Organic compounds -- part of the class 532-570 series – Organic compounds – Nitriles
Patent
1996-08-05
1998-12-08
Raymond, Richard L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitriles
546291, 546292, 5483381, 548542, 548547, 558 6, 560 18, 560 34, 560 42, C07C23350, C07C23346
Patent
active
058471928
ABSTRACT:
Boron compound complexing reagents and methods of synthesizing these reagents are disclosed. These reagents, including those shown as General Formula I and General Formula II may be used, after further reactions described herein, to complex with boronic compounds, such as phenylboronic acid or derivatives thereof. ##STR1##
REFERENCES:
patent: 2548257 (1951-07-01), Goldberg et al.
patent: 4269605 (1981-05-01), Dean et al.
patent: 4281181 (1981-07-01), Nagasawa et al.
patent: 4496722 (1985-01-01), Gallop et al.
patent: 4713346 (1987-12-01), Gallop et al.
patent: 4783487 (1988-11-01), Brune
patent: 4851443 (1989-07-01), Brune
patent: 4894229 (1990-01-01), Polson et al.
patent: 4910300 (1990-03-01), Urdea et al.
patent: 5002883 (1991-03-01), Bieniarz et al.
patent: 5045451 (1991-09-01), Uhr et al.
patent: 5093232 (1992-03-01), Urdea et al.
patent: 5183653 (1993-02-01), Linder et al.
patent: 5464861 (1995-11-01), Dobrusin et al.
A.M. Thompson et al., "Tyrosine Kinase Inhibitors. 2. Synthesis of 2,2'-Dithobis (1H-indole-3-alkanamides) and Investigation of Their Inhibitory Activity against Epidermal Growth Factor Receptor and pp60v-src Protein Tyrosine Kinases," Journal of Medicinal Chemistry, vol. 37, No. 5, 4 Mar. 1994 pp. 598-609.
PCT International Search Report, PCT/US97/13143, mailed Nov. 7, 1997.
Bailey et al., Chemical Abstracts, vol. 111, abstract 130131, 1988.
Ciba Inc., Chemical Abstracts, vol. 66, abstract 85610, 1966.
Wilcheck, M. & Bayer E.A., "Introduction to Avidin-Biotin Technology"; Methods in Enzymology; vol. 184; 1990 (USA).
Kessler et al.; "Non-radioactive Labeling and Detection of Nucleic Acids"; Biol. Chem. Hoppe-Seyler; vol. 371, pp. 917-927; 1990 (USA).
Singhal, R.P. & DeSilva, S.S.M.; "Boronate Affinity Chromatography"; Advances in Chromatography; vol. 31, pp. 293-335; 1992 (USA).
Mazzeo, J.R. & Krull, I.S.; "Immobilized Boronates for the Isolation and Separation of Bioanalytes"; Biochromatography; vol. 4, pp. 124-130; 1989.
Bergold, A. & Scouten, W.H., "Borate Chromatography"; Solid Phase Biochemistry; Ch. 4, pp. 149-187; 1983 (USA).
Lorand, J.P. & Edwards, J.O.; "Polyol Complexes and Structure of the Benzeneboronate Ion"; J. Org. Chem., vol. 24, p. 769; 1959 (USA).
Bowie, R.A. & Musgrave, O.C.; "Organoboron Compounds. Part V.* The Hydrolysis of Cyclic Phenylboronates"; J. Amer. Chem. Soc.; pp. 3945-3949; 1963 (USA).
Sienkiewicz, P.A. & Roberts, D.C.; "pH Dependence of Boronic Acid-Diol Affinity in Aqueous Solution"; J. Inorg. Nucl. Chem.; vol. 42, pp. 1559-1571; 1980 (USA).
Tanner, D.W. & Bruice, T.C.; "Boric Acid Esters" J. Amer. Chem. Soc.vol. 89, pp. 6954-6971; 1967 (USA).
Kliegel, W. & Nanninga, D.; "Borchelate von Salicylaldoxim und Derivaten"; Monatshefte Fur Chemie; vol. 114, pp. 465-484; 1983 (FRG).
Imagawa et al.; "Characteristics and Evaluation of Antibody-Horseradish Perioxidase Conjugates, etc."; J. Applied Biochemistry; vol. 4, pp. 41-57; 1982 (USA).
Kessler, C.; Advances in Mutagenesis Research (Obe, G. ed.); pp. 105-152; Springer-Verlag, Berlin/Heidelberg; 1990 (USA).
Brinkley, M.; "A Brief Survey of Methods for Preparing Protein Conjugates with Dyes, Haptens, and Cross Linking Reagents"; Bioconjugate Chem.; vol. 3, pp. 2-13; 1992 (USA).
Linder et al.; "Technetium Labeling of Monoclonal Antibodies with Functionalized BATOs 1. TcCI(DMG).sub.3 PITC"; Bioconjugate Chem.; vol. 2, pp. 160-170; 1991 (USA).
Linder et al.; "Technetium Labeling of Monoclonal Antibodies with Functionalized BATOs 2. TcCI(DMG).sub.3 CPITC Labeling of B72.3, etc" Bioconjugate Chem.; vol. 2, pp. 407-415; 1991 (USA).
Burnett et al.; "Synthesis of a Fluorscent Boronic Acid Which Reversibly Binds to Cell Walls, etc."; Biochem. Biophys. Research Commun.; vol. 96, pp. 157-162; 1980 (USA).
Steinberg, G.M. & Swidler, R.; "The Benzohydroxamate Anion"; J. Org. Chem. vol.; vol. 30, pp. 2362-2365; 1965 (USA).
