860035-10-5

Basic information

• Product Name: Propanoic acid, 2-Methyl-, 1-[[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]oxy]ethyl ester
• Synonyms: Propanoic acid, 2-Methyl-, 1-[[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]oxy]ethyl ester;1-((2,5-dioxopyrrolidin-1-yloxy)carbonyloxy)ethyl isobutyrate
• CAS NO: 860035-10-5
• Molecular Formula: C₁₁H₁₅NO₇
• Molecular Weight: 273.2393
• EINECS: -0
• Mol File: 860035-10-5.mol

Chemical Properties

• Boiling Point: 347.6±44.0 °C(Predicted)
• Appearance: /
• Density: 1.32±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Propanoic acid, 2-Methyl-, 1-[[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]oxy]ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Propanoic acid, 2-Methyl-, 1-[[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]oxy]ethyl ester(860035-10-5)
• EPA Substance Registry System: Propanoic acid, 2-Methyl-, 1-[[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]oxy]ethyl ester(860035-10-5)

Safety Data

• Hazardous Substances Data: 860035-10-5(Hazardous Substances Data)

Usage

Uses

Used in Flavoring and Fragrance Industry:
Propanoic acid, 2-Methyl-, 1-[[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]oxy]ethyl ester is used as a flavoring agent for its fruity odor, adding a pleasant aroma to various food and beverage products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Propanoic acid, 2-Methyl-, 1-[[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]oxy]ethyl ester is used as a solvent in the manufacturing process, aiding in the dissolution and stability of active pharmaceutical ingredients.
Used in Food Product Industry:
Propanoic acid, 2-Methyl-, 1-[[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]oxy]ethyl ester is used as a solvent in the production of food products, enhancing the solubility and stability of various ingredients.
Used in Plasticizer Production:
This chemical compound is utilized in the production of plasticizers, which are additives used to increase the flexibility and workability of plastics.
Used as an Intermediate in Organic Synthesis:
Propanoic acid, 2-Methyl-, 1-[[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]oxy]ethyl ester serves as an intermediate in the synthesis of other organic compounds, contributing to the formation of various chemical products.

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 860035-07-0 O-(1-isobutanoyloxyethyl) S-methyl thiocarbonate 
• 937-14-4 3-chloro-benzenecarboperoxoic acid 
• 860035-08-1 O-(1-isobutanoyloxyethyl) S-tert-butyl thiocarbonate 
• 1207383-11-6 1-((4-(methylsulfonyl)phenoxy)carbonyloxy)ethyl isobutyrate 

Downstream Products

• 478296-72-9 gabapentin enacarbil 
• 1057258-24-8 3-{[1-isobutanoyloxyethoxy]carbonylamino}propyl phosphonous acid 
• 918448-02-9 trans-4-{[1-(2-methylpropanoyloxy)ethoxycarbonyl]-aminomethyl}-cyclohexanecarboxylic acid 
• 1206514-65-9 2-[(1-acetyl-4-{hydroxy-[1-(1-isobutyryloxy-ethoxycarbonylamino)ethyl]phosphinoylmethyl}piperidine-4-carbonyl)amino]-ropionic acid 
• 1206514-64-8 2-[(1-{hydroxy-[1-(1-isobutyryloxy-ethoxycarbonylamino)ethyl]phosphinoylmethyl}cyclopentanecarbonyl)amino]propionic acid 

Relevant articles and documents

Synthesis, bioconversion, pharmacokinetic and pharmacodynamic evaluation of N-isopropyl-oxy-carbonyloxymethyl prodrugs of CZh-226, a potent and selective PAK4 inhibitor

We have previously disclosed compound 3 (CZh-226), a potent and selective PAK4 inhibitor, but its development was delayed due to poor oral pharmacokinetics. In an attempt to improve this issue, we synthesised a series of prodrugs by masking its terminal nitrogen of the piperazine moiety. Most synthesised prodrugs of 3 have low or no inhibition of PAK4 activity. The stability of synthetic prodrugs was evaluated in PBS, SGF, SIF, rat plasma and liver S9 fraction. Of these, prodrug 19 was not only stable under both acidic and neutral conditions but also could be quickly converted to parent drug 3 in rat plasma and liver S9 fraction. Such effective conversion into parent drug 3 was observed in rats, providing higher exposure of 3 compared to its direct administration. When given via oral route at daily doses of 25 and 50 mg/kg, the prodrug 19 was effective and well tolerated in mouse model of HCT-116 and B16F10.

