Abstract: The present invention includes a method for the treatment of age-related macular degeneration, glaucoma, or diabetic retinopathy in a human that comprises administering to the human a therapeutically effective amount of N-acetylcysteine amide (NACA) or (2R,2R?)-3,3?-disulfanediyl bis(2-acetamidopropanamide) (diNACA) sufficient to treat or reduce the symptoms of the age-related macular degeneration, glaucoma, or diabetic retinopathy.
Abstract: The present invention includes pharmaceutical composition comprising (2R,2R?)-3,3?-disulfanediyl bis(2-acetamidopropanamide)(diNACA) or D3-N-acetyl cysteine amide, or a physiologically acceptable salt thereof, having a deuterium enrichment above the natural abundance of deuterium, and derivatives or solids thereof, and methods of using diNACA to treat eye diseases and other diseases associated with oxidative damage including, e.g., antivenom, beta-thallassemia, cataract, chronic obstructive pulmonary disease, macular degeneration, contrast-induced nephropathy, asthma, lung contusion, methamphetamine-induced oxidative stress, multiple sclerosis, Parkinson's disease, platelet apoptosis, Tardive dyskinesia, Alzheimer disease, HIV-1-associated dementia, mitochondrial diseases, myocardial myopathy, neurodegenerative diseases, pulmonary fibrosis, skin pigmentation, skin in need of rejuventation, antimicrobial infection, Friedreich's ataxia.
Abstract: The present invention includes methods for making and isolating N-acetylcysteine amide, (2R,2R?)-3,3?-disulfanediyl bis(2-acetamidopropanamide, diNACA), intermediates and derivatives thereof comprising: contacting cystine with an alcohol and a chlorinating reagent to form an organic solution containing L-cystine dimethylester dihydrochloride; combining dried or undried L-cystine dimethylester dihydrochloride with a triethylamine, an acetic anhydride, and an acetonitrile to form a di-N-acetylcystine dimethylester; mixing dried di-N-acetylcystine dimethylester with ammonium hydroxide to form a di-N-acetylcystine amide (diNACA); and separating dried di-N-acetylcystine dimethylester into N-acetylcysteine amide with dithiothreitol, triethylamine and an alcohol.
Type:
Grant
Filed:
July 2, 2021
Date of Patent:
January 10, 2023
Assignee:
NACUITY PHARMACEUTICALS, INC.
Inventors:
G. Michael Wall, Douglas G. Johnson, Anja Rubenstein, Rodney Tucker, Josh Bolger
Abstract: The present invention includes methods for making and isolating N-acetylcysteine amide, intermediates and derivatives thereof comprising: contacting cystine with an alcohol and a chlorinating reagent to form an organic solution containing L-cystine dimethylester dihydrochloride; combining dried or undried L-cystine dimethylester dihydrochloride with a triethylamine, an acetic anhydride, and an acetonitrile to form a di-N-acetylcystine dimethylester; mixing dried di-N-acetylcystine dimethylester with ammonium hydroxide to form a di-N-acetylcystine amide; and separating dried di-N-acetylcystine dimethylester into N-acetylcysteine amide with dithiothreitol, triethylamine and an alcohol.
Type:
Grant
Filed:
September 20, 2018
Date of Patent:
March 17, 2020
Assignee:
NACUITY PHARMACEUTICALS, INC.
Inventors:
G. Michael Wall, Doug Johnson, Anja Rubenstein, Rodney Tucker, Josh Bolger
Abstract: The present application discloses an efficient process for the preparation of N-acetyl-L-cysteine amide (NACA) starting with N-acetyl-L-cysteine.
Type:
Grant
Filed:
September 6, 2017
Date of Patent:
February 13, 2018
Assignee:
NACUITY PHARMACEUTICALS, INC.
Inventors:
John C. Warner, Srinavasa Cheruku, Sambaiah Thota, John W. Lee
Abstract: The present application discloses an efficient process for the preparation of N-acetyl-L-cysteine amide (NACA) starting with N-acetyl-L-cysteine.
Type:
Grant
Filed:
March 27, 2015
Date of Patent:
September 19, 2017
Assignee:
NACUITY PHARMACEUTICALS, INC
Inventors:
John C. Warner, Srinavasa Cheruku, Sambaiah Thota, John W. Lee