US 12,240,829 B2
Prostaglandin receptor EP2 antagonists, derivatives, and uses related thereto
Thota Ganesh, Atlanta, GA (US); Raymond J. Dingledine, Atlanta, GA (US); Radhika Amaradahi, Atlanta, GA (US); and Shabber Mohammed, Atlanta, GA (US)
Assigned to Emory University, Atlanta, GA (US)
Appl. No. 17/440,437
Filed by Emory University, Atlanta, GA (US)
PCT Filed Mar. 19, 2020, PCT No. PCT/US2020/023659
§ 371(c)(1), (2) Date Sep. 17, 2021,
PCT Pub. No. WO2020/191208, PCT Pub. Date Sep. 24, 2020.
Claims priority of provisional application 62/821,163, filed on Mar. 20, 2019.
Prior Publication US 2022/0162186 A1, May 26, 2022
Int. Cl. C07D 401/14 (2006.01); A61P 35/00 (2006.01); C07D 403/12 (2006.01)
CPC C07D 401/14 (2013.01) [A61P 35/00 (2018.01); C07D 403/12 (2013.01)] 2 Claims
 
1. A compound having Formula III,

OG Complex Work Unit Chemistry
or pharmaceutically acceptable salt or prodrug thereof, wherein:
a dotted line represents a double or single bond,
n is 1, 2, 3, or 4;
Q is CH, N, or NX6;
W is N or C;
R1, R2, and R3 are each, the same or different, hydrogen, alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl)2amino, alkylsulfinyl, alkylsulfonyl, arylsulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R1, R2, and R3 are optionally substituted with one or more, the same or different, R10;
X1, X2, X3, and X4 are each, the same or different, hydrogen, alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl)2amino, alkylsulfinyl, alkylsulfonyl, arylsulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein X1, X2, X3, and X4 are optionally substituted with one or more, the same or different, X10;
X5 and X6 are each, the same or different, hydrogen or alkyl, wherein X5 and X6 are optionally substituted with one or more, the same or different, X10;
X10 is alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl)2amino, alkylsulfinyl, alkylsulfonyl, arylsulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein X10 is optionally substituted with one or more, the same or different, X11;
X11 is halogen, nitro, cyano, hydroxy, trifluoromethoxy, trifluoromethyl, amino, formyl, carboxy, carbamoyl, mercapto, sulfamoyl, methyl, ethyl, methoxy, ethoxy, acetyl, acetoxy, methylamino, ethylamino, dimethylamino, diethylamino, N-methyl-N-ethylamino, acetylamino, N-methylcarbamoyl, N-ethylcarbamoyl, N,N-dimethylcarbamoyl, N,N-diethylcarbamoyl, N-methyl-N-ethylcarbamoyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, mesyl, ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, N-methylsulfamoyl, N-ethylsulfamoyl, N,N-dimethylsulfamoyl, N,N-diethylsulfamoyl, N-methyl-N-ethylsulfamoyl, carbocyclyl, aryl, or heterocyclyl;
R10 is alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl)2amino, alkylsulfinyl, alkylsulfonyl, arylsulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R10 is optionally substituted with one or more, the same or different, R11;
R11 is alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl)2amino, alkylsulfinyl, alkylsulfonyl, arylsulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R11 is optionally substituted with one or more, the same or different, R12; and
R12 is halogen, nitro, cyano, hydroxy, trifluoromethoxy, trifluoromethyl, amino, formyl, carboxy, carbamoyl, mercapto, sulfamoyl, methyl, ethyl, methoxy, ethoxy, acetyl, acetoxy, methylamino, ethylamino, dimethylamino, diethylamino, N-methyl-N-ethylamino, acetylamino, N-methylcarbamoyl, N-ethylcarbamoyl, N,N-dimethylcarbamoyl, N,N-diethylcarbamoyl, N-methyl-N-ethylcarbamoyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, mesyl, ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, N-methylsulfamoyl, N-ethylsulfamoyl, N,N-dimethylsulfamoyl, N,N-diethylsulfamoyl, N-methyl-N-ethylsulfamoyl, carbocyclyl, aryl, or heterocyclyl.