- ORGANOMETALLIC COMPLEXES, ORGANIC ELECTROLUMINESCENCE DEVICE USING THE SAME AND DISPLAY
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The present invention relates to an organic metal complex, an organic electroluminescence device using the same and a display device, and provided is an organic metal complex indicated as chemical formula 1 below. [Chemical Formula 1] Definition of the chemical formula 1 exists in the application.
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Paragraph 0122; 0123; 0132; 0133
(2020/03/17)
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- NOVEL TETRAHYDROPYRIDOPYRIMIDINES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION
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The present invention provides novel compounds having the general formula: wherein R1, R2 and R3 are as described herein, compositions including the compounds and methods of using the compounds.
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Page/Page column 20; 21
(2018/05/24)
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- Design, Synthesis, and Evaluation of Tetrahydropyrrolo[1,2-c]pyrimidines as Capsid Assembly Inhibitors for HBV Treatment
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The discovery of novel tetrahydropyrrolo[1,2-c]pyrimidines derivatives from Bay41-4109 as hepatitis B virus (HBV) inhibitors is herein reported. The structure-activity relationship optimization led to one highly efficacious compound 28a (IC50 = 10 nM) with good PK profiles and the favorite L/P ratio. The hydrodynamic injection model in mice clearly demonstrated the efficacy of 28a against HBV replication.
- Li, Xiaolin,Zhou, Kai,He, Haiying,Zhou, Qiong,Sun, Ya,Hou, Lijuan,Shen, Liang,Wang, Xiaofei,Zhou, Yuedong,Gong, Zhen,He, Shibo,Jin, Huangtao,Gu, Zhengxian,Zhao, Shuyong,Zhang, Long,Sun, Chunyan,Zheng, Shansong,Cheng, Zhe,Zhu, Yidong,Zhang, Minghui,Li, Jian,Chen, Shuhui
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supporting information
p. 969 - 974
(2017/09/23)
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- Investigation of carbon-2 substituted imidazoles and their corresponding ionic liquids
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The functionality at the C-2 position of the imidazole ring plays a key role in defining the chemical properties of the imidazoles and their corresponding ionic liquids. Imidazoles 1-6 with different C-2 functionality were synthesized and their corresponding ionic liquids were systematically investigated. Based on their physical properties the six imidazoles can be divided into three groups. (1) The imidazoles 2 and 3 are capable of self-polymerization to form poly(ionic liquid)s, and they are characterized with a strong leaving group at the C-2 position. (2) The imidazoles 4 and 5 can form ionic liquids, but they are very sensitive to moisture. (3) The imidazoles 1 and 6 can form stable ionic liquids, and their stabilities were influenced by the electronic effects of the substituents at the C-2 position.
- Liao, Chen,Zhu, Xiang,Sun, Xiao-Guang,Dai, Sheng
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supporting information; experimental part
p. 5308 - 5310
(2011/10/30)
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- Physicochemical properties of imidazolium-derived ionic liquids with different C-2 substitutions
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Five room temperature ionic liquids based on C-2 substituted imidazolium cations and bis(trifluoromethanesulfonyl)imide (TFSI) anions were synthesized and their physicochemical properties: thermal property, density, viscosity, ionic conductivity, self-diffusion coefficients, and electrochemical stability, were systematically investigated. The temperature dependence of both viscosity and ionic conductivities of these ionic liquids can be described by the Vogel-Fulcher-Tamman (VFT) equation. Compared with the reference, 1-propyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, the introduction of functional groups at the C-2 position generally increased the viscosity and lowered the ionic conductivity. The introduction of an ether group (-CH2OCH2CH2CH2CH3) at the C-2 position not only enhanced the reduction stability of the ionic liquids but also exhibited the lowest solid electrolyte interfacial resistance (R SEI). In contrast, the introduction of a cyano group (-CN) at the C-2 position not only decreased the reduction stability but also adversely increased the SEI resistance. The effect of the C-2 substitution on the reduction stability was explained by the change in the energy level of the lowest unoccupied molecular orbital. The self-diffusion coefficients (D) of each ion were measured by pulsed field gradient nuclear magnetic resonance (PFG-NMR). The lithium transference number (tLi) of 0.5 M LiTFSI/IL solutions calculated from the self-diffusion coefficients was in the range of 0.04 to 0.09.
