US 11,655,247 B2
Nanoluc suicide substrates
Brock Binkowski, Sauk City, WI (US); Mary P. Hall, Waunakee, WI (US); Thomas Machleidt, Madison, WI (US); Joel Walker, San Luis Obispo, CA (US); and Wenhui Zhou, San Luis Obispo, CA (US)
Assigned to Promega Corporation, Madison, WI (US)
Filed by PROMEGA CORPORATION, Madison, WI (US)
Filed on Apr. 30, 2019, as Appl. No. 16/399,410.
Claims priority of provisional application 62/665,346, filed on May 1, 2018.
Prior Publication US 2019/0337939 A1, Nov. 7, 2019
Int. Cl. C07D 471/04 (2006.01); C07D 519/00 (2006.01); C12Q 1/66 (2006.01); G01N 33/52 (2006.01); G01N 33/533 (2006.01); G01N 33/542 (2006.01)
CPC C07D 471/04 (2013.01) [C07D 519/00 (2013.01); C12Q 1/66 (2013.01); G01N 33/52 (2013.01); G01N 33/533 (2013.01); G01N 33/542 (2013.01); G01N 2458/15 (2013.01)] 9 Claims
 
1. A compound of formula (I)

OG Complex Work Unit Chemistry
or a tautomer or a salt thereof, wherein:
R1 is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocycle, or optionally substituted cycloalkyl, wherein R1 is substituted with at least one group that is -Q-L-Z;
Q is —O—, —NRQ—, —NRQ—CO—, —CO—NRQ—, —O—CO—NRQ—, or —NRQ—CO—O—;
L is —(CR1aR1b)m—, —(CR1xR1y—CR1xR1y—O)t1—(CR1xR1y)t2—Q1—, —(CR1xR1y)t2-A-(CR1xR1y—CR1xR1y—O)t1-Q1-, wherein each Q1 is independently a bond, —O—, or —NRQ—, and A is a bond, —O—, —NRQ—, —NRQ—CO—, —CO—NRQ—, —O—CO—NRQ—, or —NRQ—CO—O—;
Z is —COOR2, —SO2—OR3, —PO(OR4)(OR5), halo, azide, C2-C10 alkynyl, a biotin moiety, —NR6R7, or —NR8—CO—R9;
R2, R3, R4, R5, R8, R9, R10, R11, and R12 at each occurrence are independently hydrogen, optionally substituted C1-C8 alkyl, optionally substituted aryl, optionally substituted cycloalkyl, optionally substituted heteroaryl, optionally substituted heterocycle, optionally substituted heteroalkyl, or an energy acceptor;
R6 and R7 at each occurrence are independently hydrogen, optionally substituted C1-C8 alkyl, optionally substituted aryl, optionally substituted cycloalkyl, optionally substituted heteroaryl, optionally substituted heterocycle, optionally substituted heteroalkyl, or an energy acceptor; or R6 and R7, together with the nitrogen atom to which they are attached, together form an optionally substituted ring;
R1a, R1b, RQ, RQ1, R1x, and R1y at each occurrence are independently hydrogen, C1-C4 alkyl, or C1-C4 haloalkyl;
q is 0, 1, or 2;
m at each occurrence is independently 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12;
t1 at each occurrence is independently 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; and
t2 is an integer from 0-5;
wherein, when a group is optionally substituted, it is either unsubstituted or substituted with one or more substituents independently selected from halogen, ═O, ═S, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkoxy, heteroalkyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, heterocycle, cycloalkylalkyl, heteroarylalkyl, arylalkyl, hydroxy, hydroxyalkyl, alkoxy, alkoxyalkyl, aryloxy, benzyloxy, amino, alkylamino, acylamino, aminoalkyl, arylamino, sulfonylamino, sulfinylamino, sulfonyl, alkylsulfonyl, arylsulfonyl, aminosulfonyl, sulfinyl, —COOH, amide, carbamate, and acyl; and
wherein the compound is not 4-[4-[[8-benzyl-6-(4-hydroxyphenyl)-3-oxo-7H-imidazo[1,2-a]pyrazin-2-yl]methyl]phenoxy]butanoic acid.