- Full functionalization of the 7-azaindole scaffold by selective metalation and sulfoxide/magnesium exchange
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Filling positions: 7-Azaindoles are important targets in the pharmaceutical industry. All five carbon positions of the azaindole ring system can be functionalized in a predictable manner starting from the appropriately substituted azaindole 1 by directed metalation and halogen/magnesium and sulfoxide/magnesium exchange. The products are fully substituted azaindoles of type 2.
- Barl, Nadja M.,Sansiaume-Dagousset, Elodie,Karaghiosoff, Konstantin,Knochel, Paul
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Read Online
- Synthesis and Structure-Activity Relationships of 3,5-Disubstituted-pyrrolo[2,3- b]pyridines as Inhibitors of Adaptor-Associated Kinase 1 with Antiviral Activity
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There are currently no approved drugs for the treatment of emerging viral infections, such as dengue and Ebola. Adaptor-associated kinase 1 (AAK1) is a cellular serine-threonine protein kinase that functions as a key regulator of the clathrin-associated host adaptor proteins and regulates the intracellular trafficking of multiple unrelated RNA viruses. Moreover, AAK1 is overexpressed specifically in dengue virus-infected but not bystander cells. Because AAK1 is a promising antiviral drug target, we have embarked on an optimization campaign of a previously identified 7-azaindole analogue, yielding novel pyrrolo[2,3-b]pyridines with high AAK1 affinity. The optimized compounds demonstrate improved activity against dengue virus both in vitro and in human primary dendritic cells and the unrelated Ebola virus. These findings demonstrate that targeting cellular AAK1 may represent a promising broad-spectrum antiviral strategy.
- Verdonck, Sven,Pu, Szu-Yuan,Sorrell, Fiona J.,Elkins, Jon M.,Froeyen, Mathy,Gao, Ling-Jie,Prugar, Laura I.,Dorosky, Danielle E.,Brannan, Jennifer M.,Barouch-Bentov, Rina,Knapp, Stefan,Dye, John M.,Herdewijn, Piet,Einav, Shirit,De Jonghe, Steven
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p. 5810 - 5831
(2019/07/04)
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- Simple preparation method of 5-halogenated-7-azaindole
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The invention discloses a simple preparation method of 5-halogenated-7-azaindole. The method comprises: carrying out a 1,4-addition reaction on 4,4-dialkoxy n-butyronitrile (II) and 2,3-dihalogenatedacrolein (III) in the presence of a solvent and a catalyst to generate 2,3-dihalogenated-4-cyano-6,6-dialkoxy n-hexanal (IV), and carrying out a cyclization reaction on the 2,3-dihalogenated-4-cyano-6,6-dialkoxy n-hexanal, an alkali, ammonia and an ammonium salt to prepare the 5-halogenated-7-azaindole (I). According to the present invention, the method has characteristics of inexpensive and easily available raw materials, short process route, less wastewater discharge, easy environmental protection, convenient reaction operation, high reaction selectivity, high product purity, high yield andlow cost, and is suitable for the environmentally-friendly industrial production of 5-halogenated-7-azaindole.
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Paragraph 0046-0049
(2019/10/01)
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- Method for synthesizing 5-bromo-7-azaindole
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The invention provides a method for synthesizing 5-bromo-7-azaindole, and belongs to the field of medicinal chemical synthesis. The method comprises the following steps: reacting a raw material 1,1,3,3-tetramethoxypropane 2 with bromine to obtain an intermediate 3, preparing an intermediate 4 from an intermediate 3 under the action of an alkali, and reacting the intermediate 4 with 2-aminopyrroleto obtain the 5-bromo-7-azaindole 1. The method has the advantages of few reaction steps, easily available raw materials, high yield, small pollution, and easiness in amplified production.
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Paragraph 0019; 0031-0032
(2019/06/07)
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- A medicine intermediate 5 - bromo -7 - aza indole synthesis method
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The present invention discloses a pharmaceutical intermediate 5 - bromo - 7 - aza indole synthesis method, comprises the following steps: to 2 - nitro - 3 - methyl - 5 - bromo pyridine as raw materials, and DMA and DMF mixture prepared by the reaction of 2 - nitro - 3 - dimethylamine vinyl - 5 - bromo pyridine, after the reaction with the aniline - sodium, to obtain 5 - bromo - 7 - azaindole. The application of the synthesis method is simple in operation, mild condition, less by-products, the product has high purity, product yield is relatively high.
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Paragraph 0022; 0028; 0031; 0034; 0035; 0040; 0046
(2019/03/28)
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- Preparation method for 5-bromo-7-azindole
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The invention belongs to the technical field of preparation of 5-bromo-7-azindole, in particular to a preparation method for the 5-bromo-7-azindole. The method comprises the following steps: taking 2-amino-5-bromopyridine as a raw material, and performing the steps in sequence: (1) introducing iodine through an iodine reagent; (2) performing a coupling reaction with methylbutynol; and (3) performing a ring-closing reaction under the catalysis of inorganic strong base to prepare the 5-bromo-7-azindole, wherein the catalyst adopted in the coupling reaction in the step (2) is bis(benzonitrile)palladium dichloride or [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloromethane dichloride complex compound. According to the preparation method, cheap 2-amino-5-bromopyridine is taken as the rawmaterial in the step (1); the catalyst with high catalyzing efficiency and a solvent which is easy to treat are adopted; purifying steps in each step are simple; the yield is high; and the and the yield of the finally prepared product, namely, the 5-bromo-7-azindole, can reach over 93 percent.
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- Synthesis method of 5-bromo-7-azaindole
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The invention relates to a synthesis method of 5-bromo-7-azaindole. With 7-azaindole as a raw material, conjugation of the five-membered ring of indole is damaged by low-pressure liquid-phase hydrogenation, and a key medical intermediate 5-bromo-7-azaindole is prepared through oxybromination and nonmetal oxydehydrogenation. The product purity is higher than or equal to 99%. Bromine atoms are introduced by an oxybromination technology, the utilization rate of the bromine atoms exceeds 98%, the use of bromine is avoided, and the problem that a large amount of bromine-containing waste liquid is generated in original technology is solved. According to the synthesis method provided by the invention, through nonmetal catalytic dehydrogenation, heavy metal catalysis is avoided, the problem of heavy metal residue easily occurring in the product is solved, and the safety of medicine products is ensured. The reaction efficiency can be effectively improved, the reaction time is shortened, and thetotal reaction yield is increased; moreover, industrial waste liquid and residue is reduced, industrial popularization is facilitated, and remarkably high economic benefits are created.
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Paragraph 0042; 0054-0057; 0070-0073; 0086-0089
(2018/06/26)
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- Synthetic method of 5-bromo-7-azaindole
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The invention discloses a synthetic method of 5-bromo-7-azaindole. According to the synthetic method, 2, 5-dibromo-2-aminopyridine and 3, 3-diethoxy methyl propionate are subjected to synthesis so asto obtain (E)-3-((3, 5-dibromopyridine-2-yl)imino)methyl propionate; and (E)-3-((3, 5-dibromopyridine-2-yl)imino)methyl propionate is subjected to synthesis so as to obtain 5-bromo-1H-pyrrole [2, 3-b] pyrimidine-3-methyl carboxylate; and 5-bromo-1H-pyrrole [2, 3-b] pyrimidine-3-methyl carboxylate is subjected to synthesis so as to obtain 5-bromo-7-azaindole. Reaction steps are few; operation is convenient; reaction steps are high in yield; industrialized production can be realized; quintal grade production can be realized; and relatively high product yield is ensured.
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Paragraph 0033; 0034; 0039; 0040
(2019/01/08)
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- Preparation method of 5-bromine-7-azaindole
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The invention discloses a preparation method of 5-bromine-7-azaindole. The method includes the steps that a, 2-amino-3-methyl-5-bromopyridine and triethyl orthoformate are utilized for obtaining N-(3-methyl-5-bromopyridine-2-radical) ethyl imidoformate; b, N-(3-methyl-5-bromopyridine-2-radical) ethyl ethyl imidoformate and N-methylaniline react to obtain N-(3-methyl-5-bromopyridine-2-radical)-N'-methyl-N'-benzamidine; c, N-(3-methyl-5-bromopyridine-2-radical)-N'-methyl-N'-benzamidine is subjected to a ring closing reaction under the effect of alkali, so that 5-bromine-7-azaindole is obtained.By synthesizing the imino acid ester compound, the one-step nucleophilic reaction is performed, then ring closing is performed, and finally 5-bromine-7-azaindole is obtained; synthesizing can be completed through three steps. The preparation method is easy to operate and suitable for industrialized production.
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Paragraph 0041; 0042; 0044; 0046
(2018/11/22)
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- Preparation method of ABT-199 intermediate
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The invention discloses a preparation method of an ABT-199 intermediate, namely a preparation method of 5-bromo-7-azaindole. The preparation method is specifically as follows: the 5-bromo-7-azaindoleis finally synthesized in three steps from 2-amino-3-methyl-5-bromopyridine as a starting material. By the preparation method, a reaction condition is mild, the operation is easy, anhydrous and oxygen-free operation is not required, high temperature and high pressure are not required, and the safety is high; the yield in a reaction step is high; raw materials are easy to obtain and low in cost; heavy metal is not required to be used for a catalytic reaction; by a production technology, industrialization can be achieved, and hundred kilogram-level production can be performed.
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- Preparation method of 5-bromo-7-azaindole
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The invention belongs to the technical field of preparation of pharmaceutical intermediates and particularly relates to a preparation method of 5-bromo-7-azaindole. The target product, 5-bromo-7-azaindole, is prepared by: subjecting 2-aminopyridine as a raw material to bromination to obtain 5-bromo-2-aminopyridine, subjecting 5-bromo-2-aminopyridine to iodination to obtain 5-bromo-3-iodo-2-aminopyridine, subjecting 5-bromo-3-iodo-2-aminopyridine Sonogashira coupling and deprotection reaction to obtain 5-bromo-3-alkynyl-2-aminopyridine, and carrying out intramolecular ring-closing reaction. Thepreparation method herein has the advantages of low cost, good access to materials, good implementing convenience of reaction conditions, good operation simplicity and the like; the finished 5-bromo-7-azaindole prepared by means of the preparation method has purity of 99.3% and above.
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Paragraph 0023; 0024
(2019/01/14)
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- Fragment-Based Drug Design Facilitated by Protein-Templated Click Chemistry: Fragment Linking and Optimization of Inhibitors of the Aspartic Protease Endothiapepsin
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There is an urgent need for the development of efficient methodologies that accelerate drug discovery. We demonstrate that the strategic combination of fragment linking/optimization and protein-templated click chemistry is an efficient and powerful method that accelerates the hit-identification process for the aspartic protease endothiapepsin. The best binder, which inhibits endothiapepsin with an IC50value of 43 μm, represents the first example of triazole-based inhibitors of endothiapepsin. Our strategy could find application on a whole range of drug targets.
- Mondal, Milon,Unver, M. Yagiz,Pal, Asish,Bakker, Matthijs,Berrier, Stephan P.,Hirsch, Anna K. H.
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supporting information
p. 14826 - 14830
(2016/10/11)
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- A 5-bromo-7-aza-indole synthesis process (by machine translation)
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This invention relates to a kind of 5-bromo-7-aza-indole synthesis process, the steps of: the 7-aza indole, Raney nickel, ethanol stirring and hydrogen; reacting filtering, the filter cake is washed with ethanol washing, combined filtrate, concentrated dry, be 7-aza indole [...] ; the crude product with toluene-P-sulfonic acid, methylene chloride mixed, and stirring instillment bromide ; sodium hyposulfite washing the reaction solution, the organic phase is dried with anhydrous sodium sulfate, concentrated to obtain 5-bromo-7-aza-indoline product; the product is dissolved in toluene, adding manganese dioxide, heating reflux reaction; filtering the reaction liquid, the filter cake washed with methylene chloride, combined organic phase, dried, concentrated to obtain 5-bromo-7-azaindoles crude, PE/EA mixed solution for crystallization to obtain the finished product. The invention has the advantages of low cost, simple process, the operation is simple, and the like, is suitable for large-scale factory production, this method generating the purity of the product in 99% or more, the yield of 74% or more, comprehensive utilization rate is high. (by machine translation)
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Paragraph 0016
(2017/03/08)
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- Production process of 5-bromo-7-azaindole
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The invention relates to a production process of 5-bromo-7-azaindole. The production process includes following steps: (1), using 7-azaindole as a raw material, and enabling 7-azaindole to be in catalytic hydrogenation under action of a catalyst-palladium loaded mesoporous carbon to generate dihydro-7-azaindole; (2), enabling dihydro-7-azaindole to be in bromination reaction under action of hydrogen bromide and hydrogen peroxide to generate dihydro-5-bromo-7-azaindole, where a feeding molar ratio of dihydro-7-azaindole, hydrogen bromide and hydrogen peroxide is 1:10-30:1-2, and temperature for bromination reaction is 20-30 DEG C; (3), enabling dihydro-5-bromo-7-azaindole to be in oxidative dehydrogenation under action of manganese dioxide/glacial acetic acid to generate 5-bromo-7-azaindole. The production process has the advantages of high reaction yield and low cost.
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Paragraph 0021
(2017/04/27)
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- Synthesis method of 5-bromo-7-azaindole
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The invention discloses a synthesis method of 5-bromo-7-azaindole. With 7-azaindole as the raw material, hydrogenation reduction, bromination and dehydrogenation are conducted, a platinum-carbon catalyst is added for catalyzing 7-azaindole to conduct hydrogenation to prepare dihydro-7-azaindole, catalysis efficiency is improved, and reaction energy consumption and reaction time are decreased; 5-bromo-7-azaindoline is synthesized by adding sodium bromide for catalysis, a mixture of chromic oxide, zinc oxide and magnesium oxide is added for substituting manganese dioxide for catalytic dehydrogenation reaction, reaction time can be effectively shortened, and reaction yield is increased. By means of the method, reaction efficiency can be effectively improved, reaction time is shortened, the total reaction yield is increased, process waste liquid and waste slag are reduced, industrial popularization is facilitated, and extremely high economic benefits are achieved.
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Paragraph 0140; 0141; 0149; 0150; 0151; 0152
(2016/12/01)
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- Application of 7-azaisatins in enantioselective Morita-Baylis-Hillman reaction
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7-Azaisatin and 7-azaoxindole skeletons are valuable building blocks in diverse biologically active substances. Here 7-azaisatins turned out to be more efficient electrophiles than the analogous isatins in the enantioselective Morita-Baylis-Hillman (MBH) reactions with maleimides using a bifunctional tertiary amine, β-isocupreidine (β-ICD), as the catalyst. This route allows a convenient approach to access multifunctional 3-hydroxy-7-aza-2-oxindoles with high enantiopurity (up to 94% ee). Other types of activated alkenes, such as acrylates and acrolein, could also be efficiently utilized.
- He, Qing,Zhan, Gu,Du, Wei,Chen, Ying-Chun
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p. 309 - 313
(2016/04/05)
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- Synthesizing method of 5-bromine-1H-pyrrolo[2,3-b]pyridine
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The invention particularly relates to a synthesizing method of 5-bromine-1H-pyrrolo[2,3-b]pyridine. The synthesizing method is characterized in that 1H-pyrrolo[2,3-b]pyridine is dissolved in a solvent to have bromination reaction with a brominating agent under 5-40 DEG C, and reductive dehalogenation is performed under 20-50 DEG C after the bromination reaction to obtain 5-bromine-1,3-dihydro-2H-pyrrolo[2,3-b]pyridine-2-ketone; under the effect of a reducing agent, the 5-bromine-1,3-dihydro-2H-pyrrolo[2,3-b]pyridine-2-ketone has reduction reaction in a certain solvent under 25-40 DEG C, and oxidative dehydrogenation is performed at 25-60 DEG C after the reduction reaction to obtain the 5-bromine-1H-pyrrolo[2,3-b]pyridine. The synthesizing method has the advantages that the method is simple in reaction step and mild in reaction condition, the four-step reaction is simplified into two one-pot two-step reactions, the treatment process is simplified, and the use amount of organic solvents is reduced.
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- NOVEL PROCESSES FOR THE MANUFACTURE OF PROPANE-1-SULFONIC ACID {3-[5-(4-CHLORO-PHENYL)-1H-PYRROLO[2,3-B]PYRIDINE-3-CARBONYL]-2,4-DIFLUORO-PHENYL}-AMIDE
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According to the present invention there are provided novel processes for the manufacture of the compound of formula (1) as well as novel synthesis routes for key intermediates used in those processes.
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Page/Page column 30
(2012/02/05)
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- Novel Processes for the manufacture of Propane-1-sulfonic acid -amide
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According to the present invention there are provided novel processes for the manufacture of the compound of formula 1 as well as intermediates and novel synthesis routes for key intermediates used in those processes.
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Page/Page column 13
(2012/02/03)
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- AZAINDOLE GLUCOKINASE ACTIVATORS
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Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of metabolic diseases and disorders such as, for example, type II diabetes mellitus.
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Page/Page column 16
(2011/06/26)
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- NOVEL PROCESS FOR THE MANUFACTURE OF 5-HALOGENATED-7-AZAINDOLES
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The present invention provides a novel method for manufacturing the compound of formula (I) wherein X is -Cl or-Br.
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Page/Page column 7
(2011/10/05)
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- NOVEL PROCESS FOR THE MANUFACTURE OF 5-HALOGENATED-7-AZAINDOLES
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The present invention provides a novel method for manufacturing the compound of formula (I) wherein X is —Cl or —Br.
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Page/Page column 3-4
(2011/10/04)
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- PROCESS FOR THE MANUFACTURE OF 5-HALOGENATED-7-AZAINDOLES
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The present invention provides a novel method for manufacturing the compound of formula (I); wherein X is -C1 or -Br.
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Page/Page column 7
(2011/10/05)
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- PROCESS FOR THE MANUFACTURE OF PHARMACEUTICALLY ACTIVE COMPOUNDS
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According to the present invention there are provided novel processes for the manufacture of the compound of formula 1 as well as novel synthesis routes for key intermediates used in those processes.
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Page/Page column 12
(2011/02/25)
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- New bimetallic reactivity in Pt2II,III/Pt2 IV,IV transformation mediated by a benzene ring
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A new Pt2 II,II complex with the formula Pt 2(TPAB)Me4 (1), where TPAB = 1,2,4,5-tetrakis(5-(/p-C 7H15Ph)-7-azaindol- l-yl)benzene, has been synthesized. This molecule has excellent solubility in common solvents, which enabled our investigation of its reactions with a variety of oxidants to form Pt2 IV,IV species and the reverse reactions of the Pt2IV,IV species back to 1 via reduction. Despite the lack of direct Pt- ... -Pt interactions, the two Pt centers in 1 display distinct bimetallic cooperativity mediated by the central phenyl ring of the TPAB ligand. The most unusual finding is that the reactivity of 1 with MeOTf is highly dependent on the amount of molecular oxygen present in the reaction medium. In the absence Of O 2, the reaction of 1 with MeOTf produced [Pt2 IV,IV(TPAB)Me6][OTf]2 (6), while in the presence of O2, complex 7, Pt2IV,IV(TP AB)Me4(OTf)2, was obtained. Compound 1 was found to react readily with O2 at one atmosphere and ambient temperature to produce an insoluble and not yet fully characterized solid that further reacts with MeOTf to produce 7 quantitatively. NMR and single-crystal X-ray diffraction analyses established that the two PtIV centers in 6 are five-coordinate with a squarepyramidal geometry, while in 7 the two Pt IV centers are six-coordinate with an octahedral geometry. Most significantly, the central phenyl ring of the TPAB ligand was transformed to a cyclohexyldienyl in 7, while it remains unchanged in 6. Complex 1 also reacts readily with other oxidants such as CHCl3, PhICl2, Br 2 (CBr4), I2, and H2O2 to produce Pt2IV,IV(TPAB)Me4X2 (X = Cl, 2; Br, 3; I,4; OH, 5). The structures of 2-5 are similar to that of 7, showing the generality of the central phenyl ring mediated oxidation of the Pt2IV,IV system. Complexes 2 and 7 can be reduced and converted back to complex 1 via reactions with BH4-, as established by NMR experiments.
- Zhao, Shu-Bin,Cui, Qian,Wang, Suning
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scheme or table
p. 998 - 1003
(2010/04/25)
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- HISTAMINE H3 INVERSE AGONISTS AND ANTAGONISTS AND METHODS OF USE THEREOF
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Provided herein are fused imidazolyl compounds, methods of synthesis, and methods of use thereof. The compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, such as neurological disorders and metabolic disorders. Compounds provided herein inhibit the activity of histamine H3 receptors and modulate the release of various neurotransmitters, such as histamine, acetylcholine, norepinephrine, and dopamine (e.g. at the synapse). Pharmaceutical formulations containing the compounds and their methods of use are also provided herein.
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Page/Page column 113-114
(2010/08/18)
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- PYRAZOLE COMPOUNDS
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The present invention is directed to compounds of Formula (I) and to pharmaceutically acceptable salts thereof, their synthesis, and their use as Raf inhibitors.
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Page/Page column 72-73
(2009/03/07)
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- 7-azaindol-3-ylacrylamides active as kinase inhibitors
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Compounds represented by Formula (I) wherein R1 and R2 are as defined in the specification, compositions thereof, and methods of use thereof.
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Page/Page column 101
(2009/07/10)
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- NEW IMIDAZOLONE DERIVATIVES, PREPARATION THEREOF AS DRUGS, PHARMACEUTICAL COMPOSITIONS, AND USE THEREOF AS PROTEIN KINASE INHIBITORS, IN PARTICULAR CDC7
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The present invention relates to imidazolone derivatives of formula (I) to methods of preparing such derivatives, intermediates thereto, pharmaceutical compositions comprising such derivatives, and methods of inhibiting protein kinase, and methods of treatment comprising administration of such derivatives.
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Page/Page column 40
(2009/10/17)
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- FUSED RING HETEROCYCLE KINASE MODULATORS
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The present invention provides fused ring heterocycles as kinase modulators, pharmaceutical compositions containing these modulators, and methods of using these modulators to treat diseases mediated by kinase activity.
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Page/Page column 70-71
(2008/12/04)
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- NOVEL ANTIMALARIA AGENT CONTAINING HETEROCYCLIC COMPOUND
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Disclosed is an antimalarial agent containing a compound represented by the formula: [wherein A1 represents a 3-pyridyl group that may have a substituent, a 6-quinolyl group that may have a substituent, or the like; X1 represents a group represented by the formula -C(=O)-NH- or the like; E represents a furyl group, a thienyl group or a phenyl group; with the proviso that A1 may have one to three substituents, and E has one of two substituents] or a salt thereof or hydrates thereof.
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Page/Page column 63
(2008/06/13)
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- INDOLE DERIVATIVES
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The invention concerns indole derivatives of Formula (I) or pharmaceutically-acceptable salts thereof, wherein each of Ring A, m, R1, R2, n, R3 and G1 has any of the meanings defined hereinbefore in the description; processes for their preparation, pharmaceutical compositions containing them and their use in therapy, for example in the treatment of disease mediated by a PI3K enzyme and/or a mTOR kinase.
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Page/Page column 81
(2008/06/13)
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- Method for synthesis of AZA-annelated pyrroles, thiophenes, and furans
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Methods of synthesis of intermediates that are useful as bioisosteres of the indole, benzofuran and benzothiophene scaffold are disclosed.
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Page/Page column 9
(2008/06/13)
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- Pyrrolo-pyridine kinase modulators
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The present invention provides novel pyrrolo-pyridine kinase modulators and methods of using the novel pyrrolo-pyridine kinase modulators to treat diseases mediated by kinase activity.
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Page/Page column 75
(2010/02/15)
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- NOVEL ANTIFUNGAL AGENT COMPRISING HETEROCYCLIC COMPOUND
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The present invention provides an antifungal agent represented by the formula: [wherein A1 represents a 3-pyridyl group which may have a substituent, a quinolyl group which may have a substituent, or the like; X1 represents a group represented by the formula -NH-C(=O)-, a group represented by the formula -C(=O)-NH-, or the like; E represents a furyl group, a thienyl group, a pyrrolyl group, a phenyl group, a pyridyl group, a tetrazolyl group, a thiazolyl group or a pyrazolyl group; with the proviso that A1 may have 1 to 3 substituents, and E has one or two substituents].
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Page/Page column 71
(2010/11/08)
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- Synthesis of 7-azaserotonin: Its photophysical properties associated with excited state proton transfer reaction
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We report the synthesis of 3-(2-aminoethyl)-5-ol-1H-pyrrolo[2,3-b]pyridine (7-azaserotonin), which may potentially serve as an agonist or antagonist of serotonin receptors. In alcohols, the solvent (e.g., ethanol) catalyzed proton-transfer reaction takes place for 7-azaserotonin in the excited state, resulting in dual emission. Conversely, excited-state deprotonation takes place in neutral aqueous solution. The unique excitation behavior makes 7-azaserotonin versatile as a potential bioprobe. Copyright
- Wu, Pei-Wen,Hsieh, Wan-Ting,Cheng, Yi-Ming,Wei, Ching-Yen,Chou, Pi-Tai
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p. 14426 - 14427
(2008/01/27)
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- PPAR ACTIVE COMPOUNDS
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Compounds are described that are active on PPARs, including pan-active compounds. Also described are methods for developing or identifying compounds having a desired selectivity profile.
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Page 158-159
(2008/06/13)
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- SYNTHESIS
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The present invention provides a novel substituted azaindoline intermediate of formula (I) and a method for its synthesis. The novel substitued azaindoline intermediate (I) is provided for use in the manufacture of 5-substituted 7-azaindolines and 5-substituted 7-azaindoles.
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- Substituted phenylalkanoic acid derivatives and use thereof
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A compound represented by the formula (I) or a salt thereof: wherein n represents an integer of 1 to 3, R represents an alkyl group having 3 to 8 carbon atoms, a group represented by the following formula: R1(CH2)k— (wherein k represents 0 or an integer of 1 to 3; R1 represents a saturated cyclic alkyl group having 3 to 7 carbon atoms or a saturated condensed cyclic alkyl group having 6 to 8 carbon atoms, and the group R1 may be substituted with a lower alkyl group having 1 to 4 carbon atoms) and the like, and Ar represents a condensed bicyclic group such as naphthalen-1-yl group, which has suppressing action on prostaglandin and leukotriene production and is useful for prophylactic and/or therapeutic treatment of various inflammatory diseases and the like caused by these lipid mediators.
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- Synthesis of new melatonin analogues from dimers of azaindole and indole by use of Suzuki homocoupling
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N-{2-[3′-(2-Acetylaminoethyl)-1H,1′H-[5,5′]biindol-3-yl]- and N-{2-[1′-(2-acetylaminoethyl)-1′H-[5, 5′]biindol-1-yl]ethyl}acetamide (2,3) and their analogues in 7-azaindole series (4,5) were synthesized by palladium catalysed reaction starting from indole or 7-azaindole using [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium, as catalyst.
- Guillard, Jerome,Larraya, Carlos,Viaud-Massuard, Marie-Claude
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p. 865 - 877
(2007/10/03)
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- Polycyclic azaindole compounds
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The invention relates to compounds of formula (I): wherein: G1represents an alkylene chain as defined in the description, A represents R2and R3represent hydrogen, alkyl, alkoxy or hydroxy or together form oxo, R4and R5represent hydrogen or together form aryl, R1is as defined in the description. and medicinal products containing the same which are useful in treating or preventing melatoninergic disorders.
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- Synthesis of new melatoninergic ligands including azaindole moiety
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A novel series of melatonin analogues, based on the azaindole nucleus is described. These compounds are prepared in several steps directly from the commercial available 7-azaindole or from substituted amino-, iodo- or/and nitropyridines using a catalysed palladium reaction or vicarious nucleophilic substitution of hydrogen (VNS) in order to elaborate the 6-, 5- and 4- azaindole derivatives respectively.
- Mazéas, Daniel,Guillaumet, Gérald,Viaud, Marie-Claude
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p. 1065 - 1080
(2007/10/03)
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