Process for the synthesis of oligomeric compounds

Details Process for the synthesis of oligomeric compounds Process for the synthesis of oligomeric compounds

1998-02-10

2000-02-01

Crane, L. Eric

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

Organic compounds

Carbohydrates or derivatives

536 243, 536 245, 536 267, 536 2534, C07H 2102, C07H 2104

Patent

active

060204753

ABSTRACT:
Synthetic processes are provided wherein oligomeric compounds are prepared having phosphodiester, phosphorothioate, and phosphorodithioate covalent linkages. Also provided are synthetic intermediates useful in such processes.

REFERENCES:
patent: Re34069 (1992-09-01), Koster
patent: 3687808 (1972-08-01), Merigan et al.
patent: 4415732 (1983-11-01), Caruthers et al.
patent: 4458066 (1984-07-01), Caruthers et al.
patent: 4500707 (1985-02-01), Caruthers et al.
patent: 4668777 (1987-05-01), Caruthers et al.
patent: 4725677 (1988-02-01), Koster et al.
patent: 4816571 (1989-03-01), Andrus et al.
patent: 4973679 (1990-11-01), Caruthers et al.
patent: 5026838 (1991-06-01), Nojiri et al.
patent: 5132418 (1992-07-01), Caruthers et al.
patent: 5185334 (1993-02-01), Solomon et al.
patent: 5210264 (1993-05-01), Yau
patent: 5212295 (1993-05-01), Cook
patent: 5527899 (1996-06-01), Froehler
patent: 5554746 (1996-09-01), Ravikumar et al.
patent: 5571902 (1996-11-01), Ravikumar et al.
patent: 5705621 (1998-01-01), Ravikumar
patent: 5714597 (1998-02-01), Ravikumar et al.
patent: 5760209 (1998-06-01), Cheruvallah et al.
patent: 5783690 (1998-07-01), Cheruvallah et al.
Watanabe et al., "Utilization of O-Xylylene N, N-Diethylphosphoramidite for the Synthesis of Phosphoric Diesters," Tetrahedron Letters, 33(10), 1313-1316 (Mar. 3, 1992).
Andrade et al., "Efforts Toward Synthesis of Oligonucleotides for Commercialization," Nucleosides & Nucleotides, 16(7-9), 1617-1620 (Sep. 15, 1996).
Cheruvallah et al.(III), "Solution Phase Synthesis of an Oligodeoxyribonucleotide Phosphorthioate for Therapeutic Applications," Nucleosides & Nucleotides, 16(7-9), 1625-1628 (Sep. 15, 1996).
Krotz et al., "Improved Impurity Profile of Phosphorothioate Oligonucleotides Through the Use of Dimeric Phosphoramidite Synthons," Nucleosides & Nucleotides, 16(7-9), 1637-1640 (Sep. 15, 1996).
Agrawal, S., Eds., Protocols for Oligonucleotides and Analogs, 1993, Humana Press, Totowa, NJ.
Alul, R.H. et al., "Oxalyl-CPG: a labile support for synthesis of sensitive oligonucleotide derivatives", Nuc. Acid Res., 1991, 19, 1527-1532 (No. 7).
Ausubel, F.M. et al., Eds., Current Protocols in Molecular Biology, 1993, Current Publications.
Bannwarth, W., "Synthesis of Oligodeoxynucleotides by the Phosphite-Triester Method Using Dimer Units and Different Phosphorous-Protecting Groups", Helvetica Chim. Acta, 1985, 68, 1907-1913.
Beaucage, S.L. et al., "Advances in the Synthesis of Oligonucleotides by the Phosphoramidite Approach", Tetrahedron, 1992, 48, 2223-2311 (No. 12).
Bielinska, A. et al., "Regulation of Gene Expression with Double-Stranded Phosphorothioate Oligonucleotides", Science, 1990, 250, 997-1000 (Nov. 16, 1990).
Brown, T. et al., "Modern machine-aided methods of oligodeoxyribonucleotide synthesis", Oligonucleotides and Analogs, Ekstein, F., eds., IRL Press, Oxford, 1-24.
Cook, P.D., "Medicinal chemistry of antisense oligonucleotides--future opportunities", Anti-Cancer Drug Design, 1991, 6, 585-607.
Delgado, C. et al., "The Uses and Properties of PEG-Linked Proteins", Crit. Rev. in Therapeutic Drug Carrier Sys., 1992, 9, 249-304.
Efimov, V.A. et al., "New efficient sulfurizing reagents for the preparation of oligodeoxyribonucleotide phosphorothioate analogues", Nucl. Acids. Res., 1995, 23, 4029-4033 (Issue No. 20).
Englisch, U. et al., "Chemically Modified Oligonucleotides as Probes and Inhibitors", Angew. Chem. Int. Ed. Eng., 1991, 30, 613-629, No. 6, Jun. 1991.
Greene et al., Protective Groups in Organic Synthesis, 1991, 2nd Ed., John Wiley & Sons.
