Patent
Polymorph of N,N-diethyl-4-(3-fluorophenyl-piperidin-4-ylidene-methyl)-benzamide hydrochloride salt
| العنوان: | Polymorph of N,N-diethyl-4-(3-fluorophenyl-piperidin-4-ylidene-methyl)-benzamide hydrochloride salt |
|---|---|
| Patent Number: | 8,148,406 |
| تاريخ النشر: | April 03, 2012 |
| Appl. No: | 11/575841 |
| Application Filed: | October 05, 2005 |
| مستخلص: | Polymorphs of N,N-diethyl-4-(3-fluorophenyl-piperidin-4-ylidene-methyl)-benzamide hydrochloride salt, methods of making these polymorphs and uses thereof are described. |
| Inventors: | Black, Simon Nicholas (Macclesfield, GB); Cook, Steve (Wilmington, DE, US); Diorazio, Louis Joseph (Macclesfield, GB); Hulsizer, James (Wilmington, DE, US); Moore, Gary (Wilmington, DE, US); Quigley, Kathryn (Macclesfield, GB) |
| Assignees: | AstraZeneca AB (Sodertalje, SE) |
| Claim: | 1. Polymorph A of N,N-diethyl-4-(3-fluorophenyl-piperidin-4-ylidene-methyl)-benzamide hydrochloride salt, said polymorph A having a 13 C solid state NMR spectrum substantially as shown in FIG. 2 . |
| Claim: | 2. Polymorph B of N,N-diethyl-4-(3-fluorophenyl-piperidin-4-ylidene-methyl)-benzamide hydrochloride salt, said polymorph B having a 13 C solid state NMR spectrum substantially as shown in FIG. 2 . |
| Claim: | 3. Polymorph A of N,N-diethyl-4-(3-fluorophenyl-piperidin-4-ylidene-methyl)-benzamide hydrochloride salt as claimed in claim 1 , prepared by a process comprising: combining N,N-diethyl-4-(3-fluorophenyl-piperidin-4-ylidene-methyl)-benzamide hydrochloride salt and a solvent selected from the group consisting of isopropanol, butanol and acetone at a temperature between 20° C. and 80° C.; warming said N,N-diethyl-4-(3-fluorophenyl-piperidin-4-ylidene-methyl)-benzamide hydrochloride salt and solvent to at least 50° C. for at least one hour to achieve a solution; cooling said solution to a temperature of less than 35° C. to achieve crystallization of said N,N-diethyl-4-(3-fluorophenyl-piperidin-4-ylidene-methyl)-benzamide hydrochloride salt; optionally seeding said solution with a polymorph A seed; and recovering said crystallized polymorph A. |
| Claim: | 4. The polymorph of claim 3 , prepared by a process wherein said solvent is isopropanol. |
| Claim: | 5. Polymorph B of N,N-diethyl-4-(3-fluorophenyl-piperidin-4-ylidene-methyl)-benzamide hydrochloride salt, as claimed in claim 2 , prepared by a process comprising: combining N,N-diethyl-4-(3-fluorophenyl-piperidin-4-ylidene-methyl)-benzamide hydrochloride salt and a solvent selected from the group consisting of isopropanol, butanol and acetone at a temperature between 20° C. and 80° C.; warming said N,N-diethyl-4-(3-fluorophenyl-piperidin-4-ylidene-methyl)-benzamide hydrochloride salt and solvent to at least 50° C. for at least one hour to achieve a solution; cooling said solution to a temperature of less than 35° C. to achieve crystallization of said N,N-diethyl-4-(3-fluorophenyl-piperidin-4-ylidene-methyl)-benzamide hydrochloride salt; optionally seeding said solution with a polymorph B seed; and recovering said crystallized polymorph B. |
| Claim: | 6. The polymorph of claim 5 , prepared by a process wherein said solvent is isopropanol. |
| Claim: | 7. A pharmaceutical composition comprising a polymorph according to claim 1 and a pharmaceutically acceptable carrier. |
| Claim: | 8. A pharmaceutical composition comprising a polymorph according to claim 2 and a pharmaceutically acceptable carrier. |
| Claim: | 9. A method for the treatment of pain in a warm-blooded animal, comprising the step of administering to said animal in need of such treatment a therapeutically effective amount of a pharmaceutical composition according to claim 7 . |
