- Synthesis of new type diacetal trioxa-cage compounds via an intramolecular nucleophilic addition of the hydroxy group to the carbonyl oxide group
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The synthesis of diacetal trioxa-cage compounds with a new type of skeleton is reported. Ozonolysis of the diols 2a-f, 21, 24, and 33 in CH2C12 at -78 C followed by reduction with Me2S gave the diacetal trioxa-cages 3a-f, 22, 25, and 34 in 70-80% yields, respectively. A mechanism via an intramolecular nucleophilic addition of the hydroxy group of the diols to the carbonyl oxide group is proposed for the formation of the diacetal trioxa-cages. The effect of the number of carbon atoms at the bridge of the diols on the formation of the diacetal trioxa-cage skeleton was examined. Ozonolysis of the diols 13 and 15 under the same reaction conditions gave compounds 16 and 18, respectively. No detectable amount of the trioxa-cages 17 and 19 was obtained. For the synthesis of the diacetal trioxa-cages 28a-c and 31, which possess an alkene bond intact, Ozonolysis of the diols 27a-c and 30 was performed by controlling the amount of ozone.
- Wu Hsien-Jen,Chao, Ching-Shiun,Lin Chu-Chung
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- PHASE TRANSITIONS IN BICYCLIC COMPOUNDS.
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The thermal properties of bicyclic and cyclic compounds obtained by DSC show that substituents such as the anhydride, nitrile, and carbonyl groups retain the polymorphic phase properties of the parent ring systems while groups such as the imide, methylimide, and carboxylic acid exclude the appearance of a disordered solid phase. The phase properties of chloro and hydroxyl derivatives investigated and more varied and depend on the position of these groups on the ring. The variety of compounds studied shows that hysteresis is a common occurrence in all of these ring systems.
- Weinstein,Leffler,Currie
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- Soluble polyacetylene derivatives by chain-growth polymerization of dienes
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A new method for the fabrication of soluble polyacetylene derivatives was developed based on bromination-dehydrobromination of bicyclic diene polymers. High molecular weight polymer precursors were synthesized by radical 1,4-polymerization of the corresponding dienes, which contained a bicyclo[2.2.2]octane skeleton. Polymer precursors with narrow molecular distributions were prepared by nitroxide-mediated polymerization of the bicyclic diene monomers. Regioselective elimination from the brominated polymer afforded a polyacetylene derivative contaning bicyclic substituents, which was readily soluble in common organic solvents. The polymer electronic bandgap, obtained by optical and electrochemical measurements, was in the range 1.4-1.7 eV. Low bandgap values were attributed to the conformational inflexibility of the bicyclic substituent forcing coplanar orientation of the backbone double bonds. Solid-state conductivity of the produced polymer in the undoped form was measured to be 1.5 × 10-5 S/m. This new synthetic method allows for the chain-growth production of polyacetylene derivatives that possess favorable electronic properties and superior solubility characteristics to pristine polyacetylene.
- Luo, Kai,Kim, Sung Jin,Cartwright, Alexander N.,Rzayev, Javid
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- Heterocyclic compounds and, their compositions and their use as anti-influenza virus drugs (by machine translation)
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The invention provides a class of heterocyclic (I) compounds or pharmaceutically acceptable salts thereof as shown in formula (I) or a preparation method thereof as well A as a preparation method and application of the compounds in. preparation of drugs for treating or, preventing influenza viruses RNA. (by machine translation)
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Paragraph 0082-0085
(2020/01/03)
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- INHIBITORS OF INFLUENZA VIRUS REPLICATION AND USES THEREOF
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Provided herein is inhibitors of influenza virus replication and uses thereof. Specifically, provided herein a novel class of compounds as inhibitors of influenza virus replication, preparation methods thereof, pharmaceutical compositions containing these compounds, and uses of these compounds and pharmaceutical compositions thereof in the treatment of influenza.
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Paragraph 00253
(2018/07/31)
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- INHIBITORS OF INFLUENZA VIRUS REPLICATION AND USES THEREOF
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The invention provides a class of compounds as inhibitors of influenza virus replication, preparation methods thereof, pharmaceutical compositions containing these compounds, and uses of these compounds and pharmaceutical compositions thereof in the treatment of influenza.