Iyer, R.P. et al., "3H-1,2-Benzodithiole-3-one 1,1-Dioxide as an Improved Sulfurizing Reagent in the Solid-Phase Synthesis of Oligodeoxyribonucleoside Phosphorothioates", J. Am. Chem. Soc., 1990, 112, 1253-1254.
Iyer, R.P. et al., "The Automated Synthesis of Sulfur-Containing Oligodeoxyribonucleotides Using 3H-1,2-Benzodithiol-3-one 1,1-Dioxide as Sulfur-Transfer Reagent", J. Org. Chem., 1990, 55, 4693-4699, No. 15.
Kamer, P.C.J. et al., "An Efficient Approach Toward the Synthesis of Phosphorothioate Diesters via the Schonberg Reaction", Tetrahedron Letts., 1989, 30, 6757-6760, No. 48.
Kroschwitz, J.I., "Polynucleotides", Concise Encyclopedia of Polymer Science and Engineering, 1990, John Wiley & Sons, New York, 858-859.
Kumar, G. et al., "Improvements in Oligodeoxyribonucleotide Synthesis: Methyl N,N-Dialkylphosphoramidite Dimer Units for Solid Support Phosphite Methodology", J. Org. Chem., 1984, 49, 4905-4912, No. 25.
Miura, K. et al., "Blockwise Mechanical Synthesis of Oligonucleotides by the Phosphoramidite Method", Chem. Pharm. Bull., 1987, 35, 833-836, No. 2.
Ouchi, T. et al., "Synthesis and Antitumor Activity of Poly(Ethylene Glycol)s Linked to 5'-Fluorouracil via a Urethane or Urea Bond", Drug Des. & Disc., 1992, 9, 93-105.
Pierce, M.E. et al., "Stereoselective Synthesis of HIV-1 Protease Inhibitor, DMP 323", J. Org. Chem., 1996, 61, 444-450, No. 2.
Rao, M.V. et al., "Dibenzoyl Tetrasulphide--A Rapid Sulphur Transfer Agent in the Synthesis of Phosphorothioate Analogues of Oligonucleotides", Tetrahedron Letts., 1992, 33, 4839-4842, No. 33.
Ravasio, N. et al., "Selective Hydrogenations Promoted by Copper Catalysts. 1. Chemoselectivity, Regioselectivity, and Stereoselectivity in the Hydrogenation of 3-Substituted Steroids", J. Org. Chem., 1991, 56, 4329-4333, No. 13.
Sambrook, J. et al., Eds., Molecular Cloning, A Laboratory Manual, 1989, 2nd Ed., Cold Spring Harbor Laboratory Press.
Sanghvi, Antisense Research and Application, 1993, Ch. 15, Crooke, S.T. et al., Eds., CRC Press.
Secrist, J.A. et al., "Synthesis and Biological Activity of 4'-Thionucleosides", 10th International Rountable: Nucleosides, Nucleotides and their Biological Applications, Sep. 16-20 1985, Abstract 21, Park City, Utah, 40.
Stec, W.J. et al., "Stereospecific Synthesis of P-chiral Analogs of oligonucleotides", Methods in Molecular Biology, 20, 1993, Chapter 14, Humana Press, Totowa, NJ, 285-313.
Stec, W.J. et al., "Novel route to oligo(deoxyribonucleoside phosphorothioates). Stereocontrolled synthesis of P-chiral oligo(deoxyribonucleoside phosphorothioates)", Nucl. Acids Res., 1991, 19, 5883-5888, No. 21.
Stec et al., "Bis (O,O-Diisopropoxy Phosphinothioyl)Disulfide--A Highly Efficient Sulfurizing Reagent for Cost-Effective Synthesis of Oligo(Nucleoside Phosphorothioate)s", Tetrahedron Letts., 1993, 34, 5317-5320, No. 33.
Vu, H., "Internucleotide Phosphite Sulfurization with Tetraethyl Thiuram Disulfide. Phosphorothioate Oligonucleotide Synthesis via Phosphoramidite Chemistry", Tetrahedron Letts., 1991, 32, 3005-3008, No. 26.
Wolter, A. et al., Polymer Support Oligonucleotide Synthesis XX: Synthesis of a Henhectacosa Deoxynucleotide by use of a Dimeric Phosphoramidite Nucleosides & Nucleotides, 1986, 5, 65-77.
Wright, P. et al., "Large Scale Synthesis of Oligonucleotides bia Phosphora;midite Nulceosides and a High-loaded Poylstyrene Support", Tetrahedron Letts., 1993, 34, 3373-3376, No. 21.
Wu, H. et al., "Inhibition of in vitro transcription by specific double-stranded oligodeoxyribonucleotides", Gene, 1990, 89, 203-209.
Xu, Q. et al., "Use of 1,2,4-dithiazolidine (DtsNH) and 3-ethoxy-1,2,4-dithiazoline-5-one (EDITH) for synthesis of phosphorothioate-containing oligodeoxyribonucleotides", Nucl. Acids Res., 1996, 24, 1602-1607, No. 9.
Xu, Q. et al., "Efficient introduction of phosphorothioates into RNA oligonucleotides by 3-ethoxy-1,2,4-dithiazoline-5-one (EDITH)", Nucl. Acids Res., 1996, 24, 3643-3644, No. 18.
Aldrich Chemical Company Catalog, 1994-1995, p. 32.

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