An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals

Beilstein Journal of Organic Chemistry

Volumn 7, Issue , 2011, Pages 442-495

  Baumann, Marcus ^a   Baxendale, Ian R ^a   Ley, Steven V ^a   Nikbin, Nikzad ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Five membered rings; Heterocycles; Medicinal chemistry; Pharmaceuticals; Synthesis

Indexed keywords

EID: 79955053789     PISSN: 18605397     EISSN: 18605397     Source Type: Journal    
DOI: 10.3762/bjoc.7.57     Document Type: Review

References (142)

1. MIDAS World Review (TM), January 2009 - December 2009, IMS Health Incorporated.
2. McGrath, N. A.; Brichacek, M.; Njardarson, J. T. J. Chem. Educ. 2010, 87, 1348-1349. doi:10.1021/ed1003806.
3. Roth, B. D.; Blankley, C. J.; Chucholowski, A. W.; Ferguson, E.; Hoefle, M. L.; Ortwine, D. F.; Newton, R. S.; Sekerke, C. S.; Sliskovic, D. R.; Wilson, M. J. Med. Chem. 1991, 34, 357-366. doi:10.1021/jm00105a056.
4. Roth, B. D. Trans-6-[2-(3- or 4-carboxamido-substituted pyrrol-1-yl)alkyl]-4-hydroxypyran-2-one Inhibitors of Cholesterol Synthesis. U.S. Patent 4, 681, 893, July 21, 1987.
5. Sagyam, R. R.; Padi, P. R.; Ghanta, M. R.; Vurimidi, H. J. Heterocycl. Chem. 2007, 44, 923-926. doi:10.1002/jhet.5570440429.
6. Butler, D. E.; Deering, C. F.; Millar, A.; Nanninga, T. N.; Roth, B. D. Improved Process for Trans-6-[2-(substituted-pyrrole-1-yl)alkyl]pyran-2-one Inhibitors of Cholesterol Synthesis. WO Patent 89/07598, Aug 24, 1989.
7. Butler, D. E.; Le, T. V.; Millar, A.; Nanninga, T. N. Process for the Synthesis of (5R)-1, 1-Dimethylethyl-6-cyano-5-hydroxy-3-oxohexanoate. U.S. Patent 5, 155, 251, Oct 13, 1992.
8. Gajiwala, K. S.; Wu, J. C.; Christensen, J.; Deshmukh, G. D.; Diehl, W.; DiNitto, J. P.; English, J. M.; Greig, M. J.; He, Y.-A.; Jacques, S. L.; Lunney, E. A.; McTigue, M.; Molina, D.; Quenzer, T.; Wells, P. A.; Yu, X.; Zhang, Y.; Zou, A.; Emmett, M. R.; Marshall, A. G.; Zhang, H.-M.; Demetri, G. D. Proc. Natl. Acad. Sci. U. S. A. 2009, 106, 1542-1547. doi:10.1073/pnas.0812413106.
9. Lednicer, D. Indolones. In The Organic Chemistry of Drug Synthesis, Vol. 7; Wiley-Interscience: Hoboken, New Jersey, 2008; pp 148-152.
10. Vaidyanathan, R. The SUTENT® Story. In Process Chemistry in the Pharmaceutical Industry; Gadamasetti, K.; Braish, T., Eds.; Taylor & Francis: Boca Raton, Florida, 2008; Vol. 2, pp 49-64.
11. Pete, B.; Bitter, I.; Szántay, C. Jr.; Schön, I.; Töke, L. Heterocycles 1998, 48, 1139-1149. doi:10.3987/COM-97-8087.
12. Oxford, A. W. Indole Derivative. U.S. Patent 5, 037, 845, Aug 6, 1991.
13. Japp, F. R.; Klingemann, F. Chem. Ber. 1887, 20, 2942-2944. doi:10.1002/cber.188702002165.
14. Pete, B.; Bitter, I.; Harsányi, K.; Töke, L. Heterocycles 2000, 53, 665-673. doi:10.3987/COM-99-8815.
15. Kim, D.-W.; Ko, Y. K.; Kim, S. H. Synthesis 1992, 12, 1203-1204. doi:10.1055/s-1992-26333.
16. Albinson, F. D.; MacKinnon, J. W. M.; Crookes, D. L. Preparation of Indole Derivatives. U.S. Patent 5, 103, 020, April 7, 1992.
