Synthetic approaches to the 2010 new drugs

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 3, 2012, Pages 1155-1174

  Liu, Kevin K C ^a   Sakya, Subas M ^a   O'Donnell, Christopher J ^a   Flick, Andrew C ^a   Ding, Hong X ^b  

^a PFIZER INC   (United States)

^b Shenogen Pharma Group   (China)

Author keywords

Medicine; New chemical entities; New drug molecules; Synthesis; Therapeutic agents

Indexed keywords

ALOGLIPTIN; BAZEDOXIFENE; CABAZITAXEL; CLOZAPINE; DIQUAFOSOL; DIQUAS; ERIBULIN; FINGOLIMOD; HALOPERIDOL; ILOPERIDONE; KYNAPID; LANINAMIVIR; MIFAMURTIDE; NEW DRUG; OSELTAMIVIR; PERAMIVIR; PREDNISONE; PRUCALOPRIDE; RAPIACTA; ROFLUMILAST; ROMIDEPSIN; UNCLASSIFIED DRUG; VERNAKALANT; VINFLUNINE;

ASTHMA; BREAST CANCER; CHRONIC OBSTRUCTIVE LUNG DISEASE; CUTANEOUS T CELL LYMPHOMA; DIARRHEA; DRUG APPROVAL; DRUG EFFICACY; DRUG MARKETING; DRUG STRUCTURE; DRUG SYNTHESIS; DRY EYE; HUMAN; INFLUENZA; INFLUENZA A; INFLUENZA B; LUNG NON SMALL CELL CANCER; MOLECULAR RECOGNITION; MULTIPLE SCLEROSIS; NAUSEA; NEUTROPENIA; OSTEOPOROSIS; OSTEOSARCOMA; OVARY CANCER; PROSTATE CANCER; REVIEW; SCHIZOPHRENIA; SIDE EFFECT; WEIGHT REDUCTION;

CHEMISTRY TECHNIQUES, SYNTHETIC; DRUG DESIGN; MOLECULAR STRUCTURE; PHARMACEUTICAL PREPARATIONS;

EID: 84856220950     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.12.049     Document Type: Review

References (130)

