Title:
NOVEL COMPOUND BASED ON VALEROLACTONE, AND MEDICINE
Document Type and Number:
WIPO Patent Application WO/2019/160150
Kind Code:
A1
Abstract:
This novel valerolactone-based compound is represented by formula (I). [In the formula, X represents an allyl group, an aryl group, an ethynyl group, or a butenyl group. Y represents a single bond or a hydroxymethylene group, and Z represents oxygen, a methylene group, or an imide group. In the formula, Y represents a single bond or a hydroxymethylene group, m is 0 or 1, and n is 1 or 2.]
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Inventors:
KUSAMA KUNIKO (JP)
YANAI YUTA (JP)
HIROSE DAI (JP)
FURUKAWA MEGUMI (JP)
KOSUGE YASUHIRO (JP)
MATSUZAKI KEIICHI (JP)
MIURA MOTOFUMI (JP)
YANAI YUTA (JP)
HIROSE DAI (JP)
FURUKAWA MEGUMI (JP)
KOSUGE YASUHIRO (JP)
MATSUZAKI KEIICHI (JP)
MIURA MOTOFUMI (JP)
Application Number:
PCT/JP2019/005930
Publication Date:
August 22, 2019
Filing Date:
February 18, 2019
Export Citation:
Assignee:
KUSAMA KUNIKO (JP)
International Classes:
C07D307/33; A61K31/365; A61K31/366; A61P9/10; A61P25/00; A61P25/28; C07D309/30
Domestic Patent References:
| WO2010088167A1 | 2010-08-05 | |||
| WO2014081675A1 | 2014-05-30 | |||
| WO2014194292A1 | 2014-12-04 |
Foreign References:
| US4948905A | 1990-08-14 | |||
| US20120095091A1 | 2012-04-19 | |||
| JPS5657783A | 1981-05-20 | |||
| JPH04234379A | 1992-08-24 |
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MOHIDEEN, M. ET AL.: "Design, synthesis, in vitro cytotoxicity evaluation and structure-activity relationship of Goniothalamin analogs", ARCHIVES OF PHARMACAL RESEARCH, vol. 36, no. 7, 31 March 2013 (2013-03-31), pages 812 - 831, XP035312489
OTOMARU, Y. ET AL.: "Rhodium-catalyzed asymmetric 1, 4-addition of alkenylsilanes generated by hydrosilylation of alkynes: a one-pot procedure where a rhodium/(S)-binap complex catalyzes the two successive reactions", TETRAHEDRON, vol. 15, 2004, pages 2647 - 2651, XP004559144, ISSN: 0957-4166, doi:10.1016/j.tetasy.2004.07.003
FUGANTI,C. ET AL.: "On the microbial biogeneration of (R) y -jasmolactone", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 3, 1993, pages 2777 - 2780, XP026630441, ISSN: 0960-894X, doi:10.1016/S0960-894X(01)80762-9
NALLASIVAM, J. L. ET AL.: "Pd-Catalyzed Site-Selective Mono-allylic Substitution and Bis-arylation by Directed Allylic C-H Activation: Synthesis of anti-y-(Aryl,Styryl)-beta-hydroxy Acids and Highly Substituted Tetrahydrofurans", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 138, no. 40, 12 October 2016 (2016-10-12), pages 13238 - 13245, XP055632413, ISSN: 0002-7863
KANEMASA, S. ET AL.: "Synthesis of 4-[(E)-1-alkenyl]-2-hydroxybutanolides and (Z)-4-alkylidene-2-butenolides through cycloadditions using a phosphorus-functionalized nitrile oxide", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 62, no. 1, 1989, pages 171 - 179, XP055632424, ISSN: 0009-2673
LI, W. Z. ET AL.: "Chemoselective Aldol Reaction of Silyl Enolates Catalyzed by MgI2 Etherate", ORGANIC LETTERS, vol. 4, no. 20, 23 July 2002 (2002-07-23), pages 3485 - 3488, XP055632426, ISSN: 1523-7060
SUN,M. ET AL.: "α-Vinylation of amides with arylacetylenes: synthesis of allylamines under metal-free conditions", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 11, no. 41, 2013, pages 7076 - 7079, XP055632428, ISSN: 1477-0520
