Title:
NOVEL PHOSPHATE ESTER COMPOUND HAVING PYRROLOPYRIMIDINE SKELETON OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF
Document Type and Number:
WIPO Patent Application WO/2020/255978
Kind Code:
A1
Abstract:
[Problem] To provide a novel phosphate ester compound having a pyrrolopyrimidine skeleton or a pharmaceutically acceptable salt thereof which has excellent antitumor effects, and a method for preventing and/or treating a tumor that is used in combination with an alkylating agent and/or radiation therapy. [Solution] According to one embodiment of the present invention, provided are a compound represented by general formula (1) or a pharmaceutically acceptable salt thereof, and a method for preventing and/or treating a tumor that is used in combination with an alkylating agent and/or radiation therapy.
Inventors:
MIYAKOSHI HITOSHI (JP)
TANAKA NOZOMU (JP)
KOBAYAKAWA YU (JP)
TANAKA NOZOMU (JP)
KOBAYAKAWA YU (JP)
Application Number:
PCT/JP2020/023660
Publication Date:
December 24, 2020
Filing Date:
June 17, 2020
Export Citation:
Assignee:
TAIHO PHARMACEUTICAL CO LTD (JP)
International Classes:
A61P35/00; A61K31/7064; C07H19/14
Domestic Patent References:
| WO2014124430A1 | 2014-08-14 | |||
| WO2013009735A1 | 2013-01-17 | |||
| WO2014124430A1 | 2014-08-14 | |||
| WO2017165489A1 | 2017-09-28 |
Foreign References:
| JP2012517443A | 2012-08-02 | |||
| JP2012524731A | 2012-10-18 | |||
| JP2000510127A | 2000-08-08 |
Other References:
SEELA FRANK, XU KUIYING, CHITTEPU PADMAJA: "Fluorinated Pyrrolo[2,3-d]pyrimidine Nucleosides: 7- Fluoro-7-deazapurine 2′-Deoxyribofuranosides and 2′-Deoxy-2′-fluoroarabinofuranosyl Derivatives", SYNTHESIS, vol. 12, 2006, pages 2005 - 2012, XP055774462, DOI: 10.1055/s-2006-942400
SEELA FRANK, CHITTEPU PADMAJA, EICKMEIER HENNING: "4-Amino-7-(2-deoxy-2-fluoro-β- D -arabinofuranosyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine: a bis-fluorinated analogue of 2′-deoxytubercidin", ACTA CRYSTALLOGRAPHICA, vol. C62, no. 4, 2006, pages o231 - o233, XP055774474, DOI: 10.1107/S0108270106007633
LI WEI, YANG RUCHUN, XIAO QIANG: "(2 R ,3 S ,4 R ,5 R )-5-(4-Amino-5-iodo-7 H -pyrrolo[2,3- d ]pyrimidin-7-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol", ACTA CRYSTALLOGRAPHICA, vol. 70, no. 2, 2014, pages o120, XP055774480, DOI: 10.1107/S1600536813034995
SEELA FRANK, XU KUIYING: "DNA with stable fluorinated dA and dG substitutes: syntheses, base pairing and 19F-NMR spectra of 7-fluoro-7-deaza-2′-deoxyadenosine and 7-fluoro-7-deaza-2′-deoxyguanosine", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 6, no. 19, 2008, pages 3552 - 3560, XP055774483, DOI: 10.1039/ b806145a
PETR NAUŠ; PAVLA PERLÍKOVÁ; AURELIE BOURDERIOUX; RADEK POHL; LENKA SLAVĚTÍNSKÁ; IVAN VOTRUBA; GINA BAHADOR; GABRIEL BIRKUŠ; TOMÁŠ : "Sugar-modified derivatives of cytostatic 7-(het)aryl-7-deazaadenosines: 2′-C-methylribonucleosides, 2′-deoxy-2′-fluoroarabinonucleosides, arabinonucleosides and 2′-deoxyribonucleosides", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 20, no. 17, 2012, pages 5202 - 5214, XP055496940, DOI: 10.1016/ j.bmc. 2012.07.003
SEELA FRANK, CHITTEPU PADMAJA, HE YANG, HE JUNLIN, XU KUIYING: "6-AZAPYRIMIDINE AND 7-DEAZAPURINE 2′-DEOXY-2′-FLUOROARABINONUCLEOSIDES: SYNTHESIS, CONFORMATION AND PROPERTIES OF OLIGONUCLEOTIDES", NUCLEOSIDES, NUCLEOTIDES & NUCLEIC ACIDS, vol. 24, no. 5-7, 2005, pages 847 - 850, XP055774491, DOI: 10.1081/NCN-200059181
LARSEN, C. S. ET AL.: "Chapter 14 Design and application of prodrugs", TEXTBOOK OF DRUG DESIGN AND DISCOVERY, 2002, pages 460 - 514, XP055530665
BAZZANINI, R ET AL.: "Synthetic approaches to a mononucleotide prodrug of cytarabine", NUCLEOSIDES, NUCLEOTIDES & NUCLEIC ACIDS, vol. 24, no. 10-12, 2005, pages 1635 - 1649, XP008141704, DOI: 10.1080/15257770500267006
MOULDY SIOUD: "Ribozymes and siRNA Protocols", vol. 252, 2004, ISBN: 978-1-58829-226-1, article SOUMITRA BASU ,CATHERINE PAZSINT , GOPESWAR CHOWDHURY: "Analysis of Ribozyme Structure and Function by Nucleotide Analog Interference Mapping", pages: 57 - 75, XP009532949, DOI: 10.1385/1-59259-746-7:057
LI ET AL., ACTA CRYST, vol. E70, 2014, pages o120
PERLIKOVA ET AL., CHEMMEDCHEM, vol. 8, 2013, pages 832 - 846
NAUS ET AL., BIOORG. MED. CHEM, vol. 20, 2012, pages 5202 - 5214
BROWN ET AL., J MED CHEM, vol. 59, no. 14, 28 July 2016 (2016-07-28), pages 6860 - 6877
IKEHARA ET AL., CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 14, no. 12, 1966, pages 1338 - 46
GREENEWUTS: "Protective Groups in Organic Synthesis", 2014, JOHN WILEY & SONS INC.
