Probing intermolecular hydrogen bonding in sibenadet hydrochloride polymorphs by high-resolution 1H double-quantum solid-state NMR spectroscopy

Journal of Pharmaceutical Sciences

Volumn 101, Issue 5, 2012, Pages 1821-1830

  Bradley, Jonathan P ^a   Pickard, Chris J ^b   Burley, Jonathan C ^c   Martin, Dave R ^d   Hughes, Leslie P ^d   Cosgrove, Stephen D ^d   Brown, Steven P ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

^c UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^d ASTRAZENECA   (United Kingdom)

Author keywords

Analytical chemistry; Double quantum; GIPAW simulations; Hydrogen bonding; Intermolecular interactions; Magic angle spinning; NMR; Physical characterisation; Polymorphism; Solid state

Indexed keywords

HYDROGEN; SIBENADET; BETA ADRENERGIC RECEPTOR STIMULATING AGENT; DOPAMINE RECEPTOR STIMULATING AGENT; PROTON; THIAZOLE DERIVATIVE;

ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; HYDROGEN BOND; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; X RAY DIFFRACTION; CHEMICAL STRUCTURE; CHEMISTRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTUM THEORY; X RAY CRYSTALLOGRAPHY;

ADRENERGIC BETA-AGONISTS; CRYSTALLOGRAPHY, X-RAY; DOPAMINE AGONISTS; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; PROTONS; QUANTUM THEORY; THIAZOLES;

EID: 84864296794     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.23078     Document Type: Article

References (52)

