Title:
EPIDITHIODIOXOPIPERAZINE COMPOUND OR ITS DERIVATIVES, AND THE USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2014/189343
Kind Code:
A1
Abstract:
The present invention relates to an epidithiodioxopiperazine derivative represented by the Chemical Formula 1 or its reduced derivative; a method for preparing a compound represented by Chemical Formula 1 having improved intracellular permeability and mimicking the activity of 2-Cys-Prx in its reduced form in the cells; a pharmaceutical composition for preventing or treating vascular diseases comprising an epidithiodioxopiperazine compound or its derivatives or pharmaceutically acceptable salts thereof as an active ingredient; a drug delivery device for local administration including the pharmaceutical composition; and a pharmaceutical composition for inhibiting melanoma metastasis comprising the epidithiodioxopiperazine compound or its derivatives or pharmaceutically acceptable salts thereof as an active ingredient.
Inventors:
KANG SANG WON (KR)
KANG DONG HOON (KR)
LEE DOO JAE (KR)
KANG DONG HOON (KR)
LEE DOO JAE (KR)
Application Number:
PCT/KR2014/004678
Publication Date:
November 27, 2014
Filing Date:
May 26, 2014
Export Citation:
Assignee:
UNIV EWHA IND COLLABORATION (KR)
International Classes:
C07D513/08; A61K31/542; A61K31/548; A61P9/00
Domestic Patent References:
| WO2006066775A1 | 2006-06-29 | |||
| WO2006135949A2 | 2006-12-28 |
Foreign References:
| US20060083772A1 | 2006-04-20 | |||
| KR20060020140A | 2006-03-06 | |||
| KR100953326B1 | 2010-04-20 |
Other References:
JOHN E. DELORBE ET AL.: "General Approach for Preparing Epidithiodioxo- piperazines from Trioxopiperazine Precursors: Enantioselective Total Syntheses of (+)- and (-)-Gliocladine C, (+)-Leptosin D, (+)-T988C, (+)-Bionectin A, and (+)-Gliocladin A", JOURNAL OF AMERICAN CHEMICAL SOCIETY, vol. 135, no. 10, pages 4117 - 4128, XP055295514
RAMIN DUBEY ET AL.: "Suppression of Tumor Growth by Designed Dimeric Epidithiodiketopiperazine Targeting Hypoxia-Inducible Transcription Factor Complex", JOURNAL OF AMERICAN CHEMICAL SOCIETY, vol. 135, no. 11, 28 February 2013 (2013-02-28), pages 4537 - 4549, XP055295516
KRISTINA M. COOK ET AL.: "Epidithiodiketopiperazines Block the Interaction between Hypoxia-inducible Factor-1 a (HIF-1 a) and p300 by a Zinc Ejection Mechanism", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 284, no. 39, 2009, pages 26831 - 26838, XP055295517
MAYTE POZO ET AL.: "Gliotoxin Inhibits Neointimal Gtperplasia after Vascular Injury in Rats", JOURNAL OF VASCULAR RESEARCH, vol. 46, no. 4, 2009, pages 278 - 289, XP055295518
HEE SHIM CHOI ET AL.: "Discovery of gliotixin as a new small molecule targeting thioredoxin redox system", BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, vol. 359, no. 3, 2007, pages 523 - 528, XP022117680
HUI JIANG ET AL., AUSTRALIAN JOURNAL OF CHEMISTRY, vol. 46, 1993, pages 1743 - 1754
ALANNA M. HUME ET AL., BIORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 7, no. 20, 1997, pages 2645 - 2650
HILTON S. ET AL., BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 15, no. 9, 2 May 2005 (2005-05-02), pages 2239 - 2242
P. H. BERNARDO ET AL., J. BIOL. CHEM., vol. 278, pages 46549
KIRBYROBINS, THE BIOSYNTHESIS OF MYCOTOXINS, NEW YORK, 1980
SHAHLARSEN, MYCOPATHOLOGIA, vol. 116, 1991, pages 203 - 208
CURTIS ET AL., J. CHEM. SOC. PERKIN TRANS., vol. 1, 1977, pages 180 - 189
FEREZOU ET AL., NOUV. J. CHIM., vol. 1, 1977, pages 327 - 334
STILLWELL ET AL., CAN. J. MICROBIOL., vol. 20, 1974, pages 759 - 764
SEKITA ET AL., CAN. J. MICROBIOL., vol. 27, 1981, pages 766 - 772
BYENG ET AL., NAT. PROD. LETT., vol. 13, 1999, pages 213 - 222
JOSHI ET AL., J. NAT. PROD., vol. 62, 1999, pages 730 - 733
SEKITA ET AL., CAN. J. MICROBIOL, vol. 27, 1981, pages 766 - 772
TAKAHASHI ET AL., J. ANTIBIOT., vol. 47, 1994, pages 1242 - 1249
SEYA ET AL., CHEM. PHARM. BULL., vol. 34, 1986, pages 2411 - 2416
