Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1994-06-22
1996-06-11
Brust, Joseph Paul
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
548400, 548406, 548517, 548518, 548532, 548533, 548536, 548537, 548541, 548560, 548565, 548566, 548570, 548577, 435 792, 436518, C07D20700, C07D20900
Patent
active
055257348
ABSTRACT:
Disclosed are methods for synthesizing very large collections of diverse pyrrolidine compounds on solid supports and synthetic compound libraries comprising pyrrolidine groups prepared by such methods.
REFERENCES:
patent: 5143854 (1992-09-01), Pirrung et al.
Furka, et al.; Int. J. Peptide Protein Res., 37, pp. 487-493 (1991).
Ellman; Archives of Biochemistry and Biophysics, 82, pp. 70-77 (1959).
Cheung, et al.; Biochimica & Biopbysica Acta, 293, pp. 451-463 (1973).
Bull, et al.; J. of Biological Chemistry, 260, pp. 2952-2962 (1985).
Tsuge, et al.; Org. Chem., 53, pp. 1384-1391 (1988).
Petrillo, Jr., et al.; Med. Res. Rev., 2, pp. 1-41 (1982).
Gallop, et al., J. Med. Chem., 37(9):1233-1251 (29 Apr. 1994).
Gordon, et al., J. Med. Chem., 37(10):1385-1401 (1994).
Williams, et al., J. Org. Chem., 57(24):6527-6532 (1992).
Grigg, et al., Tetrahedron, 48(47)10431-10442 (1992).
Williams et al., 1992, J. Org. Chem. 57:6527-6532; Asymmetric [1,3]-Dipolar Cycloaddition Reactions: Synthesis of Highly Substituted Proline Derivatives.
Allway et al., "Chiral Co(II) and MN(II) Catalysts for the 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides Derived from Arylidene Imines of Glycine," Tetrahedron Letters, vol. 32, No. 41, pp. 5817-5820 (1991).
Aly et al., "X=Y-ZH Compounds as Potential 1,3-Dipoles. Part 41..sup.1 Azomethine Ylide Formation from the Reactions of .alpha.-Amino Acids and Esters with Alloxan (Strecker Degradation) and with 1-Phenyl-3-methylpyrazoline-4,5-dione," Tetrahedron, vol. 50, No. 3, pp. 895-906 (1994).
Amornraksa et al., "X=Y-ZH Compounds as Potential 1,3-Dipoles, Part 24..sup.1,2 Preparation and Thermal Fragmentation of Imidazolidines. Influence of Metal Salts on Pyrrolidine Versus Imidazolidine Formation," Tetrahedron, vol. 45, No. 14, pp. 4649-4668 (1989).
Ardill et al., "X=Y-ZH Systems as Potential 1,3-Dipoles. Part 19..sup.1 Intramolecular Cycloadditions of Non-Stabilized Azomethine Ylides Generated Via The Decarboxylative Route From .alpha.-Amino Acids," Tetrahedron, vol. 44, No. 15, pp. 4953-4966 (1988).
Ardill et al., "Iminium Ion Route to Azomethine Ylides from Primary and Secondary Amines," J. Chem. Soc. Chem. Commun., pp. 602-604 (1986).
Armstrong et al., "X=Y-ZH Systems as Potential 1,3-Dipoles--5.sup.1 Intramolecular Cycloadditions of Imines of .alpha.-Amino Acid Esters," Tetrahedron, vol. 41, No. 17, pp. 3547-3558 (1985).
Barr et al, "Metal Ion Catalyzed Asymmetric 1,3-Dipolar Cycloaddition Reactions of Imines of .alpha.-Amino Esters," Tetrahedron Letters, vol. 31, No. 45, pp. 6569-6572 (1990).
Barr et al., "X=Y-ZH Systems as Potential 1,3-Dipoles. Part 15.sup.1. Amine Generated Azaallyl Anions Versus Metallo-1,3-Dipoles in Cycloadditions of .alpha.-Amino Acid Esters. Facile Regio-and Stereo-Specific Formation of Pyrrolidines," Tetrahedron, vol. 44, No. 2, pp. 557-570 (1988).
Barr et al., "Ti(IV) Mediated Transesterification and Regio- and Stereo-Specific Cycloaddition of Imines of .alpha.-Amino Esters. Reversal of Normal Regiochemistry," Tetrahedron Letters, vol. 30, No. 35, pp. 4727-4730 (1989).
Boger et al., "Total Synthesis of (+)-Piperazinomycin," J. Am. Chem. Soc., vol. 115, No. 24, pp. 11426-11433 (1993).
