Title:
PHOSPHOLIPID COMPOUND CONTAINING UNSATURATED FATTY ACID DERIVATIVE HAVING CYCLOPROPANE RING
Document Type and Number:
WIPO Patent Application WO/2014/126191
Kind Code:
A1
Abstract:
The present invention addresses the problem of providing a drug having a cognitive function improving effect and antidiabetic effect.
A phospholipid compound which contains an unsaturated fatty acid having a cyclopropane ring such as 8-[2-(2-pentyl-cyclopropylmethyl)-cyclopropyl]-octanoic acid (DCP-LA), 8-(2-octylcyclopropyl)octanoic acid (DCP-OA), etc., in particular, 1,2-o-bis-[8-{2-(2-pentyl-cyclopropylmethyl)-cyclopropyl}-octanoyl]-sn-glycero-3-phosphatidylethanolamine (diDCP-LA-PE) has a cognitive function improving effect and antidiabetic effect and, therefore, is useful as a drug such as a therapeutic agent for dementia, antidiabetic drug, etc.
Inventors:
NISHIZAKI TOMOYUKI (JP)
TANAKA AKITO (JP)
TANAKA AKITO (JP)
Application Number:
PCT/JP2014/053448
Publication Date:
August 21, 2014
Filing Date:
February 14, 2014
Export Citation:
Assignee:
NISHIZAKI BIOINFORMATION RES INST (JP)
International Classes:
A61K31/683; A61K31/685; A61P3/10; A61P25/28; A61P43/00; C07F9/10; C07F9/117; G01N33/50
Domestic Patent References:
| WO2013071281A1 | 2013-05-16 | |||
| WO2002050013A1 | 2002-06-27 |
Foreign References:
| JP2011529503A | 2011-12-08 | |||
| JP2009007329A | 2009-01-15 | |||
| JP2005247728A | 2005-09-15 | |||
| JP2005247728A | 2005-09-15 |
Other References:
CHANGJIN ZHU ET AL.: "Synthesis of a novel lysophosphatidylcholine.", J.NAT. PROD., vol. 64, 2001, pages 98 - 99, XP055273529
D.L.TURNER ET AL.: "The synthesis of phosphatidylethanolamine and phosphatidylserine containing acetylenic or cyclopropane fatty acids and the activity of these phosphatides in blood coagulation.", LIPIDS, vol. 5, no. 7, 1970, pages 650 - 657, XP035174858
KAORU NAGAI ET AL.: "Dilinoleoyl- phosphatidylethanolamine from Hericium erinaceum protects against ER stress-dependent Neuro2a cell death via protein kinase C pathway.", JOURNAL OF NUTRITIONAL BIOCHEMISTRY, vol. 17, 2006, pages 525 - 530, XP024960855
TAKESHI KANNNO ET AL.: "The linoleic acid derivative DCP-LA selectively activates PKC-epsilon, possibly binding to the phosphatidylserine binding site.", JOURNAL OF LIPID RESEARCH, vol. 47, 2006, pages 1146 - 1156, XP002550145
YAGUCHI T; NAGATA T; NISHIZAKI T: "Dilinoleoylphosphatidylcholine ameliorates scopolamine-induced impairment of spatial learning and memory by targeting alpha-7 nicotinic ACh receptors", LIFE SCI, vol. 84, 2009, pages 263 - 6, XP055174884, DOI: doi:10.1016/j.lfs.2008.12.003
YAGUCHI T; NAGATA T; NISHIZAKI T.: "1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine improves cognitive decline by enhancing long-term depression", BEHAV BRAIN RES, vol. 204, 2009, pages 129 - 32, XP026422139
"Jikken Kagaku Kouza 16, synthesis of organic compound (kyo"
SUN T; WANG Q; YU Z; ZHANG Y; GUO Y; CHEN K; SHEN X; JIANG H.: "Hyrtiosal, a PTP1B inhibitor from the marine sponge Hyrtios erectus, shows extensive cellular effects on PI3K/AKT activation, glucose transport, and TGFb/Smad2 signaling", CHEMBIOCHEM, vol. 8, no. 2, 2007, pages 187 - 193
