US 12,253,526 B2
Fluorescent dye and use thereof
Daiki Hara, Kobe (JP); Takafumi Motoki, Tsukuba (JP); Yuji Kazuta, Tsukuba (JP); Yoshihiko Norimine, Tsukuba (JP); Hiroyuki Amino, Tsukuba (JP); Masatoshi Suganuma, Kobe (JP); Shingo Fujiyama, Kobe (JP); Kazuto Yamashita, Kobe (JP); Masaya Okada, Kobe (JP); Yoichi Nishikawa, Kobe (JP); and Shigeki Iwanaga, Kobe (JP)
Assigned to Eisai R&D Management Co., Ltd., Tokyo (JP); and SYSMEX CORPORATION, Kobe (JP)
Filed by Eisai R&D Management Co., Ltd., Tokyo (JP); and SYSMEX CORPORATION, Kobe (JP)
Filed on Feb. 1, 2021, as Appl. No. 17/163,993.
Claims priority of application No. 2020-016297 (JP), filed on Feb. 3, 2020.
Prior Publication US 2021/0255191 A1, Aug. 19, 2021
Int. Cl. C09B 57/00 (2006.01); G01N 21/64 (2006.01); G01N 33/58 (2006.01)
CPC G01N 33/582 (2013.01) [C09B 57/00 (2013.01); G01N 21/6428 (2013.01); G01N 21/6458 (2013.01); G01N 2021/6439 (2013.01)] 20 Claims
 
1. A fluorescent dye consisting of a compound represented by formula (I), a tautomer of the compound, or a salt of the compound or the tautomer:

OG Complex Work Unit Chemistry
(wherein:
A represents an optionally substituted C4-C7 heterocyclic ring which contains an Si atom;
X represents —NR1R2;
Y1 represents ═N+R3R4;
wherein each of the combination of R1 and R2 and the combination of R3 and R4 together form an optionally substituted N-containing C2-C12 alkyl heterocyclic ring with an N atom to which they bind,
R5 and R6 independently represent an H atom, an optionally substituted C1-C6 alkyl group, or an optionally substituted C1-C6 heteroalkyl group;
R7, R8, R9, R10 and R11 are independently selected from the group consisting of an H atom, a halogen atom, an optionally substituted C1-C6 alkyl group, an optionally substituted C1-C6 alkoxy group, an optionally substituted C1-C6 alkylthio group, an optionally substituted amino group, an optionally substituted aryl group, an optionally substituted heteroaryl group, —CO2H, —CO2−, —SO3H, —SO3−, and -L-R;
L is 1 to 16 non-hydrogen atoms wherein L optional has a linear structure, a branched structure, and/or a cyclic structure, and wherein, when there are one or more hetero atoms in the non-hydrogen atoms, the hetero atoms are contained as one or more groups independently selected from the group consisting of an ester group, an amine group, an amide group, an ether group, a thioether group and a carbonyl group;
R is selected from a hydroxy group, a carboxyl group, a sulfonate group, an unsaturated imide group, an unsaturated amide group, an unsaturated ester group, an activated carboxylic acid ester group, an amine group, an alcohol group, a nitrile group, a mercaptan group, a boronate group, a phosphoramidite group, a halogenated alkyl group, a halogenated sulfonyl group, an amide or ester group having a halogen atom at alpha-position, an isocyanate group, an isothiocyanate group, an azide group, an aldehyde group, and an acylnitrile group; and
at least one combination of adjacent two substituents among R7, R8, R9, R10 and R11 may together form a ring.