Cholesterol conjugates of 2'5'-oligoadenylate derivatives and antiviral uses thereof

US5643889A · kind A · utility

Assignee

• Temple University-of the Commonwealth System of Pennsylvania · US

Inventors

• Robert J. Suhadolnik · Roslyn, US
• Wolfgang Pfleiderer · Konstanz, DE

Key dates

• Filing date: Sep 14, 1994
• Grant date: Jul 1, 1997
• Expiry date: Sep 14, 2014

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07J51/00
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

A cholesterol-cordycepin conjugate having the formula ##STR1## wherein: n is an integer from 1 to 8; R.sub.1 is selected from the group of consisting of T, T' and Y; T is ##STR2## T' is ##STR3## where x is an integer from 1 to 18; Y is ##STR4## where m is zero, 1, 2, or 3; each R.sub.2 is independently selected from the group consisting of oxygen and sulfur; each R.sub.3 is independently selected from the group consisting of hydrogen and hydroxyl; R.sub.4 is selected from the group consisting of hydrogen, hydroxyl and T or T'; R.sub.5 is selected from the group consisting of hydrogen, hydroxyl and T or T'; provided that all R.sub.1, R.sub.4 and R.sub.5 may not be T or T'; at least one R.sub.3 is hydrogen or R.sub.4 is hydrogen; and at least one of R.sub.1, R.sub.4 and R.sub.5 must be T or T'; or a water soluble salt thereof. The compounds possess increased antiviral activity and/or metabolic stability.