- Application of 7-azaisatins in enantioselective Morita-Baylis-Hillman reaction
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7-Azaisatin and 7-azaoxindole skeletons are valuable building blocks in diverse biologically active substances. Here 7-azaisatins turned out to be more efficient electrophiles than the analogous isatins in the enantioselective Morita-Baylis-Hillman (MBH) reactions with maleimides using a bifunctional tertiary amine, β-isocupreidine (β-ICD), as the catalyst. This route allows a convenient approach to access multifunctional 3-hydroxy-7-aza-2-oxindoles with high enantiopurity (up to 94% ee). Other types of activated alkenes, such as acrylates and acrolein, could also be efficiently utilized.
- He, Qing,Zhan, Gu,Du, Wei,Chen, Ying-Chun
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supporting information
p. 309 - 313
(2016/04/05)
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- TRICYCLIC DLK INHIBITORS AND USES THEREOF
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The invention relates to compounds of formula (I) and salts thereof, wherein ring A and R1-R2 have any of the values defined in the specification. The compounds and salts are useful for treating DLK mediated disorders. The invention also provides pharmaceutical compositions comprising a compound of formula (I), or a pharmaceutically acceptable salt thereof, as well as methods of using said compounds, salts, or compositions as DLK inhibitors and for treating neurodegeneration diseases and disorders.
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Page/Page column 79-80
(2016/09/26)
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- Synthesizing method of 5-bromine-1H-pyrrolo[2,3-b]pyridine
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The invention particularly relates to a synthesizing method of 5-bromine-1H-pyrrolo[2,3-b]pyridine. The synthesizing method is characterized in that 1H-pyrrolo[2,3-b]pyridine is dissolved in a solvent to have bromination reaction with a brominating agent under 5-40 DEG C, and reductive dehalogenation is performed under 20-50 DEG C after the bromination reaction to obtain 5-bromine-1,3-dihydro-2H-pyrrolo[2,3-b]pyridine-2-ketone; under the effect of a reducing agent, the 5-bromine-1,3-dihydro-2H-pyrrolo[2,3-b]pyridine-2-ketone has reduction reaction in a certain solvent under 25-40 DEG C, and oxidative dehydrogenation is performed at 25-60 DEG C after the reduction reaction to obtain the 5-bromine-1H-pyrrolo[2,3-b]pyridine. The synthesizing method has the advantages that the method is simple in reaction step and mild in reaction condition, the four-step reaction is simplified into two one-pot two-step reactions, the treatment process is simplified, and the use amount of organic solvents is reduced.
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Paragraph 0025
(2016/12/22)
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- Design, synthesis and biological evaluation of 1H-pyrrolo[2,3-b]pyridine and 1H-pyrazolo[3,4-b]pyridine derivatives as c-Met inhibitors
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Five novel 1H-pyrrolo[2,3-b]pyridine or 1H-pyrazolo[3,4-b]pyridine derivatives, with a methylene, sulfur, sulfoxide or cyclopropyl group as a linker, were designed, synthesized and biologically evaluated against c-Met and ALK. The development of these methods of compound synthesis may provide an important reference for the construction of novel 7-azaindole and 7-azaindazole derivatives with a single atom linker. The enzyme assay and cell assay in vitro showed that compound 9 displayed strong c-Met kinase inhibition with IC50 of 22.8 nM, moderate ALK kinase inhibition, and strong cell inhibition with MKN-45 IC50 of 329 nM and EBC-1 IC50 of 479 nM. In order to find the better candidate compounds, compounds 8, 9 and 10 have been selected as tool compounds for further optimization.
- Liu, Na,Wang, Yanfen,Huang, Gongchao,Ji, Conghui,Fan, Wei,Li, Haitao,Cheng, Ying,Tian, Hongqi
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p. 146 - 158
(2016/03/12)
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- 3-SUBSTITUTED PYRAZOLES AND USE AS DLK INHIBITORS
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The present invention provides for compounds of Formula (I) and various embodiments thereof, and compositions comprising compounds of Formula (I) and various embodiments thereof. (I) In compounds of Formula I, the groups R1, R2, R3, R4, R5, R6 and R7 have the meaning as described herein. The present invention also provides for methods of using compounds of Formula I and compositions comprising compounds of Formula (I) as DLK inhibitors and for treating neurodegeneration diseases and disorders.
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Page/Page column 111
(2014/08/06)
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- New bicyclic compounds as crac channel modulators
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The present invention relates to novel compounds which are inhibitors of CRAC channel activity. This invention also relates to pharmaceutical compositions containing them, process for their preparation and their use in therapy.
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Paragraph 0104
(2014/06/24)
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- 7-AZAINDOLE INHIBITORS OF CRAC
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Disclosed are compounds of Formula (I), useful for treatment of autoimmune and inflammatory diseases associated with IL-2 inhibition via modulation of calcium release-activated calcium (CRAC) channels. Also disclosed are methods of making and using the compounds for treatment of diseases associated with CRAC channels.
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Paragraph 0185
(2013/06/28)
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- HISTAMINE H3 INVERSE AGONISTS AND ANTAGONISTS AND METHODS OF USE THEREOF
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Provided herein are fused imidazolyl compounds, methods of synthesis, and methods of use thereof. The compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, such as neurological disorders and metabolic disorders. Compounds provided herein inhibit the activity of histamine H3 receptors and modulate the release of various neurotransmitters, such as histamine, acetylcholine, norepinephrine, and dopamine (e.g. at the synapse). Pharmaceutical formulations containing the compounds and their methods of use are also provided herein.
