Granted Patent B2

US 12,709,603 · App. 18/000,908 · Granted Aug 18, 2026

Inventors: Jing Teng (Lafayette, IN); Yizheng Cao (Lafayette, IN)

Assignee: VTV THERAPEUTICS LLC

C07D277/54A61K31/426C07B2200/13

Abstract

Claims (10)

1 . An anhydrous crystalline form of {2-[3-cyclohexyl-3-(trans-4-propoxy-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid that is characterized as having:

an X-ray powder diffraction (XRPD) comprising peaks at the following diffraction angles: 11.0+0.2, 11.6 +0.2, and 17.8 +0.2 degrees two theta as measured using Cu, Kα radiation (Form B); and (i) an endothermic peak with onset at about 166° C., as determined by Differential Scanning Calorimetry (DSC), or (ii) an Infrared Spectroscopy (IR) pattern having peaks at 1310.1±2.0, 1514.4±2.0, and 1661.3±12.0cm -1 ; and a polymorphic purity of at least 95%; or

an XRPD comprising peaks at the following diffraction angles: 5.3±0.2, 8.7±0.2, and 26.4±0.2 degrees two theta as measured using Cu, Kα radiation (Form D); an endothermic peak with onset at about 147° C., as determined by DSC; and a polymorphic purity of at least 95%; or

an XRPD comprising peaks at the following diffraction angles: 5.8±0.2, 17.9±0.2, and 18.9±0.2 degrees two theta as measured using Cu, Kα radiation (Form E); an endothermic peak with onset at about 171° C., as determined by DSC; and a polymorphic purity of at least 95%.

2 . A crystalline form of {2-[3-cyclohexyl-3-(trans-4-propoxy-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid comprising Crystalline Form A and either Crystalline Form B or Crystalline Form E, wherein Crystalline Form A is characterized as having an X-ray powder diffraction (XRPD) comprising peaks at the following diffraction angles: 8.7±0.2, 16.9±0.2, 17.4±0.2, and 20.1±0.2 degrees two theta as measured using Cu, Kα radiation (Form A); and an endothermic peak with onset at about 160° C., as determined by Differential Scanning Calorimetry (DSC);

wherein Crystalline Form B is characterized as having an XRPD comprising peaks at the following diffraction angles: 11.0±0.2, 11.6±0.2, 17.8±0.2, and 21.1±0.2 degrees two theta as measured using Cu, Kα radiation (Form B); and an endothermic peak with onset at about 166° C., as determined by DSC; and

wherein Crystalline Form E is characterized as having an XRPD comprising peaks at the following diffraction angles: 5.8±0.2, 17.9±0.2, 18.9±0.2, and 20.7±0.2 degrees two theta as measured using Cu, Kα radiation (Form E); and an endothermic peak with onset at about 171° C., as determined by DSC.

3 . The anhydrous crystalline form of claim 1 , wherein {2-[3-cyclohexyl-3-(trans-4-propoxy-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid is characterized as having an XRPD comprising peaks at the following diffraction angles: 11.0±0.2, 11.6±0.2, and 17.8±0.2 degrees two theta as measured using Cu, Kα radiation (Form B); and (i) an endothermic peak with onset at about 166° C., as determined by DSC, or (ii) an IR pattern having peaks at 1310.1±2.0, 1514.4±2.0, and 1661.3±2.0 cm −1 .

4 . The anhydrous crystalline form of claim 1 , wherein {2-[3-cyclohexyl-3-(trans-4-propoxy-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid is characterized as having an XRPD comprising peaks at the following diffraction angles: 5.3±0.2, 8.7±0.2, and 26.4±0.2 degrees two theta as measured using Cu, Kα radiation (Form D); and an endothermic peak with onset at about 147° C., as determined by DSC.

5 . The anhydrous crystalline form of claim 1 , wherein {2-[3-cyclohexyl-3-(trans-4-propoxy-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid is characterized as having an XRPD comprising peaks at the following diffraction angles: 5.8±0.2, 17.9±0.2, and 18.9±0.2 degrees two theta as measured using Cu, Kα radiation (Form E); and an endothermic peak with onset at about 171° C., as determined by DSC.

Assignments (2)

Continuity (2)

References Cited (220)