IP Library Granted Patent US 12,491,173
Granted Patent B2
US 12,491,173 · App. 17/175,186 · Granted Dec 9, 2025

Metabolism-improving agent comprising rare fatty acid

Inventors: Jun Ogawa (Kyoto, JP); Shigenobu Kishino (Kyoto, JP); Teruo Kawada (Kyoto, JP); Nobuyuki Takahashi (Kyoto, JP); Tsuyoshi Goto (Kyoto, JP); Yasunori Yonejima (Muko, JP)
Assignee: Noster Inc.
A61K31/202A23L33/12A61K31/20A61K31/201
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,491,173
App. No.
17/175,186
Granted
Dec 9, 2025
Kind
B2
Abstract

The invention provides a metabolism improving agent containing a rare fatty acid such as hydroxylated fatty acid, oxo fatty acid and the like, and further, food, pharmaceutical product and the like containing the metabolism improving agent.

Claims (18)

1 . A method for treating hyperlipidemia comprising administering to a patient an effective amount of a fatty acid selected from the group consisting of 15-hydroxy-cis-11-eicosenoic acid, 15-hydroxy-cis-5,cis-8,cis-11-eicosatrienoic acid, 15-oxo-cis-11-eicosenoic acid, and 15-oxo-cis-5,cis-8,cis-11-eicosatrienoic acid.

2 . A method for treating hyperlipidemia comprising administering to a patient an effective amount of a fatty acid selected from the group consisting of 12-hydroxy-cis-8,cis-14-eicosadienoic acid, 12-hydroxy-cis-5,cis-8-eicosadienoic acid, and 12-oxo-cis-5,cis-8,cis-14-eicosatrienoic acid.

3 . A method for promoting a PPAR activity, wherein the PPAR is PPARα or PPARγ, comprising administering to a patient an effective amount of a fatty acid selected from the group consisting of 15-hydroxy-cis-11-eicosenoic acid, 15-hydroxy-cis-5,cis-8,cis-11-eicosatrienoic acid, 15-oxo-cis-11-eicosenoic acid, and 15-oxo-cis-5,cis-8,cis-11-eicosatrienoic acid.

4 . A method for promoting a PPAR activity, wherein the PPAR is PPARα or PPARγ, comprising administering to a patient an effective amount of a fatty acid selected from the group consisting of 12-hydroxy-cis-8,cis-14-eicosadienoic acid, 12-hydroxy-cis-5,cis-8-eicosadienoic acid, and 12-oxo-cis-5,cis-8,cis-14-eicosatrienoic acid.

5 . The method of claim 1 , wherein the fatty acid is 15-hydroxy-cis-11-eicosenoic acid.

6 . The method of claim 1 , wherein the fatty acid is 15-hydroxy-cis-5,cis-8,cis-11-eicosatrienoic acid.

7 . The method of claim 1 , wherein the fatty acid is 15-oxo-cis-11-eicosenoic acid.

8 . The method of claim 1 , wherein the fatty acid is 15-oxo-cis-5,cis-8,cis-11-eicosatrienoic acid.

9 . The method of claim 2 , wherein the fatty acid is 12-hydroxy-cis-8,cis-14-eicosadienoic acid.

10 . The method of claim 2 , wherein the fatty acid is 12-hydroxy-cis-5,cis-8-eicosadienoic acid.

11 . The method of claim 2 , wherein the fatty acid is 12-oxo-cis-5,cis-8,cis-14-eicosatrienoic acid.

12 . The method of claim 3 , wherein the fatty acid is 15-hydroxy-cis-11-eicosenoic acid.

13 . The method of claim 3 , wherein the fatty acid is 15-hydroxy-cis-5,cis-8,cis-11-eicosatrienoic acid.

14 . The method of claim 3 , wherein the fatty acid is 15-oxo-cis-11-eicosenoic acid.

15 . The method of claim 3 , wherein the fatty acid is 15-oxo-cis-5,cis-8,cis-11-eicosatrienoic acid.

16 . The method of claim 4 , wherein the fatty acid is 12-hydroxy-cis-8,cis-14-eicosadienoic acid.

17 . The method of claim 4 , wherein the fatty acid is 12-hydroxy-cis-5,cis-8-eicosadienoic acid.

