HALOGENATED BENZYLIDINE DERIVATIVES

Abstract

Novel Halogenated Benzylidine derivatives are provided which exhibit activity for the treatment of immunological diseases and inflammation

Claims

1. A compound of formula (I) including the analogs, tautomeric forms, stereoisomers, polymorphs, and pharmaceutically acceptable salts thereof, ##STR01100## wherein X is a halogen and Y is selected from the group consisting of a hydrogen, a halogen, a hydroxyl group, a nitro group, a cyano group, a formyl group, an amino group and a sulfonyl group, and wherein the groups represented by R1 and R3 are selected from the group consisting of linear or branched, substituted or unsubstituted (C1 to C12) alkyl groups, and substituted or unsubstituted (C1 to C12) alkoxy groups, and wherein R.sub.4 is selected from the group consisting of alaninie, glycine, arginine, aspargine, cysteine, glutamic acid, glutamine, histidine, isoleucine, leucine, lysine, methionine, ornithine, proline, serine, threonine, tryptophan, and tyrosine, which may be unsubstituted or substituted, and their derivatives such as ester and amides of carboxylic acid.

2. The compound of claim 1 wherein R.sub.4 is selected from the group consisting of halogen, alkyl, alkoxy, aryl, heteroaryl, and amino groups.

3. The compound of claim 1 wherein R.sub.4 is selected from the group consisting of an unsubstituted or substituted aryl amine, a pyridyl amine and amino benzoic acid, wherein the free amine group condenses to form the Halogenated Benzylidene compound.

4. The compound of claim 1 selected from the group consisting of: 2-[(5-Bromo-2-hydroxy-benzylidene)-amino-3-(4-hydroxy phenyl)-propionic acid methyl ester 2-[(5-Bromo-2-hydroxy-benzylidene)-amino-3-methyl butyric acid methyl ester 2-(5-Bromo-2-hydroxy-benzylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester 2-[(5-Bromo-2-hydroxy-benzylidene)-amino-3-(4-hydroxy phenyl)-propionic acid 4-Bromo-2-{[2-hydroxy-1-(4-hydroxy benzyl)-ethylamino]-Methyl}-phenol 2-(5-Bromo-2-hydroxy-benzylamino)-3-methyl-butyric acid methyl ester 2-[(5-Bromo-2-hydroxy-benzylidene)-amino]-3-methyl-butyric acid 4-Bromo-2-[(1-hydroxymethyl-2-methyl-propylimino)-methyl]-phenol (E)-4-bromo-2-((2,4-dichlorophenylimino)methyl) phenyl 4-methylbenzoate (E)-4-bromo-2-((4-chlorophenylimino)methyl)phenyl 4-methylbenzoate (E)-4-bromo-2-((2,3-dichlorophenylimino)methyl) phenyl 3-methylbenzoate (E)-4-bromo-2-((3,4-dichlorophenylimino)methyl) phenyl 4-methylbenzoate (E)-4-bromo-2-((3,5-dichlorophenylimino)methyl) phenyl 4-methylbenzoate (E)-4-bromo-2-((phenethylimino)methyl)phenyl 3-methylbenzoate (E)-4-bromo-2-((phenethylimino)methyl)phenyl 4-methylbenzoate (E)-4-bromo-2-((pyridin-3-ylimino)methyl)phenyl 4-methylbenzoate (E)-4-bromo-2-((pyridin-3-ylimino)methyl)phenyl 3-methylbenzoate (E)-3-(5-bromo-2-(nicotinoyloxy)benzylideneamino) benzoic acid (E)-4-bromo-2-((phenethylimino)methyl)phenyl isobutyrate 2-[(5-Bromo-2-isobutyryloxy-benzylidene)-amino]-3-(4-isobutyryloxy phenyl propionic acid methyl ester (E)-4-bromo-2-((4-((diethylamino)methyl)phenylimino)methyl)phenol (E)-1-(3-chlorobenzylideneamino)-2-methylpropan-1-ol (E)-1-(3-bromobenzylideneamino)-2-methylpropan-1-ol (E)-4-chloro-2-((1-hydroxy-2-methylpropylimino)methyl)phenol (E)-4-bromo-2-((1-hydroxy-2-methylpropylimino)methyl)phenol (E)-4-chloro-2-((1-hydroxy-2-methylpropylimino)methyl)phenyl isobutyrate (E)-4-bromo-2-((1-hydroxy-2-methylpropylimino)methyl)phenyl isobutyrate (E)-3-chloro-5-((1-hydroxy-2-methylpropylimino)methyl)phenyl 4-methylbenzoate (E)-3-bromo-5-((1-hydroxy-2-methylpropylimino)methyl)phenyl 4-methylbenzoate (E)-5-chloro-2-hydroxy-3-((1-hydroxy-2-methylpropylimino)methyl)phenyl 4-methylbenzoate (E)-5-bromo-2-hydroxy-3-((1-hydroxy-2-methylpropylimino)methyl)phenyl 4-methylbenzoate (E)-5-chloro-3-((1-hydroxy-2-methylpropylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate (E)-5-bromo-3-((1-hydroxy-2-methylpropylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate (E)-3-chloro-5-((1-hydroxy-2-methylpropylimino)methyl)phenyl 3-methylbenzoate (E)-3-bromo-5-((1-hydroxy-2-methylpropylimino)methyl)phenyl 3-methylbenzoate (E)-5-chloro-2-hydroxy-3-((1-hydroxy-2-methylpropylimino)methyl)phenyl 3-methylbenzoate (E)-5-bromo-2-hydroxy-3-((1-hydroxy-2-methylpropylimino)methyl)phenyl 3-methylbenzoate (E)-5-chloro-3-((1-hydroxy-2-methylpropylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate (E)-5-bromo-3-((1-hydroxy-2-methylpropylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate (E)-3-chloro-5-((1-hydroxy-2-methylpropylimino)methyl)phenyl nicotinate (E)-3-bromo-5-((1-hydroxy-2-methylpropylimino)methyl)phenyl nicotinate (E)-5-chloro-2-hydroxy-3-((1-hydroxy-2-methylpropylimino)methyl)phenyl nicotinate (E)-5-bromo-2-hydroxy-3-((1-hydroxy-2-methylpropylimino)methyl)phenyl nicotinate (E)-5-chloro-3-((1-hydroxy-2-methylpropylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate (E)-5-bromo-3-((1-hydroxy-2-methylpropylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate (E)-3-chloro-5-((1-hydroxy-2-methylpropylimino)methyl)phenyl isobutyrate (E)-3-bromo-5-((1-hydroxy-2-methylpropylimino)methyl)phenyl isobutyrate (E)-5-chloro-2-hydroxy-3-((1-hydroxy-2-methylpropylimino)methyl)phenyl isobutyrate (E)-5-bromo-2-hydroxy-3-((1-hydroxy-2-methylpropylimino)methyl)phenyl isobutyrate (E)-5-chloro-2-isobutroxy-3-((1-hydroxy-2-methylpropylimino)methyl)phenyl isobutyrate (E)-5-bromo-2-isobutroxy-3-((1-hydroxy-2-methylpropylimino)methyl)phenyl isobutyrate (E)-3-chloro-5-((1-hydroxy-2-methylpropylimino)methyl)phenol (E)-3-bromo-5-((1-hydroxy-2-methylpropylimino)methyl)phenol (E)-5-chloro-3-((1-hydroxy-2-methylpropylimino)methyl)benzene-1,2-diol (E)-5-bromo-3-((1-hydroxy-2-methylpropylimino)methyl)benzene-1,2-diol (E)-4-chloro-2-hydroxy-6-((1-hydroxy-2-methylpropylimino)methyl)phenyl isobutyrate (E)-4-bromo-2-hydroxy-6-((1-hydroxy-2-methylpropylimino)methyl)phenyl isobutyrate methyl 2-(3-chlorobenzylideneamino)-3-methylbutanoate methyl 2-(3-bromobenzylideneamino)-3-methylbutanoate methyl 2-(5-chloro-2-hydroxybenzylideneamino)-3-methylbutanoate methyl 2-(5-bromo-2-hydroxybenzylideneamino)-3-methylbutanoate methyl 2-(5-chloro-2-(isobutyryloxy)benzylideneamino)-3-methylbutanoate methyl 2-(5-bromo-2-(isobutyryloxy)benzylideneamino)-3-methylbutanoate 3-chloro-5-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate 3-bromo-5-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate 5-chloro-2-hydroxy-3-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate 5-bromo-2-hydroxy-3-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate 5-chloro-2-(isobutyryloxy)-3-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate 5-bromo-2-(isobutyryloxy)-3-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate 3-chloro-5-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate 3-bromo-5-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate 5-chloro-2-hydroxy-3-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate 5-bromo-2-hydroxy-3-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate 5-chloro-2-(isobutyryloxy)-3-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate 5-bromo-2-(isobutyryloxy)-3-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate 3-chloro-5-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl nicotinate 3-bromo-5-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl nicotinate 5-chloro-2-hydroxy-3-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl nicotinate 5-bromo-2-hydroxy-3-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl nicotinate 5-chloro-2-(isobutyryloxy)-3-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl nicotinate 5-bromo-2-(isobutyryloxy)-3-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl nicotinate methyl 2-(3-chloro-5-(isobutyryloxy)benzylideneamino)-3-methylbutanoate methyl 2-(3-bromo-5-(isobutyryloxy)benzylideneamino)-3-methylbutanoate methyl 2-(5-chloro-2-hydroxy-3-(isobutyryloxy)benzylideneamino)-3-methylbutanoate methyl 2-(5-bromo-2-hydroxy-3-(isobutyryloxy)benzylideneamino)-3-methylbutanoate methyl 2-(5-chloro-2,3-bis(isobutyryloxy)benzylideneamino)-3-methylbutanoate methyl 2-(5-bromo-2,3-bis(isobutyryloxy)benzylideneamino)-3-methylbutanoate methyl 2-(3-chloro-5-hydroxybenzylideneamino)-3-methylbutanoate methyl 2-(3-bromo-5-hydroxybenzylideneamino)-3-methylbutanoate methyl 2-(5-chloro-2,3-dihydroxybenzylideneamino)-3-methylbutanoate methyl 2-(5-bromo-2,3-dihydroxybenzylideneamino)-3-methylbutanoate methyl 2-(5-chloro-3-hydroxy-2-(3-methylbut-1-en-2-yloxy)benzylideneamino)-3-methylbutanoate methyl 2-(5-bromo-3-hydroxy-2-(3-methylbut-1-en-2-yloxy)benzylideneamino)-3-methylbutanoate 2-(3-chlorobenzylideneamino)-3-methylbutanoic acid 2-(3-bromobenzylideneamino)-3-methylbutanoic acid 2-(5-chloro-2-hydroxybenzylideneamino)-3-methylbutanoic acid 2-(5-bromo-2-hydroxybenzylideneamino)-3-methylbutanoic acid 2-(5-chloro-2-(isobutyryloxy)benzylideneamino)-3-methylbutanoic acid 2-(5-bromo-2-(isobutyryloxy)benzylideneamino)-3-methylbutanoic acid 2-(3-chloro-5-(4-methylbenzoyloxy)benzylideneamino)-3-methylbutanoic acid 2-(3-bromo-5-(4-methylbenzoyloxy)benzylideneamino)-3-methylbutanoic acid 2-(5-chloro-2-hydroxy-3-(4-methylbenzoyloxy)benzylideneamino)-3-methylbutanoic acid 2-(5-bromo-2-hydroxy-3-(4-methylbenzoyloxy)benzylideneamino)-3-methylbutanoic acid 2-(5-chloro-2-(isobutyryloxy)-3-(4-methylbenzoyloxy)benzylideneamino)-3-methylbutanoic acid 2-(5-bromo-2-(isobutyryloxy)-3-(4-methylbenzoyloxy)benzylideneamino)-3-methylbutanoic acid 2-(3-chloro-5-(3-methylbenzoyloxy)benzylideneamino)-3-methylbutanoic acid 2-(3-bromo-5-(3-methylbenzoyloxy)benzylideneamino)-3-methylbutanoic acid 2-(5-chloro-2-hydroxy-3-(3-methylbenzoyloxy)benzylideneamino)-3-methylbutanoic acid 2-(5-bromo-2-hydroxy-3-(3-methylbenzoyloxy)benzylideneamino)-3-methylbutanoic acid 2-(5-chloro-2-(isobutyryloxy)-3-(3-methylbenzoyloxy)benzylideneamino)-3-methylbutanoic acid 2-(5-bromo-2-(isobutyryloxy)-3-(3-methylbenzoyloxy)benzylideneamino)-3-methylbutanoic acid 2-(3-chloro-5-(nicotinoyloxy)benzylideneamino)-3-methylbutanoic acid 2-(3-bromo-5-(nicotinoyloxy)benzylideneamino)-3-methylbutanoic acid 2-(5-chloro-2-hydroxy-3-(nicotinoyloxy)benzylideneamino)-3-methylbutanoic acid 2-(5-bromo-2-hydroxy-3-(nicotinoyloxy)benzylideneamino)-3-methylbutanoic acid 2-(5-chloro-2-(isobutyryloxy)-3-(nicotinoyloxy)benzylideneamino)-3-methylbutanoic acid 2-(5-bromo-2-(isobutyryloxy)-3-(nicotinoyloxy)benzylideneamino)-3-methylbutanoic acid 2-(3-chloro-5-(isobutyryloxy)benzylideneamino)-3-methylbutanoic acid 2-(3-bromo-5-(isobutyryloxy)benzylideneamino)-3-methylbutanoic acid 2-(5-chloro-2-hydroxy-3-(isobutyryloxy)benzylideneamino)-3-methylbutanoic acid 2-(5-bromo-2-hydroxy-3-(isobutyryloxy)benzylideneamino)-3-methylbutanoic acid 2-(5-chloro-2,3-bis(isobutyryloxy)benzylideneamino)-3-methylbutanoic acid 2-(5-bromo-2,3-bis(isobutyryloxy)benzylideneamino)-3-methylbutanoic acid 2-(3-chloro-5-hydroxybenzylideneamino)-3-methylbutanoic acid 2-(3-bromo-5-hydroxybenzylideneamino)-3-methylbutanoic acid 2-(5-chloro-2,3-dihydroxybenzylideneamino)-3-methylbutanoic acid 2-(5-bromo-2,3-dihydroxybenzylideneamino)-3-methylbutanoic acid 2-(5-chloro-3-hydroxy-2-(isobutyryloxy)benzylideneamino)-3-methylbutanoic acid 2-(5-bromo-3-hydroxy-2-(isobutyryloxy)benzylideneamino)-3-methylbutanoic acid methyl 2-(3-chlorobenzylideneamino)-3-(4-hydroxyphenyl)propanoate methyl 2-(3-bromobenzylideneamino)-3-(4-hydroxyphenyl)propanoate methyl 2-(5-chloro-2-hydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoate methyl 2-(5-bromo-2-hydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoate methyl 2-(2-isobutricoxy-5-chlorobenzylideneamino)-3-(4-hydroxyphenyl)propanoate methyl 2-(2-isobutricoxy-5-bromobenzylideneamino)-3-(4-hydroxyphenyl)propanoate 3-chloro-5-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)phenyl 4-methylbenzoate 3-bromo-5-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)phenyl 4-methylbenzoate 5-chloro-2-hydroxy-3-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)phenyl 4-methylbenzoate 5-bromo-2-hydroxy-3-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)phenyl 4-methylbenzoate 5-chloro-3-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate 5-bromo-3-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate 3-chloro-5-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)phenyl 3-methylbenzoate 3-bromo-5-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)phenyl 3-methylbenzoate 5-chloro-2-hydroxy-3-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)phenyl 3-methylbenzoate 5-bromo-2-hydroxy-3-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)phenyl 3-methylbenzoate 5-chloro-3-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate 5-bromo-3-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate 3-chloro-5-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)phenyl nicotinate 3-bromo-5-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)phenyl nicotinate 5-chloro-2-hydroxy-3-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)phenyl nicotinate 5-bromo-2-hydroxy-3-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)phenyl nicotinate 5-chloro-3-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate 5-bromo-3-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate methyl 2-(3-isobutryateoxy-5-chlorobenzylideneamino)-3-(4-hydroxyphenyl)propanoate methyl 2-(3-isobutryateoxy-5-bromobenzylideneamino)-3-(4-hydroxyphenyl)propanoate methyl 2-(3-isobutryateoxy-5-chloro-2-hydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoate methyl 2-(3-isobutryateoxy-5-bromo-2-hydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoate methyl 2-(5-chloro-2,3-bisisobutrateoxybenzylideneamino)-3-(4-hydroxyphenyl)propanoate methyl 2-(5-bromo-2,3-bisisobutrateoxybenzylideneamino)-3-(4-hydroxyphenyl)propanoate methyl 2-(3-chloro-5-hydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoate methyl 2-(3-bromo-5-hydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoate methyl 2-(5-chloro-2,3-dihydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoate methyl 2-(5-bromo-2,3-dihydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoate methyl 2-(5-chloro-2-isobutrateoxy-3-hydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoate methyl 2-(5-bromo-2-isobutrateoxy-3-hydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoate 2-(3-chlorobenzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(3-bromobenzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(5-chloro-2-hydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(5-bromo-2-hydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(5-chloro-2-(isobutyryloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(5-bromo-2-(isobutyryloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(3-chloro-5-(4-methylbenzoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(3-bromo-5-(4-methylbenzoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(5-chloro-2-hydroxy-3-(4-methylbenzoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(5-bromo-2-hydroxy-3-(4-methylbenzoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(5-chloro-2-(isobutyryloxy)-3-(4-methylbenzoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(5-bromo-2-(isobutyryloxy)-3-(4-methylbenzoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(3-chloro-5-(3-methylbenzoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(3-bromo-5-(3-methylbenzoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(5-chloro-2-hydroxy-3-(3-methylbenzoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(5-bromo-2-hydroxy-3-(3-methylbenzoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(5-chloro-2-(isobutyryloxy)-3-(3-methylbenzoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(5-bromo-2-(isobutyryloxy)-3-(3-methylbenzoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(3-chloro-5-(nicotinoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(3-bromo-5-(nicotinoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(5-chloro-2-hydroxy-3-(nicotinoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(5-bromo-2-hydroxy-3-(nicotinoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(5-chloro-2-(isobutyryloxy)-3-(nicotinoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(5-bromo-2-(isobutyryloxy)-3-(nicotinoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(3-chloro-5-(isobutyryloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(3-bromo-5-(isobutyryloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(5-chloro-2-hydroxy-3-(isobutyryloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(5-bromo-2-hydroxy-3-(isobutyryloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(5-chloro-2,3-bis(isobutyryloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(5-bromo-2,3-bis(isobutyryloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(3-chloro-5-hydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(3-bromo-5-hydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(5-chloro-2,3-dihydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(5-bromo-2,3-dihydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(5-chloro-3-hydroxy-2-(isobutyryloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid 2-(5-bromo-3-hydroxy-2-(isobutyryloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid (Z)-3-(3-chlorobenzylideneamino)-1-hydroxy-4-(4-hydroxyphenyl)butan-2-one (Z)-3-(3-bromobenzylideneamino)-1-hydroxy-4-(4-hydroxyphenyl)butan-2-one (Z)-3-(5-chloro-2-hydroxybenzylideneamino)-1-hydroxy-4-(4-hydroxyphenyl)butan-2-one (Z)-3-(5-bromo-2-hydroxybenzylideneamino)-1-hydroxy-4-(4-hydroxyphenyl)butan-2-one (Z)-4-chloro-2-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl isobutyrate (Z)-4-bromo-2-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl isobutyrate (Z)-3-chloro-5-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate (Z)-3-bromo-5-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate (Z)-5-chloro-2-hydroxy-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate (Z)-5-bromo-2-hydroxy-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate (Z)-5-chloro-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate (Z)-5-bromo-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate (Z)-3-chloro-5-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate (Z)-3-bromo-5-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate 5-chloro-2-hydroxy-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate 5-bromo-2-hydroxy-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate 5-chloro-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate 5-bromo-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate 3-chloro-5-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl nicotinate 3-bromo-5-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl nicotinate 5-chloro-2-hydroxy-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl nicotinate 5-bromo-2-hydroxy-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl nicotinate 5-chloro-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate 5-bromo-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate 3-chloro-5-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl isobutyrate 3-bromo-5-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl isobutyrate 5-chloro-2-hydroxy-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl isobutyrate 5-bromo-2-hydroxy-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl isobutyrate 3-(5-chloro-2,3-bisisobutryloxybenzylideneamino)-1-hydroxy-4-(4-hydroxyphenyl)butan-2-one 3-(5-bromo-2,3-bisisobutryloxybenzylideneamino)-1-hydroxy-4-(4-hydroxyphenyl)butan-2-one 3-(3-chloro-5-hydroxybenzylideneamino)-1-hydroxy-4-(4-hydroxyphenyl)butan-2-one 3-(3-bromo-5-hydroxybenzylideneamino)-1-hydroxy-4-(4-hydroxyphenyl)butan-2-one 3-(5-chloro-2,3-dihydroxybenzylideneamino)-1-hydroxy-4-(4-hydroxyphenyl)butan-2-one 3-(5-bromo-2,3-dihydroxybenzylideneamino)-1-hydroxy-4-(4-hydroxyphenyl)butan-2-one 4-chloro-2-hydroxy-6-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl isobutyrate 4-bromo-2-hydroxy-6-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl isobutyrate 4-(2-(3-chlorobenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate 4-(2-(3-bromobenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate 4-(2-(5-chloro-2-hydroxybenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate 4-(2-(5-bromo-2-hydroxybenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate 4-(2-(2-isobutryloxy-5-chlorobenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate 4-(2-(2-isobutryloxy-5-bromobenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate 3-chloro-5-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate 3-bromo-5-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate 5-chloro-2-hydroxy-3-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate 5-bromo-2-hydroxy-3-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate 5-chloro-2-(isobutyryloxy)-3-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate 5-bromo-2-(isobutyryloxy)-3-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate 3-chloro-5-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate 3-bromo-5-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate 5-chloro-2-hydroxy-3-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate 5-bromo-2-hydroxy-3-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate 5-chloro-2-(isobutyryloxy)-3-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate 5-bromo-2-(isobutyryloxy)-3-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate 3-chloro-5-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl nicotinate 3-bromo-5-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl nicotinate 5-chloro-2-hydroxy-3-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl nicotinate 5-bromo-2-hydroxy-3-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl nicotinate 5-chloro-2-(isobutyryloxy)-3-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl nicotinate 5-bromo-2-(isobutyryloxy)-3-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl nicotinate 4-(2-(3-isobutryloxy-5-chlorobenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate 4-(2-(3-isobutryloxy-5-bromobenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate 4-(2-(3-isobutryloxy-5-chloro-2-hydroxybenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate 4-(2-(3-isobutryloxy-5-bromo-2-hydroxybenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate 4-(2-(2,3-bis(isobutryloxy)-5-chlorobenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate 4-(2-(2,3-bis(isobutryloxy)-5-chlorobenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate 4-(2-(3-chloro-5-hydroxybenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate 4-(2-(3-bromo-5-hydroxybenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate 4-(2-(5-chloro-2,3-dihydroxybenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate 4-(2-(5-bromo-2,3-dihydroxybenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate 4-(2-(2-isobutryloxy-5-chloro-3-hydroxybenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate 4-(2-(2-isobutryloxy-5-bromo-3-hydroxybenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate N-(3-chlorobenzylidene)-2,4-dichlorobenzenamine N-(3-bromobenzylidene)-2,4-dichlorobenzenamine 4-chloro-2-((2,4-dichlorophenylimino)methyl)phenol 4-bromo-2-((2,4-dichlorophenylimino)methyl)phenol 4-chloro-2-((2,4-dichlorophenylimino)methyl)phenyl isobutyrate 4-bromo-2-((2,4-dichlorophenylimino)methyl)phenyl isobutyrate 3-chloro-5-((2,4-dichlorophenylimino)methyl)phenyl 4-methylbenzoate 3-bromo-5-((2,4-dichlorophenylimino)methyl)phenyl 4-methylbenzoate 5-chloro-3-((2,4-dichlorophenylimino)methyl)-2-hydroxyphenyl 4-methylbenzoate 5-bromo-3-((2,4-dichlorophenylimino)methyl)-2-hydroxyphenyl 4-methylbenzoate 5-chloro-3-((2,4-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate 5-bromo-3-((2,4-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate 3-chloro-5-((2,4-dichlorophenylimino)methyl)phenyl 3-methylbenzoate 3-bromo-5-((2,4-dichlorophenylimino)methyl)phenyl 3-methylbenzoate 5-chloro-3-((2,4-dichlorophenylimino)methyl)-2-hydroxyphenyl 3-methylbenzoate 5-bromo-3-((2,4-dichlorophenylimino)methyl)-2-hydroxyphenyl 3-methylbenzoate 5-chloro-3-((2,4-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate 5-bromo-3-((2,4-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate 3-chloro-5-((2,4-dichlorophenylimino)methyl)phenyl nicotinate 3-bromo-5-((2,4-dichlorophenylimino)methyl)phenyl nicotinate 5-chloro-3-((2,4-dichlorophenylimino)methyl)-2-hydroxyphenyl nicotinate 5-bromo-3-((2,4-dichlorophenylimino)methyl)-2-hydroxyphenyl nicotinate 5-chloro-3-((2,4-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate 5-bromo-3-((2,4-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate 3-chloro-5-((2,4-dichlorophenylimino)methyl)phenyl isobutyrate 3-bromo-5-((2,4-dichlorophenylimino)methyl)phenyl isobutyrate 5-chloro-3-((2,4-dichlorophenylimino)methyl)-2-hydroxyphenyl isobutyrate 5-bromo-3-((2,4-dichlorophenylimino)methyl)-2-hydroxyphenyl isobutyrate N-(2,3-bis(isobutryloxy)-5-chlorobenzylidene)-2,4-dichlorobenzenamine N-(2,3-bis(isobutryloxy)-5-bromobenzylidene)-2,4-dichlorobenzenamine 3-chloro-5-((2,4-dichlorophenylimino)methyl)phenol 3-bromo-5-((2,4-dichlorophenylimino)methyl)phenol 5-chloro-3-((2,4-dichlorophenylimino)methyl)benzene-1,2-diol 5-bromo-3-((2,4-dichlorophenylimino)methyl)benzene-1,2-diol 4-chloro-2-((2,4-dichlorophenylimino)methyl)-6-hydroxyphenyl isobutyrate 4-bromo-2-((2,4-dichlorophenylimino)methyl)-6-hydroxyphenyl isobutyrate N-(3-chlorobenzylidene)-4-chlorobenzenamine N-(3-bromobenzylidene)-4-chlorobenzenamine 4-chloro-2-((4-chlorophenylimino)methyl)phenol 4-bromo-2-((4-chlorophenylimino)methyl)phenol 4-chloro-2-((4-chlorophenylimino)methyl)phenyl isobutyrate 4-bromo-2-((4-chlorophenylimino)methyl)phenyl isobutyrate 3-chloro-5-((4-chlorophenylimino)methyl)phenyl 4-methylbenzoate 3-bromo-5-((4-chlorophenylimino)methyl)phenyl 4-methylbenzoate 5-chloro-3-((4-chlorophenylimino)methyl)-2-hydroxyphenyl 4-methylbenzoate 5-bromo-3-((4-chlorophenylimino)methyl)-2-hydroxyphenyl 4-methylbenzoate 5-chloro-3-((4-chlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate 5-bromo-3-((4-chlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate 3-chloro-5-((4-chlorophenylimino)methyl)phenyl 3-methylbenzoate 3-bromo-5-((4-chlorophenylimino)methyl)phenyl 3-methylbenzoate 5-chloro-3-((4-chlorophenylimino)methyl)-2-hydroxyphenyl 3-methylbenzoate 5-bromo-3-((4-chlorophenylimino)methyl)-2-hydroxyphenyl 3-methylbenzoate 5-chloro-3-((4-chlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate 5-bromo-3-((4-chlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate 3-chloro-5-((4-chlorophenylimino)methyl)phenyl nicotinate 3-bromo-5-((4-chlorophenylimino)methyl)phenyl nicotinate 5-chloro-3-((4-chlorophenylimino)methyl)-2-hydroxyphenyl nicotinate 5-bromo-3-((4-chlorophenylimino)methyl)-2-hydroxyphenyl nicotinate 5-chloro-3-((4-chlorophenylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate 5-bromo-3-((4-chlorophenylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate 3-chloro-5-((4-chlorophenylimino)methyl)phenyl isobutyrate 3-bromo-5-((4-chlorophenylimino)methyl)phenyl isobutyrate 5-chloro-3-((4-chlorophenylimino)methyl)-2-hydroxyphenyl isobutyrate 5-bromo-3-((4-chlorophenylimino)methyl)-2-hydroxyphenyl isobutyrate N-(2,3-bis(isobutryloxy)-5-chlorobenzylidene)-4-chlorobenzenamine N-(2,3-bis(isobutryloxy)-5-bromobenzylidene)-4-chlorobenzenamine 3-chloro-5-((4-chlorophenylimino)methyl)phenol 3-bromo-5-((4-chlorophenylimino)methyl)phenol 5-chloro-3-((4-chlorophenylimino)methyl)benzene-1,2-diol 5-bromo-3-((4-chlorophenylimino)methyl)benzene-1,2-diol 4-chloro-2-((4-chlorophenylimino)methyl)-6-hydroxyphenyl isobutyrate 4-bromo-2-((4-chlorophenylimino)methyl)-6-hydroxyphenyl isobutyrate N-(3-chlorobenzylidene)-2,3-dichlorobenzenamine N-(3-bromobenzylidene)-2,3-dichlorobenzenamine 4-chloro-2-((2,3-dichlorophenylimino)methyl)phenol 4-bromo-2-((2,3-dichlorophenylimino)methyl)phenol 4-chloro-2-((2,3-dichlorophenylimino)methyl)phenyl isobutyrate 4-bromo-2-((2,3-dichlorophenylimino)methyl)phenyl isobutyrate 3-chloro-5-((2,3-dichlorophenylimino)methyl)phenyl 4-methylbenzoate 3-bromo-5-((2,3-dichlorophenylimino)methyl)phenyl 4-methylbenzoate 5-chloro-3-((2,3-dichlorophenylimino)methyl)-2-hydroxyphenyl 4-methylbenzoate 5-bromo-3-((2,3-dichlorophenylimino)methyl)-2-hydroxyphenyl 4-methylbenzoate 5-chloro-3-((2,3-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate 5-bromo-3-((2,3-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate 3-chloro-5-((2,3-dichlorophenylimino)methyl)phenyl 3-methylbenzoate 3-bromo-5-((2,3-dichlorophenylimino)methyl)phenyl 3-methylbenzoate 5-chloro-3-((2,3-dichlorophenylimino)methyl)-2-hydroxyphenyl 3-methylbenzoate 5-bromo-3-((2,3-dichlorophenylimino)methyl)-2-hydroxyphenyl 3-methylbenzoate 5-chloro-3-((2,3-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate 5-bromo-3-((2,3-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate 3-chloro-5-((2,3-dichlorophenylimino)methyl)phenyl nicotinate 3-bromo-5-((2,3-dichlorophenylimino)methyl)phenyl nicotinate 5-chloro-3-((2,3-dichlorophenylimino)methyl)-2-hydroxyphenyl nicotinate 5-bromo-3-((2,3-dichlorophenylimino)methyl)-2-hydroxyphenyl nicotinate 5-chloro-3-((2,3-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate 5-bromo-3-((2,3-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate 3-chloro-5-((2,3-dichlorophenylimino)methyl)phenyl isobutyrate 3-bromo-5-((2,3-dichlorophenylimino)methyl)phenyl isobutyrate 5-chloro-3-((2,3-dichlorophenylimino)methyl)-2-hydroxyphenyl isobutyrate 5-bromo-3-((2,3-dichlorophenylimino)methyl)-2-hydroxyphenyl isobutyrate N-(2,3-bis(isobutryloxy)-5-chlorobenzylidene)-2,3-dichlorobenzenamine N-(2,3-bis(isobutryloxy)-5-bromobenzylidene)-2,3-dichlorobenzenamine 3-chloro-5-((2,3-dichlorophenylimino)methyl)phenol 3-bromo-5-((2,3-dichlorophenylimino)methyl)phenol 5-chloro-3-((2,3-dichlorophenylimino)methyl)benzene-1,2-diol 5-bromo-3-((2,3-dichlorophenylimino)methyl)benzene-1,2-diol 4-chloro-2-((2,3-dichlorophenylimino)methyl)-6-hydroxyphenyl isobutyrate 4-bromo-2-((2,3-dichlorophenylimino)methyl)-6-hydroxyphenyl isobutyrate N-(3-chlorobenzylidene)-3,5-dichlorobenzenamine N-(3-bromobenzylidene)-3,5-dichlorobenzenamine 4-chloro-2-((3,5-dichlorophenylimino)methyl)phenol 4-bromo-2-((3,5-dichlorophenylimino)methyl)phenol 4-chloro-2-((3,5-dichlorophenylimino)methyl)phenyl isobutyrate 4-bromo-2-((3,5-dichlorophenylimino)methyl)phenyl isobutyrate 3-chloro-5-((3,5-dichlorophenylimino)methyl)phenyl 4-methylbenzoate 3-bromo-5-((3,5-dichlorophenylimino)methyl)phenyl 4-methylbenzoate 5-chloro-3-((3,5-dichlorophenylimino)methyl)-2-hydroxyphenyl 4-methylbenzoate 5-bromo-3-((3,5-dichlorophenylimino)methyl)-2-hydroxyphenyl 4-methylbenzoate 5-chloro-3-((3,5-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate 5-bromo-3-((3,5-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate 5-chloro-3-((3,5-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate 5-bromo-3-((3,5-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate 5-chloro-3-((3,5-dichlorophenylimino)methyl)-2-hydroxyphenyl 3-methylbenzoate 5-bromo-3-((3,5-dichlorophenylimino)methyl)-2-hydroxyphenyl 3-methylbenzoate 5-chloro-3-((3,5-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate 5-bromo-3-((3,5-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate 3-chloro-5-((3,5-dichlorophenylimino)methyl)phenyl nicotinate 3-bromo-5-((3,5-dichlorophenylimino)methyl)phenyl nicotinate 5-chloro-3-((3,5-dichlorophenylimino)methyl)-2-hydroxyphenyl nicotinate 5-bromo-3-((3,5-dichlorophenylimino)methyl)-2-hydroxyphenyl nicotinate 5-chloro-3-((3,5-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate 5-bromo-3-((3,5-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate 3-chloro-5-((3,5-dichlorophenylimino)methyl)phenyl isobutyrate 3-bromo-5-((3,5-dichlorophenylimino)methyl)phenyl isobutyrate 5-chloro-3-((3,5-dichlorophenylimino)methyl)-2-hydroxyphenyl isobutyrate 5-bromo-3-((3,5-dichlorophenylimino)methyl)-2-hydroxyphenyl isobutyrate N-(2,3-bis(isobutryloxy)-5-chlorobenzylidene)-3,5-dichlorobenzenamine N-(2,3-bis(isobutryloxy)-5-bromobenzylidene)-3,5-dichlorobenzenamine 3-chloro-5-((3,5-dichlorophenylimino)methyl)phenol 3-bromo-5-((3,5-dichlorophenylimino)methyl)phenol 5-chloro-3-((3,5-dichlorophenylimino)methyl)benzene-1,2-diol 5-bromo-3-((3,5-dichlorophenylimino)methyl)benzene-1,2-diol 4-chloro-2-((3,5-dichlorophenylimino)methyl)-6-hydroxyphenyl isobutyrate 4-bromo-2-((3,5-dichlorophenylimino)methyl)-6-hydroxyphenyl isobutyrate N-(3-chlorobenzylidene)-2-phenylethanamine N-(3-bromobenzylidene)-2-phenylethanamine 4-chloro-2-((phenethylimino)methyl)phenol 4-bromo-2-((phenethylimino)methyl)phenol 4-chloro-2-((phenethylimino)methyl)phenyl isobutyrate 4-bromo-2-((phenethylimino)methyl)phenyl isobutyrate 3-chloro-5-((phenethylimino)methyl)phenyl 4-methylbenzoate 3-bromo-5-((phenethylimino)methyl)phenyl 4-methylbenzoate 5-chloro-2-hydroxy-3-((phenethylimino)methyl)phenyl 4-methylbenzoate 5-bromo-2-hydroxy-3-((phenethylimino)methyl)phenyl 4-methylbenzoate 5-chloro-2-(isobutyryloxy)-3-((phenethylimino)methyl)phenyl 4-methylbenzoate 5-bromo-2-(isobutyryloxy)-3-((phenethylimino)methyl)phenyl 4-methylbenzoate 3-chloro-5-((phenethylimino)methyl)phenyl 3-methylbenzoate 3-bromo-5-((phenethylimino)methyl)phenyl 3-methylbenzoate 5-chloro-2-hydroxy-3-((phenethylimino)methyl)phenyl 3-methylbenzoate 5-bromo-2-hydroxy-3-((phenethylimino)methyl)phenyl 3-methylbenzoate 5-chloro-2-(isobutyryloxy)-3-((phenethylimino)methyl)phenyl 3-methylbenzoate 5-bromo-2-(isobutyryloxy)-3-((phenethylimino)methyl)phenyl 3-methylbenzoate 3-chloro-5-((phenethylimino)methyl)phenyl nicotinate 3-bromo-5-((phenethylimino)methyl)phenyl nicotinate 5-chloro-2-hydroxy-3-((phenethylimino)methyl)phenyl nicotinate 5-bromo-2-hydroxy-3-((phenethylimino)methyl)phenyl nicotinate 5-chloro-2-(isobutyryloxy)-3-((phenethylimino)methyl)phenyl nicotinate 5-bromo-2-(isobutyryloxy)-3-((phenethylimino)methyl)phenyl nicotinate 3-chloro-5-((phenethylimino)methyl)phenyl isobutyrate 3-bromo-5-((phenethylimino)methyl)phenyl isobutyrate 5-chloro-2-hydroxy-3-((phenethylimino)methyl)phenyl isobutyrate 5-bromo-2-hydroxy-3-((phenethylimino)methyl)phenyl isobutyrate N-(2,3-bis(isobutryloxy)-5-chlorobenzylidene)-2-phenylethanamine N-(2,3-bis(isobutryloxy)-5-bromobenzylidene)-2-phenylethanamine 3-chloro-5-((phenethylimino)methyl)phenol 3-bromo-5-((phenethylimino)methyl)phenol 5-chloro-3-((phenethylimino)methyl)benzene-1,2-diol 5-bromo-3-((phenethylimino)methyl)benzene-1,2-diol 4-chloro-2-hydroxy-6-((phenethylimino)methyl)phenyl isobutyrate 4-bromo-2-hydroxy-6-((phenethylimino)methyl)phenyl isobutyrate N-(3-chlorobenzylidene)-4-((diethylamino)methyl)benzenamine N-(3-bromobenzylidene)-4-((diethylamino)methyl)benzenamine 4-chloro-2-((4-((diethylamino)methyl)phenylimino)methyl)phenol 4-bromo-2-((4-((diethylamino)methyl)phenylimino)methyl)phenol 4-chloro-2-((4-((diethylamino)methyl)phenylimino)methyl)phenyl isobutyrate 4-bromo-2-((4-((diethylamino)methyl)phenylimino)methyl)phenyl isobutyrate 3-chloro-5-((4-((diethylamino)methyl)phenylimino)methyl)phenyl 4-methylbenzoate 3-bromo-5-((4-((diethylamino)methyl)phenylimino)methyl)phenyl 4-methylbenzoate 5-chloro-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-hydroxyphenyl 4-methylbenzoate 5-bromo-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-hydroxyphenyl 4-methylbenzoate 5-chloro-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate 5-bromo-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate 3-chloro-5-((4-((diethylamino)methyl)phenylimino)methyl)phenyl 3-methylbenzoate 3-bromo-5-((4-((diethylamino)methyl)phenylimino)methyl)phenyl 3-methylbenzoate 5-chloro-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-hydroxyphenyl 3-methylbenzoate 5-bromo-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-hydroxyphenyl 3-methylbenzoate 5-chloro-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate 5-bromo-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate 3-chloro-5-((4-((diethylamino)methyl)phenylimino)methyl)phenyl nicotinate 3-bromo-5-((4-((diethylamino)methyl)phenylimino)methyl)phenyl nicotinate 5-chloro-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-hydroxyphenyl nicotinate 5-bromo-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-hydroxyphenyl nicotinate 5-chloro-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate 5-bromo-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate 3-chloro-5-((4-((diethylamino)methyl)phenylimino)methyl)phenyl isobutyrate 3-bromo-5-((4-((diethylamino)methyl)phenylimino)methyl)phenyl isobutyrate 5-chloro-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-hydroxyphenyl isobutyrate 5-bromo-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-hydroxyphenyl isobutyrate N-(2,3-bis(isobutryloxy)-5-chlorobenzylidene)-4-((diethylamino)methyl)benzenamine N-(2,3-bis(isobutryloxy)-5-bromobenzylidene)-4-((diethylamino)methyl)benzenamine 3-chloro-5-((4-((diethylamino)methyl)phenylimino)methyl)phenol 3-bromo-5-((4-((diethylamino)methyl)phenylimino)methyl)phenol 5-chloro-3-((4-((diethylamino)methyl)phenylimino)methyl)benzene-1,2-diol 5-bromo-3-((4-((diethylamino)methyl)phenylimino)methyl)benzene-1,2-diol 4-chloro-2-((4-((diethylamino)methyl)phenylimino)methyl)-6-hydroxyphenyl isobutyrate 4-bromo-2-((4-((diethylamino)methyl)phenylimino)methyl)-6-hydroxyphenyl isobutyrate N-(3-chlorobenzylidene)pyridin-3-amine N-(3-bromobenzylidene)pyridin-3-amine 4-chloro-2-((pyridin-3-ylimino)methyl)phenol 4-bromo-2-((pyridin-3-ylimino)methyl)phenol 4-chloro-2-((pyridin-3-ylimino)methyl)phenyl isobutyrate 4-bromo-2-((pyridin-3-ylimino)methyl)phenyl isobutyrate 3-chloro-5-((pyridin-3-ylimino)methyl)phenyl 4-methylbenzoate 3-bromo-5-((pyridin-3-ylimino)methyl)phenyl 4-methylbenzoate 5-chloro-2-hydroxy-3-((pyridin-3-ylimino)methyl)phenyl 4-methylbenzoate 5-bromo-2-hydroxy-3-((pyridin-3-ylimino)methyl)phenyl 4-methylbenzoate 5-chloro-2-(isobutyryloxy)-3-((pyridin-3-ylimino)methyl)phenyl 4-methylbenzoate 5-bromo-2-(isobutyryloxy)-3-((pyridin-3-ylimino)methyl)phenyl 4-methylbenzoate 3-chloro-5-((pyridin-3-ylimino)methyl)phenyl 3-methylbenzoate 3-bromo-5-((pyridin-3-ylimino)methyl)phenyl 3-methylbenzoate 5-chloro-2-hydroxy-3-((pyridin-3-ylimino)methyl)phenyl 3-methylbenzoate 5-bromo-2-hydroxy-3-((pyridin-3-ylimino)methyl)phenyl 3-methylbenzoate 5-chloro-2-(isobutyryloxy)-3-((pyridin-3-ylimino)methyl)phenyl 3-methylbenzoate 5-bromo-2-(isobutyryloxy)-3-((pyridin-3-ylimino)methyl)phenyl 3-methylbenzoate 3-chloro-5-((pyridin-3-ylimino)methyl)phenyl nicotinate 3-bromo-5-((pyridin-3-ylimino)methyl)phenyl nicotinate 5-chloro-2-hydroxy-3-((pyridin-3-ylimino)methyl)phenyl nicotinate 5-bromo-2-hydroxy-3-((pyridin-3-ylimino)methyl)phenyl nicotinate 5-chloro-2-(isobutyryloxy)-3-((pyridin-3-ylimino)methyl)phenyl nicotinate 5-bromo-2-(isobutyryloxy)-3-((pyridin-3-ylimino)methyl)phenyl nicotinate 3-chloro-5-((pyridin-3-ylimino)methyl)phenyl isobutyrate 3-bromo-5-((pyridin-3-ylimino)methyl)phenyl isobutyrate 5-chloro-2-hydroxy-3-((pyridin-3-ylimino)methyl)phenyl isobutyrate 5-bromo-2-hydroxy-3-((pyridin-3-ylimino)methyl)phenyl isobutyrate N-(2,3-bis(isobutryloxy)-5-chlorobenzylidene)pyridin-3-amine N-(2,3-bis(isobutryloxy)-5-bromobenzylidene)pyridin-3-amine 3-chloro-5-((pyridin-3-ylimino)methyl)phenol 3-bromo-5-((pyridin-3-ylimino)methyl)phenol 5-chloro-3-((pyridin-3-ylimino)methyl)benzene-1,2-diol 5-bromo-3-((pyridin-3-ylimino)methyl)benzene-1,2-diol 4-chloro-2-hydroxy-6-((pyridin-3-ylimino)methyl)phenyl isobutyrate 4-bromo-2-hydroxy-6-((pyridin-3-ylimino)methyl)phenyl isobutyrate 3-(3-chlorobenzylideneamino)benzoic acid 3-(3-bromobenzylideneamino)benzoic acid 3-(5-chloro-2-hydroxybenzylideneamino)benzoic acid 3-(5-bromo-2-hydroxybenzylideneamino)benzoic acid 3-(5-chloro-2-(isobutyryloxy)benzylideneamino)benzoic acid 3-(5-bromo-2-(isobutyryloxy)benzylideneamino)benzoic acid 3-(3-chloro-5-(4-methylbenzoyloxy)benzylideneamino)benzoic acid 3-(3-bromo-5-(4-methylbenzoyloxy)benzylideneamino)benzoic acid 3-(5-chloro-2-hydroxy-3-(4-methylbenzoyloxy)benzylideneamino)benzoic acid 3-(5-bromo-2-hydroxy-3-(4-methylbenzoyloxy)benzylideneamino)benzoic acid 3-(5-chloro-2-(isobutyryloxy)-3-(4-methylbenzoyloxy)benzylideneamino)benzoic acid 3-(5-bromo-2-(isobutyryloxy)-3-(4-methylbenzoyloxy)benzylideneamino)benzoic acid 3-(3-chloro-5-(3-methylbenzoyloxy)benzylideneamino)benzoic acid 3-(3-bromo-5-(3-methylbenzoyloxy)benzylideneamino)benzoic acid 3-(5-chloro-2-hydroxy-3-(3-methylbenzoyloxy)benzylideneamino)benzoic acid 3-(5-bromo-2-hydroxy-3-(3-methylbenzoyloxy)benzylideneamino)benzoic acid 3-(5-chloro-2-(isobutyryloxy)-3-(3-methylbenzoyloxy)benzylideneamino)benzoic acid 3-(5-bromo-2-(isobutyryloxy)-3-(3-methylbenzoyloxy)benzylideneamino)benzoic acid 3-(3-chloro-5-(nicotinoyloxy)benzylideneamino)benzoic acid 3-(3-bromo-5-(nicotinoyloxy)benzylideneamino)benzoic acid 3-(5-chloro-2-hydroxy-3-(nicotinoyloxy)benzylideneamino)benzoic acid 3-(5-bromo-2-hydroxy-3-(nicotinoyloxy)benzylideneamino)benzoic acid 3-(5-chloro-2-(isobutyryloxy)-3-(nicotinoyloxy)benzylideneamino)benzoic acid 3-(5-bromo-2-(isobutyryloxy)-3-(nicotinoyloxy)benzylideneamino)benzoic acid 3-(3-chloro-5-(isobutyryloxy)benzylideneamino)benzoic acid 3-(3-bromo-5-(isobutyryloxy)benzylideneamino)benzoic acid 3-(5-chloro-2-hydroxy-3-(isobutyryloxy)benzylideneamino)benzoic acid 3-(5-bromo-2-hydroxy-3-(isobutyryloxy)benzylideneamino)benzoic acid 3-(2,3-bis(isobutryloxy)-5-chlorobenzylideneamino)benzoic acid 3-(2,3-bis(isobutryloxy)-5-bromobenzylideneamino)benzoic acid 3-(3-chloro-5-hydroxybenzylideneamino)benzoic acid 3-(3-bromo-5-hydroxybenzylideneamino)benzoic acid 3-(5-chloro-2,3-dihydroxybenzylideneamino)benzoic acid 3-(5-bromo-2,3-dihydroxybenzylideneamino)benzoic acid 3-(5-chloro-3-hydroxy-2-(isobutyryloxy)benzylideneamino)benzoic acid, and 3-(5-bromo-3-hydroxy-2-(isobutyryloxy)benzylideneamino)benzoic acid.

