- New and potent quinuclidine-based antimicrobial agents
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Developing new antibiotics is currently very important since antibiotic resistance is one of the biggest problems of global health today. In the search for a new class of potential antimicrobial agents, ten new compounds were designed and synthesized based on the quinuclidinium heterocyclic core and the oxime functional group. The antimicrobial activity was assessed against a panel of representative gram-positive and gram-negative bacteria. All compounds demonstrated potent activity against the tested microorganisms, with the minimum inhibitory concentration (MIC) values ranging from 0.25 to 256.00 μg/mL. Among the tested compounds, two quaternary compounds, para-N-chlorobenzyl and meta-N-bromobenzyl quinuclidinium oximes, displayed the most potent and broad-spectrum activity against both gram-positive and gram-negative bacterial strains (MIC values from 0.25 to 4.00 μg/mL), with the lowest value for the important multidrug resistant gram-negative pathogen Pseudomonas aeruginosa. In the case of Klebsiella pneumoniae, activity of those compounds are 256-fold and 16-fold better than gentamicin, respectively. MTT assays showed that compounds are nontoxic for human cell lines. Multi-way analysis was used to separately reduce dimensionality of quantum chemical data and biological activity data to obtain a regression model and the required parameters for the enhancement of biological activity.
- Kastelic, Andreja Radman,Od?ak, Renata,Pezdirc, Iskra,Sovi?, Karlo,Hrenar, Tomica,Ga?parovi?, Ana ?ipak,Sko?ibu?i?, Mirjana,Primo?i?, Ines
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Read Online
- Three new quinuclidine-based structures: Second harmonic generation response for 1,2-bis(1-azoniabicyclo[2.2.2]octan-3-ylidene)-hydrazine dichloride
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The crystal structures of three quinuclidine-based compounds, namely (1-azabicyclo[2.2.2]octan-3-ylidene)hydrazine monohydrate, C7H13N3.H2O(1), 1,2-bis(1-azabicyclo[2.2.2]octan-3-ylidene)hydrazine, C14H22N4 (2), and 1,2-bis-(1-azoniabicyclo[2.2.2]octan-3-ylidene)hydrazine dichloride, C14H24N42+.2Cl (3), are reported. In the crystal structure of 1, the quinuclidine-substituted hydrazine and water molecules are linked through N—H…O and O—H…N hydrogen bonds, forming a two-dimensional array. The compound crystallizes in the centrosymmetric space group P21/c. Compound 2 was refined in the space group Pccn and exhibits no hydrogen bonding. However, its hydrochloride form 3 crystallizes in the noncentrosymmetric space group Pc. It shows a three-dimensional network structure via intermolecular hydrogen bonding (N—H…C and N/C—H…Cl). Compound 3, with its acentric structure, shows strong second harmonic activity.
- Qiao, Liang,Chen, Xiao-Gang,Gao, Ji-Xing,Ai, Yong
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Read Online
- Highly efficient and practical aerobic oxidation of alcohols by inorganic-ligand supported copper catalysis
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The oxidation of alcohols to aldehydes or ketones is a highly relevant conversion for the pharmaceutical and fine-chemical industries, and for biomass conversion, and is commonly performed using stoichiometric amounts of highly hazardous oxidants. The aerobic oxidation of alcohols with transition metal complex catalysts previously required complicated organic ligands and/or nitroxyl radicals as co-catalysts. Herein, we report an efficient and eco-friendly method to promote the aerobic oxidation of alcohols using an inorganic-ligand supported copper catalyst 1, (NH4)4[CuMo6O18(OH)6], with O2 (1 atm) as the sole oxidant. Catalyst 1 is synthesized directly from cheap and commonly available (NH4)6Mo7O24·4H2O and CuSO4, which consists of a pure inorganic framework built from a central CuII core supported by six MoVIO6 inorganic scaffolds. The copper catalyst 1 exhibits excellent selectivity and activity towards a wide range of substrates in the catalytic oxidation of alcohols, and can avoid the use of toxic oxidants, nitroxyl radicals, and potentially air/moisture sensitive and complicated organic ligands that are not commercially available. Owing to its robust inorganic framework, catalyst 1 shows good stability and reusability, and the catalytic oxidation of alcohols with catalyst 1 could be readily scaled up to gram scale with little loss of catalytic activity, demonstrating great potential of the inorganic-ligand supported Cu catalysts in catalytic chemical transformations.
