U.S. patents available from 1976 to present.
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Lactone stable formulation of 10-hydroxy 7-ethyl camptothecin and methods for uses thereof

Patent 5447936 Issued on September 5, 1995. Estimated Expiration Date: Icon_subject December 22, 2013. Estimated Expiration Date is calculated based on simple USPTO term provisions. It does not account for terminal disclaimers, term adjustments, failure to pay maintenance fees, or other factors which might affect the term of a patent.

Patent References

Re32518

3219529

3699230

3894029

Camptothecin analogues
Patent #: 4031098
Issued on: 06/21/1977
Inventor: Sugasawa

Topical and other type pharmaceutical formulations containing isosorbide carrier
Patent #: 4082881
Issued on: 04/04/1978
Inventor: Chen, et al.

Dimethyl isosorbide in liquid formulation of aspirin
Patent #: 4228162
Issued on: 10/14/1980
Inventor: Luzzi ,   et al.

Wax emulsion
Patent #: 4339276
Issued on: 07/13/1982
Inventor: Yokoyama ,   et al.

4-Substituted-3-hydroxy-3-pyrroline-2,5-dione inhibitors of glycolic acid oxidase
Patent #: 4342776
Issued on: 08/03/1982
Inventor: Cragoe, Jr. ,   et al.

Camptothecin derivatives
Patent #: 4399282
Issued on: 08/16/1983
Inventor: Miyasaka ,   et al.

More ...

Inventors

Assignee

Application

No. 172620 filed on 12/22/1993

US Classes:

514/283Ring nitrogen in the pentacyclo ring system is shared by five-membered cyclo and six-membered cyclo (e.g., vincamine, etc.)

Examiners

Primary: Daus, Donald G.

Attorney, Agent or Firm

Foreign Patent References

  • 2087209 CA. 01/19/1993
  • 0074256 EP. 03/19/1983
  • 0074770 EP. 03/19/1983
  • 0088642 EP. 09/19/1983
  • 0220601 EP. 05/19/1987
  • 58-154583 JP. 09/19/1983
  • 58-154584 JP. 09/19/1983
  • 59-5188 JP. 01/19/1984
  • 59-51287 JP. 03/19/1984
  • 59-51289 JP. 03/19/1984
  • 59-227884 JP. 12/19/1984
  • 61-50985 JP. 03/19/1986
  • 85319 JP 04/19/1986
  • 61-85389 JP. 04/19/1986
  • 62-195384 JP. 08/19/1987
  • 238098 JP. 10/19/1988
  • 232888 JP 10/19/1991
  • 139187 JP 05/19/1992

International Class

A61K 031/475

Abstract

10-hydroxy 7-ethyl camptothecin (HECPT), an active metabolite of the camptothecin analog CPT-11, is poorly soluble in water. Because of its poor water solubility, HECPT has not been directly administered by parenteral or oral routes in human patients for the purpose of inhibiting the growth of cancer cells. There is also unpredictable interpatient variability in the metabolic production of HECPT from CPT-11 which limits the utility of CPT-11. This invention overcomes these limitations by teaching novel pharmaceutically acceptable lactone stable HECPT formulations for the direct administration of HECPT. The claimed invention also describes novel dosages, schedules, and routes of administration of the lactone stable HECPT formulations to patients with various forms of cancer.

