Levodopa prodrug mesylate, compositions thereof, and uses thereof

1. A compound, crystalline (2R)-2-phenylcarbonyloxypropyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate mesylate.

2. The compound of claim 1 , having characteristic peaks (°2θ) at 5.0±0.2°, 8.5±0.2°, 13.6±0.2°, 15.0±0.2°, 17.0±0.2°, 17.7±0.2°, 20.4±0.2°, 21.1±0.2°, 25.0±0.2°, 25.8±0.2°, 28.2±0.2°, 30.1±0.2°, and 37.6±0.2° in an X-ray powder diffraction pattern measured using Cu Kα radiation.

3. The compound of claim 1 , wherein the compound is characterized by a differential scanning calorimetry thermogram having an endothermic peak at about 164.5±2.5° C.

4. A pharmaceutical composition comprising a pharmaceutically acceptable vehicle and a therapeutically effective amount of the compound of claim 1 .

5. The pharmaceutical composition of claim 4 , and at least one other diastereomer of crystalline 2-phenylcarbonyloxypropyl-2-amino-3-(3,4-dihydroxyphenyl)propanoate mesylate wherein the diastereomeric purity of crystalline (2R)-2-phenylcarbonyloxypropyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate mesylate is at least about 90%.

6. The pharmaceutical composition of claim 4 , comprising an L-aromatic amino acid decarboxylase inhibitor.

7. The pharmaceutical composition of claim 4 , comprising a catechol-O-methyltransferase inhibitor.

8. The pharmaceutical composition of claim 4 , formulated for sustained release oral administration.

9. The compound of claim 1 , having characteristic diffraction peaks(°2θ)at 4.7±0.2°, 5.0±0.2°, 8.5±0.2°, 9.6±0.2°, 13.6±0.2°, 15.0±0.2°, 17.0±0.2°, 17.4±0.2°, 17.7±0.2°, 19.1±0.2°, 19.5±0.2°, 20.0±0.2°, 20.4±0.2°, 21.1±0.2°, 22.3±0.2°, 22.9±0.2°, 23.1±0.2°, 23.3±0.2°, 24.3±0.2°, 25.0 ±0.2°, 25.3±0.2°, 25.7±0.2°, 25.8±0.2°, 26.9±0.2°, 27.3±0.2°, 28.2±0.2°, 30.1±0.2°, 30.5±0.2°, 32.0±0.2°, 33.8±0.2°, 34.3±0.2°, 37.6±0.2°, and 38.4±0.2° in an X-ray powder diffraction pattern measured using Cu Kα radiation.

10. The compound of claim 1 wherein the compound is characterized by a differential scanning calorimetry thermogram having an endothermic peak at 165.8±1.1° C. at a scan rate of 10° C./min or 15° C./min.

11. The compound of claim 1 , wherein the compound exhibits a melting point from about 157° C. to about 162° C.

12. The compound of claim 1 , wherein the compound exhibits a melting point from 160.5° C. to 161.3° C.

13. The pharmaceutical composition of claim 4 , and at least one other diastereomer of crystalline 2-phenylcarbonyloxypropyl-2-amino-3-(3,4-dihydroxyphenyl)propanoate mesylate wherein the diastereomeric purity of crystalline (2R)-2-phenylcarbonyloxypropyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate mesylate is at least about 95%.

14. The pharmaceutical composition of claim 4 , and at least one other diastereomer of crystalline 2-phenylcarbonyloxypropyl-2-amino-3-(3,4-dihydroxyphenyl)propanoate mesylate wherein the diastereomeric purity of crystalline (2R)-2-phenylcarbonyloxypropyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate mesylate is at least about 99%.

15. The pharmaceutical composition of claim 4 , and at least one other diastereomer of crystalline 2-phenylcarbonyloxypropyl-2-amino-3-(3,4-dihydroxyphenyl)propanoate mesylate wherein the compositional purity of crystalline (2R)-2-phenylcarbonyloxypropyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate mesylate is at least about 95%.

16. The pharmaceutical composition of claim 4 , and at least one other diastereomer of crystalline 2-phenylcarbonyloxypropyl-2-amino-3-(3,4-dihydroxyphenyl)propanoate mesylate wherein the compositional purity of crystalline (2R)-2-phenylcarbonyloxypropyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate mesylate is at least about 97%.

17. The pharmaceutical composition of claim 4 , comprising an L-aromatic amino acid decarboxylase inhibitor and a catechol-O-methyltransferase inhibitor.