- METHOD FOR PRODUCING CYCLIC ESTER
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In a method for producing a cyclic ester according to an embodiment of the present invention, a mixture (I) containing an aliphatic polyester, a specific polyalkylene glycol diether, and a sulfonic acid compound as a thermal stabilizer is prepared and heated in predetermined conditions to obtain a mixture (II) in a state of solution. Furthermore, heating of the mixture (II) is continued to distill, together with the polyalkylene glycol diether, a cyclic ester formed by the depolymerization reaction, and thus a distillate (III) is obtained. The cyclic ester is recovered from the distillate (III). At this time, a specific solubilizing agent is added to at least one of the mixture (I) or (II). In this production method, the sulfonic acid compound as the thermal stabilizer is contained in the mixtures (I) and (II) and the distillate (III).
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Paragraph 0113-0115; 0120
(2020/12/25)
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- Rosuvastatin calcium intermediate, preparation method thereof and application of intermediate
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The invention discloses a rosuvastatin calcium intermediate, a preparation method thereof and an application of the intermediate. The synthesis process of the intermediate is environmentally friendly,simple and convenient to operate and low in EHS (environment health safety) risk, raw materials are easily available, and used chemical reagents are low in toxicity and low in price, so that the synthesis process of the intermediate is a green synthesis process suitable for industrial production. In addition, the intermediate is applied to synthesis of rosuvastatin calcium and key intermediates thereof, has short route and high yield, effectively reduces the industrial production cost of rosuvastatin calcium, and has a higher industrial application prospect.
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Paragraph 0055-0057
(2019/04/17)
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- CHROMENOPYRIDINE DERIVATIVES AS PHOSPHATIDYLINOSITOL PHOSPHATE KINASE INHIBITORS
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The invention relates to inhibitors of PI5P4K inhibitors useful in the treatment of cancers, neurodegenerative diseases, inflammatory disorders, and metabolic diseases, having the Formula (I); where A1, A2, G, R1, R2, R3, R4, and W are described herein.
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Paragraph 0468
(2019/07/13)
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- CHEMICAL COMPOUNDS
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The invention is directed to substituted heteroaryl derivatives. Specifically, the invention is directed to compounds according to Formula Q: wherein D, L, M, W, X, Y, and Z are defined herein. The compounds of the invention are inhibitors of DNA methyltransferase (DNMT) activity - including DNMT1, DNMT3a, or DNMT3b- and are useful in the treatment of cancer and hyperproliferative diseases. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting DNMT activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention
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Page/Page column 113
(2013/05/21)
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- Ruthenium-Catalyzed Oxidative Cleavage of Alkynes to Carboxylic Acids
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We describe an efficient method for the oxidative cleavage of alkynes to carboxylic acids using a combination of RuO2/Oxone/NaHCO3 in a CH3CN/H2O/EtOAc solvent system. Both internal and terminal alkynes, regardless of their electron density, can be oxidized to carboxylic acids in excellent yield (up to 99%). 1H NMR spectroscopy and ESI-MS experiments provided evidence for α-diketones and anhydrides as possible intermediates in these oxidation reactions.
- Yang, Dan,Chen, Fei,Dong, Ze-Min,Zhang, Dan-Wei
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p. 2221 - 2223
(2007/10/03)
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- A novel access to 2-aminofuranones via cyclization of functionalized γ-hydroxy-α,β-butenoates derived from N-hydroxybenzotriazole esters of α-hydroxy acids
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The reaction between the N-hydroxybenzotriazole esters of substituted glycolic acids and alkyl cyanoacetates or malononitrile leads to the synthesis of γ-hydroxy-functionalized butenoates which are cyclized under mild conditions to the corresponding 2-amino-3,5-disubstituted-4-furanones. That the products are optically active is confirmed by measurements of their optical rotations. On the other hand, replacement of N-hydroxybenzotriazole by N-hydroxysuccinimide might lead to by-products depending on the functionalized glycolic acid used.
- Athanasellis, Giorgos,Detsi, Anastasia,Prousis, Kyriakos,Igglessi-Markopoulou, Olga,Markopoulos, John
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p. 2015 - 2022
(2007/10/03)
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- The design, synthesis and biological evaluation of neuraminic acid-based probes of Vibrio cholerae sialidase
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A molecular modelling study using the program GRID has been used to investigate the structural requirements of a potential inhibitor binding to Vibrio cholerae sialidase. A number of favourable interactions were predicted between the sialidase and Neu2en derivatives containing hydroxyl- or halogen-substituted acyl groups on the C-5 amine. As a result of this study, a detailed analysis of the interactions of C-5-substituted Neu2en derivatives with the active site of V. cholerae sialidase was undertaken using a conformational searching routine based on molecular dynamics. Based on the results of these molecular design studies several N-acyl-Neu2en-based probes were prepared and evaluated for sialidase inhibition. As envisaged, and pleasingly, the designed compounds were found to be accommodated by the enzyme's active site architecture, and to be strong inhibitors of V. cholerae sialidase. Copyright (C) 2000 Elsevier Science Ltd.
