Metal alkoxide taxane derivatives

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C549S511000

Reexamination Certificate

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07074945

ABSTRACT:
A process for preparing N-acyl, N-sulfonyl and N-phosphoryl substituted isoserine esters in which a metal alkoxide is reached with a β-lactam.

REFERENCES:
patent: 4814470 (1989-03-01), Colin et al.
patent: 4857653 (1989-08-01), Colin et al.
patent: 4876399 (1989-10-01), Holton et al.
patent: 4924011 (1990-05-01), Denis et al.
patent: 4924012 (1990-05-01), Colin et al.
patent: 4942184 (1990-07-01), Haugwitz et al.
patent: 4960790 (1990-10-01), Stella et al.
patent: 5015744 (1991-05-01), Holton
patent: 5059699 (1991-10-01), Kingston et al.
patent: 5136060 (1992-08-01), Holton
patent: 5175315 (1992-12-01), Holton
patent: 5227400 (1993-07-01), Holton et al.
patent: 5229526 (1993-07-01), Holton
patent: 5274124 (1993-12-01), Holton
patent: 5384399 (1995-01-01), Holton
patent: 5430160 (1995-07-01), Holton
patent: 5466834 (1995-11-01), Holton
patent: 5532363 (1996-07-01), Holton
patent: 5539103 (1996-07-01), Holton
patent: 5574156 (1996-11-01), Holton
patent: 5717115 (1998-02-01), Holton
patent: 5723634 (1998-03-01), Holton
patent: 5760219 (1998-06-01), Holton et al.
patent: 6069260 (2000-05-01), Holton
patent: 6124481 (2000-09-01), Holton
patent: 6479678 (2002-11-01), Holton
patent: 0247378 (1987-12-01), None
patent: 0253738 (1988-01-01), None
patent: 0253739 (1988-01-01), None
patent: 0336840 (1989-10-01), None
patent: 0336841 (1989-10-01), None
patent: 0400971 (1990-12-01), None
patent: 1193252 (2003-11-01), None
patent: WO 92/09589 (1992-06-01), None
patent: WO 93/06079 (1993-04-01), None
Aoyama et al. “Photochemical Reactions of N-Benzoylformyl-N-(Phenylthiocarbonyl)-Amines. A Novel Photocyclization Involving 1,4-Phenylthio Migration” Tetrahedron Letters (1983), pp. 1169-1170, vol. 24. No. 11, XP002224840, Elsevier Science Publishers, Amsterdam, NL.
Bartholomew et al. “A Novel Rearrangement Reaction Conversion of 3-(Chloromethyl)azetidin-2-ones to Azetidine-3-Carboxylic Acid Esters” Tetrahedron Letters, vol. 32. No. 36 (1981) pp. 4795-4798.
Chan et al. “Taxa-4(16), 11-diene-5α, 9α, 10α, 13α-tetraol, a New Taxane Derivative from the Heartwood of Yew (T. baccataL.): X-Ray Analysis of a p-Bromobenzoate Derivative” Chem. Commun., vol. 874 (1966) pp. 923-925.
Chen et al. “Taxol Structure—Activity Relationships: Synthesis and Biologial Evaluation of 2-Deoxytaxol” Tetrahedron Letters, vol. 34. No. 20 (1993) pp. 3205-2306.
Della Casa De Marcano et al. The Isolation of Seven New Taxane Derivatives from the Heartwood of Yew (Taxus baccataL.) Chem. Communications (1969) p. 1281.
Denis et al. “A Highly Efficient Practical Approach to Natural Taxol” Journal of American Chemical Society, vol. 110. No. 17 (1988) pp. 5917-5919.
Deutsch et al. “Synthesis of Congeners and Prodrugs. 3. Water-Soluble Prodrugs of Taxol with Potent Antitumor Activity” Journal of Medicinal Chemistry, vol. 32, No. 4 (1989) pp. 788-792.
European Patent Office “EP 1 193 252 A3 Annex to the European Search Report on European Patent Application No. EP 02 00 0688”, European Patent Office, 13-12-2002, pp. 5.
Ettouati et al. “Plantes de Nouvelle-Caledonie. 114. Taxanes isoles des feuillesd'Austrotaxus spicataCompton (Taxacees)” Bull. Soc. Chim. France (1988) p. 749.
Farina et al. “The Chemistry of Taxanes: Unexpected Rearrangement of Baccatin III During Chemoselective Debenzoylation with Bu3SnOMe/LiCI” Tetrahedron Letters, vol. 33, No. 28 (1992) pp. 3979-3982.
Frappier et al. “Alcaloïdes Peptidiques-Xa. Approche de Ia Synthese des Alcaloïdes Peptidiques 1. Réactivité de N-Tosyláziridines Vis-à-Vis de Réactifs Nucléophiles” Tetrahedron (1978), pp 2911-2916, vol. 34, No. 19. XP002224841, Elsevier Science Publishers, Amsterdam, NL.
Holton et al. “A Synthesis of Taxusin”, Journal of American Chemical Society, vol. 110 (1958) pp. 6558-6560.
