Critical assessment of pharmaceutical processes - A rationale for changing the synthetic route

Chemical Reviews

Volumn 106, Issue 7, 2006, Pages 3002-3027

  Butters, Mike ^a   Catterick, David ^b   Craig, Andrew ^b   Curzons, Alan ^b   Dale, David ^c   Gillmore, Adam ^c   Green, Stuart P ^c   Marziano, Ivan ^c   Sherlock, Jon Paul ^a   White, Wesley ^a  

^a ASTRAZENECA   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

^c PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYST ACTIVITY; HYDROGENATION; MOLECULAR STRUCTURE; PROCESS ENGINEERING; SAFETY FACTOR; SYNTHESIS (CHEMICAL);

PHARMACEUTICAL PROCESSES; PROCESS ASSESSMENT; SYNTHETIC ROUTE;

DRUG PRODUCTS;

DRUG;

CHEMISTRY; DRUG LEGISLATION; LEGAL ASPECT; METHODOLOGY; REVIEW; SAFETY; STANDARD; SYNTHESIS;

CHEMISTRY, PHARMACEUTICAL; LEGISLATION, DRUG; PHARMACEUTICAL PREPARATIONS; SAFETY;

EID: 33746908147     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr050982w     Document Type: Review

References (122)

1. Pressures on the Pharmaceutical Industry: Pharmaceutical Companies Overview 2003. www.bcc.ecnext.com (accessed Feb 2006).
2. http://trade.gov/td/chemicals/drugpricingstudy.pdf (accessed Feb 2006).
3. Neil Grubert, M. A. International Trends in Pharmaceutical Regulatory Affairs; Pharmaceutical Industry Dynamics 2003. www.dresources.com (accessed Feb 2006).
4. Brummel, R. N. Creativity on large scale: Lesson from scale up. Book of Abstracts; 219th American Chemical Society National Meeting, San Francisco, CA, March 26-30, 2000.
5. Gadamasetti, K. G.; Editor. Process Chemistry in the Pharmaceutical Industry; Marcel Dekker Inc.: 1999.
6. Rogers, R.; Hallam, S. Process Saf. Environ. Prot. 1991, 69, 149.
7. Lewis, R. J. Sax's Dangerous Properties of Industrial Materials, 10th ed.; Wiley: New York, 1999; 3-Volune Set.
8. Sanderson, D. M.: Earnshaw, C. G. Hum. Exp. Toxicol. 1991, 10 (4), 261.
9. Lee, S. A. J. Fluorine Chem. 2001, 109 (1), 55.
10. Edited by Urben, P. G.; Compiled by Pitt, M. J. Bretherick's Handbook of Reactive Chemicals, 6th ed.; Butterworth-Heinemann Ltd: Oxford, 1999.
11. National Fire Protection Association's Manual of Hazardous Chemical Reactions, 5th ed.; NFPA: Boston, 1975.
12. (a) Craven, A. Inst. Chem. Eng. Symp. Ser. 1987, 102, 97.
13. (b) Barton, J., Rogers, R., Eds. Chemical Reaction Hazards, 2nd ed.; Institution of Chemical Engineers: Rugby, U.K., 1997.
14. Frurip, D. J.; Freedman, E.; Hertel, G. R. International Symposium on Runaway Reactions, Boston, 1989; CCPS/Institute of Chemical Engineers: New York, 1989; p 39.
15. Lambert, P.; Amery, G. Int. Symp. Runaway React. AIChE: New York, 1989; p 525.
16. Dale, D. J. Org. Process Res. Dev. 2002, 6 (6), 933.
17. Radex. www.systag.ch/e520rxco.htm (accessed Feb 2006).
