BACKGROUND OF THE INVENTION US 5, 216,167 discloses 2-ethoxy-4-{[3-methyl-1-(2-piperidin- 1-yl-phenyl)-butylcarbamoyl]-methyl}-benzoic acid. The compound exhibits blood-glucose lowering action with lower toxicity, and may be safely administered, orally or parenterally, as it is or advantageously as a pharmaceutical composition comprising an effective amount of the compound or its pharmacologically acceptable salt and a pharmacologically acceptable carrier, excipient or diluent therefor, in the form of powder, granule, tablet, hard capsule, soft capsule, dry syrup, suppository, injection or the like.

. US 6,143, 769 discloses (S)-(+)-2-ethoxy-4-{[3-methyl-1-(2- <BR> <BR> <BR> <BR> pi peridin-t-yl-phenyl)-butylcarbamoyl]-methyl}-benzoic acid which is currently marketed for treatment of Type II diabetes.

The present invention discloses a novel salt of 2-ethoxy-4- {[3-methyl-1-(2-piperidin-1-yl-phenyl)-butylcarbamoyl]-methy l}- benzoic acid or (S)-(+)-2-Ethoxy-4-{[3-methyl-t-(2-piperidin-t-yl-

phenyl)-butylcarbamoyl]-methyl}-benzoic acid, namely sodium salt of 2-ethoxy-4-{[3-methyl-1-(2-piperidin-1-yl-phenyl)- butylcarbamoyl]-methyl}-benzoic acid or sodium salt of (S)- (+)-2- <BR> <BR> <BR> <BR> Ethoxy-4-{[3-methyl-t-(2-piperidin-t-yl-phenyl)-butylcarbamo yl]- methyl}-benzoic acid (FORMULA I), which is useful in the, treatment of Type II diabetes. This compound shows good stability in solid form. Also this compound is significantly soluble in water or aqueous media whereas the free acid, namely (S)- (+)-2-ethoxy-4- {[3-methyl-1-(2-piperidin-1-yl-phenyl)-butylcarbamoyl]-methy l}- benzoic acid, is practically insoluble in water.

SUMMARY OF THE INVENTION The present invention relates to a novel compound of formula I, which is sodium salt of 2-ethoxy-4-{[3-methyl-1-(2-piperidin-1-yl- phenyl)-butylcarbamoyl]-methyl}-benzoic acid or sodium salt of (S)-(+)-2-ethoxy-4-{[3-methyl-1-(2-piperidin-1-yl-phenyl)- butylcarbamoyl]-methyl}-benzoic acid (FORMULA I), to a novel process for preparing this compound, to a pharmaceutical composition containing this compound and to the prophylactic and/or therapeutic use of the compound and composition.

FORMULA I

The present invention provides a compound of formula I, for use in the treatment of and/or prophylaxis of hyperglycemia.

The stability and water solubility of this compound provides for significant advantages in formulation, bioavailability and bulk handling.

DETAILED DESCRIPTION OF THE INVENTION Accordingly, the present invention provides a novel compound of formula I.

FORMULA I The compound of formula I is sodium salt of 2-ethoxy-4-{[3- methyl-1-(2-piperidin-1-yl-phenyl)-butylcarbamoyl]-methyl}- benzoic acid or sodium salt of (S)-(+)-2-ethoxy-4-{[3-methyl-1-(2- piperidin-1-yl-phenyl)-butylcarbamoyl]-methyl}-benzOic acid.

The currently marketed (S)-(+)-2-ethoxy-4-{[3-methyl-1-(2- piperidin-l-yl-phenyl)-butylcarbamoyl]-methyl}-benzOic acid is insoluble in water (The Merck Index Online, 2003).

The compound of present invention is freely soluble in water.

This has significant pharmacokinetic advantage and enhances bioavailability.

As stated the compound of the invention is significantly soluble in water and aqueous media. A convenient method for determining the stability of the compounds of the invention in

aqueous solution involves determining the degree of precipitation of the parent free base from an aqueous solution of the test compound at known conditions of temperature and over known periods of time. We have found that the compound of formula I show good stability in aqueous conditions.

The quantitative analysis of the test may be carried out using conventional methods e. g. HPLC.

