Synthesis and characterization of metabolites and potential impurities of balsalazide disodium, an anti-inflammatory drug

Synthetic Communications

Volumn 40, Issue 15, 2010, Pages 2241-2253

  Khan, Md Umar ^a,b   Baseer, M A ^b   Kumar, S Ranjith ^a   Saravanakumar, M ^a   Prasannanjali, A G ^a   Gupta, P Badarinadh ^a   Kaushik, Vipin K ^a   Handa, Vijay K ^a   Islam, Aminul ^a  

^a Aurobindo Pharma Ltd   (India)

^b Organic Chemistry Research Laboratory   (India)

Author keywords

5 Aminosalicylic acid; balsalazide; diazo coupling; impurities; synthesis

Indexed keywords

BALSALASIDE BETA ALANINE; BALSALAZIDE; BALSALAZIDE 3 ISOMER; BIPHENYL AZO SALICYLIC ACID; BIS AZO DIACID; BIS AZO SALICYLIC ACID; BIS AZO TRIACID; DECARBOXY BALSAZIDE; DES BETA ALANINE BALSALAZIDE; DRUG METABOLITE; UNCLASSIFIED DRUG;

ARTICLE; DRUG IMPURITY; DRUG METABOLISM; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 77954532062     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903221068     Document Type: Article

References (24)

1. Rasmussen, S. N.; Binder, V.; Maier, K.; Bondesen, S.; Fischer, C.; Klotz, U.; Hansen, S. H.; Hvidberg, E. F. Treatment of Crohn's disease with peroral 5-aminosalicylic acid. Gastroenterology 1983, 85(6), 1350-1353.
2. Campieri, M.; Lanfranchi, G. A.; Bazzocchi, G.; Brignola, C.; Sarti, F.; Franzin, G.; Battocchia, A.; Labo, G.; Dal Monte, P. R. Treatment of ulcerative colitis with high-dose 5-aminosalicylic acid enemas. Lancet 1981, 2(8241), 270-271. (Pubitemid 11042737)
3. Friedman, L. S.; Richter, J. M.; Kirkham, S. E.; DeMonaco, H. J.; May, R. J. 5-Amino-salicylic acid enemas in refractory distal ulcerative colitis: A randomized, controlled trial. Am. J. Gastroenterol. 1986, 81, 412-418.
4. Chan, R. P.; Pope, D. J.; Gilbert, A. P.; Sacra, P. J.; Baron, J. H.; Lennard-Jones, J. E. Studies of two novel sulfasalazine analogs, ipsalazide and balsalazide. Dig. Dis. Sci. 1983, 28(7), 609-615.
5. 1) following a single oral dose. Glycyx Pharmaceuticals Limited, Bermuda, Harris project No. 20060, 1998 (data on file).
6. Azad Khan, A. K.; Piris, J.; Truelove, S. C. An experiment to determine the active therapeutic moiety of sulphasalazine. Lancet 1977, 2(8044), 892-895.
7. Van Hees, P. A.; Bakker, J. H.; van Tongeren, J. H. Effect of sulphapyridine, 5-aminosa-licylic acid, and placebo in patients with idiopathic proctitis: A study to determine the active therapeutic moiety of sulphasalazine. Gut 1980, 21, 632-635.
8. Campieri, M.; Lanfranchi, G. A.; Bazzocchi, G.; Brignola, C.; Sarti, F.; Franzin, G.; Battocchia, A.; Labo, G.; Dal Monte, P. R. Treatment of ulcerative colitis with high-dose 5-aminosalicylic acid enemas. Lancet 1981, 2(8241), 270-271. (Pubitemid 11042737)
9. Rao, S. S.; Cann, P. A.; Holdsworth, C. D. Clinical experience of the tolerance of mesalazine and olsalazine in patients intolerant of sulphasalazine. Scand. J. Gastroenterol. 1987, 3, 332-336.
10. Riley, S. A.; Lecarpentier, J.; Mani, V.; Goodman, M. J.; Mandal, B. K.; Turnberg, L. A. Sulphasalazine-induced seminal abnormalities in ulcerative colitis: Results of mesalazine substitution. Gut 1987, 8, 1008-1012.
11. Nielsen, O. H. Sulfasalazine intolerance: A retrospective survey of the reasons for discontinuing treatment with sulfasalazine in patients with chronic inflammatory bowel disease. Scand. J. Gastroenterol. 1982, 3, 389-393.
12. Das, K. M.; Eastwood, M. A.; McManus, J. P.; Sircus, W. Adverse reactions during salicylazosulfapyridine therapy and the relation with drug metabolism and acetylator phenotype. N. Engl. J. Med. 1973, 289(10), 491-495.
13. Levine, D. S.; Riff, D. S.; Pruitt, R.; Wruble, L.; Koval, G.; Sales, D.; Bell, J. K.; Johnson, L. K. A randomized, double blind, dose-response comparison of balsalazide (6.75 g), balsalazide (2.25g) and mesalamine (2.4g) in the treatment of active, mild-to-moderate ulcerative colitis. Am. J. Gastroenterology 2002, 97(6), 1398-1407.
14. 3A (R): Impurities in New Drug Substances; ICH Guidelines: Geneva, Switzerland, 2002.
15. Eckardt, C. G. Wolf.; Nageib, M.; Bhaskar, R. G. 2007, Safe process for the preparation of balsalazide [P]. US Patent 7,271,253 B1, Sept. 18.
16. Yuzhu, C.; Jun, X.; Puhai, W.; Zongkang, L. Synthesis of balsalazide disodium. Huaxi Yaoxue Zazhi. 2004, 19(6), 431-433.
17. Li, S.; Juan, W.; Xiao-li, C.; Quan, Z. Improvement on synthesis of balsalazide. Huaxue Gongye Yu Gongcheng. 2005, 22(4), 313-315.
18. Huijun, S.; Gang, F.; Song, W. Improvement on synthesis of balsalazide disodium. Zhongguo Yaowu Huaxue Zazhi. 2001, 11(2), 110-111, 114.
19. Zhenhua, S.; Jian, D.; Qi, N.; Xiuping, Z. Synthesis of balsalazide sodium. Zhongguo Yiyao Gongye Zazhi. 2003, 34(11), 537-538.
20. 1). Physicians' Desk Reference, 62nd ed.; Thomson Healthcare: Montvale, NJ, 2008; pp. 2784-2786.
21. Chan, R. P. K. 1983, 2-Hydroxy-5-phenylazobenzoic acid derivatives and method of treating ulcerative colitis therewith. US Patent 4,412,992; Nov. 1.
22. Gomberg, M.; Bachmann, W. E. The synthesis of biaryl compounds by means of the diazo reaction. J. Am. Chem. Soc. 1924, 46(10), 2339-2343.
23. Beadle, J. R.; Korzeniowski, S. H.; Rosenberg, D. E.; Garcia-Slanga, B. J.; Gokel, G. W. Phase-transfer-catalyzed Gomberg-Bachmann synthesis of unsymmetrical biarenes: A survey of catalysts and substrates. J. Org. Chem. 1984, 49(9), 1594-1603.
24. Gurczynski, M.; Tomasik, P. Solvent effect on the Gomberg-Bachmann-Hey arylation of pyridine. Org. Prep. Proced. Int. 1991, 23, 438.