Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2011-06-14
2011-06-14
Nolan, Jason M (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
07960559
ABSTRACT:
The tetracycline class of antibiotics has played a major role in the treatment of infectious diseases for the past 50 years. However, the increased use of the tetracyclines in human and veterinary medicine has led to resistance among many organisms previously susceptible to tetracycline antibiotics. The recent development of a modular synthesis of tetracycline analogs through a chiral enone intermediate has allowed for the efficient synthesis of novel tetracycline analogs never prepared before. The present invention provides a more efficient route for preparing the enone intermediate.
REFERENCES:
patent: 2482055 (1949-09-01), Duggar et al.
patent: 3019260 (1962-01-01), McCormick et al.
patent: 3109007 (1963-10-01), Blackwood et al.
patent: RE26253 (1967-08-01), Petisi et al.
patent: 3338963 (1967-08-01), Petisi et al.
patent: 3502660 (1970-03-01), Butler et al.
patent: 3509184 (1970-04-01), Conover et al.
patent: 3697552 (1972-10-01), Conover et al.
patent: 3699117 (1972-10-01), Butler et al.
patent: 3772363 (1973-11-01), Conover et al.
patent: 3829453 (1974-08-01), Conover et al.
patent: 3849493 (1974-11-01), Conover et al.
patent: 3862225 (1975-01-01), Conover et al.
patent: 3947517 (1976-03-01), Muxfeldt et al.
patent: 3962330 (1976-06-01), Cotti et al.
patent: 3983173 (1976-09-01), Hartung et al.
patent: 4052467 (1977-10-01), Mills et al.
patent: 4060605 (1977-11-01), Corti et al.
patent: 4066694 (1978-01-01), Blackwood et al.
patent: 4418060 (1983-11-01), Kahan nee Laszlo
patent: 4597904 (1986-07-01), Page et al.
patent: 5362754 (1994-11-01), Raad et al.
patent: 5529990 (1996-06-01), Hlavka et al.
patent: 5538954 (1996-07-01), Koch et al.
patent: 5589470 (1996-12-01), Levy et al.
patent: 5688516 (1997-11-01), Raad et al.
patent: 5811412 (1998-09-01), Levy et al.
patent: 5834450 (1998-11-01), Su et al.
patent: 6143161 (2000-11-01), Heggie et al.
patent: 6165999 (2000-12-01), Vu et al.
patent: 6506740 (2003-01-01), Ashley et al.
patent: 6509319 (2003-01-01), Raad et al.
patent: 6617318 (2003-09-01), Nelson et al.
patent: 6624168 (2003-09-01), Nelson et al.
patent: 6638532 (2003-10-01), Rudnic et al.
patent: 6642270 (2003-11-01), Nelson et al.
patent: 6683068 (2004-01-01), Nelson et al.
patent: 6818634 (2004-11-01), Nelson et al.
patent: 6818635 (2004-11-01), Nelson et al.
patent: 6841546 (2005-01-01), Draper et al.
patent: 6846939 (2005-01-01), Nelson et al.
patent: 6849615 (2005-02-01), Nelson et al.
patent: 7001918 (2006-02-01), Huss et al.
patent: 7763735 (2010-07-01), Myers et al.
patent: 2002/0045602 (2002-04-01), Nelson et al.
patent: 2002/0103171 (2002-08-01), Nelson et al.
patent: 2002/0111335 (2002-08-01), Nelson et al.
patent: 2002/0128237 (2002-09-01), Nelson et al.
patent: 2002/0128238 (2002-09-01), Nelson et al.
patent: 2002/0132798 (2002-09-01), Nelson et al.
patent: 2002/0136766 (2002-09-01), Rudnic et al.
patent: 2002/0193354 (2002-12-01), Nelson et al.
patent: 2003/0055025 (2003-03-01), Nelson et al.
patent: 2003/0096008 (2003-05-01), Rudnic et al.
patent: 2003/0100017 (2003-05-01), Draper et al.
patent: 2003/0153537 (2003-08-01), Levy et al.
patent: 2003/0166585 (2003-09-01), Draper et al.
patent: 2004/0048835 (2004-03-01), Nelson et al.
patent: 2004/0063674 (2004-04-01), Levy et al.
patent: 2004/0067912 (2004-04-01), Hlavka et al.
patent: 2005/0282782 (2005-12-01), Martin
patent: 2005/0282787 (2005-12-01), Myers et al.
patent: 2007/0066253 (2007-03-01), Sorrells et al.
patent: 2010/0130451 (2010-05-01), Myers et al.
patent: 1 124 160 (2002-09-01), None
patent: 2 279 720 (1976-02-01), None
patent: 973022 (1964-10-01), None
patent: 1013576 (1965-12-01), None
patent: 1013906 (1965-12-01), None
patent: 1019562 (1966-02-01), None
patent: 1019563 (1966-02-01), None
patent: WO 95/22529 (1995-08-01), None
patent: WO 01/98236 (2001-12-01), None
patent: WO 01/98259 (2001-12-01), None
patent: WO 01/98260 (2001-12-01), None
patent: WO 02/04404 (2002-01-01), None
patent: WO 02/04406 (2002-01-01), None
patent: WO 02/04407 (2002-01-01), None
patent: WO 02/12170 (2002-02-01), None
patent: WO 02/072532 (2002-09-01), None
patent: WO 02/085303 (2002-10-01), None
patent: WO 03/005971 (2003-01-01), None
patent: WO 03/057169 (2003-07-01), None
patent: WO 03/076424 (2003-09-01), None
patent: WO 2005/112945 (2005-12-01), None
patent: WO 2005/112985 (2005-12-01), None
patent: WO 2007/117639 (2007-10-01), None
patent: WO 2007/118237 (2007-10-01), None
patent: WO 2008/127361 (2008-10-01), None
U.S. Appl. No. 60/790,413, filed Apr. 7, 2006, Myers.