1. T.N.K. Raju Lancet 355 2000 1022
2. J. Li, and K.K.-C. Liu Mini-Rev. Med. Chem. 4 2004 207
3. K.K.-C. Liu, J. Li, and S. Sakya Mini-Rev. Med. Chem. 4 2004 1105
4. J. Li, K.K.-C. Liu, and S. Sakya Mini-Rev. Med. Chem. 5 2005 1133
5. S.M. Sakya, K.K.-C. Liu, and J. Li Mini-Rev. Med. Chem. 7 2007 429
6. K.K.-C. Liu, S.M. Sakya, and J. Li Mini-Rev. Med. Chem. 7 2007 1255
7. K.K.-C. Liu, S.M. Sakya, C.J. O'Donnell, and J. Li Mini-Rev. Med. Chem. 8 2008 1526
8. K.K.-C. Liu, S.M. Sakya, C.J. O'Donnell, and J. Li Mini-Rev. Med. Chem. 9 2009 1655
9. K.K.-C. Liu, S.M. Sakya, C.J. O'Donnell, A.C. Flick, and J. Li Bioorg. Med. Chem. 19 2011 1136
10. A.I. Graul, and E. Cruces Drugs Today 47 2011 27
11. C.F. Deacon Diabetes Obes. Metab. 13 2011 7
12. S.H. Havale, and M. Pal Bioorg. Med. Chem. 17 2009 1783
13. J. Feng, Z. Zhang, M.B. Wallace, J.A. Stafford, S.W. Kaldor, D.B. Kassel, M. Navre, L. Shi, R.J. Skene, T. Asakawa, K. Takeuchi, R. Xu, D.R. Webb, and S.L. Gwaltney II J. Med. Chem. 50 2007 2297
14. Feng, J.; Gwaltney, S. L., II; Stafford, J. A.; Zhang, Z.; Elder, B. J.; Isbester, P. K.; Palmer, G. J.; Salsbury, J. S.; Ulysse, L. WO 2007035629 A2, 2007.
15. Ludescher, J.; Wieser, J.; Laus, G. WO 2010072680 A1, 2010.
16. Marom, E.; Mizhiritskii, M.; Rubnov, S. WO 2010109468 A1, 2010.
17. A.W.C. Kung, E.Y.W. Chu, and L. Xu Expert Opin. Pharmacother. 10 2009 1377
18. J. Waalen J. Exp. Pharmacol. 2 2010 121
19. Jirman, J.; Richter, J. WO 2008098527 A1, 2008.
20. Sanganabhatla, S.; Srivastava, S.; Deore, D. B.; Crasto, A. M.; Khan, M. A. U.S. 20100310870 A1, 2010.
21. Joshi, S.; Bhuta, S.; Talukdar, S.; Sawant, S.; Venkatraman, D. WO 2010118997 A1, 2010.
22. Bandichhor, R.; Lekkala, A. R.; Haldar, P.; Mylavarapu, R. K.; Golla, C. M.; Vagwala, R.; Karri, V. K.; Akula, S. WO 2011022596 A2, 2011.
23. C.J. Paller, and E.S. Antonarakis Drug Des. Dev. Ther. 5 2011 117
24. D.G. Kingston J. Nat. Prod. 72 2009 507
25. Bouchard, H.; Bourzat, J.-D.; Commercon, A. U.S. 2001051736 A1, 2001.
26. Chattopadhyay, S. K.; Srivastava, S.; Mehta, V. K. U.S. 6437154, 2002.
27. K.K. Nichols, B. Yerxa, and D.J. Kellerman Expert Opin. Invest. Drugs 13 2004 47
28. W. Pendergast, B.R. Yerxa, J.G. Douglass III, S.R. Shaver, R.W. Dougherty, C.C. Redick, I.F. Sims, and J.L. Rideout Bioorg. Med. Chem. Lett. 11 2001 157
29. Yerax, B. R.; Pendergast, W. WO 9905155 A2, 1999.
30. W. Zheng, B.M. Seletsky, M.H. Palme, P.J. Lydon, L.A. Singer, C.E. Chase, C.A. Lemelin, Y. Shen, H. Davis, L. Tremblay, M.J. Towle, K.A. Salvato, B.F. Wels, K.K. Aalfs, Y. Kishi, B.A. Littlefield, and M.J. Yu Bioorg. Med. Chem. Lett. 14 2004 5551
31. Y. Wang, N. Serradell, J. Bolós, and E. Rosa Drugs Future 32 2007 681
32. H. Chiba, and K. Tagami J. Synth. Org. Chem. Jpn. 69 2011 600
33. H. Choi, D. Demeke, F.-A. Kang, Y. Kishi, K. Nakajima, P. Nowak, Z.-K. Wan, and C. Xie Pure Appl. Chem. 75 2003 1
34. Kishi, Y.; Fang, F.; Forsyth, C. J.; Scola, P. M.; Yoon, S. K. WO 9317690 A1, 1993.
35. Littlefield, B. A.; Palme, M.; Seletsky, B. M.; Towle, M. J.; Yu, M. J.; Zheng, W. WO 9965894 A1, 1999.
