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WO2022040644A3 - Beta-hydroxybutyric acid compositions and methods for oral delivery of ketone bodies - Google Patents

Beta-hydroxybutyric acid compositions and methods for oral delivery of ketone bodies Download PDF

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Publication number
WO2022040644A3
WO2022040644A3 PCT/US2021/050302 US2021050302W WO2022040644A3 WO 2022040644 A3 WO2022040644 A3 WO 2022040644A3 US 2021050302 W US2021050302 W US 2021050302W WO 2022040644 A3 WO2022040644 A3 WO 2022040644A3
Authority
WO
WIPO (PCT)
Prior art keywords
beta
hydroxybutyric acid
oral delivery
gels
suspensions
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2021/050302
Other languages
French (fr)
Other versions
WO2022040644A2 (en
Inventor
Gary MILLET
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Axcess Global Sciences LLC
Original Assignee
Axcess Global Sciences LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US16/996,509 external-priority patent/US10973786B2/en
Priority claimed from US17/210,646 external-priority patent/US11806324B2/en
Priority to EP21859286.3A priority Critical patent/EP4200274A4/en
Application filed by Axcess Global Sciences LLC filed Critical Axcess Global Sciences LLC
Priority to CA3192343A priority patent/CA3192343A1/en
Priority to JP2023512075A priority patent/JP2023541360A/en
Priority to MX2023001899A priority patent/MX2023001899A/en
Priority to CN202180070607.5A priority patent/CN116940352A/en
Priority to AU2021327408A priority patent/AU2021327408A1/en
Publication of WO2022040644A2 publication Critical patent/WO2022040644A2/en
Publication of WO2022040644A3 publication Critical patent/WO2022040644A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Diabetes (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Nutrition Science (AREA)
  • Polymers & Plastics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Child & Adolescent Psychology (AREA)
  • Food Science & Technology (AREA)
  • Mycology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Cosmetics (AREA)

Abstract

Beta-hydroxybutyric acid compositions for oral delivery are substantially free of beta-hydroxybutyrate salts and are effective in rapidly raising blood ketone levels without causing acute acidosis or gastrointestinal (GI) distress when consumed in sufficiently dilute form and/or as a gel or suspension. By excluding beta-hydroxybutyrate salts (e.g., less than 1% by weight) containing alkali or alkaline earth metal ions, beta-hydroxybutyric acid solutions, gels, or suspensions can deliver exogenous ketone bodies without significantly altering electrolyte balance. Although aqueous beta-hydroxybutyric acid solutions are moderately acidic with a pH of about 3.5 to 4, when diluted with sufficient water, the water acts as a pseudo buffering agent that offsets otherwise harsh acidic effects when consumed orally. Gels and suspensions can also ameliorate acidic effects by partially encapsulating the beta-hydroxybutyric acid. Beta-hydroxybutyric acid can be enriched with the R- or the S-enantiomer, a racemic mixture, pure R-beta-hydroxybutyric acid, or pure S-beta-hydroxybutyric acid.
PCT/US2021/050302 2020-08-18 2021-09-14 Beta-hydroxybutyric acid compositions and methods for oral delivery of ketone bodies Ceased WO2022040644A2 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
AU2021327408A AU2021327408A1 (en) 2020-08-18 2021-09-14 Beta-hydroxybutyric acid compositions and methods for oral delivery of ketone bodies
CN202180070607.5A CN116940352A (en) 2021-03-24 2021-09-14 Compositions and methods for oral delivery of ketone bodies
EP21859286.3A EP4200274A4 (en) 2020-08-18 2021-09-14 BETA-HYDROXYBUTYRIC ACID COMPOSITIONS AND METHODS FOR ORAL ADMINISTRATION OF KETONE BODIES
CA3192343A CA3192343A1 (en) 2020-08-18 2021-09-14 Beta-hydroxybutyric acid compositions and methods for oral delivery of ketone bodies
JP2023512075A JP2023541360A (en) 2021-03-24 2021-09-14 Beta-hydroxybutyric acid compositions and methods for oral delivery of ketone bodies
MX2023001899A MX2023001899A (en) 2021-03-24 2021-09-14 Beta-hydroxybutyric acid compositions and methods for oral delivery of ketone bodies.

