Synthetic approaches to the 2008 new drugs

Mini-Reviews in Medicinal Chemistry

Volumn 9, Issue 14, 2009, Pages 1655-1675

  Liu, Kevin K C ^a   Sakya, Subas M ^a   O'Donnell, Christopher J ^a   Li, Jin ^b  

^a PFIZER INC   (United States)

^b Shenogen Pharma Group   (China)

Author keywords

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

Indexed keywords

17 METHYLNALTREXONE BROMIDE; ALVIMOPAN; BIOLIMUS A9; BLONANSERIN; CALCIUM CHANNEL BLOCKING AGENT; CEFTOBIPROLE MEDOCARIL; CHOLINE DERIVATIVE; CHOLINE FENOFIBRATE; CLEVIDIPINE; CLEVIDIPINE BUTYRATE; DABIGATRAN ETEXILATE; DESVENLAFAXINE; ETRAVIRINE; FENOFIBRIC ACID; FESOTERODINE; HARKOSERIDE; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE INHIBITOR; LEXISCAN; METHYLNALTREXONE BROMIDE; NEW DRUG; OPIATE ANTAGONIST; PIRESPA; PIRFENIDONE; RAPAMYCIN DERIVATIVE; REGADENOSON; RIVAROXABAN; SITAFLOXACIN; SUGAMMADEX; TAFLUPROST; TRILIPIX; UNCLASSIFIED DRUG; ZEFTERA;

ABNORMALLY HIGH SUBSTRATE CONCENTRATION IN BLOOD; ADENOIDITIS; BOLUS INJECTION; BRONCHITIS; COMMUNITY ACQUIRED PNEUMONIA; CONSTIPATION; DRUG APPROVAL; DRUG BIOAVAILABILITY; DRUG EFFICACY; DRUG ELUTING STENT; DRUG INHIBITION; DRUG MECHANISM; DRUG METABOLISM; DRUG SAFETY; DRUG STRUCTURE; DRUG SYNTHESIS; DYSLIPIDEMIA; EPILEPSY; FIBROMYALGIA; FIBROSING ALVEOLITIS; FOCAL EPILEPSY; GLAUCOMA; HOSPITAL ACQUIRED PNEUMONIA; HOT FLUSH; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS 1 INFECTION; HYPERCHOLESTEROLEMIA; HYPERGLYCERIDEMIA; HYPERTENSION; ILEUS; INFECTIOUS PNEUMONIA; INFLAMMATION; INTESTINE FUNCTION DISORDER; INTRAOCULAR HYPERTENSION; LARYNGOPHARYNGITIS; MAJOR DEPRESSION; MOLECULAR RECOGNITION; NEUROFIBROMA; NEUROFIBROMATOSIS; NEUROPATHIC PAIN; NIGHT SWEAT; OVERACTIVE BLADDER; PHARMACOLOGIC STRESS TESTING; PNEUMONIA; POSTOPERATIVE COMPLICATION; POSTOPERATIVE ILEUS; RESPIRATORY TRACT INFLAMMATION; RESTENOSIS; REVIEW; SCHIZOPHRENIA; SECONDARY INFECTION; SKIN INFECTION; THROMBOSIS; URGE INCONTINENCE; VENOUS THROMBOEMBOLISM;

EID: 77949901282     PISSN: 13895575     EISSN: None     Source Type: Journal    
DOI: 10.2174/138955709791012201     Document Type: Review

References (81)

