Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2005-02-01
2005-02-01
Lipman, Bernard (Department: 1713)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C549S354000, C549S355000, C549S381000, C549S385000, C549S386000, C549S396000, C549S398000, C549S399000, C549S400000, C549S401000, C549S403000, C549S406000, C549S407000
Reexamination Certificate
active
06849746
ABSTRACT:
A process is disclosed for the production of polyphenol oligomers having n polyphenol monomeric units, n being an integer from 2-18. The process includes coupling of a protected polyphenol, having protected phenolic hydroxyl groups, with a C-4 functionalized polyphenol monomer. The protected polyphenol may be a protected polyphenol monomer or a protected polyphenol oligomer having 2-17 monomeric units. Advantageously, polyphenol monomeric units forming the polyphenol oligomers may be the same or different flavanoid compounds.
REFERENCES:
patent: 5554645 (1996-09-01), Romanczyk et al.
patent: 5912363 (1999-06-01), Nafisi-Movaghar et al.
patent: 15 18 003.7 (1969-01-01), None
patent: 0039844 (1978-11-01), None
patent: 0096 007 (1983-12-01), None
patent: 0216 936 (1987-04-01), None
patent: WO 9013304 (1990-11-01), None
patent: 58 154571 (1983-09-01), None
patent: 06 248677 (1987-03-01), None
patent: 4-190774 (1992-07-01), None
patent: WO 9736597 (1997-10-01), None
Nonaka et al., “Tannins and Related Compounds. Part 13. Isolation and Structure of Trimeric, Tetrameric, and Pentameric Proanthicyanidins from Cinnamon”,J. Chem. Soc. Perkin. Trans.,1983, p. 2139-2145.
Morimoto et al., “Tannins and Related Compounds. XXXV. Proanthocyanidins with a Doubly Linked Unit from the Root Bark ofCinnamomum sieboldiiMeiser”,Chem. Pharm. Bull,1985, 33(10) 4338-4345.
Roux et al., “The Direct Biomimetric Synthesis, Structure and Absolute Configuration of Angular and Linear Condensed Tannins”,Fortschr. Chem. Org. Naturst.,1982, 41:48.
Balas, L., et al.,Magnetic Resonance in Chemistry,vol. 32, p386-393 (1994).
Balde, A.M. et al.,Phytochemistry,vol. 30, No. 12. p. 4129-4135 (1991).
Botha, J.J. et al.,J. Chem. Soc.,Perkin I, 1235-1245 (1981).
Botha, J.J. et al.,J. Chem. Soc.,Perkin I, 527-533 (1982).
Boukharta, M. et al, Presented at the XVIth International Conference of the Groupe Polyphenols, Libson, Portugal, Jul. 13-16, 1992.
Chu S.-C., et al.,J. of Natural Products,55 (2), 179-183 (1992).
Coetzee, J. et al.,Tetrahedron,54, 9153-9160 (1998).
Creasy, L.L. et al., “Structure of Condensed Tannins,”Nature,208, 1965, pp. 151-153.
Miura, S. et al.,Chem. Abstr.,1983, 99, 158183r.
Miura, S. et al.,Radioisotopes,32, 225-230 (1983).
Newman, R.H.,Magnetic Resonance in Chemistry25:118-124 (1987).
Nonaka G-I.,Chem. Pharm. Bull.31 (11)3906-3914 (1983).
Nonaka G-I., et alJ. Chem. Soc. Perkin Trans.,I: p. 2139-2145 (1983).
Nonaka, G. et al., “Tannins and Related Compounds,”Chem. Pharm. Bull.,35(1), pp. 149-155, 1987.
Okuda, T. et al, Molecular Structures and Pharmacological activities of Polyphenols—Oligomeric Hydrolyzable Tannins and Others—Presented at the XVIth International Conference of the Groupe Polyphenols, Lisbon, Portugal, Jul. 13-16, 1992.
Pierre, M.C., et al.,Tetrahedron Letters,38, (32), 5639-5642 (1997).
Porter, L.J. “Flavans and Proanthocyanidins” from “The Flavonoids” Ed. J.B. Harborne, Chapmen and Hall Ltd., p 21-62 (1988).
Romanczyk, Jr., et al., “Antineoplastic cocoa extracts and methods for making and using the same,” U.S. patent application Ser. No. 5,554,645 (issued Sep. 10, 1996).
Roux & Ferreira,Fortschritte d. Chemie Org. Naturst.,pp. 47-76 (1982).
Roux, D.G. et al,J. Agric. Food Chem.28:216-222 (1980).
Roux, D.G. et al.,Progress in the Chemistry of Organic Natural Products,41, 46-76 (1982).
Roux, D.G., et al., “The Direct Biomimetic Synthesis, Structure and Absolute Configuration of Angular and Linear Condensed Tannins,”Chem. Org. Natural,41, 1981, pp. 48-76.
Schlama, T. et al., “Total Synthesis of Halomon,”Angew. Chem. Int. Edgl.,1998, 37, pp. 2085-2087.
Steenkamp, J.A., et al.,Tetrahedron Letters,26, (25) 3045-3048 (1985).
Steynberg, P. et al.,Tetrahedron,54, 8153-8158 (1998).
