CA3131442A1 - Methods of making deuterium-enriched n-acetylcysteine amide (d-naca) and (2r,2r')-3,3'-disulfanediyl bis(2-acetamidopropanamide) (dinaca) and using d-naca and dinaca to treat diseases involving oxidative stress - Google Patents

Methods of making deuterium-enriched n-acetylcysteine amide (d-naca) and (2r,2r')-3,3'-disulfanediyl bis(2-acetamidopropanamide) (dinaca) and using d-naca and dinaca to treat diseases involving oxidative stress

Info

Publication number
CA3131442A1
CA3131442A1 CA3131442A CA3131442A CA3131442A1 CA 3131442 A1 CA3131442 A1 CA 3131442A1 CA 3131442 A CA3131442 A CA 3131442A CA 3131442 A CA3131442 A CA 3131442A CA 3131442 A1 CA3131442 A1 CA 3131442A1
Authority
CA
Canada
Prior art keywords
naca
mol
dinaca
acetamidopropanamide
deuterium
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.)
Pending
Application number
CA3131442A
Other languages
English (en)
French (fr)
Inventor
G. Michael Wall
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.)
Nacuity Pharmaceuticals Inc
Original Assignee
Nacuity Pharmaceuticals Inc
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
Application filed by Nacuity Pharmaceuticals Inc filed Critical Nacuity Pharmaceuticals Inc
Publication of CA3131442A1 publication Critical patent/CA3131442A1/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/40—Y being a hydrogen or a carbon atom
    • C07C323/41—Y being a hydrogen or an acyclic carbon atom
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0048—Eye, e.g. artificial tears
    • 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
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • 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
    • 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
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • 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
    • A61K9/08—Solutions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • 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
    • A61P27/12—Ophthalmic agents for cataracts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
    • C07C319/12—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by reactions not involving the formation of mercapto groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/22—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/22—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
    • C07C319/24—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides by reactions involving the formation of sulfur-to-sulfur bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/26—Separation; Purification; Stabilisation; Use of additives
    • C07C319/28—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05—Isotopically modified compounds, e.g. labelled
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Ophthalmology & Optometry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Cardiology (AREA)
  • Psychiatry (AREA)
  • Pulmonology (AREA)
  • Dermatology (AREA)
  • Biochemistry (AREA)
  • Toxicology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CA3131442A 2017-11-09 2018-11-06 Methods of making deuterium-enriched n-acetylcysteine amide (d-naca) and (2r,2r')-3,3'-disulfanediyl bis(2-acetamidopropanamide) (dinaca) and using d-naca and dinaca to treat diseases involving oxidative stress Pending CA3131442A1 (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US201762583984P 2017-11-09 2017-11-09
US62/583,984 2017-11-09
US201762587246P 2017-11-16 2017-11-16
US62/587,246 2017-11-16
US16/180,984 2018-11-05
US16/180,984 US20190135741A1 (en) 2017-11-09 2018-11-05 Methods of Making Deuterium-Enriched N-acetylcysteine Amide (D-NACA) and (2R, 2R')-3,3'-Disulfanediyl BIS(2-Acetamidopropanamide) (DINACA) and Using D-NACA and DINACA to Treat Diseases Involving Oxidative Stress
CA3046363A CA3046363C (en) 2017-11-09 2018-11-06 Methods of making deuterium-enriched n-acetylcysteine amide (d-naca) and (2r,2r')-3,3'-disulfanediyl bis(2-acetamidopropanamide) (dinaca) and using d-naca and dinaca to treat diseases involving oxidative stress

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA3046363A Division CA3046363C (en) 2017-11-09 2018-11-06 Methods of making deuterium-enriched n-acetylcysteine amide (d-naca) and (2r,2r')-3,3'-disulfanediyl bis(2-acetamidopropanamide) (dinaca) and using d-naca and dinaca to treat diseases involving oxidative stress

Publications (1)

Publication Number Publication Date
CA3131442A1 true CA3131442A1 (en) 2019-05-16

Family

ID=66328243

Family Applications (2)

