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Preface l H E ANTICANCER TAXANES PACLITAXEL AND DOCETAXEL are the most promising new chemotherapeutic agents developed for cancer treatment in the past decade. Early concerns about paclitaxel's lack of activity against certain leukemia models, limited availability, and problems with its formulation almost prevented its development as a clinical agent. But then, clinical trials conducted in the late 1980s and early 1990s demonstrated impressive clinical activities against advanced ovarian and breast cancer. The U.S. Food and Drug Adminstration has approved the clinical use of paclitaxel for these two types of cancer. Recent clinical trials have shown that paclitaxel and docetaxel may also be useful agents for the treatment of non-small-cell lung cancer, head and neck cancer, and other types of cancers. The promising clinical activities of the anticancer taxanes combined with potential problems due to limited supply generated a multitude of programs worldwide, such as broader clinical trials and in-depth clinical evaluation of anticancer taxanes, efforts to provide an adequate supply of paclitaxel for clinical trials and for cancer patients, development of better drug formulations, biochemical studies to elucidate the precise mechanism of action, chemical studies to obtain structure-activity information, development of second-generation paclitaxel analogues, elaboration of semisynthetic methods for the large-scale production of the anticancer taxanes, and efforts directed at the total synthesis of paclitaxel. Chemistry plays a pivotal role in many of these endeavors, and so the American Chemical Society held its first symposium on paclitaxel in 1992. Because of continued excitement about the anticancer taxanes, three divisions of the A C S held a series of symposia on taxane research in 1994. The Division of Chemical Health and Safety asked Thomas T. Chen to organize their symposium entitled "Symposium on the Cellular Mechanism of Action and Toxicity of Taxol." He is grateful for the support of this symposium from Glaxo, SmithKline Beecham, T P L Phytogen, the University of Tennessee Physicians' Medical Education and Research Foundation and the Graduate School. For the Division of Medicinal Chemistry, Gunda I. Georg and Dolatrai (Dinesh) M . Vyas organized a symposium entitled "Advances in the Medicinal Chemistry of Taxol and Taxoids." They acknowledge the financial contributions from BristolMyers Squibb to make the symposium possible. Iwao Ojima organized N O T E : Paclitaxel is the generic name for Taxol, which is now a registered trademark. Docetaxel is the generic name for Taxotere, which is also a registered trademark.
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the symposium "Advances in the Chemistry of Taxane and Taxoid Anticancer Agents," for the Division of Organic Chemistry. He gratefully acknowledges support from Bristol-Myers Squibb, Rhone-Poulenc Rorer, Indena, and Abbott for this symposium. The publication of the symposium contributions provides comprehensive coverage of the newest research results in a timely fashion to interested chemists, biochemists, biologists, clinicians, and other scientists in the United States and abroad. This book contains 24 chapters, ranging in content from recent clinical results, paclitaxel formulation problems, metabolism studies, taxane biosynthesis, tubulin biochemistry to medicinal chemistry, semisynthesis, and total synthesis of anticancer taxanes. It is the first multi-author, comprehensive overview of important areas of taxane research, containing a multitude of previously unpublished research results. With the publication of this book, the authors hope to further stimulate the interest and the ongoing research activites in the exciting area of anticancer taxanes. We dedicate this book to people who live with cancer. G U N D A I. G E O R G
Department of Medicinal Chemistry University of Kansas Lawrence, KS 66045-2506 T H O M A S T. C H E N
Departments of Zoology and Obstetrics and Gynecology University of Tennessee Knoxville, T N 37996 IWAO OJIMA
Department of Chemistry State University of New York at Stony Brook Stony Brook, N Y 11794-3400 D O L A T R A I (DINESH) M . V Y A S
Bristol-Myers Squibb PRI 5 Research Parkway Wallingford, C T 06492-7660 September 29, 1994
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Brief History of the Discovery and Development of Taxane Anticancer Agents (1-3) 1962
Collection of Taxus brevifolia in the Gifford Pinchot National Forest in the State of Washington by USDA botanist Arthur Barkley as a result of a collaborate effort between the USDA and the NCI Plant Program under the direction of Jonathan Hartwell.
1964
Cytotoxicity of bark extracts to KB cells established. Shipment of 30 lbs. of bark to Monroe Wall at the Research Triangle Institute (RTI).
1966
Isolation of taxol (K172) and cytotoxic activity of the pure compound against KB cells by the Wall group.
1967
Disclosure of taxol isolation at the American Chemical Society National Meeting in Miami Beach in Florida by the Wall group.
1971
Publication of the structure and biological activity of taxol in the Journal of the American Chemical Society by M . Wall with M . Wani and H. Taylor (RTI) and A. McPhail and P. Coggon (Duke University).
1974
Activity in the in vivo B16 (ip, ip) melanoma model (NCI).
1977
Championed by Matthew Suffness, taxol becomes an NCI development candidate.
