Process for the synthesis of oligomeric compounds

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C536S023100, C536S024300, C536S024500, C536S025330, C536S025340

Reexamination Certificate

active

07041816

ABSTRACT:
Synthetic processes are provided wherein oligomeric compounds are prepared having phosphodiester, phosphorothioate, phosphorodithioate, or other covalent linkages. The oligomers have substantially reduced exocyclic adducts deriving from acrylonitrile or related contaminants.

REFERENCES:
patent: 3687808 (1972-08-01), Merigan et al.
patent: 4415732 (1983-11-01), Caruthers et al.
patent: 4417046 (1983-11-01), Hsiung
patent: 4426517 (1984-01-01), Hsiung
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: 4672110 (1987-06-01), Letsinger
patent: 4725677 (1988-02-01), Köster et al.
patent: 4835263 (1989-05-01), Nguyen et al.
patent: 4973679 (1990-11-01), Caruthers et al.
patent: 5132418 (1992-07-01), Caruthers et al.
patent: RE34069 (1992-09-01), Köster et al.
patent: 5210264 (1993-05-01), Yau
patent: 5212295 (1993-05-01), Cook
patent: 5362866 (1994-11-01), Arnold, Jr.
patent: 5514789 (1996-05-01), Kempe
patent: 5589586 (1996-12-01), Holmberg
patent: 5686599 (1997-11-01), Tracz
patent: 5750672 (1998-05-01), Kempe
patent: 5804683 (1998-09-01), Usman et al.
patent: 5936077 (1999-08-01), Pfleiderer et al.
patent: 5977343 (1999-11-01), Tracz
patent: 6054576 (2000-04-01), Bellon et al.
patent: 6162909 (2000-12-01), Bellon et al.
patent: 6166197 (2000-12-01), Cook et al.
patent: 6172209 (2001-01-01), Manoharan et al.
patent: 6271358 (2001-08-01), Manoharan et al.
patent: 6303773 (2001-10-01), Bellon et al.
patent: 6465628 (2002-10-01), Ravikumar et al.
patent: 6649751 (2003-11-01), Usman et al.
patent: 6664388 (2003-12-01), Nelson
patent: 6673918 (2004-01-01), Bellon et al.
patent: 2002/0072593 (2002-06-01), Sinha
patent: 2003/0181712 (2003-09-01), Nelson
patent: 19627898 (1998-01-01), None
patent: 0514513 (1992-11-01), None
patent: 1028124 (2000-08-01), None
patent: 62-043997 (1987-02-01), None
patent: WO 97 29780 (1997-08-01), None
patent: WO 00/46231 (2000-08-01), None
patent: WO 01/96358 (2001-12-01), None
Hsiung et al., “Further Improvements on the Phosphodiester Synthesis of Deoxyribonucleotides and the Oligonucleotide Directed Site-Specific Mutagenesis ofE. coliLipoprotein Gene,”Nucleic Acids Research, 11(10), 3227-3239 (May 25, 1983).
Ohtsuka et al. (I), “Studies on Transfer Ribonucleic Acids and Related Compounds. XVL. Synthesis of Ribooligonucleotides Using a Photosensitive o-Nitrobenzyl Protection for the 2'-Hydroxyl Group,”Chemical&Pharmaceutical Bulletin(Japan),25(5), 949-959 (May, 1997).
Ohtsuka et al. (II), “Synthesis ofE. colitRNAfMetFragments,” presented at the Fourth Symposium on Nucleic Acid Chemistry, Kyoto, Japan, Nov. 26-27, 1976,Nucleic Acids Research Symposium Series, Sepcial Publication No. 2,E. Coast (ed.), IRL Press, Ltd, London, England, pp. s77-s80 (1976).
Caruthers, “DNA Synthesis for Nonchemists: The Phosphoramidite Method on Silica Supports,” Chapter 3 inSynthesis and Applications of DNA and RNA,S. A. Narang (ed.), Academic Press, Inc., 1987, New York, NY, only pp. 47-94 supplied.
Schulhof et al., “Facile Removal of New Base Protecting Groups Useful in Oligonucleotide Synthesis,”Tetrahedron Letters, 28(1), 51-54 (1987).
Alul, R.H. et al., “Oxalyl-CPG: a labil support for synthesis of sensitive oligonucleotide derivatives”,Nucl. Acad Res.,1991, 19, 1527-1532.