Application Number Title Priority Date Filing Date
CA3131442A Pending CA3131442A1 (en) 2017-11-09 2018-11-06 Methods of making deuterium-enriched n-acetylcysteine amide (d-naca) and (2r,2r')-3,3'-disulfanediyl bis(2-acetamidopropanamide) (dinaca) and using d-naca and dinaca to treat diseases involving oxidative stress
CA3046363A Active CA3046363C (en) 2017-11-09 2018-11-06 Methods of making deuterium-enriched n-acetylcysteine amide (d-naca) and (2r,2r')-3,3'-disulfanediyl bis(2-acetamidopropanamide) (dinaca) and using d-naca and dinaca to treat diseases involving oxidative stress

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA3046363A Active CA3046363C (en) 2017-11-09 2018-11-06 Methods of making deuterium-enriched n-acetylcysteine amide (d-naca) and (2r,2r')-3,3'-disulfanediyl bis(2-acetamidopropanamide) (dinaca) and using d-naca and dinaca to treat diseases involving oxidative stress

Country Status (9)

Country Link
US (2) US20190135741A1 (https=)
EP (1) EP3534890A4 (https=)
JP (1) JP2021502323A (https=)
KR (2) KR20220016304A (https=)
CN (1) CN111201017A (https=)
AU (4) AU2018365900B2 (https=)
CA (2) CA3131442A1 (https=)
RU (1) RU2019126848A (https=)
WO (1) WO2019094383A1 (https=)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12472157B2 (en) 2014-11-07 2025-11-18 Nacuity Pharmaceuticals, Inc. Treatment of retinitis pigmentosa with n-acetylcysteine amide
US11091433B2 (en) * 2017-09-20 2021-08-17 Nacuity Pharmaceutials, Inc. Method for preparation of N-acetyl cysteine amide and derivatives thereof
US20230159448A1 (en) * 2017-09-20 2023-05-25 Nacuity Pharmaceuticals, Inc. Method for Preparation of N-Acetyl Cysteine Amide and Derivatives Thereof
US11548851B2 (en) 2017-09-20 2023-01-10 Nacuity Pharmaceuticals, Inc. Method for preparation of n-acetyl cysteine amide and derivatives thereof
US20190135741A1 (en) 2017-11-09 2019-05-09 Nacuity Pharmaceuticals, Inc. Methods of Making Deuterium-Enriched N-acetylcysteine Amide (D-NACA) and (2R, 2R')-3,3'-Disulfanediyl BIS(2-Acetamidopropanamide) (DINACA) and Using D-NACA and DINACA to Treat Diseases Involving Oxidative Stress
WO2020146660A1 (en) 2019-01-11 2020-07-16 Nacuity Pharmaceuticals, Inc. N-acetylcysteine amide (naca) and (2r,2r')-3-3'-disulfanediyl bis (2-acetamidopropanamide) (dinaca) for prevention and treatment of radiation pneumonitis and treatment of pulmonary function in cystic fibrosis
EP3908271A4 (en) 2019-01-11 2022-10-26 NaCuity Pharmaceuticals, Inc. N-ACETYLCYSTEINE AMIDE (NACA) AND (2R,2R')-3,3'-DISULFANDIYL BIS-(2-ACETAMIDOPROPANAMIDE) (DINACA) FOR THE PREVENTION AND TREATMENT OF RADIATION DERMATITIS AND SKIN LIGHTENING AND IMPROVEMENT
EP3908341A4 (en) 2019-01-11 2022-03-02 NaCuity Pharmaceuticals, Inc. TREATMENT OF AGE-RELATED MACULAR DEGENERATION, GLAUCOMA AND DIABETIC RETINOPATHY WITH N-ACETYLCYSTEINE AMIDE (NACA) OR (2R,2R')-3,3'-BIS(2-ACETAMIDOPROPANAMIDE) DISULFANEDIYL (DINACA)
EP4054553A4 (en) * 2019-11-08 2023-11-29 Retina Foundation of the Southwest JOINTS AND IMPLANTS FOR THE TREATMENT OF EYE DISEASES
WO2021146556A1 (en) * 2020-01-16 2021-07-22 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Real-time monitoring of in vivo free radical scavengers through hyperpolarized n-acetyl cysteine isotopes
AU2021209953B2 (en) * 2020-01-24 2024-08-22 Nacuity Pharmaceuticals, Inc. Prodrug for the treatment of disease and injury of oxidative stress
US20210378993A1 (en) * 2020-06-08 2021-12-09 Nacuity Pharmaceuticals, Inc. Treatment of cystinosis
US11883426B2 (en) * 2020-08-08 2024-01-30 Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Treatment for methamphetamine cardiovascular disease
US20220304955A1 (en) * 2021-03-23 2022-09-29 Nacuity Pharmaceuticals, Inc. Treatment of ferroptosis
CA3242202A1 (en) 2022-01-26 2023-08-03 Universidade De Aveiro IONIC LIQUID-BASED FORMULATIONS FOR THE PREVENTION OR TREATMENT OF NEUROLOGICAL DISEASES
WO2026015776A1 (en) * 2024-07-12 2026-01-15 Nacuity Pharmaceuticals, Inc. Method for preparation of n-acetyl cysteine amide or di- n-acetyl cysteine amide and derivatives

