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

C536S025340

Reexamination Certificate

active

11024958

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: 6858715 (2005-02-01), Ravikumar et al.
patent: 2002/0072593 (2002-06-01), Sinha
patent: 2003/0181712 (2003-09-01), Nelson
patent: 196 27 898 (1998-01-01), None
patent: 0 514 513 (1996-01-01), None
patent: 1 028 124 (2000-08-01), None
patent: 62-42997 (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
Alul, R. H. et al, “Oxalyl-CPG: a labile support for synthesis of sensitive oligonucleotide derivatives,”Nucleic Acids Res. (1991) 19(7): 1527-1532.
Bannwarth, W., “Synthesis of Oligodeoxynucleotides by the Phosphite-Triester Method Using Dimer Units and Different Phosphorus-Protecting Goups,”Helv. Chim. Acta(1985) 68: 1907-1913.
Beaucage, S. L. et al., “Advances in the Synthesis of Oligonucleotides by the Phosphoramidite Approach,”Tetrahedron(1992) 48(12): 2223-2311.
Boal, J. H. et al., “Cleavage of oligodeoxyribonucleotides from controlled-pore glass supports and their rapid deprotection by gaseous amines,”Nucleic Acids Res. (1996) 24(15): 3115-3117.
Brown, T. et al., “Modern machine-aided methods of oligodeoxyribonucleotide synthesis,”Oligonucleotides and Analogs A Practical Approach(1991), Chp. 1, Eckstein, F. (ed), IRL Press, Oxford, pp. 1-24.
Cook, P. D., “Medicinal chemistry of antisense oligonucleotides—future opportunities,”Anti-Cancer Drug Design(1991) 6: 585-607.
Caruthers, M. H., “DNA Synthesis for Nonchemists: The Phosphoramidite Method on Silica Supports,”Synthesis and Applications of DNA and RNA(1987), Narang, S. A. (ed.). Academic Press, Inc., Orlando, pp. 47-94.
Delgado, C. et al., “The Uses and Properties of PEG-Linked Proteins,”Crit. Rev. In Therap. Drug Carriers Sys. (1992) 9(3,4): 249-304.
Efimov, V. A. et al., “New efficient sulfurizing reagents for the preparation of oligodeoxyribonucleotide phosphorothioate analoques,”Nucleic Acids Res. (1995) 23(20): 4029-4033.
Englisch, U. et al., “Chemically Modified Oligonucleotides as Probes and Inhibitors,”Angew. Chem. Int. Ed. Eng. (1991) 30(6): 613-629.
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(7): 3080-3087.
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.
Hogy, L. L. et al., “In Vivo Interaction of Acrylonitrile and 2-Cyanoethylene Oxide with DNA in Rats,”Cancer Res. (1986) 46(8): 3932-3938.
Hsiung, H. et al., “Further improvements on the phosphodiester synthesis of deoxyriboligonucleotides and the oligonucleotide directed site-specific mutagenesis ofE.colilipoprotein gene,”Nucleic Acids Research(1983) 11(10): 3227-3239. (May 25, 1983).
Iyer, R. P. et al., “The Automated Synthesis of Sulfur-Containing Oligodeoxyribonucleotides Using 3H-1,2-Benzodithiol-3-one 1,1-Dioxide as a Sulfer-Transfer Reagent,”J. Am. Chem. Soc. (1990) 55(15): 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 Phophorothioates,”J. Am. Chem. Soc. (1990) 112(3): 1253-1254.
Kamer, P. C. J. et al., “An Efficient Approach Toward the Synthesis of Phosphorothioate Diesters via the Schönberg Reaction,”Tetrahedron Letts. (1989) 30(48): 6757-6760.
Kroschwitz, J. I., “Polynucleotides,”Concise Encyclopedia of Polymer Science and Engineering(1990) John Wiley & Sons, New York, pp. 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(25): 4902-4912.
Martin, P., “Ein neuer Zugang zu 2′-O-Alkylribonucleosiden und Eigenschaften deren Oligonucleotide,”Helvetica Chimica Acta(1995) 78: 486-504.
Miura, K. et al., “Blockwise Mechanical Synthesis of Oligonucleotides by the Phosphoramidite Method,”Chem. Pharm. Bull. (1987) 35(2): 833-836.
Mullah, B. et al., “Automated Synthesis of Double Dye-Labeled Oligonucleotides using Tetramethylrhodamine (TAMRA) Solid Supports,”Tetra Letts. (1997) 38(33): 5751-5754.
Ohtsuka, E. et al., “Studies on Transfer Ribonucleic Acids and Related Compounds. XVI. Synthesis of Ribooligonucleotides Using a Photosensitive o-Nitrobenzyl Protection for the 2′-Hydroxyl Group,”Chemical&Pharmaceutical Bulletin(1997) 25(5): 949-959. (May 1997).
Ohtsuka, E. et al., “Synthesis ofE.colitRNAfMetfragments”,Nucleic Acids Research Symposium Series, Special Publication No. 2 (1976), pp. s77-s80.
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,”Nucleic 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(33): 4839-4842.
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(13): 4329-4333.
Sanghvi, Y.S., “Heterocyclic Base Modifications in Nucleic acids and their Applications in Antisense Oligonucleotides,”Antisense Research and Applications(1993) Chp. 15, CRC Press, Boca Raton, pp. 273-288.
Schulhof, J. C. et al., “Facile Removal of New Base Protecting Groups Useful in Oligonucleotide Synthesis,”Tetrahedron Letts. (1987) 28(1): 51-54.
S

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-3809560

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