Other References

  • Akimoto, K., et al., Selective and Sensitive Determination of Lactone and Hydroxy Acid Forms of Camptothecin and Two Derivatives (CPT-11 and SN-38) by High-Performance Liquid Chromatography with Fluorescence Detection. Journal of Chromatography, 588:165-170, 1991
  • Baer, Ora, Taxotere, Topotecan, and CPT-11: Clinical Trails Confirm Early Promise. Oncology Times, pp. 8-10, May 1993
  • Barilero et al., Simultaneous Determination of the Camptothecin Analogue CPT-11 and Its Active Metabolite SN-38 by High Performance Liquid Chromatography: Application to Plasma Pharmacokinetic Studies in Cancer Patients. J. Chromat. 575:275-280: 1992
  • Bates et al., Solubilizing Properties of Bile Salt Solutions I--Effect of Temperature and Bile Salt Concentration on Solubilizattion of Glute-ethimide, Griseofulvin and Hexestrol. Journal of Pharmaceutical Sciences, 55:191-199, 1966
  • Bates et al., Rates of Dissolution of Griseofulvin and Hexestrol in Bile Salt Solutions. Chem. Abstracts 65:8680b, 1966
  • Bates et al., Solubilizing Properties of Bile Salt Solutions on Gluteththimide, Griseofulvin, and Hexestrol. Chem. Abstracts 65:9517e, 1966; 65:15165a, 1966
  • Clavel, M. et al., Phase I Study of the Camptothecin Analogue CPT-11, Administered Daily for 3 Consecutive Days. Proc. Amer. Assoc. Cancer Res. 3:83, 1992
  • Creavan, P. J., Plasma Camptothecin (NSC 100880) Levels During a 3-Day Course of Treatment: Relation to Dose and Toxicity. Cancer Chemotherapy Rep. 56:573-578, 1972
  • Culine, S., Phase I Study of the Camptothecin Analogue CPT-11, Using a Weekly Schedule. Proc. of Amer. Soc. Clin. Onc. 11:110, 1992
  • Eckardt, J. et al., Topoisomerase I Inhibitors: Promising Novel Compounds. Div. of Med. Oncology, U. of Tex. Health Sci., 1993
  • Fukuoka, M. et al., A Phase II Study of CPT-11, A New Derivative of Camptothecin, for Previously Untreated Non Small-Cell Lung Cancer. J. Clin. Onc. 10(1):16-20, 1992
  • Giovanella, B. C. et al., DNA Topoisomerase I--Targeted Chemotherapy of Human Colan Cancer in Xenografts. Science 246:1046-1048, 1989
  • Gottlieb, J. A., Preliminary Pharmacologic and Clinical Evaluation of Camptothecin Sodium (NSC-100880). Cancer Chemotherapy Rep. 54:461-470, 1970
  • Gottlief, J. A., Treatment of Maglignant Melanoma with Camptothecin (NSC-100880), Cancer Chemotherapy Rep. 57:103-105, 1972
  • Hsiang et al., Arrest of Replication Forks by Drug-stabilized Topisomerase I-DNA Cleavable Complexes as a Mechanism of Cell Killing by Camptothecin Analogues. Cancer Res. 49:5077-5082, 1989
  • Jaxel, C. et al., Structure Activity Study of the Actions of Camptothecin Derivatives on Mammalian Topisomerase I: Evidence for a Specific Receptor Site and a Relation to Antitumor Activity. Cancer Res. 49:1465-1469, 1989
  • Kaneda, N. et al., Metabolism and Pharmacokinetics of the Camptothecin Analogue CPT-11 in the Mouse. Cancer Reserch 50:1715-1720, 1990
  • Kano Y. et al., Effects of CPT-11 in Combination With Other Anti-Cancer Agents in Culture. Int. J. Cancer 50:604-610, 1992
  • Kanzawa F. et al., Role of Carboxylesterase on Metabolism of Camptothecin Analog (CPT-11) in Non-Small Cell Lung Cancer Cell Line PC-7 Cells (Meeting Abstract), Proc. Annual Meet. Am. Assoc. Cancer Res. 33:A2552, 1992
  • Kawato, Y. et al., Intracellular Roles of SN-38, a Metabolite of the Camptothecin Derivative CPT-11, in the Antitumor Effect of CPT-11. Cancer Res. 51:4187-4191, 1991
  • Kingsbury, W. D. et al., Synthesis of Water-Soluble (Aminoalkyl) Camptothecin Analogues: Inhibition of Topoisomerase I and Antitumor Activity. J. Med. Chem. 34:98-107, 1991
  • Kunimoto, T. et al., Antitumor Activity of 7-Ethyl-10-[4-(1-Piperidino)-1-piperidino] Carbonyloxy-Camptothecin, a Novel Water Soluble Derivative of Camptothecin Against Murine Tumors. Cancer Res. 47:5944-5947, 1987
  • Malone et al., Desoxycholic Acid Enhancement of Orally Administered Reserpine. Journal of Pharmaceutical Sciences, 55:972-974, 1966
  • Masuda, N. et al., CPT-11: A New Derivative of Camptothecin for the Treatment of Refractory or Relapsed Small-Cell Lung Cancer. J. Clin. Onc. 10(8):1225-1229, 1992
  • Moertel, C. G., Phase II Study of Camptothecin (NSC-100880) in the Treatment of Advanced Gastrointestinal Cancer. Cancer Chemotheraphy Rep. 57:103-105, 1972
  • Muggia, F. M., Phase I Clinical Trial of Weekly and Daily Treatment with Camptothecin (NSC-100880): Correlation With Preclinical Studies. Cancer Chemotherapy Rep. 55:515-521, 1972