- Liao, Chen,Shao, Nan,Han, Kee Sung,Sun, Xiao-Guang,Jiang, De-En,Hagaman, Edward W.,Dai, Sheng
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experimental part
p. 21503 - 21510
(2012/03/10)
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- Synthesis and SAR of 6-chloro-4-fluoroalkylamino-2-heteroaryl-5-(substituted)phenylpyrimidines as anti-cancer agents
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The synthesis and SAR of a series of 6-chloro-4-fluoroalkylamino-2-heteroaryl-5-(substituted)phenylpyrimidines as anti-cancer agents are described. This series of 2-heteroarylpyrimidines was developed by modifying a series of anti-tumor [1,2,4]triazolo[1,5-a]pyrimidines and 2-cyanoaminopyrimidines we reported earlier. For the 2-heteroaryl group, the best activity is obtained when the heteroaryl group has a nitrogen atom at the ortho-position to the pyrimidyl core. The structure-activity relationship for the rest of the molecule in this 2-heteroarylpyrimidine series mimics that of the [1,2,4]triazolo[1,5-a]pyrimidine series. Like triazolopyrimidines and 2-cyanoaminopyrimidines, the 2-heteroarylpyrimidines retain the capability to overcome multidrug resistance due to Pgp. Mechanism of action studies showed that the lead compounds behaved in the same manner as triazolopyrimidines and 2-cyanoaminopyrimidines. The lead compounds in this series are more potent than the corresponding triazolopyrimidines in vitro and in vivo. Compound 21 (PTI-868) showed tumor growth inhibition in several nude mouse xenograft models, and was selected to advance to preclinical development.
- Zhang, Nan,Ayral-Kaloustian, Semiramis,Nguyen, Thai,Hernandez, Richard,Lucas, Judy,Discafani, Carolyn,Beyer, Carl
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experimental part
p. 111 - 118
(2011/02/25)
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- INHIBITORS OF HEPATITIS C VIRUS PROTEASE, AND COMPOSITIONS AND TREATMENTS USING THE SAME
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The present invention provides compounds of formula (I), (II) or (IV), or pharmaceutically acceptable salts and solvates thereof, which are useful as inhibitors of the Hepatitis C virus (HCV) protease enzyme and are also useful for the treatment of HCV infections in HCV--infected mammals, including humans. The present invention also provides pharmaceutical compositions comprising compounds of formula (I), (II) or (IV), their pharmaceutically acceptable salts and solvates. Furthermore, the present invention provides intermediate compounds and methods useful in the preparation of compounds of formulas (I), (II) and (IV).
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Page/Page column 143-144
(2008/06/13)
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- 5-arylpyrimidines as anticancer agents
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This invention relates to certain 5-arylpyrimidine compounds or a pharmaceutically acceptable salt thereof, and compositions containing said compounds or a pharmaceutically acceptable salt thereof, wherein said compounds are anti-cancer agents useful for
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Page/Page column 43
(2008/06/13)
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- Synthesis and biological activity of nitro heterocycles analogous to megazol, a trypanocidal lead
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As part of our efforts to develop new compounds aimed at the therapy of parasitic infections, we synthesized and assayed analogues of a lead compound megazol, 5-(1-methyl-5-nitro-1H-2-imidazolyl)-1,3,4-thiadiazol-2-amine, CAS no. 19622-55-0), in vitro. We first developed a new route for the synthesis of megazol. Subsequently several structural changes were introduced, including substitutions on the two rings of the basic nucleus, replacement of the thiadiazole by an oxadiazole, replacement of the nitroimidazole part by a nitrofurane or a nitrothiophene, and substitutions on the exocyclic nitrogen atom for evaluation of an improved import by the glucose or the purine transporters. Assays of the series of compounds on the protozoan parasites Trypanosoma brucei, Trypanosoma cruzi, and Leishmania donovani, as either extracellular cells or infected macrophages, indicated that megazol was more active than the derivatives. Megazol was then evaluated on primates infected with Trypanosoma brucei gambiense, including late-stage central nervous system infections in combination with suramin. Full recovery was observed in five monkeys in the study with no relapse of parasitemia within a 2 year follow-up. Because there is a lack of efficacious treatments for sleeping sickness in Africa and Chagas disease in South America, megazol is proposed as a potential alternative. The mutagenicity of this compound is at present being reevaluated, and metabolism is also under investigation prior to possible further developments.
- Chauvière, Gérard,Bouteille, Bernard,Enanga, Bertin,De Albuquerque, Cristina,Croft, Simon L.,Dumas, Michel,Périé, Jacques
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p. 427 - 440
(2007/10/03)
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- Synthesis of heteroarenecarbonitriles by electrophilic cyanation; Reaction of metalated heteroarenes with p-toluenesulfonyl cyanide
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Several heteroarenecarbonitriles (5) were synthesized in moderate yields from heteroarenes (3) through metalation, followed by electrophilic cyanation using p-toluenesulfonyl cyanide. Similarly, trimethylsilylheteroarenes (8) were converted to heteroarenecarbonitriles (5) in good yields by treatment with p-toluenesulfonyl cyanide.
- Nagasaki, Izuru,Suzuki, Yumiko,Iwamoto, Ken-Ichi,Higashino, Takeo,Miyashita, Akira
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p. 443 - 450
(2007/10/03)
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- Transfer of Alkoxycarbonyl from Alkyl Imidazolium-2-carboxylates to Benzyl Alcohol, a Cyclohexanone Enamine and Diethylamine
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Alkylimidazole-2-carboxylates may be alkylated with methyl triflate to give the corresponding N-methylimidazolium salts.These salts react with benzyl alcohol in the presence of 1,4-diazabicyclooctane, with 1-(pyrrolidin-1-yl)cyclohexene and with diethylamine to give benzyl alkyl carbonates, an enamino ester and a urethane respectively; in one case a tetrahedral intermediate is observed.The corresponding phenyl ester was consumed without attack by benzyl alcohol at the carbonyl group.A 2-cyanoimidazolium salt underwent similar ill-defined consumption whereas a 2-dimethylaminocarbonyl derivative remained unchanged. 2-Methylsulfonylimidazolium salts suffered attack by benzyl alcohol at the ring C-2.
