- METHODS AND COMPOSITIONS FOR MODULATING SPLICING
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Described herein are small molecule splicing modulator compounds that modulate splicing of mRNA, such as pre-mRNA, encoded by genes, and methods of use of the small molecule splicing modulator compounds for modulating splicing and treating diseases and conditions.
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Paragraph 01005
(2020/08/22)
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- CHROMEN-4-ONE DERIVATIVES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS DISEASE
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The present invention provides novel compounds having the general formula (I) wherein R1 to R6, and m are as described herein, compositions including the compounds and methods of using the compounds.
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- Enhanced antibacterial activity of endo-nortropine substituted (C-7) fluoroquinolones against V. cholerae, S. aureus and B. subtilis
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Introduction: Bacterial infections account for maximum deaths worldwide than for any other single cause. Methods: Here in, we report a convenient synthesis of new fluoroquinolone molecules substituted with endo-nortropine and its derivatives at C-7position. All the synthesized molecules, when screened for their antibacterial activity by agar diffusion method against Vibrio cholerae, Bacillus subtilis, Staphylococcus aureus and Escherichia coli were found to be active against the first three strains. The shortlisted compounds in the series, RG and RO, were further evaluated to determine their MIC values by micro-dilution broth assay. Result & Conclusion: Compound RG was ten times more effective in case of S. aureus (15.0 nM), two times in case of V. cholerae (3.7 nM) and the same as that of standard drug Levofloxacin in case of Bacillus subtilis (7.8 nM). Compound RO also displayed an impressive MIC value (62.5 nM) in case of S. aureus as compared to control (125 nM). The results have been supported by in-silico docking studies, where increased hydrogen bonding interactions in case of RG as compared to standard drug levofloxacin with DNA gyrase (2XCT) of S. aureus resulted in decreased energy of the former.
- Salunke, Ramkrushna Ashok,Sidhu, Chandni,Kumar, Ashok,Pinnaka, Anil Kumar,Bansal, Baldev Raj,Chhibber, Manmohan
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p. 895 - 904
(2018/09/10)
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- Small Molecule Antagonists of the Nuclear Androgen Receptor for the Treatment of Castration-Resistant Prostate Cancer
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After a high-throughput screening campaign identified thioether 1 as an antagonist of the nuclear androgen receptor, a zone model was developed for structure-activity relationship (SAR) purposes and analogues were synthesized and evaluated in a cell-based luciferase assay. A novel thioether isostere, cyclopropane (1S,2R)-27, showed the desired increased potency and structural properties (stereospecific SAR response, absence of a readily oxidized sulfur atom, low molecular weight, reduced number of flexible bonds and polar surface area, and drug-likeness score) in the prostate-specific antigen luciferase assay in C4-2-PSA-rl cells to qualify as a new lead structure for prostate cancer drug development.
- Johnson, James K.,Skoda, Erin M.,Zhou, Jianhua,Parrinello, Erica,Wang, Dan,O'Malley, Katherine,Eyer, Benjamin R.,Kazancioglu, Mustafa,Eisermann, Kurtis,Johnston, Paul A.,Nelson, Joel B.,Wang, Zhou,Wipf, Peter
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supporting information
p. 785 - 790
(2016/08/24)
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- Highly efficient aerobic oxidation of alcohols by using less-hindered nitroxyl-radical/copper catalysis: Optimum catalyst combinations and their substrate scope
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The oxidation of alcohols into their corresponding carbonyl compounds is one of the most fundamental transformations in organic chemistry. In our recent report, 2-azaadamantane N-oxyl (AZADO)/copper catalysis promoted the highly chemoselective aerobic oxidation of unprotected amino alcohols into amino carbonyl compounds. Herein, we investigated the extension of the promising AZADO/copper-catalyzed aerobic oxidation of alcohols to other types of alcohol. During close optimization of the reaction conditions by using various alcohols, we found that the optimum combination of nitroxyl radical, copper salt, and solution concentration was dependent on the type of substrate. Various alcohols, including highly hindered and heteroatom-rich ones, were efficiently oxidized into their corresponding carbonyl compounds under mild conditions with lower amounts of the catalysts.
