# US 5,703,096 A · Oxime derivatives, their preparation and their therapeutic use

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- Number: US 5,703,096 A
- Document ID: US5703096A
- Status: Granted
- Kind: A
- Application number: 08/539,541
- Filed: 1995-10-05
- Granted: 1997-12-30
- Earliest claimed: 1994-10-07
- Assignees: Sankyo Company, Limited
- Inventors: Hiroaki Yanagisawa; Takashi Fujita; Koichi Fujimoto; Takao Yoshioka; Kunio Wada; Minoru Oguchi; Toshihiko Fujiwara; Hiroyoshi Horikoshi
- Web page: https://patentgrep.com/patent/US5703096A

## CPC

- C07D 263/44: Two oxygen atoms
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- C07D 271/07: with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D 277/34: Oxygen atoms
- C07D 417/12: linked by a chain containing hetero atoms as chain links
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Compounds of formula (I): ##STR1## wherein: R.sup.1 is hydrogen or alkyl; R.sup.2 is alkylene; R.sup.3 is hydrogen, alkyl, alkoxy, alkylthio, halogen, nitro group, amino group, monoalkylamino, dialkylamino, aryl, or aralkyl; X is aryl, or aromatic heterocyclic; Y is oxygen, sulfur or a group of formula >N-R.sup.4, in which R.sup.4 is hydrogen, alkyl or acyl; and Z is a group of formula (Za), (Zb), (Zc) or (Zd): ##STR2## and salts thereof can be used to treat or prevent are included those arising from hyperlipidemia, hyperglycemia, obesity, impaired glucose tolerance (IGT), insulin resistant non-IGT (NGT), non-diagnostic glucose tolerance, insulin resistance, diabetic complications, fatty liver, polycystic ovary syndrome (PCOS) and gestational diabetes mellitus (GDM); in addition the compounds of the present invention have aldose reductase inhibitory activity.

## Claims

### Claim 1

A compound of formula (I): ##STR15## wherein: R.sup.1 represents a hydrogen atom or an alkyl group having from 1 to 6 carbon atoms;
R.sup.2 represents an alkylene group having from 2 to 6 carbon atoms;
R.sup.3 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, an alkoxy group having from 1 to 4 carbon atom, an alkylthio group having from 1 to 4 carbon atoms, a halogen atom, a nitro group, an amino group, a monoalkylamino group having from 1 to 4 carbon atoms, a dialkylamino group whose alkyl groups are the same or different and each has from 1 to 4 carbon atoms, an aryl group having from 6 to 10 carbon atoms in a carbocyclic ring which is unsubstituted or is substituted by at least one of the following substituents .alpha., or an aralkyl group in which an alkyl group having from 1 to 4 carbon atoms is substituted by an aryl group as defined above;
X represents an aryl group having from 6 to 10 carbon atoms in a carbocyclic ring which is unsubstituted or is substituted by at least one of the following substituents .alpha., or an aromatic heterocyclic group having one or two rings, of which at least one is heterocyclic, said group being unsubstituted or being substituted by at least one of the following substituents .alpha.;
said substituents .alpha. are selected from the group consisting of:
alkyl groups having from 1 to 6 carbon atoms;
halogenated alkyl groups having from 1 to 4 carbon atoms;
hydroxy groups;
acyloxy groups having from 1 to 4 carbon atoms;
alkoxy groups having from 1 to 4 carbon atoms;
alkylenedioxy groups having from 1 to 4 carbon atoms;
aralkyloxy groups in which an alkoxy group having from 1 to 4 carbon atoms is substituted by an aryl group having from 6 to 10 carbon atoms in a carbocyclic ring which is unsubstituted or is substituted by at least one of the following substituents .beta.;
alkylthio groups having from 1 to 4 carbon atoms;
alkylsulfonyl groups having from 1 to 4 carbon atoms;
halogen atoms;
nitro groups;
amino groups;
monoalkylamino groups having from 1 to 4 carbon atoms;
dialkylamino groups, whose alkyl groups are the same or different and each is an alkyl group having from 1 to 4 carbon atoms;
aralkyl groups in which an alkyl group having from 1 to 4 carbon atoms is substituted by an aryl group having from 6 to 10 carbon atoms in a carbocyclic ring which is unsubstituted or is substituted by at least one of the following substituents .beta.;
aryl groups having from 6 to 10 carbon atoms in a carbocyclic ring which is unsubstituted or is substituted by at least one of the following substituents .beta.;
aryloxy groups in which the aryl part has from 6 to 10 carbon atoms in a carbocyclic ring which is unsubstituted or is substituted by at least one of the following substituents .beta.;
arylthio groups in which the aryl part has from 6 to 10 carbon atoms in a carbocyclic ring which is unsubstituted or is substituted by at least one of the following substituents .beta.;
arylsulfonyl groups in which the aryl part has from 6 to 10 carbon atoms in a carbocyclic ring which is unsubstituted or is substituted by at least one of the following substituents .beta.;
arylsulfonylamino groups in which the aryl part has from 6 to 10 carbon atoms in a carbocyclic ring which is unsubstituted or is substituted by at least one of the following substituents .beta., and in which the nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms;
groups of formula --R.sup.X ;
groups of formula --OR.sup.X ;
groups of formula --SR.sup.X ;
groups of formula --SO.sub.2 R.sup.X ; and
groups of formula --N(R.sup.Z)SO.sub.2 R.sup.X ;
in which R.sup.X represents a pyridyl heterocyclic group or an aromatic heterocyclic ring having 5 ring atoms of which from 1 to 3 are selected from the group consisting of nitrogen, oxygen and sulfur atoms or a fused ring system in which such an aromatic heterocyclic ring is fused to an aryl group having from 6 to 10 carbon atoms in a carbocyclic ring; and R.sup.Z represents an alkyl group having from 1 to 6 carbon atoms;
said substituents .beta. are selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, halogenated alkyl groups having from 1 to 4 carbon atoms, alkoxy groups having from 1 to 4 carbon atoms, halogen atoms, and alkylenedioxy groups having from 1 to 4 carbon atoms;
Y represents an oxygen atom, a sulfur atom or a group of formula >N--R.sup.4, in which R.sup.4 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms or an acyl group having from 1 to 8 carbon atoms; and
Z represents a group of formula (Za), (Zb), (Zc) or (Zd): ##STR16## and salts thereof with the proviso that at least one of R.sup.3 and X contains a pyridyl group.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R.sup.1 represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms.

### Claim 3 (depends on 1)

The compound of claim 1, wherein R.sup.1 represents a hydrogen atom or an alkyl group having from 1 to 3 carbon atoms.

### Claim 4 (depends on 1)

The compound of claim 1, wherein R.sup.1 represents a hydrogen atom, a methyl or ethyl group.

### Claim 5 (depends on 1)

The compound of claim 1, wherein R.sup.1 represents a methyl or ethyl group.

### Claim 6 (depends on 1)

The compound of claim 1, wherein R.sup.2 represents an alkylene group having from 2 to 5 carbon atoms.

### Claim 7 (depends on 1)

The compound of claim 1, wherein R.sup.2 represents an alkylene group having 2 or 3 carbon atoms.

### Claim 8 (depends on 1)

The compound of claim 1, wherein R.sup.2 represents an ethylene, trimethylene or methylethylene group.

### Claim 9 (depends on 1)

The compound of claim 1, wherein R.sup.2 represents an ethylene group.

### Claim 10 (depends on 1)

The compound of claim 1, wherein R.sup.3 represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, an alkoxy group having 1 or 2 carbon atoms, an alkylthio group having 1 or 2 carbon atoms or a halogen atom.