1. Tishmack PA, Bugay DE, Byrn SR. 2003. Solid-state nuclear magnetic resonance spectroscopy-Pharmaceutical applications. J Pharm Sci 92:441-474.
2. Berendt RT, Sperger DM, Isbester PK, Munson EJ. 2006. Solid-state NMR spectroscopy in pharmaceutical research and analysis. Trends Anal Chem 25:977-984.
3. Harris RK. 2006. NMR studies of organic polymorphs and solvates. Analyst 131:351-373.
4. Harris RK. 2007. Applications of solid-state NMR to pharmaceutical polymorphism and related matters. J Pharm Pharmacol 59:225-239.
5. Geppi M, Mollica G, Borsacchi S, Veracini CA. 2008. Solid-state NMR studies of pharmaceutical systems. Appl Spectrosc Rev 43:202-302.
6. Vogt FG. 2010. Evolution of solid-state NMR in pharmaceutical analysis. Future Med Chem 2:915-921.
7. Brown SP. 2007. Probing proton-proton proximities in the solid state. Prog Nucl Magn Reson Spectrosc 50:199-251.
8. Griffin JM, Martin DR, Brown SP. 2007. Distinguishing anhydrous and hydrous forms of an active pharmaceutical ingredient in a tablet formulation using solid-state NMR spectroscopy. Angew Chem Int Ed Engl 46:8036-8038.
9. Vogt FG, Katrincic LM, Long ST, Mueller RL, Carlton RA, Sun YT, Johnson MN, Copley RCB, Light ME. 2008. Enantiotropically-related polymorphs of {4-(4-Chloro-3-fluorophenyl)-2-4-(methyloxy)phenyl-1, 3-thiazol-5-yl} acetic acid: Crystal structures and multinuclear solid-state NMR. J Pharm Sci 97:4756-4782.
10. Vogt FG, Clawson JS, Strohmeier M, Edwards AJ, Pham TN, Watson SA. 2009. Solid-state NMR analysis of organic cocrystals and complexes. Cryst Growth Des 9:921-937.
11. Salager E, Stein RS, Pickard CJ, Elena B, Emsley L. 2009. Powder NMR crystallography of thymol. Phys Chem Chem Phys 11:2610-2621.
12. 1 relaxation measurements. Mol Pharm 7:1677-1691.
13. Khan M, Enkelmann V, Brunklaus G. 2010. Crystal engineering of pharmaceutical co-crystals: Application of methyl paraben as molecular hook. J Am Chem Soc 132:5254-5263.
14. Harris RK, Hodgkinson P, Zorin V, Dumez JN, Elena-Herrmann B, Emsley L, Salager E, Stein RS. 2010. Computation and NMR crystallography of terbutaline sulfate. Magn Reson Chem 48:S103-S112.
15. Bettini R, Menabeni R, Tozzi R, Pranzo MB, Pasquali I, Chierotti MR, Gobetto R, Pellegrino L. 2010. Didanosine polymorphism in a supercritical antisolvent process. J Pharm Sci 99:1855-1870.
16. 1H solid-state NMR spectroscopy. Cryst Growth Des 11:3463-3471.
17. Bonnert RV, Brown RC, Chapman D, Cheshire DR, Dixon J, Ince F, Kinchin EC, Lyons AJ, Davis AM, Hallam C, Harper ST, Unitt JF, Dougall IG, Jackson DM, McKechnie K, Young A, Simpson WT. 1998. Dual D-2-receptor and beta(2)-adrenoceptor agonists for the treatment of airway diseases. 1. Discovery and biological evaluation of some 7-(2-aminoethyl)-4-hydroxybenzothiazol-2(3H)-one analogues. J Med Chem 41:4915-4917.
18. Giles ME, Thomson C, Eyley SC, Cole AJ, Goodwin CJ, Hurved PA, Morlin AJG, Tornos J, Atkinson S, Just C, Dean JC, Singleton JT, Longton AJ, Woodland I, Teasdale A, Gregertsen B, Else H, Athwal MS, Tatterton S, Knott JM, Thompson N, Smith SJ. 2004. Development of a manufacturing process for sibenadet hydrochloride, the active ingredient of Viozan. Org Proc Res Dev 8:628-642.
19. Cosgrove SD, Steele G, Austin TK, Plumb AP, Stensland B, Ferrari E, Roberts KJ. 2005. Understanding the polymorphic behavior of sibenadet hydrochloride through detailed studies integrating structural and dynamical assessment. J Pharm Sci 94:2403-2415.
20. Sakellariou D, Lesage A, Hodgkinson P, Emsley L. 2000. Homonuclear dipolar decoupling in solid-state NMR using continuous phase modulation. Chem Phys Lett 319:253-260.
21. Elena B, de Paepe G, Emsley L. 2004. Direct spectral optimisation of proton-proton homonuclear dipolar decoupling in solid-state NMR. Chem Phys Lett 398:532-538.
22. Sommer W, Gottwald J, Demco DE, Spiess HW. 1995. Dipolar heteronuclear multiple-quantum NMR-spectroscopy in rotating solids. J Magn Reson Ser A 113:131-134.
23. Schnell I, Lupulescu A, Hafner S, Demco DE, Spiess HW. 1998. Resolution enhancement in multiple-quantum MAS NMR spectroscopy. J Magn Reson 133:61-69.
24. 1H double-quantum CRAMPS NMR spectroscopy. J Am Chem Soc 126:13230-13231.
25. Hohwy M, Jakobsen HJ, Eden M, Levitt MH, Nielsen NC. 1998. Broadband dipolar recoupling in the nuclear magnetic resonance of rotating solids: A compensated C7 pulse sequence. J Chem Phys 108:2686-2694.
