Title:
CONJUGATE COMPOUNDS OF URSODEOXYCHOLIC, BERBERINE OR L-CARNITINE, AND COMPOSITIONS AND METHODS THEREOF
Document Type and Number:
WIPO Patent Application WO/2016/161921
Kind Code:
A1
Abstract:
Conjugate compounds having at least one of a moiety derived from ursodeoxycholic acid, or eicosapentaenoic acid, or docosahexaenoic acid, or rhein, or R- (+) -α-lipoic acid, or ursolic acid, or corosolic acid, or hydroxycitric acid, or cinnamic acid, or cholic acid, or oleanolic acid, or salicylic acid, or betulinic acid, or chlorogenic acid, or caffeic acid, or bassic acid, or acetyl L-carnitine, or S-allyl cysteine sulphoxide, or S-methyl cysteine sulfoxide, or pantothenic acid, or ascorbic acid, or retinoic acid, or nicotinic acid, or biotin, or a derivative or analog thereof, and a moiety derived from berberine or L-carnitine or metformin or unsaturated fatty acid, or a derivative or analog thereof, pharmaceutical compositions, methods of preparation and use of these conjugates in treating and/or preventing, for example, liver diseases or disorders, various diabetes, diabetic complications, dyslipidemia, obesity, metabolic syndromes, pre-diabetes, muscle atrophy, inflammation, and cancers are disclosed. The compounds are also useful in improving liver functions in chronic viral associated liver diseases and alcohol-related liver diseases.
Inventors:
LIU LIPING (US)
Application Number:
PCT/CN2016/078414
Publication Date:
October 13, 2016
Filing Date:
April 05, 2016
Export Citation:
Assignee:
SHENZHEN HIGHTIDE BIOPHARMACEUTICAL LTD (CN)
International Classes:
C07D455/03; A61K31/155; A61K31/20; A61K31/205; A61K31/4375; A61P1/16; A61P3/06; A61P3/10; A61P29/00; C07C57/02; C07C229/22; C07C279/26
Domestic Patent References:
| WO2007095760A1 | 2007-08-30 | |||
| WO2016015634A1 | 2016-02-04 |
Foreign References:
| CN101935319A | 2011-01-05 | |||
| CN103319479A | 2013-09-25 | |||
| CN101113149A | 2008-01-30 | |||
| CN103702668A | 2014-04-02 | |||
| CN102225913A | 2011-10-26 | |||
| CN1917779A | 2007-02-21 | |||
| CN103989677A | 2014-08-20 |
Other References:
JIA, XINGMEI.: "New use of Berberine in clinical", CHINESE COMMUNITY DOCTORS, vol. 14, no. 9, 31 December 2012 (2012-12-31), pages 216, XP009507272, ISSN: 1007-614X
ZHOU, YOUYA ET AL.: "The Physiological Function and Application of L-carnitine", JOURNAL OF HEBEI NORMAL UNIVERSITY ( NATURAL SCIENCE, vol. 25, no. 1, 31 March 2001 (2001-03-31), pages 99 - 101, XP009507269, ISSN: 1000-5854
TANG, KEJIAN.: "Progress of clinical application of L-carnitine", JOURNAL OF HEBEI UNITED UNIVERSITY( HEALTH SCIENCES, vol. 14, no. 6, 30 November 2012 (2012-11-30), pages 799 - 801, XP009507259, ISSN: 2095-2694
LI, XIN ET AL.: "Effect of metformin on non-alcoholic fatty liver disease in type II diabetic rats", GUANGXI MEDICAL JOURNAL, vol. 37, no. 3, 31 March 2015 (2015-03-31), pages 292 - 295, XP009507260, ISSN: 0253-4304
LIU, GENSHENG ET AL.: "Protective effect of dietary monounsaturated fatty acid on cardiovascular system", JOURNAL OF HYGIENE RESEARCH, vol. 35, no. 3, 31 May 2006 (2006-05-31), pages 357 - 359, XP009507246, ISSN: 1000-8020