Family Cites Families (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3252866A (en) 1965-06-28 1966-05-24 Mead Johnson & Co 2-hydrocarbon substituted-amido mercaptopropionamides in hair waving compositions and processes
US5874468A (en) 1996-12-26 1999-02-23 Yissum Brain targeted low molecular weight hydrophobic antioxidant compounds
US6420429B1 (en) 1997-12-23 2002-07-16 Yissum Research Development Company Of The Hebrew University Of Jerusalem Brain targeted low molecular weight hydrophobic antioxidant compounds
US20030027745A1 (en) 2001-06-13 2003-02-06 Repine John E. Diagnostic and prognostic method for evaluating ocular inflammation and oxidative stress and the treatment of the same
BE1014949A3 (fr) 2001-08-14 2004-07-06 Probiox Procede de detection de stress oxydant et trousse pour sa mise en oeuvre.
US20060211628A1 (en) 2002-08-02 2006-09-21 Daphne Atlas Treatment of multiple sclerosis with brain targeted anti oxidant compounds
US8993627B2 (en) 2005-04-21 2015-03-31 Sentient Lifesciences, Inc. N-acetylcysteine amide (NAC amide) for the treatment of diseases and conditions associated with oxidative stress
US20090234011A1 (en) 2005-04-21 2009-09-17 Goldstein Glenn A N-acetylcysteine amide (nac amide) for the treatment of diseases and conditions associated with oxidative stress
JP4840804B2 (ja) 2006-01-20 2011-12-21 学校法人慶應義塾 酸化ストレスの判定方法
WO2010048716A1 (en) 2008-10-29 2010-05-06 Pacific Therapeutics Ltd. Composition and method for treating fibrosis
US20120150029A1 (en) 2008-12-19 2012-06-14 University Of Miami System and Method for Detection and Monitoring of Ocular Diseases and Disorders using Optical Coherence Tomography
WO2011044230A2 (en) 2009-10-06 2011-04-14 Goldstein Glenn A N-acetylcysteine amide (nac amide) for the treatment of diseases and conditions
EP2397125A1 (en) 2010-06-15 2011-12-21 Histocell, S.L. Antioxidant composition
US20120142550A1 (en) 2010-12-06 2012-06-07 Zehnder James L Vanin 1 as a Peripheral Blood Oxidative Stress Sensor
WO2013138744A1 (en) 2012-03-16 2013-09-19 M. Alphabet 1, Llc Compositions for the treatment of skin disorders
AU2013299785B2 (en) 2012-08-06 2017-09-07 Baylor College Of Medicine Therapeutics dispensing device and methods of making same
EP2928562A4 (en) 2012-12-06 2016-06-22 Stealth Peptides Int Inc PEPTIDE THERAPEUTIC PRODUCTS AND METHODS OF USE
US20150328337A1 (en) 2012-12-19 2015-11-19 The Johns Hopkins University Protection from oxidative damage by gene transfer by glutamate cysteine ligase and glutathione synthase