### Claim 11 (depends on 1)

The compound of claim 1, wherein R.sup.3 represents a hydrogen atom.

### Claim 12 (depends on 1)

The compound of claim 1, wherein X represents: an aryl group, which has from 6 to 10 ring carbon atoms and is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.1, defined below; or an aromatic heterocyclic group which has from 5 to 10 ring atoms in one or two rings, of which atoms from 1 to 3 are hetero-atoms selected from the group consisting of nitrogen, oxygen and sulfur atoms, said group being unsubstituted or being substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.1, defined below;
said substituents .alpha..sup.1 being selected from the group consisting of:
alkyl groups having from 1 to 6 carbon atoms,
halogenated alkyl groups having from 1 to 4 carbon atoms,
hydroxy groups,
acyloxy groups having from 1 to 4 carbon atoms,
alkoxy groups having from 1 to 4 carbon atoms,
alkylenedioxy groups having from 1 to 4 carbon atoms,
aralkyloxy groups having a total of from 7 to 12 carbon atoms,
alkylthio groups having from 1 to 4 carbon atoms,
alkylsulfonyl groups having from 1 to 4 carbon atoms,
halogen atoms,
aralkyl groups having a total of from 7 to 12 carbon atoms,
phenyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenoxy groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenylthio groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenylsulfonyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenylsulfonylamino groups in which the phenyl group is unsubstituted or is substituted by from 1 to 3 of substituents .beta..sup.1, defined below, and the nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyridyloxy, pyridylthio and pyridylsulfonyl groups,
imidazolyl groups in which a nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
pyridylsulfonylamino groups in which the amino group is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
said substituents .beta..sup.1 being selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, halogenated alkyl groups having from 1 to 4 carbon atoms, alkoxy groups having from 1 to 4 carbon atoms, halogen atoms and alkylenedioxy groups having from 1 to 4 carbon atoms.

### Claim 13 (depends on 1)

The compound of claim 1, wherein X represents: an aryl group, which has from 6 to 10 ring carbon atoms and is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.2, defined below; or an aromatic heterocyclic group which has from 5 to 10 ring atoms in one or two rings, of which atoms from 1 to 3 are hetero-atoms selected from the group consisting of nitrogen, oxygen and sulfur atoms, said group being unsubstituted or being substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.2, defined below;
said substituents .alpha..sup.2 being selected from the group consisting of:
alkyl groups having from 1 to 6 carbon atoms,
halogenated alkyl groups having from 1 to 4 carbon atoms,
hydroxy groups,
alkanoyloxy groups having from 1 to 4 carbon atoms,
alkoxy groups having from 1 to 4 carbon atoms,
alkylenedioxy groups having from 1 to 4 carbon atoms,
aralkyloxy groups having a total of from 7 to 12 carbon atoms,
alkylthio groups having from 1 to 4 carbon atoms,
alkylsulfonyl groups having from 1 to 4 carbon atoms,
fluorine atoms, chlorine atoms and bromine atoms,
aralkyl groups having a total of from 7 to 12 carbon atoms,
phenyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenoxy groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenylthio groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenylsulfonyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenylsulfonylamino groups in which the phenyl group is unsubstituted or is substituted by from 1 to 3 of substituents .beta..sup.1, defined below, and the nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
furyl thienyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyridyloxy, pyridylthio and pyridylsulfonyl groups;
imidazolyl groups in which a nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
pyridylsulfonylamino groups in which the amino group is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
said substituents .beta..sup.1 being selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, halogenated alkyl groups having from 1 to 4 carbon atoms, alkoxy groups having from 1 to 4 carbon atoms, halogen atoms and alkylenedioxy groups having from 1 to 4 carbon atoms.

### Claim 14 (depends on 1)

The compound of claim 1, wherein X represents a phenyl, naphthyl, imidazolyl, oxazolyl, pyridyl, indolyl, quinolyl or isoquinolyl group, each of which is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.3, defined below;
said substituents .alpha..sup.3 are selected from the group consisting of:
alkyl groups having from 1 to 6 carbon atoms,
halogenated alkyl groups having from 1 to 4 carbon atoms,
hydroxy groups,
alkanoyloxy groups having from 1 to 4 carbon atoms,
alkoxy groups having from 1 to 4 carbon atoms,
the methylenedioxy group,
aralkyloxy groups having a total of from 7 to 12 carbon atoms,
alkylthio groups having from 1 to 4 carbon atoms,
alkylsulfonyl groups having from 1 to 4 carbon atoms,
fluorine, chlorine and bromine atoms,
aralkyl groups having a total of from 7 to 12 carbon atoms,
phenyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.2, defined below,
phenoxy groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.2, defined below,
phenylthio groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.2, defined below,
phenylsulfonyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.2, defined below,
phenylsulfonylamino groups in which the phenyl group is unsubstituted or is substituted by from 1 to 3 of substituents .beta..sup.2, defined below, and the nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
furyl, thienyl, oxazolyl, isoxazolyl, thiazblyl, pyridyl, pyridyloxy, pyridylthio and pyridylsulfonyl groups;
imidazolyl groups in which a nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
pyridylsulfonylamino groups in which the amino group is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
said substituents .beta..sup.2 are selected from the group consisting of methyl groups, trifluoromethyl groups, methoxy groups, fluorine atoms and methylenedioxy groups.

### Claim 15 (depends on 1)

The compound of claim 1, wherein X represents a phenyl, naphthyl, imidazolyl, oxazolyl, pyridyl, indolyl, quinolyl or isoquinolyl group, each of which is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.4, defined below;
said substituents .alpha..sup.4 are selected from the group consisting of:
alkyl groups having from 1 to 6 carbon atoms,
halogenated alkyl groups having from 1 to 4 carbon atoms,
hydroxy groups,
alkanoyloxy groups having from 1 to 4 carbon atoms,
alkoxy groups having from 1 to 4 carbon atoms,
methylenedioxy, benzyloxy, phenethyloxy and naphthylmethyloxy groups,
alkylthio groups having from 1 to 4 carbon atoms,
alkylsulfonyl groups having from 1 to 4 carbon atoms,
fluorine, chlorine and bromine atoms,
the benzyl group,
phenyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.2, defined below,
phenoxy groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.2, defined below,
the phenylthio, phenylsulfonyl, phenylsulfonylamino, N-methylphenylsulfonylamino, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyridyloxy, pyridylthio, pyridylsulfonyl, pyridylsulfonylamino and N-methylpyridylsulfonylamino groups,
imidazolyl groups in which a nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms.

### Claim 16 (depends on 1)

The compound of claim 1, wherein X represents a phenyl, naphthyl, pyridyl, indolyl, quinolyl or isoquinolyl group, each of which is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.5, defined below;
said substituents .alpha..sup.5 are selected from the group consisting of:
alkyl groups having from 1 to 3 carbon atoms,
the trifluoromethyl, difluoromethyl, fluoromethyl, hydroxy, formyloxy and acetoxy groups,
alkoxy groups having from 1 to 3 carbon atoms,
the methylenedioxy, benzyloxy, methylthio, ethylthio, methylsulfonyl and ethylsulfonyl groups,
the fluorine, chlorine and bromine atoms, and
the benzyl, phenyl, 4-methylphenyl, 4-trifluoromethylphenyl, 4-methoxyphenyl, 4-fluorophenyl, 3,4-methylenedioxyphenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino, N-methylphenylsulfonylamino, furyl, thienyl, oxazolyl, thiazolyl, imidazolyl, N-methylimidazolyl, pyridyl, pyridyloxy, pyridylthio, pyridylsulfonyl, pyridylsulfonylamino and/or N-methylpyridylsulfonylamino groups.

