- 3-(5-METHOXY-1-OXOISOINDOLIN-2-YL)PIPERIDINE-2,6-DIONE DERIVATIVES AND USES THEREOF
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The present disclosure relates to compounds of formula (I') and pharmaceutical compositions and their use in reducing Widely Interspaced Zinc Finger Motifs (WIZ) expression levels, or inducing fetal hemoglobin (HbF) expression, and in the treatment of inherited blood disorders (e.g., hemoglobinopathies, e.g., beta-hemoglobinopathies), such as sickle cell disease and beta-thalassemia.
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Page/Page column 328-329
(2021/06/26)
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- Robust cobalt oxide catalysts for controllable hydrogenation of carboxylic acids to alcohols
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The selective catalytic hydrogenation of carboxylic acids is an important process for alcohol production, while efficient heterogeneous catalyst systems are still being explored. Here, we report the selective hydrogenation of carboxylic acids using earth-abundant cobalt oxides through a reaction-controlled catalysis process. The further reaction of the alcohols is completely hindered by the presence of carboxylic acids in the reaction system. The partial reduction of cobalt oxides by hydrogen at designated temperatures can dramatically enhance the catalytic activity of pristine samples. A wide range of carboxylic acids with a variety of functional groups can be converted to the corresponding alcohols at a yield level applicable to large-scale production. Cobalt monoxide was established as the preferred active phase for the selective hydrogenation of carboxylic acids.
- Song, Song,Wang, Dong,Di, Lu,Wang, Chuanming,Dai, Weili,Wu, Guangjun,Guan, Naijia,Li, Landong
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p. 250 - 257
(2018/02/20)
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- Selective Hydrogenation of Carboxylic Acids to Alcohols or Alkanes Employing a Heterogeneous Catalyst
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The chemoselective hydrogenation of carboxylic acids to either alcohols or alkanes is reported, employing a heterogeneous bimetallic catalyst consisting of rhenium and palladium supported on graphite. α-Chiral carboxylic acids were hydrogenated without loss of optical purity. The catalyst displays a reverse order of reactivity upon hydrogenation of different carboxylic functions with esters being less reactive than amides and carboxylic acids. This allows for chemoselective hydrogenation of an acid in the presence of an ester or an amide function.
- Ullrich, Johannes,Breit, Bernhard
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p. 785 - 789
(2018/02/14)
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- Preparation method of tetrahydro-3-furanmethanol
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The invention relates to the field of preparation of insecticides, in particular to a preparation method of tetrahydro-3-furanmethanol. The method comprises the steps as follows: 13.6 g of sodium ethoxide and 0.5 g of sodium iodide are dissolved in 120 mL of absolute ethyl alcohol, 32 g of diethyl malonate is dropwise added in an ice-water bath, the temperature is controlled at 20 DEG C or below,stirring is performed continuously for 1 h after addition, then 30.3 g of ethyl bromoacetate is slowly added, the temperature is increased to 50-60 DEG C after addition, stirring is performed for about 8 h, ethyl bromoacetate is detected to be used up through gas chromatography, a heating reaction is stopped, the system is cooled to the room temperature, 10 mL of a saturated ammonium chloride solution is added with stirring, the system is adjusted to be neutral or slightly acid, solvent ethyl alcohol is evaporated, residues are dissolved in 100 mL of water and 100 mL of ethyl acetate for extraction, solution separation is performed, an organic phase is separated, the solvent ethyl acetate is removed from the organic phase, reduced pressure distillation is performed through an oil pump, andthe first fraction point, namely, a triethyl 1,1,2-ethanetricarboxylate product, is collected. The process is simple, safety in actual production is guaranteed, and the product with higher yield is obtained.
