22766-68-3

Usage

Uses

Used in Pharmaceutical Industry:
1-Azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester is used as a reactant for the synthesis of azoniabicyclooctanes, which are known as muscarinic acetylcholine receptor antagonists. These antagonists are crucial in the development of medications targeting various conditions, such as Alzheimer's disease, urinary incontinence, and overactive bladder.
In the synthesis process, Ethyl 4-Quinuclidinecarboxylate serves as a key building block, contributing to the formation of the azoniabicyclooctane structure. Its reactivity and structural properties make it an essential component in the creation of these therapeutic agents.

Upstream product

• 22766-67-2 1-azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester hydrochloride 
• 939900-20-6 C₁₀H₁₉NO₃ 
• 1126-09-6 4-carbethoxypiperidine 
• 142851-03-4 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate 
• 1276088-72-2 ethyl-4-(2-chloroethyl)-piperidine-4-carboxylate hydrochloride 
• 869112-14-1 1-(2-chloroethyl)-4-piperidinecarboxylic acid ethyl ester 

Downstream Products

• 26608-58-2 4-hydroxymethylquinuclidine 
• 55022-91-8 quinuclidine-4-carbaldehyde 
• 869112-31-2 4-[hydroxy(diphenyl)methyl]-1-(2-hydroxyethyl)-1-azoniabicyclo[2.2.2]octane bromide 
• 22766-67-2 1-azabicyclo[2.2.2]octane-4-carboxylic acid ethyl ester hydrochloride 
• 461648-39-5 α,α-diphenyl-1-azabicyclo[2.2.2]octane-4-methanol 
• 45651-41-0 4-Methyl-chinuclidin 

Relevant academic research and scientific papers

A More Sustainable Process for Preparation of the Muscarinic Acetylcholine Antagonist Umeclidinium Bromide

A more sustainable process for the synthesis of the long-acting muscarinic acetylcholine antagonist umeclidinium bromide is described. Specifically, we report the synthesis of ethyl 1-(2-chloroethyl)-4-piperidinecarboxylate, a key intermediate in the prep

Preparation method of umeclidinium bromide intermediate

The invention relates to a preparation method of an umeclidinium bromide intermediate. The preparation method comprises the following steps: in a solvent, carrying out cyclization reaction on a compound as shown in a formula I, and conducting salifying wi

Method for synthesizing intermediate of high-purity Umeclidinium bromide

The invention discloses a method for synthesizing intermediates 1-(2-chloroethyl) piperidine-4-formate and quinuclidin-4-carboxylic ester of Umeclidinium bromide, and particularly discloses a method for synthesizing an intermediate 1-(2-chloroethyl) piperidine-4-formate and quinuclidin-4-carboxylic ester of Umeclidinium bromide. According to the method, crude products of the intermediates 1-(2-chloroethyl) piperidine-4-formate and quinuclidin-4-carboxylate are purified in a molecular distillation or reduced pressure distillation mode, and the high-purity medical intermediates are obtained. Thepurification cost can be effectively reduced through molecular distillation or vacuum distillation, the yield is improved, and the product purity can reach 99% or above. According to the present invention, with the synthesis method, the 1-(2-chloroethyl) piperidine-4-formate and the quinuclidin-4-carboxylate are prepared, the process route is short, the amplified production is easy, and the yieldis high. The method has the characteristics of novel process, high yield, low cost, high product purity and the like.

PROCESS FOR THE PREPARATION OF UMECLIDINIUM BROMIDE

The present invention discloses processes comprising a) reacting ethyl isonipecotate with 1 -bromo-2- chloroethane in the presence of an organic base in a solvent to form ethyl 1 -(2-chloroethyl)piperidine- 4-carboxylate (II) or a salt thereof. Process st

Halogen-Bonded Supramolecular Capsules in the Solid State, in Solution, and in the Gas Phase

Supramolecular capsules were assembled by neutral halogen bonding (XB) and studied in the solid state, in solution, and in the gas phase. The geometry of the highly organized capsules is shown by an X-ray crystal structure which features the assembly of t

Quinuclidine derivative, method for preparing same and application of quinuclidine derivative

The invention relates to a quinuclidine derivative, a pharmaceutically acceptable salt, pro-drug and solvent compound of the quinuclidine derivative, a method for preparing the quinuclidine derivative, a drug composition with the quinuclidine derivative and the pharmaceutically acceptable salt, pro-drug and solvent compound and pharmaceutical application of the quinuclidine derivative. The quinuclidine derivative, the pharmaceutically acceptable salt, pro-drug and solvent compound, the method, the drug composition and the pharmaceutical application have the advantage that the compound is excellent in M3 receptor antagonist activity and accordingly can be used as a novel efficient drug for chronic obstructive pulmonary diseases.

METHODS OF PREPARATION OF MUSCARINIC ACETYLCHOLINE RECEPTOR ANTAGONISTS

The present application describes novel intermediates useful in the synthesis of mAChRs and methods for preparing these intermediates, comprising a compound of Formula (II): wherein, P is a suitably nitrogen protecting group; R is selected from the group consisting of C1-8alkyl, C2-8alkenyl, C2-8alkynyl, C3-6cycloalkyl, C3-6cycloalkenyl, heterocyclic, heterocyclic C1-4alkyl, aryl, aryl C1-4alkyl and heteroaryl C1-4alkyl; and Y is a suitable leaving group.

Discovery of novel 1-azoniabicyclo[2.2.2]octane muscarinic acetylcholine receptor antagonists

A novel 4-hydroxyl(diphenyl)methyl substituted quinuclidine series was discovered as a very promising class of muscarinic antagonists. The structure-activity relationships of the connectivity of the diphenyl moiety to the quinuclidine core and around the ring nitrogen side chain are described. Computational docking studies using an homology model of the M3 receptor readily explained the observed structure-activity relationship of the various compounds. Compound 14o was identified as a very potent, slowly reversible M3 antagonist with a very long in vivo duration of bronchoprotection.

Muscarinic acetylcholine receptor antagonists

Muscarinic Acetylcholine Receptor Antagonists and methods of using them are provided.

MUSCARINIC ACETYLCHOLINE RECEPTOR ANTAGONISTS FIELD OF THE INVENTION

Muscarinic Acetylcholine Receptor Antagonists and methods of using them are provided.