215447-89-5

Usage

Uses

Used in Pharmaceutical Industry:
Benazepril hydrochloride is used as an antihypertensive agent for the treatment of high blood pressure (hypertension). It functions by inhibiting the angiotensin-converting enzyme, which in turn reduces the production of angiotensin II, a potent vasoconstrictor. This leads to vasodilation and a decrease in blood pressure, providing relief for patients suffering from hypertension.
Additionally, as an ACE inhibitor, benazepril hydrochloride is also used to treat congestive heart failure and certain types of chronic kidney disease, as it can help improve the heart's function and slow the progression of kidney damage in some cases.

Upstream product

• 64920-29-2 2-oxo-4-phenylbutanoic acid ethyl ester 
• 86499-53-8 (3S)-3-amino-1-(carboxymethyl)-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one sodium salt 
• 4424-80-0 2,3,4,5-tetrahydro-1H-1-benzo[b]azepin-2-one 
• 92278-69-8 ethyl 3-azido-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one-1-acetate 
• 859635-53-3 3-[[1-(t-butoxy-carbonyl)-3-phenyl-(1S)-propyl]amino]-2,3,4,5-tetrahydro-2-oxo-1H-1-(3S)-benzazepine-1-acetic acid ethyl ester 
• 86541-75-5 benazepril 
• 90315-82-5 ethyl (R)-2-hydroxy-4-phenylbutyrate 
• 159974-68-2 (R)-3,4-dihydroxy-1-phenylbutan-1-one 
• 156386-82-2 trans-γ-3-benzoylprop-2-en-1-ol 
• 109010-59-5 (R)-2-<(4-nitrobenzolsulfonyl)oxy>-4-phenylbuttersaeure-ethylester 
• 29678-81-7 (R)-2-hydroxy4-phenylbutanoic acid 
• 146912-66-5 (R)-2-hydroxy-4-oxo-4-phenylbutanoic acid 
• 1005327-17-2 (R)-1-phenyl-2-(2-phenyl-1,3,2-dioxaborolan-4-yl)ethanone 
• 86499-52-7 (S)-3-amino-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one 

Relevant academic research and scientific papers

Synthesis and biological properties of (carboxyalkyl)amino-substituted bicyclic lactam inhibitors of angiotensin converting enzyme

Syntheses of the potent angiotensin converting enzyme inhibitor (3S)-1-(carboxymethyl)-3-[[(1S)-1-carboxy-3-phenylpropyl]amino]-2,3,4,5 -tetrahydro-1H-[1]benzazepin-2-one (CGS 14831) and the related monoester prodrug (17a; CGS 14824A) are described together with preparative details for six- and eight-membered ring analogues. Inhibitory potencies and in vivo biological activity of the compounds are discussed. The data indicate that 17a has a biological profile comparable to that of enalapril.

Use of convertible isocyanides for the synthesis of benazepril hydrochloride

Herein, we have described a novel and concise synthesis of the potent angiotensin-converting enzyme (ACE) inhibitor, benazepril hydrochloride (7) in trifluoroethanol via an Ugi three-component reaction in shorter reaction times. The key step is the trifluoroacetic acid-mediated hydrolysis of secondary amides (4a and 4b) followed by esterification as a domino process to form corresponding ethyl ester (6). Mainly two universal convertible isocyanides (1a and 1b) were used for the synthesis of benazepril hydrochloride. Graphic abstract: [Figure not available: see fulltext.] Synopsis: An efficient synthesis of benazepril hydrochloride using Ugi three-component reaction.

Synthesis method of benazepril intermediate and benazepril hydrochloride

The invention relates to a synthesis method of a benazepril intermediate and a benazepril hydrochloride. The synthesis method comprises: carrying out a reaction on 3-bromo-2,3,4,5-tetrahydro-1H-[1]-benzoazepine-2-keto-1-tert-butyl acetate and (S)-homophenylalanine, and carrying out dynamic kinetic resolution to obtain a benazepril intermediate; and carrying out an esterification reaction, and introducing hydrogen chloride gas to obtain a benazepril hydrochloride refined product. According to the invention, the benazepril hydrochloride is efficiently prepared by utilizing a dynamic kinetic resolution technology, so the steps are short, the operation is simple, the total yield is high, the atom economy is high, the environmental pollution is small, and the method is suitable for industrial production.

