394735-17-2

Usage

Uses

Used in Chemical Research:
Ethyl 2-amino-3-cyclobutylpropanoate is utilized as a research compound for studying its chemical properties and potential applications in various fields. Its unique structure and functional groups make it an interesting subject for scientific investigation.
Used in Industrial Applications:
Ethyl 2-amino-3-cyclobutylpropanoate is employed in industrial processes, where its specific chemical characteristics may be harnessed for the development of new materials or the improvement of existing ones. The exact nature of these applications may vary depending on the industry and the specific requirements of the process.

InChI:InChI=1/C9H17NO2/c1-2-12-9(11)8(10)6-7-4-3-5-7/h7-8H,2-6,10H2,1H3

Upstream product

• 17247-58-4 (Bromomethyl)cyclobutane 
• 69555-14-2 ethyl N-diphenylmethylene glycine 
• 1025799-39-6 2-(benzhydrylidene-amino)-3-cyclobutyl-propionic acid ethyl ester 

Downstream Products

• 1606172-09-1 benzyl 4-chloro-1-cyclobutyl-3-oxobutan-2-yl carbamate 
• 1606172-10-4 benzyl 4,4-dichloro-1-cyclobutyl-3-oxobutan-2-yl carbamate 
• 1606172-08-0 ethyl 2-(benzyloxycarbonylamino)-3-cyclobutyl propanoate 
• 565456-74-8 C₉H₁₇NO₂*ClH 
• 565456-75-9 2-(tert-butoxycarbonylamino)-3-cyclobutylpropanoic acid 
• 816430-02-1 ethyl 2-(tert-butoxycarbonylamino)-3-cyclobutylpropanoate 
• 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 
• 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 
• 1036931-36-8 3-amino-4-cyclobutyl-2-hydroxybutanamide hydrochloride 
• 394735-22-9 tert-butyl 4-amino-1-cyclobutyl-3-hydroxy-4-oxobutan-2-ylcarbamate 
• 394730-60-0 boceprevir 
• 394735-18-3 tert-butyl 3-cyclobutyl-1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate 
• 394735-20-7 (2-cyano-1-cyclobutylmethyl-2-hydroxyethyl)carbamic acid tert-butyl ester 
• 394735-19-4 (2-cyclobutyl-1-formylethyl)carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

A New and convenient synthesis of the boceprevir P1 fragment, β-aminoα-hydroxy amide

A new and convenient synthesis of the P1 fragment of HCV inhibitor, boceprevir is described. This approach efficiently provides P1 fragment of boceprevir using simple and easy handling reagents suitable for scale up. This synthetic route involves the conversion of ester intermediate into novel intermediate, α-chloro ketone via chloroacetate Claisen condensation, followed by further simple conversions to β-amino-α-hydroxy amide, P1 fragment of boceprevir in high yield.

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

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.

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

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, or inhibiting cathepsin activity in a subject using the same, in which the mean volume of distribution/bioavailability (Vd/F) of the compound as measured in the plasma of the subject is greater than about 1000 L.

Administration of HCV protease inhibitors in combination with food to improve bioavailability

Methods of treating, preventing or ameliorating one or more symptoms of hepatitis C in a subject comprising the step of administering at least one HCV protease inhibitor in combination with food are provided. Also provided are methods of increasing bioavailability of an HCV protease inhibitor and methods of increasing serum levels of an HCV protease inhibitor in a subject. All methods comprise adminstering at least one HCV protease inhibitor in combination with food, the at least one HCV protease inhibitor selected from the group consisting of compounds of Formulae I-XXVI, described herein. Administration of compounds of the present invention in combination with food provides improved bioavailability and increased peak serum levels of the compounds as compared to administration without food.

NOVEL KETOAMIDES WITH CYCLIC P4'S AS INHIBITORS OF NS3 SERINE PROTEASE OF HEPATITIS C VIRUS

The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.

3,4-(cyclopentyl)-fused proline compounds as inhibitors of hepatitis C virus NS3 serine protease

The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.

NOVEL COMPOUNDS AS INHIBITORS OF HEPATITIS C VIRUS NS3 SERINE PROTEASE

The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.

NOVEL COMPOUNDS AS INHIBITORS OF HEPATITIS C VIRUS NS3 SERINE PROTEASE

The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.