Azo dyes having a 6-hydroxy-pyridone-2 coupling component radical having a substituent in the 1-position

Claim 2

A compound of the formula wherein D is (a) thiazolyl, (b) substituted thiazolyl each substituent of which is independently chloro, bromo, nitro, cyano, methyl, phenyl, methylsulfonyl or ethylsulfonyl, (c) benzothiazolyl, (d) substituted benzothiazolyl each substituent of which is independently chloro, bromo, cyano, nitro, methyl, ethyl, methoxy, ethoxy, methylsulfonyl, ethylsulfonyl, cyanoethylsulfonyl, sulfamoyl or methylsulfamoyl, (e) pyrazolyl, (f) substituted pyrazolyl each substituent of which is independently cyano, methyl or phenyl, (g) thiadiazolyl, (h) methylthiadiazolyl, (i) imidazolyl, (j) substituted imidazolyl each substituent of which is independently nitro or methyl, (k) thienyl, (l) substituted thienyl each substituent of which is independently nitro or acetyl or ##STR122## B 1 is (a) alkyl of 1 to 4 carbon atoms, (b) substituted alkyl of 1 to 4 carbon atoms each substituent of which is independently chloro, bromo, hydroxy, cyano, methoxy or ethoxy, (c) phenyl, (d) substituted phenyl each substituent of which is independently chloro, bromo, methyl, methoxy, nitro, methoxycarbonyl, ethoxycarbonyl, methylsulfamoyl, dimethylsulfamoyl, cyano or acetamido, (e) naphthyl, (f) methoxynaphthyl, (g) ethoxynaphthyl, (h) thienyl, (i) methylthienyl, (j) furyl, (k) thiazolyl, (l) pyridyl, (m) imidazolyl or (n) benzimidazolyl, B 2 is cyano, acetyl, propionyl, methylsulfonyl, ethylsulfonyl, benzoyl, phenylsulfonyl, nicotinoyl, carbamoyl, methylcarbamoyl, dimethylcarbamoyl, ethylcarbamoyl or diethylcarbamoyl, and B 3 is (a) alkyl of 1 to 4 carbon atoms, (b) substituted alkyl of 1 to 4 carbon atoms each substituent of which is independently chloro, bromo, hydroxy, cyano, methoxy, ethoxy, methoxyethoxy, cyanoethoxy, phenoxyethoxy, acetyl, propionyl, benzoyl, formyloxy, acetoxy, propionyloxy, methoxypropionyloxy, acryloyloxy, benzoyloxy, methoxycarbonyl, ethoxycarbonyl, ethoxyethoxycarbonyl, cyanomethoxycarbonyl, phenoxycarbonyl, methoxycarbonyloxy, ethoxycarbonyloxy, phenoxycarbonyloxy, carbamoyl, methylcarbamoyl, dimethylcarbamoyl, methylcarbamoyloxy, ethylcarbamoyloxy, phenylcarbamoyloxy, methoxycarbonylethoxy, 5-chlorofuryl-2-, methylsulfonyloxy, ethylsulfonyloxy, phenylsulfonyloxy, vinylsulfonyloxy, phenoxysulfonyl, phenthioethylsulfonyl or vinylsulfonyl, (c) cyclohexyl, (d) trimethylcyclohexyl, (e) methylamino, (f) dimethylamino, (g) ethylamino, (h) diethylamino, (i) hydroxyethylamino, (j) di-(β-cyanoethyl)amino, (k) di(acetoxyethyl)amino, (l) phenylamino, (m) ethoxyethylamino, (n) formamido, (o) acetamido, (p) propionamido, (q) benzamido, (r) N-piperazino, (s) N-piperidino, (t) N-morpholino or ##STR123##

Claim 3

A compound of the formula ##STR124## wherein D is substituted phenyl, wherein each substituent of substituted phenyl is chloro, bromo, nitro, lower alkyl, lower alkoxy, cyano, lower alkoxycarbonyl, sulfamoyl, N-lower alkylsulfamoyl, N,N-dilower alkylsulfamoyl, N-lower alkylsulfamoyloxy or N,N-dilower alkylsulfamoyloxy, R 2 is cyano or lowr alkanoyl, R 3 ' is chloro, lower alkyl or lower alkoxy, R 4 is lower alkyl or lower alkyl monosubstituted by hydroxy or lower alkoxy, and n is 0 or 1.