18. Mettler-Toledo (RC-1). mettler-toledo.mt.com/quickcal (accessed Feb 200).
19. Hazard Evaluation Laboratories (SIMULAR). helgroup.co.uk/home/ reactor-systems/process-scale-up/simular-en.html (accessed Feb 2006).
20. Setaram (DRC). www.setaram.fr/fichiers/produit/drc_gb200392941710630.pdf (accessed Feb 2006).
21. Chemisens. www.alliedchemicaltech.com/reaction (accessed Feb 2006).
22. ARC. www.thermalhazardtechnology.com/products/urc.htm (accessd Feb 2006).
23. PHI-TEC. www.helgroup.co.uk/home/consultancy/reaction-hazards-sp.html (accessed Feb 2006).
24. APTAC. www.tiaxllc.com/technologies/techa_tiaxproducts.php (accessed Feb 2006).
25. ARSST. www.arsst.com (accessed Feb 2006).
26. VSP2. www.fauske.com/VSP2.asp (accessed Feb 2006).
27. www.johnmorris.com.au/html/Hel/adiabatic_high_pressure_dewar.htm (accessed Feb 2006).
28. (a) Hofelich, T. C.; Thomas, R. C. The Use/Misuse of the 100 °C Rule in the interpretation of Thermal Hazard Tests. International Symposium on Runaway Reactions, Boston, 1989; CCPS/Institute of Chemical Engineers: New York, 1989; p 74.
29. (b) Stoessel, F.; Fierz, H.; Lerena, P.; Kille, G. Org. Process Res. Dev. 1997, 1 (6), 428.
30. Ragan, J. A.; am Ende, D. J.; Brenek, S. J.; Eisenbeis, S. A.; Singer, R. A.; Tickner, D. L.; Teixeira, J. J., Jr.; Vanderplas, B. C.; Weston, N. Org. Process Res. Dev. 2003, 7 (2), 155.
31. Ennis, D. S.; Lathbury, D. C.; Wanders, A.; Watts, D. Org. Process Res. Dev. 1998, 2, 287.
32. Ashcroft, C. P.; Challenger, S.; Derrick, A. M.; Storey, R.; Thomson, M. N. Org. Process Res. Dev. 2003, 7, 362.
33. (a) Anon. Org. Synth. 1966, 46, 105.
34. (b) Berthold, W. Proc. 3rd Int. Symp. Loss Prev. Safety Prom. Chem. Ind., 1431, Basle, SSCI 1980.
35. Barker, A. C.; Boardman, K. A.; Broady, S. D.; Moss, W. O.; Patel, B.; Senior, M. W.; Warren, K. E. H. Org. Process. Res. Dev. 1999, 3(4), 253.
36. Anon. Vinyl bromide. Dangerous Prop. Ind. Mater. Rep. 1989, 9 (1), 80;
37. Chem. Abstr. 1989, 110, 198295 AN 1989:198295.
38. http://oaspub.epa.gov/webi/meta_first_new2.try_these_first and www.epa.gov/srs/ (accessed Feb 2006).
39. http://www.environment-agency.gov.uk/netregs/legislation/287972/652894/ 658261/?lang=_e (accessed Feb 2006).
40. Constable, D. J. C.; Curzons, A. D.; Freitas dos Santos, L. M.; Geen, G. R.; Hannah, R. E.; Hayler, J. D.; Kitteringham, J.; McGuire, M. A.; Richardson, J. E.; Smith, P.; Webb, R. L.; Yu, M. Green Chem. 2001, 3, 7.
41. Constable, D. J. C.; Curzons, A. D.; Cunningham, V. L. Green Chem. 2002, 4, 521.
42. Constable, D. J. C.; Curzons, A. D.; Cunningham, V. L.; Mortimer, D. N. Green Chem. 2001, 3, 1.
43. Jimenez-Gonzalez, C.; Constable, D. J. C.; Curzons, A. D.; Cunningham, V. L. Clean Technol. Environ. Policy 2002, 4, 44.
44. Fujita, K. Org. Lett. 2004, 6 (20), 3525.
45. Goldwater, L. J. Sci. Am. 1971, 224 (5), 15.
