Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Reexamination Certificate
2007-10-08
2010-06-22
Anderson, Rebecca L (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
Reexamination Certificate
active
07741480
ABSTRACT:
The present invention provides a novel process for preparation of 5-aminomethyl substituted oxazolidinones, key intermediates for oxazolidinone antibacterials including linezolid. Thus linezolid is prepared bya) reacting 3-fluoro-4-morpholinyl aniline with R-epichlorohydrin;b) subjecting N-[3-Chloro-2-(R)-hydroxypropyl]-3-fluoro-4-morpholinyl aniline produced above to carbonylation;c) reacting (5R)-5-(chloromethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone produced above with potassium phthalimide;d) reacting (S)-N-[[3-[3-Fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]phthalimide produced above with hydrazine hydrate; ande) reacting S-N-[[3-[3-Fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine produced above with acetic anhydride to produce linezolid.
REFERENCES:
patent: 5688792 (1997-11-01), Barbachyn et al.
patent: 5837870 (1998-11-01), Pearlman et al.
patent: 6444813 (2002-09-01), Bergren
patent: 6559305 (2003-05-01), Bergren
patent: 6750341 (2004-06-01), Krochmal et al.
patent: 7307163 (2007-12-01), Rao
patent: 7351824 (2008-04-01), Rao et al.
patent: 7429661 (2008-09-01), Rao et al.
patent: 7524954 (2009-04-01), Rao et al.
patent: 2002/0095054 (2002-07-01), Pearlman
patent: 2004/0102523 (2004-05-01), Broquaire et al.
patent: 2006/0142283 (2006-06-01), Aronhime et al.
patent: 2006/0247435 (2006-11-01), Rao
patent: 2008/0021215 (2008-01-01), Rao et al.
patent: 1355165 (2002-06-01), None
patent: 004024 (1979-02-01), None
patent: 50827 (1981-10-01), None
patent: 0275742 (1987-12-01), None
patent: 1255754 (2005-06-01), None
patent: 2506769 (1978-06-01), None
patent: 9507271 (1994-08-01), None
patent: 9737980 (1997-12-01), None
patent: WO 9737980 (1997-12-01), None
patent: 9924393 (1998-10-01), None
patent: 0170170 (2001-09-01), None
patent: WO 0170170 (2001-09-01), None
patent: 02085849 (2002-10-01), None
patent: WO 02085849 (2002-10-01), None
patent: 2005099353 (2004-04-01), None
patent: 2005099353 (2005-10-01), None
K.V.S.R. Krishna Reddy, S. Mahender Rao, G. Om Reddy, T. Suresh, J. Moses Babu, P.K.Dubey, K. Vyas, Isolation and Characterization of Process-Related Impurities in Linezolid, Journal of Pharmaceutical and biomedical Analysis 30 (2002) 635-642.
Braj B. Lohray, Sundarababu Baskaran, B. Srinivasa Rao, B. Yadi Reddy and I. Nageswara Rao, A Short Synthesis of Oxazolidinone Derivatives Linezolid and Eperezolid: A New Class of Antibacterials, Tetrahedron Letters 40 (1989) 4855-4856.
Steven J. Brickner, et al., Synthesis and Antibactreial Activity of U-100592 and U-100766, Two Oxazolidinone Antibactrial Agents for the Potential Treatment of Multidrug-Resistant Gram-Positive Bacterial Infections, J. Med chem 1996, 39, 673-679.
U.S. Appl. No. 10/524,478, filed Feb. 11, 2005.
U.S. Appl. No. 11/861,340, filed Sep. 26, 2007.
U.S. Appl. No. 11/861,406, filed Sep. 26, 2007.
U.S. Appl. No. 11/861,433, filed Sep. 26, 2007.
U.S. Appl. No. 11/868,662, filed Oct. 8, 2007.
Bernstein “Polymorphism in Molecular Crystals”, p. 117-118, 272 (2002).
Davidovich et al. “Detection of polymorphism by Powder X-Ray Diffraction: Interference by Preferred Orientation”, Am. Pharm. Rev., vol. 7(1), p. 10, 12, 14, 16, 100 (2004).
US Pharmacopia, #23 National Formulary #18, p. 1843-1844 (1995).
Banga S. Chawla G. Bansal AK, New trends in crystallization of active pharmaceutical ingredients, Business Briefing: Pharmagenerics 2004, Nov. 1-5.
The United States Pharmacopoeia, 23rd Edition, National Formulary #18, U.S. Pharmacopoeia Convention, Inc., Rockville, MD, 1995, pp. 1843-1844.
European and Japanese Pharmacopoeias as part of the International Harmonization Procedure (Pharmeuropa, vol. 14, No. 1, Jan. 2002, p. 185-191).
International Search Report dated Oct. 16, 2003.
Chawla et al. Challenges in Polymorphism of Pharmaceuticals, CRIPS, vol. 5, No. 1, Jan.-Mar. 2004.
Newman et al., Solid-state analysis of the active pharmaceutical ingredient in drug products, DDT, vol. 8, No. 19, Oct. 2003, pp. 898-905.
Bernstein “Polymorphism in Molecular crystals” p. 117-118, 272(2002).
U.S. Appl. No. 11/868,633, filed Oct. 8, 2007.
Chawla et al. Challenges in Polymorphism of Pharmaceuticals, CRIPS vol. 5, No. 1, Jan.-Mar. 2004.
Banga S. Chawla G. Bansal AK. New trends in crystallization of active pharmaceutical ingredients, Business Briefing: Pharmagenerics 2004, Nov. 1-5.
Krishna Reddy Pingili
Mohan Rao Dodda
Anderson Rebecca L
Caesar Rivise Bernstein Cohen & Pokotilow Ltd.
Symed Labs Limited
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