### Claim 17 (depends on 1)

The compound of claim 1, wherein X represents a phenyl, naphthyl, pyridyl, quinolyl or isoquinolyl group, each of which is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.6, defined below;
said substituents .alpha..sup.6 are selected from the group consisting of: methyl, ethyl, isopropyl, trifluoromethyl, hydroxy, acetoxy, methoxy, ethoxy, isopropoxy, methylenedioxy, benzyloxy, methylthio, ethylthio, methylsulfonyl, ethylsulfonyl, benzyl, phenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino, N-methylphenylsulfonylamino, pyridyl, pyridyloxy, pyridylthio, pyridylsulfonyl, pyridylsulfonylamino and N-methylpyridylsulfonylamino groups and chlorine atoms.

### Claim 18 (depends on 1)

The compound of claim 1, wherein X represents a phenyl group which is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.7, defined below;
said substituents .alpha..sup.7 are selected from the group consisting of: methyl, hydroxy, acetoxy, benzyl, phenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino, N-methylphenylsulfonylamino, pyridyl, pyridyloxy, pyridylthio and pyridylsulfonyl groups and chlorine atoms.

### Claim 19 (depends on 1)

The compound of claim 1, wherein X represents a pyridyl group which is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.8, defined below;
said substituents .alpha..sup.8 are selected from the group consisting of: methoxy, ethoxy, isopropoxy, benzyloxy, methylthio, ethylthio, methylsulfonyl, ethylsulfonyl, benzyl, phenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino and N-methylphenylsulfonylamino groups.

### Claim 20 (depends on 1)

The compound of claim 1, wherein Y represents an oxygen atom, a sulfur atom or a group of formula >N--R.sup.4 in which R.sup.4 represents a hydrogen atom, an alkyl group having from 1 to 3 carbon atoms or an alkanoyl group having from 2 to 5 carbon atoms.

### Claim 21 (depends on 1)

The compound of claim 1, wherein Y represents an oxygen atom.

### Claim 22 (depends on 1)

The compound of claim 1, wherein Z represents a 2,4-dioxothiazolidin-5-ylmethyl, 2,N-dioxooxazolidin-5-ylmethyl or 3,5-dioxooxadiazolidin-2-ylmethyl group.

### Claim 23 (depends on 1)

The compound of claim 1, wherein Z represents a 2,4-dioxothiazolidin-5-ylmethyl or 2,4-dioxooxazolidin-5-ylmethyl group.

### Claim 24 (depends on 1)

The compound of claim 1, wherein Z represents a 2,4-dioxothiazolidin-5-ylmethyl group.

### Claim 25 (depends on 1)

The compound of claim 1, wherein:
R.sup.1 represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms;
R.sup.2 represents an alkylene group having from 2 to 5 carbon atoms;
R.sup.3 represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, an alkoxy group having 1 or 2 carbon atoms, an alkylthio group having 1 or 2 carbon atoms or a halogen atom;
X represents: an aryl group, which has from 6 to 10 ring carbon atoms and is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.1, defined below; or an aromatic heterocyclic group which has from 5 to 10 ring atoms in one or two rings, of which atoms from 1 to 3 are hetero-atoms selected from the group consisting of nitrogen, oxygen and sulfur atoms, said group being unsubstituted or being substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.1, defined below;
said substituents .alpha..sup.1 being selected from the group consisting of:
alkyl groups having from 1 to 6 carbon atoms,
halogenated alkyl groups having from 1 to 4 carbon atoms,
hydroxy groups,
acyloxy groups having from 1 to 4 carbon atoms,
alkoxy groups having from 1 to 4 carbon atoms,
alkylenedioxy groups having from 1 to 4 carbon atoms,
aralkyloxy groups having a total of from 7 to 12 carbon atoms,
alkylthio groups having from 1 to 4 carbon atoms,
alkylsulfonyl groups having from 1 to 4 carbon atoms,
halogen atoms,
aralkyl groups having a total of from 7 to 12 carbon atoms,
phenyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenoxy groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenylthio groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenylsulfonyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenylsulfonylamino groups in which the phenyl group is unsubstituted or is substituted by from 1 to 3 of substituents .beta..sup.1, defined below, and the nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyridyloxy, pyridylthio and pyridylsulfonyl groups,
imidazolyl groups in which a nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
pyridylsulfonylamino groups in which the amino group is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
said substituents .beta..sup.1 being selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, halogenated alkyl groups having from 1 to 4 carbon atoms, alkoxy groups having from 1 to 4 carbon atoms, halogen atoms and alkylenedioxy groups having from 1 to 4 carbon atoms;
Y represents an oxygen atom, a sulfur atom or a group of formula >N--R.sup.4 in which R.sup.4 represents a hydrogen atom, an alkyl group having from 1 to 3 carbon atoms or an alkanoyl group having from 2 to 5 carbon atoms; and
Z represents a 2,4-dioxothiazolidin-5-ylmethyl, 2,4-dioxooxazolidin-5-ylmethyl or 3,5-dioxooxadiazolidin-2-ylmethyl group.

### Claim 26 (depends on 1)

The compound of claim 1, wherein:
R.sup.1 represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms;
R.sup.2 represents an alkylene group having from 2 to 5 carbon atoms;
R.sup.3 represents a hydrogen atom;
X represents: an aryl group, which has from 6 to 10 ring carbon atoms and is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.2, defined below; or an aromatic heterocyclic group which has from 5 to 10 ring atoms in one or two rings, of which atoms from 1 to 3 are hetero-atoms selected from the group consisting of nitrogen, oxygen and sulfur atoms, said group being unsubstituted or being substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.2, defined below;
said substituents .alpha..sup.2 being selected from the group consisting of:
alkyl groups having from 1 to 6 carbon atoms,
halogenated alkyl groups having from 1 to 4 carbon atoms,
hydroxy groups,
alkanoyloxy groups having from 1 to 4 carbon atoms,
alkoxy groups having from 1 to 4 carbon atoms,
alkylenedioxy groups having from 1 to 4 carbon atoms,
aralkyloxy groups having a total of from 7 to 12 carbon atoms,
alkylthio groups having from 1 to 4 carbon atoms,
alkylsulfonyl groups having from 1 to 4 carbon atoms,
fluorine atoms, chlorine atoms and bromine atoms,
aralkyl groups having a total of from 7 to 12 carbon atoms,
phenyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenoxy groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenylthio groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenylsulfonyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenylsulfonylamino groups in which the phenyl group is unsubstituted or is substituted by from 1 to 3 of substituents .beta..sup.1, defined below and the nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyridyloxy, pyridylthio and pyridylsulfonyl groups;
imidazolyl groups in which a nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
pyridylsulfonylamino groups in which the amino group is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
said substituents .beta..sup.1 being selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, halogenated alkyl groups having from 1 to 4 carbon atoms, alkoxy groups having from 1 to 4 carbon atoms, halogen atoms and alkylenedioxy groups having from 1 to 4 carbon atoms;
Y represents an oxygen atom; and
Z represents a 2,4-dioxothiazolidin-5-ylmethyl or 2,4-dioxooxazolidin-5-ylmethyl group.

