394735-19-4

Usage

Uses

Used in Pharmaceutical Research:
Tert-butyl (1-cyclobutyl-3-oxopropan-2-yl)carbamate is used as a building block for the preparation of various compounds with potential biological activities, contributing to the development of new drug candidates.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, tert-butyl (1-cyclobutyl-3-oxopropan-2-yl)carbamate is utilized as a precursor for synthesizing compounds with therapeutic potential, aiding in the advancement of treatments for various diseases.
Used in Enzyme Inhibition Studies:
tert-butyl (1-cyclobutyl-3-oxopropan-2-yl)carbaMate is employed as a tool for studying enzyme inhibition and the mechanisms of action, which is crucial for understanding the interactions between drugs and biological targets.
Used in Neurological Disorder Treatment:
Tert-butyl (1-cyclobutyl-3-oxopropan-2-yl)carbamate has been investigated for its potential use in the treatment of neurological disorders, highlighting its possible role in managing or alleviating symptoms associated with such conditions.
Used in Cancer Therapy:
tert-butyl (1-cyclobutyl-3-oxopropan-2-yl)carbaMate is also being explored for its potential application in cancer treatment, indicating its possible contribution to oncology research and the development of novel therapeutic strategies against cancer.

InChI:InChI=1/C12H21NO3/c1-12(2,3)16-11(15)13-10(8-14)7-9-5-4-6-9/h8-10H,4-7H2,1-3H3,(H,13,15)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 816429-99-9 SCH 503034D 
• 17247-58-4 (Bromomethyl)cyclobutane 
• 1025799-39-6 2-(benzhydrylidene-amino)-3-cyclobutyl-propionic acid ethyl ester 
• 816430-02-1 ethyl 2-(tert-butoxycarbonylamino)-3-cyclobutylpropanoate 
• 394735-17-2 ethyl 2-amino-3-cyclobutylpropanoate 
• 565456-75-9 2-(tert-butoxycarbonylamino)-3-cyclobutylpropanoic acid 
• 394735-18-3 tert-butyl 3-cyclobutyl-1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate 

Downstream Products

• 394735-20-7 (2-cyano-1-cyclobutylmethyl-2-hydroxyethyl)carbamic acid tert-butyl ester 
• 394730-60-0 boceprevir 
• 394735-22-9 tert-butyl 4-amino-1-cyclobutyl-3-hydroxy-4-oxobutan-2-ylcarbamate 
• 1036931-36-8 3-amino-4-cyclobutyl-2-hydroxybutanamide hydrochloride 
• 394735-28-5 (1R,2S,5S)-N-(4-amino-1-cyclobutyl-3-hydroxy-4-oxobutan-2-yl)-3-((S)-2-(3-(tert-butyl)ureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicylo[3.1.0]-hexane-2-carboxamide 
• 394735-25-2 {(S)-2-[(1R,2S,5S)-2-(2-Carbamoyl-1-cyclobutylmethyl-2-hydroxy-ethylcarbamoyl)-6,6-dimethyl-3-aza-bicyclo[3.1.0]hex-3-yl]-1-cyclohexyl-2-oxo-ethyl}-carbamic acid tert-butyl ester 
• 1373318-77-4 C₇⁽¹³⁾CH₁₆N₂O₂*ClH 

Relevant academic research and scientific papers

PROCESS FOR PREPARATION OF BOCEPREVIR AND INTERMEDIATES THEREOF

THE PRESENT INVENTION RELATES TO AN IMPROVED PROCESS FOR THE PREPARATION OF (1R,5S)-N-[3-AMINO-1-(CYCLOBUTYLMETHYL)-2,3-DIOXOPROPYL]-3-[2(S)-[[[(1,1-DIMETHYLETHYL)AMINO]CARBONYL] AMINO]-3,3-DIMETHYL-1-OXOBUTYL]-6,6-DIMETHYL-3-AZABICYCLO[3.1.0]HEXAN-2(S)-CARBOXAMIDE AND ITS INTERMEDIATES

Synthesis of [14C]boceprevir, [13C 3]boceprevir, and [D9]boceprevir, a hepatitis C virus protease inhibitor

Boceprevir is a hepatitis C virus (HCV) NS3 protease inhibitor for HCV treatment. [14C]Boceprevir (SCH 503034, trade name Victrelis) was synthesized from K14CN in 11 steps with an overall yield of 16.4%. [13C3]Boceprevir was synthesized in 16 steps with a 2.5% overall yield. The carbon-13 in the molecule was distributed along the peptide chain. [D9]Boceprevir was synthesized from [D9]-t- butylamine in four steps with an overall yield of 69%. Copyright 2012 John Wiley & Sons, Ltd. Boceprevir is an HCV NS3 protease inhibitor for HCV treatment. [14C]Boceprevir (SCH 503034, trade name Victrelis) was synthesized from K14CN in 11 steps with an overall yield of 16.4%. [13C3] Boceprevir was synthesized in 16 steps with a 2.5% overall yield. The carbon-13 in the molecule was distributed along the peptide chain. [D9]Boceprevir was synthesized from [D9]-t-butylamine in 4 steps with an overall yield of 69%.

