IP Library Granted Patent US 12,251,367
Granted Patent B2
US 12,251,367 · App. 18/518,044 · Granted Mar 18, 2025

Medium chain triglyceride compositions

Inventors: Bernard Cuenoud (Cully, CH); Mojgan Masoodi (Eclublens, CH)
Assignee: SOCIÉTÉ DES PRODUITS NESTLÉ S.A.
A61K31/21A23K20/158A23L33/12A23V2002/00
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 12,251,367
App. No.
18/518,044
Granted
Mar 18, 2025
Kind
B2
Abstract

A composition comprising medium-chain triglycerides (MCTs) wherein the composition comprises (i) a MCT comprising three fatty acid moieties each with 8 carbon atoms (MCT-C8) and (ii) a MCT comprising three fatty acid moieties each with 10 carbon atoms (MCT-C10); wherein the ratio of MCT-C8 to MCT-C10 is from 10:90 to 90:10 (mol/mol) and wherein the combined amount of MCT-C8 and MCT-C10 make up at least 50 mol % of the MCTs in the composition.

Claims (22)

1. A method of treating an individual having a brain energy deficiency condition or disease, the method comprising administering a composition comprising medium-chain triglycerides (MCTs) to the individual, wherein the MCTs comprise:

a MCT comprising three fatty acid moieties each with 8 carbon atoms (MCT-C8); and

a MCT comprising three fatty acid moieties each with 10 carbon atoms (MCT-C10);

wherein the ratio of the MCT-C8 to the MCT-C10 is from 10:90 to 90:10 (mol/mol), and

wherein the combined amount of MCT-C 8 and MCT-C 10 is at least 50 mol % of the MCTs in the composition, and

wherein the composition provides increased ketones and/or fatty acids as compared to a composition comprising MCTs comprising three fatty acids moieties each with a mix of C8 and C10 moieties attached and having the same C8/C10 ratio and molar amounts.

2. The method according to claim 1 wherein the ratio of MCT-C8 to MCT-C10 is 20:80 to 85:15 (mol/mol).

3. The method according to claim 1 wherein the combined amount of MCT-C8 and MCT-C10 is at least 90 mol % of the MCTs in the composition.

4. A method of treating an individual having a brain energy deficiency condition or disease, the method comprising administering a composition comprising medium-chain triglycerides (MCTs) to the individual, wherein the MCTs comprise:

a MCT comprising three fatty acid moieties each with 8 carbon atoms (MCT-C8); and

a MCT comprising three fatty acid moieties each with 10 carbon atoms (MCT-C10); and

wherein the ratio of the MCT-C8 to the MCT-C10 is from 50:50 to 67:33 (mol/mol), and

wherein the composition provides increased ketones and/or fatty acids as compared to a composition comprising MCTs comprising three fatty acids moieties each with a mix of C8 and C10 moieties attached and having the same C8/C10 ratio and molar amounts.

5. The method according to claim 1 , wherein the three fatty acid moieties each with 8 carbon atoms are octanoic acid moieties, and/or the three fatty acid moieties each with 10 carbon atoms are decanoic acid moieties.

6. The method according to claim 1 , wherein the composition further comprises one or more agents that promote or sustain neurologic health or enhance cognitive function, wherein the one or more agents are selected from the group consisting of vitamins, choline, phosphatidylserine, alpha-lipoic acid, CoQ10, acetyl-L-carnitine, herbal extracts, omega-3 or omega-6 polyunsaturated fatty acids, aliphatic ester, fish oil extracts, and mixtures thereof.

7. The method according to claim 4 , wherein the three fatty acid moieties each with 8 carbon atoms are octanoic acid moieties, and/or the three fatty acid moieties each with 10 carbon atoms are decanoic acid moieties.

8. The method according to claim 4 , wherein the composition further comprises one or more agents that promote or sustain neurologic health or enhance cognitive function, wherein the one or more agents are selected from the group consisting of vitamins, choline, phosphatidylserine, alpha-lipoic acid, CoQ10, acetyl-L-carnitine, herbal extracts, omega-3 or omega-6 polyunsaturated fatty acids, aliphatic ester, fish oil extracts, and mixtures thereof.

