149709-63-7

Basic information

• Product Name: LCZ 696 Impurity C
• Synonyms: LCZ 696 Impurity C;(2S,4S)-Sacubitril;4-(((2S,4S)-1-([1,1'-biphenyl]-4-yl)-5-ethoxy-4-methyl-5-oxopentan-2-yl)amino)-4-oxobutanoic acid;[1,1'-Biphenyl]-4-pentanoic acid, γ-[(3-carboxy-1-oxopropyl)amino]-α-methyl-, ethyl ester, [S-(R*,R*)]- (9CI);Sacubitril Impurity C
• CAS NO: 149709-63-7
• Molecular Formula: C24H29NO5
• Molecular Weight: 411.49076
• Mol File: 149709-63-7.mol
• Article Data: 37

Chemical Properties

• Boiling Point: 656.9±55.0 °C(Predicted)
• Appearance: /
• Density: 1.151±0.06 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.72±0.10(Predicted)
• Stability: Moisture Sensitive
• CAS DataBase Reference: LCZ 696 Impurity C(CAS DataBase Reference)
• NIST Chemistry Reference: LCZ 696 Impurity C(149709-63-7)
• EPA Substance Registry System: LCZ 696 Impurity C(149709-63-7)

Safety Data

• Hazardous Substances Data: 149709-63-7(Hazardous Substances Data)

Usage

Description

LCZ 696 Impurity C, also known as (2S,4S)-Sacubitril, is an impurity found in Sacubitril (S080895), which is an antihypertensive drug. It is a pharmaceutical compound with potential applications in the medical field due to its association with the active drug.

Uses

Used in Pharmaceutical Industry:
LCZ 696 Impurity C is used as an impurity in the production of Sacubitril (S080895) for its role in the development of antihypertensive drugs. The presence of this impurity may affect the efficacy, safety, and quality of the final drug product, making it essential to monitor and control its levels during the manufacturing process.
Used in Research and Development:
LCZ 696 Impurity C is used as a research compound to study its properties, potential interactions with other substances, and its role in the overall effectiveness of Sacubitril (S080895) as an antihypertensive drug. This research can help in understanding the drug's mechanism of action, optimizing its formulation, and improving its therapeutic potential.
Used in Quality Control and Regulatory Compliance:
LCZ 696 Impurity C is used as a reference material in the quality control and regulatory compliance processes for Sacubitril (S080895). It helps ensure that the drug meets the required standards for purity, potency, and safety, and that the manufacturing process is consistent and reliable.
Used in Drug Safety Assessment:
LCZ 696 Impurity C is used in drug safety assessment to evaluate the potential risks and side effects associated with its presence in the final drug product. This information is crucial for determining the acceptable levels of the impurity in the drug and for setting appropriate safety guidelines for its use in patients.

Upstream product

• 108-30-5 succinic acid anhydride 
• 753421-85-1 ethyl (γS)-γ-amino-α-methyl<1,1'-biphenyl>-4-pentanoate 
• 108-91-8 cyclohexylamine 
• 149690-13-1 ethyl (2S,4S)-4-amino-5-[(1,1'-biphenyl)-4-yl]-2-methylpentanoate hydrochloride 
• 149690-05-1 α-ethyl (αR,γS)-γ-<(3-carboxy-1-oxopropyl)amino>-α-methyl<1,1'-biphenyl>-4-pentanoate monosodium salt 
• 1639970-62-9 (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-(2,5-dioxopyrrol-1-yl)-2-methylpentanoic acid 
• 1038924-97-8 (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-(2,5-dioxopyrrol-1-yl)-2-methyl pentanoate 

Downstream Products

• 149709-63-7 α-ethyl (αS,γS)-γ-<(3-carboxy-1-oxopropyl)amino>-α-methyl<1,1'-biphenyl>-4-pentanoate 
• 149690-05-1 α-ethyl (αR,γS)-γ-<(3-carboxy-1-oxopropyl)amino>-α-methyl<1,1'-biphenyl>-4-pentanoate monosodium salt 

Relevant articles and documents

Preparation method of sacubitril valsartan sodium

The invention provides a preparation method of sacubitril valsartan sodium, and belongs to the field of medical chemistry. The preparation method comprises the following steps: by using a compound S309A03 as a raw material, carrying out hydrogenation reaction to generate a compound BPA08, reacting the compound BPA08 in ethanol to generate a compound SAC01, reacting the compound SAC01 with succinicanhydride to generate a compound SAC02, optionally reacting the compound SAC02 with sodium hydroxide, and reacting the compound SAC03 with calcium chloride to generate a compound SAC04; and subjecting the compound SAC04 to acid treatment to obtain a compound YJX01, and enabling the compound YJX01 to react with VST in a single solvent in the presence of sodium hydroxide to prepare the compound YJX02. The preparation method disclosed by the invention is simple to operate, the time required by the process is reduced, the total yield of the process route is greatly improved, an unexpected technical effect is obtained, impurities in the process are removed, and a product with higher purity is obtained. The method has mild process conditions and easily available raw materials, and is suitable for industrial amplification.

Preparation method of neprilysin inhibitor intermediate

The invention discloses a preparation method for an enkephalinase inhibitor intermediate. According to the preparation method, a target compound with a formula I as described in the specification is prepared by using a compound as shown in a formula IV which is described in the specification as an initial material through a reaction with few steps, wherein the compound with the formula I can be used for preparation of an enkephalinase inhibitor drug namely Sacubtril. In the formula I and the formula IV, R is selected from the group consisting of H, methyl, ethyl or other lower alkyl.

Optimization and process improvement for LCZ696 by employing quality by design (QbD) principles

Efforts toward optimization and improvement for the synthesis of LCZ696 employing design of experiment (DoE) principles are described. By increasing the purity of intermediates and mitigating impurity risk during each step, a telescoped process was developed via removal of isolation of intermediates with the overall yield increased by 28.5% from 45.3% to 73.8%. And the whole production cycle was also shortened from 12 days to 7 days with simplified operations and restored process greenness. Meanwhile, the corresponding impurity profile was thus studied in detail and well documented.