17. Zhou, G.; Ting, P.; Aslanian, R.; Piwinski, J. J. Org. Lett. 2008, 10, 2517-2520. doi:10.1021/ol800785g.
18. Blatcher, P.; Carter, M.; Hornby, R.; Owen, M. Process for the Preparation of N-Methyl-3-(1-methyl-4-piperidinyl)-4-indole-5- ethanesulphonamide. WO Patent 95/091166, April 6, 1995.
19. Buckingham, J.; Glen, R. C.; Hill, A. P.; Hyde, R. M.; Martin, G. R.; Robertson, A. D.; Salmon, J. A.; Woollard, P. M. J. Med. Chem. 1995, 38, 3566-3580. doi:10.1021/jm00018a016.
20. Voslar, M.; Zatopkova, M.; Ridvan, L.; Pekarek, T. A. Method for the Preparation of Zolmitriptan. WO Patent 2008/104134, Sept 4, 2008.
21. Baker, R.; Matassa, V. G.; Street, L. J. Triazole Containing Indole Derivatives. U.S. Patent 5, 298, 520, March 29, 1994.
22. Street, L. J.; Baker, R.; Davey, W. B.; Guiblin, A. R.; Jelley, R. A.; Reeve, A. J.; Routledge, H.; Sternfeld, F.; Watt, A. P. J. Med. Chem. 1995, 38, 1799-1810. doi:10.1021/jm00010a025.
23. Koilpillai, J. P.; Subramanian, M.; Mallela, U.; Boddu, V. B.; Dandala, R.; Meenakshisunderam, S. An Improved Process for the Preparation of Rizatriptan. WO Patent 2008/075163, June 26, 2008.
24. Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652-7662. doi:10.1021/jo9803277.
25. Chen, C.-y.; Lieberman, D. R.; Larsen, R. D.; Reamer, R. A.; Verhoeven, T. R.; Reider, P. J.; Cottrell, I. F.; Houghton, P. G. Tetrahedron Lett. 1994, 35, 6981-6984. doi:10.1016/0040-4039(94)88204-5.
26. Muddasani, P. R.; Hanumara, S. R.; Kagitha, R.; Nannapaneni, V. C. Improved Process for the Preparation of Rizatriptan Benzoate. WO Patent 2006/137083, Dec 28, 2006.
27. Chen, C. Y.; Larsen, R. D.; Verhoeven, T. R. Palladium Catalyzed Ring Closure of Triazolyl Tryptamine. WO Patent 95/32197, Nov 30, 1995.
28. Macor, J. E.; Wythes, M. J. Indole Derivatives. U.S. Patent 5, 545, 644, Aug 13, 1996.
29. Perkins, J. F. Process for the Preparation of 3-Acylindoles. Eur. Patent 1088817A2, April 4, 2001.
30. Ashcroft, C. P. Modified Fischer Indole Synthesis for Eletriptan. WO Patent 2005/103035, Nov 3, 2005.
31. Bischler, A. Chem. Ber. 1892, 25, 2860-2879. doi:10.1002/cber. 189202502123.
32. Sridharan, V.; Perumal, S.; Avendaño, C.; Menéndez, J. C. Synlett 2006, 2006, 91-95. doi:10.1055/s-2005-922760. (Pubitemid 43082396)
33. Repič, O.; Prasad, K.; Lee, G. T. Org. Process Res. Dev. 2001, 5, 519-527. doi:10.1021/op0100450.
34. Walkup, R. E.; Linder, J. Tetrahedron Lett. 1985, 26, 2155-2158. doi:10.1016/S0040-4039(00)98949-4.
35. Godfrey, N.; Coates, I. H.; Bell, J. A.; Humber, D. C.; Ewan, G. B. Process for Preparing N-Heterocyclic Compounds. U.S. Patent 4, 957, 609, Sept 18, 1990.
36. Iida, H.; Yuasa, Y.; Kibayashi, C. J. Org. Chem. 1980, 45, 2938-2942. doi:10.1021/jo01303a003.
37. Oxford, A. W.; Eldred, C. D.; Coates, I. H.; Bell, J. A.; Humber, D. C.; Ewan, G. B. Process for Preparing Tetrahydrocarbazolones. U.S. Patent 4, 739, 072, April 19, 1988.
