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Last Updated: April 3, 2025

Claims for Patent: 9,062,014

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Summary for Patent: 9,062,014

Title:	Crystalline forms of (R)-5-[3-chloro-4-(2,3-dihydroxy-propoxy)-benz[Z]ylidene]-2-([Z]-propylim- ino)-3-0-tolyl-thiazolidin-4-one
Abstract:	The invention relates to crystalline forms of (R)-5-[3-chloro-4-(2,3-dihydroxy-propoxy)-benz[Z]ylidene]-2-([Z]-propylim- ino)-3-o-tolyl-thiazolidin-4-one, processes for the preparation thereof, pharmaceutical compositions containing said crystalline forms, and their use as compounds improving vascular function and as immunomodulating agents, either alone or in combination with other active compounds or therapies.
Inventor(s):	Bonham; Nicholas (Oxford, GB), Buchmann; Stephan (Allschwil, CH), Eberlin; Alex (Cambridge, GB), Imboden; Christoph (Hofstetten, CH), Von Raumer; Markus (Allschwil, CH)
Assignee:	ACTELION PHARMACEUTICALS LTD. (Allschwil, CH)
Application Number:	13/125,102
Patent Litigation and PTAB cases:	See patent lawsuits and PTAB cases for patent 9,062,014
Patent Claims:	1. A crystalline form of the compound (R)-5-[3-chloro-4-(2,3-dihydroxy-propoxy)-benz[Z]ylidene]-2-([Z]-propylim- ino)-3-o-tolyl-thiazolidin-4-one containing from 0 to 0.5 equivalents of H.sub.2O per equivalent of (R)-5-[3-chloro-4-(2,3-dihydroxy-propoxy)-benz[Z]ylidene]-2-([Z]-propylim- ino)-3-o-tolyl-thiazolidin-4-one, characterised by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2.theta.: 7.0.degree., 11.2.degree., and 12.6.degree., wherein the X-ray powder diffraction diagram is obtained by using Cu K.alpha.1 radiation (.lamda.=1.5406 .ANG.), and wherein the accuracy of the 2.theta. values is in the range of +/- 0.2.degree.. 2. The crystalline form according to claim 1, characterized by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2.theta.: 7.0.degree., 11.2.degree., 12.6.degree., 16.6.degree., 18.8.degree., 21.3.degree., 23.6.degree., and 26.0.degree., wherein the X-ray powder diffraction diagram is obtained by using Cu K.alpha.1 radiation (.lamda.=1.5406 .ANG.). 3. The crystalline form according to claim 1, which has a melting point of about 113.degree. C. as determined by differential scanning calorimetry. 4. The crystalline form according to claim 1 containing 0.5 equivalents of H.sub.2O per equivalent of (R)-5-[3-chloro-4-(2,3-dihydroxy-propoxy)-benz[Z]ylidene]-2-([Z]-propylim- ino)-3-o-tolyl-thiazolidin-4-one. 5. The crystalline form according to claim 2 containing 0.5 equivalents of H.sub.2O per equivalent of (R)-5-[3-chloro-4-(2,3-dihydroxy-propoxy)-benz[Z]ylidene]-2-([Z]-propylim- ino)-3-o-tolyl-thiazolidin-4-one. 6. The crystalline form according to claim 2, which has a melting point of about 113.degree. C. as determined by differential scanning calorimetry. 7. The crystalline form according to claim 4, which has a melting point of about 113.degree. C. as determined by differential scanning calorimetry. 8. The crystalline form according to claim 5, which has a melting point of about 113.degree. C. as determined by differential scanning calorimetry. 9. A pharmaceutical composition comprising the crystalline form according to claim 1 and a pharmaceutically acceptable carrier. 10. A method of treatment or prophylaxis of rejection of transplanted organs selected from kidney, liver, heart and lung; or graft-versus-host diseases brought about by stem cell transplantation; or a method of treatment of any of the following disorders: autoimmune syndromes selected from rheumatoid arthritis, multiple sclerosis, psoriasis, psoriatic arthritis, Crohn's disease, and Hashimoto's thyroiditis; and atopic dermatitis, wherein said method comprises administering to a subject in need thereof an effective amount of the crystalline form according to claim 1. 11. A crystalline form of the compound (R)-5-[3-chloro-4-(2,3-dihydroxy-propoxy)-benz[Z]ylidene]-2-([Z]-propylim- ino)-3-o-tolyl-thiazolidin-4-one containing from 0 to 0.5 equivalents of H.sub.2O per equivalent of (R)-5-[3-chloro-4-(2,3-dihydroxy-propoxy)-benz[Z]ylidene]-2-([Z]-propylim- ino)-3-o-tolyl-thiazolidin-4-one, characterised by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2.theta.: 10.5.degree., 22.2.degree., and 23.4.degree., wherein the X-ray powder diffraction diagram is obtained by using Cu K.alpha.1 radiation (.lamda.=1.5406 A), and wherein the accuracy of the 28 values is in the range of +/- 0.2.degree.. 12. The crystalline form according to claim 11, characterised by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2.theta.: 10.5.degree., 11.1.degree., 11.4.degree., 13.6.degree., 13.9.degree., 16.3.degree., 20.8.degree., 22.2.degree., 23.4.degree., 24.1.degree., 25.7.degree., 27.7.degree., 27.9.degree., 28.7.degree., and 29.3.degree., wherein the X-ray powder diffraction diagram is obtained by using Cu K.alpha.1 radiation (.lamda.=1.5406 .ANG.). 13. The crystalline form according to claim 11, which has a melting point of about 133.degree. C. as determined by differential scanning calorimetry. 14. The crystalline form according to claim 11, wherein the compound (R)-5-[3-chloro-4-(2,3-dihydroxy-propoxy)-benz[Z]ylidene]-2-([Z]-propylim- ino)-3-o-tolyl-thiazolidin-4-one is in anhydrous form. 15. The crystalline form according to claim 12, wherein the compound (R)-5-[3-chloro-4-(2,3-dihydroxy-propoxy)-benz[Z]ylidene]-2-([Z]-propylim- ino)-3-o-tolyl-thiazolidin-4-one is in anhydrous form. 16. The crystalline form according to claim 12, which has a melting point of about 133.degree. C. as determined by differential scanning calorimetry. 17. The crystalline form according to claim 14, which has a melting point of about 133.degree. C. as determined by differential scanning calorimetry. 18. The crystalline form according to claim 15, which has a melting point of about 133.degree. C. as determined by differential scanning calorimetry. 19. A pharmaceutical composition comprising the crystalline form according to claim 11 and a pharmaceutically acceptable carrier. 20. A method of treatment or prophylaxis of rejection of transplanted organs selected from kidney, liver, heart and lung; or graft-versus-host diseases brought about by stem cell transplantation; or a method of treatment of any of the following disorders: autoimmune syndromes selected from rheumatoid arthritis, multiple sclerosis, psoriasis, psoriatic arthritis, Crohn's disease; and Hashimoto's thyroiditis; and atopic dermatitis, wherein said method comprises administering to a subject in need thereof an effective amount of the crystalline form according to claim 11.

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