- Synthesis process of diclofenac sodium
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The invention provides a synthesis process of diclofenac sodium, which is obtained by acylation reaction of o-aminobenzene acetate with 2 and 6 - dichlorophenoxy acetic acid respectively and acylation with chlorobenzoyl chloride followed by nucleophilic substitution with 2, 6 - dichlorophenol or 2 and 6 -dichlorophenol. Is hydrolyzed to give sodium diclofenac sodium. The synthesis process is simplified, the reaction condition is mild, and the yield and industrial popularization and application are facilitated.
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- NovelN-transfer reagent for converting α-amino acid derivatives to α-diazo compounds
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A novel universalN-transfer reagent for direct and effective transformation of α-amino ketones, acetamides, and esters to the corresponding α-diazo products under mild basic conditions has been developed. This one-step synthetic approach not only allows for generation of α-substituted-α-diazo carbonyl compounds from α-amino acid derivatives but also permits preparation of α-diazo dipeptides fromN-terminal dipeptides (32 examples, up to 91%).
- Lu, Guan-Han,Huang, Tzu-Chia,Hsueh, Hsiao-Chin,Yang, Shin-Cherng,Cho, Ting-Wei,Chou, Ho-Hsuan
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supporting information
p. 4839 - 4842
(2021/05/25)
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- Synthetic method of poly-substituted dimethyl amino phenyl acetic acid compound
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The invention relates to a synthesis method of a poly-substituted dimethyl amino phenyl acetic acid compound. The synthesis method comprises the following steps: carrying out methyl esterification reaction on a compound shown in a formula I to obtain a co
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Paragraph 0046-0049; 0088-0091
(2021/03/05)
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- Gold(I)-Thiolate Oligomers for Catalytic Hydrogenation of Nitroaromatics in Aqueous and Organic Medium
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Thiolated gold nanoclusters (AuNCs) have been introduced to efficiently and selectively catalyze the hydrogenation of nitroaromatics due to the strong interaction of their S?Au-S staple motifs with the nitro groups of nitroaromatics. However, without a gold core, gold(I)-thiolate oligomers (AuSOs) with S?Au-S staple motifs are rarely explored as catalysts for nitroaromatics. Here, we report a straightforward strategy for the synthesis of AuSOs through hydroxyl radical-induced leaching of glutathione-capped gold nanoparticles (GSH-AuNPs). Raman spectroscopy and matrix-assisted laser desorption/ionization-time of flight mass spectrometry demonstrated that hydroxyl radical-triggered etching of the GSH-AuNPs resulted in the production of AuSOs, including Au4(GSH)7 and Au7(GSH)9. The AuSOs were found to catalyze NaBH4-mediated hydrogenation of 4-nitrophenol to 4-aminophenol with a chemoselectivity of ~100 percent and a normalized rate constant (Knor) of 4.8×105 s? g?1. In addition to the high affinity of the S?Au?S staple motifs for 4-nitrophenol, the unusual catalytic activity of the AuSOs was attributable to the fact that they efficiently catalyzed the production of H2 from NaBH4 and the reaction of dissolved oxygen and NaBH4. The chemoselectivity and applicability of the AuSOs were further verified by performing the catalytic reaction of methyl 2-(2-nitrophenyl) acetate or methyl 4-nitrobenzoate with NaBH4.
