Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1995-05-31
1997-12-16
Shah, Mukund J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
514203, 514208, 514205, 514206, 540229, 540226, 540227, 540225, C07D50160, A61K 31545
Patent
active
056985479
ABSTRACT:
The present invention includes novel (7R)-7-(acylamino)-3-(arylthio)-3-cephem-4-carboxylic acids or their pharmacologically acceptable salts which exhibit antibiotic activity against a wide spectrum of organisms including organisms which are resistant to .beta.-lactam antibiotics and are useful as antibacterial agents. The invention also relates to novel intermediates useful for making the novel compounds of the present invention and to novel methods for producing the novel compounds and intermediate compounds.
REFERENCES:
patent: 3992377 (1976-11-01), Chauvette et al.
patent: 4066641 (1978-01-01), Hamashima et al.
patent: 4123528 (1978-10-01), Cama et al.
patent: 4150156 (1979-04-01), Beattie et al.
patent: 4153714 (1979-05-01), Ponsford
patent: 4256739 (1981-03-01), Woodward et al.
patent: 4782145 (1988-11-01), Brighty et al.
patent: 4870168 (1989-09-01), Baker et al.
patent: 4992542 (1991-02-01), Christensen et al.
patent: 5025006 (1991-06-01), Dininno et al.
patent: 5077287 (1991-12-01), Temansky
patent: 5138048 (1992-08-01), Tambuinni et al.
patent: 5162521 (1992-11-01), Farina et al.
patent: 5196528 (1993-03-01), Perboni et al.
patent: 5205006 (1993-04-01), Panasuk
Aszodi et al., "Synthesis and Antibacterial Activity of Isocephems," Recent Advances in the Chemistry of .beta.-Lactam Antibiotics, Special Publication No. 70, pp. 350-364, Cambridge, England, Jul. 3-6 (1988).
Afonso et al., "New Synthesis of Penems, the Oxalimide Cyclization Reaction," J. Amer. Chem. Soc. 104:6138-6139 (1982).
Baldwin and Cooper, "Direct 6-Methoxylation of Penicillin Derivatives. A Convenient Pathway to Substituted .beta.-Lacatam Antibiotics," J. Amer. Chem. Soc. 95:2401-2404 (1973).
Barrett, A.G.M., "Amide Transacylation in Penicillin and Cephalosporin Derivatives," J.C.S. Perkin I pp. 1629-1633 (1979).
Basker et al., "Synthesis and Antibacterial Activity of C-2 Carboxyethenylthio-Carbapenem Derivatives," J. Antibiotics XLIII:847-857 (1990).
Bateson et al., "Synthesis of Acid Analogues," J.C.S. Chem. Comm. 185-186 (1980).
Chauvette, "Chemistry of Cephalosporin Antibiotics. XXI. Conversion of Penicillin to Cephalexin," J. Org. Chem. 36:1259-1267 (1971).
Chen et al., "Study of Preparative Separation of Cephalosporins by Centrifugal TLC," Kangshengsu 14:161-167 (1989).
Doyle et al., "Nuclear analogs of .beta.-lactam antibiotics. XIII. Structure activity relationships in the isocephalosporin series,"0 Can. J. Chem. 58:2508-2523 (1980).
Duan et al., "Solvent Optimization of Reversed Phase High Performance Liquid Chromatographic Separation by Orthogonal Design," Zhongguo Yaoka Daxue Xuebao 18:126-129 (1987).
Ernest et al. "119.2-Oxocephems and 2-Acetylpenems--Selective Formation in an Intramolecular Witting Reaction," Helvetica Chimica Acta 64:1303-1311 (1981).
Farina et al., "A General Route to 3'Functionalized 3-Norcephalosporins," J. Org. Chem. 54:4962-4966 (1989).
Fetter and Lempert, "Simple and Condensed .beta.-Lactams. Part 8--The Preparation and Reactions of Some 4-Oxo-azetidin-2-ylaectic Acid Derivatives, and a synthesis of p-Nitrobenzyl (5RS, 6SR)-2-(2-Formylamino-ethylthio)-6-(2-methyl-1,3-dioxolan-2-yl) carbapen-2-em-3-carboxlyate, a Compound Related to the Antibiotic Thienamycin," J. Chem. Research, pp. 0349-0367 (1987).
Firestone and Christensen, "Functionalization of Penicillins at Carbon 6 via N-Acylimines. 6-Hydroxypenicillin. Substituted Penicillins and Cephalosporins. VIII," J. Org. Chem. 38:1436-1437 (1973).
Hamashima et al., "Synthetic Studies on .beta.-Lacatam Antibiotics. 19. Synthesis of 3-Nor-Type-1-Oxacephems," Tetrahedron Lett. 51:4947-4950 (1979).
Hatanaka and Ishimaru, "A Simple Synthesis of (.+-.)-1-Carbacephem Derivatives," Tetrahedron Lett. 24:4837-4838 (1983).
Kamachi et al., "Direct Introduction of a Formamido Group into the 7.alpha.(6.alpha.)-Position of Cephalosporins (Penicillins)," J. Antiobiotics pp. 820-829 (1990).
Kang, H.Y., "Synthesis and Biological Evaluation of New Aminothiazolyl Cephalosporins with Elongated Side Chains," Bull. Korean Chem. Soc. 12:666-673 (1991).
