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Developments around the bioactive diketopiperazines: a patent review

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Pages 1415-1433 | Published online: 21 Aug 2013

Bibliography

  • Borthwick AD. 2,5-diketopiperazines: synthesis, reactions, medicinal chemistry, and bioactive natural products. Chem Rev 2012;112:3641-716
  • Cornacchia C, Cacciatore I, Baldassarre L, et al. 2,5-Diketopiperazines as neuroprotective agents. Mini Rev Med Chem 2012;12:2-12
  • Eriko I, Yoshitaka H, Mikiko S. Epipolythiodiketopiperazine alkaloids: total syntheses and biological activities. J Chem 2011;51:420-33
  • Minelli A, Bellezza I, Grottelli S, et al. Focus on cyclo-(His-Pro): history and perspectives as antioxidant peptide. Amino Acids 2008;35:283-9
  • Martins MB, Carvalho I. Diketopiperazines: biological activity and synthesis. Tetrahedron 2007;63:9923-32
  • Huang R, Zhou X, Xu T, et al. Diketopiperazines from marine organisms. Chem Biodivers 2010;7:2809-29
  • Fischer PM. Diketopiperazines in peptide and combinatorial chemistry. J Pept Sci 2003;9:9-35
  • Dinsmore JC, Beshore DC. Recent advances in the synthesis of diketopiperazaines. Tetrahedron 2002;58:3297-312
  • Guo XC, Zheng L, Zhou WH, et al. Research advance on diketopiperazines produced by marine microorganism. Microbiology 2009;36:1596-603
  • Lin H, Wang D. Progress in the synthesis of diketopiperazines. Acta Pharm Sin 2003;38:395-400
  • Ortho Pharmarceutical Corperation. Immunoregulatory diketopiperazine compounds. US4289759; 1981
  • Ortho Pharmarceutical Corperation. Immunoregulatory diketopiperazine compounds. US4331595; 1982
  • Development Institure, Inc. at Montana State University. Method of inducing chlorosis in a knapweed plant. US4929270; 1990
  • Fujisawa Pharmaceutical Co., Ltd. Piperazine compound as PAF-antagonist. US4940709; 1990
  • Snow Brand Milk Prod. Co., Ltd. New diketopiperazine derivative and immunosuppressive agent containing the same as active ingredient. JP3176478; 1991
  • Kanebo Ltd. Anti-neoplastic agent. JP5163148; 1993
  • The University of Maryland at Baltimore. Histidyl-proline diketopiperazine (cyclo-(His-Pro)), a CNS-active pharmacologic agent. US5418218; 1995
  • Prasad C. Histidyl-proline diketopiperazine and method of use. WO0201956; 2002
  • Kaiyo Bio Technol Kenkyusho: KK, Shizuoka Prefecture. Chitinase inhibitor. JP8277203; 1996
  • Teika Seiyaku. Remedy for inflammatiory disease containing diketopiperazine derivative. JP2000327575; 2000
  • Dmi Biosciences, Inc. Method of using diketopiperazines and composition containing them. WO200211676; 2002
  • Dmi Biosciences, Inc. Treatment of T-cell-mediated diseases. WO2004103304; 2004
  • Dmi Biosciences, Inc. Treatment of T-cell-mediated diseases. CN101279094; 2008
  • Georgetown University. Cyclic dipeptides and azetidinone compounds and their use in treating CNS injury and neurodegenerative disorders. US20070161640; 2007
  • Università Deglistudi di Udine. Antifungal compositions containing the endophyte fungus Alternaria alrernata and/or its metabolites, as antagonist agents of Plasmopara viticola. WO2008007251; 2008
  • Dmi Biosciences, Inc. Therapeutic Methods and compounds. WO2009146320; 2009
  • Suntory Holdings Ltd and Cerebos Pacific Ltd. Leaning motivation improvers. WO2011077760; 2011
  • Dmi Acquisition Corp. Treatment of diseases. US2012172294; 2012
  • Dmi Acquisition Corp. Treatment of diseases. US2012058934; 2012