36. T.D. Aicher, K.R. Buszek, F.G. Fang, C.J. Forsyth, S.H. Jung, Y. Kishi, M.C. Matelich, P.M. Scola, D.M. Spero, and S.K. Yoon J. Am. Chem. Soc. 114 1992 3162
37. Austad, B.; Chase, C. E.; Fang, F. G. WO 2005118565 A1, 2005.
38. Chase, C.; Endo, A.; Fang, F. G.; Li, J. WO 2009046308 A1, 2009.
39. L.J. Scott CNS Drugs 25 2011 673
40. S.W. Paugh, S.G. Payne, S.E. Barbour, S. Milstien, and S. Spiegel FEBS Lett. 554 2003 189
41. A. Billich, F. Bornancin, P. Dévay, D. Mechtcheriakova, N. Urtz, and T. Baumruker J. Biol. Chem. 278 2003 47408
42. T. Sanchez, T. Estrada-Hernandez, J.H. Paik, M.T. Wu, K. Venkataraman, V. Brinkmann, K. Claffey, and T. Hla J. Biol. Chem. 278 2003 47281
43. R. Albert, K. Hinterding, V. Brinkmann, D. Guerini, C. Muller-Hartwieg, H. Knecht, C. Simeon, M. Streiff, T. Wagner, K. Welzenbach, F. Zecri, M. Zollinger, N. Cooke, and E. Francotte J. Med. Chem. 48 2005 5373
44. S. Balasubramaniam, S. Annamalai, and I.S. Aidhen Synlett 2007 2841
45. P. Durand, P. Peralba, F. Sierra, and P. Renaut Synthesis 2000 505
46. F.W. Foss Jr., T.P. Mathews, Y. Kharel, P.C. Kennedy, A.H. Snyder, M.D. Davis, K.R. Lynch, and T.L. Macdonald Bioorg. Med. Chem. 17 2009 6123
47. J.J. Hale, L. Yan, W.E. Neway, R. Hajdu, J.D. Bergstrom, J.A. Milligan, G.-J. Shei, G.L. Chrebet, R.A. Thornton, D. Card, M. Rosenbach, H. Rosen, and S. Mandala Bioorg. Med. Chem. 12 2004 4803
48. K. Hinterding, R. Albert, and S. Cottens Tetrahedron Lett. 43 2002 8095
49. K. Hinterding, S. Cottens, R. Albert, F. Zecri, P. Buehlmayer, C. Spanka, V. Brinkmann, P. Nussbaumer, P. Ettmayer, K. Hoegenauer, N. Gray, and S. Pan Synthesis 2003 1667
50. B. Kalita, N.C. Barua, M. Bezbarua, and G. Bez Synlett 2001 1411
51. S. Kim, H. Lee, M. Lee, and T. Lee Synthesis 2006 753
52. M. Kiuchi, K. Adachi, T. Kohara, M. Minoguchi, T. Hanano, Y. Aoki, T. Mishina, M. Arita, N. Nakao, M. Ohtsuki, Y. Hoshino, K. Teshima, K. Chiba, S. Sasaki, and T. Fujita J. Med. Chem. 43 2000 2946
53. M. Kiuchi, K. Adachi, A. Tomatsu, M. Chino, S. Takeda, Y. Tanaka, Y. Maeda, N. Sato, N. Mitsutomi, K. Sugahara, and K. Chiba Bioorg. Med. Chem. 13 2005 425
54. Z. Li, and R. Bittman J. Org. Chem. 72 2007 8376
55. X. Lu, C. Sun, W.J. Valentine, S. E, J. Liu, G. Tigyi, and R. Bittman J. Org. Chem. 74 2009 3192
56. N. Matsumoto, R. Hirose, S. Sasaki, and T. Fujita Chem. Pharm. Bull. 56 2008 595
57. S. Nakayama, Y. Uto, K. Tanimoto, Y. Okuno, Y. Sasaki, H. Nagasawa, E. Nakata, K. Arai, K. Momose, T. Fujita, T. Hashimoto, Y. Okamoto, Y. Asakawa, S. Goto, and H. Hori Bioorg. Med. Chem. 16 2008 7705
58. G. Seidel, D. Laurich, and A. Fürstner J. Org. Chem. 69 2004 3950
59. S. Sugiyama, S. Arai, M. Kiriyama, and K. Ishii Chem. Pharm. Bull. 53 2005 100
60. C. Sun, and R. Bittman J. Org. Chem. 71 2006 2200
61. S. Takeda, M. Chino, M. Kiuchi, and K. Adachi Tetrahedron Lett. 46 2005 5169
62. R. Zhu, A.H. Snyder, Y. Kharel, L. Schaffter, Q. Sun, P.C. Kennedy, K.R. Lynch, and T.L. Macdonald J. Med. Chem. 50 2007 6428
63. Gidwani, R. M.; Hiremath, C. WO 2011009634 A2, 2011.
64. H.A.M. Mucke, and J. Castañer Drugs Future 25 2000 29
