Title:
ABIETANE-TYPE DITERPENE COMPOUND HAVING LIPID-LOWERING ACTIVITY, METHOD FOR PREPARING SAME, AND USE OF SAME
Document Type and Number:
WIPO Patent Application WO/2016/192631
Kind Code:
A1
Abstract:
The present invention provides an abietane-type diterpene compound having lipid-lowering activity, a method for preparing same, and use of same. Specifically, the compound has the structure shown in formula I. The definitions of the groups are discussed in the specification. The compound of the present invention has activity of increasing in vivo or in vitro ingestion of low-density lipoprotein, and has a potential to be used as a novel lipid-lowering drug.
Inventors:
YE YANG (CN)
WANG YIPING (CN)
YAO SHENG (CN)
ZHAO JING (CN)
TANG CHUNPING (CN)
XU WENWEI (CN)
KE CHANGQIANG (CN)
XI CONG (CN)
WANG YIPING (CN)
YAO SHENG (CN)
ZHAO JING (CN)
TANG CHUNPING (CN)
XU WENWEI (CN)
KE CHANGQIANG (CN)
XI CONG (CN)
Application Number:
PCT/CN2016/084358
Publication Date:
December 08, 2016
Filing Date:
June 01, 2016
Export Citation:
Assignee:
SHANGHAI INST MATERIA MEDICA CAS (CN)
International Classes:
C07D493/08; A61K31/366; A61P3/06; C07C43/23; C07C62/32; C07C62/36; C07D303/02; C07D307/77; C07D311/80; C07D317/70; C07D319/14
Foreign References:
| CN102295545A | 2011-12-28 | |||
| CN105801396A | 2016-07-27 | |||
| CN104557823A | 2015-04-29 | |||
| CN101633660A | 2010-01-27 |
Other References:
ZHANG, CHENGLU ET AL.: "Total synthesis of 3-carbonyl-10-demethyl-12-hydroxyabietane", JOURNAL OF LIAONING NORMAL UNIVERSITY ( NATURAL SCIENCE EDITION, vol. 34, no. 1, 31 March 2011 (2011-03-31), pages 71 - 73
LU , YI ET AL.: "Abietane diterpenes from Callicarpa pedunculata", NATURAL PRODUCT RESEARCH AND DEVELOPMENT, vol. 23, no. 1, 31 January 2011 (2011-01-31), pages 66 - 68
MATSUMOTO, TAKASHI. ET AL.: "Rearrangement of the angular methyl group in dehydroabietic acid derivatives.", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 41, no. 11, 30 November 1993 (1993-11-30), pages 1960 - 1964, XP055332836
KUO, YUEH-HSIUNG ET AL.: "Diterpenes from the heartwood of Juniperus formosana Hay. var. concolor Hay.", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 44, no. 8, 31 August 1996 (1996-08-31), pages 1431 - 1435, XP055332840
MATSUMOTO, TAKASHI ET AL.: "A new synthesis of 3-oxosapriparaquinone, a diterpene from Salvia prionitis Hance (Labiatae).", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 44, no. 8, 31 August 1996 (1996-08-31), pages 1588 - 1590, XP008082875
ARIHARA, SHIGENOBU ET AL.: "A new abietane and two dimeric abietane diterpenes from the black heartwood of Cryptomeria japonica.", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 52, no. 3, 31 March 2004 (2004-03-31), pages 354 - 358, XP018003259
HSIEH, CHIN-LIN ET AL.: "Novel Terpenoids from Calocedrus macrolepis var. formosana.", CHEMISTRY & BIODIVERSITY., vol. 8, 31 December 2011 (2011-12-31), pages 1901 - 1907, XP055332842
YOSHIKAWA, KAZUKO ET AL.: "Novel abietane diterpenoids and aromatic compounds from Cladonia rangiferina and their antimicrobial activity against antibiotics resistant bacteria.", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 56, no. 1, 31 January 2008 (2008-01-31), pages 89 - 92, XP055332843
WENKERT, ERNEST ET AL.: "Synthesis of some drimanic sesquiterpenes .", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 86, no. 10, 31 December 1964 (1964-12-31), pages 2044 - 2050, XP055127053
YAO, SHENG ET AL.: "Abietane Diterpenoids from the Bark of Cryptomeria fortunei.", JOURNAL OF NATURAL PRODUCTS, vol. 71, no. 7, 31 December 2008 (2008-12-31), pages 1242 - 1246, XP018027314
BURNELL, ROBERT H. ET AL.: "The structures of the nellionols. Synthesis of model abieta-8, 11, 13-trien-7-ones. Synthesis of 5-dehydronellionol trimethyl ether.", CANADIAN JOURNAL OF CHEMISTRY., vol. 62, no. 12, 31 December 1984 (1984-12-31), pages 2822 - 2829, XP055127054
LU , YI ET AL.: "Abietane diterpenes from Callicarpa pedunculata", NATURAL PRODUCT RESEARCH AND DEVELOPMENT, vol. 23, no. 1, 31 January 2011 (2011-01-31), pages 66 - 68
MATSUMOTO, TAKASHI. ET AL.: "Rearrangement of the angular methyl group in dehydroabietic acid derivatives.", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 41, no. 11, 30 November 1993 (1993-11-30), pages 1960 - 1964, XP055332836
KUO, YUEH-HSIUNG ET AL.: "Diterpenes from the heartwood of Juniperus formosana Hay. var. concolor Hay.", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 44, no. 8, 31 August 1996 (1996-08-31), pages 1431 - 1435, XP055332840
MATSUMOTO, TAKASHI ET AL.: "A new synthesis of 3-oxosapriparaquinone, a diterpene from Salvia prionitis Hance (Labiatae).", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 44, no. 8, 31 August 1996 (1996-08-31), pages 1588 - 1590, XP008082875
ARIHARA, SHIGENOBU ET AL.: "A new abietane and two dimeric abietane diterpenes from the black heartwood of Cryptomeria japonica.", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 52, no. 3, 31 March 2004 (2004-03-31), pages 354 - 358, XP018003259
HSIEH, CHIN-LIN ET AL.: "Novel Terpenoids from Calocedrus macrolepis var. formosana.", CHEMISTRY & BIODIVERSITY., vol. 8, 31 December 2011 (2011-12-31), pages 1901 - 1907, XP055332842
YOSHIKAWA, KAZUKO ET AL.: "Novel abietane diterpenoids and aromatic compounds from Cladonia rangiferina and their antimicrobial activity against antibiotics resistant bacteria.", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 56, no. 1, 31 January 2008 (2008-01-31), pages 89 - 92, XP055332843
WENKERT, ERNEST ET AL.: "Synthesis of some drimanic sesquiterpenes .", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 86, no. 10, 31 December 1964 (1964-12-31), pages 2044 - 2050, XP055127053
YAO, SHENG ET AL.: "Abietane Diterpenoids from the Bark of Cryptomeria fortunei.", JOURNAL OF NATURAL PRODUCTS, vol. 71, no. 7, 31 December 2008 (2008-12-31), pages 1242 - 1246, XP018027314
BURNELL, ROBERT H. ET AL.: "The structures of the nellionols. Synthesis of model abieta-8, 11, 13-trien-7-ones. Synthesis of 5-dehydronellionol trimethyl ether.", CANADIAN JOURNAL OF CHEMISTRY., vol. 62, no. 12, 31 December 1984 (1984-12-31), pages 2822 - 2829, XP055127054
Attorney, Agent or Firm:
XU & PARTNERS, LLC. (CN)
上海一平知识产权代理有限公司 (CN)
上海一平知识产权代理有限公司 (CN)
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