133910-00-6

Basic information

• Product Name: N-Trityl Losartan Carboxaldehyde
• Synonyms: 2-butyl-4-chloro-1-((2-(2-trityl-2H-tetrazol-5-yl)-[1,1-biphenyl]-4-yl)methyl)-1H-imidazole-5-carbaldehyde(WXG02231)
• CAS NO: 133910-00-6
• Molecular Formula: C₄₁H₃₅ClN₆O
• Molecular Weight: 663.2092
• Mol File: 133910-00-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-Trityl Losartan Carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: N-Trityl Losartan Carboxaldehyde(133910-00-6)
• EPA Substance Registry System: N-Trityl Losartan Carboxaldehyde(133910-00-6)

Safety Data

• Hazardous Substances Data: 133910-00-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-Trityl Losartan Carboxaldehyde is used as a chemical intermediate for the synthesis of EXP 3174, which is a metabolite of Losartan. This makes it valuable in the development and production of pharmaceuticals, particularly those related to the treatment of hypertension and cardiovascular diseases.

Upstream product

• 83857-96-9 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde 
• 133051-88-4 N-(triphenylmethyl)-5-<4'-(bromomethyl)biphenyl-2-yl>tetrazole 
• 57598-33-1 2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline 
• 114772-53-1 2-Cyano-4'-methylbiphenyl 
• 79047-41-9 2-n-butyl-4-chloro-5-hydroxymethylimidazole 
• 74201-13-1 N-(2-hydroxy-1,1-dimethyl)-2-methoxybenzamide 
• 84392-32-5 4,4-dimethyl-2-(4'-methyl-biphenyl-2-yl)-4,5-dihydrooxazole 
• 133909-97-4 N-(trityl)-5-[4?-(methyl)biphenyl-2-yl]-2H-tetrazole 
• 579-75-9 2-Methoxybenzoic acid 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 171515-67-6 2-n-butyl-1-{[2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl]methyl}-1H-imidazole-5-carbaldehyde 
• 76-83-5 trityl chloride 
• 114798-36-6 EXP 3179 
• 124750-99-8 cozaar 

Downstream Products

• 124751-01-5 <2-butyl-4-chloro-1-<<2'-(1H-tetrazol-5-yl)biphenyl-4-yl>methyl>imidazol-5-yl>phenylmethanol 
• 114798-36-6 2-n-Butyl-4-chloro-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-imidazole-5-carboxaldehyde 
• 133909-99-6 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol 
• 1370339-88-0 [3-(3,4-bis-benzyloxy-phenyl)propyl](2-n-butyl-5-chloro-3-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-imidazol-4-ylmethyl)amine 
• 124750-92-1 2-n-butyl-5-chloro-3-[2'-(2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-imidazole-4-carboxylic acid 
• 114798-36-6 EXP 3179 
• 1370339-80-2 1-((2'-(2H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-butyl-4-chloro-1H-imidazole-5-carbaldehyde oxime 

Relevant articles and documents

Synthesis and evaluation of new designed multiple ligands directed towards both peroxisome proliferator-activated receptor-γ and angiotensin II type 1 receptor

Because of the complex biological networks, many pathologic disorders fail to be treated with a molecule directed towards a single target. Thus, combination therapies are often necessary, but they have many drawbacks. An alternative consists in building molecules intended to interact with multiple targets, called designed multiple ligands. We followed such a strategy in order to treat metabolic syndrome, by setting up molecules directed towards both type 1 angiotensin II (AT1) receptor and peroxisome proliferator-activated receptor-γ (PPAR-γ). For this purpose, many molecules were prepared by merging both pharmacophores following three different strategies. Their ability to activate PPAR-γ and to block AT1 receptors were evaluated in vitro. This strategy led to the preparation of many new PPAR-γ activating and AT1 blocking molecules. Among them, some exhibited both activities, highlighting the convenience of this approach.

A process for the preparation of losartan derivatives by chlorination and reduction of the respective 1H-imidazole-5-carbaldehydes

The invention provides a process for the preparation of a sartan derivative of formula (I): wherein R = C2-C7 straight or branched alkyl or C3-C9 cycloalkyl, or a pharmaceutically acceptable salt thereof, comprising the steps of chlorinating and reducing, in any order, a compound of formula (III): wherein R is defined as above to form a compound of formula (VI), wherein R is defined as above and then deprotecting said compound of formula (VI) to obtain the sartan derivative of formula (I), and optionally converting said sartan derivative into one of its pharmaceutically acceptable salts. A preferred embodiment of this invention is a process for the preparation of losartan and, particularly, its potassium salt.

PROCESS FOR PREPARING BIPHENYLTETRAZOLE COMPOUNDS

Method for the preparing biphenyltetrazole compounds which are angiotensin II receptor antagonists or which are useful intermediates to prepare angiotensin II receptor antagonists. An illustrative biphenyl tetrazole compound is 2-n-butyl-4-chloro-1-[(2'-(tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imi dazole-5-methanol, potassium salt.

Practical Synthesis and Regioselective Alkylation of Methyl 4(5)-(Pentafluoroethyl)-2-propylimidazole-5(4)-carboxylate To Give DuP 532, a Potent Angiotensin II Antagonist

DuP 532 (2), which is a potent angiotensin II receptor antagonist, has been prepared by two different routes.One route, which is more practical for large-scale synthesis, required the preparation of methyl 4(5)-(pentafluoroethyl)-2-propylimidazole-5(4)-carboxylate (9).This imidazole was synthesized in five steps from commercially available 11 in 32percent overall yield.Alternate perfluoroalkylation methods of the iodoimidazole precursor 14 are presented.Imidazole 9 is remarkably stable to basic conditions and is alkylated by 2--4'-(bromomethyl) -1,1'-biphenyl (8), giving only the desired regioisomer.A comparison of the alkylation of the trisubstituted precursors and analogues to 9 with 8 indicate that even under mildly basic conditions (K2CO3/DMF), the mechanism is SE2cB (anionic), except for 2-propyl-4(5)-(hydroxymethyl)imidazole (11) which alkylates as a neutral species (SE2')

Tetrazolylphenylboronic acid intermediates for the synthesis of AII receptor antagonists

Novel tetrazolylphenylboronic acids, methods for their preparation, and their use in the syntheses of angiotensin II receptor antagonists are disclosed.

Nonpeptide Angiotensin II Receptor Antagonists: The Discovery of a Series of N-(Biphenylylmethyl)imidazoles as Potent, Orally Active Antihypertensives

A new series of nonpeptide angiotensin II (AII) receptor antagonists has been prepared.These N-(biphenylylmethyl)imidazoles, e.g. 2-butyl-1--4-chloro-5-(hydroxymethyl)imidazole, differ from the previously reported N-(benzamidobenzyl)imidazoles and related compounds in that they produce a potent antihypertensive effect upon oral administration; the earlier series generally were active only when administered intravenously.It has been found that the acidic group at the 2'-position of the biphenyl is essential.Only ortho-substituted acids possess both high affinity for the AII receptor and good oral antihypertensive potency.The carboxylic acid group has been replaced with a variety of acidic isosteres, and the tetrazole ring has been found to be the most effective.The tetrazole derivative, DuP 753, is currently in development for the treatment of hypertension.