4-(1-hydroxy-2-substituted amino)ethyl-5-hydroxy-2(5H)-furanones as anti-inflammatory agents

US5081147A · kind A · utility

Assignee

• Allergan, Inc. · US

Inventor

• Gary Lee · Dayuan District, TW

Key dates

• Filing date: Mar 15, 1990
• Grant date: Jan 14, 1992
• Expiry date: Mar 15, 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## where R.sub.1 is H or alkyl of 1 to 20 carbons, CO--R.sub.1 *, CO--O--R.sub.1 *, CO--NH--R.sub.1 *, or PO(OR.sub.1 *).sub.2, PO(OR.sub.1 *)R.sub.1 * where R.sub.1 * independently is H, alkyl of 1 to 20 carbons, phenyl, or substituted phenyl; PA0 R.sub.2 is H or alkyl of 1 to 20 carbons; PA0 X is H, R.sub.3, CO--R.sub.3, CO--O--R.sub.3, CO--NH--R.sub.3, CO--N--(R.sub.3).sub.2, PO(OR.sub.3).sub.2, PO(OR.sub.3)R.sub.3, and R.sub.3 independently is H, phenyl, substituted phenyl, alkyl of 1 to 20 carbons or is alkyl of 1 to 20 carbons substituted with a hydroxyl, alkoxy, substituted amino, thioalkoxy or with a COR.sub.3 * group where R.sub.3 * is H, lower alkyl, OH, OR.sub.3 **, NH.sub.2, NHR.sub.3 ** or N(R.sub.3 **).sub.2 group wherein R.sub.3 ** independently is H or lower alkyl, with the proviso that when X is CO--O--R.sub.3 or is CO--NH--R.sub.3 then R.sub.3 is not hydrogen; PA0 Y is H, R.sub.4, CO--R.sub.4, CO--O--R.sub.4, CO-N-piperazinyl, CO-N-substituted N-piperazinyl, CO-N-morpholinyl, CO-N-substituted N-morpholinyl, CO--NH--R.sub.4, or CO--N(R.sub.4).sub.2, PO(OR.sub.4).sub.2, PO(OR.sub.4)R.sub.4, SO.sub.2 OR.sub.4, or SO.sub.2 R.sub.4, where…