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Paragraph 00244
(2018/07/05)
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- Synthesis of propellanes containing a bicyclo[2.2.2]octene unit: Via the Diels-Alder reaction and ring-closing metathesis as key steps
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The synthesis of propellanes containing bicyclo[2.2.2]octene via olefin metathesis approach is less explored. Herein, we describe a simple and convenient method to synthesize propellane derivatives containing a bicyclo[2.2.2]octene unit which are structurally similar to 11β-HSD1 inhibitors by sequential usage of the Diels-Alder reaction, C-allylation and ring-closing metathesis (RCM) as the key steps. Additionally, we expanded this approach to an endo-tricyclo[4.2.2.02,5]decene derivative which is a useful monomer for polymer synthesis and we have also synthesized basketene and anthracene-based propellanes using the same strategy.
- Kotha, Sambasivarao,Pulletikurti, Sunil
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p. 14906 - 14915
(2018/04/30)
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- 6,7-DIAZAINDAZOLE AND 6,7-DIAZAINDOLE DERIVATIVES AND USE IN TREATMENT, AMELIORATION OR PREVENTION OF INFLUENZA THEREOF
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Provided herein is a compound of formula (I), optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, prodrug, codrug, cocrystal, tautomer, racemate, enantiomer, or diastereomer or mixture thereof, which is useful in treating, ameliorating or preventing influenza.
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Page/Page column 53
(2017/09/02)
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- PYRIDINE AND PYRIMIDINE DERIVATIVES AND THEIR USE IN TREATMENT, AMELIORATION OR PREVENTION OF INFLUENZA
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Provided herein is a compound of formula (I), optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, prodrug, codrug, cocrystal, tautomer, racemate, enantiomer,or diastereomer or mixture thereof, which is useful in treating, ameliorating or preventing influenza.
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Page/Page column 73
(2017/09/02)
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- PYRIDINE AND PYRIMIDINE DERIVATIVES AND THEIR USE IN TREATMENT, AMELIORATION OR PREVENTION OF INFLUENZA
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Provided herein is a compound of formula (I), optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, prodrug, codrug, cocrystal, tautomer, racemate, enantiomer,or diastereomer or mixture thereof, which is useful in treating, ameliorating or preventing influenza.
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Page/Page column 81; 82
(2017/12/28)
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- BICYCLIC PYRIDINE AND PYRIMIDINE DERIVATIVES AND THEIR USE IN THE TREATMENT， AMELIORATION OR PREVENTION OF INFLUENZA
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The present invention relates to a compound having the formula (I), optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, prodrug, codrug, cocrystal, tautomer, racemate, enantiomer, or diastereomer or mixture thereof, which is useful in treating, ameloriating or preventing influenza.
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Page/Page column 75; 76
(2017/12/27)
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- 4, 7-DIAZAINDOLE AND 4, 7-DIAZAINDAZOLE DERIVATIVES AND THEIR USE IN THE TREATMENT, AMELIORATION OR PREVENTION OF INFLUENZA
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The present invention relates to a compound having the formula (I), optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, prodrug, codrug, cocrystal, tautomer, racemate, enantiomer, or diastereomer or mixture thereof, which is useful in treating, ameloriating or preventing influenza.
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Page/Page column 41
(2017/12/28)
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- PYRIMIDINE AND PYRIDINE DERIVATIVES AND USE IN TREATMENT, AMELIORATION OR PREVENTION OF INFLUENZA THEREOF
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Provided herein is a compound of formula (I), optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, prodrug, codrug, cocrystal, tautomer, racemate, enantiomer, or diastereomer or mixture thereof, which is useful in treating, ameliorating or preventing influenza.
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Page/Page column 144
(2017/12/28)
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- 5, 7-DIAZAINDOLE AND 5, 7-DIAZAINDAZOLE DERIVATIVES AND THEIR USE IN THE TREATMENT, AMELIORATION OR PREVENTION OF INFLUENZA
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The present invention relates to a specific compound having the formula (I), optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, prodrug, codrug, cocrystal, tautomer, racemate, enantiomer, or diastereomer or mixture thereof, which is useful in treating, ameloriating or preventing influenza.
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(2017/12/27)
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- PHARMACEUTICAL COMPOSITION FOR USE IN THE TREATMENT AND PREVENTION OF ORTHOPOXVIRUS INFECTIONS AND ASSOCIATED DISEASES
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Pharmaceutical compositions containing di, tri, and tetracyclic acylhydrazide derivatives of the formula below, for use in the treatment or prophylaxis of viral infections and diseases associated therewith, particularly those viral infections and associated diseases caused by the orthopoxvirus.
