Title:
NUCLEOSIDE DERIVATIVE AND USE THEREFOR
Document Type and Number:
WIPO Patent Application WO/2018/110678
Kind Code:
A1
Abstract:
[Problem] To provide a nucleoside that is more practical for RNA pharmaceuticals and other applications and a use therefor. [Solution] A nucleoside derivative indicated by formula (1) or (2) or a salt thereof. (In formula (1), R1 indicates a hydrogen atom, a hydroxyl group, a hydroxyl group having a hydrogen atom substituted by an alkyl group or an alkenyl group, or a protected group. In formula (2), X indicates a halogen atom. In formulas (1) and (2), R2 and R4 can be the same or different and indicate a hydrogen atom, a protecting group for a hydroxyl group, a phosphate group, a protected phosphate group, or –P(=0)nR5R6 (n indicates 0 or 1 and R5 and R6 can be the same or different and indicate either a hydrogen atom, a hydroxyl group, a protected hydroxyl group, a thiol group, a protected thiol group, a lower alkoxy group, a cyano lower alkoxy group, an amino group, or a substituted amino group. When n is 1, however, R5 and R6 are never both hydrogen atoms.) R3 indicates NHR7 having a linking group for each (R7 indicating a hydrogen atom, an alkyl group, an alkenyl group, or a protecting group for an amino group), an azide group, an amidino group, or a guanidino group. B indicates a purine-9-yl group, a 2-oxo-pyrimidin-1-yl group, a substituted purine-9-il group, or a substituted 2-oxo-pyrimidin-1-yl group.)
Inventors:
UENO YOSHIHITO (JP)
Application Number:
PCT/JP2017/044995
Publication Date:
June 21, 2018
Filing Date:
December 14, 2017
Export Citation:
Assignee:
UNIV GIFU (JP)
International Classes:
C07H19/06; A61K47/26; C07H19/067; C07H21/02; C07H21/04; C12N15/09
Domestic Patent References:
| WO2015200219A1 | 2015-12-30 | |||
| WO2014112463A1 | 2014-07-24 |
Foreign References:
| JP2005533517A | 2005-11-10 | |||
| JP2000512853A | 2000-10-03 | |||
| JPH11130793A | 1999-05-18 | |||
| US5446137A | 1995-08-29 |
Other References:
UENO, YOSHIHITO ET AL.: "Synthesis of Oligonucleotides Modified with Polyamines and Their Properties as Antisense and Antigene Molecules", JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY, vol. 61, no. 9, 1 January 2003 (2003-01-01), Japan, pages 890 - 899, XP055612212, DOI: 10.5059/yukigoseikyokaishi.61.890
ATSUMI, N. ET AL.: "Nucleosides and nucleotides. Part 214: thermal stability of triplexes containing 4'a -C-Aminoalky 1-2'-deoxynucleosides", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 10, no. 9, 2002, pages 2933 - 2939, XP055496997
UENO, Y. ET AL.: "Nucleosides and Nucleotides. Part 206: Introduction of lipophilic groups into 4'a -C- (2-aminoethy 1) thymidine-containing phosphodiester oligodeoxynucleotides and thermal stabilities of the duplexes", TETRAHEDRON, vol. 56, no. 40, 2000, pages 7903 - 7907, XP004217291
KANAZAKI, M. ET AL.: "Highly Nuclease-Resistant Phosphodiester-Type Oligodeoxynucleotides Containing 4'a -C-Aminoalkylthymidines Form Thermally Stable Duplexes with DNA and RNA. A Candidate for Potent Antisense Molecules", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 122, no. 11, 2000, pages 2422 - 2432, XP055510260