18 . The method of claim 4 , wherein the fatty acid is 12-oxo-cis-5,cis-8,cis-14-eicosatrienoic acid.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 18, 2024
From: OGAWA, JUN; KISHINO, SHIGENOBU; KAWADA, TERUO; TAKAHASHI, NOBUYUKI; GOTO, TSUYOSHI; YONEJIMA, YASUNORI
To: KYOTO UNIVERSITY; NITTO PHARMACEUTICAL INDUSTRIES, LTD.
Reel/Frame 068942/0231 →
CORRECTIVE ASSIGNMENT TO CORRECT THE THE PROPERTY TYPE FROM APPLICATION NUMBER TO PATENT NUMBER FOR 10952983 AND 10975397 PREVIOUSLY RECORDED AT REEL: 68851 FRAME: 663. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Oct 18, 2024
From: KYOTO UNIVERSITY
To: NOSTER INC.
Reel/Frame 069207/0122 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 9, 2024
From: KYOTO UNIVERSITY
To: NOSTER INC.
Reel/Frame 068851/0663 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 14, 2021
From: NITTO PHARMACEUTICAL INDUSTRIES, LTD.
To: NOSTER INC.
Reel/Frame 055920/0263 →
Priority Claims (1)
JP 2014-011871 · Jan 24, 2014 · national
Continuity (3)
Division 16710302 · Dec 11, 2019
Division 15113654
Related Publication 20210236448A1 · Aug 5, 2021
References Cited (53)
US 20020151734A1 · Schwartzman · 2002 [cited by examiner]
US 20040197882A1 · Saitoh · 2004 [cited by examiner]
US 20060217441A1 · Akimoto et al. · 2006 [cited by applicant]
US 20110028538A1 · Chang · 2011 [cited by applicant]
US 20150125911A1 · Ogawa et al. · 2015 [cited by applicant]
US 20150342916A1 · Ogawa et al. · 2015 [cited by applicant]
US 20160000739A1 · Ogawa et al. · 2016 [cited by applicant]
JP 2006521368A · 2006 [cited by applicant]
JP 2009051732A · 2009 [cited by applicant]
JP 2011184411A · 2011 [cited by applicant]
KR 2006038832A · 2006 [cited by examiner]
KR 100793081B1 · 2008 [cited by examiner]
WO WO2007069758A1 · 2007 [cited by examiner]
WO WO2007090162A2 · 2007 [cited by applicant]
WO WO2008125928A2 · 2008 [cited by applicant]
WO WO2009096579A1 · 2009 [cited by applicant]
WO WO2010039529A2 · 2010 [cited by applicant]
WO WO2013168310A1 · 2013 [cited by applicant]
WO WO2014069227A1 · 2014 [cited by applicant]
WO WO2014129384A1 · 2014 [cited by applicant]
Kämmerer et al., “13-hydroxy linoleic acid increases expression of the cholesterol transporters ABCA1, ABCG1 and SR-BI and stimulates apoA-I-dependent cholesterol efflux in RAW264.7 macrophages,” Lipids in Health and Di… [cited by examiner]
Woo et al., “The Edible Red Algae, Gracilaria verrucose, Inhibits Lipid Accumulation and ROS Production, but Improves Glucose Uptake in 3T3-L1 Cells,” Phytotherapy Research 27:1102-1105 (2013). (Year: 2013). [cited by examiner]
Kim et al., “Potent PPARa Activator Derived from Tomato Juice, 13- oxo-9,11-Octadecadienoic Acid, Decreases Plasma and Hepatic Triglyceride in Obese Diabetic Mice,” PLOS One Feb. 2012, vol. 7, Issue 2. (Year: 2012). [cited by examiner]
(Z)-13-Oxo-9-octadecenoic acid (HMDB0029796) (Sep. 11, 2012). (Year: 2012). [cited by examiner]
Lacoste et al., “Hyperlipidemia and Coronary Disease,” Circulation vol. 92, Nol. 11 (1995). (Year: 1995). [cited by examiner]
Kishimoto et al., “Two Distinct Pathways for the Formation of Hydroxy FA from Linoleic Acid by Lactic Acid Bacteria,” Lipids, vol. 38 , No. 12 (2003). (Year: 2003). [cited by examiner]
Almeida et al., “Increased Lipid Oxidation Causes Oxidative Stress, Increased Peroxisome Proliferator-activated Receptor-γ Expression, and Diminished Pro-osteogenic Wnt Signaling in the Skeleton,” [cited by applicant]
Baker et al., “Fatty Acid Transduction of Nitric Oxide Signaling,” [cited by applicant]