### Claim 27 (depends on 1)

The compound of claim 1, wherein:
R.sup.1 represents a hydrogen atom or an alkyl group having from 1 to 3 carbon atoms;
R.sup.2 represents an alkylene group having 2 or 3 carbon atoms;
R.sup.3 represents a hydrogen atom;
X represents a phenyl, naphthyl, imidazolyl, oxazolyl, pyridyl, indolyl, quinolyl or isoquinolyl group, each of which is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.3, defined below;
said substituents .alpha..sup.3 are selected from the group consisting of:
alkyl groups having from 1 to 6 carbon atoms,
halogenated alkyl groups having from 1 to 4 carbon atoms,
hydroxy groups,
alkanoyloxy groups having from 1 to 4 carbon atoms,
alkoxy groups having from 1 to 4 carbon atoms,
the methylenedioxy group,
aralkyloxy groups having a total of from 7 to 12 carbon atoms,
alkylthio groups having from 1 to 4 carbon atoms,
alkylsulfonyl groups having from 1 to 4 carbon atoms,
fluorine, chlorine and bromine atoms,
aralkyl groups having a total of from 7 to 12 carbon atoms,
phenyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.2, defined below,
phenoxy groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.2, defined below,
phenylthio groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.2, defined below,
phenylsulfonyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.2, defined below,
phenylsulfonylamino groups in which the phenyl group is unsubstituted or is substituted by from 1 to 3 of substituents .beta..sup.2 defined below, and the nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyridyloxy, pyridylthio and pyridylsulfonyl groups;
imidazolyl groups in which a nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
pyridylsulfonylamino groups in which the amino group is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
said substituents .beta..sup.2 are selected from the group consisting of methyl groups, trifluoromethyl groups, methoxy groups, fluorine atoms and methylenedioxy groups;
Y represents an oxygen atom; and
Z represents a 2,4-dioxothiazolidin-5-ylmethyl group.

### Claim 28 (depends on 1)

The compound of claim 1, wherein:
R.sup.1 represents a hydrogen atom, a methyl or ethyl group;
R.sup.2 represents an ethylene, trimethylene or methylethylene group;
R.sup.3 represents a hydrogen atom;
X represents a phenyl, naphthyl, imidazolyl, oxazolyl, pyridyl, indolyl, quinolyl or isoquinolyl group, each of which is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.4, defined below;
said substituents .alpha..sup.4 are selected from the group consisting of:
alkyl groups having from 1 to 6 carbon atoms,
halogenated alkyl groups having from 1 to 4 carbon atoms,
hydroxy groups,
alkanoyloxy groups having from 1 to 4 carbon atoms,
alkoxy groups having from 1 to 4 carbon atoms,
methylenedioxy, benzyloxy, phenethyloxy and naphthylmethyloxy groups,
alkylthio groups having from 1 to 4 carbon atoms,
alkylsulfonyl groups having from 1 to 4 carbon atoms,
fluorine, chlorine and bromine atoms,
the benzyl group,
phenyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.2, defined below,
phenoxy groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.2, defined below,
the phenylthio, phenylsulfonyl, phenylsulfonylamino, N-methylphenylsulfonylamino, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyridyloxy, pyridylthio, pyridylsulfonyl, pyridylsulfonylamino and N-methylpyridylsulfonylamino groups,
imidazolyl groups in which a nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms;
Y represents an oxygen atom; and
Z represents a 2,4-dioxothiazolidin-5-ylmethyl group.

### Claim 29 (depends on 1)

The compound of claim 1, wherein:
R.sup.1 represents a hydrogen atom, a methyl or ethyl group;
R.sup.2 represents an ethylene, trimethylene or methylethylene group;
R.sup.3 represents a hydrogen atom;
X represents a phenyl, naphthyl, pyridyl, indolyl, quinolyl or isoquinolyl group, each of which is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.5, defined below;
said substituents .alpha..sup.5 are selected from the group consisting of:
alkyl groups having from 1 to 3 carbon atoms,
the trifluoromethyl, difluoromethyl, fluoromethyl, hydroxy, formyloxy and acetoxy groups,
alkoxy groups having from 1 to 3 carbon atoms,
the methylenedioxy, benzyloxy, methylthio, ethylthio, methylsulfonyl and ethylsulfonyl groups,
the fluorine, chlorine and bromine atoms, and
the benzyl, phenyl, 4-methylphenyl, 4-trifluoromethylphenyl, 4-methoxyphenyl, 4-fluorophenyl, 3,4-methylenedioxyphenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino, N-methylphenylsulfonylamino, furyl, thienyl, oxazolyl, thiazolyl, imidazolyl, N-methylimidazolyl, pyridyl, pyridyloxy, pyridylthio, pyridylsulfonyl, pyridylsulfonylamino and/or N-methylpyridylsulfonylamino groups;
Y represents an oxygen atom; and
Z represents a 2,4-dioxothiazolidin-5-ylmethyl group.

### Claim 30 (depends on 1)

The compound of claim 1, wherein:
R.sup.1 represents a hydrogen atom, a methyl or ethyl group;
R.sup.2 represents an ethylene group;
R.sup.3 represents a hydrogen atom;
X represents a phenyl, naphthyl, pyridyl, quinolyl or isoquinolyl group, each of which is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.6, defined below;
said substituents .alpha..sup.6 are selected from the group consisting of: methyl, ethyl, isopropyl, trifluoromethyl, hydroxy, acetoxy, methoxy, ethoxy, isopropoxy, methylenedioxy, benzyloxy, methylthio, ethylthio, methylsulfonyl, ethylsulfonyl, benzyl, phenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino, N-methylphenylsulfonylamino, pyridyl, pyridyloxy, pyridylthio, pyridylsulfonyl, pyridylsulfonylamino and N-methylpyridylsulfonylamino groups and chlorine atoms;
Y represents an oxygen atom; and
Z represents a 2,4-dioxothiazolidin-5-ylmethyl group.

### Claim 31 (depends on 1)

The compound of claim 1, wherein:
R.sup.1 represents a methyl or ethyl group;
R.sup.2 represents an ethylene group;
R.sup.3 represents a hydrogen atom;
X represents a phenyl group which is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.7, defined below;
said substituents .alpha..sup.7 are selected from the group consisting of: methyl, hydroxy, acetoxy, benzyl, phenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino, N-methylphenylsulfonylamino, pyridyl, pyridyloxy, pyridylthio and pyridylsulfonyl groups and chlorine atoms;
Y represents an oxygen atom; and
Z represents a 2,4-dioxothiazolidin-5-ylmethyl group.

### Claim 32 (depends on 1)

The compound of claim 1, wherein:
R.sup.1 represents a methyl or ethyl group;
R.sup.2 represents an ethylene group;
R.sup.3 represents a hydrogen atom;
X represents a pyridyl group which is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.8, defined below;
said substituents .alpha..sup.8 are selected from the group consisting of: methoxy, ethoxy, isopropoxy, benzyloxy, methylthio, ethylthio, methylsulfonyl, ethylsulfonyl, benzyl, phenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino and N-methylphenylsulfonylamino groups;
Y represents an oxygen atom; and
Z represents a 2,4-dioxothiazolidin-5-ylmethyl group.

### Claim 33 (depends on 1)

The compound of claim 1, selected from the group consisting of 5-(4-{2-›1-(4-2'-pyridylphenyl)ethylideneaminooxy!ethoxy}benzyl)thiazolidi ne-2,4-dione and pharmaceutically acceptable salts thereof.

### Claim 34 (depends on 1)

The compound of claim 1, selected from the group consisting of 5-(4-{2-›1-(4-3'-pyridylphenyl)ethylideneaminooxy!ethoxy}benzyl)thiazolidi ne-2,4-dione and pharmaceutically acceptable salts thereof.