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Paragraph 0008
(2018/04/02)
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- Insecticide dinotefuran intermediate 3 - hydroxy methyl tetrahydrofuran synthetic method
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The invention discloses a synthetic method of pesticide dinotefuran intermediate 3-hydroxymethyl tetrahydrofuran, and the synthetic method is as follows: reacting compound succinic acid dialkyl ester with formic acid alkyl ester in the presence of a strong alkali to obtain a compound III, then obtaining a compound II by a reduction reaction, finally, in the presence of an acid catalyst, obtaining a compound shown as formula I by a dehydration cyclization reaction, and R or R ' respectively independently represents C1-5 alkyl. The synthetic method is low in raw material cost, simple in reaction operation, less in pollution, high in yield of each step, 99% in the yield of the reducing step, and suitable for industrial production.
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- Production technology for 3-hydroxymethyltetrahydrofuran
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The invention discloses a production technology for 3-hydroxymethyltetrahydrofuran, and belongs to the field of pesticide intermediate synthetic processes. The production technology is capable of using 2-butene-1,4-diol as a starting raw material, and synthesizing the 3-hydroxymethyltetrahydrofuran through a three-step reaction of dehydration cyclization, hydroformylation and reduction. The production technology is moderate in reaction conditions, low in cost, less in three wastes, and suitable for the industrial production.
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Paragraph 0033; 0034; 0037; 0043
(2018/10/19)
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- ISOINDOLINONE INHIBITORS OF THE MDM2-P53 INTERACTION HAVING ANTICANCER ACTIVITY
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The invention provides a compound of formula (I): (I) or tautomer or a solvate or a pharmaceutically acceptable salt thereof, wherein the various substituents are as defined in the claims. Also provided are pharmaceutical compositions containing the compounds of formula (I), processes for making the compounds and the medical uses of the compounds.
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Page/Page column 211; 212
(2017/05/07)
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- Novel process for synthesizing 3-tetrahydrofurfuryl carbinol through Prins reaction
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The invention discloses a novel process for synthesizing 3-tetrahydrofurfuryl carbinol through Prins reaction, and solves the problems that in the preparation process in the prior art, the raw materials have high price; the production cost is raised; in the production process, a great amount of heat can be released; inflammable and explosive gas of hydrogen gas can be easily generated; risk can be brought to the production. The process comprises the following steps that 1, in an organic solvent, 2,5-dihydrofuran takes reaction with paraformaldehyde and chlorine hydride under the effect of a catalyst A to obtain chloromethyl-2,5-dihydrofuran; 2, the chloromethyl-2,5-dihydrofuran is hydrolyzed in a sodium hydroxide solution to obtain hydroxymethyl-2,5-dihydrofuran; distillation is performed to obtain a coarse product; (3) the coarse product of the hydroxymethyl-2,5-dihydrofuran is reduced by the hydrogen gas under the effect of the catalyst B to obtain 3-tetrahydrofurfuryl carbinol; filtering is performed; filter liquid is rectified to obtain a pure product. The novel process has the advantages that the raw material cost is low; the three-waste discharge is little; the process is simple, and the like.
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Paragraph 0034; 0038; 0042; 0046; 0050; 0054; 0058; 0062
(2017/10/13)
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- New process for synthesizing tetrahydrofuran-3-methanol by adopting one-pot method
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The invention discloses a new process for synthesizing tetrahydrofuran-3-methanol by adopting a one-pot method. The problems that reaction pressure in the prior art is higher so that equipment cost is increased and the recycling of ammonia gas and hydrogen is difficult are solved. The process comprises the following steps: carrying out reaction between 2,5-dihydrofuran and methanol aqueous solution at a reaction temperature of 100 to 130 DEG C in a solvent A under an effect of a catalyst A to generate 3-hydroxymethyl-2,5-dihydrofuran, and evaporating the solvent A to dryness; adding a solvent B and the organic solvent A into the generated 3-hydroxymethyl-2,5-dihydrofuran, reducing the 3-hydroxymethyl-2,5-dihydrofuran into 3- tetrahydrofuran methanol by hydrogen under an effect of a catalyst B; then filtering the 3- tetrahydrofuran methanol; evaporating the solvent B to dryness; carrying out rectification to obtain a pure product. The process has the advantages of low cost of raw materials, stable process, applicability to industrialization and the like.
