Pharmaceutically acceptable salts of [3-(4- {2-butyl-1-[4-(4-chloro-phenoxy)-phenyl]-1H-imidazol-4-yl} -phenoxy)-propyl]-diethyl-amine

1. A crystalline form of a saccharinate, vanillate, fumarate, galactarate, hippurate, L-malate, oxalate, or mesylate salt of [3-(4-{2-butyl-1-[4-(4-chlorophenoxy)phenyl]-1H-imidazol-4-yl}phenoxy)-propyl]-diethylamine, wherein: the pharmaceutically acceptable acid is selected from the group consisting of

a) the crystalline form of the saccharinate salt is characterized by at least two of the following features (I-i)-(I-iv):

(I-i) an X-ray Powder Diffraction (XRPD) pattern having peaks at 2θ angles of 18.1, 21.1, and 25.7°±0.2°;

(I-ii) a Differential Scanning Calorimetry (DSC) profile as shown in FIG. 3 ;

(I-iii) a TGA profile as shown in FIG. 3 ; or

(I-iv) a 13C Solid-state Nuclear Magnetic Resonance (SSNMR) spectrum as shown in FIG. 53 ;

b) the crystalline form of the vanillate salt is characterized by at least two of the following features (I-i)-(I-iv):

(I-i) an XRPD pattern having peaks at 2θ angles of 7.6°, 15.2°, and 18.2°±0.2°;

(I-ii) a DSC profile as shown in FIG. 6 ;

(I-iii) a TGA profile as shown in FIG. 6 ; or

(I-iv) a 13C SSNMR spectrum as shown in FIG. 54 ;

c) the crystalline form of the fumarate salt is characterized by at least two of the following features (I-i)-(I-iv):

(I-i) an XRPD pattern having peaks at 2θ angles of 16.6°, 18.0°, and 21.5°±0.2°;

(I-ii) a DSC profile as shown in FIG. 13 ;

(I-iii) a TGA profile as shown in FIG. 13 ; or

(I-iv) a 13C SSNMR spectrum as shown in FIG. 57 ;

d) the crystalline form of the galactarate salt is characterized by at least two of the following features (I-i)-(I-iv):

(I-i) an XRPD pattern having peaks at 2θ angles of 8.0°, 14.6°, and 19.7°±0.2°;

(I-ii) a DSC profile as shown in FIG. 19 ;

(I-iii) a TGA profile as shown in FIG. 19 ; or

(I-iv) a 13C SSNMR spectrum as shown in FIG. 59 ;

e) the crystalline form of the hippurate salt is characterized by at least two of the following features (I-i)-(I-iv):

(I-i) an XRPD pattern having peaks at 2θ angles of 3.4°, 20.2°, and 20.9°±0.2°;

(I-ii) a DSC profile as shown in FIG. 29 ;

(I-iii) a TGA profile as shown in FIG. 29 ; or

(I-iv) a 13C SSNMR spectrum as shown in FIG. 62 ;

f) the crystalline form of the L-malate salt is characterized by at least two of the following features (I-i)-(I-iv):

(I-i) an XRPD pattern having peaks at 2θ angles of 3.7°, 17.2°, and 19.0°±0.2°;

(I-ii) a DSC profile as shown in FIG. 32 ;

(I-iii) a TGA profile as shown in FIG. 32 ; or

(I-iv) a 13C SSNMR spectrum as shown in FIG. 63 ;

g) the crystalline form of the oxalate salt is characterized by at least two of the following features (I-i)-(I-iv):

(I-i) an XRPD pattern having peaks at 2θ angles of 16.1°, 17.8°, and 21.9°±0.2°;

(I-ii) a DSC profile as shown in FIG. 34 ;

(I-iii) a TGA profile as shown in FIG. 34 ; or

(I-iv) a 13C SSNMR spectrum as shown in FIG. 64 ;

h) the crystalline form of the mesylate salt is characterized by at least two of the following features (I-i)-(I-iv):

(I-i) an XRPD pattern having peaks at 2θ angles of 20.3°, 22.4°, and 23.5°±0.2°;

(I-ii) a DSC profile as shown in FIG. 43 ;

(I-iii) a TGA profile as shown in FIG. 43 ; or

(I-iv) a 13C SSNMR spectrum as shown in FIG. 66 .

