67346-49-0

Usage

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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Relevant academic research and scientific papers

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.

Formoterol, pharmaceutically acceptable salt thereof and preparation method of intermediate

The invention relates to formoterol, a pharmaceutically acceptable salt thereof and a preparation method of an intermediate. The method for purifying the formoterol intermediate (a compound shown as aformula V) comprises the following steps of: I) perform

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.

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 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

The asymmetric synthesis of (R,R)-formoterol via transfer hydrogenation with polyethylene glycol bound Rh catalyst in PEG2000 and water

(R,R)-formoterol was synthesized in seven steps with 4-hydroxyl-3-nitro- acetophenone as the starting material. The key intermediate, the chiral secondary alcohol 4, was prepared via Rh-catalyzed asymmetric transfer hydrogenation with (S,S)-PEGBsDPEN as the ligand and sodium formate as the hydrogen donor under mild conditions. With a mixture of PEG 2000 and water as the reaction media, the catalyst system could be recycled four times.

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.

AN IMPROVED PROCESS FOR THE PREPARATION OF HIGH PURITY FORMOTEROL AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS

The present invention relates to an improved process for the preparation of high purity formoterol and its pharmaceutically acceptable salts of Formula-I(C).

Compositions and methods for inducing adipose tissue cell death

Pharmaceutical compositions, methods for increasing the rate of apoptosis in adipose tissue cells, and methods of reducing adipose tissue mass in a host, are described. One exemplary pharmaceutical composition, among others, includes at least one catecholamine in combination with a pharmaceutically acceptable carrier. The catecholamine is present in a dosage level effective to increase the rate of apoptosis in adipose tissue cells in a host.

Administration of medicinal dry powders

A method as well as a therapeutic metered combined dose are disclosed for a combined administration of medicinal dry powders. A metered medicinal dry powder combined dosage comprising at least two medicaments of separate dry powder formulations is prepared, whereby the metered powder quantity per medicament is deposited in a dose forming step creating the medicinal combined dose. The deposits of the at least two medicaments are suitably kept separated from each other, such that the medicaments cannot detrimentally interact after forming of the combined dose, and the medicinal combined dose is introduced into an inhaler device for a delivery of the powder dose during the course of a single inhalation. The therapeutic metered medicinal, combined dosage of finely divided dry medication powders disclosed comprises metered quantities of at least two medicaments, separately deposited and the medicinal combined dosage is adapted for a user initiated delivery of the dosage during a single inhalation through an inhaler device. The at least two medicaments of the medicinal combined dosage will generally be aerosolized simultaneously or sequentially during the inhalation such that a large proportion of each medicament will settle in the intended target area of the airways and lungs of a user.