Thiazolidine derivatives, their preparation and compositions containing them

Claim 2

Compounds of formula (I): ##STR19## in which: R 1 and R 2 are the same or different and each represents hydrogen or a C 1 -C 5 alkyl group; R 3 represents hydrogen; C 1 -C 6 aliphatic acyl; (C 5 -C 7 cycloalkane)carbonyl; benzoyl, benzoyl substituted with one to three substituents selected from the group of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, hydroxy, halogen, nitro, amino and di(C 1 -C 4 alkyl)amino; naphthoyl; 4-7 membered heterocyclic acyl wherein heterocyclic moiety has O, S or N hetero atoms; phenyl(C 2 -C 3 )aliphatic acyl; cinnamoyl; (C 1 -C 6 alkoxy)carbonyl; or benzoyloxycarbonyl; R 4 and R 5 are the same or different and each represents hydrogen, a C 1 -C 5 alkyl group or a C 1 -C 5 alkoxy group, or R 4 and R 5 together represent a C 1 -C 4 alkylenedioxy group; n is 1, 2 or 3; W represents the --CH 2 --, >CO or >CH--OR 6 group (in which R 6 represents any one of the atoms or groups defined for R 3 and may be the same as or different from R 3 ); and Y and Z are the same or different and each represents the oxygen atom or the imino group; and pharmaceutically acceptable salts thereof.

Claim 3

Compounds as claimed in claim 1, in which; R 3 represents hydrogen, a C 1 -C 6 aliphatic acyl group, one of said aromatic acyl groups or one of said heterocyclic acyl groups.

Claim 4

Compounds as claimed in claim 1, in which: Y represents an oxygen atom; R 1 and R 2 are the same or different and each represents hydrogen or a C 1 -C 5 alkyl group; R 3 represents hydrogen, a C 1 -C 6 aliphatic acyl group, one of said aromatic acyl groups or a pyridinecarbonyl group; and R 4 and R 5 are the same or different and each represents hydrogen, a C 1 -C 5 alkyl group or a C 1 or C 2 alkoxy group.

Claim 5

Compounds as claimed in claim 3, in which: R 1 , R 2 , R 4 and R 5 are the same or different and each represents hydrogen or a C 1 -C 5 alkyl group; n is 1 or 2; and W represents the --CH 2 -- or >CO group.

Claim 6

Compounds as claimed in claim 4, in which R 3 represents a hydrogen atom, a C 1 -C 5 aliphatic acyl group, or the benzoyl or nicotinoyl group.

Claim 7

Compounds as claimed in claim 5, in which: R 1 and R 4 are the same or different and each represents a C 1 -C 5 alkyl group; R 2 and R 5 are the same or different and each represents the hydrogen atom or the methyl group; and R 3 represents hydrogen or a C 1 -C 4 aliphatic acyl group.

Claim 8

Compounds as claimed in claim 1, in which: W represents the --CH 2 -- or >CO group; Y and Z both represent oxygen atoms; n is 1 or 2; R 1 and R 4 are the same or different and each represents a C 1 -C 4 alkyl group; R 2 and R 5 are the same or different and each represents the hydrogen atom or the methyl group; and R 3 represents hydrogen or a C 1 -C 4 aliphatic acyl group.

Claim 9

Compounds as claimed in claim 7, in which n is 1.

Claim 10

Compounds as claimed in claim 7 or claim 8, in which W represents the --CH 2 -- group.

