Ranirestat

Base Information

• Chemical Name: Ranirestat
• CAS No.: 147254-64-6
• Molecular Formula: C17H11 Br F N3 O4
• Molecular Weight: 420.194
• UNII: Z26P56GFTV
• DSSTox Substance ID: DTXSID80163642
• Nikkaji Number: J1.030.857G
• Wikipedia: Ranirestat
• Wikidata: Q7293074
• NCI Thesaurus Code: C96307
• Pharos Ligand ID: VYW9L1LV1CL4
• Metabolomics Workbench ID: 149445
• ChEMBL ID: CHEMBL334830
• Mol file: 147254-64-6.mol

Synonyms:2-(4-bromo-2-fluorobenzyl)-1,2,3,4-tetrahydropyrrolo(1,2-a)pyrazine-4-spiro-3'-pyrrolidine-1.2',3,5'-tetrone;AS 3201;AS-3201;ranirestat;SX 3030;SX 3202;SX-3030;SX-3202

Chemical Property of Ranirestat

Chemical Property:

• Melting Point: 192-193℃
• Boiling Point: 702.7°Cat760mmHg
• PKA: 10.48±0.20(Predicted)
• Flash Point: 378.8°C
• PSA: 91.97000
• Density: 1.83g/cm³
• LogP: 1.52790
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 418.99170
• Heavy Atom Count: 26
• Complexity: 689

Purity/Quality:

99% ^*data from raw suppliers

Ranirestat ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(=O)NC(=O)C12C(=O)N(C(=O)C3=CC=CN23)CC4=C(C=C(C=C4)Br)F
• Isomeric SMILES: C1C(=O)NC(=O)[C@@]12C(=O)N(C(=O)C3=CC=CN23)CC4=C(C=C(C=C4)Br)F
• Recent ClinicalTrials: Evaluating the Efficacy and Safety of Oral Ranirestat (40 and 80 mg) in Mild to Moderate Diabetic Sensorimotor Polyneuropathy
• Recent EU Clinical Trials: A 2-year, Randomized, Double-blind, Placebo-controlled, Multi-center,
• Recent NIPH Clinical Trials: Clinical Pharmacology study for AS-3201 in renal impairment subjects
• Uses: Ranirestat is an aldose reductase inhibitor used for the treatment of diabetic sensorimotor polyneuropathy.

Technology Process of Ranirestat

There total 10 articles about Ranirestat 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: 95.0%

(S)-methyl 4-(2-amino-2-oxoethyl)-2-(4-bromo-2-fluorobenzyl)-1,3-dioxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-4-carboxylate (1211939-75-1) → ranirestat (147254-64-6)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

DOI:10.1021/ol100167w

Reference yield: 71.0%

4-bromo-2-fluorobenzylamine (112734-22-2) + R-(-)-3-ethoxycarbonyl-3-(2-(trichloroacetyl)pyrrol-1-yl)pyrrolidin-2,5-dione (159213-26-0) → ranirestat (147254-64-6)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 5h;

DOI:10.1021/ja0752585

Reference yield: 58.0%

(2R)-2-ethoxycarbonyl-2-(pyrrol-1-yl)succinimide diisopropylamine salt (1000784-39-3) + 4-bromo-2-fluorobenzylamine (112734-22-2) → ranirestat (147254-64-6)

Guidance literature:

(2R)-2-ethoxycarbonyl-2-(pyrrol-1-yl)succinimide diisopropylamine salt; With sulfuric acid; water; In ethyl acetate;

With trifluoroacetyl chloride; In ethyl acetate; for 6h; Heating / reflux;

4-bromo-2-fluorobenzylamine; With water; sodium hydrogencarbonate; diisopropylamine; more than 3 stages;

upstream raw materials:

R-(-)-3-ethoxycarbonyl-3-(2-(trichloroacetyl)pyrrol-1-yl)pyrrolidin-2,5-dione

4-bromo-2-fluorobenzylamine

(R)-ethyl-3-amino-2,5-dioxopyrrolidine-3-carboxylate

ethyl 2,5-dioxo-3-(1H-pyrrol-1-yl)pyrrolidine-3-carboxylate

Refernces

• 1、 -. "Process for production of 2,5 dioxopyrrolidine 3 carboxylate". Page/Page column 8. . Retrieved 2011/08/08.
• 2、 -. "3-HYDRAZINO-2,5-DIOXOPYRROLIDINE-3-CARBOXYLATES, PROCESS FOR PRODUCTION OF THE SAME, AND USE OF THE SAME". Page/Page column 10. . Retrieved 2009/10/18.