- Wilson, Jennifer C.,Thomson, Robin J.,Dyason, Jeffrey C.,Florio, Pas,Quelch, Kaylene J.,Abo, Samia,Von Itzstein, Mark
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- Synthesis of 3-acetoxyazetidin-2-ones and 3-hydroxyazetidin-2-ones with antifungal and antibacterial activity
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The synthesis of a series of 3-acetoxyazetidin-2-ones 3a-n and 3-hydroxyazetidin-2-ones 6a-j is reported together with the antibacterial and antifungal evaluation of these compounds. An additional series of 3-acetoxyazetidin-2-ones 11a-h which possess a free carboxylic acid group on the N-1 aryl ring were obtained by treatment of suitably substituted Schiff bases 10a-h with acetoxyacetyl chloride. The novel bicyclic structures 7-acetoxy-6-phenyl-5-thia-1-azabicyclo[4.2.0]octan-8-one 13 and 7-hydroxy-6-phenyl-5-thia-1-azabicyclo[4.2.0]octan-8-one 14 were also obtained. Many of the compounds displayed antifungal activity in vitro when evaluated against the pathogenic fungi Cryptococcus neoformans, Candida albicans, Candida tropicalis, Candida parapsilosis, Candida glabrata, and Trichosporon cutaneum, while 3-acetoxyazetidin-2-ones 11a-h containing a free carboxylic acid group on the N-1 aryl ring displayed antibacterial activity against Staphylococcus aureus, Proteus vulgaris, Pseudomonas aeruginosa, Bacillus subtilis, Klebsiella aerogenes and Escherischia coli.
- Walsh,Meegan,Prendergast,Al Nakib
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p. 989 - 1000
(2007/10/03)
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- Hydrogen-bond-mediated folding in depsipeptide models of β-turns and α-helical turns
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The folding of several depsipeptides constructed from α-amino acids [L-proline (P) and L-alanine (A)] and α-hydroxy acids [L-lactic acid (L) and glycolic acid (G)] has been examined in methylene chloride solution by variable- temperature IR spectroscopy. Additional studies have been conducted in some cases, involving variable-temperature 1H NMR spectroscopy and molecular mechanics calculations. The depsipeptides include three-residue molecules (PLL, ALL, and PLG) that can form a 13-membered-ring amide-to-amide hydrogen bond, which, for a peptide backbone, would correspond to a single turn of an α-helix. These depsipeptides can also form 10-membered-ring amide-to-ester hydrogen bonds, which would correspond to β-trun formation for a peptide backbone. For PLL and PLG, distinct N-H stretch bands can be identified for three folding patterns: non-hydrogen-bonded, β-turn, and α-helical turn. IR-based van't Hoff analyses for PLL indicate that the α-helical turn and the β-turn are both modestly enthalpically favored relative to the non-hydrogen-bonded state, but neither turn is enthalpically preferred over the other. For PLG, in contrast, the α-helical turn appears to be enthalpically preferred over both of the alternative folding patterns. Comparison between PLL and ALL indicates that the N-terminal proline residue favors α-helical turn formation. The strengths of amide-to-amide and amide-to-ester hydrogen bonds have been compared in the context of a β-turn geometry by analyzing LG and AG in CH2Cl2. The amide-to-amide hydrogen bond is enthalpically favored by ca. 1.6 kcal/mol, but formation of this enthalpically stronger intramolecular hydrogen bond is more costly entropically. Extrapolation from the behavior of these depsipeptides leads us to predict that for tripeptides in a nonpolar environment, a β-turn will generally be enthalpically preferred over an isolated α-helical turn. β-Turn folding has previously been widely studied in model peptides and depsipeptides; however, the present report appears to represent the first experimental effort to model formation of a single α-helical turn.
- Gallo, Elizabeth A.,Gellman, Samuel H.