### Claim 35 (depends on 1)

The compound of claim 1, selected from the group consisting of 5-(4-{2-›1-(4-4'-pyridylphenyl)ethylideneaminooxy!ethoxy}benzyl)thiazolidi ne-2,4-dione and pharmaceutically acceptable salts thereof.

### Claim 36 (depends on 1)

The compound of claim 1, selected from the group consisting of 5-(4-{2-›1-(2-phenyl-5-pyridyl)ethylideneaminooxy!ethoxy}benzyl)thiazolidi ne-2,4-dione and pharmaceutically acceptable salts thereof.

### Claim 37 (depends on 1)

The compound of claim 1, selected from the group Consisting of 5-(4-{2-›1-(2-methoxy-5-pyridyl)ethylideneaminooxy!ethoxy}benzyl)thiazolid ine-2,4-dione and pharmaceutically acceptable salts thereof.

### Claim 38 (depends on 1)

The compound of claim 1, selected from the group consisting of 5-(4-{2-›1-(2-ethoxy-5-pyridyl)ethylideneaminooxy!ethoxy}benzyl)thiazolidi ne-2,4-dione and pharmaceutically acceptable salts thereof.

### Claim 39 (depends on 1)

The compound of claim 1, selected from the group consisting of 5-(4-{2-›1-(2-isopropoxy-5-pyridyl)ethylideneaminooxy!ethoxy}benzyl)thiazo lidine-2,4-dione and pharmaceutically acceptable salts thereof.

### Claim 40 (depends on 1)

The compound of claim 1, selected from the group consisting of 5-(4-{2-›1-(2-benzyl-5-pyridyl)ethylideneaminooxy!ethoxy}benzyl)thiazolidi ne-2,4-dione and pharmaceutically acceptable salts thereof.

### Claim 41 (depends on 1)

A pharmaceutical composition for the treatment or prophylaxis of diabetes, hyperlipemia, hyperglycemia, obesity, arteriosclerosis, essential hypertension, cachexia, psoriasis, osteoporosis, impaired glucose tolerance, insulin resistant non-impaired glucose tolerance, non-diagnostic glucose tolerance, insulin resistance, diabetic complications, fatty liver, polycystic ovary syndrome and gestational diabetes mellitus, and complications thereof, which composition comprises an effective amount of an active compound in admixture with a pharmaceutically acceptable carrier or diluent, wherein said active compound is selected from the group consisting of compounds of formula (I), as claimed in claim 1, and salts thereof.

### Claim 42 (depends on 41)

The composition of claim 41, wherein:
R.sup.1 represents a .hydrogen atom or an alkyl group having from 1 to 4 carbon atoms;
R.sup.2 represents an alkylene group having from 2 to 5 carbon atoms;
R.sup.3 represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, an alkoxy group having 1 or 2 carbon atoms, an alkylthio group having 1 or 2 carbon atoms or a halogen atom;
X represents: an aryl group, which hag from 6 to 10 ring carbon atoms and is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.1, defined below; or an aromatic heterocyclic group which has from 5 to 10 ring atoms in one or two rings, of which atoms from 1 to 3 are hetero-atoms selected from the group consisting of nitrogen, oxygen and sulfur atoms, said group being unsubstituted or being substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.1, defined below;
said substituents .alpha..sup.1 being selected from the group consisting of:
alkyl groups having from 1 to 6 carbon atoms,
halogenated alkyl groups having from 1 to 4 carbon atoms,
hydroxy groups,
acyloxy groups having from 1 to 4 carbon atoms,
alkoxy groups having from 1 to 4 carbon atoms,
alkylenedioxy groups having from 1 to 4 carbon atoms,
aralkyloxy groups having a total of from 7 to 12 carbon atoms,
alkylthio groups having from 1 to 4 carbon atoms,
alkylsulfonyl groups having from 1 to 4 carbon atoms,
halogen atoms,
aralkyl groups having a total of from 7 to 12 carbon atoms,
phenyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenoxy groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenylthio groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenylsulfonyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenylsulfonylamino groups in which the phenyl group is unsubstituted or is substituted by from 1 to 3 of substituents .beta..sup.1, defined below, and the nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyridyloxy, pyridylthio and pyridylsulfonyl groups,
imidazolyl groups in which a nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
pyridylsulfonylamino groups in which the amino group is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
said substituents .beta..sup.1 being selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, halogenated alkyl groups having from 1 to 4 carbon atoms, alkoxy groups having from 1 to 4 carbon atoms, halogen atoms and alkylenedioxy groups having from 1 to 4 carbon atoms;
Y represents an oxygen atom, a sulfur atom or a group of formula >N--R.sup.4, in which R.sup.4 represents a hydrogen atom, an alkyl group having from 1 to 3 carbon atoms or an alkanoyl group having from 2 to 5 carbon atoms; and
Z represents a 2,4-dioxothiazolidin-5 -ylmethyl, 2,4- dioxooxazolidin-5-ylmethyl or 3,5- dioxooxadiazolidin-2-ylmethyl group.

### Claim 43 (depends on 41)

The composition of claim 41, wherein:
R.sup.1 represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms;
R.sup.2 represents an alkylene group having from 2 to 5 carbon atoms;
R.sup.3 represents a hydrogen atom;
X represents: an aryl group, which has from 6 to 10 ring carbon atoms and is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.2, defined below; or an aromatic heterocyclic group which has from 5 to 10 ring atoms in one or two rings, of which atoms from 1 to 3 are hetero-atoms selected from the group consisting of nitrogen, oxygen and sulfur atoms, said group being unsubstituted or being substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.2, defined below;
said substituents .alpha..sup.2 being selected from the group consisting of:
alkyl groups having from 1 to 6 carbon atoms,
halogenated alkyl groups having from 1 to 4 carbon atoms,
hydroxy groups,
alkanoyloxy groups having from 1 to 4 carbon atoms,
alkoxy groups having from 1 to 4 carbon atoms,
alkylenedioxy groups having from 1 to 4 carbon atoms,
aralkyloxy groups having a total of from 7 to 12 carbon atoms,
alkylthio groups having from 1 to 4 carbon atoms,
alkylsulfonyl groups having from 1 to 4 carbon atoms,
fluorine atoms, chlorine atoms and bromine atoms,
aralkyl groups having a total of from 7 to 12 carbon atoms,
phenyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenoxy groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenylthio groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenylsulfonyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenylsulfonylamino groups in which the phenyl group is unsubstituted or is substituted by from 1 to 3 of substituents .beta..sup.1, defined below, and the nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyridyloxy, pyridylthio and pyridylsulfonyl groups;
imidazolyl groups in which a nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
pyridylsulfonylamino groups in which the amino group is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
said substituents .beta..sup.1 being selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, halogenated alkyl groups having from 1 to 4 carbon atoms, alkoxy groups having from 1 to 4 carbon atoms, halogen atoms and alkylenedioxy groups having from 1 to 4 carbon atoms;
Y represents, an oxygen atom; and
Z represents a 2,4-dioxothiazolidin-5-ylmethyl or 2,4-dioxooxazolidin-5-ylmethyl group.

