Lipoxygenase and cyclooxygenase inhibiting compounds

A compound or pharmaceutically acceptable salt thereof of formula ##STR57## wherein A is selected from the group consisting of

• (a) unsubstituted carbocyclic aryl
• (b) carbocyclic aryl substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms,
• hydroxyalkyl of one to six carbon atoms,
• alkoxy of one to twelve carbon atoms,
• alkoxyalkoxyl in which the two alkoxy portions are independently of one to six carbon atoms,
• alkylthio of one to six carbon atoms,
• hydroxy,
• halogen,
• cyano,
• amino,
• alkylamino of one to six carbon atoms,
• dialkylamino in which the two alkyl groups are independently of one to six carbon atoms,
• alkanoylamino of from two to eight carbon atoms,
• N-alkanoyl-N-alkylamino in which the alkanoyl is of two to eight carbon atoms and the alkyl group is of one to six carbon atoms,
• alkylaminocarbonyl of two to eight carbon atoms,
• dialkylaminocarbonyl in which the two alkyl groups are independently of one to six carbon atoms,
• carboxyl,
• alkoxycarbonyl of two to eight carbon atoms,
• unsubstituted phenyl,
• phenyl, substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms,
• alkoxy of one to six carbon atoms,
• hydroxy or
• halogen,
• unsubstituted phenoxy,
• phenoxy, substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms,
• alkoxy of one to six carbon atoms,
• hydroxy or
• halogen,
• unsubstituted phenylthio,
• phenylthio, substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms,
• alkoxy of one to six carbon atoms,
• hydroxy or
• halogen,
• unsubstituted phenylalkyl wherein the alkyl portion is of one to twelve carbon atoms,
• phenylalkyl wherein the alkyl portion is of one to twelve carbon atoms and the phenyl moiety is substituted with alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms,
• alkoxy of one to six carbon atoms,
• hydroxy or
• halogen,
• unsubstituted pyridyl,
• pyridyl, substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms,
• alkoxy of one to six carbon atoms,
• hydroxy or
• halogen,
• unsubstituted pyridyloxy,
• pyridyloxy, substituted with alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms,
• alkoxy of one to six carbon atoms,
• hydroxy or
• halogen,
• unsubstituted pyridylalkyl wherein the alkyl portion is of one to twelve carbon atoms,
• pyridylalkyl wherein the alkyl portion is of one to twelve carbon atoms and the pryidyl portion is substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms,
• alkoxy of one to six carbon atoms,
• hydroxy or
• halogen;
• (c) unsubstituted furyl,
• (d) furyl substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms,
• halogen,
• unsubstituted phenyl,
• phenyl, substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms,
• alkoxy of one to six carbon atoms,
• hydroxy or
• halogen,
• unsubstituted phenoxy,
• phenoxy, substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms,
• alkoxy of one to six carbon atoms,
• hydroxy or
• halogen,
• unsubstituted phenylthio,
• phenylthio, substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms,
• alkoxy of one to six carbon atoms,
• hydroxy or
• halogen,
• unsubstituted phenylalkyl wherein the alkyl portion is of one to twelve carbon atoms,
• phenylalkyl wherein the alkyl portion is of one to twelve carbon atoms and the phenyl moiety is substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms,
• alkoxy of one to six carbon atoms,
• hydroxy or
• halogen,
• unsubstituted pyridyl,
• pyridyl, substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms,
• alkoxy of one to six carbon atoms,
• hydroxy or
• halogen,
• unsubstituted pyridyloxy,
• pyridyloxy, substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms,
• alkoxy of one to six carbon atoms,
• hydroxy or
• halogen,
• unsubstituted pyridylalkyl wherein the alkyl portion is of one to twelve carbon atoms,
• pyridylalkyl wherein the alkyl portion is of one to twelve carbon atoms and the pryidyl portion is substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms,
• alkoxy of one to six carbon atoms,
• hydroxy or
• halogen;
• (e) unsubstituted benzo[b]furyl,
• (f) benzo[b]furyl substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms;
• alkoxyl of one to six carbon atoms,
• hydroxy, or
• halogen;
• (g) unsubstituted thienyl,
• (h) thienyl substituted with