- Sasano, Yusuke,Kogure, Naoki,Nishiyama, Tomohiro,Nagasawa, Shota,Iwabuchi, Yoshiharu
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p. 1004 - 1009
(2015/03/31)
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- MUSCARINIC RECEPTOR AGONISTS
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This invention relates to compounds that are agonists of the muscarinic M1 receptor and which are useful in the treatment of muscarinic M1 receptor mediated diseases. Also provided are pharmaceutical compositions containing the compounds and the therapeutic uses of the compounds. Compounds provided are of formula where m, p, q, W, Z, Y, X1, X2, R1, R2 R3 and R4 are as defined herein.
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Page/Page column 49; 50
(2015/12/09)
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- Highly chemoselective aerobic oxidation of amino alcohols into amino carbonyl compounds
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The direct oxidation of unprotected amino alcohols to their corresponding amino carbonyl compounds has often posed serious challenges in organic synthesis and has constrained chemists to adopting an indirect route, such as a protection/deprotection strategy, to attain their goal. Described herein is a highly chemoselective aerobic oxidation of unprotected amino alcohols to their amino carbonyl compounds in which 2-azaadamantane N-oxyl (AZADO)/copper catalysis is used. The catalytic system developed leads to the alcohol-selective oxidation of various unprotected amino alcohols, carrying a primary, secondary, or tertiary amino group, in good to high yield at ambient temperature with exposure to air, thus offering flexibility in the synthesis of nitrogen-containing compounds. Strong as an ox: The highly chemoselective aerobic oxidation of unprotected amino alcohols to their corresponding amino carbonyl compounds has been achieved by using 2-azaadamantane N-oxyl (AZADO)/copper catalysis. This catalytic system oxidizes not only alcohols with tertiary amino groups but also those with secondary and primary amines in good to high yield at ambient temperature in air. bpy=2,2-bipyridyl, DMAP=4-(N,N-dimethylamino)pyridine.
- Sasano, Yusuke,Nagasawa, Shota,Yamazaki, Mai,Shibuya, Masatoshi,Park, Jaiwook,Iwabuchi, Yoshiharu
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supporting information
p. 3236 - 3240
(2014/04/03)
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- INHIBITORS OF LEUKOTRIENE A4 HYDROLASE
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The present invention is directed to compounds encompassed by the Formula (I), pharmaceutical compositions thereof, methods for inhibiting LTA-4 hydrolase, and methods for the treatment of a disease and disorder which is ameliorated by the inhibition of LTA4-h activity. Non-limiting examples of such diseases and conditions include inflammatory and autoimmune diseases and disorders.
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Page/Page column 39
(2014/10/04)
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- Anti-prion activities and drug-like potential of functionalized quinacrine analogs with basic phenyl residues at the 9-amino position
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In this paper, we report the synthesis and cell-based anti-prion activity of quinacrine analogs derived by replacing the basic alkyl side chain of quinacrine with 4-(4-methylpiperazin-I-yl)phenyl, (1-benzylpiperidin-4-yl) and their structural variants. Several promising analogs were found that have a more favorable anti-prion profile than quinacrine in terms of potency and activity across different prion-infected murine cell models. They also exhibited greater binding affinities for a human prion protein fragment (hPrP121-231) than quinacrine, and had permeabilities on the PAMPA-BBB assay that fall within the range of CNS permeant candidates. When evaluated on bidirectional assays on a Pgp overexpressing cell line, one analog was less susceptible to Pgp efflux activity compared to quinacrine. Taken together, the results point to an important role for the substituted 9-amino side chain attached to the acridine, tetrahydroacridine and quinoline scaffolds. The nature of this side chain influenced cell-based potency, PAMPA permeability and binding affinity to hPrP121-231.