Claim 11

Compounds as claimed in claim 1, selected from the group consisting of: 5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(2-ethyl-6-hydroxy-5,7,8-trimethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(6-hydroxy-5,7,8-trimethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-{4-[2-(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)ethoxy]benzyl}thiazolidine-2,4-dione 5-{4-[2-(7-t-butyl-6-hydroxy-2-methylchroman-2-yl)ethoxy]benzyl}thiazolidine-2,4-dione 5-{4-[2-(6-hydroxy-7,8-dimethoxy-2,5-dimethylchroman-2-yl)ethoxy]benzyl}thiazolidine-2,4-dione 5-[4-(6-hydroxy-2,7-dimethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(6-hydroxy-2-isobutyl-5,7,8-trimethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one 5-[4-(7-t-butyl-6-hydroxy-2-methylchroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one 5-[4-(2-ethyl-6-hydroxy-5,7,8-trimethylchroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one 5-[4-(6-hydroxy-5,7,8-trimethylchroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one 5-[4-(6-hydroxy-2,7-dimethylchroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one 5-[4-(6-acetoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(6-benzoyloxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(6-butyryloxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(2,5,7,8-tetramethyl-6-nicotinoyloxychroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(6-hydroxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(7-t-butyl-6-hydroxy-2-methyl-4-oxochroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(6-hydroxy-2-isobutyl-5,7,8-trimethyl-4-oxochroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(6-hydroxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one 5-[4-(7-t-butyl-6-hydroxy-2-methyl-4-oxochroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one 5-[4-(6-hydroxy-2-isobutyl-5,7,8-trimethyl-4-oxochroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one 5-[4-(6-acetoxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(6-acetoxy-5,7,8-trimethylchroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one 5-{4-[2-(6-acetoxy-7-t-butyl-2-methylchroman-2-yl)ethoxy]benzyl}-2-iminothiazolidin-4-one 5-{4-[2-(6-acetoxy-7,8-dimethoxy-2,5-dimethylchroman-2-yl)ethoxy]benzyl}-2-iminothiazolidin-4-one and pharmaceutically acceptable salts thereof.

Claim 12

The compound as claimed in claim 1, 5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione and pharmaceutically acceptable salts thereof.

Claim 13

The compound as claimed in claim 1, 5-[4-(2-ethyl-6-hydroxy-5,7,8-trimethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione and pharmaceutically acceptable salts thereof.

Claim 14

The compound as claimed in claim 1, 5-{4-[2-(7-t-butyl-6-hydroxy-2-methylchroman-2-yl)ethoxy]benzyl}thiazolidine-2,4-dione and pharmaceutically salts thereof.

Claim 15

The compound as claimed in claim 1, 5-[4-(6-hydroxy-2-isobutyl-5,7,8-trimethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione and pharmaceutically acceptable salts thereof.

Claim 16

The compound as claimed in claim 1, 5-[4-(6-acetoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione and pharmaceutically acceptable salts thereof.

Claim 17

The compound as claimed in claim 1, 5-[4-(6-butyryloxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione and pharmaceutically acceptable salts thereof.

Claim 18

The compound as claimed in claim 1, 5-[4-(6-hydroxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione and pharmaceutically acceptable salts thereof.

Claim 19

The compound as claimed in claim 1, 5-[4-(7-t-butyl-6-hydroxy-2-methyl-4-oxochroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione and pharmaceutically acceptable salts thereof.

Claim 20

Compounds of formula (1a): ##STR20## in which: R 1 and R 2 are the same or different and each represents hydrogen or a C 1 -C 5 alkyl group; R 3 represents hydrogen; C 1 -C 6 aliphatic acyl; (C 5 -C 7 cycloalkane)carbonyl; benzoyl, benzoyl substituted with one to three substitutents selected from the group of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, hydroxy, halogen, nitro, amino and di(C 1 -C 4 alkyl)amino; naphthoyl; 4-7 membered heterocyclic acyl wherein heterocyclic moiety has O, S or N hetero atoms; phenyl(C 2 -C 3 )aliphatic acyl; cinnamoyl; (C 1 -C 6 alkoxy)carbonyl; or benzoyloxycarbonyl; R 4 and R 5 are the same or different and each represents hydrogen, a C 1 -C 5 alkyl group or a C 1 -C 5 alkoxy group, or R 4 and R 5 together represent a C 1 -C 4 alkylenedioxy group; n is 1, 2 or 3; and Y and Z are the same or different and each represents the oxygen atom or the imino group; and pharmaceutically acceptable salts thereof.

Claim 21

Compounds of formula (1a): ##STR20## in which: R 1 and R 2 are the same or different and each represents hydrogen or a C 1 -C 5 alkyl group; R 3 represents hydrogen; C 1 -C 6 aliphatic acyl; (C 5 -C 7 cycloalkane)carbonyl; benzoyl, benzoyl substituted with one to three substitutents selected from the group of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, hydroxy, halogen, nitro, amino and di(C 1 -C 4 alkyl)amino; naphthoyl; 4-7 membered heterocyclic acyl wherein heterocyclic moiety has O, S or N hetero atoms; phenyl(C 2 -C 3 )aliphatic acyl; cinnamoyl; (C 1 -C 6 alkoxy)carbonyl; or benzoyloxycarbonyl; R 4 and R 5 are the same or different and each represents hydrogen, a C 1 -C 5 alkyl group or a C 1 -C 5 alkoxy group, or R 4 and R 5 together represent a C 1 -C 4 alkylenedioxy group; n is 1, 2 or 3; and Y and Z are the same or different and each represents the oxygen atom or the imino group; and pharmaceutically acceptable salts thereof.

