US4906662A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Phenol derivatives, their preparation and the use thereof
Assignee: Otsuka Pharmaceutical Factory Inc
•
Filing: 1987-01-27
•
Granted: 1990-03-06
•
Expires: 2007-01-27
Abstract
Abstract Disclosed are phenol derivatives of the formula ##STR1## wherein R 1 is a substituted phenyl group, R 2 and R 3 are C 1 -C 6 alkyl group and of the formula ##STR2## wherein R 8 , R 9 and R 10 are C 1 -C 6 alkyl and the like and A is H, C 1 -C 6 alkylsulfonyl and the like substituents. These compounds and some related compounds have anti-inflammatory activity and lipoxygenase inhibitory activity.
Inventors
- 👤 Kinji Hashimoto
- 👤 Kiyoto Goto
- 👤 Ken-ichi Kanai
- 👤 Yoshiaki Tsuda
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 19:42
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/16; C07D295/18; C07D295/182; C07D295/185; A; A61; A61P; A61P25/00; A61P25/04; A61P29/00; A61P37/00; A61P37/08; A61P7/00; A61P7/02; A61P7/10; A61P9/00; A61P9/12; C07C; C07C255/00; C07C311/00; C07C311/15; C07C311/16; C07C311/30; C07C311/37; C07C311/38; C07C317/00; C07C317/26; C07C317/32; C07C317/34; C07C323/00; C07C323/50; C07C323/62; C07C323/63; C07D295/192
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
614 words
A compound selected from the group consisting of: (1) a compound of the formula ##STR105## wherein R 1 represents a phenyl group having 1-3 substituents selected from the class consisting of cyano group, carbamoyl group, nitro group, sulfamoyl group, hydroxy-C 1 -C 6 alkyl group, C 1 -C 6 -alkyoxycarbonyl-Cl-C 6 alkyl group, carboxy-C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 1 -C 6 alkylthio group, phenylthio group ad C 1 -C 6 alkysulfonyl group, and a salt thereof; (2) a compound of the formula ##STR106## wherein R 2 and R 3 are as defined above and R 4 represents a tri(C 1 -C 6 alkoxy) phenyl group, dihalophenyl group or a group of the formula ##STR107## wherein R 5 is hydroxy-C 1 -C 6 alkyl or carboxyl-C 1 -C 6 alkyl group and R 6 is hydroxyl group, halogen atom or C 1 -C 6 alkyl group, and a salt thereof; (3) a compound of the formula ##STR108## wherein R 7 represents a phenyl group having a substituent selected from the class consisting of fluoro, 2-chloro, C 1 -C 6 alkoxy, carboxyl, n-butyl, amino, hydroxyl and N,N-di(C 1 -C 6 alkyl) amino groups, or R 7 represents a phenyl group having carboxyl and C 1 -C 6 alkyl groups as the substituent, a phenyl group having carboxyl and hydroxyl groups as the substituent, a phenyl group having carboxyl group and halogen atom as the substituent, a phenyl group having hydroxyl group and halogen atom as the substituent, or a phenyl group having C 1 -C 6 alkoxy and hydroxy group as the substituent, and a salt thereof; and (4) a compound of the formula ##STR109## wherein R 8 and R 9 are the same and each represent tertbutyl group, R 10 represents hydrogen atom or C 1 -C 6 alkyl group, or R 9 and R 10 , taken together with the phenyl ring to which they are attached, form a fused ring of the formula ##STR110## and A represents: a hydrogen atom, C 1 -C 6 alkylsulfonyl group, C 1 -C 6 alkoxycarbonyl group, piperidinocarbonyl group, phenyl-C 1 -C 6 alkylcarbamoyl group, C 1 -C 12 alkylcarbamoyl group, C 3 -C 8 cycloalkylcarbamoyl group, C 2 -C 6 alkenyl group having a substituent selected from the class consisting of C 1 -C 6 alkoxy-carbonyl, carboxyl, C 1 -C 6 acyl, C 1 -C 6 alkylcarbamoyl and C 3 -C 8 cycloalkylcarbamoyl groups, C 1 -C 6 alkyl group having a substituent selected from the class consisting of C 3 -C 8 cycloalkyl-carbamoyl, C 1 -C 6 alkylcarbamoyl, phenyl-C 1 -C 6 alkyl-carbamoyl, piperidinocarbonyl, morpholinocarbonyl and hydrazinocarbonyl groups, carboxy-C 1 -C 6 alkyl group, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl group, C 1 -C 6 alkyl group, carboxyl group, C 1 -C 6 alkoxy group, halogen atom, or a group --NR 11 R 12 , wherein R 11 is hydrogen atom or C 1 -C 6 alkyl group, and R 12 is C 1 -C 6 alkyl group having a phenyl group as the substituent, phenyl group, benzoyl group which may optionally have C 1 -C 6 alkyl group as the substituent, C 1 -C 6 acyl group which may optionally have C 1 -C 6 alkoxycarbonyl group as the substituent, C 1 -C 6 alkylsulfonyl group or phenylsulfonyl group; with the proviso that when R 10 is hydrogen atom, the group A does not represent hydrogen atom, carboxy-C 1 -C 6 alkyl group, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl group, C 1 -C 6 alkyl group, carboxyl group, C 1 -C 6 alkoxy group or halogen atom; and a salt thereof.
