188730-94-1

Basic information

• Product Name: Oxirane, [3-nitro-4-(phenylMethoxy)phenyl]-, (2R)-
• Synonyms: Oxirane, [3-nitro-4-(phenylMethoxy)phenyl]-, (2R)-;(2R)-2-(3-nitro-4-phenylmethoxyphenyl)oxirane;ForMoterol int1
• CAS NO: 188730-94-1
• Molecular Formula: C₁₅H₁₃NO₄
• Molecular Weight: 271.26802
• Mol File: 188730-94-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 438.502 °C at 760 mmHg
• Flash Point: 195.617 °C
• Appearance: /
• Density: 1.323 g/cm³
• CAS DataBase Reference: Oxirane, [3-nitro-4-(phenylMethoxy)phenyl]-, (2R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxirane, [3-nitro-4-(phenylMethoxy)phenyl]-, (2R)-(188730-94-1)
• EPA Substance Registry System: Oxirane, [3-nitro-4-(phenylMethoxy)phenyl]-, (2R)-(188730-94-1)

Safety Data

• Hazardous Substances Data: 188730-94-1(Hazardous Substances Data)

Usage

Description

Oxirane, [3-nitro-4-(phenylmethoxy)phenyl]-, (2R)-, also known as Maraviroc, is a chemical compound that functions as an antiretroviral medication specifically designed for the treatment of HIV-1 infection. It operates by obstructing the virus's entry into cells, thereby curtailing the virus's dissemination throughout the body. Maraviroc is a member of the CCR5 antagonist class of drugs, which are tailored to target the CCR5 co-receptor present on the surface of immune cells. This targeted approach allows for a more precise intervention in the treatment of HIV-1 infection.

Uses

Used in Pharmaceutical Industry:
Maraviroc is utilized as an antiretroviral agent for the treatment of HIV-1 infection. It is used to block the entry of the virus into cells, which is crucial for reducing the viral load in the body. Oxirane, [3-nitro-4-(phenylmethoxy)phenyl]-, (2R)-'s mechanism of action involves targeting the CCR5 co-receptor, which is a key point of entry for the virus into immune cells.
Used in Combination Therapy for HIV-1 Infection:
Maraviroc is often used in conjunction with other antiretroviral drugs as part of a combination therapy. This approach is beneficial as it can help to reduce the HIV viral load more effectively and increase CD4 cell counts in patients with HIV-1 infection. The combined use of Maraviroc with other medications can lead to a more comprehensive management of the infection and improved patient outcomes.
Used in Research and Development for HIV Treatments:
Beyond its clinical applications, Maraviroc also serves as a valuable compound in the ongoing research and development of new HIV treatments. Its unique mechanism of action as a CCR5 antagonist provides insights into the development of targeted therapies that can potentially lead to more effective and less toxic treatments for HIV-1 infection.

Upstream product

• 299964-35-5 (+/-)-2-bromo-1-(4-benzyloxy-3-nitrophenyl)ethanol 
• 299964-37-7 Acetic acid (S)-1-(4-benzyloxy-3-nitro-phenyl)-2-bromo-ethyl ester 
• 188690-82-6 (R)-2-bromo-1-(4-benzyloxy-3-nitrophenyl)ethanol 
• 43229-01-2 4-benzyloxy-3-nitrophenacyl bromide 
• 14347-05-8 4-benzyloxy-3-nitroacetophenone 

Downstream Products

• 1262020-50-7 (R,R)-1-(4-benzyloxy-3-nitro-phenyl)-2-[[2-(4-methoxy-phenyl)-1-methyl-ethyl]-(1-phenyl-ethyl)-amino]-ethanol 
• 1316100-17-0 (R,R)-N-(2-benzyloxy-5-{1-hydroxy-2-[[2-(4-methoxy-phenyl)-1-methyl-ethyl]-(1-phenyl-ethyl)-amino]-ethyl}-phenyl)-formamide 
• 1315510-05-4 (R,R)-1-(3-amino-4-benzyloxy-phenyl)-2-[[2-(4-methoxy-phenyl)-1-methyl-ethyl]-(1-phenyl-ethyl)-amino]-ethanol 
• 357408-71-0 (2S)-2-[N-benzyl-N-[(2R)-2-[4-(benzyloxy)-3-nitrophenyl]-2-hydroxyethyl]amino]-3-(4-methoxyphenyl)-1-propanol 
• 259799-03-6 (1R)-1-(3-amino-4-benzyloxyphenyl)-2-[N-benzyl-[3,3-bis[4-[(methoxy-carbonyl)amino]phenyl]propyl]amino]ethanol 
• 188690-83-7 N-[5-[(1R)-Hydroxy-2-[[(1R)-methyl-2-(4-methoxyphenyl)ethyl](phenylmethyl)amino]ethyl]-2-(phenylmethoxy)phenyl]-formamide 
• 289657-26-7 (R,R)-3-amino-α-[[[2-(4-methoxyphenyl)-1-methylethyl](phenyl methyl)amino]methyl]-4-(phenylmethoxy)-benzenemethanol 
• 67346-51-4 N-(2-Hydroxy-5-{(R)-1-hydroxy-2-[(S)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethyl}-phenyl)-formamide 
• 408497-91-6 N-(2-Benzyloxy-5-{(R)-1-hydroxy-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethyl}-phenyl)-formamide 
• 245759-61-9 (R)-1-(4-Benzyloxy-3-nitro-phenyl)-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethanol 
• 299964-43-5 (R)-1-(3-Amino-4-benzyloxy-phenyl)-2-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethanol 
• 73573-87-2 (R,R)-formoterol 

Relevant articles and documents

PROCESSES FOR PREPARING SUBSTANTIALLY PURE ARFORMOTEROL AND ITS INTERMEDIATES

Provided herein are improved, convenient and industrially advantageous processes for the preparation of N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[[(1R)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]formamide (Arformoterol) or a pharmaceutically acceptable salt thereof, in high yield and purity. Provided further herein is an improved and industrially advantageous process for the preparation of a substantially enantiomerically pure arformoterol intermediate, (R)-4-methoxy-α-methyl-N-(phenylmethyl)benzeneethanamine.

Process for the manufacturing of pharmaceutically active compounds

A process for making a compound of formula 1 or a salt thereof, wherein: R1 and R2 are each independently H, halogen, or C1-4-alkyl, or R1 and R2 together are C1-6-alkylene; and R3 /s

Enantio- and diastereoselective synthesis of all four stereoisomers of formoterol

Enantioselective syntheses of all four stereoisomers of formoterol are accomplished using asymmetric catalytic borane reductions with chiral oxazaborolidines as reducing agents.