252017-04-2

Basic information

• Product Name: AZD7545
• Synonyms: AZD7545;AZD7545/AZD-7545;4-[[3-Chloro-4-[[(2R)-3,3,3-trifluoro-2-hydroxy-2-methyl-1-oxopropyl]amino]phenyl]sulfonyl]-N,N-dimethylbenzamide;(R)-4-(3-chloro-4-(3,3,3-trifluoro-2-hydroxy-2-methylpropanamido)phenylsulfonyl)-N,N-dimethylbenzamide;AZD7545,(R)-4-(3-chloro-4-(3,3,3-trifluoro-2-hydroxy-2-methylpropanamido)phenylsulfonyl)-N,N-dimethylbenzamide
• CAS NO: 252017-04-2
• Molecular Formula: C₁₉H₁₈ClF₃N₂O₅S
• Molecular Weight: 478.8698296
• Product Categories: API;Inhibitors
• Mol File: 252017-04-2.mol

Chemical Properties

• Boiling Point: 683.1±55.0 °C(Predicted)
• Appearance: /
• Density: 1.473±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: ≥21.85 mg/mL in DMSO; insoluble in H2O; ≥15.63 mg/mL in EtOH with ultrasonic
• PKA: 10.39±0.29(Predicted)
• CAS DataBase Reference: AZD7545(CAS DataBase Reference)
• NIST Chemistry Reference: AZD7545(252017-04-2)
• EPA Substance Registry System: AZD7545(252017-04-2)

Safety Data

• Hazardous Substances Data: 252017-04-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
AZD 7545 is used as a therapeutic agent for the treatment of metabolic disorders, particularly those related to glucose metabolism and insulin resistance. Its ability to increase PDH activity and improve glucose profiles in obese, insulin-resistant rats makes it a promising candidate for the development of treatments for conditions such as type 2 diabetes and obesity.
Used in Research Applications:
AZD 7545 is used as a research tool for studying the role of PDH kinases in cellular metabolism and the regulation of glucose homeostasis. Its selective inhibition of PDK2, PDK1, and PDK3 allows researchers to investigate the specific functions and interactions of these enzymes in various cellular processes, contributing to a better understanding of metabolic pathways and the development of targeted therapies for related diseases.

references

[1] morrell j a, orme j, butlin r j, et al. azd7545 is a selective inhibitor of pyruvate dehydrogenase kinase 2. biochemical society transactions, 2003, 31(6): 1168-1170.[2] mayers r m, butlin r j, kilgour e, et al. azd7545, a novel inhibitor of pyruvate dehydrogenase kinase 2 (pdhk2), activates pyruvate dehydrogenase in vivo and improves blood glucose control in obese (fa/fa) zucker rats. biochemical society transactions, 2003, 31(6): 1165-1167.

Upstream product

• 79-37-8 oxalyl dichloride 
• 252016-13-0 (R)-N-[2-chloro-4-(4-carboxyphenylsulphonyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide 
• 1360607-88-0 C₁₃H₁₀ClNO₂S 
• 1083428-66-3 C₁₅H₁₅ClN₂OS 
• 1360607-89-1 4-((3-chloro-4-(3,3,3-trifluoro-2-hydroxy-2-methylpropanamido)phenyl)thio)N,N-dimethylbenzamide 
• 1286573-32-7 C₇H₅ClN₂S 
• 1360607-85-7 C₁₃H₉ClN₂S 
• 1194-02-1 4-fluorobenzonitrile 
• 95-51-2 o-chloroaniline 
• 586-75-4 4-chlorobenzoyl chloride 
• 1122-40-3 2-chloro-4-mercaptoaniline 
• 3226-47-9 4-amino-3-chlorophenyl thiocyanate 
• 18469-37-9 4-bromo-N,N-dimethylbenzamide 
• 586-76-5 4-Bromobenzoic acid 

Relevant articles and documents

Process development and scale-up of AZD7545, a PDK inhibitor

A brief comparison of the early manufacturing routes to AZD7545 is given. Process development of the preferred long-term manufacturing route is reported in detail, and changes from the initial kilogram-scale route are discussed. Scale-up experience from t

Kepner-Tregoe decision analysis as a tool to aid route selection. Part 2. Application to AZD7545, a PDK inhibitor

Kepner-Tregoe decision analysis was formally used as an aid to route selection, as outlined in the preceding paper. Over 40 paper routes were assessed for suitability for both immediate and longer term manufacture of AZD7545, a compound in the early stages of development. Eight routes were then investigated in full in the laboratory, and a further four in part, over a period of 3-4 months. From this exercise, the preferred long-term manufacturing route was identified before the first pilot scale manufacture had been completed. This route selection exercise worked well in this case where a large number of potential routes had to be considered using limited resources. It was also an effective means of bringing some long-term manufacturing issues to the fore at an early stage in development.

Use of compounds for the elevation of pyruvate dehydrogenase activity

The use of compounds of the formula (I), and salts thereof; and pharmaceutically acceptable in vivo cleavable prodrugs of said compound of formula (I); and pharmaceutically acceptable salts of said compound or said prodrugs: wherein: Ring C is phenyl or a carbon linked heteroaryl ring substituted as defmed within; R1is an ortho substituent as defined within; n is 1 or 2; A—B is a linking group as defined within; R2and R3are as defined within; R4is hydroxy, hydrogen, halo, amino or methyl; in the manufacture of a medicament for use in the elevation of PDH activity in warm-blooded animals such as humans is described. Pharmaceutical compositions, methods and processes for preparation of compounds of formula (I) are also described.