Synthesis of protected pyrrolobenzodiazepines

Details Synthesis of protected pyrrolobenzodiazepines Synthesis of protected pyrrolobenzodiazepines

2008-09-30

2008-09-30

Kifle, Bruck (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

C548S539000, C560S024000, C560S032000

Reexamination Certificate

active

10571274

ABSTRACT:
A method of synthesis of a N-10 protected PBD compound of formula (I):via an intermediate of formula (II) or formula (V):

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: 5418241 (1995-05-01), Jegham 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 D (1987-03-01), None
patent: 1299198 D (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 D (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 D (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
Weidner-Wells et al. (Journal of Organic Chemistry (1989), 54(24), 5746-58).
Adams et al., “Molecular modelling of a sequence-specific DNA-binding agent based on the pyrrolo[2,1-c][1,4]benzodiazepines,” Pharm. Pharmacol. Commun. (1999) 5:555-560.
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,”J. 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).
Baraldi, P.G. et al., “[2,1-c][1,4]benzodiazepine (PBD)-distamycin hybrid inhibits DNA binding to transcription factor Sp1,” Nucleotides and Nucleic Acids (2000) 19(8):1219-1229.
Bayley, H. et al., “Photoactivatable drugs,”TIPS, 8, 138-143 (1987).
Berge et al., “Pharmaceutical Salts,” J. Pharm. Sci. (1977) 66:1-19.
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).
Borgatti, M. et al., “Inhibition of NF-kB/DNA interactions and HIV-1 LTR directed transcription by hybrid molecules containing pyrrolo [2,1-c][1,4] benzodiazepine (PBD) and oligopyrrole carriers,” Drug Development Research (2003) 60(3):173-185.
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).
Bose, D.S. et al., “Effect of linker length on DNA-binding affinity, cross-linking efficiency and cytotoxicity of C8 linked pyrrolobenzodiazepine dimers,” J. Chem. Soc. Chem. Commun. (1992) 20:1518-1520.
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).
Chen, Z. et al., “A novel approach to the synthesis of cytotoxic C2-C3 unsaturated pyrrolo[2,1-c][1,4]benzodiazepines (PBDs) with conjugated acrylyl C2-substiuents,” Biorg. Med. Chem. Lett. (2004) 14:1547-1549.
Cho, C Y et al., “An Unnatural Biopolymer”,Science, 261: 1303-1305 (1993).
Cooper, N. et al., “Synthesis of novel PBDs as anti-tumour agents,” Chem. Commun. (2002) 16:1764-1765.
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 the c-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).
De Groot, FMH et al., “Synthe

Affiliated with

Also associated with

Rating

Synthesis of protected pyrrolobenzodiazepines does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Synthesis of protected pyrrolobenzodiazepines, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of protected pyrrolobenzodiazepines will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3931738