4-(1-amino-ethyl)-cyclohexylamine derivatives

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C514S300000, C544S048000, C544S051000, C544S105000, C546S122000

Reexamination Certificate

active

08044044

ABSTRACT:
The invention relates to compounds of formula (I) wherein R0represents H or OH; R1represents alkoxy; U and W represent N, V represents CH and R2represents H or F, or U and V represent CH, W represents N and R2represents H or F, or U and V represent N, W represents CH and R2represents H, or U represents N, V represents CH, W represents CRaand R2represents H; Rarepresents CH2OH or alkoxycarbonyl; A represents the group CH═CH—B or a binuclear heterocyclic system D, B representing a mono- or di-substituted phenyl group wherein the substituents are halogen atoms and D representing one of the following groups wherein Z represents CH or N, and Q represents O or S; and to salts of such compounds. These compounds are useful as antibacterial agents.

REFERENCES:
patent: 5536725 (1996-07-01), Cullen et al.
patent: WO 00/24717 (2000-05-01), None
patent: WO 03/051887 (2003-06-01), None
patent: WO 03/087098 (2003-10-01), None
patent: WO 2004/002992 (2004-01-01), None
patent: WO 2004/035569 (2004-04-01), None
patent: WO 2004/058144 (2004-07-01), None
patent: WO 2006/021448 (2006-03-01), None
patent: WO 2006/032466 (2006-03-01), None
patent: WO 2006/046552 (2006-05-01), None
patent: WO 2006/093253 (2006-09-01), None
Blakemore, P., “The Modified Julia Olefination: Alkene Synthesis via the Condensation of Metallated Hetroarylalkylsulfones with Carbonyl Compounds”, Journal Chem. Soc., Perkin Trans. 1 (2002), 2563-2585 28.
Corey, E. J. et al., A Synthetic Method for Formyl-Ethynyl Conversion (RCHO RC=CH or RC=CR) Tetrahedron Letters (1972), No. 36, 3769-3772.
DeLoux, L. and Srebnik, M., “Asymmetric Boron-Catalyzed Reactions”, Chem. Rev. (1993), 93, 763-764, 15.
Dess, D. et al., “A Useful 12-I-5 Triacetoxyperiodinane (the Dess-Martin Periodinane) for the Selective Oxidation of Primary or Secondary Alcohols and a Variety of Related 12-I-5 Species”, Journal American Chemical Society (1991), 113, pp. 7277-7287.
Echavarren, A., “Palladium-Catalyzed Coupling of Aryl Triflates with Organostannanes”, Journal of American Chemical Soc. (1987), 109, 5478 32.
Fukuyuma, T., 2-and 4 Nitrobenzenesulfamides Exceptionally Versatile Means for Preparation of Secondary Amines and Protection of Amines, Tetrahedron Letters (1995), vol. 36, 6373.
Gould, P., “Salt Selection for Basic Drugs”, International Journal of Pharmaceutics, (1986), 33, pp. 201-217.
Greene, T.W., “Protection for the Amino Group”, Protecting Groups in Organic Synthesis, 3rdEd (1999), pp. 494-653.
Greene, T.W., “Protection for the Carboxyl Group”, Protecting Groups in Organic Synthesis 3rd Ed; 1999, 369 441; T.W. Greene, P.G.M. Wuts.
Hanessian, S. et al., “Generation of Functional Diversity Via Nitroaldol Condensations of α-Aminaacid Aldehydes—A New and Stereocontrolled Route to Acyclic 1,3-Diamino-2-Alcohols”, Tetrahedron Letters, vol. 37, No. 7, pp. 987-990, (1996).
Heck, R., “Palladium-Catalyzed Vinylation of Organic Halides”, Org. Resct. (1982), 27, 345-390.
Hodgson, D.M. et al., “Extended Scope of Dirhodium (II)-Catalysed Enantioselective Intramolecular 1,3-Dipolar Cycloadditions of Carbonyl Ylides with Alkene and Alkyne Dipolarophiles”, Synlett (2003), 59-62.