U.S. Appl. No. 60/850,859, filed Oct. 11, 2006, Myers et al.
International Search Report and Written Opinion for PCT/US2007/081076 mailed Dec. 15, 2008.
International Preliminary Report on Patentability for PCT/US2007/081076 mailed Apr. 23, 2009.
Supplementary European Search Report for EP 05779988.4 mailed Jun. 9, 2009.
International Search Report and Written Opinion for PCT/US2005/017831 mailed May 4, 2006.
International Preliminary Report on Patentability for PCT/US2005/017831 mailed Nov. 30, 2006.
International Search Report and Written Opinion for PCT/US2007/008647 mailed Mar. 14, 2008.
International Preliminary Report on Patentability for PCT/US2007/008647 mailed Oct. 16, 2008.
Notice of Allowance mailed Apr. 7, 2010 U.S. Appl. No. 11/870,772.
Office Communication mailed Oct. 27, 2009 for U.S. Appl. No. 11/133,789.
Notice of Allowance mailed Feb. 22, 2010 for U.S. Appl. No. 11/133,789.
Akgun et al., Metalation of 0-Halostyrenes Oxides. Preparation of Benzocyclobutenols. J. Org. Chem. 1981;46:2730-2734.
Allen et al., A Powerful o-Quinone Dimethide Strategy for Intermolecular Diels—Alder Cycloadditions. J. Am. Chem. Soc. 2000;122:571-575.
Allen et al., The Total Synthesis of (±)-Rishirilide B. Am. Chem. Soc. 2001;123:351-352.
Amaro et al., Synthesis of Tetracyclic Hydroxyquinones by Cycloaddition Reactions With Dienols. Tetrahedron Lett. 1979:3983-3986.
Ballard et al., A Biotech Route to Polyphenylene. J. Chem. Soc. Chem. Commun 1983:954-955.
Barr et al., Zirconocene(iso-butyl) Chloride: In Situ Generation of a Zirconocene(methyl) Chloride Equivalent for Use in Organic Synthesis. Tetrahedron Lett. 1991;32:5465-5468.
Beard et al., Inhibition of Mammalian Protein Synthesis by Antibiotics. Pharmacol. Revs. 1969;21: 213-245.
Becker et al., Oxidative Formation and Photochemical Isomerization of Spiro-Epoxy-2,4-Cyclohexadienones. Tetrahedron Lett. 1972;13:4205-4208.
Beereboom et al., Further 6-Deoxytetracycline Studies: Effect of Aromatic Substituents on Biological Activity. J. Am. Chem. Soc. 1960;82:1003-1004.
Berge et al., Pharmaceutical Salts. J. Pharmaceutical Sciences 1977;66:1-19.
Berk et al., Preparations and Reactions of Functionalized Benzylic Organometallics of Zinc and Copper. Organometallics. 1990;9:3053-3064.
Boothe et al., Identification of an Antibiotic Polyacetylene From Clitocybe Diatreta As a Suberamic Acid Ene-Diyne. J. Am. Chem. Soc.1953;75:4621.
Boudier et al., New Applications of Polyfunctional Organometallic Compounds in Organic Synthesis Frequently used abbreviations are defined at the end of the article. Angew Chem Int Ed Engl. Dec. 15, 2000;39(24):4414-4435.
Brodersen et al.,The Structural Basis for the Action of the Antibiotics Tetracycline, Pactamycin, and Hygromycin B on the 30S Ribosomal Subunit. Cell. 2000;103:1143-1154.
Brown et al., Activities of the Glycylcyclines N, N-Dimethylglycylamido-Minocycline and N,N-Dimethylglycylamido-6-Deoxytetracycline Against Nocardia spp. And Tetracycline-Resistant Isolates of Rapidly Growing Mycobacteria. Antimicrob. Agents Chemother. 1996;40:874-878.
Brubaker et al., A practical, enantioselective synthetic route to a key precursor to the tetracycline antibiotics. Org Lett. Aug. 30, 2007;9(18):3523-5. Epub Aug. 11, 2007.
Burdett, Purification and Characterization of Tet(M), a Protein That Renders Ribosomes Resistant to Tetracycline. J. Biol. Chem. 1991;266:2872-2877.
Burke, Flexible tetracycline synthesis yields promising antibiotics. Nat Chem Biol. Feb. 2009;5(2):77-9.
Bush et al., Taking Inventory: Antibacterial Agents Currently At or Beyond Phase 1. Curr. Opin.
Brubaker Jason D.
Myers Andrew G.
Baker C. Hunter
Nolan Jason M
President and Fellows of Harvard College
Wolf Greenfield & Sacks P.C.
LandOfFree
Synthesis of enone intermediate does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Synthesis of enone intermediate, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of enone intermediate will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2620412