- Formation and cleavage of C-H, C-C, and C-O bonds of ortho-methyl- substituted anisoles by late transition metals
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2,6-Dimethyl-substituted anisoles can be converted into the corresponding 2-ethyl-6-methylphenols in a several-step reaction mediated by a TpMe2Ir(III) complex; use of the 13C-enriched anisoles, ArO13CH3/s
- Lara, Patricia,Paneque, Margarita,Poveda, Manuel L.,Salazar, Veronica,Santos, Laura L.,Carmona, Ernesto
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Read Online
- Synthesis of Highly Substituted Phenols and Benzenes with Complete Regiochemical Control
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Substituted phenols are requisite molecules for human health, agriculture, and diverse synthetic materials. We report a chemical synthesis of phenols, including penta-substituted phenols, that accommodates programmable substitution at any position. This method uses a one-step conversion of readily available hydroxypyrone and nitroalkene starting materials to give phenols with complete regiochemical control and in high chemical yield. Additionally, the phenols can be converted into highly and even fully substituted benzenes.
- Zhang, Xiaojie,Beaudry, Christopher M.
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supporting information
p. 6086 - 6090
(2020/08/12)
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- Novel S1P1 receptor agonists - Part 3: From thiophenes to pyridines
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In preceding communications we summarized our medicinal chemistry efforts leading to the identification of potent, selective, and orally active S1P 1 agonists such as the thiophene derivative 1. As a continuation of these efforts, we replaced the thiophene in 1 by a 2-, 3-, or 4-pyridine and obtained less lipophilic, potent, and selective S1P1 agonists (e.g., 2) efficiently reducing blood lymphocyte count in the rat. Structural features influencing the compounds' receptor affinity profile and pharmacokinetics are discussed. In addition, the ability to penetrate brain tissue has been studied for several compounds. As a typical example for these pyridine based S1P 1 agonists, compound 53 showed EC50 values of 0.6 and 352 nM for the S1P1 and S1P3 receptor, respectively, displayed favorable PK properties, and penetrated well into brain tissue. In the rat, compound 53 maximally reduced the blood lymphocyte count for at least 24 h after oral dosing of 3 mg/kg.
- Bolli, Martin H.,Abele, Stefan,Birker, Magdalena,Bravo, Roberto,Bur, Daniel,De Kanter, Ruben,Kohl, Christopher,Grimont, Julien,Hess, Patrick,Lescop, Cyrille,Mathys, Boris,Müller, Claus,Nayler, Oliver,Rey, Markus,Scherz, Michael,Schmidt, Gunther,Seifert, Jürgen,Steiner, Beat,Velker, J?rg,Weller, Thomas
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p. 110 - 130
(2014/02/14)
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- PYRIDIN-4-YL DERIVATIVES
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The invention relates to compounds of the Formula (I), Formula (I) wherein R1 and R2 are as described in the description, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immuno
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Page/Page column 15
(2014/09/29)
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- Heterogeneous copper-catalyzed hydroxylation of aryl iodides under air conditions
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In this work, the ligand-free heterogeneous copper Cu-g-C3N 4 was synthesized and used for the hydroxylation of aryl iodides to synthesize phenols using cheap bases. The catalyst was conveniently prepared, air-tolerant, reusable and scalable, and is very efficient for a wide range of substrates. The synthesis of substituted phenols can be carried out under air conditions and has great potential for practical applications. This journal is the Partner Organisations 2014.
- Ding, Guodong,Han, Hongling,Jiang, Tao,Wu, Tianbin,Han, Buxing
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supporting information
p. 9072 - 9075
(2014/08/05)
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- Novel S1P1 receptor agonists - Part 1: From pyrazoles to thiophenes
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From a high-throughput screening campaign aiming at the identification of novel S1P1 receptor agonists, the pyrazole derivative 2 emerged as a hit structure. Medicinal chemistry efforts focused not only on improving the potency of the compound but in particular also on resolving its inherent instability issue. This led to the discovery of novel bicyclo[3.1.0]hexane fused thiophene derivatives. Compounds with high affinity and selectivity for S1P1 efficiently reducing the blood lymphocyte count in the rat were identified. For instance, compound 85 showed EC50 values of 7 and 2880 nM on S1P1 and S1P3, respectively, had favorable pharmacokinetic properties in rat and dog, distributed well into brain tissue, and efficiently and dose dependently reduced the blood lymphocyte count in the rat. After oral administration to spontaneously hypertensive rats, the S1P 1 selective compound 85 showed no effect on mean arterial blood pressure and affected the heart rate during the wake phase of the animals only.
- Bolli, Martin H.,Müller, Claus,Mathys, Boris,Abele, Stefan,Birker, Magdalena,Bravo, Roberto,Bur, Daniel,Hess, Patrick,Kohl, Christopher,Lehmann, David,Nayler, Oliver,Rey, Markus,Meyer, Solange,Scherz, Michael,Schmidt, Gunther,Steiner, Beat,Treiber, Alexander,Velker, J?rg,Weller, Thomas
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p. 9737 - 9755
(2014/01/06)
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- NOVEL THIOPHENE DERIVATIVES AS SPHINGOSINE-1-PHOSPHATE-1 RECEPTOR AGONISTS
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The invention relates to novel thiophene derivatives, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunosuppressive agents.
