Claims
- 1. A thiazolidinone compound having the general formula: ##STR8## wherein: W represents a sulfur atom or an oxygen atom, and X represents a group having the formula --N(R.sup.1)--; or
- X represents a sulfur atom or an oxygen atom, and W represents a group having the formula --N(R.sup.1)--;
- R.sup.1 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms or an alkyl group having from 1 to 4 carbon atoms substituted by an aryl group as defined below;
- R.sup.2 and R.sup.3 may be the same or different and each represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, an alkyl group having from 1 to 4 carbon atoms substituted by an aryl group as defined below, an aryl group as defined below, or a 5- or 6-membered aromatic heterocyclic group containing 1 to 3 hetero groups selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atoms, said aromatic heterocyclic group being unsubstituted or being substituted by a substituent selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, halogen atoms, amino groups and mono- and di-alkylamino groups wherein the or each alkyl group has from 1 to 6 carbon atoms;
- R.sup.4 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms or an alkyl group having from 1 to 4 carbon atoms substituted by an aryl group as defined below;
- R.sup.5 represents a cycloalkyl group having from 3 to 8 carbon atoms, said group optionally containing a ring nitrogen atom, said group being substituted by a group having the formula --B--ONO.sub.2 and said group further optionally being substituted by an alkyl group having from 1 to 6 carbon atoms, wherein B represents a single bond or an alkylene group having from 1 to 6 carbon atoms;
- A represents a single bond or an alkylene group having from 1 to 6 carbon atoms; and
- said aryl group represents an aryl group having from 6 to 10 carbon atoms which may optionally be substituted by a substituent selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, alkoxy groups having from 1 to 6 carbon atoms, halogen atoms, amino groups, mono- and di- alkylamino groups wherein the or each alkyl group has from 1 to 6 carbon atoms, and nitro groups;
- and pharmacologically acceptable salts thereof.
- 2. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein W represents a sulfur atom or an oxygen atom and X represents a group having the formula --NR.sup.1 --; or X represents a sulfur atom and W represents a group having the formula --NR.sup.1 --.
- 3. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein W represents a sulfur atom or an oxygen atom and X represents a group having the formula --NR.sup.1 --.
- 4. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein W represents a sulfur atom and X represents a group having the formula --NR.sup.1 --.
- 5. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein R.sup.1 represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, a benzyl group or a phenethyl group.
- 6. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein R.sup.1 represents a hydrogen atom, a methyl group or a benzyl group.
- 7. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein R.sup.1 represents a hydrogen atom.
- 8. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein R.sup.2 and R.sup.3 may be the same or different and each represents:
- a hydrogen atom;
- an alkyl group having from 1 to 4 carbon atoms;
- an alkyl group having from 1 to 4 carbon atoms substituted by a phenyl group which may be unsubstituted or substituted by a substituent selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, alkoxy groups having from 1 to 4 carbon atoms, hydroxy groups, halogen atoms and nitro groups;
- a naphthylmethyl group;
- a phenyl group which may be unsubstituted or substituted by a substitutent selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, alkoxy groups having from 1 to 4 carbon atoms, hydroxy groups, halogen atoms and nitro groups;
- a naphthyl group, or
- a furyl, thienyl, pyridyl, oxazolyl, thiazolyl, isoxazolyl or isothiazolyl group which may be optionally substituted by a substituent selected from the group consisting of alkyl groups having 1 or 2 carbon atoms, fluorine atom and chlorine atoms.
- 9. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein R.sup.2 and R.sup.3 may be the same or different and each represents:
- a hydrogen atom;
- a methyl group;
- an ethyl group;
- a benzyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and chlorine atoms;
- a phenethyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and chlorine atoms;
- a phenyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and chlorine atoms;
- a furyl group;
- a thienyl group; or a pyridyl group.
- 10. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein:
- R.sup.2 represents a hydrogen atom, a methyl group, an ethyl group, a benzyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups and hydroxyl groups, a phenyl group which may be optionally substituted by a methyl group or a methoxy group, or a thienyl group; and
- R.sup.3 represents a hydrogen atom; or
- R.sup.2 and R.sup.3 each represent a methyl group.
- 11. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein:
- R.sup.2 represents a hydrogen atom, a methyl group, a benzyl group which may be optionally substituted by a methyl group or a methoxy group, or a phenyl group; and
- R.sup.3 represents a hydrogen atom; or
- R.sup.2 and R.sup.3 each represent a methyl group.
- 12. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein R.sup.2 represents a hydrogen atom, a methyl group or a benzyl group, and R.sup.3 represents a hydrogen atom.
- 13. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein R.sup.2 represents a hydrogen atom and R.sup.3 represents a hydrogen atom.
- 14. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein R.sup.4 represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, a benzyl group or a phenethyl group.
- 15. The thiazolidinonelcompound or a pharmacologically acceptable salt thereof according to claim 1, wherein R.sup.4 represents a hydrogen atom, a methyl group or a benzyl group.
- 16. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein R.sup.4 represents a hydrogen atom.
- 17. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein R.sup.5 represents a cycloalkyl group having from 3 to 6 carbon atoms, a pyrrolidinyl group or a piperidinyl group, said cycloalkyl group, pyrrolidinyl group or piperidinyl group being substituted by a group having the formula --B--ONO.sub.2 and further being optionally substituted by a methyl group, wherein B represents a single bond, a methylene group, an ethylene group, a trimethylene group or a tetramethylene group.
- 18. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein R.sup.5 represents a cyclopropyl group, cyclopentyl group or cyclohexyl group, said groups being substituted by a group having the formula --B--ONO.sub.2 wherein B represents a methylene group, an ethylene group, a trimethylene group or a tetramethylene group.
- 19. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein R.sup.5 represents a cyclopentyl group or a cyclohexyl group, said groups being substituted by a group having the formula --B--ONO.sub.2 wherein B represents a methylene group, an ethylene group, a trimethylene group or a tetramethylene group.
- 20. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein R.sup.5 represents a 2- or 3-nitroxymethylcyclopentyl group, a 2- or 3-(2-nitroxyethyl)cyclopentyl group, a 2- or 3-(3-nitroxypropyl)cyclopentyl group, a 2- or 3-(4-nitroxybutyl)cyclopentyl group, a 2-, 3- or 4-nitroxycyclohexyl group, a 2-, 3- or 4-nitroxymethylcyclohexyl group, a 2-, 3- or 4-(2-nitroxyethyl)cyclohexyl group, a 2-, 3- or 4-(3-nitroxypropyl)cyclohexyl group, a 2-, 3- or 4-(4-nitroxybutyl)cyclohexyl group, a 3-, 4-, 5- or 6-nitroxymethylpiperidin-2-yl group or a 3-, 4-, 5- or 6-nitroxymethyl-1-methylpiperidin-2-yl group.