  • Allied Chem Corp. Method of combation nematods employing N,N′-disubstituted-2,5-diketopiperazaines. US3692908; 1972
  • Merck & Co., Inc., USA. Inhibitors of farnesyl-protein transferase. WO9736888; 1997
  • Smithkline Beecham Corp. Hemoregulatory compounds. WO9718214; 1997
  • Affymax Technologies NV. Collagenase-1 and stromelysin-1 inhibitors, pharmaceutical compositions comprising same and methods of their use. US5932579; 1999
  • Ontogen Corp. Piperazines as inhibitors of fructose-1,6-bisphosphatase (FBPase). WO9947549; 1999
  • Novoscience Pharma, Inc. Diketopiperazine derivatives to inhibit thrombin. WO0140224; 2001
  • Mitsubishi Chemical Industries, Ltd. N2-Arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof. US4258192; 1981
  • Mitsubishi Chemical Industries, Ltd. N2-Arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof. US4201863; 1980
  • Celltech R & D, Inc., USA. Pharmaceutical uses and synthesis of diketopiperazine. US20020187984; 2002
  • Glaxo Group Ltd. Substituted diketopiperazines for the treatment of benign prostatic hyperplasia. WO2005000311; 2005
  • Glaxo Group Ltd. Substituted diketopiperazines and their use as oxytocin antagonists. WO2005000840; 2005
  • Glaxo Group Ltd. Novel compounds. WO2006000399; 2006
  • Glaxo Group Ltd. Substituted diketopiperazines as oxytocin antagonists. WO2006000400; 2006
  • Glaxo Group Ltd. Substituted diketopiperazines as oxytocin antagonists. WO2006000759; 2006
  • Glaxo Group Ltd. 1,6-disubstituted-(3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-2,5-piperazinedione derivatives as oxytocin receptor antagonists for the treatment of pre-term labor, dysmenorrhea and endometriosis. WO2006067462; 2006
  • Glaxo Group Ltd. Substituted diketopiperazines as oxytocin antagonists. WO03053443; 2003
  • Borthwick AD, Liddle J. The design of orally bioavailable 2,5-diketopiperazine oxytocin antagonists: from concept to clinical candidate for premature labor. Med Res Rev 2011;31:576-604
  • Borthwick AD, Liddle J, Davies DE, et al. Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency. J Med Chem 2012;55:783-96
  • Ono Pharmaceutical Co., Ltd. Triazaspiro[5.5]undecane derivatives and drugs containing the same as the active ingredient. WO02074770; 2002
  • Maeda K, Nakata H, Koh Y, et al. Spirodiketopiperazine-based CCR5 inhibitor which preserves CC-chemokine/CCR5 interactions and exerts potent activity against R5 Human immunodeficiency virus type 1 in vitro. J Virol 2004;78:8654-62
  • Nichols WG, Steel HM, Bonny T, et al. Hepatotoxicity observed in clinical trials of aplaviroc (GW873140). Antimicrob Agents Chemother 2008;52:858-65
  • Adkison KK. Pharmacokinetics and short-term safety of 873140, a novel CCR5 antagonist, in healthy adult subjects. Antimicrob Agents Chemother 2005;49:2802-6
  • Progenics Pharmaceuticals, Inc. Methods of inhibiting infection by diverse subtypes of drug-resistant HIV-1. WO 2009134401; 2009
  • Miyoshi T, Miyairi N, Aoki H, et al. Bicyclomycin, a new antibiotic. I. Taxonomy, isolation, and characterization. J Antibiot 1972;25:569-75
  • Fujisawa Pharmaceutical Co., Ltd. Bicyclomycin derivatives. US4215043; 1976
  • Williams RM, Durham CA. Bicyclomycin: synthetic, mechanistic, and biological studies. Chem Rev 1988;88:511-40
  • Kohn H, Widger WC. The molecular basis for the mode of action of bicyclomycin. Drug Targets Infect Disord 2005;5:273-95
  • Fujisawa Pharmaceutical Co., Ltd. Bicyclomycin as an animal growth promotion. US4209518; 1978
  • Novartis Animal Health Australasia PTY Ltd and Microbial Screening Technologies PTY Ltd. Terpenylated diketopiperazines (drimentines). WO9809968; 1998
