100202-39-9

Usage

Uses

Used in Pharmaceutical Industry:
3-Azetidinecarboxylic Acid, Methyl Ester, Hydrochloride is used as a key intermediate compound for the synthesis of various pharmaceuticals. Its unique chemical structure allows it to be a versatile building block in the development of new drugs.
Used in Treatment of Metabolic Disorders:
3-Azetidinecarboxylic Acid, Methyl Ester, Hydrochloride is used as a precursor in the preparation of inhibitors for human glycogen phosphorylase. These inhibitors have potential therapeutic applications in the treatment of hyperglycemia, hyperinsulinemia, hyperlipidemia, insulin resistance, and tissue ischemia. By targeting glycogen phosphorylase, these inhibitors can help regulate glucose metabolism and improve the symptoms associated with these metabolic disorders.

InChI:InChI=1/C5H9NO2.ClH/c1-8-5(7)4-2-6-3-4;/h4,6H,2-3H2,1H3;1H

Upstream product

• 53871-06-0 1-(diphenylmethyl)-3-methoxycarbonylazetidine 
• 67-56-1 methanol 
• 36476-78-5 3-azetidinecarboxylic acid 

Downstream Products

• 610791-05-4 azetidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester 
• 362703-02-4 C₂₄H₂₄N₂O₄ 
• 937055-18-0 methyl 1-(3-((4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl)propanoyl)-3-azetidinecarboxylate 
• 1220971-99-2 methyl 1-((5-(5-(3,4-diethoxyphenyl)-1,2,4-oxadiazol-3-yl)benzofuran-2-yl)methyl)azetidine-3-carboxylate 
• 1226694-59-2 1-(2-{6-methyl-8-[4-(1-phenyl-1H-pyrazol-3-ylmethyl)-[1,4]diazepan-1-yl]quinolin-7-yloxy}acetyl)azetidine-3-carboxylic acid methyl ester 
• 1229705-62-7 methyl 1-{2-tris(4-methoxyphenyl)methoxyethyl}azetidine-3-carboxylate 
• 1229705-60-5 methyl 1-(4,4-diphenylbut-3-en-1-yl)azetidine-3-carboxylate 
• 1236148-78-9 methyl 1-(4-cyanobenzyl)azetidine-3-carboxylate 
• 1160956-13-7 1-((2S)-3-{4-[5-(5-Diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-2-hydroxy-propyl)-azetidine-3-carboxylic acid 
• 757239-60-4 O₁-benzyl-O₃-methylazetidine-1,3-dicarboxylate 
• 1344707-41-0 (R/S)-methyl 1-(3-(2-hydroxy-2-(4-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetamido)propanoyl)azetidine-3-carboxylate 
• 1351945-09-9 7-(hydroxymethyl)-1-methyl-4-oxo-N-(2-(trifluoromethyl)-4-biphenylyl)-1,4-dihydro-3-quinolinecarboxamide 
• 1372633-66-3 methyl 1-((1-methyl-4-oxo-3-(2-(trifluoromethyl)biphenyl-4-ylcarbamoyl)-1,4-dihydroquinolin-7-yl)methyl)azetidine-3-carboxylate 
• 1422170-09-9 methyl 1-((3,5-dimethylisoxazol-4-yl)(5-(2-(((2,4-dimethylphenyl)(phenyl)methyl)amino)-2-oxoethyl)benzofuran-2-yl)methyl)azetidine-3-carboxylate 

Relevant academic research and scientific papers

Ferulic acid amide derivatives with varying inhibition of amyloid-β oligomerization and fibrillization

Alzheimer's disease (AD) is a progressive neurodegenerative disorder characterized, in part, by the misfolding, oligomerization and fibrillization of amyloid-β (Aβ). Evidence suggests that the mechanisms underpinning Aβ oligomerization and subsequent fibrillization are distinct, and may therefore require equally distinct therapeutic approaches. Prior studies have suggested that amide derivatives of ferulic acid, a natural polyphenol, may combat multiple AD pathologies, though its impact on Aβ aggregation is controversial. We designed and synthesized a systematic library of amide derivatives of ferulic acid and evaluated their anti-oligomeric and anti-fibrillary capacities independently. Azetidine tethered, triphenyl derivatives were the most potent anti-oligomeric agents (compound 2i: IC50 = 1.8 μM ± 0.73 μM); notably these were only modest anti-fibrillary agents (20.57% inhibition of fibrillization), and exemplify the poor correlation between anti-oligomeric/fibrillary activities. These data were subsequently codified in an in silico QSAR model, which yielded a strong predictive model of anti-Aβ oligomeric activity (κ = 0.919 for test set; κ = 0.737 for validation set).

Carbonyl azetidine substituted naphthalimide fluorescent dye as well as synthesis method and application thereof

The invention provides a novel carbonyl azetidine substituted naphthalimide fluorescent dye as well as synthesis and application thereof. The dye takes 1, 8-naphthalimide as a fluorophore parent, and the fourth site of the 1, 8-naphthalimide is covalently connected with carbonyl azetidine. The novel fluorescent dye has excellent fluorescence intensity and light stability, so that the novel fluorescent dye has wide application prospects in the fields of fluorescence detection, fluorescence imaging and the like, especially in the emerging fields of single molecule detection, super-resolution fluorescence imaging and the like. R1 is H, C1-4 alkyl and aryl, R2 is shown in the specification, and in R2, X1 is H, C1-2 alkyl, X2 is C1-2 alkyl or shown in the specification, X3 is C1-2 alkyl or shown in the specification, and X4 is C1-2 alkyl.