- You, Jyun-Guo,Jin, Dun-Yuan,Tseng, Wei-Bin,Tseng, Wei-Lung,Lin, Po-Chiao
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p. 4558 - 4567
(2020/08/19)
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- A synthesis method of diclofenac (by machine translation)
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The present invention provides a diclofenac synthetic method, which belongs to the technical field of drug synthesis; synthetic method of this invention the specific reaction steps are as follows: step 1): compound (a) in the presence of sodium methoxide/methanol reaction, to obtain compound (b); step 2): compound (b) with a compound (c) in the presence of an alkali reaction, to obtain compound (d); step 3): compound (d) with a compound (e) in the organic solvent, under the action of catalyst reaction, to obtain compound (f); the method of raw materials are easy, simple operation, high yield, low cost, less wastes, high safety, is suitable for industrial production. (by machine translation)
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Paragraph 0052; 0058; 0059
(2019/10/23)
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- Metal-Free Tandem Rearrangement/Lactonization: Access to 3,3-Disubstituted Benzofuran-2-(3H)-ones
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A novel metal-free synthesis of 3,3-disubstituted benzofuran-2-(3H)-ones through reacting α-aryl-α-diazoacetates with triarylboranes is presented. Initially, triarylboranes were successfully investigated in α-arylations of α-diazoacetates, however in the presence of a heteroatom in the ortho position, the boron enolate intermediate undergoes an intramolecular rearrangement to form a quaternary center. The intermediate cyclizes to afford valuable 3,3-disubstituted benzofuranones in good yields.
- Santi, Micol,Ould, Darren M. C.,Wenz, Jan,Soltani, Yashar,Melen, Rebecca L.,Wirth, Thomas
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p. 7861 - 7865
(2019/04/25)
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- Synthetic method of diclofenac sodium (by machine translation)
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The invention belongs to the technical field of pharmaceutical chemical synthesis, specific non-steroidal anti-inflammatory analgesic synthetic method of diclofenac sodium. Synthetic method of this invention the reaction steps are as follows: by the phenylacetic acid nitration reaction layer which O-nitrophenyl acetate (2); by the compound (2) by hydrogenation reduction reaction O-amino acetate (3); by the compound (3) amino through amidation, to obtain 2 - (2 - benzamido-phenyl) acetate (4); by the compound (4) with thionyl chloride produce chlorinated imine intermediate, then under the action of the inorganic base with 2, 6 - dichlorophenol condensation preparation (E) - Methyl - 2 - (2 - ((2, 6 - dichloro phenoxy) (phenyl) methylene amino) phenyl) ester (5); by the compound (5) by the Chapman rearrangement reaction for preparing methyl 2 - (2 - (N- (2, 6 - Dichlorophenyl) benzoyl amino) phenyl) ester (6); by the compound (6) by hydrolysis to prepare diclofenac sodium. Benzene acetic acid methyl ester calculation, the overall yield is 67%. The method of the invention raw materials are easy, economic cost, simple operation, mild reaction conditions, the industrial production is easy. (by machine translation)
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- Enantioselective Synthesis of trans-2,3-Dihydro-1H-indoles Through C–H Insertion of α-Diazocarbonyl Compounds
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A stereoselective synthesis of 2,3-dihydro-1H-indoles with a RhII-catalyzed C–H insertion is reported. The α-diazo carbonyl intermediates can be obtained by a diazo-transfer reaction of 2-aminophenylacetic acids. Optimization and kinetic studie
- Santi, Micol,Müller, Simon T. R.,Folgueiras-Amador, Ana A.,Uttry, Alexander,Hellier, Paul,Wirth, Thomas
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p. 1889 - 1893
(2017/04/21)
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- CYCLOPROPANECARBOXAMIDO-SUBSTITUTE AROMATIC COMPOUNDS AS ANTI-TUMOR AGENTS
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Provided are cyclopropanecarboxamido-substituted aromatic compounds that inhibit protein kinases and their use in anti-tumor area. In particular, tyrosine-kinase inhibitors and Raf-kinase inhibitors as anti-tumor agents, their preparation, pharmaceutical composition, and their use in the treatment of cancer are also provided.
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- Visible-Light-Induced Meerwein Cascade Reactions for the Preparation of α-Aryl Esters
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A practical strategy has been developed for preparation of α-aryl ester derivatives by using a visible-light-induced Meerwein cascade reaction. This method uses molecular oxygen as an oxidant at room temperature without the need of hazardous reagents or harsh reaction conditions and provides a straightforward approach to pharmaceutically and synthetically useful α-aryl esters in moderate to good yields from simple and readily available starting materials. Oxindoles were also prepared by this protocol. A new strategy for the synthesis of α-aryl esters has been reported. This protocol utilizes acrylonitrile as a "bridge molecule" to combine a visible-light-induced Meerwein reaction and a hydrolysis reaction to generate α-aryl esters. This method was also employed for the preparation of oxindoles.
