JP2021502323A5 - - Google Patents
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- Publication number
- JP2021502323A5 JP2021502323A5 JP2019535295A JP2019535295A JP2021502323A5 JP 2021502323 A5 JP2021502323 A5 JP 2021502323A5 JP 2019535295 A JP2019535295 A JP 2019535295A JP 2019535295 A JP2019535295 A JP 2019535295A JP 2021502323 A5 JP2021502323 A5 JP 2021502323A5
- Authority
- JP
- Japan
- Prior art keywords
- mol
- disulfandylbis
- acetamide
- propanamide
- pharmaceutical composition
- 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
Links
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 27
- 239000008194 pharmaceutical composition Substances 0.000 claims 19
- 229910052805 deuterium Inorganic materials 0.000 claims 15
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 10
- 201000010099 disease Diseases 0.000 claims 9
- 238000000034 method Methods 0.000 claims 9
- UJCHIZDEQZMODR-BYPYZUCNSA-N (2r)-2-acetamido-3-sulfanylpropanamide Chemical compound CC(=O)N[C@@H](CS)C(N)=O UJCHIZDEQZMODR-BYPYZUCNSA-N 0.000 claims 8
- 239000003814 drug Substances 0.000 claims 8
- 229940124597 therapeutic agent Drugs 0.000 claims 8
- DVOVBGJJSFSOPZ-UHFFFAOYSA-N 2-acetamidopropanamide Chemical compound NC(=O)C(C)NC(C)=O DVOVBGJJSFSOPZ-UHFFFAOYSA-N 0.000 claims 5
- YVDBIXASASLJPM-BYPYZUCNSA-N (2r)-n-acetyl-2-amino-3-sulfanylpropanamide Chemical class CC(=O)NC(=O)[C@@H](N)CS YVDBIXASASLJPM-BYPYZUCNSA-N 0.000 claims 3
- 239000000654 additive Substances 0.000 claims 3
- 239000002671 adjuvant Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- PNROREDTZJCOHF-UHFFFAOYSA-N 2-(3,5-dichlorophenoxy)acetonitrile Chemical compound ClC1=CC(Cl)=CC(OCC#N)=C1 PNROREDTZJCOHF-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 206010003591 Ataxia Diseases 0.000 claims 2
- 208000002177 Cataract Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 208000034656 Contusions Diseases 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- 208000012661 Dyskinesia Diseases 0.000 claims 2
- 241000713772 Human immunodeficiency virus 1 Species 0.000 claims 2
- 208000021642 Muscular disease Diseases 0.000 claims 2
- 201000009623 Myopathy Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000007014 Retinitis pigmentosa Diseases 0.000 claims 2
- 229960004308 acetylcysteine Drugs 0.000 claims 2
- 230000000996 additive effect Effects 0.000 claims 2
- 230000001147 anti-toxic effect Effects 0.000 claims 2
- 230000006907 apoptotic process Effects 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 230000009519 contusion Effects 0.000 claims 2
- 230000007850 degeneration Effects 0.000 claims 2
- 230000003111 delayed effect Effects 0.000 claims 2
- 208000030533 eye disease Diseases 0.000 claims 2
- 208000017169 kidney disease Diseases 0.000 claims 2
- 210000004072 lung Anatomy 0.000 claims 2
- 208000012268 mitochondrial disease Diseases 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 230000002107 myocardial effect Effects 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 230000004792 oxidative damage Effects 0.000 claims 2
- 230000036542 oxidative stress Effects 0.000 claims 2
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 2
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 claims 1
- 235000019393 L-cystine Nutrition 0.000 claims 1
- 239000004158 L-cystine Substances 0.000 claims 1
- 238000005481 NMR spectroscopy Methods 0.000 claims 1
- 208000012641 Pigmentation disease Diseases 0.000 claims 1
- SUSMHLGLLFPYER-UHFFFAOYSA-N acetamide;propanamide Chemical compound CC(N)=O.CCC(N)=O SUSMHLGLLFPYER-UHFFFAOYSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 1
- 235000018417 cysteine Nutrition 0.000 claims 1
- 229960003067 cystine Drugs 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000008929 regeneration Effects 0.000 claims 1
- 238000011069 regeneration method Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 0 *C(N[C@@](CS)C(N)=O)=O Chemical compound *C(N[C@@](CS)C(N)=O)=O 0.000 description 1
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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2021502323A JP2021502323A (ja) | 2021-01-28 |
| JP2021502323A5 true JP2021502323A5 (https=) | 2021-12-02 |
Family
ID=66328243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019535295A Pending JP2021502323A (ja) | 2017-11-09 | 2018-11-06 | 重水素濃縮ｎ−アセチルシステインアミド（ｄ−ｎａｃａ，ｄｅｕｔｅｒｉｕｍ−ｅｎｒｉｃｈｅｄ ｎ−ａｃｅｔｙｌｃｙｓｔｅｉｎｅ ａｍｉｄｅ）及び（２ｒ，２ｒ’）−３，３’−ジスルファンジイルビス（２−アセトアミドプロパンアミド）（ｄｉｎａｃａ）を作製する、並びに酸化ストレスが関与する疾患を治療するためにｄ−ｎａｃａ及びｄｉｎａｃａを使用する方法 |
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 (3) | AU2018365900B2 (https=) |
| CA (2) | CA3046363C (https=) |
| RU (1) | RU2019126848A (https=) |
| WO (1) | WO2019094383A1 (https=) |
Families Citing this family (17)
| 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 |
Family Cites Families (33)
| 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 |
| 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 |
| 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 |
| CA3017797A1 (en) * | 2016-03-17 | 2017-09-21 | Thiogenesis Therapeutics, Inc. | Compositions for controlled release of cysteamine and systemic treatment of cysteamine sensitive disorders |
| CA3076392A1 (en) | 2017-09-20 | 2019-03-28 | Thiogenesis Therapeutics, Inc. | Methods for the treatment of cysteamine sensitive disorders |
| CN111386255B (zh) | 2017-09-20 | 2021-11-23 | 纳崔泰制药有限公司 | 用于制备n-乙酰基半胱氨酸酰胺及其衍生物的方法 |
| 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 |
-
2018
- 2018-11-05 US US16/180,984 patent/US20190135741A1/en not_active Abandoned
- 2018-11-06 AU AU2018365900A patent/AU2018365900B2/en active Active
- 2018-11-06 EP EP18876329.6A patent/EP3534890A4/en not_active Withdrawn
- 2018-11-06 CN CN201880047207.0A patent/CN111201017A/zh active Pending
- 2018-11-06 CA CA3046363A patent/CA3046363C/en active Active
- 2018-11-06 KR KR1020227002489A patent/KR20220016304A/ko not_active Ceased
- 2018-11-06 RU RU2019126848A patent/RU2019126848A/ru unknown
- 2018-11-06 CA CA3131442A patent/CA3131442A1/en active Pending
- 2018-11-06 KR KR1020207016592A patent/KR102357471B1/ko active Active
- 2018-11-06 WO PCT/US2018/059446 patent/WO2019094383A1/en not_active Ceased
- 2018-11-06 JP JP2019535295A patent/JP2021502323A/ja active Pending
-
2020
- 2020-07-14 US US16/928,927 patent/US11753370B2/en active Active
- 2020-09-01 AU AU2020227015A patent/AU2020227015B2/en active Active
-
2022
- 2022-11-25 AU AU2022275499A patent/AU2022275499B9/en active Active
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