- Bakhtiar, Cuross,Smith, Edward H.
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p. 239 - 244
(2007/10/02)
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- Phosphotriesters Approach to the Synthesis of Oligonucleotides: A Reappraisal
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The phosphotriester approach to the synthesis of oligodeoxyribo- and oligoribo-nucleotides in solution has been reinvestigated.The efficacy of mesitylene-2-sulfonyl chloride (MSCl) 15a, 2,4,6-triisopropylbenzenesulfonyl chloride (TrisCl) 15b, 4-bromobenzenesulfonyl chloride 15c, naphthalene-1-sulfonyl chloride 39, and 2- and 4-nitrobenzenesulfonyl chlorides 40a and 40b, respectively, as activating agents has been examined.The latter arenesulfonyl chlorides have been used in conjunction with the following nucleophilic catalysts: 1-methylimidazole, 3-nitro-1H-1,2,4-triazole 19, 5-(3-nitrophenyl)-1H-tetrazole 20a, 5-(3,5-dinitrophenyl)-1H-tetrazole 20b, 5-(1-methylimidazol-2-yl)-1H-tetrazole 21, 5--1H-tetrazole 22, 4-ethoxypyridine 1-oxide 14a, 4,6-dinitro-1-hydroxybenzotriazole 29a, 1-hydroxy-4-nitro-6-(trifluoromethyl)benzotriazole 29b, 1-hydroxy-5-phenyltetrazole 30a and 1-hydroxy-5-(3-nitrophenyl)tetrazole 30b.The rates of formation and yields of the fully protected dideoxyribonucleoside and diribonucleoside phosphates 37 and 47, respectively, were determined using various combinations of activating agents and nucleophilic catalysts.Although 2- and 4-nitrobenzenesulfonyl chlorides 40a and 40b, respectively, proved to be the most powerful activating agents, their use in the deoxy-series led to the formation of by-products and hence to unsatisfactory isolated yields of the dideoxyribonucleoside phosphate 37.
- Reese, Colin B.,Pei-Zhuo, Zhang
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p. 2291 - 2302
(2007/10/02)
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- 2,2'-bi-1H-imidazoles
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This invention relates to novel derivatives of 2,2'-bi-1H-imidazoles, to the processes and intermediates used in their preparation, to their ability to exert the pharmacologic effects of lowering high blood pressure and of increasing heart contractile force and to their use as chemotherpauetic agents useful in treating cardiac insufficiency and hypertension.
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- Cyanogen Bromide-Dimethylaminopyridine (CAP): A Convenient Source of Positive Cyanide for the Synthesis of 2-Cyanoimidazoles
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Dimethylaminopyridine activates cyanogen bromide towards C-C bond formation by forming 1-cyano-4-dimethylaminopyridinium bromide.The latter serves as a convenient reagent for the synthesis of 2-cyanoimidazoles.
- Whitten, Jeffrey P.,McCarthy, James R.,Matthews, Donald P.
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p. 470 - 472
(2007/10/02)
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- Anodic Cyanation of 1-Methylimidazoles
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The electrooxidation of several 1-methylimidazoles was performed in MeOH that contains NaCN at a platinum anode in a divided cell.Replacement of an aromatic hydrogen by a cyano group occurred.With 1,2,4,5-tetramethylimidazole, the 2,5-addition of cyano groups to the imidazole ring was achieved, and besides side-chain substitution occurred concurrently.
- Yoshida, Kunihisa,Kitabayashi, Hirohito
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p. 3693 - 3696
(2007/10/02)
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- N-CYANO-N'-ALKYLIMIDAZOLIUM YLIDS AS NOVEL INTERMEDIATES TO 2-CYANOIMIDAZOLES
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N-Substituted imidazoles were readily converted to 2-cyanoimidazoles by treatment with cyanogen chloride followed by triethylamine.The utilization of the SEM protecting group provided a facile entry to N-unsubstituted 2-cyanoimidazoles.
- McCarthy, James R.,Matthews, Donald P.,Whitten, Jeffrey P.
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p. 6273 - 6276
(2007/10/02)
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- Competing Pathways in the Phototransposition of Pyrazoles
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Cyano-substituted pyrazoles transpose photochemically into imidazoles by two concurrent paths: (a) 1,5-interchange, probably by 2,5-bonding to a diazabicyclopentene which isomerises by nitrogen 'walk' before rearomatisation, and (b) 2,3-interchange, probably via an intermediate azirine; in sharp contrast, 1,5-dimethyl-3-trifluoromethylpyrazole phototransposes exclusively by the former path.
- Barltrop, John A.,Day, A. Colin,Mack, Arthur G.,Shahrisa, Aziz,Wakamatsu, Shigeru
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p. 604 - 606
(2007/10/02)
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