Alternative Synthesis of Bilastine

REFERENCES

• Orjales , A. V. ; Rubio , V. ; Bordell , M. Benzimidazole derivatives with antihistaminic activity. US Patent 5877187, 1999.
   Google Scholar
• Corcóstegui , R. ; Labeaga , L. ; Innerárity , A. ; Berisa , A. ; Orjales , A. V. Preclinical pharmacology of bilastine, a new selective histamine H1 receptor antagonist . Drugs R. D. 2005 , 6 , 371 – 384 .
   PubMedGoogle Scholar
• Corcóstegui , R. ; Labeaga , L. ; Innerárity , A. ; Berisa , A. ; Orjales , A. V. In vivo pharmacological characterization of bilastine, a potent and selective histamine H1 receptor antagonist . Drugs R. D. 2006 , 7 , 219 – 231 .
   PubMedGoogle Scholar
• Sommer , E. ; Weber , K. ; Lucero , M. L. ; Arteche , J. ; Orjales , A. Oncogenicity risk assessment of bilastine: A novel antihistamine compound . Toxicol. Lett. 2008 , 180 ( 1 ), S156 .
   Google Scholar
• Ganza , A. ; Gonzalo , A. ; Lucera , M. L. ; Orjales , A. Toxicokinetics of bilastine in animals: The effects of dose and route of administration . Toxicol. Lett. 2008 , 180 ( 1 ), S70 .
   Google Scholar
• Bachert , C. ; Kuna , P. ; Sanquer , F. ; Ivan , P. ; Dimitrov , V. ; Gorina , M. M. ; van de Heyning , P. ; Loureiro , A. Comparison of the efficacy and safety of bilastine 20 mg vs desloratadine 5 mg in seasonal allergic rhinitis patients . Allergy 2009 , 64 , 158 – 165 .
   PubMed Web of Science ®Google Scholar
• Orjales , A. V. ; Bordell Martin , M. ; Canal Mori , G. ; Blanco Fuente , H. ; Lucero de Pablo , M. L. ; Mosquera Pestaña , R. WO Patent 089425, 2003.
   Google Scholar
• Orjales , A. V. ; Rubio-Royo , V. New piperidine derivatives of benzimidazole as antihistanminic and antiallergic agents. ES Patent 2048109, 1994.
   Google Scholar
• Orjales , A. V. ; Rubio-Royo , V. ; Bordell Martin , M. Benzene ethanol derivative for antihistamine products consists of a composition based on a methyl bromobenzene acetate. ES Patent 2151442, 2000.
   Google Scholar
• A modified approach to 4 in which the dimethyloxazoline is installed first and the dimethylation conducted second, using KHMDS/MeI, has also been reported but was not evaluated: D'Ambra, T. E.; Pilling, G. M. WO Patent 972313, 1997.
   Google Scholar
• Krolski , M. E. ; Renaldo , A. F. ; Rudisill , D. E. ; Stille , J. K. Palladium-catalyzed coupling of 2-bromoanilines with vinylstannanes . J. Org. Chem. 1988 , 53 , 1170 – 1176 .
   Web of Science ®Google Scholar
• Chen , C. ; Nagy , G. ; Walker , A. V. ; Maurer , K. ; McShea , A. ; Moeller , K. D. Building addressable libraries: The use of a mass spectrometry cleavable linker for monitoring reactions on a microelectrode array . J. Am. Chem. Soc. 2006 , 128 , 16020 – 16021 .
   PubMed Web of Science ®Google Scholar
• Brown , H. C. ; Murray , K. J. ; Murray , L. J. ; Snover , J. A. ; Zweifel , G. Hydroboration V: A study of convenient new preparative procedures for the hydroboration of olefins . J. Am. Chem. Soc. 1960 , 82 , 4233 .
   Web of Science ®Google Scholar
• Suseela , Y. ; Perisamy , M. Convenient method for the preparation of catecholborane and promotion of the formation of alkenyl catecholborane using BH3 complexes . J. Organomet. Chem. 1993 , 450 , 47 .
   Web of Science ®Google Scholar
• Bennasar , M. L. ; Roca , T. ; Monerris , M. ; Gracia-Diaz , D. Sequential N-acylamide methylenation-enamide ring-closing metathesis: Construction of benzo-fused nitrogen heterocycles . J. Org. Chem. 2006 , 71 , 7028 – 7034 .
   PubMed Web of Science ®Google Scholar
• Brown , H. C. ; Subba Rao , B. C. Hydroboration I: The reaction of olefins with sodium borohydride–aluminum chloride: A convenient route to organoboranes and anti-Markownikoff hydration of olefins . J. Am. Chem. Soc. 1959 , 81 , 6423 .
   Web of Science ®Google Scholar