Carbonyl azetidine substituted coumarin fluorescent dye as well as synthesis method and application thereof

The invention provides a novel carbonyl azetidine substituted coumarin fluorescent dye as well as synthesis and application thereof. The structural innovation of the dye is that carbonyl azetidine is covalently linked to the No.7 site of a coumarin parent. The novel fluorescent dye has excellent fluorescence intensity and light stability, so that the novel fluorescent dye has wide application prospects in the fields of fluorescence detection, fluorescence imaging and the like, especially in the emerging fields of single molecule detection, super-resolution fluorescence imaging and the like. R1 is C1-4 alkyl, and R2 is shown in the specification, X1 is H or C1-2 alkyl, X2 is C1-2 alkyl or shown in the specification, X3 is C1-2 alkyl or shown in the specification, and X4 is C1-2 alkyl.

Carbonyl azetidine substituted NBD fluorescent dye as well as synthesis method and application thereof

The invention provides a novel carbonyl azetidine substituted NBD fluorescent dye as well as synthesis and application thereof. The structure of the dye is characterized in that carbonyl azetidine is covalently connected to the fourth site of a 4-chloro-7-nitrobenzene-2-oxa-1, 3-diazole (NBD) parent. The novel fluorescent dye has excellent fluorescence intensity and light stability, so that the novel fluorescent dye has wide application prospects in the fields of fluorescence detection, fluorescence imaging and the like, especially in the emerging fields of single molecule detection, super-resolution fluorescence imaging and the like. R1 is as described in the specification, X1 is H or C1-2 alkyl, X2 is C1-2 alkyl or as described in the specification, x3 is C1-2 alkyl or as described in the specification, and X4 is C1-2 alkyl.

CASPASE INHIBITOR AND PHARMACEUTICAL COMPOSITION, USE AND THERAPEUTIC METHOD THEREOF

Disclosed are a class of compounds as a caspase inhibitor, and in particular the compound as shown in formula (I) or a pharmaceutically acceptable salt thereof, and the use of the compound in treating caspase-related diseases.

PROCESS FOR THE PREPARATION OF 2-(3-(FLUOROMETHYL)AZETIDIN-1-YL)ETHAN-1-OL

Methods of making 2-(3-(fluoromethyl)azetidin-1-yl)ethan-1-ol 9, an intermediate useful for the synthesis of estrogen receptor modulating compounds are described.

Discovery of a 1-Methyl-3,4-dihydronaphthalene-Based Sphingosine-1-Phosphate (S1P) Receptor Agonist Ceralifimod (ONO-4641). A S1P1 and S1P5 Selective Agonist for the Treatment of Autoimmune Diseases

The discovery of 1-({6-[(2-methoxy-4-propylbenzyl)oxy]-1-methyl-3,4-dihydronaphthalen-2-yl}methyl)azetidine-3-carboxylic acid 13n (ceralifimod, ONO-4641), a sphingosine-1-phosphate (S1P) receptor agonist selective for S1P1 and S1P5, is described. While it has been revealed that the modulation of the S1P1 receptor is an effective way to treat autoimmune diseases such as relapsing-remitting multiple sclerosis (RRMS), it was also reported that activation of the S1P3 receptor is implicated in some undesirable effects. We carried out a structure-activity relationship (SAR) study of hit compound 6 with an amino acid moiety in the hydrophilic head region. Following identification of a lead compound with a dihydronaphthalene central core by inducing conformational constraint, optimization of the lipophilic tail region led to the discovery of 13n as a clinical candidate that exhibited >30 000-fold selectivity for S1P1 over S1P3 and was potent in a peripheral lymphocyte lowering (PLL) test in mice (ED50 = 0.029 mg/kg, 24 h after oral dosing).

HETERO-HALO INHIBITORS OF HISTONE DEACETYLASE

This invention provides compounds that are inhibitors of HDAC2. The compounds (e.g., compounds according to Formula I, II or any of Compounds 100-128 or any of those in Tables 2 or 3) accordingly are useful for treating, alleviating, or preventing a condition in a subject such as a neurological disorder, memory or cognitive function disorder or impairment, extinction learning disorder, fungal disease or infection, inflammatory disease, hematological disease, or neoplastic disease, or for improving memory or treating, alleviating, or preventing memory loss or impairment.

MONOBACTAMS

The present invention is directed to a new class of monobactam derivatives and their use for treating bacterial infections.

Structure-activity relationship studies of S1P agonists with a dihydronaphthalene scaffold

Structure-activity relationship (SAR) of sphingosine-1-phosphate receptor agonists with a dihydronaphthalene scaffold was investigated. Compound 1 was modified to improve S1P1 agonistic activity and in vivo peripheral lymphocyte lowering (PLL) activity without impairing selectivity over S1P 3 agonistic activity. A detailed SAR study of the terminal lipophilic part revealed that the introduction of substituents on the propylene linker and the terminal benzene ring influences in vitro and PLL activities. Compound 6n bearing a (S)-methyl group at the 2-position on the propylene linker and chlorine at the para-position on the terminal benzene ring showed potent hS1P1 agonistic activity with excellent selectivity over hS1P 3 and in vivo PLL activity in mice.