Claim 22

Compounds of formula (Ib): ##STR21## in which: R 1 and R 2 are the same or different and each represents hydrogen or a C 1 -C 5 alkyl group; R 3 represents hydrogen; C 1 -C 6 aliphatic acyl; (C 5 -C 7 cycloalkane)carbonyl; benzoyl, benzoyl substituted with one to three substituents selected from the group of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, hydroxy, halogen, nitro, amino and di(C 1 -C 4 alkyl)amino; naphthoyl; 4-7 membered heterocyclic acyl wherein heterocyclic moiety has O, S or N hetero atoms; phenyl(C 2 -C 3 )aliphatic acyl; cinnamoyl; (C 1 -C 6 alkoxy)carbonyl; or benzoyloxycarbonyl; R 4 and R 5 are the same or different and each represents hydrogen, a C 1 -C 5 alkyl group or a C 1 -C 5 alkoxy group, or R 4 and R 5 together represent a C 1 -C 4 alkylenedioxy group; n is 1, 2 or 3; and Y and Z are the same or different and each represents the oxygen atom or the imino group; and pharmaceutically acceptable salts thereof.

Claim 23

Compounds of formula (Ib): ##STR21## in which: R 1 and R 2 are the same or different and each represents hydrogen or a C 1 -C 5 alkyl group; R 3 represents hydrogen; C 1 -C 6 aliphatic acyl; (C 5 -C 7 cycloalkane)carbonyl; benzoyl, benzoyl substituted with one to three substituents selected from the group of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, hydroxy, halogen, nitro, amino and di(C 1 -C 4 alkyl)amino; naphthoyl; 4-7 membered heterocyclic acyl wherein heterocyclic moiety has O, S or N hetero atoms; phenyl(C 2 -C 3 )aliphatic acyl; cinnamoyl; (C 1 -C 6 alkoxy)carbonyl; or benzoyloxycarbonyl; R 4 and R 5 are the same or different and each represents hydrogen, a C 1 -C 5 alkyl group or a C 1 -C 5 alkoxy group, or R 4 and R 5 together represent a C 1 -C 4 alkylenedioxy group; n is 1, 2 or 3; and Y and Z are the same or different and each represents the oxygen atom or the imino group; and pharmaceutically acceptable salts thereof.

Claim 24

Compounds of formula (Ic): ##STR22## in which: R 1 and R 2 are the same or different and each represents hydrogen or a C 1 -C 5 alkyl group; R 3 represents hydrogen; C 1 -C 6 aliphatic acyl; (C 5 -C 7 cycloalkane)carbonyl; benzoyl, benzoyl substituted with one to three substituents selected from the group of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, hydroxy, halogen, nitro, amino and di(C 1 -C 4 alkyl)amino; naphthoyl; 4-7 membered heterocyclic acyl wherein heterocyclic moiety has O, S or N hetero atoms; phenyl(C 2 -C 3 )aliphatic acyl; cinnamoyl; (C 1 -C 6 alkoxy)carbonyl; or benzoyloxycarbonyl; R 4 and R 5 are the same or different and each represents hydrogen, a C 1 -C 5 alkyl group or a C 1 -C 5 alkoxy group, or R 4 and R 5 together represent a C 1 -C 4 alkylenedioxy group; n is 1, 2 or 3; R 6 represents any one of the atoms or groups defined for R 3 and may be the same as or different from R 3 ; and Y and Z are the same or different and each represents the oxygen atom or the imino group; and pharmaceutically acceptable salts thereof.