Claim 4

A compound of the formula ##STR124## wherein D is substituted phenyl, wherein each substituent of substituted phenyl is chloro, bromo, nitro, lower alkyl, lower alkoxy, cyano, lower alkoxycarbonyl, sulfamoyl, N-lower alkylsulfamoyl, N,N-dilower alkylsulfamoyl, N-lower alkylsulfamoyloxy or N,N-dilower alkylsulfamoyloxy, R 2 is cyano or lowr alkanoyl, R 3 ' is chloro, lower alkyl or lower alkoxy, R 4 is lower alkyl or lower alkyl monosubstituted by hydroxy or lower alkoxy, and n is 0 or 1.

Claim 5

A compound of the formula ##STR125## wherein D is (a) phenyl, (b) substituted phenyl each substituent of which is independently chloro, bromo, hydroxy, cyano, thiocyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, formyl, acetyl, propionyl, benzoyl, methylbenzoyl, methoxycarbonyl, ethoxycarbonyl, ethoxycarbonyloxy, benzyloxycarbonyloxy, acetoxy, propionyloxy, benzoyloxy, methoxyethoxycarbonyl, acetamido, propionamido, benzamido, methoxycarbonylamino, ethoxycarbonylamino, methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, chloromethylsulfonyl, sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, di-(hydroxyethyl)sulfamoyl, cyclohexylsulfamoyl, phenylsulfamoyl, chloromethylsulfamoyl, methoxyphenylsulfamoyl, benzylsulfamoyl, N-piperidinosulfonyl, N-morpholinosulfonyl, methylsulfonyloxy, ethylsulfonyloxy, ethoxyethylsulfonyloxy, propylsulfonyloxy, hexylsulfonyloxy, cyclohexylsulfonyloxy, cyanoethylsulfonyloxy, phenylsulfonyloxy, chloromethylsulfonyloxy, sulfamoyloxy, N-morpholinosulfonyloxy, methoxyphenylsulfonyloxy, ethyleneaminosulfonyloxy, methylsulfamoyloxy, ethylsulfamoyloxy, propylsulfamoyloxy, butylsulfamoyloxy, dimethylsulfamoyloxy, diethylsulfamoyloxy, dipropylsulfamoyloxy, dibutylsulfamoyloxy, phenylsulfamoyloxy, N-phenyl-N-methylsulfamoyloxy, N-phenyl-N-ethylsulfamoyloxy, methoxyphenylsulfamoyloxy, phenylamino, nitrophenylamino, dinitrophenylamino, phenyl, acetamidophenyl, phenylsulfamoylphenyl, phenylazo or nitrophenylazo, (c) naphthyl, (d) substituted naphthyl each substituent of which is independently methoxy, ethoxy, phenylazo or dimethylsulfamoyl, (e) thiazolyl, (f) substituted thiazolyl each substituent of which is independently chloro, bromo, nitro, cyano, methyl, phenyl, methylsulfonyl or ethylsulfonyl, (g) benzothiazolyl, (h) substituted benzothiazolyl each substituent of which is independently chloro, bromo, cyano, nitro, methyl, ethyl, methoxy, ethoxy, methylsulfonyl, ethylsulfonyl, cyanoethylsulfonyl, sulfamoyl or methylsulfamoyl, (i) pyrazolyl, (j) substituted pyrazolyl each substituent of which is independently cyano, methyl or phenyl, (k) thiadiazolyl, (l) methylthiadiazolyl, (m) imidazolyl, (n) substituted imidazolyl each substituent of which is independently nitro or methyl, (o) thienyl, (p) substituted thienyl each substituent of which is independently nitro or acetyl or ##STR126## B 1 is (a) alkyl of 1 to 4 carbon atoms, (b) substituted alkyl of 1 to 4 carbon atoms each substituent of which is independently chloro, bromo, hydroxy, cyano, methoxy or ethoxy, (c) phenyl, (d) substituted phenyl each substituent of which is independently chloro, bromo, methyl, methoxy, nitro, methoxycarbonyl, ethoxycarbonyl, methylsulfamoyl, dimethylsulfamoyl, cyano or acetamido, (e) naphthyl, (f) methoxynaphthyl, (g) ethoxynaphthyl, (h) thienyl, (i) methylthienyl, (j) furyl, (k) thiazolyl, (l) pyridyl, (m) imidazolyl or (n) benzimidazolyl, B 2 is cyano, acetyl, propionyl, methylsulfonyl, ethylsulfonyl, benzoyl, phenylsulfonyl, nicotinoyl, carbamoyl, methylcarbamoyl, dimethylcarbamoyl, ethylcarbamoyl or diethylcarbamoyl, and B 3 is methylamino, dimethylamino, ethylamino, diethylamino, hydroxyethylamino, di-(β-cyanoethyl)amino, di-(acetoxyethyl)amino, phenylamino, ethoxyethylamino, formamido, acetamido, propionamido, benzamido, N-piperazino, N-piperidino or N-morpholino.

