- Advanced Real-Time Process Analytics for Multistep Synthesis in Continuous Flow**
-
In multistep continuous flow chemistry, studying complex reaction mixtures in real time is a significant challenge, but provides an opportunity to enhance reaction understanding and control. We report the integration of four complementary process analytical technology tools (NMR, UV/Vis, IR and UHPLC) in the multistep synthesis of an active pharmaceutical ingredient, mesalazine. This synthetic route exploits flow processing for nitration, high temperature hydrolysis and hydrogenation reactions, as well as three inline separations. Advanced data analysis models were developed (indirect hard modeling, deep learning and partial least squares regression), to quantify the desired products, intermediates and impurities in real time, at multiple points along the synthetic pathway. The capabilities of the system have been demonstrated by operating both steady state and dynamic experiments and represents a significant step forward in data-driven continuous flow synthesis.
- Sagmeister, Peter,Lebl, René,Castillo, Ismael,Rehrl, Jakob,Kruisz, Julia,Sipek, Martin,Horn, Martin,Sacher, Stephan,Cantillo, David,Williams, Jason D.,Kappe, C. Oliver
-
supporting information
p. 8139 - 8148
(2021/03/01)
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- Functional Group-Directed Photochemical Reactions of Aromatic Alcohols, Amines, and Thiols Triggered by Excited-State Hydrogen Detachment: Additive-free Oligomerization, Disulfidation, and C(sp2)-H Carboxylation with CO2
-
Exploring new types of photochemical reactions is of great interest in the field of synthetic chemistry. Although excited-state hydrogen detachment (ESHD) represents a promising prospective template for additive-free photochemical reactions, applications of ESHD in a synthetic context remains scarce. Herein, we demonstrate the expansion of this photochemical reaction toward oligomerization, disulfidation, and regioselective C(sp2)-H carboxylation of aromatic alcohols, thiols, and amines. In the absence of any radical initiators in tetrahydrofuran upon irradiation with UV light (λ = 280 or 300 nm) under an atmosphere of N2 or CO2, thiols and catechol afforded disulfides and oligomers, respectively, as main products. Especially, the photochemical disulfidation proceeded highly selectively with the NMR and quantum yields of up to 69 and 0.46%, respectively. In stark contrast, the photolysis of phenylenediamines and aminophenols results in photocarboxylation in the presence of CO2 (1 atm). p-Aminophenol was quantitatively carboxylated by photolysis for 17 h with a quantum yield of 0.45%. Furthermore, the photocarboxylation of phenylenediamines and aminophenols proceeds in a highly selective fashion on the aromatic C(sp2)-H bond next to a functional group, which is directed by the site-selective ESHD of the functional groups for the formation of aminyl and hydroxyl radicals.
- Abe, Kanae,Nakada, Akinobu,Matsumoto, Takeshi,Uchijyo, Daiki,Mori, Hirotoshi,Chang, Ho-Chol
-
p. 959 - 969
(2020/12/23)
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- Method for synthesizing mesalazine
-
A method for synthesizing mesalazine is disclosed. The method comprises the following steps: 1) adding p-nitrophenol, p-toluenesulfonic acid, absolute ethyl alcohol and hexamethylenetetramine, stopping heating after the reaction is finished, heating to room temperature while stirring with ice water, separating out solids, filtering, washing and drying to obtain 5-nitrosalicylaldehyde; 2) adding the 5-nitrosalicylaldehyde, potassium tert-butoxide, copper salt and acetonitrile, adding tert-butyl hydroperoxide while stirring, after the reaction is finished, performing vacuum concentration to remove the solvent, pouring cold water into residues, stirring, performing suction filtration, adjusting the pH value of the filtrate with hydrochloric acid, performing suction filtration, and drying to obtain 5-nitrosalicylic acid; and 3) adding stannous chloride dihydrate, concentrated hydrochloric acid, the 5-nitrosalicylic acid and ethanol, carrying out vacuum concentration after the reaction is finished, dissolving residues in water, adjusting the pH value with a concentrated hydrochloric acid solution, standing for crystallization, carrying out suction filtration, washing filter cake with water, and drying to obtain mesalazine. No isomer is generated, and the yield is high; the method does not need high-temperature and high-pressure conditions; the reaction cost is low; and raw materialsand auxiliary materials with high toxicity and heavy environmental pollution are not used.