- Nguyen, Thuy,Sakasegawa, Yuji,Doh-Ura, Katsumi,Go, Mei-Lin
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experimental part
p. 2917 - 2929
(2011/07/08)
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- The discovery of tropane derivatives as nociceptin receptor ligands for the management of cough and anxiety
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The discovery of 1 as a high-affinity ligand for the nociceptin receptor has led to the synthesis of a series of tropane (8-methyl-8-azabicyclo[3.2.1]octane) derivatives as optimized ligands. These compounds exhibit high affinity for the nociceptin recept
- Ho, Ginny D.,Anthes, John,Bercovici, Ana,Caldwell, John P.,Cheng, Kuo-Chi,Cui, Xiaoming,Fawzi, Ahmad,Fernandez, Xiomara,Greenlee, William J.,Hey, John,Korfmacher, Walter,Lu, Sherry X.,McLeod, Robbie L.,Ng, Fay,Torhan, April Smith,Tan, Zheng,Tulshian, Deen,Varty, Geoffrey B.,Xu, Xiaoying,Zhang, Hongtao
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scheme or table
p. 2519 - 2523
(2009/12/25)
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- TROPANE DERIVATIVES USEFUL AS PESTICIDES
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Compounds of formula (I) wherein the substituents have the meanings assigned to them in claim 1, are useful as pesticides.
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Page/Page column 34-35
(2009/03/07)
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- Modulators of muscarinic receptors
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The present invention relates to modulators of muscarinic receptors. The present invention also provides compositions comprising such modulators, and methods therewith for treating muscarinic receptor mediated diseases.
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Page/Page column 120
(2010/11/29)
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- Use of a compound having a monogalactosyldiacylglycerol synthase inhibitory activity as herbicide or algaecide, herbicide and algaecide compositions
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The invention relates to the use of compounds having a monogalactosyldiacylglycerol (MGDG) synthase inhibitory activity as herbicide or algaecide, and to herbicide and algaecide compositions containing at least one of these compounds.
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Page/Page column 15
(2009/01/20)
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- Two-step synthesis of achiral dispiro-1,2,4,5-tetraoxanes with outstanding antimalarial activity, low toxicity, and high-stability profiles
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A rapid, two-step synthesis of a range of dispiro-1,2,4,5-tetraoxanes with potent antimalarial activity both in vitro and in vivo has been achieved. These 1,2,4,5-tetraoxanes have been proven to be superior to 1,2,4-trioxolanes in terms of stability and to be superior to trioxane analogues in terms of both stability and activity. Selected analogues have in vitro nanomolar antimalarial activity and good oral activity and are nontoxic in screens for both cytotoxicity and genotoxicity. The synthesis of a fluorescent 7-nitrobenza-2-oxa-1,3-diazole (NBD) tagged tetraoxane probe and use of laser scanning confocal microscopy techniques have shown that tagged molecules accumulate selectively only in parasite infected erythrocytes and that intraparasitic formation of adducts could be inhibited by co-incubation with the iron chelator desferrioxamine (DFO).
- Ellis, Gemma L.,Amewu, Richard,Sabbani, Sunil,Stocks, Paul A.,Shone, Alison,Stanford, Deborah,Gibbons, Peter,Davies, Jill,Vivas, Livia,Charnaud, Sarah,Bongard, Emily,Hall, Charlotte,Rimmer, Karen,Lozanom, Sonia,Jesús, María,Gargallo, Domingo,Ward, Stephen A.,O'Neill, Paul M.
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p. 2170 - 2177
(2008/12/21)
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- DISPIRO TETRAOXANE COMPOUNDS
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A compound having the formula (I) wherein ring A represents a substituted or unsubstituted monocyclic or multicyclic ring; m=any positive integer; n=0-5; X=CH and Y=-C(O)NR1R2, -NR1R2 or -S(O)2R4, where R1, R2 and R4 are each individually selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted amine, substituted or unsubstituted carbocyclic ring, substituted or unsubstituted heterocyclic ring, or any combination thereof, or R1 and R2 are linked so as to form part of a substituted or unsubstituted heterocyclic ring, or X=N and Y=-S(O)2R3 or -C(O)R3, where R3 is selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted amine, substituted or unsubstituted carbocyclic ring, substituted or unsubstituted heterocyclic ring or any combination thereof.
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Page/Page column 86
(2008/06/13)
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- Development of CXCR3 antagonists. Part 3: Tropenyl and homotropenyl-piperidine urea derivatives
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The optimization of a series of 1-aryl-3-piperidinyl urea derivatives is described in which incorporation of tropenyl and homotropenyl moieties has led to significant improvements in activity and drug-like properties. Replacement of the central piperidine
- Watson, Robert J.,Allen, Daniel R.,Birch, Helen L.,Chapman, Gayle A.,Galvin, Frances C.,Jopling, Louise A.,Knight, Roland L.,Meier, Dorica,Oliver, Kathryn,Meissner, Johannes W.G.,Owen, David A.,Thomas, Elizabeth J.,Tremayne, Neil,Williams, Sophie C.
