Chemistry: analytical and immunological testing – Nitrogen containing – Amine and quaternary ammonium
Reexamination Certificate
2007-06-12
2007-06-12
Soderquist, Arlen (Department: 1743)
Chemistry: analytical and immunological testing
Nitrogen containing
Amine and quaternary ammonium
C422S051000, C422S051000, C422S067000, C422S069000, C422S082050, C422S082080, C422S082090, C436S052000, C436S057000, C436S086000, C436S087000, C436S088000, C436S089000, C436S090000, C436S107000, C436S108000, C436S111000, C436S112000, C436S113000, C436S166000, C436S169000, C436S172000, C436S518000, C436S524000, C436S527000, C436S528000, C436S529000, C436S530000, C436S531000, C436S532000, C436S533000, C436S534000
Reexamination Certificate
active
09983743
ABSTRACT:
A compound linked to a solid support (R) through a divalent linker moiety (X) and which is represented by the following formula:is disclosed. In particular, the 1-hydroxybenzotriazole-6-carboxylic acid is directly linked to the support under mild conditions (i.e., in aqueous or organic solvents at neutral pH and at room temperature). The polymer bound 1-hydroxybenzotriazole-6-carboxylic acid can be used for the derivatization of amines as well as for single step amino group modification of proteins, peptides, and amines via acylation or sulfonylation reactions. A flow through device and method for the single step amino group modifications of proteins, peptides, and amines is disclosed. Also disclosed is a flow through device for the detection of amines in a sample. Additionally, a device and method for the detection of amines in a sample using 1-hydroxybenzotriazole-6-carboxylic acid is disclosed. In a preferred embodiment, the device is used to detect the presence of amines in a spoiled meat product. Diagnostic kits for detecting the presence of amines is also disclosed.
REFERENCES:
patent: 3725380 (1973-04-01), Konig et al.
patent: 4370312 (1983-01-01), Jung et al.
patent: 4868167 (1989-09-01), Mokotoff et al.
patent: 4923901 (1990-05-01), Koester et al.
patent: 5183740 (1993-02-01), Ligler et al.
patent: 5202451 (1993-04-01), Fritzberg et al.
patent: 5204242 (1993-04-01), Junius-Comer et al.
patent: 5403698 (1995-04-01), Tachiki et al.
patent: 5496700 (1996-03-01), Ligler et al.
patent: 5549974 (1996-08-01), Holmes
patent: 5576216 (1996-11-01), Patchornik
patent: 5585275 (1996-12-01), Hudson et al.
patent: 5789172 (1998-08-01), Still et al.
patent: 5917015 (1999-06-01), Jensen et al.
patent: 2002/0035222 (2002-03-01), Oh et al.
patent: 2002/0076835 (2002-06-01), Ede et al.
patent: 488152 (1993-06-01), None
patent: 98/03452 (1998-01-01), None
Popova, A. Doklady Bolgarskoi Akademii Nauk 1966, 19, 77-80.
Heusel, G. et al, Angewandte Chemie 1977, 89, 681-682.
Moss, R. A. et al, Tetrahedron Letters 1977, 3851-3854.
Kuzmic, P. et al, Analytical Biochemistry 1992, 205, 65-69.
Shriver-Lake, L. C. et al, ACS Symposium Series 1996, 646(Environmental Immunochemical Methods), 46-55.
Kunugi, S. et al, Bulletin of the Chemistry Society of Japan 1996, 69, 1747-1753.
Charles, P. T. et al, SPIE 1997, 3105(Chemical, Biochemical, and Environmental Fiber Sensors 1X), 80-87.
Bart, J. C. et al, Sensors and Actuators B 1997, 38-39, 411-418.
Paio, A. et al, Journal of Combinatorial Chemistry 1999, 1, 317-325.
Piletsky, S. A. et al, Fresenius' Journal of Analytical Chemistry 1999, 364, 512-516.
Chinchilla, R. et al, Tetrahedron Letters 2000, 41, 2463-2466.
Yang, M. et al, Analytica Chimica Acta 2000, 409, 45-53.
Goldstein, H. et al, Helvetica Chimica Acta 1949, 32, 2334-2339, no month.
Nova Biochem Catalog 1999, p. 214, product No. 01-64-0179, no month.
Chang, Y.-T. et al, Bioorganic & Medicinal Chemistry Letters 1999, 9, 2479-2482, no month.
Lu, C. et al, Proc. China-U.S. Bilateral Symp. Polym. Chem. Phys. 1981, Meeting date 1979, 101-112.
Berrada, A. et al, Bulletin de la Societe Chimoque de France 1989, 511-514.
Scheuerman, R. A. et al, Tetrahedron Letters 2000, 41, 6531-6535.
Schiemann, K. et al, Journal of Organic Chemistry 1999, 64, 4972-4975.
Mutter, M., Tetrahedron Letters 1978, 2839-2842.
Combs, A. P. et al, Tetrahedron Letters 1999, 40, 1623-1626.
Rano, T.A., et al., “Solid Phase Synthesis of Aryl Ethers Via The Mitsunobu Reaction”, Tetrahedron Letters, 36, 22, 3789-3792 (1995).
Deshpande, M.S., “Formation of Carbon—Carbon Bond on Solid Support: Application of the Stille Reaction”, Tetrahedron Letters, 35, 31, 5613-5614 (1994).
Forman, F.W., et al., “Solid-Phase Synthesis of Biaryls via the Stille Reaction”, J. Org. Chem., 60, 523-528 (1995).
