- Synthesis method for 4-Aaminotetrahydropyran synthesis
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The invention discloses a synthesis method for 4-aminotetrahydropyran. The method comprises the steps that tetrahydro-2H-pyran-4-carboxylic acid is dissolved in water, the temperature is increased to60-70 DEC G by heating, ammonia water is added dropwisely under the condition of stirring, stirring reaction is conducted for 1-2 hours after dropwise adding is completed, the temperature is decreasedto the room temperature after the reaction is completed to obtain tetrahydro-2H-pyran-4-carboxamide mixed solution; cooling is conducted on the prepared tetrahydro-2H-pyran-4-carboxamide mixed solution to reduce the temperature to 5-10 DEC G, NaOH solution is added, NaBrO solution is added dropwisely in the mixed solution after the mixed solution is stirred uniformly, after the dropwise adding iscompleted, the reaction is performed constantly for 1-2 hours under the temperature of 5-10 DEC G, the temperature is decreased to the room temperature after the temperature is increased to 50-60 DECG to perform the reaction constantly for 1 hour, extraction is conducted by using dichloromethane, an organic phase is combined, and after the dichloromethane is removed by distillation through reducing pressure, recrystallization is conducted to obtain the 4-aminotetrahydropyran. The method has the advantages of being simple to operate, mild in condition, less in byproducts, high in product purity, and higher in product yield.
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Paragraph 0021; 0029; 0034; 0034; 0037; 0038; 0039-0041
(2018/06/23)
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- Preparation method of important intermediate 4-aminotetrahydropyran
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The invention discloses a preparation method of an important intermediate 4-aminotetrahydropyran. The method comprises the following steps that tetrahydro-4-pyranol is dissolved in polyethylene glycol-200, a prepared Cu-Mo/TS-1 composite is added, a mixture is heated to 60-80 DEG C, under a stirring condition, ammonium hydroxide is added into the mixture dropwise, after dropping is completed, heat-preservation stirring reaction is carried out for 5-6 h, and filtering, extraction and recrystallization are conducted to prepare the 4-aminotetrahydropyran. The preparation method is simple to operate, conditions are mild, by-products are few, the product purity is high, and the product yield is high.
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Paragraph 0019-0025; 0026-0032; 0033-0039; 0040-0053; 0055
(2018/12/14)
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- Heterogeneous Catalytic Reductive Amination of Carbonyl Compounds with Ni-Al Alloy in Water as Solvent and Hydrogen Source
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The heterogeneous catalytic reductive amination of carbonyl compounds has been achieved by reactions of ammonium hydroxide and various amines with ketones and aldehydes. The process is based on the application of Raney type Ni-Al alloy in an aqueous medium. The reaction of the carbonyl compounds with the amine provided the corresponding Schiff bases that immediately underwent a reduction to provide primary and secondary amines as products. The controlled reaction of the Al content of the alloy with the solvent water generates hydrogen, and the in situ formed Raney Ni serves as a hydrogenation catalyst. The method is a simple and efficient way of preparing a broad variety of primary and secondary amines.
- Sch?fer, Christian,Ni?anci, Bilal,Bere, Matthew P.,Da?tan, Arif,T?r?k, Béla
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p. 3127 - 3133
(2016/09/09)
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- 4-Aminotetrahydropyrans process for one-pot synthesis
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The invention discloses a one-kettle method synthesis process of 4-aminotetrahydropyran. The synthesis process comprises the following steps: synthesizing 4-carboxamide tetrahydropyran by taking 4-cyano-tetrahydropyran and a sodium hydroxide solution (or a potassium hydroxide solution) as raw materials, further slowly adding a sodium hypochlorite solution (or a sodium hypobromite solution) into 4-carboxamide tetrahydropyran, then heating till reflux, and performing decarboxylation to generate a product, namely 4-aminotetrahydropyran. All the reaction raw materials are placed into one kettle for reaction, the appropriate reaction conditions are selected for synthesizing 4-aminotetrahydropyran, and the synthesis process has the advantages of high selectivity, few impurities, no need of separating intermediate products, high yield and high practical value.
