Crystalline forms of (r)-3-[n-(3'-chlorobiphenyl-4-ylmethyl)-n'-(3-hydroxyisoxazole-5-carbonyl)hydrazino]-2-hydroxypropionic acid isopropyl ester

A crystalline (R)-3-[N-(3′-chlorobiphenyl-4-ylmethyl)-N′—(3-hydroxyisoxazole-5-carbonyl)hydrazino]-2-hydroxypropionic acid isopropyl ester, selected from:

• a neutral monohydrate Form 1 characterized by a powder x-ray diffraction pattern comprising diffraction peaks at 2θ values of 8.26±0.20, 14.68±0.20, 15.64±0.20, 16.36±0.20, 18.52±0.20, 20.40±0.20, 21.08±0.20, 21.48±0.20, 21.68±0.20, 23.18±0.20, 24.50±0.20, 24.80±0.20, 25.34±0.20, and 26.56±0.20;
• a neutral Form 2 characterized by a powder x-ray diffraction pattern comprising diffraction peaks at 2θ values of 7.48±0.20, 8.02±0.20, 9.38±0.20, 12.24±0.20, 14.86±0.20, 18.72±0.20, 20.94±0.20, 21.34±0.20, 22.32±0.20, and 24.68±0.20;
• a neutral solvated Form 2′ characterized by a powder x-ray diffraction pattern comprising diffraction peaks at 2θ values of 7.26±0.20, 8.05±0.20, 12.20±0.20, 14.48±0.20, 15.84±0.20, 16.22±0.20, 18.78±0.20, 20.60±0.20, 21.29±0.20, 21.74±0.20, 23.10±0.20, 24.16±0.20, and 24.44±0.20;
• a neutral anhydrous Form 3 characterized by a powder x-ray diffraction pattern comprising diffraction peaks at 2θ values of 8.12±0.20, 8.86±0.20, 11.92±0.20, 13.68±0.20, 16.10±0.20, 18.12±0.20, 18.46±0.20, 19.06±0.20, 19.48±0.20, 20.60±0.20, 21.28±0.20, 24.46±0.20, 25.94±0.20, and 26.40±0.20;
• a neutral anhydrous Form 4 characterized by a powder x-ray diffraction pattern comprising diffraction peaks at 2θ values of 8.70±0.20, 13.00±0.20, 16.00±0.20, 16.94±0.20, 17.36±0.20, 18.72±0.20, 19.00±0.20, 19.78±0.20, 20.24±0.20, 21.70±0.20, 23.68±0.20, and 27.94±0.20;
• a tromethamine salt characterized by a powder x-ray diffraction pattern comprising diffraction peaks at 2θ values of 6.94±0.20, 9.00±0.20, 12.36±0.20, 13.74±0.20, 16.58±0.20, 17.12±0.20, 18.32±0.20, 19.86±0.20, 20.28±0.20, 21.36±0.20, 23.82±0.20, and 27.00±0.20;
• an L-lysine salt characterized by a powder x-ray diffraction pattern comprising diffraction peaks at 2θ values of 3.10±0.20, 9.13±0.20, 10.12±0.20, 12.14±0.20, 18.33±0.20, 18.54±0.20, 20.14±0.20, 20.88±0.20, 21.72±0.20, 23.12±0.20, and 24.58±0.20;
• and
• a meglumine salt characterized by a powder x-ray diffraction pattern comprising diffraction peaks at 2θ values of 6.10±0.20, 8.72±0.20, 10.20±0.20, 12.24±0.20, 15.32±0.20, 17.04±0.20, 18.46±0.20, 19.40±0.20, 20.46±0.20, 21.12±0.20, 23.12±0.20, and 25.96±0.20.