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Paragraph 0095; 0096
(2016/08/03)
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- Solvent-free Diels-Alder reaction in a closed batch system
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Solvent-free Diels-Alder reactions were carried out by heating a mixture of a volatile diene, such as 1,3-butadiene, isoprene, or 2,3-dimethyl-1,3- butadiene, and a dienophile, such as methyl vinyl ketone, methyl acrylate, or maleic anhydride, in a closed batch reactor. High yields of Diels-Alder products were obtained without using solvents and catalysts within a short reaction time in most of the reactions. In particular, several reactions of dienophiles with 1,3-butadiene, which is known as a diene with low reactivity because of its gaseous form, also proceeded with high yields of Diels-Alder products in the closed batch reactor under conditions pressured by the reactant vapor. Solvent-free reactions provided high yields compared to reactions in solvent since the reaction heat directly resulted in increasing the reaction temperature and pressure. Energy in the exothermic reaction was used effectively in the closed batch system under solvent-free conditions.
- Sun, Daolai,Sato, Fumiya,Yamada, Yasuhiro,Sato, Satoshi
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p. 276 - 282
(2013/05/08)
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- INHIBITORS OF INFLUENZA VIRUSES REPLICATION
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Compound according to Formula (I): or a pharmaceutically acceptable salt thereof, wherein the values of Structural Formula (I) are as described herein. A pharmaceutical composition comprises an effective amount of such a compound or pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, adjuvant or vehicle. Uses of inhibiting the replication of influenza viruses in a biological sample or patient, of reducing the amount of influenza viruses in a biological sample or patient.
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Paragraph 00265
(2014/01/08)
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- INHIBITORS OF INFLUENZA VIRUSES REPLICATION
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Methods of inhibiting the replication of influenza viruses in a biological sample or patient, of reducing the amount of influenza viruses in a biological sample or patient, and of treating influenza in a patient, comprises administering to said biological sample or patient an effective amount of a compound represented by Structural Formula (I): or a pharmaceutically acceptable salt thereof, wherein the values of Structural Formula (I) are as described herein. A compound is represented by Structural Formula (I) or a pharmaceutically acceptable salt thereof, wherein the values of Structural Formula (I) are as described herein. A pharmaceutical composition comprises an effective amount of such a compound or pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, adjuvant or vehicle.
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Page/Page column 80
(2012/06/30)
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- INHIBITORS OF INFLUENZA VIRUSES REPLICATION
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Methods of inhibiting the replication of influenza viruses in a biological sample or patient, of reducing the amount of influenza viruses in a biological sample or patient, and of treating influenza in a patient, comprises administering to said biological sample or patient an effective amount of a compound represented by Structural Formula (I): or a pharmaceutically acceptable salt thereof, wherein the values of Structural Formula (I) are as described herein. A compound is represented by Structural Formula (I) or a pharmaceutically acceptable salt thereof, wherein the values of Structural Formula (I) are as described herein. A pharmaceutical composition comprises an effective amount of such a compound or pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, adjuvant or vehicle.
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(2012/06/30)
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- INHIBITORS OF INFLUENZA VIRUSES REPLICATION
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Methods of inhibiting the replication of influenza viruses in a biological sample or patient, of reducing the amount of influenza viruses in a biological sample or patient, and of treating influenza in a patient, comprises administering to said biological sample or patient an effective amount of a compound represented by Structural Formula (I): or a pharmaceutically acceptable salt thereof, wherein the values of Structural Formula (I) are as described herein. A compound is represented by Structural Formula (I) or a pharmaceutically acceptable salt thereof, wherein the values of Structural Formula (I) are as described herein. A pharmaceutical composition comprises an effective amount of such a compound or pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, adjuvant or vehicle.
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Page/Page column 86
(2012/06/30)
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- Synthesis and transformations of di-endo-3-aminobicyclo-[2.2.2]oct-5-ene-2- carboxylic acid derivatives
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all-endo-3-amino-5-hydroxybicyclo[2.2.2]octane-2-carboxylic acid (13) and allendo-5-amino-6-(hydroxymethyl)bicyclo[2.2.2]octan-2-ol (10) were prepared via dihydro-1,3-oxazine or γ-lactone intermediates by the stereoselective functionalization of an Nprotected derivative of endo-3-aminobicyclo[2.2.2]oct- 5-ene-2-carboxylic acid (2). Ring closure of β-amino ester 4 resulted in tricyclic pyrimidinones 15 and 16. The structures, stereochemistry and relative configurations of the synthesized compounds were determined by IR and NMR.
