4664-08-8Relevant academic research and scientific papers
High-yield synthesis method of methyl 4-aminonicotinate
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Paragraph 0024-0027; 0033-0036; 0042-0045, (2021/09/08)
The invention discloses a high-yield synthesis method of methyl 4-aminonicotinate, which comprises the following steps: by taking 3, 4-dipicolinic acid as a raw material, carrying out intramolecular dehydration substitution, ammonia ammonification, improved NBS Hofmann rearrangement and hydrolysis to obtain the methyl 4-aminonicotinate. The synthesis method disclosed by the invention is simpler to operate, mild in reaction condition and higher in total yield, and has an extremely high application value.
The synthesis of 7,8,9,10-Tetrafluoroellipticine
James Gruver,Onyango, Evans O.,Gribble, Gordon W.
, p. 144 - 152 (2018/07/05)
We have synthesized a novel ellipticine analogue, 7,8,9,10-Tetrafluoroellipticine, in nine steps from hexafluorobenzene and ethyl cyanoacetate, via 1-(phenysulfonyl)-4,5,6,7-Tetrafluoroindole. The key step is lithiation of the indole and subsequent coupling with 3,4-pyridinedicarboxylic acid anhydride to afford a ketolactam. Reaction of the lactam with methyllithium followed by reduction with sodium borohydride yields 7,8,9,10-Tetrafluoroellipticine. formula presented.
A cedar Joan maleic acid salt preparation method
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Paragraph 0042; 0043; 0044, (2017/08/25)
The invention provides a pixantrone maleate synthesis method which has the advantages of high yield, low impurity content, simple process and easiness in large-scale production. In the method, pyridine-3,4-dicarboxylic acid is used as a starting raw material which reacts with acetic anhydride to obtain pyridine-3,4-dicarboxylic anhydride; the pyridine-3,4-dicarboxylic anhydride conducts an Friedel-Crafts acylation reaction with 1,4-difluorobenzene, and the obtained mixture is subjected to catalytic cyclization to obtain a key intermediate; the intermediate reacts with amino-protected ethylenediamine to obtain protecting group-containing pixantrone; and after that, deprotection and salifying are performed to obtain the target product. In the Friedel-Crafts acylation reaction of the method, an n-hexane solution of sulfuric acid is used as a catalyst, thus the use is convenient, the aftertreatment is simple, and the potential risk in production is eliminated; the Cbz or Fmoc protected ethylenediamine reacts with substituted anthraquinone and then the protecting group is removed through catalytic hydrogenation to obtain pixantrone; the process effectively inhibits side reactions and reduces the impurity content; and meanwhile, the aftertreatment is simplified, and the yield increase is facilitated.
ISOQUINOLINESULFONYL DERIVATIVE AS RHO KINASE INHIBITOR
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Paragraph 0132; 0133, (2017/06/12)
The present invention discloses a class of isoquinolinesulfonyl derivatives as RHO kinase inhibitors, and pharmaceutical compositions thereof, and relates to pharmaceutically acceptable uses thereof. Specifically, the present invention relates to a compound as represented by formula (I), or a pharmaceutically acceptable salt thereof.
PYRIDAZINE DERIVATIVES AS HEDGEHOG PATHWAY INHIBITORS
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Paragraph 00183, (2015/01/16)
This invention relates to novel compounds. The compounds of the invention are hedgehog pathway agonists. Specifically, the compounds of the invention are useful as Smoothened (SMO) agonists. The invention also contemplates the use of the compounds for treating conditions treatable by the inhibition of the Hedgehog pathway and SMO, for example cancer.
HETEROCYCLIC COMPOUNDS AS HEDGEHOG SIGNALING PATHWAY INHIBITORS
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Paragraph 00234, (2014/12/12)
This invention relates to novel compounds of formula (I). The compounds of the invention are hedgehog pathway antagonists. Specifically, the compounds of the invention are useful as Smoothened (SMO) inhibitors. The invention also contemplates the use of the compounds for treating conditions treatable by the inhibition of the Hedgehog pathway and SMO, for example cancer.
Design and synthesis of 6-fluoro-2-naphthyl derivatives as novel CCR3 antagonists with reduced CYP2D6 inhibition
Sato, Ippei,Morihira, Koichiro,Inami, Hiroshi,Kubota, Hirokazu,Morokata, Tatsuaki,Suzuki, Keiko,Iura, Yosuke,Nitta, Aiko,Imaoka, Takayuki,Takahashi, Toshiya,Takeuchi, Makoto,Ohta, Mitsuaki,Tsukamoto, Shin-ichi
, p. 8607 - 8618 (2008/12/23)
In our previous study on discovering novel types of CCR3 antagonists, we found a fluoronaphthalene derivative (1) that exhibited potent CCR3 inhibitory activity with an IC50 value of 20 nM. However, compound 1 also inhibited human cytochrome P450 2D6 (CYP2D6) with an IC50 value of 400 nM. In order to reduce its CYP2D6 inhibitory activity, we performed further systematic structural modifications on 1. In particular, we focused on reducing the number of lipophilic moieties in the biphenyl part of 1, using C log D7.4 values as the reference index of lipophilicity. This research led to the identification of N-{(3-exo)-8-[(6-fluoro-2-naphthyl)methyl]-8-azabicyclo[3.2.1]oct-3-yl}-3-(piperidin-1-ylcarbonyl)isonicotinamide 1-oxide (30) which showed comparable CCR3 inhibitory activity (IC50 = 23 nM) with much reduced CYP2D6 inhibitory activity (IC50 = 29,000 nM) compared with 1.
Hetero-annulated indazoles
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, (2008/06/13)
This invention is directed to heteroannulated indazoles namely to 2,5-disubstituted quinolino-, isoquinolino-, phthalazino-, and quinoxalino- annulated indazole-6(2H)-ones and related mono N-oxides. These compounds have been shown to have antitumor activity.
2-aminoalkyl-5-aminoalkylamino substituted-isoquinoindazole-6(2H)-ones
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, (2008/06/13)
This invention is directed to 2-aminoalkyl-5-aminoalkylamino substituted isoquino [8,7,6-cd]indazole-6-(2H)-ones and to 2-aminoalkyl-5-aminoalkylamino substituted-isoquino [5,6,7-cd] indazole-6(2H)-ones. These compounds have been shown to have antitumor activity.