- Niu, Teng-Fei,Li, Liang,Ni, Bang-Qing,Bu, Mei-Jie,Cai, Chun,Jiang, Hui-Liang
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p. 5775 - 5780
(2015/09/15)
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- CYCLOPROPANECARBOXAMIDO-SUBSTITUTE AROMATIC COMPOUNDS AS ANTI-TUMOR AGENTS
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Provided are cyclopropanecarboxamido-substituted aromatic compounds that inhibit protein kinases and their use in anti-tumor area. In particular, tyrosine-kinase inhibitors and Raf-kinase inhibitors as anti-tumor agents, their preparation, pharmaceutical composition, and their use in the treatment of cancer are also provided.
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- HETEROCYCLIC COMPOUNDS AND METHODS OF USE THEREOF
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Provided herein are heterocyclyl compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. The compounds provided herein are useful for the treatment, prevention, and/or management of various neurological disorders, including but not limited to, psychosis and schizophrenia.
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- Intramolecular C-O/C-S bond insertion of α-diazoesters for the synthesis of 2-aryl-4H-benzo[d][1,3]oxazine and 2-aryl-4H-benzo[d][1,3]thiazine derivatives
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An intramolecular C-O insertion of 2-(2-arylamidophenyl)-2-diazoacetate has been achieved using a catalytic amount of copper triflate under mild conditions to produce 2-aryl-4H-benzo[d][1,3]oxazine-4-carboxylate in good yields. In addition, 2-diazo-2-(2-a
- Reddy, B. V. Subba,Babu, R. Anji,Ramana Reddy,Reddy, B. Jagan Mohan,Sridhar
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p. 44629 - 44633
(2014/12/10)
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- Catalysis in polysiloxane gels: Platinum-catalyzed hydrosilylation of polymethylhydrosiloxane leading to reusable catalysts for reduction of nitroarenes
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Novel polysiloxane gels, to which platinum species are encapsulated, are prepared by treatment of polymethylhydrosiloxane with alkenes in the presence of Karstedt's catalyst. These gels act as reusable catalysts in the reduction of functionalized nitroarenes with H2 to the corresponding substituted anilines without leaking the catalyst species.
- Motoyama, Yukihiro,Kamo, Kazuyuki,Nagashima, Hideo
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supporting information; experimental part
p. 1345 - 1348
(2009/09/29)
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- TARGETING DIAZO PRODRUGS FOR THE TREATMENT OF GASTROINTESTINAL DISEASES
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Provided herein are compounds, compositions and methods for decreasing NFkB DNA-binding activity in a patient comprising administering of a therapeutically effective amount of a compound or composition of the application to the patient to reduce, alleviate or treat various gastrointestinal diseases, such as inflammatory bowel disease (IBD).
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Page/Page column 42-43
(2009/03/07)
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- Lewis acid catalyzed indole synthesis via intramolecular nucleophilic attack of phenyldiazoacetates to iminium ions
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(Chemical Equation Presented) Lewis acids catalyze the cyclization of methyl phenyldiazoacetates with an ortho-imino group, prepared from o-aminophenylacetic acid, to give 2,3-substituted indoles in quantitative yields.
- Zhou, Lei,Doyle, Michael P.
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scheme or table
p. 9222 - 9224
(2010/03/01)
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- Substituted Sulfonamide Compounds
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Substituted sulfonamide compounds corresponding to formula I pharmaceutical compositions comprising them, a process for preparing them, and the use of such compounds to treat or inhibit pain and other disorders or disease states.
