Glycosylated analogs of camptothecin

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

536 41, 536 172, 536 179, 536 181, A61K 3170, C07H 1524

Patent

active

056772866

ABSTRACT:
The present invention relates to chemotherapeutic agents, and more particularly, to novel analogs of camptothecin. The camptothecin analogs display increased solubility through the hydrophilicity of added non-ionic sugar substituents. In accordance with the present invention, a member from the class of novel camptothecin analogs is to be delivered in vivo as a chemotherapeutic agent to fight cancer growth in the body.

REFERENCES:
patent: Re32518 (1987-10-01), Miyasaka et al.
patent: 5278296 (1994-01-01), Klemke
patent: 5446047 (1995-08-01), Sanishefsky et al.
W. J. Slichenmyer et al., "The Current Status of Camptothecin Analogues as Antitumor Agents," J. Nat'l. Cancer Inst. 85:271 (1993).
W. D. Kingsbury et al., "Synthesis of Water-Soluble (Aminoalkyl)camptothecin Analogues: Inhibition of Topoisomerase I and Antitumor Activity," J. Med. Chem. 34:98 (1991).
S. Sawada et al., "Synthesis and Antitumor Activity Of 20(S)-Camptothecin Derivatives: Carbamate-Linked, Water-Soluble Derivatives of 7-Ethyl-10-hydroxycamptothecin," Chem. Pharm. Bull. 39:1446 (1991).
Y. Kawato 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 (1991).
N. Aimi et al., "Chaboside, First Natural Glycocamptothecin Found from Ophiorrhiza pumila," Tetrahedron Lett., 31:5169 (1990).
K. Toshima and K. Katsuta, "Recent Progress in O-Glycosylation Methods and Its Application to Natural Products Synthesis," Chem. Rev. 93:1503 (1993).
R. R. Schmidt, "New Methods for the Synthesis of Glycosides and Oligosaccharides--Are There Alternatives to the Koenigs-Knorr Method?" Angew. Chem. Int. Ed. Engl. 25:212 (1986).
N. K. Kochetkov, "Recent Developments in the Synthesis of Polysaccharides and Stereospecificity of the Glycosylation Reactions," Stud. Nat. Prod. Chem. 14:201 (1994).
M. E. Wall et al., "Plant Antitumor Agents. 30. Synthesis and Structure Activity of Novel Camptothecin Analogs," J. Med. Chem. 36:2689 (1993).
R.K. Johnson et al., "Preclinical Profile of SK and F 104684, A Water-Soluble Analog of Camptothecin (Meeting Abstract)," In Proc. on the Sixth NCI-EORTC Symp. on New Drugs in Cancer Therapy, Amsterdam, Mar., 1989.
L. Brown and R. Thomas, "O-Glycosidation: Application to the Synthesis of Drug Molecules," Aust. J. Pharm. Sci. 8:1 (1979).
Y.-H. Ji et al., "Monophosphoric Acid Diesters of 7.beta.-Hydroxycholesterol and of Pyrimidine Nucleosides as Potential Antitumor Agents: Synthesis and Preliminary Evaluation of Antitumor Activity," J. Med. Chem. 33:2264 (1990).
V. Stella et al., J. Med. Chem. 35:145 (1992).
H.-W. Kleeman et al., "Renin Inhibitory Pentols Showing Improved Enterol Bioavailability," J. Med. Chem. 35:559 (1992).
E. Fischer and K. Zach, "Reduktion der Acetobromglucose und ahnlicher Stoffe," Preuss. Akad. Wiss. 16:311 (1913).
R. J. Ferrier et al., "Unsaturated Carbohydrates. Part IX. Synthesis of 2,3-Dideoxy-.alpha.-D-erythro-hex-2-enopyranosides from Tri-O-acetyl-D-glucal," J. Chem. Soc. C 570 (1969).
B. Helferich, "The Glycals," Adv. Carbohydrate Chem. 7:209 (1952).
R. J. Ferrier, "Unsaturated Carbohydrates. Part II. Three Reactions Leading to Unsaturated Glycopyranosides," J. Chem. Soc. 5443 (1964).
R. J. Ferrier et al., "The Reaction Between 3,4,6-Tri-O-acetyl-D-glucal and p-Nitrophenol," J. Chem. Soc. 3667 (1962).
U. Hacksell and G. D. Daves, Jr., "Stereocontrolled Palladium(II)-Mediated Coupling of Furanoid Glycals with a Pyrimidinylmercuric Salt. Facile C-Nucleoside Synthesis," J. Org. Chem. 48:2870 (1983).
T. Mossmann, "Rapid Colorimetric Assay for Cellular Growth and Survival: Application to Proliferation and Cytotoxicity Assays," J. Immun. Meth. 65:55 (1983).
S. Sawada et al., "Chemical Modification of an Antitumor Alkaloid Camptothecin: Synthesis and Antitumor Activity of 7-c-substituted Camptothecins," Chem. Pharm. Bull. 39:2574 (1991).
M. Sugimori et al. "Antitumor Agents. 7. Synthesis and Antitumor Activity of Novel Hexacyclic Camptothecin Analogues," J. Med. Chem. 37:3033 (1994).
G. J. Creemers et al., "Topoisomerase I Inhibitors: Topotecan and Irenotecan," Cancer Treatment Rev. 20:73 (1994).
H. A. Burris, III, et al., "Topoisomerase I Inhibitors: An Overview of the Camptothecin Analogs," New Drug Therapy 8:333 (1994).
T. Yaegashi et al., "Chemical Modification of an Antitumor Alkaloid, 20(S)-Camptothecin: Glycosides, Phosphates and Sulfates of 7-Ethyl-10-hydroxycamptothecin," Chem. Pharm. Bull., 40:131 (1992).
K.-A. Karlsson, "Glycobiology: A Growing Field for Drug Design," TiPS 12:265 (1991).
B. K. Carte et al., "Isolation and Characterization of a Presumed Biosynthetic Precursor of Camptothecin from Extracts of Camptotheca acuminata," Tetrahedron 46:2747 (1990).
N. Aimi et al., "Pumiloside and Deoxypumiloside; Plausible Intermediates of Camptothecin Biosynthesis," Tetrahedron Lett., 30:4991 (1989).
M. J. Luzzio et al., "Synthesis and Antitumor Activity of Novel Water Soluble Derivatives of Camptothecin as Specific Inhibitors of Topoisomerase I," J. Med. Chem. 38:395 (1995).
Cassidy, J. et al., "New Drugs in Clinical Development in Europe," New Drug Therapy 8:289 (1994).
H. Takano et al., "DNA Topoisomerase-targeting Antitumor Agents and Drug Resistance," Anti-Cancer Drugs 3:323 (1992).
D. E. Uehling et al., "Synthesis, Topoisomerase I Inhibitory Activity, and in Vivo Evaluation of 11-Azacamptothecin Analogs," J. Med. Chem. 38:1106 (1995).
R. T. Crow et al., "Structural Modifications of Camptothecin and Effects of Topoisomerase I Inhibition," J. Med. Chem. 35:4160 (1992).
A. Tanizawa et al., "Comparison of Topoisomerase I Inhibition, DNA Damage, and Cytotoxicity of Camptothecin Derivatives Presently in Clinical Trails," J. Natl. Cancer Inst. 86:836 (1994).
T.A. Houston, Thesis, University of Michigan, (Oct. 15, 1993).

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Glycosylated analogs of camptothecin does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Glycosylated analogs of camptothecin, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Glycosylated analogs of camptothecin will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-1555363

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.