Pyrrolbenzodiazepines

Details Pyrrolbenzodiazepines Pyrrolbenzodiazepines

2006-05-23

2006-05-23

Coleman, Brenda (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C540S486000, C540S496000

Reexamination Certificate

active

07049311

ABSTRACT:
Compounds of formula (Ia) and (Ib) wherein A is CH2, or a single bond; R2is selected from: R, OH, OR, CO2H, CO2R, COH, COR, SO2R, CN; R6, R7and R9are independently selected from H, R, OH, OR, halo, amino, NHR, nitro, Me3Sn; and R8is selected from H, R, OH, OR, halo, amino, NHR, nitro, Me3Sn, where R is as defined above, or the compound is a dimer with each monomer being the same or different and being of formula (Ia) or (Ib), where the R8groups of the monomers form together a bridge having the formula —X—R′—X— linking the monomers, where R′ is an alkylene chain containing from 3 to 12 carbon atoms, which chain may be interrupted by one or more hetero-atoms and/or aromatic rings and may contain one or more carbon—carbon double or triple bonds, and each X is independently selected from O, S, or N; except that in a compound of formula (Ia) when A is a single bond, then R2is not CH═CH(CONH2) or CH═CH(CONMe2). Other related compounds are also disclosed

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: 0239400 (1987-09-01), None
patent: 2 027 356 (1969-12-01), None
patent: 2 586 683 (1987-03-01), None
patent: 1 299 198 (1972-12-01), None
patent: 53-82792 (1978-07-01), None
patent: 57 131 791 (1982-08-01), None
patent: 58 180 487 (1983-10-01), None
patent: WO 88/07378 (1988-10-01), None
patent: WO 89/10140 (1989-11-01), None
patent: WO 92/19620 (1992-11-01), None
patent: WO 93/18045 (1993-09-01), None
patent: WO 97/01560 (1997-01-01), None
patent: WO 00/12506 (2000-03-01), None
patent: WO 00/12507 (2000-03-01), None
Katritzky et al., Heterocyclic Chemistry, John Wiley & Sons, Inc., 1960, pp. 247-253.
Grant et al., Grant and Hackh's Chemical Dictionary, McGraw-Hill Book Company, 1987, p. 282.
Suggs et al., Synthesis and Structure of Anthramycin Analogs Via Hydride Reduction of Dilactams, Tetrahedron Letters, vol. 26, No. 40, pp. 4871-4874, 1985.
Foloppe, M.P., et al., “DNA-binding properties of pyrrolo[2,1-c][1,4]benzodiazepine N10-C11 amidines”Eur. J. Med. Chem., 31, 407-410 (1996).
Kamal, A., et al., “An Efficient Synthesis of Pyrrolo[2,1-c][1,4]benzodiazepine Antibiotics via Reductive Cyclization”Bioorganic&Medicinal Chemical Letters, 7, 14, 1825-1828 (1997).
Kamal, A., et al., “Synthesis of Pyrrolo[2,1-c][1,4]benzodiazepine Antibiotics: Oxidation of Cyclic Secondary Amine With TPAP”Tetrahedron Ltrs, 53, 9, 3223-3230 (1997).
Thurston, D.E., et al., “Synthesis of Sequence-Selective C8-Linked Pyrrolo[2,1-c][1,4]benzodiazepine DNA Interstrand Cross-Linked Agents”J. Org. Chem., 61, 8141-8147 (1996).
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).
Chemical Abstract No. 171573p, O'Neil, “The synthesis of Functionalized Pyrrolo-[2,1-c][1,4]-Benzodiazepines”,Chemical Abstracts, vol. 126, No. 13, 618 (1997) and entire article.
Chemical Abstract No. 4427a, Umezawa, “Mazethramycins”Chemical Abstracts, vol. 90, No. 1, 428, (1979).
Chemical Abstract No. 239940r, Farmer, “DNA binding properties of a new class of linked anthramycin analogs”,Chemical Abstracts, vol. 114, No. 25, 25 (1991) and entire article.
Gregson, S. J. 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).
O'Neil, I. A. et al., “DPPE: A Convenient Replacement for Triphenylphosphine in the Staudinger and Mitsunobu Reactions”,Tetrahedron Letters, vol. 39, No. 42, 7787-7790 (1998).
Guiotto A. et al., “Synthesis of novel C7-aryl substituted pyrrolo [2,1-c][1,4]benzodiazepines (PBDs) via Pro-N10-troc protection and suzuki coupling”,Bioorgnainc&Medicinal Chemistry Letters, vol. 8, No. 21, 3017-3018 (1998).
