2- and 5-alkyl and phenyl substituted 4-(1-hydroxy, 1-acyloxy or 1-carbamoyloxy)-5-hydroxy-2 (5H)-furanones as anti-inflammatory agents

A compound of the formula ##STR14## where:

• R.sub.1 independently is H, phenyl, C.sub.1 -C.sub.6 alkyl substituted phenyl, halogen substituted phenyl, or alkyl or 1 to 6 carbons and n is an integer having the values of 1 or 2, and where when n is 1 the R.sub.1 group is attached to one of the 3 and the 5 positions of the 2-furanone, when n is 2 then the R.sub.1 groups are attached to both the 3 and 5 positions, with the proviso that when n is 1 then R.sub.1 is not H;
• Y.sub.1 is CO--R.sub.3 where R.sub.3 is CH.sub.3 --or phenyl;
• Y.sub.2 is H, an alkyl group of 6 to 25 carbons, phenyl, naphthyl, phenyl (C.sub.1 -C.sub.20)alkyl--, naphthyl (C.sub.1 -C.sub.20)alkyl--, halogen substituted phenyl, C.sub.1 -C.sub.6 alkyl substituted phenyl, halogen substituted naphthyl, C.sub.1 -C.sub.6 substituted naphthyl, and
• Y.sub.3 is H, alkyl of 1 to 20 carbons, CO--R.sub.4, CO--O--R.sub.4, CO--NH--R.sub.4, PO(OR.sub.4).sub.2 or PO(OR.sub.4)R.sub.4, where R.sub.4 independently is H, alkyl of 1 to 20 carbons, phenyl, halogen substituted phenyl or C.sub.1 -C.sub.6 alkyl substituted phenyl, with the proviso that when Y.sub.3 is COOR.sub.4 or CONHR.sub.4 then R.sub.4 is not H, or a pharmaceutically acceptable salt thereof.

A compound of the formula ##STR15## where:

• R.sub.1 independently is H, phenyl, C.sub.1 -C.sub.6 alkyl substituted phenyl, halogen substituted phenyl, or alkyl of 1 to 6 carbons, n is 2 and the R.sub.1 groups are attached to both the 3 and 5 positions,
• Y.sub.1 is H, alkyl of 1 to 20 carbons, phenyl C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.20 alkenyl containing one or more olephinic bonds, PO(OH).sub.2, PO(OH)OR.sub.2, PO(OH)R.sub.2, PO(OR.sub.2).sub.2, where R.sub.2 is independently alkyl of 1 to 20 carbons, phenyl, or halogen substituted phenyl or C.sub.1 -C.sub.6 alkyl substituted phenyl, further Y.sub.1 is CO--R.sub.3, CO--OR.sub.3, CONHR.sub.3, SO.sub.2 R.sub.3, SO.sub.2 NHR.sub.3, (CH.sub.2).sub.p --O--R.sub.3, or (CH.sub.2).sub.p --O--(CH.sub.2).sub.m --O--R.sub.3, where p, and m, are integers and are independently 1 to 20 and R.sub.3 is H, C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.20 alkenyl containing one or more olefinic bonds, phenyl, halogen substituted phenyl or C.sub.1 -C.sub.6 alkyl substituted phenyl, with the proviso that when Y.sub.1 is CO--OR.sub. 3, and CONHR.sub.3 then R.sub.3 is not hydrogen;
• Y.sub.2 is H, and
• Y.sub.3 is H, alkyl of 1 to 20 carbons, CO--R.sub.4, CO--O--R.sub.4, CO--NH--R.sub.4, PO(OR.sub.4).sub.2 or PO(OR.sub.4)R.sub.4, where R.sub.4 independently is H, alkyl of 1 to 20 carbons, phenyl, halogen substituted phenyl or C.sub.1 -C.sub.6 alkyl substituted phenyl, with the proviso that when Y.sub.3 is COOR.sub.4 or CONHR.sub.4 then R.sub.4 is not H, or a pharmaceutically acceptable salt thereof.

A compound of the formula ##STR16## where:

• R.sub.1 independently is H, phenyl, C.sub.1 -c.sub.6 alkyl substituted phenyl, halogen substituted phenyl, or alkyl or 1 to 6 carbons and n is an integer having the values of 1 or 2, and where when n is 1 the R.sub.1 group is attached to one of the 3 and the 5 positions of the 2-furanone, when n is 2 then the R.sub.1 groups are attached to both the 3 and 5 positions, with the proviso that when n is 1 then R.sub.1 is not H;
• Y.sub.1 is H, alkyl of 1 to 20 carbons, phenyl C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.20 alkenyl containing one or more olephinic bonds, PO(OH).sub.2, PO(OH)OR.sub.2, PO(OH)R.sub.2, PO(OR.sub.2).sub.2, where R.sub.2 is independently alkyl of 1 to 20 carbons, phenyl, or halogen substituted phenyl or C.sub.1 -C.sub.6 alkyl substituted phenyl, further Y.sub.1 is CO--R.sub.3, CO--OR.sub.3, CONHR.sub.3, SO.sub.2 R.sub.3, SO.sub.2 NHR.sub.3, (CH.sub.2).sub.p --O--R.sub.3, or (CH.sub.2).sub.p --O--(CH.sub.2).sub.m --O--R.sub.3 where p, and m, are integers and are independently 1 to 20 and R.sub.3 is H, C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.20 alkenyl containing one or more olefinic bonds, phenyl, halogen substituted phenyl or C.sub.1 -C.sub.6 alkyl substituted phenyl, with the proviso that when Y.sub.1 is CO--OR.sub.3 , and CONHR.sub.3 then R.sub.3 is not hydrogen;
• Y.sub.2 is alkyl or 8 to 25 carbons, and
• Y.sub.3 is H, alkyl of 1 to 20 carbons, CO--R.sub.4, CO--O--R.sub.4, CO--NH--R.sub.4, PO(OR.sub.4).sub.2 or PO(OR.sub.4)R.sub.4, where R.sub.4 independently is H, alkyl of 1 to 20 carbons, phenyl, halogen substituted phenyl or C.sub.1 -C.sub.6 alkyl substituted phenyl, with the proviso that when Y.sub.3 is COOR.sub.4 or CONHR.sub.4 then R.sub.4 is not H, or a pharmaceutically acceptable salt thereof.