Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2011-08-16
2011-08-16
Skowronek, Karlheinz R (Department: 1613)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C548S221000
Reexamination Certificate
active
07999115
ABSTRACT:
The invention relates to compounds of formula (I) wherein R1represents H, alkyl, alkoxy, cyano or halogen; one of U and X represents CH or N and the other represents CH, or, in the case of U, may also represent CRaand, in the case of X, may also represent CRb; Rarepresents halogen; Rbrepresents halogen or alkoxy; B represents N, D represents CH2and A represents CH(OH)CH2or CH2CH2, or B represents CH, D represents CH2or O and A represents OCH2, CH2CH(OH), CH(OH)CH2, CH(OH)CH(OH), CH═CH, CH2CH2or NHCO, or also B represents C(OH), D represents CH2and A represents OCH2, CH2CH(OH), CH(OH)CH2, CH(OH)CH(OH), CH═CH, CH2CH2Or NHCO; R2represents H, alkyl, alkenyl, hydroxyalkyl or alkoxycarbonylalkyl; and E represents naphthyl or a binuclear heterocyclic group; and to salts of such compounds. These compounds are useful as antimicrobial agents.
REFERENCES:
patent: 4244961 (1981-01-01), Kluge et al.
patent: 4353901 (1982-10-01), Clark
patent: 438233 (1991-07-01), None
patent: WO 96/33195 (1996-10-01), None
patent: WO 00/40554 (2000-07-01), None
patent: WO 00/78748 (2000-12-01), None
patent: WO 02/08224 (2002-01-01), None
patent: WO 03/087098 (2003-10-01), None
patent: WO 03/095438 (2003-11-01), None
patent: WO 2004/002490 (2004-01-01), None
patent: WO 2004/014361 (2004-02-01), None
patent: WO 2004/022558 (2004-03-01), None
patent: WO 2004/035569 (2004-04-01), None
patent: WO 2004/089947 (2004-10-01), None
patent: WO 2006/021448 (2006-03-01), None
patent: WO 2006/032466 (2006-03-01), None
patent: WO 2006/046552 (2006-04-01), None
patent: WO 2006/038172 (2008-04-01), None
Henry Chambers, Antimicrobial Agents; General Considerations, in Goodman & Gilman's the Pharmacological Basis of Therapeutics 1143 (10th ed. 2001).
Alfred Burger, Isosterism and Bioisosterism in Drug Design, in Progress in Drug Research 287-328 (Ernst Jucker, ed., Birkhauser Verlag, 1991).
George Patani & Edmond LaVoie, Bioisosterism: A Rational Approach in Drug Design, 96 Chem. Rev. 3147 (1996).
Gould, et al. “Salt selection for basic drugs,” International Journal of Pharmaceutics, vol. 33, pp. 201-217, (1986).
Mitsunobu, Oyo, “The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products,” Department of Chemistry, College of Science and Engineering, Aoyama Gakuin University, Tokyo, Japan, Synthesis, pp. 1-28, 1981.
Benz, Günter, “2.3: Synthesis of Amides and Related Compounds,” Comprehensive Organic Synthesis, B.M. Trost and I. Fleming, Eds; Pergamon Press: New York, vol. 6, pp. 381-417, 1991.
Palucki, M. et al., “Synthesis of Oxygen Heterocycles via a Palladium-Catalyzed C-O Bond-Forming Reaction,” Journal of the American Chemical Society, vol. 118, pp. 10333-10334, 1996.
Klapars, A. et al., “A General and Efficient Copper Catalyst for the Amidation of Aryl Halides,” Journal of the American Chemical Society, vol. 124, pp. 7421-7428, 2002.
Kolb, H. et al., “Catalytic Asymmetric Dihydroxylation,” Chemical Review for the American Chemical Society, vol. 94, pp. 2483-2547, 1994.
Blakemore, Paul, “The modified Julia olefination: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds,” Journal of the Royal Society of Chemistry, Perkin Trans. 1, pp. 2563-2585, 2002.
Echavarren, A. et al., “Palladium-catalyzed coupling of aryl triflates with organostannanes,” Journal of the American Chemical Society, vol. 109, pp. 5478-5486, 1987.
Kocienski, P.J., “Protecting Groups,” Thieme-Foundations of Organic Chemistry Series, pp. 1-2, 1994.
Corey, E.J. et al., “Dimethyloxosulfonium Methylide ((CH)SOCH) and Dimethylsulfonium Methylide ((CH)SCH). Formation and Application to Organic Synthesis,” Journal of the American Chemical Society, vol. 87, pp. 1353-1364, 1965.
Borredon, E. et al., “Epoxydation en milieu heterogene solide-liquide: Effet des interactions a l'interface sur la stabilite de l'ylure de dimethylsulfonium—Consequences sur la stereochimie de la reaction d'epoxydation,” Tetrahedron Letters, vol. 28, No. 17, pp. 1877-1880, 1987.
