1103522-45-7

Basic information

• Product Name: ACT-132577
• Synonyms: ACT-132577;N-[5-(4-Bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy]-4-pyrimidinyl]sulfamide;N-Despropyl Macitentan;Aprocitentan
• CAS NO: 1103522-45-7
• Molecular Formula: C₁₆H₁₄Br₂N₆O₄S
• Molecular Weight: 546.19316
• Product Categories: APIS
• Mol File: 1103522-45-7.mol

Chemical Properties

• Boiling Point: 705.0±70.0 °C(Predicted)
• Appearance: /
• Density: 1.841±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly, Heated), Methanol (Slightly, Heated)
• PKA: 13.56±0.60(Predicted)
• CAS DataBase Reference: ACT-132577(CAS DataBase Reference)
• NIST Chemistry Reference: ACT-132577(1103522-45-7)
• EPA Substance Registry System: ACT-132577(1103522-45-7)

Safety Data

• Hazardous Substances Data: 1103522-45-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
ACT-132577 is used as a therapeutic agent for the treatment of pulmonary arterial hypertension (PAH). It functions as an endothelin receptor antagonist, which helps in reducing the constriction of blood vessels and improving blood flow in PAH patients. This makes it a valuable drug for managing the symptoms and progression of PAH, ultimately improving the quality of life for those affected by the condition.

Upstream product

• 1246922-88-2 2-((5-bromopyrimidin-2-yl)oxy)ethan-1-ol 
• 441796-08-3 N-[5-(4-bromophenyl)-6-(2-hydroxyethoxy)-4-pyrimidinyl]-N'-benzyl-sulfamide 
• 441797-42-8 N-[5-(4-bromophenyl)-6-chloro-4-pyrimidinyl]-N'-benzyl-sulfamide 
• 706811-25-8 5-(4-bromophenyl)-4,6-dihydroxypyrimidine 
• 149506-35-4 2-(4-bromophenyl)-malonic acid dimethyl ester 
• 146533-41-7 5-(4-bromophenyl)-4,6-dichloropyrimidine 
• 1878-68-8 2-(4-bromophenyl)-acetic acid 
• 41841-16-1 (4-bromo-phenyl)-acetic acid methyl ester 
• 441796-09-4 benzylsulfamic acid {5-(4-bromophenyl)-6-[2-(5-bromopyrimidin-2-yloxy)-ethoxy]-pyrimidine-4-yl}-amide 

Relevant articles and documents

CRYSTALLINE FORMS OF A 4-PYRIMIDINESULFAMIDE DERIVATIVE APROCITENTAN

The present invention concerns novel crystalline forms of {5-(4-bromo-phenyl)-6 [2 (5 bromo-pyrimidin-2-yloxy)-ethoxy]-pyrimidin-4-yl}-sulfamide, processes for the preparation thereof, pharmaceutical compositions comprising said crystalline forms, pharmac

COMBINATION OF A 4-PYRIMIDINESULFAMIDE DERIVATIVE WITH AN SGLT-2 INHIBITOR FOR THE TREATMENT OF ENDOTHELIN RELATED DISEASES

The present invention concerns the compound aprocitentan, {5-(4-bromo-phenyl)-6-[2-(5-bromo-pyrimidin-2-yloxy)-ethoxy]-pyrimidin-4-yl}-sulfamide and its use as endothelin receptor antagonist, in combination with an SGLT-2 inhibitor. The invention further

PROCESS FOR MANUFACTURING PYRIMIDINE SULFAMIDE DERIVATIVES

The invention relates to a process for manufacturing the compound of formula I wherein R is H, (C1-C6)alkyl or benzyl, or a salt thereof, said process comprising the reaction of the compound of formula I-1 wherein X is Br, Cl or F, or a salt thereof, with the compound of formula I-2 wherein R is H, C1-C6)alkyl or benzyl, or a salt thereof, in the presence of a base, and, when X is Br or Cl, in the presence of tetra-n-butyl ammonium fluoride hydrate or cesium fluoride. The invention further relates to the compound of formula I-1 and uses thereof.

4-PYRIMIDINESULFAMIDE DERIVATIVE

The invention relates to the compound of structural formula (I) and the salts thereof. Said compound is useful as endothelin receptor antagonist. The invention further relates to a process for preparing said compound.

The discovery of N -[5-(4-bromophenyl)-6-[2-[(5-bromo-2-pyrimidinyl)oxy] ethoxy]-4-pyrimidinyl]- N ′-propylsulfamide (macitentan), an orally active, potent dual endothelin receptor antagonist

Starting from the structure of bosentan (1), we embarked on a medicinal chemistry program aiming at the identification of novel potent dual endothelin receptor antagonists with high oral efficacy. This led to the discovery of a novel series of alkyl sulfamide substituted pyrimidines. Among these, compound 17 (macitentan, ACT-064992) emerged as particularly interesting as it is a potent inhibitor of ETA with significant affinity for the ET B receptor and shows excellent pharmacokinetic properties and high in vivo efficacy in hypertensive Dahl salt-sensitive rats. Compound 17 successfully completed a long-term phase III clinical trial for pulmonary arterial hypertension.

4-PYRIMIDINESULFAMIDE DERIVATIVE

The invention relates to the compound of structural formula (I) and the salts thereof. Said compound is useful as endothelin receptor antagonist. The invention further relates to a process for preparing said compound.