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US 9,242,917 B2Granted
Crystal forms of a HCV protease inhibitor
AssigneeMerck Sharp & Dohme Corp.
InventorsGregory L Beutner, Robert M Wenslow, Jr., Eric J Choi, Clinton Scott Shultz, Jeremy Scott, Juan D Arredondo, Laura Artino
Life of this patent
Estimating the term…
Abstract
The present invention relates to different forms of a HCV inhibitory compound.
Claims6
Compound A having a form selected from the group consisting of:
- a) Hydrate III, wherein Hydrate III is characterized by (i) an X-ray powder diffraction pattern obtained using copper Kα radiation which comprises 2Θ values in degrees of about 20.5, 5.0, and 18.2;
- and/or (ii) a solid state carbon-13 CPMAS NMR comprising peaks at about 5.14, 6.31, 12.49, 18.35, 26.81, 28.03, 30.33, 31.27, 34.95, 35.99, 38.68, 42.01, 54.93, 56.39, 60.14, 74.20, 107.02, 120.11, 121.60, 129.73, 134.35, 135.95, 142.89, 148.47, 155.37, 157.32, 160.90, 168.32, 172.17, and 175.53 ppm;
- b) Hydrate II, wherein Hydrate II is characterized by an X-ray powder diffraction pattern obtained using copper Kα radiation which comprises 2Θ values in degrees of about 11.7, 16.6, and 11.2;
- c) a crystalline Na salt characterized by an X-ray powder diffraction pattern obtained using copper Kα radiation which comprises 2Θ values in degrees of about 18.4, 9.1, and 9.8;
- d) Hydrate I, wherein Hydrate I is characterized by (i) an X-ray powder diffraction pattern obtained using copper Kα radiation which comprises 2Θ values in degrees of about 8.6, 20.6, and 26.6;
- and/or (ii) a solid state carbon-13 CPMAS NMR comprising peaks at about 4.22, 7.23, 11.45, 17.79, 24.04, 26.95, 28.29, 31.15, 32.47, 32.47, 33.46, 34.03, 35.74, 42.32, 53.50, 56.05, 56.96, 77.49, 108.95, 119.65, 122.55, 131.05, 133.13, 135.38, 142.28, 150.78, 156.03, 157.99, 161.36, 171.40, 173.42, 174.30 ppm;
- e) Hydrate IV, wherein Hydrate IV is characterized by (i) an X-ray powder diffraction pattern obtained using copper Kα radiation which comprises 2Θ values in degrees of about 14.7, 11.5, and 7.1;
- and/or (ii) a solid state carbon-13 CPMAS NMR comprising peaks at about 3.90, 5.30, 6.99, 10.49, 13.13, 17.81, 24.73, 27.52, 28.14, 29.42, 31.02, 32.80, 36.08, 39.22, 42.45, 53.62, 55.93, 59.14, 60.76, 74.77, 109.22, 111.19, 11.38, 120.24, 122.50, 133.96, 139.74, 147.2, 148.90, 154.65, 158.25, 159.53, 160.12, 170.14, 171.05, 172.08, 173.47, and 174.46 ppm;
- f) Hydrate V, wherein Hydrate V is characterized by (i) an X-ray powder diffraction pattern obtained using copper Kα radiation which comprises 2Θ values in degrees of about 9.1, 18.3, and 19.8;
- and/or (ii) a solid state carbon-13 CPMAS NMR comprising peaks at about 7.86, 8.92, 13.10, 18.31, 23.72, 27.44, 28.47, 30.77, 35.79, 36.25, 37.15, 37.15, 42.95, 53.13, 55.67, 57.31, 60.47, 62.06, 75.09, 110.59, 112.24, 118.32, 132.18, 134.05, 135.83, 139.88, 148.30, 155.19, 157.97, 159.41, 170.31 and 175.20;
- and
- g) Hydrate VI, wherein Hydrate VI is characterized by (i) an X-ray powder diffraction pattern obtained using copper Kα radiation which comprises 2Θ values in degrees of about 20.5, 12.8, and 19.4;
- and/or (ii) a solid state carbon-13 CPMAS NMR comprising peaks at about 4.87, 6.24, 11.70, 12.85, 18.36, 26.55, 28.31 m 31.51, 34.98, 38.47, 42.09, 54.27, 56.12, 60.10, 73.49, 73.97, 105.91, 108.04, 118.39, 119.75, 121.33, 129.96, 133.87, 136.13, 142.26, 142.97, 146.85, 148.36, 154.97, 157.32, 160.71, 168.23, 172.21 and 175.34 ppm.
10 more elements
Dependencies are inferred from the claim text.