N-[5-(aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)-phenyl]-acetamide free base hemihydrate, methods of manufacture and uses thereof

1 - 11 . (Canceled).

12 . A N-[5-(amino-sulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamide free base hemihydrate having the molecular formula C 18 H 18 N 4 O 3 S 2 x 0.5 H 2 O.

13 . The N-[5-(amino-sulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamide free base hemihydrate of claim 1 , which has a relative molecular mass of M r 411.50.

14 . The N-[5-(amino-sulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamide free base hemihydrate of claim 1 , which comprises XRPD peaks at 5.9, 11.7, 15.5 and 18.7 2theta.

15 . The N-[5-(amino-sulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamide free base hemihydrate of claim 1 which has a melting point of 205° C. to 211° C.

16 . The N-[5-(amino-sulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamide free base hemihydrate of claim 1 which has a calculated pKa value of 4.53.

17 . The N-[5-(amino-sulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamide free base hemihydrate of claim 1 which has an octanol/water partition coefficient of 0.911±0.891 at 25° C.

18 . The N-[5-(amino-sulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamide free base hemihydrate of claim 1 which has a stability at a pH in the range of 4.5 to 7.0 of 90-100%.

19 . A pharmaceutical composition comprising N-[5-(amino-sulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamide free base hemihydrate of claim 1 wherein said composition further comprises at least one pharmaceutically acceptable excipient.

20 . A method of treating or preventing herpes virus infections comprising administering an effective amount of the pharmaceutical composition of claim 8 to a patient in need thereof.

21 . A medicament comprising N-[5-(amino-sulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamide free base hemihydrate.

22 . A method of manufacturing N-[5-(amino-sulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamide free base hemihydrate having the molecular formula C 18 H 18 N 4 O 3 S 2 x 0.5 H 2 O, wherein said method comprises

coupling (4-pyridine-2-yl-phenyl)-acetic acid and aminothiazole sulfonic acid amide using standard reaction conditions (N-Ethyl-N′-(3-dimethylaminopropyl)-carbodiimide hydrochloride (EDC x HCl), tetrahydrofuran (THF)/N-methylpyrrolidone (NMP), and

recrystallizing N-[5-(amino-sulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamide free base hemihydrate from THF/water.

23 . The method of claim 11 , wherein said method additionally comprises:

a) Mixing (4-pyridine-2-yl-phenyl)-acetic acid and aminothiazole sulfonic acid amide in N-Methylpyrrolidone (NMP);

b) Cooling the mixture obtained in step a);

c) Adding N-Ethyl-N′-(3-dimethylaminopropyl)-carbodiimide hydrochloride (EDC x HCl) to said mixture obtained in step b);

d) Stirring the solution obtained in step c) and addition to purified H 2 O;

e) Filtering the solution obtained in step d);

f) Washing the product cake obtained in step e);

g) Drying the product obtained in step f);

h) Adding H 2 O to the solution obtained in step g);

i) Stirring the suspension obtained in step h);

j) Cooling the suspension obtained in step i);

k) Stirring the suspension obtained in step j);

l) Isolating the product by filtration of the suspension obtained in step k);

m) Washing the product obtained in step 1) with H 2 O;

n) Drying the product obtained in step m).

24 . The method of claim 12 , wherein step g) further comprises dissolving the dried product in a mixture of THF and water.

25 . The method of claim 12 , wherein the drying in step n) is at 65° C. under vacuum until the criterion for water content is reached.

26 . A pharmaceutical composition comprising a free base hemihydrate of N-[5-(aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamide obtained by the method of claim 11 .