- Wei, Zheyu,Ru, Shi,Zhao, Qixin,Yu, Han,Zhang, Gang,Wei, Yongge
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supporting information
p. 4069 - 4075
(2019/08/07)
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- Transfer-dehydrogenation of secondary alcohols catalyzed by manganese NNN-pincer complexes
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Novel catalytic systems based on pentacarbonylmanganese bromide and stable NNN-pincer ligands are presented for the transfer-dehydrogenation of secondary alcohols to give the corresponding ketones in good to excellent isolated yields. Best results are obtained using di-picolylamine derivatives as ligands and acetone as an inexpensive hydrogen acceptor. Besides high activity for benzylic substrates, aliphatic alcohols, as well as steroid derivatives, are readily oxidized in the presence of the optimal phosphorus-free catalyst.
- Budweg, Svenja,Junge, Kathrin,Beller, Matthias
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supporting information
p. 14143 - 14146
(2019/12/02)
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- Directional Intermolecular Interactions for Precise Molecular Design of a High- Tc Multiaxial Molecular Ferroelectric
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Quasi-spherical molecules have recently been developed as promising building blocks for constructing high-performance molecular ferroelectrics. However, although the modification of spherical molecules into quasi-spherical ones can efficiently lower the crystal symmetry, it is still a challenge to precisely arouse a low-symmetric polar crystal structure. Here, by introducing directional hydrogen-bonding interactions in the molecular modification, we successfully reduced the cubic centrosymmetric Pm3m space group of [quinuclidinium]ClO4 at room temperature to the orthorhombic polar Pna21 space group of [3-oxoquinuclidinium]ClO4. Different from the substituent groups of -OH, -CH3, and -CH2, the addition of a -O group with H-acceptor to [quinuclidinium]+ forms directionally N-H?O-C hydrogen-bonded chains, which plays a critical role in the generation of polar structure in [3-oxoquinuclidinium]ClO4. Systematic characterization indicates that [3-oxoquinuclidinium]ClO4 is an excellent molecular ferroelectric with a high Curie temperature of 457 K, a large saturate polarization of 6.7 μC/cm2, and a multiaxial feature of 6 equiv ferroelectric axes. This work demonstrates that the strategy of combining quasi-spherical molecule building blocks with directional intermolecular interactions provides an efficient route to precisely design new eminent molecular ferroelectrics.
- Yang, Chen-Kai,Chen, Wang-Nan,Ding, Yan-Ting,Wang, Jing,Rao, Yin,Liao, Wei-Qiang,Xie, Yongfa,Zou, Wennan,Xiong, Ren-Gen
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p. 1781 - 1787
(2019/01/26)
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- Highly practical and efficient preparation of aldehydes and ketones from aerobic oxidation of alcohols with an inorganic-ligand supported iodine catalyst
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Herein, we divulge an efficient protocol for aerobic oxidation of alcohols with an inorganic-ligand supported iodine catalyst, (NH4)5[IMo6O24]. The catalyst system is compatible with a wide range of groups and exhibits high selectivity, and shows excellent stability and reusability, thus serving as a potentially greener alternative to the classical transformations.
- Zhang, Mengqi,Zhai, Yongyan,Ru, Shi,Zang, Dejin,Han, Sheng,Yu, Han,Wei, Yongge
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supporting information
p. 10164 - 10167
(2018/09/13)
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- Chemoselective Continuous Ru-Catalyzed Hydrogen-Transfer Oppenauer-Type Oxidation of Secondary Alcohols
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A continuous flow method for the selective oxidation of secondary alcohols is reported. The method is based on an Oppenauer-type ruthenium-catalyzed hydrogen-transfer process that uses acetone as both solvent and oxidant. The process utilizes a low loading (1 mol%) of the commercially available ruthenium catalyst [Ru(p-cymene)Cl2]2 and triethylamine as a base and can be successfully applied to a range of different substrates, with a good level of functional group tolerance.
- Labes, Ricardo,Battilocchio, Claudio,Mateos, Carlos,Cumming, Graham R.,De Frutos, Oscar,Rincón, Juan A.,Binder, Kellie,Ley, Steven V.
