Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – Synthesis of peptides
Reexamination Certificate
2011-07-19
2011-07-19
Russel, Jeffrey E (Department: 1654)
Chemistry: natural resins or derivatives; peptides or proteins;
Peptides of 3 to 100 amino acid residues
Synthesis of peptides
C530S345000
Reexamination Certificate
active
07981999
ABSTRACT:
The present invention provides novel peptidomimetic macrocycles and methods for their preparation and use, as well as amino acid analogs and macrocycle-forming linkers, and kits useful in their production. In various embodiments, the peptidomimetic macrocycles are of Formula I:The linker L includes a triazole moiety. Peptidomimetic macrocycles according to the invention may exhibit increased α-helical or beta sheet structure in aqueous solution compared to a corresponding non-macrocyclic polypeptide.
REFERENCES:
patent: 4000259 (1976-12-01), Garsky
patent: 4191754 (1980-03-01), Veber et al.
patent: 5364851 (1994-11-01), Joran
patent: 5446128 (1995-08-01), Kahn
patent: 5622852 (1997-04-01), Korsmeyer
patent: 5650133 (1997-07-01), Carvalho et al.
patent: 5663316 (1997-09-01), Xudong
patent: 5708136 (1998-01-01), Burrell et al.
patent: 5811515 (1998-09-01), Grubbs et al.
patent: 5817752 (1998-10-01), Yu
patent: 5824483 (1998-10-01), Houston, Jr. et al.
patent: 5834209 (1998-11-01), Korsmeyer
patent: 5840833 (1998-11-01), Kahn
patent: 5856445 (1999-01-01), Korsmeyer
patent: 5859184 (1999-01-01), Kahn et al.
patent: 5955593 (1999-09-01), Korsmeyer
patent: 5965703 (1999-10-01), Horne et al.
patent: 5998583 (1999-12-01), Korsmeyer
patent: 6153391 (2000-11-01), Picksley et al.
patent: 6169073 (2001-01-01), Halazonetis et al.
patent: 6271198 (2001-08-01), Braisted et al.
patent: 6326354 (2001-12-01), Gross et al.
patent: 6613874 (2003-09-01), Mazur et al.
patent: 6703382 (2004-03-01), Wang et al.
patent: 6713280 (2004-03-01), Huang et al.
patent: 7064193 (2006-06-01), Cory et al.
patent: 7083983 (2006-08-01), Lane et al.
patent: 7192713 (2007-03-01), Verdine et al.
patent: 7202332 (2007-04-01), Arora et al.
patent: 7247700 (2007-07-01), Korsmeyer et al.
patent: 7705118 (2010-04-01), Arora et al.
patent: 7723469 (2010-05-01), Walensky et al.
patent: 7786072 (2010-08-01), Verdine et al.
patent: 2003/0166138 (2003-09-01), Kinsella et al.
patent: 2004/0106548 (2004-06-01), Schmidt et al.
patent: 2004/0152708 (2004-08-01), Li et al.
patent: 2004/0171809 (2004-09-01), Korsmeyer et al.
patent: 2005/0119167 (2005-06-01), Abbenante et al.
patent: 2005/0222427 (2005-10-01), Sharpless et al.
patent: 2005/0250680 (2005-11-01), Walensky et al.
patent: 2006/0014675 (2006-01-01), Arora et al.
patent: 2006/0111411 (2006-05-01), Cooper et al.
patent: 2008/0213175 (2008-09-01), Kolb et al.
patent: 2009/0047711 (2009-02-01), Nash
patent: 2009/0088553 (2009-04-01), Nash
patent: 2009/0149630 (2009-06-01), Walensky et al.
patent: 2009/0176964 (2009-07-01), Walensky et al.
patent: 2009/0275519 (2009-11-01), Nash et al.
patent: 2009/0326192 (2009-12-01), Nash et al.
patent: 2010/0081611 (2010-04-01), Bradner et al.
patent: 2010/0168388 (2010-07-01), Bernal et al.
patent: 2010/0184628 (2010-07-01), Nash
patent: 2010/0184645 (2010-07-01), Verdine et al.
patent: 2010/0210515 (2010-08-01), Nash et al.
patent: 2010/0216688 (2010-08-01), Nash et al.
patent: 2010/0234563 (2010-09-01), Arora et al.
patent: 2010/0273704 (2010-10-01), Korsmeyer et al.
patent: 2010/0298201 (2010-11-01), Nash et al.
patent: 1583730 (2005-02-01), None
patent: 1452868 (2004-09-01), None
patent: WO 89/09233 (1989-10-01), None
patent: WO 93/01203 (1993-01-01), None
patent: WO 94/25482 (1994-11-01), None
patent: WO 95/00534 (1995-01-01), None
patent: WO 96/28449 (1996-09-01), None
patent: WO 97/00267 (1997-01-01), None
patent: WO 97/30072 (1997-08-01), None
patent: WO 98/46631 (1998-10-01), None
patent: WO 02/072597 (2002-09-01), None
patent: WO 03/059933 (2003-07-01), None
patent: WO 03/059933 (2004-01-01), None
patent: WO 2004/058804 (2004-07-01), None
patent: WO 2004/077062 (2004-09-01), None
patent: WO 2004/077062 (2005-01-01), None
patent: WO 2005007675 (2005-01-01), None
patent: WO 2004/077062 (2005-02-01), None
patent: WO 2005/040202 (2005-05-01), None
patent: WO 2005/044839 (2005-05-01), None
patent: WO 2005/040202 (2005-06-01), None
patent: WO 2005/044839 (2005-07-01), None
patent: WO 2005/090388 (2005-09-01), None
patent: WO 2006/078161 (2006-07-01), None
van Maarseveen et al. Efficient Route to C2 Symmetric Heterocyclic Backbone Modified Cyclic Peptides. Organic Letters. 2005, vol. 7, No. 20, pp. 4503-4506.
