Telmisartan

Base Information

• Chemical Name: Telmisartan
• CAS No.: 144701-48-4
• Molecular Formula: C33H30N4O2
• Molecular Weight: 514.627
• Hs Code.: 2933995300
• European Community (EC) Number: 620-494-7
• NSC Number: 759811
• UNII: U5SYW473RQ
• DSSTox Substance ID: DTXSID8023636
• Nikkaji Number: J556.167A
• Wikipedia: Telmisartan
• Wikidata: Q733186
• NCI Thesaurus Code: C47746
• RXCUI: 73494
• Pharos Ligand ID: UXX5QY748TGQ
• Metabolomics Workbench ID: 43221
• ChEMBL ID: CHEMBL1017
• Mol file: 144701-48-4.mol

Synonyms:4'-((1,4'-dimethyl-2'-propyl(2,6'-bi-1H-benzimidazol)-1'-yl)methyl)-(1,1'-biphenyl)-2-carboxylic acid;BIBR 277;BIBR-277;Micardis;Pritor;telmisartan

Chemical Property of Telmisartan

Chemical Property:

• Appearance/Colour: White or off white crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 261-263 °C
• Refractive Index: 1.624
• Boiling Point: 771.9 °C at 760 mmHg
• PKA: 3.86±0.36(Predicted)
• Flash Point: 420.6 °C
• PSA: 72.94000
• Density: 1.24 g/cm³
• LogP: 7.26440
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO: >5 mg/mL at 60 °C
• Water Solubility.: insoluble
• XLogP3: 6.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 514.23687621
• Heavy Atom Count: 39
• Complexity: 831

Purity/Quality:

99% ^*data from raw suppliers

Telmisartan ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Angiotensin II Receptor Antagonists
• Canonical SMILES: CCCC1=NC2=C(N1CC3=CC=C(C=C3)C4=CC=CC=C4C(=O)O)C=C(C=C2C)C5=NC6=CC=CC=C6N5C
• Recent ClinicalTrials: Improving 24-hour Blood Pressure in Obstructive Sleep Apnea
• Recent EU Clinical Trials: Feasibility of Aggressive Albuminuria Reduction in Biopsy-Proven Diabetic Nephropathy - A Pilot Study
• Recent NIPH Clinical Trials: Effect of telmisartan on patients with renal dysfunction
• Pharmacological Profile: Telmisartan is a selective angiotensin II type 1 receptor antagonist (ARB), also known as an angiotensin receptor blocker. It has a unique pharmacologic profile with partial agonistic activity on peroxisome proliferator-activated receptor 纬 (PPAR纬).; Unlike other ARBs, telmisartan has a long half-life of about 24 hours, resulting in sustained blood pressure reduction and prolonged action. It exhibits high lipophilicity, facilitating oral absorption, tissue distribution, and cell penetration, leading to a larger volume of distribution.
• Clinical Uses: Telmisartan is used primarily for the management of hypertension, either as monotherapy or in combination with other antihypertensive agents. Considered a first-line drug for mild-to-moderate hypertension with an excellent safety profile. It is also utilized in the treatment of hypertension-related cardiovascular end-organ damage.
• Clinical Uses: Telmisartan's dual activity as an ARB and partial PPAR纬 agonist provides multiple clinical benefits, including anti-diabetic and cardiovascular effects. Animal studies suggest that telmisartan is more effective in improving metabolic syndrome compared to other ARBs, with benefits in insulin resistance, lipid profile, and blood pressure control.
• Potential Use in Covid-19: Telmisartan, along with other ARBs, has been proposed as a potential treatment for COVID-19-induced lung inflammation due to its anti-inflammatory properties.
• Pharmacokinetics and Binding Affinity: Telmisartan has a very low binding affinity for angiotensin II type 2 receptors (AT2) and minimal binding to other receptors such as catecholamine, acetylcholine, dopamine, serotonin, and histamine. It is primarily eliminated through feces, distinguishing it from other ARBs that undergo renal excretion to varying extents.

Technology Process of Telmisartan

There total 69 articles about Telmisartan 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: 98.7%

4'-[[2-n-propyl-4-methyl-6-(1-methyl-benzimidazol-2-yl)-1H-benzimidazol-1-yl]-methyl]-2-cyano-biphenyl (144702-27-2) → telmisatran (144701-48-4)

Guidance literature:

4'-[[2-n-propyl-4-methyl-6-(1-methyl-benzimidazol-2-yl)-1H-benzimidazol-1-yl]-methyl]-2-cyano-biphenyl; With sodium hydroxide; water; In ethylene glycol; for 8h; Heating / reflux;

With acetic acid; In water; ethylene glycol; at 20 ℃; pH=4; Product distribution / selectivity;

Reference yield: 98.6%

4'-[[4-methyl-6-(1-methyl-1H-benzimidazol-2-yl)-2-propyl-1H-benzimidazol-1-yl]methyl]biphenyl-2-carboxylic acid methyl ester (528560-93-2) → telmisatran (144701-48-4)

Guidance literature:

4'-[[4-methyl-6-(1-methyl-1H-benzimidazol-2-yl)-2-propyl-1H-benzimidazol-1-yl]methyl]biphenyl-2-carboxylic acid methyl ester; With methanol; sodium hydroxide; water; for 2h; Heating / reflux;

With acetic acid; In water;

Reference yield: 95.0%

2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)benzimidazole (152628-02-9) + 4'-bromomethylbiphenyl-2-carboxylic acid (150766-86-2) → telmisatran (144701-48-4)

Guidance literature:

2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)benzimidazole; With sodium hydride; In N,N-dimethyl-formamide; at 0 - 5 ℃; for 1h;

4'-bromomethylbiphenyl-2-carboxylic acid; In N,N-dimethyl-formamide; at 10 ℃; Solvent; Reagent/catalyst; Temperature;

upstream raw materials:

tert-butyl 4'-[[2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)-benzimidazol-1-yl]-methyl]-biphenyl-2-carboxylate

4'-[[2-n-propyl-4-methyl-6-(1-methyl-benzimidazol-2-yl)-1H-benzimidazol-1-yl]-methyl]-2-cyano-biphenyl

methyl 4-amino-3-methylbenzoate

N-methylbenzene-1,2-diamine dihydrochloride

Downstream raw materials:

telmisartan tert-butylamine salt

telmisartan choline salt

4'-[[2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)-benzimidazol-1-yl]-methyl]-biphenyl-2-carboxylic acid ammonium salt

telmisartan meglumine salt

Refernces

Trifluoromethylation of Benzoic Acids: An Access to Aryl Trifluoromethyl Ketones

10.1021/acs.orglett.1c01720

The study presents an efficient method for the trifluoromethylation of benzoic acids using TMSCF3 (trimethylsilyl trifluoromethane) to produce aryl trifluoromethyl ketones. The reaction involves anhydrides as in situ activating reagents, with trifluoroacetic anhydride (TFAA) and 4-dimethylaminopyridine (DMAP) playing crucial roles in activating the carboxylic acids and facilitating nucleophilic addition. CsF (cesium fluoride) is used to enhance the yield of the desired products. The reaction is conducted in PhOMe (anisole) solvent under nitrogen at 120 °C for 15 hours. The study demonstrates a wide substrate scope, including various carboxylic acids with different functional groups, and shows high functional group tolerance. Notably, bioactive molecules such as adapalin, probenecid, and telmisartan can also be trifluoromethylated using this method, highlighting its potential in drug design and development. The reaction conditions are relatively mild, and the process is scalable, making it a practical and environmentally benign approach for synthesizing aryl trifluoromethyl ketones.