1450824-22-2

Usage

Uses

Used in Pharmaceutical Industry:
TD 139 is used as a therapeutic agent for treating pulmonary fibrosis, a chronic and progressive lung disease characterized by the thickening and scarring of lung tissue. It specifically targets idiopathic pulmonary fibrosis in mammals, which is a form of the disease with no known cause.
The compound's ability to inhibit galectins makes it a promising candidate for the development of new treatments for pulmonary fibrosis, as these proteins have been implicated in the pathogenesis of the disease. By blocking the activity of galectins, TD 139 may help to reduce the inflammation and fibrosis associated with the condition, potentially improving the quality of life and life expectancy for patients suffering from pulmonary fibrosis.

Upstream product

• 138922-03-9 phenyl 4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 1193784-34-7 phenyl 2-O-acetyl-4,6-O-benzylidene-1-thio-3-O-trifluoromethanesulfonyl-β-D-galactopyranoside 
• 1185735-68-5 phenyl 2-O-acetyl-4,6-O-benzylidene-1-thio-3-O-trifluoromethanesulfonyl-β-D-gulopyranoside 
• 1185735-69-6 phenyl 2-O-acetyl-3-azido-4,6-O-benzylidene-3-deoxy-1-thio-β-D-galactopyranoside 
• 1193784-35-8 phenyl 2-O-acetyl-3-azido-3-deoxy-1-thio-β-D-galactopyranoside 
• 1193784-36-9 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-4-azido-6-(phenylthio)tetrahydro-2H-pyran-3,5-diyl diacetate 
• 155301-09-0 2,4,6-tri-O-acetyl-3-azido-3-deoxy-β-D-galactopyranosyl bromide 
• 1193784-38-1 2,2‘,4,4’,5,5‘,6,6‘-hexa-O-acetyl-3,3‘-diazido-3,3‘-dideoxy-1,1‘-sulfanediyl-di-β-D-galactopyranoside 
• 1193784-39-2 bis-(3-azido-3-deoxy-β-D-galactopyranosyl)-sulfane 
• 2561-17-3 1-ethynyl-3-fluoro-benzene 
• 1185735-67-4 phenyl 2-O-acetyl-4,6-O-benzyliden-1-thio-β-D-gulopyranoside 
• 71676-30-7 phenyl 4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside 

Relevant academic research and scientific papers

LARGE SCALE PROCESS OF 3,3'-DIDEOXY-3,3'-BIS-[4-(3-FLUOROPHENYL)-1H-1,2,3-TRIAZOL-1-YL]-1,1'-SULFANEDIYL-DI-BETA-D-GALACTOPYRANOSIDE

The present invention relates to a process for preparing a compound of formula (I), wherein said process is suitable for large scale synthesis.

Efficient synthesis of a galectin inhibitor clinical candidate (TD139) using a Payne rearrangement/azidation reaction cascade

Selective galectin inhibitors are valuable research tools and could also be used as drug candidates. In that context, TD139, a thiodigalactoside galectin-3 inhibitor, is currently being evaluated clinically for the treatment of idiopathic pulmonary fibrosis. Herein, we describe a new strategy for the preparation of TD139. Starting from inexpensive levoglucosan, we used a rarely employed reaction cascade: Payne rearrangement/azidation process leading to 3-azido-galactopyranose. The latter intermediate was efficiently converted into TD139 in a few simple and practical steps.

SYNTHESIS OF 3-AZIDO-3-DEOXY-D-GALACTOPYRANOSE

The present application provides a synthetic method for production of 3-azido-3-deoxy-D-galactopyranose. Also provided are methods of using the 3-azido-3-deoxy-D-galactopyranose in the manufacture of galactoside galectin antagonists, such as TD139 (GB0139), GB1107, GB2064, and GB1211.

The sulfur crosslinking disaccharide compound (by machine translation)

[Problem] to improve the yield of the synthesis method of the compound disaccharide sulfur crosslinking. The present invention is [a], (I) shows a formula, 2S, 4aR, 6S, 7R, 8R, 8aR) (phenylthio) phenyl 3, 2 a-d -2 - -6 - Hexahydropyrano: [1, 3] dioxin - 7, 8 - diol synthesized from the start, the total yield of the improved conventional method, sulfur-linked disaccharide compound production. [1 A][Drawing] no (by machine translation)

GALACTOPYRANOSIDE DERIVATIVE

PROBLEM TO BE SOLVED: To provide galactopyranoside derivatives that can be used for the synthesis of various sugar derivatives. SOLUTION: The present invention provides a galactopyranoside derivative represented by formula (I) (R1's each represent -C (=O) R5, or are bound to each other to be a phenyl group-substituted methylene; R2 is hydroxylazide or the like; R3 is H, methyl, nitro or Cl; R4 is a phenylthio or bromo group). SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

Galectin-3-Binding Glycomimetics that Strongly Reduce Bleomycin-Induced Lung Fibrosis and Modulate Intracellular Glycan Recognition

Discovery of glycan-competitive galectin-3-binding compounds that attenuate lung fibrosis in a murine model and that block intracellular galectin-3 accumulation at damaged vesicles, hence revealing galectin-3–glycan interactions involved in fibrosis progression and in intracellular galectin-3 activities, is reported. 3,3′-Bis-(4-aryltriazol-1-yl)thiodigalactosides were synthesized and evaluated as antagonists of galectin-1, -2, -3, and -4 N-terminal, -4 C-terminal, -7 and -8 N-terminal, -9 N-terminal, and -9 C-terminal domains. Compounds displaying low-nanomolar affinities for galectins-1 and -3 were identified in a competitive fluorescence anisotropy assay. X-ray structural analysis of selected compounds in complex with galectin-3, together with galectin-3 mutant binding experiments, revealed that both the aryltriazolyl moieties and fluoro substituents on the compounds are involved in key interactions responsible for exceptional affinities towards galectin-3. The most potent galectin-3 antagonist was demonstrated to act in an assay monitoring galectin-3 accumulation upon amitriptyline-induced vesicle damage, visualizing a biochemically/medically relevant intracellular lectin–carbohydrate binding event and that it can be blocked by a small molecule. The same antagonist administered intratracheally attenuated bleomycin-induced pulmonary fibrosis in a mouse model with a dose/response profile comparing favorably with that of oral administration of the marketed antifibrotic compound pirfenidone.

Novel Galactoside Inhibitor of Galectins

The present invention relates to a compound of the general formula (I): The compound of formula (I) is suitable for treating pulmonary fibrosis, such as Idiopathic pulmonary fibrosis in a mammal. Furthermore the present invention concerns a method of monitoring development or progression of pulmonary fibrosis in a human subject, a method of monitoring or predicting exacerbation of symptoms in a human subject with pulmonary fibrosis as well as a method for treatment of pulmonary fibrosis, such as Idiopathic pulmonary fibrosis in a human subject having a galectin-3 level indicative of pulmonary fibrosis or exacerbation of symptoms.

METHODS, COMPOSITIONS AND KITS FOR TREATING, MODULATING, OR PREVENTING OCULAR ANGIOGENESIS OR FIBROSIS IN A SUBJECT USING A GALECTIN PROTEIN INHIBITOR

Methods and kits using a pharmaceutical composition for use in inhibiting ocular angiogenesis or fibrosis are provided herein, such that composition includes a pharmaceutically suitable carrier or diluent and an amount of the inhibitor composition effective to inhibit the angiogenesis or the fibrosis by inhibiting expression and/or activity of a galectin protein or a portion thereof.