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p. 147 - 151
(2008/09/17)
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- Structure-activity relationships for a novel series of dopamine D2-like receptor ligands based on N-substituted 3-aryl-8-azabicyclo[3.2.1]octan-3-ol
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Discovering dopamine D2-like receptor subtype-selective ligands has been a focus of significant investigation. The D2R-selective antagonist 3-[4-(4-chlorophenyl)-4-hydroxypiperidinyl]methylindole (1, L741,626; K i(D2R/D3R) = 11.2:163 nM) has previously provided a lead template for chemical modification. Herein, analogues have been synthesized where the piperidine was replaced by a tropane ring that reversed the selectivity seen in the parent compound, in human hD2LR- or hD3R-transfected HEK 293 cells (31, Ki(D2R/D3R) = 33.4: 15.5 nM). Further exploration of both N-substituted and aryl ring-substituted analogues resulted in the discovery of several high affinity D2R/D3R ligands with 3-benzofurylmethyl-substituents (e.g., 45, Ki(D2R/D3R) = 1.7:0.34 nM) that induced high affinity not achieved in similarly N-substituted piperidine analogues and significantly (470-fold) improved D3R binding affinity compared to the parent ligand 1. X-ray crystallographic data revealed a distinctive spatial arrangement of pharmacophoric elements in the piperidinol vs tropine analogues, providing clues for the diversity in SAR at the D2 and D3 receptor subtypes.
- Paul, Noel M.,Taylor, Michelle,Kumar, Rakesh,Deschamps, Jeffrey R.,Luedtke, Robert R.,Newman, Amy Hauck
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body text
p. 6095 - 6109
(2009/10/01)
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- Diamine derivatives as inhibitors of leukotriene A4 hydrolase
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This invention is directed to compounds of formula (I): where r, q, R, R2, R3, R4, R5a, R5b, R5c, R6a, R6b, R6c, R7, R8, and R9
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Page/Page column 68
(2010/11/27)
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- CYCLOALKANOPYRIDINE DERIVATIVE
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Provided are cycloalkanopyridine derivatives of formula [I]: [wherein the symbols are the same as those stated in the description]. The compounds act as a nociceptin receptor antagonist, and are useful as medicines for diseases associated with a nociceptin receptor, for example, as a reliever against tolerance to a narcotic analgesic; a reliever against dependence on or addiction to a narcotic analgesic; an analgesic enhancer; an antiobesitic or appetite suppressor; a treating or prophylactic agent for cognitive impairment and dementia/amnesia; an agent for treating developmental cognitive abnormality; a remedy for schizophrenia; an agent for treating neurodegenerative diseases; an anti-depressant or treating agent for affective disorder; a treating or prophylactic agent for diabetes insipidus; a treating or prophylactic agent for polyuria; or a remedy for hypotension.
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Page/Page column 43
(2010/11/24)
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- BICYCLIC FIVE-MEMBERED HETEROARYL DERIVATIVES AND THEIR USE AS RENIN INHIBITORS
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The invention relates to novel five-membered heteroaryl derivatives and the use thereof as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions comprising one or more of those compounds and especially their use as inhibitors of renin.
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Page/Page column 28-29
(2010/11/23)
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- Stereoselective synthesis of conformationally constrained tropane analogues: 6-Chloro-2,5-diazatetracyclo[8.5.0.02,13.0 4,9]pentadeca-4,6,8-triene-11-one and 6-chloro-2,7-diazatetracyclo- [8.5.0.02,13.04,9]pentadeca-4,6,8-triene-11-one
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Two conformationally constrained tropane derivatives were prepared as rigid nicotinic acetylcholine receptor ligands. A palladium catalyzed intramolecular α-arylation reaction was employed to generate the tricyclic compounds in good yields from N-(bromo-chloropyridylmethyl)-8-azabicyclo[3.2.1]octan-3-ones.