- 21. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein R.sup.5 represents a 2- or 3-nitroxymethylcyclopentyl group, a 2-, 3- or 4-nitroxycyclohexyl group, a 2-, 3- or 4-nitroxymethylcyclohexyl group, a 2-, 3- or 4-(2-nitroxyethyl)cyclohexyl group, a 2-, 3- or 4-(3-nitroxypropyl)cyclohexyl group or a 2-, 3- or 4-(4-nitroxybutyl)cyclohexyl group.
- 22. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein R.sup.5 represents a 3-nitroxymethylcyclopentyl group, a 4-nitroxycyclohexyl group, a 2-, 3- or 4-nitroxymethylcyclohexyl group, a 3- or 4-(2-nitroxyethyl)cyclohexyl group, a 3- or 4-(3-nitroxypropyl)cyclohexyl group or a 3- or 4-(4-nitroxybutyl)cyclohexyl group.
- 23. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein R.sup.5 represents a 3- or 4-nitroxymethylcyclohexyl group, a 4-(2-nitroxyethyl)cyclohexyl group, a 4-(3-nitroxypropyl)cyclohexyl group or a 4-(4-nitroxybutyl)cyclohexyl group.
- 24. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein R.sup.5 represents a 4-nitroxymethylcyclohexyl group.
- 25. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 26. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein A represents a methylene group or an ethylene group.
- 27. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein A represents a methylene group.
- 28. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein:
- W represents a sulfur atom or an oxygen atom, and X represents a group having the formula --NR.sup.1 --; or X represents a sulfur atom, and W represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, a benzyl group or a phenethyl group;
- R.sup.2 and R.sup.3 may be the same or different and each represents
- a hydrogen atom,
- an alkyl group having from 1 to 4 carbon atoms,
- an alkyl group having from 1 to 4 carbon atoms substituted by a phenyl group which may be unsubstituted or substituted by a substituent selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, alkoxy groups having from 1 to 4 carbon atoms, hydroxy groups, halogen atoms and nitro groups,
- a naphthylmethyl group,
- a phenyl group which may be unsubstituted or substituted by a substitutent selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, alkoxy groups having from 1 to 4 carbon atoms, hydroxy groups, halogen atoms and nitro groups,
- a naphthyl group, or
- a furyl, thienyl, pyridyl, oxazolyl, thiazolyl, isoxazolyl or isothiazolyl group which may be optionally substituted by a substituent selected from the group consisting of alkyl groups having 1 or 2 carbon atoms, fluorine atom and chlorine atoms,
- R.sup.4 represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, a benzyl group or a phenethyl group;
- R.sup.5 represents a cycloalkyl group having from 3 to 6 carbon atoms, a pyrrolidinyl group or a piperidinyl group, said cycloalkyl group, pyrrolidinyl group or piperidinyl group being substituted by a group having the formula --B--ONO.sub.2 and further being optionally substituted by a methyl group, wherein B represents a single bond, a methylene group, an ethylene group, a trimethylene group or a tetramethylene group; and
- A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 29. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein:
- W represents a sulfur atom or an oxygen atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.2 and R.sup.3 may be the same or different and each represents
- a hydrogen atom,
- a methyl group,
- an ethyl group,
- a benzyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and chlorine atoms,
- a phenethyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and chlorine atoms,
- a phenyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and and chlorine atoms,
- a furyl group,
- a thienyl group, or
- a pyridyl group;
- R.sup.4 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.5 represents a cycloalkyl group having from 3 to 6 carbon atoms, a pyrrolidinyl group or a piperidinyl group, said cycloalkyl group, pyrrolidinyl group or piperidinyl group being substituted by a group having the formula --B--ONO.sub.2 and further being optionally substituted by a methyl group, wherein B represents a single bond, a methylene group, an ethylene group, a trimethylene group or a tetramethylene group; and
- A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 30. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup. --;
- R.sup.1 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.2 and R.sup.3 may be the same or different and each represents
- a hydrogen atom,
- a methyl group,
- an ethyl group,
- a benzyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and chlorine atoms,
- a phenethyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and and chlorine atoms,
- a phenyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and and chlorine atoms,
- a furyl group,
- a thienyl group, or
- a pyridyl group;
- R.sup.4 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.5 represents a cycloalkyl group having from 3 to 6 carbon atoms, a pyrrolidinyl group or a piperidinyl group, said cycloalkyl group, pyrrolidinyl group or piperidinyl group being substituted by a group having the formula --B--ONO.sub.2 and further being optionally substituted by a methyl group, wherein B represents a single bond, a methylene group, an ethylene group, a trimethylene group or a tetramethylene group; and
- A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 31. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.2 represents a hydrogen atom, a methyl group, an ethyl group, a benzyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups and hydroxyl groups, a phenyl group which may be optionally substituted by a methyl group or a methoxy group, or a thienyl group; and
- R.sup.3 represents a hydrogen atom; or
- R.sup.2 and R.sup.3 each represent a methyl group;
- R.sup.4 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.5 represents a cyclopropyl group, cyclopentyl group or cyclohexyl group, said groups being substituted by a group having the formula --B--ONO.sub.2 wherein B represents a methylene group, an ethylene group, a trimethylene group or a tetramethylene group; and
- A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 32. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.2 represents a hydrogen atom, a methyl group, a benzyl group which may be optionally substituted by a methyl group or a methoxy group, or a phenyl group, and
- R.sup.3 represents a hydrogen atom; or
- R.sup.2 and R.sup.3 each represent a methyl group;
- R.sup.4 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.5 represents a cyclopentyl group or a cyclohexyl group, said groups being substituted by a group having the formula --B--ONO.sub.2 wherein B represents a methylene group, an ethylene group, a trimethylene group or a tetramethylene group; and
- A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 33. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.2 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.3 represents a hydrogen atom;
- R.sup.4 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.5 represents a 2- or 3-nitroxymethylcyclopentyl group, a 2- or 3-(2-nitroxyethyl)cyclopentyl group, a 2- or 3-(3-nitroxypropyl)cyclopentyl group, a 2- or 3-(4-nitroxybutyl)cyclopentyl group, a 2-, 3- or 4-nitroxycyclohexyl group, a 2-, 3- or 4-nitroxymethylcyclohexyl group, a 2-, 3- or 4-(2-nitroxyethyl)cyclohexyl group, a 2-, 3- or 4-(3-nitroxypropyl)cyclohexyl group, a 2-, 3- or 4-(4-nitroxybutyl)-cyclohexyl group, a 3-, 4-, 5- or 6-nitroxymethylpiperidin-2-yl group or a 3-, 4-, 5- or 6-nitroxymethyl-1-methylpiperidin-2-yl group; and
- A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 34. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein;
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom;
- R.sup.2 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.3 represents a hydrogen atom;
- R.sup.4 represents a hydrogen atom;
- R.sup.5 represents a 2- or 3-nitroxymethylcyclopentyl group, a 2-, 3- or 4-nitroxycyclohexyl group, a 2-, 3- or 4-nitroxymethylcyclohexyl group, a 2-, 3- or 4-(2-nitroxyethyl)cyclohexyl group, a 2-, 3- or 4-(3-nitroxypropyl)cyclohexyl group or a 2-, 3- or 4-(4-nitroxybutyl)cyclohexyl group; and
- A represents a methylene group or an ethylene group.
