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Details for Patent: 6,686,475

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Details for Patent: 6,686,475

Title: Compounds
Abstract:Compounds of formula (I): ##STR1## or a tautomeric form thereof, or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate thereof, wherein: A.sup.1 represents a substituted or unsubstituted aromatic heterocyclyl group; R.sup.1 represents a hydrocarbon atom, an alkyl group, an acyl group, an aralkyl group, wherein the aryl moiety may be substituted or unsubstituted, or a substituted or unsubstituted aryl group; R.sup.2 and R.sup.3 each represent hydrogen, or R.sup.2 and R.sup.3 together represent a bond; A.sup.2 represents a benzene ring having a total up to five substituents; and n represents an integer in the range of from 2 to 6; pharmaceutical compositions containing such compounds and the use of such compounds and compositions in medicine.
Inventor(s): Hindley; Richard Mark (Epsom, GB)
Assignee: Beecham Group p.l.c. (Brentford, GB)
Filing Date:Feb 07, 2002
Application Number:10/071,824
Claims:1. A process for preparing a compound of formula (I): ##STR93##

or a tautomeric form thereof and/or a pharmaceutically acceptable salt thereof and/or a pharmaceutically acceptable solvate thereof, wherein: A.sup.1 represents a substituted or unsubstituted, single ring aromatic heterocyclyl group having 4 to 7 ring atoms and comprising up to 4 hetero atoms selected from oxygen, sulphur and nitrogen, the substituents for the heterocyclyl group being up to 4 substituents selected from the group consisting of: C.sub.1-12 -alkyl, C.sub.1-12 -alkoxy, aryl and halogen or any two substituents on adjacent carbon atoms, together with the carbon atoms to which they are attached, may form an aryl group, and wherein the carbon atoms of the aryl group represented by the said two substituents may themselves be substituted or unsubstituted; R.sup.1 represents a hydrogen atom, a C.sub.1-12 -alkyl group, a C.sub.1-6 -alkylcarbonyl group, an aryl-C.sub.1-12 -alkyl group, the aryl moiety being substituted or unsubstituted, or a substituted or unsubstituted aryl group; any aryl group being phenyl or naphthyl optionally substituted with up to five groups selected from halogen, C.sub.1-12 -alkyl, phenyl, C.sub.1-12 -alkoxy, halo-C.sub.1-12 -alkyl, hydroxy, amino, nitro, carboxy, C.sub.1-12 -alkoxycarbonyl, C.sub.1-12 -alkoxycarbonyl-C.sub.1-12 -alkyl, C.sub.1-12 -alkylcarbonyloxy, and C.sub.1-12 -alkylcarbonyl; R.sup.2 and R.sup.3 each represent hydrogen, or R.sup.2 and R.sup.3 together represent a bond; A.sup.2 represents a benzene ring having three optional substituents which may be selected from halogen, substituted or unsubstituted alkyl or alkoxy, substituents for the alkyl group being selected from the group consisting of halogen, C.sub.1-12 -alkyl, phenyl, C.sub.1-12 -alkoxy, halo-C.sub.1-12 -alkyl, hydroxy, amino, nitro, carboxy, C.sub.1-12 -alkoxycarbonyl, C.sub.1-12 -alkoxycarbonyl-C.sub.1-12 -alkyl, C.sub.1-12 -alkylcarbonyloxy, and C.sub.1-12 -alkylcarbonyl; and n represents an integer in the range of from 2 to 6; wherein the process comprises reacting a compound of formula (III): ##STR94## wherein R.sup.2, R.sup.3 and A.sup.2 are as defined in relation to formula (I), and R.sup.a is a moiety convertible to a moiety of formula (f): ##STR95## wherein R.sup.1, A.sup.1, and n are as defined in relation to formula (I), with an appropriate reagent capable of converting R.sup.a to the said moiety (f); and thereafter optionally carrying out one or more of the following steps: (i) converting a compound of formula (I) to a further compound of formula (I); and/or (ii) preparing a pharmaceutically acceptable salt of the compound of formula (I) and/or a pharmaceutically acceptable solvate thereof.

