Novel heterocyclic analogs of diphenylethylene compounds

A compound represented by the following formula 1:

• wherein Z is
• n, m, q and r independently represent integers from zero to 4 provided that n+m≦4 and q+r≦4;
• p and s independently represent integers from zero to 5 provided that p+s≦5;
• a, b and c represent double bonds which may be present or absent;
• when present, the double bonds may be in the E or Z configuration and, when absent, the resulting stereocenters may have the R- or S-configuration;
• R independently represents a hydrogen atom;
• linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• —CO2Z′;
• —CO2R′″;
• —NH2;
• —NHR′″;
• —NR2′″;
• —OH;
• —OR′″;
• —CONR2″″;
• halogen atom;
• optionally substituted linear or branched C1-C20 alkyl;
• optionally substituted linear or branched C2-C20 alkenyl;
• R′ independently represents a hydrogen atom;
• linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• —CO2Z′;
• —CO2R′″;
• —NH2;
• —NHR′″;
• —NR2′″;
• —OR′″;
• —CONR2″″;
• halogen atom;
• optionally substituted linear or branched C1-C20 alkyl;
• optionally substituted linear or branched C2-C20 alkenyl;
• R″ independently represents a hydrogen atom;
• linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• —CO2Z′;
• —CO2R′″;
• —NH2;
• —NHR′″;
• —NR2′″;
• —OH;
• —OR′″;
• halogen atom;
• optionally substituted linear or branched C1-C20 alkyl;
• optionally substituted linear or branched C2-C20 alkenyl;
• R′″ independently represents a linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• or —(CH2)x—Ar, where x represents an integer from 1 to 6 and Ar represents aryl;
• R″″ independently represents a hydrogen atom;
• optionally substituted C1-C20 alkyl;
• optionally substituted C1-C20 alkoxy;
• optionally substituted C2-C20 alkenyl;
• optionally substituted C6-C10 aryl;
• or NR2″″ represents a cyclic moiety;
• Z′ represents a hydrogen atom or a pharmaceutically acceptable counter-ion;
• A, A′ and A″ each independently represent a hydrogen atom;
• C1-C20 acylamino;
• C1-C20 acyloxy;
• C1-C20 alkanoyl;C1-C20 alkoxycarbonyl;
• C1-C20 alkoxy;
• C1-C20 alkylamino;
• C1-C20 alkylcarboxylamino;
• carboxyl;
• cyano;
• halo;
• or hydroxy;
• B, B′ and B″ each independently represent;
• C2-C20 alkenoyl;
• aroyl;
• aralkanoyl;
• nitro;
• optionally substituted, linear or branched C1-C20 alkyl;
• or optionally substituted, linear or branched C2-C20 alkenyl;
• or A and B jointly, A′ and B′ jointly, or A″ and B″ jointly, independently represent a methylenedioxy or ethylenedioxy group;
• and
• X and X′ independently represent >NH, >NR′″, —O—, or —S—.

A pharmaceutical composition comprising:

