WO2025058667A2 - Prevention and treatment of conditions using ethyl pyruvate - Google Patents
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
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- 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
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
- A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
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- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/455—Nicotinic acids, e.g. niacin; Derivatives thereof, e.g. esters, amides
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- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
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- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
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- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7084—Compounds having two nucleosides or nucleotides, e.g. nicotinamide-adenine dinucleotide, flavine-adenine dinucleotide
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
Definitions
- This present application is generally related to the prevention and treatment of conditions using ethyl pyruvate and combinations of ethyl pyruvate with one or more additional therapeutic agents.
- Metabolic intermediates such as sodium pyruvate, calcium pyruvate, and nicotinamide have therapeutic potential for certain diseases or conditions.
- these compounds have been effective at treating glaucoma in certain preclinical animal models, by reducing intraocular pressure (“IOP”) through metabolic modulation and/or providing neuroprotection.
- IOP intraocular pressure
- WO 2017/070647 Al Jeffrey M. Harder et al., Disturbed Glucose and Pyruvate Metabolism in Glaucoma with Neuroprotection by Pyruvate or Rapamycin, 117 Proc. Nat’ 1 Acad. Sci. 33619 (2020); Pete A. Williams et al., Vitamin B3 Modulates Mitochondrial Vulnerability and Prevents Glaucoma in Aged Mice, 355 Science 756 (2017).
- a method of treating or preventing a condition in a subject comprising administering to the subject a therapeutically effective amount of ethyl pyruvate, or a derivative or analog thereof, or a pharmaceutical composition thereof; wherein the condition is selected from the group consisting of an ocular disease or disorder, a neurodegenerative disease or disorder, a vascular disease or disorder, a metabolic disease or disorder, an inflammatory disease or disorder, a disease or disorder involving abnormal cell death or oxidation, a disease or disorder linked to one or more Lmxlb mutations, and a combination thereof.
- a method of reducing or preventing elevated intraocular pressure comprising administering a therapeutically effective amount of ethyl pyruvate, or a derivative or analog thereof, or a pharmaceutical composition thereof, to the subject.
- a method of reducing or preventing damage or dysfunction to a subject’s eye tissues comprising administering a therapeutically effective amount of ethyl pyruvate, or a derivative or analog thereof, or a pharmaceutical composition thereof, to the subject.
- the subject is pregnant and the ethyl pyruvate is administered during prenatal care to protect the child from developing dysfunction/ disease. Treatment can continue for the child after birth either by direct administration to the child or through the mother via breast milk or a combination thereof.
- a method of reducing or preventing damage or dysfunction to tissues involved in ocular fluid drainage in a subject comprising administering a therapeutically effective amount of ethyl pyruvate, or a derivative or analog thereof, or a pharmaceutical composition thereof, to the subject.
- a method of reducing or preventing developmental malformations, disease dependent malformations or dysfunctions in a subject’s eye is described, the method comprising administering a therapeutically effective amount of ethyl pyruvate, or a derivative or analog thereof, or a pharmaceutical composition thereof, to the subject.
- the method further comprises administering one or more additional therapeutic agents, or one or more pharmaceutical compositions thereof, to the subject.
- the one or more additional therapeutic agents are selected from the group consisting of an antioxidant agent, an antiinflammatory agent, an agent that modulates metabolism, an agent that modulates the integrated stress response, an agent that modulates the unfolded protein response, an agent that modulates forms of autophagy, an agent that modulates the expression or activity of genes controlling or mediating antioxidant or other protective responses, an anti-cell death agent, a senolytic agent, an agent that modulates the mitochondria or mitophagy, an antiaging agent, an agent that modulates intraocular pressure, a resilience-boosting agent, an antifibrotic agent, an agent that prevents epithelial mesenchymal transition or endothelial mesenchymal transition, a neuroprotective agent, a gene therapy agent, and a combination thereof.
- an antioxidant agent an antiinflammatory agent
- an agent that modulates metabolism an agent that modulates the integrated stress response
- an agent that modulates the unfolded protein response an agent that modulates forms of autophagy
- any one of the embodiments disclosed herein may be properly combined with any other embodiment disclosed herein.
- the combination of any one of the embodiments disclosed herein with any other embodiments disclosed herein is expressly contemplated.
- the selection of one or more embodiments for one substituent group can be properly combined with the selection of one or more particular embodiments for any other substituent group.
- Such combination can be made in any one or more embodiments of the application described herein or any formula described herein.
- Figure 1 shows ethyl pyruvate protected against high IOP, according to one or more embodiments.
- Figure 2 shows ethyl pyruvate alone or in combination with nicotinamide lessened IOP elevation, according to one or more embodiments.
- Figure 3 shows ethyl pyruvate in combination with other therapeutic agents afforded increased disease protection, according to one or more embodiments.
- Figure 4 shows ethyl pyruvate rescued ocular developmental abnormalities, according to one or more embodiments.
- Figure 5 shows ethyl pyruvate prevented increased anterior chamber depth and reduced anterior chamber deepening, according to one or more embodiments.
- Figure 6 shows ethyl pyruvate in combination with additional therapeutic agents afforded increased disease protection, according to one or more embodiments.
- Figure 7 shows sodium pyruvate did not impact IOP elevation or developmental abnormalities.
