Processes for the preparation of (R)-2-(7-4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[B]indol-3-yl)acetic acid and salts thereof

US9175320B2 · kind B2 · utility

Assignee

• Arena Pharmaceuticals, Inc. · US

Inventors

• Antonio Garrido Montalban · San Diego, US
• Daniel J. Buzard · San Diego, US
• John DeMattei · San Diego, US
• Tawfik Gharbaoui · Escondido, US
• Stephen R. Johannsen · San Diego, US
• Ashwin M. Krishnan · San Diego, US
• Young Mi Kuhlman · Plainsboro, US
• You-An Ma · Poway, US
• Michael John Martinelli · Indianapolis, US
• Suzanne Michiko Sato · San Diego, US
• Dipanjan Sengupta · Goleta, US

Key dates

• Filing date: Aug 20, 2014
• Grant date: Nov 3, 2015
• Expiry date: Aug 20, 2034

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07B2200/13
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The present invention relates to processes and intermediates useful in the preparation of (R)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid of Formula (Ia) and salts thereof, an S1P1 receptor modulator that is useful in the treatment of S1P1 receptor-associated disorders, for example, diseases and disorders mediated by lymphocytes, transplant rejection, autoimmune diseases and disorders, inflammatory diseases and disorders (e.g., acute and chronic inflammatory conditions), cancer, and conditions characterized by an underlying defect in vascular integrity or that are associated with angiogenesis such as may be pathologic (e.g., as may occur in inflammation, tumor development and atherosclerosis).