2. The process according to claim 1, wherein a product of the process is 5-(4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl)-2,4-thiazolidinedione or a tautomeric form thereof and/or a pharmaceutically acceptable salt thereof and/or a pharmaceutically acceptable solvate thereof.

3. The process according to claim 2, wherein the product comprises a solvate.

4. The process according to claim 3, wherein the solvate comprises a hydrate.

5. The process according to claim 2, wherein the product comprises 5-(4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl)-2,4-thiazolidinedione or a tautomeric form thereof.

6. The process according to claim 2, wherein the product comprises a pharmaceutically acceptable salt.

7. The process according to claim 6, wherein the salt comprises a salt of the thiazolidinedione moiety.

8. The process according to claim 7, wherein the salt comprises a metal salt.

9. The process according to claim 8, wherein the metal salt comprises an alkali metal salt.

10. The process according to claim 9, wherein the alkali metal salt comprises a lithium salt.

11. The process according to claim 9, wherein the alkali metal salt comprises a sodium salt.

12. The process according to claim 9, wherein the alkali metal salt comprises a potassium salt.

13. The process of claim 1 comprising step (i), wherein said step (i) comprises reducing a compound of formula (I) wherein R.sup.2 and R.sup.3 together represent a bond, to a compound of formula (I) wherein R.sup.2 and R.sup.3 each represent hydrogen.

14. The process of claim 13, wherein a product of the process is 5-(4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl)-2,4-thiazolidinedione, or a tautomeric form thereof, and/or a pharmaceutically acceptable salt thereof, and/or a pharmaceutically acceptable solvate thereof.

15. The process of claim 13, wherein said reduction includes catalytic reduction.

16. The process of claim 15, wherein the catalytic reduction employs a palladium on carbon catalyst.

17. The process of claim 13, wherein said reduction includes use of a metal/solvent reducing system.

18. The process of claim 17 wherein the metal/solvent reducing system comprises magnesium in methanol.

19. A process for preparing a compound of formula (I): ##STR96##

or a tautomeric form thereof and/or a pharmaceutically acceptable salt thereof and/or a pharmaceutically acceptable solvate thereof, wherein: A.sup.1 represents a substituted or unsubstituted, single ring aromatic heterocyclyl group having 4 to 7 ring atoms and comprising up to 4 hetero atoms selected from oxygen, sulphur and nitrogen, the substituents for the heterocyclyl group being up to 4 substituents selected from the group consisting of: C.sub.1-12 -alkyl, C.sub.1-12 -alkoxy, aryl and halogen or any two substituents on adjacent carbon atoms, together with the carbon atoms to which they are attached, may form an aryl group, and wherein the carbon atoms of the aryl group represented by the said two substituents may themselves be substituted or unsubstituted; R.sup.1 represents a hydrogen atom, a C.sub.1-12 -alkyl group, a C.sub.1-6 -alkylcarbonyl group, an aryl-C.sub.1-12 -alkyl group, the aryl moiety being substituted or unsubstituted, or a substituted or unsubstituted aryl group; any aryl group being phenyl or naphthyl optionally substituted with up to five groups selected from halogen, C.sub.1-12 -alkyl, phenyl, C.sub.1-12 -alkoxy, halo-C.sub.1-12 -alkyl, hydroxy, amino, nitro, carboxy, C.sub.1-12 -alkoxycarbonyl, C.sub.1-12 -alkoxycarbonyl-C.sub.1-12 -alkyl, C.sub.1-12 -alkylcarbonyloxy, and C.sub.1-12 -alkylcarbonyl; R.sup.2 and R.sup.3 each represent hydrogen, or R.sup.2 and R.sup.3 together represent a bond; A.sup.2 represents a benzene ring having three optional substituents which may be selected from halogen, substituted or unsubstituted alkyl or alkoxy, substituents for the alkyl group being selected from the groups consisting of halogen, C.sub.1-12 -alkyl, phenyl, C.sub.1-12 -alkoxy, halo-C.sub.1-12 -alkyl, hydroxy, amino, nitro, carboxy, C.sub.1-12 -alkoxycarbonyl, C.sub.1-12 -alkoxycarbonyl-C.sub.1-12 -alkyl, C.sub.1-12 -alkylcarbonyloxy, and C.sub.1-12 -alkylcarbonyl; and n represents an integer in the range of from 2 to 6; wherein the process comprises reacting a compound of formula (VIII): ##STR97## wherein R.sup.1, A.sup.1, A.sup.2, and n are as defined in relation to formula (I) with 2,4-thiazolidinedione; and thereafter optionally carrying out one or more of the following steps: (i) converting a compound of formula (I) to a further compound of formula (I); and/or (ii) preparing a pharmaceutically acceptable salt of the compound of formula (I) and/or a pharmaceutically acceptable solvate thereof.

