Novel pyridazinylhydrazones and method of administering same

A compound of the formula ##STR11## wherein K is a group having the formula ##STR12## wherein R.sup.3 is hydrogen, C.sub.1 to C.sub.10 alkyl, C.sub.3 to C.sub.7 cycloalkyl, trifluoromethyl, phenyl, phenyl substituted by chloro, nitro, at least one methoxy, pyridyl or C.sub.1 to C.sub.4 alkoxycarbonyl;

• R.sup.4 and R.sup.5 are each hydrogen, C.sub.1 to C.sub.4 alkyl, or C.sub.1 to C.sub.4 alkoxycarbonyl;
• R.sup.6 is carboxyl, --CONHNH.sub.2, --CONH.sub.2 or --CO.sub.2 R.sup.9 wherein
• R.sup.9 is C.sub.1 to C.sub.9 alkyl, C.sub.2 to C.sub.4 hydroxyalkyl or C.sub.3 to C.sub.7 cycloalkyl;
• and
• n is 0, 1, 2, 3, 4 or 5;
• or
• K is selected from the group which consists of:
• 1. 7,7-trimethyl-2-bicyclo(2,2,1)heptylidene-2,2-dimethyl-3-bicyclo(2,2,1)h eptylideno,
• 1-(2,6,6-trimethyl-1-cyclohexenyl)-1-ethylideno,
• 1-methyl-4-isopropenyl-2-cyclohex-6-enylideno,
• 1-(2-bicyclo[2,2,1]hept-5-enyl)-1-ethylideno,
• 1-methyl-4-isopropyl-3-cyclohexylideno,
• 1-methyl-4-isopropylideno-3-cyclohexylideno,
• 2-methyl-1-cyclohexylideno,
• 2,6-dimethyl-1-cyclohexylideno,
• 2-(ethoxycarbonyl)-1-cyclohexylideno,
• 2-carboxy-1-cyclohexylideno,
• ethoxycarbonyl-methylideno, and
• carboxymethylideno;
• or a pharmaceutically acceptable salt thereof.

A compound of the formula ##STR13## wherein K is a group having the formula ##STR14## wherein R.sup.3 is hydrogen, C.sub.1 to C.sub.10 alkyl, trifluoromethyl, phenyl, phenyl substituted by chloro, nitro, at least one methoxy, pyridyl or C.sub.1 to C.sub.4 alkoxycarbonyl;

• R.sup.4 and R.sup.5 are each hydrogen or C.sub.1 to C.sub.4 alkyl;
• R.sup.6 is carboxyl, --CONHNH.sub.2, --CONH.sub.2 or --CO.sub.2 R.sup.9
• wherein
• R.sup.9 is C.sub.1 to C.sub.9 alkyl, or C.sub.3 to C.sub.7 cycloalkyl;
• and
• n is 0, 1, 2, 3, 4 or 5;
• or
• K is selected from the group which consists of:
• 1. 7,7-trimethyl-2-bicyclo(2,2,1)heptylidene-2,2-dimethyl-3-bicyclo(2,2,1)h eptylideno,
• 1-(2,6,6-trimethyl-1-cyclohexenyl)-1-ethylideno,
• 1-methyl-4-isopropenyl-2-cyclohex-6-enylideno,
• 1-(2-bicyclo[2,2,1]hept-5-enyl)-1-ethylideno,
• 1-methyl-4-isopropyl-3-cyclohexylideno,
• 1-methyl-4-isoropylideno-3-cyclohexylideno,
• 2-methyl-1-cyclohexylideno,
• 2,6-dimethyl-1-cyclohexylideno,
• 2-(ethoxycarbonyl)-1-cyclohexylideno, and
• 2-carboxy-1-cyclohexylideno;
• or a pharmaceutically acceptable salt thereof.

A compound of the formula ##STR15## wherein K is a group having the formula ##STR16## wherein R.sup.3 is alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy group;

• R.sup.4 and R.sup.5 are each hydrogen, alkyl having 1 to 4 carbon atoms, or alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy group;
• R.sup.6 is hydrogen, carboxyl, or the group --CO.sub.2 R.sup.9
• wherein
• R.sup.9 is alkyl having 1 to 9 carbon atoms;
• and
• n is 0, 1, 2, 3, 4 or 5;
• or a pharmaceutically acceptable salt thereof.

A compound of the formula ##STR17## wherein K is a group having the formula ##STR18## wherein R.sup.3 is alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy group;

• R.sup.4 and R.sup.5 are each hydrogen, alkyl having 1 to 4 carbon atoms, or alkoxy carbonyl having 1 to 4 carbon atoms in the alkoxy group;
• R.sup.6 is hydrogen, carboxy, or the group --CO.sub.2 R.sup.9
• wherein
• R.sup.9 is alkyl having 1 to 9 carbon atoms;
• and
• n is 0, 1, 2, 3, 4, or 5;
• or a pharmaceutically acceptable salt thereof.