1. Raju, T. N. K. The Nobel chronicles. 1988: James Whyte Black, (b 1924), Gertrude Elion (1918-99), and George H Hitchings (1905-98). Lancet, 2000, 355, 1022.
2. Li, J.; Liu, K.-C. Synthetic approaches to the 2002 new drugs. Mini-Rev. Med. Chem., 2004, 4, 207-33.
3. Liu, K.-C.; Li, J.; Sakya, S. M. Synthetic approaches to the 2003 new drugs. Mini-Rev. Med. Chem., 2004, 4, 1105-25.
4. Li, J.; Liu, K.-C.; Sakya, S. M. Synthetic approaches to the 2004 new drugs. Mini-Rev. Med. Chem., 2005, 5, 1133-1144.
5. Sakya, S. M.; Liu, K.-C.; Li, J. Synthetic approaches to the 2005 new drugs. Mini-Rev. Med. Chem., 2007, 7, 429-450.
6. Liu, K.-C.; Sakya, S. M.; Li, J. Synthetic approaches to the 2006 new drugs. Mini-Rev. Med. Chem., 2007, 7, 1255-1269.
7. Liu, K.-C.; Sakya, S. M.; O'Donnell, C. J.; Li, J. Synthetic approaches to the 2007 new drugs. Mini-Rev. Med. Chem., 2008, 8, 1526-1548.
8. Graul, A. I.; Revel, L.; Barrionuevo, M.; Cruces, E.; Rosa, E.; Vergés, C.; Lupone, B.; Diaz, N.; Castañer, R. The Year's New Drugs and Biologics-2008. Drug News Perspect., 2009, 22, 7-29.
9. Alvimopan Drugs R D, 2006, 245-253.
10. Zimmerman, D. M.; Gidda, J. S.; Cantrell, B. E.; Schoepp, D. D.; Johnson, B. G.; Leander, J. D. Discovery of a Potent, Peripherally Selective trans-3,4-Dimethyl-4-(3-hydroxyphenyl)piperidine Opioid Antagonist for the Treatment of Gastrointestinal Motility Disorders. J. Med. Chem., 1994, 37, 2262-2265.
11. Werner, J. A.; Cerbone, L. R.; Frank, S. A.; Ward, J. A.; Labib, P.; Tharp-Taylor, R. W.; Ryan, C. W. Synthesis of trans-3,4-Dimethyl-4-(3- hydroxyphenyl)piperidine Opioid Antagonists: Application of the Cis-Thermal Elimination of Carbonates to Alkaloid Synthesis. J. Org. Chem., 1996, 61, 587-597.
12. Le bourdonnec, B.; Dolle, R. Novel Processes for the preparation of peripheral opiod antagonist compounds and intermediates thereto. WO 04014310 A2, 2004.
13. Buehler, J. D. Compositions Containing Opiod Antagonists. WO 07047935, 2007.
14. a) Grube, Eberhard; Buellesfeld, Lutz. BioMatrix Biolimus A9 - eluting coronary stent: a next-generation drug-eluting stent for coronary artery disease. Expert Rev. Med. Devices, 2006, 3, 731-41;
15. b) Betts, R. E.; Savage, D. R.; Shulze, J. E. 42-O-Alkoxyalkyl rapamycin derivatives and compositions comprising same. US 20050101624 A1, 2005.
16. Heading, C. E. Blonanserin Curr. Opin. CPNS Invest. Drugs 2000, 2, 79-84.
17. Blonanserin Drugs R D, 1999, 2 , 49-50.
18. Ochi, T.; Sakamoto, M.; Minamida, A.; Suzuki, K.; Ueda, T.; Une, T.; Toda, H.; Matsumoto, K.; Terauchi, Y. Syntheses and properties of the major hydroxy metabolites in humans of blonanserin AD-5423, a novel antipsychotic agent Bioorg. Med. Chem. Lett., 2005, 15, 1055-1059.
19. Hino, K.; Kai, N.; Sakamoto, M.; Kon, T.; Oka, M.; Furakawa, K.; Ochi, Y. 2-(1-piperazinyl)-4-phenylcycloalkanopyridine derivatives, processes for the production thereof, and pharmaceutical composition containing the same. EP 0385237 A2, 1990.
20. Page, M. G. P. Anti-MRSA B-lactams in development. Curr. Opin. Pharm., 2006, 6, 480-485.
21. Sorbera, L. A.; Castañer, J.; Castañer, R. M..Ceftobiprole/Ceftobiprole Medocaril. Drugs Future 2005, 30(1), 11-22.