US9763902B2 (en) 2014-03-28 2017-09-19 Nacuity Pharmaceuticals, Inc Method for preparation of N-acetyl cysteine amide
US12472157B2 (en) 2014-11-07 2025-11-18 Nacuity Pharmaceuticals, Inc. Treatment of retinitis pigmentosa with n-acetylcysteine amide
WO2016077467A1 (en) 2014-11-11 2016-05-19 The Johns Hopkins University Biomarkers useful in the treatment of subjects having diseases of the eye
JP7418958B2 (ja) * 2016-03-17 2024-01-22 チオジェネシス セラピューティクス， インコーポレイテッド システアミンの制御放出のための組成物及びシステアミン感受性障害の全身治療
JP7208982B2 (ja) 2017-09-20 2023-01-19 チオジェネシス セラピューティクス， インコーポレイテッド システアミン感受性障害の治療方法
EP3684756A4 (en) * 2017-09-20 2020-10-28 NaCuity Pharmaceuticals, Inc. SYNTHESIS OF N-ACETYLCYSTEIN AMIDE AND ITS DERIVATIVES
WO2019060704A1 (en) 2017-09-22 2019-03-28 University Of Florida Research Foundation DEVICES AND METHODS FOR REDUCTION OF IN VIVO CYSTINE CRYSTALS
US20190135741A1 (en) 2017-11-09 2019-05-09 Nacuity Pharmaceuticals, Inc. Methods of Making Deuterium-Enriched N-acetylcysteine Amide (D-NACA) and (2R, 2R')-3,3'-Disulfanediyl BIS(2-Acetamidopropanamide) (DINACA) and Using D-NACA and DINACA to Treat Diseases Involving Oxidative Stress
WO2019097434A1 (en) 2017-11-17 2019-05-23 Mahmood Piraee Combinations of lanosterol or 25-hydroxycholesterol including derivatives thereof useful in the treatment of lens disorders
US20190151271A1 (en) 2017-11-21 2019-05-23 The Johns Hopkins University Compositions and methods for treatment of eye diseases
CN108618993B (zh) 2018-07-16 2021-07-27 广东格烯生物科技股份有限公司 一种美白组合物及其制备方法和应用
WO2020102810A1 (en) 2018-11-16 2020-05-22 University Of Pittsburgh - Of The Commonwealth System Of Higher Education Thermoresponsive gel eye drop for ocular delivery of cysteamine
WO2020146660A1 (en) 2019-01-11 2020-07-16 Nacuity Pharmaceuticals, Inc. N-acetylcysteine amide (naca) and (2r,2r')-3-3'-disulfanediyl bis (2-acetamidopropanamide) (dinaca) for prevention and treatment of radiation pneumonitis and treatment of pulmonary function in cystic fibrosis
EP3908341A4 (en) 2019-01-11 2022-03-02 NaCuity Pharmaceuticals, Inc. TREATMENT OF AGE-RELATED MACULAR DEGENERATION, GLAUCOMA AND DIABETIC RETINOPATHY WITH N-ACETYLCYSTEINE AMIDE (NACA) OR (2R,2R')-3,3'-BIS(2-ACETAMIDOPROPANAMIDE) DISULFANEDIYL (DINACA)
EP3908271A4 (en) 2019-01-11 2022-10-26 NaCuity Pharmaceuticals, Inc. N-ACETYLCYSTEINE AMIDE (NACA) AND (2R,2R')-3,3'-DISULFANDIYL BIS-(2-ACETAMIDOPROPANAMIDE) (DINACA) FOR THE PREVENTION AND TREATMENT OF RADIATION DERMATITIS AND SKIN LIGHTENING AND IMPROVEMENT