• a therapeutically effective amount of a compound represented by the following formula 1:
• wherein Z is
• n, m, q and r independently represent integers from zero to 4 provided that n+m≦4 and q+r≦4;
• p and s independently represent integers from zero to 5 provided that p+s≦5;
• a, b and c represent double bonds which may be present or absent;
• when present, the double bonds may be in the E or Z configuration and, when absent, the resulting stereocenters may have the R- or S-configuration;
• R and R′ each independently represent a hydrogen atom;
• linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• —CO2Z′;
• —CO2R′″;
• —NH2;
• —NHR′″;
• —NR2′″;
• —OH;
• —OR′″;
• —CONR2″″;
• halogen atom;
• optionally substituted linear or branched C1-C20 alkyl;
• optionally substituted linear or branched C2-C20 alkenyl;
• R″ independently represents a hydrogen atom;
• linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• —CO2Z′;
• —CO2R′″;
• —NH2;
• —NHR′″;
• —NR2′″;
• —OH;
• —OR′″;
• halogen atom;
• optionally substituted linear or branched C1-C20 alkyl;
• optionally substituted linear or branched C2-C20 alkenyl;
• R′″ independently represents a linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• or —(CH2)x—Ar, where x represents an integer from 1 to 6 and Ar represents aryl;
• R″″ independently represents a hydrogen atom;
• optionally substituted C1-C20 alkyl;
• optionally substituted C1-C20 alkoxy;
• optionally substituted C2-C20 alkenyl;
• optionally substituted C6-C10 aryl;
• or NR2″″ represents a cyclic moiety;
• Z′ represents a hydrogen atom or a pharmaceutically acceptable counter-ion;
• A, A′ and A″ each independently represent a hydrogen atom;
• C1-C20 acylamino;
• C1-C20 acyloxy;
• C1-C20 alkanoyl;C1-C20 alkoxycarbonyl;
• C1-C20 alkoxy;
• C1-C20 alkylamino;
• C1-C20 alkylcarboxylamino;
• carboxyl;
• cyano;
• halo;
• or hydroxy;
• B, B′ and B″″ each independently represent;
• C2-C20 alkenoyl;
• aroyl;
• aralkanoyl;
• nitro;
• optionally substituted, linear or branched C1-C20 alkyl;
• or optionally substituted, linear or branched C2-C20 alkenyl;
• or A and B jointly, A′ and B′ jointly, or A″ and B″ jointly, independently represent a methylenedioxy or ethylenedioxy group;
• and
• X and X′ independently represent >NH, >NR′″, —O—, or —S—;
• in a physiologically acceptable carrier.

A pharmaceutical composition comprising:

• a therapeutically effective amount of a compound represented by the following formula 1:
• wherein Z is
• n, m, q and r independently represent integers from zero to 4 provided that n+m≦4 and q+r≦4;
• p and s independently represent integers from zero to 5 provided that p+s≦5;
• a, b and c represent double bonds which may be present or absent;
• when present, the double bonds may be in the E or Z configuration and, when absent, the resulting stereocenters may have the R- or S-configuration;
• R independently represents a hydrogen atom;
• linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• —CO2Z′;
• —CO2R′″;
• —NH2;
• —NHR′″;
• —NR2′″;
• —OH;
• —OR′″;
• —CONR2″″;
• halogen atom;
• optionally substituted linear or branched C1-C20 alkyl;
• optionally substituted linear or branched C2-C20 alkenyl;
• R′ independently represents a hydrogen atom;
• linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• —CO2Z′;
• —CO2R′″;
• —NH2;
• —NHR′″;
• —NR2′″;
• —OR′″;
• —CONR2″″;
• halogen atom;
• optionally substituted linear or branched C1-C20 alkyl;
• optionally substituted linear or branched C2-C20 alkenyl;
• R″ independently represents a hydrogen atom;
• linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• —CO2Z′;
• —CO2R′″;
• —NH2;
• —NHR′″;
• —NR2′″;
• —OH;
• —OR′″;
• halogen atom;
• optionally substituted linear or branched C1-C20 alkyl;
• optionally substituted linear or branched C2-C20 alkenyl;
• R′″ independently represents a linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• or —(CH2)x—Ar, where x represents an integer from 1 to 6 and Ar represents aryl;
• R″″ independently represents a hydrogen atom;
• optionally substituted C1-C20 alkyl;
• optionally substituted C1-C20 alkoxy;
• optionally substituted C2-C20 alkenyl;
• optionally substituted C6-C10 aryl;
• or NR2″″represents a cyclic moiety;
• Z′ represents a hydrogen atom or a pharmaceutically acceptable counter-ion;
• A, A′ and A″ each independently represent a hydrogen atom;
• C1-C20 acylamino;
• C1-C20 acyloxy;
• C1-C20 alkanoyl;C1-C20 alkoxycarbonyl;
• C1-C20 alkoxy;
• C1-C20 alkylamino;
• C1-C20 alkylcarboxylamino;
• carboxyl;
• cyano;
• halo;
• or hydroxy;
• B, B′ and B″ each independently represent;
• C2-C20 alkenoyl;
• aroyl;
• aralkanoyl;
• nitro;
• optionally substituted, linear or branched C1-C20 alkyl;
• or optionally substituted, linear or branched C2-C20 alkenyl;
• or A and B jointly, A′ and B′ jointly, or A″ and B″ jointly, independently represent a methylenedioxy or ethylenedioxy group;
• and
• X and X′ independently represent >NH, >NR′″, —O—, or —S—;
• in a physiologically acceptable carrier.