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Paragraph 0025-0048
(2017/10/26)
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- A synthetic method of the dinotefuran (by machine translation)
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The invention discloses a method for synthesis of dinotefuran, to γ - butyrolactone as raw materials, by Aldol condensation, also the original two-step by the reaction of 3 - hydroxy methyl tetrahydrofuran, then by the Gabriel synthesis of 3 - tetrahydrofuran methyl amine, dimethyl carbonate (DMC) as methylation reagent with the urea synthesis O - methyl isourea, re-nitration synthetic O - methyl - N - nitro-isourea, then with the methylamine reaction synthesis of 1, 3 - dimethyl - 2 - nitro-isourea, final 3 - tetrahydrofuran methylamine with 1, 3 - dimethyl - 2 - nitro-isourea through SN2 Bimolecular nucleophilic substitution reaction, one-step synthesis of dinotefuran. The present invention uses non of dimethyl carbonate as the methylating reagent, the methylation reaction yield ≥ 95%, O - methyl isourea content ≥ 96%, the by-product is carbon dioxide and methanol, process and environmental protection, the overall yield of the dinotefuran ≥ 50%. Synthetic method of this invention to reduce the production cost at the same time, with three wastes, after treatment is simple, the advantages of the environment friendly, and is suitable for industrial production, bring about significant economic benefits. (by machine translation)
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Paragraph 0049; 0068; 0087
(2017/08/27)
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- Synthesis method of tetrahydro-3-furfuryl alcohol
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The invention discloses a synthesis method of tetrahydro-3-furfuryl alcohol, and solves the problems of complicated route, operation difficulty, many three wastes and high cost of 3-hydroxymethyl-tetrahydrofuran synthesis in the prior art. The method comprises the following steps of (1) in an organic solvent, performing reaction on malonic acid and chlorohydrin under the existence of a catalyst A to produce ethyl oxalyl chloride; (2) performing closed loop reaction on the ethyl oxalyl chloride under the alkali effect to produce 3-formic acid-gamma-butyrolactone; (3) performing reduction and purification on the 3-formic acid-gamma-butyrolactone under the conditions of a reducing agent and a catalyst B to obtain 3-hydroxymethyl-tetrahydrofuran. The synthesis method has the advantages that the post treatment is simple; green and environment-friendly effects are achieved; the cost is low; the operation is simple; the yield is high, and the like.
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Paragraph 0030
(2017/09/18)
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- 3-PHOSPHOGLYCERATE DEHYDROGENASE INHIBITORS AND USES THEREOF
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The present invention provides compounds, compositions thereof, and methods of using the same.
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Paragraph 00595-00597
(2017/10/06)
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- TRIAZOLOPYRAZINONES AS PDE1 INHIBITORS
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The present invention provides triazolopyrazinones as PDE1 inhibitors and their use as a medicament, in particular for the treatment of neurodegenerative disorders and psychiatric disorders.
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Page/Page column 43
(2016/05/02)
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- Method for synthesizing 3-tetrahydrofurfuryl alcohol
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The invention relates to a method for synthesizing 3-tetrahydrofurfuryl alcohol. According to the technical scheme, 2-bromoethanol and diethyl malonate serve as starting materials, under the alkaline condition, 2-hydroxyethyl-diethyl malonate is generated through a reaction, hydrolysis is conducted on the 2-hydroxyethyl-diethyl malonate to generate 2-hydroxyethyl-malonate, catalyzing and high-pressure hydrotreatment are conducted on the 2-hydroxyethyl-malonate to generate 2-hydroxymethyl-1,4-butanediol, and dehydration cyclization is conducted on the 2-hydroxyethyl-1,4-butanediol to generate the 3-tetrahydrofurfuryl alcohol. According to the method for synthesizing the 3-tetrahydrofurfuryl alcohol, the yield can reach over 85 percent, the purity can reach above 95 percent, the reaction condition is mild, the cost is low, operation is easy, and the method has the advantage of being suitable for industrial production.
