Back to results
US 11,883,383 B2Granted
Pharmaceutically acceptable salts of [3-(4- {2-butyl-1-[4-(4-chloro-phenoxy)-phenyl]-1H-imidazol-4-yl} -phenoxy)-propyl]-diethyl-amine
AssigneevTv Therapeutics LLC
InventorJuan Hu
Life of this patent
Estimating the term…
Abstract
The present invention relates to pharmaceutically acceptable salts of [3-(4-{2-butyl-1-[4-(4-chloro-phenoxy)-phenyl]-1H-imidazol-4-yl}-phenoxy)-propyl]-diethylamine (“COMPOUND I”) useful in the treatment of RAGE mediated diseases.
Claims8
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.
46 more elements
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.
9 more elements
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.
10 more elements
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.
9 more elements
Dependencies are inferred from the claim text.