UEMATSU, AZUSA ET AL.: "Synthesis and properties of 4'-C-guanidinomethyl-2'-O-methyl modified-RNA", PROCEEDINGS OF THE 3RD ANNUAL MEETING OF THE NUCLEIC ACIDS PHARMACEUTICAL SOCIETY OF JAPAN; JULY 12-14, 2017, vol. 3, 1 July 2017 (2017-07-01), pages 88, XP009519731
MAEDA, YUSUKE ET AL.: "P-27 Synthesis and properties of 4'-C-aminoethyl-2'-F modified nucleic acids", PROCEEDINGS OF THE 3RD ANNUAL MEETING OF THE NUCLEIC ACID PHARMACEUTICAL SOCIETY OF JAPAN; JULY 12-14, 2017, vol. 3, 1 July 2017 (2017-07-01), pages 85, XP009519732
KOIZUMI, KANA ET AL.: "Synthesis and properties of 4'-C-aminoalkyl-2'-O-methyl modified-RNA", THE CHEMICAL SOCIETY OF JAPAN SPRING ANNUAL MEETING, vol. 97, no. 4C2-29, 3 March 2017 (2017-03-03), pages 85, XP009515420
"Protective Groups in Organic Synthesis", 2007, JOHN WILEY AND SONS
J. PHARM. SCI., vol. 1-19, 1977
BIOORGANIC & MEDICINAL CHEMISTRY, vol. 11, 2003, pages 2211 - 2226
BIOORGANIC & CHEMISTRY LETTERS, 1999, pages 2667 - 2672
THE JOURNAL OF ORGANIC CHEMISTRY, vol. 78, 2013, pages 9956 - 9962
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
ATSUMI, N. ET AL.: "Nucleosides and nucleotides. Part 214: thermal stability of triplexes containing 4'a -C-Aminoalky 1-2'-deoxynucleosides", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 10, no. 9, 2002, pages 2933 - 2939, XP055496997
UENO, Y. ET AL.: "Nucleosides and Nucleotides. Part 206: Introduction of lipophilic groups into 4'a -C- (2-aminoethy 1) thymidine-containing phosphodiester oligodeoxynucleotides and thermal stabilities of the duplexes", TETRAHEDRON, vol. 56, no. 40, 2000, pages 7903 - 7907, XP004217291
KANAZAKI, M. ET AL.: "Highly Nuclease-Resistant Phosphodiester-Type Oligodeoxynucleotides Containing 4'a -C-Aminoalkylthymidines Form Thermally Stable Duplexes with DNA and RNA. A Candidate for Potent Antisense Molecules", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 122, no. 11, 2000, pages 2422 - 2432, XP055510260
UEMATSU, AZUSA ET AL.: "Synthesis and properties of 4'-C-guanidinomethyl-2'-O-methyl modified-RNA", PROCEEDINGS OF THE 3RD ANNUAL MEETING OF THE NUCLEIC ACIDS PHARMACEUTICAL SOCIETY OF JAPAN; JULY 12-14, 2017, vol. 3, 1 July 2017 (2017-07-01), pages 88, XP009519731
MAEDA, YUSUKE ET AL.: "P-27 Synthesis and properties of 4'-C-aminoethyl-2'-F modified nucleic acids", PROCEEDINGS OF THE 3RD ANNUAL MEETING OF THE NUCLEIC ACID PHARMACEUTICAL SOCIETY OF JAPAN; JULY 12-14, 2017, vol. 3, 1 July 2017 (2017-07-01), pages 85, XP009519732
KOIZUMI, KANA ET AL.: "Synthesis and properties of 4'-C-aminoalkyl-2'-O-methyl modified-RNA", THE CHEMICAL SOCIETY OF JAPAN SPRING ANNUAL MEETING, vol. 97, no. 4C2-29, 3 March 2017 (2017-03-03), pages 85, XP009515420
"Protective Groups in Organic Synthesis", 2007, JOHN WILEY AND SONS
J. PHARM. SCI., vol. 1-19, 1977
BIOORGANIC & MEDICINAL CHEMISTRY, vol. 11, 2003, pages 2211 - 2226
BIOORGANIC & CHEMISTRY LETTERS, 1999, pages 2667 - 2672
THE JOURNAL OF ORGANIC CHEMISTRY, vol. 78, 2013, pages 9956 - 9962
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
Attorney, Agent or Firm:
KAI-U PATENT LAW FIRM (JP)
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