Omidenepag isopropyl is a novel, selective, non-prostanoid EP2 receptor agonist. It can be used for treatment of open-angle glaucoma and ocular hypertension. Omidenepag isopropyl is a prodrug that is converted by hydrolysis of its isopropyl ester to the active metabolite omidenepag.[5] Omidenepag is a selective prostaglandin E2 receptor agonist. It was approved for medical use in Japan in 2018, and in the United States in September 2022.
This synthetic route was from WO2009113600.
Step 1.1 Reagents: Sodium hydride
Solvents: Dimethylformamide ; 20 min, cooled; 1 h, rt
Step 1.2 10 min, cooled; 1 h, rt
Step 2.1 Reagents: Calcium chloride
Solvents: Ethanol ; 20 min, cooled
Step 2.2 Reagents: Sodium borohydride
Solvents: Tetraglyme ; 20 min, < 35 °C; 15 min, rt
Step 3.1 Reagents: Tributylphosphine , N,N,N′,N′-Tetramethylazodicarboxamide
Solvents: Tetrahydrofuran ; 11 h, rt
Step 4.1 Reagents: Hydrochloric acid
Solvents: Tetrahydrofuran ; 14 h, rt
Step 5.1 Reagents: Hydrochloric acid
Solvents: Isopropanol , 1,4-Dioxane ; 16 h, rt
Preparation of pyridylaminoacetic acids for treatment of respiratory diseases
By: Iwamura, Ryo; et al
World Intellectual Property Organization, WO2009113600 A1 2009-09-17