- Figure 8 shows ethyl pyruvate alone, nicotinamide alone as well as the combination of ethyl pyruvate and nicotinamide protects from glaucomatous optic nerve damage, according to one or more embodiments.
- Figures 9A and 9C are 3D fluorescent images of tissue volumes for trabecular meshwork and Schlemm’s canal, respectively.
- Figures 9B and 9D are box plots for the corresponding data showing that the combination of ethyl pyruvate and nicotinamide rescues developmental anomalies of the ocular drainage tissues, according to one or more embodiments.
- Figure 10 shows that treatment of mice harboring an early onset Lmxlb developmental glaucoma model with ethyl pyruvate (2000 mg/kg/day) and NAM (550 mg/kg/day) profoundly prevented cell death.
- the present application in accordance with one aspect, is directed to a method of treating or preventing a condition in a subject, wherein the method includes administering to the subject a therapeutically effective amount of ethyl pyruvate, or a derivative or analog thereof, or a pharmaceutical composition thereof.
- the condition is selected from the group consisting of an ocular disease or disorder, a neurodegenerative disease or disorder, a vascular disease or disorder, a metabolic disease or disorder, an inflammatory disease or disorder, a disease or disorder involving abnormal cell death or oxidation, a disease or disorder linked to one or more Lmxlb mutations, and a combination thereof.
- Glaucoma refers to an eye disease that results in damage to the retina and optic nerve and visual dysfunction or vision loss. Glaucoma occurs more commonly among older people. Vision loss from glaucoma is permanent and is irreversible. Glaucoma is typically associated with elevated intraocular pressure but glaucoma also includes normal tension glaucoma (NTG), which is a form of primary open angle glaucoma (POAG). Glaucoma may also be the result of traumatic neural injury.
- NTG normal tension glaucoma
- POAG primary open angle glaucoma
- normal intraocular pressure in humans refers to a human subject having an IOP value of 10 mmHg to 21 mmHg. Some individuals, however, may develop optic nerve damage despite a normal IOP (known as normal-tension glaucoma).
- high IOP intraocular pressure
- high IOP high intraocular pressure in humans refers to a human subject having an IOP value greater than 21 mmHg (or 2.8 kPa). High IOP is known to be a risk factor for glaucoma. Some individuals, however, may have high IOP for years and never develop glaucoma or optic nerve damage.
- prevention of high intraocular pressure includes avoiding the development of high intraocular pressure, reducing the risk or chance of eventually developing high intraocular pressure, delaying the onset or progression of high intraocular pressure, or reducing the severity of neuronal damage/extent of neuronal death/loss among a population of neurons should high intraocular pressure eventually develop.
- treatment is an approach for obtaining beneficial or desired results, including clinical results.
- beneficial or desired clinical results may include, but are not limited to, alleviation or amelioration of one or more symptoms or conditions, diminution of extent of disease, a stabilized (ie., not worsening) state of disease, preventing spread of disease, delay or slowing of disease progression, amelioration or palliation of the disease state and remission (whether partial or total), whether detectable or undetectable.
- the condition is an ocular disease or disorder.
- the ocular disease or disorder comprises elevated intraocular pressure, one or more changes to the structure or function of one or more ocular tissues, abnormal cell death, or a combination thereof.
- the one or more changes to the structure or function of one or more ocular tissues comprise malformation or dysfunction of ocular drainage structures, one or more developmental anomalies, neural or non-neural cell degeneration, dysfunction, or death, or a combination thereof.
- the one or more changes to the structure or function of one or more ocular tissues result from environmental exposure, disease, aging, metabolic anomaly, mitochondrial anomaly, genetic variant or epigenetic differences, or a combination thereof.
- the one or more developmental anomalies comprise changes to anterior chamber depth, pupil abnormalities, iridocorneal adhesions, trabecular meshwork, Schl emm’s canal, cornea or a combination thereof.
- the neural or non-neural cell degeneration or dysfunction comprises neurodegeneration and/or neural dysfunction in the subject’s retinal ganglion cells.
- malformation or malfunction of the ocular drainage tissues includes Schl emm’s canal, trabecular meshwork, or a combination thereof.
- the ocular disease or disorder is a neurodegenerative disease or disorder. In some embodiments, the ocular disease or disorder is glaucoma.
- the condition is a neurodegenerative disease not directly affecting the ocular system.
- the condition comprises late onset neurodegeneration.
- the condition is Alzheimer’s disease or Parkinson’s disease.
- the disease or disorder linked to one or more Lmxlb mutations is a disease or disorder of the brain or kidney.
- the one or more Lmxlb variants lead to cell stress, developmental anomalies, cell death, and/or elevated IOP, which in turn may lead to a further disease or condition.
- Lmxlb mutations cause developmental defects, organ disease (e.g., kidney disease), ocular disease (e.g., glaucoma), and/or neurodegenerative disease (e.g., Alzheimer’s disease and Parkinson’s disease).
- Lmxlb-associated diseases or conditions present with different ages of onset.
- the condition is age-related macular degeneration. In some embodiments, the condition is traumatic glaucoma.
- the condition comprises a retinal pigment epithelium.
- the method further includes administering one or more additional therapeutic agents, or one or more pharmaceutical compositions thereof, to the subject.
