5176-22-7

Usage

Uses

Used in Pharmaceutical Development:
3-Hydroxymethylquinuclidine is used as a therapeutic agent for the treatment of neurodegenerative diseases such as Alzheimer's. Its cholinergic receptor antagonist properties make it a candidate for managing cognitive decline and other symptoms associated with such conditions.
Used in Drug Addiction Treatment:
3-HMQ is also being studied for its potential in treating drug addiction, leveraging its interaction with the cholinergic system to potentially reduce cravings and support recovery processes.
Used in Organic Synthesis:
In the field of organic synthesis, 3-Hydroxymethylquinuclidine serves as a versatile building block. It is utilized for the preparation of various pharmaceutical compounds, contributing to the development of new medications and therapeutics.
Used in Research:
3-HMQ is used as a research compound to further explore its pharmacological properties and potential applications in medicine, including its mechanism of action and safety profile in treating different conditions.

InChI:InChI=1/C8H15NO/c10-6-8-5-9-3-1-7(8)2-4-9/h7-8,10H,1-6H2

Upstream product

• 6238-33-1 3-quinuclidinecarboxylic acid ethyl ester 
• 5176-21-6 1-azabicyclo[2.2.2]octane-3-carboxaldehyde 
• 242810-00-0 3-Methoxymethylquinuclidine-3-ol 
• 60-29-7 diethyl ether 
• 75208-40-1 quinuclidine-3-carboxylic acid 

Downstream Products

• 64099-45-2 3-chloromethyl-1-azabicyclo[2.2.2]octane 
• 138874-55-2 (3R)-1-azabicyclo[2.2.2]octan-3-ylmethanol 
• 88644-21-7 [(3S)-quinuclidin-3-yl]methanol 
• 138740-84-8 phenoxymethyl-1-aza-bicyclo[2.2.2]octane 

Relevant academic research and scientific papers

PURIFICATION OF 3-ETHOXYCARBONYLQUINUCLIDINE AND ITS CONVERSION TO 3-QUINUCLIDINECARBOXYLIC ACID AND 3-QUINUCLIDINYLMETHANOL

3-Ethoxycarbonylquinuclidine obtained by the Grob method is a mixture of 3-ethoxycarbonyl-1-azabicyclo- and, according to 13C NMR data, 5-ethoxycarbonyl-5-azatricyclo2,7>octanes (about 16:2:1). 3-Ethoxy-carbonylquinuclidine was purified by recrystallization of the hydrochloride, hydrolyzed by water to 3-quinuclidinecarboxylic acid, and reduced by LiAlH4 to 3-quinuclidinylmethanol.

AMINOESTER DERIVATIVES

The invention relates to novel compounds which are both phosphodiesterase 4 (PDE4) enzymeinhibitorsand muscarinic M3 receptor antagonists, methods of preparing such compounds, compositions containing them and therapeutic use thereof.

AMINOESTER DERIVATIVES USEFUL IN THE TREATMENT OF COPD

The invention relates to novel compounds which are both phosphodiesterase 4 (PDE4) enzyme inhibitors and muscarinic M3 receptor antagonists, methods of preparing such compounds, compositions containing them and therapeutic use thereof.

Preparation of quinuclidine-3-methanol

A process for the preparation of quinuclidine-3-methanol comprising reacting quinuclidine-3-one acid addition salt with an alkali metal cyanide in an aqueous media to obtain 3-cyano-3-hydroxy-quinuclidine, reacting the latter with anhydrous methanol in the presence of hydrogen chloride gas followed by treatment with aqueous alkali to obtain methyl 3-hydroxy-quinuclidine-3-carboxylate, reacting the latter with thionyl chloride to form methyl 1-azabicyclo(2,2,2)oct-2-ene-3-carboxylate, hydrogenating the latter with Raney nickel to obtain methyl 1-azabicyclo(2,2,2)octane-3-carboxylate and reducing the latter to obtain quinuclidine-3-methanol which is an intermediate for mequitazine which is useful as an antihistaminic.

FURAN DERIVATIVES HAVING ANTI-ULCER ACTIVITY

Compounds of formula (I): STR1 wherein: A represents a CH-NO 2 group or a N-CN group;B represents CH 2, O, S or a direct bond;R represents a bicyclic or polycyclic residue, variously substituted and functionalized;R 1 and R 2, which may be the same or different, are hydrogen or C 1-C 4 alkyl groups; andn and m, which may be the same or different, are 0, 1, 2, 3 or 4; are valuable pharmacological agents.

Process for the preparation of derivatives of quinuclidine substituted in the 3 position

Process for the preparation of compounds of the formula: STR1 in which X is H, Cl, Br, I or OH, in which 3-methylene quinuclidine is reacted with an aluminum hydride, in an appropriate solvent and in the presence of a catalytic quantity of a halide of a transition metal, the molar ratio EQU1 being at least equal to 0.6, the product formed is reacted in situ with an ester, and then the product thus formed is reacted in situ with an electrophilic reactant which is capable of yielding an atom or group X as defined with reference to formula (I). The compounds of formula (I) can be used for the preparation of medicaments.