Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2007-01-30
2007-01-30
Coleman, Brenda (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C540S543000, C540S581000
Reexamination Certificate
active
10877067
ABSTRACT:
The present invention concerns a new general process for asymmetric hemisynthesis of harringtonines and their analogs, that are alkaloids used in chemotherapy. This process comprises direct esterification of a natural cephalotaxine with an acylating compound constituted of a side chain precursor which backbone and functionalization are entirely preformed. The invention also concerns a natural, synthetic or semi-synthetic harringtonines including their tautomeric forms and their salts of the following formula:wherein n=2 (i.e. harringtonine) or n=3 (i.e. homoharringtonine),in which the total content of impurities, possibly including enantiomeric forms, is lower than 1%, and/or the content of the major impurity is lower than 0.9%, and/or the chromatographic assay exhibits a harringtonines content higher than 97.5%.
REFERENCES:
patent: 2889339 (1959-06-01), Levy et al.
patent: 2889340 (1959-06-01), Levy et al.
patent: 3246038 (1966-04-01), Eiter et al.
patent: 3725437 (1973-04-01), Nagoya et al.
patent: 3855245 (1974-12-01), Koyama et al.
patent: 3870727 (1975-03-01), Powell et al.
patent: 4042617 (1977-08-01), Kogure et al.
patent: 4131747 (1978-12-01), Kurono et al.
patent: 4132720 (1979-01-01), Mohrbacher et al.
patent: 4152214 (1979-05-01), Delfel et al.
patent: 4154840 (1979-05-01), Ondetti et al.
patent: 4178286 (1979-12-01), Wasserman et al.
patent: 4203996 (1980-05-01), Mikolajczak et al.
patent: 4252728 (1981-02-01), Delay
patent: 4409236 (1983-10-01), Bosies et al.
patent: 4430339 (1984-02-01), Eistetter et al.
patent: 4619888 (1986-10-01), Kawata et al.
patent: 4849524 (1989-07-01), Henning et al.
patent: 4870208 (1989-09-01), Chan et al.
patent: 5081240 (1992-01-01), Bousquet et al.
patent: 5084582 (1992-01-01), Genet et al.
patent: 5256803 (1993-10-01), Duchesne et al.
patent: 5334730 (1994-08-01), Fritz-Langhals
patent: 5502221 (1996-03-01), Sayo et al.
patent: 5677470 (1997-10-01), Tsujihara et al.
patent: 5834467 (1998-11-01), Kalish et al.
patent: 6107291 (2000-08-01), Russo-Rodriguez et al.
patent: 6613900 (2003-09-01), Robin et al.
patent: 6831180 (2004-12-01), Robin et al.
patent: 2002/0128258 (2002-09-01), Robin et al.
patent: 2004/0082565 (2004-04-01), Brown
patent: 2776292 (1999-09-01), None
patent: 58032880 (1983-02-01), None
patent: 92/01696 (1992-01-01), None
Kano et al., In Vitro Cytotoxic Effects of a Tyrosine Kinase Inhibitor STI571 in Combination With Commonly Used Antileukemic Agents, Blood, vol. 97, No. 7, pp. 1999-2007, Apr. 1, 2001.
O'Brien et al., Sequential Homoharringtonine and Interferon-.alpha. in the Treatment of Early Chronic Phase Chronic Myelogenous Leukemia, Blood, vol. 93, No. 12, pp. 4149-4153, Jun. 15, 1999.
Medline abstract of Witte et al., A Phase II Trial of Homoharringtonine and Caracemide in the Treatment of Patients With Advanced Large Bowel Cancer, New Drugs, vol. 17, No. 2, pp. 173-177, 1999.
Y. Leroux, “Obtention de nitriles tetrahydrfuranniques et tetrahydropyranniques par action du CuCN sur les c'etones gamma et delta halogenees”, Bulletin De La Societe Chimique De France; No. 1, 1968, pp. 344-351, XP002087586, Paris, France.
S. Hiranuma et al, “Studies in cephalotaxus alkaloids. Stereospecific total synthesis of homoharringtonine” Journal of Organic Chemistry, vol. 48, No. 26, 1983, pp. 5321-5326.
