Pyrrolobenzodiazepines

Details Pyrrolobenzodiazepines Pyrrolobenzodiazepines

2006-04-21

2009-11-03

Kifle, Bruck (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C540S496000

Reexamination Certificate

active

07612062

ABSTRACT:
Compounds of the formula: (I) or solvate thereof, wherein: R2is an optionally substituted C5-20aryl group; R6and R9are independently selected from H, R, OH, OR, SH, SR, NH2, NHR, NRR′, nitro, Me3Sn and halo; where R and R′ are independently selected from optionally substituted C1-12alkyl, C3-20heterocyclyl and C5-20aryl groups; R7is selected from H, R, OH, OR, SH, SR, NH2, NHR, NHRR′, nitro, Me3Sn and halo; R″ is a C3-12alkylene group, which chain may be interrupted by one or more heteroatoms and/or aromatic rings; X is selected from O, S, or NH; z is 2 or 3; M is a monovalent pharmaceutically acceptable cation; R2′, R6′, R7′, R9′, X′ and M′ are selected from the same groups as R2, R6, R7, R9, X and M respectively, or M and M′ may together represent a divalent pharmaceutically acceptable cation.

REFERENCES:
patent: 4309437 (1982-01-01), Ueda et al.
patent: 5418241 (1995-05-01), Jegham et al.
patent: 6562806 (2003-05-01), Thurston et al.
patent: 6608192 (2003-08-01), Thurston et al.
patent: 6747144 (2004-06-01), Thurston et al.
patent: 6909006 (2005-06-01), Thurston et al.
patent: 7049311 (2006-05-01), Thurston et al.
patent: 7067511 (2006-06-01), Thurston et al.
patent: 7265105 (2007-09-01), Thurston et al.
patent: 7407951 (2008-08-01), 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: 2006/0264622 (2006-11-01), Howard et al.
patent: 2007/0072846 (2007-03-01), Vishnuvajjala et al.
patent: 2007/0173497 (2007-07-01), Howard et al.
patent: 2007/0185073 (2007-08-01), Howard et al.
patent: 2007/0191309 (2007-08-01), Howard et al.
patent: 2007/0191349 (2007-08-01), Howard et al.
patent: 2007/0249591 (2007-10-01), Howard et al.
patent: 2008/0090812 (2008-04-01), Pepper et al.
patent: 2008/0214525 (2008-09-01), Howard et al.
patent: 1193270 (2002-04-01), None
patent: 2053894 (1981-02-01), None
patent: 58180487 (1983-10-01), None
patent: WO 93/18045 (1993-09-01), None
patent: 00/12506 (2000-03-01), None
patent: 00/12507 (2000-03-01), None
patent: 00/12509 (2000-03-01), None
patent: WO 00/12508 (2000-03-01), 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 2005/042535 (2005-05-01), None
patent: WO 2005/085250 (2005-09-01), None
patent: WO 2005/085251 (2005-09-01), None
patent: WO 2005/085259 (2005-09-01), None
patent: WO 2005/085260 (2005-09-01), None
patent: WO 2005/110423 (2005-11-01), None
Althius, T. H. and Hess, H. J., “Synthesis and Identification of the Major Metabolites of Prazosin Formed in Dog and Rat,”J. Medicinal Chem. (1977) 20(1):146-148.
Arima et al., “Studies on Tomaymycin, a New Antibiotic. I. Isolation and Properties of Tomaymycin,”J. Antibiotics(1972) 25:437-444.
Berge et al., “Pharmaceutical Salts,” J. Pharm. Sci. (1977) 66:1-19.
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).
Gregson, S. et al., “Synthesis of a novel C2/C2′-exo unsaturated pyrrolobenzodiazepine cross-linking agent with remarkable DNA binding affinity and cytotoxicity,”Chemical Communications, 797-798 (1999).
Gregson, S.J. et al., “Linker length modulates DNA cross-linking reactivity and cytotoxic potency of C8/C8′ ether-linked C2-exo-unsaturated pyrrolo[2,1-c][1,4]benzodiazepine (PBD) dimers,” J. Med. Chem. (2004) 1161-1174.
Hara et al., “DC 102, a new glycosidic pyrrolo(1,4)benzodiazepine antibiotic produced bystreptomycessp.”,J. Antibiotics, 41, 702-704 (1988).
Hochlowski, J. et al., “Abbeymycin, a new anthramycin-type antibiotic produced by a streptomycete,”J. Antibiotics, 40, 145-148 (1987).
