Cyclopropylindole derivatives

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C548S433000, C548S450000

Reexamination Certificate

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06909006

ABSTRACT:
Compounds of formula (III) or (V), wherein is a solid support; L is a linking group or a single bond; T is a combinatorial unit; n is a positive integer, where if n is greater than 1, each T may be different: X is an electrophilic leaving group; Y is selected from NH-Prot, O-Prot, S-Prot, NO2, —NHOH. N3, NHR, NRR, N═NR, N(O)RR, NHSO2R, N═N═PhR, SR or SSR, where Prot represents a protecting group; A and B collectively represent a fused benzene or pyrrole ring (in either orientation), which is optionally substituted by up to respectively 4 or 2 groups independently selected from R, OH, OR, halo, nitro, amino, Me3Sn, CO2H, CO2R, R1is a nitrogen protecting group, where if Y includes a protecting group, these protecting groups are orthogonal and R2and R7are independently selected from H, R, OH, OR, halo, nitro, amino, Me3Sn, and other related compounds and collections of compounds.

REFERENCES:
patent: 3523941 (1970-08-01), Leimgruber et al.
patent: 3524849 (1970-08-01), Batcho 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
patent: 2 586 683 (1987-03-01), None
patent: 1 299 198 (1972-12-01), None
patent: 57-131791 (1982-08-01), None
patent: 58180487 (1983-10-01), None
patent: WO 88/04659 (1988-06-01), None
patent: WO 91/16324 (1991-10-01), None
patent: WO 92/19620 (1992-11-01), None
patent: WO 96/23947 (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 00/12506 (2000-03-01), None
Boger et al. Journal of the American Chemical Society (1992), 114(25), 10056-8.
Althuis, T.H. et al., “Synthesis and identification of the major metabolites of Prazosin formed in dog and rat,” 20:1, 146-149 (1977).
Aristoff, P.A. et al., “Synthesis of CBI-PDE-I-Dimer, the benzannelated analogue of CC-1065,”J.Org.Chem., 57, 6234-6239 (1992).
Aristoff, P.A. et al., “Synthesis of biochemical evaluation of the CBI-PDE-I-dimer, a benzannelated analog of (+)-CC-1065 that also produces delayed toxicity in mice,”J.Med.Chem., 36, 1956-1963 (1993).
Baraldi, P.G. et al., “Design, synthesis and biological activity of a pyrrolo [2,I-c][1,4] benzodiazepine (PBD)-distamycin hybrid,”Bioorg. Med. Chem. Ltrs., 8, 3019-3024 (1998).
Bi, Y. et al, “Building blocks for peptide and carbamate libraries,”Bioorg. Med. Chem. Ltrs, 6:19, 2299-2300 (1996).
Bi, Y., et al, “Building blocks for peptide and carbamate libraries,”Chemical Abstracts, 300965y, 125:23, p. 1013 (1996).
Boger, D.L., “Design, synthesis, and evaluation of DNA minor groove binding agents: the duocarmycins,”Pure&Appl. Chem., 66:4, 837-844 (1994).
Boger, D.L. et al., “Total synthesis and evaluation of ±-N-(tert-butyloxycarbonyl)-CBI (±)-CBI-CDPI1, and (±)-CBI-CDPI2CC-1065 functional agents incorporating the equivalent 1,2,9,9a-tetrahydrocycloprop[1,2-c]benz[1,2-e]indol-4-one(CBI) left-hand subunit,”J. Am. Chem Soc., 111:16, 6461-6453 (1989).
Boger, D.L. et al., “Synthesis of N-(tert-butyloxycarbonyl)-CBI,CBI,CBI-CDPII,and CBI-CDPI2: Enhanced functional analogues of CC-1065 incorporating the 1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (CBI) left-hand subunit,”.Org. Chem., 55:23, 5823-5832 (1990).
