US 12,297,171 B2
EP2 antagonist compounds
Matthew Alexander James Duncton, San Bruno, CA (US); Vladimir V. Senatorov, Jr., Oakland, CA (US); Aaron R. Friedman, Berkeley, CA (US); and Steven Howard Olson, San Diego, CA (US)
Assigned to Reservoir Neuroscience, Inc., San Francisco, CA (US)
Filed by Reservoir Neuroscience, Inc., Emeryville, CA (US)
Filed on Dec. 22, 2023, as Appl. No. 18/395,348.
Application 18/395,348 is a continuation of application No. PCT/US2022/034903, filed on Jun. 24, 2022.
Claims priority of provisional application 63/214,635, filed on Jun. 24, 2021.
Prior Publication US 2024/0182411 A1, Jun. 6, 2024
Int. Cl. C07D 205/04 (2006.01); C07D 207/09 (2006.01); C07D 401/04 (2006.01); C07D 403/04 (2006.01)
CPC C07D 205/04 (2013.01) [C07D 207/09 (2013.01); C07D 401/04 (2013.01); C07D 403/04 (2013.01)] 17 Claims
 
1. A compound having the structure of Formula (I):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt, or solvate thereof; wherein:
R1 is —C(O)NRdRe;
Rd is —CN, C1-C6 alkyl, C1-C6 deuteroalkyl, C1-C6 fluoroalkyl, C1-6 alkoxy, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted C2-C6 heterocycloalkyl, —OH, OR1d, —SOR1d, or —SO2R1d; wherein R1d is substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted 3- to 6-membered heterocycloalkyl, substituted or unsubstituted phenyl, or substituted or unsubstituted 5- to 6-membered heteroaryl; wherein if R1d is substituted then it is substituted with one or more R14;
Re is hydrogen, C1-C6 alkyl, C1-C6 deuteroalkyl, C1-C6 fluoroalkyl, C1-6 alkoxy, substituted or unsubstituted C3-C6 cycloalkyl, or substituted or unsubstituted C2-C6 heterocycloalkyl;
or Rd and Re are taken together with the N atom to which they are attached to form a substituted or unsubstituted C2-C6 heterocycloalkyl;
R2 is hydrogen, C1-C6 alkyl, C1-C6 deuteroalkyl, or C1-C6fluoroalkyl;
R3 is hydrogen, C1-C6 alkyl, C1-C6 deuteroalkyl, C1-C6 fluoroalkyl, substituted or unsubstituted C3-C6 cycloalkyl, or substituted or unsubstituted C2-C6 heterocycloalkyl;
or R2 and R3 are taken together with the carbon atom to which they are attached to form a carbonyl (C═O) or thiocarbonyl (C═S);
or R2 and R3 are taken together with the carbon atom to which they are attached to form a ring B that is a substituted or unsubstituted C3-C6 cycloalkyl, or substituted or unsubstituted C2-C6 heterocycloalkyl, wherein if the ring B is substituted then it is substituted with one or more R12;
Z is N or CR8;
L is absent or —NH—;
R4, R5, R7, and R8 are each independently hydrogen, halogen, —CN, C1-C6 alkyl, C1-C6 deuteroalkyl, C1-C6 fluoroalkyl, —OR16, —C(═O)R16, —CO2R16, —C(═O)N(R16)2, —N(R16)2, or —NR16C(═O)R16;
R6 is hydrogen, halogen, —CN, C1-C6 alkyl, C1-C6 deuteroalkyl, C1-C6 fluoroalkyl, —OR16, —C(═O)R16, —CO2R16, —C(═O)N(R16)2, —N(R16)2, —NR16C(═O)R16, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted C2-C6heterocycloalkyl, substituted or unsubstituted phenyl, or substituted or unsubstituted heteroaryl; wherein if R6 is substituted then it is substituted with one or more R13;
ring A is a substituted or unsubstituted phenyl, or substituted or unsubstituted heteroaryl;
each R9, R10, R11, R12, R13, and R14 is independently hydrogen, deuterium, halogen, C1-C6 alkyl, C1-C6 deuteroalkyl, C1-C6 fluoroalkyl, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted C2-C6 heterocycloalkyl, —CN, —OR16, —C(═O)R16, —CO2R16, —C(═O)N(R16)2, —N(R16)2, or —NR16C(═O)R16;
each R16 is independently hydrogen, C1-C6 alkyl, C1-C6 deuteroalkyl, C1-C6 fluoroalkyl, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted C2-C6 heterocycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted heteroaryl, -alkyl-(substituted or unsubstituted phenyl), -alkyl-(substituted or unsubstituted heteroaryl), -alkyl-(substituted or unsubstituted C3-C6cycloalkyl), -alkyl-(substituted or unsubstituted C2-C6 heterocycloalkyl);
or both R16 are taken together with the N atom to which they are attached to form a substituted or unsubstituted C2-C6 heterocycloalkyl;
R18 and R19 are each independently hydrogen, deuterium, C1-C6 alkyl, C1-C6 deuteroalkyl, or C1-C6fluoroalkyl;
or R18 and R19 are taken together with the carbon atom to which they are attached to form a ring E that is a C3-C6cycloalky, or C2-C6 heterocycloalkyl;
m is 1 or 2; and
n is 0, 1, 2, 3, or 4.