Claim 25

Compounds of formula (Ic): ##STR22## in which: R 1 and R 2 are the same or different and each represents hydrogen or a C 1 -C 5 alkyl group; R 3 represents hydrogen; C 1 -C 6 aliphatic acyl; (C 5 -C 7 cycloalkane)carbonyl; benzoyl, benzoyl substituted with one to three substituents selected from the group of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, hydroxy, halogen, nitro, amino and di(C 1 -C 4 alkyl)amino; naphthoyl; 4-7 membered heterocyclic acyl wherein heterocyclic moiety has O, S or N hetero atoms; phenyl(C 2 -C 3 )aliphatic acyl; cinnamoyl; (C 1 -C 6 alkoxy)carbonyl; or benzoyloxycarbonyl; R 4 and R 5 are the same or different and each represents hydrogen, a C 1 -C 5 alkyl group or a C 1 -C 5 alkoxy group, or R 4 and R 5 together represent a C 1 -C 4 alkylenedioxy group; n is 1, 2 or 3; R 6 represents any one of the atoms or groups defined for R 3 and may be the same as or different from R 3 ; and Y and Z are the same or different and each represents the oxygen atom or the imino group; and pharmaceutically acceptable salts thereof.

Claim 26

Compounds as claimed in claim 1 or claim 19, which are salts with cations.

Claim 27

Compounds as claimed in claim 1 or claim 19, in the form of the sodium salt.

Claim 28

A pharmaceutical composition for the treatment of hyperlipaemia or hyperglycaemia, which comprises at least one active compound in admixture with a pharmaceutically acceptable carrier or diluent, wherein said active compound is selected from compounds of formula (I): ##STR23## in which: R 1 and R 2 are the same or different and each represents hydrogen or a C 1 -C 5 alkyl group; R 3 represents hydrogen; C 1 -C 6 aliphatic acyl; (C 5 -C 7 cycloalkane)carbonyl; benzoyl, benzoyl substituted with one to three substituents selected from the group of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, hydroxy, halogen, nitro, amino and di(C 1 -C 4 alkyl)amino; naphthoyl; 4-7 membered heterocyclic acyl wherein heterocyclic moiety has O, S or N hetero atoms; phenyl(C 2 -C 3 )aliphatic acyl; cinnamoyl; (C 1 -C 6 alkoxy)carbonyl; or benzoyloxycarbonyl; R 4 and R 5 are the same or different and each represents hydrogen, a C 1 -C 5 alkyl group or a C 1 -C 5 alkoxy group, or R 4 and R 5 together represent a C 1 -C 4 alkylenedioxy group; n is 1, 2 or 3; W represents the --CH 2 --, >CO or >CH--OR 6 group (in which R 6 represents any one of the atoms or groups defined for R 3 and may be the same as or different from R 3 ); and Y and Z are the same or different and each represents the oxygen atom or the imino group; and pharmaceutically acceptable salts thereof.

Claim 29

A pharmaceutical composition for the treatment of hyperlipaemia or hyperglycaemia, which comprises at least one active compound in admixture with a pharmaceutically acceptable carrier or diluent, wherein said active compound is selected from compounds of formula (I): ##STR23## in which: R 1 and R 2 are the same or different and each represents hydrogen or a C 1 -C 5 alkyl group; R 3 represents hydrogen; C 1 -C 6 aliphatic acyl; (C 5 -C 7 cycloalkane)carbonyl; benzoyl, benzoyl substituted with one to three substituents selected from the group of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, hydroxy, halogen, nitro, amino and di(C 1 -C 4 alkyl)amino; naphthoyl; 4-7 membered heterocyclic acyl wherein heterocyclic moiety has O, S or N hetero atoms; phenyl(C 2 -C 3 )aliphatic acyl; cinnamoyl; (C 1 -C 6 alkoxy)carbonyl; or benzoyloxycarbonyl; R 4 and R 5 are the same or different and each represents hydrogen, a C 1 -C 5 alkyl group or a C 1 -C 5 alkoxy group, or R 4 and R 5 together represent a C 1 -C 4 alkylenedioxy group; n is 1, 2 or 3; W represents the --CH 2 --, >CO or >CH--OR 6 group (in which R 6 represents any one of the atoms or groups defined for R 3 and may be the same as or different from R 3 ); and Y and Z are the same or different and each represents the oxygen atom or the imino group; and pharmaceutically acceptable salts thereof.

Claim 30

Compositions as claimed in claim 24, in which: R 3 represents hydrogen, a C 1 -C 6 aliphatic acyl group, one of said aromatic acyl groups or one of said heterocyclic acyl groups.

