Non-azo and azo compounds containing at least one 4,6-diamino-1-substituted-5-substituted carbamoylpyrid-2-one group

Claim 2

A compound of the formula ##STR95## wherein each R is independently --N(R 1 ) 2 , --N.sup.⊕ (R 1 ) 3 A.sup.⊖ or hydroxy, wherein each R 1 is independently hydrogen; C 1-12 alkyl; C 1-12 alkyl substituted by halo, cyano, hydroxy, phenyl or carbamoyl; cyclohexyl; cyclohexyl substituted by 1 to 3 C 1-4 alkyl groups; phenyl or phenyl substituted by 1 to 3 C 1-4 alkyl groups or --N(R 1 ) 2 is piperidino, morpholino, piperazino, N'-C 1-4 alkylpiperazino or pyrrolidino, each R 2 is independently C 1-12 alkyl; C 1-12 alkyl substituted by halo, cyano, hydroxy, phenyl or carbamoyl; cyclohexyl; cyclohexyl substituted by 1 to 3 C 1-4 alkyl groups; phenyl or phenyl substituted by 1 to 3 C 1-4 alkyl groups or --N.sup.⊕ (R 2 ) 3 is N-R 2 -piperidinium, N-R 2 -morpholinium, N-R 2 -piperazinium, N-R 2 -N'-C 1-4 alkylpiperazinium, N-R 2 -pyrrolidinium, pyridinium or pyridinium substituted by 1 to 3 C 1-4 alkyl groups, wherein R 2 is as defined above, and A.sup.⊖ is a non-chromophoric anion, each T is independently C 1-12 alkylene or C 3-12 alkenylene, and Z is hydrogen or --N═N--D, wherein D is a diazo component radical.

Claim 3

A compound according to claim 1 wherein Z is --N═N--D.

Claim 4

A compound according to claim 1 wherein Z is hydrogen.