Claim 6

A compound of the formula ##STR125## wherein D is (a) phenyl, (b) substituted phenyl each substituent of which is independently chloro, bromo, hydroxy, cyano, thiocyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, formyl, acetyl, propionyl, benzoyl, methylbenzoyl, methoxycarbonyl, ethoxycarbonyl, ethoxycarbonyloxy, benzyloxycarbonyloxy, acetoxy, propionyloxy, benzoyloxy, methoxyethoxycarbonyl, acetamido, propionamido, benzamido, methoxycarbonylamino, ethoxycarbonylamino, methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, chloromethylsulfonyl, sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, di-(hydroxyethyl)sulfamoyl, cyclohexylsulfamoyl, phenylsulfamoyl, chloromethylsulfamoyl, methoxyphenylsulfamoyl, benzylsulfamoyl, N-piperidinosulfonyl, N-morpholinosulfonyl, methylsulfonyloxy, ethylsulfonyloxy, ethoxyethylsulfonyloxy, propylsulfonyloxy, hexylsulfonyloxy, cyclohexylsulfonyloxy, cyanoethylsulfonyloxy, phenylsulfonyloxy, chloromethylsulfonyloxy, sulfamoyloxy, N-morpholinosulfonyloxy, methoxyphenylsulfonyloxy, ethyleneaminosulfonyloxy, methylsulfamoyloxy, ethylsulfamoyloxy, propylsulfamoyloxy, butylsulfamoyloxy, dimethylsulfamoyloxy, diethylsulfamoyloxy, dipropylsulfamoyloxy, dibutylsulfamoyloxy, phenylsulfamoyloxy, N-phenyl-N-methylsulfamoyloxy, N-phenyl-N-ethylsulfamoyloxy, methoxyphenylsulfamoyloxy, phenylamino, nitrophenylamino, dinitrophenylamino, phenyl, acetamidophenyl, phenylsulfamoylphenyl, phenylazo or nitrophenylazo, (c) naphthyl, (d) substituted naphthyl each substituent of which is independently methoxy, ethoxy, phenylazo or dimethylsulfamoyl, (e) thiazolyl, (f) substituted thiazolyl each substituent of which is independently chloro, bromo, nitro, cyano, methyl, phenyl, methylsulfonyl or ethylsulfonyl, (g) benzothiazolyl, (h) substituted benzothiazolyl each substituent of which is independently chloro, bromo, cyano, nitro, methyl, ethyl, methoxy, ethoxy, methylsulfonyl, ethylsulfonyl, cyanoethylsulfonyl, sulfamoyl or methylsulfamoyl, (i) pyrazolyl, (j) substituted pyrazolyl each substituent of which is independently cyano, methyl or phenyl, (k) thiadiazolyl, (l) methylthiadiazolyl, (m) imidazolyl, (n) substituted imidazolyl each substituent of which is independently nitro or methyl, (o) thienyl, (p) substituted thienyl each substituent of which is independently nitro or acetyl or ##STR126## B 1 is (a) alkyl of 1 to 4 carbon atoms, (b) substituted alkyl of 1 to 4 carbon atoms each substituent of which is independently chloro, bromo, hydroxy, cyano, methoxy or ethoxy, (c) phenyl, (d) substituted phenyl each substituent of which is independently chloro, bromo, methyl, methoxy, nitro, methoxycarbonyl, ethoxycarbonyl, methylsulfamoyl, dimethylsulfamoyl, cyano or acetamido, (e) naphthyl, (f) methoxynaphthyl, (g) ethoxynaphthyl, (h) thienyl, (i) methylthienyl, (j) furyl, (k) thiazolyl, (l) pyridyl, (m) imidazolyl or (n) benzimidazolyl, B 2 is cyano, acetyl, propionyl, methylsulfonyl, ethylsulfonyl, benzoyl, phenylsulfonyl, nicotinoyl, carbamoyl, methylcarbamoyl, dimethylcarbamoyl, ethylcarbamoyl or diethylcarbamoyl, and B 3 is methylamino, dimethylamino, ethylamino, diethylamino, hydroxyethylamino, di-(β-cyanoethyl)amino, di-(acetoxyethyl)amino, phenylamino, ethoxyethylamino, formamido, acetamido, propionamido, benzamido, N-piperazino, N-piperidino or N-morpholino.

