4-(oxygen, sulfur or nitrogen substituted)-methyl 5-hydroxy-2(5H)-furanones as anti-inflammatory agents

US5037811A · kind A · utility

Assignee

• Allergan, Inc. · US

Inventor

• Gary Lee · Dayuan District, TW

Key dates

• Filing date: Apr 17, 1990
• Grant date: Aug 6, 1991
• Expiry date: Apr 17, 2010

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D307/60
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Compounds of the formula ##STR1## in which R.sub.1 is H or alkyl of 1 to 20 carbons, CO--R.sub.1.sup.* CO--O--R.sub.1.sup.* CO--NH--R.sub.1.sup.* or PO(OR.sub.1.sup.*).sub.2 or PO(OR.sub.1.sup.*)R.sub.1.sup.* where R.sub.1.sup.* independently is H, alkyl of 1 to 20 carbons, phenyl, or substituted phenyl; X is O, S, SO--, SO.sub.2, NH--, or NR.sub.2 where R.sub.2 is phenyl, substituted phenyl or alkyl of 1 to 20 carbons, and Y is alkyl having at least 6 carbon atoms, arylalkyl, aryl, substituted aryl, substituted arylalkyl, alkenyl containing one or more olephinic bonds and at least 6 carbon atoms, CO--R.sub.3, CO--OR.sub.3, CONHR.sub.3, SO.sub.2 R.sub.3, SO.sub.2 NHR.sub.3 where R.sub.3 is aryl, substituted aryl, substituted arylalkyl, alkyl, alkenyl containing one or more olephinic bonds, further Y is (CH.sub.2).sub.n --O--R.sub.4, or (CH.sub.2).sub.n --O--(CH.sub.2).sub.m --O--R.sub.4, where n, and m, are integers and are independently 1 to 25 and R.sub.4 is phenyl, substituted phenyl or alkyl of one to 20 carbons, still further Y is PO(OH).sub.2, PO(OH)OR.sub.5, PO(OH)R.sub.5 PO(OR.sub.5).sub.2, where R.sub.5 is independently phenyl, substituted phenyl, alkyl or 1 to 20 carbons …