Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2006-10-24
2006-10-24
Berch, Mark L. (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
07125986
ABSTRACT:
Compounds of formula I:wherein R1, R2, R3, R4and n have any of the values defined in the specification, and their pharmaceutically acceptable salts, are useful for inhibiting β-lactamase enzymes, for enhancing the activity of β-lactam antibiotics, and for treating β-lactam resistant bacterial infections in a mammal. The invention also provides pharmaceutical compositions, processes for preparing compounds of formula I, and novel intermediates useful for the synthesis of compounds of formula I.
REFERENCES:
patent: 4053468 (1977-10-01), Holden
patent: 4356174 (1982-10-01), Barth
patent: 4512999 (1985-04-01), Adam-Molina et al.
patent: 4559157 (1985-12-01), Smith et al.
patent: 4608392 (1986-08-01), Jacquet et al.
patent: 4820508 (1989-04-01), Wortzman
patent: 4826833 (1989-05-01), Chen
patent: 4861768 (1989-08-01), Torii et al.
patent: 4912213 (1990-03-01), Taniguchi et al.
patent: 4938949 (1990-07-01), Borch et al.
patent: 4992478 (1991-02-01), Geria
patent: 5597817 (1997-01-01), Buynak et al.
patent: 5629306 (1997-05-01), Buynak et al.
patent: 5637579 (1997-06-01), Hubschwerlen et al.
patent: 5681563 (1997-10-01), Buynak et al.
patent: 5760027 (1998-06-01), Buynak et al.
patent: 6156745 (2000-12-01), Buynak et al.
patent: 6391855 (2002-05-01), Blaschuk et al.
patent: 6395726 (2002-05-01), Lin et al.
patent: 2708219 (1977-09-01), None
patent: 0041047 (1981-12-01), None
patent: 0050805 (1982-05-01), None
patent: 0150984 (1985-08-01), None
patent: 0170192 (1986-02-01), None
patent: 0367606 (1990-05-01), None
patent: 0043546 (1992-01-01), None
patent: 2043639 (1980-10-01), None
patent: 55-136288 (1980-10-01), None
patent: 57-99590 (1982-06-01), None
patent: 58-59990 (1983-04-01), None
patent: 61-109791 (1986-05-01), None
patent: 62-198687 (1987-09-01), None
patent: 64-66189 (1989-03-01), None
patent: 7-82273 (1995-03-01), None
patent: WO-96/17849 (1996-06-01), None
patent: WO-98/24793 (1998-06-01), None
patent: WO-00/63213 (2000-10-01), None
patent: WO-03/020732 (2003-03-01), None
Abd El-Nabi, H. A., “Novel Heterocycles: A covenient Synthesis of Pyrrolo [2,3-d]pyrazole; Cycloaddition reaction of N-aryl(methyl)pyrrol-2,3-Diones to diazomethane and olefins”,Tetrahedron, 53(5), (Feb. 1997),1813-1822.
Adam, Solange , “Synthesis of Methylene (R)-6-acetonylidene-3-methyl-7-oxo-4-thia-1- azabicyclo [3.2.0] hept-2-ene-carboxylate pivalate”,Heterocycles, 22(7), Columbus, Ohio, U.S.,(1984),1509-1512.
Arisawa, M. , et al., “6-Acetylmethylenepenicillanic Acid (Ro 15-1903), A Potent B-Lactamase Inhibitor. I. Inhibition of Chromosomally and R-Factor-Mediated B-Lactamases”,The Journal of Antibiotics, 35(11), (Nov. 1982),1578-1583.
Beharry, Zanna , “Penicillin-Derived Inhibitors of the B-Lactamase fromBacillus anthracis”,ICAAC Poster # C1-679, Chicago, IL, (2003),6 pgs.
Bennett, I. S., et al., “6-(Substituted Methylene)Penems, Potent Broad Spectrum Inhibitors of Bacterial B-Lactamse. V. Chiral 1,2,3-Triazolyl Derivatives”.The Journal of Antibiotics, 44(9), (Sep. 1991),969-978.
Billups, W. E., et al., “Generation of Simple Methylenecyclopropenes as Reactive Intermediates”,Tetrahedron, 37, (1981),3215-3220.
Bitha, P. , et al., “6-(1-Hydroxyalkyl)Penam Sulfone Derivatives as Inhibitors of .beta.-Lactamases I”,Bioorganic&Medicinal Letters, 9(7), (1999),991-996.
Bitha, P. , et al., “6-(1-Hydroxyalkyl)Penam Sulfone Derivatives as Inhibitors of .beta.-Lactamases II”,Bioorganic&Medicinal Chemistry Letters, 9(7), (1999),997-1002.
Black, Jennifer , “Detection of Plasmid-Mediated AmpC B-Lactamases (pAmpCs) in Disk Tests Based on B-Lactamase Inhibitors (BLIs) Ro 48-1220 (RO) and LN-2-128 (LN)”,43rd ICAAC Poster # D-258, (2003),6 pgs.
Blacklock, Thomas J., “A Versatile Synthesis of 1,1-Dioxo 7-Substituted Cephems: Preparation of the Human Leukocyte Elastase (HLE) Inhibitor 1,1-Dioxo-trans-7-methoxycephalosporanic Acid tert-Butyl Ester”,J. Org. Chem., 54, (1989),3907-3913.