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supporting information
p. 1419 - 1422
(2017/09/23)
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- A process for preparing (R)- 3 - quinine alcohol method (by machine translation)
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The present invention provides a process for preparing (R)- 3 - quinine alcohol method. A process for preparing (R)- 3 - quinine alcohol method, characterized in that comprises the following steps: 1) the first 3 - quinine cyclic ketone hydrochloride in alkali solution salt obtained under the action of the 3 - quinine cycloketones; 2) under oxygen free conditions then, the use of chiral catalyst (S, S) xylskewphosRuBr2 QUIMA and alkali under the action of the 3 - quinine cycloketones asymmetric hydrogenation reduction to obtain (R)- 3 - quinine alcohol. The beneficial effect of the present invention is: to achieve the conversion rate of raw materials 99.5% or more, the product ee value reaches 95% or more. (by machine translation)
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Paragraph 0047; 0048
(2017/11/16)
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- Structure-property relationship of quinuclidinium surfactants-Towards multifunctional biologically active molecules
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Motivated by diverse biological and pharmacological activity of quinuclidine and oxime compounds we have synthesized and characterized novel class of surfactants, 3-hydroxyimino quinuclidinium bromides with different alkyl chains lengths (CnQNOH; n = 12, 14 and 16). The incorporation of non conventional hydroxyimino quinuclidinium headgroup and variation in alkyl chain length affects hydrophilic-hydrophobic balance of surfactant molecule and thereby physicochemical properties important for its application. Therefore, newly synthesized surfactants were characterized by the combination of different experimental techniques: X-ray analysis, potentiometry, electrical conductivity, surface tension and dynamic light scattering measurements, as well as antimicrobial susceptibility tests. Comprehensive investigation of CnQNOH surfactants enabled insight into structure-property relationship i.e., way in which the arrangement of surfactant molecules in the crystal phase correlates with their solution behavior and biologically activity. The synthesized CnQNOH surfactants exhibited high adsorption efficiency and relatively low critical micelle concentrations. In addition, all investigated compounds showed very potent and promising activity against Gram-positive and clinically relevant Gram-negative bacterial strains compared to conventional antimicrobial agents: tetracycline and gentamicin. The overall results indicate that bicyclic headgroup with oxime moiety, which affects both hydrophilicity and hydrophobicity of CnQNOH molecule in addition to enabling hydrogen bonding, has dominant effect on crystal packing and physicochemical properties. The unique structural features of cationic surfactants with hydroxyimino quinuclidine headgroup along with diverse biological activity have made them promising structures in novel drug discovery. Obtained fundamental understanding how combination of different functionalities in a single surfactant molecule affects its physicochemical properties represents a good starting point for further biological research.
- Sko?ibu?i?, Mirjana,Od?ak, Renata,?tefani?, Zoran,Kri?i?, Ivana,Kri?to, Lucija,Jovi?, Ozren,Hrenar, Tomica,Primo?i?, Ines,Jura?in, Darija
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p. 548 - 559
(2016/02/18)
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- HETEROCYCLIC COMPOUNDS FOR USE IN THE TREATMENT OF PI3K-GAMMA MEDIATED DISORDERS
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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.
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Paragraph 001338
(2015/11/10)
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- Highly chemoselective aerobic oxidation of amino alcohols into amino carbonyl compounds
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The direct oxidation of unprotected amino alcohols to their corresponding amino carbonyl compounds has often posed serious challenges in organic synthesis and has constrained chemists to adopting an indirect route, such as a protection/deprotection strategy, to attain their goal. Described herein is a highly chemoselective aerobic oxidation of unprotected amino alcohols to their amino carbonyl compounds in which 2-azaadamantane N-oxyl (AZADO)/copper catalysis is used. The catalytic system developed leads to the alcohol-selective oxidation of various unprotected amino alcohols, carrying a primary, secondary, or tertiary amino group, in good to high yield at ambient temperature with exposure to air, thus offering flexibility in the synthesis of nitrogen-containing compounds. Strong as an ox: The highly chemoselective aerobic oxidation of unprotected amino alcohols to their corresponding amino carbonyl compounds has been achieved by using 2-azaadamantane N-oxyl (AZADO)/copper catalysis. This catalytic system oxidizes not only alcohols with tertiary amino groups but also those with secondary and primary amines in good to high yield at ambient temperature in air. bpy=2,2-bipyridyl, DMAP=4-(N,N-dimethylamino)pyridine.