5. The compound of claim 1 wherein said compound is a hydrochloride, hydrobromide, sodium, potassium or magnesium salt.

6. A method for the preparation of halogenated benzylidene derivatives of formula (I), ##STR01101## wherein X is a halogen and Y is selected from the group consisting of a hydrogen, a halogen, a hydroxyl group, a nitro group, a cyano group, a formyl group, an amino group and a sulfonyl group, and wherein the groups represented by R1 and R3 are selected from the group consisting of linear or branched, substituted or unsubstituted (C1 to C12) alkyl groups, and substituted or unsubstituted (C1 to C12) alkoxy groups, and wherein R.sub.4 is selected from the group consisting of alaninie, glycine, arginine, aspargine, cysteine, glutamic acid, glutamine, histidine, isoleucine, leucine, lysine, methionine, omithine, proline, serine, threonine, tryptophan, and tyrosine, which may be unsubstituted or substituted, and their derivatives such as ester and amides of carboxylic acid, wherein said method comprises the reaction as follows: ##STR01102##

7. A method for treating a disease or physiological condition comprising administering an effective amount of a compound of formula (I) as defined in claim 1 to a patient in need thereof, wherein the disease or physiological condition is selected from the group consisting of: an autoimmune disease, inflammation, and an immunological disease.

8. The method of claim 7 wherein the disease is multiple sclerosis.

9. The method of claim 7 wherein the disease is rheumatoid arthritis.

10. The method of claim 7 wherein the disease is rheumatoid arthritis.

11. The method of claim 7 wherein the disease is inflammation mediated by cyclooxygenase.

12. The method of claim 7 wherein the disease is inflammation mediated by cytokines.

13. The compound of claim 1 selected from the group consisting of: TABLE-US-00003 R1 = R3 = H R.sub.4 is bonded through N, R.sub.2 in cases is bonded through O S. No R4 R2 Y X IUPAC 1. H H Cl (E)-1-(3- chlorobenzylidene- amino)- 2-methylpropan-1-ol 2. H H Br (E)-1-(3- bromobenzylidene- amino)- 2-methylpropan-1-ol 3. H OH Cl (E)-4-chloro-2-((1- hydroxy-2- methylpropyl- imino)methyl)phenol 4. H OH Br (E)-4-bromo-2-((1- hydroxy-2- methylpropyl- imino)methyl)phenol 5. H Cl (E)-4-chloro-2-((1- hydroxy-2- methylpropyl- imino)meth- yl)phenyl isobutyrate 6. H Br (E)-4-bromo-2-((1- hydroxy-2- methylpropyl- imino)meth- yl)phenyl isobutyrate 7. H Cl (E)-3-chloro-5-((1- hydroxy-2- methylpropyl- imino)meth- yl)phenyl 4- methylbenzoate 8. H Br (E)-3-bromo-5-((1- hydroxy-2- methylpropyl- imino)meth- yl)phenyl 4- methylbenzoate 9. OH Cl (E)-5-chloro-2-hydroxy- 3-((1-hydroxy-2- methylpropyl- imino)meth- yl)phenyl 4- methylbenzoate 10. OH Br (E)-5-bromo-2-hydroxy- 3-((1-hydroxy-2- methylpropyl- imino)meth- yl)phenyl 4- methylbenzoate 11. Cl (E)-5-chloro-3-((1- hydroxy-2- methylpropyl- imino)meth- yl)-2- (isobutyryloxy)phenyl 4- methylbenzoate 12. Br (E)-(5-bromo-3-((1- hydroxy-2- methylpropyl- imino)meth- yl)-2- (isobutyryloxy)phenyl 4- methylbenzoate 13. H Cl (E)-3-chloro-5-((1- hydroxy-2- methylpropyl- imino)meth- yl)phenyl 3- methylbenzoate 14. H Br (E)-3-bromo-5-((1- hydroxy-2- methylpropyl- imino)meth- yl)phenyl 3- methylbenzoate 15. OH Cl (E)-5-chloro-2-hydroxy- 3-((1-hydroxy-2- methylpropyl- imino)meth- yl)phenyl 3- methylbenzoate 16. OH Br (E)-5-bromo-2-hydroxy- 3-((1-hydroxy-2- methylpropyl- imino)meth- yl)phenyl 3- methylbenzoate 17. Cl (E)-5-chloro-3-((1- hydroxy-2- methylpropyl- imino)meth- yl)-2- (isobutyryloxy)phenyl 3- methylbenzoate 18. Br (E)-5-bromo-3-((1- hydroxy-2- methylpropyl- imino)meth- yl)-2- (isobutyryloxy)phenyl 3- methylbenzoate 19. H Cl (E)-3-chloro-5-((1- hydroxy-2- methylpropyl- imino)meth- yl)phenyl nicotinate 20. H Br (E)-3-bromo-5-((1- hydroxy-2- methylpropyl- imino)meth- yl)phenyl nicotinate 21. OH Cl (E)-5-chloro-2-hydroxy- 3-((1-hydroxy-2- methylpropyl- imino)meth- yl)phenyl nicotinate 22. OH Br (E)-5-bromo-2-hydroxy- 3-((1-hydroxy-2- methylpropyl- imino)meth- yl)phenyl nicotinate 23. Cl (E)-5-chloro-3-((1- hydroxy-2- methylpropyl- imino)meth- yl)-2- (isobutyryloxy)phenyl nicotinate 24. Br (E)-5-bromo-3-((1- hydroxy-2- methylpropyl- imino)meth- yl)-2- (isobutyryloxy)phenyl nicotinate 25. H Cl (E)-3-chloro-5-((1- hydroxy-2- methylpropyl- imino)meth- yl)phenyl isobutyrate 26. H Br (E)-3-bromo-5-((1- hydroxy-2- methylpropyl- imino)meth- yl)phenyl isobutyrate 27. OH Cl (E)-5-chloro-2-hydroxy- 3-((1-hydroxy-2- methylpropyl- imino)meth- yl)phenyl isobutyrate 28. OH Br (E)-5-bromo-2-hydroxy- 3-((1-hydroxy-2- methylpropyl- imino)meth- yl)phenyl isobutyrate 29. Cl (E)-5-chloro-2- isobutroxy-3-((1- hydroxy-2- methylpropyl- imino)meth- yl)phenyl isobutyrate 30. Br (E)-5-bromo-2- isobutroxy-3-((1- hydroxy-2- methylpropyl- imino)meth- yl)phenyl isobutyrate 31. OH H Cl (E)-3-chloro-5-((1- hydroxy-2- methylpropyl- imino)meth- yl)phenol 32. OH H Br (E)-3-bromo-5-((1- hydroxy-2- mehtylpropyl- imino)meth- yl)phenol 33. OH OH Cl (E)-5-chloro-3-((1- hydroxy-2- methylpropyl- imino)meth- yl)benzene-1,2-diol 34. OH OH Br (E)-5-bromo-3-((1- hydroxy-2- methylpropyl- imino)meth- yl)benzene-1,2-diol 35. OH Cl (E)-4-chloro-2-hydroxy- 6-((1-hydroxy-2- methylpropyl- imino)meth- yl)phenyl isobutyrate 36. OH Br (E)-4-bromo-2-hydroxy- 6-((1-hydroxy-2- methylpropyl- imino)meth- yl)phenyl isobutyrate 37. H H Cl methyl 2-(3- chlorobenzyl- ideneamino)- 3-methylbutanoate 38. H H Br methyl 2-(3- bromobenzyl- ideneamino)- 3-methylbutanoate 39. H OH Cl methyl 2-(5-chloro-2- hydroxybenzyl- ideneamino)- 3-methylbutanoate 40. H OH Br methyl 2-(5-bromo-2- hydroxybenzyli- deneamino)- 3-methylbutanoate 41. H Cl methyl 2-(5-chloro-2- (isobutyryloxy)benzyl- ideneamino)-3- methylbutanoate 42. H Br methyl 2-(5-bromo-2- (isobutyrloxy)benzyl- ideneamino)-3- methylbutanoate 43. H Cl 3-chloro-5-((1-methoxy- 3-methyl-1-oxobutan-2- ylimino)methyl)phenyl 4- methylbenzoate 44. H Br 3-bromo-5-((1-methoxy- 3-methyl-1-oxobutan-2- ylimino)methyl)phenyl 4- methylbenzoate 45. OH Cl 5-chloro-2-hydroxy-3- ((1-methoxy-3-methyl-1- oxobutan-2- ylimino)methyl)phenyl 4- methylbenzoate 46. OH Br 5-bromo-2-hydroxy-3- ((1-methoxy-3-methyl-1- oxobutan-2- ylimino)methyl)phenyl 4- methylbenzoate 47. Cl 5-chloro-2- (isobutyryloxy)-3-((1- methoxy-3-methyl-1- oxobutan-2- ylimino)methyl)phenyl 4- methylbenzoate 48. Br 5-bromo-2- (isobutyryloxy)-3-((1- methoxy-3-methyl-1- oxobutan-2- ylimino)methyl)phenyl 4- methylbenzoate 49. H Cl 3-chloro-5-((1-methoxy- 3-methyl-1-oxobutan-2- ylimino)methyl)phenyl 3- methylbenzoate 50. H Br 3-bromo-5-((1-methoxy- 3-methyl-1-oxobutan-2- ylimino)methyl)phenyl 3- methylbenzoate 51. OH Cl 5-chloro-2-hydroxy-3- ((1-methoxy-3-methyl-1- oxobutan-2- ylimino)methyl)phenyl 3- methylbenzoate 52. OH Br 5-bromo-2-hydroxy-3- ((1-methoxy-3-methyl-1- oxobutan-2- ylimino)methyl)phenyl 3- methylbenzoate 53. Cl 5-chloro-2- (isobutyryloxy)-3-((1- methoxy-3-methyl-1- oxobutan-2- ylimino)methyl)phenyl 3- methylbenzoate 54. Br 5-bromo-2- (isobutyryloxy)-3-((1- methoxy-3-methyl-1- oxobutan-2- ylimino)methyl)phenyl 3- methylbenzoate 55. H Cl 3-chloro-5-((1-methoxy- 3-methyl-1-oxobutan-2- ylimino)methyl)phenyl nicotinate 56. H Br 3-bromo-5-((1-methoxy- 3-methyl-1-oxobutan-2- ylimino)methyl)phenyl nicotinate 57. OH Cl 5-chloro-2-hydroxy-3- ((1-methoxy-3-methyl-1- oxobutan-2- ylimino)methyl)phenyl nicotinate 58. OH Br 5-bromo-2-hydroxy-3- ((1-methoxy-3-methyl-1- oxobutan-2- ylimino)methyl)phenyl nicotinate 59. Cl 5-chloro-2- (isobutyryloxy)-3-((1- methoxy-3-methyl-1- oxobutan-2- ylimino)methyl)phenyl nicotinate 60. Br 5-bromo-2- (isobutyryloxy)-3-((1- methoxy-3-methyl-1- oxobutan-2- ylimino)methyl)phenyl nicotinate 61. H Cl methyl 2-(3-chloro-5- (isobutyryloxy)benzyl- ideneamino)-3- methylbutanoate 62. H Br methyl 2-(3-bromo-5- (isobutyryloxy)benzyl- ideneamino)-3- methylbutanoate 63. OH Cl methyl 2-(5-chloro-2- hydroxy-3-(iso- butyryloxy)benzylidene- amino)-3- methylbutanoate 64. OH Br methyl 2-(5-bromo-2- hydroxy-3-(iso- butyryloxy)benzylidene- amino)-3- methylbutanoate 65. Cl methyl 2-(5-chloro-2,3- bis(isobutyryl- oxy)benzyli- deneamino)-3- methylbutanoate 66. Br methyl 2-(5-bromo-2,3- bis(isobutyryl- oxy)benzyli- deneamino)-3- methylbutanoate 67. OH H Cl methyl 2-(3-chloro-5- hydroxybenzylidene- amino)-3-methylbutanoate 68. OH H Br methyl 2-(3-bromo-5- hydroxybenzylidene- amino)-3-methylbutanoate 69. OH OH Cl methyl 2-(5-chloro-2,3- dihydroxybenzyl- ideneamino)-3- methylbutanoate 70. OH OH Br methyl 2-(5-bromo-2,3- dihydroxybenzyl ideneamino)-3- methylbutanoate 71. OH Cl methyl 2-(5-chloro-3- hydroxy-2-(3-methylbut- 1-en-2-yloxy)benzyl- ideneamino)- 3-methylbutanoate 72. OH Br methyl 2-(5-bromo-3- hydroxy-2-(3-methylbut- 1-en-2-yloxy)benzyl- ideneamino)- 3-methylbutanoate 73. H H Cl 2-(3-chlorobenzyl- ideneamino)- 3-methylbutanoic acid 74. H H Br 2-(3-bromobenzyl- ideneamino)- 3-methylbutanoic acid 75. H OH Cl 2-(5-chloro-2-hydroxy- benzylideneamino)- 3-methylbutanoic acid 76. H OH Br 2-(5-bromo-2-hydroxy- benzylideneamino)- 3-methylbutanoic acid 77. H Cl 2-(5-chloro-2-(iso- butyryloxy)benzylidene- amino)-3- methylbutanoic acid 78. H Br 2-(5-bromo-2-(iso- butyryloxy)benzylidene- amino)-3- methylbutanoic acid 79. H Cl 2-(3-chloro-5-(4- methylbenzoyl- oxy)benzyl- ideneamino)-3- methylbutanoic acid 80. H Br 2-(3-bromo-5-(4- methylbenzoyl- oxy)benzyl- ideneamino)-3- methylbutanoic acid 81. OH Cl 2-(5-chloro-2-hydroxy-3- (4- methylbenzoyl- oxy)benzyl- ideneamino)-3- methylbutanoic acid 82. OH Br 2-(5-bromo-2-hydroxy-3- (4- methylbenzoyl- oxy)benzyl- ideneamino)-3- methylbutanoic acid 83. Cl 2-(5-chloro-2- (isobutyryloxy)-3-(4- methylbenzoyl- oxy)benzyl- ideneamino)-3- methylbutanoic acid 84. Br 2-(5-bromo-2- (isobutyryloxy)-3-(4- methylbenzoyl- oxy)benzyl- ideneamino)-3- methylbutanoic acid 85. H Cl 2-(3-chloro-5-(3- methylbenzoyl- oxy)benzyl- ideneamino)-3- methylbutanoic acid 86. H Br 2-(3-bromo-5-(3- methylbenzoyl- oxy)benzyl- ideneamino)-3- methylbutanoic acid 87. OH Cl 2-(5-chloro-2-hydroxy-3- (3- methylbenzoyl- oxy)benzyl- ideneamino)-3- methylbutanoic acid 88. OH Br 2-(5-bromo-2-hydroxy-3- (3- methylbenzoyl- oxy)benzyl- ideneamino)-3- methylbutanoic acid 89. Cl 2-(5-chloro-2- (isobutyryloxy)-3-(3- methylbenzoyl- oxy)benzyl- ideneamino)-3- methylbutanoic acid 90. Br 2-(5-bromo-2- (isobutyryloxy)-3-(3- methylbenzoyl- oxy)benzyl- ideneamino)-3- methylbutanoic acid 91. H Cl 2-(3-chloro-5-(nico- tinoyloxy)benzylidene- amino)-3- methylbutanoic acid 92. H Br 2-(3-bromo-5-(nico- tinoyloxy)benzylidene- amino)-2- methylbutanoic acid 93. OH Cl 2-(5-chloro-2-hydroxy-3- (nicotinoyl- oxy)benzylidne- amino)-3- methybutanoic acid 94. OH Br 2-(5-bromo-2-hydroxy-3- (nicotinoyloxy)benzyl- ideneamino)-3- methylbutanoic acid 95. Cl 2-(5-chloro-2- (isobutyryloxy)-3-(nico- tinoyloxy)benzylidene- amino)-3- methylbutanoic acid 96. Br 2-(5-bromo-2- (isobutyryloxy)-3- (nicotinoyl- oxy)benzylidne- amino)-3- methylbutanoic acid 97. H Cl 2-(3-chloro-5-(iso- butyryloxy)benzylidene- amino)-3- methylbutanoic acid 98. H Br 2-(3-bromo-5-(iso- butyryloxy)benzylidene- amino)-3- methylbutanoic acid 99. OH Cl 2-(5-chloro-2-hydroxy-3- (isobutyryloxy)benzyl- ideneamino)-3- methylbutanoic acid 100. OH Br 2-(5-bromo-2-hydroxy-3- (isobutyryl- oxy)benzylidne- amino)-3- methylbutanoic acid 101. Cl 2-(5-chloro-2,3- bis(isobutyryl- oxy)benzyli- deneamino)-3- methylbutanoic acid 102. Br 2-(5-bromo-2,3- bis(isobutyryl- oxy)benzyli- deneamino)-3- methylbutanoic acid 103. OH H Cl 2-(3-chloro-5-hydroxy- benzylideneamino)- 3-methylbutanoic acid 104. OH H Br 2-(3-bromo-5-hydroxy- benzylideneamino)- 3-methylbutanoic acid 105. OH OH Cl 2-(5-chloro-2,3- dihydroxybenzyl- ideneami- no)-3-methylbutanoic acid 106. OH OH Br 2-(5-bromo-2,3- dihydroxybenzyl- ideneami- no)-3-methylbutanoic acid 107. OH Cl 2-(5-chloro-3-hydroxy-2- (isobutyryloxy)benzyl- ideneamino)-3- methylbutanoic acid 108. OH Br 2-(5-bromo-3-hydroxy-2- (isobutyryloxy)benzyl- ideneamino)-3- methylbutanoic acid 109. H H Cl methyl 2-(3- chlorobenzyl- ideneamino)- 3-(4- hydroxyphenyl)pro- panoate 110. H H Br methyl 2-(3- bromobenzyl- ideneamino)- 3-(4- hydroxyphenyl)pro- panoate 111. H OH Cl methyl 2-(5-chloro-2- hydroxybenzylidene- amino)-3-(4- hydroxyphenyl)pro- panoate 112. H OH Br methyl 2-(5-bromo-2- hydroxybenzylidene- amino)-3-(4- hydroxyphenyl)pro- panoate 113. H Cl methyl 2-(2-isobutricoxy- 5-chlorobenzyl- ideneamino)- 3-(4- hydroxyphenyl)pro- panoate 114. H Br methyl 2-(2-isobutricoxy- 5-bromo- benzylideneamino)- 3-(4- hydroxyphenyl)pro- panoate 115. H Cl 3-chloro-5-((3-(4- hydroxyphenyl)-1- methoxy-1-oxopropan-2- ylimino)methyl)phenyl 4- methylbenzoate 116. H Br 3-bromo-5-((3-(4- hydroxyphenyl)-1- methoxy-1-oxopropan-2- ylimino)methyl)phenyl 4- methylbenzoate 117. OH Cl 5-chloro-2-hydroxy-3- ((3-(4-hydroxyphenyl)-1- methoxy-1-oxopropan-2- ylimino)methyl)phenyl 4- methylbenzoate 118. H Br 5-bromo-2-hydroxy-3- ((3-(4-hydroxyphenyl)-1- methoxy-1-oxopropan-2- ylimino)methyl)phenyl 4- methylbenzoate 119. Cl 5-chloro-3-((3-(4- hydroxyphenyl)-1- methoxy-1-oxopropan-2- ylimino)methyl)-2- (isobutyryloxy)phenyl 4- methylbenzoate 120. Br 5-bromo-3-((3-(4- hydroxyphenyl)-1- methoxy-1-oxopropan-2- ylimino)methyl)-2- (isobutyryloxy)phenyl 4- methylbenzoate 121. H Cl 3-chloro-5-((3-(4- hydroxyphenyl)-1- methoxy-1-oxopropan-2- ylimino)methyl)phenyl 3- methylbenzoate 122. H Br 3-bromo-5-((3-(4- hydroxyphenyl)-1- methoxy-1-oxopropan-2- ylimino)methyl)phenyl 3- methylbenzoate 123. OH Cl 5-chloro-2-hydroxy-3- ((3-(4-hydroxyphenyl)-1- methoxy-1-oxopropan-2- ylimino)methyl)phenyl 3- methylbenzoate 124. OH Br 5-bromo-2-hydroxy-3- ((3-(4-hydroxyphenyl)-1- methoxy-1-oxopropan-2- ylimino)methyl)phenyl 3- methylbenzoate 125. Cl 5-chloro-3-((3-(4- hydroxyphenyl)-1- methoxy-1-oxopropan-2- ylimino)methyl)-2- (isobutyryloxy)phenyl 3- methylbenzoate 126. Br 5-bromo-3-((3-(4- hydroxyphenyl)-1- methoxy-1-oxopropan-2- ylimino)methyl)-2- (isobutyryloxy)phenyl 3- methylbenzoate 127. H Cl 3-chloro-5-((3-(4- hydroxyphenyl)-1- methoxy-1-oxopropan-2- ylimino)methyl)phenyl- nicotinate 128. H Br 3-bromo-5-((3-(4- hydroxyphenyl)-1- methoxy-1-oxopropan-2- ylimino)methyl)phenyl- nicotinate 129. OH Cl 5-chloro-2-hydroxy-3- ((3-(4-hydroxyphenyl)-1- methoxy-1-oxopropan-2- ylimino)methyl)phenyl- nicotinate 130. OH Br 5-bromo-2-hydroxy-3- ((3-(4-hydroxyphenyl)-1- methoxy-1-oxopropan-2- ylimino)methyl)phenyl- nicotinate 131. Cl 5-chloro-3-((3-(4- hydroxyphenyl)-1- methoxy-1-oxopropan-2- ylimino)methyl)-2- (isobutyryloxy)phenyl- nicotinate 132. Br 5-bromo-3-((3-(4- hydroxyphenyl)-1- methoxy-1-oxopropan-2- ylimino)methyl)-2- (isobutyryloxy)phenyl- nicotinate 133. H Cl methyl 2-(3- isobutryateoxy-5- chlorobenzyl- ideneamino)- 3-(4- hydroxyphenyl)pro- panoate 134. H Br methyl 2-(3- isobutryateoxy-5- bromobenzyl- ideneamino)- 3-(4- hydroxyphenyl)pro- panoate 135. OH Cl methyl 2-(3- isoburyateoxy-5-chloro- 2-hydroxy- benzylideneamino)- 3-(4- hydroxyphenyl)propanoate 136. OH Br methyl 2-(3- isobutryateoxy-5-bromo- 2-hydroxy- benzylideneamino)- 3-(4- hydroxyphenyl)pro- panoate 137. Cl methyl 2-(5-chloro-2,3- bisisobutrateoxybenzyl- ideneamino)-3-(4- hydroxyphenyl)pro- panoate 138. Br methyl 2-(5-bromo-2,3- bisiobutrateoxy- benzylideneamino)-3-(4- hydroxyphenyl)pro- panoate 139. OH H Cl methyl 2-(3-chloro-5- hydroxybenzylidene- amino)-3-(4- hydroxyphenyl)pro- panoate 140. OH H Br methyl 2-(3-bromo-5- hydroxybenzyl- ideneamino)-3-(4- hydroxyphenyl)pro- panoate 141. OH OH Cl methyl 2-(5-chloro-2,3- dihydroxybenzyl- ideneami- no)-3-(4- hydroxyphenyl)pro- panoate 142. OH OH Br methy l2-(5-bromo-2,3- dihydroxybenzylidene- amino)-3-(4- hydroxyphenyl)pro- panoate 143. OH Cl methyl 2-(5-chloro-2- isobutrateoxy-3- hydroxybenzylidene- amino)-3-(4- hydroxyphenyl)pro- panoate 144. OH Br methyl 2-(5-bromo-2- isobutrateoxy-3- hydroxybenzylidene- amino)-3-(4- hydroxyphenyl)pro- panoate 145. H H Cl 2-(3-chloro- benzylideneamino)- 3-(4- hydroxyphenyl)propanoic acid 146. H H Br 2-(3-bromo- benzylideneamino)- 3-(4-hydroxy- phenyl)propanoic acid 147. H OH Cl 2-(5-chloro-2-hydroxy- benzylideneamino)- 3-(4-hydroxy- phenyl)propanoic acid 148. H OH Br 2-(5-bromo-2-hydroxy- benzylideneamino)- 3-(4-hydroxy- phenyl)propanoic acid 149. H Cl 2-(5-chloro-2-(iso- butyryloxy)benzylidene- amino)-3-(4-hydroxy- phenyl)propanoic acid 150. H Br 2-(5-bromo-2-(iso- butyryloxy)benzylidene- amino)-3-(4-hy- droxyphenyl)propanoic acid 151. H Cl 2-(3-chloro-5-(4- methylbenzoyl- oxy)benzyl- ideneamino)-3-(4- hydroxy- phenyl)propanoic acid 152. H Br 2-(3-bromo-5-(4- methylbenzoyl- oxy)benzyl- ideneamino)-3-(4- hydroxy- phenyl)propanoic acid 153. OH Cl 2-(5-chloro-2-hydroxy-3- (4- methylbenzoyl- oxy)benzyl- ideneamino)-3-(4- hydroxy- phenyl)propanoic acid 154. OH Br 2-(5-bromo-2-hydroxy-3- (4- methylbenzoyl- oxy)benzyl- ideneamino)-3-(4- hydroxy- phenyl)propanoic acid 155. Cl 2-(5-chloro-2- (isobutyryloxy)-3-(4- methylbenzoyl- oxy)benzyl- ideneamino)-3-(4- hydroxy- phenyl)propanoic acid 156. Br 2-(5-bromo-2- (isobutyryloxy)-3-(4- methylbenzoyl- oxy)benzyl- ideneamino)-3-(4- hydroxy- phenyl)propanoic acid 157. H Cl 2-(3-chloro-5-(3- methylbenzoyl- oxy)benzyl- ideneamino)-3-(4- hydroxy- phenyl)propanoic acid 158. H Br 2-(3-bromo-5-(3- methylbenzoyl- oxy)benzyl- ideneamino)-3-(4- hydroxy- phenyl)propanoic acid 159. OH Cl 2-(5-chloro-2-hydroxy-3- (3- methylbenzoyl- oxy)benzyl- ideneamino)-3-(4- hydroxy- phenyl)propanoic acid 160. OH Br 2-(5-bromo-2-hydroxy-3- (3- methylbenzoyl- oxy)benzyl- ideneamino)-3-(4- hydroxy- phenyl)propanoic acid 161. Cl 2-(5-chloro-2- (isobutyryloxy)-3-(3- methylbenozyl- oxy)benzyl- ideneamino)-3-(4- hydroxy- phenyl)propanoic acid 162. Br 2-(5-bromo-2- (isobutyryloxy)-3-(3- methylbenzoyl- oxy)benzyl- ideneamino)-3-(4- hydroxy- phenyl)propanoic acid 163. H Cl 2-(3-chloro-5-(nico- tinoyloxy)benzylidene- amino)-3-(4- hydroxy- phenyl)propanoic acid 164. H Br 2-(3-bromo-5-(nico- tinoyloxy)benzylidene- amino)-3-(4- hydroxy- phenyl)propanoic acid 165. OH Cl 2-(5-chloro-2-hydroxy-3- (nicotinoyloxy)benzyl- ideneamino)-3-(4- hydroxy- phenyl)propanoic aicd 166. OH Br 2-(5-bromo-2-hydroxy-3- (nicotinoyloxy)benzyl- ideneamino)-3-(4- hydroxy- phenyl)propanoic acid 167. Cl 2-(5-chloro-2- (isobutyryloxy)-3-(nico- tinoyloxy)benzylidene- amino)-3-(4- hydroxy- phenyl)propanoic acid 168. Br 2-(5-bromo-2- (isobutyryloxy)-3- (nicotinoyloxy)benzyl- ideneamino)-3-(4- hydroxy- phenyl)propanoic acid 169. H Cl 2-(3-chloro-4-(iso- butyryloxy)benzylidene- amino)-3-(4- hydroxy- phenyl)propanoic acid 170. H Br 2-(3-bromo-5-(iso- butyryloxy)benzylidine- amino)-3-(4- hydroxy- phenyl)propanoic acid 171. OH Cl 2-(5-chloro-2-hydroxy-3- (isobutyryloxy)benzyl- idineamino)-3-(4- hydroxy- phenyl)propanoic acid 172. OH Br 2-(5-bromo-2-hydroxy-3- (isobutyryloxy)benzyl- ideneamino)-3-(4- hydroxy- phenyl)propanoic acid 173. Cl 2-(5-chloro-2,3- bis(isobutyryl- oxy)benzyli- deneamino)-3-(4- hydroxyphenyl)ropanoic acid 174. Br 2-(5-bromo-2,3- bis(isobutyryl- oxy)benzyli- deneamino)-3-(4- hydroxy- phenyl)propanoic acid 175. OH H Cl 2-(3-chloro-5-hydroxy- benzylideneamino)- 3-(4-hydroxy- phenyl)propanoic acid 176. OH H Br 2-(3-bromo-5-hydroxy- benzylideneamino)- 3-(4-hydroxy- phenyl)propanoic acid 177. OH OH Cl 2-(5-chloro-2,3-di- hydroxybenzylideneami- no)-3-(4-hydroxy- phenyl)propanoic acid 178. OH OH Br 2-(5-bromo-2,3- dihydroxybenzyl- ideneami- no)-3-(4-hydroxy- phenyl)propanoic acid 179. OH Cl 2-(5-chloro-3-hydroxy-2- (isobutyryloxy)benzyl- ideneamino)-3-(4- hydroxy phenyl)propanoic acid 180. OH Br 2-(5-bromo-3-hydroxy-2- (isobutyryloxy)benzyl- ideneamino)-3-(4- hydroxy- phenyl)propanoic aicd 181. H H Cl (Z)-3-(3- chlorobenzyl- ideneamino)- 1-hydroxy-4-(4- hydroxyphenyl)butan-2- one 182. H H Br (Z)-3-(3- bromobenzyl- ideneamino)- 1-hydroxy-4-(4- hydroxyphenyl)butan-2- one 183. H OH Cl (Z)-3-(5-chloro-2-hy- droxybenzylideneamino)- 1-hydroxy-4-(4- hydroxyphenyl)butan-2- one 184. H OH Br (Z)-3-(5-bromo-2-hy- droxybenzylideneamino)- 1-hydroxy-4-(4- hydroxyphenyl)butan-2- one 185. H Cl (Z)-4-chloro2-((4- hydroxy-1-(4- hydroxyphenyl)-3- oxobutan-2- ylimino)methyl)phenyl- isobutyrate 186. H Br (Z)-4-bromo-2-((4- hydroxy-1-(4- hydroxyphenyl)-3- oxobutan-2- ylimino)methyl)phenyl- isobutyrate 187. H Cl (Z)-3-chloro-5-((4- hydroxy-1-(4- hydroxyphenyl)-3- oxobutan-2- ylimino)meth- yl)phenyl 4- methylbenzoate 188. H Br (Z)-3-bromo-5-((4- hydroxy-1-(4- hydroxyphenyl)-3- oxobutan-2- ylimino)meth- yl)phenyl 4- methylbenzoate 189. OH Cl (Z)-5-chloro-2-hydroxy- 3-((4-hydroxy-1-(4- hydroxyphenyl)-3- oxobutan-2-yl- imino)methyl)phenyl 4- methylbenzoate 190. OH Br (Z)-5-bromo-2-hydroxy- 3-((4-hydroxy-1-(4- hydroxyphenyl)-3- oxobutan-2-yl- imino)methyl)phenyl 4- methylbenzoate 191. Cl (Z)-5-chloro-3-((4- hydroxy-1-(4- hydroxyphenyl)-3- oxobutan-2- ylimino)methyl)-2- (isobutyryloxy)phenyl 4- methylbenzoate 192. Br (Z)-5-bromo-3-((4- hydroxy-1-(4- hydroxyphenyl)-3- oxobutan-2- ylimino)methyl)-2- (isobutyryloxy)phenyl 4- methylbenzoate 193. H Cl (Z)-3-chloro-5-((4- hydroxy-1-(4- hydroxypehnyl)-3- oxobutan-2-yl- imino)methyl)phenyl 3- methylbenzoate 194. H Br (Z)-3-bromo-5-((4- hydroxy-1-(4- hydroxyphenyl)-3- oxobutan-2-yl- imino)methyl)phenyl 3- methylbenzoate 195. OH Cl 5-chloro-2-hydroxy-3- ((4-hydroxy-1-(4- hydroxyphenyl)-3- oxobutan-2-yl- imino)methyl)phenyl 3- methylbenzoate 196. OH Br 5-bromo-2-hydroxy-3- ((4-hydroxy-1-(4- hydroxyphenyl)-3- oxobutan-2-yl- imino)methyl)phenyl 3- methylbenzoate 197. Cl 5-chloro-3-((4-hydroxy- 1-(4-hydroxyphenyl)-3- oxobutan-2- ylimino)methyl)-2- (isobutyryloxy)phenyl 3- methylbenzoate 198. Br 5-bromo-3-((4-hydroxy- 1-(4-hydroxyphenyl)-3- oxobutan-2- ylimino)methyl)-2- (isobutyryloxy)phenyl 3- methylbenzoate 199. H Cl 3-chloro-5-((4-hydroxy- 1-(4-hydroxyphenyl)-3- oxobutan-2- ylmino)methyl)phenyl nicotinate 200. H Br 3-bromo-5-((4-hydroxy- 1-(4-hydroxyphenyl)-3- oxobutan-2- ylimino)methyl)phenyl nicotinate 201. OH Cl 5-chloro-2-hydroxy-3- ((4-hydroxy-1-(4- hydroxyphenyl)-3- oxobutan-2- ylimino)methyl)phenyl nicotinate 202. OH Br 5-bromo-2-hydroxy-3- ((4-hydroxy-1-(4- hydroxyphenyl)-3- oxobutan-2- ylimino)methyl)phenyl nicotinate 203. Cl 5-chloro-3-((4-hydroxy- 1-(4-hydroxyphenyl)-3- oxobutan-2- ylimino)methyl)-2- (isobutyryloxy)phenyl nicotinate 204. Br 5-bromo-3-((4-hydroxy- 1-(4-hydroxyphenyl)-3- oxobutan-2- ylimino)methyl)-2- (isobutyryloxy)phenyl nicotinate 205. H Cl 3-chloro-5-((4-hydroxy- 1-(4-hydroxyphenyl)-3- oxobutan-2- ylimino)methyl)phenyl isobutyrate 206. H Br 3-bromo-5-((4-hydroxy- 1-(4-hydroxyphenyl)-3- oxobutan-2- ylimino)methyl)phenyl isobutyrate 207. OH Cl 5-chloro-2-hydroxy-3- ((4-hydroxy-1-(4- hydroxyphenyl)-3- oxobutan-2- ylimino)methyl)phenyl isobutyrate 208. OH Br 5-bromo-2-hydroxy-3- ((4-hydroxy-1-(4- hydroxyphenyl)-3- oxobutan-2- ylimino)methyl)phenyl isobutyrate 209. Cl 3-(5-chloro-2,3-bis- isobutryloxybenzylidene- amino)-1-hydroxy-4- (4-hydroxyphenyl)butan- 2-one 210. Br 3-(5-bromo-2,3-bis- isobutrylxoybenzylidene- amino)-1-hydroxy-4- (4-hydroxyphenyl)butan- 2-one 211. OH H Cl 3-(3-chloro-5-hy- droxybenzylideneamino)- 1-hydroxy-4-(4- hydroxyphenyl)butan-2- one 212. OH H Br 3-(3-bromo-5-hy- droxybenzylideneamino)- 1-hydroxy-4-(4- hydroxyphenyl)butan-2- one 213. OH OH Cl 3-(5-chloro-2,3- dihydroxybenzyl- ideneami- no)-1-hydroxy-4-(4- hydroxyphenyl)butan-2- one 214. OH OH Br 3-(5-bromo-2,3- dihydroxy- benzylideneami- no)-1-hydroxy-4-(4- hydroxyphenyl)butan-2- one 215. OH Cl 4-chloro-2-hydroxy-6- ((4-hydroxy-1-(4- hydroxyphenyl)-3- oxobutan-2- ylimino)methyl)phenyl- isobutyrate 216. OH Br 4-bromo-2-hydroxy-6- ((4-hydroxy-1-(4- hydroxyphenyl)-3- oxobutan-2- ylimino)methyl)phenyl- isobutyrate 217. H H Cl 4-(2-(3-chloro- benzylideneamino)- 4-methoxy-3- oxobutyl)phenyl- isobutyrate 218. H H Br 4-(2-(3-bromo- benzylideneamino)- 4-methoxy-3- oxobutyl)phenyl- isobutyrate 219. H OH Cl 4-(2-(5-chloro-2-hy- droxybenzylideneamino)- 4-methoxy-3- oxobutyl)phenyl- isobutyrate 220. H OH Br 4-(2-(5-bromo-2-hy- droxybenzylideneamino)- 4-methoxy-3- oxobutyl)phenyl- isobutyrate 221. H Cl 4-(2-(2-isobutryloxy)-5- chlorobenzylidene- amino)- 4-methoxy-3- oxobutyl)phenyl- isobutyrate 222. H Br 4-(2-(2-isobutryloxy-5- bromobenzyl- ideneamino)- 4-methoxy-3- oxobutyl)phenyl- isobutyrate 223. H Cl 3-chloro-5-((1-(4- (isobutyryloxy)phenyl)- 4-methoxy-3-oxobutan- 2-ylimino)methyl)phenyl 4-methylbenzoate 224. H Br 3-bromo-5-((1-(4- (isobutyryloxy)phenyl)- 4-methoxy-3-oxobutan- 2-ylimino)methyl)phenyl 4-methylbenzoate 225. H Cl 5-chloro-2-hydroxy-3- ((1-(4- (isobutyryloxy)phenyl)- 4-methoxy-3-oxobutan- 2-ylimino)methyl)phenyl 4-methylbenzoate 226. OH Br 5-bromo-2-hydroxy-3- ((1-(4- (isobutyryloxy)phenyl)- 4-methoxy-3-oxobutan- 2-ylimino)methyl)phenyl 4-methylbenzoate 227. Cl 5-chloro-2- (isobutyryloxy)-3-((1-(4- (isobutyryloxy)phenyl)- 4-methoxy-3-oxobutan- 2-ylimino)methyl)phenyl 4-methylbenzoate 228. Br 5-bromo-2- (isobutyryloxy)-3-((1-(4- (isobutyryloxy)phenyl)- 4-methoxy-3-oxobutan- 2-ylimino)methyl)phenyl 4-methylbenzoate 229. H Cl 3-chloro-5-((1-(4- (isobutyryloxy)phenyl)- 4-methoxy-3-oxobutan- 2-ylimino)methyl)phenyl 3-methylbenzoate 230. H Br 3-bromo-5-((1-(4- (isobutyryloxy)phenyl)- 4-methoxy-3-oxobutan- 2-ylimino)methyl)phenyl 3-methylbenzoate 231. OH Cl 5-chloro-2-hydroxy-3- ((1-(4- (isobutyryloxy)pheny)- 4-methoxy-3-oxobutan- 2-ylimino)methyl)phenyl 3-methylbenzoate 232. OH Br 5-bromo-2-hydroxy-3- ((1-(4- (isobutyryloxy)phenyl)- 4-methoxy-3-oxobutan- 2-ylimino)methyl)phenyl 3-methylbenzoate 233. Cl 5-chloro-2- (isobutyryloxy)-3-((1-(4- (isobutyryloxy)phenyl)- 4-methoxy-3-oxobutan- 2-ylimino)methyl)phenyl 3-methylbenzoate 234. Br 5-bromo-2- (isobutyryloxy)-3-((1-(4- (isobutyryloxy)phenyl)- 4-methoxy-3-oxobutan- 2-ylimino)methyl)phenyl 3-methylbenzoate 235. H Cl 3-chloro-5-((1-(4- (isobutyryloxy)phenyl)- 