CA3046363C - 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 Download PDF

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CA3046363C
CA3046363C CA3046363A CA3046363A CA3046363C CA 3046363 C CA3046363 C CA 3046363C CA 3046363 A CA3046363 A CA 3046363A CA 3046363 A CA3046363 A CA 3046363A CA 3046363 C CA3046363 C CA 3046363C
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acetamidopropanamide
dinaca
bis
naca
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CA3046363A1 (en
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G. Michael Wall
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Nacuity Pharmaceuticals Inc
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    • 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
    • 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
    • A61K9/0012—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
    • 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
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    • 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
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
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    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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    • 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
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    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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    • C07B2200/07—Optical isomers

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  • Health & Medical Sciences (AREA)
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  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hospice & Palliative Care (AREA)
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  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CA3046363A 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 Active CA3046363C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA3131442A 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

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
PCT/US2018/059446 WO2019094383A1 (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 Child Applications (1)

Application Number Title Priority Date Filing Date
CA3131442A Division 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

Publications (2)

Publication Number Publication Date
CA3046363A1 CA3046363A1 (en) 2019-05-16
CA3046363C true CA3046363C (en) 2023-06-20

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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
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

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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

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US (2) US20190135741A1 (https=)
EP (1) EP3534890A4 (https=)
JP (1) JP2021502323A (https=)
KR (2) KR20220016304A (https=)
CN (1) CN111201017A (https=)
AU (3) AU2018365900B2 (https=)
CA (2) CA3046363C (https=)
RU (1) RU2019126848A (https=)
WO (1) WO2019094383A1 (https=)

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JP2021502323A (ja) 2021-01-28
EP3534890A4 (en) 2019-11-27
KR20220016304A (ko) 2022-02-08
AU2022275499B9 (en) 2026-04-23
US20190135741A1 (en) 2019-05-09
CN111201017A (zh) 2020-05-26
CA3046363A1 (en) 2019-05-16
WO2019094383A1 (en) 2019-05-16
RU2019126848A (ru) 2021-02-26
CA3131442A1 (en) 2019-05-16
AU2020227015B2 (en) 2022-09-29
US11753370B2 (en) 2023-09-12
EP3534890A1 (en) 2019-09-11
AU2018365900A1 (en) 2019-06-20
AU2025200018A1 (en) 2025-01-23
AU2018365900B2 (en) 2020-06-18
KR20200084343A (ko) 2020-07-10
KR102357471B1 (ko) 2022-02-08
AU2022275499A1 (en) 2023-01-05
US20200385342A1 (en) 2020-12-10
AU2022275499B2 (en) 2024-10-17

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