  • Lilly Icos Llc. Tetracyclic diketopiperazine compounds as PDEV inhibitors. WO0194347; 2001
  • Icos Corp. Tetracyclic derivatives, process of preparation and use. US5859006; 1999
  • Coward RM, Carson CC. Tadalafil in the treatment of erectile dysfunction. Ther Clin Risk Manag 2008;4:1315-30
  • Wyeth Holdings Corp. Reversal of multidrug resistance in human colon carcinoma cells. US6537964; 2003
  • Neuren Pharmaceuticals Ltd. Neuroprotective bicyclic compounds and methods for their use. WO2005023815; 2005
  • Rikagaku Kenkyuzyo. Triprostatins manufacture with Aspergillus. JP09059275; 1997
  • Takeo U, Masuo K, Cui CB, et al. Tryprostatin A, a specific and novel inhibitor of microtubule assembly. Biochem J 1998;333:543-8
  • Huboldt-Universitàt Zu Berlin. Uses of tryprostatin for the reversal of cancer drug resistance. WO2004087162; 2004
  • Council of Scientific and Industrial Research. Chrysogenazine obtained from fungus Penicillium chrysogenum having antibacterial activity. WO2005063740; 2005
  • Shenyang Pharmaceutical University. Antineoplastic active substance of diketopiperazine PJ147and PJ157. CN101041640; 2007
  • Shenyang Pharmaceutical University. Method for synthesizing antitumor compound of diketopiperazine PJ147. CN101255139; 2008
  • Shenyang Pharmaceutical University. New diketone piperazidine-like derivative and application thereof. CN101935306; 2011
  • Institute of Oceanology Chinese Academy of Sciences. The application of an indolyl diketopiperazine compound. CN102669110; 2012
  • Institute of Oceanology Chinese Academy of Sciences. An indolyl diketopiperazine-like derivative, its preparation method and application. CN102675293; 2012
  • The United States of America as represented by the Secretary of Agriculture, University of Iowa Research Foundation and Biotechnology Research and Development Corpor. N-Methylepiamauromine epiamauromine and cycloechinulin antiinsectan metabolites. WO9301718; 1993
  • Institute of Pharmacology and Toxicology of Academy of Military Medical Sciences. Diketopiperazine compound as well as composition, preparation method and application thereof. CN102020649; 2011
  • Ocean University of China. A tryptophan- and proline-derived indole diketopiperazine alkaloid, its preparation method and application. CN102268005; 2011
  • Xenova Ltd Pharmaceutical. Diketopiperazine compounds. WO9404512; 1994
  • Xenova Ltd Pharmaceutical. Diketopiperazine compounds. WO9532190; 1995
  • Nippon Steel Corp. Cell division inhibitors and process for producing the same. WO2001053290; 2001
  • Nereus Pharmaceuticals, Inc. Phenylahistin and the phenylahistin analogs, a new class of anti-tumor compounds. US6358957; 2002
  • Nicholson B, Kenneth GL, Millera BR. NPI-2358 is a tubulin-depolymerizing agent: in-vitro evidence for activity as a tumor vascular-disrupting agent. Anti Cancer Drugs 2006;17:25-30
  • Mayer AM, Glaser KB, Cuevas C, et al. The odyssey of marine pharmaceuticals: a current pipeline perspective. Trends Pharmacol Sci 2010;31:255-65
  • Korea Research Institute of Bioscience and Biotechnology. Penicillium sp. F70614(KCTC 8918P) and an α-glucosidase inhibitor. KR20010025876; 2001
  • Xiamen University. Manufacture of diketopiperazine derivative by fermentation of Papularia. CN1667126; 2004
  • Shenyang Pharmaceutical University. Manufcature of antitumoric thiopiperazinedione derivative with Aspergillus fumigates. CN102051394; 2011