PROCESS FOR THE SYNTHESIS OF 3-AMINO-3-CYCLOBUTYLMETHYL-2-HYDROXYPROPIONAMIDE OR SALTS THEREOF

A process for preparing 3-amino-3-cyclobutylmethyl-2-hydroxypropionamide of the Formula I: [Chemical formula should be inserted here as it appears in the paper abstract.] or a salt thereof involves providing a compound of the Formula VI described herein in a solution comprising predominately dimethylsulfoxide (DMSO) and converting this compound directly to the compound of the Formula VIII described herein without working up or isolating the intermediate compound of the Formula VII described herein.

INHIBITORS OF CATHEPSIN B

The present invention is directed to a method of using compounds of Formula (I) to inhibit Cathepsin B. Specifically the compounds of the present invention are useful as therapeutic agents for the treatment of tumor invasion, metastasis, Alzheimer's Disease, arthritis, inflammatory diseases such as chronic and acute pancreatitis, inflammatory airway disease, and bone and joint disorders, including osteoporosis, osteoarthritis, rheumatoid arthritis, psoriasis, and other autoimmune disorders, liver fibrosis, including liver fibrosis associated with HCV, all types of steatosis (including non-alcoholic steatohepatitis) and alcohol-associated steatohepatitis, non-alcoholic fatty liver disease, forms of pulmonary fibrosis including idiopathic pulmonary fibrosis, pathological diagnosis of interstitial pneumonia following lung biopsy, renal fibrosis, cardiac fibrosis, retinal angiogenesis and fibrosis/gliosis in the eye, schleroderma, and systemic sclerosis. The compounds of Formula (I) are also useful for treating subjects with both HCV and fibrosis in a mammal, particularly liver fibrosis, and subjects affirmatively diagnosed or at risk for both HCV and liver fibrosis.

Pharmaceutical formulations and methods of treatment using the same

Pharmaceutical formulations containing at least one compound of Formulae I-XXVI herein and at least one surfactant. Pharmaceutically acceptable carriers and excipients may also be included in the formulations. The formulations of the present invention are suited for use in single unit dosages.

Liver/plasma concentration ratio for dosing hepatitis C virus protease inhibitor

Compositions and therapeutic combinations are provided including at least one compound selected from the group consisting of compounds of Formulae I to XXVI as defined herein as well as methods of treatment, prevention or amelioration of one or more symptoms of hepatitis C, treating disorders associated with HCV virus, modulating activity of HCV protease, in which liver to plasma concentration ratio of the compound ranges from about 2:1 to about 10:1.

Controlled-release formulation

Controlled-release dosage formulations including at least one compound of Formulae I to XXVI herein and a controlled-release carrier and methods of treatment using the same are provided.

Novel inhibitors of hepatitis C NS3-NS4A serine protease derived from 2-aza-bicyclo[2.2.1]heptane-3-carboxylic acid

Prolonged hepatitis C infection is the leading cause for cirrhosis of the liver and hepatocellular carcinoma. The etiological agent HCV virus codes a single polyprotein of ～3000 amino acids that is processed with the help of a serine protease NS3A to prod

Discovery of (1R,5S)-N-[3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3- [2(S)-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6, 6-dimethyl-3-azabicyclo[3.1.0]hexan-2(S)-carboxamide (SCH 503034), a selective, potent, orally bioavailable hepatitis C virus NS3 protease inhibitor: A potential therapeutic agent for the treatment of hepatitis C infection

Hepatitis C virus (HCV) infection is the major cause of chronic liver disease, leading to cirrhosis and hepatocellular carcinoma, which affects more than 170 million people worldwide. Currently the only therapeutic regimens are subcutaneous interferon-α or polyethylene glycol (PEG)-interferon-α alone or in combination with oral ribavirin. Although combination therapy is reasonably successful with the majority of genotypes, its efficacy against the predominant genotype (genotype 1) is moderate at best, with only about 40% of the patients showing sustained virological response. Herein, the SAR leading to the discovery of 70 (SCH 503034), a novel, potent, selective, orally bioavailable NS3 protease inhibitor that has been advanced to clinical trials in human beings for the treatment of hepatitis C viral infections is described. X-ray structure of inhibitor 70 complexed with the NS3 protease and biological data are also discussed.

Methods of treating hepatitis C virus

Methods for preventing, ameliorating or treating one or more symptoms of Hepatitis C virus (HCV), modulating HCV protease activity and/or inhibiting cathepsin activity in a subject, wherein the methods comprise administering to a subject in need of such treatment a dosage formulation containing at least one compound of Formulae I-XXVI herein, wherein the dosage formulation is capable of maintaining an average Cmin plasma concentration of the compound at or above 10 ng/ml.