Total synthesis of 20(S) and 20(R)-camptothecin and compthothecin derivatives
Patent 5053512 Issued on October 1, 1991. Estimated Expiration Date: April 17, 2010. 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.
546/41, Plural ring hetero atoms in the hexacyclo ring system546/48, Three or more ring hetero atoms in the pentacyclo ring system546/92Plural chalcogens bonded directly to ring carbons of the tricyclo ring system
The invention relates to a method of producing 20(S)-comptothecin, 20(R)-camptothecin and analogs thereof. The method involves the resolution of an mixture of enantiomers of an intermediate lactone.
Other References
Cancer Research, (1989) vol. 49, 4385-5489, "DNA Topoisomerase I-Meditated DNA Cleavage and Cytotixicity of Camptothecin Analogues", Hisang et al
Cancer Research, (1989), vol. 49, 1465-1469, "Structure-Activity Study of the Actions of Camptothecin Derivatives on Mammalian Topoisomerase I . . . " Jaxel et al
The Journal of Biological Chemistry, (1985, 260, 14873-14878, "Camptothecin Induces Protein-Linked DNA Breaks Via Mammalian DNA Topoisomerase I" Hsiang et al
J. Med. Chem., (1980), 23, 544-560, "Plant Antitumor Agents. 18.1 Synthesis and Bilogical Activity of Camptothecin Analogues", Wani et al
J. Med. Chem., (1986), 29, 1553-1555, "Plant Antitumor Agents 22.1 Isolation of 11-Hydroxycamptothecin from Camptotheca Acuminata Decne . . . " Wall et al
Journal of Labelled Compounds and Radiopharmaceuticals, (1981), 18, 319-329, "The Preparation of Tritium and Deuterium-Labelled Camptothecin", Ronman et al
J. Medicinal Chemistry, (1987), 30, 1774-1779, "Plant Antitumor Agents 25.1 Total Synthesis and Antileukemic Activity of Ring A . . . " Wani et al
J. Medicinal Chemistry, (1990), 33, 972-978, "Plant Antitumor Agents. 29.1 Synthesis and Biological Activity of Ring D and Ring 3 . . . " Nicholas et al
J. Org. Chem. (1974), 39, 303-311, "Synthesis of Some De and CDE Ring Analogs of Camptothecin", Plattner et al
J. of Am. Chem. Soc. (1972), 94, 8615, "Synthesis of Some De and CDE Ring Analogs of Camptothecin" Plattner et al
J. Org. Chem., (1974), 39, 3430-3432, "Synthesis of Biological Evaluation of De-AB-Camptothecin", Danishefsky et al
Govindachari et al., 453-454, "9-Methoxycamptothecin. A New Alkaloid from Mappia Foetida Miers"
Chem. Ber., (1978), 111, 3403-3411, "Total Synthesis of 7-Methoxycamptothecin", Baxmann et al
Proc Annu. Meet. Am. Assoc. Cancer Res, (1988), 29, A1080, "Structure-Activity Study of the Relation Between Topoisomerase I Inhibition and Antitumor". . . Abstract
Proc. Annu. Meet. Am. Assoc. Cancer Res. (1989), 8, A1019, "A Clinical Study of a Camptothecin Derivative, CPT-11 on Hematological Malignancies", (MTG Abstract)
J. Med. Chem., (1989), 32, 715-720, "Modification of the Hydroxy Lactone Ring of Camptothecin: Inhibition of Mammalian Topoisomerase I and . . . ", Mong et al. Abstract
Science, (1989), 246, 1046-1048, "DNA Topoisomerase I-Targeted Chemotherapy of Human Colon Cancer in Xenografts", Giovanella et al
Proc. Annu. Meet. Am. Assoc. Cancer Res. (1989), A2476, "Structure-Activity Studies of 20(S)-Captothecin Analogs" (Meeting Abstract)
Baxmann et al., Chem Berichte, vol. 111, pp. 3403-3411 (1978)
Yang et al., Chemical Abstracts, vol. 100: 13943w (1984)
Yakult Honsha Co., Chemical Abstracts, vol. 101: 130670r (1984), Abstract of Japan Kokai 59 46,284
Hsu et al., Chemical Abstracts, vol. 90: 28930k (1979)
Yang et al., Chemical Abstracts, vol. 100: 139434w (1984)
Tien et al., Chemical Abstracts, vol. 92: 37766e (1980)
Gunasekera et al., Chemical Abstracts, vol. 92: 18799b (1980)
Chen et al., Chemical Abstracts, vol. 94: 90169e (1981)
Kametani et al., Chemical Abstracts, vol. 94: 4143n (1981)
Cai et al., Chemical Abstracts, vol. 95: 133209h (1981)
Miyasaka et al., Chemical Abstracts, vol. 96: 69271p (1982)
Yakult Honsha Co., Chemical Abstracts, vol. 97: 188278b (1982) Abstract of Japan Kokai 82 116,015
Luo et al., Chemical Abstracts, vol. 101: 78770z (1984)
Nagata et al., Chemical Abstracts, vol. 100: 167724j (1984)
Fukada et al., Chemical Abstracts, vol. 103: 64374c (1985)
Wani et al., J. Med. Chem. 23(5), pp. 554-560 (1980)
Wani et al., J. Med. Chem. 29(11), pp. 2358-2363 (11/86)
Govindachari et al., Ind. J. Chem. 10(4), pp. 453-454 (1972)
Pan et al., Chemical Abstracts, vol. 84: 115629p (1976
April 17, 2010. 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.