LABIO, vol. 21, no. 30, October 2007 (2007-10-01), pages 27
SEELA FRANK, CHITTEPU PADMAJA, EICKMEIER HENNING: "4-Amino-7-(2-deoxy-2-fluoro-β- D -arabinofuranosyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine: a bis-fluorinated analogue of 2′-deoxytubercidin", ACTA CRYSTALLOGRAPHICA, vol. C62, no. 4, 2006, pages o231 - o233, XP055774474, DOI: 10.1107/S0108270106007633
LI WEI, YANG RUCHUN, XIAO QIANG: "(2 R ,3 S ,4 R ,5 R )-5-(4-Amino-5-iodo-7 H -pyrrolo[2,3- d ]pyrimidin-7-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol", ACTA CRYSTALLOGRAPHICA, vol. 70, no. 2, 2014, pages o120, XP055774480, DOI: 10.1107/S1600536813034995
SEELA FRANK, XU KUIYING: "DNA with stable fluorinated dA and dG substitutes: syntheses, base pairing and 19F-NMR spectra of 7-fluoro-7-deaza-2′-deoxyadenosine and 7-fluoro-7-deaza-2′-deoxyguanosine", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 6, no. 19, 2008, pages 3552 - 3560, XP055774483, DOI: 10.1039/ b806145a
PETR NAUŠ; PAVLA PERLÍKOVÁ; AURELIE BOURDERIOUX; RADEK POHL; LENKA SLAVĚTÍNSKÁ; IVAN VOTRUBA; GINA BAHADOR; GABRIEL BIRKUŠ; TOMÁŠ : "Sugar-modified derivatives of cytostatic 7-(het)aryl-7-deazaadenosines: 2′-C-methylribonucleosides, 2′-deoxy-2′-fluoroarabinonucleosides, arabinonucleosides and 2′-deoxyribonucleosides", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 20, no. 17, 2012, pages 5202 - 5214, XP055496940, DOI: 10.1016/ j.bmc. 2012.07.003
SEELA FRANK, CHITTEPU PADMAJA, HE YANG, HE JUNLIN, XU KUIYING: "6-AZAPYRIMIDINE AND 7-DEAZAPURINE 2′-DEOXY-2′-FLUOROARABINONUCLEOSIDES: SYNTHESIS, CONFORMATION AND PROPERTIES OF OLIGONUCLEOTIDES", NUCLEOSIDES, NUCLEOTIDES & NUCLEIC ACIDS, vol. 24, no. 5-7, 2005, pages 847 - 850, XP055774491, DOI: 10.1081/NCN-200059181
LARSEN, C. S. ET AL.: "Chapter 14 Design and application of prodrugs", TEXTBOOK OF DRUG DESIGN AND DISCOVERY, 2002, pages 460 - 514, XP055530665
BAZZANINI, R ET AL.: "Synthetic approaches to a mononucleotide prodrug of cytarabine", NUCLEOSIDES, NUCLEOTIDES & NUCLEIC ACIDS, vol. 24, no. 10-12, 2005, pages 1635 - 1649, XP008141704, DOI: 10.1080/15257770500267006
MOULDY SIOUD: "Ribozymes and siRNA Protocols", vol. 252, 2004, ISBN: 978-1-58829-226-1, article SOUMITRA BASU ,CATHERINE PAZSINT , GOPESWAR CHOWDHURY: "Analysis of Ribozyme Structure and Function by Nucleotide Analog Interference Mapping", pages: 57 - 75, XP009532949, DOI: 10.1385/1-59259-746-7:057
LI ET AL., ACTA CRYST, vol. E70, 2014, pages o120
PERLIKOVA ET AL., CHEMMEDCHEM, vol. 8, 2013, pages 832 - 846
NAUS ET AL., BIOORG. MED. CHEM, vol. 20, 2012, pages 5202 - 5214
BROWN ET AL., J MED CHEM, vol. 59, no. 14, 28 July 2016 (2016-07-28), pages 6860 - 6877
IKEHARA ET AL., CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 14, no. 12, 1966, pages 1338 - 46
GREENEWUTS: "Protective Groups in Organic Synthesis", 2014, JOHN WILEY & SONS INC.
LABIO, vol. 21, no. 30, October 2007 (2007-10-01), pages 27
Attorney, Agent or Firm:
KOBAYASHI Hiroshi et al. (JP)
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