Holton “Synthesis at the Taxane Ring System” Journal of American Chemical Society, vol. 106 (1984) pp. 5731-5732.
Just et al. “Beta-Lactams. XI. Synthesis of N-Phosphorylated Mono-and Bicyclic Beta-Lactams1” Canadian Journal of Chemistry (1983), pp. 1730-1735. vol. 61, No. 8, XP002224842, National Research Council, Ottawa. CA.
Kaiser et al. “Synthesis of Esters of Acid-Unstable Alcohols by Meand of n-Butyllithium” Journal of Organic Chemistry, vol. 35(1970) pp. 1198-1199.
Kingston et al. “The Taxane Diterpenoids” Progress in the Chemistry of Organic Natural Products, Wein, NY Springer-Verlag, 1993.
Kingston et al. New Taxanes from Taxus Brevifolia, Journal of Natural Products, vol. 45, No. 4 (1982) pp. 466-470.
Klein “Synthesis of 9-Dihydrotaxol: A Novel Bioactive Taxane” Tetrahedron Letters, vol. 34, No. 13 (1993) pp. 2047-2050.
Liu et al. “Constituents of the Heartwood of Taiwan Yew” Tai'wan Ko'hsueh, vol. 38 (1984) pp. 119-125.
Magri et al. “Modified Taxols, 4. Synthesis and Biological Activity of Taxols Modified in the Side Chain” Journal of Natural Products, vol. 51, No. 2 (1988) pp. 298-306.
Miller et al. “Antileukemic Alkanoids fromTaxus wallichiana Zucc.” Journal of Organic Chemistry, vol. 46, No. 7 (1981) pp. 1469-1474.
Mukerjee et al. “β-Lactams: Retrospect and Prospect” Tetrahedron, vol. 34, No. 52 (1978) pp. 1731-1767.
Ojima et al. “A Highly Efficient Route to Tacotere by the Beta-Lectam Synthon Method” Tetrahedron Letters (Jun. 25, 1993), pp 4149-4152, vol. 34, No. 26, XP000561213, Elsevier Science Publishers, Amsterdam, NL.
Ojima et al. “Efficient and Practical Asymmetric Synthesis of the Taxol C-13 Side Chain, N-Be nzoyl-(2R,3S)-3-phenylisoserine, and Its Analogues via Chiral 3-Hydroxy-4-aryl-β-lactams through Chiral Ester Enolate-Imine Cyclocondensation” Journal of Organic Chemistry, vol. 56, No. 5 (1991) pp. 1681-1683.
Ojima et al. “N-Acyl-3-Hydroxy-β-Lactams as Key Intermediates for Taxotere and its Analogs” Bioorganic and Medicinal Chemistry Letters, vol. 3, No. 11 (1993) pp. 2479-2482.
Ojima et al. “New and Efficient Approaches to the Semisynthesis of Taxol and its C-13 Side-Chain Analogs by Means of β-Lactam Synthon Method” Tetrahedron, vol. 48, No. 34 (1992) pp. 6985-7012.
Ojima et al. “Synthesis and Biological Activity of 3'-alkyl- and 3'-alkenyl-3'-dephenyldocetaxels” Bioorganic and Medicinal Chemistry Letters. vol. 4, No. 21 (1994) pp. 2631-2634.
Ojima et al. “Synthesis and Structure-Activity Relationships of Novel Nor-Seco Analogs of Taxol and Taxotere” Journal of Organic Chemistry (Feb. 2, 1994), pp 515-517, vol. 59, No. 3, XP001094357, American Chemical Society, Washington, DC.
Ojima et al. Synthesis of Novel 3′-Trifluoromethyl Taxoids Through Effective Kinetic Resolution of Racemic 4-CF3-β-Lactams with Baccatins, Chirality, vol. 9 (1997) pp. 487-494.
Palomo et al. “Highly Stereoselective Synthesis of α-Hydroxy β-Amino Acids Through β-Lactams: Application to the Synthesis of the Taxol and Bestatin Side Chains And Related Systems” Tetrahedron Letters, vol. 31, No. 44 (1990) pp. 6429-6432.
Samaranayake et al. “Modified Taxols. 5.1 Reaction of Taxol with Electrophilic Reagents and Preparation of a Rearranged Taxol Derivative with Tubulin Assembly Activity” Journal of Organic Chemistry, vol. 56, No. 7 (1991) pp. 5114-5119.
Schultz et al. “Synthesis of New N-Radicals of Tetrazan-l-yl” Chemical Abstracts, vol. 108, No. 37298C (1988) p. 581.
Senilh et al. “Chime Organique Biologique-Hemisynthese de nouveaux analogueś du taxol. Etude de leur interaction avec Ia tubuline” C.R. Acad. Sci. Paris, Serie II, t..299, No. 15 (1984) pp. 1039-1043.
Wani et al. “Plant Antitumor Agents. VI. The Isolation and Structure of Taxol, A Novel Antileukemic and Antitumor Agent from Taxus Brevifolia” Journal of American Chemical Socie

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