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Paragraph 0011; 0048-0052
(2020/08/25)
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- One-pot catalytic synthesis method of 5-aminosalicylic acid
-
According to the invention, an aniline synthesis method of 5-aminosalicylic acid is improved, and a one-pot catalytic synthesis method of 5-aminosalicylic acid is provided. The method comprises the following steps: reacting aniline with sodium nitrite to generate aniline diazonium liquid; coupling the aniline diazonium solution with salicylic acid under an alkaline condition to generate a 5-(phenylazo)salicylic acid sodium salt solution; directly adding a recyclable catalyst palladium on carbon or raney nickel without separating the 5-(phenylazo) salicylic acid sodium salt, feeding hydrogen for reduction, filtering out the catalyst after the reduction reaction is finished, distilling aniline, adjusting the pH value with hydrochloric acid, and crystallizing the reaction product to obtain the 5-aminosalicylic acid. According to the method, the operation steps are reduced, the yield is increased, the wastewater discharge is reduced, and the industrial production process of the 5-aminosalicylic acid is optimized.
- -
-
Paragraph 0013; 0026-0049
(2020/08/27)
-
- Salicylic acid azo 8-hydroxyquinoline and preparation method and application thereof
-
The invention relates to salicylic acid azo 8-hydroxyquinoline and a preparation method, an identification method and application thereof, and belongs to the field of applied chemistry. The chemical expression of the salicylic acid azo 8-hydroxyquinoline is 5Am-8Hq, and the molecular structural formula is shown as follows (please see the specifications for the formula). The preparation method of the salicylic acid azo 8-hydroxyquinoline comprises the steps that phenylamine, 8-hydroxyquinoline and 5-aminosalicylic acid are taken as main raw materials, and a novel salicylic acid azo 8-hydroxyquinoline (Am-8Hq) host compound is prepared on the basis of a phenylamine diazo coupling method. Through infrared, ultraviolet and molecular fluorescence spectrometry, the structure of the salicylic acid azo 8-hydroxyquinoline and interaction behavior of the salicylic acid azo 8-hydroxyquinoline with various negative ions are studied, a novel system which is high in sensitivity, good in selectivityand capable of realizing naked eye detection of ultraviolet sensing negative ions is established, hypochlorite negative ions can be identified and quantitatively detected in water, acetonitrile and methyl alcohol, and the salicylic acid azo 8-hydroxyquinoline has an obvious identification effect only on the hypochlorite negative ions in different polar solvents.
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Paragraph 0042; 0047; 0051; 0054-0056
(2019/11/12)
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- A US salad qin industrial preparation method (by machine translation)
-
The invention discloses a US salad qin industrial preparation method, characterized in that the preparation method is as follows: 1) to 2 - chloro - 5 - nitro-benzoic acid (I) as the starting material, the addition of a base, in a certain temperature lower substitution reaction to produce 2 - hydroxy - 5 - nitro-benzoic acid (intermediate II); 2) a certain pressure and temperature, and the catalyst, under alkaline conditions, for the finished product to the United States of Raney nickel reduction of nitro salad qin. The process of the invention the synthesis cost is low, mild reaction conditions, the whole process uses water as solvent, without the use of toxic reagent, catalyst recycled, the whole process of the green production; the product obtained by the process for high yield, with better purity. (by machine translation)
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Paragraph 0015-0020
(2018/03/24)
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- A 2 - hydroxy - 5 - aminobenzoic acid preparation method
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The invention provides a preparation method of 2-hydroxy-5-aminobenzoic acid, comprises the following steps: carrying out Kolbe-Schmitt reaction on p-aminophenol as an initial raw material to obtain the target compound with high yield under the effect of a catalytic carrier or solid alkali or under the direct catalytic carrier effect on the p-aminophenol. The path is simple and short, the used catalytic carrier is capable of improving the heat transfer effect, reducing the energy consumption and improving the yield. Furthermore, the catalytic carrier is non-wear to the equipment, the security is improved, the purifying treatment is convenient, and the preparation method is suitable for the industrial production.
