Smithkline Beecham Corporation

Michael John Sasse

Paul David James Blackler

David C Lee

Robert Gordon Giles

Stephen Moore

Ian Robert Lynch

Bernadette Marie Choudary

A hydrate of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, maleic acid salt., characterized in that it:

Substituted thiazolidinedione derivative, process for its preparation and its pharmaceutical use

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; and/or (ii) a Raman spectrum containing peaks at 1751, 1243 and 602 cm; 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.

Thiazolidinedione derivative and its use as antidiabetic

A hydrate of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, maleic acid salt, characterized in that it: (i) comprises water in the range of from 0.4 to 2.5% w/w; and (ii) provides an infra red spectrum containing peaks at 1749, 1703, 1645, 1623, 1365 and 736 cm; and/or (iii) provides an X-ray powder diffraction (XRPD) pattern substantially as set out in FIG. II and/or (iv) provides a Raman spectrum containing peaks at 3106, 3069, 3002, 2961, 1750, 1718, 1684, 1385, 1335, 1229, 1078, 917, 428 and 349 cmand/or (iv) provides a solid-state nuclear magnetic resonance spectrum containing chemical shifts substantially as set out in Table I; a process for the preparation of such a compound, a pharmaceutical composition containing such a compound and the use of such a compound or composition in medicine.

5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2, 4-dione, maleic acid salt, hydrate as pharmaceutical

A hydrate of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, maleic acid salt, characterized in that it: (i) comprises water in the range of from 0.2 to 1.1% w/w; and (ii) provides an infrared spectrum containing peaks at 764 and 579 cm; and/or (iii) provides an X-ray powder diffraction (XRPD) pattern substantially as set out in FIG. II; a process for the preparation of such a compound, a pharmaceutical composition containing such a compound and the use of such a compound or composition in medicine.

Hydrate of 5-[4-[2-(N-methyl-N-(2-pyridil)amino)ethoxy]benzyl]thiazolidine-2,4-dione maleic acid salt

A polymorphic form of 5-&lsqb;4-&lsqb;2-(N-methyl-N-(2-pyridyl)amino)ethoxy&rsqb;-benzyl&rsqb;thiazolidine-2,4-dione, maleic acid salt (the &ldquo;Polymorph&rdquo;) characterized in that it: (i) provides an infra red spectrum containing peaks at 1360, 1326, 1241, 714 and 669 cm ; and/or (ii) provides a Raman spectrum containing peaks at 1581, 768, 670, 271 and 226 cm ; and/or (iii) provides a solid-state nuclear magnetic resonance spectrum containing peaks at chemical shifts substantially as set out in Table I; and/or (iv) provides an X-ray powder diffraction (XRPD) pattern containing peaks substantially as set out in Table II; a process for preparing such a compound, a pharmaceutical composition containing such a compound and the use of such a compound in medicine.

The present invention provides a novel hydrate of 5-&lsqb;4-&lsqb;2-(N-methyl-N-(2-pyridyl)amino)ethoxy&rsqb;benzyl&rsqb;thiazolidine-2,4-dione, maleic acid.

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Tunbridge Wells, United Kingdom

Michael John Sasse