- Protein kinase inhibitor and use thereof
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The present invention provides a compound of formula 1 having an activity of inhibiting protein kinase and its use.
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Paragraph 0091; 0102-0103
(2021/01/21)
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- Preparation method of 2-amino substituted six-membered nitrogen-containing heterocycle complex
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The invention discloses a preparation method of a 2-amino substituted six-membered nitrogen-containing heterocycle complex. The preparation method comprises the following steps: mix 2-fluorine substituted six-membered nitrogen-containing heterocycle complex and amidine hydrochloride salt compound, and then react under the action of a alkaline substance to obtain a 2-amino substituted six-memberednitrogen-containing heterocycle complex. Preferably, the 2-amino substituted six-membered nitrogen-containing heterocycle complex is a 2-amino pyridine compound, a 2-aminopyrimidine compound or a 2-aminopyrazine compound. Compared with the prior art, the method has the advantages of simple synthesis conditions, less reaction steps, mild reaction conditions, low cost of the catalyst used, less waste discharge and good functional group tolerance.
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Paragraph 0025; 0026; 0079
(2019/02/08)
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- Transition-metal-free access to 2-aminopyridine derivatives from 2-fluoropyridine and acetamidine hydrochloride
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Under catalyst-free conditions, an efficient method for the synthesis of 2-aminopyridine derivatives through the nucleophilic substitution and hydrolysis of 2-fluoropyridine and acetamidine hydrochloride has been developed. This amination uses inexpensive acetamidine hydrochloride as the ammonia source and has the advantages of a high yield, high chemoselectivity and wide substrate adaptability. The results suggest that other N-heterocycles containing fluorine substituents can also complete the reaction via these reaction conditions and yield the target products.
- Li, Yibiao,Huang, Shuo,Liao, Chunshu,Shao, Yan,Chen, Lu
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supporting information
p. 7564 - 7567
(2018/11/02)
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- Catalytic application of 1,3,5-triazine-pentaethylenehexamine polymer-supported palladium nanoparticles in the convenient reduction of nitroarenes with sodium borohydride or hydrazine
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The catalytic activity of 1,3,5-triazine-pentaethylenehexamine (TAPEHA) polymer-supported Pd nanoparticles was investigated in the reduction of nitro arenes to the corresponding amines by NaBH4 or N2H4 .H2 O. Optimized reaction conditions for both systems were successfully tested on 20 nitroarenes with different characteristics. Considerably high yields (80%-98% in NaBH4 and 85%-98% in N2H4) were obtained in a short time and at ambient temperature. In addition to these methods being selective against other reducible functionalities such as -CN, -Br, -Cl, and -I, the catalyst can be recovered easily and reused more than ten times.
- Gen?, Hayriye,Zengin, Mustafa,Kü?ükislamo?lu, Mustafa,Imamoglu, Mustafa,Toplan, Hüseyin ?zkan,Arslan, Mustafa
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p. 784 - 792
(2017/11/20)
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- Efficient reductions of various nitroarenes with scrap automobile catalyst and NaBH4
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The effect of scrap automobile catalyst (SAC), a waste material, was investigated as a catalyst for the reduction of nitroarenes to the corresponding amines with sodium borohydride in aqueous ethanol at 5-25 °C. Along with the observed high conversions, the SAC and NaBH4 combination also exhibits a selectively catalyzed reduction in compounds containing other reducible functionalities, such as CN, Br, Cl and I. Recycling automobile wastes into a catalyst for organic reactions will offer both environmental protection and economic advantages. As a result, an effective, easy to use, low-priced and reliable method has been developed.
