Compounds of the saframycin-ecteinascidin series, uses, and...

Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...

Reexamination Certificate

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Reexamination Certificate

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06936714

ABSTRACT:
Compounds of the saframycin-ecteinascidin series with cytotoxic properties having the following general formula, their uses and synthesis, are disclosed:wherein R1and R4is H, a C1to C4alkyl group, or an acyl group;wherein R2is an ether, ester, amide, or a phthalimide group;wherein R3is ═O, OH, an ether group, an acyl group such as OC(O)Me, OC(O)Bn and OC(O)Et, or a sulfide group; wherein R5is H, halogen, OH, an ether group, an acyl group, or an amide group; wherein R6is ═O, OH, OCH3, CN, or an acyloxy group;wherein R7, is ═O, OH, halogen, an ether group, or an acyl group; wherein R8and R9are independently H, CH3, OCH3, OC2H5, CF3, halogen such as Br and F, or R8and R9are joined together as a methylenedioxy group, or other five or six membered ring; wherein R10and R11are independently CH3, OCH3, OC2H5, SCH3, or SC2H5; wherein R12is H, a C1to C4alkyl group, or an acyl group; and wherein the chiral center marked * has the R or the S configuration.

REFERENCES:
patent: 5721362 (1998-02-01), Corey
patent: 6124292 (2000-09-01), Corey
patent: 6348467 (2002-02-01), Corey
patent: 6686470 (2004-02-01), Danishefsky
patent: 6809099 (2004-10-01), Myers et al.
patent: 2003/0008873 (2003-01-01), Myers et al.
patent: WO 9951238 (1999-10-01), None
patent: WO 0018233 (2000-04-01), None
Arai T. et al., “New antibiotics saframycins A, B, C, D and E,”J Antibiot.(Tokyo) 1977, vol. 30, No. 11, p.p. 1015-1018.
Bobbitt, J. et al., “Isoquinolines. III. A New Synthesis of 1,2,3,4-tetrahydro isoquinolines,”J. Org. Chem.1965, vol. 30, p.p. 2247-2250.
Cabre-Castellvi, J. et al., “Convenient Synthesis of Carboxilic Acid Anhydrides using N,N-Bis[2-oxo-3-oxazol idinyl]phosphorodiamidic Chloride,”Synthesis1981, No. 7, p.p. 616-620.
Caldwell C. et al., “Synthesis of the Lipophilic Side Chain of the Cyclic Hexa-depsipeptide Antibiotic L-156, 602,”J. Org. Chem.1990, vol. 44, p.p. 2355-2361.
Caron, M. et al., “Highly Enantioselective Solvolyses of L- and D-Phenylalanine p-Nitrophenyl Esters by an L-Histidyl Dipeptide in Surfacant Coaggregates Formed by Cholesterol-Containing Amphiphiles,”J. Org. Chem.1988, vol. 53, No. 21, p.p. 5187-5189.
Corey, E. et al., “Enantioselective Total Synthesis of Ecteinacidin 743,”J. Am. Chem. Soc.1996, vol. 118, p.p. 9202-9203.
Danishefsky, S. et al., “Total synthesis of Quinocarcinol Methyl Ester,”J. Am. Chem. Soc.1985, vol. 107, No. 5, p.p. 1421-1423.
Fukuyama, T. et al., “Total Synthesis of(±) Saframycin A,”J. Am. Chem. Soc.1990, vol. 112, No. 8, p.p. 3712-3713.
Fukuyama, T. et al., “A Sterocontrolled Total Synthesis of (±) Reniramycin A,”Tetrahedron Lett.1990, vol. 31, No. 42, p.p. 5989-5992.
Fukuyama, T. et al., “Stereocontrolled total Synthesis of (±) Saframycin B,”J. Am. Chem. Soc.1982, vol. 104, No. 118, p.p. 4957-4958.
Gao, Y. et al., “Catalytic Asymmetric Epoxidation and Kinetic Resolution: Modified Procedures Including in Situ Derivatization,”J. Am. Chem. Soc.1987, vol. 109, No. 18, p.p. 5765-5780.
Guan, Y. et al., “Molecular and crystal structures of ecteinascidins: potent antitumor compounds from the Caribbean tunicate Ecteinascidia tur binata,”J. Biomol Struct. Dyn.1993, vol. 10, No. 5, p.p. 793-817.
Kishi, K. et al., “Structure-activity relationships of saframycins,”J Antibiot.(Tokyo) 1984, vol. 37, No. 8, p.p. 847-852.
Kitahara, Y. et al., “Synthesis of 4,7-Indolequinones. The Oxidative Demethylation of 4,7 Dimethoxyindoles with Ceric Ammonium Nitrate,”Chem. Phar. Bull.(Japan) 1985, vol. 33, No. 5, p.p. 2122-2128.
Kubo, A. et al., “Stereoselective total Synthesis of (±) Saframycin B,”J. Org. Chem.1988, vol. 53, No. 18, p.p. 4295-4310.
Martinez, E. et al., “Phthalascidin, a synthetic antitumor agent with potency and mode of action comparable to ecteinacidin 743,”Proc. Natl. Acad. Sci.1999, vol. 96, p.p. 3496-3501.
Medina, E. et al., “Enantioselective synthesis of N-Boc-1-naphthylglycine,”Tetrahedron Asym.1997, vol. 8, No. 10, p.p. 1581-1586.
Mikami, Y. et al., “Saframycin S, a new saframycin group antibiotic,”J. Pharmacobiodyn.1981, No. 4, p.p. 282-286.
Myers, A. et al. “A concise, Stereocontrolled Synthesis of (−) Saframycin A by the Directed Condensation of a-Amino Aldehyde Precursors,”J. Am. Chem. Soc.1999, vol. 121, No. 43, p.p. 10828-10829.
Sakai, R. et al., “Additional antitumor ecteinacidins from a Caribbean tunicate: Crystal structures and activites in vivo,”Proc. Natl. Acad. Sci.1992, vol. 89, p.p. 11456-11460.
Sakai, R. et al., “Ecteinascidins: Putative Biosynthetic Precursors and Absolute Stereochemistry,”J. Am. Chem. Soc.1996, vol. 118, No. 35, p.p. 9017-9023.
Sharpless, K. B. et al., “The Osmium-Catalyzed Asymmetric Dihydroxylation: A New Ligand Class and a Process Improvement,”J. Org. Chem.1992, vol., 57, No. 6, p.p. 2768-2771.
Zhou et al., “A novel face specific Mannich closure providing access to the saframycin-ecteinascidin series of piperazine based alkaloids,”Tetrahedron Letters2000, vol. 41, p.p. 2043-2046.
Zhou et al., “Synthetic explorations in the saframycin ecteinascidin series: construction of major chiral subunits through catalytic asymmetric induction,”Tetrahedron Letters2000, vol. 41, p.p. 2039-2042.

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