4-methoxy-3-oxobutan- 2-ylimino)methyl)phenyl nicotinate 236. H Br 3-bromo-5-((1-(4- (isobutyryloxy)phenyl)- 4-methoxy-3-oxobutan- 2-ylimino)methyl)phenyl nicotinate 237. OH Cl 5-chloro-2-hydroxy-3- ((1-(4- (isobutyryloxy)phenyl)- 4-methoxy-3-oxobutan- 2-ylimino)methyl)phenyl nicotinate 238. OH Br 5-bromo-2-hydroxy-3- ((1-(4- (isobutyryloxy)phenyl)- 4-methoxy-3-oxobutan- 2-ylimino)methyl)phenyl nicotinate 239. Cl 5-chloro-2- (isobutyryloxy)-3-((1-(4- (isobutyryloxy)phenyl)- 4-methoxy-3-oxobutan- 2-ylimino)methyl)phenyl nicotinate 240. Br 5-bromo-2- (isobutyryloxy)-3-((1-(4- (isobutyryloxy)phenyl)- 4-methoxy-3-oxobutan- 2-ylimino)methyl)phenyl nicotinate 241. H Cl 4-(2-(3-isoburyloxy-5- chlorobenzyl- ideneamino)- 4-methoxy-3- oxobutyl)phenyl isobutyrate 242. H Br 4-(2-(3-isobutryloxy-5- bromobenzyl- ideneamino)- 4-methoxy-3- oxobutyl)phenyl isobutyrate 243. OH Cl 4-(2-(3-isobutryloxy-5- chloro-2-hydroxy- benzylideneamino)- 4-methoxy-3- oxobutyl)phenyl isobutyrate 244. OH Br 4-(2-(3-isobutryloxy-5- bromo-2-hydroxy- benzylideneamino)- 4-methoxy-3- oxobutyl)phenyl isobutyrate 245. Cl 4-(2-(2,3- bis(isobutryloxy)-5- chlorobenzyl- ideneamino)- 4-methoxy-3- oxobutyl)phenyl isobutyrate 246. Br 4-(2-(2,3- bis(isobutryloxy)-5- chlorobenzyl- ideneamino)- 4-methoxy-3- oxobutyl)phenyl isobutyrate 247. OH H Cl 4-(2-(3-chloro-5-hy- droxybenzylideneamino)- 4-methoxy-3- oxobutyl)phenyl isobutyrate 248. OH H Br 4-(2-(3-bromo-5-hy- droxybenzylideneamino)- 4-methoxy-3- oxobutyl)phenyl isobutyrate 249. OH OH Cl 4-(2-(5-chloro-2,3- dihydroxy- benzylideneami- no)-4-methoxy-3- oxobutyl)phenyl isobutyrate 250. OH OH Br 4-(2-(5-bromo-2,3-di- hydroxybenzylideneami- no)-4-methoxy-3- oxobutyl)phenyl isobutyrate 251. OH Cl 4-(2-(2-isobutryloxy-5- chloro-3-hydroxy- benzylideneamino)- 4-methoxy-3- oxobutyl)phenyl isobutyrate 252. OH Br 4-(2-(2-isobutryloxy-5- bromo-3-hydroxy- benzylideneamino)- 4-methoxy-3- oxobutyl)phenyl isobutyrate 253. H H Cl N-(3-chlorobenzylidene)- 2,4-dichloro- benzenenamine 254. H H Br N-(3-bromobenzylidene)- 2,4-dichloro- benzeneamine 255. H OH Cl 4-chloro-2-((2,4- dichlorophenylimino) methyl)phenol 256. H OH Br 4-bromo-2-((2,4-di- chlorophenylimino)meth- yl)phenol 257. H Cl 4-chloro-2-((2,4-di- chlorophenylimino)meth- yl)phenyl isobutyrate 258. H Br 4-bromo-2-((2,4-di- chlorophenylimino)meth- yl)phenyl isobutyrate 259. H Cl 3-chloro-5-((2,4-di- chlorophenylimino)meth- yl)phenyl 4- methylbenzoate 260. H Br 3-bromo-5-((2,4-di- chlorophenylimino)meth- yl)phenyl 4- methylbenzoate 261. OH Cl 5-chloro-3-((2,4-di- chlorophenylimino)meth- yl)-2-hydroxyphenyl 4- methylbenzoate 262. OH Br 5-bromo-3-((2,4-di- chlorophenylimino)meth- yl)-2-hydroxyphenyl 4- methylbenzoate 263. Cl 5-chloro-3-((2,4-di- chlorophenylimino)meth- yl)-2- (isobutyryloxy)phenyl 4- methylbenzoate 264. Br 5-bromo-3-((2,4-di- chlorophenylimino)meth- yl)-2- (isobutyryloxy)phenyl 4- methylbenzoate 265. H Cl 3-chloro-5-((2,4-di- chlorophenylimino)meth- yl)phenyl 3- methylbenzoate 266. H Br 3-bromo-5-((2,4-di- chlorophenylimino)meth- yl)phenyl 3- methylbenzoate 267. OH Cl 5-chloro-3-((2,4-di- chlorophenylimino)meth- yl)-2-hydroxyphenyl 3- methylbenzoate 268. OH Br 5-bromo-3-((2,4-di- chlorophenylimino)meth- yl)-2-hydroxyphenyl 3- methylbenzoate 269. Cl 5-chloro-3-((2,4- dichlorophenyl- imino)meth- yl)-2- (isobutyryloxy)phenyl 3- methylbenzoate 270. Br 5-bromo-3-((2,4- dichlorophenyl- imino)meth- yl)-2- (isobutyryloxy)phenyl 3- methylbenzoate 271. H Cl 3-chloro-5-((2,4- dichloro- phenylimino)meth- yl)phenyl nicotinate 272. H Br 3-bromo-5-((2,4- dichloro- phenylimino)meth- yl)phenyl nicotinate 273. OH Cl 5-chloro-3-((2,4- dichloro- phenylimino)meth- yl)-2-hydroxyphenyl nicotinate 274. OH Br 5-bromo-3-((2,4- dichloro- phenylimino)meth- yl)-2-hydroxyphenyl nicotinate 275. Cl 5-chloro-3-((2,4- dichloro- phenylimino)meth- yl)-2- (isobutyryloxy)phenyl nicotinate 276. Br 5-bromo-3-((2,4- dichloro- phenylimino)meth- yl)-2- (isobutyryloxy)phenyl nicotinate 277. H Cl 3-chloro-5-((2,4- dichloro- phenylimino)meth- yl)phenyl isobutyrate 278. H Br 3-bromo-5-((2,4- dichloro- phenylimino)meth- yl)phenyl isobutyrate 279. OH Cl 5-chloro-3-((2,4- dichloro- phenylimino)meth- yl)-2-hydroxyphenyl isobutyrate 280. OH Br 5-bromo-3-((2,4- dichloro- phenylimino)meth- yl)-2-hydroxyphenyl isobutyrate 281. Cl N-(2,3-bis(isobutryloxy)- 5-chlorobenzylidene)- 2,4-dichlorobenzenamine 282. Br N-(2,3-bis(isobutryloxy)- 5-bromobenzylidene)- 2,4-dichlorobenzenamine 283. OH H Cl 3-chloro-5-((2,4- dichloro- phenylimino)meth- yl)phenol 284. OH H Br 3-bromo-5-((2,4- dichloro- phenylimino)meth- yl)phenol 285. OH OH Cl 5-chloro-3-((2,4- dichloro- phenylimino)meth- yl)benzene-1,2-diol 286. OH OH Br 5-bromo-3-((2,4- dichloro- phenylimino)meth- yl)benzene-1,2-diol 287. OH Cl 4-chloro-2-((2,4- dichloro- phenylimino)meth- yl)-6-hydroxyphenyl isobutyrate 288. OH Br 4-bromo-2-((2,4- dichloro- phenylimino)meth- yl)-6-hydroxyphenyl isobutyrate 289. H H Cl N-(3-chlorobenzylidene)- 4-chlorobenzenamine 290. H H Br N-(3-bromobenzylidene)- 4-chlorobenzenamine 291. H OH Cl 4-chloro-2-((4- chlorophenylimino)meth- yl)phenol 292. H OH Br 4-bromo-2-((4- chlorophenylimino)meth- yl)phenol 293. H Cl 4-chloro-2-((4- chlorophenylimino)meth- yl)phenyl isobutyrate 294. H Br 4-bromo-2-((4- chlorophenylimino)meth- yl)phenyl isobutyrate 295. H Cl 3-chloro-5-((4- chlorophenylimino)meth- yl)phenyl 4- methylbenzoate 296. H Br 3-bromo-5-((4- chlorophenylimino)meth- yl)phenyl 4- methylbenzoate 297. OH Cl 5-chloro-3-((4- chlorophenylimino)meth- yl)-2-hydroxyphenyl 4- methylbenzoate 298. OH Br 5-bromo-3-((4- chlorophenylimino)meth- yl)-2-hydroxyphenyl 4- methylbenzoate 299. Cl 5-chloro-3-((4- chlorophenylimino)meth- yl)-2- (isobutyryloxy)phenyl 4- methylbenzoate 300. Br 5-bromo-3-((4- chlorophenylimino)meth- yl)-2- (isobutyryloxy)phenyl 4- methylbenzoate 301. H Cl 3-chloro-5-((4- chlorophenylimino)meth- yl)phenyl 3- methylbenzoate 302. H Br 3-bromo-5-((4- chlorophenylimino)meth- yl)phenyl 3- methylbenzoate 303. OH Cl 5-chloro-3-((4- chlorophenylimino)meth- yl)-2-hydroxyphenyl 3- methylbenzoate 304. OH Br 5-bromo-3-((4- chlorophenylimino)meth- yl)-2-hydroxyphenyl 3- methylbenzoate 305. Cl 5-chloro-3-((4- chlorophenylimino)meth- yl)-2- (isobutyryloxy)phenyl 3- methylbenzoate 306. Br 5-bromo-3-((4- chlorophenylimino)meth- yl)-2- (isobutyryloxy)phenyl 3- methylbenzoate 307. H Cl 3-chloro-5-((4- chlorophenylimino)meth- yl)phenyl nicotinate 308. H Br 3-bromo-5-((4- chlorophenylimino)meth- yl)phenyl nicotinate 309. OH Cl 5-chloro-3-((4- chlorophenylimino)meth- yl)-2-hydroxyphenyl nicotinate 310. OH Br 5-bromo-3-((4- chlorophenylimino)meth- yl)-2-hydroxyphenyl nicotinate 311. Cl 5-chloro-3-((4- chlorophenylimino)meth- yl)-2- (isobutyryloxy)phenyl nicotinate 312. Br 5-bromo-3-((4- chlorophenylimino)meth- yl)-2- (isobutyryloxy)phenyl nicotinate 313. H Cl 3-chloro-5-((4- chlorophenylimino)meth- yl)phenyl isobutyrate 314. H Br 3-bromo-5-((4- chlorophenylimino)meth- yl)phenyl isobutyrate 315. OH Cl 5-chloro-3-((4- chlorophenylimino)meth- yl)-2-hydroxyphenyl isobutyrate 316. OH Br 5-bromo-3-((4- chlorophenylimino)meth- yl)-2-hydroxyphenyl isobutyrate 317. Cl N-(2,3-bis(isobutryloxy)- 5-chlorobenzylidene)-4- chlorobenzeneamine 318. Br N-(2,3-bis(isobutryloxy)- 5-bromobenzylidene)-4- chlorobenzeneamine 319. OH H Cl 3-chloro-5-((4- chlorophenylimino)meth- yl)phenol 320. OH H Br 3-bromo-5-((4- chlorophenylimino)meth- yl)phenol 321. OH OH Cl 5-chloro-3-((4- chlorophenylimino)meth- yl)benzene-1,2-diol 322. OH OH Br 5-bromo-3-((4- chlorophenylimino)meth- yl)benzene-1,2-diol 323. OH Cl 4-chloro-2-((4- chlorophenylimino)meth- yl)-6-hydroxyphenyl- isobutyrate 324. OH Br 4-bromo-2-((4- chlorophenylimino)meth- yl)-6-hydroxyphenyl- isobutyrate 325. H H Cl N-(3-chlorobenzylidene)- 2,3-dichlorobenzenamine 326. H H Br N-(3-bromobenzylidene)- 2,3-dichlorobenzenamine 327. H OH Cl 4-chloro-2-((2,3- dichloro- phenylimino)meth- yl)phenol 328. H OH Br 4-bromo-2-((2,3- dichlorophenylimino)meth- yl)phenol 329. H Cl 4-chloro-2-((2,3- dichloro- phenylimino)meth- yl)phenyl isobutyrate 330. H Br 4-bromo-2-((2,3- dichloro- phenylimino)meth- yl)phenyl isobutyrate 331. H Cl 3-chloro-5-((2,3- dichloro- phenylimino)meth- yl)phenyl 4- methylbenzoate 332. H Br 3-bromo-5-((2,3- dichloro- phenylimino)meth- yl)phenyl 4- methylbenzoate 333. OH Cl 5-chloro-3-((2,3- dichloro- phenylimino)meth- yl)-2-hydroxyphenyl 4- methylbenzoate 334. OH Br 5-bromo-3- ((2,3- dichloro- phenylimino)meth- yl)-2-hydroxyphenyl 4- methylbenzoate 335. Cl 5-chloro-3-((2,3- dichloro- phenylimino)meth- yl)-2- (isobutyryloxy)phenyl 4- methylbenzoate 336. Br 5-bromo-3-((2,3- dichloro- phenylimino)meth- yl)-2- (isobutyryloxy)phenyl 4- methylbenzoate 337. H Cl 3-chloro-5-((2,3- dichloro- phenylimino)meth- yl)phenyl 3- methylbenzoate 338. H Br 3-bromo-5-((2,3- dichloro- phenylimino)meth- yl)phenyl 3- methylbenzoate 339. OH Cl 5-chloro-3-((2,3- dichloro- phenylimino)meth- yl)-2-hydroxyphenyl 3- methylbenzoate 340. OH Br 5-bromo-3-((2,3- dichloro- phenylimino)meth- yl)-2-hydroxyphenyl 3- methylbenzoate 341. Cl 5-chloro-3-((2,3- dichloro- phenylimino)meth- yl)-2- (isobutyryloxy)phenyl 3- methylbenzoate 342. Br 5-bromo-3-((2,3- dichloro- phenylimino)meth- yl)-2- (isobutyryloxy)phenyl 3- methylbenzoate 343. H Cl 3-chloro-5-((2,3- dichloro- phenylimino)meth- yl)phenyl nicotinate 344. H Br 3-bromo-5-((2,3- dichloro- phenylimino)meth- yl)phenyl nicotinate 345. OH Cl 5-chloro-3-((2,3- dichloro- phenylimino)meth- yl)-2-hydroxyphenyl nicotinate 346. OH Br 5-bromo-3-((2,3- dichloro- phenylimino)meth- yl)-2-hydroxpheny nicotinate 347. Cl 5-chloro-3-((2,3- dichloro- phenylimino)meth- yl)-2- (isobutyryloxy)phenyl nicotinate 348. Br 5-bromo-3-((2,3- dichloro- phenylimino)meth- yl)-2- (isobutyryloxy)phenyl nicotinate 349. H Cl 3-chloro-5-((2,3- dichloro- phenylimino)meth- yl)phenyl isobutyrate 350. H Br 3-bromo-5-((2,3- dichloro- phenylimino)meth- yl)phenyl isobutyrate 351. OH Cl 5-chloro-3-((2,3- dichloro- phenylimino)meth- yl)-2-hydroxyphenyl isobutyrate 352. OH Br 5-bromo-3-((2,3- dichloro- phenylimino)meth- yl)-2-hydroxyphenyl- isobutyrate 353. Cl N-(2,3-bis(isobutryloxy)- 5-chlorobenzylidene)- 2,3-dichlorobenzenamine 354. Br N-(2,3-bis(isobutryloxy)- 5-bromobenzylidene)- 2,3-dichlorobenzenamine 355. OH H Cl 3-chloro-5-((2,3- dichloro- phenylimino)meth- yl)phenol 356. OH H Br 3-bromo-5-((2,3- dichloro- phenylimino)meth- yl)phenol 357. OH OH Cl 5-chloro-3-((2,3- dichloro- phenylimino)meth- yl)benzene-1,2-diol 358. OH OH Br 5-bromo-3-((2,3- dichloro- phenylimino)meth- yl)benzene-1,2-diol 359. OH Cl 4-chloro-2-((2,3- dichloro- phenylimino)meth- yl)-6-hydroxyphenyl- isobutyrate 360. OH Br 4-bromo-2-((2,3- dichloro- phenylimino)meth- yl)-6-hydroxyphenyl- isobutyrate 361. H H Cl N-(3-chlorobenzylidene)- 3,5-dichlorobenzeneamine 362. H H Br N-(3-bromobenzylidene)- 3,5-dichlorobenzeneamine 363. H OH Cl 4-chloro-2-((3,5- dichloro- phenylimino)meth- yl)phenol 364. H OH Br 4-bromo-2-((3,5- dichloro- phenylimino)meth- yl)phenol 365. H Cl 4-chloro-2-((3,5- dichloro- phenylimino)meth- yl)phenyl isobutyrate 366. H Br 4-bromo-2-((3,5- dichloro- phenylimino)meth- yl)phenyl isobutyrate 367. H Cl 3-chloro-5-((3,5- dichloro- phenylimino)meth- yl)phenyl 4- methylbenzoate 368. H Br 3-bromo-5-((3,5- dichloro- phenylimino)meth- yl)phenyl 4- methylbenzoate 369. OH Cl 5-chloro-3-((3,5- dichloro- phenylimino)meth- yl)-2-hydroxyphenyl 4- methylbenzoate 370. OH Br 5-bromo-3-((3,5- dichloro- phenylimino)meth- yl)-2-hydroxyphenyl 4- methylbenzoate 371. Cl 5-chloro-3-((3,5- dichloro- phenylimino)meth- yl)-2- (isobutyryloxy)phenyl 4- methylbenzoate 372. Br 5-bromo-3-((3,5- dichloro- phenylimino)meth- yl)-2- (isobutyryloxy)phenyl 4- methylbenzoate 373. H Cl 5-chloro-3-((3,5- dichloro- phenylimino)meth- yl)-2- (isobutyryloxy)phenyl 3- methylbenzoate 374. H Br 5-bromo-3-((3,5- dichloro- phenylimino)meth- yl)-2- (isobutyryloxy)phenyl 3- methylbenzoate 375. OH Cl 5-chloro-3-((3,5- dichloro- phenylimino)meth- yl)-2-hydroxyphenyl 3- methylbenzoate 376. OH Br 5-bormo-3-((3,5- dichloro- phenylimino)meth- yl)-2-hydroxyphenyl 3- methylbenzoate 377. Cl 5-chloro-3-((3,5- dichloro- phenylimino)meth- yl)-2- (isobutyryloxy)phenyl 3- methyblenozate 378. Br 5-bromo-3-((3,5- dichloro- phenylimino)meth- yl)-2- (isobutyryloxy)phenyl 3- methylbenzoate 379. H Cl 3-chloro-5-((3,5- dichloro- phenylimino)meth- yl)phenyl nicotinate 380. H Br 3-bromo-5-((3,5- dichloro- phenylimino)meth- yl)phenyl nicotinate 381. OH Cl 5-chloro-3-((3,5- dichloro- phenylimino)meth- yl)-2-hydroxyphenyl nicotinate 382. OH Br 5-bromo-3-((3,5- dichloro- phenylimino)meth- yl)-2-hydroxyphenyl nicotinate 383. Cl 5-chloro-3-((3,5- dichloro- phenylimino)meth- yl)-2- (isobutyryloxy)phenyl nicotinate 384. Br 5-bromo-3-((3,5- dichloro- phenylimino)meth- yl)-2- (isobutyryloxy)phenyl nicotinate 385. H Cl 3-chloro-5-((3,5- dichloro- phenylimino)meth- yl)phenyl isobutyrate 386. H Br 3-bromo-5-((3,5- dichloro- phenylimino)meth- yl)phenyl isobutyrate 387. OH Cl 5-chloro-3-((3,5- dichloro- phenylimino)meth- yl)-2-hydroxyphenyl isobutyrate 388. OH Br 5-bromo-3-((3,5- dichloro- phenylimino)meth- yl)-2-hydroxyphenyl isobutyrate 389. Cl N-(2,3-bis(isobutryloxy)- 5-chlorobenzylidene)- 3,5-dichloro- benzeneamine 390. Br N-(2,3-bis(isobutryloxy)- 5-bromobenzylidene)- 3,5- dichlorobenzeneamine 391. OH H Cl 3-chloro-5-((3,5- dichloro- phenylimino)meth- yl)phenol 392. OH H Br 3-bromo-5-((3,5- dichloro- phenylimino)meth- yl)phenol 393. OH OH Cl 5-chloro-3-((3,5- dichloro- phenylimino)meth- yl)benzene-1,2-diol 394. OH OH Br 5-bromo-3-((3,5- dichloro- phenylimino)meth- yl)benzene-1,2-diol 395. OH Cl 4-chloro-2-((3,5- dichloro- phenylimino)meth- yl)-6-hydroxyphenyl isobutyrate 396. OH Br 4-bromo-2-((3,5- dichlorophenyl- imino)meth- yl)-6-hydroxyphenyl isobutyrate 397. H H Cl N-(3-chlorobenzylidene)- 2-phenylethanamine 398. H H Br N-(3-bromobenzylidene)- 2-phenylethanamine 399. H OH Cl 4-chloro-2-((phenethyl- imino)methyl)phenol 400. H OH Br 4-bromo-2- ((phenethyl- imino)methyl) phenol 401. H Cl 4-chloro-2- ((phenethyl- imino)methyl) phenyl isobutyrate 402. H Br 4-bromo-2- ((phenethyl- imino)methyl) phenyl isobutyrate 403. H Cl 3-chloro-5- ((phenethyl- imino)methyl) phenyl 4- methylbenzoate 404. H Br 3-bromo-5- ((phenethyl- imino)methyl) phenyl 4- methylbenzoate 405. OH Cl 5-chloro-2-hydroxy-3- ((phenethyl- imino)methyl) phenyl 4- methylbenzoate 406. OH Br 5-bromo-2-hydroxy-3- ((phenethyl- imino)methyl) phenyl 4- methylbenzoate 407. Cl 5-chloro-2- (isobutyryloxy)-3- ((phenethyl- imino)methyl) phenyl 4- methylbenzoate 408. Br 5-bromo-2- (isobutyryloxy)-3- ((phenethyl- imino)methyl) phenyl 4- methylbenzoate 409. H Cl 3-chloro-5- ((phenethyl- imino)methyl) phenyl 3- methylbenzoate 410. H Br 3-bromo-5- ((phenethyl- imino)methyl) phenyl 3- methylbenzoate 411. OH Cl 5-chloro-2-hydroxy-3- ((phenethyl- imino)methyl) phenyl 3- methylbenzoate 412. OH Br 5-bromo-2-hydroxy-3- ((phenethyl- imino)methyl) phenyl 3- methylbenzoate 413. Cl 5-chloro-2- (isobutyryloxy)-3- ((phenethyl- imino)methyl) phenyl 3- methylbenzoate 414. Br 5-bromo-2- (isobutyryloxy)-3- ((phenethyl- imino)methyl) phenyl 3- methylbenzoate 415. H Cl 3-chloro-5- ((phenethyl- imino)methyl) phenyl nicotinate 416. H Br 3-bromo-5- ((phenethyl- imino)methyl) phenyl nicotinate 417. OH Cl 5-chloro-2-hydroxy-3- ((phenethyl- imino)methyl) phenyl nicotinate 418. OH Br 5-bromo-2-hydroxy-3- ((phenethyl- imino)methyl) phenyl nicotinate 419. Cl 5-chloro-2- (isobutyryloxy)-3- ((phenethyl- imino)methyl) phenyl nicotinate 420. Br 5-bromo-2- (isobutyryloxy)-3- ((phenethyl- imino)methyl) phenyl nicotinate 421. H Cl 3-chloro-5- ((phenethyl- imino)methyl) phenyl isobutyrate 422. H Br 3-bromo-5- ((phenethyl- imino)methyl) phenyl isobutyrate 423. OH Cl 5-chloro-2-hydroxy-3- ((phenethyl- imino)methyl) phenyl isobutyrate 424. OH Br 5-bromo-2-hydroxy-3- ((phenethyl- imino)methyl) phenyl isobutyrate 425. Cl N-(2,3-bis(isobutryloxy)- 5-chlorobenzylidene)-2- phenylethanamien 426. Br N-(2,3-bis(isobutryloxy)- 5-bromobenzylidene)-2- phenylethanamine 427. OH H Cl 3-chloro-5- ((phenethyl- imino)methyl) phenol 428. OH H Br 3-bromo-5- ((phenethyl- imino)methyl) phenol 429. OH OH Cl 5-chloro-3- ((phenethyl- imino)methyl) benzene-1,2-diol 430. OH OH Br 5-bromo-3- ((phenethyl- imino)methyl) benzene-1,2-diol 431. OH Cl 4-chloro-2-hydroxy-6- ((phenethyl- imino)methyl) phenyl isobutyrate 432. OH Br 4-bromo-2-hydroxy-6- ((phenethyl- imino)methyl) phenyl isobutyrate 433. H H Cl N-(3-chloro- benzylidene)- 4- ((dimethylamino)methyl) benzenamine 434. H H Br N-(3-bromobenzylidene)- 4-((diethyl- amino)methyl)benzen- amine 435. H OH Cl 4-chloro-2-((4-((di- ethylamino)methyl)phen- ylimino)methyl)phen- ol 436. H OH Br 4-bromo-2-((4-((di- ethylamino)methyl)phen- ylimino)methyl)phen- ol 437. H Cl 4-chloro-2-((4-((di- ethylamino)methyl)phen- ylimino)methyl)phen- yl isobutyrate 438. H Br 4-bromo-2-((4-((di- ethylamino)methyl)phen- ylimino)methyl)phen- yl isobutyrate 439. H Cl 3-chloro-5-((4-((di- ethylamino)methyl)phen- ylimino)methyl)phen- yl 4-methylbenzoate 440. H Br 3-bromo-5-((4-((di- ethylamino)methyl)phen- ylimino)methyl)phen- yl 4-methylbenzoate 441. OH Cl 5-chloro-3-((4-((di- ethylamino)methyl)phen- ylimino)methyl)-2- hydroxyphenyl 4- methylbenzoate 442. OH Br 5-bromo-3-((4-((di- ethylamino)methyl)phen- ylimino)methyl)-2- hydroxyphenyl 4- methylbenzoate 443. Cl 5-chloro-3-((4-((di- ethylamino)methyl)phen- ylimino)methyl)-2- (isobutyryloxy)phenyl 4- methylbenzoate 444. Br 5-bromo-3-((4-((di- ethylamino)methyl)phen- ylimino)methyl)-2- (isobutyryloxy)phenyl 4- methylbenzoate 445. H Cl 3-chloro-5-((4-((di- ethylamino)methyl)phen- ylimino)methyl)phen- yl 3-methylbenzoate 446. H Br 3-bromo-5-((4-((di- ethylamino)methyl)phen- ylimino)methyl)phen- yl 3-methylbenzoate 447. OH Cl 5-chloro-3-((4-((di- ethylamino)methyl)phen- ylimino)methyl)-2- hydroxyphenyl 3- methylbenzoate 448. OH Br 5-bromo-3-((4-((di- ethylamino)methyl)phen- ylimino)methyl)-2- hydroxyphenyl 3- methylbenzoate 449. Cl 5-chloro-3-((4-((di- ethylamino)methyl)phen- imino)methyl)-2- (isobutyryloxy)phenyl 3- methylbenzoate 450. Br 5-bromo-3-((4-((di- ethylamino)methyl)phen- ylimino)methyl)-2- (isobutyryloxy)phenyl 3- methylbenzoate 451. H Cl 3-chloro-5-((4-((di- ethylamino)methyl)phen- ylimino)methyl)phen- yl nicotinate 452. H Br 3-bromo-5-((4-((di- ethylamino)methyl)phen- ylimino)methyl)phen- yl nicotinate 453. OH Cl 5-chloro-3-((4-((di- ethylamino)methyl)phen- ylimino)methyl)-3- hydroxyphenyl nicotinate 454. OH Br 5-bromo-3-((4-((di- ethylamino)methyl)phen- ylimino)methyl)-2- hydroxyphenyl nicotinate 455. Cl 5-chloro-3-((4-((di- ethylamino)methyl)phen- ylimino)methyl)-2- (isobutyryloxy)phenyl nicotinate 456. Br 5-bromo-3-((4-((di- ethylamino)methyl)phen- ylimino)methyl)-2- (isobutyryloxy)phenyl nicotinate 457. H Cl 3-chloro-5-((4-((di- ethylamino)methyl)phen- ylimino)methyl)phen- yl isobutyrate 458. H Br 3-bromo-5-((4-((di- ethylamino)methyl)phen- ylmino)methyl)phen- yl isobutyrate 459. OH Cl 5-chloro-3-((4-((di- ethylamino)methyl)phen- ylmimino)methyl)-2- hydroxyphenyl isobutyrate 460. OH Br 5-bromo-3-((4-((di- ethylamino)methyl)phen- ylimino)methyl)-2- hydroxyphenyl isobutyrate 461. Cl N-(2,3-bis(isobutryloxy)- 5-chlorobenzylidene)-4- ((diethylamino)meth- yl)benzenamine 462. Br N-(2,3-bis(isobutryloxy)- 5-bromobenzylidene)-4- ((diethylamino)meth- yl)benzenamine 463. OH H Cl 3-chloro-5-((4-((di- ethylamino)methyl)phen- ylimino)methyl)phen- ol 464. OH H Br 3-bromo-5-((4-((di- ethylamino)methyl)phen- ylimino)methyl)phen- ol 465. OH OH Cl 5-chloro-3-(4-((di- ethylamino)methyl)phen- ylimino)methyl)benzene- 1,2-diol 466. OH OH Br 5-bromo-3-((4-((di- ethylamino)methyl)phen- ylinon)methyl)benzene- 1,2-diole 467. OH Cl 4-chloro-2-((4-((di- ethylamino)methyl)phen- ylimino)methyl)-6- hydroxyphenyl isobutyrate 468. OH Br 4-bromo-2-((4-((di- ethylamino)methyl)phen- ylimino)methyl)-6- hydroxyphenyl isobutyrate 469. H H Cl N-(3- chlorobenzyl- idene)pyridin-3-amine 470. H H Br N-(3- bromobenzyl- idene)pyridin-3-amine 471. H OH Cl 4-chloro-2-((pyridin-3- ylimino)methyl)phenol 472. H OH Br 4-bromo-2-((pyridin-3- ylimino)methyl)phenol 473. H Cl 4-chloro-2-((pyridin-3- ylmino)methyl)phenyl isobutyrate 474. H Br 4-bromo-2-((pyridin-3- ylimino)methyl)phenyl isobutyrate 475. H Cl 3-chloro-5-((pyridin-3- ylimino)meth- yl)phenyl 4-methyl- benzoate 476. H Br 3-bromo-5-((pyridin-3- ylmino)methyl)phenyl 4- methylbenzoate 477. OH Cl 5-chloro-2-hydroxy-3- ((pyridin-3- ylmino)methyl)phenyl 4- methylbenzoate 478. OH Br 5-bromo-2-hydroxy-3- ((pyridin-3- ylimin)methyl)phenyl 4- methylbenzoate 479. Cl 5-chloro-2- (isobutyryloxy)-3- ((pyridin-3- ylmino)methyl)phenyl 4- methylbenzoate 480. Br 5-bromo-2- (isobutyryloxy)-3- ((pyridin-3-yl- imino)mehtyl)phenyl 4- methylbenzoate 481. H Cl 3-chloro-5-((pyridin-3- ylimino)methyl)phenyl 3-methylbenzoate 482. H Br 3-bromo-5-((pyridin-3- ylimino)methyl)phenyl 3-methylbenzoate 483. OH Cl 5-chloro-2-hydroxy-3- ((pyridin-3- ylmino)methyl)phenyl 3- methylbenzoate 484. OH Br 5-bromo-2-hydroxy-3- ((pyridin-3- ylmino)methyl)phenyl 3- methylbenzoate 485. Cl 5-chloro-2- (isobutyryloxy)-3- ((pyridin-3- ylimino)methyl)phenyl 3-methylbenzoate 486. Br 5-bromo-2- (isobutyryloxy)-3- ((pyridin-3- ylmino)methyl)phenyl 3- methylbenzoate 487. H Cl 3-chloro-5-((pyridin-3- ylimino)methyl)phenyl nicotinate 488. H Br 3-bromo-5-((pyridin-3- ylmino)methyl)phenyl nicotinate 489. OH Cl 5-chloro-2-hydroxy-3- ((pyridin-3- ylmino)methyl)phenyl nicotinate 490. OH Br 5-bromo-2-hydroxy-3- ((pyridin-3- ylimino)methyl)phenyl nicotinate 491. Cl 5-chloro-2- (isobutyryloxy)-3- ((pyridin-3- ylmino)methyl)phenyl nicotinate 492. Br 5-bromo-2- (isobutyryloxy)-3- ((pyridin-3- ylimino)methyl)phenyl nicotinate 493. H Cl 3-chloro-5-((pyridin-3- ylimino)methyl)phenyl isobutyrate 494. H Br 3-bromo-5-((pyridin-3- ylimno)methyl)phenyl isobutyrate 495. OH Cl 5-chloro-2-hydroxy-3- ((pyridin-3- ylimino)methyl)phenyl isobutyrate 496. OH Br 5-bromo-2-hydroxy-3- ((pyridin-3- ylimino)methyl)phenyl isobutyrate 497. Cl N-(2,3-bis(isobutryloxy)- 5-chlorobenzyl- idene)pyridin-3-amine 498. Br N-(2,3-bis(isobutryloxy)- 5-bromobenzyl- idene)pyridin-3-amine 499. OH H Cl 3-chloro-5-((pyridin-3- ylimino)methyl)phenol 500. OH H Br 3-bromo-5-((pyridin-3- ylmino)methyl)phenol 501. OH OH Cl 5-chloro-3-((pyridin-3- ylimino)methyl)benzene- 1,2-diol 502. OH OH Br 5-bromo-3-((pyridin-3- ylimino)methyl)benzene- 1,2-diol 503. OH Cl 4-chloro-2-hydroxy-6- ((pyridin-3- ylimino)methyl)phenyl isobutyrate 504. OH Br 4-bromo-2-hydroxy-6- ((pyridin-3- ylimino)methyl)phenyl isobutyrate 505. H H Cl 3-(3- chlorobenzylideneamino) benzoic acid 506. H H Br 3-(3- bromobenzylideneamino) benzoic acid 507. H OH Cl 3-(5-chloro-2- hydroxybenzyl- ideneamino) benzoic acid 508. H OH Br 3-(5-bromo-2- hydroxybenzyl- ideneamino) benzoic acid 509. H Cl 3-(5-chloro-2-(iso- butyryloxy)benzylidene- amino)benzoic acid 510. H Br 3-(5-bromo-2-(iso- butyryloxy)benzylidene- amino)benzoic acid 511. H Cl 3-(3-chloro-5-(4- methylbenzoyl- oxy)benzyl- ideneamino)benzoic acid 512. H Br 3-(3-bromo-5-(4- methylbenzoyl- oxy)benzy- ideneamino)benzoic acid 513. OH Cl 3-(5-chloro-2-hydroxy-3- (4-methylbenzoyl- oxy)benzyl- ideneamino)benzoic acid 514. OH Br 3-(5-bromo-2-hydroxy-3- (4-methylbenzoyl- oxy)benzyl- ideneamino)benzoic acid 515. Cl 3-(5-chloro-2- (isobutyryloxy)-3-(4- methylbenzoyl- oxy)benzyl- ideneamino)benzoic acid 516. Br 3-(5-bromo-2- (isobutyryloxy)-3-(4- methylbenzoyl- oxy)benzyl- ideneamino)benzoic acid 517. H Cl 3-(3-chloro-5-(3- methylbenzoyl- oxy)benzyl- ideneamino)benzoic acid 518. H Br 3-(3-bromo-5-(3- methylbenzoyl- oxy)benzyl- ideneamino)benzoic acid 519. OH Cl 3-(5-chloro-2-hydroxy-3- (3-methylbenzoyl- oxy)benzyl- ideneamino)benzoic acid 520. OH Br 3-(5-bromo-2-hydroxy-3- (3-methylbenzoyl- oxy)benzyl- ideneamino)benzoic acid 521. Cl 3-(5-chloro-2- (isobutyryloxy)-3-(3- methylbenzoyl- oxy)benzyl- ideneamino)benzoic acid 522. Br 3-(5-bromo-2- (isobutyryloxy)-3-(3- methylbenzoyl- oxy)benzyl- ideneamino)benzoic acid 523. H Cl 3-(3-chloro-5-(ni- cotinoyloxy)benzylidene- amino)benzoic acid 524. H Br 3-(3-bromo-5-(ni- cotinoyloxy)benzylidene- amino)benzoic acid 525. OH Cl 3-(5-chloro-2-hydroxy-3- (nicotinoyloxy)benzyl- ideneamino)benzoic acid 526. OH Br 3-(5-bromo-2-hydroxy-3- (nicotinoyloxy)benzyl- ideneamino)benzoic acid 527. Cl 3-(5-chloro-2- (isobutyryloxy)-3-(nico- tinoyloxy)benzylidene- amino)benzoic acid 528. Br 3-(5-bromo-2- (isobutyryloxy)-3-(nico- tinoyloxy)benzylidene- amino)benzoic acid 529. H Cl 3-(3-chloro-5-(iso- butyryloxy)benzylidene- amino)benzoic acid 530. H Br 3-(3-bromo-5-(iso- butyryloxy)benzylidene- amino)benzoic acid 531. OH Cl 3-(5-chloro-2-hydroxy-3- (isobutyryloxy)benzyli- deneamino)benzoic acid 532. OH Br 3-(5-bromo-2-hydroxy-3- (isobutyryloxy)benzyl- ideneamino)benzoic acid 533. Cl 3-(2,3-bis(isobutryloxy)- 5-chloro- benzylideneamino) benzoic acid 534. Br 3-(2,3-bis(isobutryloxy)- 5-bromo- benzylideneamino) benzoic acid 535. OH H Cl 3-(3-chloro-5- hydroxy- benzylideneamino) benzoic acid 536. OH H Br 3-(3-bromo-5- hydroxy- benzylideneamino) benzoic acid 537. OH OH Cl 3-(5-chloro-2,3- dihydroxybenzyl- ideneami- no)benzoic acid 538. OH OH Br 3-(5-bromo-2,3- dihydroxybenzyl- ideneami- no)benzoic acid 539. OH Cl 3-(5-chloro-3-hydroxy-2- (isobutyryloxy)benzyl- ideneamino)benzoic acid 540. OH Br 3-(5-bromo-3-hydroxy-2- (isobutyryloxy)benzyl- ideneamino)benzoic acid and the compounds where the double bond to R.sub.4 is hydrogenated as represented below, TABLE-US-00004 S. No. R4 R2 Y X IUPAC 541. H OH Br methyl 2-(5-bromo-2- hydroxybenzylamino)-3- (4- hydroxyphenyl)propanoate 542. H OH Br methyl 2-(5-bromo-2- hydroxybenzylamino)-3- methylbutanoate