22. Angehrn, P.; Hebeisen, P.; Heinze-Krauss, I.; Page, M.; Runtz, V. Vinyl pyrrolidine cephalosporins with basic substituents. EP 0849269 A1, 1998.
23. Hebeisen, P.; Hilpert, H.; Humm, R. (Basilea Pharmaceutica AG). New process for the preparation of vinyl-pyrrolidinone cephalosporine derivs. WO 0190111 A1, 2001.
24. Hebeisen, P.; Gross, G.; Heinze-Krauss, I.; Hubschwerlen, C.; Schmitt-Hoffmann, A.H.; Theil, F.P. Synthesis, physicochemical and pharmacokinetic properties of water soluble prodrugs of Ro 63-9141/000. 38th Intersci. Conf. Antimicrob. Agents Chemother., (Sept 24-27, San Diego) 1998, Abst. F-26.
25. Hebeisen, P.; Hubschwerlen, C.; Specklin, J.-L. (Basilea Pharmaceutica AG). Derivs. of 3-(2-oxo-[1,3.]bipyrrolidinyl-3-ylidenemethyl)- cephems, WO 9965920, 1999.
26. Spurr, P.; Trickes, G. New process for the manufacture of cephalosporin derivatives. EP 1067131 A1, 2000.
27. Teraji, S.; Sakane, K.; Goto, J. 7-amino-thiadiazole oxyimino derivatives of cephem and cepham compounds. US 4381299, 1983.
28. Clink, R. D.; Paterson JR., J. B.; Gao, Y.; Zhang, G. G. Z.; Long, M. A.; Morris, J. B.; Rosenberg, J. Salts for fenofibric acid and pharmaceutical formulations thereof. US 20050148594 A1, 2005.
29. Davis, R. D.; Fitzgerald, R. N.; Gao, J. Improved method for the synthesis of 2-methyl-2-aryloxypropanoic acid derivatives. Synthesis, 2004, 1959-1962.
30. Bourgogne, J-P.; Sornay, R. New procedures for the preparation of fibrates. EP 0245156 B1, 1990.
31. Dellis, P.; Nasar, Kamel Process for preparing quaternary acid and ammonium salts. US 20080275270 A1, 2008.
32. Nordlander, M.; Sjoequist, P.-O.; Ericsson, H.; Ryden, L. Pharmacodynamic, pharmacokinetic and clinical effects of clevidipine , an ultrashort-acting calcium antagonist for rapid blood pressure control. Cardiovasc. Drug Rev., 2004, 22, 227-250.
33. Andersson, K. H.; Nordlander, M.; Westerlund, R. C. Preparation of short-acting 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate calcium-antagonist antihypertensives. WO 9512578, 1995.
34. Sorbera, L. A.; Castañer, J.; Castañer, R. M..Dabigatran Etexilate. Drugs Future, 2005, 30, 877-885.
35. Hauel, N. H.; Nar, H.; Priepke, H.; Ries, U.; Stassen, J. M.; Wienen, W. Structure-based design of novel potent nonpeptide thrombin inhibitors. J. Med. Chem., 2002, 45, 1757-1766.
36. Hauel, N.; Priepke, H.; Ries, U.; Stassen, J. M.; Wienen, W. (Boehringer Ingelheim Pharma KG). Disubstituted. bicyclic heterocycles, their production and use as medicaments. WO 98037075, 1998.
37. Hauel, N.; Priepke, H.; Ries, U.; Stassen, J. M., Wienen, W. (Boehringer Ingelheim Pharma KG). Disubstituted Bicyclic Heterocycles, the preparations and use thereof as pharmaceutical compositions. US 6087380, 2000.
38. Zerban, G.; Hausherr, A.; Hamm, R.; Koch, G.; Schlarn, K. Improved process for the preparation of the salts of 4-(benzimidazolylmethylamino)- benzamides. WO 070717142 A1, 2007;
39. ibid. WO 07071743 A1, 2007.
40. Sorbera, L. A.; Bolós, J.; Serradell, N. Desvenlafaxine succinate: antidepressant, treatment of postmenopausal syndrome, 5-HT and norepinephrine reuptake inhibitor. Drugs Future, 2006, 31, 304-9.
41. a) Pae, C.-U. Desvenlafaxine: a new antidepressant or just another one? Expert. Opin.Pharmacol., 2009, 10, 875-87;