38. Daugan, A. C.-M. Tetracyclic Derivatives; Process of Preparation and Use. U.S. Patent 5, 859, 006, Jan 12, 1999.
39. Daugan, A. C.-M. Tetracyclic Derivatives, Process of Preparation and Use. U.S. Patent 6, 025, 494, Feb 15, 2000.
40. Shi, X.-X.; Liu, S.-L.; Xu, W.; Xu, Y.-L. Tetrahedron: Asymmetry 2008, 19, 435-442. doi:10.1016/j.tetasy.2007.12.017.
41. Yue, T.-L.; Cheng, H.-Y.; Lysko, P. G.; McKenna, P. J.; Feuerstein, R.; Gu, J.-L.; Lysko, K. A.; Davis, L. L.; Feuerstein, G. J. Pharmacol. Exp. Ther. 1992, 263, 92-98.
42. Lauer, K.; Kiegel, E. Process for the Preparation of 4-Hydroxycarbazole. U.S. Patent 4, 273, 711, June 16, 1981.
43. Huang, S.; Yu, H.; Sun, X.; Gao, W. Zhongguo Yaowu Huaxue Zazhi 2000, 10, 293-295.
44. Demerson, C. A.; Humber, L. G.; Dobson, T.; Jirkovsky, I. L. Certain pyrano[3, 4-B]indoles and thiopyrano[3, 4-B]indoles. U.S.Patent 3, 393, 178, Feb 17, 1976.
45. Demerson, C. A.; Humber, L. G. Process for Preparing 1, 8-Diethyl-1, 3, 4, 9-tetrahydropyrano(3, 4-b)-indole-1-acetic acid, Etodolac. U.S. Patent 4, 585, 877, April 29, 1986.
46. Vincenzo, G.; Franco, P. 3-(2-Trialkylsilyloxy)ethyl-7-ethyl-1H-indoles and Method for their Preparation. U.S. Patent 5, 599, 946, Feb 4, 1997.
47. Woods, M.; Dyer, U. C.; Andrews, J. F.; Morfitt, C. N.; Valentine, R.; Sanderson, J. Org. Process Res. Dev. 2000, 4, 418-426. doi:10.1021/op000014p.
48. De Gasparo, M.; Catt, K. J.; Inagami, T.; Wright, J. W.; Unger, T. Pharmacol. Rev. 2000, 52, 415-472.
49. Bühlmayer, P.; Furet, P.; Criscione, L.; de Gasparo, M.; Whitebread, S.; Schmidlin, T.; Lattmann, R.; Wood, J. Bioorg. Med. Chem. Lett. 1994, 4, 29-34. doi:10.1016/S0960-894X(01)81117-3. (Pubitemid 24128681)
50. Shi, Y.-J.; Frey, L. F.; Tschaen, D. M.; Verhoeven, T. R. Synth. Commun. 1993, 23, 2623-2630. doi:10.1080/00397919308012598.
51. Griffiths, G. J.; Hauck, M. B.; Imwinkelried, R.; Kohr, J.; Roten, C. A.; Stucky, G. C.; Gosteli, J. J. Org. Chem. 1999, 64, 8084-8089. doi:10.1021/jo9824910. (Pubitemid 29529211)
52. Zhong, Y.-L.; Lee, J.; Reamer, R. A.; Askin, D. Org. Lett. 2004, 6, 929-931. doi:10.1021/ol036423y. (Pubitemid 38402664)
53. Yanagisawa, H.; Fujimoto, K.; Amemiya, Y.; Shimoji, Y.; Kanazaki, T.; Koike, H.; Sada, T. Angiotensin II Antagonist 1-Biphenylmethylimidazole Compounds and their Therapeutic Use. U.S. Patent 5, 616, 599, April 1, 1997.
54. Yanagisawa, H.; Amemiya, Y.; Kanazaki, T.; Shimoji, Y.; Fujimoto, K.; Kitahara, Y.; Sada, T.; Mizuno, M.; Ikeda, M.; Miyamoto, S.; Furukawa, Y.; Koike, H. J. Med. Chem. 1996, 39, 323-338. doi:10.1021/jm950450f. (Pubitemid 26027038)
55. Tyers, M. B.; Coates, I. H.; Humber, D. C.; Ewan, G. B.; Bell, J. A. Method for Treating Nausea and Vomiting. U.S. Patent 4, 753, 789, June 28, 1988.