Berendsen, H. A glimpse of the Holy Grail? Science. Oct. 23, 1998;282(5389):642-3.
Bock, et al. 1,2,3-Triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptide mimics. Org Biomol Chem. Mar. 21, 2007;5(6):971-5.
Bradley, et al. Limits of cooperativity in a structurally modular protein: response of the Notch ankyrin domain to analogous alanine substitutions in each repeat. J Mol Biol. Nov. 22, 2002;324(2):373-86.
Definition of Analog from http://cancerweb.ncl.ac.uk/cgi-bin/omd?query=analog. pp. 1-5. Accessed Jul. 7, 2005.
Designing Custom Peptides. From SIGMA Genosys. pp. 1-2. Accessed Dec. 16, 2004.
European search report dated Mar. 2, 2010 for Application No. 8730678.3.
International search report dated Apr. 28, 2008 for PCT Application No. US2007/87615.
International search report dated Sep. 25, 2008 for PCT Application No. US2008/54922.
Jackson, et al. General approach to the synthesis of short α-helical peptides. Journal of the American Chemical Society. 1991;113(24) 9391-9392.
Ngo, et al. Computational complexity, protein structure prediction, and the levinthal paradox. The Protein Folding Problem and Tertiary Structure Prediction. K. Merc Jr. and S. Le Grand Edition. 1994, pp. 491-495.
Rudinger, J. Characteristics of the amino acids as components of a peptide hormone sequence. Peptide Hormones. JA Parsons Edition. University Park Press. Jun. 1976, pp. 1-7.
Schinzel, et al. The phosphate recognition site ofEscherichia colimaltodextrin phosphorylase. FEBS Lett. Jul. 29, 1991;286(1-2):125-8.
Solution phase synthesis from http://www.combichemistry.com/solution—phase—synthesis.html. P.1. Accessed Aug. 6, 2009.
Taylor, J. The synthesis and study of side-chain lactam-bridged peptides. Biopolymers. 2002;66(1):49-75.
Voet, et al. Biochemistry, Second Edition. John Wiley & Sons, Inc. 1995, pp. 235-241.
Andrews, et al. Forming Stable Helical Peptides Using Natural and Artificial Amino Acids. Tetrahedron. 1999; 55:11711-11743.
Angell, et al. Peptidomimetics via copper-catalyzed azide-alkyne cycloadditions. Chem Soc Rev. Oct. 2007;36(,10):1674-89.
Angell, et al. Ring closure to beta-turn mimics via copper-catalyzed azide/alkyne cycloadditions. J Org Chem. Nov. 11, 2005;70(23):9595-8.
Baell, et al. Prospects for targeting the Bcl-2 family of proteins to develop novel cytotoxic drugs. Biochem Pharm. 2002; 64:851-863.
Barker, et al. Cyclic RGD peptide analogues as antiplatelet antithrombotics. J Med Chem. May 29, 1992;35(11):2040-8. (Abstract only).
Blackwell, et al. Highly effiecient synthesis of covalently cross-linked peptide helices by ring-closing metathesis. Agnew Chem Int Ed. 1998;37(23):3281-3284.
Blackwell, et al. Ring-closing metathesis of olefinic peptides: design, synthesis, and structural characterization of macrocyclic helical peptides. J Org Chem. Aug. 10, 2001;66(16):5291-302.
Brunel, et al. Synthesis of constrained helical peptides by thioether ligation: application to analogs of gp41. Chem Commun (Camb). May 28, 2005;(20):2552-4.
Burrage, et al. Biomimetic synthesis of lantibiotics. Chemistry. Apr. 14, 2000;6(8):1455-66.
Cantel, et al. Synthesis and Conformational Analysis of a Cyclic Peptide Obtained viaitoi+∝Intramolecular Side-Chain to Side-Chain Azide-Alkyne 1,3-Dipolar Cycloaddition. JOC Featured Article. Published on the web May 20, 2008.
Choi, et al. Application of azide-alkyne cycloaddition ‘click chemistry’ for the synthesis of Grb2 SH2 domain-binding macrocycles. Bioorg Med Chem Lett. Oct. 15, 2006;16(20):5265-9.
Dimartino et al. Solid-phase synthesis of hydrogen-bond surrogate-derived alpha-helices. Org Lett. Jun. 9, 2005;7(12):2389-92.
Feng et al. Solid-phase SN2 macrocyclization reactions to form beta-turn mimics. Org Lett. Jul. 15, 1999;1(1):121-4.
Galande, et al. Thioether side chain cyclization for helical peptide form
Aileron Therapeutics, Inc.
Russel Jeffrey E
Wilson Sonsini Goodrich & Rosati
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