Description

BRIEF DESCRIPTION OF FIGURES

[0013] FIG. 1 shows that the group of mice administered with Compound 1 showed a 66% decrease of IL-6 from the LPS group.

[0014] FIG. 2 shows that mice administered with Compound 1 showed a 59% decrease of TNF-α from the LPS group.

[0015] FIG. 3 shows that the group of rats administered with Compound 2 showed a 37% decrease in right hind leg volume.

[0016] FIG. 4 shows that rats administered with Compound 2 showed a 23% decrease in right hind leg volume (FIG. 4A). The group of rats administered with Compound 2 showed a 31% decrease in right hind leg thickness (FIG. 4B).

[0017] FIG. 5 shows that rats administered with Compound 2 showed a 30% decrease in right hind leg volume (FIG. 5A). The right hind leg thickness was measured using calipers. The group of rats administered with Compound 2 showed a 12% decrease in right hind leg thickness (FIG. 5B).

[0018] FIG. 6 Compound 2, when administered at dose of 50 mg/kg p.o., has shown demonstrable effect in gastric irritation model. From the quantitative data on the lines and lesions it is observed that the lines produced are reduced by 47% when Compound 2 is given along with Aspirin.

[0019] FIG. 7 shows that mice administered with Compound 2 showed a 49% decrease of TNF-α(FIG. 7A), 62% decrease of IL-6 (FIG. 7B) and 51% decrease of IL-1B (FIG. 7C) from the LPS group.

[0020] FIG. 8 shows that mice administered with Compound 2 showed a 57% decrease of TNF-α from the LPS group.

[0021] FIG. 9 shows that at the end of the study period of 21 days, the group of mice administered with compound 2 showed a significant (P<0.02) increase by 56% in body weight, compared with the vehicle DSS group.

[0022] FIG. 10 shows at the end of the study period of 21 days, the group of mice administered with Compound 2 showed a significant (P<0.02) decrease by 16% in Disease Activity Index, compared with the vehicle DSS group.

[0023] FIG. 11 shows that at the end of the study period of 21 days, the group of mice administered with Compound 2 showed a 10% increase in colon length, compared with the vehicle DSS group.

[0024] FIG. 12 shows that at the end of the study period of 30 days, the group of rats administered with Compound 2 showed a significant (P<0.02) decrease by 42%, from the vehicle control group in clinical scores

[0025] FIG. 13 shows that at the end of the study period of 30 days, the group of rats administered with Compound 2 showed a decrease by 4% in their number of limbs showing arthritic symptoms, from the vehicle control group.

[0026] FIG. 14 shows that at the end of the study period of 30 days, the group of rats administered with Compound 2 showed a significant (P<0.009) decrease by 33% in their Arthritic Index, from the vehicle control group.

[0027] FIG. 15 shows that the group of rats administered with Compound 3 showed a 7% decrease in right hind leg volume.

[0028] FIG. 16 shows mice administered with Compound 3 showed a 64% decrease in TNF-α(FIG. 16A), 63% decrease in IL-6 (FIG. 16B), and 58% decrease in IL-1B (FIG. 16C) from the LPS group.

[0029] FIG. 17 shows that rats administered with Compound 4 showed a 7% decrease in right hind leg volume.

[0030] FIG. 18 shows that mice administered with Compound 4 showed a 74% decrease in TNF-α (FIG. 18A), 62% decrease in IL-6 (FIG. 18B), and 80% decrease in IL-1B (FIG. 18C) from the LPS group.

[0031] FIG. 19 shows that the group of rats administered with Compound 5 showed a 6% decrease in right hind leg volume (FIG. 19A). The group of rats administered with Compound 5 showed a 6% decrease in right hind leg thickness (FIG. 19B).

[0032] FIG. 20 shows that the group of mice administered with Compound 5 showed a 68% decrease in TNF-α(FIG. 20A), 85% decrease in IL-6 (FIG. 20B), and 82% decrease in IL-1B (FIG. 20C) from the LPS group.

[0033] FIG. 21 The group of mice administered with Compound 6 showed a 50% decrease in TNF-α (FIG. 21A), 74% decrease in IL-6 (FIG. 21B), and 77% decrease in IL-1B (FIG. 21C) from the LPS group.

[0034] FIG. 22 shows that rats administered with Compound 7 showed a 10% decrease in right hind leg volume (FIG. 22A). The group of rats administered with Compound 7 showed a 8% decrease in right hind leg thickness (FIG. 22B).

[0035] FIG. 23 shows that mice administered with Compound 7 showed a 34% decrease in TNF-α (FIG. 23A), 80% decrease in IL-6 (FIG. 23B), and 68% decrease in IL-1B (FIG. 23C) from the LPS group.

[0036] FIG. 24 shows that mice administered with Compound 7 showed a 46% decrease in TNF-α from the LPS group.

[0037] FIG. 25 shows that the group of rats administered with Compound 8 showed a 40% decrease in right hind leg volume.

[0038] FIG. 26 shows that the group of rats administered with Compound 8 showed a 32% decrease in right hind leg volume (FIG. 26A). The group of rats administered with Compound 8 showed a 31% decrease in right hind leg thickness (FIG. 26B).

[0039] FIG. 27 shows that a dose dependent increase in the number of injured hemorrhagic lines (range 6-32) and lesions (range 6-22) were observed in the group of mice administered with Aspirin. A similar dose dependent increase in the number of injured hemorrhagic lines (range 2-20) and lesions (range 3-15) were observed in the group of mice administered with Indomethacin. In the group of mice administered with Compound 8, fewer injured hemorrhagic lines (range <1 to 2) and lesions (range <1 to 3) were observed.

[0040] FIG. 28 shows that the stomach from the Control group of mice did not show any hemorrhagic lines or lesions (FIG. 28A). The stomachs from the Aspirin (FIG. 28B) and Indomethacin (FIG. 28C) groups of mice showed hemorrhagic lines and lesions. The stomach from the group of mice administered with Compound 8 did not show any hemorrhagic lines or lesions (FIG. 28D).

[0041] FIG. 29 shows that the group of mice administered with Compound 8 showed an 84% decrease in TNF-α(FIG. 29A), 90% decrease in IL-6 (FIG. 29B), and 94% decrease in IL-1B (FIG. 29C) from the LPS group.

[0042] FIG. 30 shows that at the end of the study period of 21 days, the group of mice administered with Compound 8 showed an increase by 9% in body weight, compared with the vehicle DSS group.

[0043] FIG. 31 shows that at the end of the study period of 21 days, the group of mice administered with Compound 8 showed a significant (P<0.02) decrease by 29% in Disease Activity Index, compared with the vehicle DSS group.

[0044] FIG. 32 shows that at the end of the study period of 21 days, the group of mice administered with Compound 8 showed a 10% increase in colon length, compared with the vehicle DSS group.

[0045] FIG. 33 shows that at the end of the study period of 30 days, the group of rats administered with Compound 8 showed a significant (P<0.02) decrease by 41%, from the vehicle control group in clinical scores

[0046] FIG. 34 shows that at the end of the study period of 30 days, the group of rats administered with Compound 8 showed a decrease by 10% in their number of limbs showing arthritic symptoms, from the vehicle control group.

[0047] FIG. 35 shows that at the end of the study period of 30 days, the group of rats administered with Compound 8 showed a significant (P<0.0003) decrease by 36% in their Arthritic Index, from the vehicle control group.

[0048] FIG. 36 shows that mice administered with Compound 9 showed a 20% decrease in TNF-α from the LPS group.

[0049] FIG. 37 shows that mice administered with Compound 10 showed a 61% decrease in TNF-α from the LPS group.

[0050] FIG. 38 shows that mice administered with Compound 10 showed a 53% decrease in IL-6 from the LPS group.

[0051] FIG. 39 shows that at the end of the study period of 30 days, the group of rats administered with Compound 11 showed a significant (P<0.02) decrease by 15%, from the vehicle control group in clinical scores

[0052] FIG. 40 shows that the group of mice administered with Compound 12 showed a significant decrease (P<0.0001) by 99% of TNF-α from the Control LPS group.

[0053] FIG. 41 shows that mice administered with Compound 12 showed a decrease by 16% of TNF-α(FIG. 41A) and a significant decrease (P<0.015) by 60% of IL-6 (FIG. 41B), compared from the control LPS group.

[0054] FIG. 42 shows that at the end of the study period of 21 days, the group of mice administered with Compound 12 showed an increase by 44% in body weight, compared with the vehicle DSS group.

[0055] FIG. 43 shows that at the end of the study period of 21 days, the group of mice administered with Compound 12 showed a significant (P<0.002) decrease by 23% in Disease Activity Index, compared with the vehicle DSS group.

[0056] FIG. 44 shows that at the end of the study period of 21 days, the group of mice administered with Compound 12 showed a 9% increase in colon length, compared with the vehicle DSS group.

[0057] FIG. 45 shows that at the end of the study period of 30 days, the group of rats administered with Compound 12 showed a decrease by 7%, from the vehicle control group in the clinical scores.

DETAILED DESCRIPTION OF THE INVENTION

[0058] In an embodiment of the present invention, the group represented as X can be selected from any halogen such as Fluorine, Chlorine, Bromine and Iodine, and Y is selected from hydrogen, halogen such as fluorine, chlorine, bromine or iodine; hydroxyl, nitro, cyano, formyl, amino or sulfonyl groups and the like.

[0059] In an embodiment of the present invention, the groups represented by R.sub.1 and R.sub.3 are selected from linear or branched, substituted or unsubstituted (C.sub.1 to C.sub.12) alkyl groups such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, hexyl, octyl, nonyl and the like; substituted or unsubstituted (C.sub.1 to C.sub.12) alkoxy group such as methoxy, ethoxy, propoxy, butoxy and the like.

[0060] In an embodiment of the present invention, the amino acid group represented by R.sub.4 is selected from alaninie, glycine, arginine, aspargine, cysteine, glutamic acid, glutamine, histidine, isoleucine, leucine, lysine, methionine, ornithine, proline, serine, threonine, tryptophan, tyrosine and the like, which may be unsubstituted or substituted and their derivatives such as ester and amides of carboxylic acid. The preferred substituents are selected from halogen, alkyl, alkoxy, aryl, heteroaryl, amino and the like. R.sub.4 always condenses through the free amino group of the amino acid as represented by N—R.sub.4 in FIG. 1.

[0061] In an embodiment of the present invention, the group R.sub.4 is represented by unsubstituted or substituted aryl amines, pyridyl amine and amino benzoic acid wherein the free amine group condenses to form the Halogenated Benzylidene compound.

[0062] Pharmaceutically acceptable salts forming part of this invention include base addition salts such as alkali metal salts like Li, Na, and K salts, alkaline earth metal salts like Ca and Mg salts, salts of organic bases such as lysine, arginine, guanidine, diethanolamine, chlorine and the like, ammonium or substituted ammonium salts. Salts may include acid addition salts which are sulphates, nitrates, phosphates, perchlorates, borates, hydrohalides, acetates, tartarates, maleates, citrates, succinates, palmoates, methanesulphonates, benzoates, ascorbates, glycerophosphates, ketoglutarates and the like. Pharmaceutically acceptable solvates may be hydrates or comprising other solvents of crystallization such as alcohols.

[0063] More preferably, the present innovation relates to novel Halogenated Benzylidene derivatives of formula (I),

##STR00002##

their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates, novel intermediates and pharmaceutical composites containing them, wherein, the group represented as X is always selected from halogens such as Fluorine, Chlorine, Bromine and Iodine, and Y is selected from hydrogen, halogen such as fluorine, chlorine, bromine or iodine; hydroxyl, nitro, cyano, formyl, amino or sulfonyl groups and the like, the groups represented by R.sub.1 and R.sub.3 are preferentially Hydrogen but can also be selected from linear or branched, substituted or unsubstituted (C.sub.1 to C.sub.12) alkyl groups such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, hexyl, octyl, nonyl and the like; substituted or unsubstituted (C.sub.1 to C.sub.12) alkoxy group such as methoxy, ethoxy, propoxy, butoxy and the like; R.sub.2 corresponds to a free hydroxyl group or extended chain through an alkyloxy ester or un-substituted or substituted aryloxy ester groups; and the amine group represented by R.sub.4 is selected from amino acids such as alaninie, glycine, arginine, aspargine, cysteine, glutamic acid, glutamine, histidine, isoleucine, leucine, lysine, methionine, ornithine, proline, serine, threonine, tryptophan, tyrosine and the like, which may be substituted or unsubstituted and their derivatives such as ester and amides of carboxylic acid. The preferred substituents are selected from halogen, alkyl, alkoxy, aryl, heteroaryl, amino and the like and also R.sub.4 corresponds to un-substituted or substituted aryl amines, pyridyl amine and amino benzoic acid wherein the free amine group condenses to form the Halogenated Benzylidene compounds. The double bond to R.sub.4 can in some compounds be saturated and they are also included in the list of patented compounds.