A method of treating diabetes comprising:

• administering to a subject suffering from a diabetic condition, a therapeutically effective amount of a compound represented by the following formula 1:
• wherein Z is
• n, m, q and r independently represent integers from zero to 4 provided that n+m≦4 and q+r≦4;
• p and s independently represent integers from zero to 5 provided that p+s≦5;
• a, b and c represent double bonds which may be present or absent;
• when present, the double bonds may be in the E or Z configuration and, when absent, the resulting stereocenters may have the R- or S-configuration;
• R and R′ each independently represent a hydrogen atom;
• linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• —CO2Z′;
• —CO2R′″;
• —NH2;
• —NHR′″;
• —NR2′″;
• —OH;
• —OR′″;
• —CONR2″″;
• halogen atom;
• optionally substituted linear or branched C1-C20 alkyl;
• optionally substituted linear or branched C2-C20 alkenyl;
• R″ independently represents a hydrogen atom;
• linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• —CO2Z′;
• —CO2R′″;
• —NH2;
• —NHR′″;
• —NR2′″;
• —OH;
• —OR′″;
• halogen atom;
• optionally substituted linear or branched C1-C20 alkyl;
• optionally substituted linear or branched C2-C20 alkenyl;
• R′″ independently represents a linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• or —(CH2)x—Ar, where x represents an integer from 1 to 6 and Ar represents aryl;
• R″″ independently represents a hydrogen atom;
• optionally substituted C1-C20 alkyl;
• optionally substituted C1-C20 alkoxy;
• optionally substituted C2-C20 alkenyl;
• optionally substituted C6-C10 aryl;
• or NR2″″ represents a cyclic moiety;
• Z′ represents a hydrogen atom or a pharmaceutically acceptable counter-ion;
• A, A′ and A″ each independently represent a hydrogen atom;
• C1-C20 acylamino;
• C1-C20 acyloxy;
• C1-C20 alkanoyl;C1-C20 alkoxycarbonyl;
• C1-C20 alkoxy;
• C1-C20 alkylamino;
• C1-C20 alkylcarboxylamino;
• carboxyl;
• cyano;
• halo;
• or hydroxy;
• B, B′ and B″ each independently represent;
• C2-C20 alkenoyl;
• aroyl;
• aralkanoyl;
• nitro;
• optionally substituted, linear or branched C1-C20 alkyl;
• or optionally substituted, linear or branched C2-C20 alkenyl;
• or A and B jointly, A′ and B′ jointly, or A″ and B″ jointly, independently represent a methylenedioxy or ethylenedioxy group;
• and
• X and X′ independently represent >NH, >NR′″, —O—, or —S—;
• in a physiologically acceptable carrier.

A method of treating diabetes comprising:

• administering to a subject suffering from a diabetic condition, a therapeutically effective amount of a compound represented by the following formula 1:
• wherein Z is
• n, m, q and r independently represent integers from zero to 4 provided that n+m≦4 and q+r≦4;
• p and s independently represent integers from zero to 5 provided that p+s≦5;
• a, b and c represent double bonds which may be present or absent;
• when present, the double bonds may be in the E or Z configuration and, when absent, the resulting stereocenters may have the R- or S-configuration;
• R independently represents a hydrogen atom;
• linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• —CO2Z′;
• —CO2R′″;
• —NH2;
• —NHR′″;
• —NR2′″;
• —OH;
• —OR′″;
• —CONR2″″;
• halogen atom;
• optionally substituted linear or branched C1-C20 alkyl;
• optionally substituted linear or branched C2-C20 alkenyl;
• R′ independently represents a hydrogen atom;
• linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• —CO2Z′;
• —CO2R′″;
• —NH2;
• —NHR′″;
• —NR2′″;
• —OR′″;
• —CONR2″″;
• halogen atom;
• optionally substituted linear or branched C1-C20 alkyl;
• optionally substituted linear or branched C2-C20 alkenyl;
• R″ independently represents a hydrogen atom;
• linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• —CO2Z′;
• —CO2R′″;
• —NH2;
• —NHR′″;
• —NR2′″;
• —OH;
• —OR′″;
• halogen atom;
• optionally substituted linear or branched C1-C20 alkyl;
• optionally substituted linear or branched C2-C20 alkenyl;
• R′″ independently represents a linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• or —(CH2)x—Ar, where x represents an integer from 1 to 6 and Ar represents aryl;
• R″″ independently represents a hydrogen atom;
• optionally substituted C1-C20 alkyl;
• optionally substituted C1-C20 alkoxy;
• optionally substituted C2-C20 alkenyl;
• optionally substituted C6-C10 aryl;
• or NR2″″ represents a cyclic moiety;
• Z′ represents a hydrogen atom or a pharmaceutically acceptable counter-ion;
• A, A′ and A″ each independently represent a hydrogen atom;
• C1-C20 acylamino;
• C1-C20 acyloxy;
• C1-C20 alkanoyl;C1-C20 alkoxycarbonyl;
• C1-C20 alkoxy;
• C1-C20 alkylamino;
• C1-C20 alkylcarboxylamino;
• carboxyl;
• cyano;
• halo;
• or hydroxy;
• B, B′ and B″ each independently represent;
• C2-C20alkenoyl;
• aroyl;
• aralkanoyl;
• nitro;
• optionally substituted, linear or branched C1-C20 alkyl;
• or optionally substituted, linear or branched C2-C20 alkenyl;
• or A and B jointly, A′ and B′ jointly, or A″ and B″ jointly, independently represent a methylenedioxy or ethylenedioxy group;
• and
• X and X′ independently represent >NH, >NR′″, —O—, or —S—;
• in a physiologically acceptable carrier.

A method of treating inflammation or inflammatory disease comprising:

• administering to a subject suffering from such condition, a therapeutically effective amount of a compound represented by the following formula 1:
• wherein Z is
• n, m, q and r independently represent integers from zero to 4 provided that n+m≦4 and q+r≦4;
• p and s independently represent integers from zero to 5 provided that p+s≦5;
• a, b and c represent double bonds which may be present or absent;
• when present, the double bonds may be in the E or Z configuration and, when absent, the resulting stereocenters may have the R- or S-configuration;
• R and R′ each independently represent a hydrogen atom;
• linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• —CO2Z′;
• —CO2R′″;
• —NH2;
• —NHR′″;
• —NR2′″;
• —OH;
• —OR′″;
• —CONR2″″;
• halogen atom;
• optionally substituted linear or branched C1-C20 alkyl;
• optionally substituted linear or branched C2-C20 alkenyl;
• R″ independently represents a hydrogen atom;
• linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• —CO2Z′;
• —CO2R ′″;
• —NH2;
• —NHR′″;
• —NR2′″;
• —OH;
• —OR′″;
• halogen atom;
• optionally substituted linear or branched C1-C20 alkyl;
• optionally substituted linear or branched C2-C20 alkenyl;
• R′″ independently represents a linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• or —(CH2)x—Ar, where x represents an integer from 1 to 6 and Ar represents aryl;
• R″″ independently represents a hydrogen atom;
• optionally substituted C1-C20 alkyl;
• optionally substituted C1-C20 alkoxy;
• optionally substituted C2-C20 alkenyl;
• optionally substituted C6-C10 aryl;
• or NR2″″ represents a cyclic moiety;
• Z′ represents a hydrogen atom or a pharmaceutically acceptable counter-ion;
• A, A′ and A″ each independently represent a hydrogen atom;
• C1-C20 acylamino;
• C1-C20 acyloxy;
• C1-C20 alkanoyl;C1-C20 alkoxycarbonyl;
• C1-C20 alkoxy;
• C1-C20 alkylamino;
• C1-C20 alkylcarboxylamino;
• carboxyl;
• cyano;
• halo;
• or hydroxy;
• B, B′ and B″ each independently represent;
• C2-C20 alkenoyl;
• aroyl;
• aralkanoyl;
• nitro;
• optionally substituted, linear or branched C1-C20 alkyl;
• or optionally substituted, linear or branched C2-C20 alkenyl;
• or A and B jointly, A′ and B′ jointly, or A″ and B″ jointly, independently represent a methylenedioxy or ethylenedioxy group;
• and
• X and X′ independently represent >NH, >NR′″, —O—, or —S—;
• in a physiologically acceptable carrier.