20. The process according to claim 19, wherein a product of the process is 5-(4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl)-2,4-thiazolidinedione or a tautomeric form thereof and/or a pharmaceutically acceptable salt thereof and/or a pharmaceutically acceptable solvate thereof.

21. The process according to claim 20, wherein the product comprises a solvate.

22. The process according to claim 21, wherein the solvate comprises a hydrate.

23. The process according to claim 20, wherein the product comprises 5-(4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl)-2,4-thiazolidinedione or a tautomeric form thereof.

24. The process according to claim 20, wherein the product comprises a pharmaceutically acceptable salt.

25. The process according to claim 24, wherein the salt comprises a salt of the thiazolidinedione moiety.

26. The process according to claim 25, wherein the salt comprises a metal salt.

27. The process according to claim 26, wherein the metal salt comprises an alkali metal salt.

28. The process according to claim 27, wherein the alkali metal salt comprises a lithium salt.

29. The process according to claim 27, wherein the alkali metal salt comprises a sodium salt.

30. The process according to claim 27, wherein the alkali metal salt comprises a potassium salt.

31. The process of claim 19 comprising step (i), wherein said step (i) comprises reducing a compound of formula (I) wherein R.sup.2 and R.sup.3 together represent a bond, to a compound of formula (I) wherein R.sup.2 and R.sup.3 each represent hydrogen.

32. The process of claim 31, wherein a product of the process is 5-(4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl)-2,4-thiazolidinedione, or a tautomeric form thereof, and/or a pharmaceutically acceptable salt thereof, and/or a pharmaceutically acceptable solvate thereof.

33. The process of claim 31 wherein said reduction includes catalytic reduction.

34. The process of claim 33 wherein the catalytic reduction employs a palladium on carbon catalyst.

35. The process of claim 34 wherein said reduction includes use of a metal/solvent reducing system.

36. The process of claim 35 wherein the metal/solvent reducing system comprises magnesium in methanol.

37. The process of claim 19 wherein the reaction of the compound of formula (VIII) and 2,4-thiazolidinedione is carried out in solvent at the reflux temperature of the solvent and in the presence of a catalyst.

38. The process of claim 37 wherein water produced in the reaction is removed from the reaction mixture.

39. A process for preparing 5-(4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl)-2,4-thiazolidinedione or a tautomeric form thereof and/or a pharmaceutically acceptable salt thereof and/or a pharmaceutically acceptable solvate thereof, wherein the process comprises reducing 5-(4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzylidene)-2,4,thiazolidined ione to form 5-(4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl)-2,4-thiazolidinedione; and thereafter optionally preparing a pharmaceutically acceptable salt of 5-(4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl)-2,4-thiazolidinedione and/or a pharmaceutically acceptable solvate thereof.

40. The process of claim 39, wherein said reduction includes catalytic reduction.

41. The process of claim 39, wherein the catalytic reduction employs a palladium on carbon catalyst.

42. The process of claim 39, wherein said reduction includes use of a metal/solvent reducing system.

43. The process of claim 39, wherein the metal/solvent reducing system comprises magnesium in methanol.
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