- Cheng, Jie,Xu, Liang,Stevens, Edwin D.,Trudell, Mark L.,Izenwasser, Sari,Wade, Dean
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p. 569 - 574
(2007/10/03)
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- Modulation of selective serotonin reuptake inhibitor and 5-HT1A antagonist activity in 8-aza-bicyclo[3.2.1]octane derivatives of 2,3-dihydro-1,4-benzodioxane
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2,3-Dihydro-1,4-benzodioxanes with aryl 8-aza-bicyclo[3.2.1]oct-3-ene attachments 2 produce compounds with potent 5-HT-T affinity, and weak 5-HT 1A affinity and α1 affinity. This compares with 2,3-dihydro-1,4-benzodioxanes containing 8-aza-bicyclo[3.2.1] octan-3-ol attachments 4 which possess potent 5-HT1A affinity, moderate to good selectivity over α1 and little 5-HT-T affinity. A 3-benzothiophene analogue of 4 (30) was synthesized which possesses potent 5-HT1A affinity and especially good selectivity over both α1 and 5-HT-T.
- Gilbert, Adam M.,Stack, Gary P.,Nilakantan, Ramaswamy,Kodah, Jason,Tran, Megan,Scerni, Rosemary,Shi, Xiaojie,Smith, Deborah L.,Andree, Terrance H.
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p. 515 - 518
(2007/10/03)
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- Novel aryloxy-8-azabicyclo[3.2.1]oct-3-enes with 5-HT transporter and 5-HT1A affinity
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Joining aryl 8-azabicyclo[3.2.1]oct-3-enes with aryloxyethanes and aryloxypropanes produces novel series of compounds 11 and 12 with potent 5-HT-T affinity and moderately potent 5-HT1A affinity. Moreover, several of these compounds possess func
- Gilbert, Adam M.,Coleman, Thomas,Kodah, Jason,Mewshaw, Richard E.,Scerni, Rosemary,Schechter, Lee E.,Smith, Deborah L.,Andree, Terrance H.
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p. 5281 - 5284
(2007/10/03)
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- 1- (2H-PYRAZOL -3-YL) -3YL) {4-`1- (BENZOYL) -PIPERIDIN-4-YLMETHYL!-PHENYL}-UREA DERIVATIVES AND RELATED COMPOUNDS AS INHBITORS OF P38 KINASE AND/OR TNF INHIBITORS FOR THE TREATMENT OF IMFLAMMATIONS
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The present invention provides compounds of Formula (I) Wherein ( ) is an optional ethylene bridge; R1 is alkyl, cycloalkyl, aryl or aryl substituted with one or more substituents selected from alkyl, alkoxy and amino, or R1 is pyridyl or pyridyl substitu
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- CHEMICAL COMPOUNDS
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Compounds of formula (I): compositions comprising them, processes for preparing them and their use in medical therapy (for example modulating CCR5 receptor activity in a warm blooded animal).
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- Design and synthesis of novel CCR3 antagonists
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As part of our investigation into the development of potent CCR3 antagonists, a series of piperidine analogues was designed and prepared. Exploration of the piperidine core examined both the basicity and the location of a nitrogen, as well as conformational variants. The bicyclo-piperidine 24c was found to be the most potent inhibitor of CCR3 with an IC50 of 0.0082 μM in the binding assay and 0.0024 μM in the chemotaxis assay.
- Gong, Leyi,Hogg, J. Heather,Collier, James,Wilhelm, Robert S.,Soderberg, Carol
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p. 3597 - 3600
(2007/10/03)
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- A modified palladium catalysed reductive amination procedure
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New, extended applications of a modified palladium catalysed reductive amination procedure are described; a mechanistic hypothesis alternative to the common imine pathway is proposed. This versatile method advances the usual reductive amination processes
- Berdini, Valerio,Cesta, Maria C,Curti, Roberto,D'Anniballe, Gaetano,Bello, Nicoletta Di,Nano, Giuseppe,Nicolini, Luca,Topai, Alessandra,Allegretti, Marcello
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p. 5669 - 5674
(2007/10/03)
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- Crowded piperidines with intramolecularly hydrogen-bonded nitrogen: Synthesis and conformation study
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2,2,6,6-Tetramethyl substituted piperidines with a β-branched N-alkyl substituent were synthesized by the photoreaction of N-Me precursors with ketones. The main conformation features of these sterically-hindered amines (established by NMR and IR spectroscopy) are a ring in the chair form, an eclipsed conformation for the N-substituent and an intramolecular OH···N bond. High barriers for the geminal substituent topomerization were measured for these piperidines at different temperatures by means of line-shape analysis of the temperature-dependent 13C and 1H NMR spectra. An MM3-derived conformation scheme indicated that, for one of the studied analogues, the rotation of the N-substituent determines a slow topomerization rate. A new mechanism of nitrogen inversion - a concerted hydrogen-bond dissociation/nitrogen inversion process - is considered for hydrogen-bonded amines.