Thurston, D. E., et al., “Effect of A-ring modifications on the DNA-binding behavior and cytotoxicity of pyrrolo[2,1-c][1,4]benzodiazepines”,Journal of Medicinal Chemistry, vol. 42, 1951-1964 (1999).
Chemical Abstract No. 72145x, Fujisawa, “Benzodiazepine derivatives”,Chemical Abstracts, vol. 98, No. 9, 638 (1983).
Leimgruber et al.,J. Am. Chem. Soc., 87, 5793-5795 (1965).
Leimgruber et al.,J. Am. Chem. Soc., 87, 5791-5793 (1965).
Thurston et al.,Chem. Rev., 1994, 433-465 (1994).
Hochlowski et al.,J. Antibiotics, 40, 145-148 (1987).
Konishi et al.,J. Antibiotics, 37, 200-206 (1984).
Thurston et al.,Chem. Brit., 26, 767-772 (1990).
Rose et al.,Tetrahedron, 48, 751-758 (1992).
Kunimoto et al.,J. Antibiotics, 33, 665-667 (1980).
Takeuchi et al.,J. Antibiotics, 29, 93-96 (1976).
Tsunakawa, et al.,J. Antibiotics, 41, 1366-1373 (1988).
Shimizu et al.,J. Antibiotics, 29, 2492-2503 (1982).
Langley and Thurston,J. Org. Chem., 52, 91-97 (1987).
Hara et al.,J. Antibiotics, 41, 702,704 (1988).
Itoh et al.,J. Antibiotics, 41, 1281-1284 (1988).
Leber et al.,J. Am. Chem. Soc., 110, 2992-2993 (1988).
Arima et al.,J. Antibiotics, 25, 437-444 (1972).
Kohn,Antibiotics III, Springer-Verlag, NY, 3-11 (1975).
Hurley and Needham-VanDevanter,Acc. Chem. Res., 19, 230-237 (1986).
Leimgruber, W., Batcho, A. D., Czajkowski, R. J.,J. Am. Chem. Soc., 90, 5641 (1968).
Bridges, R. J., Stanley, M. S., Anderson, M. W., Cotman, C. W., Chamberlain, R. A.,J. Med. Chem., 34, 717 (1991).
Dangles, O., Guibé, F., Balavoine, G., Lavielle, S., Marquet, A.,J. Org. Chem., 52, 4984 (1987).
Althuis, T. H. and Hess, H. J.,J. Medicinal Chem., 20(1), 146-266 (1977).
Thurston, D.E., “Advances in the study of Pyrrolo[2,1-c][4,1] benzodiazepine (PBD) Antitumour Antibiotics”,Molecular Aspects of Anticancer Drug-DNA interactions, Neidle, S., Waring, M.J. eds., Macmillan Press Ltd., 1: 54-88 (1993).
Gregson, S.J., et al., “Design, Synthesis and Evaluation of a Novel Pyrrolobenzodiazepine DNA-Interactive Agent with Highly Efficient Cross-Linking Ability and Potent Cytotoxicity”,J. Med. Chem., 44: 737-748 (2001).
Gregson, S.J., et al., “Effect of C2-exo Unsaturation on the Cytotoxicity and DNA-Binding Reactivity of Pyrrolo[2,1-c]1,4benzodiazepines”,Bioorganic&Medicinal Chemistry Letters, 10: 1845-1847 (2000).
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).
Wilson, S.C. et al., “Design, Synthesis, and Evaluation of a Novel Sequence-Selective Epoxide-Containing DNA Cross-Linking Agent Based on the Pyrrolo[2,1-c][1,4]benzodiazepine System”,J. Med. Chem., 42:4028-4041 (1999).
Thurston, D.E., et al., “Effect of A-Ring Modifications on the DNA-Binding Behavior and Cytotoxicity of Pyrrolo[2,1-c][1,4]benzodiazepines”J. Med. Chem., 42: 1951-1964 (1999).
Nagasaka. T., et al.,Tetrahedron Letters, vol. 30, No. 14, 1871-72 (1989).
Fukuyama, T., et al.,Tetrahedron Letters, vol. 34, No. 16, 2577-2580 (1993).
Wilson, S.C., et al.,Tetrahedron Letters, vol. 36, No. 35, 6333-6336 (1995).
Nagasaka. T., et al.,J. of Organic Chemistry, vol. 36, No. 20, 6797-6801 (1998).
Baraldi, P.G., et al.,Bioorganic&Medicinal Chemistry Letters, vol. 8, No. 21, 3019-3024 (1998).
Bi, Y., et al.,Bioorganic&Medicinal Chemistry Letters, vol. 6, No. 19, 2299-2300 (1996).
Chemical Abstracts No. 139983k. Fujisawa,Chemical Abstracts, vol. 99, No. 17, 603 (1983).
Thurston, D.E., et al.,Chemical Communications, 563-565 (1996).
Chemical Abstracts No. 300965y, Bi, Y., et al.,Chemical Abstracts, vol. 125, No. 23, 1013 (1996).
Albericio, F. et al., “NPE-Resin, A New Approach to the Solid-Phase Synthesis of Protected Peptides and Oligonucleotides II. Synthesis of Protected Peptid

Affiliated with

Also associated with

Rating

Pyrrolbenzodiazepines does not yet have a rating. At this time, there are no reviews or comments for this patent.

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

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3562191