YU , SEN ET AL.: "Pharmacokinetics of berberine, palmatine, coptisine, epiberberine and jatrorrhizine from Coptidis Rhizoma in diabetic rats", JOURNAL OF CHINA PHARMACEUTICAL UNIVERSITY, vol. 39, no. 6, 31 December 2008 (2008-12-31), pages 526 - 529, XP009507268, ISSN: 1000-5048
YUAN, BIN ET AL.: "Analysis on replacement of traditional chinese medicine bear bile with bile acids based on drug properties", CHINA JOURNAL OF CHINESE MATERIA MEDICA, vol. 39, no. 4, 28 February 2014 (2014-02-28), pages 738 - 743, XP055319438, ISSN: 1001-5302
LIAO, XIANGNING.: "Ursodeoxycholic acid treatment curative effect observation on non- alcoholic fatty liver", CHINA HEALTH INDUSTRY, 31 December 2014 (2014-12-31), pages 114 - 115, XP009507271, ISSN: 1672-5654
CAO, YU.: "potent antioxidant alpha lipoic acid in human body", HEILONGJIANG MEDICINE JOURNAL, vol. 21, no. 2, 31 December 2008 (2008-12-31), pages 64, XP009507270, ISSN: 1006-2882
ZHANG, MINGFA ET AL.: "Diabetes pharmacology of oleanolic acid and ursolic acid", SHANGHAI MEDICAL & PHARMACEUTICAL JOURNAL, vol. 31, no. 8, 31 December 2010 (2010-12-31), pages 347 - 350, XP009507261, ISSN: 1006-1533
ZANG, HENGJIA.: "Application in preventing muscle atrophy of apple", JIANSHENKEXUE, 31 December 2011 (2011-12-31), pages 8, XP009507267, ISSN: 1008-0295
YUAN, ERDONG.: "Development of Research on Hydroxycitric Acid", SICHUAN FOOD AND FERMENTATION, vol. 42, no. 2, 31 December 2006 (2006-12-31), pages 19 - 23, XP009507247, ISSN: 1671-6892
ZHAO, XIAO ET AL.: "Advancement of chlorogenic acid", THE PROCEEDINGS OF THE SEVENTH SYMPOSIUM ON CLINICAL MEDICINE, 1 November 2014 (2014-11-01), pages 123 - 124, XP009507237
LIU, KAI ET AL.: "Brief introduction of study on pharmacological effects of Rhein", CHINESE ARCHIVES OF TRADITIONAL CHINESE MEDICINE, vol. 22, no. 9, 30 September 2004 (2004-09-30), pages 1732 - 1734, XP009507248, ISSN: 1673-7717
CHEN, RUI ET AL.: "Research progress of omega-3 fatty acids for preventing and treating cardiovascular disease", JOURNAL OF JIANGSU UNIVERSITY(MEDICINE EDITION, vol. 22, no. 1, 31 January 2012 (2012-01-31), pages 90 - 92, XP009507258, ISSN: 1671-7783
LI, HAIYAN ET AL.: "Research Progress of Corosolic Acid", CHINESE ARCHIVES OF TRADITIONAL CHINESE MEDICINE, vol. 29, no. 11, 30 November 2011 (2011-11-30), pages 2422 - 2424, XP009507228, ISSN: 1673-7717
See also references of EP 3280712A4
ZHOU, YOUYA ET AL.: "The Physiological Function and Application of L-carnitine", JOURNAL OF HEBEI NORMAL UNIVERSITY ( NATURAL SCIENCE, vol. 25, no. 1, 31 March 2001 (2001-03-31), pages 99 - 101, XP009507269, ISSN: 1000-5854
TANG, KEJIAN.: "Progress of clinical application of L-carnitine", JOURNAL OF HEBEI UNITED UNIVERSITY( HEALTH SCIENCES, vol. 14, no. 6, 30 November 2012 (2012-11-30), pages 799 - 801, XP009507259, ISSN: 2095-2694
LI, XIN ET AL.: "Effect of metformin on non-alcoholic fatty liver disease in type II diabetic rats", GUANGXI MEDICAL JOURNAL, vol. 37, no. 3, 31 March 2015 (2015-03-31), pages 292 - 295, XP009507260, ISSN: 0253-4304
