Tert-butyl (s)-(1-(5-fluoro-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)propyl)carbamate precursor of a quinazolinone inhibitor of human phosphatidylinositol 3-kinase delta and a process for preparing thereof

US10906907B2 · 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: May 21, 2019
• Grant date: Feb 2, 2021
• Expiry date: May 21, 2039

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 preparation and use of the compound tert-butyl (S)-(1-(5-fluoro-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)propyl)carbamate of formula (110) 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.