US 11,807,643 B2
Fluorescent dyes
Kevin P. Lund, Sunnyvale, CA (US); Dmitri Sergueev, Sunnyvale, CA (US); and Alexander Gall, Sunnyvale, CA (US)
Assigned to Cepheid, Sunnyvale, CA (US)
Filed by Cepheid, Sunnyvale, CA (US)
Filed on Jul. 13, 2021, as Appl. No. 17/374,514.
Claims priority of provisional application 63/052,862, filed on Jul. 16, 2020.
Prior Publication US 2022/0017531 A1, Jan. 20, 2022
Int. Cl. C07D 491/052 (2006.01); C09B 11/24 (2006.01); C12Q 1/686 (2018.01)
CPC C07D 491/052 (2013.01) [C09B 11/24 (2013.01); C12Q 1/686 (2013.01)] 36 Claims
 
1. A compound represented by Formula I:

OG Complex Work Unit Chemistry
or a stereoisomer, a salt, or a tautomer thereof,
wherein:
X is H, halogen, or C1-C5 alkyl;
R1, R2, R3, and R4 are independently H or optionally substituted C1-C6 alkyl;
R5, R6, R7, R8, and R9 are independently H, halogen, or optionally substituted C1-C6 alkyl;
L1 is an optionally substituted C2-C10 alkylene or optionally substituted C2-C50 heteroalkylene;
L2 and L3 are independently an optionally substituted C2-C10 alkylene or optionally substituted C2-C30 heteroalkylene;
Q1 is a hydroxyl protecting group;
Z is CH, N, NHC(O)N, or OC(O)N;
Y is OH, OP(OCH2CH2CN)NR10R11 or a solid support; and
R10 and R11 are independently optionally substituted C1-C6 alkyl,
wherein optionally substituted alkyl refers to alkyl optionally substituted with F, Cl, Br, I, ═O, ═N—CN, ═N—OR, ═NR, OR, NR2, SR, SO2R, SO2NR2, NRSO2R, NRCONR2, NRC(O)OR, NRC(O)R, CN, C(O)OR, C(O)NR2, OC(O)R, C(O)R, or NO2, wherein each R is independently H, C1-C8 alkyl, C2-C8 heteroalkyl, C1-C8 acyl, C2-C8 heteroacyl, C2-C8 alkenyl, C2-C8 heteroalkenyl, C2-C8 alkynyl, C2-C8 heteroalkynyl, C6-C10 aryl, or C5-C10 heteroaryl, and each R is optionally substituted with F, Cl, Br, I, ═O, ═N—CN, ═N—OW, ═NR′, OR′, NR′2, SR′, SO2R′, SO2NR′2, NR′SO2R′, NR′CONR′2, NR′C(O)OR′, NR′C(O)R′, CN, C(O)OR′, C(O)NR′2, OC(O)R′, C(O)R′, and NO2, wherein each R′ is independently H, C1-C8 alkyl, C2-C8 heteroalkyl, C1-C8 acyl, C2-C8 heteroacyl, C6-C10 aryl, or C5-C10 heteroaryl,
wherein optionally substituted heteroalkylene refers to heteroalkylene optionally substituted with C1-C6 alkyl, C2-C6 heteroalkyl, alkynyl, F, Cl, Br, I, N3, OR, NR2, SR, SO2R, SO2NR2, NRSO2R, NRCONR2, NRC(O)OR, NRC(O)R, CN, C(O)OR, C(O)NR2, OC(O)R, C(O)R, oxo, and NO2, wherein each R is independently H, C1-C6 alkyl, or C2-C6 heteroalkyl,
wherein heteroalkylene, heteroalkyl, heteroalkenyl, heteroalkynyl, and heteroacyl, refer to the corresponding hydrocarbon wherein one or more chain carbon atoms have been replaced by a heteroatom selected from the group consisting of N, O, S, and P, and
wherein heteroaryl refers to a monocyclic or fused bicyclic aromatic ring system which contains as ring members one or more heteroatoms selected from the group consisting of N, O, and S.