42. b) Yang, L.P.H.; Plosker, G.L. Desvenlafaxine extended release. CNS Drugs, 2008, 22, 1061-1069.
43. For a review of the preparation of venlafaxine see: The Art of Drug Synthesis. Johnson, D. S.; Li, J. J., Eds.; Wiley, 2007, p. 203.
44. Hadfield, A.F.; Shah, S.M.; Winkley, M.W.; Sutherland, K.W.; Provost, J.A.; Park, A.; Shipplett, R. A.; Russell, B. W.; Weber, B. T. Novel succinate salt of O-desmethyl-venlafaxine. WO 02064543, 2002.
45. Gore, V.G.; Kulkarni, V.S.; Wakchaure, V.S.; Hublikar, M.G.; Wavhal, S.R. Process for the preparation of O-desmethyl venlafaxine. WO 08093142 A1, 2008.
46. Knoll, B. M.; Vento, S.; Temesgen, Z. Etravirine. Drugs Today, 2008, 44, 23-33.
47. Haslinger, B. A.; Arendt, G. TMC-125 Tibotec. Curr. Opin. Invest. Drugs, 2004, 5, 208-13.
48. Ludovici, D.W.; De Corte, B.L.; Kukla, M.J.; Ye, H.; Ho, C. Y.; Lichtenstein, M. A.; Kavash, R. W.; Andries, K.; de Bethune, M-P.; Azijn, H.; Pauwels, R.; Lewi, P. J.; Heeres, J.; Koymans, L. M. H.; de Jonge, M. R.; Van Aken, K. J. A.; Daeyaert, F. F. D.; Das, K.; Arnold, E.; Jansen, P. A. J. Evolution of anti-HIV drug candidates. Part 3: Diarylpyrimidine (DAPY) analogues. Bioorg. Med. Chem. Lett., 2001, 11, 2235-2239.
49. Verreck, G.; Baert, L. Antiviral compositions. WO 0122938 A1, 2001.
50. De Corte, B.; De Jonge, M.. R.; Heeres, J.; Ho, C. Y.; Janssen, Paul, A. J.; Kavash, R. W.; Koymans, L. M. H.; Kukla, M., J.; Ludovici, D. W.; Van Aken, K. J. A. HIV replication inhibiting pyrimidines. WO 0027825, 2000.
51. Guillemont, J. E. G.; Mordant, C. I. HIV inhibiting 6-substituted pyrimidines. WO 08080964 A1, 2008.
52. Heeres, J.; Lewi, P. J.; Leemans, R.; Moens, L. J. R. HIV inhibiting 2-(4-cyanophenyl)- pyrimidine derivatives. WO 06079656 A1, 2006.
53. De Kock, H. A.; Wigerinck, P.P.T.B.P. HIV inhibiting 2-(4-cyanophenyl)-6- hydroxylaminopyrimidines. WO 06094930 A1, 2006.
54. 3 Antagonist. Drugs Future, 2003, 28, 647-651.
55. Meese, C. Stable salts of novel derivatives of 3,3-diphenylpropylamines. US 6585650 B1, 2005.
56. Ahman, J. B.; Dillon, B. R.; Pettman, A. J. Process for the production of benzopyran-2-ol derivatives. WO 138440 A1, 2007.
57. McIntyre, J. A.; Castañer, J.; Martin, L. Lacosamide, antiepileptic drug, treatment of neuropathic pain, NMDA glycine-site antagonist. Drugs Future, 2004, 29, 992-997.
58. a) Choi, D.; Stables, J.P.; Kohn, H. Synthesis and anticonvulsant activities of N-benzyl-2-acetamidopropionamide derivatives. J. Med. Chem., 1996, 39, 1907-16;
59. b) Kohn, H. Anticonvulsant enantiomeric amino acid derivatives. US 5773475, 1998.;
60. c) Kohn, H.; Andurkar, S. V. Anticonvulsant enantiomeric amino acid derivatives. US 6048899, 2000.
61. Riedner, J.; Dunne, G. Synthesis Scheme for Lacosamide. US 0027137 (A1), 2008.
62. Chen, T.-Y.; Rosow, C.E. Methylnaltexone bromide: Opioid receptor antagonist, treatment of constipation, treatment of postoperative ileus. Drugs Future, 2007, 32, 771-775.
63. Cantrell, G. L.; Halvachs, R. E. Process for the preparation of quaternary N-alkyl morphinan alkaloid salts. US 0014771 A1, 2006.
64. Phillips, J. R.; Blatt, M. L.; Ozes, N. O. Pirfenidone and interferon gamma-1B inhibit the profibrotic effect of osteopontin Chest,2006, 130(4, Suppl.): 229S.