- Palko, Marta,Sohar, Pal,Fueloep, Ferenc
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scheme or table
p. 7691 - 7705
(2011/11/04)
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- A Tin-tungsten mixed oxide as an efficient heterogeneous catalyst for C-C Bond Bond-Forming reactions
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The tin-tungsten mixed oxide prepared by the calcination of the tin-tungsten hydroxide precursor with a Sn/W molar ratio of 2 at 800 °C (SnW2-800) acts as an effective and reusable solid catalyst for C-C bond-forming reactions, such as the cyclization of citronellal, the Diels-Alder reaction, and the cyanosilylation of carbonyl compounds with trimethylsilyl cyanide (TMSCN). Various kinds of structurally diverse aliphatic, aromatic, and unsaturated, heteroatom-containing substrates could be converted into the desired products in high to excellent yields. The observed catalyses for these reactions were truly heterogeneous and the recovered catalyst could be reused several times without an appreciable loss of its high catalytic performance. The Bronsted acid sites generated on the aggregated polytungstate species on SnW2-800 likely play an important role in the C-C bond-forming reactions.
- Ogasawara, Yoshiyuki,Uchida, Sayaka,Yamaguchi, Kazuya,Mizuno, Noritaka
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experimental part
p. 4343 - 4349
(2009/11/30)
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- Catalyst economy. Part 2: Sequential metathesis - Kharasch sequences using the Grubbs metathesis catalysts
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Sequential ring-closing metathesis (RCM)-Kharasch cyclizations are promoted by the Grubbs metathesis catalysts and provide rapid access to bicyclic lactones and lactams.
- Edlin, Chris D.,Faulkner, James,Quayle, Peter
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p. 1145 - 1151
(2007/10/03)
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- Structural investigations into the retro-Diels-alder reaction. Experimental and theoretical studies
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The manifestations of the retro-Diels Alder reaction in the ground-state structures of a range of cyclopentadiene and cyclohexadiene cycloadducts 9-15 have been investigated by a combination of techniques. These include low-temperature X-ray crystallography, density functional calculations (B3LYP/6-31G(d,p)) on both the ground states and transition states, and the measurement of 13C-13C coupling constants. We have found that the carbon - carbon bonds (labeled bonds a and b), which break in the rDA, are longer in the cycloadducts 9-15 than in their corresponding saturated analogues 9s-15s, which cannot undergo the rDA reaction. The degree of carbon - carbon bond lengthening appears to be related to the reactivity of the cycloadduct, thus the more reactive benzoquinone cycloadducts 5b and 13 have longer carbon - carbon bonds. Those cycloadducts 14 and 15 which are predicted to undergo asynchronous reactions show differing degrees of carbon - carbon bond lengthening, reflecting the differing degrees of bond breaking at the calculated transition states for the rDA.
- Birney, David,Lim, Tang Kuan,Koh, Joanne H. P.,Pool, Brett R.,White, Jonathan M.
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p. 5091 - 5099
(2007/10/03)
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- Ionic liquids as powerful media in scandium triflate catalysed Diels-Alder reactions: Significant rate acceleration, selectivity improvement and easy recycling of catalyst
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Ionic liquids act as powerful media (or additives) in scandium triflate catalysed Diels-Alder reactions not only for facilitating of catalyst recovery but also for accelerating reaction rate and improving selectivity.
- Song,Shim,Roh,Lee,Choi
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p. 1122 - 1123
(2007/10/03)
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- Scandium perfluoroalkanesulfonate-catalyzed Diels-Alder reactions in an organic solvent
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Scandium perfluoroalkanesulfonate-catalyzed Diels-Alder reactions proceeded smoothly in dry dichloromethane in the presence of molecular sieves (MS) 5 ?. It was found that water interfered with the reactions, contrary to most rare earth-catalyzed reactions that proceed smoothly in aqueous media. Among scandium perfluoroalkanesulfonates tested, scandium triflate (Sc(OTf)3), scandium pentafluoroethanesulfonate (Sc(OSO2C2F5)3), and scandium nonafluorobutanesulfonate (Sc(OSO2C4F9)3) gave the highest yields and selectivities.