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Paragraph 0025; 0027-0033
(2018/04/02)
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- 4-substituted pyridine-2-formamide compound, preparation method thereof and application
-
The invention discloses a 4-substituted pyridine-2-formamide compound, a preparation method thereof and an application. The 4-substituted pyridine-2-formamide compound has a structure as shown in a formula I, and the chemical name of the compound is 4-{4-[3-(4-chlorine-3-trifluoromethyl-phenyl)-ureide]-3-carboxyl phenoxy}-N-picoline-2-carboxylic methylamine. According to the preparation method of the 4-substituted pyridine-2-formamide compound, 4-chlorine-2-picolinic acid serves as an initial raw material, and the compound in the formula I is prepared by acylating chlorination, amination, substitution reaction and condensation reaction. The 4-substituted pyridine-2-formamide compound retains a Sorafenib efficacy structure, 5-aminosalicylic acid or aminosalicylic acid ester achieving a positive pharmacological function in the metabolic process replaces p-aminophenol with large toxic and side effects, efficacy can be improved, and the toxic and side effects are reduced.
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-
Paragraph 0086; 0088; 0089
(2018/03/28)
-
- Computational and synthetic approaches for developing Lavendustin B derivatives as allosteric inhibitors of HIV-1 integrase
-
Through structure-based virtual screening and subsequent activity assays of selected natural products, Lavendustin B was previously identified as an inhibitor of HIV-1 integrase (IN) interaction with its cognate cellular cofactor, lens epithelium-derived growth factor (LEDGF/p75). In order to improve the inhibitory potency we have employed in silico-based approaches. Particularly, a series of new analogues was designed and docked into the LEDGF/p75 binding pocket of HIV-1 IN. To identify promising leads we used the Molecular Mechanics energies combined with the Generalized Born and Surface Area continuum solvation (MM-GBSA) method, molecular dynamics simulations and analysis of hydrogen bond occupancies. On the basis of these studies, six analogues of Lavendustine B, containing the benzylamino-hydroxybenzoic scaffold, were selected for synthesis and structure activity-relationship (SAR) studies. Our results demonstrated a good correlation between computational and experimental data, and all six analogues displayed an improved potency for inhibiting IN binding to LEDGF/p75 in?vitro to respect to the parent compound Lavendustin B. Additionally, these analogs show to inhibit weakly LEDGF/p75-independent IN catalytic activity suggesting a multimodal allosteric mechanism of action. Nevertheless, for the synthesized compounds similar profiles for HIV-1 inhibition and cytoxicity were highlighted. Taken together, our studies elucidated the mode of action of Lavendustin B analogs and provided a path for their further development as a new promising class of HIV-1 integrase inhibitors.
- Agharbaoui, Fatima E.,Hoyte, Ashley C.,Ferro, Stefania,Gitto, Rosaria,Buemi, Maria Rosa,Fuchs, James R.,Kvaratskhelia, Mamuka,De Luca, Laura
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p. 673 - 683
(2016/08/12)
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- COMPOSITIONS AND METHODS FOR THE TREATMENT OF INFLAMMATORY BOWEL DISEASE
-
The invention relates to the compounds of formula I and formula II or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I or formula II; and methods for treating or preventing inflammatory bowel disease may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of gastrointestinal diseases and inflammation such as inflammatory bowel disease, ulcerative colitis, mild-to-moderate Crohn's disease, rheumatoid arthritis, inflammatory arthritis, psoriatic arthritis, liver cirrhosis and idiopathic urticaria.
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Paragraph 0131; 0132
(2016/06/01)
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- Compositions and methods for the treatment of inflammatory bowel disease
-
The invention relates to the compounds of formula I and formula II or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I or formula II; and methods for treating or preventing inflammatory bowel disease may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of gastrointestinal diseases and inflammation such as inflammatory bowel disease, ulcerative colitis, mild-to-moderate Crohn's disease, rheumatoid arthritis, inflammatory arthritis, psoriatic arthritis, liver cirrhosis and idiopathic urticaria.
