Asymmetric Synthesis of the Open-Angle Glaucoma Drug Netarsudil

Asymmetric Synthesis of Netarsudil: A New Therapeutic for Open-Angle Glaucoma: M. A. deLong, J. M. Sturdivant
Synthesis 2018, DOI: 10.1055/s-0037-1610310


Glaucoma is an eye disease that seriously affects the quality of life of 70 million patients worldwide and can lead to blindness. It is characterized by elevated intraocular pressure, which increases the risk of optic nerve damage. Netarsudil – an α-aryl β-amino isoquinoline amide which inhibits the Rho-associated protein kinase (ROCK) – is the active agent of the anti-glaucoma drug Rhopressa™. Researchers based at Aerie Pharmaceuticals Inc., Durham (USA) have recently reported a stereocontrolled approach to this molecule, applicable to large-scale synthesis.

Dr. Jill Sturdivant said: “A chiral amidation agent, 2,2,2 trichloro-1,1-dimethylethyl chloroformate, was successfully used in the key step of the six-step asymmetric synthesis of the first FDA approved ROCK inhibitor netarsudil, which allowed kilo-scale synthesis and commercialization of this important new ocular therapeutic agent, indicated for the reduction of elevated intraocular pressure (IOP) in patients with open-angle glaucoma or ocular hypertension.”
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