DICKMEISS,G. ET AL.: "Organocatalytic asymmetric desymmetrization-fragmentation of cyclic ketones", ANGEWANDTE CHEMIE , INTERNATIONAL EDITION, vol. 48, no. 36, 2009, pages 6650 - 6653, XP055632432, ISSN: 1433-7851
DATABASE REGISTRY [online] 5 March 2019 (2019-03-05), retrieved from STN Database accession no. 1623052-49-2
NAGI, R. K. ET AL.: "Synthesis and biological evaluation of sapinofuranones A, B and 1,2,3-triazole-sapinofuranone hybrids as cytotoxic agents", RSC ADVANCES, vol. 6, no. 103, 2016, pages 101501 - 101512, XP055632440, ISSN: 2046-2069
MOHIDEEN, M. ET AL.: "Design, synthesis, in vitro cytotoxicity evaluation and structure-activity relationship of Goniothalamin analogs", ARCHIVES OF PHARMACAL RESEARCH, vol. 36, no. 7, 31 March 2013 (2013-03-31), pages 812 - 831, XP035312489
OTOMARU, Y. ET AL.: "Rhodium-catalyzed asymmetric 1, 4-addition of alkenylsilanes generated by hydrosilylation of alkynes: a one-pot procedure where a rhodium/(S)-binap complex catalyzes the two successive reactions", TETRAHEDRON, vol. 15, 2004, pages 2647 - 2651, XP004559144, ISSN: 0957-4166, doi:10.1016/j.tetasy.2004.07.003
FUGANTI,C. ET AL.: "On the microbial biogeneration of (R) y -jasmolactone", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 3, 1993, pages 2777 - 2780, XP026630441, ISSN: 0960-894X, doi:10.1016/S0960-894X(01)80762-9
NALLASIVAM, J. L. ET AL.: "Pd-Catalyzed Site-Selective Mono-allylic Substitution and Bis-arylation by Directed Allylic C-H Activation: Synthesis of anti-y-(Aryl,Styryl)-beta-hydroxy Acids and Highly Substituted Tetrahydrofurans", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 138, no. 40, 12 October 2016 (2016-10-12), pages 13238 - 13245, XP055632413, ISSN: 0002-7863
KANEMASA, S. ET AL.: "Synthesis of 4-[(E)-1-alkenyl]-2-hydroxybutanolides and (Z)-4-alkylidene-2-butenolides through cycloadditions using a phosphorus-functionalized nitrile oxide", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 62, no. 1, 1989, pages 171 - 179, XP055632424, ISSN: 0009-2673
LI, W. Z. ET AL.: "Chemoselective Aldol Reaction of Silyl Enolates Catalyzed by MgI2 Etherate", ORGANIC LETTERS, vol. 4, no. 20, 23 July 2002 (2002-07-23), pages 3485 - 3488, XP055632426, ISSN: 1523-7060
SUN,M. ET AL.: "α-Vinylation of amides with arylacetylenes: synthesis of allylamines under metal-free conditions", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 11, no. 41, 2013, pages 7076 - 7079, XP055632428, ISSN: 1477-0520
DICKMEISS,G. ET AL.: "Organocatalytic asymmetric desymmetrization-fragmentation of cyclic ketones", ANGEWANDTE CHEMIE , INTERNATIONAL EDITION, vol. 48, no. 36, 2009, pages 6650 - 6653, XP055632432, ISSN: 1433-7851
DATABASE REGISTRY [online] 5 March 2019 (2019-03-05), retrieved from STN Database accession no. 1623052-49-2
NAGI, R. K. ET AL.: "Synthesis and biological evaluation of sapinofuranones A, B and 1,2,3-triazole-sapinofuranone hybrids as cytotoxic agents", RSC ADVANCES, vol. 6, no. 103, 2016, pages 101501 - 101512, XP055632440, ISSN: 2046-2069
Attorney, Agent or Firm:
OHGA, Shinji et al. (JP)
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