Catechol carboxylic acids

A lipoxygenase inhibiting pharmaceutical composition comprising an effective amount of a compound of the formula ##STR51## wherein, R.sup.1 is ##STR52## acetyl, hydrogen, hydroxy or alkanoyloxy, R.sub.2 is ##STR53## hydroxy, hydrogen or alkanoyloxy, wherein R is hydrogen, lower alkyl or (CH.sub.2).sub.n --N--(lower alkyl).sub.2,

• R.sub.3 is hydrogen, lower alkyl or amino,
• R.sub.4 is hydrogen, lower alkyl, halogen or amino, and
• A is ##STR54## wherein, R.sub.5 is hydrogen, benzoyl or alkanoyl of 1 to 7 carbon atoms, R.sub.6 is hydrogen, halogen, lower alkyl, cycloalkyl, phenyl or phenyl bearing one or two substituents independently selected from the group consisting of halogen, trifluoromethyl, lower alkyl, lower alkoxy, nitro, amino, lower alkylamino and di-lower alkylamino, and R.sub.7 and R.sub.8, independently, are hydrogen, lower alkyl or halogen, or R.sub.9 is hydrogen or lower alkyl, R.sub.10 is hydrogen, lower alkyl or halogen, R.sub.11 is hydrogen, lower alkyl, cycloalkyl or halogen, m is 0 or 1, n is an integer of 2 to 10, provided, that no more than one of R.sub.1 or R.sub.2 can be hydroxy, alkanoyloxy or ##STR55## or, when R is hydrogen, a salt thereof with a pharmaceutically acceptable base, or when R is --(CH.sub.2).sub.n --N--(lower alkyl).sub.2 an addition salt thereof with a pharmaceutically acceptable acid and an inert carrier material.

A method of inhibiting lipoxygenase in a host requiring such treatment which comprises administering an effective amount of a compound ##STR60## wherein, R.sup.1 is ##STR61## acetyl, hydrogen, hydroxy or alkanoyloxy, R.sub.2 is ##STR62## hydroxy, hydrogen or alkanoyloxy, wherein R is hydrogen, lower alkyl or --(CH.sub.2).sub.n --N--(lower alkyl).sub.2,

• R.sub.3 is hydrogen, lower alkyl or amino,
• R.sub.4 is hydrogen, lower alkyl, halogen or amino, and
• A is ##STR63## wherein, R.sub.5 is hydrogen, benzoyl or alkanoyl of 1 to 7 carbon atoms, R.sub.6 is hydrogen, halogen, lower alkyl, cycloalkyl, phenyl or phenyl bearing one or two substituents independently selected from the group consisting of halogen, trifluoromethyl, lower alkyl, lower alkoxy, nitro, amino, lower alkylamino and di-lower alkylamino, and R.sub.7 and R.sub.8, independently, are hydrogen, lower alkyl or halogen, or R.sub.9 is hydrogen or lower alkyl, R.sub.10 is hydrogen, lower alkyl or halogen, R.sub.11 is hydrogen, lower alkyl, cycloalkyl or halogen, m is 0 or 1, n is an integer of 2 to 10, provided, that no more than one of R.sub.1 or R.sub.2 can be hydroxy, alkanoyloxy, or ##STR64## or a salt thereof with a pharmaceutically acceptable base when R is hydrogen or when R is --(CH.sub.2).sub.n --N--(lower alkyl).sub.2, an addition salt thereof with a pharmaceutically acceptable acid.

A pharmaceutical composition useful for the treatment of inflammatory bowel disease which comprises a compound of the formula ##STR69## wherein R.sub.1 is carboxy or acetyl, R.sub.2 is hydroxy, R.sub.3 is hydrogen or propyl, R.sub.4 is hydrogen or chloro, n is an integer from 2 to 10, R.sub.5 is hydrogen or acetyl, R.sub.6 is hydrogen, lower alkyl, phenyl or phenyl bearing one or two substituents independently selected from the group consisting of halogen, trifluoromethyl, lower alkyl, lower alkoxy, nitro, amino, lower alkylamino and di-lower alkylamino, and R.sub.7 and R.sub.8 are hydrogen, and an inert carrier material.

A method for the treatment of inflammatory bowel disease in a host requiring such treatment which comprises administering an effect amount of a compound of the formula ##STR70## wherein R.sub.1 is carboxy or acetyl, R.sub.2 is hydroxy, R.sub.3 is hydrogen or propyl, R.sub.4 is hydrogen or chloro, n is an integer from 2 to 10, R.sub.5 is hydrogen or acetyl, R.sub.6 is hydrogen, halogen, lower alkyl phenyl or phenyl bearing one or two substituents independently selected from the group consisting of halogen, trifluoromethyl, lower alkyl, lower alkoxy, nitro, amino, lower alkylamino and di-lower alkylamino, and R.sub.7 and R.sub.8 are hydrogen.