[0064] The formula of the useful compounds synthesized in this present are listed below. [0065] 2-[(5-Bromo-2-hydroxy-benzylidene)-amino-3-(4-hydroxy phenyl)-propionic acid methyl ester (Compound 1) [0066] 2-[(5-Bromo-2-hydroxy-benzylidene)-amino-3-methyl butyric acid methyl ester (Compound 2) [0067] 2-(5-Bromo-2-hydroxy-benzylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester (Compound 3) [0068] 2-[(5-Bromo-2-hydroxy-benzylidene)-amino-3-(4-hydroxy phenyl)-propionic acid [0069] 4-Bromo-2-{[2-hydroxy-1-(4-hydroxy benzyl)-ethylamino]-Methyl}-phenol (Compound 4) [0070] 2-(5-Bromo-2-hydroxy-benzylamino)-3-methyl-butyric acid methyl ester (Compound 5) [0071] 2-[(5-Bromo-2-hydroxy-benzylidene)-amino]-3-methyl-butyric acid (Compound 6) [0072] 4-Bromo-2-[(1-hydroxymethyl-2-methyl-propylimino)-methyl]-phenol (Compound 7) [0073] (E)-4-bromo-2-((2,4-dichlorophenylimino)methyl) phenyl 4-methylbenzoate (Compound 8) [0074] (E)-4-bromo-2-((4-chlorophenylimino)methyl)phenyl 4-methylbenzoate (Compound 9) [0075] (E)-4-bromo-2-((2,3-dichlorophenylimino)methyl) phenyl 3-methylbenzoate (Compound 10) [0076] (E)-4-bromo-2-((3,4-dichlorophenylimino)methyl) phenyl 4-methylbenzoate [0077] (E)-4-bromo-2-((3,5-dichlorophenylimino)methyl) phenyl 4-methylbenzoate [0078] (E)-4-bromo-2-((phenethylimino)methyl)phenyl 3-methylbenzoate [0079] (E)-4-bromo-2-((phenethylimino)methyl)phenyl 4-methylbenzoate [0080] (E)-4-bromo-2-((pyridin-3-ylimino)methyl)phenyl 4-methylbenzoate [0081] (E)-4-bromo-2-((pyridin-3-ylimino)methyl)phenyl 3-methylbenzoate (Compound 11) [0082] (E)-3-(5-bromo-2-(nicotinoyloxy)benzylideneamino) benzoic acid (Compound 12) [0083] (E)-4-bromo-2-((phenethylimino)methyl)phenyl isobutyrate [0084] 2-[(5-Bromo-2-isobutyryloxy-benzylidene)-amino]-3-(4-isobutyryloxy phenyl propionic acid methyl ester [0085] (E)-4-bromo-2-((4-((diethylamino)methyl)phenylimino)methyl)phenol [0086] (E)-1-(3-chlorobenzylideneamino)-2-methylpropan-1-ol [0087] (E)-1-(3-bromobenzylideneamino)-2-methylpropan-1-ol [0088] (E)-4-chloro-2-((1-hydroxy-2-methylpropylimino)methyl)phenol [0089] (E)-4-bromo-2-((1-hydroxy-2-methylpropylimino)methyl)phenol [0090] (E)-4-chloro-2-((1-hydroxy-2-methylpropylimino)methyl)phenyl isobutyrate [0091] (E)-4-bromo-2-((1-hydroxy-2-methylpropylimino)methyl)phenyl isobutyrate [0092] (E)-3-chloro-5-((1-hydroxy-2-methylpropylimino)methyl)phenyl 4-methylbenzoate [0093] (E)-3-bromo-5-((1-hydroxy-2-methylpropylimino)methyl)phenyl 4-methylbenzoate [0094] (E)-5-chloro-2-hydroxy-3-((1-hydroxy-2-methylpropylimino)methyl)phenyl 4-methylbenzoate [0095] (E)-5-bromo-2-hydroxy-3-((1-hydroxy-2-methylpropylimino)methyl)phenyl 4-methylbenzoate [0096] (E)-5-chloro-3-((1-hydroxy-2-methylpropylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate [0097] (E)-5-bromo-3-((1-hydroxy-2-methylpropylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate [0098] (E)-3-chloro-5-((1-hydroxy-2-methylpropylimino)methyl)phenyl 3-methylbenzoate [0099] (E)-3-bromo-5-((1-hydroxy-2-methylpropylimino)methyl)phenyl 3-methylbenzoate [0100] (E)-5-chloro-2-hydroxy-3-((1-hydroxy-2-methylpropylimino)methyl)phenyl 3-methylbenzoate [0101] (E)-5-bromo-2-hydroxy-3-((1-hydroxy-2-methylpropylimino)methyl)phenyl 3-methylbenzoate [0102] (E)-5-chloro-3-((1-hydroxy-2-methylpropylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate [0103] (E)-5-bromo-3-((1-hydroxy-2-methylpropylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate [0104] (E)-3-chloro-5-((1-hydroxy-2-methylpropylimino)methyl)phenyl nicotinate [0105] (E)-3-bromo-5-((1-hydroxy-2-methylpropylimino)methyl)phenyl nicotinate [0106] (E)-5-chloro-2-hydroxy-3-((1-hydroxy-2-methylpropylimino)methyl)phenyl nicotinate [0107] (E)-5-bromo-2-hydroxy-3-((1-hydroxy-2-methylpropylimino)methyl)phenyl nicotinate [0108] (E)-5-chloro-3-((1-hydroxy-2-methylpropylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate [0109] (E)-5-bromo-3-((1-hydroxy-2-methylpropylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate [0110] (E)-3-chloro-5-((1-hydroxy-2-methylpropylimino)methyl)phenyl isobutyrate [0111] (E)-3-bromo-5-((1-hydroxy-2-methylpropylimino)methyl)phenyl isobutyrate [0112] (E)-5-chloro-2-hydroxy-3-((1-hydroxy-2-methylpropylimino)methyl)phenyl isobutyrate [0113] (E)-5-bromo-2-hydroxy-3-((1-hydroxy-2-methylpropylimino)methyl)phenyl isobutyrate [0114] (E)-5-chloro-2-isobutroxy-3-((1-hydroxy-2-methylpropylimino)methyl)phenyl isobutyrate [0115] (E)-5-bromo-2-isobutroxy-3-((1-hydroxy-2-methylpropylimino)methyl)phenyl isobutyrate [0116] (E)-3-chloro-5-((1-hydroxy-2-methylpropylimino)methyl)phenol [0117] (E)-3-bromo-5-((1-hydroxy-2-methylpropylimino)methyl)phenol [0118] (E)-5-chloro-3-((1-hydroxy-2-methylpropylimino)methyl)benzene-1,2-diol [0119] (E)-5-bromo-3-((1-hydroxy-2-methylpropylimino)methyl)benzene-1,2-diol [0120] (E)-4-chloro-2-hydroxy-6-((1-hydroxy-2-methylpropylimino)methyl)phenyl isobutyrate [0121] (E)-4-bromo-2-hydroxy-6-((1-hydroxy-2-methylpropylimino)methyl)phenyl isobutyrate [0122] methyl 2-(3-chlorobenzylideneamino)-3-methylbutanoate [0123] methyl 2-(3-bromobenzylideneamino)-3-methylbutanoate [0124] methyl 2-(5-chloro-2-hydroxybenzylideneamino)-3-methylbutanoate [0125] methyl 2-(5-bromo-2-hydroxybenzylideneamino)-3-methylbutanoate [0126] methyl 2-(5-chloro-2-(isobutyryloxy)benzylideneamino)-3-methylbutanoate [0127] methyl 2-(5-bromo-2-(isobutyryloxy)benzylideneamino)-3-methylbutanoate [0128] 3-chloro-5-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate [0129] 3-bromo-5-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate [0130] 5-chloro-2-hydroxy-3-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate [0131] 5-bromo-2-hydroxy-3-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate [0132] 5-chloro-2-(isobutyryloxy)-3-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate [0133] 5-bromo-2-(isobutyryloxy)-3-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate [0134] 3-chloro-5-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate [0135] 3-bromo-5-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate [0136] 5-chloro-2-hydroxy-3-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate [0137] 5-bromo-2-hydroxy-3-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate [0138] 5-chloro-2-(isobutyryloxy)-3-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate [0139] 5-bromo-2-(isobutyryloxy)-3-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate [0140] 3-chloro-5-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl nicotinate [0141] 3-bromo-5-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl nicotinate [0142] 5-chloro-2-hydroxy-3-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl nicotinate [0143] 5-bromo-2-hydroxy-3-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl nicotinate [0144] 5-chloro-2-(isobutyryloxy)-3-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl nicotinate [0145] 5-bromo-2-(isobutyryloxy)-3-((1-methoxy-3-methyl-1-oxobutan-2-ylimino)methyl)phenyl nicotinate [0146] methyl 2-(3-chloro-5-(isobutyryloxy)benzylideneamino)-3-methylbutanoate [0147] methyl 2-(3-bromo-5-(isobutyryloxy)benzylideneamino)-3-methylbutanoate [0148] methyl 2-(5-chloro-2-hydroxy-3-(isobutyryloxy)benzylideneamino)-3-methylbutanoate [0149] methyl 2-(5-bromo-2-hydroxy-3-(isobutyryloxy)benzylideneamino)-3-methylbutanoate [0150] methyl 2-(5-chloro-2,3-bis(isobutyryloxy)benzylideneamino)-3-methylbutanoate [0151] methyl 2-(5-bromo-2,3-bis(isobutyryloxy)benzylideneamino)-3-methylbutanoate [0152] methyl 2-(3-chloro-5-hydroxybenzylideneamino)-3-methylbutanoate [0153] methyl 2-(3-bromo-5-hydroxybenzylideneamino)-3-methylbutanoate [0154] methyl 2-(5-chloro-2,3-dihydroxybenzylideneamino)-3-methylbutanoate [0155] methyl 2-(5-bromo-2,3-dihydroxybenzylideneamino)-3-methylbutanoate [0156] methyl 2-(5-chloro-3-hydroxy-2-(3-methylbut-1-en-2-yloxy)benzylideneamino)-3-methylbutanoate [0157] methyl 2-(5-bromo-3-hydroxy-2-(3-methylbut-1-en-2-yloxy)benzylideneamino)-3-methylbutanoate [0158] 2-(3-chlorobenzylideneamino)-3-methylbutanoic acid [0159] 2-(3-bromobenzylideneamino)-3-methylbutanoic acid [0160] 2-(5-chloro-2-hydroxybenzylideneamino)-3-methylbutanoic acid [0161] 2-(5-bromo-2-hydroxybenzylideneamino)-3-methylbutanoic acid [0162] 2-(5-chloro-2-(isobutyryloxy)benzylideneamino)-3-methylbutanoic acid [0163] 2-(5-bromo-2-(isobutyryloxy)benzylideneamino)-3-methylbutanoic acid [0164] 2-(3-chloro-5-(4-methylbenzoyloxy)benzylideneamino)-3-methylbutanoic acid [0165] 2-(3-bromo-5-(4-methylbenzoyloxy)benzylideneamino)-3-methylbutanoic acid [0166] 2-(5-chloro-2-hydroxy-3-(4-methylbenzoyloxy)benzylideneamino)-3-methylbutanoic acid [0167] 2-(5-bromo-2-hydroxy-3-(4-methylbenzoyloxy)benzylideneamino)-3-methylbutanoic acid [0168] 2-(5-chloro-2-(isobutyryloxy)-3-(4-methylbenzoyloxy)benzylideneamino)-3-methylbutanoic acid [0169] 2-(5-bromo-2-(isobutyryloxy)-3-(4-methylbenzoyloxy)benzylideneamino)-3-methylbutanoic acid [0170] 2-(3-chloro-5-(3-methylbenzoyloxy)benzylideneamino)-3-methylbutanoic acid [0171] 2-(3-bromo-5-(3-methylbenzoyloxy)benzylideneamino)-3-methylbutanoic acid [0172] 2-(5-chloro-2-hydroxy-3-(3-methylbenzoyloxy)benzylideneamino)-3-methylbutanoic acid [0173] 2-(5-bromo-2-hydroxy-3-(3-methylbenzoyloxy)benzylideneamino)-3-methylbutanoic acid [0174] 2-(5-chloro-2-(isobutyryloxy)-3-(3-methylbenzoyloxy)benzylideneamino)-3-methylbutanoic acid [0175] 2-(5-bromo-2-(isobutyryloxy)-3-(3-methylbenzoyloxy)benzylideneamino)-3-methylbutanoic acid [0176] 2-(3-chloro-5-(nicotinoyloxy)benzylideneamino)-3-methylbutanoic acid [0177] 2-(3-bromo-5-(nicotinoyloxy)benzylideneamino)-3-methylbutanoic acid [0178] 2-(5-chloro-2-hydroxy-3-(nicotinoyloxy)benzylideneamino)-3-methylbutanoic acid [0179] 2-(5-bromo-2-hydroxy-3-(nicotinoyloxy)benzylideneamino)-3-methylbutanoic acid [0180] 2-(5-chloro-2-(isobutyryloxy)-3-(nicotinoyloxy)benzylideneamino)-3-methylbutanoic acid [0181] 2-(5-bromo-2-(isobutyryloxy)-3-(nicotinoyloxy)benzylideneamino)-3-methylbutanoic acid [0182] 2-(3-chloro-5-(isobutyryloxy)benzylideneamino)-3-methylbutanoic acid [0183] 2-(3-bromo-5-(isobutyryloxy)benzylideneamino)-3-methylbutanoic acid [0184] 2-(5-chloro-2-hydroxy-3-(isobutyryloxy)benzylideneamino)-3-methylbutanoic acid [0185] 2-(5-bromo-2-hydroxy-3-(isobutyryloxy)benzylideneamino)-3-methylbutanoic acid [0186] 2-(5-chloro-2,3-bis(isobutyryloxy)benzylideneamino)-3-methylbutanoic acid [0187] 2-(5-bromo-2,3-bis(isobutyryloxy)benzylideneamino)-3-methylbutanoic acid [0188] 2-(3-chloro-5-hydroxybenzylideneamino)-3-methylbutanoic acid [0189] 2-(3-bromo-5-hydroxybenzylideneamino)-3-methylbutanoic acid [0190] 2-(5-chloro-2,3-dihydroxybenzylideneamino)-3-methylbutanoic acid [0191] 2-(5-bromo-2,3-dihydroxybenzylideneamino)-3-methylbutanoic acid [0192] 2-(5-chloro-3-hydroxy-2-(isobutyryloxy)benzylideneamino)-3-methylbutanoic acid [0193] 2-(5-bromo-3-hydroxy-2-(isobutyryloxy)benzylideneamino)-3-methylbutanoic acid [0194] methyl 2-(3-chlorobenzylideneamino)-3-(4-hydroxyphenyl)propanoate [0195] methyl 2-(3-bromobenzylideneamino)-3-(4-hydroxyphenyl)propanoate [0196] methyl 2-(5-chloro-2-hydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoate [0197] methyl 2-(5-bromo-2-hydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoate [0198] methyl 2-(2-isobutricoxy-5-chlorobenzylideneamino)-3-(4-hydroxyphenyl)propanoate [0199] methyl 2-(2-isobutricoxy-5-bromobenzylideneamino)-3-(4-hydroxyphenyl)propanoate [0200] 3-chloro-5-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)phenyl 4-methylbenzoate [0201] 3-bromo-5-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)phenyl 4-methylbenzoate [0202] 5-chloro-2-hydroxy-3-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)phenyl 4-methylbenzoate [0203] 5-bromo-2-hydroxy-3-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)phenyl 4-methylbenzoate [0204] 5-chloro-3-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate [0205] 5-bromo-3-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate [0206] 3-chloro-5-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)phenyl 3-methylbenzoate [0207] 3-bromo-5-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)phenyl 3-methylbenzoate [0208] 5-chloro-2-hydroxy-3-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)phenyl 3-methylbenzoate [0209] 5-bromo-2-hydroxy-3-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)phenyl 3-methylbenzoate [0210] 5-chloro-3-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate [0211] 5-bromo-3-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate [0212] 3-chloro-5-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)phenyl nicotinate [0213] 3-bromo-5-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)phenyl nicotinate [0214] 5-chloro-2-hydroxy-3-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)phenyl nicotinate [0215] 5-bromo-2-hydroxy-3-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)phenyl nicotinate [0216] 5-chloro-3-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate [0217] 5-bromo-3-((3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-ylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate [0218] methyl 2-(3-isobutryateoxy-5-chlorobenzylideneamino)-3-(4-hydroxyphenyl)propanoate [0219] methyl 2-(3-isobutryateoxy-5-bromobenzylideneamino)-3-(4-hydroxyphenyl)propanoate [0220] methyl 2-(3-isobutryateoxy-5-chloro-2-hydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoate [0221] methyl 2-(3-isobutryateoxy-5-bromo-2-hydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoate [0222] methyl 2-(5-chloro-2,3-bisisobutrateoxybenzylideneamino)-3-(4-hydroxyphenyl)propanoate [0223] methyl 2-(5-bromo-2,3-bisisobutrateoxybenzylideneamino)-3-(4-hydroxyphenyl)propanoate [0224] methyl 2-(3-chloro-5-hydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoate [0225] methyl 2-(3-bromo-5-hydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoate [0226] methyl 2-(5-chloro-2,3-dihydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoate [0227] methyl 2-(5-bromo-2,3-dihydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoate [0228] methyl 2-(5-chloro-2-isobutrateoxy-3-hydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoate [0229] methyl 2-(5-bromo-2-isobutrateoxy-3-hydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoate [0230] 2-(3-chlorobenzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0231] 2-(3-bromobenzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0232] 2-(5-chloro-2-hydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0233] 2-(5-bromo-2-hydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0234] 2-(5-chloro-2-(isobutyryloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0235] 2-(5-bromo-2-(isobutyryloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0236] 2-(3-chloro-5-(4-methylbenzoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0237] 2-(3-bromo-5-(4-methylbenzoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0238] 2-(5-chloro-2-hydroxy-3-(4-methylbenzoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0239] 2-(5-bromo-2-hydroxy-3-(4-methylbenzoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0240] 2-(5-chloro-2-(isobutyryloxy)-3-(4-methylbenzoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0241] 2-(5-bromo-2-(isobutyryloxy)-3-(4-methylbenzoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0242] 2-(3-chloro-5-(3-methylbenzoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0243] 2-(3-bromo-5-(3-methylbenzoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0244] 2-(5-chloro-2-hydroxy-3-(3-methylbenzoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0245] 2-(5-bromo-2-hydroxy-3-(3-methylbenzoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0246] 2-(5-chloro-2-(isobutyryloxy)-3-(3-methylbenzoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0247] 2-(5-bromo-2-(isobutyryloxy)-3-(3-methylbenzoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0248] 2-(3-chloro-5-(nicotinoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0249] 2-(3-bromo-5-(nicotinoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0250] 2-(5-chloro-2-hydroxy-3-(nicotinoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0251] 2-(5-bromo-2-hydroxy-3-(nicotinoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0252] 2-(5-chloro-2-(isobutyryloxy)-3-(nicotinoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0253] 2-(5-bromo-2-(isobutyryloxy)-3-(nicotinoyloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0254] 2-(3-chloro-5-(isobutyryloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0255] 2-(3-bromo-5-(isobutyryloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0256] 2-(5-chloro-2-hydroxy-3-(isobutyryloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0257] 2-(5-bromo-2-hydroxy-3-(isobutyryloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0258] 2-(5-chloro-2,3-bis(isobutyryloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0259] 2-(5-bromo-2,3-bis(isobutyryloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0260] 2-(3-chloro-5-hydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0261] 2-(3-bromo-5-hydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0262] 2-(5-chloro-2,3-dihydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0263] 2-(5-bromo-2,3-dihydroxybenzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0264] 2-(5-chloro-3-hydroxy-2-(isobutyryloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0265] 2-(5-bromo-3-hydroxy-2-(isobutyryloxy)benzylideneamino)-3-(4-hydroxyphenyl)propanoic acid [0266] (Z)-3-(3-chlorobenzylideneamino)-1-hydroxy-4-(4-hydroxyphenyl)butan-2-one [0267] (Z)-3-(3-bromobenzylideneamino)-1-hydroxy-4-(4-hydroxyphenyl)butan-2-one [0268] (Z)-3-(5-chloro-2-hydroxybenzylideneamino)-1-hydroxy-4-(4-hydroxyphenyl)butan-2-one [0269] (Z)-3-(5-bromo-2-hydroxybenzylideneamino)-1-hydroxy-4-(4-hydroxyphenyl)butan-2-one [0270] (Z)-4-chloro-2-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl isobutyrate [0271] (Z)-4-bromo-2-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl isobutyrate [0272] (Z)-3-chloro-5-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate [0273] (Z)-3-bromo-5-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate [0274] (Z)-5-chloro-2-hydroxy-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate [0275] (Z)-5-bromo-2-hydroxy-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate [0276] (Z)-5-chloro-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate [0277] (Z)-5-bromo-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate [0278] (Z)-3-chloro-5-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate [0279] (Z)-3-bromo-5-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate [0280] 5-chloro-2-hydroxy-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate [0281] 5-bromo-2-hydroxy-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate [0282] 5-chloro-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate [0283] 5-bromo-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate [0284] 3-chloro-5-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl nicotinate [0285] 3-bromo-5-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl nicotinate [0286] 5-chloro-2-hydroxy-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl nicotinate [0287] 5-bromo-2-hydroxy-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl nicotinate [0288] 5-chloro-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate [0289] 5-bromo-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate [0290] 3-chloro-5-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl isobutyrate [0291] 3-bromo-5-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl isobutyrate [0292] 5-chloro-2-hydroxy-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl isobutyrate [0293] 5-bromo-2-hydroxy-3-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl isobutyrate [0294] 3-(5-chloro-2,3-bisisobutryloxybenzylideneamino)-1-hydroxy-4-(4-hydroxyphenyl)butan-2-one [0295] 3-(5-bromo-2,3-bisisobutryloxybenzylideneamino)-1-hydroxy-4-(4-hydroxyphenyl)butan-2-one [0296] 3-(3-chloro-5-hydroxybenzylideneamino)-1-hydroxy-4-(4-hydroxyphenyl)butan-2-one [0297] 3-(3-bromo-5-hydroxybenzylideneamino)-1-hydroxy-4-(4-hydroxyphenyl)butan-2-one [0298] 3-(5-chloro-2,3-dihydroxybenzylideneamino)-1-hydroxy-4-(4-hydroxyphenyl)butan-2-one [0299] 3-(5-bromo-2,3-dihydroxybenzylideneamino)-1-hydroxy-4-(4-hydroxyphenyl)butan-2-one [0300] 4-chloro-2-hydroxy-6-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl isobutyrate [0301] 4-bromo-2-hydroxy-6-((4-hydroxy-1-(4-hydroxyphenyl)-3-oxobutan-2-ylimino)methyl)phenyl isobutyrate [0302] 4-(2-(3-chlorobenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate [0303] 4-(2-(3-bromobenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate [0304] 4-(2-(5-chloro-2-hydroxybenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate [0305] 4-(2-(5-bromo-2-hydroxybenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate [0306] 4-(2-(2-isobutryloxy-5-chlorobenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate [0307] 4-(2-(2-isobutryloxy-5-bromobenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate [0308] 3-chloro-5-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate [0309] 3-bromo-5-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate [0310] 5-chloro-2-hydroxy-3-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate [0311] 5-bromo-2-hydroxy-3-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate [0312] 5-chloro-2-(isobutyryloxy)-3-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate [0313] 5-bromo-2-(isobutyryloxy)-3-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl 4-methylbenzoate [0314] 3-chloro-5-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate [0315] 3-bromo-5-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate [0316] 5-chloro-2-hydroxy-3-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate [0317] 5-bromo-2-hydroxy-3-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate [0318] 5-chloro-2-(isobutyryloxy)-3-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate [0319] 5-bromo-2-(isobutyryloxy)-3-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl 3-methylbenzoate [0320] 3-chloro-5-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl nicotinate [0321] 3-bromo-5-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl nicotinate [0322] 5-chloro-2-hydroxy-3-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl nicotinate [0323] 5-bromo-2-hydroxy-3-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl nicotinate [0324] 5-chloro-2-(isobutyryloxy)-3-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl nicotinate [0325] 5-bromo-2-(isobutyryloxy)-3-((1-(4-(isobutyryloxy)phenyl)-4-methoxy-3-oxobutan-2-ylimino)methyl)phenyl nicotinate [0326] 4-(2-(3-isobutryloxy-5-chlorobenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate [0327] 4-(2-(3-isobutryloxy-5-bromobenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate [0328] 4-(2-(3-isobutryloxy-5-chloro-2-hydroxybenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate [0329] 4-(2-(3-isobutryloxy-5-bromo-2-hydroxybenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate [0330] 4-(2-(2,3-bis(isobutryloxy)-5-chlorobenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate [0331] 4-(2-(2,3-bis(isobutryloxy)-5-chlorobenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate [0332] 4-(2-(3-chloro-5-hydroxybenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate [0333] 4-(2-(3-bromo-5-hydroxybenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate [0334] 4-(2-(5-chloro-2,3-dihydroxybenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate [0335] 4-(2-(5-bromo-2,3-dihydroxybenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate [0336] 4-(2-(2-isobutryloxy-5-chloro-3-hydroxybenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate [0337] 4-(2-(2-isobutryloxy-5-bromo-3-hydroxybenzylideneamino)-4-methoxy-3-oxobutyl)phenyl isobutyrate [0338] N-(3-chlorobenzylidene)-2,4-dichlorobenzenamine [0339] N-(3-bromobenzylidene)-2,4-dichlorobenzenamine [0340] 4-chloro-2-((2,4-dichlorophenylimino)methyl)phenol [0341] 4-bromo-2-((2,4-dichlorophenylimino)methyl)phenol [0342] 4-chloro-2-((2,4-dichlorophenylimino)methyl)phenyl isobutyrate [0343] 4-bromo-2-((2,4-dichlorophenylimino)methyl)phenyl isobutyrate [0344] 3-chloro-5-((2,4-dichlorophenylimino)methyl)phenyl 4-methylbenzoate [0345] 3-bromo-5-((2,4-dichlorophenylimino)methyl)phenyl 4-methylbenzoate [0346] 5-chloro-3-((2,4-dichlorophenylimino)methyl)-2-hydroxyphenyl 4-methylbenzoate [0347] 5-bromo-3-((2,4-dichlorophenylimino)methyl)-2-hydroxyphenyl 4-methylbenzoate [0348] 5-chloro-3-((2,4-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate [0349] 5-bromo-3-((2,4-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate [0350] 3-chloro-5-((2,4-dichlorophenylimino)methyl)phenyl 3-methylbenzoate [0351] 3-bromo-5-((2,4-dichlorophenylimino)methyl)phenyl 3-methylbenzoate [0352] 5-chloro-3-((2,4-dichlorophenylimino)methyl)-2-hydroxyphenyl 3-methylbenzoate [0353] 5-bromo-3-((2,4-dichlorophenylimino)methyl)-2-hydroxyphenyl 3-methylbenzoate [0354] 5-chloro-3-((2,4-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate [0355] 5-bromo-3-((2,4-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate [0356] 3-chloro-5-((2,4-dichlorophenylimino)methyl)phenyl nicotinate [0357] 3-bromo-5-((2,4-dichlorophenylimino)methyl)phenyl nicotinate [0358] 5-chloro-3-((2,4-dichlorophenylimino)methyl)-2-hydroxyphenyl nicotinate [0359] 5-bromo-3-((2,4-dichlorophenylimino)methyl)-2-hydroxyphenyl nicotinate [0360] 5-chloro-3-((2,4-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate [0361] 5-bromo-3-((2,4-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate [0362] 3-chloro-5-((2,4-dichlorophenylimino)methyl)phenyl isobutyrate [0363] 3-bromo-5-((2,4-dichlorophenylimino)methyl)phenyl isobutyrate [0364] 5-chloro-3-((2,4-dichlorophenylimino)methyl)-2-hydroxyphenyl isobutyrate [0365] 5-bromo-3-((2,4-dichlorophenylimino)methyl)-2-hydroxyphenyl isobutyrate [0366] N-(2,3-bis(isobutryloxy)-5-chlorobenzylidene)-2,4-dichlorobenzenamine [0367] N-(2,3-bis(isobutryloxy)-5-bromobenzylidene)-2,4-dichlorobenzenamine [0368] 3-chloro-5-((2,4-dichlorophenylimino)methyl)phenol [0369] 3-bromo-5-((2,4-dichlorophenylimino)methyl)phenol [0370] 5-chloro-3-((2,4-dichlorophenylimino)methyl)benzene-1,2-diol [0371] 5-bromo-3-((2,4-dichlorophenylimino)methyl)benzene-1,2-diol [0372] 4-chloro-2-((2,4-dichlorophenylimino)methyl)-6-hydroxyphenyl isobutyrate [0373] 4-bromo-2-((2,4-dichlorophenylimino)methyl)-6-hydroxyphenyl isobutyrate [0374] N-(3-chlorobenzylidene)-4-chlorobenzenamine [0375] N-(3-bromobenzylidene)-4-chlorobenzenamine [0376] 4-chloro-2-((4-chlorophenylimino)methyl)phenol [0377] 4-bromo-2-((4-chlorophenylimino)methyl)phenol [0378] 4-chloro-2-((4-chlorophenylimino)methyl)phenyl isobutyrate [0379] 4-bromo-2-((4-chlorophenylimino)methyl)phenyl isobutyrate [0380] 3-chloro-5-((4-chlorophenylimino)methyl)phenyl 4-methylbenzoate [0381] 3-bromo-5-((4-chlorophenylimino)methyl)phenyl 4-methylbenzoate [0382] 5-chloro-3-((4-chlorophenylimino)methyl)-2-hydroxyphenyl 4-methylbenzoate [0383] 5-bromo-3-((4-chlorophenylimino)methyl)-2-hydroxyphenyl 4-methylbenzoate [0384] 5-chloro-3-((4-chlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate [0385] 5-bromo-3-((4-chlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate [0386] 3-chloro-5-((4-chlorophenylimino)methyl)phenyl 3-methylbenzoate [0387] 3-bromo-5-((4-chlorophenylimino)methyl)phenyl 3-methylbenzoate [0388] 5-chloro-3-((4-chlorophenylimino)methyl)-2-hydroxyphenyl 3-methylbenzoate [0389] 5-bromo-3-((4-chlorophenylimino)methyl)-2-hydroxyphenyl 3-methylbenzoate [0390] 5-chloro-3-((4-chlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate [0391] 5-bromo-3-((4-chlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate [0392] 3-chloro-5-((4-chlorophenylimino)methyl)phenyl nicotinate [0393] 3-bromo-5-((4-chlorophenylimino)methyl)phenyl nicotinate [0394] 5-chloro-3-((4-chlorophenylimino)methyl)-2-hydroxyphenyl nicotinate [0395] 5-bromo-3-((4-chlorophenylimino)methyl)-2-hydroxyphenyl nicotinate [0396] 5-chloro-3-((4-chlorophenylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate [0397] 5-bromo-3-((4-chlorophenylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate [0398] 3-chloro-5-((4-chlorophenylimino)methyl)phenyl isobutyrate [0399] 3-bromo-5-((4-chlorophenylimino)methyl)phenyl isobutyrate [0400] 5-chloro-3-((4-chlorophenylimino)methyl)-2-hydroxyphenyl isobutyrate [0401] 5-bromo-3-((4-chlorophenylimino)methyl)-2-hydroxyphenyl isobutyrate [0402] N-(2,3-bis(isobutryloxy)-5-chlorobenzylidene)-4-chlorobenzenamine [0403] N-(2,3-bis(isobutryloxy)-5-bromobenzylidene)-4-chlorobenzenamine [0404] 3-chloro-5-((4-chlorophenylimino)methyl)phenol [0405] 3-bromo-5-((4-chlorophenylimino)methyl)phenol [0406] 5-chloro-3-((4-chlorophenylimino)methyl)benzene-1,2-diol [0407] 5-bromo-3-((4-chlorophenylimino)methyl)benzene-1,2-diol [0408] 4-chloro-2-((4-chlorophenylimino)methyl)-6-hydroxyphenyl isobutyrate [0409] 4-bromo-2-((4-chlorophenylimino)methyl)-6-hydroxyphenyl isobutyrate [0410] N-(3-chlorobenzylidene)-2,3-dichlorobenzenamine [0411] N-(3-bromobenzylidene)-2,3-dichlorobenzenamine [0412] 4-chloro-2-((2,3-dichlorophenylimino)methyl)phenol [0413] 4-bromo-2-((2,3-dichlorophenylimino)methyl)phenol [0414] 4-chloro-2-((2,3-dichlorophenylimino)methyl)phenyl isobutyrate [0415] 4-bromo-2-((2,3-dichlorophenylimino)methyl)phenyl isobutyrate [0416] 3-chloro-5-((2,3-dichlorophenylimino)methyl)phenyl 4-methylbenzoate [0417] 3-bromo-5-((2,3-dichlorophenylimino)methyl)phenyl 4-methylbenzoate [0418] 5-chloro-3-((2,3-dichlorophenylimino)methyl)-2-hydroxyphenyl 4-methylbenzoate [0419] 5-bromo-3-((2,3-dichlorophenylimino)methyl)-2-hydroxyphenyl 4-methylbenzoate [0420] 5-chloro-3-((2,3-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate [0421] 5-bromo-3-((2,3-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate [0422] 3-chloro-5-((2,3-dichlorophenylimino)methyl)phenyl 3-methylbenzoate [0423] 3-bromo-5-((2,3-dichlorophenylimino)methyl)phenyl 3-methylbenzoate [0424] 5-chloro-3-((2,3-dichlorophenylimino)methyl)-2-hydroxyphenyl 3-methylbenzoate [0425] 5-bromo-3-((2,3-dichlorophenylimino)methyl)-2-hydroxyphenyl 3-methylbenzoate [0426] 5-chloro-3-((2,3-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate [0427] 5-bromo-3-((2,3-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate [0428] 3-chloro-5-((2,3-dichlorophenylimino)methyl)phenyl nicotinate [0429] 3-bromo-5-((2,3-dichlorophenylimino)methyl)phenyl nicotinate [0430] 5-chloro-3-((2,3-dichlorophenylimino)methyl)-2-hydroxyphenyl nicotinate [0431] 5-bromo-3-((2,3-dichlorophenylimino)methyl)-2-hydroxyphenyl nicotinate [0432] 5-chloro-3-((2,3-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate [0433] 5-bromo-3-((2,3-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate [0434] 3-chloro-5-((2,3-dichlorophenylimino)methyl)phenyl isobutyrate [0435] 3-bromo-5-((2,3-dichlorophenylimino)methyl)phenyl isobutyrate [0436] 5-chloro-3-((2,3-dichlorophenylimino)methyl)-2-hydroxyphenyl isobutyrate [0437] 5-bromo-3-((2,3-dichlorophenylimino)methyl)-2-hydroxyphenyl isobutyrate [0438] N-(2,3-bis(isobutryloxy)-5-chlorobenzylidene)-2,3-dichlorobenzenamine [0439] N-(2,3-bis(isobutryloxy)-5-bromobenzylidene)-2,3-dichlorobenzenamine [0440] 3-chloro-5-((2,3-dichlorophenylimino)methyl)phenol [0441] 3-bromo-5-((2,3-dichlorophenylimino)methyl)phenol [0442] 5-chloro-3-((2,3-dichlorophenylimino)methyl)benzene-1,2-diol [0443] 5-bromo-3-((2,3-dichlorophenylimino)methyl)benzene-1,2-diol [0444] 4-chloro-2-((2,3-dichlorophenylimino)methyl)-6-hydroxyphenyl isobutyrate [0445] 4-bromo-2-((2,3-dichlorophenylimino)methyl)-6-hydroxyphenyl isobutyrate [0446] N-(3-chlorobenzylidene)-3,5-dichlorobenzenamine [0447] N-(3-bromobenzylidene)-3,5-dichlorobenzenamine [0448] 4-chloro-2-((3,5-dichlorophenylimino)methyl)phenol [0449] 4-bromo-2-((3,5-dichlorophenylimino)methyl)phenol [0450] 4-chloro-2-((3,5-dichlorophenylimino)methyl)phenyl isobutyrate [0451] 4-bromo-2-((3,5-dichlorophenylimino)methyl)phenyl isobutyrate [0452] 3-chloro-5-((3,5-dichlorophenylimino)methyl)phenyl 4-methylbenzoate [0453] 3-bromo-5-((3,5-dichlorophenylimino)methyl)phenyl 4-methylbenzoate [0454] 5-chloro-3-((3,5-dichlorophenylimino)methyl)-2-hydroxyphenyl 4-methylbenzoate [0455] 5-bromo-3-((3,5-dichlorophenylimino)methyl)-2-hydroxyphenyl 4-methylbenzoate [0456] 5-chloro-3-((3,5-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate [0457] 5-bromo-3-((3,5-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate [0458] 5-chloro-3-((3,5-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate [0459] 5-bromo-3-((3,5-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate [0460] 5-chloro-3-((3,5-dichlorophenylimino)methyl)-2-hydroxyphenyl 3-methylbenzoate [0461] 5-bromo-3-((3,5-dichlorophenylimino)methyl)-2-hydroxyphenyl 3-methylbenzoate [0462] 5-chloro-3-((3,5-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate [0463] 5-bromo-3-((3,5-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate [0464] 3-chloro-5-((3,5-dichlorophenylimino)methyl)phenyl nicotinate [0465] 3-bromo-5-((3,5-dichlorophenylimino)methyl)phenyl nicotinate [0466] 5-chloro-3-((3,5-dichlorophenylimino)methyl)-2-hydroxyphenyl nicotinate [0467] 5-bromo-3-((3,5-dichlorophenylimino)methyl)-2-hydroxyphenyl nicotinate [0468] 5-chloro-3-((3,5-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate [0469] 5-bromo-3-((3,5-dichlorophenylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate [0470] 3-chloro-5-((3,5-dichlorophenylimino)methyl)phenyl isobutyrate [0471] 3-bromo-5-((3,5-dichlorophenylimino)methyl)phenyl isobutyrate [0472] 5-chloro-3-((3,5-dichlorophenylimino)methyl)-2-hydroxyphenyl isobutyrate [0473] 5-bromo-3-((3,5-dichlorophenylimino)methyl)-2-hydroxyphenyl isobutyrate [0474] N-(2,3-bis(isobutryloxy)-5-chlorobenzylidene)-3,5-dichlorobenzenamine [0475] N-(2,3-bis(isobutryloxy)-5-bromobenzylidene)-3,5-dichlorobenzenamine [0476] 3-chloro-5-((3,5-dichlorophenylimino)methyl)phenol [0477] 3-bromo-5-((3,5-dichlorophenylimino)methyl)phenol [0478] 5-chloro-3-((3,5-dichlorophenylimino)methyl)benzene-1,2-diol [0479] 5-bromo-3-((3,5-dichlorophenylimino)methyl)benzene-1,2-diol [0480] 4-chloro-2-((3,5-dichlorophenylimino)methyl)-6-hydroxyphenyl isobutyrate [0481] 4-bromo-2-((3,5-dichlorophenylimino)methyl)-6-hydroxyphenyl isobutyrate [0482] N-(3-chlorobenzylidene)-2-phenylethanamine [0483] N-(3-bromobenzylidene)-2-phenylethanamine [0484] 4-chloro-2-((phenethylimino)methyl)phenol [0485] 4-bromo-2-((phenethylimino)methyl)phenol [0486] 4-chloro-2-((phenethylimino)methyl)phenyl isobutyrate [0487] 4-bromo-2-((phenethylimino)methyl)phenyl isobutyrate [0488] 3-chloro-5-((phenethylimino)methyl)phenyl 4-methylbenzoate [0489] 3-bromo-5-((phenethylimino)methyl)phenyl 4-methylbenzoate [0490] 5-chloro-2-hydroxy-3-((phenethylimino)methyl)phenyl 4-methylbenzoate [0491] 5-bromo-2-hydroxy-3-((phenethylimino)methyl)phenyl 4-methylbenzoate [0492] 5-chloro-2-(isobutyryloxy)-3-((phenethylimino)methyl)phenyl 4-methylbenzoate [0493] 5-bromo-2-(isobutyryloxy)-3-((phenethylimino)methyl)phenyl 4-methylbenzoate [0494] 3-chloro-5-((phenethylimino)methyl)phenyl 3-methylbenzoate [0495] 3-bromo-5-((phenethylimino)methyl)phenyl 3-methylbenzoate [0496] 5-chloro-2-hydroxy-3-((phenethylimino)methyl)phenyl 3-methylbenzoate [0497] 5-bromo-2-hydroxy-3-((phenethylimino)methyl)phenyl 3-methylbenzoate [0498] 5-chloro-2-(isobutyryloxy)-3-((phenethylimino)methyl)phenyl 3-methylbenzoate [0499] 5-bromo-2-(isobutyryloxy)-3-((phenethylimino)methyl)phenyl 3-methylbenzoate [0500] 3-chloro-5-((phenethylimino)methyl)phenyl nicotinate [0501] 3-bromo-5-((phenethylimino)methyl)phenyl nicotinate [0502] 5-chloro-2-hydroxy-3-((phenethylimino)methyl)phenyl nicotinate [0503] 5-bromo-2-hydroxy-3-((phenethylimino)methyl)phenyl nicotinate [0504] 5-chloro-2-(isobutyryloxy)-3-((phenethylimino)methyl)phenyl nicotinate [0505] 5-bromo-2-(isobutyryloxy)-3-((phenethylimino)methyl)phenyl nicotinate [0506] 3-chloro-5-((phenethylimino)methyl)phenyl isobutyrate [0507] 3-bromo-5-((phenethylimino)methyl)phenyl isobutyrate [0508] 5-chloro-2-hydroxy-3-((phenethylimino)methyl)phenyl isobutyrate [0509] 5-bromo-2-hydroxy-3-((phenethylimino)methyl)phenyl isobutyrate [0510] N-(2,3-bis(isobutryloxy)-5-chlorobenzylidene)-2-phenylethanamine [0511] N-(2,3-bis(isobutryloxy)-5-bromobenzylidene)-2-phenylethanamine [0512] 3-chloro-5-((phenethylimino)methyl)phenol [0513] 3-bromo-5-((phenethylimino)methyl)phenol [0514] 5-chloro-3-((phenethylimino)methyl)benzene-1,2-diol [0515] 5-bromo-3-((phenethylimino)methyl)benzene-1,2-diol [0516] 4-chloro-2-hydroxy-6-((phenethylimino)methyl)phenyl isobutyrate [0517] 4-bromo-2-hydroxy-6-((phenethylimino)methyl)phenyl isobutyrate [0518] N-(3-chlorobenzylidene)-4-((diethylamino)methyl)benzenamine [0519] N-(3-bromobenzylidene)-4-((diethylamino)methyl)benzenamine [0520] 4-chloro-2-((4-((diethylamino)methyl)phenylimino)methyl)phenol [0521] 4-bromo-2-((4-((diethylamino)methyl)phenylimino)methyl)phenol [0522] 4-chloro-2-((4-((diethylamino)methyl)phenylimino)methyl)phenyl isobutyrate [0523] 4-bromo-2-((4-((diethylamino)methyl)phenylimino)methyl)phenyl isobutyrate [0524] 3-chloro-5-((4-((diethylamino)methyl)phenylimino)methyl)phenyl 4-methylbenzoate [0525] 3-bromo-5-((4-((diethylamino)methyl)phenylimino)methyl)phenyl 4-methylbenzoate [0526] 5-chloro-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-hydroxyphenyl 4-methylbenzoate [0527] 5-bromo-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-hydroxyphenyl 4-methylbenzoate [0528] 5-chloro-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate [0529] 5-bromo-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-(isobutyryloxy)phenyl 4-methylbenzoate [0530] 3-chloro-5-((4-((diethylamino)methyl)phenylimino)methyl)phenyl 3-methylbenzoate [0531] 3-bromo-5-((4-((diethylamino)methyl)phenylimino)methyl)phenyl 3-methylbenzoate [0532] 5-chloro-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-hydroxyphenyl 3-methylbenzoate [0533] 5-bromo-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-hydroxyphenyl 3-methylbenzoate [0534] 5-chloro-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate [0535] 5-bromo-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-(isobutyryloxy)phenyl 3-methylbenzoate [0536] 3-chloro-5-((4-((diethylamino)methyl)phenylimino)methyl)phenyl nicotinate [0537] 3-bromo-5-((4-((diethylamino)methyl)phenylimino)methyl)phenyl nicotinate [0538] 5-chloro-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-hydroxyphenyl nicotinate [0539] 5-bromo-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-hydroxyphenyl nicotinate [0540] 5-chloro-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate [0541] 5-bromo-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-(isobutyryloxy)phenyl nicotinate [0542] 3-chloro-5-((4-((diethylamino)methyl)phenylimino)methyl)phenyl isobutyrate [0543] 3-bromo-5-((4-((diethylamino)methyl)phenylimino)methyl)phenyl isobutyrate [0544] 5-chloro-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-hydroxyphenyl isobutyrate [0545] 5-bromo-3-((4-((diethylamino)methyl)phenylimino)methyl)-2-hydroxyphenyl isobutyrate [0546] N-(2,3-bis(isobutryloxy)-5-chlorobenzylidene)-4-((diethylamino)methyl)benzenamine [0547] N-(2,3-bis(isobutryloxy)-5-bromobenzylidene)-4-((diethylamino)methyl)benzenamine [0548] 3-chloro-5-((4-((diethylamino)methyl)phenylimino)methyl)phenol [0549] 3-bromo-5-((4-((diethylamino)methyl)phenylimino)methyl)phenol [0550] 5-chloro-3-((4-((diethylamino)methyl)phenylimino)methyl)benzene-1,2-diol [0551] 5-bromo-3-((4-((diethylamino)methyl)phenylimino)methyl)benzene-1,2-diol [0552] 4-chloro-2-((4-((diethylamino)methyl)phenylimino)methyl)-6-hydroxyphenyl isobutyrate [0553] 4-bromo-2-((4-((diethylamino)methyl)phenylimino)methyl)-6-hydroxyphenyl isobutyrate [0554] N-(3-chlorobenzylidene)pyridin-3-amine [0555] N-(3-bromobenzylidene)pyridin-3-amine [0556] 4-chloro-2-((pyridin-3-ylimino)methyl)phenol [0557] 4-bromo-2-((pyridin-3-ylimino)methyl)phenol [0558] 4-chloro-2-((pyridin-3-ylimino)methyl)phenyl isobutyrate [0559] 4-bromo-2-((pyridin-3-ylimino)methyl)phenyl isobutyrate [0560] 3-chloro-5-((pyridin-3-ylimino)methyl)phenyl 4-methylbenzoate [0561] 3-bromo-5-((pyridin-3-ylimino)methyl)phenyl 4-methylbenzoate [0562] 5-chloro-2-hydroxy-3-((pyridin-3-ylimino)methyl)phenyl 4-methylbenzoate [0563] 5-bromo-2-hydroxy-3-((pyridin-3-ylimino)methyl)phenyl 4-methylbenzoate [0564] 5-chloro-2-(isobutyryloxy)-3-((pyridin-3-ylimino)methyl)phenyl 4-methylbenzoate [0565] 5-bromo-2-(isobutyryloxy)-3-((pyridin-3-ylimino)methyl)phenyl 4-methylbenzoate [0566] 3-chloro-5-((pyridin-3-ylimino)methyl)phenyl 3-methylbenzoate [0567] 3-bromo-5-((pyridin-3-ylimino)methyl)phenyl 3-methylbenzoate [0568] 5-chloro-2-hydroxy-3-((pyridin-3-ylimino)methyl)phenyl 3-methylbenzoate [0569] 5-bromo-2-hydroxy-3-((pyridin-3-ylimino)methyl)phenyl 3-methylbenzoate [0570] 5-chloro-2-(isobutyryloxy)-3-((pyridin-3-ylimino)methyl)phenyl 3-methylbenzoate [0571] 5-bromo-2-(isobutyryloxy)-3-((pyridin-3-ylimino)methyl)phenyl 3-methylbenzoate [0572] 3-chloro-5-((pyridin-3-ylimino)methyl)phenyl nicotinate [0573] 3-bromo-5-((pyridin-3-ylimino)methyl)phenyl nicotinate [0574] 5-chloro-2-hydroxy-3-((pyridin-3-ylimino)methyl)phenyl nicotinate [0575] 5-bromo-2-hydroxy-3-((pyridin-3-ylimino)methyl)phenyl nicotinate [0576] 5-chloro-2-(isobutyryloxy)-3-((pyridin-3-ylimino)methyl)phenyl nicotinate [0577] 5-bromo-2-(isobutyryloxy)-3-((pyridin-3-ylimino)methyl)phenyl nicotinate [0578] 3-chloro-5-((pyridin-3-ylimino)methyl)phenyl isobutyrate [0579] 3-bromo-5-((pyridin-3-ylimino)methyl)phenyl isobutyrate [0580] 5-chloro-2-hydroxy-3-((pyridin-3-ylimino)methyl)phenyl isobutyrate [0581] 5-bromo-2-hydroxy-3-((pyridin-3-ylimino)methyl)phenyl isobutyrate [0582] N-(2,3-bis(isobutryloxy)-5-chlorobenzylidene)pyridin-3-amine [0583] N-(2,3-bis(isobutryloxy)-5-bromobenzylidene)pyridin-3-amine [0584] 3-chloro-5-((pyridin-3-ylimino)methyl)phenol [0585] 3-bromo-5-((pyridin-3-ylimino)methyl)phenol [0586] 5-chloro-3-((pyridin-3-ylimino)methyl)benzene-1,2-diol [0587] 5-bromo-3-((pyridin-3-ylimino)methyl)benzene-1,2-diol [0588] 4-chloro-2-hydroxy-6-((pyridin-3-ylimino)methyl)phenyl isobutyrate [0589] 4-bromo-2-hydroxy-6-((pyridin-3-ylimino)methyl)phenyl isobutyrate [0590] 3-(3-chlorobenzylideneamino)benzoic acid [0591] 3-(3-bromobenzylideneamino)benzoic acid [0592] 3-(5-chloro-2-hydroxybenzylideneamino)benzoic acid [0593] 3-(5-bromo-2-hydroxybenzylideneamino)benzoic acid [0594] 3-(5-chloro-2-(isobutyryloxy)benzylideneamino)benzoic acid [0595] 3-(5-bromo-2-(isobutyryloxy)benzylideneamino)benzoic acid [0596] 3-(3-chloro-5-(4-methylbenzoyloxy)benzylideneamino)benzoic acid [0597] 3-(3-bromo-5-(4-methylbenzoyloxy)benzylideneamino)benzoic acid [0598] 3-(5-chloro-2-hydroxy-3-(4-methylbenzoyloxy)benzylideneamino)benzoic acid [0599] 3-(5-bromo-2-hydroxy-3-(4-methylbenzoyloxy)benzylideneamino)benzoic acid [0600] 3-(5-chloro-2-(isobutyryloxy)-3-(4-methylbenzoyloxy)benzylideneamino)benzoic acid [0601] 3-(5-bromo-2-(isobutyryloxy)-3-(4-methylbenzoyloxy)benzylideneamino)benzoic acid [0602] 3-(3-chloro-5-(3-methylbenzoyloxy)benzylideneamino)benzoic acid [0603] 3-(3-bromo-5-(3-methylbenzoyloxy)benzylideneamino)benzoic acid [0604] 3-(5-chloro-2-hydroxy-3-(3-methylbenzoyloxy)benzylideneamino)benzoic acid [0605] 3-(5-bromo-2-hydroxy-3-(3-methylbenzoyloxy)benzylideneamino)benzoic acid [0606] 3-(5-chloro-2-(isobutyryloxy)-3-(3-methylbenzoyloxy)benzylideneamino)benzoic acid [0607] 3-(5-bromo-2-(isobutyryloxy)-3-(3-methylbenzoyloxy)benzylideneamino)benzoic acid [0608] 3-(3-chloro-5-(nicotinoyloxy)benzylideneamino)benzoic acid [0609] 3-(3-bromo-5-(nicotinoyloxy)benzylideneamino)benzoic acid [0610] 3-(5-chloro-2-hydroxy-3-(nicotinoyloxy)benzylideneamino)benzoic acid [0611] 3-(5-bromo-2-hydroxy-3-(nicotinoyloxy)benzylideneamino)benzoic acid [0612] 3-(5-chloro-2-(isobutyryloxy)-3-(nicotinoyloxy)benzylideneamino)benzoic acid [0613] 3-(5-bromo-2-(isobutyryloxy)-3-(nicotinoyloxy)benzylideneamino)benzoic acid [0614] 3-(3-chloro-5-(isobutyryloxy)benzylideneamino)benzoic acid [0615] 3-(3-bromo-5-(isobutyryloxy)benzylideneamino)benzoic acid [0616] 3-(5-chloro-2-hydroxy-3-(isobutyryloxy)benzylideneamino)benzoic acid [0617] 3-(5-bromo-2-hydroxy-3-(isobutyryloxy)benzylideneamino)benzoic acid [0618] 3-(2,3-bis(isobutryloxy)-5-chlorobenzylideneamino)benzoic acid [0619] 3-(2,3-bis(isobutryloxy)-5-bromobenzylideneamino)benzoic acid [0620] 3-(3-chloro-5-hydroxybenzylideneamino)benzoic acid [0621] 3-(3-bromo-5-hydroxybenzylideneamino)benzoic acid [0622] 3-(5-chloro-2,3-dihydroxybenzylideneamino)benzoic acid [0623] 3-(5-bromo-2,3-dihydroxybenzylideneamino)benzoic acid [0624] 3-(5-chloro-3-hydroxy-2-(isobutyryloxy)benzylideneamino)benzoic acid [0625] 3-(5-bromo-3-hydroxy-2-(isobutyryloxy)benzylideneamino)benzoic acid