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Page/Page column 39; 40; 41; 42
(2016/12/16)
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- Preparation method of 5-aminosalicylic acid
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The invention discloses a preparation method of 5-aminosalicylic acid. The method comprises the following steps: 1, preparing 5-nitrosalicylic acid: pre-incubating a salicylic acid solution used as a material 1, a concentrated nitric acid solution used as a material 2 and concentrated sulfuric acid used as a material 3 to a reaction temperature, mixing and reacting the material 1, the material 2 and the material 3, and post-processing the obtained reaction product to obtain purified 5-nitrosalicylic acid; and 2, preparing 5-aminosalicylic acid: dissolving the purified 5-nitrosalicylic acid in a solvent, adding Na2CO3 and a catalyst PdC to obtain a material 4, and carrying out pre-incubation catalytic hydrogenation to reduce the 5-nitrosalicylic acid into 5-aminosalicylic acid. The method has the advantages of simplicity in operation, controllable heat release, short production period, good area selectivity, environmental protection and safety, and realization of high yield and high purity of the finally obtained product.
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-
Paragraph 0041; 0045; 0046
(2017/07/22)
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- Antiphlogistic enteropathy and method for treating dermatopathy compsn.
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The invention relates to the compounds of formula I and formula II or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I or formula II; and methods for treating or preventing inflammatory bowel disease may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of gastrointestinal diseases and inflammation such as inflammatory bowel disease, ulcerative colitis, mild-to-moderate Crohn's disease, rheumatoid arthritis, inflammatory arthritis, psoriatic arthritis, liver cirrhosis and idiopathic urticaria.
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Paragraph 0103; 0106; 0107; 0392; 0395; 0396
(2018/10/19)
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- Regioselective ortho-carboxylation of phenols catalyzed by benzoic acid decarboxylases: A biocatalytic equivalent to the Kolbe-Schmitt reaction
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The enzyme catalyzed carboxylation of electron-rich phenol derivatives employing recombinant benzoic acid decarboxylases at the expense of bicarbonate as CO2 source is reported. In contrast to the classic Kolbe-Schmitt reaction, the biocatalytic equivalent proceeded in a highly regioselective fashion exclusively at the ortho-position of the phenolic directing group in up to 80% conversion. Several enzymes were identified, which displayed a remarkably broad substrate scope encompassing alkyl, alkoxy, halo and amino- functionalities. Based on the crystal structure and molecular docking simulations, a mechanistic proposal for 2,6-dihydroxybenzoic acid decarboxylase is presented.
- Wuensch, Christiane,Gross, Johannes,Steinkellner, Georg,Lyskowski, Andrzej,Gruber, Karl,Glueck, Silvia M.,Faber, Kurt
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p. 9673 - 9679
(2014/03/21)
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- PREPARATION OF 5-AMINOSALICYLIC ACID BY GAS PHASE CATALYTIC CARBOXYLATION
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Disclosed is a process for preparing 5-aminosalicylic acid by gas phase catalytic carboxylation, characterized in that carbon dioxide is introduced into a system of p-acetaminophenol and a basic compound at a temperature of 150° C.?220° C. and a pressure of 0.5?5.0 MPa in the presence of a catalyst, so as to carry out a gas phase catalytic carboxylation reaction to form a 5-aminosalicylate, and the crude product 5-aminosalicylate is separated, and then acidified to prepare 5-aminosalicylic acid (5-ASA). Since the gas phase catalytic reaction replaces a solid phase thermo-chemical reaction, the reaction is significantly improved in terms of the process flow, reaction conditions, product quality and energy consumption. In addition, the reaction has a short reaction time, good selectivity, high yield and no formation of wastes during the reaction, and is suitable for industrial production.
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Paragraph 0050
(2013/11/05)
-
- Sustainable chemical process for reduction of nitro compounds (R-NO2) or nitroso compounds (R-NO) containing sulphonic or carboxylic group into corresponding amino compounds (R-NH2) with inherent recycle of all acidic streams generated in synthesis
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The process of the present invention creates a sustainable and closed water loop allowing inherent recycles of all liquid streams generated in the process. The liquid streams generated during the process of the invention are inherently recycled completely, making the process of the present invention a zero liquid discharge process which is environmentally friendly and sustainable. This invention further relates to a sustainable chemical process of reduction of R—NO2 or R—NO into corresponding R—NH2 that produces environmentally friendly R—NH2 in good yields and selectivity with large of mother liquor recycle. The process has a wide scope in that it can be applied to a number of molecules.