Claim 31

Compositions as claimed in claim 24, in which: Y represents an oxygen atom; R 1 and R 2 are the same or different and each represents hydrogen or a C 1 -C 5 alkyl group; R 3 represents hydrogen, a C 1 -C 6 aliphatic acyl group, one of said aromatic acyl groups or a pyridinecarbonyl group; and R 4 and R 5 are the same or different and each represents hydrogen, a C 1 -C 5 alkyl group or a C 1 or C 2 alkoxy group.

Claim 32

Compositions as claimed in claim 26, in which: R 1 , R 2 , R 4 and R 5 are the same or different and each represents hydrogen or a C 1 -C 5 alkyl group; n is 1 or 2; and W represents the --CH 2 -- or >CO group.

Claim 33

Compositions as claimed in claim 27, in which R 3 represents a hydrogen atom, a C 1 -C 5 aliphatic acyl group, or the benzoyl or nicotinoyl group.

Claim 34

Compositions as claimed in claim 28, in which: R 1 and R 4 are the same or different and each represents a C 1 -C 5 alkyl group; R 2 and R 5 are the same or different and each represents the hydrogen atom or the methyl group; and R 3 represents hydrogen or a C 1 -C 4 aliphatic acyl group.

Claim 35

Compositions as claimed in claim 24, in which: W represents the --CH 2 -- or >CO group; Y and Z both represent oxygen atoms; n is 1 or 2; R 1 and R 4 are the same or different and each represents a C 1 -C 4 alkyl group; R 2 and R 5 are the same or different and each represents the hydrogen atom or the methyl group; and R 3 represents hydrogen or a C 1 -C 4 aliphatic acyl group.

Claim 36

Compositions as claimed in claim 30, in which n is 1.

Claim 37

Compositions as claimed in claim 30 or claim 17, in which W represents the --CH 2 -- group.

Claim 38

Compositions as claimed in claim 24, wherein said active compound is selected from the group consisting of: 5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(2-ethyl-6-hydroxy-5,7,8-trimethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(6-hydroxy-5,7,8-trimethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-{4-[2-(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)ethoxy]benzyl}thiazolidine-2,4-dione 5-{4-[2-(7-t-butyl-6-hydroxy-2-methylchroman-2-yl)ethoxy]benzyl}thiazolidine-2,4-dione 5-{4-[2-(6-hydroxy-7,8-dimethoxy-2,5-dimethylchroman-2-yl)ethoxy]benzyl}thiazolidine-2,4-dione 5-[4-(6-hydroxy-2,7-dimethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(6-hydroxy-2-isobutyl-5,7,8-trimethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one 5-[4-(7-t-butyl-6-hydroxy-2-methylchroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one 5-[4-(2-ethyl-6-hydroxy-5,7,8-trimethylchroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one 5-[4-(6-hydroxy-5,7,8-trimethylchroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one 5-[4-(6-hydroxy-2,7-dimethylchroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one 5-[4-(6-acetoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(6-benzoyloxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(6-butyryloxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(2,5,7,8-tetramethyl-6-nicotinoyloxychroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(6-hydroxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(7-t-butyl-6-hydroxy-2-methyl-4-oxochroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(6-hydroxy-2-isobutyl-5,7,8-trimethyl-4-oxochroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(6-hydroxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one 5-[4-(7-t-butyl-6-hydroxy-2-methyl-4-oxochroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one 5-[4-(6-hydroxy-2-isobutyl-5,7,8-trimethyl-4-oxochroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one 5-[4-(6-acetoxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(6-acetoxy-5,7,8-trimethylchroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one 5-{4-[2-(6-acetoxy-7-t-butyl-2-methylchroman-2-yl)ethoxy]benzyl}-2-iminothiazolidin-4-one 5-{4-[2-(6-actoxy-7,8-dimethoxy-2,5-dimethylchroman-2-yl)ethoxy]benzyl}-2-iminothiazolidin-4-one and pharmaceutically acceptable salts thereof.

