Chemistry: analytical and immunological testing – Involving an insoluble carrier for immobilizing immunochemicals
Patent
1993-12-02
1996-08-13
Bond, Robert T.
Chemistry: analytical and immunological testing
Involving an insoluble carrier for immobilizing immunochemicals
436501, 436531, 435 71, 427 21, 427 213, 427 211, 427 223, G01N 33543
Patent
active
055455689
ABSTRACT:
Methods, compositions, and devices for synthesizing combinatorial libraries of various useful compounds, such as benzodiazepines, prostaglandins, .beta.-turn mimetics and glycerol-derived drugs is described. In order to expediently synthesize such combinatorial libraries of derivatives based upon these core structures, a general methodology for the solid phase synthesis of these derivatives is also provided. This disclosure thus also describes an important extension of solid phase synthesis methods to nonpolymeric organic compounds.
REFERENCES:
patent: 3297755 (1967-01-01), Sternbach et al.
patent: 4758623 (1988-07-01), Leznoff
patent: 4968794 (1990-11-01), Weber et al.
patent: 5082839 (1992-01-01), Weber et al.
patent: 5143854 (1992-09-01), Pirrung et al.
patent: 5288514 (1994-02-01), Ellman
patent: 5324483 (1994-06-01), Cody et al.
H okfelt, T., et al, "Distribution Patterns of CCK and CCK mRNA in some Neuronal and Non-Neuronal Tissues," Neuropeptides, 19:(Suppl.)31-43 (1991).
Woodruff, G. N., et al., "Functional Role of Brain CCK Receptors," Neuropeptides, 19:(Suppl.)45-56 (1991).
Chang, R. S. L., et al., "Biochemical and pharmacological characterization of an extremely potent and selective nonpeptide cholecystokinin antagonist," Proc. Natl. Acad. Sci. USA, 83:4923-4926 (Jul. 1986).
Davis, R., et al., "A Convergent Total Synthesis of (+)-Prostaglandin F.sub.2.alpha. Via Conjugate Addition and Regiospecific Enolate Trapping," Org. Chem., 44(22):3755-3759 (1979).
Suzuki, M., et al., "The Three-Component Coupling Synthesis of Prostaglandins," J. Am. Chem. Soc., 110:4718-4726 (1988).
Lu, Gui-shen, et al., "Improved Synthesis of 4-Alkoxybenzyl Alcohol Resin," J. Org. Chem., 46:3433-3436 (1981).
Ball, J. B., et al., "Conformational Constraints: Nonpeptide .beta.-Turn Mimics," J. of Molecular Recognition, 3(2):55-64 (1990).
Evans, D. A., et al., "The Total Syntheses of the Isodityrosine-Derived Cyclic Tripeptides OF4949-III and K-13. Determination of the Absolute Configuration of K-13," J. Am. Chem. Soc., 111:1063-1072 (1989).
Crowley, J. I., et al., "Solid-Phase Organic Synthesis: Novelty or Fundamental Concept?," Accounts of Chemical Research, 9:135-144 (1976).
Rose, G. D., et al., "Turns in Peptides and Proteins," Advances in Protein Chemistry, 37:1-109 (1985).
Taylor, R. J. K., "Organocopper Conjugate Addition-Enolate Trapping Reactions," Synthesis, pp. 364-392 (Apr. 1985).
Worster, P. M., et al., "Asymmetric Synthesis of 2-Alkylcyclohexanones on Solid Phases," Angew. Chem. Int. Ed. Engl., 18(3):221-222 (1979).
Kraus, M. A., et al., "The Directed Mixed Ester Condensation of Two Acids Bound to a Common Polymer Backbone," J. of Amer. Chem. Soc., 93(26):7325-7327 (Dec. 29, 1971).
Kaplan, B. E., et al., "Photochemical Loss of a Chloride Anion from an .alpha.-Chloroketone. The Photolysis of Exo-3-Chlorobicyclo[2.2.1]Hept-5-En-2-One in Methanol," Tetrahedron Letters, No. 55, pp. 4855-4856 (1970).
Baum, R. M., "Combinatorial Approaches Provide Fresh Leads for Medicinal Chemistry," C&EN, pp. 20-26 (Feb. 7, 1994).
Fyles, T. M., et al., "Some Solid-Phase Syntheses of the Sex Attractant of the Spruce Budworm--trans-11-Tetradecenal," J. Chem. Ecol., 4(1):109-116 (1978).
Svirskaya, P. I., et al., "Syntheses of Unconjugated (Z,Z)-Diolefinic Insect Pheromones on Insoluble Polymer Supports," J. of Chem. Ecology, 10(2):321-333 (1984).
Yedidia, V., et al., "Regioselectivity in cycloaddition reactions on solid phases," Canadian J. Chem., 58(11):1144-1150 (1980).
Svirskaya, P. I., et al., "Syntheses of Trans Alken-1-ols as Candidates for Insect Sex Attracts," J. of Chemical and Engineering Data, 24(2):152-155 (1979).
Neckers, D. C., "Solid phase synthesis," Chemtech, pp. 108-116 (Feb. 1978).
Keana, J. F. W., et al., "Functionalized Silica Gel as a Support Solid-Phase Organic Synthesis," J. of Organic Chemistry, pp. 1641-1644 (May 16, 1986).
Leznoff, C. C., et al., "The use of polymer supports in organic synthesis. VIII. Solid phase syntheses of insect sex attractants," Can. J. Chem., 55:1143-1153 (1977).
