US 11,981,964 B2
Substituted coumarin dyes and uses as fluorescent labels
Nikolai Nikolaevich Romanov, Cambridge (GB); Michael Callingham, Cambridge (GB); Carole Anastasi, Cambridge (GB); Patrick Mccauley, Cambridge (GB); Niall Hynes, Cambridge (GB); Natasha Crake, Cambridge (GB); Xiaolin Wu, Cambridge (GB); and Xiaohai Liu, Cambridge (GB)
Assigned to Illumina Cambridge Limited, Cambridge (GB)
Filed by Illumina Cambridge Limited, Cambridge (GB)
Filed on Jul. 26, 2021, as Appl. No. 17/385,232.
Claims priority of provisional application 63/057,758, filed on Jul. 28, 2020.
Prior Publication US 2022/0033900 A1, Feb. 3, 2022
Int. Cl. C07D 417/04 (2006.01); C07D 405/14 (2006.01); C07D 407/04 (2006.01); C07D 409/04 (2006.01); C07D 409/14 (2006.01); C07D 413/04 (2006.01); C07D 417/14 (2006.01); C09B 57/02 (2006.01); C12Q 1/68 (2018.01); C12Q 1/6869 (2018.01); C12Q 1/6876 (2018.01); G01N 21/64 (2006.01)
CPC C12Q 1/6876 (2013.01) [C07D 405/14 (2013.01); C07D 407/04 (2013.01); C07D 409/04 (2013.01); C07D 409/14 (2013.01); C07D 413/04 (2013.01); C07D 417/04 (2013.01); C07D 417/14 (2013.01); C09B 57/02 (2013.01); C12Q 1/6869 (2013.01); G01N 21/6428 (2013.01); G01N 2021/6439 (2013.01)] 24 Claims
 
1. A compound of Formula (II) or (II′), or a salt or mesomeric form thereof:

OG Complex Work Unit Chemistry
wherein X is S, O, or NRa;
Y is O or NH;
each R1, R2, R3 and R5 is independently H, optionally substituted C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 hydroxy alkyl, (C1-C6 alkoxy)(C1-C6 alkyl), optionally substituted amino, halo, cyano, hydroxy, nitro, sulfonyl, sulfino, sulfo, sulfonate, S-sulfonamido, N-sulfonamido, optionally substituted C3-C10 carbocyclyl, optionally substituted C6-C10 aryl, optionally substituted 5 to 10 membered heteroaryl, or optionally substituted 3 to 10 membered heterocyclyl;
R4 is —NRbRc, halo, —ORd or —OS(O)2Rd;
each of R6 and R7 is independently H, carboxyl, —C(O)NRbRc, —C(O)ORd, C1-C6 alkyl, substituted C1-C6 alkyl, C1-C6 haloalkyl, halo, optionally substituted amino, N-sulfonamido, sulfonyl, S-sulfonamido, hydroxy, cyano, nitro, optionally substituted phenyl, optionally substituted C3-C8 carbocyclyl, optionally substituted 5 to 10 membered heteroaryl, or optionally substituted 3 to 10 membered heterocyclyl; or R6 and R7 in Formula (II) together with the atoms to which they are attached form an optionally substituted C5-C8 carbocyclyl or an optionally substituted 5 to 8 membered heterocyclyl;
Ra is H or C1-C6 alkyl;
each Rb and Rc is independently H, C1-C6 alkyl, or substituted C1-C6 alkyl; or Rb and Rc together with the nitrogen atom to which they are attached form an optionally substituted 4 to 10 membered heterocyclyl; and
each Rd is independently optionally substituted C1-C6 alkyl or optionally substituted phenyl; provided that
at least one of R6 and R7, or the optionally substituted C5-C8 carbocyclyl or optionally substituted 5 to 8 membered heterocyclyl formed from R6 and R7 and the atoms to which they are attach, comprises a carboxyl; or
R4 is —NRbRc and at least one of Rb and Rc comprises a carboxyl or —C(O)ORd.