Novel and efficient method for the synthesis of racemic fexofenadine

Synthetic Communications

Volumn 41, Issue 15, 2011, Pages 2296-2303

  Raghavendra, G M ^a   Harsha, K B ^a   Vinaya, K ^a   Mantelingu, K ^a   Rangappa, K S ^a  

^a UNIVERSITY OF MYSORE   (India)

Author keywords

Fexofenadine; H1 histamine receptor; Histamine antagonists; Tetrafenadine

Indexed keywords

CUMENE; FEXOFENADINE;

ARTICLE; BROMINATION; DRUG STRUCTURE; DRUG SYNTHESIS; FRIEDEL CRAFTS REACTION; GRIGNARD REACTION; REDUCTION KINETICS; SUBSTITUTION REACTION;

EID: 79957645588     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.502986     Document Type: Article

References (30)

1. Leues, R.; Smit, R.; Timmerman, H. Molecular pharmacological aspects of histamine receptors. Pharmacol. Ther. 1999, 66, 413-463.
2. Buckley, M. G.; Walters, C.; Wong, W. M.; Cawley, M. I.; Ren, S. Mast cell activation in arthritis: Detection of a- and b-tryptase, histamine, and eosinophil cationic protein in synovial fluid. Clin. Sci. (Lon). 1997, 93, 363-370. (Pubitemid 27464300)
3. Renous, M.; Hilliquin, P.; Galoppin, L.; Florentin, I.; Menkes, C. J. H1-Antihistamines and allergic diseases. Osteoatthr. Cartil. 1996, 4, 175-179.
4. De Vos, C. H1-receptor antagonists: Effects on leukocytes, myth or reality? Clin Exp Allergy. 1999, 29, 60-63.
5. Berthon, B.; Taudou, G.; Combetters, L.; Czarlewski, W.; Carmi-Leroy, A. M. In vitro inhibition, by loratadine and descarboxyethoxyloratadine, of histamine release from human basophils, and of histamine release and intracellular calcium fluxes in rat basophilic leukemia cells (RBL-2H3). Biochem. Pharmcol. 1994, 47, 789-794.
6. Church, M. K. H1-Antihistamines and inflammation. Clin. Exp. Allergy. 2001, 31, 1341-1343.
7. Nosal, R.; Drabikova, K.; Janconova, V.; Ptrikova, M.; Fabryova, V. Antiplatelet and antiphagocyte activity of H1-antihistamines. Inflamm. Res. 2005, 54, S19-S20.
8. Honig, P. K.; Wortham, D. C.; Zamani, K.; Conner, D. P.; Mullin, J. C.; Cantilena, L. R. Changes in the Pharmacokinetics and electrocardiographic pharmacodynamics of terfenadine with concomitant administration of erythromycin. J. Clin. Pharmacol. Ther. 1992, 52, 231-238
9. Honig, P. K.; Wortham, D. C.; Zamani, K.; Conner, D. P.; Mullin, J. C.; Cantilena, L. R. Terfenadine-ketoconazole interaction: Pharmacokinetic and electrocardiographic consequences. JAMA 1993, 269, 1513-1518 (Pubitemid 23086411)
10. Woosley, L.; Young, Y.; Chin, J. W. Methods and compositions for treating allergic disorders and other disorders metabolic derivatives of terfenadine. U.S. Patent 5375693, 1994.
11. Carr, A. A.; Dolfini, J. E.; Write, G. J. Piperidine derivatives. U.S. Patent 4254130, 1981.
12. Carr, A. A.; Dolfini, J. E.; Write, G. J. 1-Piperidine-alkylene ketones, pharmaceutical compositions thereof, and method of use thereof. U.S. Patent 4285958, 1981.
13. Ambra, T. E. U.S. Patent 557610, 1996.
14. Kawai, S. H.; Hambalck, R. J.; Just, G. D. A facile synthesis of an oxidation product of terfenadine. J. Org. Chem. 1994, 59, 2620-2622. (Pubitemid 24193330)
15. Patel, S.; Waykole, L.; Repie, O.; Chen, K. M. Synthesis of terfenadine carboxylate. Synth. Commun. 1996, 26, 4699-4710. (Pubitemid 26423511)
16. Fang, Q. K.; Senanayake, C. H.; Wilkinson, H. S.; Wald, S. A.; Li, H. An efficient and facile synthesis of racemic and optically active fexofenadine. Tetrahedron Lett. 1998, 39, 2701-2704. (Pubitemid 28186654)
17. Di Giacomo, B.; Coletta, D.; Natalini, B.; Ni, M. H.; Pellicciari, R. A new synthesis of carboxyterfenadine (fexofenadine) and its bioisosteric tetrazole analogs. Farmco 1999, 54, 600-610. (Pubitemid 29462621)
18. Gross, H.; Rieche, A.; Hoft, E.; Beyer, E. Dichloromethyl methyl ether. Org. Synth. Coll. 1973, 5, 365.
19. Senanayake, C. H.; Fang, Q. K.; Wilkinson, S. H. Preparation of terfenadine and derivatives. WO Patent 9833789, 1998.
20. Senanayake, C. H.; Fang, Q. K.; Wilkinsion, S. H. Preparation of terfenadine and derivatives. Chem. Abstr. 1998, 129, 161498r.
21. King, R. C. H.; Kaminski, M. A. 4-Diphenylmethyl pipperidine derivatives and process for their preparation. WO Patent 9321156, 1993.
22. King, R. C. H.; Kaminski, M. A. 4-(Diphenylmethyl)piperidine derivatives and process for their preparation. Chem. Abstr. 1994, 120, 217287e.
23. Schroeder, C.; Huddleston, R.; Charles, R. Process for the production of the piperidine derivative fexofenadine. WO Patent 102,776, 1994, A1.
24. Schroeder, C.; Huddleston, R.; Charles, R. Preparation of fexofenadine and related compounds. Chem. Abstr. 2003, 138, 55873k.
25. Kawai, S. H.; Hambalek, R. J.; Just, G. A facile synthesis of an oxidation product of terfenadine. J. Org. Chem. 1994, 59 (9), 2620-2622. (Pubitemid 24193330)
26. Carr, A. A.; Dolfini, J. E.; Wright, G. J. Piperidine derivatives. U.S. Patent 4254129, 1981.
27. Carr, A. A.; Dolfini, J. E.; Wright, G. J. Piperidine derivatives with antihistamine action. Chem. Abst. 1981, 194, 156759e.
28. Castaldi, G.; Barreca, G.; Magron, D. Process for preparation of 4-[1-hydroxy- 4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)butyl]-α,α- dimethylbenzeneacetic acid. U.S. Patent 2002/0198233, 2002.
29. Castaldi, G.; Barreca, G.; Magron, D. A process for the preparation of 4-[1-hydroxy- 4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)-butyl]-α, α-dimethylbenzeneacetic acid. Chem. Abst. 2002, 138, 4522.
30. Corey, E. J.; Venkateswarlu, A. Protection of hydroxyl groups as tert-butyldimethylsilyl derivatives. J. Am. Chem. Soc. 1972, 94, 6190-6191.