NOVEL SALT 628

• US 20100216843A1
• Filed: 02/16/2010
• Published: 08/26/2010
• Est. Priority Date: 02/20/2009
• Status: Active Grant

• Current Assignee: Astrazeneca AB (Astrazeneca PLC)
• Original Assignee: Astrazeneca A B
• Inventors: Watts, Andrew James, Briggner, Lars-Erik, Zuban, Robert, Alcaraz, Marie-Lyne, Lönn, Hans Roland, Klingstedt, Per Thomas, Nixon, Robert Anthony
• Granted Patent: US 8,232,296 B2
• Time in Patent Office: Days
• US Class Current: 514/333
• CPC Class Codes: A61P 11/00 Drugs for disorders of the respiratory system
• CPC Class Codes: A61P 11/08 Bronchodilators
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07D 401/14 containing three or more hetero rings

Abstract

6-Methyl-5-(1-methyl-1H-pyrazol-5-yl)-N-{[5-(methylsulfonyl)pyridin-2-yl]methyl}-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide 4-methylbenzenesulfonate and a novel crystalline form thereof are disclosed together with processes for preparing such salt and form, pharmaceutical compositions comprising such a salt and form, and the methods of treatment using such a salt and form.

Claims

1. The compound 6-methyl-5-(1-methyl-1H-pyrazol-5-yl)-N-{[5-(methylsulfonyl)pyridin-2-yl]methyl}-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide 4-methylbenzenesulfonate Form A.

2. The compound according to claim 1 wherein said Form A has an X-ray powder diffraction pattern measured using CuK_α

radiation with at least one specific peak at 2θ

=about 5.1, 7.3, 8.9, 17.0 or 17.8°

.

3. The compound according to claim 1 wherein said Form A has an X-ray powder diffraction pattern measured using CuK_α

radiation with specific peaks at 2θ

=about 5.1, 7.3, 8.9, 17.0 and 17.8°

.

4. The compound according to claim 1 wherein said Form A has an X-ray powder diffraction pattern measured using CuK_α

radiation substantially the same as that shown in FIG. 1.

5. A pharmaceutical composition comprising a compound according to claim 1 in admixture with a pharmaceutically acceptable diluent or carrier.

6. A pharmaceutical composition comprising a compound according to claim 1 and dibasic calcium phosphate.

7. A pharmaceutical composition comprising a compound according to claim 1;

dibasic calcium phosphate; and

microcrystalline cellulose.

8. A pharmaceutical composition comprising a compound according to claim 1;

40% by weight or less dibasic calcium phosphate; and

microcrystalline cellulose.

9. A pharmaceutical composition comprising:

a) 0.1 to 40 parts of a compound according to claims 1;

b) 2 to 10 parts dibasic calcium phosphate;

c) 60 to 90 parts microcrystalline cellulose;

d) 2 to 10 parts of a disintegrant;

e) 0.1 to 2 parts of a surfactant; and

f) 0.1 to 3 parts of a lubricant;

wherein all parts are parts by weight of the total composition and the sum of the parts a) to f)=100.

10. A pharmaceutical composition according to any one of claims 5 to 9, which is an instant release pharmaceutical composition for oral administration.

11. A pharmaceutical composition according to claim 10 further comprising a coating.

12. A method of treating, or reducing the risk of, an inflammatory disease or condition, which comprises administering to a person suffering from or at risk of, said disease or condition, a therapeutically effective amount of a compound according to claim 1.

13. A method of treating chronic obstructive pulmonary disease (COPD), which comprises administering to a person suffering from said disease, a therapeutically effective amount of a compound according to claim 1.

14. A method of treating bronchiectasis, which comprises administering to a person suffering from bronchiectasis, a therapeutically effective amount of a compound according to claim 1.

15. A method of treating cystic fibrosis, which comprises administering to a person suffering from cystic fibrosis, a therapeutically effective amount of a compound according to claim 1.

16. A process for the preparation of a compound according to claim 1 comprising crystallisation of said Form A from a solvent selected from acetonitrile, tetrahydrofuran, cyclohexanone, butan-1-ol, butyronitrile, methyl isobutyl ketone, methyl ethyl ketone and acetone.