Claim 2
Dependent Claim
614 words
A compound selected from the group consisting of: (1) a compound of the formula ##STR105## wherein R 1 represents a phenyl group having 1-3 substituents selected from the class consisting of cyano group, carbamoyl group, nitro group, sulfamoyl group, hydroxy-C 1 -C 6 alkyl group, C 1 -C 6 -alkyoxycarbonyl-Cl-C 6 alkyl group, carboxy-C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 1 -C 6 alkylthio group, phenylthio group ad C 1 -C 6 alkysulfonyl group, and a salt thereof; (2) a compound of the formula ##STR106## wherein R 2 and R 3 are as defined above and R 4 represents a tri(C 1 -C 6 alkoxy) phenyl group, dihalophenyl group or a group of the formula ##STR107## wherein R 5 is hydroxy-C 1 -C 6 alkyl or carboxyl-C 1 -C 6 alkyl group and R 6 is hydroxyl group, halogen atom or C 1 -C 6 alkyl group, and a salt thereof; (3) a compound of the formula ##STR108## wherein R 7 represents a phenyl group having a substituent selected from the class consisting of fluoro, 2-chloro, C 1 -C 6 alkoxy, carboxyl, n-butyl, amino, hydroxyl and N,N-di(C 1 -C 6 alkyl) amino groups, or R 7 represents a phenyl group having carboxyl and C 1 -C 6 alkyl groups as the substituent, a phenyl group having carboxyl and hydroxyl groups as the substituent, a phenyl group having carboxyl group and halogen atom as the substituent, a phenyl group having hydroxyl group and halogen atom as the substituent, or a phenyl group having C 1 -C 6 alkoxy and hydroxy group as the substituent, and a salt thereof; and (4) a compound of the formula ##STR109## wherein R 8 and R 9 are the same and each represent tertbutyl group, R 10 represents hydrogen atom or C 1 -C 6 alkyl group, or R 9 and R 10 , taken together with the phenyl ring to which they are attached, form a fused ring of the formula ##STR110## and A represents: a hydrogen atom, C 1 -C 6 alkylsulfonyl group, C 1 -C 6 alkoxycarbonyl group, piperidinocarbonyl group, phenyl-C 1 -C 6 alkylcarbamoyl group, C 1 -C 12 alkylcarbamoyl group, C 3 -C 8 cycloalkylcarbamoyl group, C 2 -C 6 alkenyl group having a substituent selected from the class consisting of C 1 -C 6 alkoxy-carbonyl, carboxyl, C 1 -C 6 acyl, C 1 -C 6 alkylcarbamoyl and C 3 -C 8 cycloalkylcarbamoyl groups, C 1 -C 6 alkyl group having a substituent selected from the class consisting of C 3 -C 8 cycloalkyl-carbamoyl, C 1 -C 6 alkylcarbamoyl, phenyl-C 1 -C 6 alkyl-carbamoyl, piperidinocarbonyl, morpholinocarbonyl and hydrazinocarbonyl groups, carboxy-C 1 -C 6 alkyl group, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl group, C 1 -C 6 alkyl group, carboxyl group, C 1 -C 6 alkoxy group, halogen atom, or a group --NR 11 R 12 , wherein R 11 is hydrogen atom or C 1 -C 6 alkyl group, and R 12 is C 1 -C 6 alkyl group having a phenyl group as the substituent, phenyl group, benzoyl group which may optionally have C 1 -C 6 alkyl group as the substituent, C 1 -C 6 acyl group which may optionally have C 1 -C 6 alkoxycarbonyl group as the substituent, C 1 -C 6 alkylsulfonyl group or phenylsulfonyl group; with the proviso that when R 10 is hydrogen atom, the group A does not represent hydrogen atom, carboxy-C 1 -C 6 alkyl group, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl group, C 1 -C 6 alkyl group, carboxyl group, C 1 -C 6 alkoxy group or halogen atom; and a salt thereof.
