113791-14-3

Usage

Uses

Used in Pharmaceutical Industry:
2-Azetidinone, 3-amino-, (S)-, monoacetate is used as a key intermediate in the synthesis of various pharmaceutical drugs for its versatile reactivity and stability. It plays a crucial role in the development of new medications, contributing to the advancement of healthcare and treatment options.
Used in Neurological Disorders Treatment:
2-Azetidinone, 3-amino-, (S)-, monoacetate is used as a potential therapeutic agent for the treatment of various neurological disorders. Its unique properties and reactivity make it a promising candidate for the development of new treatments and therapies to address these complex conditions.
Used in Inflammatory Diseases Treatment:
2-Azetidinone, 3-amino-, (S)-, monoacetate is also used in the treatment of various inflammatory diseases. Its potential therapeutic applications in this area highlight its versatility and the possibility of improving patient outcomes through targeted interventions and treatments.

Upstream product

• 80082-81-1 benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate 
• 64-19-7 acetic acid 

Downstream Products

• 1619921-96-8 3-phenyl-N-[(S)-2-oxoazetidin-3-yl]propanamide 
• 1619922-06-3 4-butyl-N-[(S)-2-oxoazetidin-3-yl]benzamide 

Relevant academic research and scientific papers

CARBAMATE DERIVATIVES OF LACTAM BASED N-ACYLETHANOLAMINE ACID AMIDASE (NAAA) INHIBITORS

Described herein are compounds and pharmaceutical compositions which inhibit N-acylethanolamine acid amidase (NAAA). Described herein are methods for synthesizing the compounds set forth herein and methods for formulating these compounds as pharmaceutical compositions which include these compounds. Also described herein are methods of inhibiting NAAA in order to sustain the levels of palmitoylethanolamide (PEA) and other N-acylethanolamines (NAE) that are substrates for NAAA, in conditions characterized by reduced concentrations of NAE. Also, described here are methods of treating and ameliorating pain, inflammation, inflammatory diseases, and other disorders in which modulation of fatty acid ethanolamides is clinically or therapeutically relevant or in which decreased levels of NAE are associated with the disorder.

3-Aminoazetidin-2-one derivatives as N-acylethanolamine acid amidase (NAAA) inhibitors suitable for systemic administration

N-Acylethanolamine acid amidase (NAAA) is a cysteine hydrolase that catalyzes the hydrolysis of endogenous lipid mediators such as palmitoylethanolamide (PEA). PEA has been shown to exert anti-inflammatory and antinociceptive effects in animals by engaging peroxisome proliferator-activated receptor α (PPAR-α). Thus, preventing PEA degradation by inhibiting NAAA may provide a novel approach for the treatment of pain and inflammatory states. Recently, 3-aminooxetan-2-one compounds were identified as a class of highly potent NAAA inhibitors. The utility of these compounds is limited, however, by their low chemical and plasma stabilities. In the present study, we synthesized and tested a series of N-(2-oxoazetidin-3-yl)amides as a novel class of NAAA inhibitors with good potency and improved physicochemical properties, suitable for systemic administration. Moreover, we elucidated the main structural features of 3-aminoazetidin-2-one derivatives that are critical for NAAA inhibition. Stability is the key: α-Amino-β-lactams were synthesized as amide derivatives, and the effect of the azetidin-2-one ring, the stereochemistry at the α-position, and the functionalization of the α-amino group were studied with regard to N-acylethanolamine acid amidase inhibitory potency and hydrolytic and plasma stability.