Solid state properties of 1,2-epoxy-3-(2-methoxyphenyloxy)-propane - Valuable intermediate in non-racemic drug synthesis

Tetrahedron Asymmetry

Volumn 16, Issue 20, 2005, Pages 3361-3366

  Bredikhin, Alexander A ^a   Strunskaya, Elena I ^a   Zakharychev, Dmitry V ^a   Krivolapov, Dmitry B ^a   Litvinov, Igor A ^a   Bredikhina, Zemfira A ^a  

^a A E ARBUZOV INSTITUTE OF ORGANIC AND PHYSICAL CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 EPOXY 3 (2 METHOXYPHENYLOXY)PROPANE; GUAIFENESIN; MEPHENOXALONE; METHOCARBAMOL; MOPROLOL; PROPANE; RANOLAZINE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; CRYSTALLIZATION; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; RACEMIC MIXTURE; SOLID STATE; THERMAL ANALYSIS; X RAY ANALYSIS;

EID: 27644507024     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.09.013     Document Type: Article

References (37)

1. R.M. Hanson Chem. Rev. 91 1991 437 476
2. N. Kasai, T. Suzuki, and Y. Furukawa J. Mol. Catal. B-Enzym. 4 1998 237 252
3. C. Lauret Tetrahedron: Asymmetry 12 2001 2359 2383
4. C. Campo, E.F. Llama, J.L. Bermudez, and J.V. Sinisterra Biocatal. Biotransform. 19 2001 163 180
5. For a review see: R. Mehvar, and D.R. Brocks J. Pharm. Pharm. Sci. 4 2001 185 200
6. For the special case of moprolol see: C. Harvengt, and J.P. Desager Int. J. Clin. Pharmacol. Ther. Toxicol. 20 1982 57 61
7. L. Merlo, B. Brusoni, E. Mussini, and P. Ghirardi Boll. Soc. Ital. Cardiol. 25 1980 955 961
8. Ferrari, G.; Vecchietti, V. US Pat. 4 683 245, 1987.
9. E. Souri, M. Sharifzadeh, H. Farsam, and N. Gharavi J. Pharm. Pharmacol. 51 1999 853 855
10. W.L. Nelson, J.E. Wennerstrom, and S.R. Sankar J. Org. Chem. 42 1977 1006 1012
11. J.M. Caroon, R.D. Clark, A.F. Kluge, J.T. Nelson, A.M. Strosberg, S.H. Unger, A.D. Michel, and R.L. Whiting J. Med. Chem. 24 1981 1320 1328
12. U. Ader, and M.P. Schneider Tetrahedron: Asymmetry 3 1992 521 524
13. A. Kamal, M. Arifuddin, and M.V. Rao Tetrahedron: Asymmetry 10 1999 4261 4264
14. A.A. Bredikhin, E.I. Strunskaya, V.G. Novikova, N.M. Azancheev, D.R. Sharafutdinova, and Z.A. Bredikhina Russ. Chem. Bull., Int. Ed. 53 2004 213 218
15. [ Izv. Akad. Nauk, Ser. Khim. 2004 203 208 (in Russian)]
16. J. Jacques, A. Collet, and S.H. Wilen Enantiomers, Racemates and Resolutions 1994 Krieger Publishing Company Malabar, FL 447
17. A. Collet, M.-J. Brienne, and J. Jacques Chem. Rev. 80 1980 215 230
18. A.A. Bredikhin, S.N. Lazarev, Z.A. Bredikhina, D.V. Savel'ev, I.I. Vandyukova, A.T. Gubaidullin, and I.A. Litvinov Russ. Chem. Bull., Int. Ed. 52 2003 846 852
19. [ Izv. Akad. Nauk, Ser. Khim. 2003 806 811 (in Russian)]
20. G.W.H. Höhne, H.K. Cammenga, W. Eysel, E. Gmelin, and W. Hemminger Thermochim. Acta 160 1990 1 12
21. H.E. Gallis, F. Bougrioua, H.A.J. Oonk, P.J. van Ekeren, and J.C. van Miltenburg Thermochim. Acta 274 1996 231 242
22. A.A. Bredikhin, E.I. Strunskaya, N.M. Azancheev, and Z.A. Bredikhina Russ. Chem. Bull., Int. Ed. 47 1998 174 176
23. [ Izv. Akad. Nauk, Ser. Khim. 1998 172 175 (in Russian)]
24. Z.J. Li, M.T. Zell, E.J. Munson, and D.J.W. Grant J. Pharm. Sci. 88 1999 337 346
25. S. Houllemare-Druot, and G. Coquerel J. Chem. Soc., Perkin Trans. 2 1998 2211 2220
26. F. Dufour, G. Perez, and G. Coquerel Bull. Chem. Soc. Jpn. 77 2004 79 86
27. Crosby, J. Eur. Pat. Appl. 441 471, 1991.
28. Chem. Abstr. 115 1991 231857
29. R. Ananth, J. Chen, and W. Shum Tetrahedron: Asymmetry 6 1995 317 320
30. S.-I. Yamada, K. Morimatsu, R. Yoshioka, Y. Ozaki, and H. Seko Tetrahedron: Asymmetry 9 1998 1713 1721
31. S.E. Schaus, B.D. Brandes, J.F. Larrow, M. Tokunaga, K.B. Hansen, A.E. Gould, M.E. Furrow, and E.N. Jacobsen J. Am. Chem. Soc. 124 2002 1307 1315
32. K. Kopka, S. Wagner, B. Riemann, M.P. Law, C. Puke, S.K. Luthra, V.W. Pike, T. Wichter, W. Schmitz, O. Schober, and M. Schäfers Bioorg. Med. Chem. 11 2003 3513 3527
33. Beilsteins Handbuch Der Organischen Chemie, I Vol. 17 1934 Springer Berlin, Heidelberg p 51
34. K. Audouze, E.O. Nielsen, and D. Peters J. Med. Chem. 47 2004 3089 3104
35. A. Altomare, G. Cascarano, C. Giacovazzo, and D. Viterbo Acta Crystallogr. Sec. A. 47 1991 744 745
36. Sheldrick, G. M. shelxl97 a computer program for crystal structure determination; University of Gottingen, 1997.
37. L.H. Straver, and A.J. Schierbeek MolEN. Structure Determination System Vols. 1 and 2 1994 Nonius B. V. Delft. Netherlands