Claim 7

A compound of the formula ##STR127## wherein D is (a) phenyl, (b) substituted phenyl each substituent of which is independently chloro, bromo, hydroxy, cyano, thiocyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, formyl, acetyl, propionyl, benzoyl, methylbenzoyl, methoxycarbonyl, ethoxycarbonyl, ethoxycarbonyloxy, benzyloxycarbonyloxy, acetoxy, propionyloxy, benzoyloxy, methoxyethoxycarbonyl, acetamido, propionamido, benzamido, methoxycarbonylamino, ethoxycarbonylamino, methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, chloromethylsulfonyl, sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, di-(hydroxyethyl)sulfamoyl, cyclohexylsulfamoyl, phenylsulfamoyl, chloromethylsulfamoyl, methoxyphenylsulfamoyl, benzylsulfamoyl, N-piperidinosulfonyl, N-morpholinosulfonyl, methylsulfonyloxy, ethylsulfonyloxy, ethoxyethylsulfonyloxy, propylsulfonyloxy, hexylsulfonyloxy, cyclohexylsulfonyloxy, cyanoethylsulfonyloxy, phenylsulfonyloxy, chloromethylsulfonyloxy, sulfamoyloxy, N-morpholinosulfonyloxy, methoxyphenylsulfonyloxy, ethyleneaminosulfonyloxy, methylsulfamoyloxy, ethylsulfamoyloxy, propylsulfamoyloxy, butylsulfamoyloxy, dimethylsulfamoyloxy, diethylsulfamoyloxy, dipropylsulfamoyloxy, dibutylsulfamoyloxy, phenylsulfamoyloxy, N-phenyl-N-methylsulfamoyloxy, N-phenyl-N-ethylsulfamoyloxy, methoxyphenylsulfamoyloxy, phenylamino, nitrophenylamino, dinitrophenylamino, phenyl, acetamidophenyl, phenylsulfamoylphenyl, phenylazo or nitrophenylazo, (c) naphthyl, (d) substituted naphthyl each substituent of which is independently methoxy, ethoxy, phenylazo or dimethylsulfamoyl, (e) thiazolyl, (f) substituted thiazolyl each substituent of which is independently chloro, bromo, nitro, cyano, methyl, phenyl, methylsulfonyl or ethylsulfonyl, (g) benzothiazolyl, (h) substituted benzothiazolyl each substituent of which is independently chloro, bromo, cyano, nitro, methyl, ethyl, methoxy, ethoxy, methylsulfonyl, ethylsulfonyl, cyanoethylsulfonyl, sulfamoyl or methylsulfamoyl, (i) pyrazolyl, (j) substituted pyrazolyl each substituent of which is independently cyano, methyl or phenyl, (k) thiadiazolyl, (l) methylthiadiazolyl, (m) imidazolyl, (n) substituted imidazolyl each substituent of which is independently nitro or methyl, (o) thienyl, (p) substituted thienyl each substituent of which is independently nitro or acetyl or ##STR128## B 1 is (a) alkyl of 1 to 4 carbon atoms, (b) substituted alkyl of 1 to 4 carbon atoms each substituent of which is independently chloro, bromo, hydroxy, cyano, methoxy or ethoxy, (c) phenyl, (d) substituted phenyl each substituent of which is independently chloro, bromo, methyl, methoxy, nitro, methoxycarbonyl, ethoxycarbonyl, methylsulfamoyl, dimethylsulfamoyl, cyano or acetamido, (e) naphthyl, (f) methoxynaphthyl, (g) ethoxynaphthyl, (h) thienyl, (i) methylthienyl, (j) furyl, (k) thiazolyl, (l) pyridyl, (m) imidazolyl or (n) benzimidazolyl, B 2 is methylsulfonyl, ethylsulfonyl or phenylsulfonyl, and B 3 is (a) alkyl of 1 to 4 carbon atoms, (b) substituted alkyl of 1 to 4 carbon atoms each substituent of which is independently chloro, bromo, hydroxy, cyano, methoxy, ethoxy, methoxyethoxy, cyanoethoxy, phenoxyethoxy, acetyl, propionyl, benzoyl, formyloxy, acetoxy, propionyloxy, methoxypropionyloxy, acryloxy, benzoyloxy, methoxycarbonyl, ethoxycarbonyl, ethoxyethoxycarbonyl, cyanomethoxycarbonyl, phenoxycarbonyl, methoxycarbonyloxy, ethoxycarbonyloxy, phenoxycarbonyloxy, carbamoyl, methylcarbamoyl, dimethylcarbamoyl, methylcarbamoyloxy, ethylcarbamoyloxy, phenylcarbamoyloxy, methoxycarbonylethoxy, 5-chlorofuryl-2-, methylsulfonyloxy, ethylsulfonyloxy, phenylsulfonyloxy, vinylsulfonyloxy, phenoxysulfonyl, phenthioethylsulfonyl or vinylsulfonyl, (c) cyclohexyl, (d) trimethylcyclohexyl, (e) methylamino, (f) dimethylamino, (g) ethylamino, (h) diethylamino, (i) hydroxyethylamino, (j) di-(β-cyanoethyl)amino, (k) di(acetoxyethyl)amino, (l) phenylamino, (m) ethoxyethylamino, (n) formamido, (o) acetamido (p) propionamido, (q) banzamido, (r) N-piperazino, (s) N-piperidino, (t) N-morpholino or ##STR129##