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Paragraph 0014; 0015
(2017/02/02)
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- IMIDAZO [1, 2 - B] PYRIDAZINE - BASED COMPOUNDS, COMPOSITIONS COMPRISING THEM, AND USES THEREOF
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Imidazo[1,2-b]pyridazine-based compounds of the formula (I): are disclosed, wherein R1, R2 and R3 are defined herein. Compositions comprising the compounds and methods of their use to treat, manage and/or prevent diseases and disorders mediated by mediated by adaptor associated kinase 1 activity are also disclosed.
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Page/Page column 29
(2013/09/26)
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- Synthesis of primary amines from secondary and tertiary amines: Ruthenium-catalyzed amination using ammonia
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Splitting of secondary and tertiary amines! The first selective catalytic synthesis of primary amines from secondary and tertiary amines with ammonia is reported. The products are obtained in yields up to 84 %. Copyright
- Baehn, Sebastian,Imm, Sebastian,Neubert, Lorenz,Zhang, Min,Neumann, Helfried,Beller, Matthias
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experimental part
p. 4705 - 4708
(2011/05/12)
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- An efficient and general synthesis of primary amines by ruthenium-catalyzed amination of secondary alcohols with ammonia
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Atom efficiency and selectivity are the key features of the first homogeneously catalyzed amination of secondary alcohols with ammonia to give the corresponding primary amines (see scheme). This novel amination method relies on the commercially available catalyst [Ru3(CO)12]/ cataCXium PCy and does not require any additional source of hydrogen.
- Imm, Sebastian,Neubert, Lorenz,Neumann, Helfried,Beller, Matthias
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supporting information; experimental part
p. 8126 - 8129
(2011/02/22)
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- SOLUBLE EPOXIDE HYDROLASE INHIBITORS
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Disclosed are amide, thioamide, urea and thiourea compounds and compositions that inhibit soluble epoxide hydrolase (sEH), methods for preparing the compounds and compositions, and methods for treating patients with such compounds and compositions. The compounds, compositions, and methods are useful for treating a variety of sEH mediated diseases, including hypertensive, cardiovascular, inflammatory, and diabetic-related diseases.
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Page/Page column 23
(2009/04/24)
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- Discovery of 4-{4-[3-(pyridin-2-yl)-1H-pyrazol-4-yl]pyridin-2-yl}-N- (tetrahydro-2H-pyran-4-yl)benzamide (GW788388): A potent, selective, and orally active transforming growth factor-β type I receptor inhibitor
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Inhibitors of transforming growth factor β (TGF-β) type I receptor (ALK5) offer a novel approach for the treatment of fibrotic diseases such as renal, hepatic, and pulmonary fibrosis. The optimization of a novel phenylpyridine pyrazole series (1a) led to the identification of potent, selective, and orally active ALK5 inhibitors. The cellular potency and pharmacokinetics profiles of these derivatives were improved and several compounds presented antifibrotic activity when orally administered to rats in an acute liver model of dimethylnitrosamine- (DMN-) induced expression of collagen IA1 mRNA, a major gene contributing to excessive extra cellular matrix deposit. One of the most potent ALK5 inhibitors identified in this chemical series, compound 13d (GW788388), reduced the expression of collagen IA1 by 80% at a dose of 1 mg/kg twice a day (b.i.d.). This compound significantly reduced the expression of collagen IA1 mRNA when administered orally at 10 mg/kg once a day (u.i.d.) in a model of puromycin aminonucleoside-induced renal fibrosis.
- Gellibert, Fran?oise,De Gouville, Anne-Charlotte,Woolven, James,Mathews, Neil,Nguyen, Van-Loc,Bertho-Ruault, Cécile,Patikis, Angela,Grygielko, Eugene T.,Laping, Nicholas J.,Huet, Stéphane
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p. 2210 - 2221
(2007/10/03)
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- PROCESS FOR PRODUCTION OF 4-AMINOTETRAHYDROPYRANS AND SALTS THEREOF WITH ACIDS, INTERMEDIATES FOR THE PROCESS, AND PROCESS FOR PRODUCTION THEREOF
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The present invention relates to a process for preparing 4-aminotetrahydropyran compound and an acid salt thereof represented by the formula (2): wherein R represents a hydrogen atom or a hydrocarbon group, which comprises subjecting a 4-hydrazinotetrahydropyran compound or an acid salt thereof represented by the formula (1) : wherein R has the same meaning as defined above, to decomposition reaction in the presence of at least one compound selected from Raney nickel, noble metal catalyst and metal oxide, and a synthetic intermediate thereof and a process for preparing the same.
