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Claims for Patent: 8,426,389

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Claims for Patent: 8,426,389

Title:Crystalline form of R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-hydroxy- methyl oxazolidin-2-one dihydrogen phosphate
Abstract: A crystalline form of crystalline (R)-3-(4-(2-(2-methyltetrazol-5-yl)-pyridin-5-yl)-3-fluorophenyl)-5-hydro- xymethyl oxazolidin-2-one dihydrogen phosphate, methods of making the crystalline form and pharmaceutical compositions comprising the crystalline form are useful antibiotics. Further, the derivatives of the present invention may exert potent antibacterial activity versus various human and animal pathogens, including Gram-positive bacteria such as Staphylococi, Enterococci and Streptococi , anaerobic microorganisms such as Bacteroides and Clostridia, and acid-resistant microorganisms such as Mycobacterium tuberculosis and Mycobacterium avium. Accordingly, the compositions comprising the crystalline form may be used in antibiotics.
Inventor(s): Reichenbacher; Katharina (Riehen, CH), Duguid; Robert J. (Glenmont, NY), Ware; Jacqueline A. (Troy, NY), Phillipson; Douglas (Del Mar, CA)
Assignee: Trius Therapeutics, Inc. (San Diego, CA)
Application Number:12/699,864
Patent Claims: 1. Crystalline particles comprising at least about 96% by weight of (R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluoro-phenyl)-5-hydro- xymethyl oxazolidin-2-one dihydrogen phosphate, wherein the remainder of the crystalline particles comprises at least one compound selected from the group consisting of ##STR00022## wherein the median volume diameter of the crystalline particles is at least about 1.0 .mu.m; 90% of the total particle volume of the particles has an average diameter of at least about 45 .mu.m; and/or 10% of the total particle volume of the particles has an average diameter of at least about 0.5 .mu.m; and wherein the crystalline particles have an X-ray powder diffraction pattern comprising the following peaks: 14.7.degree., 15.2.degree., 16.6.degree., 20.3.degree., 26.8.degree., and 28.2.degree..

2. The purified crystalline particles of claim 1 further comprising less than 1% by weight of (R)-5-(chloromethyl)-3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-- 3-yl)phenyl)oxazolidin-2-one having the following structure: ##STR00023##

3. The crystalline particles of claim 2 comprising at least about 97% by weight of (R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl- )-5-hydroxymethyl oxazolidin-2-one dihydrogen phosphate.

4. The crystalline particles of claim 1 further comprising less than 1% by weight of a compound having the following structure: ##STR00024##

5. The crystalline particles of claim 4 comprising at least about 97% by weight of (R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl- )-5-hydroxymethyl oxazolidin-2-one dihydrogen phosphate.

6. Crystalline particles comprising at least about 96% by weight of (R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluoro-phenyl)-5-hydro- xymethyl oxazolidin-2-one dihydrogen phosphate; and at least one compound selected from the group consisting of ##STR00025## wherein the crystalline particles have an X-ray powder diffraction pattern comprising the following peaks: 14.7.degree., 15.2.degree., 16.6.degree., 20.3.degree., 26.8.degree., and 28.2.degree..

7. The crystalline particles of claim 1, wherein the median volume diameter is at least about 1.0 .mu.m.

8. The crystalline particles of claim 1, characterized by a DSC pattern having endo-endo peaks at about 255-258.degree. C.

9. A pharmaceutical composition comprising the crystalline particles of claim 1 and at least one pharmaceutically acceptable carrier, excipient or diluent; wherein the crystalline particles are crystalline particles in the pharmaceutical composition.

10. The pharmaceutical composition of claim 9 wherein the pharmaceutically acceptable carrier, excipient or diluent is at least one member selected from the group consisting of mannitol, polyvinylpyrrolidone, cross-linked polyvinylpyrrolidone, and magnesium stearate.

11. A reaction mixture comprising the crystalline particles of claim 6 and a base.

12. The reaction mixture of claim 11, wherein the base is sodium hydroxide.

13. A pharmaceutical composition comprising a lyophilisate of the reaction mixture of claim 11, comprising ##STR00026## wherein R.dbd.PO(ONa).sub.2.

14. A pharmaceutical composition comprising a combination of at least about 96% by weight of a compound having the following structure: ##STR00027## wherein R.dbd.PO(ONa).sub.2; and wherein the remainder of the combination comprises at least one salt of a compound selected from the group consisting of: ##STR00028## ##STR00029## at least one pharmaceutically acceptable carrier, excipient or diluent.

15. The pharmaceutical composition of claim 14 wherein the combination further comprises less than 1% by weight of ##STR00030##

16. The pharmaceutical composition of claim 15 wherein the combination comprises at least about 97% by weight of ##STR00031## wherein R.dbd.PO(ONa).sub.2.

17. The pharmaceutical composition of claim 14 wherein the combination further comprises less than 1% by weight of ##STR00032##

18. The pharmaceutical composition of claim 17 wherein the combination comprises at least about 97% by weight of ##STR00033## wherein R.dbd.PO(ONa).sub.2.

19. A method of treating a bacterial infection comprising administering an effective amount of the crystalline particles of claim 1 to a subject in need thereof.

20. A method of treating a bacterial infection comprising administering an effective amount of the pharmaceutical composition of claim 14 to a subject in need thereof.

21. A process for making the crystalline particles of claim 6, comprising drying the crystalline particles.

22. The process of claim 21 further comprising filtering the crystalline particles from a supernatant before the drying step.

23. The process of claim 22 further comprising immediately contacting a salt of crystalline (R)-3-(4-(2-(2-methyltetrazol-5-yl)-pyridin-5yl)-3-fluorophenyl)-5-hydrox- ymethyl oxazolidin-2-one dihydrogen phosphate with an acid solution to form crystallized (R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-hydrox- ymethyl oxazolidin-2-one dihydrogen phosphate before the filtering step.

24. The process of claim 23 wherein the acid solution comprises HCl and ethanol, or HCl and THF.

25. A process for making the crystalline particles of claim 1, comprising drying the crystalline particles.

26. A pharmaceutical composition comprising the crystalline particles of claim 6 and at least one pharmaceutically acceptable carrier, excipient or diluent; wherein the crystalline particles are crystalline particles in the pharmaceutical composition.

27. A method of treating a bacterial infection comprising administering an effective amount of the crystalline particles of claim 6 to a subject in need thereof.
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