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Title:
CROSSLINKED NUCLEIC ACID GUNA, METHOD FOR PRODUCING SAME, AND INTERMEDIATE COMPOUND
Document Type and Number:
WIPO Patent Application WO/2017/047816
Kind Code:
A1
Abstract:
The present invention provides a method for producing guanidine crosslinked artificial nucleic acid (abbreviated hereinafter as GuNA), and an intermediate compound for the production thereof. Specifically, the present invention provides a method for producing a compound represented by general formula I: (in the formula, R1、R2、R3、R4、R5、R6、m, and ring A are as defined in the specification) or a salt thereof wherein a reducing agent is reacted with a compound represented by general formula II: (in the formula, R1、R2、R3、R4、R5、R6、m, and ring A' are as defined in the specification).

Inventors:
OBIKA SATOSHI (JP)
KAWANISHI EIJI (JP)
SAWAMOTO HIROAKI (JP)
YAMAKOSHI SHUHEI (JP)
ARAI YUUKI (JP)
KUMAGAI SHINJI (JP)
Application Number:
PCT/JP2016/077748
Publication Date:
March 23, 2017
Filing Date:
September 20, 2016
Export Citation:
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Assignee:
MITSUBISHI TANABE PHARMA CORP (JP)
UNIV OSAKA (JP)
International Classes:
C07H9/06; C07H19/06; C07H19/16; C07H21/00
Domestic Patent References:
WO2014046212A12014-03-27
WO2007145593A12007-12-21
WO2011156202A12011-12-15
WO2014124952A12014-08-21
WO2003095467A12003-11-20
WO2014109384A12014-07-17
WO2011052436A12011-05-05
WO2015054465A12015-04-16
WO1998039352A11998-09-11
WO2005021570A12005-03-10
WO2016145142A12016-09-15
WO2016100569A12016-06-23
Foreign References:
JPH09328497A1997-12-22
JP2002521310A2002-07-16
Other References:
SHRESTHA, A.R. ET AL.: "Guanidine bridged nucleic acid (GuNA): an effect of a cationic bridged nucleic acid on DNA binding affinity", CHEM.COMMUN., vol. 50, 2014, pages 575 - 577, XP055246151
BARMAN, J. ET AL.: "2′-N-Guanidino,4′-C-ethylene bridged thymidine (GENA-T) modified oligonucleotide exhibits triplex formation with excellent enzymatic stability", RSC ADV., vol. 5, 2015, pages 12257 - 12260, XP055369015
MADSEN, A.S. ET AL.: "Large Scale Synthesis of 2′-Amino-LNA Thymine and 5-Methylcytosine Nucleosides", J.ORG.CHEM., vol. 77, 2012, pages 10718 - 10728, XP055266339
HANESSIAN, S. ET AL.: "A Constrained Tricyclic Nucleic Acid Analogue of α-l-LNA: Investigating the Effects of Dual Conformational Restriction on Duplex Thermal Stability", J.ORG.CHEM., vol. 78, 2013, pages 9064 - 9075, XP055081143
KITANO,K. ET AL.: "Synthesis of 4′-C-fluoromethylnucleosides as potential antineoplastic agents", TETRAHEDRON, vol. 53, no. 39, 1997, pages 13315 - 13322, XP004106140
SALINAS, J.C. ET AL.: "Alternative Syntheses of ( S )-cEt-BNA: A Key Constrained Nucleoside Component of Bioactive Antisense Gapmer Sequences", J.ORG.CHEM., vol. 79, 2014, pages 11651 - 11660, XP055287274
See also references of EP 3351548A4
Attorney, Agent or Firm:
SAMEJIMA, Mutsumi et al. (JP)
Mutsumi Sameshima (JP)
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