Claim 39

Compositions as claimed in claim 24, wherein said active compound is selected from the group consisting of: 5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(2-ethyl-6-hydroxy-5,7,8-trimethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-{4-[2-(7-t-butyl-6-hydroxy-2-methylchroman-2-yl)ethoxy]benzyl}thiazolidine-2,4-dione 5-[4-(6-hydroxy-2-isobutyl-5,7,8-trimethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(6-acetoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(6-butyryloxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(6-hydroxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione 5-[4-(7-t-butyl-6-hydroxy-2-methyl-4-oxochroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione and pharmaceutically acceptable salts thereof.

Claim 40

Compositions as claimed in claim 24, in which said active compound is selected from compounds of formula (1a): ##STR24## in which: R 1 and R 2 are the same or different and each represents hydrogen or a C 1 -C 5 alkyl group; R 3 represents hydrogen; C 1 -C 6 aliphatic acyl; (C 5 -C 7 cycloalkane)carbonyl; benzoyl, benzoyl substituted with one to three substituents selected from the group of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, hydroxy, halogen, nitro, amino and di(C 1 -C 4 alkyl)amino; naphthoyl; 4-7 membered heterocyclic acyl wherein heterocyclic moiety has O, S or N hetero atoms; phenyl(C 2 -C 3 )aliphatic acyl; cinnamoyl; (C 1 -C 6 alkoxy)carbonyl; or benzoyloxycarbonyl; R 4 and R 5 are the same or different and each represents hydrogen, a C 1 -C 5 alkyl group or a C 1 -C 5 alkoxy group, or R 4 and R 5 together represent a C 1 -C 4 alkylenedioxy group; n is 1, 2 or 3; and Y and Z are the same or different and each represents the oxygen atom or the imino group; and pharmaceutically acceptable salts thereof.

Claim 41

Compositions as claimed in claim 24, in which said active compound is selected from compounds of formula (Ib): ##STR25## in which: R 1 and R 2 are the same or different and each represents hydrogen or a C 1 -C 5 alkyl group; R 3 represents hydrogen; C 1 -C 6 aliphatic acyl; (C 5 -C 7 cycloalkane)carbonyl; benzoyl, benzoyl substituted with one to three substituents selected from the group of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, hydroxy, halogen, nitro, amino and di(C 1 -C 4 alkyl)amino; naphthoyl; 4-7 membered heterocyclic acyl wherein heterocyclic moiety has O, S or N hetero atoms; phenyl(C 2 -C 3 )aliphatic acyl; cinnamoyl; (C 1 -C 6 alkoxy)carbonyl; or benzoyloxycarbonyl; R 4 and R 5 are the same or different and each represent hydrogen, a C 1 -C 5 alkyl group or a C 1 -C 5 alkoxy group, or R 4 and R 5 together represent a C 1 -C 4 alkylenedioxy group; n is 1, 2 or 3; and Y and Z are the same or different and each represents the oxygen atom or the amino group; and pharmaceutically acceptable salts thereof.

Claim 42

Compositions as claimed in claim 24, in which said active compound is selected from compounds of formula (Ic): ##STR26## in which: R 1 and R 2 are the same or different and each represents hydrogen or a C 1 -C 5 alkyl group; R 3 represents hydrogen; C 1 -C 6 aliphatic acyl; (C 5 -C 7 cycloalkane)carbonyl; benzoyl, benzoyl substituted with one to three substituents selected from the group of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, hydroxy, halogen, nitro, amino and di(C 1 -C 4 alkyl)amino; naphthoyl; 4-7 membered heterocyclic acyl wherein heterocyclic moiety has O, S or N hetero atoms; phenyl(C 2 -C 3 )aliphatic acyl; cinnamoyl; (C 1 -C 6 alkoxy)carbonyl; or benzoyloxycarbonyl; R 4 and R 5 are the same or different and each represents hydrogen, a C 1 -C 5 alkyl group or a C 1 -C 5 alkoxy group, or R 4 and R 5 together represent a C 1 -C 4 alkylenedioxy group; n is 1, 2 or 3; R 6 represents any one of the atoms or groups defined for R 3 and may be the same as or different from R 3 ; and Y and Z are the same or different and each represents the oxygen atom or the imino group; and pharmaceutically acceptable salts thereof.

Claim 43

Compositions as claimed in claim 24 or claim 35, wherein said active compound is in the form of a salt with a cation.

Claim 44

Compositions as claimed in claim 24 or claim 35, wherein said active compound is in the form of the sodium salt.