Claim 5

A compound of the formula ##STR96## wherein each R' Is independently --N(R 1 ') 2 , --N.sup.⊕ (R 2 ') 3 A.sup.⊖ or hydroxy, wherein each R 1 ' is independently hydrogen; C 1-12 alkyl; C 1-12 alkyl substituted by halo, cyano, hydroxy, phenyl or carbamoyl; cyclohexyl; cyclohexyl substituted by 1 to 3 C 1-4 alkyl groups; phenyl or phenyl substituted by 1 to 3 C 1-4 alkyl groups or --N(R 1 ') 2 is piperidino, morpholino, piperazino, N'-C 1-4 alkylpiperazino or pyrrolidino, and each R 2 ' is independently C 1-12 alkyl; C 1-12 alkyl substituted by halo, cyano, hydroxy, phenyl or carbamoyl; cyclohexyl; cyclohexyl substituted by 1 to 3 C 1-4 alkyl groups; phenyl or phenyl substituted by 1 to 3 C 1-4 alkyl groups or --N.sup.⊕ (R 2 ') 3 is N-R 2 '-piperidinium, N-R 2 '-morpholinium, N-R 2 '-piperazinium, N-R 2 '-N'-C 1-4 alkylpiperazinium, N-R 2 '-pyrrolidinium, pyridinium or pyridinium substituted by 1 to 3 C 1-4 alkyl groups, each T 1 is C 1-12 alkylene or C 3-12 alkenylene, and Z' is hydrogen, R1 ? ##STR97## wherein each R 3 is independently hydrogen, halo, C 1-4 alkyl or C 1-4 alkoxy, each R 3a is independently hydrogen, halo, C 1-4 alkyl, C 1-4 alkoxy, nitro, ##STR98## wherein R 3 is as defined above, and K and X are as defined below, wherein K is ##STR99## wherein K a is ##STR100## wherein each R' and T 1 is as defined above, and each R a , R 8 , R 9 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , X and p is as defined below, each R a is --N(R 1 ') 2 or --N.sup.⊕ (R 2 ') 3 A.sup.⊖, R 8 is hydrogen, methyl, methoxy or ethoxy, R 9 is ##STR101## wherein each of R 23 , R 24 and R 25 is independently hydrogen, halo, C 1-4 alkyl, C 1-4 alkoxy, nitro or cyano, and R a and R 8 are as defined above, R 10 is C 1-4 alkyl or C 1-4 alkoxy, R 11 is C 1-4 alkyl or C 1-4 alkoxy, R 12 is hydrogen, C 1-4 alkyl, benzyl or phenyl, R 13 is hydrogen, cyano, carbamoyl, ##STR102## wherein R 26 is C 1-4 alkyl, amino, C 1-4 alkylamino, di-(C 1-4 alkyl)amino, (C 1-4 alkyl)carbamoyl or di-(C 1-4 alkyl)carbamoyl, and u is 0, 1 or 2, R 14 is hydrogen, C 1-4 alkyl, phenyl(C 1-4 alkyl), 2-cyanoethyl, 2-hydroxyethyl, --(CH 2 ) r --N(R 1a ) 2 , 3-methoxypropyl, --(CH 2 ) r --N.sup.⊕ (R 2 ') 3 A.sup.⊖ or phenylamino, wherein each R 1a is C 1-12 alkyl; C 1-12 alkyl substituted by halo, cyano, hydroxy, phenyl or carbamoyl; cyclohexyl; cyclohexyl substituted by 1 to 3 C 1-4 alkyl groups; phenyl or phenyl substituted by 1 to 3 C 1-4 alkyl groups or --N(R 1a ) 2 is piperidino, morpholino, piperazino, N'-C 1-4 alkylpiperazino or pyrrolidino, and r is 2, 3, 4, 5 or 6, each R 15 is independently hydrogen, C 1-4 alkyl, 3-methoxypropyl, 2-hydroxyethyl, 3-dimethylaminopropyl, 3-diethylaminopropyl or 3-trimethylammoniumpropyl A.sup.⊖, R 16 is hydroxy or amino, R 17 is C 1-4 alkyl, --CO--OR 32 or --CO--NR 33 R 34 , wherein R 32 is C 1-4 alkyl, R 33 is hydrogen or C 1-4 alkyl, and R 34 is hydrogen or C 1-4 alkyl, R 18 is ##STR103## wherein each of R 28 and R 29 is independently hydrogen, halo, C 1-4 alkyl, C 1-4 alkoxy, nitro, amino or acetamido, and R 30 is hydrogen or --NH--CO--(CH 2 ) m --R 35 , wherein R 35 is --N.sup.⊕ (R 2 ') 3 A.sup.⊖, ##STR104## R 19 is hydrazino, --NH--(CH 2 ) m --N(R 1 ') 2 or nitrophenylamino, R 20 is C 1-4 alkyl, benzyl or 2-cyanoethyl, R 21 is C 1-4 alkyl, --(CH 2 ) m --N.sup.⊕ (CH 3 ) 3 A.sup.⊖ or ##STR105## R 22 is ##STR106## wherein each R 31 is independently --NH--(CH 2 ) m --(R 1 ') 2 , p is a number from 1 to 3, inclusive, R' and T 1 are as defined above, and X is as defined below, X is a direct bond, linear or branched C 1-4 alkylene, ##STR107## wherein R 4 is halo, C 1-4 alkyl or C 1-4 alkoxy, each R 5 is independently hydrogen or C 1-4 alkyl, each R 6 is independently linear or branched C 1-4 alkylene, R 7 is hydroxy, halo, amino, dimethylamino, diethylamino, 2-hydroxyethylamino, di-(2-hydroxyethyl)amino, 3-dimethylaminopropropylamino, 3-diethylaminopropylamino, N-methyl-N-phenylamino or N-cyclohexyl-N-methylamino, each q is independently 1, 2, 3 or 4, and each z is independently 0, 1 or 2, with the proviso that when at least one R 3 is other than hydrogen, X is a direct bond, linear or branched C 1-4 alkylene, ##STR108## wherein R 5 , R 6 and R 7 are as defined above, wherein each A.sup.⊖ is a non-chromophoric anion, each m is independently 1, 2, 3, 4, 5 or 6, and each R 1 ' and R 2 ' is as defined above.