1978
Activity against the NCI LX-1 lung xenograft, MX-1 breast xenograft and CX-1 colon xenograft.
1978
Publication by D. A. Fuchs and R. K. Johnson on the anti-mitotic activity of taxol (Cancer Treat. Repts.).
1979
Susan Horwitz with P. Schiff and J. Fan disclose that taxol is a promoter of microtubule assembly (Nature).
1979
Pierre Potier's laboratory (Institut des Chimie des Substances Naturelles (ICSN), CNRS) in France begins bioassay-guided purification of the European yew (Taxus baccata).
1980
At NCI, Cremophor formulation selected and route and schedule dependency studies completed. Toxicology studies with taxol begin.
1980
10-Deacetylbaccatin III, isolated from Taxus baccata, identified as readily accessible starting material for the semisynthesis of anticancer taxanes by the Potier group (CNRS). xi
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1981
Rhone-Poulenc and CNRS sign a research agreement concerning anticancer taxanes.
1982
Toxicologic studies completed. Taxol approved by NCI for Investigational New Drug Application (INDA) filing.
1983
INDA filed for taxol with the Food and Drug Administration (FDA).
1984
INDA approved by FDA. Phase I clinical trials begin.
1984
Taxotere synthesized by Francoise Gueritte-Voegelein and Daniel Guenard (ICSN-CNRS).
1985
NCI approves taxol for phase II clinical trials.
1985
In vitro assays demonstrate cytotoxicity of taxotere.
1986
The first semisynthesis of taxol via the oxamination process (ICSN-CNRS and Rhone-Poulenc patent).
1986
First asymmetric synthesis of the C-13 phenylisoserine side chain of taxol by the Green group (J. Org. Chem.).
1987
Rhone-Poulenc selects taxotere for clinical development.
1988
J. Am. Chem. Soc. publication of the semisynthesis of taxol published via direct esterification of 10-deacetylbaccatin III by the groups of Potier and Greene. CNRS - Rhone-Poulenc patent on the semisynthesis of taxol and taxotere.
1989
Johns Hopkins group publish on the activity of taxol in advanced ovarian cancer (Ann. Intern. Med.).
1989
NCI issues a request for applications for a Cooperative Research and Development Agreement (CRADA) and selects Bristol-Myers Squibb as the CRADA partner.
1989
Semisynthesis of taxol by Holton via N-acyl beta-lactams. Patent on the semisynthesis of taxol.
1989
Asymmetric synthesis of beta-lactams as phenylisoserine precursors by the Georg group and the Ojima group.
1990
Phase I clinical trials of taxotere begin in Europe and the US.
1991
M . D. Anderson group publishes finding of activity of taxol in metastatic breast cancer (J. Natl. Cancer Inst.).
1991
J. Org. Chem. publication by the Ojima group and the Georg group on the asymmetric synthesis of phenylisoserine and beta-lactam intermediates.
1991
J.
Org. Chem. publication by the Green group on the semisynthesis of taxol and taxotere from phenylglycine and 10-deacetylbaccatin III.
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1992
New Drug Application (NDA) for taxol filed by Bristol-Myers Squibb.
1992
6 Month after filing, the FDA approves taxol for the treatment of refractory ovarian cancer.
1992
Phase II clinical trials for taxotere begin worldwide.
1992
Semisynthesis of taxol and taxotere via the oxazolidinone route by Commercon and collaborators at Rhone-Poulenc Rorer (Tetrahedron Lett.)
1992
Semisynthesis of taxol and taxotere through coupling of metalated baccatin III with ß-lactam intermediates by the Holton group (patent) and the Ojima group (Tetrahedron).
1993
Taxol is marketed by Bristol-Myers Squibb Co.
1993
SNDA (Supplemental NDA) for the semisynthesis of taxolfrom10deacetylbaccatin III filed by Bristol-Myers Squibb Co.
1994
Supplemental FDA approval of taxol for the treatment of metastatic breast cancer.
1994
NDA and MAA (Manufacture Approval Authorization) for the use of taxotere in the treatment of breast and lung cancers filed.
1994
J.
Am. Chem. Soc. publication by the Holton group and Nature publication by the Nicolaou group on total syntheses of taxol.
References and Notes: (1) Many other individuals, not listed in this short history, have made very significant contributions to the development of taxol and to our current understanding of the biology and chemistry of the anticancer taxanes. Most of their names and contributions can be found in the chapters and references of this book. (2) For a detailed account of the history of the development of taxol see: Suffness, M . Wall, M. In Taxol: Science and Applications; Suffness, M., Ed.; CRC: Boca Raton, FL, 1994 (in press). (3) Taxol® is a registered trademark of Bristol-Myers Squibb Company. The generic name is paclitaxel. Taxotere® is a registered trademark of Rhone-Poulenc. Its generic name is docetaxel.
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