Black et al., “Antifungal Lipids Produced by Lactobacilli and Their Structural Identification by Normal Phase LC/Atmospheric Pressure Photoionization-MS/MS,” [cited by applicant]
Fang et al., “14, 15-Dihydroxyeicosatrienoic acid activates peroxisome proliferator-activated receptor-α,” [cited by applicant]
Grechkin et al., “The lipoxygenase pathway in tulip ( [cited by applicant]
Joo et al., “Biochemical characterization and FAD-binding analysis of oleate hydratase from [cited by applicant]
Kammerer et al., “13-hydroxy linoleic acid increases expression of the cholesterol transporters ABCA1, ABCG1 and SR-BI and stimulates apoA-I-dependent cholesterol efflux in RAW264.7 macrophages,” [cited by applicant]
Kim et al., “9-oxo-10(E), 12(E)-octadecadienoic acid derived from tomato is a potent PPARα agonist to decrease triglyceride accumulation in mouse primary hepatocytes,” [cited by applicant]
Kim et al., “Potent PPARα Activator Derived from Tomato Juice, 13-oxo-9,11-Octadecadienoic Acid, Decreases Plasma and Hepatic Triglyceride in Obese Diabetic Mice,” [cited by applicant]
Nagao et al., “Conjugated Fatty Acids in Food and Their Health Benefits,” [cited by applicant]
Nagy et al., “Oxidized LDL Regulates Macrophage Gene Expression through Ligand Activation of PPARγ,” [cited by applicant]
Nakajima et al., “Synthesis of 13-Oxo-(Z)-9-octadecenoic Acid and 15-Oxo-(Z)-11-icosenoic Acid, Arrestants of [cited by applicant]
Naruhn et al., “15-Hydroxyeicosatetraenoic Acid is a Preferential Peroxisome Proliferator-Activated Receptor β/δ Agonist,” [cited by applicant]
Oh et al., “Biotransformation of Linoleic acid into Hydroxy Fatty Acids and Carboxylic Acids Using a Linoleate Double Bond Hydratase as Key Enzyme,” [cited by applicant]
Pham et al., “Activation of peroxisome proliferator-activated receptor (PPAR)-gamma by 15S-hydroxyeicosatrienoic acid parallels growth suppression of androgen-dependent prostatic adenocarcinoma cells,” [cited by applicant]
Shiraki et al., “α,β-Unsaturated Ketone Is a Core Moiety of Natural Ligands for Covalent Binding to Peroxisome Proliferator-activated Receptor γ,” [cited by applicant]
Schuchardt et al., “Comparison of free serum oxylipin concentrations in hyper- vs. normolipidemic men,” [cited by applicant]
Sokmen et al., “Anti-elastase, anti-urease and antioxidant activities of (3-13)-monohydroxyeicosanoic acid isomers,” [cited by applicant]
Takahashi et al., “Localization of 9- and 13-oxo-octadecadienoic acids in tomato fruit,” [cited by applicant]
Takeuchi et al., “Hydroxy fatty acid production by [cited by applicant]
Tanabe et al., “Production of unique hydroxy fatty acid using lactic acid bacteria,” [cited by applicant]
Waku et al., “The nuclear receptor PPARγ individually responds to serotonin- and fatty acid-metabolites,” [cited by applicant]
Waku et al., “Structural Insight into PPARγ Activation Through Covalent Modification with Endogenous Fatty Acids,” [cited by applicant]
Wauwe et al., “Suggested mechanism for the formation of 15-hydroxyeicosatrienoic acid by rat epidermal microsomes,” [cited by applicant]
Watanebe et al., “9-Oxooctadeca-10, 12-dienoic Acids as Acetyl-CoA Carboxylase Inhibitors from Red Pepper ( [cited by applicant]
Yokoi et al., “Hydroxy Monounsaturated Fatty Acids as Agonists for Peroxisome Proliferator-Activated Receptors,” [cited by applicant]
Japanese Patent Office, International Search Report in International Patent Application No. PCT/JP2015/051843 (Apr. 21, 2015). [cited by applicant]