TABLE-US-00001 [00003] R.sub.4 is bonded though N, R.sub.2 in cases is bonded through O S.No R4 R2 Y X  1. [00004] H H Cl  2. [00005] H H Br  3. [00006] H OH Cl  4. [00007] H OH Br  5. [00008] H [00009] Cl  6. [00010] H [00011] Br  7. [00012] [00013] H Cl  8. [00014] [00015] H Br  9. [00016] [00017] OH Cl  10. [00018] [00019] OH Br  11. [00020] [00021] [00022] Cl  12. [00023] [00024] [00025] Br  13. [00026] [00027] H Cl  14. [00028] [00029] H Br  15. [00030] [00031] OH Cl  16. [00032] [00033] OH Br  17. [00034] [00035] [00036] Cl  18. [00037] [00038] [00039] Br  19. [00040] [00041] H Cl  20. [00042] [00043] H Br  21. [00044] [00045] OH Cl  22. [00046] [00047] OH Br  23. [00048] [00049] [00050] Cl  24. [00051] [00052] [00053] Br  25. [00054] [00055] H Cl  26. [00056] [00057] H Br  27. [00058] [00059] OH Cl  28. [00060] [00061] OH Br  29. [00062] [00063] [00064] Cl  30. [00065] [00066] [00067] Br  31. [00068] OH H Cl  32. [00069] OH H Br  33. [00070] OH OH Cl  34. [00071] OH OH Br  35. [00072] OH [00073] Cl  36. [00074] OH [00075] Br  37. [00076] H H Cl  38. [00077] H H Br  39. [00078] H OH Cl  40. [00079] H OH Br  41. [00080] H [00081] Cl  42. [00082] H [00083] Br  43. [00084] [00085] H Cl  44. [00086] [00087] H Br  45. [00088] [00089] OH Cl  46. [00090] [00091] OH Br  47. [00092] [00093] [00094] Cl  48. [00095] [00096] [00097] Br  49. [00098] [00099] H Cl  50. [00100] [00101] H Br  51. [00102] [00103] OH Cl  52. [00104] [00105] OH Br  53. [00106] [00107] [00108] Cl  54. [00109] [00110] [00111] Br  55. [00112] [00113] H Cl  56. [00114] [00115] H Br  57. [00116] [00117] OH Cl  58. [00118] [00119] OH Br  59. [00120] [00121] [00122] Cl  60. [00123] [00124] [00125] Br  61. [00126] [00127] H Cl  62. [00128] [00129] H Br  63. [00130] [00131] OH Cl  64. [00132] [00133] OH Br  65. [00134] [00135] [00136] Cl  66. [00137] [00138] [00139] Br  67. [00140] OH H Cl  68. [00141] OH H Br  69. [00142] OH OH Cl  70. [00143] OH OH Br  71. [00144] OH [00145] Cl  72. [00146] OH [00147] Br  73. [00148] H H Cl  74. [00149] H H Br  75. [00150] H OH Cl  76. [00151] H OH Br  77. [00152] H [00153] Cl  78. [00154] H [00155] Br  79. [00156] [00157] H Cl  80. [00158] [00159] H Br  81. [00160] [00161] OH Cl  82. [00162] [00163] OH Br  83. [00164] [00165] [00166] Cl  84. [00167] [00168] [00169] Br  85. [00170] [00171] H Cl  86. [00172] [00173] H Br  87. [00174] [00175] OH Cl  88. [00176] [00177] OH Br  89. [00178] [00179] [00180] Cl  90. [00181] [00182] [00183] Br  91. [00184] [00185] H Cl  92. [00186] [00187] H Br  93. [00188] [00189] OH Cl  94. [00190] [00191] OH Br  95. [00192] [00193] [00194] Cl  96. [00195] [00196] [00197] Br  97. [00198] [00199] H Cl  98. [00200] [00201] H Br  99. [00202] [00203] OH Cl 100. [00204] [00205] OH Br 101. [00206] [00207] [00208] Cl 102. [00209] [00210] [00211] Br 103. [00212] OH H Cl 104. [00213] OH H Br 105. [00214] OH OH Cl 106. [00215] OH OH Br 107. [00216] OH [00217] Cl 108. [00218] OH [00219] Br 109. [00220] H H Cl 110. [00221] H H Br 111. [00222] H OH Cl 112. [00223] H OH Br 113. [00224] H [00225] Cl 114. [00226] H [00227] Br 115. [00228] [00229] H Cl 116. [00230] [00231] H Br 117. [00232] [00233] OH Cl 118. [00234] [00235] OH Br 119. [00236] [00237] [00238] Cl 120. [00239] [00240] [00241] Br 121. [00242] [00243] H Cl 122. [00244] [00245] H Br 123. [00246] [00247] OH Cl 124. [00248] [00249] OH Br 125. [00250] [00251] [00252] Cl 126. [00253] [00254] [00255] Br 127. [00256] [00257] H Cl 128. [00258] [00259] H Br 129. [00260] [00261] OH Cl 130. [00262] [00263] OH Br 131. [00264] [00265] [00266] Cl 132. [00267] [00268] [00269] Br 133. [00270] [00271] H Cl 134. [00272] [00273] H Br 135. [00274] [00275] OH Cl 136. [00276] [00277] OH Br 137. [00278] [00279] [00280] Cl 138. [00281] [00282] [00283] Br 139. [00284] OH H Cl 140. [00285] OH H Br 141. [00286] OH OH Cl 142. [00287] OH OH Br 143. [00288] OH [00289] Cl 144. [00290] OH [00291] Br 145. [00292] H H Cl 146. [00293] H H Br 147. [00294] H OH Cl 148. [00295] H OH Br 149. [00296] H [00297] Cl 150. [00298] H [00299] Br 151. [00300] [00301] H Cl 152. [00302] [00303] H Br 153. [00304] [00305] OH Cl 154. [00306] [00307] OH Br 155. [00308] [00309] [00310] Cl 156. [00311] [00312] [00313] Br 157. [00314] [00315] H Cl 158. [00316] [00317] H Br 159. [00318] [00319] OH Cl 160. [00320] [00321] OH Br 161. [00322] [00323] [00324] Cl 162. [00325] [00326] [00327] Br 163. [00328] [00329] H Cl 164. [00330] [00331] H Br 165. [00332] [00333] OH Cl 166. [00334] [00335] OH Br 167. [00336] [00337] [00338] Cl 168. [00339] [00340] [00341] Br 169. [00342] [00343] H Cl 170. [00344] [00345] H Br 171. [00346] [00347] OH Cl 172. [00348] [00349] OH Br 173. [00350] [00351] [00352] Cl 174. [00353] [00354] [00355] Br 175. [00356] OH H Cl 176. [00357] OH H Br 177. [00358] OH OH Cl 178. [00359] OH OH Br 179. [00360] OH [00361] Cl 180. [00362] OH [00363] Br 181. [00364] H H Cl 182. [00365] H H Br 183. [00366] H OH Cl 184. [00367] H OH Br 185. [00368] H [00369] Cl 186. [00370] H [00371] Br 187. [00372] [00373] H Cl 188. [00374] [00375] H Br 189. [00376] [00377] OH Cl 190. [00378] [00379] OH Br 191. [00380] [00381] [00382] Cl 192. [00383] [00384] [00385] Br 193. [00386] [00387] H Cl 194. [00388] [00389] H Br 195. [00390] [00391] OH Cl 196. [00392] [00393] OH Br 197. [00394] [00395] [00396] Cl 198. [00397] [00398] [00399] Br 199. [00400] [00401] H Cl 200. [00402] [00403] H Br 201. [00404] [00405] OH Cl 202. [00406] [00407] OH Br 203. [00408] [00409] [00410] Cl 204. [00411] [00412] [00413] Br 205. [00414] [00415] H Cl 206. [00416] [00417] H Br 207. [00418] [00419] OH Cl 208. [00420] [00421] OH Br 209. [00422] [00423] [00424] Cl 210. [00425] [00426] [00427] Br 211. [00428] OH H Cl 212. [00429] OH H Br 213. [00430] OH OH Cl 214. [00431] OH OH Br 215. [00432] OH [00433] Cl 216. [00434] OH [00435] Br 217. [00436] H H Cl 218. [00437] H H Br 219. [00438] H OH Cl 220. [00439] H OH Br 221. [00440] H [00441] Cl 222. [00442] H [00443] Br 223. [00444] [00445] H Cl 224. [00446] [00447] H Br 225. [00448] [00449] OH Cl 226. [00450] [00451] OH Br 227. [00452] [00453] [00454] Cl 228. [00455] [00456] [00457] Br 229. [00458] [00459] H Cl 230. [00460] [00461] H Br 231. [00462] [00463] OH Cl 232. [00464] [00465] OH Br 233. [00466] [00467] [00468] Cl 234. [00469] [00470] [00471] Br 235. [00472] [00473] H Cl 236. [00474] [00475] H Br 237. [00476] [00477] OH Cl 238. [00478] [00479] OH Br 239. [00480] [00481] [00482] Cl 240. [00483] [00484] [00485] Br 241. [00486] [00487] H Cl 242. [00488] [00489] H Br 243. [00490] [00491] OH Cl 244. [00492] [00493] OH Br 245. [00494] [00495] [00496] Cl 246. [00497] [00498] [00499] Br 247. [00500] OH H Cl 248. [00501] OH H Br 249. [00502] OH OH Cl 250. [00503] OH OH Br 251. [00504] OH [00505] Cl 252. [00506] OH [00507] Br 253. [00508] H H Cl 254. [00509] H H Br 255. [00510] H OH Cl 256. [00511] H OH Br 257. [00512] H [00513] Cl 258. [00514] H [00515] Br 259. [00516] [00517] H Cl 260. [00518] [00519] H Br 261. [00520] [00521] OH Cl 262. [00522] [00523] OH Br 263. [00524] [00525] [00526] Cl 264. [00527] [00528] [00529] Br 265. [00530] [00531] H Cl 266. [00532] [00533] H Br 267. [00534] [00535] OH Cl 268. [00536] [00537] OH Br 269. [00538] [00539] [00540] Cl 270. [00541] [00542] [00543] Br 271. [00544] [00545] H Cl 272. [00546] [00547] H Br 273. [00548] [00549] OH Cl 274. [00550] [00551] OH Br 275. [00552] [00553] [00554] Cl 276. [00555] [00556] [00557] Br 277. [00558] [00559] H Cl 278. [00560] [00561] H Br 279. [00562] [00563] OH Cl 280. [00564] [00565] OH Br 281. [00566] [00567] [00568] Cl 282. [00569] [00570] [00571] Br 283. [00572] OH H Cl 284. [00573] OH H Br 285. [00574] OH OH Cl 286. [00575] OH OH Br 287. [00576] OH [00577] Cl 288. [00578] OH [00579] Br 289. [00580] H H Cl 290. [00581] H H Br 291. [00582] H OH Cl 292. [00583] H OH Br 293. [00584] H [00585] Cl 294. [00586] H [00587] Br 295. [00588] [00589] H Cl 296. [00590] [00591] H Br 297. [00592] [00593] OH Cl 298. [00594] [00595] OH Br 299. [00596] [00597] [00598] Cl 300. [00599] [00600] [00601] Br 301. [00602] [00603] H Cl 302. [00604] [00605] H Br 303. [00606] [00607] OH Cl 304. [00608] [00609] OH Br 305. [00610] [00611] [00612] Cl 306. [00613] [00614] [00615] Br 307. [00616] [00617] H Cl 308. [00618] [00619] H Br 309. [00620] [00621] OH Cl 310. [00622] [00623] OH Br 311. [00624] [00625] [00626] Cl 312. [00627] [00628] [00629] Br 313. [00630] [00631] H Cl 314. [00632] [00633] H Br 315. [00634] [00635] OH Cl 316. [00636] [00637] OH Br 317. [00638] [00639] [00640] Cl 318. [00641] [00642] [00643] Br 319. [00644] OH H Cl 320. [00645] OH H Br 321. [00646] OH OH Cl 322. [00647] OH OH Br 323. [00648] OH [00649] Br 324. [00650] OH [00651] Br 325. [00652] H H Cl 326. [00653] H H Br 327. [00654] H OH Cl 328. [00655] H OH Br 329. [00656] H [00657] Cl 330. [00658] H [00659] Br 331. [00660] [00661] H Cl 332. [00662] [00663] H Br 333. [00664] [00665] OH Cl 334. [00666] [00667] OH Br 335. [00668] [00669] [00670] Cl 336. [00671] [00672] [00673] Br 337. [00674] [00675] H Cl 338. [00676] [00677] H Br 339. [00678] [00679] OH Cl 340. [00680] [00681] OH Br 341. [00682] [00683] [00684] Cl 342. [00685] [00686] [00687] Br 343. [00688] [00689] H Cl 344. [00690] [00691] H Br 345. [00692] [00693] OH Cl 346. [00694] [00695] OH Br 347. [00696] [00697] [00698] Cl 348. [00699] [00700] [00701] Br 349. [00702] [00703] H Cl 350. [00704] [00705] H Br 351. [00706] [00707] OH Cl 352. [00708] [00709] OH Br 353. [00710] [00711] [00712] Cl 354. [00713] [00714] [00715] Br 355. [00716] OH H Cl 356. [00717] OH H Br 357. [00718] OH OH Cl 358. [00719] OH OH Br 359. [00720] OH [00721] Cl 360. [00722] OH [00723] Br 361. [00724] H H Cl 362. [00725] H H Br 363. [00726] H OH Cl 364. [00727] H OH Br 365. [00728] H [00729] Cl 366. [00730] H [00731] Br 367. [00732] [00733] H Cl 368. [00734] [00735] H Br 369. [00736] [00737] OH Cl 370. [00738] [00739] OH Br 371. [00740] [00741] [00742] Cl 372. [00743] [00744] [00745] Br 373. [00746] [00747] H Cl 374. [00748] [00749] H Br 375. [00750] [00751] OH Cl 376. [00752] [00753] OH Br 377. [00754] [00755] [00756] Cl 378. [00757] [00758] [00759] Br 379. [00760] [00761] H Cl 380. [00762] [00763] H Br 381. [00764] [00765] OH Cl 382. [00766] [00767] OH Br 383. [00768] [00769] [00770] Cl 384. [00771] [00772] [00773] Br 385. [00774] [00775] H Cl 386. [00776] [00777] H Br 387. [00778] [00779] OH Cl 388. [00780] [00781] OH Br 389. [00782] [00783] [00784] Cl 390. [00785] [00786] [00787] Br 391. [00788] OH H Cl 392. [00789] OH H Br 393. [00790] OH OH Cl 394. [00791] OH OH Br 395. [00792] OH [00793] Cl 396. [00794] OH [00795] Br 397. [00796] H H Cl 398. [00797] H H Br 399. [00798] H OH Cl 400. [00799] H OH Br 401. [00800] H [00801] Cl 402. [00802] H [00803] Br 403. [00804] [00805] H Cl 404. [00806] [00807] H Br 405. [00808] [00809] OH Cl 406. [00810] [00811] OH Br 407. [00812] [00813] [00814] Cl 408. [00815] [00816] [00817] Br 409. [00818] [00819] H Cl 410. [00820] [00821] H Br 411. [00822] [00823] OH Cl 412. [00824] [00825] OH Br 413. [00826] [00827] [00828] Cl 414. [00829] [00830] [00831] Br 415. [00832] [00833] H Cl 416. [00834] [00835] H Br 417. [00836] [00837] OH Cl 418. [00838] [00839] OH Br 419. [00840] [00841] [00842] Cl 420. [00843] [00844] [00845] Br 421. [00846] [00847] H Cl 422. [00848] [00849] H Br 423. [00850] [00851] OH Cl 424. [00852] [00853] OH Br 425. [00854] [00855] [00856] Cl 426. [00857] [00858] [00859] Br 427. [00860] OH H Cl 428. [00861] OH H Br 429. [00862] OH OH Cl 430. [00863] OH OH Br 431. [00864] OH [00865] Cl 432. [00866] OH [00867] Br 433. [00868] H H Cl 434. [00869] H H Br 435. [00870] H OH Cl 436. [00871] H OH Br 437. [00872] H [00873] Cl 438. [00874] H [00875] Br 439. [00876] [00877] H Cl 440. [00878] [00879] H Br 441. [00880] [00881] OH Cl 442. [00882] [00883] OH Br 443. [00884] [00885] [00886] Cl 444. [00887] [00888] [00889] Br 445. [00890] [00891] H Cl 446. [00892] [00893] H Br 447. [00894] [00895] OH Cl 448. [00896] [00897] OH Br 449. [00898] [00899] [00900] Cl 450. [00901] [00902] [00903] Br 451. [00904] [00905] H Cl 452. [00906] [00907] H Br 453. [00908] [00909] OH Cl 454. [00910] [00911] OH Br 455. [00912] [00913] [00914] Cl 456. [00915] [00916] [00917] Br 457. [00918] [00919] H Cl 458. [00920] [00921] H Br 459. [00922] [00923] OH Cl 460. [00924] [00925] OH Br 461. [00926] [00927] [00928] Cl 462. [00929] [00930] [00931] Br 463. [00932] OH H Cl 464. [00933] OH H Br 465. [00934] OH OH Cl 466. [00935] OH OH Br 467. [00936] OH [00937] Cl 468. [00938] OH [00939] Br 469. [00940] H H Cl 470. [00941] H H Br 471. [00942] H OH Cl 472. [00943] H OH Br 473. [00944] H [00945] Cl 474. [00946] H [00947] Br 475. [00948] [00949] H Cl 476. [00950] [00951] H Br 477. [00952] [00953] OH Cl 478. [00954] [00955] OH Br 479. [00956] [00957] [00958] Cl 480. [00959] [00960] [00961] Br 481. [00962] [00963] H Cl 482. [00964] [00965] H Br 483. [00966] [00967] OH Cl 484. [00968] [00969] OH Br 485. [00970] [00971] [00972] Cl 486. [00973] [00974] [00975] Br 487. [00976] [00977] H Cl 488. [00978] [00979] H Br 489. [00980] [00981] OH Cl 490. [00982] [00983] OH Br 491. [00984] [00985] [00986] Cl 492. [00987] [00988] [00989] Br 493. [00990] [00991] H Cl 494. [00992] [00993] H Br 495. [00994] [00995] OH Cl 496. [00996] [00997] OH Br 497. [00998] [00999] [01000] Cl 498. [01001] [01002] [01003] Br 499. [01004] OH H Cl 500. [01005] OH H Br 501. [01006] OH OH Cl 502. [01007] OH OH Br 503. [01008] OH [01009] Cl 504. [01010] OH [01011] Br 505. [01012] H H Cl 506. [01013] H H Br 507. [01014] H OH Cl 508. [01015] H OH Br 509. [01016] H [01017] Cl 510. [01018] H [01019] Br 511. [01020] [01021] H Cl 512. [01022] [01023] H Br 513. [01024] [01025] OH Cl 514. [01026] [01027] OH Br 515. [01028] [01029] [01030] Cl 516. [01031] [01032] [01033] Br 517. [01034] [01035] H Cl 518. [01036] [01037] H Br 519. [01038] [01039] OH Cl 520. [01040] [01041] OH Br 521. [01042] [01043] [01044] Cl 522. [01045] [01046] [01047] Br 523. [01048] [01049] H Cl 524. [01050] [01051] H Br 525. [01052] [01053] OH Cl 526. [01054] [01055] OH Br 527. [01056] [01057] [01058] Cl 528. [01059] [01060] [01061] Br 529. [01062] [01063] H Cl 530. [01064] [01065] H Br 531. [01066] [01067] OH Cl 532. [01068] [01069] OH Br 533. [01070] [01071] [01072] Cl 534. [01073] [01074] [01075] Br 535. [01076] OH H Cl 536. [01077] OH H Br 537. [01078] OH OH Cl 538. [01079] OH OH Br 539. [01080] OH [01081] Cl 540. [01082] OH [01083] Br

