Drugs to prevent recurrent herpes virus infections

US5646155A · kind A · utility

Assignee

• University of Massachusetts Medical Center · US

Inventor

• George E. Wright · Worcester, US

Key dates

• Filing date: Dec 29, 1994
• Grant date: Jul 8, 1997
• Expiry date: Dec 29, 2014

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07H19/16
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

N.sup.2 -substituted alkylguanine and N.sup.2 -substituted phenylguanine compounds which prevent recurrent herpes simplex infections are disclosed. By virtue of their ability to inhibit herpes virus thymidine kinase in vivo, such compounds will prevent, reduce the frequency of, or reduce the severity of recurring HSV infections in humans. The N.sup.2 -alkylguanine compounds are of the formula: ##STR1## where R.sub.1 is a normal or branched chain C.sub.n H.sub.2n+1 (where n is 1-12); R.sub.2 is H, 2-deoxyribofuranosyl, (CH.sub.2).sub.n OH (where n is 2-5), CH.sub.2 CH(OH)CH.sub.2 OH, (CH.sub.2).sub.n --COOH (where n is 1-4), CH.sub.2 CH(OH)CH.sub.2 --O--COR.sub.4, (CH.sub.2).sub.n --O--COR.sub.4 (where n is 2-5), or (CH.sub.2).sub.n CO--OR.sub.4 (where n is 1-4); R.sub.4 is CH.sub.3, CH.sub.2 CH.sub.3, CH.sub.2 CH.sub.2 NH.sub.2, CH.sub.2 CH.sub.2 N(C.sub.2 H.sub.5).sub.2 or CH.sub.2 CH.sub.2 CO.sub.2 H; and R.sub.3 is OH, H, Cl or NH.sub.2, or a tautomer or a pharmaceutically acceptable salt thereof. The N.sup.2 -substituted phenylguanine compounds are of similar structure, where R.sub.1 is a phenyl or a phenyl substituted at the 3 and 4 positions with an H, a hydrophobic or electr…