490
Views
5
CrossRef citations to date
0
Altmetric
Review

Production of peptides as generic drugs: a patent landscape of octreotide

, , , , , , & show all
Pages 485-495 | Received 23 Nov 2015, Accepted 23 Feb 2016, Published online: 22 Mar 2016

References

  • Agyei D, Danquah MK. Industrial-scale manufacturing of pharmaceutical-grade bioactive peptides. Biotechnol Adv. 2011;29:272–277.
  • Hartmann R, Meisel H. Food-derived peptides with biological activity: from research to food applications. Curr Opin Biotechnol. 2007;18:163–169.
  • Zambrowicz A, Timmer M, Polanowski A, et al. Manufacturing of peptides exhibiting biological activity. Amino Acids. 2013;44:315–320.
  • Nestor JJ Jr. The medicinal chemistry of peptides. Curr Med Chem. 2009;16:4399–4418.
  • Frost & Sullivan.2004. [cited 2015 Nov 13]. Avalaible from: http://www.pharmamanufacturing.com/assets/Media/PublicationsArticle/Peptide.pdf
  • Fosgerau K, Hoffmann T. Peptide therapeutics: current status and future directions. Drug Discov Today. 2015;20:122–128.
  • Kolesińska B, Frączyk J, Sabatino G, et al. Sulfonates of N-triazinylammonium salts as highly efficient, inexpensive and environmentally friendly coupling reagents for peptide synthesis of as highly efficient. Chem Today. 2007;25(1):10–13.
  • Hojo K, Hara A, Kitai H. Development of a method for environmentally friendly chemical peptide synthesis in water using water-dispersible amino acid nanoparticles. Chem Cent J. 2011;5:49.
  • Hojo K, Maeda M, Kawasaki K. Solid-phase peptide synthesis in water. III. A water-soluble N-protecting group, 2-[phenyl(methyl)sulfonio]ethoxycarbonyl tetrafluoroborate, and its application to peptide synthesis. Tetrahedron. 2004;60:1875–1866.
  • Goodwin D, Simerska P, Toth I. Peptides as therapeutics with enhanced bioactivity. Curr Med Chem. 2012;19:4451–4461.
  • Rupp S. Next-generation bioproduction systems: cell-free conversion concepts for industrial biotechnology. Eng Life Sci. 2013;13:19–25.
  • Albericio F, Kruger HG. Therapeutic peptides. Future Med Chem. 2012;4:1527–1531.
  • Bray BL. Large-scale manufacture of peptide therapeutics by chemical synthesis. Nat Rev Drug Discov. 2003;2:587–593.
  • Benoiton NL. 2-Alkoxy-5(4H)-oxazolones and the enantiomerization of N-alkoxycarbonylamino acids. Biopolymers. 1996;40:245–254.
  • Sabatino G, Chelli M, Brandi A, et al. Curr Org Chem. 2004;8:291–301.
  • Sabatino G, Papini AM. Advances in automatic, manual and microwave-assisted solid-phase peptide synthesis. Curr Opin Drug Discov Devel. 2008;11:762–770.
  • Albericio F. Developments in peptide and amide synthesis. Curr Opin Chem Biol. 2004;8:211–221.
  • Albericio F, Carpino LA. Coupling reagents and activation. Method Enzymol. 1997;289:104–126.
  • Han S-Y, Kim Y-A. Recent development of peptide coupling reagents in organic synthesis. Tetrahedron. 2004;60:2447–2467.
  • Al-Warhi TI, Al-Hazimi HMA, ElFaham A. Recent development in peptide coupling reagents. J Saudi Chem Soc. 2012;16:97–116.
  • Sabatino G, Mulinacci B, Alcaro MC, et al. Assessment of new 6Cl-HOBt based coupling reagents for peptide synthesis. Part 1: coupling efficiency study. Lett Pept Sci. 2002;9:119–123.
  • Kamiński ZJ, Kolesińska B, Kolesińska J, et al. N-triazinylammonium tetrafluoroborates. A new generation of efficient coupling reagents useful for peptide synthesis. J Am Chem Soc. 2005;127:16912–16920.
  • Jastrząbek K, Kolesińska B, Sabatino G, et al. Benzyloxy derivatives of triazine-based coupling reagents designed for an efficient solid phase peptide synthesis on polystyrene resin. Int J Pept Res Ther. 2007;13:229–236.
  • Rizzolo F, Sabatino G, Chelli M, et al. A convenient microwave-enhanced solid-phase synthesis of difficult peptide sequences: case study of Gramicidin A and CSF114(Glc). Int J Pept ResTher. 2007;13:203–208.