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p. 9774 - 9788
(2007/10/02)
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- A New Chemoenzymatic Approach to the Synthesis of Penems
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A new synthesis of the valuable penem antibiotics FCE 22101 and FCE 22891 which does not require the use of expensive protecting groups is reported.A mixed carbon-silicon protection of two hydroxy groups was used, followed by a selective enzymatic hydrolysis of the resulting 8-O-protected-2-carboxylic ester (18).Lipase from Chromobacterium viscosum and lipoprotein lipase from Pseudomonas sp. gave excellent results in both free or immobilized form.
- Altamura, Maria,Cesti, Pietro,Francalanci, Franco,Marchi, Marcello,Cambiaghi, Stefano
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p. 1225 - 1229
(2007/10/02)
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- A Simple and Improved Procedure for the Conversion of Alkynes to 1,2-Diketones by Indirect Electrooxidation With Ruthenium Tetroxide as a Mediator
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Indirect electrooxidation of alkynes 1 using ruthenium tetroxide as a mediator, leading to 1,2-diones 2 in 72-87percent, is described.The electrolysis is carried out in the presence of a catalytic amount of ruthenium dioxide dihydrate in a two phase system of saturated aqueous sodium chloride and carbon tetrachloride.The overoxidation of 1,2-diones to the corresponding carboxylic acid, an unavoidable drawback generally encountered in the metal oxidation of acetylenes, is suppressed greatly by maintaining the pH of the aqueous phase at 4 and conducting the reaction at 0-5 deg C.The synthetic utility of this electrochemical oxidation is exemplified by the preparation of 2i (82percent), a key intermediate for the synthesis of furaneol 4, from the commercially available 1i.
- Torii, Sigeru,Inokuchi, Tsutomu,Hirata, Youzou
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p. 377 - 379
(2007/10/02)
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- THE RECTION OF ALDEHYDE ENOL SILYL ETHERS WITH LEAD(IV)ACETATE
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The treatment of aldehyde enol silyl ethers 1 with lead(IV)acetate (LTA) using methylene chloride as solvent gives rise to the production of α-acetoxy aldehydes 2 and glycolic ester derivatives 3 or enals 5.Structrural variations in 1 are used to explained the divergent trends.When 1 is treated with LTA/KOAc/AcOH, high yields of the corresponding α-acetoxy aldehydes 2 are obtained with the formation of 3 and 5 being subverted.
- Rubottom, George M.,Marrero, Roberto,Gruber, John M.
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p. 861 - 866
(2007/10/02)
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- New Antihypertensive Cannabinoids
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A number of azacannabinoids containing hydroxyacyl and aminoacetyl substituents on the nitrogen atom were synthesized.The hydroxyacetyl and γ-hydroxybutyryl derivatives (4a and 7b, respectively) were potent antihypertensive agents (minimum effective dose, 3-5 mg/kg, orally) of the same order of activity as the highly CNS-active N-propargyl derivatives Ia and Ib.Furthermore, 4a showed weak stimulant properties at hypotensive dose levels, in contrast to the strongly CNS-depressant action characteristic of the N-propargyl analogues (Ia,b).
- Zaugg, Harold E.,Kyncl, Jaroslav
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p. 214 - 217
(2007/10/02)
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- HOMOGENEOUS-CATALYTIC REACTIONS OF ALKENES. III. REFINEMENT OF THE MECHANISM OF DECOMPOSITION OF ORGANIC ? COMPLEX OF PALLADIUM
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The homogeneous-catalytic oxidation of ethylene in acetic acid leads to the formation of an organopalladium ?-complex , which dissociates into ethylene glycol monoacetate, vinyl acetate, and ethylidene diacetate, depending on the nature of the ligands.The various mechanisms for the decomposition of the ? complex are due to the effective positive charge at the palladium atom; the greater the charge, the more likely is migration of the hydride ion to the addend from the β-carbon atom or isomerization of the complex into the α-ethoxyethyl compound and, accordingly, the higher the yield of vinyl acetate and ethylidene diacetate.Increase in the electron density at the palladium atom leads to decomposition of the organometallic ? complex to the ethylene glycol monoacetate in the presence of water molecules.
- Devekki, A. V.,Mushenko, D. V.,Fedorov, V. S.
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p. 2250 - 2254
(2007/10/02)
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- Antibacterial agents, and 4-thio azetidinone intermediates
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This invention relates to 2-substituted and 2,6-disubstituted penem compounds of the formula STR1 wherein Y is hydrogen, halo or certain organic substituents and X represents certain organic substituents. Also included in the invention are pharmaceutically acceptable salts of the above compounds and derivatives of the above compounds in which the carboxyl group at the 3-position is protected as by an easily removable ester protecting group. The compounds of the present invention are potent antibacterial agents or are of use as intermediates in the preparation of such agents.
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