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Page/Page column 7
(2008/06/13)
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- PYRAZOLO[3,4-B]PYRIDINE COMPOUNDS, AND THEIR USE AS PHOSPHODIESTERASE INHIBITORS
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The invention relates to a compound of formula (I) or a salt thereof: wherein:R1 is C1-4alkyl, C1-3fluoroalkyl, -CH2CH2OH or -CH2CH2CO2C1-2alkyl;R2 is a hydrogen atom (H), methyl or C1fluoroalkyl;R3 is optionally substituted C3-8cycloalkyl or optionally substituted mono-unsaturated-C5-7cycloalkenyl or an optionally substituted heterocyclic group of sub-formula (aa), (bb) or (cc); in which n1 and n2 independently are 1 or 2; and in which Y is O, S, SO2, or NR10; or R3 is a bicyclic group (dd) or (ee): ; and wherein X is NR4R5 or OR5a. The compounds are phosphodiesterase (PDE) inhibitors, in particular PDE4 inhibitors. Also provided is the use of a compound of formula (I), or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for the treatment and/or prophylaxis of an inflammatory and/or allergic disease in a mammal such as a human, for example chronic obstructive pulmonary disease (COPD), asthma, or allergic rhinitis.
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- Heterocyclic amides, a process for their preparation, compositions comprising them and their use
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What is described are amides of the formula (I) and salts thereof, where the symbols and indices are as defined below: X is CH or N; Y is O or S; n is 0 or 1; R1 is (C1-C4)-haloalkyl; R2, R3 independently of one another are hydrogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl or halogen, R4 is hydrogen, (C1-C10)-alkyl, (C3-C10)-cycloalkyl, (C3-C10)-alkenyl or (C3-C10)-alkynyl, where in the alkyl, cycloalkyl, alkenyl or alkynyl groups mentioned up to three hydrogen atoms may be replaced by halogen, in the case of fluorine also up to the maximum number; R5 is an aliphatic heterocycle which contains at least one oxygen, sulfur, nitrogen and/or silicon ring atom, which is unsubstituted or substituted by one to six monovalent groups and which may be part of a spirocyclic, fused or bicyclic ring system. These compounds can be used for controlling pests.
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Page/Page column 13
(2010/02/05)
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- AMINO CYCLOBUTYLAMIDE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
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The present invention is directed to compounds of the formulas I and II : wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R15, R16, R17, R18, R19, R25, R26, Y, Z, l, m, n and the broken lines are as defined herein which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptor CCR-2.
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- Processes for producing tetrahydropyranyl-4-sulfonates and 4-aminotetrahydropyran compound
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The present invention is to provide a process for producing a tetrahydropyranyl-4-sulfonate which comprises allowing 3-buten-1-ol which is easily available to react with a formaldehyde compound and an organic sulfonic acid, and a process for producing a 4-aminotetrahydropyrane derivative, which is industrially useful, under mild conditions and by a simple and easy method to produce the 4-aminotetrahydropyrane derivative in high yield.
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- TETRAHYDROPYRANYL CYCLOPENTYL TETRAHYDROISOQUINOLINE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
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The present invention is directed to compounds of the formula I: I(wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, X, n and the dashed line are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptor CCR-2.
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Page/Page column 53
(2010/02/07)
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- Heteroalkylamino-substituted bicyclic nitrogen heterocycles
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The invention provides compounds represented by the formula: wherein R1, R2, R3, R4, and n are as defined in the Summary of the Invention; and individual isomers, racemic or non-racemic mixtures of isomers, and pharmaceutically acceptable salts thereof. The invention further relates to pharmaceutical compositions containing such compounds, methods for their use as therapeutic agents, and methods of preparation thereof.
