Method for synthesis of diketopiperazine and diketomorpholine de

Details Method for synthesis of diketopiperazine and diketomorpholine de Method for synthesis of diketopiperazine and diketomorpholine de

1996-10-11

1998-10-06

Tsang, Cecelia

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

Cyclic peptides

530334, 544170, C07K 104, C07K 512

Patent

active

058177515

ABSTRACT:
The present invention relates to the areas of organic and medicinal chemistry. More specifically, the present invention is concerned with combinatorial and solid phase methods for the synthesis of diverse diketopiperazine derivatives, and the use of such methods to create libraries of diverse diketopiperazine derivatives. The present invention has application in the areas of chemical synthesis, the screening for new diketopiperazine derivatives having beneficial medical properties and the use of such screening to provide compositions and methods including diketopiperazine derivatives for treating disease.

REFERENCES:
patent: 3752814 (1973-08-01), Fluckiger et al.
patent: 3752888 (1973-08-01), Fluckiger et al.
patent: 3923709 (1975-12-01), Worley
patent: 5147875 (1992-09-01), Coates et al.
patent: 5164388 (1992-11-01), De et al.
patent: 5288514 (1994-02-01), Ellman
patent: 5324483 (1994-06-01), Cody et al.
patent: 5475013 (1995-12-01), Talley et al.
Jun and Beck-Sickinger (1992), "Multiple peptide synthesis methods and their applications," Angewandte Chemie 31:367-383.
Armstrong, R.W. et al., "Multiple-Component Condensation Strategies for Combinatorial Library Synthesis," Acc. Chem. Res. 29:123-131 (1996).
Bertho, J.N. et al., "Amino Acid Fluorides: Their Preparation and Use in Peptide Synthesis," Tetra. Letts. 32(10) :1303-1306 (1991).
Brenner, S. et al., "Encoded combinatorial chemistry," Proc. Natl. Acad. Sci. U.S.A. 89:5381-5383 (1992).
Burger, K. et al., "3,3,3-Trifluoro-2-isocyanopropionates, new versatile building blocks for the introduction of trifluoromethyl groups into organic molecules," J. Fluorine Chem. 65:149-152 (1993).
Carpino, L.A. et al., "((9-Fluorenylmethyl)oxy)carbonyl (FMOC) Amino Acid Fluorides. Convenient New Peptide coupling Reagents Applicable to the FMOC/tert-Butyl Strategy for Solution and Solid-Phase Syntheses," J. Am. Chem. Soc. 112:9651-9652 (1990).
Chaturvedi, N.C. et al., "Analogs of Angiotensin II. I. Solid Phase Synthesis," J. Med. Chem. 13:177-181 (1970).
El Marini, A. et al., "Synthesis of Enantiomerically Pure .beta.-and .gamma.-Amino Acids from Aspartic and Glutamic Acid Derivatives," Synthesis pp. 1104-1108 (1992).
Evans, D.A. et al., "Asymmetric Alkylation Reactions of Chiral Imide Enolates. A Practical Approach to the Enantioselective Synthesis of .alpha.-Substituted Carboxylic Acid Derivatives," J. Amer. Chem. Soc. 104:1737-1739 (1982).
Giesemann, G. et al., "Synthesis of Chiral .alpha.-Isocyano Esters and other Base-sensitive Isocyanides with Oxomethylenebis-(3H.sup.+ -Imidazolium) Bis (methanesulphonate), a Versatile Dehydrating Reagent," J. Chem. Res. (S) p. 79 (1982).
Geysen, H.M. et al., "Strategies for epitope analysis using peptide synthesis," J. Immunological Methods, 102:259-274 (1987).
Giron-Forest, D.A. et al., "Bromocriptine Methanesulphonate," Analytical Profiles of Drug Substances, 8:47-81, Academic Press (1979).
Gokel, G. et al., "Four-Component Condensations and Related Reactions," Isonitrile Chemistry, Ugi, I. ed., Academic Press, New York and London, pp. 145-199 (1971).
Hasumi, K. et al., "Lateritin, a new inhibitor of Acyl-CoA:Cholesterol acyltransferase produced by Gibberella lateritium IFO 7188," J. Antibiotics 46:1782-1787 (1993).
