Lomitapide Mesylate

Base Information

• Chemical Name: Lomitapide Mesylate
• CAS No.: 202914-84-9
• Molecular Formula: C39H37F6N3O2.x(CH4O3S)
• Molecular Weight: 789.8260592
• European Community (EC) Number: 692-734-9
• UNII: X4S83CP54E
• ChEMBL ID: CHEMBL2105662
• DSSTox Substance ID: DTXSID60174170
• NCI Thesaurus Code: C83892
• RXCUI: 1364478
• Wikidata: Q27139887
• Mol file: 202914-84-9.mol

Synonyms:Lomitapide mesylate;202914-84-9;BMS 201038-04;AEGR-733 mesylate;Aegr-733 mesilate;BMS-201038-04;Lomitapide (mesylate);lomitapide mesilate;Lomitapide mesylate [USAN];UNII-X4S83CP54E;X4S83CP54E;lomitapide monomesylate;CHEBI:72299;lomitapide methanesulfonate;DTXSID60174170;202914-84-9 (mesylate);Lomitapide mesilate (JAN);Lomitapide mesylate (USAN);9H-Fluorene-9-carboxamide, N-(2,2,2-trifluoroethyl)-9-(4-(4-(((4'-(trifluoromethyl)(1,1'-biphenyl)-2-yl)carbonyl)amino)-1-piperidinyl)butyl)-, methanesulfonate;N-(2,2,2-trifluoroethyl)-9-(4-(4-(4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxamido)piperidin-1-yl)butyl)-9H-fluorene-9-carboxamide methanesulfonate;N-(2,2,2-trifluoroethyl)-9-(4-(4-(4'-(trifluoromethyl)biphenyl-2-ylcarboxamido)piperidin-1-yl)butyl)-9H-fluorene-9-carboxamide methanesulfonate;LOMITAPIDE MESILATE [JAN];9H-FLUORENE-9-CARBOXAMIDE, N-(2,2,2-TRIFLUOROETHYL)-9-(4-(4-(((4'-(TRIFLUOROMETHYL)(1,1'-BIPHENYL)-2-YL)CARBONYL)AMINO)-1-PIPERIDINYL)BUTYL)-, METHANESULPHONATE;N-(2,2,2-TRIFLUOROETHYL)-9-(4-(4-(((4'-(TRIFLUOROMETHYL)BIPHENYL-2-YL)CARBONYL)AMINO)PIPERIDIN-1-YL)BUTYL)-9H-FLUORENE-9-CARBOXAMIDE METHANESULFONATE;N-(2,2,2-TRIFLUOROETHYL)-9-(4-(4-(((4'-(TRIFLUOROMETHYL)BIPHENYL-2-YL)CARBONYL)AMINO)PIPERIDIN-1-YL)BUTYL)-9H-FLUORENE-9-CARBOXAMIDE METHANESULPHONATE;Juxtapid (TN);1-(4-(9-((2,2,2-trifluoroethyl)carbamoyl)-9H-fluoren-9-yl)butyl)-4-(((4'-(trifluoromethyl)biphenyl-2-yl)carbonyl)amino)piperidinium methanesulfonate;1-(4-{9-[(2,2,2-trifluoroethyl)carbamoyl]-9H-fluoren-9-yl}butyl)-4-({[4'-(trifluoromethyl)biphenyl-2-yl]carbonyl}amino)piperidinium methanesulfonate;N-(2,2,2-trifluoroethyl)-9-{4-(4-({(4'-(trifluoromethyl)biphenyl-2-yl)carbonyl}amino)piperidin-1-yl)butyl}-9H-fluorene-9-carboxamide methanesulfonate;N-(2,2,2-trifluoroethyl)-9-{4-[4-({[4'-(trifluoromethyl)biphenyl-2-yl]carbonyl}amino)piperidin-1-yl]butyl}-9H-fluorene-9-carboxamide methanesulfonate;Lojuxta (TN);BMS-201038 mesylate;SCHEMBL2731380;CHEMBL2105662;DTXCID8096661;EX-A502;BMS-201038MA;GLXC-25701;AMY38734;BCP10696;CIA91484;LOMITAPIDE MESILATE [WHO-DD];MFCD19443682;s7633;AKOS025149431;CCG-270481;CS-3424;LOMITAPIDE MESYLATE [ORANGE BOOK];AC-33863;AS-56518;HY-14668;FT-0700260;D09638;J-690260;Q27139887;2059395-52-5;methanesulfonic acid;N-(2,2,2-trifluoroethyl)-9-[4-[4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]piperidin-1-yl]butyl]fluorene-9-carboxamide;N-(2,2,2-trifluoroethyl)-9-(4-(4-(4-(trifluoromethyl)biphenyl-2-ylcarboxamido)piperidin-1-yl)butyl)-9H-fluorene-9-carboxamide methanesulfonate;N-(2,2,2-trifluoroethyl)-9-[4-(4-{2-[4-(trifluoromethyl)phenyl]benzamido}piperidin-1-yl)butyl]-9H-fluorene-9-carboxamide