Itagaki, N., “Organocatalytic Entry to Chiral Bicyclo [3.n.1] Alkanones via Direct Asymmetric Intramolecular Aldolization” Organic Letters (2005), 7, 4185.
Kolb, H. et al., “Catalytic Asymmetric Dihydroxylation”, Chemical Review (1994), vol. 94, pp. 2483-2547.
Ley, S. et al., “Tetrapropylammonium Perruthenate, Pr4 N+RuO4, TPAP: Catalytic Oxidant for Organic Synthesis”, Synthesis, (1994), 7, 639-666.
Luzzio, F., The Henry Reaction: Recent Examples, Tetrahedron Letters vol. 57, 915-945, (2001).
Meijere, A. and Meyer, F., “Fine Feathers Make Fine Birds: The Heck Reaction in Modern Garb”, Angew. Chem. Int. Ed. Engl. (1994), 33 (23-24), 2379-2411.
Mitsunobu, O., “The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Syntersis and Transformation of Natural Products”, Synthesis (1981), 165.
Muller, S. et al., “An Improved One-Pot Procedure for the Synthesis of Alkynes from Aldehydes”, Synlett (1996), 521-522.
Ohira, S., “Methanolysis of Dimethyl (1-Diazo-2-Oxopropyl) Phosphonate: Generation of Dimethyl (Diazomethyl) Phosphonate and Reaction with Carbonyl Compounds”, Synthetic Communications, (1989), vol. 19, 561-564.
Sato, S. et al., “One-Pot Reductive Amination of Aldehydes and Ketones with α-Picoline-Borane in Methanol, in Water, and in Neat Conditions”, Tetrahedron Letters (2004), vol. 60,7899-7906.
Schultz, H., New Catalysts for the Oxidation of Sulfides to Sulfones with Hydrogen Peroxide, Journal of Organic Chemistry (1963), vol. 28, 1140.
Shioiri, T., “Degradation Reactions”, Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; vol. 6, p. 795.
Sonogashira, K. in Metal-Catalyzed Cross Coupling Reactions, Diedrich, F., Stang, P.J., Eds; Wiley-VCH: New York 1998.
Suggs, J.W., “Facile Synthesis of 8-Substituted Quinolines”, Journal of Organic Chemistry (1980), 45,1514.
Talbot, G., “Bad Bugs Need Drugs: An Update on the Development Pipeline from the Antimicrobal Availability Task Force of the Infectious Diseases Society of America”, Clinical Infectious Diseases (2006); (42) 657-68.
Trost, B. et al., “Chemoselective Oxidation of Sulfides to Sulfones with Potassium Hydrogen Persulfate”, Tetrahedron Letters, vol. 22, No. 4, (1981), 1287-1290.
Trost, B. et al., Asymmetric Alkylation of Nitroalkanes, Angew Chern. Int. Ed. (2000), 3122-3124.
Wadsworth, W. et al., “The Utility of Phosphonate Carbanions in Olefin Synthesis”, Journal of the American Chemical Soc. (1961), vol. 83,1733 1 B.
Wright, S. et al., Convenient Preparations of T-Butyl Esters and Ethers from T-Butanol, Tetrahedron Letters, vol. 38, No. 42, pp. 7345-7348, (1997).
Zhang, H.X. et al., Palladium and Molybdenum Catalyzed Hydrostannation of Alkynes a Novel Access to Regio and Stereodefined Vinylstannanes, Journal of Organic Chemistry (1990), vol. 55, 1B57.
International Search Report for Application No. PCT/IB2007/055281 mailed Jun. 19, 2008.
Greene et al., Protective Groups in Organic Synthesis, 3rd Edition, pp. 17-245, particularly pp. 23-147, 133-139 and 142-143 (Publisher: John Wiley and Sons, Inc., New York, N.Y.) (1999).
Siegel, et al., Heterogeneous Catalytic Hydrogenation of C=C and C=C, University of Arkansas, Fayetteville, AR, Pergamon Press: New York, vol. 8, pp. 417-488 (1991).
Troy et al., Index of Remington: The Science and Practice of Pharmacy, 21stEdition, published by Lippincott Williams & Wilkins (2005).

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