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- Green catalysts derived from agricultural and industrial waste products: The preparation of phenols from CsOH and Aryl iodides using CuO on mesoporous silica
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The synthesis of CuO catalysts supported on mesoporous silica derived from rice husks and semiconductor copper from chemical mechanical planarization (Cu-CMP) wastewater is described. These catalysts are active for the coupling reaction of CsOH with aryl iodides. Low catalyst loading (1 mol-%) without the need for ancillary ligands make these very attractive "green" catalysts. The synthesis of CuO catalysts supported on mesoporous silica derived from rice husks and semiconductor copper from chemical mechanical planarization (Cu-CMP) wastewater is described. These catalysts are active for the coupling reaction of CsOH with aryl iodides. Low catalyst loading (1 mol-%) without the need for ancillary ligands make these very attractive "green" catalysts. Copyright
- Chan, Chien-Ching,Chen, Yan-Wun,Su, Chi-Shen,Lin, Hong-Ping,Lee, Chin-Fa
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experimental part
p. 7288 - 7293
(2012/01/06)
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- Pyridin-4-yl derivatives as immunomodulating agents
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The invention relates to pyridine derivatives of Formula (I) wherein A, R1, R2, R3, R4, R5, and R6 are as described in the description, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents.
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(2010/04/23)
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- AMINO-PYRIDINE DERIVATIVES AS S1P1 /EDG1 RECEPTOR AGONISTS
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The invention relates to novel amino-pyridine derivatives, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents.
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Page/Page column 17
(2010/04/30)
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- Pyridin-3-yl derivatives as immunomodulating agents
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The invention relates to pyridin-3-yl derivatives of Formula (I) wherein R1, R2, R3, R4, R5; R6 and A are as described in the description, their preparation and their use as pharmaceuticall
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(2010/07/08)
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- THIOPHENE DERIVATIVES AS AGONISTS OF S1P1/EDG1
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The invention relates to novel thiophene derivatives (1), their preparation and their use as pharmaceutically active compounds.Said compounds particularly act as immunomodulating agents. Formula (I).
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(2010/11/03)
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- PYRIDINE COMPOUNDS
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The invention relates to pyridine compounds, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents.
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Page/Page column 28
(2009/10/22)
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- NOVEL AMINOMETHYL BENZENE DERIVATIVES
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The invention relates to novel aminomethyl benzene derivatives, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents. (I) wherein A represents one of the groups (I), (I), (I) and
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Page/Page column 39; 41
(2009/10/22)
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- PYRIDIN-2-YL DERIVATIVES AS IMMUNOMODULATING AGENTS
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The invention relates to pyridine derivatives of Formula (I), wherein A, R1, R2, R3, R4, R5, R6 and R7 are as described in the description, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents.
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Page/Page column 38
(2009/10/22)
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- Selected Cgrp-Antagonists, Processes for Preparing Them and Their Use as Pharmaceutical Compositions
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The invention relates to CGRP-antagonists of general formula (I), wherein R1, R2, R3, R4 and R5 are defined in claim 1, to the tautomers, isomers, diastereomers, enantiomers, hydrates, mixtures salts and salt hydrates thereof, in particular to 10 salts thereof, which are physiologically compatible with acids or inorganic or organic bases and to compounds of general formula (I), wherein one or several hydrogen atoms are substituted by deuterium. Drugs containing said compounds, the use thereof and a method for the production thereof are also disclosed.
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Page/Page column 59
(2008/12/08)
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- PYRIDIN-4-YL DERIVATIVES AS IMMUNOMODULATING AGENTS
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The invention relates to pyridine derivatives of Formula (I) wherein A, R1, R2, R3, R4, R5, and R6 are as described in the description, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents.
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Page/Page column 55
(2008/06/13)
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- Novel Thiophene Derivatives as Spingosine-1-Phosphate-1 Receptor Agonists
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The invention relates to novel thiophene derivatives, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunosuppressive agents.
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Page/Page column 15
(2008/12/07)
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- PYRIDIN-3-YL DERIVATIVES AS IMMUNOMODULATING AGENTS
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The invention relates to pyridin-3-yl derivatives of Formula (I) wherein R1, R2, R3, R4, R5; R6 and A are as described in the description, their preparation and their use as pharmaceuticall
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Page/Page column 46
(2008/06/13)
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- AMINO- PYRIDINE DERIVATIVES AS S1P1 /EDG1 RECEPTOR AGONISTS
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The invention relates to novel amino-pyridine derivatives, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents.