Claim 8

A compound of the formula ##STR127## wherein D is (a) phenyl, (b) substituted phenyl each substituent of which is independently chloro, bromo, hydroxy, cyano, thiocyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, formyl, acetyl, propionyl, benzoyl, methylbenzoyl, methoxycarbonyl, ethoxycarbonyl, ethoxycarbonyloxy, benzyloxycarbonyloxy, acetoxy, propionyloxy, benzoyloxy, methoxyethoxycarbonyl, acetamido, propionamido, benzamido, methoxycarbonylamino, ethoxycarbonylamino, methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, chloromethylsulfonyl, sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, di-(hydroxyethyl)sulfamoyl, cyclohexylsulfamoyl, phenylsulfamoyl, chloromethylsulfamoyl, methoxyphenylsulfamoyl, benzylsulfamoyl, N-piperidinosulfonyl, N-morpholinosulfonyl, methylsulfonyloxy, ethylsulfonyloxy, ethoxyethylsulfonyloxy, propylsulfonyloxy, hexylsulfonyloxy, cyclohexylsulfonyloxy, cyanoethylsulfonyloxy, phenylsulfonyloxy, chloromethylsulfonyloxy, sulfamoyloxy, N-morpholinosulfonyloxy, methoxyphenylsulfonyloxy, ethyleneaminosulfonyloxy, methylsulfamoyloxy, ethylsulfamoyloxy, propylsulfamoyloxy, butylsulfamoyloxy, dimethylsulfamoyloxy, diethylsulfamoyloxy, dipropylsulfamoyloxy, dibutylsulfamoyloxy, phenylsulfamoyloxy, N-phenyl-N-methylsulfamoyloxy, N-phenyl-N-ethylsulfamoyloxy, methoxyphenylsulfamoyloxy, phenylamino, nitrophenylamino, dinitrophenylamino, phenyl, acetamidophenyl, phenylsulfamoylphenyl, phenylazo or nitrophenylazo, (c) naphthyl, (d) substituted naphthyl each substituent of which is independently methoxy, ethoxy, phenylazo or dimethylsulfamoyl, (e) thiazolyl, (f) substituted thiazolyl each substituent of which is independently chloro, bromo, nitro, cyano, methyl, phenyl, methylsulfonyl or ethylsulfonyl, (g) benzothiazolyl, (h) substituted benzothiazolyl each substituent of which is independently chloro, bromo, cyano, nitro, methyl, ethyl, methoxy, ethoxy, methylsulfonyl, ethylsulfonyl, cyanoethylsulfonyl, sulfamoyl or methylsulfamoyl, (i) pyrazolyl, (j) substituted pyrazolyl each substituent of which is independently cyano, methyl or phenyl, (k) thiadiazolyl, (l) methylthiadiazolyl, (m) imidazolyl, (n) substituted imidazolyl each substituent of which is independently nitro or methyl, (o) thienyl, (p) substituted thienyl each substituent of which is independently nitro or acetyl or ##STR128## B 1 is (a) alkyl of 1 to 4 carbon atoms, (b) substituted alkyl of 1 to 4 carbon atoms each substituent of which is independently chloro, bromo, hydroxy, cyano, methoxy or ethoxy, (c) phenyl, (d) substituted phenyl each substituent of which is independently chloro, bromo, methyl, methoxy, nitro, methoxycarbonyl, ethoxycarbonyl, methylsulfamoyl, dimethylsulfamoyl, cyano or acetamido, (e) naphthyl, (f) methoxynaphthyl, (g) ethoxynaphthyl, (h) thienyl, (i) methylthienyl, (j) furyl, (k) thiazolyl, (l) pyridyl, (m) imidazolyl or (n) benzimidazolyl, B 2 is methylsulfonyl, ethylsulfonyl or phenylsulfonyl, and B 3 is (a) alkyl of 1 to 4 carbon atoms, (b) substituted alkyl of 1 to 4 carbon atoms each substituent of which is independently chloro, bromo, hydroxy, cyano, methoxy, ethoxy, methoxyethoxy, cyanoethoxy, phenoxyethoxy, acetyl, propionyl, benzoyl, formyloxy, acetoxy, propionyloxy, methoxypropionyloxy, acryloxy, benzoyloxy, methoxycarbonyl, ethoxycarbonyl, ethoxyethoxycarbonyl, cyanomethoxycarbonyl, phenoxycarbonyl, methoxycarbonyloxy, ethoxycarbonyloxy, phenoxycarbonyloxy, carbamoyl, methylcarbamoyl, dimethylcarbamoyl, methylcarbamoyloxy, ethylcarbamoyloxy, phenylcarbamoyloxy, methoxycarbonylethoxy, 5-chlorofuryl-2-, methylsulfonyloxy, ethylsulfonyloxy, phenylsulfonyloxy, vinylsulfonyloxy, phenoxysulfonyl, phenthioethylsulfonyl or vinylsulfonyl, (c) cyclohexyl, (d) trimethylcyclohexyl, (e) methylamino, (f) dimethylamino, (g) ethylamino, (h) diethylamino, (i) hydroxyethylamino, (j) di-(β-cyanoethyl)amino, (k) di(acetoxyethyl)amino, (l) phenylamino, (m) ethoxyethylamino, (n) formamido, (o) acetamido (p) propionamido, (q) banzamido, (r) N-piperazino, (s) N-piperidino, (t) N-morpholino or ##STR129##

