- Strategic Approach on N-Oxides in Gold Catalysis – A Case Study
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An extensive kinetic study of selected key reactions of (oxidative) gold catalysis concentrates on the decrease of the catalytic activity due to inhibition of the gold(I) catalyst caused by pyridine derivatives that are obtained as by-products if N-oxides are applied as oxygen donors. The choice of the examined pyridine derivatives and their corresponding N-oxides has been made regardless of their commercial availability; particular attention has been paid to the practical benefit which up to now has been neglected in most of the reaction screenings. The test reactions were monitored by GC and 1H NMR spectroscopy. The received reaction constants provide information concerning a correlation between the electronic structure of the heterocycle and the catalytic activity. Based on the collected kinetic data, it was possible to develop a basic set of three N-oxides which have to be taken into account in further oxidative gold(I)-catalyzed reactions. (Figure presented.).
- Schie?l, Jasmin,Stein, Philipp M.,Stirn, Judith,Emler, Kirsten,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
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p. 725 - 738
(2018/10/20)
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- THIADIAZOLES AS CXC- AND CC- CHEMOKINE RECEPTOR LIGANDS
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Disclosed are novel compounds of Formula (IA) and the pharmaceutically acceptable salts and solvates thereof. Examples of groups comprising Substituent A include heteroaryl, aryl, heterocycloalkyl, cycloalkyl, aryl, alkynyl, alkenyl, aminoalkyl, alkyl or amino. Examples of groups comprising Substituent B include aryl and heteroaryl. Also disclosed is a method of treating a chemokine mediated diseases, such as, cancer, angiogenisis, angiogenic ocular diseases, pulmonary diseases, multiple sclerosis, rheumatoid arthritis, osteoarthritis, stroke and ischemia reperfusion injury, pain (e.g., acute pain, acute and chronic inflammatory pain, and neuropathic pain) using a compound of Formula (IA).
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Page/Page column 124
(2010/02/12)
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- ISOTHIAZOLE DIOXIDES AS CXC- AND CC- CHEMOKINE RECEPTOR LIGANDS
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Disclosed are novel compounds of the formula (IA): and the pharmaceutically acceptable salts and solvates thereof. D and E are different groups wherein one is N and the other is CR50. Examples of groups comprising Substituent A include heteroaryl, aryl, heterocycloalkyl, cycloalkyl, aryl, alkynyl, alkenyl, aminoalkyl, alkyl or amino. Examples of groups comprising Substituent B include aryl and heteroaryl. Also disclosed is a method of treating a chemokine mediated diseases, such as, cancer, angiogenisis, angiogenic ocular diseases, pulmonary diseases, multiple sclerosis, rheumatoid arthritis, osteoarthritis, stroke and cardiac reperfusion injury, pain (e.g., acute pain, acute and chronic inflammatory pain, and neuropathic pain) using a compound of formula IA.
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Page/Page column 127
(2010/02/13)
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- THIADIAZOLEDIOXIDES AND THIADIAZOLEOXIDES AS CXC- AND CC-CHEMOKINE RECEPTOR LIGANDS
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Disclosed are novel compounds of the formula (IA) and the pharmaceutically acceptable salts and solvates thereof. Examples of groups comprising Substituent A include heteroaryl, aryl, heterocycloalkyl, cycloalkyl, aryl, alkynyl, alkenyl, aminoalkyl, alkyl or amino. Examples of groups comprising Substituent B include aryl and heteroaryl. Also disclosed is a method of treating a chemokine mediated diseases, such as, cancer, angiogenisis, angiogenic ocular diseases, pulmonary diseases, multiple sclerosis, rheumatoid arthritis, osteoarthritis, stroke and cardiac reperfusion injury, acute pain, acute and chronic inflammatory pain, and neuropathic pain using a compound of formula (IA).
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- 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands
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There are disclosed compounds of the formula or a pharmaceutically acceptable salt or solvate thereof which are useful for the treatment of chemokine-mediated diseases such as acute and chronic inflammatory disorders and cancer.
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- 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands
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There are disclosed compounds of the formula or a pharmaceutically acceptable salt or solvate thereof which are useful for the treatment of chemokine-mediated diseases such as acute and chronic inflammatory disorders and cancer.
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- Nitration of Some Derivatives of 2- Methylaminopyridine N-Oxides
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The only stable products obtained from nitrations of 2-methylaminopyridine N-oxide and some derivatives, are those resulting from nitration of the pyridine ring.Thus, 2-methyl-aminopyridine N-oxide 8 is nitrated under mild conditions to yield 2-methylamino-5-nitropyridine N-oxide 9, but not 2-methylnitraminopyridine-N-oxide as might be expected.Under stronger nitrating conditions 2-methylamino-3,5-dinitropyridine N-oxide 10 is obtained. 2-Methylamino-4-nitropyridine N-oxide 1 yields 2-methylamino-4,5-dinitropyridine N-oxide 2 upon nitration.Chemical reactions which re late known compounds to the new compounds obtained, confirm the assigned structures.
- Talik, Tadeusz,Talic, Zofia
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- Reactions of N-Heteroaromatic Bases with Nitrous Acid. Part 6. Kinetics of the Nitrosation of 2- and 4-Methylaminpprridine and their 1-Oxide Derivates
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The nitrosation of 2- and 4-methylaminopyridine and their 1-oxide derivates in 0.002-5.00 M-perchoric acid is of first order in a both the amine and nitrous acid.The respective nitrosamines formed are easily denitrosated under the experimental conditions.The rate coefficients of the nitrosation increase with an increase in the concenration of perchloric acid and sodium perchlorate.In perchloric acid solution whose ionic strength is maintained constant by the addition of sodium perchlorate the rate coefficients of the nitrosation of 2- and 4-methylaminopyridine only show rectilinear dependence on the h0 parameter of the medium.The nitrosation of 2- and 4-methylaminopyridine proceeds mainly by the interaction of the nitrous acidium ion with the protonated form of these amines whilst the nitrosation of 2- and 4-methylaminopyridine 1-oxide proceeds by the simultaneous interaction of the nitrous acidium ion with the protonated and the free form of both amines.The nitrous acidium ion seems to show a distinct discrimination in its reaction with free form of the amines as evidenced by a rectilinear relationship between the rate coefficient of ther nitrosation and their Ka values.The protonated amine 1-oxides react faster than the protonated amines when the hydroxy-group is in para-position with respect to the amino-group and therefore not involved in hydrogen bonding with it.The nitrosation of free and the protonated amines involves an initial interaction between the nitrosating agent and the heteroaromatic nucleus.The present results show that the formation of the respective N-nitroso-derivate is the rate-determining stage of the diazotisation of the N-heteroaromatic amines over the whole of the acid range examined. pKa Values are recorded.
- Kalatzis, Evangelos,Papadopoulos, Panayiotis
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p. 239 - 247
(2007/10/02)
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