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

• 1012341-48-8 (2E,4R)-5-{[1,1'-biphenyl]-4-yl}-4-{[(tert-butoxy)carbonyl]amino}-2-methylpent-2-enoic acid 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 108-30-5 succinic acid anhydride 
• 1039307-95-3 (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoic acid 
• 64-17-5 ethanol 
• 1573000-36-8 (1-([1,1‘-biphenyl]-4-yl)-3-chloropropan-2-yl)pyrrolidine-2,5-dione 
• 1573000-28-8 (S)-1-([1,1’-biphenyl]-4-yl)-3-chloropropan-2-ol 
• 1038924-97-8 (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-(2,5-dioxopyrrol-1-yl)-2-methyl pentanoate 
• 1639970-62-9 (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-(2,5-dioxopyrrol-1-yl)-2-methylpentanoic acid 

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

The preparation method comprises the following steps 1-11: Wherein. ROH (Formula X) is a chiral alcohol and the like, PG is a hydroxy protecting group, a compound of Formula VI and a compound of Formula V are the chiral auxiliary of the present invention. To the invention, the chiral auxiliary base ROH compound and the chiral alcohol X (Formula VI) are used for preparing the chiral auxiliary base-type compound of formula V IV and the compound of Formula XI, and the compound of formula IV can be prepared through three-step simple operation steps of chiral auxiliary base. Be applicable to industrial production.

Preparation method of key component sacubitril of novel anti-heart-failure drug Entresto

The invention relates to a preparation method of a key component sacubitril of a novel anti-heart-failure drug Entresto. The chemical name of sacubitril is 4-(((2S,4R)-1-(1,1'-biphen-4-yl)-5-ethoxy-4-methyl-5-oxopentan-2-yl) amino)-4-oxobutyric acid. According to the method, 4-bromobiphenyl is used as an initial raw material, and the method is simple in process route, low in cost and suitable forindustrial production.

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.