Goldwasser, J. M., et al., "The solid phase synthesis of monoester monoamides and monoester monoalcohols from symmetrical diacid chlorides," Can. J. Chem., 56:1562-1568 (1978).
Fyles, T. M., et al., "The use of polymer supports in organic synthesis. XII. The total stereoselective synthesis of cis insect sex attractants on solid phases," 55:4135-4143 (1977).
Leznoff, C. C., et al., "Festphasensynthese unsymmetrischer Tetraarylporphyrine," Angew. Chem., 90(12):1001-1002 (1978).
Leznoff, C. C., et al., "Use of Insoluble Polymer Supports in Organic Synthesis. 9. Synthesis of Unsymmetrical Carotenoids on Solid Phases," J. Org. Chem., 42(19):3203-3205 (1977).
Beebe, X., et al., "Polymer-Supported Synthesis of 2,5-Disubstituted Tetrahydrofurans," J. Am. Chem. Soc., 114:10061-10062 (1992).
Sugasawa, T., et al., "1-Azacycloalkyl-1,4-benzodiazepin-2-ones with antianxiety-Antidepressant Actions," J. Med. Chem., 28(6):699-707 (1985).
O'Donnell, M. J., et al., "A Mild and Efficient Route to Schiff Base derivatives of Amino Acids," J. Org. Chem., 47:2663-2666 (1982).
Leznoff, C. C., et al., "Syntheses of Monometalated and Unsymmetrically Substituted Binuclear Phthalocyanines and a Pentanuclear Phtalocyanine by Solution and Polymer Support Methods," J. Org. Chem., 56(1):82-90 (1991).
Fyles, T. M. et al., "The use of polymer supports in organic synthesis. V. The preparation of monoacetates of symmetrical diols," Can. J. Chem., 54:935-942 (1976).
Leznoff, C. C., "Synthesis of Insect Sex Attractants on Solid Phases," J.C.S. Chem. Comm., pp. 251-252 (1976).
McArthur, C. R., et al., "Polymer supported enantioselective reactions. II. .alpha.-Methylation of cyclohexanone," Can. J. Chem., 60:1836-1841 (1982).
Leznoff, C. C., et al., "The Use of Insoluble Polymer Supports as Monoblocking Groups of Symmetrical Diacid Chlorides," Tetrahedron Letters, No. 22, pp. 1875-1878 (1977).
Dixit, D. M., et al., "Insoluble Polymer Supports as Monoblocking Agents of Symmetrical Diamines," J.C.S. Chem. Comm., pp. 798-799 (1977).
Xu, Z., et al., "The monoblocking of symmetrical diketones on insoluble polymer supports," Can. J. Chem., 61:1405-1409 (1983).
Schore, N. E., et al., "Pauson-Khand Cycloadditions on Polymer-Linked Substrates," J. Am. Chem. Soc., 112:441-442 (1990).
Moon, H., et al., "A Polymer-Supported Chiral Auxiliary Applied to the Iodolactonization reaction: Preparation of .gamma.-Butyrolactones," J. Org. Chem., 57:6088-6089 (1992).
Leznoff, C. C., "The Use of Insoluble Polymer Supports in General Organic Synthesis," Accounts of Chemical Research, 11:327-333 (1978).
Zuckermann, R. N., et al., "Efficient Method for the Preparation of Peptoids [Oligo(N-substituted glycines)] by Submonomer Solid-Phase Synthesis," J. Am. Chem. Soc., 114:10646-109647 (1992).
Baum, R., "Solid-phase synthesis of benzodiazepines," C&EN, pp. 33-34 (Jan. 18, 1993).
Hall, T. W., et al., "The Solid Phase Synthesis of Unsymmetrical Phthalocyanines," Nouveau Journal De Chimie, pp. 653-658 (1982).
Worster, P. M., et al., "Asymmetrische Synthese von 2-Alkylcyclohexanonen an festen Tr agern," Angew. Chem., 91(3):255 (1979).
Wong, J. Y., et al., "Festphasensynthese und Photochemie von 4,4'-Stilbendicarbaldehyd," Angew. Chem., 86(20):743-744 (1974).
Kirk-Othmer, Encyclopedia of Chem. Tech., 3rd Ed., vol. 18 (Wiley 1982).
Camps, F., "Organic syntheses with Functionalized polymers. IV. Synthesis of 1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-ones." Chemical Abstracts, No. 10018q, p. 841 (1975).
Bogatskii, A. V., et al., "1,4-Benzoidiazepines, their cyclic homologs and analogs. XVII. Synthesis and properties of 3-arylidene-and 3-heterylidene-1,2-dihydro-3H-1,4-benzodiazepin-2-ones," Chemical Abstracts, No. 10019r, p. 841 (1975).
DeWitt, S. H., et al., "`Diversomers`: An Approach to nonpeptide, nonoligomeric chemical diversity," Proc. Natl. Acad. Sci. USA, 90:6909-6913 (Aug. 1993).
Jung, G., et al., "Multiple Peptide Synthesis Methods and their Applications," Angew. Chem. Int. Ed. Engl., 31:367-383 (1992).
Evans, B. E., et al., "Methods for Drug Discovery: Dev
Bond Robert T.
The Regents of the University of California
LandOfFree
Solid phase and combinatorial synthesis of compounds on a solid does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Solid phase and combinatorial synthesis of compounds on a solid , we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Solid phase and combinatorial synthesis of compounds on a solid will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1047591