- PROCESS FOR PREPARING 5-[[4-[2-[5-(1-HYDROXYETHYL)-2-PYRIDINYL]ETHOXY]PHENYL]METHYL]-2,4-THIAZOLIDINEDIONE AND SALTS THEREOF
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The disclosure provides a process of making the compound of Formula I, and pharmaceutically acceptable salts thereof: and the process of making the intermediate of Formula III: wherein PG is as defined as set forth in the specification.
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Paragraph 0261; 0262
(2018/07/29)
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- 2,4-THIAZOLIDINEDIONE DERIVATIVES IN THE TREATMENT OF CENTRAL NERVOUS SYSTEM DISORDERS
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The present invention provides 5-(4-(2-(5-(1-hydroxyethyl)pyridine-2-yl)ethoxy) benzyl)thiazolidine-2,4-dione and novel stereoisomers of said compound for use in the treatment of central nervous system (NS) disorders.
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Page/Page column 23
(2015/11/17)
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- Palladium-catalyzed acetylation of arenes
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A simple method for the preparation of aryl methyl ketones is reported. The transformation involves the Pd-catalyzed coupling of an acyl anion equivalent, acetyltrimethylsilane, with aryl bromides to afford the corresponding acetylated arenes in synthetically useful yields. The methodology is tolerant of heterocycles and provides a new method for arene functionalization.
- Ramgren, Stephen D.,Garg, Neil K.
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supporting information
p. 824 - 827
(2014/03/21)
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- A convenient synthesis of the key intermediate of selective COX-2 inhibitor Etoricoxib
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An original strategy for the synthesis of ketone 1, the key intermediate for preparing Etoricoxib, an important nonsteroidal anti-inflammatory drug, has been developed. Inexpensive 5-hydroxy-2-methylpyridine was converted to the corresponding acetyl derivative in four practical synthetic steps. The following palladium-catalyzed α-arylation of acetylpicoline with 4-bromo- or 4-chlorophenyl methyl sulfone was efficiently optimized in order to afford ketone 1 in remarkable yield.
- Tartaggia, Stefano,Caporale, Andrea,Fontana, Francesco,Stabile, Paolo,Castellin, Andrea,De Lucchi, Ottorino
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p. 18544 - 18549
(2013/10/21)
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- Sustained-release composition containing tetrahydropyrido[4,3-b]indole derivatives and preparation of the derivatives
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The present invention relates to a sustained-release composition containing 2,3,4,5-tetrahydro-2,8-dimethyl-5-[2-(6-methyl-3-pyridyl)ethyl]-1H-pyrido[4,3-b]indole or a pharmaceutically acceptable salt thereof as an active ingredient, preparation thereof and the compound. The composition is suitable for oral administration by one time per day, and achieves the peak plasma concentration at 1.0 to 3 hours after oral administration. The composition is suitable for manufacturing a medicament for treatment of cognitive dysfunction syndrome, Alzheimer's disease, Parkinson's disease, Huntington's disease, or senile dementia.
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Page/Page column 5
(2012/05/21)
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- SUSTAINED RELEASE COMPOSITION CONTAINING TETRAHYDROPYRIDO Y4, 3-b¨INDOLE DERIVATIVE AND PREPARATION METHOD OF DERIVATIVE
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The present invention relates to a sustained-release composition containing 2,3,4,5-tetrahydro-2,8-dimethyl-5-[2-(6-methyl-3-pyridyl)ethyl]-1H-pyrido[4,3-b]indole or a pharmaceutically acceptable salt thereof as an active ingredient, preparation thereof and the compound. The composition is suitable for oral administration by one time per day, and achieves the peak plasma concentration at 1.0 to 3 hours after oral administration. The composition is suitable for manufacturing a medicament for treatment of cognitive dysfunction syndrome, Alzheimer's disease, Parkinson's disease, Huntington's disease, or senile dementia.