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Page/Page column 37
(2009/01/24)
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- The chemistry of homophthalic acid: a new synthetic strategy for construction of substituted isocoumarin and indole skeletons
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Homophthalic acid was reacted with thionylchloride/DMF and chloroethylformate/NEt3 in the presence and absence of NaN3. In all cases completely different isocoumarin derivatives were obtained. These unusual isocoumarin derivatives were isolated and characterized and their formation mechanisms are discussed. The homophthalic acid monomethyl ester was converted into the corresponding isocyanate. Reaction of the isocyanate with different amines produced the urea derivatives. Base-supported condensation reactions of these products gave first an indolinone derivative, which underwent further intermolecular condensation to give substituted indole derivatives. However, when the condensation reaction was carried out in the presence of acetic anhydride, the intermolecular reactions were suppressed. This methodology opens up a new way of synthesizing of various five-membered ring substituted indole derivatives.
- ?zcan, Sevil,Balci, Metin
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p. 5531 - 5540
(2008/09/21)
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- Cancer preventive agents, Part 2: Synthesis and evaluation of 2-phenyl-4-quinolone and 9-oxo-9,10-dihydroacridine derivatives as novel antitumor promoters
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2-Phenyl-4-quinolone and 9-oxo-9,10-dihydroacridine derivatives were synthesized and screened as potential antitumor promoters by examining the ability of the compounds to inhibit Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor p
- Nakamura, Seikou,Kozuka, Mutsuo,Bastow, Kenneth F.,Tokuda, Harukuni,Nishino, Hoyoku,Suzuki, Madoka,Tatsuzaki, Jin,Morris Natschke, Susan L.,Kuo, Sheng-Chu,Lee, Kuo-Hsiung
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p. 4396 - 4401
(2007/10/03)
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- Method for treating allergies using substituted pyrazoles
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A method for treating an allergic condition, including an atopic allergic condition, using substituted pyrazoles.
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- Antitumor agents. Part 226: Synthesis and cytotoxicity of 2-phenyl-4-quinolone acetic acids and their esters
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2-Phenyl-4-quinolone acetic acids and their esters were synthesized and evaluated for interaction with tubulin and for cytotoxicity against a panel of human tumor cell lines. 2-Phenyl- and 2-(2′-fluorophenyl)-4-quinolone-8- acetic acids (11 and 12) displa
- Xia, Yi,Yang, Zheng-Yu,Xia, Peng,Bastow, Kenneth F.,Nakanishi, Yuka,Nampoothiri, Priya,Hamel, Ernest,Brossi, Arnold,Lee, Kuo-Hsiung
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p. 2891 - 2893
(2007/10/03)
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- Tricyclic indole-2-carboxylic acids: Highly in vivo active and selective antagonists for the glycine binding site of the NMDA receptor
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A series of tricyclic indole-2-carboxylic acid derivatives were synthesized and evaluated by the radioligand binding assay and the anticonvulsant effects in the mouse NMDA-induced seizure model. Among them, derivatives of 3S-(-)-4 such as 3a, 3f, and 3g which had certain zwitterionic anilides showed high affinity to the NMDA-glycine binding site. The absolute configuration of 3S-(-)-4 was confirmed by X-ray crystallographic analysis. In particular, 3g (SM-31900) was found to be a highly active glycine antagonist for both in vitro and in vivo assays (Ki = 1.0 ± 0.1 nM, ED50 = 2.3 mg/kg, iv) and also showed high selectivity for the glycine site. In addition, 3g was soluble enough in aqueous media (> 10 mg/mL at pH 7.4) to use for medications by intravenous injection.
- Katayama, Seiji,Ae, Nobuyuki,Kodo, Toru,Masumoto, Shuji,Hourai, Shinji,Tamamura, Chika,Tanaka, Hiroyasu,Nagata, Ryu
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p. 691 - 701
(2007/10/03)
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- 5-SUBSTITUTED 1,1-DIOXO-`1,2,5!THIAZOLIDINE-3-ONE DERIVATIVES AS PTPASE 1B INHIBITORS
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Compounds of the formula (I) provide pharmacological agents which are inhibitors of PTPases, in particular, the compounds of formula (I) inhibit PTP-1 B and TC PTP, and thus may be employed for the treatment of conditions associated with PTPase activity.