A method of treating inflammation or inflammatory disease comprising:

• administering to a subject suffering from such condition, a therapeutically effective amount of a compound represented by the following formula 1:
• wherein Z is
• n, m, q and r independently represent integers from zero to 4 provided that n+m≦4 and q+r≦4;
• p and s independently represent integers from zero to 5 provided that p+s≦5;
• a, b and c represent double bonds which may be present or absent;
• when present, the double bonds may be in the E or Z configuration and, when absent, the resulting stereocenters may have the R- or S-configuration;
• R independently represents a hydrogen atom;
• linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• —CO2Z′;
• —CO2R′″;
• —NH2;
• —NHR′″;
• —NR2′″;
• —OH;
• —OR′″;
• —CONR2″″;
• halogen atom;
• optionally substituted linear or branched C1-C20 alkyl;
• optionally substituted linear or branched C2-C20 alkenyl;
• R′ independently represents a hydrogen atom;
• linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• —CO2Z′;
• —CO2R′″;
• —NH2;
• —NHR′″;
• —NR2′″;
• —OR′″;
• —CONR2″″;
• halogen atom;
• optionally substituted linear or branched C1-C20 alkyl;
• optionally substituted linear or branched C2-C20 alkenyl;
• R″ independently represents a hydrogen atom;
• linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• —CO2Z′;
• —CO2R′″;
• —NH2;
• —NHR′″;
• —NR2′″;
• —OH;
• —OR′″;
• halogen atom;
• optionally substituted linear or branched C1-C20 alkyl;
• optionally substituted linear or branched C2-C20 alkenyl;
• R′″ independently represents a linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• or —(CH2)x—Ar, where x represents an integer from 1 to 6 and Ar represents aryl;
• R″″ independently represents a hydrogen atom;
• optionally substituted C1-C20 alkyl;
• optionally substituted C1-C20 alkoxy;
• optionally substituted C2-C20 alkenyl;
• optionally substituted C6-C10 aryl;
• or NR2″″ represents a cyclic moiety;
• Z′ represents a hydrogen atom or a pharmaceutically acceptable counter-ion;
• A, A′ and A″ each independently represent a hydrogen atom;
• C1-C20 acylamino;
• C1-C20 acyloxy;
• C1-C20 alkanoyl;C1-C20 alkoxycarbonyl;
• C1-C20 alkoxy;
• C1-C20 alkylamino;
• C1-C20 alkylcarboxylamino;
• carboxyl;
• cyano;
• halo;
• or hydroxy;
• B, B′ and B″ each independently represent;
• C2-C20 alkenoyl;
• aroyl;
• aralkanoyl;
• nitro;
• optionally substituted, linear or branched C1-C20 alkyl;
• or optionally substituted, linear or branched C2-C20 alkenyl;
• or A and B jointly, A′ and B′ jointly, or A″ and B″ jointly, independently represent a methylenedioxy or ethylenedioxy group;
• and
• X and X′ independently represent >NH, >NR′″, —O—, or —S—;
• in a physiologically acceptable carrier.