- the one or more additional therapeutic agents are selected from the group consisting of an antioxidant agent, an anti-inflammatory agent, an agent that modulates metabolism, an agent that modulates the integrated stress response, an agent that modulates the unfolded protein response, an agent that modulates forms of autophagy, an agent that modulates the expression or activity of genes controlling or mediating antioxidant or other protective responses, a senolytic agent, an agent that modulates the mitochondria or mitophagy, an anti-aging agent, an agent that modulates intraocular pressure, a resilienceboosting agent, an antifibrotic agent, an agent that prevents epithelial mesenchymal transition or endothelial mesenchymal transition, a neuroprotective agent, a gene therapy agent, and a combination thereof.
- the agent modulates metabolism reprograms or boosts metabolism.
- the antioxidant agent reduces oxidative stress and boosts antioxidant control.
- the gene therapy agent results in genome editing, genome reprogramming, epigenetic editing, epigenetic reprogramming, or a combination thereof.
- the agent that prevents epithelial mesenchymal transition or endothelial mesenchymal transition is an anti-transforming growth factor-P (“TGFB”) or ligand trap molecule.
- TGFB anti-transforming growth factor-P
- the one or more additional therapeutic agents are selected from the group consisting of nicotinamide (NAM), nicotinamide mononucleotide, nicotinamide adenine dinucleotide, nicotinamide ribose, pyrroloquinoline quinine, N-acetyl cysteine, and a combination thereof.
- NAM nicotinamide
- nicotinamide mononucleotide nicotinamide adenine dinucleotide
- nicotinamide ribose pyrroloquinoline quinine
- N-acetyl cysteine N-acetyl cysteine
- agents that may be used in combination with ethyl pyruvate include, but are not limited to, saffron, berry extract or powder, antioxidants (e.g., billberry), flavonoids, anthocyanins, carotenoids, polyphenols, folate, xeoxanthine, polyamines (e.g., spermidine), Ginko biloba (glaucoma vitamin supplement (Glaucocetin), Co enzyme Q10, Vitamin A, Vitamin B12, Vitamin B50 complex, Vitamin C, Vitamin D, Vitamin E, betaine, choline, citi choline, Epigallocatechin-3 -gallate (EGCG and its derivatives or analogs), compounds that increase activity of Sirts including Sirt3, lutein, xeozanthine, molecules that induce genes that protect from oxidative damage, dimethylfumarate and other forms of fumarate, and antifibrotic agents (such as anti-TGFBs, curcumin, blueberry, sily
- antioxidants e
- the additional agent may be a metabolism supporting molecule, such as, but not limited to: ketones, ketone bodies- metabolites used in energy metabolism (e.g., hydroxubutarate, Beta-hydroxybutarate (BHB) and its salts, e.g., acetoacetate.
- the methods disclosed herein may also be combined with diets shown to help in glaucoma such as, but not limited to, ketogenic diet and low carb diet.
- the methods disclosed herein may also be combined with glucagon like peptide (GLP-1) agonists including, but not limited to, Exenatide, Liraglutide and Semaglutide. Taurine and creatine can also be used in combination with the methods disclosed herein.
- GLP-1 glucagon like peptide
- Additional examples useful herein also include molecules and gene therapies that increase or induce NMNAT2 (nicotinamide mononucleotide adenosyl transferase) or other NMNATs, molecules or gene therapies that induce or otherwise increase signaling of the TEK/Angiopoietin system, any molecules that increase NAD, or insulin and its derivatives, agents or gene therapies that increase Ca 2+ /calmodulin-dependent protein kinase II (CAMKII) activity/signaling, treatments that increase CNTF, BNDF or other beneficial growth factors.
- This also includes without limitation encapsulated cells in implants that release the therapeutic agent(s) including these growth factors and/or proteins, peptides, antibodies, agonists, antiinflammatory molecules, and metabolites.
- the method disclosed herein could also be combined with laser and/or other glaucoma surgeries aimed at lowering IOP, with various implanted tubes, shunts and stents that lower IOP or long-term drug formulations and delivery devices.
- Biotin, hemp seeds/powder, long chain polyunsaturated fatty acids (PUFAS)(e.g., omega 3 fatty acids), spirulina and leafy green powder or extracts can also be combined with ethyl pyruvate treatment as disclosed herein. Derivatives and analogs of the compounds disclosed herein can also be used.
- PFAS long chain polyunsaturated fatty acids
- the one or more additional therapeutic agents are administered together in a pharmaceutical composition with ethyl pyruvate. In other embodiments, the one or more additional therapeutic agents are administered separately from ethyl pyruvate. In still other embodiments, the subject is already being treated with the one or more additional therapeutic agents when the ethyl pyruvate is administered; or the subject is administered the one or more additional therapeutic agents after being administered the ethyl pyruvate.
- the ethyl pyruvate is administered in an amount sufficient to treat or prevent the condition in the subject. In some embodiments, the ethyl pyruvate is administered in an amount sufficient to prevent or reduce elevated intraocular pressure, prevent or reduce one or more changes to the structure or function of one or more ocular tissues, prevent or reduce abnormal cell death, or a combination thereof. In some embodiments, the ethyl pyruvate is administered in an amount sufficient to prevent or reduce malformation or dysfunction of ocular drainage structures, prevent or reduce one or more developmental anomalies, prevent or reduce neural or non-neural cell degeneration, dysfunction, or death, or a combination thereof.