- 35. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom;
- R.sup.2 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.3 represents a hydrogen atom;
- R.sup.4 represents a hydrogen atom;
- R.sup.5 represents a 3-nitroxymethylcyclopentyl group, a 4-nitroxycyclohexyl group, a 2-, 3- or 4-nitroxymethylcyclohexyl group, a 3- or 4-(2-nitroxyethyl)cyclohexyl group, a 3- or 4-(3-nitroxypropyl)cyclohexyl group or a 3- or 4-(4-nitroxybutyl)cyclohexyl group; and
- A represents a methylene group or an ethylene group.
- 36. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein:
- W represents a sulfur atom, and X is a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom,
- R.sup.2 represents a hydrogen atom;
- R.sup.3 represents a hydrogen atom;
- R.sup.4 represents a hydrogen atom;
- R.sup.5 represents a 3- or 4-nitroxymethylcyclohexyl group, a 4-(2-nitroxyethyl)cyclohexyl group, a 4-(3-nitroxypropyl)cyclohexyl group or a 4-(4-nitroxybutyl)cyclohexyl group; and
- A is a methylene group.
- 37. The thiazolidinone compound or a pharmacologically acceptable salt thereof according to claim 1, wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom;
- R.sup.2 represents a hydrogen atom;
- R.sup.3 represents a hydrogen atom;
- R.sup.4 represents a hydrogen atom;
- R.sup.5 represents a 4-nitroxymethylcyclohexyl group; and
- A represents a methylene group.
- 38. The thiazolidinone compound according to claim 1, selected from the group consisting of:
- N-(4-Nitroxymethylcyclohexylmethyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-5-methyl-2-oxothiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-2-oxo-5-(2-thienyl)thiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-5-(4-methoxyphenyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-5-benzyl-2-oxothiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-5-(4-methylbenzyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-5-(4-methoxybenzyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-5-methyl-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-2-oxo-5-(2-thienyl)thiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-5-(4-methoxyphenyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-5-benzyl-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-5-(4-methylbenzyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-5-(4-methoxybenzyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-�4-(2-nitroxyethyl)cyclohexylmethyl!-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-�4-(3-nitroxypropyl)cyclohexyl!ethyl!-2-oxothiazolidin-4-yl-carboxamide,
- N-�4-(3 -nitroxypropyl)cyclohexylmethyl!-2-oxothiazolidin-4-yl-carboxamide,
- N-�4-(4-nitroxybutyl)cyclohexylmethyl!-2-oxothiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-2-oxothiazolidin-5-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-4-methyl-2-oxothiazolidin-5-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-4-(4-methoxyphenyl)-2-oxothiazolidin-5-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-4-benzyl -2-oxothiazolidin-5 -yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-4-(4-methylbenzyl)-2-oxothiazolidin-5-yl-carboxamide, and
- N-(4-nitroxymethylcyclohexylmethyl)-4-(4-methoxybenzyl)-2-oxothiazolidin-5-yl-carboxamide,
- or a pharmacologically acceptable salt thereof.
- 39. A pharmaceutical composition for the treatment or prophylaxis of angina pectoris comprising an effective amount of an active compound in admixture with a pharmacologically acceptable carrier or diluent, wherein said active compound is selected from the group consisting of thiazolidinone compounds having the general formula: ##STR9## wherein: W represents a sulfur atom or an oxygen atom, and X represents a group having the formula --N(R.sup.1)--; or
- X represents a sulfur atom or an oxygen atom, and W represents a group having the formula --N(R.sup.1)--;
- R.sup.1 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms or an alkyl group having from 1 to 4 carbon atoms substituted by an aryl group as defined below;
- R.sup.2 and R.sup.3 may be the same or different and each represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, an alkyl group having from 1 to 4 carbon atoms substituted by an aryl group as defined below, an aryl group as defined below, or a 5- or 6-membered aromatic heterocyclic group containing 1 to 3 hetero groups selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atoms, said aromatic heterocyclic group being unsubstituted or being substituted by a substituent selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, halogen atoms, amino groups and mono- and di-alkylamino groups wherein the or each alkyl group has from 1 to 6 carbon atoms;
- R.sup.4 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms or an alkyl group having from 1 to 4 carbon atoms substituted by an aryl group as defined below;
- R.sup.5 represents a cycloalkyl group having from 3 to 8 carbon atoms, said group optionally containing a ring nitrogen atom, said group being substituted by a group having the formula --B--ONO.sub.2 and said group further optionally being substituted by an alkyl group having from 1 to 6 carbon atoms, wherein B represents a single bond or an alkylene group having from 1 to 6 carbon atoms;
- A represents a single bond or an alkylene group having from 1 to 6 carbon atoms; and said aryl group represents an aryl group having from 6 to 10 carbon atoms which may optionally be substituted by a substituent selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, alkoxy groups having from 1 to 6 carbon atoms, halogen atoms, amino groups, mono- and di- alkylamino groups wherein the or each alkyl group has from 1 to 6 carbon atoms, and nitro groups;
- and pharmacologically acceptable salts thereof.
