US 12,435,088 B2
Salicyl-adenosinemonosulfamate analogs and uses thereof
Derek Shieh Tan, New York, NY (US); Lisa Charlotte Standke, New York, NY (US); Luis Edmundo Nereo Quadri, New York, NY (US); Glennon Valere Bythrow, Chicago, IL (US); William Ramses Bishai, Baltimore, MD (US); and Shichun Lun, Ellicott City, MD (US)
Assigned to Memorial Sloan-Kettering Cancer Center, New York, NY (US); Research Foundation of the City University of New York, New York, NY (US); and The Johns Hopkins University, Baltimore, MD (US)
Appl. No. 17/416,976
Filed by Memorial Sloan-Kettering Cancer Center, New York, NY (US); Research Foundation of the City University of New York, New York, NY (US); and The Johns Hopkins University, Baltimore, MD (US)
PCT Filed Dec. 20, 2019, PCT No. PCT/US2019/068107
§ 371(c)(1), (2) Date Jun. 21, 2021,
PCT Pub. No. WO2020/132603, PCT Pub. Date Jun. 25, 2020.
Claims priority of provisional application 62/784,323, filed on Dec. 21, 2018.
Prior Publication US 2022/0162209 A1, May 26, 2022
Int. Cl. C07D 473/30 (2006.01); C07D 473/18 (2006.01)
CPC C07D 473/30 (2013.01) [C07D 473/18 (2013.01)] 20 Claims
 
1. A compound of Formula (I):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt, stereoisomer, or tautomer thereof, wherein:
R1 is optionally substituted alkyl, optionally substituted heteroalkyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl, or optionally substituted acyl;
each or R2 and R3 is hydrogen, halogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted acyl, —NO2, —CN, —ORe, —N(Re)2, —N3, —SO2H, —SO3H; —SH, —SRe, —SSRe, —OC(═O)Re, —OCO2Re, —OC(═O)N(Re)2, —C(═O)N(Re)2, —NC(═O)N(Re)2, —OC(═O)O(Re)2, —SO2Re, —SO2ORe, —OSO2Re, —S(═O)Re, or —OS(═O)Re;
each of R9, R10, R11 and R12 is hydrogen, halogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted acyl, —NO2, —CN, —OR4, —OR5, —ORe, —N(Re)2, —N3, —SO2H, —SO3H; —SH, —SRe, —SSRe, —OC(═O)Re, —OCO2Re, —OC(═O)N(Re)2, —OC(═O)N(Re)2, —C(═O)N(Re)2, —NC(═O)N(Re)2, —OC(═O)O(Re)2, —SO2Re, —SO2ORe, —OSO2Re, —S(═O)Re, —OS(═O)Re, or two occurrences of any R9, R10, R11 and R12 are joined to form an optionally substituted carbocyclic ring or an optionally substituted heterocyclic ring;
each of R4 and R5 is independently hydrogen, optionally substituted C1-6 alkyl, optionally substituted acyl, or an oxygen protecting group, or R4 and R5 are joined to form an optionally substituted heterocyclic ring;
X1 is a bond, —O—, —(C(Rd)2)q—, or —NRe—;
each occurrence of Rd is independently hydrogen, halogen, optionally substituted C1-6 alkyl, —ORe, or —N(Re)2;
each occurrence of Re is independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted acyl, an oxygen protecting group when attached to an oxygen atom, a nitrogen protecting group when attached to a nitrogen atom, or two Re are joined to form an optionally substituted carbocyclic, an optionally substituted aryl, an optionally substituted heterocyclic or optionally substituted heteroaryl ring;
q is 1, 2, or 3;
each occurrence of R7 is independently halogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted acyl, —NO2, —CN, —ORe, or —N(Re)2, or two R7 are joined to form an optionally substituted aryl or optionally substituted heteroaryl ring; and
n is 0, 1, 2, 3, 4, or 5.