• alkyl of one to six carbon atoms,
• unsubstituted phenyl,
• phenyl, substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms,
• alkoxy of one to six carbon atoms,
• hydroxy or
• halogen,
• unsubstituted phenoxy,
• phenoxy, substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms,
• alkoxy of one to six carbon atoms,
• hydroxy or
• halogen,
• unsubstituted phenylthio,
• phenylthio, substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms,
• alkoxy of one to six carbon atoms,
• hydroxy or
• halogen,
• unsubstituted phenylalkyl wherein the alkyl portion is of one to twelve carbon atoms,
• phenylalkyl wherein the alkyl portion is of one to twelve carbon atoms and the phenyl moiety is substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms,
• alkoxy of one to six carbon atoms,
• hydroxy or
• halogen,
• unsubstituted pyridyl,
• pyridyl, substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms,
• alkoxy of one to six carbon atoms,
• hydroxy or
• halogen,
• unsubstituted pyridyloxy,
• pyridyloxy, substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms,
• alkoxy of one to six carbon atoms,
• hydroxy or
• halogen,
• unsubstituted pyridylalkyl wherein the alkyl portion is of one to twelve carbon atoms,
• pyridylalkyl wherein the alkyl portion is of one to twelve carbon atoms and the pryidyl portion is substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms,
• alkoxy of one to six carbon atoms,
• hydroxy or
• halogen;
• (i) unsubstituted benzo[b]thienyl,
• (j) benzo[b]thienyl substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms;
• alkoxyl of one to six carbon atoms,
• hydroxy, or
• halogen;
• (k) unsubstituted pyridyl,
• (l) pyridyl substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms;
• alkoxyl of one to six carbon atoms,
• hydroxy,
• halogen,
• unsubstituted phenylalkyl wherein the alkyl portion is of one to twelve carbon atoms,
• phenylalkyl wherein the alkyl portion is of one to twelve carbon atoms and the phenyl moiety is substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms,
• alkoxy of one to six carbon atoms,
• hydroxy or
• halogen,
• (m) unsubstituted quinolyl,
• (n) quinolyl substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms;
• alkoxyl of one to six carbon atoms,
• hydroxy, or
• halogen, and
• (o) unsubstituted indolyl,
• (p) indolyl substituted with
• alkyl of one to six carbon atoms,
• haloalkyl of one to six carbon atoms;
• alkoxyl of one to six carbon atoms,
• hydroxy, or
• halogen;
• X is selected from the group consisting of
• unsubstituted alkyl of one to six carbon atoms,
• alkyl of one to six carbon atoms substituted with
• hydroxy,
• halogen,
• cyano,
• alkoxy of one to six carbon atoms,
• carboxy,
• alkoxycarbonyl of one to six carbon atoms, or
• aminocarbonyl,
• unsubstituted alkenyl of two to six carbon atoms,
• alkenyl of two to six carbon atoms substituted with
• hydroxy,
• halogen,
• cyano,
• alkoxy of one to six carbon atoms,
• carboxy,
• alkoxycarbonyl of one to six carbon atoms, or
• aminocarbonyl,
• unsubstituted alkynyl of two to six carbon atoms, and
• alkynyl of two to six carbon atoms substituted with
• hydroxy,
• halogen,
• cyano,
• alkoxy of one to six carbon atoms,
• carboxy,
• alkoxycarbonyl of one to six carbon atoms, or
• aminocarbonyl,
• R.sup.1 and R.sup.2 are independently selected from the group consisting of
• hydrogen,
• hydroxy, and
• alkyl of one to six carbon atoms,
• provided that R.sup.1 and R.sup.2 are not both hydroxyl;
• Z is a residue of a non-steroidal anti-inflammatory drug of the general formula Z--COOH, said non-steroidal anti-inflammatory drug selected from the group consisting of
• acetylsalicylic acid,
• benoxaprofen,
• benzofenac,
• bucloxic acid,
• butibufen,
• carprofen,
• cicloprofen,
• cinmetacin,
• clidanac,
• clopirac,
• diclofenac,
• etodolac,
• fenbufen,
• fenclofenac,
• fenclorac,
• fenoprofen,
• fentiazac,
• flunoxaprofen,
• flurbiprofen,
• furaprofen,
• furobufen,
• furofenac,
• ibuprofen,
• ibufenac,
• indomethacin,
• indoprofen,
• isoxepac,
• ketoprofen,
• ketorolac,
• lonazolac,
• meclofenamic acid,
• 6-methoxynaphth-2-ylacetic acid (4-MNA),
• metiazinic acid,
• miroprofen,
• naproxen,
• oxaprozin,
• oxepinac,
• pirprofen,
• pirazolac,
• protizinic acid,
• sulindac,
• suprofen,
• tiaprofenic acid,
• tolmetin, and
• zomepirac.