- 40. The pharmaceutical composition according to claim 39, wherein:
- W represents a sulfur atom or an oxygen atom, and X represents a group having the formula --NR.sup.1 --; or X represents a sulfur atom, and W represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, a benzyl group or a phenethyl group;
- R.sup.2 and R.sup.3 may be the same or different and each represents
- a hydrogen atom,
- an alkyl group having from 1 to 4 carbon atoms,
- an alkyl group having from 1 to 4 carbon atoms substituted by a phenyl group which may be unsubstituted or substituted by a substituent selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, alkoxy groups having from 1 to 4 carbon atoms, hydroxy groups, halogen atoms and nitro groups,
- a naphthylmethyl group,
- a phenyl group which may be unsubstituted or substituted by a substitutent selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, alkoxy groups having from 1 to 4 carbon atoms, hydroxy groups, halogen atoms and nitro groups,
- a naphthyl group, or
- a furyl, thienyl, pyridyl, oxazolyl, thiazolyl, isoxazolyl or isothiazolyl group which may be optionally substituted by a substituent selected from the group consisting of alkyl groups having 1 or 2 carbon atoms, fluorine atoms and chlorine atoms;
- R.sup.4 represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, a benzyl group or a phenethyl group;
- R.sup.5 represents a cycloalkyl group having from 3 to 6 carbon atoms, a pyrrolidinyl group or a piperidinyl group, said cycloalkyl group, pyrrolidinyl group or piperidinyl group being substituted by a group having the formula --B--ONO.sub.2 and further being optionally substituted by a methyl group, wherein B represents a single bond, a methylene group, an ethylene group, a trimethylene group or a tetramethylene group; and
- A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 41. The pharmaceutical composition according to claim 39, wherein:
- W represents a sulfur atom or an oxygen atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.2 and R.sup.3 may be the same or different and each represents
- a hydrogen atom,
- a methyl group,
- an ethyl group,
- a benzyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and chlorine atoms,
- a phenethyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and chlorine atoms,
- a phenyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and chlorine atoms,
- a furyl group,
- a thienyl group, or
- a pyridyl group;
- R.sup.4 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.5 represents a cycloalkyl group having from 3 to 6 carbon atoms, a pyrrolidinyl group or a piperidinyl group, said cycloalkyl group, pyrrolidinyl group or piperidinyl group being substituted by a group having the formula --B--ONO.sub.2 and further being optionally substituted by a methyl group, wherein B represents a single bond, a methylene group, an ethylene group, a trimethylene group or a tetramethylene group; and
- A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 42. The pharmaceutical composition according to claim 39, wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.2 and R.sup.3 may be the same or different and each represents
- a hydrogen atom,
- a methyl group,
- an ethyl group,
- a benzyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and chlorine atoms,
- a phenethyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and chlorine atoms,
- a phenyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and chlorine atoms,
- a furyl group,
- a thienyl group, or
- a pyridyl group;
- R.sup.4 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.5 represents a cycloalkyl group having from 3 to 6 carbon atoms, a pyrrolidinyl group or a piperidinyl group, said cycloalkyl group, pyrrolidinyl group or piperidinyl group being substituted by a group having the formula --B--ONO.sub.2 and further being optionally substituted by a methyl group, wherein B represents a single bond, a methylene group, an ethylene group, a trimethylene group or a tetramethylene group; and
- A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 43. The pharmaceutical composition according to claim 39, wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.2 represents a hydrogen atom, a methyl group, an ethyl group, a benzyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups and hydroxyl groups, a phenyl group which may be optionally substituted by a methyl group or a methoxy group, or a thienyl group; and
- R.sup.3 represents a hydrogen atom; or
- R.sup.2 and R.sup.3 each represent a methyl group;
- R.sup.4 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.5 represents a cyclopropyl group, cyclopentyl group or cyclohexyl group, said groups being substituted by a group having the formula --B--ONO.sub.2 wherein B represents a methylene group, an ethylene group, a trimethylene group or a tetramethylene group; and
- A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 44. The pharmaceutical composition according to claim 39, wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.2 represents a hydrogen atom, a methyl group, a benzyl group which may be optionally substituted by a methyl group or a methoxy group, or a phenyl group, and
- R.sup.3 represents a hydrogen atom; or
- R.sup.2 and R.sup.3 each represent a methyl group;
- R.sup.4 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.5 represents a cyclopentyl group or a cyclohexyl group, said groups being substituted by a group having the formula --B--ONO.sub.2 wherein B represents a methylene group, an ethylene group, a trimethylene group or a tetramethylene group; and
- A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 45. The pharmaceutical composition according to claim 39, wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.2 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.3 represents a hydrogen atom;
- R.sup.4 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.5 represents a 2- or 3-nitroxymethylcyclopentyl group, a 2- or 3-(2-nitroxyethyl)cyclopentyl group, a 2- or 3-(3-nitroxypropyl)cyclopentyl group, a 2- or 3-(4-nitroxybutyl)cyclopentyl group, a 2-, 3- or 4-nitroxycyclohexyl group, a 2-, 3- or 4-nitroxymethylcyclohexyl group, a 2-, 3- or 4-(2-nitroxyethyl)cyclohexyl group, a 2-, 3- or 4-(3-nitroxypropyl)cyclohexyl group, a 2-, 3- or 4-(4-nitroxybutyl)cyclohexyl group, a 3-, 4-, 5- or 6-nitroxymethylpiperidin-2-yl group or a 3-, 4-, 5- or 6-nitroxymethyl-1-methylpiperidin-2-yl group; and
- A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 46. The pharmaceutical composition according to claim 39, wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom;
- R.sup.2 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.3 represents a hydrogen atom;
- R.sup.4 represents a hydrogen atom;
- R.sup.5 represents a 2- or 3-nitroxymethylcyclopentyl group, a 2-, 3- or 4-nitroxycyclohexyl group, a 2-, 3- or 4-nitroxymethylcyclohexyl group, a 2-, 3- or 4-(2-nitroxyethyl)cyclohexyl group, a 2-, 3- or 4-(3-nitroxypropyl)cyclohexyl group or a 2-, 3- or 4-(4-nitroxybutyl)cyclohexyl group; and
- A represents a methylene group or an ethylene group.
- 47. The pharmaceutical composition according to claim 39, wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom;
- R.sup.2 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.3 represents a hydrogen atom;
- R.sup.4 represents a hydrogen atom;
- R.sup.5 represents a 3-nitroxymethylcyclopentyl group, a 4-nitroxycyclohexyl group, a 2-, 3- or 4-nitroxymethylcyclohexyl group, a 3- or 4-(2-nitroxyethyl)cyclohexyl group, a 3- or 4-(3-nitroxypropyl)cyclohexyl group or a 3- or 4-(4-nitroxybutyl)cyclohexyl group; and
- A represents a methylene group or an ethylene group.
- 48. The pharmaceutical composition according to claim 39, wherein:
- W represents a sulfur atom, and X is a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom;
- R.sup.2 represents a hydrogen atom;
- R.sup.3 represents a hydrogen atom;
- R.sup.4 represents a hydrogen atom;
- R.sup.5 represents a 3- or 4-nitroxymethylcyclohexyl group, a 4-(2-nitroxyethyl)cyclohexyl group, a 4-(3-nitroxypropyl)cyclohexyl group or a 4-(4-nitroxybutyl)cyclohexyl group; and
- A is a methylene group.