Claim 9

A compound of the formula ##STR130## wherein D is (a) phenyl, (b) substituted phenyl each substituent of which is independently chloro, bromo, hydroxy, cyano, thiocyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, formyl, acetyl, propionyl, benzoyl, methylbenzoyl, methoxycarbonyl, ethoxycarbonyl, ethoxycarbonyloxy, benzyloxycarbonyloxy, acetoxy, propionyloxy, benzoyloxy, methoxyethoxycarbonyl, acetamido, propionamido, benzamido, methoxycarbonylamino, ethoxycarbonylamino, methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, chloromethylsulfonyl, sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, di-(hydroxyethyl)sulfamoyl, cyclohexylsulfamoyl, phenylsulfamoyl, chloromethylsulfamoyl, methoxyphenylsulfamoyl, benzylsulfamoyl, N-piperidinosulfonyl, N-morpholinosulfonyl, methylsulfonyloxy, ethylsulfonyloxy, ethoxyethylsulfonyloxy, propylsulfonyloxy, hexylsulfonyloxy, cyclohexylsulfonyloxy, cyanoethylsulfonyloxy, phenylsulfonyloxy, chloromethylsulfonyloxy, sulfamoyloxy, N-morpholinosulfonyloxy, methoxyphenylsulfonyloxy, ethyleneaminosulfonyloxy, methylsulfamoyloxy, ethylsulfamoyloxy, propylsulfamoyloxy, butylsulfamoyloxy, dimethylsulfamoyloxy, diethylsulfamoyloxy, dipropylsulfamoyloxy, dibutylsulfamoyloxy, phenylsulfamoyloxy, N-phenyl-N-methylsulfamoyloxy, N-phenyl-N-ethylsulfamoyloxy, methoxyphenylsulfamoyloxy, phenylamino, nitrophenylamino, dinitrophenylamino, phenyl, acetamidophenyl or phenylsulfamoylphenyl, (c) naphthyl, (d) substituted naphthyl each substituent of which is independently methoxy, ethoxy, phenylazo or dimethylsulfamoyl, (e) thiazolyl, (f) substituted thiazolyl each substituent of which is independently chloro, bromo, nitro, cyano, methyl, phenyl, methylsulfonyl or ethylsulfonyl, (g) benzothiazolyl, (h) substituted benzothiazolyl each substituent of which is independently chloro, bromo, cyano, nitro, methyl, ethyl, methoxy, ethoxy, methylsulfonyl, ethylsulfonyl, cyanoethylsulfonyl, sulfamoyl or methylsulfamoyl, (i) pyrazolyl, (j) substituted pyrazolyl each substituent of which is independently cyano, methyl or phenyl, (k) thiadiazolyl, (l) methylthiadiazolyl, (m) imidazolyl, (n) substituted imidazolyl each substituent of which is independently nitro or methyl, (o) thienyl, (p) substituted thienyl each substituent of which is independently nitro or acetyl or ##STR131## B 1 is (a) phenyl, (b) substituted phenyl each substituent of which is independently chloro, bromo, methyl, methoxy, nitro, methoxycarbonyl, ethoxycarbonyl, methylsulfamoyl, dimethylsulfamoyl, cyano or acetamido, (c) naphthyl, (d) methoxynaphthyl, (e) ethoxynaphthyl, (f) thienyl, (g) methylthienyl, (h) furyl, (i) thiazolyl, (j) pyridyl, (k) imidazolyl or (l) benzimidazolyl, B 2 is cyano, acetyl, propionyl, methylsulfonyl, ethylsulfonyl, benzoyl, phenylsulfonyl, nicotinoyl, carbamoyl, methylcarbamoyl, dimethylcarbamoyl, ethylcarbamoyl or diethylcarbamoyl, and B 3 is (a) alkyl of 1 to 4 carbon atoms, (b) substituted alkyl of 1 to 4 carbon atoms each substituent of which is independently chloro, bromo, hydroxy, cyano, methoxy, ethoxy, methoxyethoxy, cyanoethoxy, phenoxyethoxy, acetyl, propionyl, benzoyl, formyloxy, acetoxy, propionyloxy, methoxypropionyloxy, acryloxy, benzoyloxy, methoxycarbonyl, ethoxycarbonyl, ethoxyethoxycarbonyl, cyanomethoxycarbonyl, phenoxycarbonyl, methoxycarbonyloxy, ethoxycarbonyloxy, phenoxycarbonyloxy, carbamoyl, methylcarbamoyl, dimethylcarbamoyl, methylcarbamoyloxy, ethylcarbamoyloxy, phenylcarbamoyloxy, methoxycarbonylethoxy, 5-chlorofuryl-2-, methylsulfonyloxy, ethylsulfonyloxy, phenylsulfonyloxy, vinylsulfonyloxy, phenoxysulfonyl, phenthioethylsulfonyl or vinylsulfonyl, (c) cyclohexyl, (d) trimethylcyclohexyl, (e) methylamino, (f) dimethylamino, (g) ethylamino, (h) diethylamino, (i) hydroxyethylamino, (j) di-(β-cyanoethyl)amino, (k) di(acetoxyethyl)amino, (l) phenylamino, (m) ethoxyethylamino, (n) formamido, (o) acetamido, (p) propionamido, (q) benzamido, (r) N-piperazino, (s) N-piperidino, (t) N-morpholino or ##STR132##