- Belostotskii, Anatoly M.,Gottlieb, Hugo E.,Aped, Pinchas
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p. 3016 - 3026
(2007/10/03)
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- Photochemical N-demethylation of alkaloids
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Certain alkaloids were observed to undergo N-demethylation processes under photochemical conditions. Tropine, acetyltropine, tropinone, and atropine were cleanly N-demethylated upon treatment with tetraphenylporphin, oxygen, and light. Dextromethorphan also underwent a N-demethylation reaction, but reacted further to afford an imine. In contrast, 14-acyloxycodeinones underwent a photochemically induced tandem N-demethylation-acyl migration.
- Ripper, Justin A.,Tiekink, Edward R.T.,Scammells, Peter J.
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p. 443 - 445
(2007/10/03)
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- Bridged γ-Carbolines and Derivatives Possessing Selective and Combined Affinity for 5-HT2 and D2 Receptors
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A series of 5,6,7,8,9,10-hexahydro-7,10-iminocycloheptindoles and 6,7,8,9,10,11-hexahydro-7,11-imino-5H-cyclooctindoles was prepared. Structural modifications of the lead compound, 11--5,6,7,8,9,10-hexahydro-7,10-iminocycl
- Mewshaw, Richard E.,Silverman, Lisa S.,Mathew, Rose M.,Kaiser, Carl,Sherrill, Ronald G.,et al.
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p. 1488 - 1495
(2007/10/02)
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- Synthesis and in vitro evaluation of 5,6,7,8,9,10-hexahydro-7,10- iminocyclohept[b]indoles: High-affinity ligands for the N,N'-di-o- tolylguanidine-labeled σ binding site
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A series of 5,6,7,8,9,10-hexahydro-7,10-iminocyclo[b]indoles substituted at the 5 and/or 11 positions was synthesized from tropinone. Affinity for σ binding sites was determined using [3H]-N,N'-di-o-tolylguanidine ([3H]DTG) and [sup
- Mewshaw,Sherrill,Mathew,Kaiser,Bailey,Karbon
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p. 343 - 352
(2007/10/02)
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- THE METABOLISM OF TROPINONE IN INTACT DATURA INNOXIA PLANTS
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Tropinone was synthesized by reaction of nortropinone with methyl iodide.This labelled ketone was administered to intact Datura innoxia plants (3-4 months-old) by addition to the nutrient solution in which the roots were growing.The resul
- Landgrebe, Mary E.,Leete, Edward
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p. 2521 - 2524
(2007/10/02)
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- ELECTRON-TRANSFER ACTIVATION. PHOTOCHEMICAL N-DEMETHYLATION OF TERTIARY AMINES
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DAP(2+) sensitized photooxidation of some biologically active N-methylated alkaloids affords the corresponding secondary amines in excellent yields (80-95percent).
- Santamaria, J.,Ouchabane, R.,Rigaudy, J.
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p. 2927 - 2928
(2007/10/02)
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- ELECTRON-TRANSFER ACTIVATION. SALT EFFECTS ON THE PHOTOOXADIDATION OF TERTIARY AMINES : A USEFUL N-DEMETHYLATION METHOD
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Photooxidation of tertiary methylamines sensitized by electron acceptors like 9,10-dicyanoanthracene is shown to proceed by two distinct ways depending on the presence of added salts.In the absence of added salt both nor and N-formyl compounds were obtained while with added salt the nor-derivative is obtained highly efficiently.
- Santamaria, J.,Ouchabane, R.,Rigaudy, J.
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p. 3977 - 3980
(2007/10/02)
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