- 49. The pharmaceutical composition according to claim 39, wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom;
- R.sup.2 represents a hydrogen atom;
- R.sup.3 represents a hydrogen atom;
- R.sup.4 represents a hydrogen atom;
- R.sup.5 represents a 4-nitroxymethylcyclohexyl group; and
- A represents a methylene group.
- 50. The pharmaceutical composition according to claim 39, wherein said active compound is selected from the group consisting of:
- N-(4-Nitroxymethylcyclohexylmethyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-5-methyl-2-oxothiazolidin-4-yl-carboxamide,
- N-(4-nitroxym ethylcyclohexylmethyl)-2-oxo-5-(2-thienyl)thiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-5-(4-methoxyphenyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-5-benzyl-2-oxothiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-5-(4-methylbenzyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-5-(4-methoxybenzyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-5-methyl-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-2-oxo-5-(2-thienyl)thiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-5-(4-methoxyphenyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-5-benzyl-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-5-(4-methylbenzyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-5-(4-methoxybenzyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-�4-(2-nitroxyethyl)cyclohexylmethyl!-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-�4-(3-nitroxypropyl)cyclohexyl!ethyl!-2-oxothiazolidin-4-yl-carboxamide,
- N-�4-(3-nitroxypropyl)cyclohexylmethyl!-2-oxothiazolidin-4-yl-carboxamide,
- N-�4-(4-nitroxybutyl)cyclohexylmethyl!-2-oxothiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-2-oxothiazolidin-5-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-4-methyl-2-oxothiazolidin-5-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-4-(4-methoxyphenyl)-2-oxothiazolidin-5-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-4-benzyl-2-oxothiazolidin-5-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-4-(4-methylbenzyl)-2-oxothiazolidin-5-yl-carboxamide, and
- N-(4-nitroxymethylcyclohexylmethyl)-4-(4-methoxybenzyl)-2-oxothiazolidin-5-yl-carboxamide;
- and pharmacologically acceptable salts thereof.
- 51. A method for the treatment or prophylaxis of angina pectoris comprising administering to a patient an effective amount of an active compound in admixture with a pharmacologically acceptable carrier or diluent, wherein said active compound is selected from the group consisting of thiazolidinone compounds having the general formula: ##STR10## wherein: W represents a sulfur atom or an oxygen atom, and X represents a group having the formula --N(R.sup.1)--; or
- X represents a sulfur atom or an oxygen atom, and W represents a group having the formula --N(R.sup.1)--;
- R.sup.1 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms or an alkyl group having from 1 to 4 carbon atoms substituted by an aryl group as defined below;
- R.sup.2 and R.sup.3 may be the same or different and each represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, an alkyl group having from 1 to 4 carbon atoms substituted by an aryl group as defined below, an aryl group as defined below, or a 5- or 6-membered aromatic heterocyclic group containing 1 to 3 hetero groups selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atoms, said aromatic heterocyclic group being unsubstituted or being substituted by a substituent selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, halogen atoms, amino groups and mono- and di-alkylamino groups wherein the or each alkyl group has from 1 to 6 carbon atoms;
- R.sup.4 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms or an alkyl group having from 1 to 4 carbon atoms substituted by an aryl group as defined below;
- R.sup.5 represents a cycloalkyl group having from 3 to 8 carbon atoms, said group optionally containing a ring nitrogen atom, said group being substituted by a group having the formula --B--ONO.sub.2 and said group further optionally being substituted by an alkyl group having from 1 to 6 carbon atoms, wherein B represents a single bond or an alkylene group having from 1 to 6 carbon atoms;
- A represents a single bond or an alkylene group having from 1 to 6 carbon atoms; and said aryl group represents an aryl group having from 6 to 10 carbon atoms which may optionally be substituted by a substituent selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, alkoxy groups having from 1 to 6 carbon atoms, halogen atoms, amino groups, mono- and di- alkylamino groups wherein the or each alkyl group has from 1 to 6 carbon atoms, and nitro groups;
- and pharmacologically acceptable salts thereof.
- 52. The method according to claim 51, wherein:
- W represents a sulfur atom or an oxygen atom, and X represents a group having the formula --NR.sup.1 --; or X represents a sulfur atom, and W represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, a benzyl group or a phenethyl group;
- R.sup.2 and R.sup.3 may be the same or different and each represents
- a hydrogen atom,
- an alkyl group having from 1 to 4 carbon atoms,
- an alkyl group having from 1 to 4 carbon atoms substituted by a phenyl group which may be unsubstituted or substituted by a substituent selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, alkoxy groups having from 1 to 4 carbon atoms, hydroxy groups, halogen atoms and nitro groups,
- a naphthylmethyl group,
- a phenyl group which may be unsubstituted or substituted by a substitutent selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, alkoxy groups having from 1 to 4 carbon atoms, hydroxy groups, halogen atoms and nitro groups,
- a naphthyl group, or
- a furyl, thienyl, pyridyl, oxazolyl, thiazolyl, isoxazolyl or isothiazolyl group which may be optionally substituted by a substituent selected from the group consisting of alkyl groups having 1 or 2 carbon atoms, fluorine atoms and chlorine atoms;
- R.sup.4 represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, a benzyl group or a phenethyl group;
- R.sup.5 represents a cycloalkyl group having from 3 to 6 carbon atoms, a pyrrolidinyl group or a piperidinyl group, said cycloalkyl group, pyrrolidinyl group or piperidinyl group being substituted by a group having the formula --B--ONO.sub.2 and further being optionally substituted by a methyl group, wherein B represents a single bond, a methylene group, an ethylene group, a trimethylene group or a tetramethylene group; and
- A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 53. The method according to claim 51, wherein:
- W represents a sulfur atom or an oxygen atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.2 and R.sup.3 may be the same or different and each represents
- a hydrogen atom,
- a methyl group,
- an ethyl group,
- a benzyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and chlorine atoms,
- a phenethyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and chlorine atoms,
- a phenyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and chlorine atoms,
- a furyl group,
- a thienyl group, or
- a pyridyl group;
- R.sup.4 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.5 represents a cycloalkyl group having from 3 to 6 carbon atoms, a pyrrolidinyl group or a piperidinyl group, said cycloalkyl group, pyrrolidinyl group or piperidinyl group being substituted by a group having the formula --B--ONO.sub.2 and further being optionally substituted by a methyl group, wherein B represents a single bond, a methylene group, an ethylene group, a trimethylene group or a tetramethylene group; and
