Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2006-06-27
2006-06-27
Saeed, Kamal A. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C549S400000
Reexamination Certificate
active
07067679
ABSTRACT:
Various processes are disclosed for preparing protected epicatechin oligomers having (4β,8)-interflavan linkages. In one process, a tetra-O-protected epicatechin monomer or oligomer is coupled with a protected, C-4 activated epicatechin monomer in the presence of an acidic clay such as a mortmorillonite clay. In another process, a 5,7,3′,4′-benzyl protected or a 3-acetyl-, 5,7,3′,4′-benzyl protected epicatechin or catechin monomer or oligomer is reacted with 3-O-acetyl-4-[(2-benzothiazolyl)thio]-5,7,3′,4′-tetra-O-benzylepicatechin in the presence of silver tetrafluoroborate. In another process, two 5,7,3′,4′-benzyl protected epicatechin monomers activated with 2-(benzothiazolyl)thio groups at the C-4 positions are cross-coupled in the presence of silver tetrofluoroborate. A process is also disclosed for reacting an unprotected epicatechin or catechin monomer with 4-(benzylthio)epicatechin or catechin. The use of naturally-derived and synthetically-prepared procyanidin (4β,8)4-pentamers to treat cancer is also disclosed.
REFERENCES:
patent: 4644011 (1987-02-01), Ballenegger et al.
patent: 6156912 (2000-12-01), Tückmantel et al.
patent: 6207842 (2001-03-01), Romanczyk, Jr. et al.
patent: 2003/0114691 (2003-06-01), Romanczyk, Jr. et al.
patent: 0039844 (1981-11-01), None
patent: 0216936 (1987-04-01), None
patent: 1518003 (1965-01-01), None
patent: WO 90/13304 (1990-11-01), None
patent: WO 97 36597 (1997-09-01), None
Anzinger et al., 2002, CAS: 137:44917.
Botha et al., Dept. of Chemistry, University of the Orange Free State, 1980, pp. 527-533.
Botha et al., Dept. of Chemistry, University of the Orange Free State, 1980, pp. 1235-1245.
Delcour et al., J. Chem. Soc. Perkins Trans., 1983, pp. 1711-1717.
Delcour et al., Laboratorium voor Toegepaste Organische, 1986, vol. 92 pp. 244-249.
D. Ferreira et al., Tetrahedron, 1992, vol. 48, pp. 1743-1803.
Kawamoto et al., Mokuzai Gakkaishi, 1991, vol. 37 pp. 741-747.
Kawamoto et al., Mokuzai Gakkaishi, 1991, vol. 37 pp. 488-493.
Tückmantel et al., J. Am. Chem. Soc., 1999, vol. 121 pp. 12073-12081.
Kozikowski, et al., J. Org. Chem. 2001, vol. 66, pp. 1287-1296.
Steenkamp et al., Pergamon Press Ltd., vol. 26, pp. 3045-3048.
Steynberg et al, Tetrahedron, 1998, vol. 54, pp. 8153-8158.
International Search Report PCT/US 98/21392.
Jpn. Kakar Tokyo Koho JP 6248,677 Mar 3, 1987, Chem. Abstr. vol. 107, No. 26, p. 643 (1987) Abstr. No. 107: 6996d.
“New Tannin Compound with Enzyme Inhibiting Activity is Tris-flavanol Cpd. Derives from Areca Nuts” Wep Accession No. 87-099102.
JP 58154571 Sep. 14, 1983 “Tannin Deviv. for Tanning Leather—combine with Enzyme Proteins in Living Body to Inhibit Their Function” Wep Accession No. 83-797400.
JPN. Kobai Tokkyo Kaho JP 58154571 Sep. 14, 1983 C.A. 100:136 144 R Derwent—non-certified translation.
E.J. Keagh et al. Chem. Ind (London) 1961:2100-1.
Kozikowski et al., J. Org. Chem. 2000, vol. 65, pp. 5371-5381.
International Search Report PCT/US03/31375.
Kozikowski Alan P.
Romanczyk Jr. Leo J.
Tückmantel Werner
Gibbons, Del Deo, Dolan
Kelley Margaret B.
Mars Inc.
Saeed Kamal A.
Shiao Robert
LandOfFree
Synthesis of dimeric, trimeric, tetrameric pentameric, and... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Synthesis of dimeric, trimeric, tetrameric pentameric, and..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of dimeric, trimeric, tetrameric pentameric, and... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3665859