- Kobayashi, Shu,Tsuchiya, Takehiro,Komoto, Ichiro,Matsuo, Jun-Ichi
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p. 392 - 394
(2007/10/03)
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- Aqueous catalysis: Methylrhenium trioxide (MTO) as a homogeneous catalyst for the Diels-Alder reaction
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The title compound proves to be an effective and efficient catalyst for the Diels-Alder reaction when the dienophile is an α,β-unsaturated ketone or aldehyde. It is especially effective in water. Equal amounts of any such dienophile and any of six representative dienes (isoprene, 2-methyl-1,3-pentadiene, 2,3-dimethyl-1,3-butadiene, cyclopentadiene, 1,2,3,4,5-pentamethylcyclopentadiene, and 1,3-cyclohexadiene) were used, along with 1% MTO. The reactions gave usually > 90% isolated yield of the cycloaddition product except for the larger dienophiles. Nearly exclusively, there was formed one product isomer, the same one that usually predominates. The reactions were often run in chloroform (mostly) and in other organic solvents. A select number were carried out in water, where the reactions gave a greater product yield in a considerably shorter time. Water, itself, is known to enhance the rates of Diels-Alder reactions, but MTO exerts an additional accelerating effect. Kinetics studies were carried out to show that the rate is proportional to the catalyst concentration. The products do not inhibit the reaction. The desirability of MTO as a Diels-Alder catalyst stems from a combination of favorable properties: the inertness to air/oxygen, the tolerance for many substrates, the use of an aqueous medium, and the absence of product inhibition. The initial step appears to be the (weak) coordination of the carbonyl oxygen to the electropositive rhenium center. Steric crowding around rhenium inhibits reactions of the larger dienophiles.
- Zhu, Zuolin,Espenson, James H.
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p. 3507 - 3512
(2007/10/03)
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- A Remarkably Efficient Photochemical Methodology for Endo to Exo Isomerization of Diels-Alder Cycloadducts
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Irradiation of a solution of ethanol containing Diels-Alder cycloadducts and 10-20 percent (by volume) triethylamine at 300 nm furnishes quantitative yield (>90percent) of corresponding exo isomers.A probable mechanism based on photo-induced electron transfer (PET) has been described.
- Pandey, Bipin,Athawale, Asawari A.,Reddy, Ravinder S.,Dalvi, Pramod V.,Kumar, Pradeep
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p. 1173 - 1176
(2007/10/02)
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- Synthesis of exo-Bicyclooct-5-ene-dicarboxylic Anhydrides by Thermal Isomerization of trans-Diacids
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Bicyclooct-5-ene-trans-1,2-dicarboxylic acid and substituted analogues afford mixtures of the corresponding exo- and endo-anhydrides upon heating at 250-300 deg C.This isomerization provides a practical pathway to substituted and deuterium-labeled exo-anhydrides which are otherwise difficult to obtain.A mechanistic study shows that retro-diene fragmentation is not involved in the isomerization.
- Weisz, Adrian,Mandelbaum, Asher
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p. 5812 - 5815
(2007/10/02)
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- Additions of Group 6A and 7A Electrophilic Reagents to Dimethyl endo,endo-Bicyclooct-5-ene-2,3-dicarboxylate: Competitive Formation of γ- and δ-Lactones
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The reaction of dimethyl endo,endo-bicyclooct-5-ene-2,3-dicarboxylate with chlorine, bromine, iodine, benzeneselenenyl chloride, and benzenesulphenyl chloride has been studied.Under conditions of kinetic control both γ- and δ-lactones are formed, the δ lactone being predominant except in the case of bromine.The thermodynamic product distributions favored the δ-lactone exclusively.A general mechanistic scheme is proposed.
- Garratt, Dennis G.,Ryan, M. Dominic,Beaulieu, Pierre L.
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p. 839 - 845
(2007/10/02)
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- Electrophilic additions to strained alkenes. II. The reaction of benzeneselenenyl chloride with tricyclo2,5>deca-3,7-diene derivatives
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The reactions of benzeneselenenyl chloride with three derivatives of tricyclo2,5>deca-3,7-diene have been investigated in four solvent systems: methylene chloride, acetic acid, acetic acid/LiClO4, and methanol.Under conditions of kinetic control only products of exo-anti attack upon the cyclobutene moiety are isolable when the solvent system is methylene chloride or acetic aicd.This observation also holds in acetic acid/LiClO4 except in the case of dimethyl tricyclo2,5>deca-3,7,9-triene-7,8-dicarboxylate where the major product is that of cross-bonding with solvent incorporation.In methanol products of solvent incorporation, transannular cross-bonding and lactonization (where possible) are observed.A general mechanistic scheme is proposed to account for these observations in accord with earlier results for the analogous arenesulphenylations.
- Garratt, Dennis G.,Ryan, Dominic M.,Kabo, Ann
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p. 2329 - 2339
(2007/10/02)
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