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Page/Page column 42
(2008/12/07)
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- Selected CGRP antagonists, processes for preparing them and their use as pharmaceutical compositions
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The present invention relates to the CGRP-antagonists of general formula I wherein R1, R2, R3 and R4 are defined as in claim 1, the tautomers, the isomers, the diastereomers, the enantiomers, the hydrates thereof, the mixtures thereof and the salts thereof and the hydrates of the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, as well as those compounds of general formula I wherein one or more hydrogen atoms are replaced by deuterium, pharmaceutical compositions containing these compounds, their use and processes for preparing them.
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Page/Page column 104
(2008/06/13)
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- Selected CGRP antagonists, process for their preparation as well as their use as medicaments
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Heterocyclic esters (I), their tautomers, diastereomers, enantiomers, hydrates, mixtures and (hydrated) salts, particularly physiologically acceptable salts with (in)organic acids and bases, that are antagonists of calcitonin gene-related peptide (CGRP) a
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- CGRP ANTAGONISTS, METHOD FOR THE PRODUCTION THEREOF, AND THEIR USE AS MEDICAMENTS
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The invention relates to CGRP antagonists of general formula (I) in which: R1, R2, R3, R4 and X are defined as in Claim 1, to their tautomers, isomers, diastereomers, enantiomers, hydrates, mixtures and salts as well as the hydrates of the salts, in particular, their physiologically compatible salts with inorganic or organic acids and bases, and those compounds of general formula (I) in which one or more hydrogen atoms are replaced by deuterium. The invention also relates to medicaments containing these compounds, the use thereof, and to methods for producing them.
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Page/Page column 113-114
(2008/06/13)
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- NOVEL THIOPHENE DERIVATIVES AS SPHINGOSINE-l-PHOSPHATE-1 RECEPTOR AGONISTS
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The invention relates to novel thiophene derivatives of formula (l),their preparation and their use as pharmaceutically active compounds. Said compounds particulary act as immunosuppressive agents. wherein ring A represents oxadiazole and the other substituents are as defined in the description.
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Page/Page column 52-53
(2010/11/24)
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- Halide-free ethylation of phenol by multifunctional catalysis using phosphinite ligands
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The ortho-alkylation of phenols or aniline by catalytic C-H activation and multifunctional catalysis is described. The Royal Society of Chemistry 2006.
- Carrion, M. Carmen,Cole-Hamilton, David J.
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p. 4527 - 4529
(2008/09/18)
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- Dihalopropene compounds, insecticidal/acaricidal agents containing same, and intermediates for their production
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The dihalopropene compounds of the general formula ?I! have excellent insecticidal/acaricidal activity, so that they are satisfactorily effective for the control of noxious insects, mites and ticks.
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- Dihalopropene compounds, insecticides containing them as active ingredients, and intermediates for their production
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The present invention provides dihalopropene compounds of the general formula: STR1 wherein R1 is C1 -C10 alkyl or the like; L is C(=O)NH or the like; R2, R3 and R4 are independently haloge
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- Catalytic ethylation of phenols
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Alkylation of phenol and cresols with ethanol in the presence of iron-aluminum catalyst was studied.
- Agaev,Shakhtakhtinskaya,Eminov,Guliev
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p. 651 - 653
(2007/10/03)
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- o-(α-Benzotriazolylalkyl)phenols: Versatile Intermediates for the Synthesis of Substituted Phenols
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Phenols and naphthols are benzotriazolylmethylated by 1-(hydroxymethyl)-1H-benzotriazole (13) (a formaldehyde derivative) in the o- or (if both o-positions are occupied) in the p-position.The reaction can be extended to other aldehydes in the case of the naphthols.The methylene group in the o-(benzotriazolylmethyl)phenols can be lithiated (but only after trimethylsilyl protection of the hydroxy group) and then substituted by various electrophiles.The benzotriazole residues in both the primary products and in their substituted derivatives can be displaced by the alkylanions of Grignard reagents or by hydride ions allowing the elaboration of many new types of substituted phenols. Key Words: Lithiation/ Mannich reaction/ Alkylation/ Grignard reaction/ Condensation
- Katritzky, Alan R.,Lan, Xiangfu,Lam, Jamshed N.
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p. 1809 - 1817
(2007/10/02)
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- A New Rearrangement of Alkoxybenzyl Anions
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Alkyl groups migrate from oxygen to carbon in alkyl aryl ethers which have been metalated in benzylic positions. 2,6-Dimethylanisole provides a variety of 2,6-dialkylphenols and their ethers in 45-80percent yields.Rearrangement products are obtained in 10-30percent yields from other dimethylanisoles and from methylanisoles.The reactions appear to proceed, like Wittig rearrangements, by homolytic cleavage of the alkyl-oxygen bond followed by recombination of the resulting radical pair in a different way.The rearrangements can be avoided by using methyl ethers and working at or below room temperature.
- Bates, Robert B.,Siahaan, Teruna J.,Suvannachut, Kessara
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p. 1328 - 1334
(2007/10/02)
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- Preparation of diphenolics
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A process for the production of diphenolic compounds having a divalent bridge. A first disubstituted phenol is reacted with an aldehyde in the presence of a secondary amine and excess alcohol to form an ether intermediate. The ether intermediate is reacted with a phenol having an open ortho or para position to form a diphenolic.
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