Methods for manufacturing betulinic acid

Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...

Reexamination Certificate

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C554S168000

Reexamination Certificate

active

06867314

ABSTRACT:
The present invention provides a method for preparing an ester of betulin at the 3-position, e.g., betulin-3-acetate, including the selective alcoholysis of a betulin-3,28-diester, e.g., betulin-3,28-diacetate; a method for preparing betulin-3-acetate including (1) acetylating betulin to provide betulin-3,28-diacetate and (2) the alcoholysis of betulin-3,28-diacetate to provide betulin-3-acetate; and a method for preparing betulinic acid (1) acetylating betulin to provide betulin-3,28-diacetate, (2) the alcoholysis of betulin-3,28-diacetate to provide betulin-3-acetate, (3) oxidizing betulin-3-acetate to provide betulinic aldehyde-3-acetate, (4) oxidizing betulinic aldehyde-3-acetate to provide betulinic acid-3-acetate, and (5) deprotecting betulinic acid-3-acetate to provide betulinic acid.

REFERENCES:
patent: 5481023 (1996-01-01), Kleiner et al.
patent: 5804575 (1998-09-01), Pezzuto et al.
patent: 6232481 (2001-05-01), Krasutsky et al.
patent: 6271405 (2001-08-01), Krasutsky et al.
patent: 6407270 (2002-06-01), Krasutsky et al.
patent: 0538189 (1993-04-01), None
patent: WO-9843936 (1998-10-01), None
Ekman, R., “The Suberin Monomers and Triterpenoids from the Outer Bark ofBetula verrucosaEhrh”,Holzforschung, 37, Including English Translation, (1983), pp. 205-211.
Fujioka, T., “Anti-AIDS Agents, 11. Betulinic acid and platanic acid as anti-HIV principles fromSyzigium claviflorumand the anti-HIV activity of structurally related triterpenoids”,Journal of Natural Products, 57 (2), (Feb. 1994), pp. 243-247.
Pisha, E., “Discovery of Betulinic Acid as a Selective Inhibitor of Human Melanoma that Functions by Induction of Apoptosis”,Nature Medicine, 1 (10), (Oct. 1995), pp. 1046-1051.
Ruzieka, L., “Oxidation of Betulin Monoacetate with Chromium Trioxide to Acid”,Organic Chemistry Laboratory, Federal technical University, Zurich, (1938), pp. 1706-1717 (Includes: English Translation and German Article).
Tietze, L.F., et al., “Synthesis of [13C]- and [2H]Betulin for Biological Transformations”,Liebigs Ann. Chem., (1991), pp. 1245-1249.
Xu, Y-C, et al., “A Reagent for Selective Deprotection of Alkyl Acetates”,J. Org. Chem., 61, (1996), pp. 9086-9089.

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