Swain, T., “Leucocyanidin,”Chemistry and Industry,1954, pp. 1144-1145.
Toshima, K., et al.,Chem. Rev.,93, 1503-1531 (1993).
Van Rensberg, et al.,J. Chem. Soc. Chem. Commun.24, 2705-2706.
Van Rensberg et al.,J. Chem. Soc. Chem. Commun.,24:2747-2748 (1996).
Weinges, K. et al.,Chem. Ber.,103, 2344-2349 (1970).
Delcour, J. et al., “Direct Synthesis of the Barley Proanthocyanidins Prodelphinidin B3, Prodelphinidin C2 and Two Trimeric Proanthocyanidins with a Mixed Prodelphinidin-Procyanidin Stereochemistry”,J. Inst. Brew,1986, vol. 92, pp. 244-249.
Czochanska, Z., et al.,J. Chem. Soc. Perkin 1:2278-2286 (1979).
D. Kahne et al.,J. Am. Chem. Soc.,11, 6881 (1989).
Delcour, J.A. et al., “Synthesis of Condensed Tannins. Part 9. The Condensation of Sequence of Leucocyanidin with (+)-Catechin and with resultant Procyanidins,”J. Chem. Soc. Perkin. Trans.,1983, pp. 1711-1717.
Deschner, E.E., et al.,Carcinogenesis,7, 1193-1196 (1991).
Dess, D.B. et al.,J. Am. Chem. Soc.,113, 7277-7287 (1991).
Eastmond, R., “The Separation of a Dimer of Catechin occurring in Beer,”J. Inst. Brew.,vol. 80, No. 2 (Mar./Apr. 1974), pp. 188-192.
Ferreira, D. et al.,Tetrahedron,48 (10), 1743-1803 (1992).
Foo, L.Y. & Hemingway, R.W.,J. Chem. Soc., Perkin I,1235-1245 (1981).
Foo, L.Y. et al.,J. Chem. Soc. Perkin I,1535-1543 (1983).
Foo, L.Y. et al.,J. Chem. Soc. Chem. Commun.,85-86 (1984).
Funayama, M. et al.,Biosci. Biotech. Biochem.,58(5), 817-821 (1994).
Garegg, P. J. et al., “The Synthesis of oligosaccharides for biological and medical applications”,Carbohydrate Chemistry,Clarendon Press—Oxford, p. 500-559 (1988).
Gramshaw, J.W., “Phenolic constituents of beer and brewing materials. II. The Role of Polyphenols in the Formation of Non-Biological Haze,”J. Inst. Brew.,vol. 73, No. 5 (Sep./Oct. 1967), pp. 455-472.
Ho, C.T., Lee C.Y., and Huang, M.T. Eds., Phenolic Compounds in Foods and Their Effects on Health I. Analysis, Occurrence and Chemistry, ACS Symposium Series 506, American Chemical Society, Washington, D.C. (1992).
Huang, M.T., Ho, C.T. and Lee C.Y., Eds. Phenolic Compounds in Foods and Their Effects on Health II. Antioxidants and Cancer Prevention, ACS Symposium Series 507, American Chemical Society, Washington D.C. (1992).
Hundt, H., et al., “Synthesis of Condensed Tannins. Part 3,”J.C.S. Perkin I(1981), pp. 1227-1234.
Igarashi, K.,Adv. Carbohydr. Chem. Biochem.,34, 243 (1977).
Ireland, R.E. et al.,J. Org. Chem.,58, 2899 (1993).
Kashiwada, Y., et al.,Chem. Pharm. Bull.34:4083-4091 (1986).
Kato, R., et al.,Carcinogenesis,4, 1301-1305 (1983).
Kawamoto, H, et alSynthetic Communications,26(3), 531-534 (1996).
Kawamoto, H. et al.,Mokazai Gakkaishi,37, (5) 488-493 (1991).
Kawamoto, H. et al.,Mokazai Gakkaishi,37, (5), 741-747 (1991).
Keihlmann, E. et al.,Can. J. Chem.,26, 2431-2439 (1988).
Keogh et al,Chem. Ind.(London) 2100-1 (1961).
Khanbabaee, K. et al,Tetrahedron,53:31, 10725-10732 (1997).
Kiatgrajai P., et alJ. Org. Chem.47, 2910-2912 (1982).
Kitao et al,Biosci. Biotech. Biochem.59(11), 2167-2169, (1995).
Kolodziej, H.,Phytochemistry25, 1209-1215 (1986).
Kolodziej, H.,Phytotherapy Research,9, 410-415 (1995).
Man Jong Lee, Young Yul Chang, Moo Hyun Lim,Agricultural Chemistry and Biotechnology,41(1): p. 110-117 (1998), translation from Korean.
Meyer, S.D. et al.,J. Org. Chem.,59, 7549-7552 (1994).
Kozikowski et al., J. Org. Chem. 2000, Vol. 65, pp. 5371-5381.
Kozikowski Alan P.
Lippman Marc E.
Romanczyk Jr. Leo J.
Tueckmantel Werner
Clifford Chance (US) LLP
Kelley Margaret B.
Lipman Bernard
Mars Inc.
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