9. The method according to claim 1 , wherein the ratio of the MCT-C8 to the MCT-C10 is 58:42 to 62:38 (mol/mol).

10. The method according to claim 1 , wherein the condition or disease is selected from the group consisting of a brain energy deficiency, a neurological condition, migraine, memory disorder, age-related memory disorder, brain injury, stroke, amyloid lateral sclerosis, multiple sclerosis, cognitive impairment, cognitive impairment post-intensive care, age-induced cognition impairment, Alzheimer's disease, Parkinson's disease, Huntingdon's disease, an inherited metabolic disorder, bipolar disorder, schizophrenia, epilepsy and combinations thereof.

11. The method according to claim 4 , wherein the condition or disease is selected from the group consisting of a brain energy deficiency, a neurological condition, migraine, memory disorder, age-related memory disorder, brain injury, stroke, amyloid lateral sclerosis, multiple sclerosis, cognitive impairment, cognitive impairment post-intensive care, age-induced cognition impairment, Alzheimer's disease, Parkinson's disease, Huntingdon's disease, an inherited metabolic disorder, bipolar disorder, schizophrenia, epilepsy and combinations thereof.

12. The method according to claim 10 , wherein the inherited metabolic disorder is selected from the group consisting of glucose transporter type 1 deficiency syndrome, pyruvate dehydrogenase complex deficiency, and combinations thereof.

13. The method according to claim 11 , wherein the inherited metabolic disorder is selected from the group consisting of glucose transporter type 1 deficiency syndrome, pyruvate dehydrogenase complex deficiency, and combinations thereof.

