Patent EA-005110-B1 (EA)
Title: 5-[4-[2-(n-methyl-n-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione potassium salt and its use as antidiabetic
Inventor: MILLAN MICHAEL
IPC: A61K31/4439
Filed: 2001-09-28
Abstract: 1. A compound 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione potassium salt or a pharmaceutically acceptable solvate thereof, characterised in that it provides one or more of: (i) an infrared spectrum substantially in accordance with Figure 1; (ii) a Raman spectrum substantially in accordance with Figure 2; (iii) an X-Ray powder diffraction pattern (XRPD) substantially in accordance with Table 1 or Figure 3; and (iv) a Solid State <13>C NMR spectrum substantially in accordance with Figure 4; and (v) a melting point in the range of 194 to 201 degree C. 2. A compound according to claim 1, characterised in that it provides two or more of: (i) an infrared spectrum substantially in accordance with Figure 1; (ii) a Raman spectrum substantially in accordance with Figure 2; (iii) an X-Ray powder diffraction pattern (XRPD) substantially in accordance with Table 1 or Figure 3; and (iv) a Solid State <13>C NMR spectrum substantially in accordance with Figure 4. 3. A compound according to claim 1, in a solid dosage form. 4. A compound according to claim l or claim 2, in a bulk milled form. 5. A pharmaceutical composition comprising 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione potassium salt (the Potassium Salt) or a pharmaceutically acceptable solvate thereof, according to claim 1, wherein the Potassium Salt is present in an amount providing 1, 2, 3, 4, 4 to 8 or 8 to 12 mg of 5-[4-[2(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione and a pharmaceutically acceptable carrier therefor. 6. A pharmaceutical composition according to claim 5, comprising the Potassium Salt or a pharmaceutically acceptable solvate thereof in an amount providing 1,2,3 or 4 mg of 5-[4-[2-(N-methyl-N-(2-pyridyl) amino) ethoxy] benzyl] thiazolidine-2,4-dione. 7. A pharmaceutical composition according to claim 5, comprising the Potassium Salt or a pharmaceutically acceptable solvate thereof in an amount providing 2 mg of 5-[[2-(N-methyl-N-(2-pyridyl) amino) ethoxy] benzyl]thiazolidine-2,4-dione. 8. A pharmaceutical composition according to claim 5, comprising the Potassium Salt or a pharmaceutically acceptable solvate thereof in an amount providing 4 mg of 5-[4-[2-(N-methyl-N-(2-pyridyl) amino) ethoxy] benzyl]thiazolidine-2, 4-dione. 9. A pharmaceutical composition according to claim 5, in an amount providing 8 mg of 5-[4-[2- (N-methyl-N-(2-pyridyl) amino) ethoxy] benzyl] thiazolidine-2,4-dione. 10. A pharmaceutical composition comprising 5-[4-[2-(N-methyl-N-(2-pyridyl) amino) ethoxy] benzyl] thiazolidine-2,4-dione potassium salt or a pharmaceutically acceptable solvate thereof according to claim 1 in combination with one or more other anti-diabetic agents and optionally a pharmaceutically acceptable carrier therefor. 11. A method for the treatment and/or prophylaxis of diabetes mellitus, conditions associated with diabetes mellitus and certain complications thereof, in a human or non-human mammal which comprises administering an effective, non-toxic, amount of [4-[2-(N-methyl-N-(2-pyridyl) amino) ethoxy] benzyl] thiazolidine-2,4-dione potassium salt or a pharmaceutically acceptable solvate thereof according to claim 1 to a human or non-human mammal in need thereof, wherein the Potassium Salt is present in an amount providing 1, 2, 3, 4, 4 to 8 or 8 to 12 mg of 5-[4-[2-(N-methyl-N-(2-pyridyl) amino) ethoxy] benzyl] thiazolidine-2,4-dione. 12. A method for the treatment and/or prophylaxis of diabetes mellitus, conditions associated with diabetes mellitus and certain complications thereof, in a human or non-human mammal which comprises administering an effective, non-toxic, amount of 5-[4-[2-(N-methyl-N-(2-pyridyl) amino) ethoxy] benzyl] thiazolidine-2,4-dione potassium salt or a pharmaceutically acceptable solvate thereof according to claim 1 in combination with one or more other antidiabetic agents. 13. A compound 5-[4-[2-(N-methyl-N-(2-pyridyl) amino) ethoxy] benzyl] thiazolidine-2,4-dione potassium salt or a pharmaceutically acceptable solvate thereof according to claim 1 for use as an active therapeutic substance. 14. A use of 5-[4-[2-(N-methyl-N-(2-pyridyl) amino) ethoxy] benzyl] thiazolidine-2,4-dione potassium salt or a solvate thereof according to claim 1, in an amount providing 1, 2, 3, 4, 4 to 8 or 8 to 12 mg of 5-[4-[2-(N-methyl-N-(2pyridyl) amino) ethoxy] benzyl] thiazolidine-2,4-dione for the manufacture of a medicament for the treatment and/or prophylaxis of diabetes mellitus, conditions associated with diabetes mellitus and certain complications thereof.