  • Uhlig T, Kyprianou T, Martinelli FG, et al. The emergence of peptides in the pharmaceutical business: from exploration to exploitation. EuPA Open Proteom. 2014;4:58–69.
  • Sevarino KA, Felix R, Banks CM, et al. Cell-specific processing of preprosomatostatin in cultured neuroendocrine cells. J Biol Chem. 1987;262:4987–4993.
  • Benoit R, Esch F, Bennett HP, et al. Processing of prosomatostatin. Metabolism. 1990;39:22–25.
  • Rivier JE. Somatostatin. Total solid phase synthesis. J Am Chem Soc. 1974;96:2986–2992.
  • Burgus R, Ling N, Butcher M, et al. Primary structure of somatostatin, a hypothalamic peptide that inhibits the secretion of pituitary growth hormone. Proc Natl Acad Sci USA. 1973;70:684–688.
  • Pradayrol L, Jörnvall H, Mutt V, et al. N-terminally extended somatostatin: the primary structure of somatostatin-28. FEBS Lett. 1980;109:55–58.
  • Guillemin R. Peptides in the brain: the new endocrinology of the neuron. Science. 1978;202:390–402.
  • Reichlin S. Somatostatin. N Engl J Med. 1983;309:1495–1501.
  • Reichlin S. Somatostatin (second of two parts). N Engl J Med. 1983;309:1556–1563.
  • Lewin MJ. The somatostatin receptor in the GI tract. Annu Rev Physiol. 1992;54:455–468.
  • Epelbaum J. Somatostatin in the central nervous system: physiology and pathological modifications. Prog Neurobiol. 1986;27:63–100.
  • Epelbaum J, Dournaud P, Fodor M, et al. The neurobiology of somatostatin. Crit Rev Neurobiol. 1994;8:25–44.
  • Yamada Y, Post SR, Wang K, et al. Cloning and functional characterization of a family of human and mouse somatostatin receptors expressed in brain, gastrointestinal tract and kidney. Proc Natl Acad Sci USA. 1992;89:251–255.
  • Patel YC. Somatostatin and its receptor family. Front Neuroendocrinol. 1999;20:157–198.
  • Weckbecker G, Lewis I, Albert R, et al. Opportunities in somatostatin research: biological, chemical and therapeutic aspects. Nat Rev Drug Discov. 2003;2:999–1017.
  • Patel YC, Srikant CB. Subtype selectivity of peptide analogs for all five cloned human somatostatin receptors (hsstr 1-5). Endocrinology. 1994;135:2814–2817.
  • Reubi JC, Schaer JC, Waser B, et al. Expression and localization of somatostatin receptor SSTR1, SSTR2, and SSTR3 messenger RNAs in primary human tumors using in situ hybridization. Cancer Res. 1994;54:3455–3459.
  • Reubi JC, Waser B, Schaer JC, et al. Somatostatin receptor sst1-sst5 expression in normal and neoplastic human tissues using receptor autoradiography with subtype-selective ligands. Eur J Nucl Med. 2001;28:836–846.
  • Lamberts SW, Van Der Lely AJ, De Herder WW, et al. Octreotide. N Engl J Med. 1996;334:246–254.
  • Veber DF, Freidinger RM, Perlow DS, et al. A potent cyclic hexapeptide analogue of somatostatin. Nature. 1981;292:55–58.
  • Brady SF, Freidinger RM, Paleveda WJ, et al Large-scale synthesis of a cyclic hexapeptide analogue of somatostatin. J Org Chem. 1987;52:764–769.
  • Freidinger RM. Design and synthesis of novel bioactive peptides and peptidomimetics. J Med Chem. 2003;46(26):5553–5566.
  • Janecka A, Zubrzycka M, Janecki T. Somatostatin analogs. J Pept Res. 2001;58:91–107.
  • Pless J. The history of somatostatin analogs. J Endocrinol Invest. 2005;28:1–4.
  • Veber DF, Saperstein R, Nutt RF, et al A super active cyclic hexapeptide analog of somatostatin. Life Sci. 1984;34:1371–1378.
  • Freidinger RM, Paleveda WJ, Colton CD, et al. Large-scale synthesis of a cyclic hexapeptide analogue of somatostatin. J Org Chem. 1987;52:764–769.
  • Lewis I, Bauer W, Albert R, et al A novel somatostatin mimic with broad somatotropin release inhibitory factor receptor binding and superior therapeutic potential. J Med Chem. 2003;46:2334–2344.