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Page/Page column 6-7; 15
(2012/03/08)
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- PROCESS FOR PREPARING 1-(6-METHYLPYRIDIN-3-YL)-2-[4-(METHYLSULFONYL)PHENYL]ETHANONE, AN INTERMEDIATE OF ETORICOXIB
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A process for preparing 1-(6-methylpyridin-3-yl)-2-[4-(methyl sulfonyl)phenyl]ethanone, an intermediate of the synthesis of Etoricoxib. The synthesis of the intermediates useful for such preparation is also described.
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- Improved process for preparing 1-(6-methylpyridin-3-yl)-2-[4-(methylsulfonyl)phenyl]ethanone, an intermediate of etoricoxib
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The present invention relates to a process for preparing 1-(6-methylpyridin-3-yl)-2-[4-(methylsulfonyl)phenyl]ethanone, an intermediate of the synthesis of Etoricoxib. The synthesis of the intermediates useful for such preparation is also described.
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- SYNTHESIS OF 9-(ARYLALKYL)-1,2,3,4-TETRAHYDRO-Υ-CARBOLINE AND ANALOGUES AND INTERMEDIATES
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The present invention pertains generally to methods of preparing certain 9-(arylalkyl)- 1,2,3,4-tetrahydro-Υ-carboline compounds and their analogues, and especially to methods of preparing dimebon. The present invention also pertains to methods of preparing certain intermediate compounds which find use in the synthesis of the 9-(arylalkyl)-1,2,3,4-tetrahydro-γ-carboline compounds.
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Page/Page column 58
(2010/07/02)
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- METHODS AND COMPOSITIONS RELATED TO WRAPPING OF DEHYDRONS
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This application describes a novel technology in drug discovery and drug-based imaging/detection: the wrapping technology. This technology is based on identified singularities in the structure of soluble proteins. In contrast with drug-design approaches based on standard structural considerations, the packing of a protein, or more precisely, its dehydron pattern, may be used as a selectivity filter to design small-molecule inhibitors. The wrapping technology described herein is a novel form of rational drug design for avoiding side effects in drug therapy and sharpening the inhibitory impact of drugs on the oncokinome.
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Page/Page column 40-41
(2008/12/06)
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- SUBSTITUTED PYRIDYLMETHYL BICYCLOCARBOXYAMIDE COMPOUNDS
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This invention provides a compound of the formula (I): wherein A1 is N and A2 is CR7, or A1 is CR7 and A2 is N; Y1, Y2 and Y3 are each independently CH or N, Y4 and Y5 are each independently CR8 or N, with the proviso that when one of Y1, Y2, Y3, Y4 and Y5 is N, the others are not N; R1 and R2 are each independently hydrogen, halogen, (C1-C6)alkyl, halo(C1-C6)alkyl or hydroxy(C1-C6)alkyl; R3 and R8 are each independently hydrogen, halogen, hydroxy, (C1-C6)alkyl, hydroxy(C1-C6)alkoxy, (C1-C6)alkoxy-(C1-C6)alkyl, (C1-C6)alkoxy-(C1-C6)alkoxy, halo(C1-C6)alkyl, (C1-C6)alkylthio, (C1-C6)alkylsulfinyl or (C1-C6)alkylsulfonyl; R4 is halogen, (C1-C6)alkyl, (C3-C6)cycloalkyl, halo(C1-C6)alkyl, hydroxy(C1-C6)alkyl, halo(C1-C6)alkoxy, hydroxy(C1-C6)alkoxy, (C1-C6)alkoxy-(C1-C6)alkyl, (C1-C6)aIkoxy-(C1-C6)alkoxy, halo(C1-C6)alkylsuIfonyl, halo(C1-C6)alkylsulfinyl, halo(C1-C6)alkylthio, [(C1-C6)alkyl]NH- or [(C1-C6)alkyl]2N-; and R5, R6 and R7 are each independently hydrogen, halogen, (C1-C6)alkyl, hydroxy(C1-C6)alkyI, or (C1-C6)alkoxy; or a pharmaceutically acceptable salt, solvate thereof. These compounds are useful for the treatment of disease conditions caused by overactivation of the VR1 receptor such as pain, or the like in mammal. This invention also provides a pharmaceutical composition comprising the above compound.
