Oxazinones and methods for their use and synthesis

Details Oxazinones and methods for their use and synthesis Oxazinones and methods for their use and synthesis

2005-03-01

2005-03-01

Raymond, Richard L. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C514S228800, C544S063000, C544S068000

Reexamination Certificate

active

06861416

ABSTRACT:
The invention pertains, at least in part, to new intermediates and synthetic methods for the stereospecific synthesis of oxazinone compounds, which are useful, for example, as antibiotics. The invention also pertains to novel olefinic oxazinone compounds, methods for their synthesis, and methods of using these compounds for the synthesis of oxazinones. The invention also pertains to methods for using the compounds to treat bacterial associated states in subjects.

REFERENCES:
patent: 4013653 (1977-03-01), Wolfe
patent: 4775670 (1988-10-01), Sykes et al.
patent: 4822788 (1989-04-01), Kishimoto et al.
patent: 5552543 (1996-09-01), Wolfe et al.
patent: 6399600 (2002-06-01), Wolfe et al.
patent: 62-215585 (1987-09-01), None
patent: 9207837 (1992-05-01), None
CVhemical Abstract DN 117:69872, also cited as WO 9207837.*
Baldwin et al. “The synthesis of potential γ-lactam antibiotics containing a cycloserine nucleus.”Tetrahedron Letters(1990) 31(15):2211-2212.
Barlos et al. “Anwendung von N-Tritylmethionin zur Darstellung von biologisch und synthetisch interessanten Heterocyclen.”Liebigs Ann. Chem(1988) pp. 1127-1133 (Engl. abstr.).
Bruncko et al. “N-bromoacetamide. A new nitrogen source for the catalytic asymmetric aminohydroxylation of olefins.”Angew. Chem. Int. Ed. Engl.(1997) 36(13/14):1483-1486.
Frankel et al. “DL-Cyclocanaline (cyclohomoserine) and related compoubds.”J. Chem. Soc. Secition C: Organic Chemistry(1969) pp. 1746-1749.
Furrow et al. “Practical Access to Highly Enantioenriched C-3 Building Blocks via Hydrolytic Kinetic Resolution.”J. Org. Chem.(1998) 63:6776-6777.
Gao et al. “Asymmetric synthesis of both enantiomers of tomoxetine and fluoxetine. Selective reduction of 2,3-epoxycinnamyl alcohol with red-A1.”J. Org. Chem.(1988) 53:4081-4084.
Hatayama et al. “Highly enantioselective epoxidation of 2,2-dimethylchromenes.”Synlett.(1992) 407-409.
Hora, “Synthesis of 7-α-Acetylthio-(6′R)-6′-Methyl-3′-Oxotetrahydro-1,1′2′-Oxazino[4′,5′:13β,17β]-18-Norandrost-4-En-3-One.”Collection Czechoslov. Chem. Commun.(1967) 32:2820-2825.
Hora, “Synthesis of Steroidal Tetrahydro-1,2-Oxazine-3-One Derivatives.”Collection Czechoslov. Chem. Commun.(1965) 30:70-80.
Hou et al. “Desymmetric ring-opening of meso-epoxides with anilines: a simple way to chiral β-amino alcohols.”Tetrahedron: Asymmetry(1998) 9:1747-1752.
Jacobson et al. “Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane.”J. Am. Chem. Soc.(1991) 113:7063-7064.
Karpeiskii et al. “The Mechanism of Reaction of Cycloserine and Related Compounds with Aspartate-Glutamate Transaminase.”Biokhimiya(1963) 28(2):345-352.
Khomutov et al. “Synthesis of Cyclocanaline (Homocycloserine) and Related Compounds.”Izvestiya Akademii Nauk SSSR(1962) 12:2161-2166Chemical Abstracts13944, 1963.
Khomutov et al. “Synthesis of Tetrahyro-1, 2-Oxazin-3-One.”Izvestiya Akademii Nauk SSSR, Otdelenie Khimicheskikh Nauk(1962) 6:1074-1076Chemical Abstracts13754a, 1962.
Khomutov et al. “The Relationship Between Biological Activity and Chemical Properties.”Biokhimiya(1961) 26(5): 772-781.
Khomutov, “Synthesis of O-Substituted Hydroxylamines.”Zhurnal Obshchei Khimii(1961) 31(6):1992-1995.
Khomutov et al. “On Some Cycloserine Derivatives Possessing Antituberculose activity.”Voprosy Meditsinskoi Khimii(1962) 8:389-391 (English abstr.).
Kotsuki et al. “High pressure-promoted uncatalyzed hydrolysis of epoxides.”Tet. Lett.34:4031-4034.
Kuehl et al. “Communications to the Editor: A-4-Amino-3-Isoxazolidone, A New Antibiotic.”J. Am. Chem. Soc.(Apr./Jun. 1955) 77:2344-23450.
