19817-07-3Relevant articles and documents
Quinuclidine chemistry: Autocondensation reactions of 3 quinuclidinone
Sandmann,McHugh Jr
, p. 890 - 891 (1977)
During the synthesis of 3-hydroxy-3-ethinylquinuclidine (I), two additional products were isolated and identified as (E)-3-[2-(3-oxoquinuclidine)]quinuclidylidene (III) and (E)-3-[2-(3-hydroxy-3-ethinylquinuclidine)]quinuclidylidene (V). The base-catalyzed auto-condensation of 3-quinuclidinone resulted in the α,β-unsaturated ketone dimer (III) as a single isomer. The geometric configuration was deduced by examination of the NMR spectra of the methyl iodide salt. Compound V was thus the result of attack on the carbonyl carbon of III by the acetylide anion. The isolation and identification of these compounds clarified the reported differences in the physical properties of I and its analogs.
Potent anti-muscarinic activity in a novel series of quinuclidine derivatives
Starck, Jean-Philippe,Talaga, Patrice,Quere, Luc,Collart, Philippe,Christophe, Bernard,Brutto, Patrick Lo,Jadot, Sophie,Chimmanamada, Dinesh,Zanda, Matteo,Wagner, Alain,Mioskowski, Charles,Massingham, Roy,Guyaux, Michel
, p. 373 - 377 (2006)
The synthesis and biological evaluation of a novel family of M3 muscarinic antagonists are described. A systematic modification of the substituents to a novel alkyne-quinuclidine scaffold yielded original compounds displaying potent in vitro an
Design of α7 nicotinic acetylcholine receptor ligands using the (het)Aryl-1,2,3-triazole core: Synthesis, in vitro evaluation and SAR studies
Ouach, Aziz,Pin, Frederic,Bertrand, Emilie,Vercouillie, Johnny,Gulhan, Zuhal,Mothes, Céline,Deloye, Jean-Bernard,Guilloteau, Denis,Suzenet, Franck,Chalon, Sylvie,Routier, Sylvain
, p. 153 - 164 (2015/11/18)
We report here the synthesis of a large library of 1,2,3-triazole derivatives which were in vitro tested as α7 nAchR ligands. The SAR study revealed that several crucial factors are involved in the affinity of these compounds for α7 nAchR such as a (R) quinuclidine configuration and a mono C-3 quinuclidine substitution. The triazole ring was substituted by a phenyl ring bearing small OMe/CH2F groups or fluorine atom and by several heterocycles such as thiophenes, furanes, benzothiophenes or benzofuranes. Among the 30 derivatives tested, the two derivatives 10 and 39 with Ki in the nanomolar range were identified (2.3 and 3 nM respectively). They exhibited a strict selectivity toward the α4β2 nicotinic receptor (up to 1 μM) but interacted with the 5HT3 receptors with Ki around 3 nM. Synthesis, SAR studies and a full description of the derivatives are reported.
HETEROCYCLIC COMPOUNDS AND USES THEREOF
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Paragraph 00684, (2015/04/22)
Compounds and pharmaceutical compositions that modulate kinase activity, including PI3 kinase activity, and compounds, pharmaceutical compositions, and methods of treatment of diseases and conditions associated with kinase activity, including PI3 kinase activity, are described herein.
HETEROCYCLIC COMPOUNDS FOR USE IN THE TREATMENT OF PI3K-GAMMA MEDIATED DISORDERS
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Paragraph 001340, (2015/11/10)
Compounds and pharmaceutical compositions that modulate kinase activity, including PI3 kinase activity, and compounds, pharmaceutical compositions, and methods of treatment of diseases and conditions associated with kinase activity, including PI3 kinase activity, are described herein.
1,4-DISUBSTITUTED 1,2,3-TRIAZOLES, METHODS FOR PREPARING SAME, AND DIAGNOSTIC AND THERAPEUTIC USES THEREOF
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Paragraph 0561; 0562; 0563, (2014/02/16)
A compound having the following general formula (I): wherein: X is a nitrogen atom and Y is a carbon atom; orX is a carbon atom and Y is a nitrogen atom;the Ar group is an aryl or heteroaryl group; andthe RN and RN′ groups, together with the carbon atoms
Heterocyclic derivatives
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, (2008/06/13)
Compounds of formula (I) wherein R1 is hydrogen or hydroxy; R2 is hydrogen; or R1 and R2 are joined together so that CR1 14 CR2 is a double bond; X is selected from --Ch2 CH
Quinuclidine derivatives as squalene synthase inhibitors
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, (2008/06/13)
Compounds of formula (I) and their pharmaceutically acceptable salts in which R1 is hydrogen or hydroxy; R2 is hydrogen; or R1 and R2 are joined together so that CR1 -CR2 is a double bond; X is selected from --CH2 CH2 --, --CH=CH--, --C C--, --CH2 O--, --CH2 NH--, --NHCH2 --, --CH2 CO--, --COCH2 --, --CH2 S-- and --SCH2 --; Ar1 is a phenylene moiety; Ar2 is a heteroaryl moiety; and wherein one or both of Ar1 and Ar2 may optionally bear one or more substituents independently selected from halogeno, hydroxy, amino, nitro, cyano, carboxy, carbamoyl, alkyl, alkenyl, alkynyl, alkoxy, alkylamino, di-alkylamino, N-alkylcarbamoyl, di-N,N-alkylcarbamoyl, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, halogeno-alkyl, carboxyalkyl and alkanoylamino; provided that when R1 is hydroxy, X is not selected from --NHCH2 -- and --SCH2 --; are inhibitors of squalene synthase and hence useful in treating medical conditions in which a lowering of cholesterol is beneficial, such as hypercholesterolemia and atherosclerosis. Processes for preparing these derivatives, pharmaceutical compositions containing them are also described together with their use in medicine.
Quinclidine derivatives as squalene synthase inhibitors
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, (2008/06/13)
Quinuclidine derivatives of formula, and their pharmaceutically acceptable salts, in which: R1 is hydrogen or hydroxy; R2 is hydrogen; pr R1 and R2 are joined together so that CR1 -CR2 is a