PROTEASOME INHIBITING ?-LACTAM PRODRUGS USEFUL FOR THE TREATMENT OF CANCER AND NEURODEGENERATIVE DISORDERS

The present invention relates generally to proteasome inhibiting β-lactam compounds useful for the treatment of cancer and neurodegenerative disorders. The invention also provides pharmaceutical compositions and extended release formulations of said compounds, and medical uses of said compounds and/or pharmaceutical compositions to treat cancer and neurodegenerative disorders.

COMPOUNDS FOR TREATMENT OF NEURODEGENERATIVE DISEASES

Novel compounds of formula (II) are disclosed. Compounds of formula (II) comprise ornithine derivatives or compounds that can metabolize under physiological conditions to ornithine. The pH and plasma stability of compounds of formula (II) is also described. Also disclosed are methods for the treatment of neurodegenerative diseases such as Alzheimer's Disease using compounds of formula (II).

ORAL DOSAGE FORMS HAVING A HIGH LOADING OF A GABAPENTIN PRODRUG

Sustained release oral dosage forms with a high loading of a gabapentin prodrug are disclosed.

METHODS OF SYNTHESIZING N-HYDROXYSUCCINIMIDYL CARBONATES

The present disclosure relates to methods of synthesizing N-hydroxysuccinimidyl-carbonate intermediates from the corresponding sulfones useful in the preparation of 1-(acyloxy)-alkyl carbamate prodrugs.

Acyloxyalkyl carbamate prodrugs, methods of synthesis, and use

Acyloxyalkyl carbamate prodrugs of 3-aminopropylphosphonous acid, 3-aminopropylphosphinic acid, and analogs thereof, pharmaceutical compositions comprising acyloxyalkyl carbamate prodrugs of 3-aminopropylphosphonous acid, 3-aminopropylphosphinic acid, and analogs thereof, methods of making prodrugs of 3-aminopropylphosphonous acid, 3-aminopropylphosphinic acid, and analogs thereof, methods of using prodrugs of 3-aminopropylphosphonous acid, 3-aminopropylphosphinic acid, and analogs thereof and pharmaceutical compositions thereof for treating or preventing diseases or disorders such as spasticity or gastroesophageal reflux disease are disclosed. Acyloxyalkyl carbamate prodrugs of 3-aminopropylphosphonous acid, 3-aminopropylphosphinic acid, and analogs thereof and sustained release oral dosage forms thereof, which are suitable for oral administration, are also disclosed.

Acyloxyalkyl carbamate prodrugs of sulfinic acids, methods of synthesis, and use

Acyloxyalkyl carbamate prodrugs of 3-aminopropylsulfinic acid and analogs thereof, pharmaceutical compositions of 3-aminopropylsulfinic acid and analogs thereof, methods of making prodrugs of 3-aminopropylsulfinic acid and analogs thereof, methods of using prodrugs of 3-aminopropylsulfinic acid and analogs thereof, and pharmaceutical compositions thereof for treating or preventing diseases or disorders such as spasticity or gastroesophageal reflux disease are disclosed. Acyloxyalkyl carbamate prodrugs of 3-aminopropylsulfinic acid and analogs thereof and sustained release oral dosage forms thereof, which are suitable for oral administration, are also disclosed.

SYNTHESIS OF ACYLOXYALKYL CARBAMATE PRODRUGS AND INTERMEDIATES THEREOF

Methods for synthesis of 1-(acyloxy)-alkyl carbamates, particularly, the synthesis of 1-(acyloxy)-alkyl carbamate prodrugs of primary or secondary amine containing drugs are described. Also described are methods for synthesis of 1-(acyloxy)-alkyl N-hydroxysuccinimidyl carbonates which are useful intermediates in the synthesis of 1-(acyloxy)-alkyl carbamates are also described.