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 (Aug. 22, 1985).
Beaucage, S.L. et al., “Advances in the Synthesis of Oligonucleotides by the Phsophoramidite Approach”,Tetrahedron,1992, 48, 2223-2311.
Brown, T. et al., “Modern machine-aided methods of oligodeoxyribonucleotide synthesis”,Oligonucleotides and Analogs A Practical Approach,1991, Chapter 1, Ekstein, F., ed., 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.
Englisch, U. et al., “Chemicaly Modified Oligonucleotides as Probes and Inhibitors”,Angew. Chem. Int. Ed. Eng.,1991, 30, 613-629 (Jun., 1991).
Eritja, R. et al., “A Synthetic Procedure for the Preparation of Oligonucleotides Without Using Ammonia and Its Application for the Synthesis of Oligonucleotides Containing O-4-Alkyl Thymidines”,Tetrahedron,1992, 48(20), 4171-4182.
Geiger, L.E. et al., “Metabolism of Acrylonitrile by Isolated Rat Hepatocytes”,Cancer Res.,1983, 43, 3080-3087 (Jul., 1983).
Griffey, R.H. et al., “2′-O-Aminopropyl Ribonucleotides: A Zwitterionic Modification that Enhances the Exonuclease Resistance and Biological Activity of Antisense Oligonucleotides”,J. Med. Chem.,1996, 39(26):, 5100-5109 (Dec. 1, 1996).
Hogy, L.L. et al., “In Vivo Interaction of Acrylonitrile and 2-Cyanoethylene Oxide with DNA in Rats”,Cancer Res.,1986, 46, 3932-3938 (Aug., 1986).
Iyer, R.P. et al., “The Automated Synthesis of Sulfur-Containing Oligodeoxyribonucleotides Using 3H-1,2-Benzodithiol-3-one 1,1-Dioxide as a Sulfur-Transfer Reagent”,J. Org. Chem.,1990, 55, 4693-4699.
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.
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.
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.
Miura, K. et al., “Blockwise Mechanical Synthesis of Oligonucleotides by the Phosphoramidite Method”,Chem Pharm. Bull.,1987, 35, 833-836.
Mullah, B. et al., “Automated Synthesis of Double Dye-Labeled Oligonculetides using Tetramethylrhodamine (TAMRA) Solid Supports,”Tetra. Letts.,1997, 38(33), 5751-5754.
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.
Pon, R.T. et al., “Hydroquinone-O, O-diacetic acid (‘Q-linker’) as a replacement for succinyl and oxalyl linker arms in solid phase oligonucleotide synthesis,”Nucl. Acids Res.,1997, 25(18), 3629-3635.
Rao, M. V. et al., “Dibenzoyl Tetrasulphide-A Rapid Sulphur Transfer Agent in the Synthesis of Phosphorothioate Analogues of Oligonucleotides”,Tetra. Letts.,1992, 33, 4839-4842.
Ravasio, N. et al., “Selective Hydrogenations Promoted by Copper Catalysts. 1. Chemoselectivity, Regioselectivity, and Steroselectivity in the Hydrogenation of 3-Substituted Steroids”,J. Org. Chem.,1991, 56, 4329-4333.
Sanghvi, Y.S., “Heterocyclic Base Modifications in Nucleic acids and their Applications in Antisense Oligonucleotides”,Antisense Research and Applications,1993, Chapter 15, CRC Press, Boca Raton, 273-288.
Secrist, J.A. et al., “Synthesis and Biological Activity of 4′-Thionucleosides”,10th International Roundtable: Nucleosides, Nucleotides and their Biological Applications,Sep. 16-20, 1992, Abstract 21, Park City, Utah, 40.
Sobkowski, M. et al., “The Reactions of H-Phosphonates

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Process for the synthesis of oligomeric compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.

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

Rate now

     

Profile ID: LFUS-PAI-O-3622614

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.