67346-49-0

Basic information

• Product Name: (R,R)-Formoterol
• Synonyms: N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino]ethyl]phenyl]formamide;4-[(1R)-2-[[(1R)-2-(4-Methoxyphenyl)-1-methylethyl]amino]-1-hydroxyethyl]-2-(formylamino)phenol;N-[2-Hydroxy-5-[(1R)-1-hydroxy-2-[[(αR)-α-methyl-4-methoxyphenethyl]amino]ethyl]phenyl]formamide;N-[2-Hydroxy-5-[(R)-1-hydroxy-2-[[(R)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]formamide;Arformoterol;(R,R)-Formoterol;Formamide, N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[[(1R)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-;Formamide, N-[2-hydroxy-5-[1-hydroxy-2-[[2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]-, [R-(R*,R*)]-
• CAS NO: 67346-49-0
• Molecular Formula: C19H24N2O4
• Molecular Weight: 344.4049
• Mol File: 67346-49-0.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 603.2°Cat760mmHg
• Flash Point: 318.6°C
• Appearance: /
• Density: 1.233g/cm³
• Refractive Index: 1.604
• CAS DataBase Reference: (R,R)-Formoterol(CAS DataBase Reference)
• NIST Chemistry Reference: (R,R)-Formoterol(67346-49-0)
• EPA Substance Registry System: (R,R)-Formoterol(67346-49-0)

Safety Data

• Hazardous Substances Data: 67346-49-0(Hazardous Substances Data)

Usage

Description

(R,R)-Formoterol, also known as Arformoterol, is a selective long-acting b2-agonist used as an inhalation solution for the treatment of bronchoconstriction associated with chronic obstructive pulmonary disease (COPD). It is the active (R,R)-enantiomer of the previously marketed b2-agonist formoterol, which is registered as a racemic mixture. The mechanism of action involves activation of adenyl cyclase, leading to increased production of cyclic adenosine monophosphate (cAMP) via ATP, resulting in relaxation of the bronchial smooth muscle and prevention of mast cells from releasing inflammatory mediators. (R,R)-Formoterol has high binding affinity for the human b2 receptor and is significantly more potent than the corresponding (S,S)-enantiomer and racemic formoterol.

Uses

Used in Respiratory Medicine:
(R,R)-Formoterol is used as a bronchodilator for the treatment of chronic obstructive pulmonary disease (COPD), which includes conditions such as chronic bronchitis and emphysema. It helps to relax the bronchial smooth muscle and alleviate bronchoconstriction, improving breathing for patients with COPD.
Used in Pharmaceutical Industry:
(R,R)-Formoterol is used as an active pharmaceutical ingredient in the development of inhalation solutions for the treatment of respiratory diseases. Its high potency and selectivity for the b2 receptor make it a valuable component in the formulation of effective bronchodilator medications.
Brand Name:
The brand name for (R,R)-Formoterol is Brovana, which is administered by inhalation, generally as the tartrate salt, for the treatment of COPD.

InChI:InChI=1/C20H25NO4/c1-14(11-15-4-7-17(25-2)8-5-15)3-9-19(23)16-6-10-20(24)18(12-16)21-13-22/h4-8,10,12-14,19,23-24H,3,9,11H2,1-2H3,(H,21,22)/t14-,19-/m0/s1

Upstream product

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• 67346-60-5 (R)-(-)-1-(4'-methoxyphenyl)-2-benzylaminopropane 
• 188730-96-3 (S)-4-benzyloxy-3-nitrostyrene oxide 
• 193761-53-4 (S)-1-(4-(benzyloxy)-3-nitrophenyl)-2-bromoethanol 
• 289657-25-6 (S)-1-(3-Amino-4-benzyloxy-phenyl)-2-{benzyl-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethyl]-amino}-ethanol 
• 67346-59-2 (S)-(-)-1-(4'-methoxyphenyl)-2-benzylaminopropane 
• 188730-94-1 (R)-1-(4-benzyloxy-3-nitrophenyl)oxirane 
• 188690-82-6 (R)-2-bromo-1-(4-benzyloxy-3-nitrophenyl)ethanol 
• 43229-65-8 [2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amine 
• 51582-41-3 2-(3-benzyloxy-4-nitrophenyl)oxirane 
• 43229-67-0 1-(4-benzyloxy-3-nitrobenzene)-2-{benzyl-[2-(4-methoxyphenyl)-1-methylethyl]amino}ethanol 
• 43229-68-1 1-(4-benzyloxy-3-aminobenzene)-2-{benzyl-[2-(4-methoxyphenyl)-1-methylethyl]amino}ethanol 
• 43229-69-2 N-[5-(2-{Benzyl-[2-(4-methoxy-phenyl)-1-methyl-ethyl]-amino}-1-hydroxy-ethyl)-2-benzyloxy-phenyl]-formamide; compound with (E)-but-2-enedioic acid 

Relevant articles and documents

Preparation method and application of formoterol and medicinal salt thereof

The invention provides a preparation method and application of formoterol and medicinal salt thereof, and relates to the technical field of chemical synthesis. The preparation method of formoterol comprises the following steps: reacting a compound shown as a formula I under the action of a palladium-containing catalyst, a hydrogen donor and an alkali reagent to obtain a compound shown as a formulaII, wherein the hydrogen donor is a combination of formic acid and ammonium formate. The compound shown in the formula I contains O-benzyl, N-benzyl, formyl and methoxyl at the same time, hydrogen can be slowly and continuously generated under the action of a palladium-containing catalyst by adopting the combination of a hydrogen donor and an alkali reagent, a method for directly introducing hydrogen in the conventional technology is replaced, benzyl of O-benzyl and N-benzyl on the compound shown in the formula I can be removed, formyl and methoxyl are not affected, the yield and purity of the product are guaranteed, reaction conditions are mild, technological operation is safe and easy to control, and the method is simple, convenient and easy to implement and suitable for large-scale production.

PROCESS FOR THE PREPARATION OF ARFORMOTEROL OR SALT THEREOF

Provided is an improved process for the preparation of arformoterol L-(+)-tartrate, and more specifically provided is a novel process for the preparation of arformoterol L-(+)-tartrate via arformoterol D-(?)-tartrate.

Process for preparation of intermediates of arformoterol

An improved method for the preparation of optically pure isomers of Formoterol is disclosed, particularly the (R,R)-isomer.A method of preparation of substantially enantiomerically pure (R,R)-1-(4-Benzyloxy-3-nitro-phenyl)-2-[[2-(4-methoxy-phenyl)-1-methyl-ethyl]-(1-phenyl-ethyl)-amino]-ethanol to use in the production of (R,R)-Formoterol is also disclosedAn improved method for the preparation of optically pure isomers of Formoterol is disclosed, particularly the (R,R)-isomer. A method of preparation of substantially enantiomerically pure (R,R)-1-(4-Benzyloxy-3-nitro-phenyl)-2-[[2-(4-methoxy-phenyl)-1-methyl-ethyl]-(1-phenyl-ethyl)-amino]-ethanol to use in the production of (R,R)-Formoterol is also disclosed