46. (a) Dale, D. J.; Dunn, P. J.; Golightly, C.; Hughes, M. L.; Levett, P. C.; Pearce, A. K.; Searle, P. M.; Ward, G.; Wood, A. S. Org Process Res. Dev. 2000, 4 (1), 17.
47. (b) Dunn, P. J.; Galvin, S.; Hettenbach, K. Green Chem. 2004, 6, 43.
48. Andrews, I. P.; Atkins, R. J.; Breen, G. F.; Carey, J. S.; Forth, M. A.; Morgan, D. O.; Shamji, A.; Share, A. C.; Smith, S. A. C.; Walsgrove, T. C.; Wells, A. S. Org. Process Res. Dev. 2003, 7, 655.
49. Atkins, R. J.; Banks, A.; Bellingham, R. K.; Breen, G. F.; Carey, J. S.; Etridge, S. K.; Hayes, J. F.; Hussain, N.; Morgan, D. O.; Oxley, P.; Passey, S. C.; Walsgrove, T. C.; Wells, A. S. Org. Process Res. Dev. 2003, 7, 663.
50. http://www.unodc.org/unodc/index.html (accessed Feb 2006).
51. http://www.incb.org/incb/index.html (accessed Feb 2006).
52. http://www.opsi.gov.uk/and http://www.usdoj.gov/dea/index.htm (accessed Feb 2006).
53. (a) http://www.whitehousedrugpolicy.gov/index.html (accessed Feb 2006).
54. (b) http://www.deadiversion.usdoj.gov/index.html (accessed Feb 2006).
55. (a) Dack, K. N.; Maguire, R. J. (Pfizer Limited, U.K.; Pfizer Inc.). PCT Int. Appl. 2004, WO 2004056750; Chem. Abstr. 2004, 141, 106197.
56. (b) Boswell, R. F.; Lo, Y. S. (Boehringer Ingelheim Chemicals, Inc., USA). 2002 US Pat. 6399828; Chem. Abstr. 2002, 137, 5982.
57. (c) Song, Z. J.; Zhao, M.; Frey, L.; Li, J.; Tan, L.; Chen, C. Y.; Tschaen, D. M.; Tillyer, R.; Grabowski, E. J. J.; Volante, R.; Reider, P. J.; Kato, Y.; Okada, S.; Nemoto, T.; Sato, H.; Akao, A.; Mase, T. Org. Lett. 2001, 3(21), 3357.
58. (d) Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119 (28), 6496.
59. http://www.cas.org/ (accessed Feb 2006).
60. http://www.dti.gov.uk/index.html and http://www.state.gov/ (accessed Feb 2006).
61. http://www.hse.gov.uk/comah (accessed Feb 2006).
62. http://www.osha.gov/ (accessed Feb 2006).
63. http://www.epa.gov/ (accessed Feb 2006).
64. am Ende, D. J.; Vogt, P. F. Org. Process Res. Dev. 2003, 7 (6), 1029.
65. http://www.hse.gov.uk/index.htm (accessed Feb 2006).
66. Details of EUSES can be found at the European Chemicals Bureau at http://ecb.jrc.it/ (accessed Feb 2006).
67. European Chemical Substances Information System - ESIS. http://ecb.jrc.it/ (accessed Feb 2006).
68. Jackson, H. Basic Intellectual Property Concepts. Patent Strategy: For Researchers and Research Managers, 2nd ed.; John Wiley & Sons Ltd: Chichester, 2001; Chapter 1.
69. Simmons, E. S. Drug Discovery Today 1998, 3 (2), 52.
70. Cabri, W.; Di Fabio, R. From Bench to Market: The Evolution of Chemical Synthesis; Oxford University Press: Oxford, 2000; p 168.
71. (a) Burk, M. J.; de Koning, P. D.; Grote, T. D.; Hoekstra, M. S.; Hoge, G.; Jennings, R. A.; Skissell, W.; Le, T. V.; Lennon, I. C.; Mulhern, T. A.; Ramsden, J. A.; Wade, R. A. J. Org. Chem. 2003, 68 (14), 5731.