Claim 6

A compound of the formula ##STR96## wherein each R' Is independently --N(R 1 ') 2 , --N.sup.⊕ (R 2 ') 3 A.sup.⊖ or hydroxy, wherein each R 1 ' is independently hydrogen; C 1-12 alkyl; C 1-12 alkyl substituted by halo, cyano, hydroxy, phenyl or carbamoyl; cyclohexyl; cyclohexyl substituted by 1 to 3 C 1-4 alkyl groups; phenyl or phenyl substituted by 1 to 3 C 1-4 alkyl groups or --N(R 1 ') 2 is piperidino, morpholino, piperazino, N'-C 1-4 alkylpiperazino or pyrrolidino, and each R 2 ' is independently C 1-12 alkyl; C 1-12 alkyl substituted by halo, cyano, hydroxy, phenyl or carbamoyl; cyclohexyl; cyclohexyl substituted by 1 to 3 C 1-4 alkyl groups; phenyl or phenyl substituted by 1 to 3 C 1-4 alkyl groups or --N.sup.⊕ (R 2 ') 3 is N-R 2 '-piperidinium, N-R 2 '-morpholinium, N-R 2 '-piperazinium, N-R 2 '-N'-C 1-4 alkylpiperazinium, N-R 2 '-pyrrolidinium, pyridinium or pyridinium substituted by 1 to 3 C 1-4 alkyl groups, each T 1 is C 1-12 alkylene or C 3-12 alkenylene, and Z' is hydrogen, R1 ? ##STR97## wherein each R 3 is independently hydrogen, halo, C 1-4 alkyl or C 1-4 alkoxy, each R 3a is independently hydrogen, halo, C 1-4 alkyl, C 1-4 alkoxy, nitro, ##STR98## wherein R 3 is as defined above, and K and X are as defined below, wherein K is ##STR99## wherein K a is ##STR100## wherein each R' and T 1 is as defined above, and each R a , R 8 , R 9 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , X and p is as defined below, each R a is --N(R 1 ') 2 or --N.sup.⊕ (R 2 ') 3 A.sup.⊖, R 8 is hydrogen, methyl, methoxy or ethoxy, R 9 is ##STR101## wherein each of R 23 , R 24 and R 25 is independently hydrogen, halo, C 1-4 alkyl, C 1-4 alkoxy, nitro or cyano, and R a and R 8 are as defined above, R 10 is C 1-4 alkyl or C 1-4 alkoxy, R 11 is C 1-4 alkyl or C 1-4 alkoxy, R 12 is hydrogen, C 1-4 alkyl, benzyl or phenyl, R 13 is hydrogen, cyano, carbamoyl, ##STR102## wherein R 26 is C 1-4 alkyl, amino, C 1-4 alkylamino, di-(C 1-4 alkyl)amino, (C 1-4 alkyl)carbamoyl or di-(C 1-4 alkyl)carbamoyl, and u is 0, 1 or 2, R 14 is hydrogen, C 1-4 alkyl, phenyl(C 1-4 alkyl), 2-cyanoethyl, 2-hydroxyethyl, --(CH 2 ) r --N(R 1a ) 2 , 3-methoxypropyl, --(CH 2 ) r --N.sup.