Claim 3
Dependent Claim
118 words
A compound as defined in claim 1 which is selected from the group consisting of: (1) a compound of the formula (1) wherein R 1 is a phenyl group having cyano or hydroxy-C 1 -C 6 alkyl group as the substituent, (2) a compound of the formula (2) wherein R 6 is a halogen atom, (3) a compound of the formula (3) wherein R 7 is a fluorophenyl group, and (4) a compound of the formula (4) wherein A is a hydrogen atom, C 2 -C 6 alkenyl group having a carboxyl or C 1 -C 6 alkoxy group, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl group, C 1 -C 6 alkyl group or halogen atom.
Claim 4
Dependent Claim
24 words
A compound as defined in claim 1 which is selected from the group consisting of: 2,6-di-tert-butyl-4-(4-chloro-2-hydroxymethylphenylamino)phenol, 2,6-di-tert-butyl-4-(2-hydroxymethylphenylamino)phenol, 2-(3,5-di-tert-butyl-4-hydroxyphenylamino)cinnamic acid, 2,6-di-tert-butyl-4-(4-cyanophenylamino)phenol, 2,6-di-tert-butyl-4-(4-fluorophenylamino)phenol, 2-methyl-4-phenylamino-5,6,7,8-tetrahydronaphthol, and 2-methyl-4-(4-methoxycarbonylemethylphenylamino)-5,6,7,8-tetrahydrohaphthol
Claim 5
Dependent Claim
24 words
An anti-inflammatory composition comprising an effective amount of at least one compound as defined in claim 1 in admixture with a pharmaceutically acceptable carrier.
Claim 6
Dependent Claim
27 words
A pharmaceutical composition for inhibiting lipoxygenase comprising an effective amount of at least one compound as defined in claim 1 in admixture with a pharmaceutically acceptable carrier.
Claim 7
Independent Claim
463 words
A method for treating inflammation in a patient comprising administering to said patient an effective amount of at least one compound selected from the group consisting of: (a) a compound of the formula ##STR111## wherein R 1a represents unsubstituted phenyl group or a phenyl group having 1-3 substituents selected from the class consisting of cyano group, carbamoyl group, nitro group, sulfamoyl group, hydroxy-C 1 -C 6 alkyl group, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl group, carboxy-C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 1 -C 6 acyl group, C 1 -C 6 alkylthio group, phenylthio group, C 1 -C 6 alkylsulfonyl group, amino group, C 1 -C 6 alkoxy group, hydroxyl group, C 1 -C 6 alkyl group and halogen atom, and R 2 and R 3 are the same or different and represent C 1 -C 6 alkyl group and a salt thereof; and (b) a compound of the formula ##STR112## wherein R 8 , R 9 and R 10 are as defined in the formula (4) above, and Aa represents: a hydrogen atom, C 1 -C 6 alkylsulfonyl group, C 1 -C 6 alkoxycarbonyl group, piperidinocarbonyl group, phenyl-C 1 -C 6 alkylcarbamoyl group, C 1 -C 12 alkylcarbamoyl group, C 3 -C 8 cycloalkylcarbamoyl group, C 2 -C 6 alkenyl group having a substituent selected from the class consisting of C 1 -C 6 alkoxycarbonyl, carboxyl, C 1 -C 6 acyl, C 1 -C 6 alkylcarbamoyl and C 3 -C 8 cycloalkylcarbamoyl groups, C 1 -C 6 alkyl group having a substituent selected from the class consisting of C 3 -C 8 cycloalkylcarbamoyl, C 1 -C 6 alkylcarbamoyl, phenyl-C 1 -C 6 alkylcarbamoyl, piperidinocarbonyl, morpholinocarbonyl and hydrazinocarbonyl groups, carboxy-C 1 -C 6 alkyl group, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl group, C 1 -C 6 alkyl group, carboxy group, C 1 14 C 6 alkoxy group, halogen atom, or a group --NR 11 R 12a (wherein R 11 is hydrogen atom or C 1 -C 6 alkyl group, and R 12a is C 1 -C 6 alkyl group, C 1 -C 6 alkyl group having a phenyl group as the substituent, phenyl group, benzoyl group which may optionally have C 1 -C 6 alkyl as the substituent, C 1 -C 6 acyl group which may optionally have C 1 -C 6 alkoxycarbonyl group as the substituent, C 1 -C 6 alkylsulfonyl group or phenylsulfonyl group); with the proviso that when R 10 is hydrogen atom, the group Aa does not represent hydrogen atom, carboxy-C 1 -C 6 alkyl group, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl group, C 1 -C 6 alkyl group, carboxyl group, C 1 -C 6 alkoxy group or halogen atom, and a salt thereof.