Assignments (2)
MERGER Recorded Nov 27, 2023
From: NESTEC S.A.
To: SOCIÉTÉ DES PRODUITS NESTLÉ S.A.
Reel/Frame 065666/0160 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 27, 2023
From: CUENOUD, BERNARD; MASOODI, MOJGAN
To: NESTEC S.A.
Reel/Frame 065676/0539 →
Priority Claims (1)
EP 15197934 · Dec 4, 2015 · regional
Continuity (3)
Continuation 17158328 · Jan 26, 2021
Division 15780492
Related Publication 20240082199A1 · Mar 14, 2024
References Cited (43)
US 9447016B2 · Boulos et al. · 2016 [cited by applicant]
US 9763971B2 · Groenendijk et al. · 2017 [cited by applicant]
US 10548866B2 · Williams et al. · 2020 [cited by applicant]
US 11000496B2 · Cuenoud · 2021 [cited by examiner]
US 11857527B2 · Cuenoud · 2024 [cited by examiner]
US 20010006959A1 · Palzkill et al. · 2001 [cited by applicant]
US 20020006959A1 · Henderson · 2002 [cited by applicant]
US 20070179197A1 · Henderson · 2007 [cited by applicant]
US 20150164840A1 · O'Donnell et al. · 2015 [cited by applicant]
US 20160038552A1 · Bredesen et al. · 2016 [cited by applicant]
CN 101405054A · 2009 [cited by applicant]
EP 2351491A · 2011 [cited by applicant]
EP 2484358A1 · 2012 [cited by applicant]
JP 2013543882A · 2013 [cited by applicant]
JP 2014534225A · 2014 [cited by applicant]
JP 5702292B2 · 2015 [cited by applicant]
JP 2015522256A · 2015 [cited by applicant]
JP 2016514673A · 2016 [cited by applicant]
WO 0182928A1 · 2001 [cited by applicant]
WO 2010052847A1 · 2010 [cited by applicant]
WO 20150052847A · 2010 [cited by applicant]
WO 2013186570A1 · 2013 [cited by applicant]
Rebello et al., “Pilot Feasibility and Safety Study Examining the Effect of Medium Chain Triglyceride Supplementation in Subjects with Mild Cognitive Impairment: A Randomized Controlled Trial”, BBA Clinical, vol. 3, Jan… [cited by applicant]
Odle et al., “Utilization of Medium-Chain Triglycerides by Neonatal Piglets: Chain Length of Even- and Odd-Carbon Fatty Acids and Apparent Digestion/Absorption and Hepatic Metabolism”, The Journal of Nutrition, vol. 121… [cited by applicant]
European Office Action for Appl No. 16 809 686.5-1112 dated Apr. 28, 2023. [cited by applicant]
Galante et al., “Medium-Chain Triglycerides”, Handbook of Functional Lipids, 2005, pp. 177-183. [cited by applicant]
Brazil Office Action for Appl No. BR112018009288-6 dated Jun. 5, 2023. [cited by applicant]
Veggiotti et al., Dietary Treatments and New Therapeutic Perspective in GLUT1 Deficiency Syndrome, Current Treatment Options in Neurology vol. 16, Article No. 291 (2014). [cited by applicant]
Hughes et al., The ketogenic diet component decanoic acid increases mitochondrial citrate synthase and complex I activity in neuronal cells, J Neurochem, May 2014;129(3):426-33. [cited by applicant]
Sato, “Plasma ketone levels in neonatal calves fed medium chain triglycerides in milk”, Journal of Veterinary Medical Science—Nihon Juigaku Zasshi, Japanese Society of Veterinary Science, Tokyo, Jp, vol. 56, No. 4, Aug.… [cited by applicant]
Tetrick et al., Blood D-(-)-3-hydroxybutyrate concentrations after oral administration of trioctanoin, trinonanoin, or tridecanoin to newborn rhesus monkeys ( [cited by applicant]
Henderson et al, “Study of the ketogenic agent AC-1202 in mild to moderate Alzheimer's disease: a randomized, double-blind, placebo-controlled, multicenter trial”, Nutrition & Metabolism, Biomed Central. London, GB, vol… [cited by applicant]
Japanese Office Action for Patent Appl. 2018-525699 dated Oct. 12, 2021. [cited by applicant]
Tetrick et al. “Blood D-(-)-3-Hydroxybutyrate Concentrations after Oral Administration of Trioctanoin, Trinonanoin, or Tridecanoin to Newborn Rhesus Monkeys ( [cited by applicant]
Chang et al., “Seizure Control by Decanoic Acid through Direct AMPA Receptor Inhibition”, Brain, vol. 139(Pt 2), 2016, pp. 431-443. [cited by applicant]
Hughes et al., The Ketogenic Diet Component Decanoic Acid increases Mitochondrial Citrate Synthase and Complex I Activity in Neuronal Cells, Journal of Neurochemistry, vol. 129, 2014, 426-433. [cited by applicant]
Malapaka et al., “Identification and Mechanism of 10-Carbon Fatty Acid as Modulating Ligand of Peroxisome Proliferator-Activated Receptors”, Journal of Biological Chemistry, vol. 287, Issue No. 1, Jan. 2, 2012, pp. 183-… [cited by applicant]
Wilde, “MCT Oil vs Brain Octane Oil”, Retrieved from https://blog.livehelfi.com/en/mct-oil-vs-brain-octane-oil, Jun. 8, 2015, pp. 1-7. [cited by applicant]
Japan Patent Office Communication for Application No. P2018-525699, Dispatch No. 241166, Dispatch Date Jun. 23, 2020, 8 pages. [cited by applicant]
China Patent Office Communication for Application No. 201680067187.4, dated Jun. 3, 2020, 10 pages. [cited by applicant]
Nishi et al. (Changes in subcellular distribution of n-octanoyl or n-decanoyl ghrelin in ghrelin-producing cells. Front. Endocrinol., Jul. 9, 2013. [cited by applicant]
Gahete et al. (U Role of ghrelin system in neuroprotection and cognitive functions: Implications in Alzheimer's disease Peptides vol. 32, Issue 11, Nov. 2011, pp. 2225-2228. [cited by applicant]
Communication for Application No. 16809686.5 dated May 31, 2022. [cited by applicant]