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Page/Page column 14-16
(2012/08/27)
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- Enzyme-responsive controlled release of covalently bound prodrug from functional mesoporous silica nanospheres
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I want to break free: Mesoporous silica nanoparticles are functionalized with sulfasalazine (SZ; see scheme), a prodrug of 5-aminosalicylic acid (5-ASA) and sulfapyridine, to generate enzyme-responsive nanocarriers. In the presence of the colon-specific e
- Popat, Amirali,Ross, Benjamin P.,Liu, Jian,Jambhrunkar, Siddharth,Kleitz, Freddy,Qiao, Shi Zhang
-
supporting information
p. 12486 - 12489
(2013/02/23)
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- SUSTAINABLE CHEMICAL PROCESS FOR REDUCTION OF NITRO COMPOUNDS (R-NO2) OR NITROSO COMPOUNDS (R-NO) CONTAINING SULPHONIC OR CARBOXYLIC GROUP INTO CORRESPONDING AMINO COMPOUNDS (R-NH2) WITH INHERENT RECYCLE OF ALL ACIDIC STREAMS GENERATED IN SYNTHESIS
-
The process of the present invention creates a sustainable and closed water loop allowing inherent recycles of all liquid streams generated in the process. The liquid streams generated during the process of the invention are inherently recycled completely, making the process of the present invention a zero liquid discharge process which is environmentally friendly and sustainable. This invention further relates to a sustainable chemical process of reduction of R- NO2 or R-NO into corresponding R-NH2 that produces environmentally friendly R-NH2 in good yields and selectivity with large of mother liquor recycle. The process has a wide scope in that it can be applied to a number of molecules.
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Page/Page column 46; 49
(2011/05/06)
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- Synthesis and characterization of ruthenium(III) chloride complexes with some 1,2-disubstituted benzimidazoles and their catalytic activity
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Reaction of ruthenium(III) chloride with 2-mono substituted and 1,2-disubstituted benzimidazoles yield the complexes of the formulae RuCl 3Ly.nH2O [L = 2-o-hydroxyphenylbenzimidazole (oHPB), y = 3, n = 0; L = 2-p-hydroxyphenylbenzimidazole (pHPB), y = 2, n = 3], and RuCl3L2.H2O [L = 1-o-hydroxybenzyl-2-o-hydroxyphenylbenzimidazole (oHBPB), 1-m-hydroxybenzyl-2-m-hydroxyphenylbenzimidazole (mHBPB), and 1-p-hydroxybenzyl-2-p-hydroxyphenylbenzimidazole (pHBPB)]. The complexes are characterized by elemental analysis, conductivity measurements, infrared, electronic, 1H- and 13C-NMR spectral studies, as well as by thermal analysis. The complexes exhibit octahedral geometry. Some of the complexes act as potential catalyst towards transferhydrogenation. Copyright Taylor & Francis Group, LLC.
- Krishnamurthy
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scheme or table
p. 590 - 597
(2011/10/03)
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- Synthesis of 5-aminosalicylic acid using kolbe-schmidt reaction under supercritical conditions
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5-Aminosalicylic acid is one of the preferred drugs in clinical treatment of inflammatory bowel disease, so it has important significance to investigate the process of its preparation. In this work, 5-aminosalicylic acid was synthesized by Kolbe-Schmidt reaction under supercritical conditions. Supercritical CO2 serves as both reactant and reaction medium in the reaction. The effects of various conditions, such as pressure, temperature, reaction time and stir speed, on the yield of 5-aminosalicylic acid were investigated. As the supercritical CO2 has high diffusion coefficient, high solubility, high mass transfer efficiency and effective heat transfer capacity, the reaction can be carried out in a homogenizing situation. The experimental results show that more than 90.5 % of the yield of 5-aminosalicylic acid can be obtained under the optimal reaction parameters such as pressure (9.0 MPa), temperature (140 °C), reaction time (2.5 h) and stir speed (300 rpm). The results indicate that, in supercritical state, Kolbe-Schmidt reaction can be carried out with high speed at much lower temperature compared to that of the traditional technology and the product quality and production efficiency is also enhanced.