Claim 10

A compound of the formula ##STR130## wherein D is (a) phenyl, (b) substituted phenyl each substituent of which is independently chloro, bromo, hydroxy, cyano, thiocyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, formyl, acetyl, propionyl, benzoyl, methylbenzoyl, methoxycarbonyl, ethoxycarbonyl, ethoxycarbonyloxy, benzyloxycarbonyloxy, acetoxy, propionyloxy, benzoyloxy, methoxyethoxycarbonyl, acetamido, propionamido, benzamido, methoxycarbonylamino, ethoxycarbonylamino, methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, chloromethylsulfonyl, sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, di-(hydroxyethyl)sulfamoyl, cyclohexylsulfamoyl, phenylsulfamoyl, chloromethylsulfamoyl, methoxyphenylsulfamoyl, benzylsulfamoyl, N-piperidinosulfonyl, N-morpholinosulfonyl, methylsulfonyloxy, ethylsulfonyloxy, ethoxyethylsulfonyloxy, propylsulfonyloxy, hexylsulfonyloxy, cyclohexylsulfonyloxy, cyanoethylsulfonyloxy, phenylsulfonyloxy, chloromethylsulfonyloxy, sulfamoyloxy, N-morpholinosulfonyloxy, methoxyphenylsulfonyloxy, ethyleneaminosulfonyloxy, methylsulfamoyloxy, ethylsulfamoyloxy, propylsulfamoyloxy, butylsulfamoyloxy, dimethylsulfamoyloxy, diethylsulfamoyloxy, dipropylsulfamoyloxy, dibutylsulfamoyloxy, phenylsulfamoyloxy, N-phenyl-N-methylsulfamoyloxy, N-phenyl-N-ethylsulfamoyloxy, methoxyphenylsulfamoyloxy, phenylamino, nitrophenylamino, dinitrophenylamino, phenyl, acetamidophenyl or phenylsulfamoylphenyl, (c) naphthyl, (d) substituted naphthyl each substituent of which is independently methoxy, ethoxy, phenylazo or dimethylsulfamoyl, (e) thiazolyl, (f) substituted thiazolyl each substituent of which is independently chloro, bromo, nitro, cyano, methyl, phenyl, methylsulfonyl or ethylsulfonyl, (g) benzothiazolyl, (h) substituted benzothiazolyl each substituent of which is independently chloro, bromo, cyano, nitro, methyl, ethyl, methoxy, ethoxy, methylsulfonyl, ethylsulfonyl, cyanoethylsulfonyl, sulfamoyl or methylsulfamoyl, (i) pyrazolyl, (j) substituted pyrazolyl each substituent of which is independently cyano, methyl or phenyl, (k) thiadiazolyl, (l) methylthiadiazolyl, (m) imidazolyl, (n) substituted imidazolyl each substituent of which is independently nitro or methyl, (o) thienyl, (p) substituted thienyl each substituent of which is independently nitro or acetyl or ##STR131## B 1 is (a) phenyl, (b) substituted phenyl each substituent of which is independently