Hemisynthetic method and new compounds

Details Hemisynthetic method and new compounds Hemisynthetic method and new compounds

2007-07-10

2007-07-10

Habte, Kahsay (Department: 1624)

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

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

C540S466000

Reexamination Certificate

active

09979404

ABSTRACT:
Methods are provided for preparing a compound with a fused ring structure of formula (XIV) which comprises one or more reactions starting from a 21-cyano compound of formula (XVI) where typically: R1is an amidomethylene group or an acyloxymethylene group; R5and R8are independently chosen from —H, —OH or —OCOCH2OH, or R5and R8are both keto and the ring A is a p-benzoquinone ring; R14aand R14bare both —H ozone is —H and the other is —OH, —OCH3or —OCH2CH3, or R14aand R14btogether form a keto group; and R15and R18are independently chosen from —H or —OH, or R5and R8are both keto and the ring A is a p-benzoquinone ring. In modified starting materials, the 21-cyano group can be replaced by other groups introduced using nucleophilic reagents.

REFERENCES:
patent: 5089273 (1992-02-01), Rinehart et al.
patent: 5149804 (1992-09-01), Rinehart et al.
patent: 5256663 (1993-10-01), Rinehart et al.
patent: 5478932 (1995-12-01), Rinehart et al.
patent: 5654426 (1997-08-01), Rinehart et al.
patent: 5721362 (1998-02-01), Corey et al.
patent: 5985876 (1999-11-01), Rinehart et al.
patent: 6124292 (2000-09-01), Corey
patent: 6124293 (2000-09-01), Rinehart et al.
patent: 6316214 (2001-11-01), Rinehart et al.
patent: 6348467 (2002-02-01), Corey
patent: 6686470 (2004-02-01), Danishefsky et al.
patent: 6867334 (2005-03-01), Rinehart et al.
patent: 0 309 477 (1991-11-01), None
patent: 59-225189 (1984-12-01), None
patent: 60-84288 (1985-05-01), None
patent: 2003/0216397 (2003-11-01), None
patent: 2004/0002602 (2004-01-01), None
patent: 2004/0019056 (2004-01-01), None
patent: WO 87/07610 (1987-12-01), None
patent: WO 92/09607 (1992-06-01), None
patent: WO 98/12198 (1998-03-01), None
patent: WO 98/46080 (1998-10-01), None
patent: WO 99/51238 (1999-10-01), None
patent: WO 99/58125 (1999-11-01), None
patent: WO 00/18233 (2000-04-01), None
patent: WO 01/77115 (2001-10-01), None
patent: WO 01/87894 (2001-11-01), None
patent: WO 01/87895 (2001-11-01), None
Corey et al. (J. Am. Chem. Soc., vol. 118, 1996, pp. 9202-9203).
Ryuichi Sakai et al., Ecteinascidins: Putative Blosynthetic Precursors and Absolute Stereochemistry, J. Am. Chem. Soc., vol. 118, 1996, pp. 9017-9023, XP002925426.
A. H. Parulekar et al, Bioactivity and Chemical Ecology of Some Intertidal Animals, Bioactivity and Chemical Ecology, 29-35.
E.J. Corey et al., Enantioselective Total Synthesis of Ecteinascidin, J. Am. Chem. Soc. , vol. 118, 1996, pp. 9202-9203, XP002925428.
J. William Lown et al. , Molecular Mechanisms of Binding and Single -Strand Scission of Deoxyribonucleic Acid by the Antitumor Antibiotics, Biochemistry, vol. 21, No. 3, 1982, XP002925424.
Katsukiyo Yazawa et al., Bioconversions of Saframycin a Specific to Some Genera of Actinomycetes, The J. Antibiotics, vol. XXXV, No. 7, 1982, 915-917.
Takemitsu Asaoka, A New Saframycin, Saframycin R, The J. Antibiotics, vol. XXXV, No. 12, 1982, 1708-1710.
Tadashi Arai, Increased Production of Saframycin A and Isolation of Saframycin S, The J. Antibiotics, vol. XXXV, No. 9, 1980, 951-960.
Arai, T. et al., New Antibiotics, Saframycins A, B, C, D, and E, The J. Antibiotics, vol. XXX, No. 11, 1977, 1015-1018.
Yoshifumi Ikeda et al. , Safracins, New Antitumor Antibiotics, The J. Antibiotics, vol. XXXVI, No. 10, 1983, 1279-1283.
J. Williams Lown, Structure and Confirmation of Saframycin R Determine by High Field H and C NMR and its Interactions with DNA in Solution, The J. Antibiotics, vol. XXXVI, No. 97, 1983, 1183-1194.
Katsuhiro Takahashi et al., Microbial Conversion of Saframycin A to 25-Dihydrosaframycin A and 21-Decyano-25-Dihydrosaframycin A (25-Dihydrosaframycin B) and their Biological Activities, The J. Antibiotics, vol. XXXV, No. 2, 1983, 196-202.
Yoshifumi Ikeda, Safracins, New Antitumor Anitibiocics, The J. Antibiotics, vol. XXXV, No. 10, 1983, 1284-1289.