| Claim: | 10. A method for the treatment of anxiety in a warm-blooded animal, comprising the step of administering to said animal in need of such treatment a therapeutically effective amount of a pharmaceutical composition according to claim 7 . |
| Claim: | 11. A method for the treatment of pain in a warm-blooded animal, comprising the step of administering to said animal in need of such treatment a therapeutically effective amount of a pharmaceutical composition according to claim 8 . |
| Claim: | 12. A method for the treatment of anxiety in a warm-blooded animal, comprising the step of administering to said animal in need of such treatment a therapeutically effective amount of a pharmaceutical composition according to claim 8 . |
| Current U.S. Class: | 514/331 |
| Patent References Cited: | 2898339 August 1959 Wheeler et al. 4581171 April 1986 Kennis et al. 4816586 March 1989 Portoghese 4939137 July 1990 Russell et al. 5140029 August 1992 Kennis et al. 5574159 November 1996 Chang et al. 5683998 November 1997 Shibayama et al. 6187792 February 2001 Delorme et al. 6455545 September 2002 Delorme et al. 6693117 February 2004 Delorme et al. 2004/0171612 September 2004 Delorme et al. 9315062 August 1993 9723466 July 1997 9828275 July 1998 9933806 July 1999 0174804 October 2001 0174806 October 2001 0248122 June 2002 2004101522 November 2004 |
| Other References: | Morissette et al. “High-throughput crystallization: polymorphs, salts, co-crystals and solvates of pharmaceutical solids.” Advanced Drug Delivery Reviews, 2004, 56, 275-300. cited by examiner Vippagunta, Sudha R. “Crystalline Solids.” Advanced Drug Delivery Reviews 48(2001): 3-26. cited by examiner Barber et al., “Antinociceptive Effects of the 5-HT2 Antagonist Ritanserin in Rats: Evidence for an Activation of Descending Monoaminergic Pathways in the Spinal Cord,” Neurosci. Letters, 1989, vol. 99, pp. 234-238. cited by other Bilsky, et al., “SNC 80, a Selective, Nonpeptidic and Systemically Active Opioid Delta Agonist,” J. Pharmacol. Experi. Ther., 1995, vol. 273, pp. 359-366. cited by other Greene, “Protective Groups in Organic Synthesis,” Wiley & Sons, 1982, pp. 218-220, 232, 233, 251. cited by other Takemori, et al., “Selective Natrexone-Derived Opinoid Receptor Agonists,” Annu. Ref. Pharmacol. Toxicol., 1992, vol. 32, pp. 239-269. cited by other Wei, Z. et al., “N,N-Diethyl-4-(phenylpiperidin-4-ylidenemethyl)benzamide: A Novel, Exceptionally Selective, Potent alpha Opioid Receptor Agonist with Oral Bioavailability and Its Analogues,” J. Med. Chem., 2000, vol. 43, pp. 3895-3905. cited by other Zhang et al., “Probes for Narcotic Receptor Mediated Phenomena. 26. 1-3 Synthesis and Biological Examiner of Diarylmethylpiperazines and Diarylmethylpiperidines as Novel, Nonpeptidic Delta Opioid Receptor Ligands,” J. Med. Chem., 1999, vol. 42, pp. 5455-5463. cited by other International-Type Search Report issued for SE 0402485-7 on Apr. 15, 2005. cited by other International Search Report issued for PCT/SE2005/001469 on Dec. 20, 2005. cited by other Caira, “Crystalline Polymorphism of Organic Compounds,” Topics in Current Chemistry, 1998, pp. 163-208, vol. 198, Springer Verlag Berlin Heidelberg. cited by other Extended European search report issued for 05789875.1 on Apr. 14, 2010. cited by other |
| Assistant Examiner: | Otton, Alicia L |
| Primary Examiner: | Anderson, Rebecca |
| Attorney, Agent or Firm: | Mitchell, Kenneth F. |
| رقم الانضمام: | edspgr.08148406 |
| قاعدة البيانات: | USPTO Patent Grants |
| الوصف غير متاح. |