- Genc, Hayriye
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- The synthesis of a dopamine D2 partial agonist for the treatment of schizophrenia
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The synthesis of the phosphoric acid salt of dopamine D2 partial agonist 2-{4-[4-(7-fluoro-naphthalen-1-yl)-piperazin-1-yl]- butoxy}-5,6,7,9-tetrahydro- 1,7,9-triaza-benzocyclohepten-8- one (1) is reported. The most prominent feature of the molecule is a seven-membered ring urea functionality that has been prepared via an efficient one-pot, three-step transformation. The original synthesis from the Medicinal Chemistry group provided precursor 13 in 10 steps and 2% overall yield, required four chromatographies and employed unsafe reagents such as 2-iodoxybenzoic acid (IBX) and HClO4. The optimized synthetic route for the preparation of phosphate salt 1 consists of 12 linear steps with a 10% overall yield. Safer and more robust reaction conditions have been developed with only one required chromatography. Another key step in the synthesis is the coupling of iodide 25 with naphthalenopiperazine 12 to provide 13. Due to the difficulty to purify this intermediate, a protocol had to be developed to obtain crude material with the required purity, suitable for use in the subsequent salt formation step. Finally, considerable work was carried out to determine the most stable polymorph of the API. As a result, a robust set of conditions has been developed for the formation of phosphoric acid salt 1, providing the desired polymorph in excellent yield and purity.
- Magano, Javier,Acciacca, Alison,Akin, Anne,Collman, Benjamin M.,Conway, Brian,Waldo, Michael,Chen, Michael H.,Mennen, Kenneth E.
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experimental part
p. 555 - 566
(2010/04/22)
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- PROCESS FOR THE SYNTHESIS OF DIAMINOPYRIDINE AND RELATED COMPOUNDS
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A process is provided for the synthesis of a diaminopyridine, such as 2,6-diaminopyridine and related compounds, which are used industrially as compounds and as components in the synthesis of a variety of useful materials. The synthesis proceeds by means of a chlorine-ammonia displacement in the presence of a copper source.
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Page/Page column 18
(2009/03/07)
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- PROCESS FOR THE SYNTHESIS OF DIAMINOPYRIDINE AND RELATED COMPOUNDS
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A process is provided for the synthesis of a diaminopyridine, such as 2, 6-diaminopyridine and related compounds, which are used industrially as compounds and as components in the synthesis of a variety of useful materials. The synthesis proceeds by means of a chlorine-ammonia displacement in the presence of a copper source.
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Page/Page column 18
(2009/03/07)
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- Voltammetric, potentiometric and spectrophotometric studies of some hydrazones and their metal complexes in ethanolic-aqueous buffered solutions
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The electrochemical behavior of some hydrazones derived from 6-chloro-2-hydrazinopyridine in the Britton-Robinson universal buffer of pH 2-11 containing 35% ethanol was investigated at the mercury electrode using dc-polarography, controlled-potential coulometry, and cyclic voltammetry techniques. The examined hydrazones were reduced in solutions of pH 2 single bond. The mechanistic pathway of the electrode reaction of the studied compounds was elucidated and discussed. The pK a values of the examined hydrazones and the stoichiometry of their complexes in solution with some transition metal ions were determined spectrophotometrically. The dissociation constants and the thermodynamic parameters of the investigated hydrazones, and the stability constants of their metal complexes in solution were determined potentiometrically. Springer-Verlag 2006.
- Ghoneim, Mohammed M.,El-Hallag, Ibrahim S.,El-Baradie, Kamal Y.,El-Desoky, Hanaa S.,El-Attar, Mona A.
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p. 285 - 299
(2007/10/03)
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- N,N-bond-forming heterocyclization: Synthesis of 3-alkoxy-2H-indazoles
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A one-step heterocyclization of o-nitrobenzylamines to 3-alkoxy-2H- indazoles is reported. The electronic nature of the nitrophenyl group, the steric and electronic nature of the R1-functionalized benzylic amine, and the nature of the alcoholic solvent affect the efficiency of this heterocyclization reaction (~40-90%).
- Mills, Aaron D.,Nazer, Musa Z.,Haddadin, Makhluf J.,Kurth, Mark J.
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p. 2687 - 2689
(2007/10/03)
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- Combination of FBPase inhibitors and insulin sensitizers for the treatment of diabetes
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Pharmaceutical compositions containing an FBPase inhibitor and an insulin sensitizer are provided as well as methods for treating diabetes and diseases responding to increased glycemic control, an improvement in insulin sensitivity, a reduction in insulin levels, or an enhancement of insulin secretion.