Claim 8
Independent Claim
463 words
A method for treating inflammation in a patient comprising administering to said patient an effective amount of at least one compound selected from the group consisting of: (a) a compound of the formula ##STR111## wherein R 1a represents unsubstituted phenyl group or a phenyl group having 1-3 substituents selected from the class consisting of cyano group, carbamoyl group, nitro group, sulfamoyl group, hydroxy-C 1 -C 6 alkyl group, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl group, carboxy-C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 1 -C 6 acyl group, C 1 -C 6 alkylthio group, phenylthio group, C 1 -C 6 alkylsulfonyl group, amino group, C 1 -C 6 alkoxy group, hydroxyl group, C 1 -C 6 alkyl group and halogen atom, and R 2 and R 3 are the same or different and represent C 1 -C 6 alkyl group and a salt thereof; and (b) a compound of the formula ##STR112## wherein R 8 , R 9 and R 10 are as defined in the formula (4) above, and Aa represents: a hydrogen atom, C 1 -C 6 alkylsulfonyl group, C 1 -C 6 alkoxycarbonyl group, piperidinocarbonyl group, phenyl-C 1 -C 6 alkylcarbamoyl group, C 1 -C 12 alkylcarbamoyl group, C 3 -C 8 cycloalkylcarbamoyl group, C 2 -C 6 alkenyl group having a substituent selected from the class consisting of C 1 -C 6 alkoxycarbonyl, carboxyl, C 1 -C 6 acyl, C 1 -C 6 alkylcarbamoyl and C 3 -C 8 cycloalkylcarbamoyl groups, C 1 -C 6 alkyl group having a substituent selected from the class consisting of C 3 -C 8 cycloalkylcarbamoyl, C 1 -C 6 alkylcarbamoyl, phenyl-C 1 -C 6 alkylcarbamoyl, piperidinocarbonyl, morpholinocarbonyl and hydrazinocarbonyl groups, carboxy-C 1 -C 6 alkyl group, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl group, C 1 -C 6 alkyl group, carboxy group, C 1 14 C 6 alkoxy group, halogen atom, or a group --NR 11 R 12a (wherein R 11 is hydrogen atom or C 1 -C 6 alkyl group, and R 12a is C 1 -C 6 alkyl group, C 1 -C 6 alkyl group having a phenyl group as the substituent, phenyl group, benzoyl group which may optionally have C 1 -C 6 alkyl as the substituent, C 1 -C 6 acyl group which may optionally have C 1 -C 6 alkoxycarbonyl group as the substituent, C 1 -C 6 alkylsulfonyl group or phenylsulfonyl group); with the proviso that when R 10 is hydrogen atom, the group Aa does not represent hydrogen atom, carboxy-C 1 -C 6 alkyl group, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl group, C 1 -C 6 alkyl group, carboxyl group, C 1 -C 6 alkoxy group or halogen atom, and a salt thereof.
Claim 9
Dependent Claim
123 words
A method as defined in claim 6 wherein the compound is selected from the group consisting of: (a) a compound of the formula (5) wherein R 1a is unsubstituted phenyl group, phenyl group having a halogen atom and hydroxy-C 1 -C 6 alkyl group as the substituent, phenyl group having hydroxy-C 1 -C 6 alkyl group as the substituent, cyanophenyl group or halophenyl group and R 2 and R 3 are the same or different and each represent C 1 -C 6 alkyl group, and (b) a compound of the formula (7) wherein R 8 , R 9 and R 10 are as defined in the formula (7) and Aa is C 2 -C 6 alkenyl group having carboxyl group as the substituent.
