Title:
NOVEL COMPOUND, AND ENZYME INHIBITOR AND ABP COMPRISING RELATED NOVEL COMPOUND
Document Type and Number:
WIPO Patent Application WO/2020/189734
Kind Code:
A1
Abstract:
Provided is a compound or salt thereof represented by formula (I) below [In formula (I), R1 represents –COOH or –CY1Y2OH (where, Y1 and Y2 each represent a hydrogen atom or a detectable marker), A1 represents a sugar or an aglycone, X represents a hydrogen atom, an alkyl group with 1-4 carbon atoms or a halogen atom, and an OH group may be modified].
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Inventors:
HIRAI GO (JP)
KIMURO YUSUKE (JP)
MORITA MASAKI (JP)
DOI KAZUKI (JP)
KIMURO YUSUKE (JP)
MORITA MASAKI (JP)
DOI KAZUKI (JP)
Application Number:
PCT/JP2020/012093
Publication Date:
September 24, 2020
Filing Date:
March 18, 2020
Export Citation:
Assignee:
UNIV KYUSHU NAT UNIV CORP (JP)
International Classes:
A61P3/08; A61K31/7028; A61K31/7034; A61K31/704; A61P3/10; A61P43/00; C07H15/04; C07H15/203; C07J9/00; C12N9/99; C12N15/11; C12Q1/00
Foreign References:
| JP2018016579A | 2018-02-01 |
Other References:
SILVIA MIRANDA ANA M. GÓMEZ J. CRISTÓBAL LÓPEZ: "Front Cover: Diversity‐Oriented Synthetic Endeavors of Newly Designed Ferrier and Ferrier‐Nicholas Systems Derived from 1‐C‐Alkynyl‐2‐deoxy‐2‐C‐Methylene Pyranosides", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2018, no. 39, 3 September 2018 (2018-09-03), pages 5355 - 5374, XP055741265
TETRAHEDRON, vol. 73, no. 27-28, 2017, pages 3923 - 3931
PETER W. MOORE, JULIA K. SCHUSTER, RUSSELL J. HEWITT, M. RHIA L. STONE, ... JOANNE E. HARVEY: "Divergent synthesis of 2-C-branched pyranosides and oxepines from 1,2-gem-dibromocyclopropyl carbohydrates", TETRAHEDRON, vol. 70, no. 39, 24 June 2014 (2014-06-24), pages 7032 - 7043, XP055741271
RASHMI ROY PARASURAMAN RAJASEKARAN ASADULLA MALLICK YASHWANT D. VANKAR: "Gold(III) Chloride and Phenylacetylene: A Catalyst System for the Ferrier Rearrangement, and O‐Glycosylation of 1‐O‐Acetyl Sugars as Glycosyl Donors", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2014, no. 25, September 2014 (2014-09-01), pages 5564 - 5573, XP055741274
CARBOHYDRATE RESEARCH, vol. 346, no. 13, 2011, pages 1654 - 1661
JOURNAL OF ORGANIC CHEMISTRY, vol. 75, no. 3, 2010, pages 955 - 958
PARAMATHEVAR NAGARAJ, NAMAKKAL G. RAMESH: "Stereoselective synthesis of 2-C-methylene glycosides and disaccharides via direct allylic substitution of hydroxy group in benzylated glycals", TETRAHEDRON, vol. 66, no. 3, 22 November 2009 (2009-11-22) - 2010, pages 599 - 604, XP027534274
NAGARAJ PARAMATHEVAR, RAMESH NAMAKKAL G.: "InCl 3 -Catalyzed Rapid 1,3-Alkoxy Migration in Glycal Ethers: Stereoselective Synthesis of Unsaturated α- O -Glycosides and an α,α-(1→1)-Linked Disaccharide", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 27, September 2008 (2008-09-01), pages 4607 - 4614, XP055741291
SUDHIR KASHYAP, SRINIVASA RAO VIDADALA, SRINIVAS HOTHA: "Synthesis of C-2 methylene glycosides from C-2 propargyloxymethyl glycals exploiting the alkynophilicity of AuCl3", TETRAHEDRON LETTERS, vol. 48, no. 51, 30 October 2007 (2007-10-30), pages 8960 - 8962, XP022355448
