(S)-2-(1-aminopropyl)-5-fluoro-3-phenylquinazolin-4(3H)-one precursor of a quinazolinone as inhibitor of human phosphatidylinositol 3-kinase delta

US10336756B2 · kind B2 · utility

Assignee

• ICOS CORPORATION · US

Inventors

• Edward A. Kesicki · Bothell, US
• Kerry W. Fowler · Seattle, US
• Danwen Huang · New York, US
• Hua Chee Ooi · Kirkland, US
• Amy Oliver · Bothell, US
• Kamal D. Puri · Seattle, US
• Fuqiang Ruan · Bellevue, US
• Jennifer Treiberg · Redmond, US

Key dates

• Filing date: Aug 13, 2015
• Grant date: Jul 2, 2019
• Expiry date: Aug 13, 2035

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D487/04
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

Compounds that inhibit PI3Kδ activity, including compounds that selectively inhibit PI3Kδ activity, are disclosed. Methods of preparing such compounds are also disclosed, including the use of (S)-2-(1-aminopropyl)-5-fluoro-3-phenylquinazolin-4(3H)-one as a precursor to synthesize an exemplary compound disclosed in this application, (S)-2-(1-((9H-purin-6-yl)amino)propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one. Methods of inhibiting phosphatidylinositol 3-kinase delta isoform (PI3Kδ) activity, and methods of treating diseases, such as disorders of immunity and inflammation in which PI3Kδ plays a role in leukocyte function, using the compounds also are disclosed.