US 12,221,447 B2
Methods and compositions for drugs to treat ophthalmic diseases
Scott W. Cousins, Durham, NC (US); Priyatham S. Mettu, Durham, NC (US); and David M. Gooden, Durham, NC (US)
Assigned to Duke University, Durham, NC (US)
Appl. No. 17/269,830
Filed by Duke University, Durham, NC (US)
PCT Filed Aug. 20, 2019, PCT No. PCT/US2019/047309
§ 371(c)(1), (2) Date Feb. 19, 2021,
PCT Pub. No. WO2020/041344, PCT Pub. Date Feb. 27, 2020.
Claims priority of provisional application 62/719,938, filed on Aug. 20, 2018.
Prior Publication US 2021/0198266 A1, Jul. 1, 2021
Int. Cl. C07D 487/04 (2006.01); A61P 27/02 (2006.01); A61P 37/06 (2006.01); C07D 471/06 (2006.01)
CPC C07D 487/04 (2013.01) [A61P 27/02 (2018.01); A61P 37/06 (2018.01); C07D 471/06 (2013.01)] 18 Claims
 
1. A compound having the Formula (XX):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt, solvate, or hydrate thereof,
wherein X is oxygen (O);
wherein Y is NR4;
wherein R1 is —CH2COOH, —COOH, —CH2COOCR7, —COOR7; —CH2CONH2, —CONH2, —CH2CONR5R6, or —CONR5R6;
wherein each R2 and R3 are independently hydrogen (H), C1-C10 alkyl, —OR7, —OCH2CH2OR7, —OCH2CH2NR5R6, —OCH2CH2COOR7 or —OCH2CH2PO3H;
wherein R4 hydrogen (H), C1-C10 alkyl, —CH2CN, —CH2C(O)NH2, —CH2COOH, —CH2SO2CH3, —CH2CH2NH2, —CH2CH2OH, —CH2thienyl, —CH2furanyl, —CH2CH2heterocycle, —CH2CH2cycloalkyl, —CH2CH2heterocycloalkyl, —CH2CHOCH2OH or —(CH2)nZ(CH2)mCH3, where n is an integer from 1 to 5, m is an integer from 0 to 5, and Z is oxygen (O) or sulfur(S);
wherein each R5 and R6 are independently hydrogen (H), C1-C5 alkyl, or R5 and R6 together may a 3 to 7-member cycloalkyl ring; and
wherein R7 is C1-C5 alkyl.