Claim 10
Dependent Claim
25 words
A method as defined in claim 6 wherein the compound is selected from the group consisting of: 2,6-di-tert-butyl-4-(4-chloro-2-hydroxymethylphenylamino)phenol, 2,6-di-tert-butyl-4-(2-hydroxymethylphenylamino)phenol, 2-(3,5-di-tert-butyl-4-hydroxyphenylamino)cinnamic acid, 2,6-di-tert-butyl-4-(4-cyanophenylamino)phenol, 2,6-di-tert-butyl-4-(4-fluorophenylamino)phenol and 2,6-di-tert-butyl-4-phenylaminophenol.
Claim 11
Independent Claim
467 words
A method for inhibiting lipoxygenase in a patient comprising administering to said patient an effective amount of at least one compound selected from the group consisting of: (a) a compound of the formula ##STR113## wherein R 1b represents unsubstituted phenyl group or a phenyl group having 1-3 substituents selected from the class consisting of carboxyl group, cyano group, carbamoyl group, nitro group, sulfamoyl group, hydroxy-C 1 -C 6 alkyl group, C 1 -C 6 alkoxycarbonyl C 1 -C 6 -alkyl group, carboxy-C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 1 -C 6 acyl group, C 1 -C 6 alkylthio group, phenylthio group, C 1 -C 6 alkylsulfonyl group, amino group, C 1 -C 6 alkoxy group, hydroxyl group, C 1 -C 6 alkyl group and halogen atom, and R 2 and R 3 each are the same or different and represent C 1 -C 6 alkyl group and a salt thereof; and (b) a compound of the formula ##STR114## wherein R 8 , R 9 and R 10 are as defined in the formula (4) above, and Aa represents: a hydrogen atom, C 1 -C 6 alkylsulfonyl group, C 1 -C 6 alkoxycarbonyl group, piperidinocarbonyl group, phenyl-C 1 -C 6 alkylcarbamoyl group, C 1 -C 12 alkylcarbamoyl group, C 3 -C 8 cycloalkylcarbamoyl group, C 2 -C 6 alkenyl group having a substituent selected from the class consisting of C 1 -C 6 alkoxycarbonyl, carboxyl, C 1 -C 6 acyl, C 1 -C 6 alkylcarbamoyl and C 3 -C 8 cycloalkylcarbamoyl groups, C 1 -C 6 alkyl group having a substituent selected from the class consisting of C 3 -C 8 cycloalkylcarbamoyl, C 1 -C 6 alkylcarbamoyl, phenyl-C 1 -C 6 alkylcarbamoyl, piperidinocarbonyl, morpholinocarbonyl and hydrazinocarbonyl groups, carboxy-C 1 -C 6 alkyl group, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl group, C 1 -C 6 alkyl group, carboxyl group, C 1 -C 6 alkoxy group, halogen atom, or a group --NR 11 R 12a (wherein R 11 is hydrogen atom or C 1 -C 6 alkyl group, and R 12a is C 1 -C 6 alkyl group, C 1 -C 6 alkyl group having a phenyl group as the substituent, phenyl group, benzoyl group which may optionally have C 1 -C 6 alkyl group as the substituent, C 1 -C 6 acyl group which may optionally have C 1 -C 6 alkoxycarbonyl group as the substituent, C 1 -C 6 alkylsulfonyl group or phenylsulfonyl group); with the proviso that when R 10 is hydrogen atom, the group Aa does not represent hydrogen atom, carboxy-C 1 -C 6 alkyl group, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl group, C 1 -C 6 alkyl group, carboxyl group, C 1 -C 6 alkoxy group or halogen atom, and a salt thereof.