  • Weckbecker G, Lewis I, Albert R, et al Oppurtinities in somatostatin research: biological and therapeutic aspects. Nat Review Drug Discov. 2003;2:999–1017.
  • Bauer W, Briner U, Doepfner W, et al. SMS 201-995: a very potent and selective octapeptide analogue of somatostatin with prolonged action. Life Sci. 1982;31:1133–1140.
  • Marbach P, Briner U, Lemaire M, et al. From somatostatin to sandostatin: pharmacodynamics and pharmacokinetics. Metabolism. 1992;41:7–10.
  • Reubi JC, Schär JC, Waser B, et al. Affinity profiles for human somatostatin receptor subtypes SST1-SST5 of somatostatin radiotracers selected for scintigraphic and radiotherapeutic use. Eur J Nucl Med. 2000;27:273–282.
  • Deghenghi R, Papotti M, Ghigo E, et al Somatostatin octapeptides (lanreotide, octreotide, vapreotide, and their analogs) share the growth hormone–releasing peptide receptor in the human pituitary gland. Endocrine. 2001;14(1):29–33.
  • Fields GB, Tian Z, Barany G. Principles and practice of solid-phase peptide synthesis. In: Grant GA, ed. Synthetic peptides: A user’s guide. New York: Freeman WH & Co; 1992.
  • Marbach P, Bauer W, Bodmer D, et al. Discovery and development of somatostatin agonists. In: Borchardt RT, Freidinger RM, Sawyer TK, et al. editors. Integration of pharmaceutical discovery and development: case histories. New York: Kluwer; 2002. p. 183–205.
  • Neugebauer W, Escher E. Solid-phase synthesis of C-terminal peptide amino alcohols. Helv Chim Acta. 1989;72:1319–1323.
  • Neugebauer W, Lefevre MR, Laprise R, et al. Peptides: chemistry, structure and biology. Marshal GR, Rivier JE, eds. Leiden: ESCOM; 1990.
  • Mergler M, Hellstern H, Wirth W, et al. A. new acid-labile linker for the solid-phase synthesis of peptides with C-terminal threoninol. In abstracts of the twelfth american peptide symposium, june 16-21,1991, Boston, MA. Cambridge: Massachusetts Institute of Technology; 1991. p. P–292.
  • Mergler M, Nyfeler R. Rapid synthesis of fully protected peptide alcohols. Peptides 1992. Schneider CH, Eberle AN, eds. Leiden: ESCOM; 1993.
  • Edwards WB, Fields CG, Anderson CJ, et al. Generally applicable, convenient solid-phase synthesis and receptor affinities of octreotide analogs. J Med Chem. 1994;37:3749–3757.
  • Wenschuh H, Beyermann M, Haber H, et al. Stepwise automated solid phase synthesis of naturally occurring peptaibols using Fmoc amino acid fluorides. J Org Chem. 1995;60:405–410.
  • Barlos K, Gatos D, Kallitsis J, et al. Darstellung geschützter peptid-fragmente unter einsatz substituierter triphenylmethyl-harze. Tetrahedron Lett. 1989;30:3943–3946.
  • Arano Y, Akizawa H, Uezono T, et al. Conventional and high-yield synthesis of DTPA-conjugated peptides: application of a monoreactive DTPA to DTPA-D-Phe1-octreotide synthesis. Bioconjug Chem. 1997;8:442–446.
  • Institute of Nuclear Energy Research, Taiwan Hsieh YT, Chang SR, Chyi SY, et al. Process for preparing octreotide and derivatives thereof US 6476186. 2002
  • Teva Pharmaceuticals USA Tovi A, Eidelman C, Shushan S, et al. Process for production of cyclic peptides. WO2004092202. 2004.
  • Schmidt MA, Wilhelm RR, Srinivasan A. In Abstracts of the fifteenth american peptide symposium. Nashville. Nashville (TN): American Peptide Society; p. 2–109. 1997 June 14–19.
  • Alsina J, Chiva C, Ortiz M, et al. Active carbonate resins for solid-phase synthesis through the anchoring of a hydroxyl function. Synthesis of cyclic and alcohol peptides. Tetrahedron Lett. 1997;38:883–886.
  • Zheng A, Shan D, Wang B. A redox-sensitive resin linker for the solid phase synthesis of C-terminal modified peptides. J Org Chem. 1999;64:156–161.
  • Mergler M, Dick F, Gosteli J, et al. Solid phase synthesis of fully protected peptide alcohols. Tetrahedron Lett. 1999;40:4663–4664.
