Coupling agents for peptide synthesis

Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system

Reexamination Certificate

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C544S232000

Reexamination Certificate

active

07812158

ABSTRACT:
The present invention is directed to compounds of the formula (I) and (II) or salts thereof or N-oxides and their use in peptide synthesis.

REFERENCES:
patent: 5698675 (1997-12-01), Carpino
patent: 6277858 (2001-08-01), Walter
patent: 0638842 (1995-02-01), None
patent: 2193213 (1988-02-01), None
patent: 2005007634 (2005-01-01), None
patent: WO 2005/007634 (2005-01-01), None
Carpino et al. J. Org. Chem. 2004, 69, 54-61.
F. Hoffmann, L. Jāger, C Griehl; Synthesis and Chemical Constitution of Diphenoxyphosphoryl Derivatives and Phosphonium Salts as Coupling Reagents for Peptide Segment Condensation; Phosphorus, Sulfur and Silicon, 2003, vol. 178:299-309; Taylor & Francis.
Griehl C, Jager L, Plass M and Kolbe A; Carboxyactivation of Peptide Fragments with New Coupling Reagents in Peptides, 1996 Proceedings of the 24thEuropean Peptide Symposium Sep. 8-13, 1996; 437-438, The European Peptide Society, (Robert Ramage & Roger Epton, Eds.) 1998.
Carpino L, Xia J and El-Faham A; 3-Hydroxy-4-oxo-3,4-dihydro-5-azabenzo-1,2,3-triazene; J. Org. Chem. 2004, 69, 54-61.
Carpino L, Xia J, Zhang C, and El-Faham A; Organophosphorus and Nitro-Substituted Sulfonate Esters of 1-Hydroxy-7-azabenzotriazole as Highly Efficient Fast-Acting Peptide Coupling Reagents; J. Org. Chem. 2004, 69, 62-71.
Chemical Abstracts, vol. 71, No. 9, 1969, Columbus, Ohio, US; abstract No. 39003u, p. 303 col. 1 XP002505421 *abstract* & JP 06 908508 B (Yoshitomi) Apr. 21, 1969.
Carpino L A et al: “Efficiency in peptide coupling: 1-hydroxy-7-azabenzotriozole vs 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine” Journal of Organic Chemicstry, American Chemcial Society, Easton,; US, vol. 60, Jan. 1, 1995, pp. 3561-3564, XP002982632 ISSN: 0022-3263 *p. 3561*.
S. Kim: “benzotriazol-l-yl diethyl phosphate.” Tetrahedron Letters, vol. 26, No. 10, 1985, pp. 1341-1342, XP002505418 Nlelsevier, Amsterdam. *p. 1341.*
Campagne J-M et al: “(1H-Benzotriazol-1-Yloxy)Tris(Dimethylamino)Phosphonium Hexafluorophosphate-and (1H-Benzotriazol-1-Yloxy)Tripyroolidinophosp Honium Hexafluorophosphate-Mediated Activation of Monophosphonate Esters:Synthesis of Mixed Phosphonate Diesters, the Reactivity of the Benzotriazolyl Phosphoneic Esters Vs TH” Journal of Organic Chemistry, American Chemcial Society, Easton,; US, vol. 60, No. 16, 1, 1995.
I. Furukawa et al.: “synthesis of polymaides with [(1,2,3-benzotriazine-4-one(-3-yl]diphenyl phosphate as a new activating agent.” Journal of Macromolecular Sci.-Chemistry, vol. a26, No. 5, 1989, pp. 761-771, XP008098954 en *p. 761-p. 764; compount BTDP*.
M. Goodman et al.: “new reagents, reactions, and peptidomimetics for drug design” Biopolymers, vol. 60, No. 3, 2001, pp. 229-245, XP002505419 us *p. 229-p. 236*.
L. Carpino et al.: “3-hydroxy-4-oxo-3, 4-dihydro-5-azabenzo-1,2,3-triazine.” Journal of Organic Chemistry., vol. 69, No. 1, 2004, pp. 54-61, XP002505420 USAmerican Chemical Society. Easton. *p. 54-p. 56*.

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