chloro, bromo, methyl, methoxy, nitro, methoxycarbonyl, ethoxycarbonyl, methylsulfamoyl, dimethylsulfamoyl, cyano or acetamido, (c) naphthyl, (d) methoxynaphthyl, (e) ethoxynaphthyl, (f) thienyl, (g) methylthienyl, (h) furyl, (i) thiazolyl, (j) pyridyl, (k) imidazolyl or (l) benzimidazolyl, B 2 is cyano, acetyl, propionyl, methylsulfonyl, ethylsulfonyl, benzoyl, phenylsulfonyl, nicotinoyl, carbamoyl, methylcarbamoyl, dimethylcarbamoyl, ethylcarbamoyl or diethylcarbamoyl, and B 3 is (a) alkyl of 1 to 4 carbon atoms, (b) substituted alkyl of 1 to 4 carbon atoms each substituent of which is independently chloro, bromo, hydroxy, cyano, methoxy, ethoxy, methoxyethoxy, cyanoethoxy, phenoxyethoxy, acetyl, propionyl, benzoyl, formyloxy, acetoxy, propionyloxy, methoxypropionyloxy, acryloxy, benzoyloxy, methoxycarbonyl, ethoxycarbonyl, ethoxyethoxycarbonyl, cyanomethoxycarbonyl, phenoxycarbonyl, methoxycarbonyloxy, ethoxycarbonyloxy, phenoxycarbonyloxy, carbamoyl, methylcarbamoyl, dimethylcarbamoyl, methylcarbamoyloxy, ethylcarbamoyloxy, phenylcarbamoyloxy, methoxycarbonylethoxy, 5-chlorofuryl-2-, methylsulfonyloxy, ethylsulfonyloxy, phenylsulfonyloxy, vinylsulfonyloxy, phenoxysulfonyl, phenthioethylsulfonyl or vinylsulfonyl, (c) cyclohexyl, (d) trimethylcyclohexyl, (e) methylamino, (f) dimethylamino, (g) ethylamino, (h) diethylamino, (i) hydroxyethylamino, (j) di-(β-cyanoethyl)amino, (k) di(acetoxyethyl)amino, (l) phenylamino, (m) ethoxyethylamino, (n) formamido, (o) acetamido, (p) propionamido, (q) benzamido, (r) N-piperazino, (s) N-piperidino, (t) N-morpholino or ##STR132##

Claim 11

The compound according to claim 3 having the formula ##STR133##

Claim 12

The compound according to claim 3 having the formula ##STR134##

Claim 13

The compound according to claim 3 having the formula ##STR135##

Claim 14

The compound according to claim 3 having the formula ##STR136##

Claim 15

The compound according to claim 5 having the formula ##STR137##

Claim 16

The compound according to claim 5 having the formula ##STR138##

Claim 17

The compound according to claim 5 having the formula ##STR139##

Claim 18

The compound of the formula ##STR140##

Claim 19

The compound of the formula ##STR140##

Claim 20

The compound the formula ##STR141##

Claim 21

The compound the formula ##STR141##

Claim 22

The compound according to claim 3 having the formula ##STR142##

Claim 23

The compound of the formula ##STR143##

Claim 24

The compound of the formula ##STR143##