Title:
TERPENOID DERIVATIVE
Document Type and Number:
WIPO Patent Application WO/2014/148455
Kind Code:
A1
Abstract:
Provided is a novel terpenoid derivative which exhibits anti-inflammatory action and cytoprotective action by activating Keap1/Nrf2/ARE signal transduction pathways. Terpenoid derivative A is represented by formula (1).
Inventors:
KOMORIYA SATOSHI (JP)
NAKAGAMI YASUHIRO (JP)
HATANO EMIKO (JP)
OHNUKI TAKASHI (JP)
MASUDA KAYOKO (JP)
IIZUKA MAYUMI (JP)
ONO YASUNORI (JP)
NAKAGAMI YASUHIRO (JP)
HATANO EMIKO (JP)
OHNUKI TAKASHI (JP)
MASUDA KAYOKO (JP)
IIZUKA MAYUMI (JP)
ONO YASUNORI (JP)
Application Number:
PCT/JP2014/057222
Publication Date:
September 25, 2014
Filing Date:
March 18, 2014
Export Citation:
Assignee:
DAIICHI SANKYO CO LTD (JP)
International Classes:
C07J63/00; A61K31/56; A61K31/58; A61P1/16; A61P9/10; A61P11/00; A61P11/06; A61P13/02; A61P13/12; A61P21/00; A61P25/14; A61P25/16; A61P25/28; A61P27/02; A61P27/06; A61P27/12; A61P27/14; C12N1/14; C12P33/00; C12P33/06; C12R1/645; C12R1/785
Domestic Patent References:
| WO2013188818A1 | 2013-12-19 | |||
| WO1999065478A1 | 1999-12-23 | |||
| WO2012125488A1 | 2012-09-20 | |||
| WO2011130302A2 | 2011-10-20 | |||
| WO2009146216A2 | 2009-12-03 | |||
| WO2009129546A1 | 2009-10-22 | |||
| WO2009129548A1 | 2009-10-22 | |||
| WO2009023232A1 | 2009-02-19 | |||
| WO2004064723A2 | 2004-08-05 | |||
| WO2009089545A1 | 2009-07-16 |
Foreign References:
| JP2001525665A | 2001-12-11 | |||
| JP2011500754A | 2011-01-06 | |||
| JPH06247894A | 1994-09-06 |
Other References:
HONDA T ET AL.: "Design and synthesis of 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid, a novel and highly active inhibitor of nitric oxide production in mouse macrophages", BIOORG MED CHEM LETT., vol. 8, 1998, pages 2711 - 2714, XP004139606
HONDA T ET AL.: "A novel dicyanotriterpenoid, 2-cyano-3,12-dioxooleana-1,9(11)-dien-28- onitrile, active at picomolar concentrations for inhibition of nitric oxide production", BIOORG MED CHEM LETT., vol. 12, 2002, pages 1027 - 1030, XP002456641
INT. J. BIOCHEM. CELL. BIOL., vol. 44, 2012, pages 1315 - 1320
CLIN. PHARMACOL. THER., vol. 92, 2012, pages 340 - 348
ADV. PHARMACOL., vol. 63, 2012, pages 43 - 79
MED. RES. REV., vol. 32, 2012, pages 687 - 726
MOL. ASPECTS. MED., vol. 32, 2011, pages 234 - 246
FREE RADIC BIOL. MED., vol. 51, 2011, pages 216 - 224
"Front Biosci.", vol. 4, 2012, pages: 141 - 115
CURR. MED. CHEM., vol. 18, 2011, pages 931 - 942
J. PHARMACOL. EXP. THER., vol. 335, 2010, pages 2 - 12
INT. J. NEPHROL., 2012, pages 321714
PROC. NATL. ACAD. SCI. USA, vol. 106, 2009, pages 250 - 255
TRENDS MOL. MED., vol. 17, 2011, pages 363 - 371
TOXICOL. APPL. PHARMACOL., vol. 244, 2010, pages 43 - 56
FREE RADIC BIOL. MED., vol. 48, 2010, pages 357 - 371
J. NUTR. BIOCHEM., vol. 23, 2012, pages 1201 - 1206
J. BIOL. CHEM., vol. 285, 2010, pages 40581 - 40592
THE JOURNAL OF THE JAPANESE BIOCHEMICAL SOCIETY, vol. 81, 2009, pages 447 - 9
BIOORG. MED. CHEM. LETT., vol. 8, 1998, pages 2711 - 2714
SYNTHESIS SCHEME 2 IN BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 8, no. 17, 1998, pages 2711 - 2714
BIOORGANIC MEDICINAL CHEMISTRY LETTERS, vol. 7, 1997, pages 1623 - 1628
BIOORGANIC MEDICINAL CHEMISTRY LETTERS, vol. 8, 1998, pages 2711 - 2714