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Paragraph 0007; 0022
(2017/01/17)
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- A 3-hydroxy methyl tetrahydrofuran method for the synthesis of
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The invention discloses a synthetic method for 3-hydroxylmethal tetrahydrofuran. The synthetic method comprises the following steps: with 2-chloroethanol and diethyl malonate as raw materials, reacting under the action of alkaline in the presence of an organic solvent or in absence of a solvent to obtain an intermediate 2-ethoxy-diethyl succinate; then, reducing the intermediate 2-ethoxy-diethyl succinate by virtue of metal borohydride to obtain 2-hydroxymethyl-1,4-butanediol; and finally, producing 3-hydroxylmethal tetrahydrofuran under the action of a dehydrating agent. According to the synthetic method, the usage amount of the reducing agent metal borohydride is remarkably lowered, and yield of a byproduct sodium metaborate is reduced at the same time. The invention provides the synthetic method for the drug intermediate 3-hydroxylmethal tetrahydrofuran.
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Paragraph 0023
(2017/03/08)
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- Ruthenium-catalyzed hydroformylation/reduction of olefins to alcohols: Extending the scope to internal alkenes
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In the presence of 2-phosphino-substituted imidazole ligands and Ru 3(CO)12 or Ru(methylallyl)2(COD) direct hydroformylation and hydrogenation of alkenes to alcohols takes place. In addition to terminal alkenes, also more challenging internal olefins are converted preferentially to industrially important linear alcohols in high yield (up to 88%) and regioselectivity (n:iso up to 99:1).
- Wu, Lipeng,Fleischer, Ivana,Jackstell, Ralf,Profir, Irina,Franke, Robert,Beller, Matthias
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supporting information
p. 14306 - 14312
(2013/10/21)
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- Heterocyclic antiviral compounds
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This invention relates to piperidine derivatives of formula I wherein R1, R2 and R3 are as defined herein useful in the treatment of a variety of disorders, including those in which the modulation of CCR5 receptors is impl
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Page/Page column 17
(2009/12/04)
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- PURINE DERIVATIVES AS IMMUNOMODULATORS
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The present invention includes novel compounds useful in the treatment of various disorders in particular infectious diseases, cancer, and allergic diseases and other inflammatory conditions for example allergic rhinitis and asthma, and as vaccine adjuvants
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- 4-AMINO-BENZAMIDE DERIVATIVES AS 5-HT4 RECEPTOR AGONISTS FOR THE TREATMENT OF GASTROINTESTINAL, NEUROLOGICAL AND CARDIOVASCULAR DISORDERS
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The present invention relates to novel benzamide derivatives of formula (I) having pharmacological activity, to processes for their preparation, to compositions containing them and to their use in the treatment of diseases treatable by 5-HT4 agonism.
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Page/Page column 37
(2010/11/28)
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- Novel and efficient catalytic route for the syntheses of tetrahydrofurans useful in the preparation of neonicotinoid insecticides
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Neonicotinoids are good alternatives to the widely used organophosphate insecticides (OP) and have gained enormous importance because of their low toxicity in vertebrates. An environmentally benign route for the synthesis of 3-(hydroxy-methyl)tetrahydrofuran useful in the preparation of a neonicotinoid insecticide viz. MTI-446 is described. Principles of green chemistry such as hydroformylation, single-pot transketalization, and intramolecular cyclocondensation through catalytic reactions were adopted. The process reported here is superior to the existing methods with respect to lower salt formation and higher atom economy, and it was extended to the preparation of a novel intermediate, 3,3-bis(hydroxymethyl)tetrahydrofuran, conceived to be useful in the preparation of new insecticides.
