170687-82-8

Basic information

• Product Name: (R)-N-(2-(benzyloxy)-5-(2-broMo-1-hydroxyethyl)phenyl)MethanesulfonaMide
• Synonyms: (R)-N-(2-(benzyloxy)-5-(2-broMo-1-hydroxyethyl)phenyl)MethanesulfonaMide;(R)-N-[5-(2-Bromo-1-hydroxyethyl)-2-(phenylmethoxy)phenyl]methanesulfonamide
• CAS NO: 170687-82-8
• Molecular Formula: C₁₆H₁₈BrNO₄S
• Molecular Weight: 400.28742
• Mol File: 170687-82-8.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Density: 1.546
• CAS DataBase Reference: (R)-N-(2-(benzyloxy)-5-(2-broMo-1-hydroxyethyl)phenyl)MethanesulfonaMide(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-N-(2-(benzyloxy)-5-(2-broMo-1-hydroxyethyl)phenyl)MethanesulfonaMide(170687-82-8)
• EPA Substance Registry System: (R)-N-(2-(benzyloxy)-5-(2-broMo-1-hydroxyethyl)phenyl)MethanesulfonaMide(170687-82-8)

Safety Data

• Hazardous Substances Data: 170687-82-8(Hazardous Substances Data)

Upstream product

• 14347-25-2 2-Bromo-1-[4-phenylmethoxy-3-[(methylsulfonyl)amino]phenyl]ethanone 
• 124-63-0 methanesulfonyl chloride 
• 333796-54-6 (1R)-1-[3-amino-4-(phenylmethoxy)phenyl]-2-bromoethan-1-ol 
• 823-96-1 Trimethylboroxine 
• 22348-32-9 (R)-α,α-diphenylprolinol 
• 6322-56-1 4'-hydroxy-3'-nitroacetophenone 
• 14347-05-8 4-benzyloxy-3-nitroacetophenone 
• 43229-01-2 4-benzyloxy-3-nitrophenacyl bromide 
• 14347-15-0 1-[4-phenylmethoxy-3-aminophenyl]ethanone 
• 14347-08-1 1-[4-Phenylmethoxy-3-[(methylsulfonyl)amino]phenyl]ethanone 
• 100-39-0 benzyl bromide 
• 188690-82-6 (R)-2-bromo-1-(4-benzyloxy-3-nitrophenyl)ethanol 

Downstream Products

• 861448-79-5 (3-{2-[(2R)-2-(4-benzyloxy-3-methanesulfonylaminophenyl)-2-(tert-butyldimethylsilanyloxy)ethylamino]-2-methylpropyl}phenyl)acetic acid methyl ester 
• 861448-88-6 methyl (3-{2-[((2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-{4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-2-methylpropyl}phenyl)acetate 
• 861448-89-7 (3-{2-[(2R)-2-(tert-butyldimethylsilyloxy)-2-(4-hydroxy-3-methanesulfonylaminophenyl)ethylamino]-2-methylpropyl}phenyl)acetic acid 
• 862540-80-5 2-[3-(2-{[(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-{4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl]amino}-2-methylpropyl)phenyl]-N-[(4'-hydroxybiphenyl-3-yl)methyl]acetamide 
• 861448-91-1 ethyl (3-{2-[((2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-{4-benzyloxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-2-methylpropyl}phenyl)acetate 
• 861448-92-2 ethyl (R)-2-(3-{2-[2-hydroxy-2-(4-benzyloxy-3-methanesulfonamidophenyl)ethylamino]-2-methylpropyl}phenyl)acetate 
• 861448-93-3 [3-(2-{[(2R)-2-{4-(benzyloxy)-3-[(methylsulfonyl)amino]phenyl}-2-hydroxyethyl]amino}-2-methylpropyl)phenyl]acetic acid 
• 921598-25-6 2-(3-{2-[((2R)-2-{4-benzyloxy-3-[(methylsulfonyl)amino]phenyl}-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)amino]-2-methylpropyl}phenyl)-N-[(4'-hydroxybiphenyl-3-yl)methyl]-acetamide 
• 373360-06-6 4-(4-{4-[(2R)-2-hydroxy-2-(4-hydroxy-3-methanesulfonylaminophenyl)ethylamino]piperidin-1-yl}phenylsulfamoyl)phenoxyacetic acid methyl ester 
• 373360-02-2 methyl 3-[(4-{4-[((2R)-2-hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-1-piperidinyl}anilino)sulfonyl]-2-thiophenecarboxylate 

Relevant articles and documents

Microbial synthesis of chiral intermediates for β-3-receptor agonists

Chiral intermediates were prepared by biocatalytic processes for the chemical synthesis of β-3-receptor agonists. These include: (i) the microbial reduction of 4-benzyloxy-3-methanesulfonylamino-2′-bromoacetophenone 1 to the corresponding (R)-alcohol 2 by

Inhalation by design: Novel ultra-long-acting β2- adrenoreceptor agonists for inhaled once-daily treatment of asthma and chronic obstructive pulmonary disease that utilize a sulfonamide agonist headgroup

A novel series of potent and selective sulfonamide derived β2-adrenoreceptor agonists are described that exhibit potential as inhaled ultra-long-acting bronchodilators for the treatment of asthma and chronic obstructive pulmonary disease. Analogues from this series mediate very long-lasting smooth muscle relaxation in guinea pig tracheal strips. The sulfonamide agonist headgroup confers high levels of intrinsic crystallinity that could relate to the acidic sulfonamide motif supporting a zwitterionic form in the solid state. Optimization of pharmacokinetic properties was achieved through targeted introduction of a phenolic moiety to support rapid phase II clearance, thereby minimizing systemic exposure following inhalation and reducing systemically mediated adverse events. Compound 38 (PF-610355) is identified as a clinical candidate from this series, with in vivo duration of action studies confirming its potential for once-daily use in humans. Compound 38 is currently in advanced phase II clinical studies.

Sulfonamide derivatives for the treatment of diseases

The invention relates to compounds of formula (1) and to processes for the preparation of, intermediates used in the preparation of, compositions containing and the uses of, such derivatives. The compounds according to the present invention are useful in