US 12,497,515 B2
Fluorogenic pH-sensitive compounds and their methods of use
Yi-Zhen Hu, Eugene, OR (US); Aimei Chen, Eugene, OR (US); Daniel Beacham, Eugene, OR (US); Chrisgen Vonnegut, Springfield, OR (US); and Krishnamurthy Nacharaju, Eugene, OR (US)
Assigned to Life Technologies Corporation, Carlsbad, CA (US)
Filed by LIFE TECHNOLOGIES CORPORATION, Carlsbad, CA (US)
Filed on Jan. 23, 2024, as Appl. No. 18/419,897.
Application 18/419,897 is a continuation of application No. 17/498,377, filed on Oct. 11, 2021, granted, now 11,952,495.
Claims priority of provisional application 63/091,156, filed on Oct. 13, 2020.
Prior Publication US 2024/0228785 A1, Jul. 11, 2024
Int. Cl. C09B 11/24 (2006.01); G01N 21/64 (2006.01)
CPC C09B 11/24 (2013.01) [G01N 21/6428 (2013.01); G01N 2021/6439 (2013.01)] 15 Claims
 
1. A compound chosen from a compound of Formula (I):

OG Complex Work Unit Chemistry
its corresponding compound of Formula (II)

OG Complex Work Unit Chemistry
wherein,
O—X—Y is chosen from:

OG Complex Work Unit Chemistry
R1, R2, R3, and R4 are each independently chosen from H, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cyano, halo, hydroxy, nitro, sulfo, sulfonyl, sulfonyloxy, thioacyl, thiol, alkylthio, substituted alkylthio, acyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, cycloalkyl, substituted cycloalkyl, heterocyclyl, and substituted heterocyclyl; and
D is

OG Complex Work Unit Chemistry
wherein
R5, R6, R7 and R8 are each independently chosen from H and alkyl; and
R9, R10, R11 and R12 are each independently chosen from H, alkyl, sulfo and sulfonyl; or
R8 is taken together with R12 and the atoms to which they are attached to form an optionally substituted fused ring;
or R9 is taken together with R5 and the atoms to which they are attached to form an optionally substituted fused ring;
or R10 is taken together with R7 and the atoms to which they are attached to form an optionally substituted fused ring;
or R11 is taken together with R6 and the atoms to which they are attached to form an optionally substituted fused ring, and salts thereof.