2. A crystalline form of a gentisate salt of [3-(4-{2-butyl-1-[4-(4-chlorophenoxy)phenyl]-1H-imidazol-4-yl}phenoxy)-propyl]-diethylamine, wherein the crystalline form is:

a) characterized by at least two of the following features (I-i)-(I-iv):

(I-i) an X-ray Powder Diffraction (XRPD) pattern having peaks at 2θ angles of 7.5°, 21.2°, and 24.7°±0.2°;

(I-ii) a Differential Scanning calorimetry (DSC) profile as shown in FIG. 37 ;

(I-iii) a Thermogravimetry Analysis (TGA) profile as shown in FIG. 37 ; or

(I-iv) a 13C Solid-state Nuclear Magnetic Resonance (SSNMR) spectrum as shown in FIG. 65 ; or

b) characterized by at least two of the following features (I-i)-(I-iii):

(I-i) an XRPD pattern having peaks at 2θ angles of 13.3°, 18.4°, and 21.2°±0.2°;

(I-ii) a DSC profile as shown in FIG. 40 ; or

(I-iii) a TGA profile as shown in FIG. 40 .

3. A crystalline form of a hydrobromide salt of [3-(4-{2-butyl-1-[4-(4-chlorophenoxy)phenyl]-1H-imidazol-4-yl}phenoxy)-propyl]-diethylamine, wherein the crystalline form is:

a) characterized by at least two of the following features (I-i)-(I-iv):

(I-i) an X-ray Powder Diffraction (XRPD) pattern having peaks at 2θ angles of 4.1°, 13.1°, and 16.4°±0.2°;

(I-i) a Differential Scanning calorimetry (DSC) profile as shown in FIG. 45 ;

(I-iii) a Thermogravimetric Analysis (TGA) profile as shown in FIG. 45 ; or

(I-iv) a 13C Solid-state Nuclear Magnetic Resonance (SSNMR) spectrum as shown in FIG. 67 ; or

b) characterized by at least two of the following features (I-i)-(I-iv):

(I-i) an XRPD pattern having peaks at 2θ angles of 9.3°, 20.9°, and 23.0°±0.2°;

(I-ii) a DSC profile as shown in FIG. 47 ;

(I-iii) a TGA profile as shown in FIG. 47 ; or

(I-iv) a 13C SSNMR spectrum as shown in FIG. 68 .

4. A crystalline form of a 4-aminosalicylate salt of [3-(4-{2-butyl-1-[4-(4-chlorophenoxy)phenyl]-1H-imidazol-4-yl}phenoxy)-propyl]-diethylamine, wherein the crystalline form of is:

a) characterized by at least two of the following features (I-i)-(I-iii):

(I-i) an X-ray Powder Diffraction (XRPD) pattern having peaks at 2θ angles of 17.1°, 19.2°, and 21.5°±0.2°;

(I-ii) a Differential Scanning calorimetry (DSC) profile as shown in FIG. 50 ; or

(I-iii) a Thermogravimetric Analysis (TGA) profile as shown in FIG. 50 ; or

b) characterized by at least two of the following features (I-i)-(I-iii):

(I-i) an XRPD pattern having peaks at 2θ angles of 7.1°, 19.2°, and 20.9°±0.2°;

(I-ii) a DSC profile as shown in FIG. 52 ;

(I-iii) a TGA profile as shown in FIG. 52 ; or

(I-iv) a 13C Solid-state Nuclear Magnetic Resonance (SSNMR) spectrum as shown in FIG. 69 .

5. A pharmaceutical composition comprising the crystalline form of claim 1 and one or more pharmaceutically acceptable carriers or diluents.

6. A pharmaceutical composition comprising the crystalline form of claim 2 and one or more pharmaceutically acceptable carriers or diluents.

7. A pharmaceutical composition comprising the crystalline form of claim 3 and one or more pharmaceutically acceptable carriers or diluents.

8. A pharmaceutical composition comprising the crystalline form of claim 4 and one or more pharmaceutically acceptable carriers or diluents.