ERNST-RUSSELL ET AL., AUST. J. CHEM., vol. 52, 1999, pages 279 - 283
MOERMAN ET AL., TOXICOL. APPL. PHARMACOL., vol. 190, 2003, pages 232 - 240
KAWAHARA ET AL., J. CHEM. SOC. PERKIN TRANS., vol. 1, 1987, pages 2099 - 2101
DEFFIEUX ET AL., ACTA CHRISTALLOGR., vol. B33, 1977, pages 1474 - 1478
KLEINWACHTER ET AL., J. ANTIBIOT., vol. 54, 2001, pages 521 - 525
NEUSS ET AL., ANTIMICROB. AGENTS CHEMOTHER., vol. 8, 1968, pages 213 - 219
KAWAHARA ET AL., CHEM. PHARM. BULL., vol. 37, 1989, pages 2592 - 2595
M. H. CHOI ET AL., NATURE, vol. 435, 2005, pages 347
D. H. KANG ET AL., MOL. CELL, vol. 44, 2011, pages 656
ERIC J. TOPOL: "Interventional Cardiology", 1994, SAUNDERS COMPANY
BLINDT ET AL., INT. J. ARTIF. ORGANS, vol. 22, 1999, pages 843
See also references of EP 2958926A4
RAMIN DUBEY ET AL.: "Suppression of Tumor Growth by Designed Dimeric Epidithiodiketopiperazine Targeting Hypoxia-Inducible Transcription Factor Complex", JOURNAL OF AMERICAN CHEMICAL SOCIETY, vol. 135, no. 11, 28 February 2013 (2013-02-28), pages 4537 - 4549, XP055295516
KRISTINA M. COOK ET AL.: "Epidithiodiketopiperazines Block the Interaction between Hypoxia-inducible Factor-1 a (HIF-1 a) and p300 by a Zinc Ejection Mechanism", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 284, no. 39, 2009, pages 26831 - 26838, XP055295517
MAYTE POZO ET AL.: "Gliotoxin Inhibits Neointimal Gtperplasia after Vascular Injury in Rats", JOURNAL OF VASCULAR RESEARCH, vol. 46, no. 4, 2009, pages 278 - 289, XP055295518
HEE SHIM CHOI ET AL.: "Discovery of gliotixin as a new small molecule targeting thioredoxin redox system", BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, vol. 359, no. 3, 2007, pages 523 - 528, XP022117680
HUI JIANG ET AL., AUSTRALIAN JOURNAL OF CHEMISTRY, vol. 46, 1993, pages 1743 - 1754
ALANNA M. HUME ET AL., BIORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 7, no. 20, 1997, pages 2645 - 2650
HILTON S. ET AL., BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 15, no. 9, 2 May 2005 (2005-05-02), pages 2239 - 2242
P. H. BERNARDO ET AL., J. BIOL. CHEM., vol. 278, pages 46549
KIRBYROBINS, THE BIOSYNTHESIS OF MYCOTOXINS, NEW YORK, 1980
SHAHLARSEN, MYCOPATHOLOGIA, vol. 116, 1991, pages 203 - 208
CURTIS ET AL., J. CHEM. SOC. PERKIN TRANS., vol. 1, 1977, pages 180 - 189
FEREZOU ET AL., NOUV. J. CHIM., vol. 1, 1977, pages 327 - 334
STILLWELL ET AL., CAN. J. MICROBIOL., vol. 20, 1974, pages 759 - 764
SEKITA ET AL., CAN. J. MICROBIOL., vol. 27, 1981, pages 766 - 772
BYENG ET AL., NAT. PROD. LETT., vol. 13, 1999, pages 213 - 222
JOSHI ET AL., J. NAT. PROD., vol. 62, 1999, pages 730 - 733
SEKITA ET AL., CAN. J. MICROBIOL, vol. 27, 1981, pages 766 - 772
TAKAHASHI ET AL., J. ANTIBIOT., vol. 47, 1994, pages 1242 - 1249
SEYA ET AL., CHEM. PHARM. BULL., vol. 34, 1986, pages 2411 - 2416
ERNST-RUSSELL ET AL., AUST. J. CHEM., vol. 52, 1999, pages 279 - 283
MOERMAN ET AL., TOXICOL. APPL. PHARMACOL., vol. 190, 2003, pages 232 - 240
KAWAHARA ET AL., J. CHEM. SOC. PERKIN TRANS., vol. 1, 1987, pages 2099 - 2101
DEFFIEUX ET AL., ACTA CHRISTALLOGR., vol. B33, 1977, pages 1474 - 1478
KLEINWACHTER ET AL., J. ANTIBIOT., vol. 54, 2001, pages 521 - 525
NEUSS ET AL., ANTIMICROB. AGENTS CHEMOTHER., vol. 8, 1968, pages 213 - 219
KAWAHARA ET AL., CHEM. PHARM. BULL., vol. 37, 1989, pages 2592 - 2595
M. H. CHOI ET AL., NATURE, vol. 435, 2005, pages 347
D. H. KANG ET AL., MOL. CELL, vol. 44, 2011, pages 656
ERIC J. TOPOL: "Interventional Cardiology", 1994, SAUNDERS COMPANY
BLINDT ET AL., INT. J. ARTIF. ORGANS, vol. 22, 1999, pages 843
See also references of EP 2958926A4
Attorney, Agent or Firm:
SON, Min (6th Floor163, YangJaeCheon-ro,Gangnam-gu, Seoul 135-855, KR)
Download PDF:
Previous Patent: CATALYST FOR PREPARING ACROLEIN AND ACRYLIC ACID, AND METHOD FOR PREPARING SAME
Next Patent: CACHE DEVICE AND CACHE OPERATION METHOD
Next Patent: CACHE DEVICE AND CACHE OPERATION METHOD