Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2007-11-06
2007-11-06
Anderson, Rebecca (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
11361457
ABSTRACT:
The present invention provides improved methods of converting R—N-(4-morpholiyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl azide (III) to the intermediate S—N-(4-morpholinyl-3-fluorophenyl)-2-oxo-5-oxazolidinyl-methyl amine (II) that involve the production of fewer by-products than previous methods. The amine (II) may then be converted into linezolid (I) of high chemical purity with respect to the inactive R-enantiomer and bis-linezolid (IV), and is in high yield, without the need for tedious, complicated purification steps, such as chromatography.
REFERENCES:
patent: 4705799 (1987-11-01), Gregory
patent: 5688792 (1997-11-01), Barbachyn et al.
patent: 6333198 (2001-12-01), Edmeades et al.
patent: 6444813 (2002-09-01), Bergren
patent: 6559305 (2003-05-01), Bergren
patent: 2001100437 (2001-11-01), None
patent: 2 168 560 (2001-08-01), None
patent: 0 311 090 (1989-04-01), None
patent: 0 352 781 (1990-01-01), None
patent: 0 717 738 (1999-10-01), None
patent: 0 963 980 (1999-12-01), None
patent: WO 93/09103 (1993-05-01), None
patent: WO 95/07271 (1995-03-01), None
patent: WO 01/57035 (2001-08-01), None
patent: WO 03/093247 (2003-11-01), None
patent: WO 2004/026848 (2004-04-01), None
patent: WO 2005/035530 (2005-04-01), None
Brickner, et al., “Synthesis And Antibacterial Activity Of U-100592 And U-100766, Two Oxazolidinone Antibacterial Agents For The Potential Treatment Of Multidrug-Resistant Gram-Positive Bacterial Infections”,Journal of Medicinal Chemistry, vol. 39, No. 3, pp. 673-679, (1996).
Reddy, et al. “Isolation and Characterization of Process-Related Impurities in Linezolid”Journal of Pharmaceutical and Biomedical Analysis, vol. 30, pp. 635-642 (2002).
Perrault, et al., “The Synthesis Of N-Aryl-5(S)-Aminoethyl-2-Oxazolidinone Antibacterials And Derivatives In One Step From Aryl Carbamates”,Organic Process Research&Development, vol. 7, No. 4., pp. 533-546 (2003).
Peng, et al. “Determination of Linezolid In Plasma by Reversed-Phase High-Performance Liquid Chromatography”Journal of Pharmaceutical and Biomedical Analysis, vol. 20, pp. 65-73 (1999).
Gregory, et al. “Antibacterials. Synthesis and Structure-Activity Studies of 3-Aryl-2-Oxooxazolidines. 2. The “A” Group.”Journal of Medicinal Chemistry, vol. 33, No. 9, pp. 2569-2578 (1990).
Gregory, et al. “Antibacterials. Synthesis and Structure-Activity Studies of 3-Aryl-2-Oxooxazolidines. 1. The “B” Group.”Journal of Medicinal Chemistry, vol. 32, No. 8, pp. 1673-1681 (1989).
Sbardella, et al. “Synthesis and In Vitro Antimycobacterial Activity of Novel 3-(1H-Pyrrol-1-yl)-2-Oxazolidinone Analogues of PNU-100480”Bioorganic&Medicinal Chemistry Letters, vol. 14, pp. 1537-1541 (2004).
Emea—European Medicines Agency “ICH Topic Q 3 A (R1)—Impurities in new Drug Substances” CPMP/ICH/2737/99 (2002).
Emea—European Medicines Agency “ICH Topic Q 2 (R1)—Validation of Analytical Procedures: Text and Methodology” CPMP/ICH/381/95 (1995).
Sheradsky “Azides as Synthetic Starting Materials”The Chemistry of The Azido Group(Ed. S. Patai) Interscience Publishers, Chapter 6, pp. 331-395 (1971).
Merck Index, 13th Edition, Monograph No. 5526, CAS Registry No. 165800-03-3, pp. 986, (2001).
Snyder, et al.,Introduction To Modern Liquid Chromatography, 2ndEd., pp. 549-572, John Wiley & Sons, Inc. (1979).
Strobel, et al.,Chemical Instrumentation: A Systematic Approach, 3rdEd., pp. 391-393, 879-894, 922-952, 953, (1989).
Brittain (Ed.)Polymorphism in Pharmaceutical Solids, Drugs and the Pharmaceutical Sciences vol. 95, pp. 1-2, 178-179, 236, Marcel Dekker, Inc. New York, New York, (1999).
Grant “Theory and Origin of Polymorphism”Polymorphism in Pharmaceutical Solids, Drugs and the Pharmaceutical Sciencesvol. 95 (Ed. Brittain), Marcel Dekker, Inc., pp. 1-33, (1999).
Guillory “Generation of Polymorphs, Hydrates, Solvates, and Amorphous Solids”Polymorphism in Pharmaceutical Solids, Drugs and the Pharmaceutical Sciencesvol. 95 (Ed. Brittain), Marcel Dekker, Inc., pp. 183-226, (1999).
Byrn, et al.,Solid-State Chemistry Of Drugs, 2ndEd., p. 4, (1999).
Perry's Chemical Engineers' Handbook, 6thEd., pp. 20-54 to 20-57, (1984).
Rouhi, “The Right Stuff”,Chemical&Engineering News, pp. 32-35, (2003).
US Pharmacopia # 23, National Formulary # 18, pp. 1843-1844, (1995).
Braude Viviana
Fine Serguei
Nidam Tamar
Anderson Rebecca
Young Shawquia
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