- Lü, Hailiang,Liu, Junqi,Xing, Cunzhang,Tan, Mingchen,Gao, Fei
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experimental part
p. 3819 - 3823
(2012/01/05)
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- Molecular nanofibers of olsalazine form supramolecular hydrogels for reductive release of an anti-inflammatory agent
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Conjugation of tripeptide derivatives with olsalazine, a clinically used anti-inflammatory prodrug, yields small molecules that self-assemble in water to form supramolecular hydrogels that undergo a gel-to-sol phase transition upon reduction, resulting in the controlled release of 5-aminosalicylic acid as the anti-inflammatory agent. This methodology will ultimately lead to new biomaterials for site-specific drug delivery.
- Li, Xinming,Li, Jiayang,Gao, Yuan,Kuang, Yi,Shi, Junfeng,Xu, Bing
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p. 17707 - 17709
(2011/03/16)
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- Synthesis, kinetic studies and pharmacological evaluation of mutual azo prodrugs of 5-aminosalicylic acid for colon-specific drug delivery in inflammatory bowel disease
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Colon-specific mutual azo prodrugs of 5-aminosalicylic acid with essential amino acids were synthesized for the management of inflammatory bowel disease. The structures were confirmed by elemental and spectral analyses. 85-88% release of 5-aminosalicylic acid was achieved in rat fecal matter with half-lives ranging from 140 to 160 min, following first order kinetics. The prodrugs exhibited comparable ameliorating effect as that of sulfasalazine on trinitrobenzenesulfonic acid-induced experimental colitis in rats with a better safety profile.
- Dhaneshwar, Suneela S.,Gairola, Neha,Kandpal, Mini,Vadnerkar, Gaurav,Bhatt, Lokesh,Rathi, Badal,Kadam
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experimental part
p. 3922 - 3929
(2009/12/04)
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- RETRACTED ARTICLE: Synthesis, kinetic studies and pharmacological evaluation of mutual azo prodrug of 5-aminosalicylic acid for colon-specific drug delivery in inflammatory bowel disease
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Mutual azo prodrug of 5-aminosalicylic acid with l-tyrosine was synthesized by coupling l-tyrosine with salicylic acid, for targeted drug delivery to the inflamed gut tissue in inflammatory bowel disease. The structure was confirmed by elemental analysis, IR and NMR spectroscopy. In vitro kinetic studies in rat fecal matter showed 87.18% release of 5-aminosalicylic acid with a half-life of 140.28 min, following first order kinetics. Therapeutic efficacy of the carrier system and the mitigating effect of the azo conjugate were evaluated in trinitrobenzenesulfonic acid-induced experimental colitis model. Myeloperoxidase activity was determined by the method of Krawisz et?al. The synthesized prodrug was found to produce comparable mitigating effect as that of sulfasalazine on colitis in rats.
- Dhaneshwar, Suneela S.,Kandpal, Mini,Vadnerkar, Gaurav,Rathi, Badal,Kadam
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p. 885 - 890
(2008/03/17)
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- Bioadhesive anti-inflammatory pharmaceutical compositions
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Disclosed are compounds having the formula wherein R2is hydrogen, a monomeric glycoside or an oligomeric glycoside, R3is hydrogen, a monomeric glycoside, an oligomeric glycoside, or a group having the formula R is a lower alkylene, R′ is selected from the group consisting of moieties having the formula where X=0 or 1, Y=0 or 1, R1is hydrogen or a pharmacologically active drug residue, R8a pharmacologically active drug residue, R4, R5, and R6are independently hydrogen, alkyl, aryl, aralkyl, and cycloalkyl or together form a nitrogen-containing ring, and R7is hydroxyl or hydroxyalkyl.
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Page/Page column 20-21
(2008/06/13)
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- 1,3-Dihydroxybenzene derivatives and colorants containing said compounds
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1,3-Dihydroxybenzene derivatives of general formula (I) or (Ia) or physiologically tolerated, water-soluble thereof wherein R′1 denotes substituted pyridyl group, a pyrimidyl group, a group of formula (IIa) or (IIIa) and the dyeing agents for keratin fibers containing these compounds.
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- Pharmaceutical compounds for treating copd
-
Use of an MPO inhibitor for the treatment of COPD.
