Pyridylmethyl esters of selected bio-affecting carboxylic acids

Claim 1

A compound selected from the group consisting of: (a) compounds having the structural formula ##STR459## wherein R 1 and R 2 , which can be the same or different, are each hydrogen, C 1 -C 5 alkyl, C 1 -C 5 alkoxy, C 1 -C 5 alkylthio, phenyl, or substituted phenyl having one or more substituents each of which is selected from the group consisting of C 1 -C 5 alkyl, C 1 -C 5 alkoxy, chloro and dialkylamino wherein the alkyl portions, which can be the same or different, each have 1 to 5 carbon atoms, with the proviso that when R 1 is alkoxy or alkylthio, then R 2 cannot be alkoxy or alkylthio; X and X', which can be the same or different, are each hydrogen, C 1 -C 5 alkyl, carboxy, C 2 -C 6 alkoxycarbonyl, halo, C 1 -C 5 alkoxy, dialkylcarbamyl wherein the alkyl portions, which can be the same or different, each have 1 to 5 carbon atoms, phenyl, or substituted phenyl having one or more substituents each of which is selected from the group consisting of C.sub. 1 -C 5 alkyl, C 1 -C 5 alkoxy, C 1 -C 6 alkanoyl, C 1 -C 6 alkanoyloxy, halo, cyano, C 2 -C 6 alkoxycarbonyl, C 1 -C 5 alkylthio, nitro, C 1 -C 5 haloalkyl have one or more halo substituents, carboxy, C 1 -C 5 alkylsulfonyl, dialkylamino wherein the alkyl portions, which can be the same or different, each have 1 to 5 carbon atoms, and dialkylcarbamyl wherein the alkyl portions, which can be the same or different, each have 1 to 5 carbon atoms; the pyridyl ring is oriented such that it is attached to the ##STR460## portion of the molecule via a carbon-carbon bond; and R--COO-- is the acyloxy residue of: (1) a monocarboxylic acid selected from the group consisting of indomethacin, aspirin, naproxen, sulindac, tolmetin, diflunisal, flurbiprofen, indoprofen, fenclozic acid, ketoprofen, alclofenac, bucloxic acid, cinchophen, pirprofen, fluprofen, flutiazin, clometacin, flufenisal, salsalate, ibuprofen, ibufenac, cinmetacin, furobufen and prodolic acid; (2) a steroidal monocarboxylic acid having the structural formula ##STR461## wherein R 4 is hydrogen, fluoro, chloro, or methyl; R 5 is hydrogen, fluoro or chloro; R 6 is hydrogen, methyl, hydroxy or --OCOR 8 wherein R 8 is C 1 -C 7 straight or branched alkyl or phenyl; R 7 is hydrogen, hydroxy, or --OCOR 8 wherein R 8 is as defined above, with the proviso that when R 6 is hydroxy or --OCOR 8 and R 7 is other than hydrogen, then R 6 and R 7 are identical; or R 6 and R 7 are combined to form a divalent radical of the type ##STR462## wherein R 9 and R 10 , which can be the same or different, are each C 1 -C 7 straight or branched alkyl or phenyl; Z is carbonyl or β-hydroxymethylene; the wavy line at the 16-position indicates the α or β-configuration; and the dotted line in ring A indicates that the 1,2-linkage is saturated or unsaturated; (3) a cephalosporin antibiotic having one carboxylic acid function; (4) a penicillin antibiotic having one carboxylic acid function; or (5) a monocarboxylic acid selected from the group consisting of γ-aminobutyric acid, captopril and valproic acid; (b) compounds having the structural formula ##STR463## wherein the groups attached to each end of the divalent --OOC--R'--COO-- residue are identical to each other; R 1 , R 2 , X, X' and the orientation of the pyridyl ring are as defined with respect to formula (I) above; and --OOC--R'--COO-- is the di(acyloxy) residue of: (1) a cephalosporin antibiotic having two carboxylic acid functions; (2) a penicillin antibiotic having two carboxylic acid functions; or (3) the dicarboxylic acid, methotrexate; and (c) the non-toxic pharmaceutically acceptable acid addition salts, quaternary ammonium salts, and N-oxides of the compounds of formulas (I) and (II) above.