SYNTHESIS SCHEME 1 IN BIOORGANIC MEDICINAL CHEMISTRY LETTERS, vol. 12, no. 15, 2002, pages 1027 - 1030
BIOORGANIC MEDICINAL CHEMISTRY LETTERS, vol. 12, 2002, pages 1027 - 1030
SYNTHESIS SCHEME 1 IN BIOORGANIC MEDICINAL CHEMISTRY LETTERS, vol. 12, no. 4, 2002, pages 1027 - 1030
KORNERUP, A.; WANSCHER, J. H.: "Methuen handbook of colour", 1978, ERYE METHUEN
DOMSCH, K.H.; W. GAMS; T.-H. ANDERSON: "Compendium of Soil Fungi", 2007, pages: 672
NITE PATENT MICROORGANISMS DEPOSITARY (NPMD), BIOLOGICAL RESOURCE CENTER, NATIONAL INSTITUTE OF TECHNOLOGY AND EVALUATION (ADDRESS: 2-5-8 KAZUSAKAMATARI, KISARAZU-SHI, CHIBA, JAPAN, 18 December 2012 (2012-12-18)
CHEM BIOL INTERACT, vol. 181, 2009, pages 366
FOOD CHEM TOXICOL, vol. 49, 2011, pages 2081
ANAL BIOCHEM, vol. 169, 1998, pages 328
METHODS ENZYMOL, vol. 382, 2004, pages 243
INVEST OPHTHALMOL VIS SCI, vol. 41, 2000, pages 887
HONDA T ET AL.: "A novel dicyanotriterpenoid, 2-cyano-3,12-dioxooleana-1,9(11)-dien-28- onitrile, active at picomolar concentrations for inhibition of nitric oxide production", BIOORG MED CHEM LETT., vol. 12, 2002, pages 1027 - 1030, XP002456641
INT. J. BIOCHEM. CELL. BIOL., vol. 44, 2012, pages 1315 - 1320
CLIN. PHARMACOL. THER., vol. 92, 2012, pages 340 - 348
ADV. PHARMACOL., vol. 63, 2012, pages 43 - 79
MED. RES. REV., vol. 32, 2012, pages 687 - 726
MOL. ASPECTS. MED., vol. 32, 2011, pages 234 - 246
FREE RADIC BIOL. MED., vol. 51, 2011, pages 216 - 224
"Front Biosci.", vol. 4, 2012, pages: 141 - 115
CURR. MED. CHEM., vol. 18, 2011, pages 931 - 942
J. PHARMACOL. EXP. THER., vol. 335, 2010, pages 2 - 12
INT. J. NEPHROL., 2012, pages 321714
PROC. NATL. ACAD. SCI. USA, vol. 106, 2009, pages 250 - 255
TRENDS MOL. MED., vol. 17, 2011, pages 363 - 371
TOXICOL. APPL. PHARMACOL., vol. 244, 2010, pages 43 - 56
FREE RADIC BIOL. MED., vol. 48, 2010, pages 357 - 371
J. NUTR. BIOCHEM., vol. 23, 2012, pages 1201 - 1206
J. BIOL. CHEM., vol. 285, 2010, pages 40581 - 40592
THE JOURNAL OF THE JAPANESE BIOCHEMICAL SOCIETY, vol. 81, 2009, pages 447 - 9
BIOORG. MED. CHEM. LETT., vol. 8, 1998, pages 2711 - 2714
SYNTHESIS SCHEME 2 IN BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 8, no. 17, 1998, pages 2711 - 2714
BIOORGANIC MEDICINAL CHEMISTRY LETTERS, vol. 7, 1997, pages 1623 - 1628
BIOORGANIC MEDICINAL CHEMISTRY LETTERS, vol. 8, 1998, pages 2711 - 2714
SYNTHESIS SCHEME 1 IN BIOORGANIC MEDICINAL CHEMISTRY LETTERS, vol. 12, no. 15, 2002, pages 1027 - 1030
BIOORGANIC MEDICINAL CHEMISTRY LETTERS, vol. 12, 2002, pages 1027 - 1030
SYNTHESIS SCHEME 1 IN BIOORGANIC MEDICINAL CHEMISTRY LETTERS, vol. 12, no. 4, 2002, pages 1027 - 1030
KORNERUP, A.; WANSCHER, J. H.: "Methuen handbook of colour", 1978, ERYE METHUEN
DOMSCH, K.H.; W. GAMS; T.-H. ANDERSON: "Compendium of Soil Fungi", 2007, pages: 672
NITE PATENT MICROORGANISMS DEPOSITARY (NPMD), BIOLOGICAL RESOURCE CENTER, NATIONAL INSTITUTE OF TECHNOLOGY AND EVALUATION (ADDRESS: 2-5-8 KAZUSAKAMATARI, KISARAZU-SHI, CHIBA, JAPAN, 18 December 2012 (2012-12-18)
CHEM BIOL INTERACT, vol. 181, 2009, pages 366
FOOD CHEM TOXICOL, vol. 49, 2011, pages 2081
ANAL BIOCHEM, vol. 169, 1998, pages 328
METHODS ENZYMOL, vol. 382, 2004, pages 243
INVEST OPHTHALMOL VIS SCI, vol. 41, 2000, pages 887
Attorney, Agent or Firm:
ISHIBASHI Koki et al. (JP)
Kimiki Ishibashi (JP)
Kimiki Ishibashi (JP)
Download PDF: