- Molecular energetics of alkyl substituted pyridine N-oxides: An experimental study
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The standard (p° = 0.1 MPa) energies of combustion in oxygen, at T = 298.15 K, for the solid compounds 2-methylpyridine-N-oxide (2-MePyNO), 3-methylpyridine-N-oxide (3-MePyNO) and 3,5-dimethylpyridine-N-oxide (3,5-DMePyNO) were measured by static-bomb calorimetry, from which the respective standard molar enthalpies of formation in the condensed phase were derived. The standard molar enthalpies of sublimation, at the same temperature, were measured by Calvet microcalorimetry. From the standard molar enthalpy of formation in gaseous phase, the molar dissociation enthalpies of the N-O bonds were derived, and compared with values of the dissociation enthalpies of other N-O bonds available for other pyridine-N-oxide derivatives.
- Cabral, Joana I. T. A.,Monteiro, Ricardo A. R.,Rocha, Marisa A. A.,Santos, Luis M.N.B.F.,Acree Jr., William E.,Ribeiro Da Silva, Maria D. M. C.
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- Method for synthesizing pyridine-N-oxide through catalytic oxidation by continuous non-solvent method
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The invention discloses a method for synthesizing pyridine-N-oxide through catalytic oxidation by a continuous non-solvent method, and belongs to the field of chemical synthesis. The method is characterized by comprising the following steps: mixing metered pyridine or alkyl pyridine with an oxidizing agent in proportion, carrying out a reaction in a continuous tubular reactor filled with an immobilized catalyst, and distilling off excess water after the reaction is finished to obtain a pyridine-N-oxide or alkyl pyridine-N-oxide product, wherein the catalyst is cross-linked polystyrene resin immobilized with active substance anions and has a quaternary ammonium salt group. Compared with the prior art, the method for synthesizing the pyridine-N-oxide through catalytic oxidation by the continuous non-solvent method can realize continuous production of the pyridine-N-oxide, is environment-friendly, energy-saving and high in conversion rate, and has very good promotion and application values.
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Paragraph 0051-0057
(2020/08/06)
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- The M?CPbA?NH3(G) system: A safe and scalable alternative for the manufacture of (substituted) pyridine and quinoline N?oxides?
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An improved, safe, and scalable isolation process for (substituted) pyridine and quinoline N-oxides in quantitative yields along with high purities using the m-CPBA?NH3(g) system is described. The safety was assessed by reaction calorimetry and differential scanning calorimetry studies for possible hazards during the conversion and isolation steps. Careful interpretation of the data substantiated the safety and scalability. The process flow is simplified to meet the industrial requirements of safety, cost-effectiveness, and utility minimization. The reaction was safely demonstrated at a 2.5 kg scale.
- Palav, Amey,Misal, Balu,Ernolla, Anilkumar,Parab, Vinod,Waske, Prashant,Khandekar, Dileep,Chaudhary, Vinay,Chaturbhuj, Ganesh
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supporting information
p. 244 - 251
(2019/03/17)
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- A pyridine nitrogen oxide high-efficient, multi-phase catalytic preparation method
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The invention discloses a high efficient heterogeneous catalytic preparation method of pyridine oxynitride. In the provided preparation method, mono-substituted or poly-substituted pyridines or pyridine derivatives are taken as the primary raw materials, titanium dioxide loaded on tungsten (WO3/TiO2) is taken as the catalyst, hydrogen peroxide is taken as the oxidizing agent, and reactions are carried out in a water solution at a room temperature so as to obtain the target product. Compared with the prior art, the preparation method has the following advantages: (1) the provided oxidation method, no acetic acid is used, and thus the requirements on equipment are greatly reduced; (2) a heterogeneous catalytic method is adopted to prepare pyridine oxynitride, the catalyst can be separated from the reaction system through simple filtration or centrifugation, and the operation is convenient; (3) titanium dioxide loaded on tungsten is taken as the catalyst, pyridine oxynitride is prepared by one step in a water solution at a room temperature, the reaction conditions are mild, and the pollution to the environment is little.
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Paragraph 0053; 0057; 0058; 0059; 0060; 0097; 0101-0103
(2017/08/25)
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- Catalyst-free and selective oxidation of pyridine derivatives and tertiary amines to corresponding N-oxides with 1,2-diphenyl-1,1,2,2-tetrahydroperoxyethane
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The catalyst-free oxidation of various pyridine derivatives and tertiary amines to their corresponding N-oxides with 1,1,2,2-tetrahydroperoxy-1,2-diphenylethane as an efficient oxidant has been developed. The methodology proved to tolerate a number of functional groups. The reactions proceeded smoothly under solvent-free and mild conditions at room temperature. All the products were easily extracted from the reaction mixtures in excellent yields. Graphical abstract: The catalyst-free oxidation of various pyridine derivatives and tertiary amines to their corresponding N-oxides with 1,1,2,2-tetrahydroperoxy-1,2-diphenylethane as an efficient oxidant has been developed. The methodology proved to tolerate a number of functional groups. The reactions proceeded smoothly under solvent-free and mild conditions at room temperature. All the products were easily extracted from the reaction mixtures in excellent yields.
- Azarifar, Davood,Mahmoudi, Boshra
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p. 645 - 651
(2016/02/19)
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- DIMETHYLBENZOIC ACID COMPOUNDS
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The present invention provides a compound of the Formula I: wherein A is: and W, Y, X, R1, R2, R3, and R4 are as defined herein, or a pharmaceutically acceptable salt thereof, for use as an inhibitor of the EP4 receptor.
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Page/Page column 34
(2015/07/07)
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- Controlled oxygen release from pyridone endoperoxides promotes cell survival under anoxic conditions
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In tissue engineering, survival of larger constructs remains challenging due to limited supply of oxygen caused by a lack of early vascularization. Controlled release of oxygen from small organic molecules represents a possible strategy to prevent cell death under anoxic conditions. A comprehensive study of methylated pyridone-derived endoperoxides has led to the development of water-soluble molecules that undergo retro-Diels-Alder reactions in aqueous environment releasing oxygen in high yield and with half-lives of up to 13 h. These molecules in combination with vitamin C as singlet oxygen quencher significantly improved survival of 3T3 fibroblasts and rat smooth muscle cells challenged with oxygen-depleted conditions.
- Benz, Sebastian,N?tzli, Sarah,Siegel, Jay S.,Eberli, Daniel,Jessen, Henning J.
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p. 10171 - 10182
(2014/01/17)
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- PYRIDINE- 2- DERIVATIVES AS SMOOTHENED RECEPTOR MODULATORS
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The present application relates to compounds of Formula (I), and Formula (II), or pharmaceutically acceptable salt thereof, wherein A, X, Y, Z, e, f, R1, R2, R3, R4, R5, R5b, R6, R7, R8, R9, R10, R11,R20, R21, R22 and R23 are defined herein. These novel pyridine derivatives that are useful in therapy, in particular for treating diseases or conditions mediated by Smo, including the treatment of abnormal cell growth, such as cancer, in mammals. Additional embodiments relate to methods of using such compounds in the treatment of abnormal cell growth in mammals, especially humans, and to pharmaceutical compositions containing such compounds.
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Page/Page column 64
(2012/05/05)
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- Syntheses of sterically hindered zwitterionic pyridinium phenolates as model compounds in nonlinear optics
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Pyridinium phenolates possess a dissymmetric delocalised π-electron system providing a huge quadratic nonlinearity. They are a promising class of molecules for applications in photoelectronics and photonics. Semiempirical calculations indicate that the interplanar angle between the two aromatic rings leads to enhancement in the NLO properties of these compounds. The confirmation of this feature may be provided by the study of a new series of sterically hindered pyridinium phenolates 2a-e bearing two tert-butyl substituents at the ortho position(s) of the phenolate functionality. Such bulky groups would enhance the solubility of zwitterions in organic solvents and would limit the formation of aggregates. Their efficient preparations by using Suzuki cross-coupling reactions involving 3,5-dialkylated 4-bromopyridine N-oxides are described herein. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Diemer, Vincent,Chaumeil, Helene,Defoin, Albert,Fort, Alain,Boeglin, Alex,Carre, Christiane
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experimental part
p. 1767 - 1776
(2009/04/11)
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- NOVEL SULFONYL DERIVATIVES
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Sulfonyl derivatives represented by the following general formula (I): Q1-Q2-T1-Q3-SO2-QA and drugs containing the same (wherein Q1 is an optionally substituted, saturated or unsaturated, five- or six-membered cyclic hydrocarbon group, a five- or six-membered heterocyclic group, or the like; Q2 is a single band, oxygen, sulfur, C1-C6 alkylene or the like; QA is optionally substituted arylalkenyl, heteroarylalkenyl or the like; and T1 is carbonyl or the like). These compounds have potent FXa-inhibitory effects and promptly exert satisfactory and persistent antithrombotic effects through oral administration, thus being useful as anticoagulant agents little accompanied with side effects.
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- A simple and efficient method for the preparation of N- heteroaromatic N-oxides
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Urea-hydrogen peroxide/formic acid system has shown utility for mild and safe N-oxidation of N-heteroaromatic compounds.
- Balicki, Roman,Golinski, Jerzy
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p. 1529 - 1534
(2007/10/03)
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- Tricyclic carbamate compounds useful for inhibition of G-protein function and for treatment of proliferative diseases
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A method of inhibiting Ras function and therefore inhibiting cellular growth is disclosed. The method comprises the administration of a compound of Formula 1.0 Also disclosed are novel compounds of the formulas: Also disclosed are processes for making 3-substituted compounds of the Formulas 1.1, 1.2 and 1.3. Further disclosed are novel compounds which are intermediates in the processes for making the 3-substituted compounds of Formulas 1.1, 1.2, and 1.3.
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- 4a, 5a, 8a, 8b-tetrahydro-6H-ptrrolo [3,4':4,5]furo(3,2-b) pyridine-6,8[7H]-dione derivatives for use in controlling endoparasites and a method of producing said derivatives
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PCT No. PCT/EP96/04346 Sec. 371 Date Apr. 15, 1998 Sec. 102(e) Date Apr. 15, 1998 PCT Filed Oct. 7, 1996 PCT Pub. No. WO97/14695 PCT Pub. Date Apr. 24, 1997The present invention relates to the use of 4a, 5a, 8a, 8b-tetrahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione derivatives of the general formula (I) and salts thereof, in which the radicals R1 to R5 have the meaning given in the description, and to novel 4a, 5a, 8a, 8b-tetrahydro-6H-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8(7H)-dione derivatives and processes for their preparation.
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- Tricyclic carbamate compounds useful for inhibition of G-protein function and for treatment of proliferative diseases
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A method of inhibiting Ras function and therefore inhibiting cellular growth is disclosed. The method comprises the administration of a compound of Formula 1.0 STR1 Also disclosed are novel compounds of the formulas: STR2 Also disclosed are processes for making 3-substituted compounds of the Formulas 1.1, 1.2 and 1.3. Further disclosed are novel compounds which are intermediates in the processes for making the 3-substituted compounds of Formulas 1.1, 1.2, and 1.3.
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- Tricyclic amide and urea compounds useful for inhibition of g-protein function and for treatment of proliferative diseases
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A method of inhibiting Ras function and therefore inhibiting the abnormal growth of cells is disclosed. The method comprises the administration of a compound of Formula 1.0: STR1 to a biological system. In particular, the method inhibits the abnormal growth of cells in a mammal such as a human being. Novel compounds of formulas 5.0, 5.1 and 5.2, wherein R is --C(R20)(R21)(R46), and 5.3, 5.3A and 5.3B, wherein R is --N(R25)(R48), are disclosed. Also disclosed are processes for making 3-substituted compounds of Formulas 5.0, 5.1, 5.2 and 5.3. Further disclosed are novel compounds which are intermediates in the process for making 3-substituted compounds of Formulas 5.0, 5.1, 5.2 and 5.3.
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- Tricyclic amide and urea compounds useful for inhibition of G-protein function and for treatment of proliferative diseases
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Novel compounds of Formula (7.0a), (7.0b) or (7.0c): STR1 are disclosed. Also disclosed is a method of inhibiting Ras function and therefore inhibiting the abnormal growth of cells. The method comprises administering a compound of the formula (7.0a), (7.0b) or (7.0c) to a biological system. In particular, the method inhibits the abnormal growth of cells in a mammal such as a human being.
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- AN IMPROVED PROCEDURE FOR THE PREPARATION OF AROMATIC HETEROCYCLIC N-OXIDES
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An improved procedure for the preparation of aromatic heterocyclic N-oxide is described.Nitrogen containing heterocyclic compounds gave their N-oxides in excellent yields by the reaction of m-CPBA in DMF/MeOH in the presence of HF in a short time under mild reaction conditions.The presence of HF and MeOH is crucial for the reaction.
- Rhie, Soo Young,Ryu, Eung K.
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p. 323 - 328
(2007/10/03)
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- Bis-benzo or benzopyrido cyclohepta piperidene, piperidylidene and piperazine compounds, compositions and methods of use
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Bis-benzo or benzopyrido piperidene, piperidylidene and piperazine compounds of the formula: STR1 and pharmaceutically acceptable salts thereof are disclosed, wherein Z represents --(C(Ra)2)m --Y--(C(Ra)2)n -- or STR2 The compounds of Formula I possess anti-allergic and anti-inflammatory activity. Methods for preparing and using the compounds are also described.
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- Effect of Metal Ions on the Bromination of 3,5-Dimethylpyridine-N-oxide in Acetic Acid
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The influence of metal ions on γ-bromination and N-O bond reduction of 3,5-dimethylpyridine-N-oxide (2) in acetic acid is described. Keywords: Derivatives of 3,5-dimethylpyridine; Bromination; Reduction; metal ions.
- Klan, P.
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p. 327 - 330
(2007/10/02)
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- Heterocyclic n-oxide derivatives of substituted benzo[5,6]cycloheptapyridines, compositions and methods of use
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Heterocyclic N-oxide derivatives of substituted benzo[5,6]cycloheptapyridines, and pharmaceutically acceptable salts and solvates thereof are disclosed, which possess anti-allergic and anti-inflammatory activity. Methods for preparing and using the compounds are also described.
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- Benzopyrido piperidine, piperidylidene and piperazine compounds, compositions, methods of manufacture and methods of use
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Novel benzopyrido piperidiene, piperidylidene and piperazine compounds of the generalized formula STR1 are disclosed as useful for the treatment of asthma, allergy and inflammation. Novel pharmaceutical compositions containing such compounds and processes for producing the compounds are also disclosed.
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- 3,5-dimethyl-4-methoxypyridine derivatives
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A process for the preparation of compounds of formula I STR1 in which X is the radical OH or Cl, by the catalytic hydrogenation of 3,5-dimethyl-4-methoxy-2-cyanopyridine, subsequent reaction of the resulting 3,5-dimethyl-4-methoxy-2-aminomethylpyridine to give 3,5-dimethyl-4-methoxy-2-hydroxymethylpyridine and, if desired, chlorination to give 3,5-dimethyl-4-methoxy-2-chloromethylpyridine, and the novel intermediate 3,5-dimethyl-4-methoxy-2-aminomethylpyridine.
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- Synthese regioselective par voie organometallique de pyridines, 4-picolines et 3,5-lutidines substituees en 2 par un groupe insature et/ou fonctionnel
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A regioselective one-pot synthesis of 2-substituted pyridine derivatives from N-alkoxycarboxylpyridinium salts and α-unsaturated organozinc compounds is described.Similarly, functional alkynyl organomagnesium compounds lead to 2-alkynyl-ω-functional pyridines, from which (E)-2-alkenyl or 2-alkyl-ω-functional pyridines can be obtained by partial or complete reduction.
- Al-Arnaout, A.,Courtois, G.,Miginiac, L.
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p. 139 - 154
(2007/10/02)
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- Certain pyridyl-N-oxide intermediates for the preparation of omeprazole
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Novel compounds of the formula STR1 wherein R is H or CH3, a process for their preparation, and their use as intermediates in the preparation of pharmaceutically useful compounds, e.g. substituted benzimidazoles containing a pyridine radical, i.a. omeprazole.
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