As mentioned above the compound of the invention is indicated as having useful therapeutic properties.

The present invention accordingly provides a compound of formula I, for use as an active therapeutic substance.

Thus the present invention provides a compound of formula I, for use in the treatment of and/or prophylaxis of hyperglycemia.

Accordingly, the present invention also provides a pharmaceutical composition comprising a compound of formula I and a pharmaceutically acceptable carrier therefor.

Usually the pharmaceutical compositions of the present invention will be adapted for oral administration, although compositions for administration by other routes, such as by injection and percutaneous absorption are also envisaged.

Particularly suitable compositions for oral administration are unit dosage forms such as tablets and capsules. Other fixed unit dosage forms, such as powders presented in sachets, may also be used.

The present invention further provides a method for the treatment and/or prophylaxis of hyperglycemia in a human or non- human mammal, which comprises administering an effective, non-

toxic, amount of a compound of formula I, to a hyperglycemic human or non-human mammal in need thereof.

The compound of formula I is obtained by the reaction between (S)-(+)-2-ethoxy-4-{[3-methyl-1-(2-piperidin-1-yl-phenyl)- butylcarbamoyl]-methyl}-benzoic acid and a source of sodium counter-ion. The reaction is generally carried out under conventional salt forming conditions, for example by admixing (S)- (+)-2-ethoxy-4-{[3-methyl-t-(2-piperidin-1-yl-phenyl)- butylcarbamoyl]-methyl}-benzoic acid and the suitable source of counter-ion, e. g. sodium methoxide, sodium hydroxide, sodium carbonate, sodium bicarbonate, in approximately equimolar amounts but preferably using an excess of the source of counter- ion, in a suitable solvent, generally a Cl-4 alkanolic solvent such as methanol, ethanol, other aprotic solvents like acetonitrile or water immiscible organic solvent like ethyl acetate or isobutyl acetate, at a temperature which provides a suitable rate of formation of the required product, generally at an elevated temperature and thereafter isolating the product.

The following Example illustrates the invention but does not limit it in any way.

EXAMPLES Example 1 To a solution of (S)-(+)-2-ethoxy-4-{[3-methyl-1-(2-piperidin- t-yl-phenyl)-butylcarbarnoyl]-methyl}-benzoic acid (S 9, 0.011 mol) in ethyl acetate (50 mi), sodium methoxide (0.6 g, 0.011 mol) was added. After stirring for 3 hours, the reaction mixture was filtered to afford title compound.

Example 2 To a solution of (S) r (+)-2-ethoxy-4-{[3-methyl-1-(2-piperidin- l-yl-phenyl)-butylcarbamoyl]-methyl}-benzoic acid (100 g, 0.22 mol) in acetonitrile (500 ml), sodium methoxide (12 g, 0.22 mol) was added. After stirring for 2 hours, the reaction mixture was filtered to afford title compound.

Example 3 To a solution of (S)-(+)-2-ethoxy-4-{[3-methyl-t-(2-piperidin- 1-yl-phenyl)-butylcarbamoyl]-methyl-benzoic acid (100 g, 0.22 mol) in isobutyl acetate (500 ml), sodium methoxide. (12 g, 0.22 mol) was added. After stirring for3 hours, the reaction mixture was filtered to afford title compound.

Example 4 To a solution of 2-ethoxy-4-{[3-methyl-1-(2-piperidin-1-yl- phenyl)-butylcarbamoyl]-methyl}-benzoic acid (5 g, 0.011 mol) in ethyl acetate (50 ml), sodium carbonate (1. 2 g, 0.011 mol) was added. After stirring for 3 hours, the reaction mixture was filtered to afford title compound.

Example 5 To a solution of 2-ethoxy-4-{[3-methyl-1-(2-piperidin-1-yl- phenyl)-butylcarbamoyl]-methyl}-benzoic acid (5 g, 0.011 mol) in methanol (50 ml), a solution of sodium hydroxide (0.44 g, 0. 011 mol) in methanol (10 ml) was added. After stirring for 1 hour, the reaction mixture was concentrated and ethyl acetate (25 ml) was added under stirring. The mixture was filtered to afford title compound.