88644-21-7

Upstream product

• 242810-00-0 3-Methoxymethylquinuclidine-3-ol 
• 75208-40-1 quinuclidine-3-carboxylic acid 
• 5176-22-7 3-hydroxymethyl-1-azabicyclo[2.2.2]octane 
• 84-31-1 quininone 
• 130-95-0 quinine 
• 103027-51-6 2-[(3R,4S)-3-ethenylpiperidin-4-yl]ethan-1-ol 
• 1311205-56-7 (3R)-3-ethenyl-1-azabicyclo[2.2.2]octane 
• 1311205-55-6 (3R,4S)-4-(2-chloroethyl)-3-ethenylpiperidine 
• 52346-11-9 tert-butyl 2-[(3R,4S)-3-ethenylpiperidin-4-yl]acetate 
• 60-29-7 diethyl ether 
• 5176-21-6 1-azabicyclo[2.2.2]octane-3-carboxaldehyde 
• 6238-33-1 3-quinuclidinecarboxylic acid ethyl ester 

Downstream Products

• 138874-55-2 (3R)-1-azabicyclo[2.2.2]octan-3-ylmethanol 

Relevant academic research and scientific papers

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.

VINYL QUINUCLIDINE USEFUL AS A SYNTHESIS INTERMEDIATE IN THE PREPARATION OF (R)-MEQUITAZINE

The present invention relates to the use of the vinyl quinuclidine enantiomer (R) of the following formula 2 as a synthesis intermediate in the preparation of (R)-mequitazine.

Asymmetric synthesis of (+)-mequitazine from quinine

The first asymmetric synthesis of the antihistaminic drug mequitazine is reported. Our approach started from quinine, a Cinchona alkaloid, whose chiral information was exploited for setting up the stereogenic center of (+)-mequitazine.

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.

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.

QUINUCLIDINE BORANES AS INTERMEDIATES IN FORMATION AND ISOLATION OF FUNCTIONALIZED QUINUCLIDINE SYSTEMS

Stable N-borane complexes of quinuclidine systems are useful both as N-protected intermediates (in alkylation and hydroboration/oxidation reactions) and as derivatives which facilitate isolation/purification and subsequent characterization.Deprotection is readily effected using acidic oxidation of hydride.

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.