AU2018365900B2 - 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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AU2018365900B2
AU2018365900B2 AU2018365900A AU2018365900A AU2018365900B2 AU 2018365900 B2 AU2018365900 B2 AU 2018365900B2 AU 2018365900 A AU2018365900 A AU 2018365900A AU 2018365900 A AU2018365900 A AU 2018365900A AU 2018365900 B2 AU2018365900 B2 AU 2018365900B2
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mol
dinaca
naca
acetamidopropanamide
disulfanediyl bis
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AU2018365900A1 (en
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G. Michael Wall
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Nacuity Pharmaceuticals Inc
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AU2018365900A 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 AU2018365900B2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU2020227015A AU2020227015B2 (en) 2017-11-09 2020-09-01 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
AU2022275499A AU2022275499B9 (en) 2017-11-09 2022-11-25 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
AU2025200018A AU2025200018B2 (en) 2017-11-09 2025-01-02 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

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AU2018365900A1 AU2018365900A1 (en) 2019-06-20
AU2018365900B2 true AU2018365900B2 (en) 2020-06-18

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AU2018365900A Active AU2018365900B2 (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
AU2020227015A Active AU2020227015B2 (en) 2017-11-09 2020-09-01 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
AU2022275499A Active AU2022275499B9 (en) 2017-11-09 2022-11-25 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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AU2020227015A Active AU2020227015B2 (en) 2017-11-09 2020-09-01 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
AU2022275499A Active AU2022275499B9 (en) 2017-11-09 2022-11-25 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=)
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Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR112017009584A2 (pt) 2014-11-07 2017-12-26 Nacuity Pharmaceuticals Inc tratamento de retinite pigmentosa com n-acetilcisteína amida
US11548851B2 (en) 2017-09-20 2023-01-10 Nacuity Pharmaceuticals, Inc. Method for preparation of n-acetyl cysteine amide and derivatives thereof
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
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
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)
US12458608B2 (en) 2019-01-11 2025-11-04 Nacuity Pharmaceuticals, Inc. N-Acetylcysteine Amide (NACA) and (2R,2R′)-3,3′ disulfanediyl BIS(2-acetamidopropanamide) (DINACA) for the prevention and treatment of radiation dermatitis and skin lightening, skin whitening and skin improvement
US20220409526A1 (en) * 2019-11-08 2022-12-29 Retina Foundation Of The Southwest Compounds and implants for treating ocular disorders
US20230068456A1 (en) * 2020-01-16 2023-03-02 The United States Of America, As Represented By The Secretary, Department Of Health And Human Servic Real-time monitoring of in vivo free radical scavengers through hyperpolarized n-acetyl cysteine isotopes
CA3167959A1 (en) * 2020-01-24 2021-07-29 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
EP4469044B1 (en) 2022-01-26 2026-04-08 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
WO2026015780A1 (en) * 2024-07-12 2026-01-15 Nacuity Pharmaceuticals, Inc. Method for preparation of n-acetyl cysteine amide, derivatives and tablets thereof

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006116353A2 (en) * 2005-04-21 2006-11-02 Goldstein Glenn N-acetylcysteine amide (nac amide) for the treatment of diseases and conditions associated with oxidative stress
WO2017161318A1 (en) * 2016-03-17 2017-09-21 Thiogenesis Therapeutics, Inc. Compositions for controlled release of cysteamine and systemic treatment of cysteamine sensitive disorders
WO2019060623A1 (en) * 2017-09-20 2019-03-28 Nacuity Pharmaceuticals, Inc. PROCESS FOR THE SYNTHESIS OF N-ACETYLCYSTEINE AMIDE AND ITS DERIVATIVES

Family Cites Families (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3340147A (en) 1965-06-28 1967-09-05 Mead Johnson & Co Amides of n-acylated cysteines
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
US5874468A (en) 1996-12-26 1999-02-23 Yissum Brain targeted low molecular weight hydrophobic antioxidant compounds
AU2002345699A1 (en) 2001-06-13 2002-12-23 Webb-Waring Institute For Biomedical Research A 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.
AU2003247144B2 (en) 2002-08-02 2007-11-29 Mor Research Applications Ltd. 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
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
CA2741954A1 (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
JP2016506391A (ja) 2012-12-06 2016-03-03 ステルス ペプチドズ インターナショナル インコーポレイテッド ペプチド治療薬およびその使用方法
WO2014100361A1 (en) 2012-12-19 2014-06-26 The Johns Hopkins University Protection from oxidative damage by gene transfer by glutamate cysteine ligase and glutathione synthase
EP3122342B1 (en) 2014-03-28 2020-09-23 NaCuity Pharmaceuticals, Inc. Method for the preparation of n-acetyl cysteine amide
BR112017009584A2 (pt) * 2014-11-07 2017-12-26 Nacuity Pharmaceuticals Inc tratamento de retinite pigmentosa com n-acetilcisteína amida
US11268964B2 (en) 2014-11-11 2022-03-08 The Johns Hopkins University Biomarkers useful in the treatment of subjects having diseases of the eye
CA3076392A1 (en) 2017-09-20 2019-03-28 Thiogenesis Therapeutics, Inc. Methods for the treatment of cysteamine sensitive disorders
US20200253867A1 (en) 2017-09-22 2020-08-13 University Of Florida Research Foundation Devices and methods for reducing cystine crystals in vivo
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
US20200281944A1 (en) 2017-11-17 2020-09-10 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
US12599577B2 (en) 2018-11-16 2026-04-14 University of Pittsburgh—of the Commonwealth System of Higher Education Thermoresponsive gel eye drop for ocular delivery of cysteamine
US12458608B2 (en) 2019-01-11 2025-11-04 Nacuity Pharmaceuticals, Inc. N-Acetylcysteine Amide (NACA) and (2R,2R′)-3,3′ disulfanediyl BIS(2-acetamidopropanamide) (DINACA) for the prevention and treatment of radiation dermatitis and skin lightening, skin whitening and skin 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)
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

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006116353A2 (en) * 2005-04-21 2006-11-02 Goldstein Glenn N-acetylcysteine amide (nac amide) for the treatment of diseases and conditions associated with oxidative stress
WO2017161318A1 (en) * 2016-03-17 2017-09-21 Thiogenesis Therapeutics, Inc. Compositions for controlled release of cysteamine and systemic treatment of cysteamine sensitive disorders
WO2019060623A1 (en) * 2017-09-20 2019-03-28 Nacuity Pharmaceuticals, Inc. PROCESS FOR THE SYNTHESIS OF N-ACETYLCYSTEINE AMIDE AND ITS DERIVATIVES

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