13959-02-9Relevant articles and documents
High-yield synthesis method of methyl 3-aminoisonicotinate
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Paragraph 0013; 0015; 0019; 0023, (2020/05/01)
The invention belongs to the field of chemical pharmacy, and particularly discloses a high-yield synthesis method of methyl 3-aminoisonicotinate. According to the high-yield synthesis method, 4-picolinic acid is used as a raw material and subjected to brominating, ammonifying and esterifying to obtain methyl 3-aminoisonicotinate. The high-yield synthesis method of methyl 3-aminoisonicotinate has the advantages of mild reaction conditions, high total yield, realization of repeated use of a 3-bromo-4-picolinic acid reaction waste filtrate, improvement of the utilization rate of the raw material,reduction of resource waste, maximum reduction of the production cost of the whole process, and extremely high application value.
Method for synthesizing 3-bromoisonicotinic acid intermediate
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Paragraph 0010, (2019/07/04)
The invention relates to a method for synthesizing a 3-bromoisonicotinic acid intermediate, and belongs to the technical field of pharmaceutical intermediates. The process comprises the following steps: 4-methylpyridine is adopted as a raw material, and the 4-methylpyridine is reacted with bromine under the catalysis of an aluminum trichloride catalyst to form intermediate 3-bromo-4-methylpyridine; and a novel catalyst Co0.27CuO3 is added, oxygen is introduced for oxidization to form the target product 3-bromoisonicotinic acid. According to the method provided by the invention, in the oxidation reaction process, water is used as a solvent, the novel catalyst Co0.27CuO3 is introduced, the oxygen is used as an oxidant to replace a traditional KMnO4 oxidant, so that pollution of heavy metalsto the environment can be avoided; because the novel catalyst is not affected by the reaction environment, catalytic activity of the novel catalyst is not reduced, and after 25 cycles, activity of thecatalyst is not significantly reduced; and the method has the advantages of greatly improving the yield, reducing the costs, improving the safety, saving the energy, and the like, and conforms to modern chemical industry production requirements of a green reaction.
Structure-based design, synthesis and evaluation in vitro of arylnaphthyridinones, arylpyridopyrimidinones and their tetrahydro derivatives as inhibitors of the tankyrases
Kumpan, Katerina,Nathubhai, Amit,Zhang, Chenlu,Wood, Pauline J.,Lloyd, Matthew D.,Thompson, Andrew S.,Haikarainen, Teemu,Lehti?, Lari,Threadgill, Michael D.
supporting information, p. 3013 - 3032 (2015/08/03)
Abstract The tankyrases are members of the PARP superfamily; they poly(ADP-ribosyl)ate their target proteins using NAD+ as a source of electrophilic ADP-ribosyl units. The three principal protein substrates of the tankyrases (TRF1, NuMA and axin) are involved in replication of cancer cells; thus inhibitors of the tankyrases may have anticancer activity. Using structure-based drug design and by analogy with known 3-arylisoquinolin-1-one and 2-arylquinazolin-4-one inhibitors, series of arylnaphthyridinones, arylpyridinopyrimidinones and their tetrahydro-derivatives were synthesised and evaluated in vitro. 7-Aryl-1,6-naphthyridin-5-ones, 3-aryl-2,6-naphthyridin-1-ones and 3-aryl-2,7-naphthyridin-1-ones were prepared by acid-catalysed cyclisation of the corresponding arylethynylpyridinenitriles or reaction of bromopyridinecarboxylic acids with β-diketones, followed by treatment with NH3. The 7-aryl-1,6-naphthyridin-5-ones were methylated at 1-N and reduced to 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones. Cu-catalysed reaction of benzamidines with bromopyridinecarboxylic acids furnished 2-arylpyrido[2,3-d]pyrimidin-4-ones. Condensation of benzamidines with methyl 1-benzyl-4-oxopiperidine-3-carboxylate and deprotection gave 2-aryl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ones, aza analogues of the known inhibitor XAV939. Introduction of the ring-N in the arylnaphthyridinones and the arylpyridopyrimidinones caused >1000-fold loss in activity, compared with their carbocyclic isoquinolinone and quinazolinone analogues. However, the 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones showed excellent inhibition of the tankyrases, with some examples having IC50 = 2 nM. One compound (7-(4-bromophenyl)-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-one) showed 70-fold selectivity for inhibition of tankyrase-2 versus tankyrase-1. The mode of binding was explored through crystal structures of inhibitors in complex with tankyrase-2.