Chemical Property of Lomitapide Mesylate

Chemical Property:

• PSA: 124.19000
• LogP: 9.68660
• Storage Temp.: Inert atmosphere,Room Temperature
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 10
• Exact Mass: 789.26711156
• Heavy Atom Count: 55
• Complexity: 1200

Purity/Quality:

97% ^*data from raw suppliers

LomitapideMesylate >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CS(=O)(=O)O.C1CN(CCC1NC(=O)C2=CC=CC=C2C3=CC=C(C=C3)C(F)(F)F)CCCCC4(C5=CC=CC=C5C6=CC=CC=C64)C(=O)NCC(F)(F)F
• Recent EU Clinical Trials: A Phase 3, Single-arm, Open-label, International, Multi-center Study to Evaluate the Efficacy and Safety of Lomitapide in Pediatric Patients with Homozygous Familial Hypercholesterolemia on Stable Lipid-lowering Therapy
• Description: Lomitapide is an orally active microsomal triglyceride transfer protein (MTP) inhibitor for the treatment of hypercholesterolemia. The drug was developed by Aegerion Pharmaceuticals Inc. and licensed to Bristol–Myers Squibb Co. and the University of Pennsylvania. Lomitapide effectively lowered LDL–cholesterol, both as a single agent and in combination with commonly prescribed lipid-lowering therapies. Sold under the trade name Juxtapid, the drug offers a new treatment option to patients who cannot tolerate statin therapy or who experience insufficient LDL–cholesterol reduction with the currently available therapies, such as patients with homozygous familial hypercholesterolemia caused by mutations in the LDLR gene.

Technology Process of Lomitapide Mesylate

There total 24 articles about Lomitapide Mesylate 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: 100.0%

9-[4-[4-[[[4'-(trifluoromethyl)[1,1'-biphenyl]-2-yl]carbonyl]amino]-1-piperidinyl]butyl]-N-(2,2,2-trifluoroethyl)-9H-fluorene-9-carboxamide (182431-12-5) + methanesulfonic acid (75-75-2,98527-29-8) → N-(2,2,2-trifluoroethyl)-9-[4-[4-[[[4’-(trifluoromethyl)[1,1‘-biphenyl]-2-yl]carbonyl]amino]-1-piperidinyl]butyl]-9H-fluorene-9-carboxamide methanesulfonate (202914-84-9)

Guidance literature:

In ethyl acetate; at 20 ℃; for 2h; Temperature; Solvent;

Reference yield:

9H-fluorene-9-carboxylic acid (1989-33-9) → N-(2,2,2-trifluoroethyl)-9-[4-[4-[[[4’-(trifluoromethyl)[1,1‘-biphenyl]-2-yl]carbonyl]amino]-1-piperidinyl]butyl]-9H-fluorene-9-carboxamide methanesulfonate (202914-84-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: thionyl chloride / N,N-dimethyl-formamide / 0.5 h / 0 °C

2.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 0 °C

2.2: 16 h / 0 - 20 °C

3.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 24 h / 70 °C

4.1: sodium hydroxide; water / methanol; tetrahydrofuran / 24 h / 0 - 20 °C

5.1: triethylamine; chloroformic acid ethyl ester / dichloromethane / 1.75 h / 0 °C

5.2: 1.5 h / 0 - 20 °C

6.1: methanol / 3 h / 20 °C

With thionyl chloride; water; chloroformic acid ethyl ester; potassium carbonate; triethylamine; potassium iodide; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

4'-(trifluoromethyl)-2-biphenylcarboxylic acid (84392-17-6) → N-(2,2,2-trifluoroethyl)-9-[4-[4-[[[4’-(trifluoromethyl)[1,1‘-biphenyl]-2-yl]carbonyl]amino]-1-piperidinyl]butyl]-9H-fluorene-9-carboxamide methanesulfonate (202914-84-9)

Guidance literature:

Multi-step reaction with 4 steps

1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 10 h / 25 - 30 °C

2: ammonium formate; palladium 10% on activated carbon / methanol / 20 °C / Reflux

3: potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 25 - 30 °C

4: ethyl acetate / 2 h / 20 °C

With palladium 10% on activated carbon; ammonium formate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium iodide; In methanol; ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

9-[4-[4-[[[4'-(trifluoromethyl)[1,1'-biphenyl]-2-yl]carbonyl]amino]-1-piperidinyl]butyl]-N-(2,2,2-trifluoroethyl)-9H-fluorene-9-carboxamide

methanesulfonic acid

9H-fluorene-9-carboxylic acid

methyl 9H-fluorene-9-carboxylate

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