LIN Z; ZHANG Y; ZHANG Y; SHEN H; HU L; JIANG H; SHEN X: "Oleanolic acid derivative NPLC441 potently stimulates glucose transport in 3T3-L1 adipocytes via a multi-target mechanism", BIOCHEM PHARMACOL, vol. 76, no. 10, 2008, pages 1251 - 1262, XP025573141, DOI: doi:10.1016/j.bcp.2008.08.016
ZHANG Y; ZHANG H; YAO XG; SHEN H; CHEN J; LI C; CHEN L; ZHENG M; YE J; HU L: "+)-Rutamarin as a dual inducer of both GLUT4 translocation and expression efficiently ameliorates glucose homeostasis in insulin-resistant mice", PLOS ONE, vol. 7, no. 2, 2012, pages E31811
MAARBJERG SJ; SYLOW L; RICHTER EA: "Current understanding of increased insulin sensitivity after exercise-emerging candidates", ACTA PHYSIOL, vol. 202, 2011, pages 323 - 335
BRYANT NJ; GOVERS R; JAMES DE: "Regulated transport of the glucose transporter GLUT4", NAT REV MOL CELL BIOL, vol. 3, 2002, pages 267 - 277
KIKKAWA ET AL., J. BIOL. CHEM., vol. 257, 1982, pages 13341
BRYANT NJ ET AL., NAT REV MOL CELL BIOL, vol. 3, 2002, pages 267 - 277
NEUROSCIENCE, vol. 130, no. 1, 2005, pages 207 - 213
YAGUCHI T; NAGATA T; MUKASA T; FUJIKAWA H; YAMAMOTO H; YAMAMOTO S; ISO H; TANAKA A; NISHIZAKI T: "Linoleic acid derivative DCP-LA improves learning impairment in SAMP8", NEUROREPORT, vol. 17, no. 1, 2006, pages 105 - 108
SHIMIZU T; KANNO T; TANAKA A; NISHIZAKI T.: "a,p-DCP-LA selectively activates PKC- and stimulates neurotransmitter release with the highest potency among 4 diastereomers", CELL PHYSIOL BIOCHEM, vol. 27, no. 2, 2011, pages 149 - 158, XP055088919
KANNO T; YAGUCHI T; SHIMIZU T; TANAKA A; NISHIZAKI T.: "8-[2-(2-Pentyl-cyclopropylmethyl)-cyclopropyl]-octanoic acid and its diastereomers improve age-related cognitive deterioration", LIPIDS, vol. 47, no. 7, 2012, pages 687 - 695, XP035075618, DOI: doi:10.1007/s11745-012-3677-y
SAMPSONA SR; COOPERB DR: "Specific protein kinase C isoforms as transducers and modulators of insulin signaling", MOL GENET METAB, vol. 89, no. 1-2, 2006, pages 32 - 47
STOCKLI J; FAZAKERLEY DJ; JAMES DE: "GLUT4 exocytosis", J CELL SCI, vol. 124, 2011, pages 4147 - 4159
BABA Y ET AL., J AM CHEM SOC, vol. 125, 2003, pages 9740 - 9749
RICE RL ET AL., BIOCHEMISTRY, vol. 36, 1997, pages 15965 - 15974
KANNO T ET AL., J LIPID RES, vol. 47, 2006, pages 1146 - 1156
See also references of EP 2957285A4
D.L.TURNER ET AL.: "The synthesis of phosphatidylethanolamine and phosphatidylserine containing acetylenic or cyclopropane fatty acids and the activity of these phosphatides in blood coagulation.", LIPIDS, vol. 5, no. 7, 1970, pages 650 - 657, XP035174858
KAORU NAGAI ET AL.: "Dilinoleoyl- phosphatidylethanolamine from Hericium erinaceum protects against ER stress-dependent Neuro2a cell death via protein kinase C pathway.", JOURNAL OF NUTRITIONAL BIOCHEMISTRY, vol. 17, 2006, pages 525 - 530, XP024960855
TAKESHI KANNNO ET AL.: "The linoleic acid derivative DCP-LA selectively activates PKC-epsilon, possibly binding to the phosphatidylserine binding site.", JOURNAL OF LIPID RESEARCH, vol. 47, 2006, pages 1146 - 1156, XP002550145
