3'-aminocarbonyloxy paclitaxels

Details 3'-aminocarbonyloxy paclitaxels 3'-aminocarbonyloxy paclitaxels

1996-07-08

1997-06-03

McKane, Joseph K.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514 63, 514444, 514449, 549 4, 549 60, 549214, 549472, 549473, 549510, A61K 31335, A61K 3134, A61K 3138, C07D40502

Patent

active

056355319

ABSTRACT:
The present invention concerns novel paclitaxel derivatives, their use as antitumor agents, and pharmaceutical formulations.

REFERENCES:
patent: 4814470 (1989-03-01), Colin et al.
patent: 4942184 (1990-07-01), Haugwitz et al.
patent: 4960790 (1990-10-01), Stella et al.
patent: 5059699 (1991-10-01), Kingston et al.
patent: 5227400 (1993-07-01), Holton et al.
patent: 5229526 (1993-07-01), Holton
patent: 5254580 (1993-10-01), Chen et al.
patent: 5272171 (1993-12-01), Ueda et al.
patent: 5283253 (1994-02-01), Holton et al.
patent: 5294637 (1994-03-01), Chen et al.
patent: 5319112 (1994-06-01), Kingston et al.
patent: 5338872 (1994-08-01), Holton et al.
patent: 5352806 (1994-10-01), Gunawardana et al.
patent: 5395850 (1995-03-01), Roth
patent: 5466834 (1995-11-01), Holton
patent: 5468769 (1995-11-01), Klein et al.
patent: 5478854 (1995-12-01), Farina et al.
patent: 5489589 (1996-02-01), Wittman et al.
patent: 5489601 (1996-02-01), Holton et al.
patent: 5539103 (1996-07-01), Holton
E.K. Rowinsky and R.C. Donehower, "The Clinical Pharmacology and Use of Antimicrotubule Agents in Cancer Chemotherapeutics," Pharmac. Ther., 52:35-84, 1991.
C.M. Spencer and D. Faulds, "Paclitaxel, A Review of its Pharmacodynamic and Pharmacokinetic Properties and Therapeutic Potential in the Treatment of Cancer," Drugs, 48(5), 794-847, 1994.
K.C. Nicolaou, et al., "Chemistry and Biology of Taxol," Angew. Chem., Int. Ed. Engl., 33:15-44, 1994.
Greene and Wuts, Protective Groups in Organic Synthesis, 2nd Ed., John Wiley & Sons, and McOmie, 1991.
Protective Groups in Organic Chemistry, Ed. J.F.W. McOmie, Plenum Press, 1973.
I. Ojima, et al. "New and Efficient Approaches to the Semi-Synthesis of Taxol and its C-13 Side Chain Analogs by Means of .beta.-Lactam Synthon Method," Tetrahedron Letters, 48(34), 6985-7012, 1992.
I. Ojima, et al., "A Highly Efficient Route to Taxotere by the .beta.-Lactam Synthon Method," Tetrahedron Letters, 34(26), 4149-4152, 1993.
R. Brieva, et al, J. Org. Chem., 58, 1068-1075, 1993.
S.-H. Chen, et al, "First Syntheses of Novel Paclitaxel (Taxol) Analogs Modified at the C4-Position," J. Org. Chem., 59, pp. 6156-6158, 1994.
S.-H. Chen, et al, "Structure-Activity Relationships of Taxol: Synthesis and Biological Evaluation of C2 Taxol Analogs," Bioorganic and Medicinal Chemistry Letters, vol. 4, No. 3, pp. 479-482, 1994.
R.A. Johnson, "Taxol Chemistry. 7-O-Triflates as Precursors to Olefins and Cyclopropanes," Tetrahedron Letters, vol. 35, No. 43, pp. 7893-7896, 1994.
X. Liang and G.I. Kingston, "Synthesis and Biological Evaluation of Paclitaxel Analogs Modified in Ring C," Tetrahedron Letters, vol. 36, No. 17, pp. 2901-2904, 1995.
G. Roth, et al, "Reaction of Paclitaxel and 10-Desacetyl Baccatin III with Diehylamino Sulfurtrifluoride," Tetrahedron Letters, vol. 36, No. 10, pp. 1609-1612, 1995.
S.-H. Chen, et al, "The Chemistry of Taxanes: Reaction of Taxol and Baccatin Derivatives with Lewis Acids in Aprotic and Protic Media," Tetrahedron Letters, vol. 49, No. 14, pp. 2805-2828, 1993.
L.L. Klein, "Synthesis of 9-Dihydrotaxol: A Novel Bioactive Taxane," Tetrahedron Letters, vol. 34, No. 13, pp. 2047-2050, 1993.
Physician's Desk Reference, 49th Edition, Medical Economics, p. 682, 1995.
N. Gerber, et al, "Safety, Tolerance and Pharmacokinetics of Intravenous Doses of the Phosphate Ester of 3-Hydroxymethyl-5,5-Diphenylhydantoin: A New Prodrug of Phenytoin," J. Clin. Pharmacol., 28, pp. 1023-1032, 1988.
J. Kant, et al, "A Chemoselective Approach to Functionalize the C-10 Position of 10-Deacetylbaccatin III. Synthesis and Biological Properties of Novel C-10 Taxel Analogues," Tetrahedron Letters, 35, No. 31, pp. 5543-5546, 1994.