- Sasano, Yusuke,Nagasawa, Shota,Yamazaki, Mai,Shibuya, Masatoshi,Park, Jaiwook,Iwabuchi, Yoshiharu
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supporting information
p. 3236 - 3240
(2014/04/03)
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- METHOD FOR OXIDIZING ALCOHOLS
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A method for oxidizing an alcohol, wherein oxidation is performed in the presence of a compound represented by the following formula (I) and a bulk oxidant, which enables efficient oxidation of secondary alcohols as well as primary alcohols, and can attain high reaction efficiency even when air is used as a bulk oxidant.
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Paragraph 0119; 0120
(2013/06/05)
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- Efficient aerobic oxidation of secondary alcohols at ambient temperature with an ABNO/NOx catalyst system
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New highly practical methods are presented for aerobic oxidation of secondary alcohols with a nitroxyl radical in combination with HNO3, NaNO2, or both as cocatalysts. Diverse nitroxyls are compared, including several novel bicyclic derivatives. Catalyst systems with the readily available nitroxyls, 9-azabicyclo[3.3.1]nonane-N-oxyl (ABNO) and 9-azabicyclo[3.3.1]nonan-3-one-N-oxyl (keto-ABNO), are optimized in acetic acid or acetonitrile as the solvent. The reactions are compatible with substrates bearing diverse functional groups and proceed efficiently under mild conditions at ambient pressure and temperature.
- Lauber, Markus B.,Stahl, Shannon S.
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p. 2612 - 2616
(2013/11/19)
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- Oxidation of alcohols to carbonyl compounds with diisopropyl azodicarboxylate catalyzed by nitroxyl radicals
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A nitroxyl-radical-catalyzed oxidation of alcohols using diisopropyl azodicarboxylate (DIAD) as the terminal oxidantis reported. A variety of primary and secondary alcohols including aliphatic, benzylic, and allylic alcohols are efficiently oxidized to their corresponding aldehydes and ketones without overoxidation to carboxylic acid. 1,2-Diols are oxidized to hydroxyl ketones or diketones depending on the amount of DIAD used.
- Hayashi, Masaki,Shibuya, Masatoshi,Iwabuchi, Yoshiharu
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experimental part
p. 3005 - 3009
(2012/05/04)
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- METHOD FOR PRODUCING COMPOUND WITH CARBONYL GROUP BY USING RUTHENIUM CARBONYL COMPLEX HAVING TRIDENTATE LIGAND AS DEHYDROGENATION OXIDATION CATALYST
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Provided by the present invention is a method for efficient oxidation of alcohols by using, as a catalyst for dehydrogenation oxidation, a ruthenium complex which can be easily produced and easily handled and is obtainable at a relatively low cost. The invention relates to a method of producing a compound having a carbonyl group by dehydrogenation oxidation of alcohols by using as a catalyst the ruthenium carbonyl complex represented by the following general formula (1) RuXY(CO)(L) (1) (in the general formula (1), X and Y may be the same or different from each other and represent an anionic ligand, and L represents a tridentate aminodiphosphine ligand).
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Page/Page column 46-48
(2012/11/07)
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- 9-azanoradamantane N-Oxyl (Nor-AZADO): A highly active organocatalyst for alcohol oxidation
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A highly active organocatalyst for alcohol oxidation has been developed. 9-Azanoradamantane N-oxyl (Nor-AZADO 4), constituting an unhindered, stable nitroxyl radical, exhibits superior catalytic activity to 2,2,6,6- tetramethylpiperidine-1-oxyl (TEMPO) and AZADOs in the oxidation of alcohols to their corresponding carbonyl compounds.
- Hayashi, Masaki,Sasano, Yusuke,Nagasawa, Shota,Shibuya, Masatoshi,Iwabuchi, Yoshiharu
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experimental part
p. 1570 - 1573
(2012/01/05)
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- AZONIA BICYCLOALKANES AS M3 MUSCARINIC ACETYLCHOLIN RECEPTOR ANTAGONISTS
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This invention relates to M3 antagonists of formula (I): wherein R2, R4, R5, R6, W, V, A, D, X, t, u and v are as defined herein; pharmaceutical compositions containing them; methods for their preparation; and their use in the treatment of diseases where enhanced M3 receptor activation is implicated.
