Structure determination of enalapril maleate Form II from high-resolution X-ray powder diffraction data

Journal of Pharmaceutical Sciences

Volumn 92, Issue 9, 2003, Pages 1844-1853

  Kiang, Y H ^a   Huq, Ashfia ^b   Stephens, Peter W ^b   Xu, Wei ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

^b STONY BROOK UNIVERSITY   (United States)

Author keywords

Crystal structure determination; Enalapril maleate; Monte Carlo Simulated Annealing; Polymorphism; X ray powder diffraction (XRPD) pattern

Indexed keywords

DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; ENALAPRIL MALEATE;

ARTICLE; BINDING SITE; CALCULATION; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; DRUG DETERMINATION; DRUG POTENCY; DRUG STRUCTURE; ENERGY; ENZYME ACTIVE SITE; FOURIER TRANSFORMATION; HYDROGEN BOND; INFRARED SPECTROSCOPY; MATHEMATICAL COMPUTING; MOLECULAR DYNAMICS; MONTE CARLO METHOD; PROTEIN CONFORMATION; RAMAN SPECTROMETRY; REDUCTION; THERMAL ANALYSIS; X RAY POWDER DIFFRACTION;

EID: 0042285950     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1002/jps.10430     Document Type: Article

References (38)

1. Ondetti MA, Rubin B, Cushman DW. 1977. Design of specific inhibitors of angiotensin-converting enzyme: New class of orally active antihypertensive agents. Science 196:441-444.
2. Patchett AA, Harris E, Tristram EW, Wyvratt MJ, Wu MT, Taub D, Peterson ER, Ikeler TJ, ten Broeke J, Payne LG, Ondeyka DL, Thorsett ED, Greenlee WJ, Lohr NS, Hoffsommer RD, Joshua H, Ruyle WV, Rothrock JW, Aster SD, Maycock AL, Robinson FM, Hirschmann R, Sweet CS, Ulm EH, Gross DM, Vassil TC, Stone CA. 1980. A new class of angiotensin-converting enzyme inhibitors. Nature 288: 280-283.
3. Fujinaga M, James MNG. 1980. SQ 14,225: 1-(D-3-mercapto-2-methylpropionyl)L-proline. Acta Crystallogr B 36:3196-3199.
4. Précigoux G, Geoffre S, Leroy F. 1986. N-(1-ethoxy-carbonyl-3-phenylpropyl)-L-alanyl-L-prolinium-hydrogen maleate (1/1), enalapril (MK-421). Acta Crystallogr C 42:1022-1024.
5. In Y, Shibata M, Doi M, Ishida T, Inoue M, Sasaki Y, Morimoto S. 1986. Conformational similarities of angiotensin-converting enzyme inhibitors: X-ray crystal structures. Chem Commun 473-474.
6. Wyvratt M, Tristram EW, Ikeler TJ, Lohr NS, Joshua H, Springer JP, Byron HA, Patchett AA. 1984. Reductive amination of ethyl 2-oxo-4-phenyl-butamoate with L-alanyl-L-proline. Synthesis of enalapril maleate. J Org Chem 49:2816-2819.
7. Paulus EF, Hennings R, Urbach H. 1987. Structure of the angiotensin-converting enzyme inhibitor ramiprilat (HOE 498 diacid). Acta Crystallogr C 43:941-945.
8. Luger P, Schnorrenberg G. 1987. A highly potent angiotensin converting enzyme inhibitor: (S,S,S)-5-[N-(1-carboxy-3-phenylpropyl)alanyl]-4,5,6,7-tet-rahydrothieno[3,2-c] pyridine-4-carboxylic acid monohydrate, SBG 107. Acta Crystallogr C 43: 484-488.
9. Attwood MR, Francis RJ, Hassall CH, Krohn A, Lawton G, Natoff IL, Nixon JS, Redshaw S, Thomas WA. 1984. New potent inhibitors of angiotensin converting enzyme. FEBS Lett 165:201-206.
10. Attwood MR, Hassall CH, Krohn A, Lawton G, Redshaw SJ. 1986. The design and synthesis of the angiotensin-converting enzyme inhibitor cilazapril and related bicyclic compounds. J Chem Soc Perkin Trans 1011-1019.
11. Thorsett ED, Harris EE, Aster SD, Peterson ER, Synder JP, Springer JP, Hirshfield J, Tristram EW, Patchett AA, Ulm EH, Vassil TC. 1986. Conformationally restricted inhibitors of angiotensin converting enzyme: Synthesis and computations. J Med Chem 29:251-260.
12. Pascard C, Guilhem J, Vincent M, Rémond G, Portevin B, Laubie M. 1991. Configuration and preferential solid-state conformations of perindoprilat (S-9780). Comparison with the crystal structures of other ACE inhibitors and conclusions related to structure-activity relationships. J Med Chem 34:663-669.
13. 13C NMR. J Mol Struct 238: 325-334.
