- NAPHTHO[2,1 -D]THIAZOLE DERIVATIVES, COMPOSITIONS THEREOF AND METHODS OF TREATING DISORDERS
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The present application relates to the compounds of formula (I) that inhibit CDK9, pharmaceutical compositions thereof and methods of making and using the same.
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Paragraph 0143
(2021/05/29)
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- Synthetic method for anti-leptospira drug ethyl imidazolate
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The invention discloses a synthetic method for the anti-leptospira drug ethyl imidazolate. The synthetic method comprises the following steps: adding ethyl 2,5-dihydroxyimidazole-4-carboxylate and a potassium sulfate solution into a reaction vessel, controlling a stirring speed, increasing a temperature, and continuing a reaction; and raising the temperature, adding a dicyclohexylamine solution, adding dicobalt octacarbonyl powder in batches, continuing the reaction, lowering the temperature, allowing a solid to be precipitated, washing the solid with a sodium nitrate solution a plurality of times, then washing the solid with a cyclohexane solution, carrying out recrystallization in a tripropylene glycol monomethyl ether solution, and then carrying out dehydration with a dehydrating agentso as to obtain the finished ethyl imidazolate.
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Paragraph 0012; 0014-0025
(2018/07/30)
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- Efficient synthesis method of pharmaceutical intermediate 1H-imidazole-4-formic acid
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The invention discloses an efficient synthesis method of a pharmaceutical intermediate 1H-imidazole-4-formic acid. The efficient synthesis method specifically comprises the following steps: firstly, preparing a titanium dioxide/titanium niobate compound catalyst; then taking 2-thiol-4-imidazole ethyl formate as a raw material; preparing 1H-imidazole-4-ethyl formate under the action of a hydrogen peroxide solution and a compound catalyst; then enabling the 1H-imidazole-4-ethyl formate to react with alkali liquid to prepare a target product. The efficient synthesis method disclosed by the invention has a simple reaction process and raw materials are cheap and easy to obtain; the prepared target product is simple to separate and the yield reaches 90 percent or more.
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Paragraph 0022-0026; 0028-0032; 0034-0038; 0040-0044; 0046
(2018/12/14)
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- HETEROAROMATIC NMDA RECEPTOR MODULATORS AND USES THEREOF
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Disclosed herein, in part, are heteroaromatic compounds and methods of use in treating neuropsychiatric disorders, e.g., schizophrenia and major depressive disorder. Pharmaceutical compositions and methods of making heteroaromatic compounds are provided. The compounds are contemplated modulate the NMDA receptor.
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Paragraph 00345
(2017/07/27)
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- Synthesis method of 4(5)-hydroxymethylimidazole
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The invention discloses a synthesis method of 4(5)-hydroxymethylimidazole. With 4,5-imidazoledicarboxylic acid as the raw material, decarboxylic reaction, esterification reaction and reduction reaction are conducted, manganese dioxide solid, ferric sulfate powder and a loaded Ni-Cu/SiO2 catalyst are added for catalytic reaction, reaction efficiency is improved, and reaction operation is simplified; meanwhile, the reaction process is improved, that is, the precipitation of 4(5)-imidazole carboxylic acid imidazole is promoted by adding sodium nitrate solid 5, the addition of concentrated sulfuric acid and a sodium hydroxide solution for neutralizing concentrated sulfuric acid is reduced by adding a catalyst, reaction consumption is reduced, reaction efficiency is improved, reaction operation is simplified, and high industrial popularization value is achieved.
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Paragraph 0072; 0073
(2016/12/01)
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- Preparation method of 1H-imidazole-4-carboxylic acid
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The invention discloses a synthesis method of 1H-imidazole-4-carboxylic acid, and belongs to the field of chemical synthesis. A target compound is prepared through optimized enolization, cyclization, catalytic oxidation desulfurization and hydrolysis reaction with ethyl acetamidoacetate as the raw material, the yield of 1H-imidazole-4-carboxylic acid is increased, antimony butter is added as the catalyst for catalytic oxidation desulfurization reaction, the yield of 1H-imidazole-4-carboxylic acid is increased, energy consumption is lowered, and economic benefits are improved.
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Paragraph 0089; 0090; 0091; 0092; 0093; 0094
(2016/10/10)
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- Method for catalytically synthesizing 1H-imidazole-4-carboxylic acid through inorganic-salt composite catalyst
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The invention discloses a method for catalytically synthesizing 1H-imidazole-4-carboxylic acid through an inorganic-salt composite catalyst. Ethyl acetamidoacetate serves as a raw material and is enolized, cyclized, subjected to catalytic oxidation desulfurization and hydrolyzed to prepare the target compound; the method includes the three steps of preparing 2-sulfydryl-4-ethyl imidazolecarboxylate, preparing ethyl imidazole-4-carboxylate and preparing the 1H-imidazole-4-carboxylic acid; the inorganic-salt composite catalyst is prepared in the mode that barium sulfate, ferric nitrate and iron sulfate are compounded. The development method is a synthetic technology which is economical, environmentally friendly and easy to operate; the inorganic-salt composite catalyst is provided and added in an inorganic-salt solid mode, the cost of a raw material of the catalyst is low, a preparing method is environmentally friendly and simple, the selectivity of the catalytic effect of the catalyst is high, the yield is remarkably increased, by products are avoided, the catalyst can be recycled, and the quite high market promotion value is achieved.
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Paragraph 0010; 0084; 0085; 0086
(2016/10/17)
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- BENZENE SULFONAMIDES AS CCR9 INHIBITORS
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The present invention relates to compounds useful as CCR9 modulators, to compositions containing them, to methods of making them, and to methods of using them. In particular, the present invention relates to compounds capable of modulating the function of the CCR9 receptor by acting as partial agonists, antagonists or inverse agonists. Such compounds may be useful to treat, prevent or ameliorate a disease or condition associated with CCR9 activation, including inflammatory and immune disorder diseases or conditions such as inflammatory bowel diseases (IBD).
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Page/Page column 96; 97
(2015/07/15)
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- A new generation of aprotic yet Bronsted acidic imidazolium salts: Low toxicity, high recyclability and greatly improved activity
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Catalysts which have low antimicrobial toxicity and are aprotic, yet which can act as Bronsted acidic catalysts in the presence of protic additives have been developed. The catalysts are recyclable, considerably more active (i.e. can be used at 10-50 times lower loadings) and of broader scope than their antecedent generation.
- Myles, Lauren,Gore, Rohitkumar G.,Gathergood, Nicholas,Connon, Stephen J.
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supporting information
p. 2740 - 2746
(2013/10/08)
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- Synthesis and SAR of novel imidazoles as potent and selective cannabinoid CB2 receptor antagonists with high binding efficiencies
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The synthesis and structure-activity relationship studies of imidazoles are described. The target compounds 6-20 represent a novel chemotype of potent and CB2/CB1 selective cannabinoid CB2 receptor antagonists/inverse agonists with very high binding efficiencies in combination with favourable log P and calculated polar surface area values. Compound 12 exhibited the highest CB2 receptor affinity (Ki = 1.03 nM) in this series, as well as the highest CB2/CB1 subtype selectivity (>9708-fold).
- Lange, Jos H.M.,van der Neut, Martina A.W.,Wals, Henri C.,Kuil, Gijs D.,Borst, Alice J.M.,Mulder, Arie,den Hartog, Arnold P.,Zilaout, Hicham,Goutier, Wouter,van Stuivenberg, Herman H.,van Vliet, Bernard J.
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scheme or table
p. 1084 - 1089
(2010/06/11)
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- SUBSTITUTED PIPERAZINES AS CB1 ANTAGONISTS
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Compounds of Formula (I): or pharmaceutically acceptable salts, solvates, or esters thereof, are useful in treating diseases or conditions mediated by CB1 receptors, such as metabolic syndrome and obesity, neuroinflammatory disorders, cognitive disorders and psychosis, addiction (e.g., smoking cessation), gastrointestinal disorders, and cardiovascular conditions.
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Page/Page column 133
(2009/03/07)
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- Carbene reactivity of 4-diazo-4H-imidazoles toward nucleophiles and aromatic compounds
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(Chemical Equation Presented) Carbenes derived from diazoimidazolecarboxylates 4 under thermal or photochemical conditions undergo O-H and N-H insertion reactions with alcohols and amines, respectively, in moderate yield, in competition with reduction in good H-donor solvents. Dichloromethane reacts to give the corresponding 4-chloroimidazole. Aromatic hydrocarbons are excellent traps for the imidazolylidene carbene and lead to a range of arylimidazole derivatives 7. Reaction with pyridine leads to the first example of a pyridinium ylide 8 formed from an imidazolylidene carbene, whereas irradiation in hexafluorobenzene gives the imidazoazocine 11, presumably by way of an initial norcaradiene intermediate.