Also Published As

Publication number Publication date
AU2018365900A1 (en) 2019-06-20
CA3046363C (en) 2023-06-20
AU2025200018A1 (en) 2025-01-23
CA3046363A1 (en) 2019-05-16
KR102357471B1 (ko) 2022-02-08
WO2019094383A1 (en) 2019-05-16
KR20220016304A (ko) 2022-02-08
JP2021502323A (ja) 2021-01-28
US20200385342A1 (en) 2020-12-10
AU2020227015B2 (en) 2022-09-29
RU2019126848A (ru) 2021-02-26
US11753370B2 (en) 2023-09-12
AU2022275499A1 (en) 2023-01-05
AU2018365900B2 (en) 2020-06-18
EP3534890A1 (en) 2019-09-11
AU2022275499B2 (en) 2024-10-17
AU2022275499B9 (en) 2026-04-23
EP3534890A4 (en) 2019-11-27
US20190135741A1 (en) 2019-05-09
AU2020227015A1 (en) 2020-09-17
CN111201017A (zh) 2020-05-26
KR20200084343A (ko) 2020-07-10

Similar Documents

Publication Publication Date Title
AU2022275499B9 (en) Methods of making deuterium-enriched n-acetylcysteine amide (d-naca) and (2r,2r’)-3,3’-disulfanediyl bis(2-acetamidopropanamide) (dinaca) and using d-naca and dinaca to treat diseases involving oxidative stress
CN109516981B (zh) 普那布林组合物
JP2025529483A (ja) Ａｐｘ３３３０の塩及びエステルならびにその治療的使用
WO2007117544A2 (en) Carnitine conjugates of adamantanamines and neramexane derivatives as duel prodrugs for various uses
EP3426675B1 (en) Crystalline salt forms
US11434198B2 (en) Compounds and methods for the treatment of neurodegenerative diseases
JPS62198672A (ja) 新規三環式チアゼピン誘導体、その製造法および医薬組成物
CA3211395A1 (en) Compositions of essentially pure form iv of n-((r)-2,3-dihydroxypropoxy)-3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-benzamide and uses thereof
PT1043332E (pt) Dipeptídeos contendo ciclopentano-beta-aminoácidos
US7429679B2 (en) Sulphonic acid salt of sibutramine
US20240217927A1 (en) Methods of Making Deuterium-Enriched N-Acetylcysteine Amide (D-NACA) and (2R,2R)-3,3-Disulfanediyl BIS(2-Acetamidopropanamide) (DINACA) and Using D-NACA and DINACA to Treat Diseases Involving Oxidative Stress
US20230373913A1 (en) Methods of Making Deuterium-Enriched N-Acetylcysteine Amide (D-NACA) and (2R,2R)-3,3-Disulfanediyl BIS(2-Acetamidopropanamide) (DINACA) and Using D-NACA and DINACA to Treat Diseases Involving Oxidative Stress
EP4157266B1 (en) Crystalline forms of solvates of tryptophan derivatives, compositions comprising them and uses thereof
KR20190090729A (ko) 토파시티닙의 신규 염, 이의 제조방법 및 이를 포함하는 약학 조성물
HK40089977A (en) Crystalline forms of solvates of tryptophan derivatives, compositions comprising them and uses thereof
WO2021207577A1 (en) Process for producing tca cycle intermediate conjugates and polymorphs of a tca cycle intermediate conjugate
HK40086425A (zh) 秋水仙碱衍生物的制备方法及其用途
HK40006402B (en) Plinabulin compositions
HK40006402A (en) Plinabulin compositions
EP1073625A1 (en) Tilidine mesylate, processes for its preparation and pharmaceutical composition thereof

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20210921

P11 Amendment of application requested

Free format text: ST27 STATUS EVENT CODE: A-2-2-P10-P11-P100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: AMENDMENT RECEIVED - RESPONSE TO EXAMINER'S REQUISITION

Effective date: 20240829

MFA Maintenance fee for application paid

Free format text: FEE DESCRIPTION TEXT: MF (APPLICATION, 6TH ANNIV.) - SMALL

Year of fee payment: 6

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-2-2-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20241017

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-2-2-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT DETERMINED COMPLIANT

Effective date: 20241017

Free format text: ST27 STATUS EVENT CODE: A-2-2-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20241017

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: A-2-2-W10-W00-W111 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: CORRESPONDENT DETERMINED COMPLIANT

Effective date: 20250108

P11 Amendment of application requested

Free format text: ST27 STATUS EVENT CODE: A-2-2-P10-P11-P102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: AMENDMENT DETERMINED COMPLIANT

Effective date: 20250505

P13 Application amended

Free format text: ST27 STATUS EVENT CODE: A-2-2-P10-P13-X000 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: APPLICATION AMENDED

Effective date: 20250505

MFA Maintenance fee for application paid

Free format text: FEE DESCRIPTION TEXT: MF (APPLICATION, 7TH ANNIV.) - SMALL

Year of fee payment: 7

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-2-2-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20250908

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-2-2-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20250908