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-
-
- Bioadhesive pharmaceutical compositions
-
Disclosed are compounds having the formula wherein R2 is hydrogen, a monomeric glycoside or an oligomeric glycoside, R3 is hydrogen, a monomeric glycoside, an oligomeric glycoside, or a group having the formula R is a lower alkylene, R′ is selected from the group consisting of moieties having the formula where X=0 or 1, Y=0 or 1, R1 is hydrogen or a pharmacologically active drug residue, R8 a pharmacologically active drug residue, R4, R5, and R6 are independently hydrogen, alkyl, aryl, aralkyl, and cycloalkyl or together form a nitrogen-containing ring, and R7 is hydroxyl or hydroxyalkyl.
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- Bisacetamide hydrochloride: A chemoselective and inexpensive N-acetylating reagent for aminophenols
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A facile and chemoselective acetylation of aminophenols using bisacetamide hydrochloride under conventional heating and microwave irradiation has been developed. Also, a rapid method for the microwave-assisted preparation of aminophenols is described herein.
- Peng, Yanqing,Song, Gonghua,Ding, Fang
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p. 2021 - 2023
(2007/10/03)
-
- Novel breakers of advanced glycation endproducts
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Advanced glycation endproducts (AGEs) have been implicated in the pathogenesis of a variety of debilitating diseases such as diabetes, atherosclerosis, Alzheimer's and rheumatoid arthritis, as well as in the normal aging process. Seven compounds are here reported to be active in breaking AGE-protein cross-links. These compounds are 1,4-benzene-bis[4-methyleneaminophenoxyisobutyric acid] (LR102); 4-[(3,5-dichlorophenylureidophenoxyisobutyryl]-4-aminobenzoic acid (LR99); L-bis-[4-(4-chlorobenzamidophenoxyisobutyryl)cystine] (LR20); 4-(3,5-dichlorophenylureido)phenoxyisobutyryl-1-amidocyclohexane-1-carboxylic acid (LR23); methylene bis [4,4′-(2-chlorophenylureidophenoxyisobutyric acid)] (LR90); 5-aminosalicylic acid (5-ASA); and metformin. These compounds may be used to reverse the debilitating effects of those diseases in which AGEs are formed.
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- Microwave thermolysis VII: Selective diversity in the reduction using sodium hypophosphite under microwave irradiation
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The selective reduction of nitro group into amine using sodium hypophosphite under microwave irradiation is described. The rapid reaction, solvent free conditions and selectivity over common functional groups like CN, OH, COOH, CONH2 and halogens are the distinct features of the procedure.
- Meshram,Ganesh,Sekhar, K. Chandra,Yadav
-
p. 993 - 994
(2007/10/03)
-
- Basic studies on 5-(7-hydroxy-3-O-phosphonocholyl)aminosalicylic acid for the evaluation of microbial overgrowth
-
A newly synthesized conjugate of 7-hydroxy-3-O-phosphonocholic acid (ursodeoxycholic acid monophosphate) with 5-aminosalicylic acid (5-ASA-UDCA monophosphate) was investigated to determine its suitability for the evaluation of enteric bacteria. This compound, 5-ASA-UDCA monophosphate, was efficiently deconjugated by cholylglycine hydrolase to release 5-ASA, whereas it was completely resistant to deconjugation by pancreatic and intestinal mucosal enzymes. In everted gut sac experiments, 5-ASA-UDCA monophosphate was not actively absorbed from any part of the small intestine. In animal experiments, urinary excretions of N-acetyl-5-ASA (Ac-5ASA) were measured for 24 h following the oral administration of 20 mg of 5-ASA-U DCA monophosphate. Control rats excreted 276.3±89.0 μg (mean±S.E.) of Ac-5ASA, whereas the rats with intestinal bacterial overgrowth excreted more (1224.1 ± 231.5 μg; p0.01). These basic studies indicate that this compound is likely to offer a simple method for the evaluation of microbial overgrowth without the use of radioisotopes or expensive, special apparatus.