Yu, K-I., et al., “Heck Reactions In Solid Phase Synthesis”, Tetrahedron Letters. 35, 48, 8919-8922 (1994).
Hiroshige, M., et al., “Formation of C—C Bond In Solid Phase Synthesis Using The Heck Reaction”, Tetrahedron Letters, 36, 26, 4567-4570 (1995).
Chen, C., et al., “‘Analogous’ Organic Synthesis of Small-Compound Libraries: Validation of Combinatorial Chemistry in Small-Molecule Synthesis”, J. Am. Chem. Soc., 116,. 2661-2662 (1994).
Bunin, B.A., et al., “A General and Expedient Method for the Solid-Phase Synthesis of 1,4-Benzodiazepine Derivatives”. J. Am. Chem. Soc., 114, 10997-10998 (1992).
Hobbs DeWitt, S., et al., “‘Diversomers’: An Approach to Nonpeptide, Nonoligomeric Chemical Diversity”, Proc. Natl. Acad. Sci. USA. 90, 6909-6913 (1993).
Hobbs DeWitt, S., et al., “DIVERSOMER™ Technology: Solid Phase Synthesis, Automation, and Integration for the Generation of Chemical Diversity”, Drug Development Research, 33, 116-124 (1994).
Fridkin, M., et al., “A Synthesis of Cyclic Peptides Utilizing High Molecular Weight Carriers”, J. Am. Chem. Soc., 87, 20, 4645-4648 (1965).
Fridkin, M., et al., “Use of Polymers as Chemical Reagents: I. Preparation of Peptides”, J. Am. Chem. Soc. 88, 13, 3164-3165 (1966).
Kalir, R., et al., “(4-Hydroxy-3-nitro)benzylated Polystyrene: An Improved Polymeric Nitrophenol Derivative for Peptide Synthesis”, Eur. J. Biochem., 42, 151-156 (1974).
Laufer, D.A., et al., “A Reagent for Peptide Synthesis. Copoly(ethylene-N-hydroxymaleimide)”. J. Am. Chem. Soc., 90, 10, 2696-2698 (1968).
Kalir, R., et al., “New Useful Reagents for Peptide Synthesis”, Eur. J, Biochem., 59, 55-61 (1975).
Mokotoff, M., et al., “Synthesis of the C-terminal Half of Thymosinα1by the Polymeric Reagent Method”. Int. J. Peptide Protein Res., 21, 145-154 (1983).
Mokotoff. M., et al., “Thymosin-like Peptides as Potential Immunostimulants. Synthesis Via the Polymeric-Reagent Method”, J. Med. Chem., 33, 354-360 (1990).
Weinshenker. N. M., et al., “Polymeric Reagents I. Synthesis of an Insoluble Polymeric Carbobiimide”. Tetrahedron Letters. 32, 3281-3284 (1972).
Desai, M.C., et al., “Polymer Bound EDC (P-EDC): A Convenient Reagent For Formation of an Amide Bond”, Tetrahedron Letters. 34, 48, 7685-7688 (1993).
Arnold, I..D., et al., “Polymer-Supported Alkyl Azodicarboxylates for Mitsunobu Reactions”, J. Am. Chem. Soc., 111. 3973-3976 (1989).
Caputo, R., et al., “Polymer-Bound Triarylphospshine-Iodine Complexes. Convenient Coupling Reagent Systems in Peptide Synthesis”, Synthesis, 141-143 (1995).
Pop, I.E., et al., “Versatile Acylation of N-Nucleophiles Using a New Polymer-Supported I-Hydroxybenzotriazole Derivative”, J. Org. Chem., 62, 2594-2603 (1997).
Dendrinos, K., et al., “HOBT Immobilized on Macroporous Polystyrene Beads: A Useful Reagent For the Synthesis of Amides”, Chem. Commun., 499-500 (1998).
Huang, W., et al., “Synthesis of Medium Ring Lactams Via Cyclization Reactions Using Polymer Bound HOBT as Catalyst”, Tetrahedron Letters. 36, 50, 9113-9116 (1995).
Dendrinos, K.G., et al., “Synthesis of N-Hydroxysuccinimide Esters Using Polymer Bound HOBT”, Tetrahedron Letters, 39, 1321-1324 (1998).
Dendrinos, K.G., et al., “Convenient Protection of Amines as Carbamates Using Polymer-Bound HOBT as Catalyst”, J. Chem Soc., Perkin Trans., 1463-1464 (1998).
König, W., “Eine neue Methode zur Synthese von Peptiden: Aktivierung der Carboxylgruppe mit Dicyclohexycarbodiinid unter/Zusatz von I-Hydroxy-benzotriazolen”, Chem. Ber., 103, 788-798 (1970).
“Nuclear Magnetic Resonance Spectra”, Sadtler Reserach Laboratories. Inc., 28971 M (1975).
Imrie, C., et al., “Photolysis of (Arylmethyl)triphenylphosphonium Salts. Substituent. Counterion, and Solvent Effects on Reaction Products”, J. Org. Chem., 58, 5643-5649 (1993).
Kishikawa, K., et al., “Chemoselective Alcoholysis of Acylureas”, Synthesis. 173-175 (1994).
Rothwell Figg Ernst & Manbeck
Soderquist Arlen
The University of Maryland Baltimore County
LandOfFree
Amine detection method and materials does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Amine detection method and materials, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Amine detection method and materials will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3843403