Tetrahydroisoquinoline derivatives as highly selective and potent Rho kinase inhibitors

J Med Chem. 2010 Aug 12;53(15):5727-37. doi: 10.1021/jm100579r.

Abstract

Rho kinase (ROCK) is a promising drug target for the treatment of many diseases including hypertension, multiple sclerosis, cancer, and glaucoma. The structure-activity relationships (SAR) around a series of tetrahydroisoquinolines were evaluated utilizing biochemical and cell-based assays to measure ROCK inhibition. These novel ROCK inhibitors possess high potency, high selectivity, and appropriate pharmacokinetic properties for glaucoma applications. The lead compound, 35, had subnanomolar potency in enzyme ROCK-II assays as well as excellent cell-based potency (IC(50) = 51 nM). In a kinase panel profiling, 35 had an off-target hit rate of only 1.6% against 442 kinases. Pharmacology studies showed that compound 35 was efficacious in reducing intraocular pressure (IOP) in rats with reasonably long duration of action. These results suggest that compound 35 may serve as a promising agent for further development in the treatment of glaucoma.

MeSH terms

  • Animals
  • Antihypertensive Agents / chemical synthesis*
  • Antihypertensive Agents / pharmacokinetics
  • Antihypertensive Agents / pharmacology
  • Cell Line
  • Humans
  • In Vitro Techniques
  • Intraocular Pressure / drug effects
  • Isoquinolines / chemical synthesis*
  • Isoquinolines / pharmacokinetics
  • Isoquinolines / pharmacology
  • Microsomes, Liver / metabolism
  • Models, Molecular
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / pharmacokinetics
  • Pyrazoles / pharmacology
  • Rats
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tetrahydroisoquinolines / chemical synthesis*
  • Tetrahydroisoquinolines / pharmacokinetics
  • Tetrahydroisoquinolines / pharmacology
  • rho-Associated Kinases / antagonists & inhibitors*

Substances

  • 6-methoxy-N-(2-((1-methylpiperidin-4-yl)methoxy)-4-(1H-pyrazol-4-yl)phenyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide
  • Antihypertensive Agents
  • Isoquinolines
  • Pyrazoles
  • Tetrahydroisoquinolines
  • rho-Associated Kinases