56. Gitis, K. M.; Raevskaya, N. I.; Isagulyants, G. V. Russ. Chem. Bull. 1992, 41, 1551-1554. doi:10.1007/BF00863570.
57. Elz, S.; Heil, W. L. Bioorg. Med. Chem. Lett. 1995, 5, 667-672. doi:10.1016/0960-894X(95)00092-8.
58. Uchida, M.; Morita, S.; Chihiro, M.; Kanbe, T.; Yamasaki, K.; Yabuuchi, Y.; Nakagawa, K. Chem. Pharm. Bull. 1989, 37, 1517-1523.
59. Lindberg, P. L.; Von Unge, S. Compositions. U.S. Patent 5, 714, 504, Feb 3, 1998.
60. Cotton, H.; Kronström, A.; Mattson, A.; Möller, E. Novel Form of S-Omeprazole. WO Patent 98/54171, Dec 3, 1998.
61. Rainer, G.; Riedel, R.; Senn-Biffinger, J.; Klemm, K.; Schaefer, H.; Figaia, V. Fluoroalkoxysubstituted Pyridylmethylthio-(or Sulfinyl)- benzimidazoles. Eur. Patent 134400B1, March 24, 1993.
62. Hashimoto, H.; Hanaoka, T.; Kato, M. Production Method of Aminobenzene Compound. Eur. Patent 0881212B1, Dec 2, 1998.
63. Snieckus, V. Chem. Rev. 1990, 90, 879-933. doi:10.1021/cr00104a001.
64. Porcs-Makkay, M.; Mezei, T.; Simig, G. Org. Process Res. Dev. 2007, 11, 490-493. doi:10.1021/op700041z.
65. Ries, U. J.; Mihm, G.; Narr, B.; Hasselbach, K. M.; Wittneben, H.; Entzeroth, M.; van Meel, J. C. A.; Wienen, W.; Hauel, N. H. J. Med. Chem. 1993, 36, 4040-4051. doi:10.1021/jm00077a007. (Pubitemid 24024676)
66. Reddy, K. S.; Srinivasan, N.; Reddy, C. R.; Kolla, N.; Anjaneyulu, Y.; Venkatraman, S.; Bhattacharya, A.; Mathad, V. T. Org. Process Res. Dev. 2007, 11, 81-85. doi:10.1021/op060200g.
67. Rossey, G.; Long, D. Process for the Preparation of Imidazopyridines. U.S. Patent 4, 794, 185, Dec 27, 1988.
68. George, P.; Rossey, G.; Depoortere, H.; Mompon, B.; Allen, J.; Wick, A. Farmaco 1991, 46, 277-288.
69. Chernyak, N.; Gevorgyan, V. Angew. Chem., Int. Ed. 2010, 49, 2743-2746. doi:10.1002/anie.200907291.
70. Zhu, J.; Song, X.; Lin, H.-P.; Young, D. C.; Yan, S.; Marquez, V. E.; Chen, C.-S. J. Natl. Cancer Inst. 2002, 94, 1745-1757. doi:10.1093/jnci/94.23. 1745.
71. Rimon, G.; Sidhu, R. S.; Lauver, D. A.; Lee, J. Y.; Sharma, N. P.; Yuan, C.; Frieler, R. A.; Trievel, R. C.; Lucchesi, B. R.; Smith, W. L. Proc. Natl. Acad. Sci. U. S. A. 2010, 107, 28-33. doi:10.1073/pnas.0909765106.
72. Penning, T. D.; Talley, J. J.; Bertenshaw, S. R.; Carter, J. S.; Collins, P. W.; Docter, S.; Graneto, M. J.; Lee, L. F.; Malecha, J. W.; Miyashiro, J. M.; Rogers, R. S.; Rogier, D. J.; Yu, S. S.; Anderson, G. D.; Burton, E. G.; Cogburn, J. N.; Gregory, S. A.; Koboldt, C. M.; Perkins, W. E.; Seibert, K.; Veenhuizen, A. W.; Zhang, Y. Y.; Isakson, P. C. J. Med. Chem. 1997, 40, 1347-1365. doi:10.1021/jm960803q. (Pubitemid 27198082)
73. Talley, J. J.; Penning, T. D.; Collins, P. W.; Rogier, D. J. Jr.; Malecha, J. W.; Miyashiro, J. M.; Bertenshaw, S. R.; Khanna, I. K.; Granets, M. J.; Rogers, R. S.; Carters, J. S.; Docter, S. H. Substituted Pyrazolylbenzenesulfonamides for the Treatment of Inflammation. WO Patent 95/15316, June 8, 1995.
