Method for preparing...

Details Method for preparing... Method for preparing...

2011-04-26

2011-04-26

Chandrakumar, Nizal S (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

07932406

ABSTRACT:
The invention relates to a method for synthesizing 4.beta.-amino-4′-demethyl-4-desoxypodophyllotoxin of formula (1), characterized by comprising the following successive steps: a) reacting, in a pure weak acid or in a mixture consisting of acid, water and of organic solvent, without another solvent, at a temperature higher than the ambient temperature, thiourea with 4.beta.-halogenoacetamido-4′-demethyl-4-desoxypodophyllotoxin, and; b) recovering the 4.beta.-amino-4′-demethyl-4-desoxypodophyllotoxin.

REFERENCES:
patent: 2869035 (2004-04-01), None
Jirgensons et al. Synthesis 2000, 1709.
Masaki et al. Journal of the American Chemical Society, 1968, 90(16), 4509-4510.
Wang et al.Yaoxue Xuebao (1993), 28(6), 422-7.
Kamal et al., “Synthesis of 4-beta-Amido and 4-beta-Sulphonamido ANalogues of Podophyllotoxin as Potential Antitumor Agents,” Bioorganic & Medicinal Chemistry, Elsevier Science Ltd., vol. 11, No. 23, pp. 5135-5142, 2003. XP-002281030.
Jirgensons et al., “A practical synthesis of tert-alkylamines via the ritter reaction with chloroacetonitrile,” Synthesis, No. 12, pp. 1709-1712, 2000. XP-002375279.
Kamal et al., Tetrahedron Letters, An efficient reduction of azides to amines: synthesis of DNA interactive pyrrolo [2,1-c], [1,4] benzodiazephines, vol. 41, pp. 7743-7746, (2000).
Zhou et al., J. Med. Chem., “Antitumor Agents. 120. New 4-Substituted Benzylamine and Benzyl Ether Derivatives of 4′-O-Demethylepipodophyollotoxin as Potent Inhibitors of Human DNA Topoisomerase II”, vol. 34, pp. 3346-3350, (1991).
Yu et al., Tetrahedron Letters, “A Facile and Efficient Synthesis of 4β-Aminopodophyllotoxins”, vol. 40, pp. 1967-1970, (1999).
Wang et al., Chinese Chemical Letters, vol. 4, No. 4, pp. 289-290, (1993).
Bose et al., Journal of American Chemical Society, “A New Method for the Removal of Chloroacetyl Groups”, vol. 90, No. 16, pp. 4508-4509, (Jul. 31, 1968).
Kamal et al., “Synthesis of 4-beta-Amido and 4-beta-Sulphonamido Analogues of Podophyllotoxin as Potential Antitumor Agents,” Bioorganic & Medicinal Chemistry, Elsevier Science Ltd., vol. 11, No. 23, pp. 5135-5142, 2003.
Masaki et al., “A new method for the removal of chloroacetyl groups,” Journal of the American Chemical Society, vol. 90, pp. 4508-4509, 1968.
Jirgensons et al., “A practical synthesis of tert-alkylamines via the ritter reaction with chloroacetonitrile,” Synthesis, No. 12, pp. 1709-1712, 2000.

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