LIU, GENSHENG ET AL.: "Protective effect of dietary monounsaturated fatty acid on cardiovascular system", JOURNAL OF HYGIENE RESEARCH, vol. 35, no. 3, 31 May 2006 (2006-05-31), pages 357 - 359, XP009507246, ISSN: 1000-8020
YU , SEN ET AL.: "Pharmacokinetics of berberine, palmatine, coptisine, epiberberine and jatrorrhizine from Coptidis Rhizoma in diabetic rats", JOURNAL OF CHINA PHARMACEUTICAL UNIVERSITY, vol. 39, no. 6, 31 December 2008 (2008-12-31), pages 526 - 529, XP009507268, ISSN: 1000-5048
YUAN, BIN ET AL.: "Analysis on replacement of traditional chinese medicine bear bile with bile acids based on drug properties", CHINA JOURNAL OF CHINESE MATERIA MEDICA, vol. 39, no. 4, 28 February 2014 (2014-02-28), pages 738 - 743, XP055319438, ISSN: 1001-5302
LIAO, XIANGNING.: "Ursodeoxycholic acid treatment curative effect observation on non- alcoholic fatty liver", CHINA HEALTH INDUSTRY, 31 December 2014 (2014-12-31), pages 114 - 115, XP009507271, ISSN: 1672-5654
CAO, YU.: "potent antioxidant alpha lipoic acid in human body", HEILONGJIANG MEDICINE JOURNAL, vol. 21, no. 2, 31 December 2008 (2008-12-31), pages 64, XP009507270, ISSN: 1006-2882
ZHANG, MINGFA ET AL.: "Diabetes pharmacology of oleanolic acid and ursolic acid", SHANGHAI MEDICAL & PHARMACEUTICAL JOURNAL, vol. 31, no. 8, 31 December 2010 (2010-12-31), pages 347 - 350, XP009507261, ISSN: 1006-1533
ZANG, HENGJIA.: "Application in preventing muscle atrophy of apple", JIANSHENKEXUE, 31 December 2011 (2011-12-31), pages 8, XP009507267, ISSN: 1008-0295
YUAN, ERDONG.: "Development of Research on Hydroxycitric Acid", SICHUAN FOOD AND FERMENTATION, vol. 42, no. 2, 31 December 2006 (2006-12-31), pages 19 - 23, XP009507247, ISSN: 1671-6892
ZHAO, XIAO ET AL.: "Advancement of chlorogenic acid", THE PROCEEDINGS OF THE SEVENTH SYMPOSIUM ON CLINICAL MEDICINE, 1 November 2014 (2014-11-01), pages 123 - 124, XP009507237
LIU, KAI ET AL.: "Brief introduction of study on pharmacological effects of Rhein", CHINESE ARCHIVES OF TRADITIONAL CHINESE MEDICINE, vol. 22, no. 9, 30 September 2004 (2004-09-30), pages 1732 - 1734, XP009507248, ISSN: 1673-7717
CHEN, RUI ET AL.: "Research progress of omega-3 fatty acids for preventing and treating cardiovascular disease", JOURNAL OF JIANGSU UNIVERSITY(MEDICINE EDITION, vol. 22, no. 1, 31 January 2012 (2012-01-31), pages 90 - 92, XP009507258, ISSN: 1671-7783
LI, HAIYAN ET AL.: "Research Progress of Corosolic Acid", CHINESE ARCHIVES OF TRADITIONAL CHINESE MEDICINE, vol. 29, no. 11, 30 November 2011 (2011-11-30), pages 2422 - 2424, XP009507228, ISSN: 1673-7717
See also references of EP 3280712A4
Attorney, Agent or Firm:
ZHONGDING INTELLECTUAL PROPERTY AGENCY (Qinglin Road Longgang Distric, Shenzhen Guangdong 2, CN)
Download PDF:
Previous Patent: COMPOSITE SEPARATOR AND PREPARATION METHOD THEREFOR, AND LITHIUM-ION BATTERY
Next Patent: VIDEO FILE PROCESSING METHOD AND DEVICE
Next Patent: VIDEO FILE PROCESSING METHOD AND DEVICE