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US16/996,509 2020-08-18
US16/996,509 US10973786B2 (en) 2016-03-11 2020-08-18 R-beta-hydroxybutyrate, S-beta-hydroxybutyrate, and RS-beta-hydroxybutyrate mixed salt compositions
US17/210,646 2021-03-24
US17/210,646 US11806324B2 (en) 2018-04-18 2021-03-24 Beta-hydroxybutyric acid compositions and methods for oral delivery of ketone bodies

Publications (2)

Publication Number Publication Date
WO2022040644A2 WO2022040644A2 (en) 2022-02-24
WO2022040644A3 true WO2022040644A3 (en) 2022-04-07

Family

ID=80323202

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2021/050302 Ceased WO2022040644A2 (en) 2020-08-18 2021-09-14 Beta-hydroxybutyric acid compositions and methods for oral delivery of ketone bodies

Country Status (3)

Country Link
EP (1) EP4200274A4 (en)
AU (1) AU2021327408A1 (en)
WO (1) WO2022040644A2 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11026929B2 (en) 2016-04-19 2021-06-08 Keto Patent Group, Inc. Administration of berberine metabolites
US12496283B2 (en) 2016-04-19 2025-12-16 Axcess Global Sciences, Llc Administration of R-beta-hydroxybutyrate and related compounds in humans
US12329734B2 (en) 2017-12-19 2025-06-17 Axcess Global Sciences, Llc Use of S-beta-hydroxybutyrate compounds for induction and maintenance of flow
US12109182B2 (en) 2016-04-19 2024-10-08 Axcess Global Sciences, Llc Administration of R-beta-hydroxybutyrate and related compounds in humans
US12171735B2 (en) 2017-04-19 2024-12-24 Axcess Global Sciences, Llc Administration of butyrate, beta-hydroxybutyrate, cannabidiol, and related compounds in humans
US20230346699A1 (en) * 2022-04-28 2023-11-02 Axcess Global Sciences, Llc Administration of r-beta-hydroxybutyrate and related compounds in veterinary applications

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110287114A1 (en) * 2010-05-24 2011-11-24 Amerilab Technologies, Inc. Effervescent composition for forming a gelled composition, tablet for forming a gelled composition, and method of making a gelled composition
WO2018187324A1 (en) * 2017-04-04 2018-10-11 NNB Nutrition USA, LLC Preparation of (r)-3-hydroxybutyric acid or its salts by one-step fermentation
US20190177673A1 (en) * 2017-08-23 2019-06-13 KetoneAid Inc. Ketogenic beer and alcoholic beverage mixture containing non-racemic ethyl 3-hydroxybutyrate and/or 1,3 butanediol
WO2019204148A1 (en) * 2018-04-18 2019-10-24 Access Global Sciences, Llc Compositions and methods for keto stacking with beta-hydroxybutyrate and acetoacetate

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5030553B2 (en) * 2006-11-24 2012-09-19 有限会社ノーベル医学研究所 Pharmaceuticals for treating dry mice and / or salivary secretion disorders
US10245242B1 (en) * 2017-11-22 2019-04-02 Axcess Global Sciences, Llc Non-racemic beta-hydroxybutyrate compounds and compositions enriched with the R-enantiomer and methods of use
US11806324B2 (en) * 2018-04-18 2023-11-07 Axcess Global Sciences, Llc Beta-hydroxybutyric acid compositions and methods for oral delivery of ketone bodies
GB201616058D0 (en) * 2016-09-21 2016-11-02 Chain Biotechnology Ltd Probiotic composition
JP6804352B2 (en) * 2017-03-22 2020-12-23 大阪瓦斯株式会社 Collagenase MMP1 and 3 production inhibitors
CA3022995C (en) * 2018-06-12 2019-10-15 Ketofibe (9211-3133 Quebec Inc.) Novel ketogenic compounds, compositions, methods and use thereof
EP4114203A1 (en) * 2020-03-05 2023-01-11 VitaNav, Inc. COMPOSITION OF (D)-ß-HYDROXYBUTYRIC ACID, (D)-ß-HYDROXYVALERIC ACID, AND (D)-1,3 BUTANEDIOL AS A NUTRITIONAL SUPPLEMENT AND THERAPEUTIC AGENT
CN112262936A (en) * 2020-10-22 2021-01-26 珠海麦得发生物科技股份有限公司 A kind of beverage containing 3-hydroxybutyric acid and its preparation method and application

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110287114A1 (en) * 2010-05-24 2011-11-24 Amerilab Technologies, Inc. Effervescent composition for forming a gelled composition, tablet for forming a gelled composition, and method of making a gelled composition
WO2018187324A1 (en) * 2017-04-04 2018-10-11 NNB Nutrition USA, LLC Preparation of (r)-3-hydroxybutyric acid or its salts by one-step fermentation
US20190177673A1 (en) * 2017-08-23 2019-06-13 KetoneAid Inc. Ketogenic beer and alcoholic beverage mixture containing non-racemic ethyl 3-hydroxybutyrate and/or 1,3 butanediol
WO2019204148A1 (en) * 2018-04-18 2019-10-24 Access Global Sciences, Llc Compositions and methods for keto stacking with beta-hydroxybutyrate and acetoacetate

Also Published As

Publication number Publication date
EP4200274A2 (en) 2023-06-28
EP4200274A4 (en) 2024-10-23
AU2021327408A1 (en) 2023-04-20
WO2022040644A2 (en) 2022-02-24

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