- A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 54. The method according to claim 51, wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.2 and R.sup.3 may be the same or different and each represents
- a hydrogen atom,
- a methyl group,
- an ethyl group,
- a benzyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and chlorine atoms,
- a phenethyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and chlorine atoms,
- a phenyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and chlorine atoms,
- a furyl group,
- a thienyl group, or
- a pyridyl group;
- R.sup.4 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.5 represents a cycloalkyl group having from 3 to 6 carbon atoms, a pyrrolidinyl group or a piperidinyl group, said cycloalkyl group, pyrrolidinyl group or piperidinyl group being substituted by a group having the formula --B--ONO.sub.2 and further being optionally substituted by a methyl group, wherein B represents a single bond, a methylene group, an ethylene group, a trimethylene group or a tetramethylene group; and
- A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 55. The method according to claim 51, wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.2 represents a hydrogen atom, a methyl group, an ethyl group, a benzyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups and hydroxyl groups, a phenyl group which may be optionally substituted by a methyl group or a methoxy group, or a thienyl group; and
- R.sup.3 represents a hydrogen atom; or
- R.sup.2 and R.sup.3 each represent a methyl group;
- R.sup.4 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.5 represents a cyclopropyl group, cyclopentyl group or cyclohexyl group, said groups being substituted by a group having the formula --B--ONO.sub.2 wherein B represents a methylene group, an ethylene group, a trimethylene group or a tetramethylene group; and
- A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 56. The method according to claim 51, wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.2 represents a hydrogen atom, a methyl group, a benzyl group which may be optionally substituted by a methyl group or a methoxy group, or a phenyl group, and
- R.sup.3 represents a hydrogen atom; or
- R.sup.2 and R.sup.3 each represent a methyl group;
- R.sup.4 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.5 represents a cyclopentyl group or a cyclohexyl group, said groups being substituted by a group having the formula --B--ONO.sub.2 wherein B represents a methylene group, an ethylene group, a trimethylene group or a tetramethylene group; and
- A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 57. The method according to claim 51, wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.2 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.3 represents a hydrogen atom;
- R.sup.4 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.5 represents a 2- or 3-nitroxymethylcyclopentyl group, a 2- or 3-(2-nitroxyethyl)cyclopentyl group, a 2- or 3-(3-nitroxypropyl)cyclopentyl group, a 2- or 3-(4-nitroxybutyl)cyclopentyl group, a 2-, 3- or 4-nitroxycyclohexyl group, a 2-, 3- or 4-nitroxymethylcyclohexyl group, a 2-, 3- or 4-(2-nitroxyetliyl)cyclohexyl group, a 2-, 3- or 4-(3-nitroxypropyl)cyclohexyl group, a 2-, 3- or 4-(4-nitroxybutyl)cyclohexyl group, a 3-, 4-, 5- or 6-nitroxymethylpiperidin-2-yl group or a 3-, 4-, 5- or 6-nitroxymethyl-1-methylpiperidin-2-yl group; and
- A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 58. The method according to claim 51, wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom;
- R.sup.2 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.3 represents a hydrogen atom;
- R.sup.4 represents a hydrogen atom;
- R.sup.5 represents a 2- or 3-nitroxymethylcyclopentyl group, a 2-, 3- or 4-nitroxycyclohexyl group, a 2-, 3- or 4-nitroxymethylcyclohexyl group, a 2-, 3- or 4-(2-nitroxyethyl)cyclohexyl group, a 2-, 3- or 4-(3-nitroxypropyl)cyclohexyl group or a 2-, 3- or 4-(4-nitroxybutyl)cyclohexyl group; and
- A represents a methylene group or an ethylene group.
- 59. The method according to claim 51, wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom;
- R.sup.2 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.3 represents a hydrogen atom;
- R.sup.4 represents a hydrogen atom;
- R.sup.5 represents a 3-nitroxymethylcyclopentyl group, a 4-nitroxycyclohexyl group, a 2-, 3- or 4-nitroxymethylcyclohexyl group, a 3- or 4-(2-nitroxyethyl)cyclohexyl group, a 3- or 4-(3-nitroxypropyl)cyclohexyl group or a 3- or 4-(4-nitroxybutyl)cyclohexyl group, and
- A represents a methylene group or an ethylene group.
- 60. The method according to claim 51, wherein:
- W represents a sulfur atom, and X is a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom;
- R.sup.2 represents a hydrogen atom;
- R.sup.3 represents a hydrogen atom;
- R.sup.4 represents a hydrogen atom;
- R.sup.5 represents a 3- or 4-nitroxymethylcyclohexyl group, a 4-(2-nitroxyethyl)cyclohexyl group, a 4-(3-nitroxypropyl)cyclohexyl group or a 4-(4-nitroxybutyl)cyclohexyl group; and
- A is a methylene group.
- 61. The method according to claim 51, wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom;
- R.sup.2 represents a hydrogen atom;
- R.sup.3 represents a hydrogen atom;
- R.sup.4 represents a hydrogen atom;
- R.sup.5 represents a 4-nitroxymethylcyclohexyl group; and
- A represents a methylene group.
- 62. The method according to claim 51, wherein said active compound is selected from the group consisting of:
- N-(4-Nitroxymethylcyclohexylmethyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-5-methyl-2-oxothiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-2-oxo-5 -(2-thienyl)thiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-5-(4-methoxyphenyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-5-benzyl-2-oxothiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-5-(4-methylbenzyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-5-(4-methoxybenzyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-5-methyl-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-2-oxo-5-(2-thienyl)thiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-5-(4-methoxyphenyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-5-benzyl-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-5-(4-methylbenzyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-5-(4-methoxybenzyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-�4-(2-nitroxyethyl)cyclohexylmethyl!-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-�4-(3-nitroxypropyl)cyclohexyl!ethyl!-2-oxothiazolidin-4-yl-carboxamide,
- N-�4-(3-nitroxypropyl)cyclohexylmethyl!-2-oxothiazolidin-4-yl-carboxamide,
- N-�4-(4-nitroxybutyl)cyclohexylmethyl!-2-oxothiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-2-oxothiazolidin-5 -yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-4-methyl-2-oxothiazolidin-5-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-4-(4-methoxyphenyl)-2-oxothiazolidin-5-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-4-benzyl -2-oxothiazolidin-5-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-4-(4-methylbenzyl)-2-oxothiazolidin-5-yl-carboxamide, and
- N-(4-nitroxymethylcyclohexylmethyl)-4-(4-methoxybenzyl)-2-oxothiazolidin-5-yl-carboxamide;
- and pharmacologically acceptable salts thereof.