72. (b) Hoge, G.; Wu, H.-P.; Kissel, W. S.; Pflum, D. A.; Greene, D. J.; Bao, J. J. Am. Chem. Soc. 2004, 126 (19), 5966.
73. Federsel, H.-J. Chirality in Industry II; Wiley: 1997; p 225.
74. Bulteau, G. S. Aft. Pat. 6802593, 1968; Chem. Abstr. 1969, 71, 30354b.
75. Pharmaceutical R&D, Costs, Risks and Rewards; Office of Technology Assessment, Congress of the U.S.: 1993; Appendix G, p 302.
76. Kolassa, E. M. Elements of Pharmaceutical Pricing; The Pharmaceutical Products Press (Haworth Press Inc.): 1997.
77. Batch Plus. www.aspentec.com (accessed Feb 2006).
78. Moseley, J. D.; Moss, W. O.; Welham, M. J. Org. Process. Res. Dev. 2001, 5 (5), 491.
79. Dagger, R. E.; Fortunak, J. M.; Giles, R. G.; Halyer, J. D.; Howie, S. L. B.; Mastrocola, A.; Negus, A.; Oxley, P. W.; Walsgrove, T. C.; Walsh, S. E. J. Heterocycl. Chem. 1995, 32, 875.
80. Giles, R. G.; Halyer, J. D.; Howie, S. L. B.; Negus, A.; Oxley, P. W.; Walsgrove, T. C.; Whiter, M. Org. Process Res. Dev. 1998, 2, 3.
81. Challenger, S.; Derrick, A.; Mason, C. P.; Silk, T. V. Tetrahedron. Lett. 1999, 40 (11), 2187.
82. Burk, M. J.; Bienewald, F.; Challenger, S.; Derrick, A.; Ramsden, J. A. J. Org. Chem. 1999, 64 (9), 3290.
83. http://www.fda.gov/cder/OPS/default.htm (accessed Feb 2006).
84. ICHQ3A(R): Impurities In New Drug Substances. http://www.ifpma.org/ ich5q.html - Q3A(R) (accessed Feb 2006).
85. ICHQ3C: Impurities: Guideline For Residual Solvents. http://www.ifpma. org/pdfifpma/q3c.pdf (accessed Feb 2006).
86. ICHQ6A: Specifications: Test Procedures And Acceptance Criteria For New Drug Substances And New Drug Products: Chemical Substances. http://www.ifpma.org/pdfifpma/q6a.pdf (accessed Feb 2006).
87. ICH Q7A GMP for Active Pharmaceutical Ingredients. http://www.ifpma.org/ ich5q.html#GMP (accessed Feb 2006).
88. http://www.emea.eu.int/pdfs/human/qwp/013096en.pdf (accessed Feb 2006).
89. http://www.pharmtech.com/pharmtech/data/articlestandard/pharmtech/062003/ 45872/article.pdf (accessed Feb 2006).
90. (a) http://online.pheur.org/entry.html (accessed Feb 2006).
91. (b) Ciba Geigy, Neth. Pat. Appl. 6,604,752, 1966; Chem. Abstr. 1967, 67, 81925.
92. Braatz, R. D. Lasentec User Forum; New York, 2003.
93. Paul, E. Chem. Ind. (London, U.K.) 1990, 10, 320.
94. Hawkins, J. M.; Makowski, T. W. Org. Process. Res. Dev. 2001, 5 (3), 328.
95. Owen, M. R.; Luscombe, C.; Lai, L.-W.; Godbert, S.; Crookes, D. L.; Emiabata-Smith, D. Org. Process Res. Dev. 2001, 5 (3), 308.
96. Ward, H. W.; Sekulic, S. S.; Wheeler, M. J.; Taber, G.; Urbanski, F. J.; Sistare, F. E.; Norris, T.; Aldridge, P. K. Appl. Spectrosc. 1998, 52, 17.
97. LeBlond, C.; Wang, J.; Larson, R.; Orella; Sun, Y.-K. Top. Catal. 1998, 5, 149.
98. Marziano, I.; Sharp, D. C. A.; Dunn, P. J.; Hailey, P. A. Org. Process Res. Dev. 2000, 4 (5), 357.
