171723-80-1

Basic information

• Product Name: Carbamic acid, [1,1'-biphenyl]-2-yl-, 1-(phenylmethyl)-4-piperidinyl ester
• CAS NO: 171723-80-1
• Molecular Formula: C25H26N2O2
• Molecular Weight: 386.494
• Mol File: 171723-80-1.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [1,1'-biphenyl]-2-yl-, 1-(phenylmethyl)-4-piperidinyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [1,1'-biphenyl]-2-yl-, 1-(phenylmethyl)-4-piperidinyl ester(171723-80-1)
• EPA Substance Registry System: Carbamic acid, [1,1'-biphenyl]-2-yl-, 1-(phenylmethyl)-4-piperidinyl ester(171723-80-1)

Safety Data

• Hazardous Substances Data: 171723-80-1(Hazardous Substances Data)

Upstream product

• 947-84-2 2-Biphenylcarboxylic acid 
• 4727-72-4 1-benzyl-4-hydroxypiperidine 
• 17337-13-2 [1,1'-biphenyl]-2-yl-isocyanate 

Downstream Products

• 743461-40-7 biphenyl-2-ylcarbamic Acid 1-[2-Fluoro-3-(4-hydroxymethylpiperidin-1-ylmethyl)-benzyl]piperidin-4-yl Ester 
• 743461-45-2 biphenyl-2-ylcarbamic Acid 1-{3-[4-(2-Hydroxyethyl)phenoxy]propyl}piperidin-4-yl Ester 
• 743460-71-1 C₃₉H₅₃N₃O₅ 
• 743460-72-2 biphenyl-2-ylcarbamic acid 1-{9-[(R)-2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethylamino]nonyl}piperidin-4-yl ester 
• 743460-16-4 biphenyl-2-ylcarbamic acid 1-{9-[2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]nonyl}piperidin-4-yl ester 
• 1309750-29-5 C₂₀H₂₄N₂O₃ 
• 1309750-48-8 C₂₁H₂₆N₂O₃ 
• 1309750-53-5 C₂₂H₂₈N₂O₃ 
• 1309750-61-5 C₂₀H₂₂N₂O₃ 
• 1309750-62-6 C₂₁H₂₄N₂O₃ 
• 1309750-63-7 C₂₂H₂₆N₂O₃ 
• 1289178-38-6 C₃₄H₃₇N₃O₂ 
• 1289178-39-7 C₃₅H₃₉N₃O₂ 
• 1289178-40-0 C₃₆H₄₁N₃O₂ 

Relevant articles and documents

Discovery of (R)-1-(3-((2-Chloro-4-(((2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)amino)methyl)-5-methoxyphenyl)amino)-3-oxopropyl)piperidin-4-yl [1,1′-biphenyl]-2-ylcarbamate (TD-5959, GSK961081, Batefenterol): First-in-Class dual pharmacology multivalent muscarinic antagonist and β2 agonist (MABA) for the treatment of chronic obstructive pulmonary disease (COPD)

Through application of our multivalent approach to drug discovery we previously reported the first discovery of dual pharmacology MABA bronchodilators, exemplified by 1. Herein we describe the subsequent lead optimization of both muscarinic antagonist and β2 agonist activities, through modification of the linker motif, to achieve 24 h duration of action in a guinea pig bronchoprotection model. Concomitantly we targeted high lung selectivities, low systemic exposures and identified crystalline forms suitable for inhalation devices. This article culminates with the discovery of our first clinical candidate 12f (TD-5959, GSK961081, batefenterol). In a phase 2b trial, batefenterol produced statistical and clinically significant differences compared to placebo and numerically greater improvements in the primary end point of trough FEV1 compared to salmeterol after 4 weeks of dosing in patients with moderate to severe chronic obstructive pulmonary disease (COPD).

Crystalline forms of a dimethylphenyl compound

The invention relates to crystalline free base forms of biphenyl-2-ylcarbamic acid 1-[2-(4-{[(R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]methyl}-2,5-dimethylphenylcarbamoyl)ethyl]piperidin-4-yl ester or a solvate thereof. This invention also relates to pharmaceutical compositions containing or prepared from such crystalline forms; processes and intermediates useful for preparing such crystalline forms; and methods of using such crystalline forms to, for example, treat a pulmonary disorder.

Crystalline form of a biphenyl compound

The invention provides a crystalline 1,2-ethanedisulfonic acid salt of biphenyl-2-ylcarbamic acid 1-[2-(2-chloro-4-{[(R)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]methyl}-5-methoxyphenylcarbamoyl)ethyl]piperidin-4-yl ester or a solvate thereof. This invention also provides pharmaceutical compositions comprising such a salt or prepared using such a salt; processes and intermediates for preparing such a salt; and methods of using such a salt to treat a pulmonary disorder.