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Page column 145
(2010/02/07)
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- Large-scale synthesis of new cyclazines, 5-thia-1,8b-diazaacenaphthylene-3-carboxylic acid derivatives having the peripheral 12π-electron ring system
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The 5-thia-1,8b-diazaacenaphthylenes (2 and its ester, 8) are new cyclazines, in which a paramagnetic ring is present in the peripheral 12π-electron ring system. Three convenient methods of preparing 8 have been developed. One involved thioglycolation of a new compound, 5-fluoroimidazo[1,2-a]pyridine (6b), followed by the Duff reaction gave 8 in 64% yield without chromatographic purification.
- Ikemoto, Tomomi,Kawamoto, Tetsuji,Wada, Hiroki,Ishida, Toru,Ito, Tatsuya,Isogami, Yasushi,Miyano, Yoshiko,Mizuno, Yukio,Tomimatsu, Kiminori,Hamamura, Kazumasa,Takatani, Muneo,Wakimasu, Mitsuhiro
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p. 489 - 493
(2007/10/03)
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- Novel bisamidate phosphonate prodrugs
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Novel bisamidate phosphonate prodrugs of FBPase inhibitors of the Formula IA: and their use in the treatment of diabetes and other conditions associated with elevated blood glucose.
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- Heteroaromatic compounds containing a phosphonate group that are inhibitors of fructose-1,6-bisphosphatase
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FBPase inhibitors of the formula I and X are useful in the treatment of diabetes and other conditions associated with elevated blood glucose or excess glycogen storage.
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- Antiulcer Agents. 3. Structure-Activity-Toxicity Relationships of Substituted Imidazopyridines and a Related Imidazopyrazine
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Investigation of the interrelationship between structure, antiulcer activity, and toxicology screening data derived from a series of compounds selected from structure-activity studies directed toward identifying a successor to 3-(cyanomethyl)-2-methyl-8-(phenylmethoxy)imidazopyridine, Sch 28080 (1), has identified 3-(cyanomethyl)-2,7-dimethyl-8-(phenylmethoxy)imidazopyridine (5), 3-amino-2-methyl-8-(2-phenylethyl)imidazopyridine (6), and 3-amino-2-methyl-8-(phenylmethoxy)imidazopyrazine (7).These analogues exhibit a combination of antisecretory and cytoprotective activity in animal models, while eliminating the adverse effects of the prototype 1.One of these, 3-amino-2-methyl-8-(phenylmethoxy)imidazopyrazine, Sch 32651 (7), has a profile meeting all criteria.
- Kaminski, James J.,Perkins, D. G.,Frantz, J. D.,Solomon, Daniel M.,Elliott, Arthur J.,et al.
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p. 2047 - 2051
(2007/10/02)
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- Benzothiazine derivative
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N-(6-chloro-2-pyridyl)-3,4-dihydro-2-methyl-4-oxo-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide that is a novel benzothiazine derivative. The compound is characterized by a low degree of toxicity and a low incidence of gastric disorders and useful as an anti-inflammatory agent.
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- Substituent Effects on the Isomer Ratios in the Rearrangement of Some 2- and 4-Nitraminopyridines
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The preparation, and rearrangement in 92percent sulfuric acid, of 4-X-2-nitramino- (1), 2-X-4-nitramino- (2), and 6-X-2-nitramino-pyridines (3) is reported (X=H,Me,MeO,Br,Cl,CO2H).The product isomer ratios can be explained by differential electronic stabilization of the appropriate ? complexes for aromatic nitration and steric effects seem relatively unimportant.Deuteration had no effect on the product distribution
- Deady, Leslie W.,Korytsky, Olga L.,Rowe, Jeffrey E.
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p. 2025 - 2034
(2007/10/02)
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- Studies on 1,3-Benzoxazines. I. Synthesis of Primary 2-Amino-pyridines via the Reaction of Imidoyl Chlorides of 1,3-Benzoxazines with Pyridine N-Oxides
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A new synthetic method for primary 2-aminopyridine derivatives is described.Treatment of the imidoyl chlorides of 1,3-benzoxazines (1a-i) with pyridine N-oxides resulted in the introduction of an oxazine moiety into the α-position of the pyridine ring through rearrangement of the initially formed reaction adduct.Acid hydrolysis of the rearrangement products afforded 2-aminopyridine derivatives in excellent yields.When methoxypyridine N-oxides were used, products of a different type (10 and 14) were obtained.
- Wachi, Kazuyuki,Terada, Atsusuke
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p. 465 - 472
(2007/10/02)
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