65. Strupczewski, J. T.; Gardner, B. A.; Allen, R. C. U.S. 4355037 A, 1982.
66. Strupczewski, J. T.; Helsley, G. C.; Chiang, Y.; Bordeau, K. J.; Glamkowski, E. J. U.S. 5364866 A, 1994.
67. Strupczewski, J. T.; Helsley, G. C.; Chiang, Y.; Bordeau, K. J. EP 402644 A1, 1990.
68. Strupczewski, J. T.; Helsley, G. C.; Chiang, Y.; Bordeau, K. J.; Glamkowski, E. J. EP 542136 A1, 1993.
69. J.T. Strupczewski, K.J. Bordeau, Y. Chiang, E.J. Glamkowski, P.G. Conway, R. Corbett, H.B. Hartman, M.R. Szewczak, C.A. Wilmot, and G.C. Helsley J. Med. Chem. 38 1995 1119
70. Strupczewski, J. T.; Helsley, G. C.; Glamkowski, E. J.; Chiang, Y.; Bordeau, K. J.; Nemoto, P. A.; Tegeler, J. J. WO 9511680 A1, 1995.
71. Strupczewski, J. T.; Helsley, G. C.; Glamkowski, E. J.; Chiang, Y.; Bordeau, K. J.; Nemoto, P. A.; Tegeler, J. J. U.S. 5776963 A, 1998.
72. Vértessy, M. WO 2010031497 A1, 2010.
73. S. Kubo, T. Tomozawa, M. Kakuta, A. Tokumitsu, and M. Yamashita Antimicrob. Agents Chemother. 54 2010 1256
74. E. Zbiral, S. Phadtare, and W. Schmid Liebigs Ann. Chem. 1987 39
75. K. Anazawa, K. Furuhata, and H. Ogura Chem. Pharm. Bull. 36 1988 4976
76. T. Honda, T. Masuda, S. Yoshida, M. Arai, S. Kaneko, and M. Yamashita Bioorg. Med. Chem. Lett. 12 2002 1925
77. T. Masuda, S. Yoshida, M. Arai, S. Kaneko, M. Yamashita, and T. Honda Chem. Pharm. Bull. 51 2003 1386
78. T. Honda, S. Kubo, T. Masuda, M. Arai, Y. Kobayashi, and M. Yamashita Bioorg. Med. Chem. Lett. 19 2009 2938
79. Anon. Drugs R&D 2008, 9, 131.
80. J.R. Prous, and J. Castaner Drugs Future 14 1989 220
81. Baschang, G.; Tarcsay, L.; Hartmann, A.; Stanek, J. EP 0027258 A1, 1980.
82. D.E. Brundish, and R. Wade J. Labelled Compd. Radiopharm. 22 1985 29
83. Y.S. Babu, P. Chand, S. Bantia, P. Kotian, A. Dehghani, Y. El-Kattan, T.H. Lin, T.L. Hutchison, A.J. Elliott, C.D. Parker, S.L. Ananth, L.L. Horn, G.W. Laver, and J.A. Montgomery J. Med. Chem. 43 2000 3482
84. Babu, Y. S.; Chand, P.; Montgomery, J. A. WO 9933781 A1, 1999.
85. Abdel-magid, A. F.; Bichsel, H. U.; Korey, D. J.; Laufer, G. G.; Lehto, E. A.; Mattei, S.; Rey, M.; Schultz, T. W.; Maryanoff, C. WO 0100571 A1, 2001.
86. Han, X. W.; Zhang, X. J.; Fan, Q. Y.; Li, W. D.; Wang, S. X. CN 101538228 A, 2009.
87. M.R. Briejer, J.P. Bosmans, P. Van Daele, M. Jurzak, L. Heylen, J.E. Leysen, N.H. Prins, and J.A.J. Schuurkes Eur. J. Pharmacol. 423 2001 71
88. M.R. Briejer, N.H. Prins, and J.A.J. Schuurkes Neurogastroenterol. Motil. 13 2001 465
89. M. Coggrave, P.H. Wiesel, and C. Norton Cochrane Database Syst. Rev. 2006 CD002115
90. G. Coremans, R. Kerstens, M. De Pauw, and M. Stevens Digestion 67 2003 82
91. B.Y. De Winter, G.E. Boeckxstaens, J.G. De Man, T.G. Moreels, J.A.J. Schuurkes, T.L. Peeters, A.G. Herman, and P.A. Pelckmans Gut 45 1999 713
92. A.V. Emmanuel, A.J. Roy, T.J. Nicholls, and M.A. Kamm Aliment. Pharmacol. Ther. 16 2002 1347
93. J.E. Frampton Drugs 69 2009 2463
94. K. Krogh, M. Bach Jensen, P. Gandrup, S. Laurberg, J. Nilsson, R. Kerstens, and M. De Pauw Scand. J. Gastroenterol. 37 2002 431
95. D. Pau, A.J. Workman, K.A. Kane, and A.C. Rankin J. Pharmacol. Exp. Ther. 313 2005 146
