Title:
NOVEL PLASMALOGEN DERIVATIVE
Document Type and Number:
WIPO Patent Application WO/2019/208392
Kind Code:
A1
Abstract:
A compound represented by general formula (I), a racemic form thereof, or a salt of the compound or the racemic form. (In general formula (I), X represents an oxygen atom, a nitrogen atom, a sulfur atom or a carbon atom; R1 represents R1a-Y-R1b (wherein each of R1a and R1b represents a saturated or unsaturated aliphatic hydrocarbon group, an aromatic group, a heterocyclic group, or a group obtained by combining these groups; and Y represents an oxygen atom, a nitrogen atom, a sulfur atom or a carbon atom); each R2 represents a saturated or unsaturated aliphatic hydrocarbon group; and R3 represents choline, ethanolamine, inositol or serine.)
Inventors:
FUJINO TAKEHIKO (JP)
MAWATARI SHIRO (JP)
YAMASHITA TOYOHARU (JP)
KITAMURA MITSURU (JP)
OKAUCHI TATSUO (JP)
HOSSAIN SHAMIM (JP)
MAWATARI SHIRO (JP)
YAMASHITA TOYOHARU (JP)
KITAMURA MITSURU (JP)
OKAUCHI TATSUO (JP)
HOSSAIN SHAMIM (JP)
Application Number:
PCT/JP2019/016638
Publication Date:
October 31, 2019
Filing Date:
April 18, 2019
Export Citation:
Assignee:
INST OF RHEOLOGICAL FUNCTIONS OF FOOD (JP)
International Classes:
C07F9/09; A61K31/683; A61K31/685; A61P3/00; A61P3/10; A61P9/10; A61P25/00; A61P25/16; A61P25/18; A61P25/24; A61P25/28; A61P31/00; A61P37/02
Domestic Patent References:
| WO1993021191A1 | 1993-10-28 | |||
| WO2011083827A1 | 2011-07-14 | |||
| WO2010071988A1 | 2010-07-01 | |||
| WO2013037862A1 | 2013-03-21 |
Foreign References:
| JP2005529969A | 2005-10-06 | |||
| DE10152376A1 | 2003-05-15 | |||
| JP2016111929A | 2016-06-23 | |||
| JP2016045112A | 2016-04-04 | |||
| JP2006232967A | 2006-09-07 | |||
| JP2016108466A | 2016-06-20 | |||
| JP2003012520A | 2003-01-15 | |||
| JP5483846B2 | 2014-05-07 | |||
| JP2016108466A | 2016-06-20 |
Other References:
A E ROZIN , S P KABANOV , S E KUPHIYANOV , G A SEREBRENNIKOVA , R P EVSTIGNEEVA : "Mass-Spectrometry of Ether Lipids. II. Mass-Spectrometry of Ether Glycerophospholipids", BIOORGANICHESKAYA KHIMIYA, vol. 3, no. 3, 30 November 1977 (1977-11-30), pages 397 - 401, XP009524327, ISSN: 0132-3423
LI, RUOXIN ET AL.: "Sulfur-substituted phosphatidylethanolamines", JOURNAL OF ORGANIC CHEMISTRY, vol. 58, no. 7, 1993, pages 1952 - 1 9 54, XP002203063, DOI: 10.1021/jo00059a061
WICHMANN, OLIVER ET AL.: "Probing phospholipase A2 with fluo rescent phospholipid substrates", CHEMBIOCHEM, vol. 8, no. 13, 3 September 2007 (2007-09-03) - 23 May 2008 (2008-05-23), pages 1555 - 1569, XP055646058
MD. SHAMIM HOSSAIN ET AL.: "Plasmalogens rescue neuronal cell death through an activation of AKT and ERK survival signaling", PLOS ONE, vol. 8, no. 12, 2013, pages e83508
MD. SHAMIM HOSSAIN ET AL.: "Neuronal Orphan G-Protein Coupled Receptor Proteins Mediate Plasmalogens-Induced Activation of ERK and Akt Signaling", PLOS ONE, vol. 11, no. 3, 2016, pages e0150846
M. IFUKU ET AL.: "Anti-inflammatory / anti-amyloidogenic effects of plasmalogens in lipopolysaccharide-induced neuroinflammation in adult mice", J OF NEUROINFLAMMATION, vol. 9, 2012, pages 197, XP021116223, DOI: 10.1186/1742-2094-9-197
Z. GUAN ET AL.: "Decrease and Structural Modifications of Phosphatidylethanolamine Plasmalogen in the Brain with Alzheimer Disease", J NEUROPATHOL EXP NEUROL, vol. 58, no. 7, 1999, pages 740 - 747, XP008128120
D. B. GOODENOWE ET AL.: "Peripheral ethanolamine plasmalogen deficiency: a logical causative factor in Alzheimer's disease and dementia", J LIPID RES, vol. 48, 2007, pages 2485 - 2498, XP008122068, DOI: 10.1194/JLR.P700023-JLR200
