Pyrrolobenzodiazepines

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C540S496000

Reexamination Certificate

active

07407951

ABSTRACT:
Compounds of formula (I): formula (I) and salts, solvates, chemically protected forms, and prodrugs thereof, are disclosed wherein R2is selected from: an optionally substituted napthyl group; an optionally substituted thiophenyl or furanyl group; and a phenyl group substituted by: one or more chloro or fluoro groups; an ethyl or propyl group; a 4-t-butyl group; a 2-methyl group; or two methyl groups in the 2- and 6-positions.

REFERENCES:
patent: 3523941 (1970-08-01), Leimgruber et al.
patent: 3524849 (1970-08-01), Batcho et al.
patent: 4185016 (1980-01-01), Takanabe et al.
patent: 4239683 (1980-12-01), Takanabe et al.
patent: 4309437 (1982-01-01), Ueda et al.
patent: 5143854 (1992-09-01), Pirrung et al.
patent: 5545568 (1996-08-01), Ellman et al.
patent: 6562806 (2003-05-01), Thurston et al.
patent: 6608192 (2003-08-01), Thurston et al.
patent: 6660856 (2003-12-01), Wang
patent: 6747144 (2004-06-01), Thurston et al.
patent: 2003/0120069 (2003-06-01), Thurston et al.
patent: 2003/0195196 (2003-10-01), Thurston et al.
patent: 2004/0092736 (2004-05-01), Thurston et al.
patent: 2004/0198722 (2004-10-01), Thurston et al.
patent: 0239400 (1987-09-01), None
patent: 1193270 (2002-04-01), None
patent: 2027356 (1969-12-01), None
patent: 2586683 (1987-03-01), None
patent: 1299198 (1972-12-01), None
patent: 2053894 (1981-02-01), None
patent: 53-82792 (1978-07-01), None
patent: 57131791 (1982-08-01), None
patent: 58180487 (1983-10-01), None
patent: WO 88/04659 (1988-06-01), None
patent: WO 88/07378 (1988-10-01), None
patent: WO 89/10140 (1989-11-01), None
patent: WO 91/16324 (1991-10-01), None
patent: WO 92/19620 (1992-11-01), None
patent: WO 93/08288 (1993-04-01), None
patent: WO 93/18045 (1993-09-01), None
patent: WO 96/23497 (1996-08-01), None
patent: WO 97/01560 (1997-01-01), None
patent: WO 97/07097 (1997-02-01), None
patent: WO 98/11101 (1998-03-01), None
patent: WO 98/12197 (1998-03-01), None
patent: WO 99/29642 (1999-06-01), None
patent: WO 99/46244 (1999-09-01), None
patent: WO 00/12506 (2000-03-01), None
patent: WO 00/12507 (2000-03-01), None
patent: WO 00/12508 (2000-03-01), None
patent: WO 00/12509 (2000-03-01), None
patent: WO 00/64864 (2000-11-01), None
patent: WO 2004/043963 (2004-05-01), None
patent: WO 2005/023814 (2005-03-01), None
patent: WO 2005/040170 (2005-05-01), None
patent: WO 2005/085251 (2005-09-01), None
Albericio, F. et al., “NPE-Resin, A New Approach to the Solid-Phase Synthesis of Protected Peptides and Oligonucleotides II. Synthesis of Protected Peptides1,2,”Tetrahedron Letters, 32:1515-1518 (1991).
Albericio, F. et al., “NPE-resin, a new approach to the solid-phase synthesis of protected peptides and oligonucleotides,”Peptides1990, Proc. 21.sub.st Eur. Pept. Symp., 134-136 (1990).
Althius, T. H. and Hess, H. J., “Synthesis and Identification of the Major Metabolites of Prazosin Formed in Dog and Rat,”0J. Medicinal Chem., 20(1), 146-148 (1977).
Arima et al., “Studies on Tomaymycin, a New Antibiotic. I. Isolation and Properties of Tomaymycin,”J. Antibiotics, 25, 437-444 (1972).
Aristoff, J. and Johnson, P., “Synthesis of CBI-PDE-I-Dimer, the Benzannelated Analogue of CC-1065,”J. Org. Chem., 57, 6234-6239 (1992).
Bagshawe et al., “Antibody-Enzyme Conjugates Can Generate Cytotoxic Drugs from Inactive Precursors at Tumor Sites,”Antibody, Immunoconjugates, and Radiopharmaceuticals, 4, 915-922 (1991).
Baraldi, P.G. et al., “Design, synthesis and biological activity of a pyrrolo[2,1-c][1,4]benzodiazepine (PBD)-distamycin hybrid,”Bioorganic&Medicinal Chemistry Letters, vol. 8, No. 21, 3019-3024 (1998).
Baraldi, P.G. et al., “Synthesis, in Vitro Antiproliferative Activity, and DNA-Binding Properties of Hybrid Molecules Containing Pyrrolo[2,1-c][1,4]benzodiazepine and Minor-Groove-Binding Oligopyrrole Carriers,”J. Med. Chem., 42, 5131-5141 (1999).