Horwell, D.C. et al., "The Design of a Dipeptide Library for Screening at Peptide Receptor Sites," Bioorganic & Medicinal Chemistry Letters 3(5):799-802 (1993).
Hwang, S.B. et al., "Specific Receptor Sites for 1-O-Alkyl-2-O-acetyl-sn-glycero-3-phosphocholine (Platelet Activating Factor) on Rabbit Platlet and Guinea Pig Smooth Muscle Membranes," Biochemistry 22:4756-4763 (1893).
Keating, T.A. et al., "Postcondensation Modifications of Ugi Four-Component Condensation Products: 1-Isocyanocyclohexene as a Convertible Isocyanide. Mechanism of Conversion, Syntghesis of Diverse Structures, and Demonstration of Resin Capture," J. Am. Chem. Soc. 118:2574-2583 (1996).
Kim, H.J. et al, "Polymer Attached Cyclic Dipeptides as Catalysts for Enantioselective Cyanohydrin Formation," Tetrahedron: Asymmetry 3(11) :1421-1430 (1992).
Kucharczyk, N. et al., "Tetrapeptide Tachykinin Antagonists: Synthesis and Modulation of the Physiocochemical and Pharmacological Properties of a New Seris of Partially Cyclic Analogs," J. Med. Chem. 36:1654-1661 (1993).
Leznoff, C.C., The Use of Insoluble Polymer Supports in General Organic Synthesis, Accounts of Chemical Research pp. 327-333 (1978).
Palom, Y. et al., "An Acid-Labile Linker for Solid-Phase Oligoribonucleotide Synthesis Using Fmoc Group for 5'-Hydroxyl Protection," Tetra. Letts. 34(13) :2195-2198 (1993).
Rajappa, S. et al., "Piperazine-2,5-diones and Related Lactim Ethers," Adv. Heterocyclic Chem. 57:187-289 (1993).
Sammes, P.G., "Naturally Occurring 2,5-Dioxopiperazines and Related Compounds," Fortschritte Der Chemie Organischer Naturstoffe (Progress in the Chemistry of Organic Natural Products) 33:51-118 (1975).
Scott, B.O. et al., "Solid Phase Organic Synthesis (SPOS): A novel route to diketopiperazines and diketomorpholines," Molecular Diversity 1(2) :125-134 (1995).
Shen, T.Y. et al., "Characterization of a platelet-activating factor receptor antagonist isolated from haifenteng (Piper futokadsura): Specific inhibition of in vitro and in vivo platelet-activating factor induced effects," Proc. Natl. Acad. Sci. U.S.A. 82:672-676 (1985).
Shimazaki, N. et al., "Diketopiperazines as a New class of Platelet-Activating Factor Inhibitors," J. Med. Chem. 30:1706-1709 (1987).
Shimizaki, N. et al., "Diketopiperazine Derivatives, a New Series of Platelet-Activating Factor Inhibitors," Chem Pharm. Bull 35(8) :3527-3530 (1987).
Shiosaki, K. et al., "Toward development of peptidomimetics: Diketopiperazine templates fo the Trp-Met segment of CCK-4," Peptides: Chemistry Structure and Biology ESCOM Science Publishers B.V., The Netherlands, pp. 978-980 (1990).
Williams, R.M. et al., "Bicyclomycin: Synthetic, Mechanistic, and Biological Studies," Chem. Rev. 88:511-540 (1988).
Winitz, M. et al., "Studies on Diastereoisomeric .alpha.-Amino Acids and Corresponding .alpha.-Hydroxy Acids. VII. Influence of .beta.-Configuration on Enzymic Susceptibility," J. Amer. Chem. Soc. 78:2423-2430 (1956).
Zuckerman, R.N. et al., "Efficient Method for the Preparation of Peptoids Am. Chem. Soc. 114:10646-10647 (1992).

Affiliated with

Also associated with

Rating

Method for synthesis of diketopiperazine and diketomorpholine de does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Method for synthesis of diketopiperazine and diketomorpholine de, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method for synthesis of diketopiperazine and diketomorpholine de will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-78236