- the ethyl pyruvate is administered in an amount sufficient to prevent or reduce one or more changes in the subject resulting from environmental exposure, disease, aging, metabolic anomaly, mitochondrial anomaly, genetic mutation, or a combination thereof. In some embodiments, the ethyl pyruvate is administered in an amount sufficient to prevent or reduce one or more developmental anomalies in the subject, such as, but not limited to, changes to anterior chamber depth, pupil abnormalities, iridocorneal adhesions, trabecular meshwork, Schl emm’s canal, cornea or a combination thereof.
- the ethyl pyruvate is administered in an amount sufficient to prevent or reduce cell degeneration or dysfunction in the subject, such as, but not limited to, neurodegeneration and/or neural dysfunction in the subject’s retinal ganglion cells. In some embodiments, the ethyl pyruvate is administered in an amount sufficient to prevent or reduce changes or dysfunction to the subject’s ocular drainage structures, such as, but not limited to, Schl emm’s canal, trabecular meshwork, or a combination thereof.
- the ethyl pyruvate is administered in an amount sufficient to prevent or reduce a neurodegenerative disease or disorder in the subject, such as, but not limited to, glaucoma or a late onset neurodegeneration (e.g., Alzheimer’s disease or Parkinson’s disease).
- the ethyl pyruvate is administered in an amount sufficient to prevent or reduce disease or disorder linked to one or more Lmxlb mutations, such as, but not limited to, a disease or disorder of the eye, brain, or kidney.
- the ethyl pyruvate is administered in an amount sufficient to prevent or reduce a condition of aging in the subject, such as, but not limited to, age-related macular degeneration.
- the ethyl pyruvate is administered in an amount sufficient to prevent or reduce a retinal pigment epithelium in the subject.
- the amount of ethyl pyruvate sufficient to produce the effects described in the preceding paragraph will be the same when administered alone or in combination with one or more additional therapeutic agents. In some embodiments, the amount of ethyl pyruvate sufficient to produce the effects described in the preceding paragraph will be less when administered with one or more additional therapeutic agents than when administered alone.
- the subject is a mammal. In some embodiments, the subject is a mouse or rat. In some embodiments, the subject is of canine or equine origin. In some embodiments, the subject is a non-human primate. In some embodiments, the subject is a human.
- the subject has the condition. In other embodiments, the subject is at risk, including, but not limited to, genetic risk, for developing the condition. In other embodiments, the subject has the condition and is at risk, including, but not limited to, genetic risk, for developing more serious variants or complications of the condition. In some embodiments, the subject has the condition and is at risk, including, but not limited to, genetic risk, for developing additional conditions, which additional conditions may or may not be related to the original condition.
- a method of reducing or preventing elevated intraocular pressure comprising administering a therapeutically effective amount of ethyl pyruvate, or a pharmaceutical composition thereof, to the subject.
- a method of reducing or preventing damage or dysfunction to a subject’s eye tissues comprising administering a therapeutically effective amount of ethyl pyruvate, or a pharmaceutical composition thereof, to the subject.
- a method of reducing or preventing damage or dysfunction to tissues involved in ocular fluid drainage in a subject comprising administering a therapeutically effective amount of ethyl pyruvate, or a pharmaceutical composition thereof, to the subject.
- a method of reducing or preventing developmental malformations or dysfunctions in a subject’s eye comprising administering a therapeutically effective amount of ethyl pyruvate, or a pharmaceutical composition thereof, to the subject.
- the method further comprises administering one or more additional therapeutic agents, or one or more pharmaceutical compositions thereof, to the subject.
- the ethyl pyruvate is administered in an amount sufficient to reduce intraocular pressure in the subject or to prevent the subject’s intraocular pressure from increasing.
- the subject has elevated intraocular pressure and the administration of ethyl pyruvate reduces the intraocular pressure or prevents the intraocular pressure from further increasing.
- the subject does not have elevated intraocular pressure, and the administration of ethyl pyruvate prevents the subject’s intraocular pressure from increasing.
- the ethyl pyruvate is administered in an amount sufficient to prevent or reduce neurodegeneration and/or neural dysfunction in the subject’s neural and non-neural cells.
- the subject has the neurodegeneration and/or neural dysfunction and the administration of ethyl pyruvate reduces the neurodegeneration and/or neural dysfunction or prevents further neurodegeneration and/or neural dysfunction.
- the subject does not have the neurodegeneration and/or neural dysfunction and the administration of ethyl pyruvate prevents the neurodegeneration and/or neural dysfunction from developing.
- the effects of ethyl pyruvate for preventing or reducing neurodegeneration and/or neural dysfunction are related to its activity for modulation of intraocular pressure. In other embodiments, the effects of ethyl pyruvate for preventing or reducing neurodegeneration and/or neural dysfunction are independent of its activity for modulating intraocular pressure.
- the ethyl pyruvate is administered in an amount sufficient to prevent or reduce changes in the subject’s ocular drainage tissues.
- the subject has the changes in ocular drainage tissues and the administration of ethyl pyruvate reduces the changes or prevents further changes.
- the subject does not have the changes and the administration of ethyl pyruvate prevents the changes from developing.
- the effects of ethyl pyruvate for preventing or reducing changes in the subject’s ocular drainage tissues are related to its activity for modulation of intraocular pressure.
