Solid forms of selective androgen receptor modulators

1. A crystalline form of an (R) or (S)—N-(4-cyano-3-(trifluoromethyl)phenyl)-3-(4-cyanophenoxy)-2-hydroxy-2-methylpropanamide compound, characterized by:

a) an X-Ray Powder diffraction pattern displaying peaks at °2θ (d value Å) angles of about 5.6 (15.9), 7.5 (11.8), 8.6 (10.3), 9.9 (8.9), 12.4 (7.1), 15.0 (5.9), 16.7 (5.3), 17.3 (5.1), 18.0 (4.9), 18.5 (4.8), 19.3 (4.6), 19.8 (4.5), 20.6 (4.3), 21.8 (4.1), 22.3 (4.0), 23.4 (3.8), 23.9 (3.7), 24.6 (3.6), 24.9 (3.6), 25.4 (3.5), 26.0 (3.4), 26.5 (3.4), 27.8 (3.2).

2. The crystalline form of claim 1 , wherein said crystalline form is an anhydrous crystalline form.

3. The crystalline form of claim 1 , wherein said crystalline form is characterized by the characteristics listed in (a) and a melting point of about 82 ° C.

4. The crystalline form of claim 1 , wherein said crystalline form is characterized by an X-ray diffraction pattern as depicted in FIG. 4 a.

5. A solid composition comprising a crystalline form of (R) or (S)—N-(4-cyano-3-(trifluoromethyl)phenyl)-3-(4-cyanophenoxy)-2-hydroxy-2-methylpropanamide of claim 1 and a suitable carrier or diluent.

6. A process for the preparation of a crystalline form of (R) or (S)—N-(4-cyano-3-(trifluoromethyl)phenyl)-3-(4-cyanophenoxy)-2-hydroxy-2-methylpropanamide of claim 1 , said process comprising dissolving amorphous (R) or (S)—N-(4-cyano-3-(trifluoromethyl)phenyl)-3-(4-cyanophenoxy)-2-hydroxy-2-methylpropanamide in at least one organic solvent at a temperature of between about −20° C. to +5° C. under conditions permissive to crystallization, thereby obtaining said crystalline form.

7. The process of claim 6 , wherein said organic solvent comprises a mixture of a solvent and an antisolvent.

8. The process of claim 7 , wherein said mixture comprises ethyl formate and pentane in a 1:2 v/v ratio.

9. The process of claim 7 , wherein said mixture comprises methyl acetate and pentane in a 1:2 v/v ratio.

10. The composition of claim 5 , wherein said crystalline form of(R) or (S)—N-(4-cyano-3-(trifluoromethyl)phenyl)-3-(4-cyanophenoxy)-2-hydroxy-2-methylpropanamide is an anhydrous crystalline form.

11. A solid composition comprising a mixture of a crystalline form of a (R) or (S)—N-(4-cyano-3-(trifluoromethyl)phenyl)-3-(4-cyanophenoxy)-2-hydroxy-2-methylpropanamide of claim 1 and a paracrystalline form of a (R) or (S)—N-(4-cyano-3-(trifluoromethyl)phenyl)-3-(4-cyanophenoxy)-2-hydroxy-2-methylpropanamide and a suitable carrier or diluent.

12. The crystalline form of claim 1 , wherein said crystalline form is characterized by an X-ray diffraction pattern as containing the identification peaks at °2θ (d value Å) angles of about 5.6 (15.9), 7.5 (11.8), 9.9 (8.9), and 12.4 (7.1).