Title:
NUCLEOSIDE DERIVATIVE AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2019/088179
Kind Code:
A1
Abstract:
Provided are: a nucleoside that is more suitable for practical use such as an RNA medicine or the like; and the use of the nucleoside. For this purpose, provided is a nucleoside derivative represented by formula (1) or (2) or a salt thereof. [Chem. 16] (In formula (1), R1 represents a hydrogen atom, a hydroxy group, a hydroxy group in which a hydrogen atom is substituted with an alkyl group or an alkenyl group, or a protected group, and in formula (2), X represents a halogen atom. In formula (1) and formula (2), R2 and R3 may be the same or different and each represent a hydrogen atom, a protecting group for a hydroxy group, a phosphate group, a protected phosphate group, or -P(=O)nR5R6 (n represents 0 or 1, R5 and R6 may be the same or different and each represent a hydrogen atom, a hydroxy group, a protected hydroxy group, a mercapto group, a protected mercapto group, a lower alkoxy group, a cyano lower alkoxy group, an amino group, or a substituted amino group. Note that when n is 1, R5 and R6 would not simultaneously be a hydrogen atom.), each R4 represents NHR7 having a linking group (R7 represents a hydrogen atom, an alkyl group, an alkenyl group, or a protecting group for amino group), an azide group, an amidino group, or a guanidino group, and B represents one of a purin-9-yl group, a 2-oxo-pyrimidin-1-yl group, a substituted purin-9-yl group, or a substituted 2-oxo-pyrimidin-1-yl group.)
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Inventors:
UENO YOSHIHITO (JP)
MAEDA YUSUKE (JP)
KAJINO RYOHEI (JP)
MAEDA YUSUKE (JP)
KAJINO RYOHEI (JP)
Application Number:
PCT/JP2018/040544
Publication Date:
May 09, 2019
Filing Date:
October 31, 2018
Export Citation:
Assignee:
YAMASA CORP (JP)
UNIV GIFU (JP)
UNIV GIFU (JP)
International Classes:
C07H19/06; A61K31/712; A61K31/713; A61K48/00; A61P43/00; C07H19/10; C07H21/00; C07H21/02; C07H23/00; C12N15/113
Domestic Patent References:
| WO1994022454A1 | 1994-10-13 |
Foreign References:
| JPH10506915A | 1998-07-07 | |||
| JPH05148293A | 1993-06-15 | |||
| JP2017211339A | 2017-11-30 |
Other References:
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WANG,G. ET AL.: "Biophysical and biochemical properties of oligodeoxynucleotides containing 4'-C- and 5'-C-substituted thymidines", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 9, no. 6, 1999, pages 885 - 890, XP004160493
WANG, G. ET AL.: "5 -C-Branched thymidines: synthesis, stereochemistry, and incorporation into oligodeoxynucleotides", TETRAHEDRON LETTERS, vol. 37, no. 16, 1996, pages 2739 - 2742, XP004029784
HAMPTON,A. ET AL.: "Design of substrate-site-directed irreversible inhibitors of adenosine 5'-phosphate aminohydrolase. Effect of substrate substituents on affinity for the substrate site", JOURNAL OF MEDICINAL CHEMISTRY, vol. 19, no. 8, 1976, pages 1029 - 1033, XP55612847
KAZINO R.: "Synthesis of 4'C and 5'-C-aminoalkyl-modified siRNA and function evaluation", 48TH ANNUAL CONFERENCE OF NUCLEIC ACIDS THERAPEUTICS SOCIETY OF JAPAN; 11/11/2018, vol. 4, 25 June 2018 (2018-06-25), pages 81, XP009520660
KAZINO R: "Synthesis and characteristics of siRNA including 5'-C-aminopropyl-2'-O-methyl nucleoside", LECTURE PROCEEDINGS OF THE SPRING ANNUAL MEETING OF THE CHEMICAL SOCIETY OF JAPAN; MARCH 20-23, 2018, vol. 98, 6 March 2018 (2018-03-06), pages 4D7-44, XP009520662