- the effects of ethyl pyruvate for preventing or reducing changes in the subject’s ocular drainage tissues are independent of its activity for modulating intraocular pressure.
- the subject has the dysfunctions and/or developmental changes and the administration of ethyl pyruvate reduces the developmental changes or prevents further developmental changes. In other embodiments, the subject does not have the dysfunctions and/or developmental changes and the administration of ethyl pyruvate prevents the developmental changes from developing.
- the effects of ethyl pyruvate for preventing or reducing one or more dysfunctions and/or developmental changes in the subject’s eye are related to its activity for modulation of intraocular pressure. In other embodiments, the effects of ethyl pyruvate for preventing or reducing one or more dysfunctions and/or developmental changes in the subject’s eye are independent of its activity for modulating intraocular pressure.
- the disease or disorder of the eye is a non- neurodegenerative disease.
- the disease or disorder of the eye is an age-related disease or disorder.
- the disease of disorder of the eye is age-related macular degeneration.
- age-related macular degeneration includes neurodegeneration.
- age-related macular degeneration includes a retinal pigment epithelium (“RPE”).
- age-related macular degeneration includes a vascular disease or condition.
- the prevention or reduction of the subject’s elevated intraocular pressure prevents or treats a disease or disorder of the eye.
- the disease or disorder of the eye comprises non-neural cell degeneration, dysfunction, and/or death.
- the disease or disorder of the eye comprises neural cell degeneration, dysfunction, and/or death.
- the disease or disorder of the eye is a neurodegenerative disease.
- the disease or disorder of the eye is glaucoma.
- the disease or disorder of the eye is a non- neurodegenerative disease.
- the disease or disorder of the eye is an age-related disease or disorder.
- the disease of disorder of the eye is age-related macular degeneration.
- the disease or disorder of the eye is glaucoma or age-related macular degeneration.
- the prevention or reduction of the subject’s elevated intraocular pressure prevents or treats neurodegeneration and/or neural dysfunction in the subject’s retinal ganglion cells, changes in the subject’s ocular drainage tissues, and/or developmental changes in the subject’s eye.
- Ethyl pyruvate has the chemical structure
- the present disclosure also contemplates derivatives or analogs of ethyl pyruvate.
- Derivatives or analogs of ethyl pyruvate may include, but are not limited to, different ester chain lengths or substitutions, different substitutions on the acyl carbon, halogenated and isotopically-derived analogs, and isomers and combinations thereof; and pharmaceutically acceptable salts thereof.
- Derivatives or analogs of ethyl pyruvate may also include, but are not limited to, conjugates with imaging agents, macromolecules, biomacromolecules, targeting agents, and isomers and combinations thereof; and pharmaceutically acceptable salts thereof.
- Use of ethyl pyruvate or its derivatives and analogs in a pharmaceutical composition with one or more pharmaceutically acceptable excipients, and/or with one or more drug delivery or targeting vehicles, are also contemplated.
- the derivative or analog of ethyl pyruvate is selected from the group consisting of methyl pyruvate, propyl pyruvate, butyl pyruvate, pentyl pyruvate, hexyl pyruvate, octyl pyruvate, isobutyl pyruvate, isopentyl pyruvate, isoheptyl pyrvate, isooctyl pyruvate, cyclopentyl pyruvate, cyclopentylmethyl pyruvate, cyclohexyl pyruvate, cyclohexylmethyl pyruvate, butenyl pyruvate, hexenyl pyruvate, isobutenyl pyruvate, isohexenyl pyruvate, butinyl pyruvate, hexinyl
- elevated IOP is a risk factor for a disease or disorder. In some embodiments, elevated IOP is a risk factor for a disease or disorder of the eye. In some embodiments, elevated IOP is a risk factor for a non-neurodegenerative or a neurodegenerative disease or disorder of the eye. In some embodiments, elevated IOP is a risk factor for glaucoma. In some embodiments, elevated IOP is a risk factor for dysfunctions, malformations, and/or death of one or more cells, tissues, or structures in the eye.
- ethyl pyruvate protects ocular tissues from stresses due to environment, development, disease, and/or age (including, but not limited to, mitochondrial and metabolic abnormalities, Lmxlb mutation, or mutations in other genes impacting metabolism, development, and/or glaucoma.
- ethyl pyruvate protects ocular drainage structures from changes and cell death due to developmental conditions, genetic and epigenetic effects, and/or environmental and/or exposure effects. In some embodiments, ethyl pyruvate protects ocular drainage structures from malformation. In some embodiments, ethyl pyruvate protects from developmental anomalies of the eye. In some embodiments, ethyl pyruvate protects from developmental malformations that may have functional, cosmetic, and/or psychological impacts on the subject.
- ethyl pyruvate protects from dysfunction and death of cells.
- these cells may be nerve cells and/or neurons.
- ethyl pyruvate protects mice with a Lmxlb mutation.
- Lmxlb mutations cause developmental defects, kidney disease, and/or glaucoma, with different ages of onset in mice versus humans. Therefore, in some embodiments, ethyl pyruvate treatment may protect from various Lmxlb-induced diseases.
- the inventors surprisingly found that ethyl pyruvate lessens IOP elevation in mouse models comprising a genetic model resulting in cell stress, developmental anomalies, cell death, and/or high IOP. In some embodiments, one or more of these factors may lead to glaucoma.