99. Quallich, G. J. Chirality 2005, 17 (Suppl.), S120-S126.
100. Yu, L. X.; Lionberger, R. A.; Raw, A. S.; D'Costa, R.; Wu, H.; Hussain, A. S. Adv. Drug Delivery Rev. 2004, 56 (3), 349.
101. Perry's Chemical Engineers' Handbook, 7th ed.; Perry, R., Green, D., Eds.; McGraw-Hill: London, 1997.
102. Jozwiakowski, M. J. Water-Insoluble Drug Formulation. 2000; Interpharm Press: Englewood, CO, 2000; p 525.
103. (a) Marziano, I. 3rd International Workshop on Polymorphism and Crystallisation, San Francisco, 12-14 Nov 2001, Scientific Update: Mayfield, U.K., 2001.
104. (b) Chemburkar, S. R.; Bauer, J.; Deming, K.; Spiwek, H.; Patel, K.; Morris, J.; Henry, R.; Spenton, S.; Dziki, W.; Porter, W.; Quick, J.; Bauer, P.; Donaubauer, J.; Narayanon, B. A.; Soldani, M.; Riley, D.; McFarland, K. Org. Process Res. Dev. 2000, 4 (5), 413.
105. http://www.lasentec.com (accessed Feb 2006).
106. http://www.helgroup.co.uk/home/software-sp.html (accessed Feb 2006).
107. Birch, M.; Fussell, S.; Hardy, R.; Higginson, P. D.; Jupp, K.; Marziano, I. Lasentec User Forum; New York, 2003.
108. Dunn, P. J.; Hughes, M. L.; Searle, P. S.; Wood, A. S. Org. Process Res. Dev. 2003, 7, 244.
109. Ennis, D. S.; McManus, J.; Wladyslaw, W.-K.; Richardson, J.; Smith, G. E.; Carstairs, A. Org. Process Res. Dev. 1999, 3, 248.
110. Dale, D. J.; Draper, J.; Dunn, P. J.; Hughes, M. L.; Hussain, F.; Levert, P. C.; Ward, G. B.; Wood, A. S. Org. Process Res. Dev. 2002, 6 (6), 767.
111. Waite, D. C.; Mason, C. P. Org. Process Res. Dev. 1998, 2 (2), 116.
112. Ainge, D.; Vaz, L.-M. Org. Process Res. Dev. 2002, 6, 811.
113. Schmid, C. R.; Bryant, J. D.; Dowlatzedah, M.; Phillips, J. L.; Prather, D. E.; Schantz, R. D.; Sear, N. L.; Vianco, C. S. J. Org. Chem. 1991, 56, 4056.
114. Ace, K. W.; Armitage, M. A.; Bellingham, R. B.; Blackler, P. D.; Ennis, D. S.; Hussain, N.; Lathbury, D. C.; Morgan, D. O.; O'Conner, N.; Oakes, G. H.; Passey, S. C.; Powling, L. C. Org. Process Res. Dev. 2001, 5, 479.
115. Sharratt, P. N., Ed. Handbook of Batch Process Design: Kluwer Academic: 1999.
116. Ku, H.-m; et al. Chem. Eng. Prog. 1987, 83 (8), 35.
117. Manganaro, J. L. Chem. Eng. Prog. 2002, 98 (8), 70.
118. Cabri, W.; Di Fabio, R. From Bench to Market: The Evolution of Chemical Synthesis; Oxford University Press: 2000; p 214.
119. Lindberg, P.; Brandstrom, A.; Wallmark, B.; Mattsson, B.; Rikner, L.; Hoffman, K. J. Med. Res. Rev. 1990, 10, 1.
120. Olbe, L.; Carlsson, E.; Linberg, P. Nat. Rev. Drug. Discov. 2003, 2, 132.
121. Federsel, H.-J.; Larsson, M. Asymmetric Catalysis on Industrial Scale; Wiley: 2004; p 413.
122. Bentley, A.; Butters, M.; Green, S. P.; Learmonth, W. J.; MacRae, J. A.; Morland, M. C.; O'Connor, G.; Skuse, J. Org. Process Res. Dev. 2002, 6 (2), 109.