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Details for Patent: RE39384

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Details for Patent: RE39384

Title:Substituted thiazolidinedione derivatives
Abstract: A compound of formula (I): ##STR00001## .Iadd.or a tautomeric form thereof, .Iaddend.wherein: R.sup.1 represents a hydrogen atom, C.sub.1-12 alkyl, C.sub.1-12 alkoxy, C.sub.1-12 alkylcarbonyl or arylC.sub.1-12 alkyl; A.sup.1 represents hydrogen or 1 to 4 optional substituents selected from the group consisting of: C.sub.1-12 alkyl, C.sub.1-12 alkoxy, aryl, and halogen; aryl represents phenyl or naphthyl optionally substituted with up to five groups selected from halogen, C.sub.1-12 alkyl, phenyl, C.sub.1-12 alkoxy, haloC.sub.1-12 alkyl, hydroxy, nitro, C.sub.1-12 alkoxycarbonyl, C.sub.1-12 alkoxycarbonyl C.sub.1-12 alkyl, C.sub.1-12 alkoxycarbonyloxy, or C.sub.1-12 alkylcarbonyl: A.sup.2 represents a benzene ring having 1 to 3 optional substituents selected from hydrogen, halogen, C.sub.1-12 alkyl, C.sub.1-12 alkoxy; and M.sup.- represents a counter-ion other than the maleate ion.
Inventor(s): Buxton; Philip Christopher (Harlow, GB), Mackenzie; Donald Colin (St. Albans, GB)
Assignee: SmithKline Beecham p.l.c. (GB)
Filing Date:Mar 17, 2003
Application Number:10/389,381
Claims:1. A compound .[.of formula (I): ##STR00007## or a tautomeric form thereof, wherein: R.sup.1 represents a hydrogen atom, C.sub.1-12 alkyl, C.sub.1-12 alkoxy, C.sub.1-12 alkylcarbonyl or arylC.sub.1-12 alkyl; A.sup.1 represents hydrogen or 1 to 4 optional substituents selected from the group consisting of: C.sub.1-12 alkyl, C.sub.1-12 alkoxy, aryl and halogen; aryl represents phenyl or naphthyl optionally substituted with up to five groups selected from halogen, C.sub.1-12 alkyl, phenyl, C.sub.1-12 alkoxy, haloC.sub.1-12 alkyl, hydroxy, nitro, C.sub.1-12 alkoxycarbonyl, C.sub.1-12 alkoxycarbonyl, C.sub.1-12 alkoxycarbonyloxy, or C.sub.1-12 alkylcarbonyl; A.sup.2 represents a benzene ring having 1 to 3 optional substituents selected from hydrogen, halogen, C.sub.1-12 alkyl, C.sub.1-12 alkoxy; and M.sup.- represents a counter-ion other than the maleate ion.]. .Iadd.which is 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione tartaric acid salt or a tautomer of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione tartaric acid salt..Iaddend.

2. A process for the preparation of a compound .[.of formula (I).]. according to claim 1.[., or a tautomeric form thereof,.]. which process comprises reacting .[.a compound of formula (II): ##STR00008## wherein R.sup.1, A.sup.1, and A.sup.2 are as defined in relation to formula (I) in claim 1, with a source of counter-ion M.sup.- which is defined in relation to formula (I), as defined in claim 1.]. .Iadd.5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4- -dione or a tautomeric form thereof with a source of tartarate ion..Iaddend.

.Iadd.3. The compound according to claim 1, wherein the salt is in a solid form..Iaddend.

.Iadd.4. A pharmaceutical composition comprising a compound according to claim 1 and at least one pharmaceutically acceptable carrier..Iaddend.

.Iadd.5. The pharmaceutical composition according to claim 4 comprising an individual isomer of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione tartaric acid salt or a tautomer of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione tartaric acid salt..Iaddend.

.Iadd.6. The pharmaceutical composition according to claim 4 comprising a mixture of isomers of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]hiazolidine-2,4-dione tartaric acid salt or a tautomer of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione tartaric acid salt..Iaddend.

.Iadd.7. The pharmaceutical composition according to any one of claims 4 to 6, wherein the composition is in a form suitable for oral administration..Iaddend.

.Iadd.8. The pharmaceutical composition according to claim 7, wherein the form is chosen from tablets, capsules, and powders..Iaddend.

.Iadd.9. The pharmaceutical composition according to claim 7, wherein the form is a tablet..Iaddend.

.Iadd.10. The pharmaceutical composition according to claim 4, wherein the composition is in a form suitable for injection..Iaddend.

.Iadd.11. The pharmaceutical composition according to claim 4, wherein the composition is in a form suitable for percutaneous absorption..Iaddend.

.Iadd.12. The pharmaceutical composition according to claim 4, wherein the at least one pharmaceutically acceptable carrier is chosen from microcrystalline cellulose, starch, sodium starch glycollate, polyvinylpyrrolidone, polyvinylpolypyrrolidone, magnesium stearate, and sodium lauryl sulphate..Iaddend.

.Iadd.13. The pharmaceutical composition according to claim 4, wherein the at least one pharmaceutically acceptable carrier comprises a diluent, filler, disintegrant, wetting agent, lubricant, colourant, flavourant, or adjuvant..Iaddend.
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