- the mouse model is a Lmxlb mouse model. This is unexpected at least because sodium pyruvate had no effect on IOP in age-onset mouse glaucoma models, or in the early-onset Lmxlb developmental glaucoma model. For example, treatment of Lmxlb mice with about 500 mg/kg/day of sodium pyruvate had no effect on IOP at 2, 3, and 4-months post-treatment. This is also unexpected at least because calcium pyruvate had no effect on IOP in humans in prior clinical studies.
- dosages of about 2000 mg/kg/day ethyl pyruvate lessen the severity of ocular developmental abnormalities and IOP elevation in mice.
- combination of ethyl pyruvate and other agents capable of modulating metabolism affords a higher degree of protection against the severity of ocular developmental abnormalities and IOP elevation in mice compared to ethyl pyruvate alone.
- combination of ethyl pyruvate and a metabolic boosting agent affords greater protection against developmental pupil abnormalities.
- the inventors surprisingly found that ethyl pyruvate is more protective than sodium pyruvate. In some embodiments, the inventors surprisingly found that ethyl pyruvate is a superior neuroprotectant than sodium pyruvate.
- the superior properties of ethyl pyruvate as compared to existing treatments may stem from ethyl pyruvate’s enhanced stability, cell penetration properties, antioxidant properties, anti-inflammatory properties, anti-apoptotic properties, and/or metabolic (bioenergetic) properties (e.g., relative to sodium pyruvate).
- ethyl pyruvate enhanced stability, cell penetration properties, antioxidant properties, anti-inflammatory properties, anti-apoptotic properties, and/or metabolic (bioenergetic) properties (e.g., relative to sodium pyruvate).
- the enhanced antiinflammatory and anti-apoptotic properties of ethyl pyruvate may result from its molecular structure, stability, and/or enhanced ability to permeate into cells.
- This application also provides a pharmaceutical composition
- a pharmaceutical composition comprising at least one of the compounds as described herein or a pharmaceutically-acceptable salt thereof, and a pharmaceutically-acceptable carrier.
- pharmaceutically-acceptable carrier means a pharmaceutically-acceptable material, composition or vehicle, such as a liquid or solid filler, diluent, excipient, solvent or encapsulating material, involved in carrying or transporting the subject pharmaceutical agent from one organ, or portion of the body, to another organ, or portion of the body.
- a pharmaceutically-acceptable material such as a liquid or solid filler, diluent, excipient, solvent or encapsulating material, involved in carrying or transporting the subject pharmaceutical agent from one organ, or portion of the body, to another organ, or portion of the body.
- Each carrier must be “acceptable” in the sense of being compatible with the other ingredients of the formulation and pharmaceutically acceptable for the patient.
- materials which can serve as pharmaceutically-acceptable carriers include: sugars, such as lactose, glucose and sucrose; starches, such as corn starch and potato starch; cellulose, and its derivatives, such as sodium carboxymethyl cellulose, ethyl cellulose and cellulose acetate; powdered tragacanth; malt; gelatin; talc; excipients, such as cocoa butter and suppository waxes; oils, such as peanut oil, cottonseed oil, safflower oil, sesame oil, olive oil, corn oil and soybean oil; glycols, such as butylene glycol; polyols, such as glycerin, sorbitol, mannitol and polyethylene glycol; esters, such as ethyl oleate and ethyl laurate; agar; buffering agents, such as magnesium hydroxide and aluminum hydroxide; alginic acid; pyrogen-free water; isotonic saline; Ring
- compositions of the present pharmaceutical agents may be provided in the form of pharmaceutically-acceptable salts.
- pharmaceutically-acceptable salt refers to the relatively non-toxic, inorganic and organic acid addition salts of compounds of the present application.
- wetting agents, emulsifiers and lubricants such as sodium lauryl sulfate, magnesium stearate, and polyethylene oxide-polybutylene oxide copolymer as well as coloring agents, release agents, coating agents, sweetening, flavoring and perfuming agents, preservatives and antioxidants can also be present in the compositions.
- this amount will range from about 1% to about 99% of active ingredient, preferably from about 5% to about 70%, most preferably from about 10% to about 30%.
- Methods of preparing these formulations or compositions include the step of bringing into association a compound of the present invention with the carrier and, optionally, one or more accessory ingredients.
- the formulations are prepared by uniformly and intimately bringing into association a compound of the present invention with liquid carriers, or finely divided solid carriers, or both, and then, if necessary, shaping the product.
- the active ingredient is mixed with one or more pharmaceutically-acceptable carriers, such as sodium citrate or dicalcium phosphate, and/or any of the following: fillers or extenders, such as starches, lactose, sucrose, glucose, mannitol, and/or silicic acid; binders, such as, for example, carboxymethylcellulose, alginates, gelatin, polyvinyl pyrrolidone, sucrose and/or acacia; humectants, such as glycerol; disintegrating agents, such as agar-agar, calcium carbonate, potato or tapioca starch, alginic acid, certain silicates, sodium carbonate, and sodium starch glycolate; solution retarding agents, such as paraffin; absorption accelerators, such as quaternary ammonium compounds; wetting agents, such as, for example, cetylene glycol, glycerol
- a tablet may be made by compression or molding, optionally with one or more accessory ingredients.