COMPOSITION AND METHOD FOR CONTROLLING ARTHROPOD PESTS
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Page/Page column 210-211, (2011/05/06)
The present invention provides: an arthropod pests control composition comprising, as active ingredients, a condensed heterocyclic compound and a pyrethroid compound; a method for controlling arthropod pests which comprises applying effective amounts of a condensed heterocyclic compound and a pyrethroid compound to the arthropod pests or a locus where the arthropod pests inhabit; and so on.
HARMFUL ARTHROPOD CONTROL COMPOSITION, AND FUSED HETEROCYCLIC COMPOUND
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Page/Page column 126, (2011/02/18)
Disclosed is a harmful arthropod control composition comprising, as an active ingredient, a fused heterocyclic compound represented by formula (1) [wherein A1 and A2 independently represent a nitrogen atom or the like; R1 and R4 independently represent a halogen atom or the like; R2 and R3 independently represent a halogen atom or the like; R5 and R6 independently represent a linear C1-C6 hydrocarbon group which may be substituted, or the like (provided that both R5 and R6 cannot represent a hydrogen atom simultaneously); and n represents 0 or 1]. The harmful arthropod control composition has an excellent efficacy to control harmful arthropods.
HARMFUL ARTHROPOD CONTROL COMPOSITION, AND FUSED HETEROCYCLIC COMPOUND
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Page/Page column 79, (2011/04/13)
Disclosed is a harmful arthropod control composition comprising, as an active ingredient, a fused heterocyclic compound represented by formula (1) [wherein A1 and A2 independently represent a nitrogen atom or the like; R1 and R4 independently represent a halogen atom or the like; R2 and R3 independently represent a halogen atom or the like; R5 and R6 independently represent a linear C1-C6 hydrocarbon group which may be substituted, or the like (provided that both R5 and R6 cannot represent a hydrogen atom simultaneously); and n represents 0 or 1]. The harmful arthropod control composition has an excellent efficacy to control harmful arthropods.
COMPOSITION AND METHOD FOR CONTROLLING ARTHROPOD PESTS
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Page/Page column 210, (2011/04/25)
The present invention provides: an arthropod pests control composition comprising, as active ingredients, a condensed heterocyclic compound and a neonicotinoid compound; a method for controlling arthropod pests which comprises applying effective amounts of a condensed heterocyclic compound and a neonicotinoid compound to the arthropod pests or a locus where the arthropod pests inhabit; and so on.
COMPOSITION AND METHOD FOR CONTROLLING ARTHROPOD PESTS
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Page/Page column 209, (2011/05/06)
The present invention provides: an arthropod pests control composition comprising, as active ingredients, a condensed heterocyclic compound and pyriproxyfen; a method for controlling arthropod pests which comprises applying effective amounts of a condensed heterocyclic compound and pyriproxyfen to the arthropod pests or a locus where the arthropod pests inhabit; and so on.
COMPOSITION AND METHOD FOR CONTROLLING ARTHROPOD PESTS
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Page/Page column 209, (2011/05/06)
The present invention provides: an arthropod pests control composition comprising, as active ingredients, a condensed heterocyclic compound and pyridalyl; a method for controlling arthropod pests which comprises applying effective amounts of a condensed heterocyclic compound and pyridalyl to the arthropod pests or a locus where the arthropod pests inhabit; and so on.
COMPOSITION AND METHOD FOR CONTROLLING ARTHROPOD PESTS
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Page/Page column 213-214, (2011/05/06)
The present invention provides: an arthropod pests control composition comprising, as active ingredients, a condensed heterocyclic compound and a diamide compound; a method for controlling arthropod pests which comprises applying effective amounts of a condensed heterocyclic compound and a diamide compound to the arthropod pests or a locus where the arthropod pests inhabit; and so on.