⊕ (R 2 ') 3 A.sup.⊖ or phenylamino, wherein each R 1a is C 1-12 alkyl; C 1-12 alkyl substituted by halo, cyano, hydroxy, phenyl or carbamoyl; cyclohexyl; cyclohexyl substituted by 1 to 3 C 1-4 alkyl groups; phenyl or phenyl substituted by 1 to 3 C 1-4 alkyl groups or --N(R 1a ) 2 is piperidino, morpholino, piperazino, N'-C 1-4 alkylpiperazino or pyrrolidino, and r is 2, 3, 4, 5 or 6, each R 15 is independently hydrogen, C 1-4 alkyl, 3-methoxypropyl, 2-hydroxyethyl, 3-dimethylaminopropyl, 3-diethylaminopropyl or 3-trimethylammoniumpropyl A.sup.⊖, R 16 is hydroxy or amino, R 17 is C 1-4 alkyl, --CO--OR 32 or --CO--NR 33 R 34 , wherein R 32 is C 1-4 alkyl, R 33 is hydrogen or C 1-4 alkyl, and R 34 is hydrogen or C 1-4 alkyl, R 18 is ##STR103## wherein each of R 28 and R 29 is independently hydrogen, halo, C 1-4 alkyl, C 1-4 alkoxy, nitro, amino or acetamido, and R 30 is hydrogen or --NH--CO--(CH 2 ) m --R 35 , wherein R 35 is --N.sup.⊕ (R 2 ') 3 A.sup.⊖, ##STR104## R 19 is hydrazino, --NH--(CH 2 ) m --N(R 1 ') 2 or nitrophenylamino, R 20 is C 1-4 alkyl, benzyl or 2-cyanoethyl, R 21 is C 1-4 alkyl, --(CH 2 ) m --N.sup.⊕ (CH 3 ) 3 A.sup.⊖ or ##STR105## R 22 is ##STR106## wherein each R 31 is independently --NH--(CH 2 ) m --(R 1 ') 2 , p is a number from 1 to 3, inclusive, R' and T 1 are as defined above, and X is as defined below, X is a direct bond, linear or branched C 1-4 alkylene, ##STR107## wherein R 4 is halo, C 1-4 alkyl or C 1-4 alkoxy, each R 5 is independently hydrogen or C 1-4 alkyl, each R 6 is independently linear or branched C 1-4 alkylene, R 7 is hydroxy, halo, amino, dimethylamino, diethylamino, 2-hydroxyethylamino, di-(2-hydroxyethyl)amino, 3-dimethylaminopropropylamino, 3-diethylaminopropylamino, N-methyl-N-phenylamino or N-cyclohexyl-N-methylamino, each q is independently 1, 2, 3 or 4, and each z is independently 0, 1 or 2, with the proviso that when at least one R 3 is other than hydrogen, X is a direct bond, linear or branched C 1-4 alkylene, ##STR108## wherein R 5 , R 6 and R 7 are as defined above, wherein each A.sup.⊖ is a non-chromophoric anion, each m is independently 1, 2, 3, 4, 5 or 6, and each R 1 ' and R 2 ' is as defined above.