- Compressed tablets may be prepared using binder (for example, gelatin or hydroxybutylmethyl cellulose), lubricant, inert diluent, preservative, disintegrant (for example, sodium starch glycolate or cross-linked sodium carboxymethyl cellulose), surface-active or dispersing agent.
- Molded tablets may be, made by molding in a suitable machine a mixture of the powdered compound moistened with an inert liquid diluent.
- the tablets, and other solid dosage forms of the pharmaceutical compositions of the present invention may optionally be scored or prepared with coatings and shells, such as enteric coatings and other coatings well known in the pharmaceutical-formulating art. They may also be formulated so as to provide slow or controlled release of the active ingredient therein.
- Liquid dosage forms for oral administration of the compounds disclosed herein include pharmaceutically acceptable emulsions, microemulsions, solutions, suspensions, syrups and elixirs.
- the liquid dosage forms may contain inert diluents commonly used in the art, such as, for example, water or other solvents, solubilizing agents and emulsifiers, such as ethyl alcohol, isobutyl alcohol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, butylene glycol, 1,3-butylene glycol, oils (in particular, cottonseed, groundnut, corn, germ, olive, castor and sesame oils), glycerol, tetrahydrofuryl alcohol, polyethylene glycols and fatty acid esters of sorbitan, and mixtures thereof.
- cyclodextrins e.g., hydroxybutyl-P-cyclo
- the oral compositions can also include adjuvants such as wetting agents, emulsifying and suspending agents, sweetening, flavoring, coloring, perfuming and preservative agents.
- adjuvants such as wetting agents, emulsifying and suspending agents, sweetening, flavoring, coloring, perfuming and preservative agents.
- Suspensions in addition to the active compounds, may contain suspending agents as, for example, ethoxylated isostearyl alcohols, polyoxyethylene sorbitol and sorbitan esters, microcrystalline cellulose, aluminum metahydroxide, bentonite, agar-agar and tragacanth, and mixtures thereof.
- suspending agents as, for example, ethoxylated isostearyl alcohols, polyoxyethylene sorbitol and sorbitan esters, microcrystalline cellulose, aluminum metahydroxide, bentonite, agar-agar and tragacanth, and mixtures thereof.
- Dosage forms for the topical or transdermal administration of a compound of this invention include powders, sprays, ointments, pastes, creams, lotions, gels, solutions, patches and inhalants.
- the active compound may be mixed under sterile conditions with a pharmaceutically acceptable carrier, and with any preservatives or buffers which may be required.
- Powders and sprays can contain, in addition to a compound of this invention, excipients such as lactose, talc, silicic acid, aluminum hydroxide, calcium silicates and polyamide powder, or mixtures of these substances.
- excipients such as lactose, talc, silicic acid, aluminum hydroxide, calcium silicates and polyamide powder, or mixtures of these substances.
- Transdermal patches have the added advantage of providing controlled delivery of a compound of the present invention to the body.
- dosage forms can be made by dissolving or dispersing the pharmaceutical agents in the medium.
- Absorption enhancers can also be used to increase the flux of the pharmaceutical agents of the invention across the skin. The rate of such flux can be controlled, by either providing a rate controlling membrane or dispersing the compound in a polymer matrix or gel.
- Ophthalmic formulations eye ointments, powders, solutions and the like, are also contemplated as being within the scope of this disclosure.
- Implants or injectables may also be used to introduce the agent into the eye. Any of the excipients disclosed herein suitable for use in these applications can be incorporated into the pharmaceutical formulations.
- the compounds of the present invention are administered as pharmaceuticals, to humans and animals, they can be given per se or as a pharmaceutical composition containing, for example, 0.1% to 99.5% (more preferably, 0.5% to 90%) of active ingredient in combination with a pharmaceutically acceptable carrier.
- dosages of from about 100 - 2000, more particularly from about 250-1000 mg/kg/day ethyl pyruvate lessen the severity of ocular developmental abnormalities and IOP elevation in mice.
- Human equivalent doses can be calculated as described in the literature.
- combination of ethyl pyruvate and other agents capable of modulating metabolism affords a higher degree of protection against the severity of ocular developmental abnormalities and IOP elevation in mice compared to ethyl pyruvate alone.
- combination of ethyl pyruvate and NAM affords greater protection against developmental pupil abnormalities.
- a dose of up to about 8000mg/kg/day in mice could be used. Again, the human equivalent dose can be calculated accordingly.
- a combination of ethyl pyruvate and NAM are particularly useful.
- the dosage of NAM is from about 100 - 2500, more particularly from about 500-1000 mg/kg/day.
- Human equivalent doses can be calculated as described in the literature. Nicotinamide riboside could also be used at similar or lower doses.
- Ethyl pyruvate showed a protective effect in mice with a Lmxlb mutation, thereby demonstrating that ethyl pyruvate treatment can protect from various Lmxlb-induced diseases.
- Lmxlb is implicated in neurodegenerative conditions like glaucoma and Parkinson’s disease.
- Genetic models having a Lmxlb mutation may result in cell stress, developmental anomalies, cell death, and/or elevated IOP, which can lead to further diseases or conditions.
- ethyl pyruvate lessened IOP and rescued ocular developmental abnormalities in mouse models of glaucoma, across multiple dosages and with or without coadministration of another therapeutic agent.