GHOSH; CHAKRABORTY R; MAITI A; PURANIK D K; V G: "Chiral 2-C-methylene glycosides and carbohydrate-derived pyrano[2,3-b][1]benzopyrans: synthesis via InCl"3 catalyzed stereoselective Ferrier rearrangement of 2-C-acetoxymethyl glycal derivatives", TETRAHEDRON LETTERS, vol. 46, no. 46, 14 November 2005 (2005-11-14), pages 8047 - 8051, XP005113203
GUPTA A; VANKAR Y D: "Synthesis of C-2 Methylene O- and C-Glycosides and Sugar Derived @a-Methylene-@d-valerolactones from C-2-Acetoxymethyl Glycals", TETRAHEDRON, vol. 56, no. 43, 20 October 2000 (2000-10-20), pages 8525 - 8531, XP004238502
JOURNAL OF CARBOHYDRATE CHEMISTRY, vol. 19, no. 6, 2000, pages 661 - 675
HANS-JÜRGEN HAMANN, EUGEN HÖFT, DANUTA MOSTOWICZ, ANATOLY MISHNEV, ... MAREK CHMIELEWSKI: "New optically pure sugar hydroperoxides. Synhtesis and use for enantioselective oxygen transfer", TETRAHEDRON, vol. 53, no. 1, 1997, pages 185 - 192, XP004105129
"Section C: Crystal Structure Communications", ACTA CRYSTALLOGRAPHICA, vol. C51, no. 4, 1995, pages 758 - 759
RAMESH N G; BALASUBRAMANIAN K K: "Mitsunobu Reaction of 1,5-Anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-hex-1-enitols and 1,5-Anhydro-2-deoxy-4,6-O-protected-hex-1-enitols. A Novel Method for the Synthesis of 2-C-Methylene Glycosides and an Useful Alternative to Ferrier Rearrangement", TETRAHEDRON, vol. 51, no. 1, 2 January 1995 (1995-01-02), pages 255 - 272, XP004104964
C. BOOMA, K.K. BALASUBRAMANIAN: "A novel tandem ferrier rearrangement-cyclisation. Synthesis of chiral pyrano[2,3-b][1]benzophyran system.", TETRAHEDRON LETTERS, vol. 34, no. 42, 1993, pages 6757 - 6760, XP055741341
BOOMA C, BALASUBRAMANIAN K K: "A New Ferrier System: 2-GAcetoxymethylglycals.1 A Convenient Entry to 2-GMethylene GI ycosides", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, vol. 1993, no. 18, 1993, pages 1394 - 1395, XP055741343
CHRISTIAN BL¸CHEL, RAMANA CHEPURI VENKATA, VASELLA ANDREA: "Synthesis of Monosaccharide-Derived Spirocyclic Cyclopropylamines and Their Evaluation as Glycosidase Inhibitors", HELVETICA CHIMICA ACTA, vol. 86, no. 9, 22 September 2003 (2003-09-22), pages 2998 - 3036, XP055741354
PREETI GUPTA YASHWANT D. VANKAR: "Facile Aza‐Claisen Rearrangement of Glycals: Application in the Synthesis of 1‐Deoxy‐L‐iminosugars", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2009, no. 12, 30 March 2009 (2009-03-30), pages 1925 - 1933, XP055741378
TETRAHEDRON, vol. 73, no. 27-28, 2017, pages 3923 - 3931
PETER W. MOORE, JULIA K. SCHUSTER, RUSSELL J. HEWITT, M. RHIA L. STONE, ... JOANNE E. HARVEY: "Divergent synthesis of 2-C-branched pyranosides and oxepines from 1,2-gem-dibromocyclopropyl carbohydrates", TETRAHEDRON, vol. 70, no. 39, 24 June 2014 (2014-06-24), pages 7032 - 7043, XP055741271
RASHMI ROY PARASURAMAN RAJASEKARAN ASADULLA MALLICK YASHWANT D. VANKAR: "Gold(III) Chloride and Phenylacetylene: A Catalyst System for the Ferrier Rearrangement, and O‐Glycosylation of 1‐O‐Acetyl Sugars as Glycosyl Donors", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2014, no. 25, September 2014 (2014-09-01), pages 5564 - 5573, XP055741274
CARBOHYDRATE RESEARCH, vol. 346, no. 13, 2011, pages 1654 - 1661
JOURNAL OF ORGANIC CHEMISTRY, vol. 75, no. 3, 2010, pages 955 - 958