A method of treating immunological disease comprising:

• administering to a subject suffering from an immunological disease a therapeutically effective amount of a compound represented by the following formula 1:
• wherein Z is
• n, m, q and r independently represent integers from zero to 4 provided that n+m≦4 and q+r≦4;
• p and s independently represent integers from zero to 5 provided that p+s≦5;
• a, b and c represent double bonds which may be present or absent;
• when present, the double bonds may be in the E or Z configuration and, when absent, the resulting stereocenters may have the R- or S-configuration;
• R and R′ each independently represent a hydrogen atom;
• linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• —CO2Z′;
• —CO2R′″;
• —NH2;
• —NHR′″;
• —NR2′″;
• —OH;
• —OR′″;
• —CONR2″″;
• halogen atom;
• optionally substituted linear or branched C1-C20 alkyl;
• optionally substituted linear or branched C2-C20 alkenyl;
• R″ independently represents a hydrogen atom;
• linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• —CO2Z′;
• —CO2R′″;
• —NH2;
• —NHR′″;
• —NR2′″;
• —OH;
• —OR′″;
• halogen atom;
• optionally substituted linear or branched C1-C20 alkyl;
• optionally substituted linear or branched C2-C20 alkenyl;
• R′″ independently represents a linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• or —(CH2)x—Ar, where x represents an integer from 1 to 6 and Ar represents aryl;
• R″″ independently represents a hydrogen atom;
• optionally substituted C1-C20 alkyl;
• optionally substituted C1-C20 alkoxy;
• optionally substituted C2-C20 alkenyl;
• optionally substituted C6-C10 aryl;
• or NR2″″ represents a cyclic moiety;
• Z′ represents a hydrogen atom or a pharmaceutically acceptable counter-ion;
• A, A′ and A″ each independently represent a hydrogen atom;
• C1-C20 acylamino;
• C1-C20 acyloxy;
• C1-C20 alkanoyl;C1-C20 alkoxycarbonyl;
• C1-C20 alkoxy;
• C1-C20 alkylamino;
• C1-C20 alkylcarboxylamino;
• carboxyl;
• cyano;
• halo;
• or hydroxy;
• B, B′ and B″ each independently represent;
• C2-C20 alkenoyl;
• aroyl;
• aralkanoyl;
• nitro;
• optionally substituted, linear or branched C1-C20 alkyl;
• or optionally substituted, linear or branched C2-C20 alkenyl;
• or A and B jointly, A′ and B′ jointly, or A″ and B″ jointly, independently represent a methylenedioxy or ethylenedioxy group;
• and
• X and X′ independently represent >NH, >NR′″, —O—, or —S—;
• in a physiologically acceptable carrier.

A method of treating immunological disease comprising:

