802904-66-1

Basic information

• Product Name: 7-Methyl-5-[(3-piperazin-1-ylMethyl)-1,2,4-oxadiazol-5-yl-]-2-[4-(trifluoroMethoxy)benzyl]-2,3-dihydro-1H-isoindol-1-one Methanesulphonate
• Synonyms: 7-Methyl-5-[(3-piperazin-1-ylMethyl)-1,2,4-oxadiazol-5-yl-]-2-[4-(trifluoroMethoxy)benzyl]-2,3-dihydro-1H-isoindol-1-one Methanesulphonate;AZD1981;1H-Indole-1-acetic acid, 4-(acetylamino)-3-[(4-chlorophenyl)thio]-2-methyl-;AZD1981, >=98%;4-(Acetylamino)-3-[(4-chlorophenyl)thio]-2-methyl-1H-indole-1-acetic acid
• CAS NO: 802904-66-1
• Molecular Formula: C25H28F3N5O6S
• Molecular Weight: 583.5799296
• EINECS: -0
• Product Categories: Inhibitors
• Mol File: 802904-66-1.mol

Chemical Properties

• Boiling Point: 676.8±55.0 °C(Predicted)
• Appearance: /
• Density: 1.37±0.1 g/cm3(Predicted)
• Solubility: insoluble in H2O; insoluble in EtOH; ≥19.8 mg/mL in DMSO
• PKA: 4.06±0.10(Predicted)
• CAS DataBase Reference: 7-Methyl-5-[(3-piperazin-1-ylMethyl)-1,2,4-oxadiazol-5-yl-]-2-[4-(trifluoroMethoxy)benzyl]-2,3-dihydro-1H-isoindol-1-one Methanesulphonate(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Methyl-5-[(3-piperazin-1-ylMethyl)-1,2,4-oxadiazol-5-yl-]-2-[4-(trifluoroMethoxy)benzyl]-2,3-dihydro-1H-isoindol-1-one Methanesulphonate(802904-66-1)
• EPA Substance Registry System: 7-Methyl-5-[(3-piperazin-1-ylMethyl)-1,2,4-oxadiazol-5-yl-]-2-[4-(trifluoroMethoxy)benzyl]-2,3-dihydro-1H-isoindol-1-one Methanesulphonate(802904-66-1)

Safety Data

• Hazardous Substances Data: 802904-66-1(Hazardous Substances Data)

Usage

Uses

AZD 1981 is an orally available selective DP2 antagonist in the treatment of asthma.

Biological Activity

azd1981 is a selective, orally bioavailable and potent antagonist of the chemoattractant receptor-homologous expressed on th2 lymphocytes receptor (crth2 or dp2) with an ic50 value of 4 nm [1].azd1981 has shown to inhibit eosinophil migration with a pic50 value of 7.6±0.1. azd1981 could block chemotaxis of dp2+ t-cell lines with a pic50 value of 7.5±0.1. azd1981 has been demonstrated to inhibit pgd2 binding to mouse, rat, rabbit, dog, guinea pig and human dp2. azd1981 could inhibit shape change induced by dp2 in dog and guinea pig granulocytes as well as in human eosinophils and basophils in blood [2].

references

[1] luker t1, bonnert r, brough s, cook ar, dickinson mr, dougall i, logan c, mohammed rt, paine s, sanganee hj, sargent c, schmidt ja,teague s, thom s. substituted indole-1-acetic acids as potent and selective crth2 antagonists-discovery of azd1981. bioorg med chem lett. 2011 nov 1;21(21):6288-92. [2] schmidt ja1, bell fm, akam e, marshall c, dainty ia, heinemann a, dougall ig, bonnert rv, sargent ca. biochemical and pharmacological characterization of azd1981, an orally available selective dp2 antagonist in clinical development for asthma. br j pharmacol. 2013 apr;168(7):1626-38.

Upstream product

• 628737-13-3 [3-(4-chlorophenylsulfanyl)-2-methyl-4-nitro-1H-indol-1-yl]acetic acid ethyl ester 
• 628737-12-2 3-(4-chlorophenylsulfanyl)-2-methyl-4-nitro-1H-indole 
• 628737-15-5 [4-amino-3-(4-chlorophenylsulfanyl)-2-methylindol-1-yl] acetic acid ethyl ester 
• 1142-19-4 4,4'-dichlorodiphenyl disulfide 
• 1260673-30-0 ethyl [3-(4-chlorophenylsulfanyl)-4-(hydroxyimino)-2-methyl-4,5,6,7-tetrahydro-1H-indol-1-yl]acetate 
• 1260673-41-3 N-[3-(4-chlorophenylsulfanyl)-2-methyl-4,5,6,7-tetrahydro-1H-indol-4-ylidene]hydroxylamine 
• 1260673-29-7 ethyl (2-methyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-1-yl)acetate 
• 1260673-40-2 3-(4-chlorophenylsulfanyl)-2-methyl-4,5,6,7-tetrahydro-1H-indol-4-one 
• 1260673-37-7 2-(2-methyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-1-yl)acetic acid 
• 1260673-36-6 [3-(4-chlorophenylsulfanyl)-2-methyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-1-yl]acetic acid 
• 1260673-31-1 ethyl [3-(4-chlorophenylsulfanyl)-2-methyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-1-yl]acetate 
• 1260673-38-8 [3-(4-chlorophenylsulfanyl)-4-(hydroxyimino)-2-methyl-4,5,6,7-tetrahydro-1H-indol-1-yl]acetic acid 
• 108-24-7 acetic anhydride 
• 1260673-33-3 ethyl [4-(hydroxyimino)-2-methyl-4,5,6,7-tetrahydro-1H-indol-1-yl]acetate 

Relevant articles and documents

Development of scalable manufacturing routes to AZD1981. Application of the Semmler-Wolff aromatisation for synthesis of the indole-4-amide Core

A safe and efficient synthesis of AZD1981 is described in which the indole 4-amide core is formed by a Semmler-Wolff aromatisation of a cyclohexenone oxime fused to a pyrrole ring. The substrate was obtained via Paal-Knorr pyrrole synthesis, followed by i

Substituted indole-1-acetic acids as potent and selective CRTh2 antagonists-discovery of AZD1981

Novel indole-3-thio-, 3-sulfonyl- and 3-oxy-aryl-1-acetic acids are reported which are potent, selective antagonists of the chemoattractant receptor-homologous expressed on Th2 lymphocytes receptor (CRTh2 or DP2). Optimization required maintenance of high

INTERMEDIATES AND PROCESSES FOR THE PREPARATION OF 4- (ACETYLAMINO) ) -3- [ (4-CHLORO-PHENYL) THIO] -2-METHYL-1H-INDOLE-1-ACETIC ACID

The invention relates to compounds of formula (X), and salts thereof, and their use as intermediates in improved manufacturing processes for the synthesis of pharmaceutical compound of formula (I): X is =0, =N-0H or =N-OC(O)Me; Y is hydrogen, PhS- or p-ch

NOVEL PROCESS

The invention relates to a novel process for the preparation of substituted indoles which are useful as therapeutic agents.

NOVEL SUBSTITUTED 3-SULFUR INDOLES

The present invention relates to substituted indoles useful as pharmaceutical compounds for treating respiratory disorders.