- Konishi, Toshio,Takahashi, Makoto,Ohta, Shunsaku
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p. 370 - 375
(2007/10/03)
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- Azo dyes having utility for ink jet printers
-
A group of compounds comprising the reaction product of a hydroxy naphthylamine sulfonic acid with a diazotized compound comprising, an aromatic azo substituted Cleves Acid such that the diazotized compound is coupled with the hydroxy naphthylamine sulfonic acid ortho to the amine group. More particularly the compounds of the invention comprise a compound having the formula: STR1 wherein R1 is an aromatic azo radical, R2 is hydrogen or an aromatic azo group and R3 is amino, substituted amino or an aromatic azo group. The invention further includes inks made from such compositions and methods for using such inks in ink jet printers.
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- Prodrug derivatives of carboxylic acid drugs
-
Novel ester derivatives of carboxylic acid medicaments of formula (I), wherein R--COO--represents the acyloxy residue of a carboxylic acid drug or medicament, n is an integrer from 1 to 3, and R1 and R2 are the same or different and are selected from a group consisting of an alkyl, an alkenyl, an aryl, an aralkyl, a cycloalkyl and which group may be unsubstituted or substituted, or R1 and R2 together with the N forms a 4-, 5-, 6- or 7-membered heterocyclic ring, which in addition to the nitrogen atom may contain one or two further heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur and which heterocyclic group may be substituted. These compounds are highly biolabile prodrug forms of the corresponding carboxylic acid compounds and are highly susceptible to undergoing enzymatic hydrolysis in vivo whereas they are highly stable in aqueous solution. The novel derivatives are less irritating to mucosa than the parent carboxylic acids and may provide an improved bio-availability of the drugs.
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- High molecular weight prodrug derivatives of antiinflammatory drugs
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Compounds of the formula 1, PS - O - A - (CH2)n- B - D (1), wherein PS-O represents an alkoxide residue of any of the free hydroxy groups of a polysaccharide (PS-OH) compound with molecular weight (Mw) of from 40,000 to 5,000,000 selected from dextran, carboxymethyl dextran, diethylaminoethyl dextran, starch, hydroxyet-hyl starch, alginates, glycogen, pullullan, agarose, cellulose, chitosan, chitin and carrageenan,A is a carbonyl group or absent,n is zero or a positive integer from 1 to 14,B is oxygen, a carbonyl group, NR wherein R is hydrogen or lower alkyl, or B is absent, and, D is (i) a group of the formula:, R1 - CO - (11), wherein R1-CO- represents the acyl residue of a carboxylic acid drug (R1-COOH) used in the treatment of inflammatory disorders; or (ii) a group of the formula:, R2 - O - (12), wherein R2-O- refers to the C-21 alkoxide residue of a known antiinflammatory steroid (R2-OH) or an alkoxide residue of any other drug or medicament containing a hydroxy functional group used in the treatment of inflammatory disorders; with the proviso that when A is absent, n is 0, and B is absent, then R1-CO- is different from the acyl residue of acetylsalicylic acid;, and non-toxic pharmaceutically acceptable acid addition salts thereof;, and non-toxic pharmaceutically acceptable cation salts thereof. Such compounds are biolabile prodrugs providing controlled release and prolonged duration of action of the parent active antiinflamma-tory agents locally at the administration site after intra-articular, intra-muscular, subcutaneous or extra-dural application while at the same time being highly stable in aqueous solution in the pH range 3--5. After oral administration of such prodrugs the parent drug is liberated selectively in the terminal ileum and the colon over an extended period of time.
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- Bisazo brown reactive dye
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A brown reactive dye represented by a free acid of the formula, STR1 wherein R is a hydrogen atom or a C1 to C4 alkyl group, X is --SO2 CH2 CH2 Cl, --SO2 CH=CH2, --SO2 CH2 CH2 OSO3 H or --SO2 CH2 CH2 OPO3 H2, rings A, B and C are each a benzene or naphthalene ring which may have other substituent, m is 0 to 3 and n is 0 to 1. This dye is suitable for dyeing cellulose fibers brown to afford dyeings superior in fastnesses, acid stability, build-up property and level dyeing property.
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- Azo dyestuffs
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Azo dyestuffs, which in the acid form, are represented by the formula: wherein A is an aromatic radical, M is a 1,4-benzene radical which may be substituted, E is the residue of a coupling component which is free from azo groups, At least one of A and M containing a phosphonic acid group, and the metal complexes of those having a metallisable group are reactive dyes suitable for use in the process of German OLS No. 2324809.
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