Claim 12
Independent Claim
467 words
A method for inhibiting lipoxygenase in a patient comprising administering to said patient an effective amount of at least one compound selected from the group consisting of: (a) a compound of the formula ##STR113## wherein R 1b represents unsubstituted phenyl group or a phenyl group having 1-3 substituents selected from the class consisting of carboxyl group, cyano group, carbamoyl group, nitro group, sulfamoyl group, hydroxy-C 1 -C 6 alkyl group, C 1 -C 6 alkoxycarbonyl C 1 -C 6 -alkyl group, carboxy-C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 1 -C 6 acyl group, C 1 -C 6 alkylthio group, phenylthio group, C 1 -C 6 alkylsulfonyl group, amino group, C 1 -C 6 alkoxy group, hydroxyl group, C 1 -C 6 alkyl group and halogen atom, and R 2 and R 3 each are the same or different and represent C 1 -C 6 alkyl group and a salt thereof; and (b) a compound of the formula ##STR114## wherein R 8 , R 9 and R 10 are as defined in the formula (4) above, and Aa represents: a hydrogen atom, C 1 -C 6 alkylsulfonyl group, C 1 -C 6 alkoxycarbonyl group, piperidinocarbonyl group, phenyl-C 1 -C 6 alkylcarbamoyl group, C 1 -C 12 alkylcarbamoyl group, C 3 -C 8 cycloalkylcarbamoyl group, C 2 -C 6 alkenyl group having a substituent selected from the class consisting of C 1 -C 6 alkoxycarbonyl, carboxyl, C 1 -C 6 acyl, C 1 -C 6 alkylcarbamoyl and C 3 -C 8 cycloalkylcarbamoyl groups, C 1 -C 6 alkyl group having a substituent selected from the class consisting of C 3 -C 8 cycloalkylcarbamoyl, C 1 -C 6 alkylcarbamoyl, phenyl-C 1 -C 6 alkylcarbamoyl, piperidinocarbonyl, morpholinocarbonyl and hydrazinocarbonyl groups, carboxy-C 1 -C 6 alkyl group, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl group, C 1 -C 6 alkyl group, carboxyl group, C 1 -C 6 alkoxy group, halogen atom, or a group --NR 11 R 12a (wherein R 11 is hydrogen atom or C 1 -C 6 alkyl group, and R 12a is C 1 -C 6 alkyl group, C 1 -C 6 alkyl group having a phenyl group as the substituent, phenyl group, benzoyl group which may optionally have C 1 -C 6 alkyl group as the substituent, C 1 -C 6 acyl group which may optionally have C 1 -C 6 alkoxycarbonyl group as the substituent, C 1 -C 6 alkylsulfonyl group or phenylsulfonyl group); with the proviso that when R 10 is hydrogen atom, the group Aa does not represent hydrogen atom, carboxy-C 1 -C 6 alkyl group, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl group, C 1 -C 6 alkyl group, carboxyl group, C 1 -C 6 alkoxy group or halogen atom, and a salt thereof.
Claim 13
Dependent Claim
73 words
A method as defined in claim 9 wherein the compound is a compound of the formula (7) wherein R 8 , R 9 and R 10 are as defined in the formula (7) and Aa is hydrogen, C 1 -C 6 alkoxy, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl, C 1 -C 6 alkyl, halogen or C 2 -C 6 alkenyl having C 1 -C 6 alkoxycarbonyl group as the substituent.
Claim 14
Dependent Claim
27 words
A method as defined in claim 9 wherein the compound is selected from the group consisting of: 2,3,6-trimethyl-4-(4-methoxyphenylamino)phenol, 2,3,6-trimethyl-4-(4-methoxycarbonylmethylphenylamino)phenol, 2,3,6-trimethyl-4-(4-methylphenylamino)phenol, 2,3,6-trimethyl-4-(4-chlorophenylamino)phenol, 2-methyl-4-phenylamino-5,6,7,8-tetrahydronaphthol, 2-methyl-4-(4-methoxycarbonylmethylphenylamino)-5,6,7,8-tetrahydronaphthol, 2,3,6-trimethyl-4-phenylaminophenol and ethyl 3-(4-hydroxy-2,3,5-trimethylphenylamino)cinnamate.
References Cited (Backward Citations)
FR1539553A
Cited
US4112229A
Cited
US4200432A
Cited
US4008043A
Cited
US4008999A
Cited
US4054147A
Cited
US4170452A
Cited
US4346105A
Cited
US4172151A
Cited
US4568684A
Cited
US4496590A
Cited
US4515980A
Cited
US4539429A
Cited
US4510139A
Cited
US4764619A
Cited
EP0211549A2
Cited
EP0212848A2
Cited
US4716178A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-03-05 | 1993-09-04 | 1994-03-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-03-05 | 1997-09-04 | 1998-03-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-03-05 | 2001-09-04 | 2002-03-06 | $7700.00 | Window Closed / Lapsed |