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- One-pot, new stereoselective synthesis of endo-tropanamine
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A palladium-catalysed reduction of ketones to primary amines by reaction with ammonium formate in aqueous methanol is described. The proposed method provides a one-pot synthesis of 3-endo-tropanamine in high yields and stereoselectivity.
- Allegretti, Marcello,Berdini, Valerio,Cesta,Curti, Roberto,Nicolini, Luca,Topai, Alessandra
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p. 4257 - 4259
(2007/10/03)
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- Imidazopyridine derivatives
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This invention relates to imidazopyridine derivatives with the general formula II: STR1 These compounds are useful as dual histamine (H1) and platelet activating factor (PAF) receptor antagonists.
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- Pyrimido [5, 4-d] pyrimidines, pharmaceuticals containing these compounds, their use and processes for their preparation
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Pyrimido[5,4-d]pyrimidines of the general formula [Figure] which have an inhibitory effect on signal transduction mediated by tyrosine kinases, their use for the treatment of oncoses, and their preparation. Exemplary compounds are: (a) 4-(5-indolylamino)-6-morpholinopyrimido[5,4-d]pyrimidine; (b) 4-(5-indolylamino)-6-[trans-(4-hydroxycyclohexyl)amino]pyrimido[5,4-d]pyrimidine; (c) 4-[(3-chloro-4-fluorophenyl)amino]-6-[4-(morpholinocarbonylmethyl)-1-piperazinyl]pyrimido[5,4-d]pyrimidine; (d) 4-[(3-chloro-4-fluorophenyl)amino]-6-[(4-morpholinyl)amino]pyrimido[5,4-d]pyrimidine; (e) 4-[(3-chloro-4-fluorophenyl)amino]-6-(4-picolylamino)pyrimido[5,4-d]pyrimidine; (f) 4-[(3-chloro-4-fluorophenyl)amino]-6-[1-trifluoroacetyl-4-piperidinylamino]pyrimido[5,4-d]pyrimidine; (g) 4-[(3-chloro-4-fluorophenyl)amino]-6-(endo-tropinylamino)pyrimido[5,4-d]pyrimidine; and, (h) 4-[(3-chloro-4-fluorophenyl)amino]-6-(exo-tropinylamino)pyrimido[5,4-d]pyrimidine.
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- Pyrimido?5,4-D!pyrimidines, medicaments comprising these compounds, their use and processes for their preparation
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The present invention relates to pyrimido?5,4-d!pyrimidines of the general formula STR1 in which Ra to Rc are as defined herein, their tautomers, their stereoisomers and their salts, in particular their physiologically tolerated salts with inorganic or organic acids or bases which have valuable pharmacological properties, in particular an inhibiting action on signal transduction mediated by tyrosine kinases, their use for the treatment of diseases, in particular tumor diseases.
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- Pyrimido[5,4]-dipyrimidines, pharmaceuticals containing them, their use and processes for the preparation thereof
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Pyrimido[5,4-d]pyrimidines of the general formula [Figure] which have an inhibitory effect on signal transduction mediated by tyrosine kinases, their use for the treatment of disorders, in particular of oncoses, and their preparation. Exemplary compounds are: 4-[(3-Chloro-4-fluorophenyl)amino]-6-[1-methyl-4-piperidinylamino]pyrimido[5,4-d]pyrimidine, and 4-[(3-Chloro-4-fluorophenyl)amino]-6-[trans-4-dimethyl-aminocycohexylamino]pyrimido[5,4-d]pyrimidine.
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- 1-benzenesulfonyl-1,3-dihydro-2H-benzimidazol-2-one derivatives
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The present invention relates to 1-benzenesulfonyl-1,3-dihydro-2H-benzimidazol-2-one derivatives of the formula: STR1 to their preparation and to the pharmaceutical compositions in which they are present. These derivatives have an affinity for the vasopressin and oxytocin receptors.
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- High potency sweetening agents
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Substituted guanidines containing a tetrazole moiety are provided as high potency sweetening agents.
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