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Page/Page column 113
(2010/08/18)
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- Synthesis of 7-azaserotonin: Its photophysical properties associated with excited state proton transfer reaction
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We report the synthesis of 3-(2-aminoethyl)-5-ol-1H-pyrrolo[2,3-b]pyridine (7-azaserotonin), which may potentially serve as an agonist or antagonist of serotonin receptors. In alcohols, the solvent (e.g., ethanol) catalyzed proton-transfer reaction takes place for 7-azaserotonin in the excited state, resulting in dual emission. Conversely, excited-state deprotonation takes place in neutral aqueous solution. The unique excitation behavior makes 7-azaserotonin versatile as a potential bioprobe. Copyright
- Wu, Pei-Wen,Hsieh, Wan-Ting,Cheng, Yi-Ming,Wei, Ching-Yen,Chou, Pi-Tai
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p. 14426 - 14427
(2008/01/27)
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- Discovery and in vitro evaluation of potent TrkA kinase inhibitors: Oxindole and aza-oxindoles
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The discovery, synthesis, potential binding mode, and in vitro kinase profile of 3-(3-bromo-4-hydroxy-5-(2′-methoxyphenyl)-benzylidene)-5-bromo- 1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one, 3-[(1-methyl-1H-indol-3-yl)methylene]- 1,3-dihydro-2H-pyrrolo[3,2-b]-pyridin-2-one as potent TrkA inhibitors are discussed.
- Wood, Edgar R.,Kuyper, Lee,Petrov, Kimberly G.,Hunter III, Robert N.,Harris, Philip A.,Lackey, Karen
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p. 953 - 957
(2007/10/03)
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- Oxindole derivatives
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The present invention is related to oxindole derivatives, compositions containing the same, and methods of use and manufacture of the same. Such compounds generally are useful pharmacologically as agents in those disease states alleviated by the alteration of mitogen activated signaling pathways in general, and in particular in the inhibition or antagonism of protein kinases, which pathologically involve aberrant cellular proliferation. Such disease states include tumor growth, restenosis, atherosclerosis, pain and thrombosis. In particular, the present invention relates to a series of substituted oxindole compounds, which exhibit Trk family protein tyrosine kinase inhibition, and which are useful in cancer therapy and chronic pain indications.
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- AZAINDOLES AS INHIBITORS OF C-JUN N-TERMINAL KINASES
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The present invention relates to novel 5-substituted 7-azaindole compounds of formula (I), their use in the inhibition of c-Jun N-terminal kinases, their use in medicine and particularly in the prevention and/or treatment of neurodegenerative disorders re
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Page/Page column 23
(2008/06/13)
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- 7-AZAINDOLES AS INHIBITORS OF C-JUN N-TERMINAL KINASES FOR THE TREATMENT OF NEURODEGENERATIVE DISORDERS
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The present invention relates to novel 3,5-substituted 7-azaindole compounds of formula (I), their use in the inhibition of c-Jun N-terminal kinases, their use in medecine and particularly in the prevention and/or treatment of neurodegenerative disorders
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Page/Page column 31-32
(2008/06/13)
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- Substituted aza-oxindole derivatives
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Substituted aza-oxindole derivatives useful as cyclin dependent kinase 11 inhibitors, for preventing/reducing the severity of epithelial cytotoxicity side-effects (e.g., alopecia, plantar-palmar syndrome, mucositis) induced by chemoptherapy and/or radiati
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- Synthesis of new melatonin analogues from dimers of azaindole and indole by use of Suzuki homocoupling
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N-{2-[3′-(2-Acetylaminoethyl)-1H,1′H-[5,5′]biindol-3-yl]- and N-{2-[1′-(2-acetylaminoethyl)-1′H-[5, 5′]biindol-1-yl]ethyl}acetamide (2,3) and their analogues in 7-azaindole series (4,5) were synthesized by palladium catalysed reaction starting from indole or 7-azaindole using [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium, as catalyst.
- Guillard, Jerome,Larraya, Carlos,Viaud-Massuard, Marie-Claude
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p. 865 - 877
(2007/10/03)
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- 3-(anilinomethylene) oxindoles
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The present invention relates generally to novel amine substituted oxindole compounds and compositions. Such compounds and compositions have utility as pharmacological agents in treating diseases or conditions alleviated by the inhibition or antagonism of
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Page column 37-38
(2010/02/04)
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- Polycyclic azaindole compounds
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The invention relates to compounds of formula (I): wherein: G1represents an alkylene chain as defined in the description, A represents R2and R3represent hydrogen, alkyl, alkoxy or hydroxy or together form oxo, R4and R5represent hydrogen or together form aryl, R1is as defined in the description. and medicinal products containing the same which are useful in treating or preventing melatoninergic disorders.
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- Synthesis of new melatoninergic ligands including azaindole moiety
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A novel series of melatonin analogues, based on the azaindole nucleus is described. These compounds are prepared in several steps directly from the commercial available 7-azaindole or from substituted amino-, iodo- or/and nitropyridines using a catalysed palladium reaction or vicarious nucleophilic substitution of hydrogen (VNS) in order to elaborate the 6-, 5- and 4- azaindole derivatives respectively.
- Mazéas, Daniel,Guillaumet, Gérald,Viaud, Marie-Claude
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p. 1065 - 1080
(2007/10/03)
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