[0626] Compounds where the double bond to R.sub.4 is hydrogenated is represented below

TABLE-US-00002 [01084] S. No R4 R2 Y X 541. [01085] H OH Br 542. [01086] H OH Br

[0627] Preferred salts for the compounds listed above are hydrochloride, hydrobromide, sodium, potassium, or magnesium.

[0628] According to another feature of this present invention, there is provided a process for the preparation of the compound represented by the formula I, wherein all symbols are as defined as earlier, as shown in Scheme 1.

##STR01087##

[0629] The reaction of a compound of general formula (1a) with a compound of general formula (2a) to produce a compound of the general formula (3a) may be carried out in an inert atmosphere which may be maintained by using inert gases such as nitrogen, argon or helium. The reaction may be carried out in a polar protic solvent like alcohols, preferably methanol or ethanol and in the presence of weak bases like DEA, TEA, Isopropylamine, pyridine, pipridine and the like, but more preferably with a base like TEA. The temperature of the reaction may range between 40 to 80° C., optimally between 60 to 80° C. and the duration may extend between 1 to 10 hours. The schiff base thus formed may be precipitated or could be extracted after suitable workup procedures such as water quenching. The resultant molecule is the halogenated benzylidine derivative of general formula (3a) where the groups have been defined earlier.

[0630] The invention is explained in detail in the examples given below which are provided by way of illustration only and therefore should not be construed to limit the scope of the invention.

Example 1

Synthesis of 2-[(5-Bromo-2-hydroxy-benzylidene)-amino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester—(Compound 1)

[0631] ##STR01088##

[0632] Step (i)

Synthesis of Tyrosine Methyl Ester Hydrochloride

[0633] Tyrosine (10.0 g) was taken in a clean and dry round bottom flask and methanol (100 ml) was added. Thionyl chloride (6.17 ml) was introduced in to the reaction mixture and it was refluxed at 70-80° C. for 6 hours with constant stirring. The excess solvent was then removed by distillation and the solid product obtained was stored under nitrogen. Yield—8.20 g

[0634] Step (ii)

Synthesis of 2-[(5-Bromo-2-hydroxy-benzylidene)-amino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester

[0635] Tyrosine methyl ester hydrochloride (8.30 g) and 5-bromo salicaldehyde (7.10 g) were taken in a clean and dry round bottom flask and methanol (100 ml) was added with constant stirring. Triethylamine (3 ml) was introduced in to the mixture and it was refluxed for 8 hours at 65-70° C. The excess solvent was then removed by distillation and the crude product was dissolved in water (150 ml). Ethyl acetate was used to extract the product from the solution and the separated organic layer was dried over sodium sulphate and then removed under reduced pressure to obtain the final product. Yield—3.14 g

[0636] NMR—8.11 (1H, s), 7.62 (1H, s), 7.29 (1H, d), 6.95 (2H, d), 6.65 (3H, m), 5.0 (2H, s), 4.35 (1H, m), 3.67 (3H, s), 3.30 (1H, m)

Example 2

Synthesis of 2-[(5-Bromo-2-hydroxy-benzylidene)-amino]-3-methyl-butyric acid methyl ester—(Compound 2)

[0637] ##STR01089##

[0638] Step (i)

Synthesis of Valine Methyl Ester Hydrochloride

[0639] Valine (50.0 g) was taken in a clean and dry round bottom flask and methanol (150 ml) was added. Thionyl chloride (34.50 ml) was introduced in to the reaction mixture and it was refluxed at 70-80° C. for 6 hours with constant stirring. The excess solvent was then removed by distillation and the solid product obtained was stored under nitrogen. Yield—75.0 g

[0640] Step (ii)

[0641] Valine methyl ester hydrochloride (75.0 g) and 5-bromo salicaldehyde (50.0 g) were taken in a clean and dry round bottom flask and methanol (250 ml) was added with constant stirring. Triethylamine (50 ml) was introduced in to the mixture and it was refluxed for 8 hours at 65-70° C. Molecular sieves were also added to scavenge the water produced during the reaction. The reaction mass was then dissolved in acetone (200 ml) and filtered to remove the undissolved material. A solid precipitate was obtained when water (500 ml) was added to the filtrate. This was then filtered and dried. Yield—54.6 g.

[0642] NMR—8.13 (1H, s), 7.62 (1H, s), 7.29 (1H, d), 6.65 (1H, d), 5.0 (1H, s), 3.95 (1H, s), 3.67 (3H, s), 2.50 (1H, m), 1.10 (1H, d)

Example 3

Synthesis of 2-(5-Bromo-2-hydroxy-benzylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester (Compound 3)

[0643] ##STR01090##

[0644] Step (i)

Synthesis of Tyrosine Methyl Ester Hydrochloride

[0645] Tyrosine (10.0 g) was taken in a clean and dry round bottom flask and methanol (100 ml) was added. Thionyl chloride (6.17 ml) was introduced in to the reaction mixture and it was refluxed at 70-80° C. for 6 hours with constant stirring. The excess solvent was then removed by distillation and the solid product obtained was stored under nitrogen. Yield—8.20 g

[0646] Step (ii)

Synthesis of 2-[(5-Bromo-2-hydroxy-benzylidene)-amino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester

[0647] Tyrosine methyl ester hydrochloride (8.30 g) and 5-bromo salicaldehyde (7.10 g) were taken in a clean and dry round bottom flask and methanol (100 ml) was added with constant stirring. Triethylamine (3 ml) was introduced in to the mixture and it was refluxed for 8 hours at 65-70° C. The excess solvent was then removed by distillation and the crude product was dissolved in water (150 ml). Ethyl acetate was used to extract the product from the solution and the separated organic layer was dried over sodium sulphate and then removed under reduced pressure to obtain the product. Yield—3.14 g

[0648] Step (iii)

[0649] 2-[(5-Bromo-2-hydroxy-benzylidene)-amino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester (6.01 g) was taken in a clean and dry round bottom flask and methanol (50 ml) was added with constant stirring. Sodium borohydride (4.05 g) was added lot by lot and the reaction mixture was stirred for 2 hours under room temperature. The solvent was removed completely and the reaction mass was acidified with 20% HCl solution. The product was extracted using ethylacetate and the separated organic layer was washed with water. It was then dried over sodium sulphate and evaporated under nitrogen to obtain the final product. Yield—3.85 g.

[0650] NMR—6.50-7.06 (Aromatic), 5.0 (2H, s), 3.81 (3H, s), 3.14 (1H, m), 2.0 (1H, s)

Example 4

Synthesis of 2-[(5-Bromo-2-hydroxy-benzylidene)-amino]-3-(4-hydroxy-phenyl)-propionic acid (Compound 4)

[0651] ##STR01091##

[0652] Step (i)

Synthesis of Tyrosine Methyl Ester Hydrochloride

[0653] Tyrosine (10.0 g) was taken in a clean and dry round bottom flask and methanol (100 ml) was added. Thionyl chloride (6.17 ml) was introduced in to the reaction mixture and it was refluxed at 70-80° C. for 6 hours with constant stirring. The excess solvent was then removed by distillation and the solid product obtained was stored under nitrogen. Yield—8.20 g

[0654] Step (ii)

Synthesis of 2-[(5-Bromo-2-hydroxy-benzylidene)-amino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester

[0655] Tyrosine methyl ester hydrochloride (8.30 g) and 5-bromo salicaldehyde (7.10 g) were taken in a clean and dry round bottom flask and methanol (100 ml) was added with constant stirring. Triethylamine (3 ml) was introduced in to the mixture and it was refluxed for 8 hours at 65-70° C. The excess solvent was then removed by distillation and the crude product was dissolved in water (150 ml). Ethyl acetate was used to extract the product from the solution and the separated organic layer was dried over sodium sulphate and then removed under reduced pressure to obtain the product. Yield—3.14 g

[0656] Step (iii)

[0657] 2-[(5-Bromo-2-hydroxy-benzylidene)-amino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester (5.0 g) was taken in a clean and dry round bottom flask and NaOH solution (3.69 g/66 ml) was added to it with constant stirring. Acetone (33 ml) was added and the mixture was maintained at room temperature for 3 hours. The reaction mixture was then cooled to 25° C. and the pH was brought to 5.5 using 1:1 HCl solution. The precipitated solid was filtered, washed with water followed by hexane and dried. Yield 2.50 g

[0658] NMR—10.21 (1H, s), 8.11 (1H, s), 6.50-7.62 (Aromatic), 5.0 (2H, s), 4.39 (1H, m), 3.02 (1H,)

Example 5

Synthesis of 4-Bromo-2-{[1-hydroxymethyl-2-(4-hydroxy-phenyl)-ethylimino]-methyl}-phenol (Compound 5)

[0659] ##STR01092##

[0660] Step (i)

Synthesis of Tyrosinol

[0661] Tyrosine (30.0 g) was taken in a clean and dry round bottom flask and tetrahydrofuran (40 ml) was added with constant stirring. Boron trifluoride ethyl ether complex (21 ml) and borane dimethylsulphide (34.5 ml) were added and the reaction mixture was refluxed at 40-50° C. for 18 hours. 6 M NaOH solution was added to the reaction mixture and it was then saturated with potassium carbonate. Chloroform was used to extract the product and the organic layer was washed with water and dried over sodium sulphate. The chloroform was then evaporated to obtain the product. Yield 7.5 g.

[0662] Step (ii)

[0663] Tyrosinol (7.50 g) and 5-bromo salicaldehyde (4.50 g) were taken in a clean and dry round bottom flask and methanol (100 ml) was added with constant stirring. The mixture was refluxed for 4 hours at 65-70° C. The excess solvent was then removed by distillation and the crude product was dissolved in water (150 ml). Chloroform was used to extract the product from the solution and the separated organic layer was dried over sodium sulphate and then removed under reduced pressure to obtain the final product. Yield—4.36 g

[0664] NMR—10.21 (1H, s), 8.11 (1H, s), 6.50-7.62 (Aromatic), 5.0 (2H, s), 4.39 (1H, m), 3.02 (1H,)

Example 6

Synthesis of 2-(5-Bromo-2-hydroxy-benzylamino)-3-methyl-butyric acid methyl ester (Compound 6)

[0665] ##STR01093##

[0666] Step (i)

Synthesis of Valine Methyl Ester Hydrochloride

[0667] Valine (50.0 g) was taken in a clean and dry round bottom flask and methanol (150 ml) was added. Thionyl chloride (34.50 ml) was introduced in to the reaction mixture and it was refluxed at 70-80° C. for 6 hours with constant stirring. The excess solvent was then removed by distillation and the solid product obtained was stored under nitrogen. Yield—75.0 g

[0668] Step (ii)

[0669] Valine methyl ester hydrochloride (75.0 g) and 5-bromo salicaldehyde (50.0 g) were taken in a clean and dry round bottom flask and methanol (250 ml) was added with constant stirring. Triethylamine (50 ml) was introduced in to the mixture and it was refluxed for 8 hours at 65-70° C. Molecular sieves were also added to scavenge the water produced during the reaction. The reaction mass was then dissolved in acetone (200 ml) and filtered to remove the undissolved material. A solid precipitate was obtained when water (500 ml) was added to the filtrate. This was then filtered and dried. Yield—54.6 g.

[0670] Step (iii)

[0671] 2-[(5-Bromo-2-hydroxy-benzylidene)-amino]-3-methyl-butyric acid methyl ester (1.3 g) was taken in a clean and dry round bottom flask and methanol (50 ml) was added with constant stirring. Sodium borohydride (0.8 g) was added lot by lot and the reaction mixture was stirred for 2 hours under room temperature. The solvent was removed completely and the reaction mass was acidified with 20% HCl solution. The product was extracted using ethylacetate and the separated organic layer was washed with water. It was then dried over sodium sulphate and evaporated under nitrogen to obtain the final product. Yield—1.0 g.

[0672] NMR—6.50-7.07 (Aromatic), 5.0 (1H, s), 3.81 (2H, d), 3.67 (3H, s), 3.44 (1H, d), 2.70 (1H, m), 2.0 (1H, d), 1.12 (6H, d)

Example 7

Synthesis of 2-[(5-Bromo-2-hydroxy-benzylidene)-amino]-3-methyl-butyric acid (Compound 7)

[0673] ##STR01094##

[0674] Step (i)

Synthesis of Valine Methyl Ester Hydrochloride

[0675] Valine (50.0 g) was taken in a clean and dry round bottom flask and methanol (150 ml) was added. Thionyl chloride (34.50 ml) was introduced in to the reaction mixture and it was refluxed at 70-80° C. for 6 hours with constant stirring. The excess solvent was then removed by distillation and the solid product obtained was stored under nitrogen. Yield—75.0 g

[0676] Step (ii)

[0677] Valine methyl ester hydrochloride (75.0 g) and 5-bromo salicaldehyde (50.0 g) were taken in a clean and dry round bottom flask and methanol (250 ml) was added with constant stirring. Triethylamine (50 ml) was introduced in to the mixture and it was refluxed for 8 hours at 65-70° C. Molecular sieves were also added to scavenge the water produced during the reaction. The reaction mass was then dissolved in acetone (200 ml) and filtered to remove the undissolved material. A solid precipitate was obtained when water (500 ml) was added to the filtrate. This was then filtered and dried. Yield—54.6 g.

[0678] Step (iii)

[0679] 2-[(5-Bromo-2-hydroxy-benzylidene)-amino]-3-methyl-butyric acid methyl (9.0 g) was taken in a clean and dry round bottom flask and NaOH solution (3.69 g/120 ml) was added to it with constant stirring. Acetone (90 ml) was added and the mixture was maintained at room temperature for 3 hours. The reaction mixture was then cooled to 25° C. and the pH was brought to 5.5 using 1:1 HCl solution. The precipitated solid was filtered, washed with water followed by hexane and dried. Yield 5.80 g

[0680] NMR—10.21 (1H, s), 8.13 (1H, s), 6.65-7.62 (Aromatic), 5.0 (1H, s), 3.89 (1H, d), 2.04 (1H, m), 1.12 (6H, d)

Example 8

Synthesis of 4-Bromo-2-[(1-hydroxymethyl-2-methyl-propylimino)-methyl]-phenol (Compound 8)

[0681] ##STR01095##

[0682] Step (i)

Synthesis of Valinol

[0683] Valine (11.7 g) was taken in a clean and dry round bottom flask and tetrahydrofuran (100 ml) was added with constant stirring. Boron trifluoride ethyl ether complex 14.2 ml) and borane dimethylsulphide (10 ml) were added and the reaction mixture was refluxed at 40-50° C. for 4 hours. The reaction mixture was acidified with 0.5N HCl and the THF layer was separated and washed twice with water. The solvent was then dried over sodium sulphate and evaporated to obtain the product. Yield 8.0 g.

[0684] Step (ii)

[0685] Valinol (10 g) and 5-bromo salicaldehyde (4.0 g) were taken in a clean and dry round bottom flask and methanol (100 ml) was added with constant stirring. TEA (1.0 ml) was added and the mixture was refluxed for 4 hours at 65-70° C. The excess solvent was then removed by distillation and the crude product was dissolved in water (150 ml). Chloroform was used to extract the product from the solution and the separated organic layer was dried over sodium sulphate and then removed under reduced pressure to obtain the final product. Yield—5.2 g

[0686] NMR—6.65-7.62 (Aromatic), 5.0 (1H, s), 3.89 (1H, d), 2.04 (1H, m), 1.12 (6H, d)

Example 9

Synthesis of 4-Methyl-benzoic acid 4-bromo-2-[(4-chloro-phenylimino)-methyl]-phenyl ester (Compound 9)

[0687] ##STR01096##

[0688] Step (i)

Synthesis of 4-Methyl-benzoic acid 4-bromo-2-formyl-phenyl ester (Compound 9)

[0689] 5-bromo salicyaldehyde (5.0 g) was taken in a clean and dry round bottom flask and chloroform (50 ml) was added with constant stirring. The reaction mixture was cooled to 10-15° C. and p-toulyl chloride (3.62 ml) was added drop wise. Stirring was continued for 15 minutes and TEA (3.0 ml) was added and the reaction was allowed to proceed for 4 hours. The reaction mixture was then transferred to a separating funnel and washed twice with water. The separated organic layer was then washed with 5% NaOH solution and then dried over sodium sulphate. The chloroform was 80% evaporated and hexane was added to obtain a solid precipitate. This precipitate was filtered and dried. Yield 7.2 g.

[0690] Step (ii)

Synthesis of 4-Methyl-benzoic acid 4-bromo-2-[(4-chloro-phenylimino)-methyl]-phenyl ester

[0691] 4-Methyl-benzoic acid 4-bromo-2-formyl-phenyl ester (4.0 g) and 4-chloro aniline (1.9 g) were taken in a clean and dry round bottom flask and methanol (40 ml) was added to it. The reaction mixture was refluxed at 60-80° C. for 3 hours following which it was transferred to a beaker containing 100 ml water and stirred for 15 minutes. The solid precipitate formed was filtered, washed with water, followed by hexane and dried. Yield 3.6 g.

[0692] NMR—8.39 (1H, s), 7.07-8.02 (Aromatic), 2.35 (3H, s)

Example 10

Synthesis of 3-Methyl-benzoic acid 4-bromo-2-[(2,3-dichloro-phenylimino)-methyl]-phenyl ester (Compound 10)

[0693] ##STR01097##

[0694] Step (i)

Synthesis of 3-Methyl-benzoic acid 4-bromo-2-formyl-phenyl ester

[0695] 5-bromo salicyaldehyde (5.0 g) was taken in a clean and dry round bottom flask and chloroform (50 ml) was added with constant stirring. The reaction mixture was cooled to 10-15° C. and m-toulyl chloride (3.62 ml) was added drop wise. Stirring was continued for 15 minutes and TEA (3.0 ml) was added and the reaction was allowed to proceed for 4 hours. The reaction mixture was then transferred to a separating funnel and washed twice with water. The separated organic layer was then washed with 5% NaOH solution and then dried over sodium sulphate. The chloroform was 80% evaporated and hexane was added to obtain a solid precipitate. This precipitate was filtered and dried. Yield 7.2 g.

[0696] Step (ii)

Synthesis of 3-Methyl-benzoic acid 4-bromo-2-[(2,3-dichloro-phenylimino)-methyl]-phenyl ester

[0697] 3-Methyl-benzoic acid 4-bromo-2-formyl-phenyl ester (4.0 g) and 2,3-dichloro aniline (1.9 g) were taken in a clean and dry round bottom flask and methanol (40 ml) was added to it. The reaction mixture was refluxed at 60-80° C. for 3 hours following which it was transferred to a beaker containing 100 ml water and stirred for 15 minutes. The solid precipitate formed was filtered, washed with water, followed by hexane and dried. Yield 3.6 g.

[0698] NMR—8.39 (1H, s), 7.01-7.90 (Aromatic), 2.35 (3H, s)

Example 11

Synthesis of [5-Bromo-2-(1-m-tolyl-vinyloxy)-benzylidine]-pyridin-3-yl-amine (Compound 11)

[0699] ##STR01098##

[0700] Step (i)

Synthesis of 4-Bromo-2-(pyridine-3-yliminomethyl)-phenol

[0701] 5-bromo salicyaldehyde (10.0 g) and 3-amino pyridine (5.85 g) were taken in a clean and dry round bottom flask and methanol (150 ml) was added with constant stirring. The reaction was refluxed at 60° C. for 6 hours. The solid product formed was filtered and washed with water, followed by hexane and dried. Yield 8.25 g.

[0702] Step (ii)

[0703] 4-Bromo-2-(pyridine-3-yliminomethyl)-phenol (5.0 g) was taken in a clean and dry round bottom flask and chloroform (100 ml) was added to it. The reaction mixture was cooled to 10° C. and m-toulyl chloride (3.62 ml) was added drop wise followed by the addition of TEA (3.58 ml). The reaction was then allowed to proceed for 6 hours at room temperature. It was then quenched by adding water. The chloroform layer was separated and washed twice with 10% NaOH solution following which it was dried over sodium sulphate and concentrated. Hexane was added to the cooled and concentrated organic layer to obtain the solid precipitate. This was then filtered and dried. Yield 4.6 g.

[0704] NMR—8.60 (1H, s), 8.1 (1H, s), 7.10-7.95 (Aromatic), 2.35 (3H, s)

Example 12

Synthesis of Nicotinic acid-4-bromo-2[(3-carboxy-phenylimino)-methyl]-phenyl ester (Compound 12)

[0705] ##STR01099##

[0706] Step (i)

Synthesis of Nicotonyl Chloride

[0707] Nicotinic acid (20.0 g) was taken in a clean and dry round bottom flask and thionyl chloride (75 ml) was added with constant stirring. The reaction was allowed to proceed for 5 hours at 70-80° C. following which the excess thionyl chloride was distilled off. Hexane was added and redistillation was performed to remove trace amounts of thionyl chloride. Yield 28.0 g.

[0708] Step (ii)

Synthesis of Nicotinicacid-4-bromo-2-formyl-phenyl ester

[0709] 5-bromo salicaldehyde (20.0 g) was taken in a clean and dry round bottom flask and chloroform (75 ml) was added with constant stirring. The temperature was brought down to 5-10° C. Nicotonyl chloride (17.5 g) was added to the reaction mixture and stirred for 15 minutes. TEA (11.32 ml) was added drop wise and the reaction was allowed to stir for 6 hours at room temperature and the quenched by transferring it to a beaker containing water. The organic layer was separated and washed with water and dried over sodium sulphate. The solvent was then removed to obtain the solid product was then filtered and dried. Yield 12.0 g.

[0710] Step (iii)

Synthesis of Synthesis of Nicotinic acid-4-bromo-2[(3-carboxy-phenylimino)-methyl]-phenyl ester

[0711] Nicotinic acid-4-bromo-2-formyl-phenyl ester (1.5 g) was taken in a clean and dry round bottom flask and methanol (30 ml) was added. The reaction mixture was stirred over an oil bath and 3-amino benzoic acid (0.715 g) was introduced lot by lot. Stirring was continued for 5 hours at 60-80° C. following which the reaction was quenched by transferring it to a beaker containing water. The solid precipitate thus formed was washed with water followed by hexane, filtered and dried. Final product yield 0.72 g.

[0712] NMR—11.01 (1H, s), 9.10 (1H, s), 8.79 (1H, d), 8.35 (1H, s), 8.17 (1H, d), 7.60-8.10 (aromatic), 7.62 (1H, s), 6.51 (1H, d)