Process for preparing atazanavir bisulfate and novel forms
A process is provided for preparing the HIV protease inhibitor atazanavir bisulfate wherein a solution of atazanavir free base is reacted with concentrated sulfuric acid in an amount to react with less than about 15% by weight of the free base, seeds of Form A crystals of atazanavir bisulfate are ad...
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Format | Patent |
Language | English |
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23.11.2010
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Abstract | A process is provided for preparing the HIV protease inhibitor atazanavir bisulfate wherein a solution of atazanavir free base is reacted with concentrated sulfuric acid in an amount to react with less than about 15% by weight of the free base, seeds of Form A crystals of atazanavir bisulfate are added to the reaction mixture, and as crystals of the bisulfate form, additional concentrated sulfuric acid is added in multiple stages at increasing rates according to a cubic equation, to effect formation of Form A crystals of atazanavir bisulfate.A process is also provided for preparing atazanavir bisulfate as Pattern C material. A novel form of atazanavir bisulfate is also provided which is Form E3 which is a highly crystalline triethanolate solvate of the bisulfate salt from ethanol. |
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AbstractList | A process is provided for preparing the HIV protease inhibitor atazanavir bisulfate wherein a solution of atazanavir free base is reacted with concentrated sulfuric acid in an amount to react with less than about 15% by weight of the free base, seeds of Form A crystals of atazanavir bisulfate are added to the reaction mixture, and as crystals of the bisulfate form, additional concentrated sulfuric acid is added in multiple stages at increasing rates according to a cubic equation, to effect formation of Form A crystals of atazanavir bisulfate.A process is also provided for preparing atazanavir bisulfate as Pattern C material. A novel form of atazanavir bisulfate is also provided which is Form E3 which is a highly crystalline triethanolate solvate of the bisulfate salt from ethanol. |
Author | Srivastava, Sushil K Lotz, Bruce T Malley, Mary F Gougoutas, Jack Z Davidovich, Martha Kim, Soojin |
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References | Earl, W.L. et al., "Measurement of 13C Chemical Shifts in Solids", Journal of Magnetic Resonance, vol. 48, pp. 35-54 (1982). U.S. Appl. No. 11/119,551, filed May 2, 2005, Kim et al. Fässler et al. (5849911) 19981200 Malamas et al. (5541205) 19960700 Malamas, M.S. at al., "Azole Phenoxy Hydroxyureas as Selective and Orally Active inhibitors of 5-Lipoxygenase", J. Med. Chem., vol. 39, No. 1, pp. 237-245 (1996). Xu, Z. et al., "Process Research and Development for an Efficient Synthesis of the HIV Protease Inhibitor BMS-232632", Organic Process Research & Development, vol. 6, No. 3, pp. 323-328 (2002). Yin, S. et al., "Simulated PXRD Patterns in Studies of the Phase Composition and Thermal Behavior of Bulk Crystalline Solids", American Pharmaceutical Review, vol. 6, No. 2, pp. 80-85 (2003). Cheng et al. (6727271) 20040400 Johannsson, G. et al., "Growth Hormone Treatment of Abdominally Obese Men Reduces Abdominal Fat Mass, Improves Glucose and Lipoprotein Metabolism, and Reduces Diastolic Blood Pressure", Journal of Clinical Endocrinology and Metabolism, vol. 82, No. 3, pp. 727-734 (1997). Kim et al. (2005/0256314) 20051100 Nakagawa et al. (4022776) 19770500 Cappola (6753012) 20040600 Venit et al. (6670344) 20031200 (WO 02/085335) 20021000 Grossman et al. (3980637) 19760900 Yu et al. (6316438) 20011100 Desai et al. (2005/0214373) 20050900 Mullin, J.W. et al., "Programmed cooling of batch crystallizers", Chemical Engineering Science, vol. 26, pp. 369-377 (1971). Grimmett et al. (6136345) 20001000 Cheng et al. (6653314) 20031100 Metz, G. et al., "Ramped-Amplitude Cross Polarization in Magic-Angle-Spinning NMR", Journal of Magnetic Resonance, Series A, vol. 110, pp. 219-227 (1994). Bauer et al. (6086919) 20000700 Robl et al. (6395767) 20020500 Cheng et al. (6414002) 20020700 Rusowicz et al. (2005/0288343) 20051200 (1 186 293) 20020300 (1 243 266) 20020900 Jones, A.G. et al., "Programmed Cooling Crystallization of Potassium Sulphate Solutions", Chemical Engineering Science, vol. 29, pp. 105-118 (1974). Goldstein, S.W. et al., "Hydroxyurea Derivatives as Hypoglycemic Agents", J, Med. Chem., vol. 36, No. 15, pp. 2238-2240 (1993). Singh et al. (6087383) 20000700 Otwinowski, Z. et al., "Processing of X-Ray Diffraction Data Collected in Oscillation Mode", Macromolecular Crystallography, Part A, Methods in Enzymology, vol. 276, Academic Press, publ., Carter, Jr., C.W. et al., eds., pp. 307-326 (1997). Desai et al. (2005/0266080) 20051200 Malamas et al. (5428048) 19950600 Zerbe (4800084) 19890100 (WO 01/52825) 20010700 Hoy et al. (5489436) 19960200 Abramowitz et al. (5158777) 19921000 MacLean (2002/0094992) 20020700 Yoon et al. (2004/0022855) 20040200 Badorc et al. (4847265) 19890700 |
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