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Claims for Patent: 7,358,366

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Claims for Patent: 7,358,366

Title:Thiazolidinedione derivative and its use as antidiabetic
Abstract:A polymorphic form of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione- , maleic acid salt (the "Polymorph") characterised in that it provides: (i) an infra red spectrum containing peaks at 1752, 1546, 1154, 621, and 602 cm.sup.-1; and/or (ii) a Raman spectrum containing peaks at 1751, 1243 and 602 cm.sup.-1; and/or (iii) a solid-state nuclear magnetic resonance spectrum containing peaks at 111.9, 114.8, 119.6, 129.2, 134.0, 138.0, 144.7, 153.2, 157.1, 170.7, 172.0, and 175.0 ppm; and/or (iv) an X-ray powder diffraction (XRPD) pattern which gives calculated lattice spacings of 6.46, 5.39, 4.83, 4.68, 3.71, 3.63, 3.58, and 3.48 Angstroms; a process for preparing such a compound, a pharmaceutical composition containing such a compound and the use of such a compound in medicine.
Inventor(s): Blackler; Paul David James (Cadiz, ES), Giles; Robert Gordon (Tonbridge, GB), Moore; Stephen (Tonbridge, GB), Sasse; Michael John (Tonbridge, GB)
Assignee: SmithKline Beecham p.l.c. (Brentford, Middlesex, GB)
Application Number:11/458,471
Patent Claims: 1. A crystalline 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione maleic acid salt which provides at least one of: (i) an infra red spectrum containing peaks at 1752, 1546, 1154, 621, and 602 cm.sup.-1; (ii) a Raman spectrum containing peaks at 1751, 1243 and 602 cm.sup.-1; (iii) a solid-state .sup.13C nuclear magnetic resonance spectrum containing peaks at 111.9, 114.8, 119.6, 129.2, 134.0, 138.0, 144.7, 153.2, 157.1, 170.7, 172.0 and 175.0 ppm; and (iv) an X-ray powder diffraction pattern which gives calculated lattice spacings of 6.46, 5.39, 4.83, 4.68, 3.71, 3.63, 3.58, and 3.48 Angstroms.

2. A crystalline 5-[4-[2-(N-methyl-N-(2-pyridyl) amino)ethoxy]benzyl]thiazolidine-2,4-dione maleic acid salt which provides each of: (i) an infra red spectrum containing peaks at 1752, 1546, 1154, 621, and 602 cm.sup.-1; (ii) a Raman spectrum containing peaks at 1751, 1243 and 602 cm.sup.-1; (iii) a solid-state .sup.13C nuclear magnetic resonance spectrum containing peaks at 111.9, 114.8, 119.6, 129.2, 134.0, 138.0, 144.7, 153.2, 157.1, 170.7, 172.0 and 175.0 ppm; and (iv) an X-ray powder diffraction pattern which gives calculated lattice spacings of 6.46, 5.39, 4.83, 4.68, 3.71, 3.63, 3.58, and 3.48 Angstroms.

3. A crystalline 5-[4-[2-(N-methyl-N-(2-pyridyl) amino)ethoxy]benzyl]thiazolidine-2,4-dione maleic acid salt, which, in a mineral oil dispersion, provides an infra red spectrum substantially in accordance with FIG. 1.

4. A crystalline 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione maleic acid salt, which provides a Raman spectrum substantially in accordance with FIG. 2.

5. A crystalline 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione maleic acid salt, which provides a solid-state .sup.13C nuclear magnetic resonance spectrum substantially in accordance with FIG. 3.

6. A crystalline 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione- , maleic acid salt, which provides an X-ray powder diffraction pattern substantially in accordance with FIG. 4.

7. A crystalline 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione maleic acid salt, which provides a solid-state .sup.13C nuclear magnetic resonance spectrum having absorbances at 38.0, 49.4, 51.9, 57.6, 62.8, 111.9, 114.8, 119.6, 129.2, 134.0, 138.0, 144.7, 153.2, 157.1, 170.7, 172.0, 175.0 +/- 0.5 ppm.

8. A crystalline 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione maleic acid salt, which provides an X-ray powder diffraction pattern having peaks with diffraction angles and calculated lattice spacings as follows: TABLE-US-00004 Diffraction Angles (.degree.2.theta.) Lattice Spacings (Angstroms) 9.2 9.63 11.6 7.65 12.3 7.17 13.7 6.46 14.0 6.32 14.7 6.03 14.9 5.95 15.3 5.77 16.4 5.39 18.4 4.83 18.7 4.74 19.0 4.68 19.3 4.59 20.0 4.44 21.0 4.22 21.9 4.07 22.5 3.94 23.3 3.81 24.0 3.71 24.5 3.63 24.9 3.58 25.6 3.48 26.2 3.40 27.2 3.28 27.7 3.22 28.7 3.11 29.2 3.05 29.6 3.02 30.2 2.96 30.8 2.90 31.0 2.88 31.7 2.82 32.3 2.77 32.9 2.72 33.4 2.68 34.2 2.62.
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