Mancuso, A. et al., “Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide ‘activated’ by oxalyl chloride,” Journal of Organic Chemistry, vol. 43, pp. 2480-2482, 1978.
Dess, D.B. et al., “Readily accessible 12-|-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones,” Journal of Organic Chemistry, vol. 48, pp. 4155-4156, 1983.
Furstoss, R. et al., “Synthesis of bridged azabicyclic ketones. Solvolysis of enol ehter and ethylene ketal N-chloramines in acidic medium,” Canadian Journal of Chemistry, vol. 54, pp. 3569-3579, 1976.
Singh, C. et al., “Protection of the Carbonyl Group as 1,2,4-Trioxane and Its Regeneration under Basic Conditions,” Organic Letters by the American Chemical Society, vol. 7, pp. 5673-5676, 2005.
Wipf, P. et al., “Total Synthesis of a Stereoisomer of Bistramide C and Assignment of Configuration of the Natural Product,” Chemistry—A European Journal, vol. 8, No. 7, pp. 1670-1681, 2002.
Suggs, J.W. et al., “Facile Synthesis of 8-substituted quinolines,” Journal of Organic Chemistry, vol. 45, pp. 1514-1515, 1980.
Miyaura, N. et al., “The Palladium-Catalyzed Cross-Coupling Reaction of Phenylboronic Acid with Haloarenes in the Presence of Bases,” Synthetic Communications, vol. 11, pp. 513-519, 1981.
Cha, J.K. et al., “Acyclic Stereocontrol Induced by Allylic Alkoxy Groups. Synthetic Applications of Stereoselective Dihydoxylation in Natural Product Synthesis,” Chemical Review for the American Chemical Society, vol. 95, pp. 1761-1795, 1995.
Zhang, H.X. et al., “Palladium- and molybdenum-catalyzed hydrostannation of alkynes. A novel access to regio- and stereodefined vinylstannanes,” Journal of Organic Chemistry, vol. 55, pp. 1857-1867, 1990.
Corey, E.J. et al., “A Synthetic method for Formyl→Ethynyl Conversion (RCHO→RC≡CH or RC≡CR),” Tetrahedron Letters, vol. 36, pp. 3769-3772, 1972.
Ohira, Susumu, “Methanolysis of Dimethyl (1-Diazo-2-oxopropyl) Phosphonate: Generation of Dimethyl (Diazomethyl) Phosphonate and Reaction with Carbonyl Compounds,” Synthetic Communications, vol. 19, pp. 561-564, 1989.
Hodgson, D. et al., “Extended Scope of Dirhodium (II)-Catalysed Enantioselective Intramolecular 1,3-Dipolar Cycloadditions of Carbonyl Ylides with Alkene and Alkyne Dipolarophiles,” Synlett, Georg Thieme Verlag Stuttgard, NY, No. 1, pp. 59-62, 2003.
Müller, S. et al., “An Improved One-Pot Procedure for the Synthesis of Alkynes from Aldehydes,” Synlett, George Thieme Verlag Stuttgard, NY, Letter received Mar. 1, 1996, pp. 521-522, 1996.
Magnus, P. et al., “A model for the proposed mechanism of action of the potent antitumor antibiotic esperamicin A1,” Journal of the American Chemical Society, vol. 110, pp. 1626-1628, 1988.
Trost, B. et al., “Chemoselective Oxidation of Sulfides to Sulfones with Potassium Hydrogen Persulfate,” Tetrahedron Letters, vol. 22, No. 14, pp. 1287-1290, 1981.
Schultz, H. et al., “New Catalysts for the Oxidation of Sulfides to Sulfones with Hydrogen Peroxide,” Journal of Organic Chemistry, vol. 28, pp. 1140-1142, 1963.
Adams, J. et al., “Synthesis of Antimalarials. VI. Synthesis of Certain 1,5-and 1,8-Naphthyridine Derivatives,” Journal of the American Chemical Society, vol. 68, pp. 1317-1319, 1946.
Williamson, Thurmond A., “The Chemistry of Quinazoline,” Heterocyclic Compounds, vol. 6, pp. 324-376, 1957.
Alonso, F. et al., “Synthesis of 3- and 4-Substituted Cyclic α=Amino Acids Structurally Related to ACPD,” Tetrahedron Letters, vol. 51, No. 37, pp. 10259-10280, 1995.
Maguire, R. et al., “Stereoselective Synthesis
Hubschwerlen Christian
Surivet Jean-Philippe
Zumbrunn-Acklin Cornelia
Actelion Pharmaceutical Ltd.
Basquill Sean
Hunton & Williams LLP
Skowronek Karlheinz R
LandOfFree
Spiro antibiotic derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Spiro antibiotic derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Spiro antibiotic derivatives will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2742941