Brenner, D. G., et al., “6-(Methoxymethylene)penicillanic Acid: Inactivator of RTEM B-Lactamse fromEscherichia coli”, Biochemistry, 23(24), (Nov. 20, 1984),5839-5846.
Buynak, John D., et al., “7-Alkylidenecephalosporin Esters as Inhibitors of Human Leukocyte Elastase”,Journal of Medicinal Chemistry, 40(21), (Oct. 10, 1997),3423-3433.
Buynak, John D., et al., “A Convenient Method for the Production of 6-Oxopenicillinates and 7-Oxocephalosporinates”,Tetrahedron Letters, 39, (1998),4945-4946.
Buynak, John D., et al., “a-Alkylidene B-Lactams. 2. A Formal Synthesis of (+)-Carpetimycin A”,Journal of Organic Chemistry, 51, (1986),1571-1574.
Buynak, John D., et al., “Catalytic Approaches to the Synthesis of B-Lactamase Inhibitors”,Tetrahedron, 56, (2000),5709-5718.
Buynak, J. D., et al., “Cephalosporin-Derived Inhibitors of beta-Lactamase. Part 4: The C3 Substituent”,Bioorganic&Medicinal Chemistry Letters, 12(12), Online Apr. 24, 2002,(Jun. 17, 2002),1663-1666.
Buynak, J. D., “Coupling Reactions of Cephalosporin Sulfones: A Stable 3-Stannylated Cephem”,Org. Lett. 2001, 3(19), Aug. 31, 2001),2953-2956.
Buynak, John D., “Penicillin-Derived Inhibitors that Simultaneously Target Both Metallo- and Serine-B-Lactamases”,Bioorganic and Medicinal Chemistry Letters, (Article in Press, available online), (Jan. 22, 2004),6 pgs.
Buynak, John D., et al., “Reactions of (Silylamino)phosphines with Epoxides and Episulfides”,Journal of Organic Chemistry, 49, (1984),1828-1830.
Buynak, John D., et al., “Stille Coupling Approaches to the Stereospecific Synthesis of 7-[(E)-Alkylidene]cephalosporins”,Tetrahedron Letters, 40, (1999),1281-1284.
Buynak, John D., “Synthesis and biological activity of 7-alkylidenecephems”,Journal of Medicinal Chemistry, 38(6), (Mar. 17, 1995),1022-1034.
Buynak, John D., et al., “Synthesis and mechanistic evaluation of 7-vinylidenecephem sulfones as B-lactamase inhibitors”,J. of Am. Chem. Soc., 116, (1994),10955-10965.
Buynak, John D., et al., “Synthesis and Reactivity of Sulfur and Silyl Substituted a-Alkylidene-B-Lactams”,Tetrahedron Letters, 26, (1985),5001-5004.
Buynak, J. D., et al., “Synthesis of 6-vinylidenepenams”,The Journal of Organic Chemistry, 58 (6), (Mar. 12, 1993),1325-1335.
Buynak, John D., et al., “Synthesis of the First 2′, 6 Bridged Penams”,J. Am. Chem. Soc., 120, (1998),6846-6847.
Buynak, John D., et al., “The Addition of Chlorosulphonyl Isocyanate to an Allenyl Acetate. The Preparation of a Versatile Intermediate for Antibiotic Synthesis”,J. Chem. Soc., Chem. Commun., (1984),948-949.
Buynak, John D., et al., “The Preparation and Use of Metallo-6-vinylidene Penams”,J. Chem. Soc., Chem. Commun., (1990),294-296.
Buynak, John D., et al., “The Preparation of the First a-Vinylidene-B-lactams”,J. Chem. Soc., Chem. Commun., (1987),735-737.
Buynak, John D., “The Preparation of the First a-Vinylidenepenams”,Tetrahedron Letters, 29, (1988),5053-5056.
Buynak, J. D., “The Synthesis and Evaluation of 2-Substituted-7-(alkylidene)cephalosporin Sulfones as beta-Lactamase Inhibitors”,Bioorganic&Medicinal Chemistry Letters, 10(9), (May 1, 2000),847-851.
Buynak, J. D., “The Synthesis and Evaluation of 3-Substituted-7-(alkylidene)cephalosporin Sulfones as beta-Lactamase Inhibitors”,Bioorganic&Medicinal Chemistry Letters, 10(9), (May 1, 2000),853-857.
Buynak, John D., “The Synthesis and Evaluation of 6-Alkylidene-2′ B-Substituted Penam Sulfones as B-Lactamase Inhibitors”,Bioorganic and Medicinal Chemistry Letters, 9, (1999),1997-2002.
Buynak, J. D., et al., “The Synthesis and Lactamase Inhibitory Activity of 6-(Carboxymethylene) Pencillins and 7-(Carboxymethylene)Cephalosporins”,Bioorganic&Medicinal Chemistry Letters, 5 (14), (199
Buynak John D.
Doppalapudi Venkata Ramana
Rao Akireddy Srinivasa
Berch Mark L.
Schwegman Lundberg Woessner & Kluth P.A.
Southern Methodist University Foundation for Research
LandOfFree
Penicillanic acid derivative compounds and methods of making does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Penicillanic acid derivative compounds and methods of making, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Penicillanic acid derivative compounds and methods of making will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3668772