KAJINO,R. ET AL.: "P012: Synthesis and Property of 5'-C-Aminoalkyl-modified siRNA", 44TH INTERNATIONAL SYMPOSIUM ON NUCLEIC ACIDS CHEMISTRY;: THE 44TH INTERNATIONAL SYMPOSIUM ON NUCLEIC ACIDS CHEMISTRY 2017 // THE 1ST ANNUAL MEETING OF JAPAN SOCIETY OF NUCLEIC ACIDS CHEMISTRY; NOVEMBER 14-16, 2017, vol. 44, 14 November 2017 (2017-11-14), pages 142 - 143, XP009520669
HELVATICA CHIMICA ACTA, vol. 83, 2000, pages 128 - 151
THE JOURNAL OF ORGANIC CHEMISTRY, vol. 77, 2012, pages 3233 - 3245
BIOORGANIC & CHEMISTRY LETTERS, 1999, pages 2667 - 2672
THE JOURNAL OF ORGANIC CHEMISTRY, vol. 78, 2013, pages 9956 - 9962
"Protective Groups in Organic Synthesis", 2007, JOHN WILEY AND SONS
J. PHARM. SCI., 1977, pages 1 - 19
BIOORGANIC & MEDICAL CHEMISTRY, vol. 11, 2003, pages 211 - 2226
BIOORGANIC & CHEMISTRY LETTERS, 1999, pages 2667 - 2672
NUCLEIC ACIDS RESEARCH, vol. 43, 2015, pages 2993 - 3011
MARIE MATURANO ET AL., EUR. J. ORG. CHEM., 2012, pages 721 - 730
WANG,G. ET AL.: "Biophysical and biochemical properties of oligodeoxynucleotides containing 4'-C- and 5'-C-substituted thymidines", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 9, no. 6, 1999, pages 885 - 890, XP004160493
WANG, G. ET AL.: "5 -C-Branched thymidines: synthesis, stereochemistry, and incorporation into oligodeoxynucleotides", TETRAHEDRON LETTERS, vol. 37, no. 16, 1996, pages 2739 - 2742, XP004029784
HAMPTON,A. ET AL.: "Design of substrate-site-directed irreversible inhibitors of adenosine 5'-phosphate aminohydrolase. Effect of substrate substituents on affinity for the substrate site", JOURNAL OF MEDICINAL CHEMISTRY, vol. 19, no. 8, 1976, pages 1029 - 1033, XP55612847
KAZINO R.: "Synthesis of 4'C and 5'-C-aminoalkyl-modified siRNA and function evaluation", 48TH ANNUAL CONFERENCE OF NUCLEIC ACIDS THERAPEUTICS SOCIETY OF JAPAN; 11/11/2018, vol. 4, 25 June 2018 (2018-06-25), pages 81, XP009520660
KAZINO R: "Synthesis and characteristics of siRNA including 5'-C-aminopropyl-2'-O-methyl nucleoside", LECTURE PROCEEDINGS OF THE SPRING ANNUAL MEETING OF THE CHEMICAL SOCIETY OF JAPAN; MARCH 20-23, 2018, vol. 98, 6 March 2018 (2018-03-06), pages 4D7-44, XP009520662
KAJINO,R. ET AL.: "P012: Synthesis and Property of 5'-C-Aminoalkyl-modified siRNA", 44TH INTERNATIONAL SYMPOSIUM ON NUCLEIC ACIDS CHEMISTRY;: THE 44TH INTERNATIONAL SYMPOSIUM ON NUCLEIC ACIDS CHEMISTRY 2017 // THE 1ST ANNUAL MEETING OF JAPAN SOCIETY OF NUCLEIC ACIDS CHEMISTRY; NOVEMBER 14-16, 2017, vol. 44, 14 November 2017 (2017-11-14), pages 142 - 143, XP009520669
HELVATICA CHIMICA ACTA, vol. 83, 2000, pages 128 - 151
THE JOURNAL OF ORGANIC CHEMISTRY, vol. 77, 2012, pages 3233 - 3245
BIOORGANIC & CHEMISTRY LETTERS, 1999, pages 2667 - 2672
THE JOURNAL OF ORGANIC CHEMISTRY, vol. 78, 2013, pages 9956 - 9962
"Protective Groups in Organic Synthesis", 2007, JOHN WILEY AND SONS
J. PHARM. SCI., 1977, pages 1 - 19
BIOORGANIC & MEDICAL CHEMISTRY, vol. 11, 2003, pages 211 - 2226
BIOORGANIC & CHEMISTRY LETTERS, 1999, pages 2667 - 2672
NUCLEIC ACIDS RESEARCH, vol. 43, 2015, pages 2993 - 3011
MARIE MATURANO ET AL., EUR. J. ORG. CHEM., 2012, pages 721 - 730
Attorney, Agent or Firm:
KAI-U PATENT LAW FIRM (JP)
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