- 63. A process for preparing a thiazolidinone compound having the general formula: ##STR11## wherein: W represents a sulfur atom or an oxygen atom, and X represents a group having the formula --N(R.sup.1)--; or
- X represents a sulfur atom or an oxygen atom, and W represents a group having the formula --N(R.sup.1)--;
- R.sup.1 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms or an alkyl group having from 1 to 4 carbon atoms substituted by an aryl group as defined below;
- R.sup.2 and R.sup.3 may be the same or different and each represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, an alkyl group having from 1 to 4 carbon atoms substituted by an aryl group as defined below, an aryl group as defined below, or a 5- or 6-membered aromatic heterocyclic group containing 1 to 3 hetero groups selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atoms, said aromatic heterocyclic group being unsubstituted or being substituted by a substituent selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, halogen atoms, amino groups and mono- and di- alkylamino groups wherein the or each alkyl group has from 1 to 6 carbon atoms;
- R.sup.4 represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms or an alkyl group having from 1 to 4 carbon atoms substituted by an aryl group as defined below;
- R.sup.5 represents a cycloalkyl group having from 3 to 8 carbon atoms, said group optionally containing a ring nitrogen atom, said group being substituted by a group having the formula --B--ONO.sub.2 and said group further optionally being substituted by an alkyl group having from 1 to 6 carbon atoms, wherein B represents a single bond or an alkylene group having from 1 to 6 carbon atoms;
- A represents a single bond or an alkylene group having from 1 to 6 carbon atoms; and said aryl group represents an aryl group having from 6 to 10 carbon atoms which may optionally be substituted by a substituent selected from the group consisting of alkyl groups having from 1 to 6 carbon atoms, alkoxy groups having from 1 to 6 carbon atoms, halogen atoms, amino groups, mono- and di- alkylamino groups wherein the or each alkyl group has from 1 to 6 carbon atoms, and nitro groups;
- or a pharmacologically acceptable salt thereof, which comprises reacting a compound having the following general formula or a reactive derivative thereof: ##STR12## wherein Wa, Xa, R.sup.2 a and R.sup.3 a have the same meanings as W, X, R.sup.2 and R.sup.3, as defined above, respectively except that an amino group or an imino group (--NH--) in any of said groups may be optionally protected,
- with a compound having the general formula, or an acid addition salt thereof: ##STR13## wherein A has the same meaning as defined above, and R.sup.4 a and R.sup.5 a have the same meanings as R.sup.4 and R.sup.5, as defined above, respectively except that an amino group or an imino group (--NH--) in either of said groups may be optionally protected; and
- if desired, eliminating a protective group such as an amino protecting group from the compound thus obtained.
- 64. The process according to claim 63, wherein the reagents and reaction conditions are chosen to prepare a thiazolidinone compound or a pharmacologically acceptable salt thereof wherein:
- W represents a sulfur atom or an oxygen atom, and X represents a group having the formula --NR.sup.1 --; or X represents a sulfur atom, and W represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, a benzyl group or a phenethyl group;
- R.sup.2 and R.sup.3 may be the same or different and each represents
- a hydrogen atom,
- an alkyl group having from 1 to 4 carbon atoms,
- an alkyl group having from 1 to 4 carbon atoms substituted by a phenyl group which may be unsubstituted or substituted by a substituent selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, alkoxy groups having from 1 to 4 carbon atoms, hydroxy groups, halogen atoms and nitro groups,
- a naphthylmethyl group,
- a phenyl group which may be unsubstituted or substituted by a substitutent selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, alkoxy groups having from 1 to 4 carbon atoms, hydroxy groups, halogen atoms and nitro groups,
- a naphthyl group, or
- a furyl, thienyl, pyridyl, oxazolyl, thiazolyl, isoxazolyl or isothiazolyl group which may be optionally substituted by a substituent selected from the group consisting of alkyl groups having 1 or 2 carbon atoms, fluorine atom and chlorine atoms;
- R.sup.4 represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, a benzyl group or a phenethyl group;
- R.sup.5 represents a cycloalkyl group having from 3 to 6 carbon atoms, a pyrrolidinyl group or a piperidinyl group, said cycloalkyl group, pyrrolidinyl group or piperidinyl group being substituted by a group having the formula --B--ONO.sub.2 and further being optionally substituted by a methyl group, wherein B represents a single bond, a methylene group, an ethylene group, a trimethylene group or a tetramethylene group; and
- A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 65. The process according to claim 63, wherein the reagents and reaction conditions are chosen to prepare a thiazolidinone compound or a pharmacologically acceptable salt thereof wherein:
- W represents a sulfur atom or an oxygen atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.2 and R.sup.3 may be the same or different and each represents
- a hydrogen atom,
- a methyl group,
- an ethyl group,
- a benzyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and chlorine atoms,
- a phenethyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and chlorine atoms,
- a phenyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and chlorine atoms,
- a furyl group,
- a thienyl group, or
- a pyridyl group;
- R.sup.4 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.5 represents a cycloalkyl group having from 3 to 6 carbon atoms, a pyrrolidinyl group or a piperidinyl group, said cycloalkyl group, pyrrolidinyl group or piperidinyl group being substituted by a group having the formula --B--ONO.sub.2 and further being optionally substituted by a methyl group, wherein B represents a single bond, a methylene group, an ethylene group, a trimethylene group or a tetramethylene group; and
- A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 66. The process according to claim 63, wherein the reagents and reaction conditions are chosen to prepare a thiazolidinone compound or a pharmacologically acceptable salt thereof wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.2 and R.sup.3 may be the same or different and each represents
- a hydrogen atom,
- a methyl group,
- an ethyl group,
- a benzyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and chlorine atoms,
- a phenethyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and chlorine atoms,
- a phenyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups, hydroxy groups, fluorine atoms and chlorine atoms,
- a furyl group,
- a thienyl group, or
- a pyridyl group;
- R.sup.4 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.5 represents a cycloalkyl group having from 3 to 6 carbon atoms, a pyrrolidinyl group or a piperidinyl group, said cycloalkyl group, pyrrolidinyl group or piperidinyl group being substituted by a group having the formula --B--ONO.sub.2 and further being optionally substituted by a methyl group, wherein B represents a single bond, a methylene group, an ethylene group, a trimethylene group or a tetramethylene group; and
- A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 67. The process according to claim 63, wherein the reagents and reaction conditions are chosen to prepare a thiazolidinone compound or a pharmacologically acceptable salt thereof wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.2 represents a hydrogen atom, a methyl group, an ethyl group, a benzyl group which may be optionally substituted by a substituent selected from the group consisting of methyl groups, methoxy groups and hydroxyl groups, a phenyl group which may be optionally substituted by a methyl group or a methoxy group, or a thienyl group; and
- R.sup.3 represents a hydrogen atom; or R.sup.2 and R.sup.3 each represent a methyl group;
- R.sup.4 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.5 represents a cyclopropyl group, cyclopentyl group or cyclohexyl group, said groups being substituted by a group having the formula --B--ONO.sub.2 wherein B represents a methylene group, an ethylene group, a trimethylene group or a tetramethylene group; and
- A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 68. The process according to claim 63, wherein the reagents and reaction conditions are chosen to prepare a thiazolidinone compound or a pharmacologically acceptable salt thereof wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.2 represents a hydrogen atom, a methyl group, a benzyl group which may be optionally substituted by a methyl group or a methoxy group, or a phenyl group, and
- R.sup.3 represents a hydrogen atom; or
- R.sup.2 and R.sup.3 each represent a methyl group;
- R.sup.4 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.5 represents a cyclopentyl group or a cyclohexyl group, said groups being substituted by a group having the formula --B--ONO.sub.2 wherein B represents a methylene group, an ethylene group, a trimethylene group or a tetramethylene group; and
- A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 69. The process according to claim 63, wherein the reagents and reaction conditions are chosen to prepare a thiazolidinone compound or a pharmacologically acceptable salt thereof wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.2 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.3 represents a hydrogen atom;
- R.sup.4 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.5 represents a 2- or 3-nitroxymethylcyclopentyl group, a 2- or 3-(2-nitroxyethyl)cyclopentyl group, a 2- or 3-(3-nitroxypropyl)cyclopentyl group, a 2- or 3-(4-nitroxybutyl)cyclopentyl group, a 2-, 3- or 4-nitroxycyclohexyl group, a 2-, 3- or 4-nitroxymethylcyclohexyl group, a 2-, 3- or 4-(2-nitroxyethyl)cyclohexyl group, a 2-, 3- or 4-(3-nitroxypropyl)cyclohexyl group, a 2-, 3- or 4-(4-nitroxybutyl)cyclohexyl group, a 3-, 4-, 5- or 6-nitroxymethylpiperidin-2-yl group or a 3-, 4-, 5- or 6-nitroxymethyl-1-methylpiperidin-2-yl group; and
- A represents a single bond or an alkylene group having 1 or 2 carbon atoms.