Kondo et al., "New 2"-Amino Derivatives of Arbekacin, Potent Aminoglycoside Antibiotics Against Methicillin-Resistant," J. Antibiotics 46:531-534 (1993).
Koppel and Koehler, "Functionalization of C.sub.6(7) of Penicillins and Cephalosporins. A One-Step Stereoselective Synthesis of 7-.alpha.-Methoxycephalosporin C," J. Amer. Chem. Soc. 95:2403-2404 (1973).
Lunn and Mason, "The Synthesis of 7.alpha.-Methoxy-7.beta.-Amidocephalosporanic Acids by Methoxylation of 7.beta.-(p-Nitrobenzyloxycarboxamido) Cephalosporanic Acid," Tetrahedron Lett. 14:1311-1313 (1974).
McCombie et al. "Synthesis of 3-Heterosubstituted Isocephem and Iso-Oxacephem Antibiotics," Tetrahedron Lett. 27:305-308 (1986).
Melillo et al., "A Practical Synthesis of (.+-.)-Thienamycin," Tetrahedron Lett. 21:2783-2786 (1980).
Mochida et al., "Synthesis and Antibacterial Activity of Novel 3-Substituted Carbacephems," J. Antibiotics vol. XLII pp. 283-292 (1989).
NCCLS publication entitled Methods for Dilution Antimicrobial Susceptibility Tests for Bacterial That Grow Aerobically--Third Edition; Approved Standard, NCCLS 13(25) (1993).
Oh and Cho, "Studies on the Synthesis and Antibacterial Activity of New Zwitterionic Carbapenems," J. Antibiotics 47:126-128 (1994).
Ohki et al., "FK037. A New Parenteral Cephalosporin With a Boraid Antibacterial Spectrum: Synthesis and Antibacterial Activity," J. Antibiotics 46:359-361 (1993).
Oida et al., "2-(Allkylthio)penem-3-carboxylic Acids. I. Synthesis of 6-Unsubstituted Penems)," Chem. Pharm. Bull. 28:3232-3243 (1980).
Perboni et al., "Ch. 2--Tribactams: A Novel Class of .beta.-Lactam Antibiotics," in Recent Advances in the Chemistry of Anti-Infective Agents, pp. 21-35, Bentley and Ponsford, eds, Royal Society of Chemistry (1993).
Phillips and O'Neill, "A Convergent Process to C-2 Substituted Penems via Addition of Thiois and Organocuprates to an O-Triflyltholketene Acetal," Tetrahedron Lett. 23:3291-3294 (1990).
Ponsford and Southgate, "Preparation of Intermediates for Thienamycin Synthesis," J.C.S. Chem. Comm. 19:846-847 (1979).
Sanders et al., "Microbiological Characterization of Everninomicins B and D," Antimicro. Agents Chemother. 6:232-238 (1974).
Shih et al., "Synthetic Carbapenem Antibiotics 1. 1-.beta.-Methylcarbapenem," Heterocycles 21:29-40 (1984).
Shibata and Sugtimura, "Synthetic Studies of 1-.beta.-Methylcarbapenem Antibiotics," J. Antibiotics 42:374-381 (1989).
Spangler et al., "Susceptibilities of Penicillin-Susceptible and -Resistant Strains of Streptococcus pneumoniae to RP 59500, Vancomycin, Erythromycin, PD 131628, Sparfloxacin, Temafloxacin, Win 57273, Ofloxacin, and Ciprofloxacin," Antimicro. Agents Chemother. 36:856-859 (1992).
Sum et al., "Glycylcyclines. 1. A New Generation of Potent Antibacterial Agents through Modification of 9-Aminotetracyclines," J. Med. Chem. 37:184-188 (1994).
Sunagawa et al., "Synthesis and Biological Properties of 1.beta.-Methyl-Carbapenems with N-Methylpyrrolidinylthio Group at C-2 Position," J. Antibiotics 45:971-976 (1992).
Sunagawa et al., "New Penem Compounds with 5'-Substituted Pyrrolidinylthio Group as a C-2 Side Chain; Comparison of their Biological Properties with Those of Carbapenem Compounds," J. Antibiotics 45:500-504 (1992).
Ternansky et al., "Discovery and Structure-Activity Relationship of a Series of 1-Carba-1-dethiacephems Exhibiting Activity against Methicillin-Resistant Staphylococcus aureus," J. Med. Chem. 36:1971-1976 (1971).
Tsubouchi et al., "A Convenient One Pot Asymmetric Synthesis of cis-.beta.-Lactams: Key Precursors for Optically Active 2-Oxaisocephems," Tetrahedron: Assymetry 5:441-452 (1994).
Tsuchiya, "Cefsulodin (SCE-129), Cefotiam (SCE-963), and Cefmenoxime (SCE-1365)," Beta-Lactam Antibiot. pp. 107-119 (1981).
Yokoo et al., "Studies on Cephalosporin Antibiotics," J. Antibiotics 44:498-506 (1991).
Yoshida et al., "An Efficient Carbapenem Synthesis via an Intramolecular Witting Reaction of New Trialkoxyphosphorane-Thiolesters," Tetrahedron Lett. 25:2793-2796 (1984).
Yoshida et al., "New Synthesis of Penems via Reducti
Cho In-Seop
Christensen Burton
Glinka Tomasz
Hecker Scott
Lee Ving J.
Microcide Pharmaceuticals, Inc.
Shah Mukund J.
Wong King Lit
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