Linker, “The Jacobsen-Katsuki epoxidation and its controversial mechanism.”ACIEE(1997) 36:2060-2.
Markova et al. “Hydroxylamine Derivatives.”Chemical Abstracts70: 66520h (1970).
Meguro et al. “Ytterbium triflate and high pressure-mediated ring opening of epoxides with amines.”J. Chem. Soc. Perkin. Trans. 1(1994) pp. 2597-2601.
Molander et al. “Reduction of vinyloxiranes with samarium diiodide. An efficient route to functionalized chiral, nonracemic (E)-allylic alcohols.”J. Org. Chem.(1986) 51:5259-5264.
O'Brien et al. “Sharpless asymmetric aminohydroxylation: Scope, limitations, and use in synthesis.”Angew. Chem. Int. Ed.(1999) 38(3):326-329.
Olah et al. “Synthetic methods and rections.43. Preparation of fluorohydrins from epoxides with pyridinium poly-hydrogen fluoride.”Isr. J. Chem.(1978) 17:148-149.
Oshima et al. “Palladium-catalyzed selective hydrogenolysis of alkenyloxiranes with formic acid. Stereoselectivity and synthetic utility.”J. Am. Chem. Soc.(1989) 111:6280-6287.
Pfenninger, “Asymmetric epoxidation of allylic alcohols: The sharpless epoxidation.”Synthesis(1986) pp. 89-116.
Procter et al. “β-Lactams From Tetrahydro-1,2-Oxazine-3,6-Diones, and a Labelling Study of the Product Stereochemistry.”Tetrahedron(1995) 51(47):12837-12842.
Rosenthal et al. “Insecticidal Properties of Some Derivatives of L-Canavanine”,J. Agric. Food Chem.(1995) 43:2728-2734.
Sharpless et al. “On the mechanism of titanium-tartrate catalyzed asymmetric epoxidation.”Pure Appl. Chem.(1983) 55:1823-1836.
Shimizu et al. “Highly selective ring opening of epoxides with silicon tetrafluoride: preparation of fluorohydrins.”Tett. Lett.(1988) 29:4101-4104.
Strominger et al. “Composition of the cell wall ofstaphylococcus aureus: Its relation to the mechanism of action of penicillin,”J. Biol. Chem.234:3263-3268 (1959).
Tabei et al. “Reaction of β-bromoacetoacetyl bromide with N-phenylhydroxylamine derivatives: synthesis of 1,2-oxazine derivatives.”Chemical Abstracts92:76436 (1980).
Tabei et al. “Reaction of β-bromoacetoacetyl bromide with N-phenylhydroxylamine derivatives: Synthesis of 1,2-oxazine derivatives.”Chem. Pharm. Bull.(1979) 27(8): 1842-6.
Tabei et al. “Organic Sulfites Containing a 1,2-Oxazine Ring.”Chem. Pharm. Bull.(1980) 28(1): 330-336.
Tao et al. “Reversal of regioselection in the asymmetric aminohydroxylation of cinnamates.”Tet. Lett.(1998) 39:2507-2510.
Umemoto et al. “Power and structure-variable fluorinating agents. The N-Fluoropyridinium salt system.” J. Am. Chem. Soc. (1990) 112:8563-75.
Wang et al. “Catalytic asymmetric dihydroxylation of cis-disubstituted olefins.”J. Am. Chem. Soc.(1992) 114:7568-7570.
Wolfe et al. “1992 p-Hydration of the Carbonyl Group. A Theoretical Study of the Cooperative Mechanism.”J. Am. Chem. Soc.(1995) 117:4240-4260.
Wolfe, “Lemieux Award lecture: Studies related to the penicillin receptor.”Canadian J. Chem.(1994) 72: 1014-32.
Wolfe et al. “A semiempirical molecular orbital study of the methanolysis of complex azetidinones. A combined MM and QM analysis of the interaction of Δ2-and Δ3-cephems with the penicillin receptor.”Canadian J. Chem.(1994) 72:1044-50.
Wolfe et al. “Ab initio molecular orbital calculations on the neutral hydrolysis and methanolysis of azetidinones, including catalysis by water. Relationship to the mechanism of action of β-lactam antibiotics.”Canadian J. Chem.(1994) 72:1033-43.
Wolfe et al. “Conformation-activity relationships and the mechanism of action of penicillin.”Canadian J. Chem.(1988) 66(11):2733-50 (English abs.).
Wolfe et al. “Interactive design and synthesis of a novel antibacterial agent.”Canadian J. Chem.(1994) 72(4):1051-65.
Wolfe et al. “MMPEP: Development and evaluation of peptide parameters for Allinger's MMP2(85) programme, including calculations on crambin and insulin.”Canadian J. Chem.(1988

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