Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Peptide containing doai
Reexamination Certificate
2006-09-21
2010-06-29
Russel, Jeffrey E (Department: 1654)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Peptide containing doai
C514S011400, C514S017400, C514S183000, C514S394000, C514S634000, C514S636000, C530S321000, C530S330000, C530S345000, C340S472000, C340S474000, C564S236000
Reexamination Certificate
active
07745392
ABSTRACT:
Disclosed herein are guanidinium containing compounds consisting of a core moiety with a plurality of side chains containing guanidinium groups. Such compounds have enhanced translocation across cellular membranes and epithelial tissues. The compounds may also have a therapeutic or other biologically active moiety attached so that these moieties may be effectively transported into a cell by the guanidinium containing compound.
REFERENCES:
patent: 5637623 (1997-06-01), Goldin et al.
patent: 6235711 (2001-05-01), Dutta
patent: 2002/0107196 (2002-08-01), Gupta
patent: 2002/0131965 (2002-09-01), Rothbard et al.
patent: 2003/0073807 (2003-04-01), Wender et al.
patent: 2005/0119167 (2005-06-01), Abbenante et al.
patent: 2007/0104645 (2007-05-01), Garlich et al.
patent: 2008/0221020 (2008-09-01), Goodman et al.
patent: WO 02065986 (2002-08-01), None
patent: WO 02069930 (2002-09-01), None
patent: WO 03049772 (2003-06-01), None
patent: WO 2005/025513 (2005-03-01), None
patent: WO 2005/035549 (2005-04-01), None
patent: WO 2006/044063 (2006-04-01), None
Edwards et al. Evaluation of Radiolabeled Type IV Collagen Fragments . . . Bioconjugate Chemistry. 2001, vol. 12, No. 6, pp. 1057-1065.
Tamamura et al. Identification of Novel Low Molecular Weight CXCR4 Antagonists . . . Journal of Medicinal Chemistry. Apr. 13, 2005, vol. 48, No. 9, pp. 3280-3289.
Zhang et al. “Solution- and Solid-Phase Syntheses of Guanidine-Bridged, Water-Soluble Linkers for Multivalent Ligand Design.” Organic Letters. 2004, vol. 6, No. 9, pp. 1377-1380.
Futaki et al., “Translocation of Branched-Chain Arginine Peptides through Cell Membranes: Flexibility in the Spatial Disposition of Positive Charges in Membrane-Permeable Peptides”,Biochemistry, 2002, 41, 7925-7930.
Futaki, “Membrane-permeable arginine-rich peptides and the translocation mechanisms”,Advanced Drug Delivery Reviews 57, 2005, 547-558.
Wright et al., “Guanidinium Rich Peptide Transporters and Drug Delivery”,Current Protein and Peptide Science, 2003, 4, 105-124.
International Search Report for PCT/US2006/036746 dated May 14, 2007.
Written Opinion for PCT/US2006/036746 dated May 14, 2007.
Klein, “Hydrogen isotope effects in the reactions catalyzed by H2-forming N5,N10-methylenetetrahydromethanopterin dehydrogenase from methanogenic Archaea,” Eur. J. Biochem., Oct. 1, 1995;233(1):372-376.
Office Action dated Oct. 17, 2008 in U.S. Appl. No. 11/525,482 filed Sep. 21, 2006.
Office Action dated Dec. 9, 2008 in U.S. Appl. No. 11/526,224 filed Sep. 22, 2006.
Diaz-Mochon et al., “Synthesis and cellular uptake of cell delivering PNA-peptide conjugates”,Chem. Commun., 2005, 3316-3318.
Dragulescu-Andrasi et al., “Cell-permeable GPNA with appropriate backbone stereochemistry and spacing binds sequence-specifically to RNA”,Chem. Commun., 2005, 2, 244-246.
Takahashi et al., “Design of a nucleobase conjugated peptide that recognizes HIV-1 RRE IIB RNA with high affinity and specificity”,Chem. Commun., 2002, 6:5, 349-350.
Zhou et al., “Novel Binding and Efficient Cellular Uptake of Guanidine-Based Peptide Nucleic Acids (GNPA)”,J. Am. Chem. Soc., 2003, 125:23, 6878-6879.
International Search Report for PCT/US2006/036743 dated Jul. 19, 2007.
Written Opinion for PCT/2006/036743 dated Jul. 19, 2007.
International Search Report for PCT/US2006/036745 dated Aug. 16, 2007.
Written Opinion for PCT/US2006/036745 dated Aug. 16, 2007.
Alm et al., “Effects of topically applied PGF2 alpha and its isopropylester on normal and glaucomatous human eyes”,Prog. Clin. Biol. Res., 1989, 312, 447-458.
Fuchs et al., “Pathway for Polyarginine Entry into Mammalian Cells Biochemistry”, 2004, 43, 2438-2444.
Jiang et al., “Tumor imaging by means of proteolytic activation of cell-penetrating peptides”,Proceedings of the National Academy of Sciences of USA, 2004, 101, 17867-17872.
Joshi, “Microparticulates for ophthalmic drug delivery”,J. Ocul. Pharmacol., 1994, 10, 29-45.
Kirschberg et al., “Arginine-based molecular transporters: the synthesis and chemical evaluation of releasable taxol-transporter conjugates”,Organic Letters, 2003, 5, 3459-3462.
Lagerholm et al., “Multicolor coding of cells with cationic peptide coated quantum dots”,Nano Letters American Chem. Soc. USA, 2004, 4, 2019-2022.
Maiolo et al., “Effects of cargo molecules on the cellular uptake of arginine-rich cell-penetrating peptides”,Biochim. Biophys. Acta, 2005, 1712, 161-172.
Mayer et al.,“Efficacy of a novel hydrogel formulation in human volunteers”,Ophthalmologica, 1996, 210, 101-103.
Mordenti et al., “Intraocular pharmacokinetics and safety of a humanized monoclonal antibody in rabbits after intravitreal administration of a solution or a PLGA microsphere formulation”,Toxicol. Sci., 1999, 52, 101-106.
Rothbard et al., “Arginine-rich molecular transporters for drug delivery; role of backbone spacing in cellular uptake”,J. Medicinal Chem., 2002, 45, 3612-3618.
Shedden et al., “Efficacy and tolerability of timolol maleate ophthalmic gel-forming solution versus timolol ophthalmic solution in adults with open-angle glaucoma or ocular hypertension: a six-month, double-masked, multicenter study”,Clin. Ther., 2001, 23, 440-450.
Thomson et al., “Fmoc mediated synthesis of Peptide Nucleic Acids”,Tetrahedron, 1995, 51(22), 6179-6194.
International Search Report for PCT/US2006/036746 dated Mar. 1, 2007.
Office Action dated Mar. 19, 2009 for U.S. Appl. No. 11/525,482, filed Sep. 21, 2006.
Office Action dated Jun. 11, 2009 for U.S. Appl. No. 11/525,482, filed Sep. 21, 2006.
Office Action dated Jun. 12, 2009 for U.S. Appl. No. 11/526,224, filed Sep. 22, 2006.
Notice of Allowability mailed Dec. 15, 2009 for U.S. Appl. No. 11/525,482, filed Sep. 21, 2006.
Hou Zheng
Liu Jian
Yu Lei
Knobbe Martens Olson & Bear LLP
Nitto Denko Corporation
Russel Jeffrey E
LandOfFree
Multi-valent guanidinium compounds for enhancing molecular... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Multi-valent guanidinium compounds for enhancing molecular..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Multi-valent guanidinium compounds for enhancing molecular... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-4248418