  • Wu Y-T, Hsieh H-P, Wu C-Y, et al. Facile solid phase synthesis of octreotide analogs using p-carboxybenzaldehyde as a novel linker to anchor Fmoc-threoninol to solid phase resins. Tetrahedron Lett. 1998;39:1783–1784.
  • Hsieh HP, Wu YT, Chen ST, et al. Direct solid-phase synthesis of octreotide conjugates: precursors for use as tumor-targeted radiopharmaceuticals. Bioorg Med Chem. 1999;7:1797–1803.
  • Institute of Nuclear Energy Research, TaiwanLee TW, Chen ST, Chang SR, et al. Synthesis of bifunctional chelating agents-peptides. US5889146. 1999.
  • Carotenuto A, D ‘Addona D, Rivalta E, et al. Synthesis of a dicarba-analog of octreotide keeping the type II’ β-turn of the pharmacophore in water solution. Lett Org Chem. 2005;2:274–279.
  • D’Addona D, Carotenuto A, Novellino E, et al. Novel sst5-selective somatostatin dicarba-analogues: synthesis and conformation-affinity relationships. J Med Chem. 2008;51:512–520.
  • Lipotec SA, SpainClemente Rodriguez FJ, Ponsati Obiols B, et al. Procedure for obtaining the somatostatin analog octreotide. EP0953577 1999 and US6346601. 2002.
  • Roux S, et al. Elimination and exchange of trifluoroacetate counter-ion from cationic peptides: a critical evaluation of different approaches. J Pept Sci. 2008;14:354–359.
  • Sandoz Ltd, SwitzerlandBauer W, Pless J Novel polypeptides, processes for their production, pharmaceutical compositions comprising said polypeptides and their use. US4395403 EP0029579. 1983.
  • Sandoz Ltd, SwitzerlandRainer A, Bauer W, Cardinaux F et al. Synthesis of peptide alcohols. GB2233652. 1991.
  • Institute of Nuclear Energy Research, TaiwanLee TW, Chen ST, Chang SR, et al. Synthesis of bifunctional chelating agents-peptides. US5889146. 1999.
  • Samukov VV, Pozdnjakov PI Synthesis in solution of octreotide using various protective groups for improved synthesis. RU 2196144. 2001.
  • Inst. of Toxic Drugs, Academy of Military Medical Sciences, PLA, Peop. Rep. ChinaLiu K, Liang Y, Li B. et al. Liquid phase synthesis of octreotide acetate. CN1355173. 2002.
  • Chaturvedi NC, et al. Novel process for production of the somatostatin analog, octreotide. Synthesis in solution of peptide fragments and their coupling using the scheme [3+3]+2 WO200303097668. 2003.
  • Eli Lilly, USA Mayer, Philip J, Zeng YL. Use of trichloroacetimidate linker for peptide synthesis. US0039161. 2004.
  • Chang chun Lifein Pharmaceutical Co., Ltd., Peop. Rep. ChinaJia Z, Wang E Solid-phase synthesis of octreotide acetate. CN1569890. 2005.
  • Chemi Spa, Cinisello Balsamo, Italy Cappelletti S, Storace O, Annoni P et al. Process for the formation of disulfide bonds in cyclic peptides. US 20050239695. 2005.
  • Dalton Chemical Lab IncIarov A, Avrutov I, Lazarowych N, et al. Process for octreotide synthesis. WO087794. 2005.
  • Wockhardt Ltd, India Singh KKL, Mukarram SMJ, Ashok DA et al. Processes for the preparation of octreotide. WO 2007110765A2. 2007.
  • Limited USV, IndiaSaksena DL, Pawar DS, et al. An improved process for synthesis of cyclic octapeptide. WO089757. 2010.
  • ZAO “Farm-Sintez”, RussiaNazarenko AB, Balaev AN, Fedorov VE Method for obtaining cyclic peptide-octreotide. RU2435780. 2010.
  • Centre National de la Recherche Scientifique (CNRS) Fr Caussil M, Martinez J, Tailhades J, Synthesis of peptide alcohols by solid phase synthesis of depsipeptides and O-N acyl-transfer reaction in solution. EP2270025 and WO2011000848. 2011.
  • Natco Pharma Limited Kota S, Tallapaneni V, Adibhatla KSBR, et al. Improved process for the preparation of octreotide by solution phase synthesis. WO132505. 2013.
  • Chemical & Biopharmaceutical Laboratories of Patras S.A. Barlos KK. Solid phase peptide synthesis via side chain attachment. WO098802. 2013.
  • Mylan Laboratories Ltd Kuppanna A, Dokka MS, Vanjivaka S, et al. Process for the preparation of octreotide acetate. WO046233A2.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.