- Smith, Matthew R.,Blake, Alexander J.,Hayes, Christopher J.,Stevens, Malcolm F. G.,Moody, Christopher J.
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experimental part
p. 9372 - 9380
(2010/03/04)
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- SUBSTITUTED PIPERAZINES AS CB1 ANTAGONISTS
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Compounds of Formula (I) or pharmaceutically acceptable salts, solvates, or esters thereof, are useful in treating diseases or conditions mediated by CB1receptors, such as metabolic syndrome and obesity, neuroinflammatory disorders, cognitive disorders and psychosis, addiction (e.g., smoking cessation), gastrointestinal disorders, and cardiovascular conditions.
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Page/Page column 314
(2009/03/07)
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- Ring-substituted imidazoles as a new class of anti-tuberculosis agents
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We describe in vitro anti-Mycobacterium tuberculosis activities of ring-substituted-1H-imidazole-4-carboxylic acid derivatives (1-6), and 3-(2-alkyl-1H-imidazol-4-yl)-propionic acid derivatives (7-13) against drug-sensitive and drug-resistant M. tuberculosis H37Rv strains. The most effective analogues, 2f (R=R1=c-C5H9), and 2h (R=R1=c-C6H11) have produced >90% inhibition at a concentration of 6.25 μg/ml in the drug-sensitive screen. Upon further evaluation against drug-resistant strains, both analogues 2f and 2h produced an MIC value of 25.0 μg/ml. The observation of significant anti-tuberculosis activity in some of these analogues describes the discovery of novel ring-substituted-1H-imidazole-4-carboxylic acid ethyl esters as a new class of anti-tuberculosis agents.
- Gupta, Preeti,Hameed, Shahul,Jain, Rahul
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p. 805 - 814
(2007/10/03)
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- Intramolecular Hydrogen Bonding in Imidazole-4(5)-alkoxycarbonyl-5(4)-carboxamide Derivatives
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The ir spectrum of imidazole derivatives, which have an alkoxycarbonyl group and a carboxamide group at the 4- and 5-positions of the imidazole ring respectively, exhibits the shift of the ester carbonyl band to a lower wave number.This phenomenon was investigated by spectroscopic measurements of a group of relevant compounds.The results indicate that the shift is caused by the intramolecular hydrogen bonds between the hydrogen atom of the amide and the carbonyl oxygen of the ester which is enhanced by the resonance stabilization of the imidazole ring.
- Yasuda, Naohiko,Nakamura, Asao,Tsuboi, Masamichi
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p. 303 - 307
(2007/10/02)
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- HIGH-YIELDING SYNTHESES OF 4(5)-SUBSTITUTED IMIDAZOLES VIA ORGANOLITHIUM INTERMEDIATES. THE UTILITY OF SULPHONAMIDE N-PROTECTION AND SILICON-CONTAINING BLOCKING GROUPS
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N-protection of imidazole as its N,N-dimethyl-sulphonamido derivative, and blocking of the 2-position with the triethylsilyl group permits regioselective 5-metallation with sec-butyl-lithium.The resulting organolithium intermediates react with a range of electrophiles and the products are easily deprotected to give the 4(5)-substituted NH-free imidazoles in good to excellent yields.Isolation of the silicon-blocked intermediate is unnecessary and, indeed, is disadvantageous to final yields, making the procedure attractively economical of time.
- Carpenter, Andrew J.,Chadwick, Derek J.
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p. 2351 - 2358
(2007/10/02)
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- New Synthesis of 2-Nitroimidazoles
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1-Triphenylmethylimidazoles are treated with n-butyllithium in tetrahydrofuran at 0 deg C to form the 2-lithio derivatives.The latter species react with n-propyl nitrate to give 1-trityl-2-nitroimidazoles which, after acid hydrolysis, provide the correspondine 2-nitroimidazoles. 2-Nitroimidazole was obtained from imidazole from overall yields of 27-35percent; 4-methyl-2-nitroimidazole was obtained in 40percent overall yield from 4-methylimidazole.Imidazole-4,5-dicarboxylic acid was converted, in several steps, to 1-tritylimidazole-4-methanil, and the latter compound was transformed into 2-nitroimidazole-4-methanol in an overall yield of 18percent.Protection of the hydroxymethyl function was found to be unnecessary during carbanion formation and nitration.Attempts to nitrate 1-methylimidazole or 1-methoxymethylimidazole by the same procedure failed.
- Davis, Dwight P.,Kirk, Kenneth L.,Cohen, Louis A.
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p. 253 - 256
(2007/10/02)
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