Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1995-01-30
1997-10-21
Trinh, Ba K.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
549511, C07D30514
Patent
active
056798075
ABSTRACT:
The invention relates to a process for converting Taxol A, B and C to Taxol primary amine which can then be easily and efficiently converted to Taxol A or docetaxel, thereby significantly increasing the yield of these products from biomass. The method includes the removal of the amide from the side-chain with Schwartz's reagent to form an imine, followed by the hydrolysis of the imine to the primary amine. The primary amine can then be converted to Taxol A or docetaxel. New Taxol imine compounds and primary amine salts have been formed by this process.
REFERENCES:
patent: 4857653 (1989-08-01), Colin et al.
patent: 4876399 (1989-10-01), Holton et al.
patent: 5015744 (1991-05-01), Holton
patent: 5319112 (1994-06-01), Kingston et al.
patent: 5356928 (1994-10-01), Murray et al.
Jitrangsri, Chote, "Approaches to the Synthesis of Modified Taxols," Dissertation submitted to the Faculty of the Virginia Polytechnic Institute and State University, UMI Dissertation Services (Aug., 1986).
D.G.I. Kingston, et al., "The Taxane Diterpenoids," Progress in the Chemistry of Organic Natural Products 61, pp. 1-206 (1993).
Gunda L. Georg, et al., "Schotten-Baumann Acylation of N-Debenzoyltaxol; An Efficient Route to N-Acyl Taxol Analogues and Their Biological Evaluation," Bioorganic & Medicinal Chemistry Letters, 4(2):335-338 (1994).
Debjani Dasgupta, et al., "Synthesis of a Photoaffinity Taxol Analogue and Its Use in Labeling Tubulin," J. Med. Chem., 37:2976-2980 (1994).
Lalith Jayasinghe, et al., "Structure-Activity Studies of Antitumor Taxanes: Synthesis of Novel C-13 Side Chain Homologated Taxol and Taxotere Analogs," J. Med. Chem., 37:2981-2984 (1994).
Charles S. Swindell, et al., "Characterization of Two Taxol Photoaffinity Analogues Bearing Azide and Benzophenone-Related Photoreactive Substiuents in the A-Ring Side Chain," J. Med. Chem., 37:1446-1449 (1994).
David J. A. Schedler, et al., "Reductive Deoxygenation by Cp.sub.2 ZrHC1: Selective Formation of Imines Via Zirconation/Hydrozirconation of Amides," Tetrahedron Letters, 34(32):5035-5038 (1993).
Alexander G. Godfrey, et al., "Reductive Deoxygenation Using Hydridozirconium Enolates: A New Synthesis of .alpha.,.beta.-Unsaturated Esters," Tetrahedron Letters, 33(49):7461-7464 (1992).
L. Mangatal, et al., "Application of the Vicinal Oxyamination Reaction with Asymmeric Induction to the Hemisynthesis of Taxol and Analogues," Tetrahedron, 45(13):4177-4190 (1989).
Cheng Xiaoqin
Murray Christopher K.
Peterson S. Kent
Zheng Qun Y.
Gyure Barbara A.
Hauser, Inc.
Trinh Ba K.
LandOfFree
Preparation of taxol and docetaxel through primary amines does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Preparation of taxol and docetaxel through primary amines, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Preparation of taxol and docetaxel through primary amines will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1007813