Pyrrolo[2,3-d] pyrimidines as antiviral agents

US6342501B1 · kind B1 · utility

Assignee

• THE REGENTS OF THE UNIVERSITY OF MICHIGAN · US

Inventors

• Leroy B. Townsend · Ann Arbor, US
• John C. Drach · Ann Arbor, US

Key dates

• Filing date: Jan 11, 1999
• Grant date: Jan 29, 2002
• Expiry date: Jan 11, 2019

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61P31/22
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

This invention relates to a novel class of 4,5,6,7-substituted non-nucleoside, non-phosphorylatable pyrrolo[2,3-d]pyrimidines which exhibit both significantly lower levels of cytotoxicity and superior antiviral activity than known nucleoside, non-nucleoside, and non-nucleoside, non-phosphorylatable pyrrolo[2,3-d]pyrimidine derivatives, particularly against human DNA viruses such as cytomegalovirus (HCMV) and herpes simplex virus type 1 (HSV-1). These compounds are represented by the following formula: wherein: R4 is —NR1R2 or oxo; R5 is —CN, or —CSNR1R2, or —CONR1R2; R6 is —H, or halo, or —NR1R2; wherein R1 and R2 are independently —H or an aliphatic group; and R7 is of the formula R3—Ar, wherein R3 is an aliphatic group and Ar is an unsubstituted aryl or an aryl independently substituted with halo, nitro, amino, or aliphatic groups; provided that when R5 is a —CN or —CSNH2, and R6 is a —H or —NH2, and Ar is a —C6H5 or a phenyl substituted with only one aliphatic group, R3 is an aliphatic group other than methyl such that —R3— is not a —CH2—; and pharmaceutically acceptable salts, …