- 70. The process according to claim 63, wherein the reagents and reaction conditions are chosen to prepare a thiazolidinone compound or a pharmacologically acceptable salt thereof wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom;
- R.sup.2 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.3 represents a hydrogen atom,
- R.sup.4 represents a hydrogen atom;
- R.sup.5 represents a 2- or 3-nitroxymethylcyclopentyl group, a 2-, 3- or 4-nitroxycyclohexyl group, a 2-, 3- or 4-nitroxymethylcyclohexyl group, a 2-, 3- or 4-(2-nitroxyethyl)cyclohexyl group, a 2-, 3- or 4-(3-nitroxypropyl)cyclohexyl group or a 2-, 3- or 4-(4-nitroxybutyl)cyclohexyl group; and
- A represents a methylene group or an ethylene group.
- 71. The process according to claim 63, wherein the reagents and reaction conditions are chosen to prepare a thiazolidinone compound or a pharmacologically acceptable salt thereof wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom;
- R.sup.2 represents a hydrogen atom, a methyl group or a benzyl group;
- R.sup.3 represents a hydrogen atom;
- R.sup.4 represents a hydrogen atom;
- R.sup.5 represents a 3-nitroxymethylcyclopentyl group, a 4-nitroxycyclohexyl group, a 2-, 3- or 4-nitroxymethylcyclohexyl group, a 3- or 4-(2-nitroxyethyl)cyclohexyl group, a 3- or 4-(3-nitroxypropyl)cyclohexyl group or a 3- or 4-(4-nitroxybutyl)cyclohexyl group; and
- A represents a methylene group or an ethylene group.
- 72. The process according to claim 63, wherein the reagents and reaction conditions are chosen to prepare a thiazolidinone compound or a pharmacologically acceptable salt thereof wherein:
- W represents a sulfur atom, and X is a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom;
- R.sup.2 represents a hydrogen atom;
- R.sup.3 represents a hydrogen atom;
- R.sup.4 represents a hydrogen atom;
- R.sup.5 represents a 3- or 4-nitroxymethylcyclohexyl group, a 4-(2-nitroxyethyl)cyclohexyl group, a 4-(3-nitroxypropyl)cyclohexyl group or a 4-(4-nitroxybutyl)cyclohexyl group; and
- A is a methylene group.
- 73. The process according to claim 63, wherein the reagents and reaction conditions are chosen to prepare a thiazolidinone compound or a pharmacologically acceptable salt thereof wherein:
- W represents a sulfur atom, and X represents a group having the formula --NR.sup.1 --;
- R.sup.1 represents a hydrogen atom;
- R.sup.2 represents a hydrogen atom;
- R.sup.3 represents a hydrogen atom;
- R.sup.4 represents a hydrogen atom;
- R.sup.5 represents a 4-nitroxymethylcyclohexyl group; and
- A represents a methylene group.
- 74. The process according to claim 63, wherein the reagents and reaction conditions are chosen to prepare a thiazolidinone compound selected from the group consisting of:
- N-(4-Nitroxymethylcyclohexylmethyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-5-methyl-2-oxothiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-2-oxo-5-(2-thienyl)thiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-5-(4-methoxyphenyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethyicyclohexyimethyl)-5-benzyl-2-oxothiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-5-(4-methylbenzyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-5-(4-methoxybenzyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-5-methyl-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-26oxo-5-(2-thienyl)thiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-5-(4-methoxyphenyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-5-benzyl-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-5-(4-methylbenzyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-(4-nitroxymethylcyclohexyl)ethyl!-5-(4-methoxybenzyl)-2-oxothiazolidin-4-yl-carboxamide,
- N-�4-(2-nitroxyethyl)cyclohexylmethyl!-2-oxothiazolidin-4-yl-carboxamide,
- N-�2-�4-(3-nitroxypropyl)cyclohexyl!ethyl!-2-oxothiazolidin-4-yl-carboxamide,
- N-�4-(3-nitroxypropyl)cyclohexylmethyl!-2-oxothiazolidin-4-yl-carboxamide,
- N-�4-(4-nitroxybutyl)cyclohexylmethyl!-2-oxothiazolidin-4-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-2-oxothiazolidin-5-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-4-methyl-2-oxothiazolidin-5-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-4-(4-methoxyphenyl)-2-oxothiazolidin-5-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-4-benzyl-2-oxothiazolidin-5-yl-carboxamide,
- N-(4-nitroxymethylcyclohexylmethyl)-4-(4-methylbenzyl)-2-oxothiazolidin-5-yl-carboxamide, and
- N-(4-nitroxymethylcyclohexylmethyl)-4-(4-methoxybenzyl)-2-oxothiazolidin-5-yl-carboxamide;
- or a pharmacologically acceptable salt thereof.
Priority Claims (1)
Number |
Date |
Country |
Kind |
6-311511 |
Dec 1994 |
JPX |
|
Parent Case Info
This application is a continuation application of International Application No. PCT/JP95/02545 filed Dec. 13, 1995.
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