Boger, D.L. et al., “An efficient synthesis of 1,2,9,9a-tetrahydrocyclopropa[c]benz[e] indol-4-one (CBI): An enhanced and simplified analog of the CC-1065 and duocarmycin alkylation subunits,”J. Org. Chem., 60:5, 1271-1275 (1995).
Boger, D.L. et al., “CBI-TMI: Synthesis and evaluation of a key analog of the duocarmycins. Validation of a direct relationship between chemical solvolytic stability and cytotoxic potency and confirmation of the structural features responisble for the distinguishing behavior of enantiomeric paris of agents,”J. Am. Chem. Soc., 116:18, 7996-8006 (1994).
Boger, D.L. et al., “CC-1065 and the duocarmycins: synthetic studies,”Chem. Rev., 97:3, 787-828 (1997).
Bose, D.S et al., “New approaches to pyrrolo[2,1-c][1,4]benzodiazepines: synthesis, DNA-binding and cytotoxicity of DC-81,”Tetrahedron, 48:4, 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., 114:12, 4939-4941 (1992).
Brown, S.C. et al., “NMR solution structure of a peptide nucleic acid complexed with RNA,”Science, 265, 777-780 (1994).
Burgess, K. et al., “Solid phase syntheses of oligoureas,”J. Am. Chem. Soc., 119:7, 1556-1564 (1997).
Burgess, K. et al., “Solid-phase syntheses of unnatural biopolymers containing repeating urea units,”Agnew. Chem. Int. Ed. Engl., 34:8, 907-909 (1995).
Cava, M.P. & Drost, K.J., “a photochemically based synthesis of the benzannelated analogue of the CC-1065 A unit,”J. Org. Chem., 56:6, 2240-2244 (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 Ltrs., 34:33, 5327-5328 (1993).
Edman, P. et al., “A protein sequenator,”European J. Biochem., 1:1, 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).
Farmer, J.D., Jr. et al., “DNA binding properties of a new class of linked anthramycin analogs,”Chemical Abstract, 239940r, 114:25, p. 25 (1991).
Figliozzi, G.M. et al., “Synthesis of N-substituted glycine peptoid libraries,”Methods in Enzymology, 267:25 437-47 (1996).
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).
Fujisawa Pharm., “Benzodiazepine derivatives,”Chemical Abstracts, 139983k, 99:17, 603 (1983).
Fujisawa Pharm., “Benzodiazepine derivatives,”Chemical Abstracts, 72145x, 98:9, 638 (1983).
Fukuyama, T. et al., “Total synthesis of (+)-porothramycin B,”Tetrahedron Ltrs., 34:16, 2577-80 (1993).
Furka, A. et al., “General method for rapid synthesis of multicomponent peptide mixtures,”In. J. Peptide Protein Res., 37 487-493 (1991).
Gregson, S.J. et al., “Synthesis of a novel C2/C2′-exo unsaturated pyrrolobenzodiazepine cross-linking agent with remarkable DNA binding affinity and cytotoxicity,”Chem. Commun., 797-798 (1999).
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,”Bioorg. Med. Chem. Ltrs., 8:21, 3017-3018 (1998).
Hara, M. et al., “A new glycosidic pyrrolo[1,4]benzodiazepine antibiotic produced byStreptomycessp.”J. Antibiotics, 41:5, 702-704 (1988).
Hochlowski, J.E. et al., “Abbeymycin, a new anthramycin-type antibiotic produced by aStreptomycete,” J. of Antibiotics, 40:2, 145-148 (1987).
Hurley, L.H. et al., “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, J. et al., “Sibanomicin, a new pyrrolo[1,4]benzodiazepine antitumor antibiotic produced by aMicromonosporasp.,”J. Antibiotics, 41:9, 1280-1284 (1988).
Jenkins, T.C. et al., “Structure of a covalent DNA minor groove adduct with a pyrrolobenzodiazepine dimer: Evidence for sequence-specif

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