Salts and ionic liquid of the antituberculosis drug S,S-ethambutol

Crystal Growth and Design

Volumn 13, Issue 4, 2013, Pages 1752-1760

  Cherukuvada, Suryanarayan ^a   Nangia, Ashwini ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ANTITUBERCULOSIS; BASIC DRUGS; DSC AND TGA; ETHAMBUTOL; LIQUID PRODUCTS; NON-HYGROSCOPIC; PROTIC ACIDS; X RAY CRYSTAL STRUCTURES;

IONIC LIQUIDS; X RAY DIFFRACTION;

SALTS;

EID: 84875802824     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg400071d     Document Type: Article

References (55)

1. Bhutani, H.; Singh, S.; Jindal, K. C.; Charkraborti, A. K. J. Pharm. Biomed. Anal. 2005, 39, 892
2. Blomberg, B.; Spinachi, S.; Fourie, B.; Laing, R. Bull. W.H.O. 2001, 79, 61
3. Wilkinson, R. G.; Shepherd, R. G.; Thomas, J. P.; Baughn, C. J. Am. Chem. Soc. 1961, 83, 2212
4. Singh, S.; Mohan, B. The International Journal of Tuberculosis and Lung Disease 2003, 7, 298
5. http://apps.who.int/prequal/whopar/whoparproducts/TB168Part6v1.pdf.
6. Bai, G.-Y.; Ning, H.-S.; Zhang, Y.-C.; Zeng, T.; Li, J.-S. Acta Crystallogr. 2006, E62, o3364
7. Godfrey, R.; Hargreaves, R.; Hitchcock, P. B. Acta Crystallogr. 1992, C48, 79
8. Bai, G.-Y.; Ning, H.-S.; Simpson, J.; Kin, X.-Y.; Li, N. Acta Crystallogr. 2006, E62, o4567
9. Mitsui Toatsu Inc. and Mitsui Pharmaceuticals Inc. G.B. Patent 1365473A, 1973.
10. Park, S.-W. (Korean Advanced Institute of Science and Technology). U.S. Patent 4450274, 1984.
11. Rubin-Preminger, J. M.; Bernstein, J.; Harris, R. K.; Evans, I. R.; Ghi, P. Y. Cryst. Growth Des. 2004, 4, 431 (CCDC Refcode CURJEE02)
12. Cherukuvada, S.; Nangia, A. CrystEngComm 2012, 14, 7840
13. Stoimenovski, J.; MacFarlane, D. R.; Bica, K.; Rogers, R. D. Pharm. Res. 2010, 27, 521
14. Bica, K.; Rogers, R. D. Chem. Commun. (Cambridge, U.K.) 2010, 46, 1215
15. Rogers, R. D.; MacFarlane, D.; Zhang, S., Guest Eds. for Themed Issue: Ionic Liquids, Chem. Commun. (Cambridge, U.K.) 2012, 48.
16. Silvester, D. S.; Compton, R. G. Z. Phys. Chem. 2006, 220, 1247
17. Trask, A. V.; Haynes, D. A.; Motherwell, W. D. S.; Jones, W. Chem. Commun. (Cambridge, U.K.) 2006, 51
18. Stoimenovski, J.; Dean, P. M.; Izgorodina, E. I.; MacFarlane, D. R. Faraday Discuss. 2012, 154, 335
19. Yoshizawa, M.; Xu, W.; Angell, C. A. J. Am. Chem. Soc. 2003, 125, 15411
20. Cambridge Structural Database, version 5.33, ConQuest 1.14, November 2011 release, August 2012, update; www.ccdc.cam.ac.uk.
21. Flack, H. D.; Bernardinelli, G. Acta Crystallogr. 1999, A55, 908
22. Flack, H. D.; Bernardinelli, G. J. Appl. Crystallogr. 2000, 33, 1143
23. th ed.; Merck Sharp & Dohme Corp.: Whitehouse Station, N.J., 2006.
24. Hamalainen, R.; Lehtinen, M.; Ahlgren, M. Arch. Pharm. (Weinheim, Ger.) 1985, 318, 26 (CCDC Refcode CURJEE)
25. Bai, G.-Y.; Zhang, C.-F.; Zhang, Y.-C.; Zeng, T.; Li, J.-S. Acta Crystallogr. 2006, E62, o2173