74. Reddy, M. V. R.; Bell, S. C. Processes for the Preparation of 1, 5-diaryl-3-substituted Pyrazoles. WO Patent 03/024958, March 27, 2003.
75. Oh, L. M. Tetrahedron Lett. 2006, 47, 7943-7946. doi:10.1016/j.tetlet. 2006.08.138. (Pubitemid 44485160)
76. Pandite, A. N.; Whitehead, B. F.; Ho, P. T. C.; Suttle, A. B. Cancer Treatment Method. WO Patent 2007/064753, June 7, 2007.
77. Harris, P. A.; Boloor, A.; Cheung, M.; Kumar, R.; Crosby, R. M.; Davis-Ward, R. G.; Epperly, A. H.; Hinkle, K. W.; Hunter, R. N. III; Johnson, J. H.; Knick, V. B.; Laudeman, C. P.; Luttrell, D. K.; Mook, R. A.; Nolte, R. T.; Rudolph, S. K.; Szewczyk, J. R.; Truesdale, A. T.; Veal, J. M.; Wang, L.; Stafford, J. A. J. Med. Chem. 2008, 51, 4632-4640. doi:10.1021/jm800566m.
78. Ray, P. C.; Bandari, M.; Qadeeruddin, M.; Manjaneyulu, G. S. Process for the Large Scale Production of Rizatriptan Benzoate. WO Patent 2007/054979, May 18, 2007.
79. Solanki, K. S.; Pal, G.; Haider, H.; Singh, M.; Kothari, J. S.; Agarwal, V. K. A Process for the Preparation of Pure Anastrozole. WO Patent 2007/054963, May 18, 2007.
80. Gaitonde, A.; Vaidaya, C.; Pawar, S. R. Process for the Preparation of Anastrozole. WO Patent 2006/000836, Jan 5, 2006.
81. Grundmann, C.; Ratz, R. J. Org. Chem. 1956, 21, 1037-1038. doi:10.1021/jo01115a610.
82. Martin, P.; Berens, U.; Boudier, A.; Dosenbach, O. Synthesis Methods and Intermediates for the Manufacture of Rizatriptan. WO Patent 2005/075422, Aug 18, 2005.
83. Kim, D.; Wang, L.; Beconi, M.; Eiermann, G. J.; Fisher, M. H.; He, H.; Hickey, G. J.; Kowalchick, J. E.; Leiting, B.; Lyons, K.; Marsilio, F.; McCann, M. E.; Patel, R. A.; Petrov, A.; Scapin, G.; Patel, S. B.; Roy, R. S.; Wu, J. K.; Wyvratt, M. J.; Zhang, B. B.; Zhu, L.; Thornberry, N. A.; Weber, A. E. J. Med. Chem. 2005, 48, 141-151. doi:10.1021/jm0493156. (Pubitemid 40105255)
84. Hansen, K. B.; Balsells, J.; Dreher, S.; Hsiao, Y.; Kubryk, M.; Palucki, M.; Rivera, N.; Steinhuebel, D.; Armstrong, J. D. III; Askin, D.; Grabowski, E. J. J. Org. Process Res. Dev. 2005, 9, 634-639. doi:10.1021/op0500786. (Pubitemid 41422489)
85. Balsells, J.; DiMichele, L.; Liu, J.; Kubryk, M.; Hansen, K.; Armstrong, J. D. III. Org. Lett. 2005, 7, 1039-1042. doi:10.1021/ol0474406. (Pubitemid 40626895)
86. Haycock-Lewandowski, S. J.; Wilder, A.; Åhman, J. Org. Process Res. Dev. 2008, 12, 1094-1103. doi:10.1021/op8000614.
87. Hester, J. P. Jr.; Rudzik, A. D.; Kamdar, B. V. J. Med. Chem. 1971, 14, 1078-1081. doi:10.1021/jm00293a015.
88. Sternbach, L. H.; Fryer, R. I.; Metlesics, W.; Reeder, E.; Sach, G.; Saucy, G.; Stempel, A. J. Org. Chem. 1962, 27, 3788-3796. doi:10.1021/ jo01058a010.