Bauer, L. & Exner, O.; "The Chemistry of Hydroxamic Acids and N-Hydroxyimides"; Angew. Chem. Internat. Edit.; vol. 13, pp. 376-384; 1974 (USA).
Cai, S.X. & Kean, J.; "o-Acetomidophenylboronate Esters Stabilized Toward Hydrolysis by an Intramolecular O-B Interation, etc."; Bioconjugate Chem.; vol. 2, pp. 317-322; 1991 (USA).
Ramalingam, K. & Nowotnik, D.; "Syntheses of Some Isothiocyanatophenylboronic Acids"; Org. Prep. Proc. Int.; vol. 23, 729-734; 1991 (USA).
Kliegel, W. & Nanninga, D.; "Borchelate Von Salicyladehydnitronen"; Journal of Organometallic Chem.; vol. 243, pp. 373-385; 1983 (USA).
Ripan et al.; "Etude Du Systeme Acide Borique-Salicylaldoxime en Solutions Aqueuses"; Revue Roumaine de Chimie; vol. 10, pp. 965-971; 1965 (FRA).
Roberts et al.; "Pluripotential Amino Acids"; Tetrahedron Letters; vol. 21, pp. 3435-3438; 1980 (USA).
Kemp, D.S. & Roberts, D.; "New Protective Groups for Peptide Synthesis--II The DOBZ Group, etc."; Tetrahedron Letters; vol. 52, pp. 4629-4632; 1975 (USA).
Kliegel, W. & Nanninga, D.; "Borchelate von N-substituierten Hydroxamsauren"; Chem. Ber.; vol. 116, pp. 2616-2629; 1983 (FRG).
Mikesova, M. & Bartusek, M.; "Reaction of Boric Acid with Salicylic and Chromotropic Acids and with Their Derivatives"; Chem. Zvesti; vol. 32(4), pp. 472-477; 1978.
Feeney, R.E., "Chemical Modification of Proteins: Comments and Perspectives"; Int. J. Peptide Protein Res.; vol. 29, pp. 145-161 (USA), 1987.
Means, G.E. & Feeney, R.E.; "Chemical Modifications of Proteins: History and Applications"; Bioconjugate Chem.; vol. 1, pp. 2-12 (USA), 1990.
O'Shannessy, D.J. & Quarles, R.H., "Labeling of the Oligosaccharide Moieties of Immunoglobulins"; J. Immunological Methods; vol. 99, pp. 153-161 (1987) (USA).
van't Reit, B., Wampler, G.L., & Elford, H.L.; "Synthesis of Hydroxy- and Amino-Substituted Benzohydroxamic Acids, etc."; J. Medicinal Chem.; vol. 22, No. 5, 589-592, 1979 (USA).
Soundararajan, et al.; "Boronic Acids for Affinity Chromatography: Spectral Methods for Determination, etc."; Analytical Biochem.; vol. 178, pp. 125-134, 1989 (USA).
Goodchild, J.; "Conjugates of Oligonucleotides and Modified Oligonucleotides: A Review of Their Synthesis and Properties"; Bioconjugate Chem.; vol. 1, No. 3, pp. 165-193, 1990 (USA).
Kessler, C.; Nonradioactive Labeling and Detection of Biomolecules; Ch. 1-3, 1992 (USA).
Meares, C.F., "Editorial: Introduction to Bioconjugate Chemistry"Bioconjugate Chem.; vol. 1, No. 1, 1990 (USA).
Waggoner, A.S., "Fluorescent Probes for Cytometry"; Flow Cytometry and Sorting; 2nd ed; pp. 209-225; 1990 (USA).
Borrebaeck, C.; "Strategy for the production of human monoclonal antibodies using in vitro activated B cells"; J. Immun. Methods; vol. 123; 157-165; 1989 (USA). 5-Dihydroxybenzyl) amino!salicylate, etc."; Chemical Abstracts; vol. 120; 322877v; 1994 (USA).
Hirano, et al.; "Silver halide color photographic material"; Chemical Abstracts; vol. 116; 140012u; 1992 (USA).
Kawasaki, et al.; "Silver halide photographic material with improved storage stability"; Chemical Abstracts; vol. 109; 160505r; 1988 (USA).
Priewe, H., et al.; "o-Hydroxybenzohydroxamic Acids"; Chemical Abstracts; vol. 52; 10184; 1958 (USA).
Regnier, G., et al., No. 473-"Acide-Pheonols", Bulletin de la Societe Chimique de France 1966, No. 9, pp. 2821-2827.
Meindl, W., et al.; "Antimykobakterielle N-Alkylbenzylamine", Arch. Pharm., 315, 941-946 (1982).
Thompson, A.M., et al.; Tyrosine Kinase Inhibitors: Synthesis of 2,2'-Dithiobis (1H-indole-3-alkanamides) and Investigation of Their Inhibitory Activity against Epidermal (cont.) Growth Factor Receptor and pp60.sup.VSRC Protein Tyrosine Kinases, J. Med. Chem., 1994, 37, 598-609.
Quelet, R., et al., No. 303-"Chloromethylation de l'acide salicylique et des ethers phenoliques correspondants", Bulletin de la Societe Chimique de France, 1969, No. 5, pp. 1698-1705.
Malmberg, H., et al.; "Stereoselectivity in the transfer of the 2-(1-dimethylaminoethyl) phenyl group, R, from LiR.sub.2 Cu and Li(R)-(2-thienyl)Cu to enones," Chem Abstracts; vol.98;71593e;1982.
Kaiser Robert J.
Lund Kevin P.
Stolowitz Mark L.
Torkelson Steven M.
Prolinx, Inc.
Raymond Richard L.
Systemix
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