- Ethyl pyruvate was sourced from Sigma-Aldrich. Ethyl pyruvate has been shown to be safe and well-tolerated across multiple mammalian species, including humans, mice, rats, and horses. See, e.g., Clinical Trial Identifier NCT00107666 (human cardiac trial, dosing ethyl pyruvate at 7.5 g (90 mg/kg) intravenously, every six hours for two days); Xiujing Sun et al., Ethyl Pyruvate Supplemented in Drinking Water Ameliorates Experimental Nonalcoholic Steatohepatitis, 137 Biomedical Pharmacotherapy 111392 (2021); Leilei Mao et al., Ethyl Pyruvate Improves White Matter Remodeling in Rats After Traumatic Brain Injury, 27 CNS Neuroscience & Therapeutics 113 (2021); C.
- Clinical Trial Identifier NCT00107666 human cardiac trial, dosing ethyl
- a dose of about 2000 mg/kg ethyl pyruvate in mice is equivalent to about 9.8 g/day for a 60 kg human.
- FIG. 3 shows that treatment of mice harboring an early onset ILmxlb developmental glaucoma model with ethyl pyruvate (2000 mg/kg/day), nicotinamide (550 mg/kg/day), and A-acetyl-L-cysteine (200 mg/kg/day) increased disease protection. Treatment began at P2 and IOP was measured at 5 weeks of age.
- Ethyl pyruvate s ability to treat or prevent IOP elevation ocular developmental abnormalities was surprising at least because such effects have not been observed with sodium pyruvate treatments.
- Figure 7 shows that treatment of mice harboring a glaucoma model with sodium pyruvate (500 mg/kg/day) had no effect on IOP elevation after two months. IOP was also measured at three and four months, and no changes were observed compared to untreated. Additionally, sodium pyruvate-treated mice showed no change in the severity of anterior eye developmental abnormalities.
- Figure 8 shows that treatment of mice harboring an early onset Lmxlb developmental glaucoma model with ethyl pyruvate (2000 mg/kg/day) resulted in lessening of glaucomatous optic nerve damage (neurodegeneration) in mice aged to six months old. This shows an extension of the protection time period to a point where the majority of the untreated mice had severe glaucoma.
- Figure 8 further shows that treatment of mice harboring an early onset Lmxlb developmental glaucoma model with nicotinamide (550 mg/kg/day) was also protective from glaucomatous optic nerve damage.
- Figure 8 further shows that treatment of mice harboring an early onset Lmxlb developmental glaucoma model with ethyl pyruvate (2000 mg/kg/day) and nicotinamide (550 mg/kg/day) was also protective from glaucomatous optic nerve damage. As shown in the plotted data, the combined treatment provided the most protection against glaucomatous optic nerve damage.
- Figure 9 shows that treatment of mice harboring an early onset Lmxlb developmental glaucoma model with ethyl pyruvate (2000 mg/kg/day) and NAM (500 mg/kg/day) administered to the mother rescued development anomalies of the ocular drainage tissues in the pup, which would also receive active from the mother’s milk after birth for the firest two to three weeks of life.
- This was a morphogenesis correction study (drainage tissue morphogenesis is complete by postnatal day 21 in mice). The mice were analyzed at 3 to 4 weeks of age. Treatment was started at birth in drinking water (prenatal administration to mother also works).
- FIG 10 shows that treatment of mice harboring an early onset Lmxlb developmental glaucoma model with ethyl pyruvate (2000 mg/kg/day) and NAM (550 mg/kg/day) profoundly prevented cell death.
- the subject mice treated from postnatal day 2 and assessed at postnatal day P10 an age where cell death is readily detected in this glaucoma model.
- Cell death was quantified as TUNEL+ cells in the TM per section. This was extrapolated to the entire TM volumes.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202480029517.5A CN121079080A (en) | 2023-03-20 | 2024-03-20 | Ethyl pyruvate for the prevention and treatment of disease |
| AU2024339814A AU2024339814A1 (en) | 2023-03-20 | 2024-03-20 | Prevention and treatment of conditions using ethyl pyruvate |
| EP24866002.9A EP4683625A2 (en) | 2023-03-20 | 2024-03-20 | Prevention and treatment of conditions using ethyl pyruvate |
| US19/334,248 US20260076935A1 (en) | 2023-03-20 | 2025-09-19 | Prevention and treatment of conditions using ethyl pyruvate |
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| US202363453419P | 2023-03-20 | 2023-03-20 | |
| US63/453,419 | 2023-03-20 |
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| US19/334,248 Continuation US20260076935A1 (en) | 2023-03-20 | 2025-09-19 | Prevention and treatment of conditions using ethyl pyruvate |
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| WO2025058667A3 WO2025058667A3 (en) | 2025-05-01 |
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| EP (1) | EP4683625A2 (en) |
| CN (1) | CN121079080A (en) |
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| US5346887A (en) * | 1987-10-06 | 1994-09-13 | Abbott Laboratories | Glaucoma treatment |
| EP3069612A3 (en) * | 2009-06-15 | 2016-10-19 | Encore Health, LLC | Dithiol compounds, derivatives, and uses therefor |
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- 2024-03-20 AU AU2024339814A patent/AU2024339814A1/en active Pending
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| US20260076935A1 (en) | 2026-03-19 |
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| AU2024339814A1 (en) | 2025-11-06 |
| EP4683625A2 (en) | 2026-01-28 |
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