### Claim 44 (depends on 41)

The composition of claim 41, wherein:
R.sup.1 represents a hydrogen atom or an alkyl group having from 1 to 3 carbon atoms;
R.sup.2 represents an alkylene group having 2 or 3 carbon atoms;
R.sup.3 represents a hydrogen atom;
X represents a phenyl, naphthyl, imidazolyl, oxazolyl, pyridyl, indolyl, quinolyl or isoquinolyl group, each of which is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.3, defined below;
said substituents .alpha..sup.3 are selected from the group consisting of:
alkyl groups having from 1 to 6 carbon atoms,
halogenated alkyl groups having from 1 to 4 carbon atoms,
hydroxy groups,
alkanoyloxy groups having from 1 to 4 carbon atoms,
alkoxy groups having from 1 to 4 carbon atoms,
the methylenedioxy group,
aralkyloxy groups having a total of from 7 to 12 carbon atoms,
alkylthio groups having from 1 to 4 carbon atoms,
alkylsulfonyl groups having from 1 to 4 carbon atoms,
fluorine, chlorine and bromine atoms,
aralkyl groups having a total of from 7 to 12 carbon atoms,
phenyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.2, defined below,
phenoxy groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.2, defined below,
phenylthio groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.2, defined below,
phenylsulfonyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .alpha..sup.2, defined below,
phenylsulfonylamino groups in which the phenyl group is unsubstituted or is substituted by from 1 to 3 of substituents .alpha..sup.2, defined below, and the nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyridyloxy, pyridylthio and pyridylsulfonyl groups;
imidazolyl groups in which a nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
pyridylsulfonylamino groups in which the amino group is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
said substituents .beta..sup.2 are selected from the group consisting of methyl groups, trifluoromethyl groups, methoxy groups, fluorine atoms and methylenedioxy groups;
Y represents an oxygen atom; and
Z represents a 2,4-dioxothiazolidin-5-ylmethyl group.

### Claim 45 (depends on 41)

The composition of claim 41, wherein:
R.sup.1 represents a hydrogen atom, a methyl or ethyl group;
R.sup.2 represents an ethylene, trimethylene or methylethylene group;
R.sup.3 represents a hydrogen atom;
X represents a phenyl, naphthyl, imidazolyl, oxazolyl, pyridyl, indolyl, quinolyl or isoquinolyl group, each of which is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.4, defined below;
said substituents .alpha..sup.4 are selected from the group consisting of:
alkyl groups having from 1 to 6 carbon atoms,
halogenated alkyl groups having from 1 to 4 carbon atoms,
hydroxy groups,
alkanoyloxy groups having from 1 to 4 carbon atoms,
alkoxy groups having from 1 to 4 carbon atoms,
methylenedioxy, benzyloxy, phenethyloxy and naphthylmethyloxy groups,
alkylthio groups having from 1 to 4 carbon atoms,
alkylsulfonyl groups having from 1 to 4 carbon atoms,
fluorine, chlorine and bromine atoms,
the benzyl group,
phenyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.2, defined below,
phenoxy groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.2, defined below,
the phenylthio, phenylsulfonyl, phenylsulfonylamino, N-methylphenylsulfonylamino, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyridyloxy, pyridylthio, pyridylsulfonyl, pyridylsulfonylamino and N-methylpyridylsulfonylamino groups,
imidazolyl groups in which a nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms;
Y represents an oxygen atom; and
Z represents a 2,4-dioxothiazolidin-5-ylmethyl group.

### Claim 46 (depends on 41)

The composition of claim 41, wherein:
R.sup.1 represents a hydrogen atom, a methyl or ethyl group;
R.sup.2 represents an ethylene, trimethylene or methylethylene group;
R.sup.3 represents a hydrogen atom;
X represents a phenyl, naphthyl, pyridyl, indolyl, quinolyl or isoquinolyl group, each of which is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.5, defined below;
said substituents .alpha..sup.5 are selected from the group consisting of:
alkyl groups having from 1 to 3 carbon atoms,
the trifluoromethyl, difluoromethyl, fluoromethyl, hydroxy, formyloxy and acetoxy groups,
alkoxy groups having from 1 to 3 carbon atoms,
the methylenedioxy, benzyloxy, methylthio, ethylthio, methylsulfonyl and ethylsulfonyl groups,
the fluorine, chlorine and bromine atoms, and
the benzyl, phenyl, 4-methylphenyl, 4-trifluoromethylphenyl, 4-methoxyphenyl, 4-fluorophenyl, 3,4-methylenedioxyphenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino, N-methylphenylsulfonylamino, furyl, thienyl, oxazolyl, thiazolyl, imidazolyl, N-methylimidazolyl, pyridyl, pyridyloxy, pyridylthio, pyridylsulfonyl, pyridylsulfonylamino and/or N-methylpyridylsulfonylamino groups;
Y represents an oxygen atom; and
Z represents a 2,4-dioxothiazolidin-5-ylmethyl group.

### Claim 47 (depends on 41)

The composition of claim 41, wherein:
R.sup.1 represents a hydrogen atom, a methyl or ethyl group;
R.sup.2 represents an ethylene group;
R.sup.3 represents a hydrogen atom;
X represents a phenyl, naphthyl, pyridyl, quinolyl or isoquinolyl group, each of which is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.6, defined below;
said substituents .alpha..sup.6 are selected from the group consisting of: methyl, ethyl, isopropyl, trifluoromethyl, hydroxy, acetoxy, methoxy, ethoxy, isopropoxy, methylenedioxy, benzyloxy, methylthio, ethylthio, methylsulfonyl, ethylsulfonyl, benzyl, phenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino, N-methylphenylsulfonylamino, pyridyl, pyridyloxy, pyridylthio, pyridylsulfonyl, pyridylsulfonylamino and N-methylpyridylsulfonylamino groups and chlorine atoms;
Y represents an oxygen atom; and
Z represents a 2,4-dioxothiazolidin-5-ylmethyl group.

### Claim 48 (depends on 41)

The composition of claim 41, wherein:
R.sup.1 represents a methyl or ethyl group;
R.sup.2 represents an ethylene group;
R.sup.3 represents a hydrogen atom;
X represents a phenyl group which is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.7, defined below;
said substituents .alpha..sup.7 are selected from the group consisting of: methyl, hydroxy, acetoxy, benzyl, phenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino, N-methylphenylsulfonylamino, pyridyl, pyridyloxy, pyridylthio and pyridylsulfonyl groups and chlorine atoms;
Y represents an oxygen atom; and
Z represents a 2,4-dioxothiazolidin-5-ylmethyl group.

### Claim 49 (depends on 41)

The composition of claim 41, wherein:
R.sup.1 represents a methyl or ethyl group;
R.sup.2 represents an ethylene group;
R.sup.3 represents a hydrogen atom;
X represents a pyridyl group which is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.8, defined below;
said substituents .alpha..sup.8 are selected from the group consisting of: methoxy, ethoxy, isopropoxy, benzyloxy, methylthio, ethylthio, methylsulfonyl, ethylsulfonyl, benzyl, phenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino and N-methylphenylsulfonylamino groups;
Y represents an oxygen atom; and
Z represents a 2,4-dioxothiazolidin-5-ylmethyl group.

### Claim 50 (depends on 41)

The composition of claim 41, wherein said active compound is selected from the group consisting of:
5-(4-{2-›1-(4-2'-pyridylphenyl)ethylideneaminooxy! ethoxy}benzyl)thiazolidine-2,4-dione;
5-(4-{2-›1-(4-3'-pyridylphenyl)ethylideneaminooxy! ethoxy}benzyl)thiazolidine-2,4-dione;
5-(4-{2-›1-(4-4'-pyridylphenyl)ethylideneaminooxy! ethoxy}benzyl)thiazolidine-2,4-dione;
5-(4-{2-›1-(2-phenyl-5-pyridyl)ethylideneaminooxy!ethoxy}benzyl)thiazolidin e-2,4-dione;
5-(4-{2-›1-(2-methoxy-5-pyridyl)ethylideneaminooxy!ethoxy}benzyl)thiazolidi ne-2,4-dione;
5-(4-{2-›1-(2-ethoxy-5-pyridyl)ethylideneaminooxy!ethoxy}benzyl)thiazolidin e-2,4-dione;
5-(4-{2-›1-(2-isopropoxy-5-pyridyl)ethylideneaminooxy!ethoxy}benzyl)thiazol idine-2,4-dione;
5-(4-{2-›1-(2-benzyl-5-pyridyl)ethylideneaminooxy!ethoxy}benzyl)thiazolidin e-2,4-dione; and
pharmaceutically acceptable salts thereof.