26. Clark SJ, Segall MD, Pickard CJ, Hasnip PJ, Probert MJ, Refson K, Payne MC. 2005. First principles methods using CASTEP. Z Kristall 220:567-570.
27. Perdew JP, Burke K, Ernzerhof M. 1996. Generalized gradient approximation made simple. Phys Rev Lett 77:3865-3868.
28. Vanderbilt D. 1990. Soft self-consistent pseudopotentials in a generalized eigenvalue formalism. Phys Rev B 41:7892-7895.
29. Pickard CJ, Mauri F. 2001. All-electron magnetic response with pseudopotentials: NMR chemical shifts. Phys Rev B 63:245101.
30. Yates JR, Pickard CJ, Mauri F. 2007. Calculation of NMR chemical shifts for extended systems using ultrasoft pseudopotentials. Phys Rev B 76:024401.
31. Harris RK, Hodgkinson P, Pickard CJ, Yates JR, Zorin V. 2007. Chemical shift computations on a crystallographic basis: Some reflections and comments. Magn Reson Chem 45:S174-S186.
32. Veshtort M, Griffin RG. 2006. SPINEVOLUTION: A powerful tool for the simulation of solid and liquid state NMR experiments. J Magn Reson 178:248-282.
33. 1H double-quantum MAS NMR: Insight from multi-spin density-matrix simulations. Phys Chem Chem Phys 11:6941-6952.
34. Madhu PK. 2009. High-resolution solid-state NMR spectroscopy of protons with homonuclear dipolar decoupling schemes under magic-angle spinning. Solid State Nucl Magn Reson 35:2-11.
35. Lesage A. 2009. Recent advances in solid-state NMR spectroscopy of spin I = 1/2 nuclei. Phys Chem Chem Phys 11:6876-6891.
36. 1H NMR Spectroscopy of Solids. Ann Rep NMR Spectrosc 72:185-223.
37. Brown SP, Spiess HW. 2001. Advanced solid-state NMR methods for the elucidation of structure and dynamics of molecular, macromolecular, and supramolecular systems. Chem Rev 101:4125-4155.
38. Brown SP. 2009. Recent advances in solid-state MAS NMR methodology for probing structure and dynamics in polymeric and supramolecular systems. Macromol Rapid Commun 30:688-716.
39. Schmidt J, Hoffmann A, Spiess HW, Sebastiani D. 2006. Bulk chemical shifts in hydrogen-bonded systems from first-principles calculations and solid-state-NMR. J Phys Chem B 110:23204-23210.
40. Uldry AC, Griffin JM, Yates JR, Perez-Torralba M, Maria MDS, Webber AL, Beaumont MLL, Samoson A, Claramunt RM, Pickard CJ, Brown SP. 2008. Quantifying weak hydrogen bonding in uracil and 4-cyano-4′-ethynylbiphenyl: A combined computational and experimental investigation of NMR chemical shifts in the solid state. J Am Chem Soc 130:945-954.
41. 13C solid-state MAS NMR spectroscopy and GIPAW chemical-shift calculations. J Phys Chem A 114:10435-10442.
42. Yates JR, Pham TN, Pickard CJ, Mauri F, Amado AM, Gil AM, Brown SP. 2005. An investigation of weak CH...O hydrogen bonds in maltose anomers by a combination of calculation and experimental solid-state NMR spectroscopy. J Am Chem Soc 127:10216-10220.
43. Madhu PK, Vinogradov E, Vega S. 2004. Multiple-pulse and magic-angle spinning aided double-quantum proton solid-state NMR spectroscopy. Chem Phys Lett 394:423-428.
44. 1H proximities in solids. J Magn Reson 196:88-91.
45. 1H homonuclear dipolar recoupling NMR spectra of biological solids at MAS rates up to 67 kHz. J Magn Reson 199:111-114.
46. Harris RK, Olivieri AC. 1992. Quadrupolar effects transferred to spin-1/2 magic-angle spinning spectra of solids. Prog Nucl Magn Reson Spectrosc 24:435-456.
47. 1H NMR. Mol Phys 104:293-304.
48. 1H magic-angle spinning NMR. J Chem Phys 125:144508.
49. Elena B, Emsley L. 2005. Powder crystallography by proton solid-state NMR spectroscopy. J Am Chem Soc 127:9140-9146.
50. Elena B, Pintacuda G, Mifsud N, Emsley L. 2006. Molecular structure determination in powders by NMR crystallography from proton spin diffusion. J Am Chem Soc 128:9555-9560.
51. Pickard CJ, Salager E, Pintacuda G, Elena B, Emsley L. 2007. Resolving structures from powders by NMR crystallography using combined proton spin diffusion and plane wave DFT calculations. J Am Chem Soc 129:8932-8933.
52. Gorelik T, Matveeva G, Kolb U, Schleuss T, Kilbinger AFM, van de Streek J, Bohle A, Brunklaus G. 2010. H-bonding schemes of di- and tri-p-benzamides assessed by a combination of electron diffraction, X-ray powder diffraction and solid-state NMR. CrystEngComm 12:1824-1832.