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Page/Page column 71
(2009/10/09)
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- AZAINDOLE DERIVATIVES WITH A COMBINATION OF PARTIAL NICOTINIC ACETYL-CHOLINE RECEPTOR AGONISM AND DOPAMINE REUPTAKE INHIBITION
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Azaindole derivatives of formula (I): wherein the symbols have the meanings given in the specification, are described. These compounds have a combination of partial nicotinic acetylcholine receptor agonism and dopamine reuptake inhibition. The invention also relates to pharmaceutical compositions containing these compounds, to methods for preparing them, methods for preparing novel intermediates useful for their synthesis, methods for preparing compositions, and uses of such compounds and compositions, for example, their use in administering them to patients to achieve a therapeutic effect in disorders in which nicotinic receptors and/or dopamine transporters are involved, or that can be treated via manipulation of those receptors
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Page/Page column 18
(2008/06/13)
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- HETEROCYCLIC DERIVATIVES AS M3 MUSCARINIC RECEPTORS
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This invention relates to M3 antagonists of formula (I) wherein R2, R4, R5, R6, W, V, A, D, X, t, u and v are as defined herein; pharmaceutical compositions containing them; methods for their preparation; and their use in the treatment of diseases where enhanced M3 receptor activation is implicated.
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Page/Page column 71
(2008/12/08)
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- Amides of acetic and propionic acids
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The invention relates to novel amides of acetic and propionic acids, methods for production and use thereof for the production of medicaments for the treatment and/or prophylaxis of diseases and for improving perception, concentration, learning ability and memory.
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Page/Page column 6
(2008/06/13)
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- 2-Azaadamantane N-oxyl (AZADO) and 1-Me-AZADO: Highly efficient organocatalysts for oxidation of alcohols
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Development of a stable nitroxyl radical class of catalysts, 2-azaadamantane N-oxyl (AZADO) and 1-Me-AZADO, for highly efficient oxidation of alcohols is described. AZADO and 1-Me-AZADO exhibit superior catalytic proficiency to TEMPO, converting various sterically hindered alcohols to the corresponding carbonyl compounds in excellent yields. Copyright
- Shibuya, Masatoshi,Tomizawa, Masaki,Suzuki, Iwao,Iwabuchi, Yoshiharu
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p. 8412 - 8413
(2007/10/03)
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- Spirocyclic quinuclidinic ether derivatives
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Compounds of formula (I) wherein n1 is 0, 1, or 2; n2 is 0, 1, or 2; X is a bond, O, S, or NR1; and Ar1 is a 5-membered aromatic ring, 6-membered aromatic ring, or a fused bicycloheterocycle. The compounds are useful in treating conditions or disorders prevented by or ameliorated by α7 nAChR ligands. Also disclosed are pharmaceutical compositions having compounds of formula (I) and methods for using such compounds and compositions.
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Page/Page column 15
(2010/02/12)
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- Spirocyclic quinuclidinic ether derivatives
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Compounds of formula (I) wherein n1 is 0, 1, or 2; n2 is 0, 1, or 2; X is a bond, O, S, or NR1; and Ar1 is a 5-membered aromatic ring, 6-membered aromatic ring, or a fused bicycloheterocycle. The compounds are useful in treating conditions or disorders prevented by or ameliorated by α7 nAChR ligands. Also disclosed are pharmaceutical compositions having compounds of formula (I) and methods for using such compounds and compositions.