Chloramphenicol base chemistry. Part 10: Asymmetric synthesis of α-hydroxy chiral alcohols via intramolecular Michael additions of γ-hydroxy-α, β-unsaturated enones with chloramphenicol base derived bifunctional urea organocatalysts

We have developed the chloramphenicol base urea-catalyzed intramolecular Michael addition of γ-hydroxy-α, β-unsaturated enones. The oxidation of the resulting products provided facile access to the corresponding α-hydroxy chiral alcohols with good efficiency and enantioselectivity, with the reaction displaying broad substrate scope. The utility of this methodology was further demonstrated by the synthesis of (R)-2-hydroxy-4-phenylbutanoate, which is a key building block for the construction of the ACE inhibitor benazepril hydrochloride.

An improved method for preparing of the benazepril hydrochloride and containing the pharmaceutical composition of the benazepril hydrochloride

The invention discloses an improved preparation method of benazepril hydrochloride and pharmaceutical composition containing the benazepril hydrochloride. With the adoption of the preparation method, the safety is high, the cost is low, the clean production value is high, industrial production is easy to realize, and meanwhile, the pharmaceutical composition is easy to prepare and use.

COMPOSITIONS AND METHODS FOR DIAGNOSING AND TREATING SALT SENSITIVITY OF BLOOD PRESSURE

To characterize the urinary exosome miRNome, microarrays were used to identify the miRNA spectrum present within urinary exosomes from ten individuals that were previously classified for their salt sensitivity status. The present application discloses distinct patterns of selected exosomal miRNA expression that were different between salt-sensitive (SS), salt-resistant (SR), and inverse salt-sensitive (ISS) individuals. These miRNAs can be useful as biomarkers either individually or as panels comprising multiple miRNAs. The present invention provides compositions and methods for identifying, diagnosing, monitoring, and treating subjects with salt sensitivity of blood pressure. The applications discloses panels of miRNAs useful for comparing profiles, and in some cases one or more of the miRNAs in a panel can be used. The miRNAs useful for distinguishing SS and SR or ISS and SR subjects. One or more of the 45 miRNAs can be used. Some of the miRNAs have not been previously reported to be circulating. See those miRNAs with asterisks in FIG. 1 and below. The present invention encompasses the use of one or more of these markers for identifying and diagnosing SR, SS, and ISS subjects.

IMPROVED PROCESS FOR CRYSTALLIZATION OF BENAZEPRIL HYDROCHLORIDE

An improved process for the crystallization of benazepril hydrochloride to obtain in at least 99.8% diastereomeric purity. The process comprises making a concentrated solution of benazepril hydrochloride in ethanol and adding the resulting solution to a non-solvent diisopropyl ether.

CRYSTALLINE POLYMORPHS OF BENAZEPRIL HYDROCHLORIDE

The present invention relates to a specific polymorph form of crystalline benazepril hydrochloride referred to as Form B, methods for producing this form of benazepril hydrochloride, compositions containing it, and methods for using it.

PROCESS FOR PREPARATION OF BENAZEPRIL

The present invention relates to an improved process for preparation of highly pure benazepril of Formula I, wherein R is hydrogen or pharmacologically acceptable salt thereof by completely eliminating the impurity of 7-bromo analogue of benazepril of Formula Ia, wherein R is bromo group.

BIS-DICARBOXYLIC ACID SALTS OF BENAZEPRIL AND PREPARATION OF BENAZEPRIL VIA THESE SALTS

Dicarboxylic acid salts of compounds of the formula (II) wherein R represents a selectively removable protecting group; and (S) denotes the (S)-configuration of the asymmetric carbon atoms, which are useful as intermediates for the preparation of benazepril or pharmaceutically acceptable salts thereof.