Cull et al., "Screening for Receptor Ligands Using Large Libraries of Peptides Linked to the C Terminus of the lac Repressor," Proc. Natl. Acad. Sci., USA, vol. 89, pp. 1865-1869 (1992).
Cwirla et al., "Peptides on Phage: A Vast Library of Peptides for Identifying Ligands," Proc. Natl. Acad. Sci., USA, vol. 87, pp. 6378-6382 (1990).
Devlin et al., "Random Peptide Libraries: A Source of Specific Protein Binding Molecules," Science, vol. 249, pp. 404-406 (1990).
Dorrity et al., "X=Y-ZH Systems as Potential 1,3-Dipoles. Part 18..sup.1 Cycloaddition of 4.pi.-Sulphinylaminomethamide Species Generated from .alpha.-Amino Acids and .alpha.-Amino Acid Esters by Sulphonyl Group Transfer..sup.2 X-Ray Crystal Structure of 4-Iso-Propyl-7-Methyl-2-Thia-6,8-Dioxo-3,7-Diazobicyclo[3.3.0]Octane S-Oxide," Tetrahedron, vol. 44, No. 15, pp. 4941-4952 (1988).
Grigg et al., "X=Y-ZH Systems As Potential 1,3-Dipoles. Part 14..sup.1 Bronsted and Lewis Acid Catalysis off Cycloadditions of Arylidene Imines of .alpha.-Amino Acid Esters..sup.2," Tetrahedron, vol. 43, No. 24, pp. 5887-5898 (1987).
Grigg et al., "The Decarboxylative Route to Azomethine Ylides. Stereochemistry of 1,3-Dipole Formation," J. Chem. Soc. Chem. Commun., pp. 47-51 (1987).
Grigg et al., "X=Y-ZH Systems As Potential 1,3-Dipoles. Part 38..sup.1 1-5-Electrocyclization of Vinyl-and Iminyl-azomethine Ylides. 2-Azaindolizines and Pyrrolo-dihydro-isoquinolines," Tetrahedron, vol. 48, No. 47, pp. 10423-10430 (1992).
Grigg et al., "The Mechanism of the Racemization of .alpha.-Amino Acids in the Presence of Aldehydes," Tetrahedron Letters, vol. 24, No. 41, pp. 4457-4460 (1983).
Grigg et al., "X=Y-ZH Systems As Potential 1,3-Dipoles. The Stereochemistry and Regiochemistry of Cycloaddition Reactions of Imines of .alpha.-Amino-Acid Esters," Tetrahedron Letters, vol. 21, pp. 2461-2464 (1980).
Grigg, "Prototropic Routes to 1,3- and 1,5-Dipoles, and 1,2-Ylides: Applications to the Synthesis of Heterocyclic Compounds," Chem. Soc. Rev., vol. 16, pp. 89-121 (1987).
Grigg et al., "X=Y-ZH Systems As Potential 1,3-Dipoles. Part 21..sup.1 Activation of the ZH Proton in Imines..sup.2, " Tetrahedron, vol. 45, No. 6, pp. 1723-1746 (1989).
Grigg, et al., "X=Y-ZH Systems As Potential 1,3-Dipoles. Part 40..sup.1 Chiral Azomethine Ylides From Homochiral Cyclic .alpha.-Amino Esters. Unusual Regiospecific Deprotonation of Iminum Ions," Tetrahedron, vol. 49, No. 38, pp. 8679-8690 (1993).
Grigg et al., "X=Y-ZH Systems As Potential 1,3-Dipoles. Part 39..sup.1 Metallo-Azomethine Ylides from Aliphatic Aldimines. Facile Regio- and Stereo-specific Cycloaddition Reactions," Tetrahedron, vol. 48, No. 47, pp. 10431-10442 (1992).
Hwang et al., "Specific Receptor Sites for 1-O-Alkyl-2-O-acetyl-sn-glycero-3-phosphocholine (Platelet Activating Factor) on Rabbit Platelet and Guinea Pig Smooth Muscle Membranes," Biochemistry, vol. 22, pp. 4756-4763 (1983).
Scott et al., "Searching for Peptide Ligands with an Epitope Library," Science, vol. 249, pp. 386-390 (1990).
Tsuge et al., "Recent Advances in Azomethine Ylide Chemistry," Advances in Heterocyclic Chemistry, vol. 45, pp. 231-349, Academic Press, Inc. (1989).
Beebe et al., "Polymer-Supported Synthesis of 2,5-Disubstituted Tetrahydrofurans," J. am. Chem. Soc., 114:10061-10062 (1992).
Gallop Mark A.
Murphy Martin A.
Affymax Technologies N.V.
Brust Joseph Paul
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