Claim 7

A compound according to claim 4 wherein Z' is ##STR109##

Claim 8

A compound according to claim 4 wherein Z' is hydrogen.

Claim 9

A compound according to claim 4 having the formula ##STR110## wherein each R" is hydroxy or --N(R 1 ") 2 , wherein each R 1 " is hydrogen or C 1-4 alkyl, Z" is hydrogen, ##STR111## wherein each R 3 ' is independently hydrogen, methyl, methoxy or chloro, R 3a ' is hydrogen, chloro, nitro, phenylazo, 3-methylphenylazo, phenoxy, 4-chlorophenoxy or 3-methoxyphenoxy, R 3b is hydrogen, chloro, nitro or methyl, and K' and X' are as defined below, and each n is 2, 3, 4, 5 or 6, wherein K' is ##STR112## wherein K a ' is ##STR113## wherein R a ', R 9 ', R 13 ', R 14 ', R 15 ', R 16 , R 18 ', R 19 ', R 20 ', R 21 ', R 22 ', X' and p are as defined below, and each n is 2, 3, 4, 5 or 6, each R a ' is --N(R 1 ") 2 or --N.sup.⊕ (R 2 ") 2 R 2b ' A.sup.⊖, wherein each R 2 " is independently C 1-4 alkyl, and R 2b ' is methyl, ethyl or benzyl, R 9 ' is ##STR114## wherein each of R 23 ', R 24 ' and R 25 ' is independently hydrogen, chloro, methyl, ethyl, methoxy or ethoxy, R 10 ' is methyl, ethyl, methoxy or ethoxy, R 11 ' is methyl, ethyl, methoxy or ethoxy, R 13 ' is hydrogen, cyano, carbamoyl, pyridinium A.sup.⊖, 3-methylpyridinium A.sup.⊖, 3-diethylcarbamoylpyridinium A.sup.⊖, 4-dimethylaminopyridinium A.sup.⊖ or ##STR115## R 14 ' is hydrogen, methyl, ethyl, benzyl, 2-phenylethyl, phenylamino, 2-hydroxyethyl, 3-methoxypropyl, 2-cyanoethyl, 3-dimethylaminopropyl, 3-trimethylammoniumpropyl A.sup.⊖ or 3-(N-benzyl-N,N-dimethylammonium)propyl A.sup.⊖, each R 15 ' is independently 2-hydroxyethyl, 3-methoxypropyl, 3-dimethylaminopropyl or 3-diethylaminopropyl, R 16 is hydroxy or amino, R 18 ' is phenyl, ##STR116## R 19 ' is --NH--(CH 2 ) 3 --N(R 1 ") 2 or 4-nitrophenylamino, R 20 ' is methyl, ethyl or benzyl, R 21 ' is methyl, ethyl, 2-trimethylammoniumethyl A.sup.⊖ or 2-pyridiniumethyl A.sup.⊖, R 22 ' is ##STR117## wherein each R 31 ' is --NH--(CH 2 ) m --N(CH 3 ) 2 or --NH--(CH 2 ) m --N(C 2 H 5 ) 2 , wherein m is 1, 2, 3, 4, 5 or 6, n is 2, 3, 4, 5, 6, p is a number from 1 to 3, inclusive, and X' is as defined below, and X' is a direct bond, --CH 2 --, --(CH 2 ) 2 --, --(CH 2 ) 3 --, --(CH 2 ) 4 --, --S--, --O--, --CH═CH--, --NH--, --NH--CO--, ##STR118## --CH 2 --CO--, --CH═CH--CO--CH═CH-- or --CO--NH--R 6 --CO--NH--, wherein R 4 ' is hydrogen, chloro, methyl or methoxy, R 6 is linear or branched C 1-4 alkylene, R 7 ' is hydroxy, chloro, amino, 2-hydroxyethylamino, di-(2-hydroxyethyl)amino, 3-diethylaminopropylamino, N-methyl-N-phenylamino or N-cyclohexyl-N-methylamino, and q is 1, 2, 3 or 4, with the proviso that when at least one R 3 ' is other than hydrogen, X' is a direct bond, --CH 2 --, --(CH 2 ) 2 --, ##STR119## wherein each A.sup.⊖ is a non-chromophoric anion, and each R 1 " is as defined above.

Claim 10

A compound according to claim 7 having the formula ##STR120## wherein K" is ##STR121## wherein p' is a number from 1 to 2, K a ', R a ', R 9 ', R 10 ', R 11 ', R 13 ', R 14 ', R 15 ', R 16 , R 18 ', R 19 ', R 20 ', R 21 ' and R 22 ' are as defined in claim 7, and R 1 ", X" and n are as defined below, each R 1 " is hydrogen or C 1-4 alkyl, each R 3 ' is independently hydrogen, methyl, methoxy or chloro, X" is a direct bond, ##STR122## wherein R 6 is a linear or branched C 1-4 alkylene, and R 7 ' is hydroxy, chloro, amino, 2-hydroxyethylamino, di-(2-hydroxyethyl)amino, 3-diethylaminopropylamino, N-methyl-N-phenylamino or N-cyclohexyl-N-methylamino, with the proviso that when at least one R 3 ' is methyl, methoxy or chloro, X" is a direct bond, and each n is 2, 3, 4, 5 or 6.

Claim 11

A compound according to claim 8 wherein each of K" and K a ' is other than ##STR123##

Claim 12

The compound according to claim 7 having the formula ##STR124##

Claim 13

The compound according to claim 7 having the formula ##STR125##

Claim 14

The compound according to claim 7 having the formula ##STR126##