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- PYRIDAZIN-3 (2H) -ONE DERIVATIVES AND THEIR USE AS PDE4 INHIBITORS
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New pyridazin-e-(2H)-one derivatives having the chemical structure of general formula (I) are disclosed; as well as processes for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of phosphodiesterase 4.
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Page/Page column 82-83
(2008/06/13)
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- A concise route to novel 1-aryl and 1-pyridyl-2-azabicyclo[2.1.1]hexanes
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A number of novel 1-aryl and 1-pyridyl-2-azabicyclo[2.1.1]hexane derivatives were prepared by an intramolecular [2+2] photocycloaddition in the presence of acetophenone as the sensitizer. Substitution of the azabicyclo[2.1.1]hexane ring was accomplished by appropriate choice of the heteroaryl ketone and allylamine starting materials. Several aryl 9a-e, g and pyridyl analogs 9h-l were prepared by this method. The structures of 9a and 9i were verified by X-ray crystallography. Several of the photoproducts 9 were converted into the corresponding N-Me and N-H 2,4-methanonicotine analogs 4 by reduction or hydrolysis of the N-carboethoxy group.
- Piotrowski, David W.
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p. 1091 - 1093
(2007/10/03)
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- Synthesis and biological activity of metabolites of the antidiabetic, antihyperglycemic agent pioglitazone
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Pioglitazone (5-(4-(2-(5-ethyl-2-pyridyl)ethoxy)benzyl)-2,4- thiazolidinedione, 2) is a prototypical antidiabetic thiazolidinedione that had been evaluated for possible clinical development. Metabolites 6-9 have been identified after dosing of rats and dogs. Ketone 10 has not yet been identified as a metabolite but has been added to the list as a putative metabolite by analogy to alcohol 6 and ketone 7. We have developed improved syntheses of pioglitazone (2) metabolites 6-9 and the putative metabolite ketone 10. These entities have been compared in the KKA(y) mouse model of human type-II diabetes to pioglitazone (2). Ketone 10 has proven to be the most potent of these thiazolidinediones in this in vivo assay. When 6-10 were compared in vitro in the 3T3-L1 cell line to 2, for their ability to augment insulin-stimulated lipogenesis, 10 was again the most potent compound with 6, 7, and 9 roughly equivalent to 2. These data suggest that metabolites 6, 7, and 9 are likely to contribute to the pharmacological activity of pioglitazone (2), as had been previously reported for ciglitazone (1).
- Tanis, Steven P.,Parker, Timothy T.,Colca, Jerry R.,Fisher, Roberta M.,Kletzein, Rolf F.
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p. 5053 - 5063
(2007/10/03)
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- REACTION OF 1-ETHOXY-1-BUTEN-3-ONE WITH AMINES
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In the reaction of 1-ethoxy-1-buten-3-one with ammonia and primary and secondary amines the alkoxy group is substituted by an amino group.In the reaction with ammonia 1-amino-1-buten-3-one condenses with the formation of 2-methyl-5-acetylpyridine.
- Markova, N. K.,Zaichenko, Yu. A.,Tsil'ko, A. E.,Maretina, I. A.
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p. 876 - 880
(2007/10/02)
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- 3-(Pyridinyl)-2-cyclohexen-1-ones
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3-(4 OR 3-Pyridinyl)-2-cyclohexen-1-ones (I) and their oxime derivatives are useful in preparing (3-aminophenyl)-pyridines, in turn, useful in preparing known antibacterial agents. Also shown is the preparation of I by starting with the reaction of methyl vinyl ketone with either 1-(pyridinyl)-1-(lower-tertiary-amino)-ethylene (II) or lower-alkyl 3-(pyridinyl)-3-oxopropanoate. Also shown is the process of converting I to its oxime, acylating the oxime and heating the acylated oxime under acidic conditions to produce N-(lower-acyl)-3-(pyridinyl)-aniline (VII), and hydrolyzing VII under aqueous alkaline conditions to produce the corresponding 3-(pyridinyl)aniline.
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