Preparation of asymmetric cyclic ureas through a monoacylated diamine intermediate

US6452000B2 · kind B2 · utility

Assignee

• Bristol-Myers Squibb Pharma Company · US

Inventors

• Benjamin R. P. Stone · West Chester, US
• Luigi Anzalone · West Chester, US
• Joseph M. Fortunak · Newark, US
• Gregory D. Harris · Wilmington, US
• Ioannis I. Valvis · Hockessin, US
• Robert E. Waltermire · Fryeburg, US

Key dates

• Filing date: Mar 7, 2001
• Grant date: Sep 17, 2002
• Expiry date: Mar 7, 2021

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D317/14
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention concerns an improved process for the preparation of asymmetric cyclic ureas as well as intermediates in the preparation of asymmetric cyclic ureas. In the process, a diamine of formula (I-a) is selectively monoacylated to give an asymmetric monoacylated diamine which can be converted into asymmetric intermediates. The asymmetric intermediates can be further alkylated, cyclized, and/or modified to give compounds which are useful as HIV protease inhibitors for the treatment of HIV infection. The invention allows for scalable preparation of a wide variety of asymmetrical cyclic ureas.