T. SANADA ET AL.: "Serum Plasmalogens in Ischemic Heart Disease", J. JAPAN ATHEROSCLEROSIS SOCIETY, vol. 11, 1983, pages 535 - 539
T. FUJINO ET AL.: "Efficacy and Blood Plasmalogen Changes by Oral Administration of Plasmalogen in Patients with Mild Alzheimer's Disease and Mild Cognitive Impairment: A Multicenter, Randomized, Double-blind, Placebo-controlled Trial", EBIOMEDICINE, vol. 17, 2017, pages 199 - 205
L. GREGOIRE ET AL.: "Plasmalogen precursor analog treatment reduces levodopa-induced dyskinesias in parkinsonian monkeys", BEHAV BRAIN RES, vol. 286, 2015, pages 328 - 337
C. FABIEN ET AL.: "Brain-Targeting Form of Docosahexaenoic Acid for Experimental Stroke Treatment: MRI Evaluation and Anti-Oxidant Impact", CURRENT NEUROVASCULAR RES, vol. 8, no. 2, 2011, pages 95 - 102
P. WANG ET AL.: "Improved Plasmalogen Synthesis Using Organobarium Intermediates", J. ORG. CHEM, vol. 72, 2007, pages 5005 - 5007,5006
See also references of EP 3786170A4
LI, RUOXIN ET AL.: "Sulfur-substituted phosphatidylethanolamines", JOURNAL OF ORGANIC CHEMISTRY, vol. 58, no. 7, 1993, pages 1952 - 1 9 54, XP002203063, DOI: 10.1021/jo00059a061
WICHMANN, OLIVER ET AL.: "Probing phospholipase A2 with fluo rescent phospholipid substrates", CHEMBIOCHEM, vol. 8, no. 13, 3 September 2007 (2007-09-03) - 23 May 2008 (2008-05-23), pages 1555 - 1569, XP055646058
MD. SHAMIM HOSSAIN ET AL.: "Plasmalogens rescue neuronal cell death through an activation of AKT and ERK survival signaling", PLOS ONE, vol. 8, no. 12, 2013, pages e83508
MD. SHAMIM HOSSAIN ET AL.: "Neuronal Orphan G-Protein Coupled Receptor Proteins Mediate Plasmalogens-Induced Activation of ERK and Akt Signaling", PLOS ONE, vol. 11, no. 3, 2016, pages e0150846
M. IFUKU ET AL.: "Anti-inflammatory / anti-amyloidogenic effects of plasmalogens in lipopolysaccharide-induced neuroinflammation in adult mice", J OF NEUROINFLAMMATION, vol. 9, 2012, pages 197, XP021116223, DOI: 10.1186/1742-2094-9-197
Z. GUAN ET AL.: "Decrease and Structural Modifications of Phosphatidylethanolamine Plasmalogen in the Brain with Alzheimer Disease", J NEUROPATHOL EXP NEUROL, vol. 58, no. 7, 1999, pages 740 - 747, XP008128120
D. B. GOODENOWE ET AL.: "Peripheral ethanolamine plasmalogen deficiency: a logical causative factor in Alzheimer's disease and dementia", J LIPID RES, vol. 48, 2007, pages 2485 - 2498, XP008122068, DOI: 10.1194/JLR.P700023-JLR200
T. SANADA ET AL.: "Serum Plasmalogens in Ischemic Heart Disease", J. JAPAN ATHEROSCLEROSIS SOCIETY, vol. 11, 1983, pages 535 - 539
T. FUJINO ET AL.: "Efficacy and Blood Plasmalogen Changes by Oral Administration of Plasmalogen in Patients with Mild Alzheimer's Disease and Mild Cognitive Impairment: A Multicenter, Randomized, Double-blind, Placebo-controlled Trial", EBIOMEDICINE, vol. 17, 2017, pages 199 - 205
L. GREGOIRE ET AL.: "Plasmalogen precursor analog treatment reduces levodopa-induced dyskinesias in parkinsonian monkeys", BEHAV BRAIN RES, vol. 286, 2015, pages 328 - 337
C. FABIEN ET AL.: "Brain-Targeting Form of Docosahexaenoic Acid for Experimental Stroke Treatment: MRI Evaluation and Anti-Oxidant Impact", CURRENT NEUROVASCULAR RES, vol. 8, no. 2, 2011, pages 95 - 102
P. WANG ET AL.: "Improved Plasmalogen Synthesis Using Organobarium Intermediates", J. ORG. CHEM, vol. 72, 2007, pages 5005 - 5007,5006
See also references of EP 3786170A4
Attorney, Agent or Firm:
TAKATSU Kazuya (JP)
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