- Potluri, Srinagesh Kumar,Ramulu, A. Raghu,Pardhasaradhi
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p. 971 - 978
(2007/10/03)
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- Process for preparing alpha- and beta-methyl-gamma-butyrolactone and 3-methyltetrahydrofuran
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The present invention pertains to a novel process for preparing alpha- and beta-methyl-gamma-butyrolactones (MeGBL) and/or 3-Methyltetrahydrofuran (MeTHF) from 3-(hydroxymethyl)tetrahydrofuran (HOMeTHF), 3-formyltetrahydrofuran (FTHF) or a mixture thereof
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- Process for the preparation of 3-methyltetrahydrofuran
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Disclosed is a process for the preparation of 3-methyltetrahydrofuran (MeTHF) from 3-(hydroxymethyl)tetrahydrofuran (HOMeTHF) or 3-formyltetrahydrofuran (FTHF) by contacting HOMeTHF or 3-formyltetrahydrofuran with a secondary alcohol in the presence of a
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- Process for the preparation of 3-methyltetrahydrofuran
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Disclosed is a process for the preparation of 3-methyltetrahydrofuran (MeTHF) from 3-(hydroxymethyl)tetrahydrofuran (HOMeTHF) by contacting HOMeTHF with hydrogen in the presence of an acidic, supported catalyst comprising a Group VIII metal.
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Page/Page column 6-7
(2008/06/13)
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- Process for the preparation of 3-hydroxymethyl tetrahydrofuran
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The present invention relates to a catalytic process for the preparation of 3-hydroxymethyl tetrahydrofuran of formula IV with hydroformylation as one of the key steps. The process comprises reacting 9-hydroxymethyl-7,12-dioxaspiro[5,6]dodecane of the formula III with an alcohol in the presence of an acid catalyst and recovering the 3-hydroxymethyl tetrahydrofuran.
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- CHIRAL SYNTHESIS VIA ORGANOBORANES. 19. THE SUCCESSFUL ONE-CARBON HOMOLOGATION OF HETEROCYCLIC BORONATE ESTERS WITH HIGH OPTICAL PURITY
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An exploratory study was undertaken to establish the applicability of the one-carbon homologation to heterocyclic boronic esters.This procedure involves the use of (cloromethyl)lithium, LiCH2Cl, generated in situ by the reaction of bromochloromethane and n-BuLi in THF at -78 deg C in the presence of an enantiomerically pure heterocyclic boronic ester.These heterocyclic boronic esters were prepared via asymmetric hydroboration of representative heterocyclic olefins bearing either an endocyclic or exocyclic double bond with either Ipc2BH or IpcBH2 in THF.
- Brown, Herbert C.,Gupta, Ashok K.,Rangaishenvi, Milind V.,Vara Prasad, J. V. N.
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p. 283 - 294
(2007/10/02)
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- The Reaction of Bis(dimethylglyoximato)(pyridine)cobalt(I), Cobaloxime(I), with 2-(Allyloxy)ethyl Halides and the Photolysis of the Resulting Organo-cobaloximes
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The reactions of 2-(allyloxy)ethyl halides with cobaloxime(I) gave (tetrahydro-3-furanyl)methylcobaloximes via an electron transfer from cobaloxime(I) to the halides to give radical anions.The rupture of a halide ion to give an organic radical and the ring closure to give a (tetrahydro-3-furanyl)methyl radical are followed by the radical coupling between the organic radical and the cobaloxime(II).The structures of the organocobaloximes were determined by the analyses of the photolysis products under aerobic or anaerobic conditions.
- Okabe, Masami,Tada, Masaru
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p. 1498 - 1503
(2007/10/02)
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- STRUCTURE AND FORMATION OF C4H7O(1+) IONS RESULTING FROM ELECTRON IMPACT INDUCED DECOMPOSITION OF CYCLIC PRECURSORS
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Possible structures and modes of formation of C4H7O(1+) ions formed by electron impact induced decomposition of tetrahydrofuran and tetrahydropyran derivates are discussed in view of labelling results and MIKE, CA, and T data.Limitations of these techniques are pointed out.
- Stolze, Rainer,Budzikiewicz, Herbert
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p. 781 - 787
(2007/10/02)
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