YAGUCHI T; NAGATA T; NISHIZAKI T: "Dilinoleoylphosphatidylcholine ameliorates scopolamine-induced impairment of spatial learning and memory by targeting alpha-7 nicotinic ACh receptors", LIFE SCI, vol. 84, 2009, pages 263 - 6, XP055174884, DOI: doi:10.1016/j.lfs.2008.12.003
YAGUCHI T; NAGATA T; NISHIZAKI T.: "1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine improves cognitive decline by enhancing long-term depression", BEHAV BRAIN RES, vol. 204, 2009, pages 129 - 32, XP026422139
"Jikken Kagaku Kouza 16, synthesis of organic compound (kyo"
SUN T; WANG Q; YU Z; ZHANG Y; GUO Y; CHEN K; SHEN X; JIANG H.: "Hyrtiosal, a PTP1B inhibitor from the marine sponge Hyrtios erectus, shows extensive cellular effects on PI3K/AKT activation, glucose transport, and TGFb/Smad2 signaling", CHEMBIOCHEM, vol. 8, no. 2, 2007, pages 187 - 193
LIN Z; ZHANG Y; ZHANG Y; SHEN H; HU L; JIANG H; SHEN X: "Oleanolic acid derivative NPLC441 potently stimulates glucose transport in 3T3-L1 adipocytes via a multi-target mechanism", BIOCHEM PHARMACOL, vol. 76, no. 10, 2008, pages 1251 - 1262, XP025573141, DOI: doi:10.1016/j.bcp.2008.08.016
ZHANG Y; ZHANG H; YAO XG; SHEN H; CHEN J; LI C; CHEN L; ZHENG M; YE J; HU L: "+)-Rutamarin as a dual inducer of both GLUT4 translocation and expression efficiently ameliorates glucose homeostasis in insulin-resistant mice", PLOS ONE, vol. 7, no. 2, 2012, pages E31811
MAARBJERG SJ; SYLOW L; RICHTER EA: "Current understanding of increased insulin sensitivity after exercise-emerging candidates", ACTA PHYSIOL, vol. 202, 2011, pages 323 - 335
BRYANT NJ; GOVERS R; JAMES DE: "Regulated transport of the glucose transporter GLUT4", NAT REV MOL CELL BIOL, vol. 3, 2002, pages 267 - 277
KIKKAWA ET AL., J. BIOL. CHEM., vol. 257, 1982, pages 13341
BRYANT NJ ET AL., NAT REV MOL CELL BIOL, vol. 3, 2002, pages 267 - 277
NEUROSCIENCE, vol. 130, no. 1, 2005, pages 207 - 213
YAGUCHI T; NAGATA T; MUKASA T; FUJIKAWA H; YAMAMOTO H; YAMAMOTO S; ISO H; TANAKA A; NISHIZAKI T: "Linoleic acid derivative DCP-LA improves learning impairment in SAMP8", NEUROREPORT, vol. 17, no. 1, 2006, pages 105 - 108
SHIMIZU T; KANNO T; TANAKA A; NISHIZAKI T.: "a,p-DCP-LA selectively activates PKC- and stimulates neurotransmitter release with the highest potency among 4 diastereomers", CELL PHYSIOL BIOCHEM, vol. 27, no. 2, 2011, pages 149 - 158, XP055088919
KANNO T; YAGUCHI T; SHIMIZU T; TANAKA A; NISHIZAKI T.: "8-[2-(2-Pentyl-cyclopropylmethyl)-cyclopropyl]-octanoic acid and its diastereomers improve age-related cognitive deterioration", LIPIDS, vol. 47, no. 7, 2012, pages 687 - 695, XP035075618, DOI: doi:10.1007/s11745-012-3677-y
SAMPSONA SR; COOPERB DR: "Specific protein kinase C isoforms as transducers and modulators of insulin signaling", MOL GENET METAB, vol. 89, no. 1-2, 2006, pages 32 - 47
STOCKLI J; FAZAKERLEY DJ; JAMES DE: "GLUT4 exocytosis", J CELL SCI, vol. 124, 2011, pages 4147 - 4159
BABA Y ET AL., J AM CHEM SOC, vol. 125, 2003, pages 9740 - 9749
RICE RL ET AL., BIOCHEMISTRY, vol. 36, 1997, pages 15965 - 15974
KANNO T ET AL., J LIPID RES, vol. 47, 2006, pages 1146 - 1156
See also references of EP 2957285A4
Attorney, Agent or Firm:
TAKASHIMA, HAJIME (JP)
Takashima 1 (JP)
Takashima 1 (JP)
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