  • Negoro, S. et al., Phase I Study of Weekly Intravenous Infusions of CPT-11, a New Derivative of Camptothecin, in the Treatment of Advanced Non-Small Cell Lung Cancer. JNCI 83(16): 1164-1168, 1991
  • Negoro, S. et al., Phase II Study of CPT-11, a New Camptothecin Derivative, in Small Cell Lung Cancer. Proc. of Amer. Soc. Clin. Onc. 10:241, 1991
  • Niimi S. et al., Mechanism of Cross-Resistance to a Captothecin Analogue (CPT-11) in a Human Ovarian Cancer Cell Line Selected by Cisplatin. Cancer Res. 52:328-333, 1992
  • Ohe,. Y. et al., Phase I Study and Pharmacokinetics of CPT-11 With 5-Day Coninuous Infusion. JNCI 84(12):972-974, 1992
  • Ohno, R. et al., An Early Phase II Study of CPT-11: A New Derivative of Camptothecin, for the Treatment of Leukemia and Lymphoma. J. Clin. Onc. 8(11): 1907-1912, 1990
  • Pommier, Y. et al., Camptothecins: Mechanism of Action and Resistance (Meeting Abstract). Cancer Investigation, Presented at the "Chemotherapy Foundation Symposium X Innovative Cancer Chemotherapy for Tomorrow," p. 3, 1992
  • Rothenberg, M. L. et al., A Phase I and Pharmacokinetic Trail of CPT-11 in Patients With Refractory Solid Tumors. Amer. Soc. Clin. Onc. 11:113, 1992
  • Rothenberg, M. L. et al., Phase I and Pharmacokinetic Trial of Weekly CPT-11. Journal of Clinical Oncology. 11:2194-2204, 1993
  • Rowinsky, E. et al., Phase I and Pharmacologic Study of CPT-11, A Semisythetic Topoisemerase I-Targeting Agent, on a Single Dose Schedule (Meeting Abstract). Proc. of Amer. Soc. Clin. Onc. 11:114, 1992
  • Sawada, S. et al., Synthesis and Antitumor Activity of 20 (S)--Camptothecin Derivatives: Carbonate-Linked. Water-Soluble, Derivatives of 7-Ethyl-10-Hydroxycamptothecin. Chem. Pharm. Bull. 39:1446-1454, 1991
  • Shimada, Y. et al., Phase II Study of CPT-11, New Camptothecin Derivative in the Patients with Metastatic Colorectual Cancer. Proc. of Amer. Soc. Clin. Onc. 10:135, 1991
  • Takeuchi, S. et al., Late Phase II Study of CPT-11, A Topoisomerase I Inhibitor , in Advanced Cerivical Carcinoma (CC) (Meeting Abstract). Proc. of Amer. Soc. Clin. Onc. 11:224, 1992
  • Wall, M. E. et al. Plant Anti-tumor Agents I--The Isolation and Stucture of Camptothecin, a Novel Alkaloidal Leulemia and Tumor Inhibitor from Camptotheca Acuminata. J. Amer. Chem. Soc. 88:3888-90, 1966
  • Westergaard et al., The Mechanism Whereby Bile Acid Mycelles Increase the Rate of Fatty Acid and Cholesterol Uptake Into the Intestinal Mucosal Cell. Journal of Clinical Investigation, 58:97-108 (1976)
  • Kawato, Y., et al., Antitumor Activity of a Camptothecin Derivative, CPT-11, Against Human Tumor Xenografts in Nude Mice. Cancer Chemother Pharmacol, 28:192-198, 1991
  • Ejima, A., et al., Antitumor Agents V.1) Synthesis and Antileukemic Activity of E-Ring-Modified (RS)-Camptothecin Analogues. Chem. Pharm. Bull., 40(3):683-688, Mar., 1992
  • Pommier, Y., et al., Chapter 9: Mammalian DNA Topoisomerase I and Its Inhibitors. In: Cancer Chemotherapy, Eds. Hickman and Tritton, Publisher: Blackwell Scientific Publications, pp. 214-250, 1993
  • Extra, J. M., et al., Phase 1 Study of CPT-11, A Camptothecin Analogue, Administered as a Weekly Infusion. Proc. Amer. Assoc. Cancer Res., 3:83, 1992
  • Rowinsky, E., et al., Phase I and Pharmacologic Studies of Topotecan, A Novel Topoisomerase I Inhibitor Without and With G-CSF. Proc. Amer. Assoc. Cancer Res., 3:83, 1992
  • Kuhn, J., et al., Pharmacokinetcis of Topotecan Following a 30 Min Infusion or 3 Day Continuous Infusion. Proc. Amer. Assoc. Cancer Res., 3:83, 1992
  • Pantazis, P., et al., Cytotoxic Efficacy of 9-Nitrocamptothecin in the Treatment of Human Malignant Melanoma Cells in Vitrol. Cancer Research, 54:771-776, Feb., 1994
  • Rowinsky, E. K., et al., Phase I and Pharmacological Study of the Novel Topoisomerase I Inhibitor 7-Ethyl-10-[4-(1-piperidino)-1-piperidino]carbonyloxycamptothecin (CPT-11) Administered as a Ninety-Minute Infusion Every 3 Weels1. Cancer Research, 54:427-436, Jan., 1994
  • Nicholas, A. W., et al., Plant Antitumor Agents. 29.1 Synthesis and Biological Activity of Ring D and Ring E Modified Analogues of Camptothecin. J. Med. Chem. 33:978-985, 1990
  • Potmesil, Milan, et al., Camptothecins: From Bench Research to Hospital Wards. Cancer Research 54:1431-1439, Mar. 1994
  • Oncology Bulletin, pp. 4-5, Apr. 199
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