89. Fustero, S.; González, J.; del Pozo, C. Molecules 2006, 11, 583-588. doi:10.3390/11080583. (Pubitemid 44343403)
90. Heeres, J.; Backx, L. J. J.; Van Cutsem, J. J. Med. Chem. 1984, 27, 894-900. doi:10.1021/jm00373a015.
91. Portmann, R. Process for preparing 1-substituted 4-cyano-1, 2, 3-triazoles. WO Patent 98/02423, Jan 22, 1998.
92. Portmann, R.; Hofmeier, C.; Burkhard, A.; Scherrer, W.; Szelagiewicz, M. Crystal modification of 1-(2, 6-difluorobenzyl)-1H-1, 2, 3-triazole-4- carboxamide and its use as antiepileptic. US Patent 6, 740, 669 B1, May 25, 2004.
93. Hudd, W. H.; Stevens, E. P. Tetrahedron Lett. 2010, 51, 3229-3231. doi:10.1016/j.tetlet.2010.04.060.
94. Wang, Y.; Li, Y.; Li, Y.; Zheng, G.; Li, Y. Method for the Production of Losartan. WO Patent 2006/081807, Aug 10, 2006.
95. Mendelovici, M.; Finkelstein, N.; Pilarski, G. Process for Preparing Cilostazol. U.S. Patent 6, 515, 128, Feb 4, 2003.
96. Nishi, T.; Nakagawa, K. Tetrazolylalkoxycarbostyryl Derivatives and Pharmaceutical Compositions Containing them. U.S. Patent 4, 277, 479, July 7, 1981.
97. Guay, D. R. P. Clin. Ther. 2002, 24, 473-489. doi:10.1016/S0149-2918(02) 85125-6. (Pubitemid 34492871)
98. Mooney, M. T.; Deguchi, S.; Tada, T.; Fujioka, M.; Okamoto, Y.; Yasuda, T. Chem. Pharm. Bull. 1995, 43, 374-377.
99. González, M.; Rodriguez, Z.; Tolón, B.; Rodriguez, J. C.; Veléz, H.; Valdez, B.; Lopéz, M. A.; Fini, A. Farmaco 2003, 58, 409-418. doi:10.1016/S0014-827X(03)00063-6. (Pubitemid 36593322)
100. Kempf, D. J.; Marsh, K. C.; Denissen, J. F.; McDonald, E.; Vasavanonda, S.; Flentge, C. A.; Green, B. E.; Fino, L.; Park, C. H.; Kong, X. P. Proc. Natl. Acad. Sci. U. S. A. 1995, 92, 2484-2488. doi:10.1073/pnas.92.7.2484.
101. Kerdesky, F. A. J.; Seif, L. S. Synth. Commun. 1995, 25, 2639-2645. doi:10.1080/00397919508011810.
102. Schneider, C.; Griss, G.; Hurnaus, R.; Kobinger, W.; Pichler, L.; Bauer, R.; Mierau, J.; Hinzen, D.; Schingnitz, G. Tetrahydrobenzothiazoles, their Production and Use as Intermediates and Pharmaceuticals. Eur. Patent 186087B1, July 2, 1986.
103. Martin Juarez, J.; Silva Guisasola, L. O. Method for the Resolution of 2-Amino-6-propylamino-4, 5, 6, 7-tetrahydrobenzothiazole and Intermediate Compounds. WO Patent 2006/120268, Nov 16, 2006.
104. Miodragović, D. U.; Bogdanović, G. A.; Miodragović, Z. M.; Radulović, M. D.; Novaković, S. B.; Kaluderović, G. N.; Kozłowski, H. J. Inorg. Biochem. 2006, 100, 1568-1574. doi:10.1016/j.jinorgbio.2006.05.009. (Pubitemid 44188905)
105. Sprague, J. M.; Land, A. H.; Ziegler, C. J. Am. Chem. Soc. 1946, 68, 2155-2159. doi:10.1021/ja01215a010.
106. Hirata, Y.; Yanagisawa, I.; Ishii, Y.; Tsukamoto, S.; Ito, N.; Isamura, Y.; Takeda, M. Guanidinothiazole Compounds, Process for Preparation and Gastric Inhibiting Compositions Containing them. U.S. Patent 4, 283, 408, Aug 11, 1981.