14. Ip DP, Brenner GS, Stevenson JM, Lindenbaum S, Douglas AW, Klein SD, McCauley JA. 1986. High resolution spectroscopic evidence and solution calorimetry studies on the polymorphs of enalapril maleate. Int J Pharm 28:83-191.
15. Byrn SR, Pfeiffer RR, Stowell JG. 1999. Solid-state chemistry of drugs, 2nd ed. West Lafayette, IN: SSCI, Inc.
16. Haleblian J, McCrone W. 1969. Pharmaceutical applications of polymorphism. J Pharm Sci 58:911-929.
17. David WIF, Shankland K, Shankland N. 1998. Routine determination of molecular crystal structures from powder diffraction data. Chem Commun 931-932.
18. Engel GE, Wilke S, König O, Harris KDM, Leusen FJJ. 1999. PowderSolve: A complete package for crystal structure solution from powder diffraction patterns. J Appl Crystallogr 32:1169-1179.
19. Pagola S, Stephens PW. 2000. Towards the solution of organic crystal structures by powder diffraction. Mater Sci Forum 321:40-45. Program and documentation available at http://powder.physics.sunysb.edu.
20. Dinnebier RE, Sieger P, Herbert N, Shankland K, David WIF. 2000. Structure characterization of three crystalline modifications of telmisartan by single crystal and high-resolution X-ray powder diffraction. J Pharm Sci 89:1465-1478.
21. Giovannini J, Perrin M-A, Louër D, Leveiller F. 2001. Ab initio crystal structure determination of three pharmaceutical compounds from X-ray powder diffraction data. Mater Sci Forum 378-381: 582-587.
22. Kariuki BM, Psallidas K, Harris KDM, Johnston RL, Lancaster RW, Staniforth SE, Cooper SM. 1999. Structure determination of a steroid directly from powder diffraction data. Chem Commun 1677-1678.
23. Tedesco E, Giron D, Pfeffer S. 2002. Crystal structure elucidation and morphology study of pharmaceuticals in development. CrystEngComm 4:393-400.
24. 15N solid-state NMR: A question of polymorphism in a given unit cell. J Phys Chem B 105: 5818-5826.
25. Andreev YG, MacGlashan GS, Bruce PG. 1997. Ab initio solution of a complex crystal structure from powder-diffraction data using simulated-annealing method and a high degree of molecular flexibility. Phys Rev B 55:12011-12017.
26. Putz H, Cshon JC, Jansen M. 1999. Combined method for ab initio structure solution from powder diffraction data. J Appl Crystallogr 32:864-870.
27. Coelho AA. 2000. Whole-profile structure solution from powder diffraction data using simulated annealing. J Appl Crystallogr 33:899-908.
28. Pagola S, Stephens PW, Bohle DS, Kosar AD, Madsen SK. 2000. The structure of malaria pigment α-haematin. Nature 404:307-310.
29. Visser JW. 1969. A fully automatic program for finding the unit cell from powder data. J Appl Crystallogr 2:89-95.
30. Material studio. 2001. San Diego, CA: Accelrys Inc.
31. Larson AC, von Dreele RB. 2000. GSAS: General structure analysis system. Los Alamos National Laboratory. Report LAUR 86-748.
32. 2. Computer simulation software package. 2001. San Diego, CA: Accelrys Inc.
33. Mayo SL, Olafson BD, Goddard WA III. 1990. DREDING: A generic force filed for molecular simulations. J Phys Chem 94:8897-8909.
34. Buttar D, Charlton MH, Docherty R, Starbuck J. 1998. Theoretical investigations of conformational aspects of polymorphism. Part 1: o-acetamidobenzamide. J Chem Soc Perkin Trans 2:763-772.
35. Payne RS, Roberts RJ, Rowe RC, Docherty R. 1999. Examples of successful crystal structure prediction: Polymorphs of primidone and progesterone. Int J Pharm 177:231-245.
36. Roberts RJ, Payne RS, Rowe RC. 2000. Mechanical property predictions for polymorphs of sulphathiazole and carbamazepine. Eur J Pharm Sci 9:277-283.
37. Frisch MJ, Trucks GW, Schlegel HB, Gill PMW, Johnson BG, Wong MW, Foresman JB, Robb MA, Head-Gordan M, Replogle ES, Gomperts R, Andres JL, Raghavachari K, Binkley JS, Gonzalez C, Martin RL, Fox DJ, Defrees DJ, Baker J, Stewart JJP, Pople JA, 1993. Gaussian 92/DFT, revision G.1. Pittsburgh, PA: Gaussian Inc.
38. Kitaigoroskii AI. 1961. Organic chemical crystallography. New York: Consultant Bureau.