Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2004-11-03
2008-09-09
Davis, Brian J (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C514S674000
Reexamination Certificate
active
07423182
ABSTRACT:
An aminated polyamine having the formula:or its possible stereoisomers or a salt thereof with a pharmaceutically acceptable acid wherein:R1and R4may be the same or different and are alkyl, aryl, aryl alkyl or cycloalkyl, optionally having an alkyl chain interrupted by at least one etheric oxygen atom;R2and R3may be the same or different and are R1, R4or H;N1, N2, N3and N4are nitrogen atoms capable of protonation at physiological pH's;ALK1, ALK2AND ALK3may be the same or different and are straight or branched chain alkylene bridging groups having 1 to 4 carbon atoms which effectively maintain a predetermined distance between the nitrogen atoms such that the polyamine upon uptake by the target cell, competitively functions in a manner wherein at least one of said bridging groups ALK1, ALK2and ALK3contains at least one —CH(NRH)— group which is not alpha- to either of the nitrogen atoms and R is H, alkyl, acyl or sulfonyl.
REFERENCES:
patent: 5091576 (1992-02-01), Bergeron
patent: 5128353 (1992-07-01), Bergeron
patent: 5173505 (1992-12-01), Bergeron
patent: 5886050 (1999-03-01), Bergeron, Jr.
patent: 5962533 (1999-10-01), Bergeron, Jr.
patent: 2003/0185778 (2003-10-01), Fahl et al.
patent: WO 91/00853 (1991-01-01), None
Janne et al., A Biochim. Biophys. Acta., vol. 473, p. 241 (1978).
Fillingame et al., Proc. Natl. Acad. Sci. U.S.A., vol. 72, p. 4042 (1975).
Metcalf et al., J. Am. Chem. Soc., vol. 100, p. 2551 (1978).
Flink et al., Nature (London), vol. 253, p. 62 (1975).
Pegg et al., Polyamine Metabolism and Function, Am. J. Cell. Physiol., vol. 243, pp. 212-221 (1982).
Dykstra et al., Science, vol. 149, p. 428 (1965).
Russell et al., Polyamines as Biochemical Markers of Normal and Malignant Growth (Raven, New York, 1978).
Hirshfield et al., J. Bacteriol., vol. 101, p. 725 (1970).
Hafner et al., J. Biol. Chem., vol. 254, p. 12419 (1979).
Cohn et al., J. Bacteriol., vol. 134, p. 208 (1978).
Pohjanpelto et al., Nature (London), vol. 293, p. 475 (1981).
Mamont et al., Biochem. Biophys. Res. Commun., vol. 81, p. 58 (1978).
Bloomfield et al., “Polyamines in Biology and Medicine”, D.R. Morris and L.J. Morton, eds., Dekker, New York, pp. 183-206 (1981).
Gosule et al., Nature, vol. 259, p. 333 (1976).
Gabbay et al., Ann. N.Y. Acad. Sci., vol. 171, p. 810 (1970).
Suwalsky et al., J.Mol. Biol., vol. 42, p. 363 (1969).
Liquori et al., J. Mol. Biol., vol. 24, p. 113 (1967).
Sjoerdsma et al., Butterworths Int. Med. Rev.: Clin. Pharmacol. Thera., vol. 35, p. 287 (1984).
Israel et al., J. Med. Chem., vol. 16, p. 1 (1973).
Morris et al., Polyamines in Biology and Medicine, Dekker, New York, p. 223 (1981).
Wang et al., Biochem. Biophys. Res. Commun., vol. 94, p. 85 (1980).
Bergeron et al., “The role of methylene backbone in the anti-proliferative activity of polyamine analogues on L1210 cells”, Cancer Res., vol. 49, pp. 2959-2964 (1989).
Bergeron et al., “Synthetic polyamine analogues as antineoplastics”, J. Med. Chem., vol. 31, pp. 1183-1190 (1988).
Porter et al., “Regulation of polyamine biosynthetic activity by spermidine and spermine— a novel antiproliferative strategy”, Polyamines in Biochemical and Clinical Research, pp. 677-690 (1988).
Libby et al., “Major increases in spermidine/spernine-N.sup.1-acetyl transferase activity by spermine analogues and their relationship to polyamine depletion and growth inhibition in L1210 cells”, Cancer Res., vol. 49, pp. 6226-6231 (1989).
Pegg et al., “Induction of spermidine/spermine N.sup.1 -acetyl transferase activity in Chinese-hamster ovary cells by N.sup.1,N.sup.1,N.sup.11 -bis(ethyl)norspennine and related compounds”, Biochem. J., vol. 267, pp. 331-338 (1990).
Porter et al., “Combined regulation of ornithine and S-adenosylmethionine decarboxylases by spermine and the spermine analogue N.sup.1 N.sup.12 -bis(ethyl)spermine”, Biochem. J., vol. 268, pp. 207-212 (1990).