### Claim 51 (depends on 1)

A method for the treatment or prophylaxis of diabetes, hyperlipemia, hyperglycemia, obesity, arteriosclerosis, essential hypertension, cachexia, psoriasis, osteoporosis, impaired glucose tolerance, insulin resistant non-impaired glucose tolerance, non-diagnostic glucose tolerance, insulin resistance, diabetic complications, fatty liver, polycystic ovary syndrome and gestational diabetes mellitus, and complications thereof in a mammal, which method comprises administering to said mammal an effective amount of an active compound, wherein said active compound is selected from the group consisting of compounds of formula (I), as claimed in claim 1, and salts thereof.

### Claim 52 (depends on 51)

The method of claim 51, wherein:
R.sup.1 represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms;
R.sup.2 represents an alkylene group having from 2 to 5 carbon atoms;
R.sup.3 represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, an alkoxy group having 1 or 2 carbon atoms, an alkylthio group having 1 or 2 carbon atoms or a halogen atom;
X represents: an aryl group, which has from 6 to 10 ring carbon atoms and is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.1, defined below; or an aromatic heterocyclic group which has from 5 to 10 ring atoms in one or two rings, of which atoms from 1 to 3 are hetero-atoms selected from the group consisting of nitrogen, oxygen and sulfur atoms, said group being unsubstituted or being substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.1, defined below;
said substituents .alpha..sup.1 being selected from the group consisting of:
alkyl groups having from 1 to 6 carbon atoms,
halogenated alkyl groups having from 1 to 4 carbon atoms,
hydroxy groups,
acyloxy groups having from 1 to 4 carbon atoms,
alkoxy groups having from 1 to 4 carbon atoms,
alkylenedioxy groups having from 1 to 4 carbon atoms,
aralkyloxy groups having a total of from 7 to 12 carbon atoms,
alkylthio groups having from 1 to 4 carbon atoms,
alkylsulfonyl groups having from 1 to 4 carbon atoms,
halogen atoms,
aralkyl groups having a total of from 7 to 12 carbon atoms,
phenyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenoxy groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenylthio groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenylsulfonyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenylsulfonylamino groups in which the phenyl group is unsubstituted or is substituted by from 1 to 3 of substituents .beta..sup.1, defined below, and the nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyridyloxy, pyridylthio and pyridylsulfonyl groups,
imidazolyl groups in which a nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
pyridylsulfonylamino groups in which the amino group is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
said substituents .beta..sup.1 being selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, halogenated alkyl groups having from 1 to 4 carbon atoms, alkoxy groups having from 1 to 4 carbon atoms, halogen atoms and alkylenedioxy groups having from 1 to 4 carbon atoms;
Y represents an oxygen atom, a sulfur atom or a group of formula >N--R.sup.4 in which R.sup.4 represents a hydrogen atom, an alkyl group having from 1 to 3 carbon atoms or an alkanoyl group having from 2 to 5 carbon atoms; and
Z represents a 2,4-dioxothiazolidin-5-ylmethyl, 2,4-dioxooxazolidin-5-ylmethyl or 3,5-dioxooxadiazolidin-2-ylmethyl group.

### Claim 53 (depends on 51)

The method of claim 51, wherein:
R.sup.1 represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms;
R.sup.2 represents an alkylene group having from 2 to 5 carbon atoms;
R.sup.3 represents a hydrogen atom;
X represents: an aryl group, which has from 6 to 10 ring carbon atoms and is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.2, defined below; or an aromatic heterocyclic group which has from 5 to 10 ring atoms in one or two rings, of which atoms from 1 to 3 are hetero-atoms selected from the group consisting of nitrogen, oxygen and sulfur atoms, said group being unsubstituted or being substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.2, defined below;
said substituents .alpha..sup.2 being selected from the group consisting of:
alkyl groups having from 1 to 6 carbon atoms,
halogenated alkyl groups having from 1 to 4 carbon atoms,
hydroxy groups,
alkanoyloxy groups having from 1 to 4 carbon atoms,
alkoxy groups having from 1 to 4 carbon atoms,
alkylenedioxy groups having from 1 to 4 carbon atoms,
aralkyloxy groups having a total of from 7 to 12 carbon atoms,
alkylthio groups having from 1 to 4 carbon atoms,
alkylsulfonyl groups having from 1 to 4 carbon atoms,
fluorine atoms, chlorine atoms and bromine atoms,
aralkyl groups having a total of from 7 to 12 carbon atoms,
phenyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenoxy groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenylthio groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenylsulfonyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.1, defined below,
phenylsulfonylamino groups in which the phenyl group is unsubstituted or is substituted by from 1 to 3 of substituents .beta..sup.1, defined below, and the nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyridyloxy, pyridylthio and pyridylsulfonyl groups;
imidazolyl groups in which a nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
pyridylsulfonylamino groups in which the amino group is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
said substituents .beta..sup.1 being selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, halogenated alkyl groups having from 1 to 4 carbon atoms, alkoxy groups having from 1 to 4 carbon atoms, halogen atoms and alkylenedioxy groups having from 1 to 4 carbon atoms;
Y represents an oxygen atom; and
Z represents a 2,4-dioxothiazolidin-5-ylmethyl or 2,4-dioxooxazolidin-5-ylmethyl group.

### Claim 54 (depends on 51)

The method of claim 51, wherein:
R.sup.1 represents a hydrogen atom or an alkyl group having from 1 to 3 carbon atoms;
R.sup.2 represents an alkylene group having 2 or 3 carbon atoms;
R.sup.3 represents a hydrogen atom;
X represents a phenyl, naphthyl, imidazolyl, oxazolyl, pyridyl, indolyl, quinolyl or isoquinolyl group, each of which is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.3, defined below;
said substituents .alpha..sup.3 are selected from the group consisting of:
alkyl groups having from 1 to 6 carbon atoms,
halogenated alkyl groups having from 1 to 4 carbon atoms,
hydroxy groups,
alkanoyloxy groups having from 1 to 4 carbon atoms,
alkoxy groups having from 1 to 4 carbon atoms,
the methylenedioxy group,
aralkyloxy groups having a total of from 7 to 12 carbon atoms,
alkylthio groups having from 1 to 4 carbon atoms,
alkylsulfonyl groups having from 1 to 4 carbon atoms,
fluorine, chlorine and bromine atoms,
aralkyl groups having a total of from 7 to 12 carbon atoms,
phenyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.2, defined below,
phenoxy groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.2, defined below,
phenylthio groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.2, defined below,
phenylsulfonyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.2, defined below,
phenylsulfonylamino groups in which the phenyl group is unsubstituted or is substituted by from 1 to 3 of substituents .beta..sup.2, defined below, and the nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyridyloxy, pyridylthio and pyridylsulfonyl groups;
imidazolyl groups in which a nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
pyridylsulfonylamino groups in which the amino group is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms,
said substituents .beta..sup.2 are selected from the group consisting of methyl groups, trifluoromethyl groups, methoxy groups, fluorine atoms and methylenedioxy groups;
Y represents an oxygen atom; and
Z represents a 2,4-dioxothiazolidin-5-ylmethyl group.