Bayley, H. et al., “Photoactivatable drugs,”TIPS, 8, 138-143 (1987).
Berry, J. M. et al., “Solid-phase synthesis of DNA-interactive pyrrolo[2,1-c][1,4]benzodiazepines,”Tetrahedron Letters, 41, 6171-6174 (2000).
Bi, Y. et al., “Building blocks for peptide and carbamate libraries”,Bioorganic&Medicinal Chemistry Letters, vol. 6, No. 19, 2299-2300 (1996).
Bi, Y., et al., “Building blocks for peptide and carbamate libraries,”Chemical Abstracts, vol. 125, No. 23, 1013 (1996).
Boger et al., “CC-1065 and the Duocarmycins: Synthetic Studies,”Chem. Rev., 97, 787-828 (1997).
Bose et al., “New Approaches to Pyrrolo[2,1-c][1,4]benzodiazepines: Synthesis, DNA-binding and cytotoxicity of DC-81,”Tetrahedron, 48, 751-758 (1992).
Bose, D.S. et al., “Rational Design of a Highly Efficient Irreversible DNA Interstrand Cross-Linking Agent Based on the Pyrrolobenzodiazepine Ring System,”J. Am. Chem. Soc., 114, 4939-4941 (1992).
Bridges, R.J. et al., “Conformationally Defined Neurotransmitter Analogues. Selective Inhibition of Glutamate Uptake by One Pyrrolidine-2,4-dicarboxylate Diastereomer,”J. Med. Chem., 34, 717-725 (1991).
Brown, S.C. et al., “NMR Solution Structure of a Peptide Nucleic Acid Complexed with RNA,”Science, 265, 777-780 (1994).
Bundgaard, H., “Design and Application of Prodrugs,”A Textbook of Drug Design and Development, eds Krogsgaard-Lassen, P., and Bundgaard, H., Harwood Academic Press, 113-135 (1991).
Burgess, K. et al., “Solid Phase Synthesis of Oligoureas”,J.Ame. Chem. Soc., 119: 1556-1564 (1997).
Burgess, K et al., “Solid Phase Synthesis of Unnatural Biopolymers Containing Repeating Urea Units,”Agnew Chem. Int. Ed. Engl, 34, No. 8:907-909 (1995).
Carruth, J.A.S., “Clinical applications for photodynamic therapy,”J. Photochem Photobiol., 9, 396-397 (1991).
Cho, C Y et al., “An Unnatural Biopolymer”,Science, 261: 1303-1305 (1993).
Courtney, S. M. et al., “A new convenient procedure for the synthesis of pyrrolo[2,1-c][1,4]benzodiazepines”,Tetrahedron Letters, vol. 34, No. 33, 5327-28 (1993).
Culver et al., “In Vivo Gene Transfer with Retroviral Vector-Producer Cells for Treatment of Experimental Brain Tumors,”Science, 256, 1550-1552 (1992).
Dalton, S. and Treisman, R, “Characterization of SAP-1, a Protein Recruited by Serum Response Factor to thec-fosSerum Response Element,”Cell, 68, 597-612 (1992).
Damayanthi, Y., et al., “Design and synthesis of novel pyrrolo [2,1-c][1,4] benzodiazepine-Lexitropsin Conjugates,”J. Org. Chem., 64, 290-292 (1999).
Dangles, O. et al., “Selective Cleavage of the Allyl and Allyloxycarbonyl Groups through Palladium-Catalyzed Hydrostannolysis with Tributyltin Hydride. Application to the Selective Protection-Deprotection of Amino Acid Derivatives and in Peptide Synthesis,”J. Org. Chem., 52, 4984-4993 (1987).
Dressman, B.A., et al., “Solid Phase Synthesis of Hydantoins Using a Carbamate Linker and a Novel Cyclization/Cleavage Step,”Tetrahedron Letters, 937-940 (1996).
Drost, K.J. and Cava, M.P., “A Photochemically Based Synthesis of the Benzannelated Analogue of the CC-1065 A Unit,”J. Org. Chem., 56:2240-2224 (1991).
Eashoo, M. et al., “Fibers from a Low Dielectric Constant Fluorinated Polyimide: Solution Spinning and Morphology Control,”J. Polymer Science, 35:173-185 (1997).
Edman, P. and Begg, G., “A Protein Sequenator,”Eur. J. Biochem., 1, 80-91 (1967).
Egholm, M et al., “Peptide Nucleic Acids (PNA). Oligonucleotide Analogues with an Achiral Peptide Backbone,”J. Am. Chem. Soc., 114, 1895-1897 (1992).
Egholm, M et al., “PNA hybridizes to complementary oligonucleotides obeying the Watson-Crick hydrogen-bonding rules,”Nature, 365, 566-568 (1993).
Englehardt et al., “Direct gene transfer of human CFTR into human bronchial epithelia of xenografts with E1-deleted adenoviruses,”Nature Genetics, 4, 27-34 (1993).
Farmer, J.D. et a

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