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Page/Page column 90
(2010/02/07)
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- DRUG DISCHARGE PUMP INHIBITORS
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A medicament for preventive and/or therapeutic treatment of a microbial infection having an activity of eliminating resistance of a microorganism with acquired resistance to an antimicrobial agent, which comprises as an active ingredient a compound represented by the following general formula (I), a physiologically acceptable salt thereof, or a hydrate thereof: wherein R1 and R2 independently represent hydrogen atom, a halogen atom, carboxyl group and the like; J1 represents a 5- or 6-membered heteroaromatic ring; W1 represents -CH=CH-, -C≡C-, -CH2CH2- and the like; A1 represents phenylene group, pyridinediyl group, furandiyl group and the like; G1 represents oxygen atom, carbonyl group, ethynyl group and the like; p represents an integer of from 0 to 3; G2 represents phenylene group, furandiyl group, tetrahydrofurandiyl group and the like; G3 represents -CH2- or single bond; m and n represent an integer of 0 or 1; and Q1 represents an acidic group.
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- Asymmetric approaches to 1,2-disubstituted mitosenes based on the intramolecular cyclization of diazoesters
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A strategy for the asymmetric synthesis of 1,2-disubstituted mitosenes is described. The key reaction is the decomposition of a meso diazoester in the presence of chiral copper(I) catalysts. Cyclization of diazoesters derived from (1R, 2S, 5R)-menthol and
- Lee, Sangku,Lim, Hee-Jong,Cha, Kobpurn Lulu,Sulikowski, Gary A.
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p. 16521 - 16532
(2007/10/03)
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- Intramolecular Aminolysis of Esters. Cyclization of Esters of (o-Aminophenyl)acetic Acid
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Rate constants have been obtained for cyclization of the methyl and trifluoroethyl esters of (o-aminophenyl)acetic acid to 2-oxindole.Cyclization occurs via both the neutral and protonated species.Hydroxide ion catalysis occurs in reactions of the methyl ester with a second-order rate constant kOH that is 100-fold greater than for hydroxide ion catalyzed hydrolysis of methyl phenylacetate.The kOH for cyclization of the trifluoroethyl ester is 60-fold larger at 30 deg C than that of the methyl ester.The log k0 vs. pH profile for the trifluoroethyl ester is bell shaped at low pH, indicating that the rate-determining step is changing with pH.Consequently, an intermediate is formed in the cyclization reaction that must be a tetrahedral addition product.This is also shown by curved plots of kobsvd vs. buffer concentration for cyclization of the methyl ester at pH less than 7, which indicate that the rate-determining step is changing with increasing buffer concentration.The rate-determining step at pH > 4 and low buffer concentration must be breakdown of a tetrahedral intermediate.The general base catalysis observed in the cyclization reaction of the methyl and trifluoroethyl esters is characterized by Broensted β coefficients of 0.5 and 0.2 respectively.Thus, in the general base-catalyzed reactions proton transfer is concerted with bond breaking, in contrast with the similar reactions of methyl 2-(aminomethyl)benzoate, in which a proton-transfer step is rate-determining. (β = 1.0).The decrease in Broensted coefficient as the leaving group is improved indicates that the general base is partially removing a proton from the neutral tetrahedral intermediate as the C-O bond breaks.Several different mechanisms and/or rate-determining steps are possible in the intramolecular aminolysis of aliphatic esters; the key features in these aminolysis reactions in regard to mechanism are the pKa of the nucleophile, the steric fit of the nucleophile to the carbonyl, and the ease of C-O bond breaking in decomposition of a tetrahedral intermediate to products.
- Fife, Thomas H.,Duddy, Neil W.
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