  • Korea Institute of Science and Technology. Aspergillus sp. KMD 901, diketopiperazines isolated from the strain, and composition containing diketopiperazines for preventing or treating cancer. KR2011045763; 2011
  • Ocean University of China. Polysulfide bond-containing piperazidine compound isolated from Oidiodendron truncatum and antitumor application thereof. CN101812079; 2010
  • Mannkind Corp. Formation of N-protected 3,6-bis(4-aminoalkyl)-2,5,diketopiperazines. WO2012109256; 2012
  • Qing Y. Synthetic methods of 3,6-bis(4-bisfumaroyl aminobutyl)-2,5-diketopiperazine and salt substitute thereof. CN101851213; 2010
  • Nanjing University of Technology. Method for preparing high-purity diketopiperazine cyclopeptide. CN102146065; 2011
  • Temple University of the Commonwealth System of Higher Education. Acylation of hindered amines and functional bis-peptides obtained thereby. US2011184171; 2011
  • Indiana University Research and Technology Corp. Ester-based peptide prodrugs. US20110065633; 2011
  • Mannkind Corp. Catalysis of diketopiperazine synthesis. US2006041133; 2006
  • Toyohashi University of Technology. Method of synthesis for cyclic peptides utilizing high temperature and high pressure water. JP2003252896; 2003
  • DMI Biosciences, Inc. Method of synthesizing diketopiperazines. WO0212201; 2002
  • Degussa A.G. Production of known and new 2,5-diketopiperazine derivatives useful for the synthesis of bioactive compounds, e.g. cyclo(Lys-Lys). DE20001019879;2001
  • Affymax Technologies N.V. UK. Method for synthesis of diketopiperazine and diketomorpholine derivatives. US5817751; 1998
  • Affymax Technologies N.V. UK. Method for the synthesis of diketopiperazines. WO9600391; 1996
  • Mitsui Toatsu Chem, Inc. Preparation of 3,6-bis[(4-hydroxyphenyl)methyl]-2,5-diketopiperazine. JP06321916; 1994
  • Ajinomoto Co., Inc. Process for preparing diketopiperazine derivatives. JP04234374; 1992
  • Monsanto Co. The compound 1,4-diisopropyl-2,5-diketopiperazine. EP0216744; 1987
  • Wang P, Xi L, Liu P, et al. Diketopiperazine derivatives from the marine-derived actinomycete Streptomyces sp. FXJ7.328. Mar Drugs 2013;11:1035-49
  • Mannkind Corp. Dry powder drug delivery system and methods. WO2011163272; 2011
  • Mannkind Corp. Val (8) glp-1 composition and method for treating functional dyspepsia and/or irritable bowel syndrome. WO2011017554; 2011
  • Mannkind Corp. Diketopiperazine microparticles with defined specific surface areas. WO2010144789; 2010
  • Mannkind Corp. An improved dry powder drug delivery system. WO2010102148; 2010
  • Mannkind Corp. Glucagon-like peptide 1 (GLP-1) pharmaceutical formulations. US2008260838; 2008
  • Mannkind Corp. Method for improving the pharmaceutic properties of microparticles comprising diketopiperazine and an active agent. US2007196503; 2007
  • Mannkind Corp. Method of drug formulation based on increasing the affinity of crystalline microparticle surfaces for active agents. US2007059373; 2007
  • Mannkind Corp. Diketopiperazine salts for drug delivery and related methods. US20060040953; 2006
  • Mannkind Corp. Cell transport compositions and uses thereof. WO2004012672; 2004
  • Pharmaceutical Discovery Corp. Compositions for treatment or prevention of bioterrorism. WO03061578; 2003
  • Emisphere Techinologies, Inc. Diketopiperazine-based delivery systems. WO9609813; 1996
  • Kamiya T, Maeno S, Hashimoto M, Mine Y. Bicyclomycina, new antibiotic. II. Structurale lucidation and acyl derivatives. J Antibiot 1972;25:576-81

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