Ipragliflozin

Base Information

• Chemical Name: Ipragliflozin
• CAS No.: 761423-87-4
• Molecular Formula: C21H21FO5S
• Molecular Weight: 404.459
• UNII: 3N2N8OOR7X
• DSSTox Substance ID: DTXSID701032738
• Nikkaji Number: J2.470.784I
• Wikipedia: Ipragliflozin
• Wikidata: Q17193526
• NCI Thesaurus Code: C166685
• Pharos Ligand ID: CPJXPDYKBUDM
• Metabolomics Workbench ID: 152812
• ChEMBL ID: CHEMBL2018096
• Mol file: 761423-87-4.mol

Synonyms:(1S)-1,5-anhydro-1-(3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl)-D-glucitol;ASP-1941;ASP1941;ipragliflozin;Suglat

Chemical Property of Ipragliflozin

Chemical Property:

• Boiling Point: 628.8±55.0 °C(Predicted)
• PKA: 13.27±0.70(Predicted)
• PSA: 118.39000
• Density: 1.452
• LogP: 2.14610
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 404.10937310
• Heavy Atom Count: 28
• Complexity: 525

Purity/Quality:

99% min ^*data from raw suppliers

Ipragliflozin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(S2)CC3=C(C=CC(=C3)C4C(C(C(C(O4)CO)O)O)O)F
• Isomeric SMILES: C1=CC=C2C(=C1)C=C(S2)CC3=C(C=CC(=C3)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)F
• Recent ClinicalTrials: Efficacy of Ipragliflozin Compared With Sitagliptin in Uncontrolled Type 2 Diabetes With Sulfonylurea and Metformin
• Recent EU Clinical Trials: Phase 2b, Double-Blind, Randomized, Multicenter, Parallel Group, Placebo-Controlled, Dose-Finding Study to Evaluate the Efficacy, Safety and Tolerability of a 12-Week Treatment with ASP1941 in Combination with Metformin in Subjects with Type 2 Diabetes Mellitus Who Have Inadequate Glycemic Control on Metformin Alone
• Recent NIPH Clinical Trials: Assessing patient body composition following treatment with sodium glucose co-transporter 2 inhibitor for type 1 diabetes mellitus
• Description: Ipragliflozin is a sodium-glucose cotransporter 2 (SGLT2) inhibitor (IC50 = 7.4 nM in CHO cells expressing the human cotransporter). It is selective for SGLT2 over SGLT1, SGLT3, SGLT4, SGLT5, and SGLT6 (IC50s = 1.9, 30.4, 15.9, 0.46, and 10.4 μM, respectively). Ipragliflozin (0.1-3 mg/kg) decreases plasma levels of insulin and glucose in an oral glucose tolerance test in a mouse model of diabetes induced by high-fat diet, streptozotocin (STZ; ), and nicotinamide . It decreases plasma and hepatic IL-6, TNF-α, chemokine (C-C motif) ligand 2 (CCL2), and C-reactive protein (CRP) levels in the same model when administered at a dose of 3 mg/kg per day for 28 days.
• Uses: Ipragliflozin is a potent and selective inhibitor of sodium-glucose cotransporter-2 (SGLT2) and can serve as a potential agent for the treatment of type 1 and type 2 diabetes.

Technology Process of Ipragliflozin

There total 33 articles about Ipragliflozin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.5%

(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-sorbitol (1034305-21-9) → (2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (761423-87-4) + (1R)-1,5-anhydro-1-{3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl}-D-glucitol

Guidance literature:

With lithium hydroxide monohydrate; water; In tetrahydrofuran; methanol; at 15 ℃; for 4h; Temperature; Reagent/catalyst; Concentration; Industrial scale;

Reference yield: 97.0%

(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-sorbitol (1034305-21-9) → (2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (761423-87-4)

Guidance literature:

(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-sorbitol; With methanol; water; sodium hydroxide; at 25 - 49.1 ℃;

With hydrogenchloride; In methanol; water; at 20.2 - 60 ℃;

Reference yield: 95.3%

(1S)-1,5-anhydro-1-{3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl}-2,3,4,6-tetra-O-pivaloyl-D-glucitol → (2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (761423-87-4)

Guidance literature:

With methanol; sodium methylate; at 65 ℃; for 3h;

DOI:10.3762/bjoc.13.105

upstream raw materials:

(1S)-1,5-anhydro-1-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-2,3,4,6-tetra-O-benzyl - D-glucitol

(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-sorbitol

(1-benzothiophen-2-yl)(5-bromo-2-fluorophenyl)methanol

2-[(5-bromo-2-fluorophenyl)methyl]-1-benzothiophene

Downstream raw materials:

Ipragliflozin L-proline

Refernces

• 1、 -. "Preparation method of diabetes-treating medicine, namely ipragliflozin or derivative thereof". . . Retrieved 2020/11/01.
• 2、 Gong, Liang,Sun, Hong-Bao,Deng, Li-Fan,Zhang, Xia,Liu, Jie,Yang, Shengyong,Niu, Dawen. "Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones to Prepare C-Aryl Glycals and Acyclic Vinyl Ethers". . . Retrieved 2019/05/22.