H.A. Bates, “Decarbonylation of tetrahydrofuran-2-carboxylic acids and tetrahydropyran-2-carboxylic acids in concentrated sulfuric acid: formation of oxonium ions”, Journal of the American Chemical Society, vol. 104, No. 9, 1982, pp. 2490-2493, XP002087583.
P.G.M. Wuts et al, “An electrochemical ketal synthesis from 2-carboxy-2-allyl-tetrahydropyrans”, Tetrahedron Letters, vol. 23, No. 39, 1982, pp. 3987-3990, XP002087584, Oxford, GB.
M. Nagai et al, “The stereochemistry of protopanaxadiol. The absolute configuration of C(20) of dammarenediol-I- and -II”, Tetrahedron Letters, No. 40, 1966, pp. 4797-4801, XP002087585, Oxford, GB.
K.L. Mikolajczack et al, “Preparation and Antitumor Activity of a Rearranged Ester of Cephalotaxine”, J. Med. Chem., Vol. 18, No. 1, pp. 63-66, (1975).
D.Z. Wang et al, Yaoxue Xuebao, vol. 27, p. 178 (1992).
D.Z. Wang et al, Yaoxue Xuebao, vol. 27, p. 173 (1992).
Thomas Hudlicky et al., “Synthesis of Cephalotaxine Alkaloids”, The Alkaloids, vol. 51, Chapter 5, pp. 639-691, 1998, Academic Press, Burlington, MA, USA.
M.A. Miah et al., “Cephalotaxine Alkaloids”, The Alkaloids, vol. 51, Chapter 2, pp. 199-264, 1998, Academic Press, Burlington, MA, USA.
Cecil R. Smith, Jr. et al., “Harringtonine and Related Cephalotaxine Esters”, Anticancer Agents based on Natural Product Models, Chapter II, vol. 16, pp. 391-416, 1980, Academic Press, New York, New York, USA.
K.L. Mikolajczak et al., “Deoxyharringtonine, a New Antitumor Alkaloid from Cephalotaxus. Structure and Synthetic Studies”, Tetrahedron, vol. 28, No. 7, pp. 1995-2001, 1972, Pergamon Press, Oxford, Great Britain.
Wen-Kui Huang et al., “Synthesis of Deoxyharringtonine and Separation of its Stereomers”, Sci. Sin., vol. 23, No. 7, pp. 835-846, 1980, Chinese Academy of Sciences, Beijing, China.
Liang Huang et al., “Cephalotaxus Alkaloids”, The Alkaloids, vol. 23, Chapter 3, pp. 157-227, 1984 Academic Press, Burlington, MA, USA.
He, et al., “Stability -indicating LC assay of and impurity identification in homoharringtonine samples”,Journ. of Pharm. Biomed. Analysis22:541-554 (2000).
Anonymous,Acta Bot. Sin.22:156 (1980) cited by Huang, L, et al., “Cephalotaxus Alkaloids”,The Alkaloidsvol. XXII, pp. 157 (1988).
International Search Report from PCT/IB02/02054 issued Nov. 18, 2002.
French Preliminary Search Report from FR 9803492, issued Dec. 14, 1998.
Ciurdaru et al., RD 103334, CA 121:255399, 1994.
Reich et al., Biorg. Med. Chem. Lett. “Derivatives of D-Penicillamine as Potential Antiarthritic Agents”, 4(9):1167-70 (1994).
Lemmens et al., Journal of Organic Chemistry, “Synthesis of α,β-Epoxyacyl Azides and Their Rearrangement to Epoxy Isocyanates and 3- and 4-Oxazolin-2-ones”, 49:2231-2235 (1984).
Johnson et al., “Dianions Derived from α-Halo Acids. The Darzens Condensation Revisited”, Journal of Organic Chemistry, 47: 1205-1212 (1982).
Newman, M.S., et al., “The Darzens Glycidic Ester Condensation”,Organic Reactions, vol. V, Chapter 10, pp. 413-440 (1949), John Wiley & Sons, New York, NY, USA.
Kulesza et al., PL 85803, CA 90: 121390 (1979).
Blanchard Julie
Chauviat Ludovic
Dhal Robert
Marie Jean-Pierre
Radosevic Nina
Buchanan & Ingersoll & Rooney PC
Coleman Brenda
Stragen Pharma S.A.
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