Raymond Cooper. et al., Structure of the Qyinone Antibiotic EM5519 and the Behavior of Qyinones in Fast Atom Bombardment Mass Spectrometry, The J. Antibiotics, vol. XXXVIII, No. 1, 1985, 24-30.
Akinori Kubo et al., Structure of Saframycin D, A New Kimeric Isoquinolinequinone Antibiotic, Chem. Pharm.Bull., vol. 35, No. 1, 1987, 440-442.
James M. Fincke et al., Antimicrobial Metabolites of the SpongeRenierasp., J. Am. Chem. Soc., vol. 104, 1982, 256-269.
Eduardo J. Martinez et al., Phthalascidin, a Synthetic Antitumor Agent with Potency and Mode of Action Comparabale to Ecteinascidin 743, Proc. Natl. Acad. Sci. USa, vol. 96, 1999, 3496-3501.
Tadashi Arai et al, Directed Biosynthesis of New Sarfamycin Derivatives with Resting Cells ofStreptomyces lavendulae, Antimicrobial Agents and Chemotherapy vol. 28, No. 1, 1985, 5-11.
T. Arai et al., The Structure of a Novel Antitumor Antibiotic, Saframycin A, 1980, 1025-1029.
Wolfram Trowitzsch-Kienast, Isolating and Structure Elucidation of Saframycin Mx 1 and Mx 2, New Anti-Tumor-Active Antibiotics fromMyxococcus xanthus, Ann. Chem., 1988, 475-481.
Tadashi Arai et al., Isoquinolineinones From Actinomycetes and Sponges, The Alcaloids, vol. XXI, 1983, 55-100.
Hai-Yin He et al., Renieramycins E from the spongeRenierasp.:Reassignment of the Stereochemistry of the Renieranycins, J. Org. Chem., vol. 54, No. 24, 1989, 5822-5824.
Katsukiyo Yazawa et al., Isolation and Structural Elucidation of New Saframycins Y3, Yd-2, Ag-1, Y2b and Y2b-d, The J. of Antibiotics, vol. XXXIX, No. 12, 1986, 1639-1650.
Yuzuru Mikami et al, Structural Studies on Minor Components of Saframycin Group Antibiotics Saframycins F, G and H The J. of Antibiotic, vol. XLI, No. 6, 1988, 734-740.
E. J. Corey et al., Enantioselective Total synthesis of Ecteinascidin 743, J. Am. Chem. Soc., vol. 118, 1996, 9202-9203.
Saframycins, Renieramycins, and, Safracins, Discovery, Isolation and Characterization, 93-118.
Raymond Cooper et al., Structure of the Qyinone Antibiotic EM5519 and the Behavior of Quinones in Fas Atom Bombardment Mass Spectrometry, The J. of Anitibiotics, vol. XXXVIII, No. 1, 1985, 24-30.
Brown, J.M., “NCI's Anticancer Drug Screening Program May Not Be Selecting for Clinically Active Compounds,” Oncol. Res. 9(5):213-215 (1997).
Draetta, G. and Pagano, M., “Annual Reports in Medicinal Chemistry, vol. 31,” Academic Press, San Diego, pp. 241-246 (1996).
Ikeda, Yoshifumi et al., “Safracins, New Antitumor Antibiotics I. Producing Organism, Fermentation and Isolation”,The Journal of Antibiotics, vol. XXXVI, No. 10, pp. 1279-1283 (1983).
Lown, J. William et al., “Molecular Mechanisms of Binding and Single-Strand Scission of Deoxyribonucleic Acid by the Antitumor Antibiotics Saframycins A and C”,Biochemistry, vol. 21, No. 3, pp. 419-428 (1982).
Martinez et al., “A New, More Efficient, and Effective Process for the Synthesis of a Key Pentacyclic Intermediate for Production of Ecteinascidin and Phthalascidin Antitumor Agents”,Organic Letters, 2(7):993-996 (2000).
Martinez et al., “Enantioselective Synthesis of Saframycin A and Evaluation of Antitumor Activity Relative to Ecteinascidin/Saframycin Hybirds”,Organic Letters,1(7):75-77 (1999).
Myers et al., “A Concise, Stereocontrolled Synthesis of (-)-Saframycin A by the Directed Condensation of α-Amino Aldehyde Precursors”,J. Am. Chem. Soc.,121:10828-10829 (1999).
Takahaski, Katsuhiro, “New Antibiotics, Saframycins A, B, C, D and E”,The Journal of Antibiotics, vol. XXX, No. 11, pp. 1015-1018 (1977).
Kania, Robert S., “The First Enantioselective Total Syntheses of Dolabellatrienone and Ecteinascidin 743”, Ph.D. Thesis, Harvard University, Sep. 1997, pp. 1-225.
Sparidans, Rolf W. et al., “Search for metabolites of ecteinascidin 743, a novel, marine-derived, anti-cancer agent, in man.”Anti-Cancer Drugs,vol. 12, pp. 653-666, (2001).
Arai, T. et al., “The Structure of a Novel Antitumor Antibiotic, Saframycin A”,Experientia, vol. 36, pp. 1025-1027 (1980).
Arai, Tadashi et al., “Increased Production of Saframycin A and Isolation of Saframycin S”,The Journal

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