96. J.H. De Maeyer, J.A.J. Schuurkes, and R.A. Lefebvre Br. J. Pharmacol. 156 2009 362
97. H.R. Irving, N. Tochon-Danguy, K.A. Chinkwo, J.G. Li, C. Grabbe, M. Shapiro, C.W. Pouton, and I.M. Coupar Pharmacology 85 2010 224
98. A.M. Ray, R.E. Kelsell, J.A. Houp, F.M. Kelly, A.D. Medhurst, H.M. Cox, and A.R. Calver Eur. J. Pharmacol. 604 2009 1
99. Baba, Y.; Usui, T.; Iwata, N. EP 640602 A1, 1995.
100. Fancelli, D.; Caccia, C.; Severino, D.; Vaghi, F.; Varasi, M. WO 9633186 A1, 1996.
101. Y. Hirokawa, I. Fujiwara, K. Suzuki, H. Harada, T. Yoshikawa, N. Yoshida, and S. Kato J. Med. Chem. 46 2003 702
102. T. Kakigami, T. Usui, K. Tsukamoto, and T. Kataoka Chem. Pharm. Bull. 46 1998 42
103. Van Daele, G. H. P.; Bosmans, J.-P. R. M. A.; Schuurkes, J. A. J. WO 9616060 A1, 1996.
104. I. Candiani, S. DeBernadinis, W. Cabri, M. Marchi, A. Bedeschi, and S. Penco Synlett 1993 269
105. S.A. Antoniu Int. J. Chron. Obstruct. Pulmon. Dis. 2011 147
106. K.F. Rabe Exp. Rev. Respir. Med. 4 2010 543
107. K.F. Rabe Br. J. Pharmacol. 163 2011 53
108. M. Sanford Drugs 70 2010 1615
109. C.S. Ulrik, and P.M.A. Calverley Clin. Respir. J. 4 2010 197
110. Bose, P.; Sachdeva, Y. P.; Rathore, R. S.; Kumar, Y. WO 2005026095 A1, 2005.
111. Lohray, B. B.; Lohray, V. B.; Dave, M. G. IN 2004MU478 A, 2007.
112. E.M. Bertino, and G.A. Otterson Expert Opin. Invest. Drugs 20 2011 1151
113. R. Furumai, A. Matsuyama, N. Kobashi, K.-H. Lee, M. Nishiyama, H. Nakajima, A. Tanaka, Y. Komatsu, N. Nishino, M. Yoshida, and S. Horinouchi Cancer Res. 62 2002 4916
114. Verdine, G. L.; Vrolijk, N. H.; Bertel, S. WO 2008083288 A2, 2008.
115. Verdine, G. L.; Vrolijk, N. H. WO 2008083290 A1, 2008.
116. T.J. Greshock, D.M. Johns, Y. Noguchi, and R.M. Williams Org. Lett. 10 2008 613
117. K.W. Li, J. Wu, W. Xing, and J.A. Simon J. Am. Chem. Soc. 118 1996 7237
118. P. Cialdella, D. Pedicino, and P. Santangeli Recent Pat. Cardiovasc. Drug Disc. 6 2011 1
119. S.T. Duggan, and L.J. Scott Drugs 71 2011 237
120. B.D. Lindsay J. Am. Coll. Cardiol. 57 2011 322
121. P. Santangeli, L. Di Biase, G. Pelargonio, J.D. Burkhardt, and A. Natale Ann. Med. 43 2011 13
122. A. Marinelli, I. Ciccarelli, and A. Capucci Clin. Invest. 1 2011 579
123. C.M. Pratt, D. Roy, C. Torp-Pedersen, D.G. Wyse, E. Toft, S. Juul-Moller, E. Retyk, and D.H. Drenning Am. J. Cardiol. 106 2010 1277
124. Jung, G.; Yee, J. G. K.; Chou, D. T. H.; Plouvier, B. M. C. WO 2006138673 A2, 2006.
125. Machiya, K.; Ike, K.; Watanabe, M.; Yoshino, T.; Okamoto, T.; Morinaga, Y.; Mizobata, S. WO 2006075778 A1, 2006.
126. Plouvier, B. M. C.; Chou, D. T. H.; Jung, G.; Choi, L. S. L.; Sheng, T.; Barrett, A. G. M.; Passafaro, M. S.; Kurz, M.; Moeckli, D.; Ulmann, P.; Hedinger, A. WO 2006088525 A1, 2006.
127. E. Fuhrmann, and J. Talbiersky Org. Process Res. Dev. 9 2005 206
128. J.A. McIntyre, and J. Castañer Drugs Future 29 2004 574
129. Jacquesy, J.-C.; Fahy, J.; Berrier, C.; Bigg, D.; Jouannetaud, M.-P.; Zunino, F.; Kruczynski, A.; Kiss, R. U.S. 5620985 A, 1997.
130. Duflos, A.; Fahy, J.; Thillaye du Boullay, V.; Barret, J.-M.; Hill, B. U.S. 6127377 A, 2000.