Basu et al., “Effect of N.sup.1,N.sup.14 -bis(ethyl)-homospermine on the growth of U-87 MG and SF-126 on human brain tumor cells”, Cancer Res., vol. 50, pp. 3137-3140 (1990).
Stewart, “The effects of structural changes in a polyamine backbone on its DNA binding properties”, Biochem. Biophys. Res. Commun., vol. 152, pp. 1441-1446 (1988).
Bergeron et al., “Synthesis of N.sup.4 -acylated N.sup.1,N.sup.8 -bis(acyl)spermidines: An approach to the synthesis of siderophores”, J. Org. Chem., vol. 45, pp. 1589-1592 (1980).
Bergeron et al., “Reagents for the selective acylation of spermidine, homospermidine and bis-> 3-aminopropylamine”, Synthesis, pp. 732-733 (1981).
Bergeron et al., “Reagents for the selective secondary functionalization of linear triamines”, Synthesis, pp. 689-692 (1982).
Bergeron et al., “Amines and polyamines from nitriles”, Synthesis, pp. 782-785 (1984).
Bergeron et al., “Reagents for the stepwise functionalization of spermidine, homospermidine and bis->3-aminopropylamine”, J. Org. Chem., vol. 49, p. 2997 (1984).
Bergeron, “Methods for the selective modification of spermidine and its homologues”, Accts. Chem. Res., vol. 19, pp. 105-113 (1986).
Bergeron et al., “Hexahydropyrimidines as masked spermidine vectors in drug delivery”, Bioorg. Chem., vol. 14, pp. 345-355 (1986).
Bergeron et al., “Reagents for the stepwise functionalization of spermine”, J. Org. Chem., vol. 53, pp. 3108-3111 (1988).
Bergeron et al., “Total synthesis of (.+−.)-15-Deoxyspergualin”, J. Org. Chem., vol. 52, pp. 1700-1703 (1987).
Bergeron et al., “The total synthesis of Alealigin”, J. Org. Chem., vol. 56, pp. 586-593 (1991).
Bergeron et al. “Synthesis of catecholamide and hydroxamate siderophores”, CRC Handbook on Microbial Iron Chelates, pp. 271-307 (1991).
Porter et al., “A comparison and characterization of growth inhibition by .alpha.-Difluoromethylomithine (DFMO), and inhibitor of omithine decarboxylase and N-sup.1,N.sup.8 -bis(ethyl)spermidine (BES), and apparent regulator of the enzyme”, Cancer Res., vol. 46, pp. 6279-6285 (1986).
Porter et al., “Relative abilities of bis(ethyl) derivatives of putrescine, spermidine and spermine to regulate polyamine biosynthesis and inhibit L1210 leukemia cell growth”, Cancer Res., vol. 47, pp. 2821-2825 (1987).
Basu et al., “Correlation between the effects of polyamine analogues on DNA conformation and cell growth”, Cancer Res., vol. 49, pp. 5591-5597 (1989).
Casero et al., “Differential response to treatment with the bis(ethyl)polyamine analogues between human small cell lung carcinoma and undifferentiated large cell lung carcinoma in culture”, Cancer Res., vol. 49, pp. 639-643 (1988).
Vertino et al., “Selective cellular depletion of mitochondrial DNA by the polyamine analog. N.Sup.1,N.sup.12—bis(ethyl)spermine, and its relationship to polyamine structure and function”, Mol. Pharm., vol. 39, pp. 487-494 (1991).
Chang et al., “Modulation of polyamine biosynthesis and transport by oncogene transfection”, Biochem. and Biophys. Res. Commun., vol. 157, pp. 264-270 (1988).
Vertino et al., “Structural determinants of spermidine-DNA interactions”, Biopolymers, vol. 26, pp. 691-703 (1987).
Bergeron et al., “Antiproliferative Properties of Polyamine Analogues: A Structure-Activity Study”, J. Med. Chem. vol. 37, pp. 3464-3476 (1994).
Bergeron et al., “The Role of Charge in Polyamine Analogue Recognition”, J. Med. Chem., vol. 38, pp. 2278-2285 (1995).
Bergeron et al., J. Med. Chem., vol. 46, pp. 5478-5483 (2003).
Communication dated May 15, 2008 in EP 04 80 0606 transmitting Supplementary Partial European Search Report.
Bergeron, Raymond J. et al.: “Synthetic Polyamine Analogs as Antineoplastics” Journal of Medicinal Chemistry, 31 (6), 1183-90 Coden; JMCMAR; ISSN 0022-2623, 1998, XP002291373. *the entire document*
Davis Brian J
Miles & Stockbridge P.C.
University of Florida
LandOfFree
Aminated polyamines does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Aminated polyamines, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Aminated polyamines will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3980332