoester or polyflourophenyl ester;
m is, at each occurrence, independently an integer of zero or greater, provided that at least one occurrence of m is an integer of one or greater; and
n is an integer of one or greater.