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Title:
METHOD FOR LIQUID-PHASE SYNTHESIS OF NUCLEIC ACID
Document Type and Number:
WIPO Patent Application WO/2014/077292
Kind Code:
A1
Abstract:
In this method, an oligonucleotide is prepared by using, as a synthesis unit, a novel nucleoside monomer compound represented by formula (I) [wherein X, R1, Y, Base, Z, Ar, R2, R3 and n are each as defined in Claim 1]. The novel nucleoside monomer compound is a nucleoside, the base moiety of which is substituted with an aromatic-hydrocarbon-ring-carbonyl or -thiocarbonyl group having at least one hydrophobic group. The method can dispense with column-chromatographic purification in every reaction, and enables base elongation not only in the 3'-direction but also in the 5'-direction, thus attaining efficient liquid-phase mass synthesis of an oligonucleotide.

Inventors:
NONOGAWA Mitsuru (17-85 Jyusohonmachi 2-chome, Yodogawa-k, Osaka-shi Osaka 24, 〒5320024, JP)
NAGATA Toshiaki (17-85 Jyusohonmachi 2-chome, Yodogawa-k, Osaka-shi Osaka 24, 〒5320024, JP)
SAITO Hideki (17-85 Jyusohonmachi 2-chome, Yodogawa-k, Osaka-shi Osaka 24, 〒5320024, JP)
YASUMA Tsuneo (17-85 Jyusohonmachi 2-chome, Yodogawa-k, Osaka-shi Osaka 24, 〒5320024, JP)
Application Number:
JP2013/080724
Publication Date:
May 22, 2014
Filing Date:
November 13, 2013
Export Citation:
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Assignee:
TAKEDA PHARMACEUTICAL COMPANY LIMITED (1-1 Doshomachi 4-chome, Chuo-ku Osaka-shi Osaka, 45, 〒5410045, JP)
International Classes:
C07H19/073; C07H19/067; C07H21/04
Domestic Patent References:
WO2005070859A12005-08-04
WO2013122236A12013-08-22
Foreign References:
JP2010275254A2010-12-09
JP2000327694A2000-11-28
JP2009185063A2009-08-20
JP2008100976A2008-05-01
Other References:
PURI NITIN ET AL: "SYNTHESIS OF 5'-POLYARENE-TETHERED OLIGO-DNAS AND THE THERMAL STABILITY AND SPECTROSCOPIC PROPERTIES OF THEIR DUPLEXES AND TRIPLEXES", TETRAHEDRON, vol. 53, no. 30, 1997, pages 10409 - 10432, XP004105925
KURATA C. ET AL: "CHARACHTERIZATION OF HIGH MOLECULAR WEIGHT IMPURITIES IN SYNTHETIC PHOSPHOROTHIOATE OLIGONUCLEOLIDES", BIOORGANIC MEDICINAL CHEMISTRY LETTERS, vol. 16, no. 3, 2006, pages 607 - 614, XP027965842
See also references of EP 2921499A4
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REESE ET AL., NUCLEOSIDES & NUCLEOTIDES, vol. 17, no. 1-3, 1998, pages 451 - 470
WUTS ET AL.: "Protective Groups in Organic Synthesis", 2006, JOHN WILEY & SONS, INC.
"Encyclopedia of Experimental Chemistry in English", 2010, THE CHEMICAL SOCIETY OF JAPAN, pages: 377 - 381
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H. VU ET AL., TETRAHEDRON LETT., vol. 32, 1991, pages 3005 - 3008
R.P. LYER ET AL., J. AM. CHEM. SOC., vol. 112, 1990, pages 1253 - 1254
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"Encyclopedia of Experimental Chemistry in English", vol. 16, 2010, THE CHEMICAL SOCIETY OF JAPAN, article "Organic Compound IV", pages: 381 - 384
Attorney, Agent or Firm:
ASAMURA PATENT OFFICE, P.C. (Tennoz Central Tower, 2-2-24 Higashi-Shinagawa Shinagawa-k, Tokyo 76, 〒1408776, JP)
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