107. Hasegawa, M. Heterocycles 1998, 47, 857-864. doi:10.3987/COM-97-S(N)89.
108. Yevich, J. P.; New, J. S.; Smith, D. W.; Lobeck, W. G.; Catt, J. D.; Minielli, J. L.; Eison, M. S.; Taylor, D. P.; Riblet, L. A.; Temple, D. L. Jr. J. Med. Chem. 1986, 29, 359-369. doi:10.1021/jm00153a010. (Pubitemid 16189496)
109. Nadkarni, D. V.; Hallissey, J. F. Org. Process Res. Dev. 2008, 12, 1142-1145. doi:10.1021/op800105j.
110. Walinsky, S. W.; Fox, D. E.; Lambert, J. F.; Sinay, T. G. Org. Process Res. Dev. 1999, 3, 126-130. doi:10.1021/op980210k.
111. Huguet Clotet, J.; Puig Torres, S. Process for the Preparation of Ziprasidone. Eur. Patent 1975169, Oct 1, 2008.
112. Price, B. J.; Clitherow, J. W.; Bradshaw, J. W. Aminoalkylfuranderivate, Verfahren zu ihrer Herstellung und diese Verbindungen erhaltende Arzneimittel. Ger. Patent 2734070, Dec 29, 1983.
113. Vlaovic, D.; Milic, B. L.; Mackenzie, K. J. Chem. Res., Synop. 1989, 6, 156-157.
114. Gever, G.; O'Keefe, C. J. Process for the Preparation of Azomethines of 5-Nitro-2-formylfurane with Hydrazine Compounds. U.S. Patent 2, 927, 110, March 1, 1960.
115. Witczak, M.; Kwiecié, H. Synth. Commun. 2005, 35, 2223-2230. doi:10.1080/00397910500182747. (Pubitemid 41176764)
116. Wang, Z. J. Synthetic Process for 2-Butyl-3-(hydroxy-3, 5-diiodobenzoyl)-benzofuran. Chin. Patent 1, 858, 042, Nov 8, 2006.
117. Ha, H. R.; Stieger, B.; Grassi, G.; Altorfer, H. R.; Follath, F. Eur. J. Clin. Pharmacol. 2000, 55, 807-814. doi:10.1007/s002280050701.
118. Vogel, V. G.; Costantino, J. P.; Wickerham, D. L.; Cronin, W. M.; Cecchini, R. S.; Atkins, J. N.; Bevers, T. B.; Fehrenbacher, L.; Pajon, E. R. Jr.; Wade, J. L. III; Robidoux, A.; Margolese, R. G.; James, J.; Lippman, S. M.; Runowicz, C. D.; Ganz, P. A.; Reis, S. E.; McCaskill-Stevens, W.; Ford, L. G.; Jordan, V. C.; Wolmark, N. JAMA, J. Am. Med. Assoc. 2006, 295, 2727-2741. doi:10.1001/jama.295.23.joc60074.
119. Jones, C. D.; Jevnikar, M. G.; Pike, A. J.; Peters, M. K.; Black, L. J.; Thompson, A. R.; Falcone, J. F.; Clemens, J. A. J. Med. Chem. 1984, 27, 1057-1066. doi:10.1021/jm00374a021.
120. Aikins, J. A.; Miller, R. S. Vinyl Sulfoxides and a Process for their Synthesis. WO Patent 96/40691, Dec 19, 1996.
121. Chakrabarti, J. K.; Hotten, T. M.; Tupper, D. E. 2- Methylthienobenzodiazepine. U.S. Patent 5, 627, 178, May 6, 1997.
122. Chakrabarti, J. K.; Hotten, T. M.; Tupper, D. E. 2- Methylthienobenzodiazepine. U.S. Patent 5, 229, 382, July 20, 1993.
123. Berglund, R. A. Intermediate Useful for the Asymmetric Synthesis of Duloxetine. U.S. Patent 5, 491, 243, Feb 12, 1996.
