67346-60-5

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(-)-1-(4'-methoxyphenyl)-2-benzylaminopropane is used as a key intermediate in the synthesis of Formoterol Fumarate (F693401) for its role in creating a medication that serves various therapeutic purposes. Formoterol Fumarate is a long-acting beta-2 adrenergic agonist (LABA) used in the treatment of asthma and chronic obstructive pulmonary disease (COPD). It helps to relax the muscles in the airways and improve breathing for patients suffering from these respiratory conditions.

Upstream product

• 122-84-9 4-methoxybenzyl methyl ketone 
• 100-46-9 benzylamine 
• 245759-64-2 N-benzyl-1-(4-methoxyphenyl)propan-2-amine mandalate salt 
• 1049695-95-5 benzyl-[2-(4-methoxy-phenyl)-1-methyl-ethyl]-amine; hydrochloride 
• 58993-79-6 (R)-(-)-p-methoxyamphetamine 
• 100-52-7 benzaldehyde 
• 104-01-8 4-Methoxyphenylacetic acid 
• 1096141-37-5 C₁₇H₁₉NO 
• 17199-29-0 (S)-Mandelic acid 
• 43229-65-8 [2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amine 
• 245759-64-2 (R)-N-benzyl-N-(1-methyl-2-p-methoxyphenylethyl)amine L-mandelate 

Downstream Products

• 1026431-67-3 C₃₉H₄₁NO₄ 
• 1042738-15-7 5-[[[(1R)-2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amino]acetyl]-8-(phenylmethoxy)-(1H)-quinolin-2-one monohydrochloride 
• 188690-83-7 N-[5-[(1R)-Hydroxy-2-[[(1R)-methyl-2-(4-methoxyphenyl)ethyl](phenylmethyl)amino]ethyl]-2-(phenylmethoxy)phenyl]-formamide 
• 245759-65-3 (R,R)-3-nitro-α-[[[2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amino]methyl]-4-(phenylmethoxy)-benzenemethanol 
• 1198769-18-4 (R)-4-benzyloxy-3-nitro-α-(N-benzyl-N-(1-methyl-2-p-methoxyphenylethyl)amino)acetophenone 
• 1122063-39-1 4-(2-(benzylamino)propyl)phenol 
• 289657-25-6 (S)-1-(3-Amino-4-benzyloxy-phenyl)-2-{benzyl-[(R)-2-(4-methoxy-phenyl)-1-methyl-ethyl]-amino}-ethanol 
• 289657-26-7 (R,R)-3-amino-α-[[[2-(4-methoxyphenyl)-1-methylethyl](phenyl methyl)amino]methyl]-4-(phenylmethoxy)-benzenemethanol 
• 73573-87-2 (R,R)-formoterol 
• 67346-50-3 (S,R)-Formoterol 

Relevant academic research and scientific papers

Direct Reductive Amination of Carbonyl Compounds with H2 Using Heterogeneous Catalysts in Continuous Flow as an Alternative to N-Alkylation with Alkyl Halides

A general continuous-flow procedure for direct reductive amination of secondary and primary amines with aromatic and aliphatic aldehydes as well as ketones is reported. The use of hydrogen gas and commercially available Pt/C as a heterogeneous catalyst is a key. In addition to exhibiting an excellent functional group tolerance, this method allows the fast formation of C?N bonds without production of any hazardous chemical waste. Applications to the synthesis of key intermediates toward active pharmaceutical ingredients (Donepezil and Arformoterol/Tamsulosin) are also described. (Figure presented.).

IRIDIUM COMPLEX

PROBLEM TO BE SOLVED: To provide an iridium complex applicable for an industrial catalyst reaction. SOLUTION: The present invention provides an iridium complex represented by the following formula [I]. In the presence of the iridium complex, a hydrogen donative compound and an imine react with each other, so that an amine can be produced. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

Use of fenoterol and fenoterol analogues in the treatment of glioblastomas and astrocytomas

This disclosure concerns the discovery of the use of fenoterol and (R,R)- and (R,S)-fenoterol analogs for the treatment of a tumor expressing a β2-adrenergic receptor, such as a primary brain tumor, including a glioblastoma or astrocytoma expressing a β2-adrenergic receptor. In one example, the method includes administering to a subject a therapeutically effective amount of fenoterol, a specific fenoterol analog or a combination thereof to reduce one or more symptoms associated with the tumor, thereby treating the tumor in the subject.

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.

Direct Asymmetric Reductive Amination for the Synthesis of Chiral β-Arylamines

The highly efficient and direct asymmetric reductive amination of arylacetones catalyzed by an iridium complex for the preparation of enantiomerically pure β-arylamines is described. The monodentate phosphoramidite ligand exhibits superb reactivity (TONs of up to 20 000) and enantioselectivity (up to 99 % ee). Additives played important roles in this reductive coupling reaction. Asymmetric reductive coupling of a ketone and an amine is a straightforward and atom-economic approach for preparing optically enriched amines. The highly efficient and direct asymmetric reductive amination of arylacetones, catalyzed by an iridium complex, supplies enantiomerically pure β-arylamines. The new phosphoramidite ligands reported show superb reactivity and enantioselectivity in this reductive coupling. M.S.=molecular sieves, TFA=trifluoroacetic acid.

METHOD FOR PRODUCING NOVEL ORGANOMETALLIC COMPLEX AND AMINE COMPOUND

The purpose of the invention is to provide a novel organometallic compound that can be utilized as a catalyst having high generality, high activity, and excellent functional group selectivity. The invention pertains to a novel organometallic compound represented by general formula (1) that catalyzes a reductive amination reaction.

Design, synthesis and evaluation of dual pharmacology β2- adrenoceptor agonists and PDE4 inhibitors

A novel series of formoterol-phthalazinone hybrids were synthesised and evaluated as dual pharmacology β2-adrenoceptor agonists and PDE4 inhibitors. Most of the hybrids displayed high β2-adrenoceptor agonist and moderate PDE4 inhibitory activities. The most potent compound, (R,R)-11c, exhibited agonist (EC50 = 1.05 nM, pEC50 = 9.0) and potent PDE4B2 inhibitory activities (IC50 = 0.092 μM).

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.

METHOD FOR PRODUCING OPTICALLY ACTIVE AMINE

The present invention provides a method for producing chiral amines, comprising asymmetric transfer hydrogenation of imine compounds in the presence of a hydrogen donor compound and an iridium(III) complex having a chiral prolinamide compound as a ligand. The present invention is useful for production of chiral amines in an efficient manner in terms of their optical and chemical yields.

PROCESS FOR THE SYNTHESIS OF ARFORMOTEROL

The present invention provides a process for preparing a compound of formula (Vl) or a salt thereof, the process comprising: (i) reacting 4-methoxyphenyl acetone with an amine of formula (VIII) under conditions of reductive amination to produce a compound of formula (II) or a salt thereof, wherein there is no isolation of an imine intermediate formed during the reductive amination; (ii) condensing the compound (II) or the acid addition salt thereof with an α-haloketone of formula (III) to produce the compound of formula (IV); (iii) reducing the compound (IV) to a compound of formula (V); and (iv) reducing the compound (V) to the compound of formula (Vl), wherein the reduction is carried out in the presence of either (1 ) a hydrogen donating compound in the presence of a hydrogen transfer catalyst; or (2) ammonium formate using a hydrogenation catalyst, wherein: R1 and R2 are independently optionally substituted arylalkyl, and Hal is selected from chloro or bromo.