A.S. Kearney and V.J. Stella, "Hydrolysis of Pharmaceutically Relevant Phosphate Monoester Monoanions: Correlation to an Established Structure-Reactivity Relationship," J. of Pharmaceutical Sciences, 82, No. 1, pp. 69-72, Jan., 1993.
A.M.P. Koskinen, et al, "Enantioselective Synthesis of the Taxol and Taxotere Side Chains," J. Chem. Soc., Chem. Commun., pp. 21-22, 1994.
K.C. Nicolaou, et al, "design, Synthesis and Biological Activity of Protaxols," Nature, 364, No. 29, pp. 464-466, Jul., 1993.
M. Safadi, et al, "Phosphoryloxymethyl Carbamates and Carbonates--Novel Water-Soluble Prodrugs for Amines and Hindered Alcohols," Pharmaceutical Research, 10, No. 9, pp. 1350-1355, 1993.
D.M. Vyas, et al, "Synthesis and Antitumor Evaluation of Water Soluble Taxol Phosphates," Bioorganic & Medicinal Chemistry Letters, 3, No. 6, pp. 1357-1360, 1993.
D.M. Vyas, et al, "Chapter 9. Phosphatase-Activated Prodrugs of Paclitaxel," Taxane Anticancer Agents: Basic Science and Current Status, pp. 124-137, American Chemical Society, Washington, D.C., G.I. Georg, et al (ED), 1995.
Z.-M. Wang, et al, "Large-Scale and Highly Enantioselective Synthesis of the Taxol C-13 Side Chain through Asymmetric Dihydroxylaion," J. Org. Chem., 59, No. 17, pp. 5104-5105, 1994.
S.-H. Chen, et al, "Taxol.RTM. Structure-Activity Relationships: Synthesis and Biological Evaluation of Taxol Analogs Modified at C-7," Bioorganic & Medicinal Chemistry Letters, vol. 4, No. 18, pp. 2223-2228, 1994.
Mahendra D. Chordia, et al., "Synthesis and Biological Evaluation of 4-Deacetoxy-paclitaxel," Tetrahedron Letters, vol. 35, No. 37, pp. 6843-6846, 1994.
K.A. Neidigh, et al, "Synthesis and Biological Evaluation of 4-Deacetyl-paclitaxel," Tetrahedron Letters, vol. 35, No. 37, pp. 6839-6842, 1994.
F.A. Holmes, et al, Taxane Anticancer Agents Basic Science and Current Status, edited by G.I. Georg, et al., 1995, American Chemical Society, Washington, D.C. 31-57.
S.G. Arbuck, et al, Taxol.RTM. Science and Applications, edited by M. Suffness, 1995 (R. C. Press Inc., Boca Raton, Florida), pp. 379-416.
J.W. Harris, et al, J. Med. Chem., 37, pp. 706-709, 1994.
A. Rahman, et al, Cancer Research, 54, pp. 5543-5546, 1994.
G. Kumar, et al, Cancer Chemother. Pharmacol., 36, pp. 129-135, 1995.
J.-N. Denis, et al, "Docetaxel (Taxotere) Derivatives: Novel NbCl.sub.3 -Based Stereoselective Approach to 2'-Methyldocetaxel," J. Chem. Soc. Perkin Trans. 1, pp. 1811-1815, 1995.
F. Gueritte-Voegelein, et al, "Chemical Studies of 10-Deacetyl Baccatin III. Hemisynthesis of Taxol Derivatives," Tetrahedron Letters, vol. 42, No. 16, pp. 4451-4460, 1986.
K. C. Nicolaou, et al, "Chemical Synthesis and Biological Evaluation of C-2 Taxoids," J. Am. Chem. Soc., 117, pp. 2409-2420, 1995.
K. V. Rao, et al, "Synthesis and Evaluation of Some 10-Mono- and 2', 10-Diesters of 10-Deacetylpaclitaxel," J. Med. Chem., 38, pp. 3411-3414, 1995.
W. C. Rose, "Evaluation of Madison 109 Lung Carcinoma as a Model for Screening Antitumor Drugs," Cancer Treatment Reports, 65, No. 3-4, pp. 299-312, Mar.-Apr. 1981.
F. Gueritte-Voegelein, et al, "Relationships Between the Structure of Taxol Analogues and Their Antimitotic Activity," J. Med. Chem., 34, pp. 992-998, 1991.
C. S. Swindell, et al, "Biologically Active Taxol Analogues with Deleted A-Ring Side Chain Substituents and Variable C-2' Configurations", J. Med. Chem., 34, pp. 1176-1184, 1991.
H. J. Williams, et al, "NMR and Molecular Modeling Study of Active and Inactive Taxol Analogues in Aqueous and Nonaqueous Solution", Can. J. Chem., 72, pp. 252-260, 1994.
D. Guenard, et al, "Taxol and Taxotere: Discovery, Chemistry, and Structure-Activity Relationships", Acc. Chem. Res., 26, pp. 160-167, 1993.
L. Mangatal, et al, "Application of the Vicinal Oxyamination Reaction with Asymmetric Induction to the Hemisynthesis of Taxol and Analogues", Tetrahedron Letters, 45, (13), pp. 4177-4190, 1989.
J. Dubois, et al, "Conformation of Taxotere.RTM. and Analogues Determined by NMR Spectroscopy and Molecular Modeling Studies", Tetrahedron Letters, 49 (30), pp. 6533-6544, 1993.

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