4-ethyl and 4-ethenyl-5-hydroxy-2(5H)-furanones substituted on alpha carbon of the ethyl or ethenyl side chain with a long chain alkyl group and on the beta carbon with a polar group, as anti-inflammatory agents

US5013850A · kind A · utility

Assignee

• Allergan, Inc. · US

Inventor

• Gary Lee · Dayuan District, TW

Key dates

• Filing date: Mar 30, 1990
• Grant date: May 7, 1991
• Expiry date: Mar 30, 2010

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07F9/65515
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Compounds of Formula 1, and of Formula 2, ##STR1## in which R.sub.1 is H or alkyl of 1 to 20 carbon, CO--R.sub.1 * CO--O--R.sub.1 * CO--NH--R.sub.1 * or PO(OR.sub.1 *).sub.2 or PO(OR.sub.1 *)R.sub.1 * where R.sub.1 * independently is alkyl of 1 to 20 carbons, phenyl, or substituted phenyl; X is long chain alkyl having at least 5 carbon atoms, long chain alkyl of at least 5 carbons substituted with an aryl group, or long chain alkyl of at least 5 carbons substituted with a substituted aryl group; Y is COOH, COOR.sub.2, CONH.sub.2, CONHR.sub.2, CON(R.sub.2).sub.2, CHO, COR.sub.2 ; COCF.sub.3, COCHF.sub.2, CH.dbd.NR.sub.2, CR.sub.2 .dbd.N--R.sub.2, CH.dbd.N--NHR.sub.2, CH.dbd.N--N(R.sub.2).sub.2, CH.dbd.NOH, CR.sub.2 .dbd.N--OH, CH.dbd.NOR.sub.2, CR.sub.2 .dbd.NOR.sub.2, CH.sub.2 OH, CHR.sub.2 OH, C(R.sub.2).sub.2 OH, CH.sub.2 OR.sub.2 * CHR.sub.2 OR.sub.2 * C(R.sub.2).sub.2 OR.sub.2 * SO.sub.2 R.sub.2, PO(OR.sub.3).sub.2, and PS(OR.sub.3).sub.2, where R.sub.2 independently is alkyl, phenyl, or substituted phenyl, R.sub.2 * is alkyl, phenyl, substituted phenyl, alkanoyl, or aroyl, and R.sub.3 is H, alkyl, phenyl or substituted phenyl; W is H, alkyl, phenyl, COOH, COOR.sub.4, CONHR.sub…