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Page/Page column 15
(2010/02/12)
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- A practical chemoenzymatic process to access (R)-quinuclidin-3-ol on scale
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(±)-3-Butyryloxyquinuclidinium butyrate 6 (2 M, 571 g/L), prepared from (±)-quinuclidin-3-ol 1 and butyric anhydride, undergoes enantioselective hydrolysis by an Aspergillus melleus protease {1.0% (w/v)} in water in the presence of Ca(OH)2 to keep the reaction at pH 7 and trap butyric acid that is introduced as part of (±)-6 and generated by the enzymatic hydrolysis. After a 24 h period, extraction with n-heptane provides (R)-quinuclidin-3-yl butyrate 5a, which, on methanolysis with Na2CO3, is converted into (R)-1, a common pharmacophore of neuromodulators acting on muscarinic receptors, in 96% ee and 42% overall yield from (±)-1. The unwanted antipode (S)-1, which is extracted into n-butanol and purified via its hydrochloride salt in 89% ee and 40% overall yield from (±)-1, can be racemized by the catalysis of Raney Co at 140°C under an atmosphere of H2 (5 kg/cm2) to regenerate (±)-1 in 97% yield.
- Nomoto, Fumiki,Hirayama, Yoshihiko,Ikunaka, Masaya,Inoue, Toru,Otsuka, Koutaro
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p. 1871 - 1877
(2007/10/03)
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- Highly pure phenothiazine compound, production method thereof, production method of intermediate therefor, and hydrate and novel crystal as starting materials for the intermediate
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According to the method of the present invention, an alkali metal compound, dimethyl sulfoxide, trimethyloxosulfonium halide and 3-quinuclidinone are added in a specific order to give the following compound [II]. This compound is, without treatment or isolation, directly reacted with an alkali metal salt of phenothiazine to give the following compound [III], from which the following compound [I] is obtained. During the production of compound [I], a by-produced acidic gas is removed and water is added to ensure industrial, safe and efficient production of compound [I] at a constantly high yield. Inasmuch as the present invention enables production of the following highly pure compound [A] by eliminating hydrogen halide of compound [I] in glyme in the presence of at least one kind of a base selected from potassium hydroxide and potassium alkoxide, compound [A] having a high purity of not less than 85 mol % can be provided.
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- A new modified "montanari oxidation process" by means of chlorine dissolved in the reaction solvent as oxidant and TEMPO as catalyst: Oxidation of 3-S-quinuclidinol to 3-quinuclidinone
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Results from a process improvement project for preparation of 3-R-quinuclidinol, a highly valuable intermediate for several muscarine-active compounds are described. The studied process was based on the kinetic resolution of racemic 3-quinuclidinol and th
- Bjorsvik, Hans-Rene,Liguori, Lucia,Costantino, Francesca,Minisci, Francesco
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p. 197 - 200
(2013/09/06)
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- Process for the preparation of optically active 3-quinuclidinol
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Optically active 3-quinuclidinol is obtained by the asymmetric hydrogenation of 3-quinuclidinone, its Lewis acid adducts or its tertiary or quaternary salts, for example, 1-(diphenylmethyl)-3-oxoquinuclidinium bromide. Rhodium/chiral diphosphine complexes with a metallocene structure are preferably used as catalysts. Optically active 3-quinuclidinol is a synthetic building block for pharmaceutical active substances (M1 receptor agonists).
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- Novel heterocycles derived from 3-acyloxy- and 3-acetamidoquinuclidines
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New quinuclidine derivatives with 3-spiro annelated oxathioline, furanone, and pyrrolinone heterocycles have been synthesized from 3-mesyloxy-, 3-acetoxy-, and 3-acetamidoquinuclidine-3-carbonitrile, respectively, by treatment with base. Treatment of 3-acetamidoquinuclidine-3-carbonitrile (3) with potassium hydride resulted in decyanation whereas alkyllithium reagents attacked the cyano group in 3 to produce the corresponding imines. Oxidative cyclization of the N-benzylated derivative of 3 with palladium acetate gave the tetracyclic compound 5-acetyl-1,4-ethano-1,2,3,4,5,6-hexahydrobenzo[c]-1,5-naphthyridine.
- Besidsky,Luthman,Hacksell
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p. 1497 - 1501
(2007/10/02)
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- GIF OXIDATION OF SOME ALICYCLIC AMINES
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The Gif oxidation of seven alicyclic tertiary amines leads essentially to the formation of lactams.The structure of the products present in trace amounts supports the mechanistic hypothesis previously advanced.The structures of the oxidation products were investigated using high performance GC-MS system.
- Boivin, J.,Gaudin, D.,Labrecque, D.,Jankowski, K.
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p. 2281 - 2282
(2007/10/02)
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