26. Bai, G.-Y.; Zhang, C.-F.; Zhang, Y.-C.; Zeng, T.; Li, J.-S. Acta Crystallogr. 2007, E63, e2
27. van Eijck, B. P.; Kroon, J. Acta Crystallogr. 2000, B56, 535
28. Silverstein, R. M.; Webster, F. X.; Kiemle, D. J. Spectrometric Identification of Organic Compounds, John Wiley & Sons: NJ, 2005.
29. Li, Z. J.; Abramov, Y.; Bordner, J.; Leonard, J.; Medek, A.; Trask, A. V. J. Am. Chem. Soc. 2006, 128, 8199
30. Vogt, F. G.; Clawson, J. S.; Strohmeier, M.; Edwards, A. J.; Pham, T. N.; Watson, S. A. Cryst. Growth Des. 2009, 9, 921
31. Maddileti, D.; Thakuria, R.; Cherukuvada, S.; Nangia, A. CrystEngComm 2012, 14, 2367
32. Nath, N. K.; Nilapwar, S.; Nangia, A. Cryst. Growth Des. 2012, 12, 1613
33. Bag, P. P.; Reddy, C. M. Cryst. Growth Des. 2012, 12, 2740
34. Bag, P. P.; Patni, M.; Reddy, C. M. CrystEngComm 2011, 13, 5650
35. Bastin, R. J.; Bowker, M. J.; Slater, B. J. Org. Process Res. Dev. 2000, 4, 427
36. Gould, P. L. Int. J. Pharm. 1986, 33, 201
37. Maiti, A.; Kumar, A.; Rogers, R. D. Phys. Chem. Chem. Phys. 2012, 14, 5139
38. Huddleston, J. G.; Visser, A. E.; Riechert, W. M.; Willauer, H. D.; Broker, G. A.; Rogers, R. D. Green Chem. 2001, 3, 156
39. Qian, Q.; Yu, P.; Cheng, H.; Wang, X.; Yang, L.; Mao, L. Electroanal. 2011, 23, 2870
40. Schultheiss, N.; Newman, A. Cryst. Growth Des. 2009, 9, 2950
41. Babu, N. J.; Nangia, A. Cryst. Growth Des. 2011, 11, 2662
42. Górniak, A.; Wojakowska, A.; Karolewicz, B.; Pluta, J. J. Therm. Anal. Calorim. 2011, 104, 1195
43. Cherukuvada, S.; Nangia, A. CrystEngComm 2012, 14, 2579
44. Moore, M. D.; Wildfong, P. L. D. Journal of Pharmaceutical Innovation 2009, 4, 36
45. Vasconcelos, T.; Sarmento, B.; Costa, P. Drug Discovery Today 2007, 12, 1068
46. Janssens, S.; Roberts, C.; Smith, E. F.; Mooter, G. V. Int. J. Pharm. 2008, 355, 100
47. SAINT-Plus, version 6.45; Bruker AXS Inc.: Madison, Wisconsin, 2003.
48. Sheldrick, G. M. SADABS, Program for Empirical Absorption Correction of Area Detector Data; University of Göttingen, Göttingen, Germany, 1997.
49. SMART, version 5.625, and SHELX-TL, version 6.12; Bruker AXS Inc.: Madison, Wisconsin, 2000.
50. Sheldrick, G. M. SHELXS-97 and SHELXL-97; University of Göttingen: Göttingen, Germany, 1997.
51. CrysAlis CCD and CrysAlis RED, version 1.171.33.55; Oxford Diffraction Ltd: Yarnton, Oxfordshire, U.K., 2008.
52. Dolomanov, O. V.; Blake, A. J.; Champness, N. R.; Schröder, M. J. Appl. Crystallogr. 2003, 36, 1283
53. Spek, A. L. PLATON, A Multipurpose Crystallographic Tool; Utrecht University: Utrecht, The Netherlands, 2002.
54. Barbour, L. J. X-Seed, Graphical Interface to SHELX-97 and POV-Ray, Program for Better Quality of Crystallographic Figures; University of Missouri-Columbia: Columbia, Missouri, 1999.
55. PowderCell, Program for Structure Visualization, Powder Pattern Calculation and Profile Fitting (http://www.ccp14.ac.uk/index.html).