PARAMATHEVAR NAGARAJ, NAMAKKAL G. RAMESH: "Stereoselective synthesis of 2-C-methylene glycosides and disaccharides via direct allylic substitution of hydroxy group in benzylated glycals", TETRAHEDRON, vol. 66, no. 3, 22 November 2009 (2009-11-22) - 2010, pages 599 - 604, XP027534274
NAGARAJ PARAMATHEVAR, RAMESH NAMAKKAL G.: "InCl 3 -Catalyzed Rapid 1,3-Alkoxy Migration in Glycal Ethers: Stereoselective Synthesis of Unsaturated α- O -Glycosides and an α,α-(1→1)-Linked Disaccharide", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 27, September 2008 (2008-09-01), pages 4607 - 4614, XP055741291
SUDHIR KASHYAP, SRINIVASA RAO VIDADALA, SRINIVAS HOTHA: "Synthesis of C-2 methylene glycosides from C-2 propargyloxymethyl glycals exploiting the alkynophilicity of AuCl3", TETRAHEDRON LETTERS, vol. 48, no. 51, 30 October 2007 (2007-10-30), pages 8960 - 8962, XP022355448
GHOSH; CHAKRABORTY R; MAITI A; PURANIK D K; V G: "Chiral 2-C-methylene glycosides and carbohydrate-derived pyrano[2,3-b][1]benzopyrans: synthesis via InCl"3 catalyzed stereoselective Ferrier rearrangement of 2-C-acetoxymethyl glycal derivatives", TETRAHEDRON LETTERS, vol. 46, no. 46, 14 November 2005 (2005-11-14), pages 8047 - 8051, XP005113203
GUPTA A; VANKAR Y D: "Synthesis of C-2 Methylene O- and C-Glycosides and Sugar Derived @a-Methylene-@d-valerolactones from C-2-Acetoxymethyl Glycals", TETRAHEDRON, vol. 56, no. 43, 20 October 2000 (2000-10-20), pages 8525 - 8531, XP004238502
JOURNAL OF CARBOHYDRATE CHEMISTRY, vol. 19, no. 6, 2000, pages 661 - 675
HANS-JÜRGEN HAMANN, EUGEN HÖFT, DANUTA MOSTOWICZ, ANATOLY MISHNEV, ... MAREK CHMIELEWSKI: "New optically pure sugar hydroperoxides. Synhtesis and use for enantioselective oxygen transfer", TETRAHEDRON, vol. 53, no. 1, 1997, pages 185 - 192, XP004105129
"Section C: Crystal Structure Communications", ACTA CRYSTALLOGRAPHICA, vol. C51, no. 4, 1995, pages 758 - 759
RAMESH N G; BALASUBRAMANIAN K K: "Mitsunobu Reaction of 1,5-Anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-hex-1-enitols and 1,5-Anhydro-2-deoxy-4,6-O-protected-hex-1-enitols. A Novel Method for the Synthesis of 2-C-Methylene Glycosides and an Useful Alternative to Ferrier Rearrangement", TETRAHEDRON, vol. 51, no. 1, 2 January 1995 (1995-01-02), pages 255 - 272, XP004104964
C. BOOMA, K.K. BALASUBRAMANIAN: "A novel tandem ferrier rearrangement-cyclisation. Synthesis of chiral pyrano[2,3-b][1]benzophyran system.", TETRAHEDRON LETTERS, vol. 34, no. 42, 1993, pages 6757 - 6760, XP055741341
BOOMA C, BALASUBRAMANIAN K K: "A New Ferrier System: 2-GAcetoxymethylglycals.1 A Convenient Entry to 2-GMethylene GI ycosides", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, vol. 1993, no. 18, 1993, pages 1394 - 1395, XP055741343
CHRISTIAN BL¸CHEL, RAMANA CHEPURI VENKATA, VASELLA ANDREA: "Synthesis of Monosaccharide-Derived Spirocyclic Cyclopropylamines and Their Evaluation as Glycosidase Inhibitors", HELVETICA CHIMICA ACTA, vol. 86, no. 9, 22 September 2003 (2003-09-22), pages 2998 - 3036, XP055741354
PREETI GUPTA YASHWANT D. VANKAR: "Facile Aza‐Claisen Rearrangement of Glycals: Application in the Synthesis of 1‐Deoxy‐L‐iminosugars", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2009, no. 12, 30 March 2009 (2009-03-30), pages 1925 - 1933, XP055741378
Attorney, Agent or Firm:
TAKATSU Kazuya (JP)
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