124. Eng, W.-S.; Burns, D. H.; Ponticello, G. S.; Selwick, H. G. Short Synthesis of 5, 6-Dihydro-(S)-4-(ethylamino)-(S)-6-[C3H3]-4H-thieno[2, 3-b]thiopyran -2-sulfonamide-7, 7-dioxide and Related Non-Radioactive Compounds. U.S. Patent 5, 441, 722, Aug 15, 1995.
125. Blacklock, T. J.; Sohar, P.; Butcher, J. W.; Lamanec, T.; Grabowski, E. J. J. J. Org. Chem. 1993, 58, 1672-1679. doi:10.1021/jo00059a013.
126. Wang, L.; Shen, J.; Tang, Y.; Chen, Y.; Wang, W.; Cai, Z.; Du, Z. Org. Process Res. Dev. 2007, 11, 487-489. doi:10.1021/op700025d.
127. Lodewijk, E.; Khatri, H. N. 2-(2-Nitrovinyl)thiophene Reduction and Synthesis of Thieno[3, 2-c]pyridine Derivatives. Eur. Patent 342, 118, Nov 15, 1989.
128. Kikuchi, C.; Hiranuma, T.; Koyama, M. Bioorg. Med. Chem. Lett. 2002, 12, 2549-2552. doi:10.1016/S0960-894X(02)00485-7. (Pubitemid 35245278)
129. Hanson, M. A.; Cherezov, V.; Griffith, M. T.; Roth, C. B.; Jaakola, V.-P.; Chien, E. Y. T.; Velasquez, J.; Kuhn, P.; Stevens, R. C. Structure 2008, 16, 897-905. doi:10.1016/j.str.2008.05.001. (Pubitemid 351778384)
130. Tosi, G.; Zironi, F.; Caselli, E.; Forni, A.; Prati, F. Synthesis 2004, 1625-1628. doi:10.1055/s-2004-822395.
131. Vest, R. D. 3, 4-Dichloro-1, 2, 5-thiadiazole and its Preparation. U.S. Patent 3, 115, 497, Dec 24, 1963.
132. Xu, J.; Shen, Y.; Xiang, L.; Deng, Y. Zhongguo Yiyao Gongye Zazhi 2005, 36, 593-595.
133. Lima, L. M.; Barreira, E. J. Curr. Med. Chem. 2005, 12, 23-49.
134. Ramakrishnam, A.; Gobind, K.; Neeraj, K.; Dnyaneshwar, S. An Improved Process for Preparation of Leflunomides. WO Patent 2007/086076, Aug 2, 2007.
135. Ikuno, K.; Yoshida, S. Method for Producing 5-Methylisoxazole. Jap. Patent 2007/320855, Dec 13, 2007.
136. Reiter, L. A. J. Org. Chem. 1987, 52, 2714-2726. doi:10.1021/jo00389a015.
137. Kennis, L. E. J.; Vanderberk, J. 3-Piperidinyl-substituted 1, 2-Benzisoxazoles and 1, 2-Benzisothiazoles. U.S. Patent 4, 804, 663, Feb 14, 1989.
138. Carey, J. S.; Laffan, D.; Thomson, C.; Williams, M. T. Org. Biomol. Chem. 2006, 4, 2337-2347. doi:10.1039/b602413k. (Pubitemid 43882754)
139. Dugger, R. W.; Ragan, J. A.; Brown Ripin, D. H. Org. Process Res. Dev. 2005, 9, 253-258. doi:10.1021/op050021j. (Pubitemid 40814299)
140. Francotte, E.; Lindner, W., Eds. Chirality in Drug Research: From Synthesis to Pharmacology; Methods and Principles in Medicinal Chemistry, Vol. 33; Wiley-VCH Verlag GmbH & Co. KgaA: Weinheim, Germany, 2006. doi:10.1002/3527609431.
141. Ojima, I., Ed. Catalytic Asymmetric Synthesis, 3rd ed.; Wiley & Sons, Inc.: Hoboken, New Jersey, 2010. doi:10.1002/9780470584248.
142. Baxendale, I. R.; Hayward, J. J.; Ley, S. V.; Tranmer, G. K. ChemMedChem 2007, 2, 768-788. doi:10.1002/cmdc.200700008.