• administering to a subject suffering from an immunological disease a therapeutically effective amount of a compound represented by the following formula 1:
• wherein Z is
• n, m, q and r independently represent integers from zero to 4 provided that n+m≦4 and q+r≦4;
• p and s independently represent integers from zero to 5 provided that p+s≦5;
• a, b and c represent double bonds which may be present or absent;
• when present, the double bonds may be in the E or Z configuration and, when absent, the resulting stereocenters may have the R- or S-configuration;
• R independently represents a hydrogen atom;
• linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• —CO2Z′;
• —CO2R′″;
• —NH2;
• —NHR′″;
• —NR2′″;
• —OH;
• —OR′″;
• —CONR2″″;
• halogen atom;
• optionally substituted linear or branched C1-C20alkyl;
• optionally substituted linear or branched C2-C20 alkenyl;
• R′ independently represents a hydrogen atom;
• linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• —CO2Z′;
• —CO2R′″;
• —NH2;
• —NHR′″;
• —NR2′″;
• —OR′″;
• —CONR2″″;
• halogen atom;
• optionally substituted linear or branched C1-C20 alkyl;
• optionally substituted linear or branched C2-C20 alkenyl;
• R″ independently represents a hydrogen atom;
• linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• —CO2Z′;
• —CO2R′″;
• —NH2;
• —NHR′″;
• —NR2′″;
• —OH;
• —OR′″;
• halogen atom;
• optionally substituted linear or branched C1-C20 alkyl;
• optionally substituted linear or branched C2-C20 alkenyl;
• R′″ independently represents a linear or branched C1-C20 alkyl;
• linear or branched C2-C20 alkenyl;
• or —(CH2)x—Ar, where x represents an integer from 1 to 6 and Ar represents aryl;
• R″″ independently represents a hydrogen atom;
• optionally substituted C1-C20 alkyl;
• optionally substituted C1-C20 alkoxy;
• optionally substituted C2-C20 alkenyl;
• optionally substituted C6-C10 aryl;
• or NR2″″ represents a cyclic moiety;
• Z′ represents a hydrogen atom or a pharmaceutically acceptable counter-ion;
• A, A′ and A″ each independently represent a hydrogen atom;
• C1-C20 acylamino;
• C1-C20 acyloxy;
• C1-C20 alkanoyl;C1-C20 alkoxycarbonyl;
• C1-C20 alkoxy;
• C1-C20 alkylamino;
• C1-C20 alkylcarboxylamino;
• carboxyl;
• cyano;
• halo;
• or hydroxy;
• B, B′ and B″ each independently represent;
• C2-C20 alkenoyl;
• aroyl;
• aralkanoyl;
• nitro;
• optionally substituted, linear or branched C1-C20 alkyl;
• or optionally substituted, linear or branched C2-C20 alkenyl;
• or A and B jointly, A′ and B′ jointly, or A″ and B″ jointly, independently represent a methylenedioxy or ethylenedioxy group;
• and
• X and X′ independently represent >NH, >NR′″, —O—, or —S—;
• in a physiologically acceptable carrier.

A pharmaceutical composition comprising a therapeutically effective amount of a compound selected from the group consisting of:

• 2-{4-[4-(2,4-dioxothiazolidin-5-ylidenemethyl)-phenoxy]-phenyl}-3-p-tolylacrylic acid,
• 2-{4-[4-(2,4-dioxothiazolidin-5-ylmethyl)-phenoxy]-phenyl}-3-p-tolylacrylic acid,
• 2-{4-[4-(2,4-dioxothiazolidin-5-ylmethyl)-phenoxy]-phenyl}-3-p-tolylacrylic acid methyl ester,
• 3-(3,5-dimethylphenyl)-2-{4-[4-(2,4-dioxothiazolidin-5-ylidenemethyl)-phenoxy]-phenyl}-acrylic acid,
• 3-(3,5-dimethylphenyl)-2-{4-[4-(2,4-dioxothiazolidin-5-ylmethyl)-phenoxy]-phenyl}-acrylic acid,
• 3-(3,5-dimethylphenyl)-2-{4-[4-(2,4-dioxothiazolidin-5-ylmethyl)-phenoxy]-phenyl}-acrylic acid methyl ester,
• 5-(4-{4-[2-(3,5-dimethylphenyl)-1-(morpholine-4-carbonyl)-vinyl]-phenoxy}-benzyl)-thiazolidine-2,4-dione,
• 5-(4-{4-[2-(4-methoxyphenyl)-vinyl]-phenoxy}-benzyl)-thiazolidine-2,4-dione,
• 5-(4-{4-[2-(3,5-dimethoxyphenyl)-vinyl]-phenoxy}-benzyl)-thiazolidine-2,4-dione,
• 5-[4-(4′-methoxybiphenyl-3-yloxy)-benzylidene]-thiazolidine-2,4-dione,
• 5-[4-(4′-methoxybiphenyl-3-yloxy)-benzyl]-thiazolidine-2,4-dione,
• 5-[4-(2′,4′-dimethoxybiphenyl-3-yloxy)-benzylidene]-thiazolidine-2,4-dione, and
• 5-[4-(3′,5′-dimethoxybiphenyl-3-yloxy)-benzyl]-thiazolidine-2,4-dione,
• together with a physiologically acceptable carrier therefor.