Enzymatic resolution of t-butyl taxane derivatives

Chemistry: molecular biology and microbiology – Process of utilizing an enzyme or micro-organism to destroy... – Resolution of optical isomers or purification of organic...

Reexamination Certificate

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C549S510000, C549S511000, C549S357000, C435S123000, C435S117000, C435S197000

Reexamination Certificate

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07063977

ABSTRACT:
A method for the resolution of a mixture of the cis or trans enantiomers of a compound of the formulawherein R1is —O—C(O)alkyl, —O—C(O)aryl or —O—C(O)cycloalkyl by contacting the mixture with a carboxylic ester hydrolase enzyme which catalyzes the stereoselective hydrolysis of the mixture and the use of such enantiomers to produce antitumor compounds which are especially suitable for oral administration.

REFERENCES:
patent: 5175315 (1992-12-01), Holton
patent: 5227400 (1993-07-01), Holton
patent: 5229526 (1993-07-01), Holton
patent: 5243045 (1993-09-01), Holton
patent: 5254580 (1993-10-01), Chen
patent: 5274124 (1993-12-01), Holton
patent: 5294637 (1994-03-01), Chen
patent: 5336785 (1994-08-01), Holton
patent: 5466834 (1995-11-01), Holton
patent: 5808102 (1998-09-01), Poss
patent: 5840929 (1998-11-01), Chen
patent: 6750246 (2004-06-01), Kadow et al.
patent: 6916942 (2005-07-01), Kadow et al.
patent: 0 590 267 (1994-04-01), None
patent: 747385 (1996-12-01), None
patent: WO 94/14787 (1994-07-01), None
patent: WO 98/53811 (1998-12-01), None
Seminars in Oncology 1999, 26 (1, Suppl 2).
Rowinsky et al. in TAXOL®: A Novel Investigational Antimicrotubule Agent, J. Natl. Cancer Instl, 82: pp. 1247-1259, 1990.
Rowinsky and Donehower in “The Clinical Pharamacology and Use of Antimicrotubule Agents in Cancer Chemotherapeutics,” Pharmac. Ther., 52:35-84, 1991.
Spencer and Faulds in “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. in “Chemistry and Biology of TAXOL®,” Angew. Chem., Int. Ed. Engl., 33: 15-44, 1994.
F.A. Holmes, et al. “Taxane Anticancer Agents Basic Science and Current Status” edited by Gunda I. Georg, Thomas T. Chen, Iwao Ojima, and Dolotrai M. Vyas, 1995, American Chemical Society, Washington, DC, 31-57.
Susan G. Arbuck and Barbara Blaylock in the book “TAXOL® Science and Applications” edited by Mathew Suffness, 1995, CRC Press Inc., Boca Raton, Florida, 379-415.
Biologically Active Taxol Analogues with Deleted A-Ring Side Chain Substituents and Variable C-2′ Configurations, J. Med. Chem., 34, pp. 1176-1184 (1991).
Structure of Taxol Analogues and Their Antimitotic, J. Med. Chem., 34, pp. 992-998 (1991).
Jorge E. Cortes and Richard Pazdur in Journal of Clinical Oncology 1995, 13(10), 2643 to 2655.
Eiseman et al., Second NCI Workshop on Taxol and Taxus (Sep. 1992).
J. Terwogt et al., from the Lancet, Jul. 25, 1998, vol. 352 p. 285.
U.S. Appl. No. 09/712,352.
Gunda I. Georg et al., Tetrahedron Letters, 1994, 35(48) 8931-8934.
S. Chen et al., in Journal of Organic Chemistry 1994, 59(21), 6156-8.
Chen, Shu-Hui. First synthesis of C-4 methyl ether paclitaxel analogs and the unexpected reactivity of 4-deacetyl-4-methyl ether baccatin III. Tetrahedron Lett. 1996, 37(23), 3935-3938.
Chen, Shu-Hui; Wei, Jian-Mei; Long, Byron H.; Fairchild, Craig A.; Carboni, Joan; Mamber, Steven W.; Rose, William C.; Johnston, Kathy; Casazza, Anna M.; et al. Novel C-4 paclitaxel (Taxol) analogs: potent antitumor agents. Boorg. Med. Chem. Lett. 1995, 5(22), 2741-6.
Chen, Shu-Hui; Fairchild, Craig; Long, Byron H. Synthesis and Biological Evaluation of Novel C-4 Aziridine-Bearing Paclitaxel (Taxol) Analogs. J. Med. Chem. 1995, 38(12), 263-7.
Uoto, Kouichi; Takenoshita, Haruhiro; Ishiyama, Takashi; Terasawa, Hirofumi; Soga, Tsunehiko, Chem. Pharm. Bull. 1997, 45(12), 2093-2095.
Samaranayake, Gamini; Neidigh, Kurt A.; Kiingston, David G. I. Modified taxols, 8. Deacylation and reacylation of Baccatin III. J. Nat. Prod. 1993, 56(6), 884-98.
Datta, Apurba; Jayasinghe, Lalith R.; Georg, Gunda I.. 4-Deacetyltaxol and 10-Acetyl-4-deacetyltaxotere: Synthesis and Biological Evaluation. J. Med. Chem. 1994, 37(24), 4258-60.
Terwogt, Jetski M. Meerum; et al. Co-administration of oral cyclosporin A enables oral therapy with paclitaxel. Clin. Cancer Res. (1990), 5(11), 3379-3384.
Hansel, Steven B. A method of making taxanes orally bioavailable by coadministration with cinchonine. PCT Int. Appl. WO 97/27855 published Aug. 7, 1997.
Pratesi G. Polizzi D, Totoreto M, Riva A, Bombardelli E, Zunino F; IND5109 a new taxane active after oral administration. Proc Am Assoc Cancer Res 1999 40 Abs 1905, Istituto Nazionale Tumori, 20133 Milan and Indena SpA, 20139, Milan, Italy.
Nicoletti ML, Rossi C, Monardo C, Stura S, Morazzoni P, Bombardelli E, Valoti G, Giavazzi R.: Antitumor efficacy of the paclitaxel analogue, IDN5109, on human ovarian cacinoma xenografts with different sensitivity to the paclitaxel. Proc Am Assoc Cancer Res 1999 40 Abs 1910.
Polizzi, Donatella; Pratesi, Graziella; Tortoreto, Monica; Supino, Rosanna; Riva, Antonella; Bombardelli, Ezio; Zunino, Franco. A novel taxane with improved tolerability and therapeutic activity in a panel of human tumor xenografts. Cancer Res. 1999, 59(5), 1036-1040.
“Protective Groups in Organic Synthesis” by T. W. Greene, John Wiley and Sons, 1981, or Fiser & Fiser.
European Patent Application No. 400,971.
T.W. Greene in Chapter 2 of “Protecting Groups in Organic Synthesis”, Third Ed., by Theodora W. Greene and Peter G. M. Wuts (1999, John Wiley & Sons, New York).

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