65. Ma, Z.; Wang, Z.; Shen, Z. Synthesis of pirfenidone. Zhong-guo Yiyao Gongye Zazhi, 2006, 37(6), 372-373.
66. 2A receptor Bioorg. Med. Chem. Lett., 2002, 12, 2935-2939.
67. 2A adenosine receptor Nucleosides, Nucleotides Nucleic Acids, 2001, 20, 343-360.
68. 2a- adenosine receptor agonist and its polymorphs WO 08143667 A1, 2008.
69. Zhao, G.; Serpllion, S.; Shryock, J.; Messina, E.; Xu, X.; Ochoa, M.; Belardinelli, L.; Hintze, T. H. Regadenoson, a novel pharmacologic stress agent for use in myocardial perfusion imaging, does not have a direct effect on the QT interval in conscious dogs. J. Cardiovasc Pharmacol., 2008, 52, 467-473.
70. Lieu, H. D.; Thomas, G. Myocardial perfusion imaging. WO 08086096 A2, 2008.
71. Escolar, G.; Villalta, J.; Casals, F.; Bozzo, J.; Serradell, N.; Bolos, J. Rivaroxaban: factor Xa inhibitor anticoagulant. Drugs Future, 2006, 31, 484-493.
72. Thomas, C.R. Method for producing 5-chloro-N-[[(5S)-2-oxo-3-[4-(3-oxo-4- morpholinyl)-phenyl]-1,3-oxazolidin-5-yl]-methyl]-2-thiophene carboxamide US 2007149522, 2007.
73. Kimura, Y.; Atarashi, S.; Kawakami, K.; Sato, K.; Hayakawa, I. (Fluorocyclopropyl)quinolones. 2. Synthesis and Stereochemical Structure -Activity Relationships of Chiral 7-(7-Amino-5-azaspiro[2.4]heptan-5-yl)-1-(2- fluorocyclopropyl)quinolone Antibacterial Agents. J. Med. Chem., 1994, 37, 3344-3352.
74. Tamura, O.; Hashimoto, M.; Kobayashi, Y.; Katoh, T.; Nakatani, K.; Kamada, M.; Hayakawa, I.; Akiba, T.; Terashima, S. Synthesis and Optical Resolution of dl-cis-2-Fluorocyclopropylamine, the Key Component of the New Generation of Quinolonecarboxylic Acid, DU-6859. Tetrahedron Lett., 1992, 33, 3483-3486.
75. Tamura, O.; Hashimoto, M.; Kobayashi, Y.; Katoh, T.; Nakatani, K.; Kamada, M.; Hayakawa, I.; Akiba, T.; Terashima, S. Synthesis and Optical Resolution of dl-cis-2-Fluorocyclopropylamine, the Key Component of the New Generation of Quinolonecarboxylic Acid, DU-6859. Tetrahedron Lett., 1992, 33, 3487-3490.
76. Kaneuchi, T.; Kimura, Y.; Yukimoto, Y. Process for preparing 8-chloroquinolone derivatives. CN1062906A, 1992.
77. Adam, J. M.; Bennett, D. J.; Bom, A.; Clark, J. K.; Feilden, H.; Hutchinson, E. J.; Palin, R.; Prosser, A.; Rees, D. C.; Rosair, G. M.; Stevenson, D.; Tarver, G. J.; Ming-Qiang Zhang, M.-Q. Cyclodextrin-Derived Host Molecules as Reversal Agents for the Neuromuscular Blocker Rocuronium Bromide: Synthesis and Structure-Activity Relationships J. Med. Chem., 2002, 45, 1806-1816.
78. Gorin, B. I.; Riopelle, R. J.; Thatcher, G. R. J. Efficient perfacial derivatization of cyclodextrins at the primary face. Tetrahedron Lett., 1996, 37, 4647-4650.
79. Zhang, M.-Q.; Palin, R.; Bennet, D. J. 6-Mercaptocyclodextrin derivatives, their preparation, and the use as reversal agents for drug-induced neuromuscular block. WO 0140316 A1, 2001.
80. Wang, Y.; Bolos, J.; Serradell, N. Tafluprost Drugs Future, 2006, 31(9), 788-792.
81. Matsumura, Y.; Mori, N.; Nakano, T.; Sasakura, H.; Matsugi, T.; Hara, H.; Morizawa, Y. Synthesis of the highly potent prostanoid FP receptor agonist, AFP-168: A novel 15-deoxy-15,15-difluoroprostaglandin F2alpha derivative Tetrahedron Lett., 2004, 45, 1527-1529