67346-59-2

Upstream product

• 122-84-9 4-methoxybenzyl methyl ketone 
• 100-46-9 benzylamine 
• 43229-65-8 [2-(4-methoxyphenyl)-1-methylethyl](phenylmethyl)amine 
• 104-01-8 4-Methoxyphenylacetic acid 
• 1096141-37-5 C₁₇H₁₉NO 
• 188690-85-9 C₈H₈O₃*C₁₇H₂₁NO 
• 64-13-1 2-amino-1-(4-methyoxyphenyl)propane 
• 100-52-7 benzaldehyde 

Downstream Products

• 67346-49-0 (S,S)-formoterol 
• 67346-51-4 N-(2-Hydroxy-5-{(R)-1-hydroxy-2-[(S)-2-(4-methoxy-phenyl)-1-methyl-ethylamino]-ethyl}-phenyl)-formamide 

Relevant academic research and scientific papers

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.

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.

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.

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.

PREPARATION OF (R,R)-FENOTEROL AND (R,R)- OR (R,S)-FENOTEROL ANALOGUES AND THEIR USE IN TREATING CONGESTIVE HEART FAILURE

This disclosure concerns the discovery of (R,R)- and (R,S)-fenoterol analogues which are highly effective at binding β2-adrenergic receptors. Exemplary chemical structures for these analogues are provided. Also provided are pharmaceutical compositions including the disclosed (R,R)-fenoterol and fenoterol analogues, and methods of using such compounds and compositions for the treatment of cardiac disorders such as congestive heart failure and pulmonary disorders such as asthma or chronic obstructive pulmonary disease.

Comparative molecular field analysis of the binding of the stereoisomers of fenoterol and fenoterol derivatives to the β2 adrenergic receptor

Stereoisomers of fenoterol and six fenoterol derivatives have been synthesized and their binding affinities for the β2 adrenergic receptor (Kiβ2-AR), the subtype selectivity relative to the β1-AR (Kiβ1-AR/K iβ2-AR) and their functional activities were determined. Of the 26 compounds synthesized in the study, submicromolar binding affinities were observed for (R,R)-fenoterol, the (R,R)-isomer of the p-methoxy, and (R,R)- and (R,S)-isomers of 1-naphthyl derivatives and all of these compounds were active at submicromolar concentrations in cardiomyocyte contractility tests. The Kiβ1-AR/K iβ2-AR ratios were >40 for (R,R)-fenoterol and the (R,R)-p-methoxy and (R,S)-1-naphthyl derivatives and 14 for the (R,R)-1-napthyl derivative. The binding data was analyzed using comparative molecular field analysis (CoMFA), and the resulting model indicated that the fenoterol derivatives interacted with two separate binding sites and one steric restricted site on the pseudo-receptor and that the chirality of the second stereogenic center affected Kiβ2 and subtype selectivity.

Hair analysis for drugs of abuse. XI. Disposition of benzphetamine and its metabolites into hair and comparison of benzphetamine use and methamphetamine use by hair analysis

In order to study the disposition of benzphetamine (BZP) and its metabolites, desmethyl benzphetamine (norBZP), p-hydroxy desmethyl benzphetamine (OHnorBZP), methamphetamine (MA) and amphetamine (AP), from plasma to hair in rats, an analytical method for identifying these drugs in plasma, urine and hair was developed with selected ion monitoring of gas chromatograph/mass spectrometry (GC/MS-SIM) results. After the intraperitoneal administration of BZP to rats (10 mg/kg/d, 10 d, n=3), concentrations of BZP and its metabolites in rat hair newly grown for 4 weeks were compared to the areas under the concentration versus time curve (AUCs) of these drugs in the rat plasma. The concentrations of BZP, norBZP, OHnorBZP, MA and AP in the rat hair were 14.8±1.4, 6.1±0.3, 2.6±0.5, 2.3±0.1 and 9.2±0.3 ng/mg, and the ratio of the concentrations in the hair to AUCs in the rat plasma was 3.0:0.1:0.1:0.6:0.2, respectively. This fact suggested that BZP tends to be readily incorporated into hair from blood. The method was applied to the determination of the metabolites in scalp hair and pubic hair of humans who orally ingested BZP (30 mg/d, 5 d, n=2). BZP, norBZP, MA and AP were detected at 0.14-0.56, 0.29-0.63, 0.10 and 1.06-1.66 ng/mg in the scalp hair and at 0.10-0.20, 0.13-0.18, trace-0.15 and 0.23 ng/mg in the pubic hair, respectively. It was shown that BZP use could be retrospectively distinguished from MA use by the detection of BZP and/or norBZP in hair.