A compound of the formula ##STR19## wherein K is a group having the formula ##STR20## wherein R.sup.3 is alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy group;

• R.sup.4 and R.sup.5 are each hydrogen or alkyl having 1 to 4 carbon atoms,
• R.sup.6 is carboxy, or the group --CO.sub.2 R.sup.9
• wherein
• R.sup.9 is alkyl having 1 to 9 carbon atoms;
• and
• n is 0, 1, 2, 3, 4 or 5;
• or a pharmaceutically acceptable salt thereof.

A compound selected from the group consisting of

• 3-(ethoxycarbonyl)-2-propylidene-(3-chloro-6-pyridazinyl)-hydrazone;
• 3-(methoxycarbonyl)-2-propylidene-(3-chloro-6-pyridazinyl)-hydrazone;
• 3-(ethoxycarbonyl)-2-butylidene-(3-chloro-6-pyridazinyl)-hydrazone;
• 5-(ethoxycarbonyl)-2-pentylidene-(3-chloro-6-pyridazinyl)-hydrazone;
• 3-(propoxycarbonyl)-2-propylidene-(3-chloro-6-pyridazinyl)-hydrazone;
• 3-(isopropoxycarbonyl)-2-propylidene-(3-chloro-6-pyridazinyl)-hydrazone;
• 3-(tert-butoxycarbonyl)-2-propylidene-(3-chloro-6-pyridazinyl)-hydrazone;
• 3-(octyloxycarbonyl)-2-propylidene-(3-chloro-6-pyridazinyl)-hydrazone;
• 3-(cyclohexyloxycarbonyl)-2-propylidene-(3-chloro-6-pyridazinyl)-hydrazone;
• 1-(ethoxycarbonyl)-3,3,3-trifluoro-2-propylidene-(3-chloro-6-pyridazinyl)-h ydrazone;
• 1-(ethoxycarbonyl)-2-phenyl-2-ethylidene-(3-chloro-6-pyridazinyl)-hydrazone
• 1-(ethoxycarbonyl)-2-(4-nitro-phenyl)-2-ethylidene-(3-chloro-6-pyridazinyl) -hydrazone;
• 1-(ethoxycarbonyl)-2-(3,4,5-trimethoxyphenyl)-2-ethylidene-(3-chloro-6-pyri dazinyl)-hydrazone;
• 1-(ethoxycarbonyl)-2-(3-pyridyl)-2-ethylidene-(3-chloro-6-pyridazinyl)-hydr azone;
• 4-carboxy-2-butylidene-(3-chloro-6-pyridazinyl)-hydrazone;
• 6-carboxy-2-hexylidene-(3-chloro-6-pyridazinyl)-hydrazone;
• 4-(methoxycarbonyl)-2-butylidene-(3-chloro-6-pyridazinyl)-hydrazone;
• 4-(tert-butoxycarbonyl)-2-butylidene-(3-chloro-6-pyridazinyl)-hydrazone;
• 6-(ethoxycarbonyl)-2-hexylidene-(3-chloro-6-pyridazinyl)-hydrazone;
• 5-carboxy-2-pentylidene-(3-chloro-6-pyridazinyl)-hydrazone;
• 4-(ethoxycarbonyl)-2-butylidene-(3-chloro-6-pyridazinyl)-hydrazone;
• 2-(ethoxycarbonyl)-1-ethylidene-(3-chloro-6-pyridazinyl)-hydrazone;
• 3-carbamoyl-2-propylidene-(3-chloro-6-pyridazinyl)-hydrazone;
• 1,7,7-trimethyl-2-bicyclo(2,2,1)heptylidene-(3-chloro-6-pyridazinyl)-hydraz one;
• 2,2-dimethyl-3-bicyclo(2,2,1)heptylidene-(3-chloro-6-pyridazinyl)-hydrazone ;
• 1-(2,6,6-trimethyl-1-cyclohexenyl)-1-ethylidene-(3-chloro-6-pyridazinyl)-hy drazone;
• 1-(2-bicyclo[2,2,1]hept-5-enyl)-1-ethylidene-(3-chloro-6-pyridazinyl)-hydra zone;
• 1-methyl-4-isopropyl-3-cyclohexylidene-(3-chloro-6-pyridazinyl)-hydrazone;
• 1-methyl-4-isopropylidene-3-cyclohexylidene-(3-chloro-6-pyridazinyl)-hydraz one;
• 2-methyl-1-cyclohexylidene-(3-chloro-6-pyridazinyl)-hydrazone;
• 2,6-dimethyl-1-cyclohexylidene-(3-chloro-6-pyridazinyl)-hydrazone;
• 2-(ethoxycarbonyl)-1-cyclohexylidene-(3-chloro-6-pyridazinyl)-hydrazone;
• and
• 2-carboxy-1-cyclohexylidene-(3-chloro-6-pyridazinyl)-hydrazone.