150726-89-9

Usage

Uses

Used in Organic Synthesis:
Dimethyl 2-(2-methoxyphenoxy)malonate is used as a synthetic intermediate for the creation of various organic compounds. Its chemical structure allows it to participate in a range of reactions, making it a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Dimethyl 2-(2-methoxyphenoxy)malonate is used as a key component in the development of new drugs. Its unique properties enable it to be incorporated into the molecular structures of potential therapeutic agents, contributing to their overall effectiveness and pharmacological profiles.
Used in Agrochemical Industry:
Dimethyl 2-(2-methoxyphenoxy)malonate is also utilized in the agrochemical industry for the synthesis of novel compounds with potential applications in pest control, crop protection, and other agricultural practices. Its incorporation into these compounds can lead to the development of more effective and environmentally friendly solutions for various agricultural challenges.
Used in Specialty Chemicals:
In the specialty chemicals sector, Dimethyl 2-(2-methoxyphenoxy)malonate is employed as a crucial ingredient in the production of various high-value chemicals. Its unique properties make it an essential component in the synthesis of compounds used in industries such as plastics, coatings, and adhesives, among others.

InChI:InChI=1/C12H14O6/c1-15-8-6-4-5-7-9(8)18-10(11(13)16-2)12(14)17-3/h4-7,10H,1-3H3

Upstream product

• 1878-85-9 (2-methoxyphenoxy)acetic acid 
• 38768-62-6 methyl (2-methoxyphenoxy) ethanoate 
• 616-38-6 carbonic acid dimethyl ester 
• 28868-76-0 2-chlorodimethylmalonate 
• 90-05-1 2-methoxy-phenol 

Downstream Products

• 202288-08-2 5-(2-methoxy-phenoxy)-1H-pyrimidine-4,6-dione 
• 329923-15-1 4,6-dihydroxy-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-pyrimidine 
• 329924-93-8 5-(o-methoxyphenoxy)-4,6-dihydroxy-2-methyl-pyrimidine 
• 150727-22-3 5-(o-methoxyphenoxy)-4,6-dihydroxy-pyrimidine 
• 167403-76-1 5-(2-methoxy-phenoxy)-2-(morpholin-4-yl)-4,6(1H,5H)-pyrimidinedione 
• 184779-24-6 4,6-dihydroxy-5-(2-methoxyphenoxy)-2-methylthiopyrimidine 
• 441797-61-1 C₂₂H₁₉ClN₆O₄S 
• 441797-50-8 C₂₃H₂₀ClN₅O₄S 
• 441797-53-1 C₂₁H₂₁ClN₄O₄S 
• 441797-63-3 C₁₈H₁₇ClN₄O₄S 
• 441797-09-7 N-(6-(2-hydroxyethoxy)-2-methylsulfanyl-5-(2-methoxyphenoxy)pyrimidin-4-yl)-N'-benzylsulfamide 
• 441797-10-0 N-(6-(2-hydroxyethoxy)-2-methylsulfonyl-5-(2-methoxyphenoxy)pyrimidin-4-yl)-N'-benzylsulfamide 
• 1393813-68-7 N-(6-(2-hydroxyethoxy)-2-(2-methoxyethoxy)-5-(2-methoxyphenoxy)pyrimidin-4-yl)-N'-benzylsulfamide 
• 473537-04-1 4,6-dichloro-5-(2-methoxy-phenoxy)-2-pyrazin-2-yl-pyrimidine 

Relevant academic research and scientific papers

Metabolism study and biological evaluation of bosentan derivatives

Bosentan, the first-in-class drug used in treatment of pulmonary arterial hypertension, is principally metabolized by the cytochromes P450, and it is responsible for cytochromes induction and drug-drug interaction events with moderate to severe consequences. A strategy to reduce drug-drug interactions consists of increasing the metabolic stability of the perpetrator, and fluorinated analogues are often designed to block the major sites of metabolism. In this paper bosentan analogues were synthesized, and their metabolism and biological activity were evaluated. All synthesized compounds showed an improved metabolic stability towards CYP2C9, with one maintaining a moderate antagonist effect towards the ETA receptor.

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.

AN IMPROVED PROCESS FOR THE PREPARATION OF BOSENTAN

The present application provides purification of Bosentan crude by making its crystalline potassium salt, which is further converted to Bosentan (I) with bis-sulfonamide (VIII) and deshydroxyethyl (IX) impurities to less than 0.2% by HPLC analysis.

Arylalkane-sulfonamides having endothelin-antagonist activity

The invention relates to novel aryl-alkane-sulfonamides and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as endothelin receptor antagonists.

Butyne diol derivatives

The present invention relates to novel butyne diol derivatives of the general formula I and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more compounds of the general formula I and especially their use as endothelin receptor antagonists.

6 alkoxy-4-pyrimidinyl bis-sulfonamides

The present invention relates to novel bis-sulfonamides represented, for example, by formula I below and a pure diastereomer, a mixture of diastereomers, a diastereomeric racemate, a mixture of diastereomeric racemates and meso-forms and a pharmaceutically acceptable salt thereof, wherein R1represents aryl; aryl-lower alkyl; aryl-lower alkenyl; heteroaryl; or heteroaryl-lower alkyl; and R2represents lower alkyl; trifluoromethyl; lower alkoxy-lower alkyl; lower alkenyl; lower alkynyl; aryl; aryl-lower alkyl; aryl-lower alkenyl; heterocyclyl; heterocyclyl-lower alkyl; heteroaryl; heteroaryl-lower alkyl; cycloalkyl; or cycloalkyl-lower alkyl. The present invention also relates to a process for manufacturing those compounds, pharmaceutical compositions containing one or more of those compounds as endothelin antagonists, and a method of treating a subject having a disorder involving endothelin with the compounds of the invention.

Synthesis and structure-activity relationships of potent and orally active sulfonamide ETB selective antagonists

The synthesis and structure-activity relationships of a series of N-pyrimidinyl benzenesulfonamides as ETB selective antagonists are described. N-Isoxazolyl benzenesulfonamide 1a, previously reported, was selected as a lead compound, and isosteric replacement of the isoxazole ring of 1a with a pyrimidine ring led to the discovery of the highly potent ETB selective antagonist 6e with oral bioavailability. Modification of the terminal aldehyde group at the 6-position of the pyrimidine ring was investigated, and malonate 15b and acylhydrazone 16f were found to be equipped to aldehyde 6e. Compound 6e showed ETB antagonistic activity on in vivo evaluation. Copyright

SULFONAMIDES

The novel sulfonamides of formula I, STR1 in which the symbols R. sup.1-R 9, R a, R b, X, Y and n have the significance given in the description and salts thereof can be used for the treatment of circulatory disorders, especially hypertension, ischemia, vasopasms and angina pectoris.