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)
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:
Assignee:
MITSUBISHI TANABE PHARMA CORP (JP)
UNIV OSAKA (JP)
UNIV OSAKA (JP)
International Classes:
C07H9/06; C07H19/06; C07H19/16; C07H21/00
Domestic Patent References:
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| WO2007145593A1 | 2007-12-21 | |||
| WO2011156202A1 | 2011-12-15 | |||
| WO2014124952A1 | 2014-08-21 | |||
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Foreign References:
| JPH09328497A | 1997-12-22 | |||
| JP2002521310A | 2002-07-16 |
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
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
Attorney, Agent or Firm:
SAMEJIMA, Mutsumi et al. (JP)
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