Howard, P.W. et al., “The design, synthesis and biological evaluation of a set of C2-aryl substituted pyrrolo[2,1-c][1,4]benzodiazepine dimers,” EJC Supplements (2006) 4(12):95—Poster Abstract 301.
Howard, P.W. et al., “Design, synthesis and biological evaluation of ZC-423, a novel C2-aryl substituted pyrrolobenzodiazepine (PBD) dimer,” Clinical Cancer Research (2005) 11(23):9015S-9016S (A205).
Hurley, L. and Needham-Vandevanter, D., “Covalent Binding of Antitumor Antibiotics in the Minor Groove of DNA. Mechanism of Action of CC-1065 and the Pyrrolo(1,4)benzodiazepines,”Acc. Chem. Res., 19, 230-237 (1986).
Itoh et al., “Sibanomicin, a new pyrrolo(1,4)benzodiazepine antitumor antibiotic produced by amicromonosporasp.”J. Antibiotics, 41, 1281-1284 (1988).
Kaneko, T. et al., “Bicyclic and tricyclic analogues of anthramycin,” J. Med. Chem. (1985) 28:388-392.
Kohn, K., “Anthramycin,”Antibiotics III, Springer-Verlag, NY, 3-11(1975).
Konishi, M. et al., “Chicamycin, a new antitumor antibiotic II. Structure determination of chicamycins A and B,”J. Antibiotics, 37, 200-206 (1984).
Kunimoto et al., “Mazethramycin, a new member of anthramycin group antibiotics,”J. Antibiotics, 33, 665-667 (1980).
Langley, D.R. and Thurston, D.E., “A versatile and efficient synthesis of carbinolamine-containing pyrrolo[1,4]benzodiazepines via the cyclization of N-92-aminobenzoyl)pyrrolidine-2-carboxaldehyde diethyl thioacetals: total synthesis of prothracarcin,”J. Org. Chem., 52, 91-97 (1987).
Langlois, N. et al., “Synthesis and cytotoxicity on sensitive and doxorubicin-resistant cell lines of new pyrrolo[2,1-c][1,4]benzodiazepines related to anthramycin,” J. Med. Chem. (2001) 44:3754-3757.
Leber, J.D. et al., “A revised structure for sibiromycin,”J. Am. Chem. Soc., 110, 2992-2993 (1988).
Leimgruber, W. et al., “Isolation and characterization of anthramycin, a new antitumor antibiotic,”J. Am. Chem. Soc., 87, 5791-5793 (1965).
Leimgruber, W. et al., “The structure of anthramycin,”J. Am. Chem. Soc., 87, 5793-5795 (1965).
Shimizu, K et al., “Prothracarcin, a Novel Antitumor Antibiotic,”J. Antibiotics, 35, 972-978 (1982).
Takeuchi, T. et al., “Neothramycins A and B, New Antitumor Antibiotics,”J. Antibiotics, 29, 93-96 (1976).
Thurston, D.E. and Thompson, A.S., “The molecular recognition of DNA,”Chem. Brit., 26, 767-772 (1990).
Thurston, D.E. and Bose, D.S., “Synthesis of DNA-Interactive Pyrrolo[2,1-c][1,4]benzodiazepines,”Chem. Rev., 94:433-465 (1994).
Tsunakawa, M. et al., “Porothramycin, a new antibiotic of the anthramycin group: Production, isolation, structure and biological activity,”J. Antibiotics, 41:1366-1373 (1988).
Umezawa, H. et al., Chemical Abstract No. 4427a, “Mazethramycins”Chemical Abstracts, vol. 90, No. 1, 428 (1979).
Workman, P. et al., “United Kingdom Co-ordinating Committee on Cancer Research (UKCCCR) guidelines for the welfare of animals in experimental neoplasia (second edition),” Br. J. Cancer (1998) 77(1):1-10.
Farmer, J.D. et al., “Synthesis and DNA crosslinking ability of a dimeric anthramycin analog,” Tetrahedron Letters (1988) 29(40):5105-5108, Abstract only.
Kamal, A. et al., “Design, synthesis and evaluation of new noncross-linking pyrrolobenzodiazepine dimers with efficient DNA binding ability and potent antitumor activity,” J. Med. Chem. (2002) 45:4679-4688.
Weidner-Wells, M.A. et al., “Photochemical approach to the synthesis of the pyrrolo[1,4]benzodiazepine antibiotics,” J. Org. Chem. (1989) 54:5746-5758.
United States Office Action for U.S. Appl. No. 09/763,813 dated Sep. 10, 2002 (11 pages).
United States Office Action for U.S. Appl. No. 09/763,813 dated Feb. 28, 2003 (8 pages).
United States Office Action for U.S. Appl. No. 09/763,813 dated May 21, 2003 (7 pages).
United States Office Action for U.S. Appl. No. 09/763,767 dated May 23, 2002 (20 pages).
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