### Claim 55 (depends on 51)

The method of claim 51, wherein:
R.sup.1 represents a hydrogen atom, a methyl or ethyl group;
R.sup.2 represents an ethylene, trimethylene or methylethylene group;
R.sup.3 represents a hydrogen atom;
X represents a phenyl, naphthyl, imidazolyl, oxazolyl, pyridyl, indolyl, quinolyl or isoquinolyl group, each of which is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.4, defined below;
said substituents .alpha..sup.4 are selected from the group consisting of:
alkyl groups having from 1 to 6 carbon atoms,
halogenated alkyl groups having from 1 to 4 carbon atoms,
hydroxy groups,
alkanoyloxy groups having from 1 to 4 carbon atoms,
alkoxy groups having from 1 to 4 carbon atoms,
methylenedioxy, benzyloxy, phenethyloxy and naphthylmethyloxy groups,
alkylthio groups having from 1 to 4 carbon atoms,
alkylsulfonyl groups having from 1 to 4 carbon atoms,
fluorine, chlorine and bromine atoms,
the benzyl group,
phenyl groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.2, defined below,
phenoxy groups which are unsubstituted or are substituted by from 1 to 3 of substituents .beta..sup.2, defined below,
the phenylthio, phenylsulfonyl, phenylsulfonylamino, N-methylphenylsulfonylamino, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyridyloxy, pyridylthio, pyridylsulfonyl, pyridylsulfonylamino and N-methylpyridylsulfonylamino groups,
imidazolyl groups in which a nitrogen atom is unsubstituted or is substituted by an alkyl group having from 1 to 6 carbon atoms;
Y represents an oxygen atom; and
Z represents a 2,4-dioxothiazolidin-5-ylmethyl group.

### Claim 56 (depends on 51)

The method of claim 51, wherein:
R.sup.1 represents a hydrogen atom, a methyl or ethyl group;
R.sup.2 represents an ethylene, trimethylene or methylethylene group;
R.sup.3 represents a hydrogen atom;
X represents a phenyl, naphthyl, pyridyl, indolyl, quinolyl or isoquinolyl group, each of which is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.5, defined below;
said substituents .alpha..sup.5 are selected from the group consisting of:
alkyl groups having from 1 to 3 carbon atoms,
the trifluoromethyl, difluoromethyl, fluoromethyl, hydroxy, formyloxy and acetoxy groups,
alkoxy groups having from 1 to 3 carbon atoms,
the methylenedioxy, benzyloxy, methylthio, ethylthio, methylsulfonyl and ethylsulfonyl groups,
the fluorine, chlorine and bromine atoms, and
the benzyl, phenyl, 4-methylphenyl, 4-trifluoromethylphenyl, 4-methoxyphenyl, 4-fluorophenyl, 3,4-methylenedioxyphenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino, N-methylphenylsulfonylamino, furyl, thienyl, oxazolyl, thiazolyl, imidazolyl, N-methylimidazolyl, pyridyl, pyridyloxy, pyridylthio, pyridylsulfonyl, pyridylsulfonylamino and/or N-methylpyridylsulfonylamino groups;
Y represents an oxygen atom; and
Z represents a 2,4-dioxothiazolidin-5-ylmethyl group.

### Claim 57 (depends on 51)

The method of claim 51, wherein:
R.sup.1 represents a hydrogen atom, a methyl or ethyl group;
R.sup.2 represents an ethylene group;
R.sup.3 represents a hydrogen atom;
X represents a phenyl, naphthyl, pyridyl, quinolyl or isoquinolyl group, each of which is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.6, defined below;
said substituents .alpha..sup.6 are selected from the group consisting of: methyl, ethyl, isopropyl, trifluoromethyl, hydroxy, acetoxy, methoxy, ethoxy, isopropoxy, methylenedioxy, benzyloxy, methylthio, ethylthio, methylsulfonyl, ethylsulfonyl, benzyl, phenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino, N-methylphenylsulfonylamino, pyridyl, pyridyloxy, pyridylthio, pyridylsulfonyl, pyridylsulfonylamino and N-methylpyridylsulfonylamino groups and chlorine atoms;
Y represents an oxygen atom; and
Z represents a 2,4-dioxothiazolidin-5-ylmethyl group.

### Claim 58 (depends on 51)

The method of claim 51, wherein:
R.sup.1 represents a methyl or ethyl group;
R.sup.2 represents an ethylene group;
R.sup.3 represents a hydrogen atom;
X represents a phenyl group which is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.7, defined below;
said substituents .alpha..sup.7 are selected from the group consisting of: methyl, hydroxy, acetoxy, benzyl, phenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino, N-methylphenylsulfonylamino, pyridyl, pyridyloxy, pyridylthio and pyridylsulfonyl groups and chlorine atoms;
Y represents an oxygen atom; and
Z represents a 2,4-dioxothiazolidin-5-ylmethyl group.

### Claim 59 (depends on 51)

The method of claim 51, wherein:
R.sup.1 represents a methyl or ethyl group;
R.sup.2 represents an ethylene group;
R.sup.3 represents a hydrogen atom;
X represents a pyridyl group which is unsubstituted or is substituted by from 1 to 3 substituents selected from the group consisting of substituents .alpha..sup.8, defined below;
said substituents .alpha..sup.8 are selected from the group consisting of: methoxy, ethoxy, isopropoxy, benzyloxy, methylthio, ethylthio, methylsulfonyl, ethylsulfonyl, benzyl, phenyl, phenoxy, phenylthio, phenylsulfonyl, phenylsulfonylamino and N-methylphenylsulfonylamino groups;
Y represents an oxygen atom; and
Z represents a 2,4-dioxothiazolidin-5-ylmethyl group.

### Claim 60 (depends on 51)

The method of claim 51, wherein said active compound is selected from the group consisting of:
5-(4-{2-›1-(4-2'-pyridylphenyl)ethylideneaminooxy!ethoxy}benzyl)thiazolidin e-2,4-dione;
5-(4-{2-›1-(4-3'-pyridylphenyl)ethylideneaminooxy!ethoxy}benzyl)thiazolidin e-2,4-dione;
5-(4-{2-›1-(4-4'-pyridylphenyl)ethylideneaminooxy!ethoxy}benzyl)thiazolidin e-2,4-dione;
5-(4-{2-›1-(2-phenyl-5-pyridyl)ethylideneaminooxy!ethoxy}benzyl)thiazolidin e-2,4-dione;
5-(4-{2-›1-(2-methoxy-5-pyridyl)ethylideneaminooxy!ethoxy}benzyl)thiazolidi ne-2,4-dione;
5-(4-{2-›1-(2-ethoxy-5-pyridyl)ethylideneaminooxy!ethoxy}benzyl)thiazolidin e-2,4-dione;
5-(4-{2-›1-(2-isopropoxy-5-pyridyl)ethylideneaminooxy!ethoxy}benzyl)thiazol idine-2,4-dione;
5-(4-{2-›1-(2-benzyl-5-pyridyl)ethylideneaminooxy!ethoxy}benzyl)thiazolidin e-2,4-dione; and
pharmaceutically acceptable salts thereof.

### Claim 61 (depends on 1)

The compound of claim 1 wherein X represents aryl group substituted by a 6-membered heterocyclic ring having nitrogen only as the heteroatom; and
R.sup.3 represents an aryl group substituted by a 6-membered heterocyclic ring having nitrogen only as the heteroatom.