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Imidazopyridine derivative compounds and use of same

A compound and solvate technology, applied in the field of imidazopyridine derivative compounds, can solve the problem of not showing enough

Pending Publication Date: 2021-09-07
HANMI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The LSD1 inhibitors studied so far do not show sufficient selective inhibitory activity against LSD1, or have side effects such as showing resistance to drugs or showing toxicity to normal cells, therefore, there are LSD1 inhibitors that cannot be effectively used for treatment Problems with cancer and neoplastic diseases

Method used

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  • Imidazopyridine derivative compounds and use of same
  • Imidazopyridine derivative compounds and use of same
  • Imidazopyridine derivative compounds and use of same

Examples

Experimental program
Comparison scheme
Effect test

preparation example

[0237] The abbreviations used in the following preparations, preparation methods and examples indicate respectively:

[0238] Protecting group (PG): protecting group

[0239] Boc-: tertiary butoxycarbonyl

[0240] POCl 3 : Phosphoryl chloride

[0241] NaCO 3 :Sodium carbonate

[0242] Ce 2 CO 3 : cesium carbonate

[0243] Na 2 SO 4 : sodium sulfate

[0244] MPLC: medium pressure liquid chromatography (medium pressure liquid chromatography)

[0245] NET 3 (TEA): Triethylamine

[0246] TLC: thin layer chromatography

[0247] PD 2 (dba) 3 : Tris(dibenzylideneacetone)dipalladium(0)

[0248] Xantphos: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

[0249] FeCl 3 : Iron(III) chloride

[0250] Celite: diatomaceous earth

[0251] CF 3 CO 2 H: Trifluoroacetate

[0252] N,N-Dimethylformamide (N,N-Dimethyl formamide): Dimethylformamide

[0253] MeOH: Methanol

[0254] EtOH: ethanol

[0255] n-Hexane (n-Hexane): hexane

[0256] Ethyl acetate (EA): ethyl acetat...

preparation example 1

[0282] Preparation Example 1: Preparation of 4-cyclopropylaniline

[0283]

[0284] Step 1) Preparation of 1-cyclopropyl-4-nitrobenzene

[0285]

[0286] 3.0 g (14.9 mmol) of 4-bromonitrobenzene and 1.7 g (19.4 mmol) of cyclopropylboronic acid were dissolved in 40 ml of toluene and 4 ml of water, respectively. To this was added 133 mg (0.6 mmol) of palladium acetate (Pd(OAc) 2 ), 418 mg (1.49 mmol) tricyclohexylphosphine (P(C 6 h 11 ) 3 ) and 6.8 g (49.2 mmol) of potassium carbonate (K 2 CO 3 ). It was purged with argon for 30 minutes, heated to a temperature in the range of 100°C to 110°C, and reacted for three hours. The reaction was identified as complete by TLC monitoring and celite filtration was performed under reduced pressure. Then, the filtered organic layer was concentrated under reduced pressure. The residue obtained by concentration was purified by column chromatography (ethyl acetate:hexane=1:9 (v / v)), whereby 2.1 g of the desired compound were obt...

preparation example 2

[0292] Preparation Example 2: Preparation of 2,6-difluoro-4-(pyrrolidin-1-yl)aniline

[0293]

[0294] At room temperature, 7.70 g (24.99 mmol) of tert-butyl (4-bromo-2,6-difluorophenyl) carbamate, 8.3 ml (99.96 mmol) of pyrrolidine, 561 mg (2.50 mol) of palladium acetate, 2.89 g (5.00 mmol) of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene and 15.29 g (49.98 mmol) of cesium carbonate dissolved in 77 ml of toluene . Then, it was purged with argon for 5 minutes, heated to a temperature of 90° C., and reacted for 12 hours. The reaction was identified as complete by TLC monitoring and celite filtration was performed under reduced pressure. Then, the filtered organic layer was concentrated under reduced pressure. The residue obtained by concentration was purified by column chromatography, whereby 4.56 g of the desired compound were obtained (yield: 61%).

[0295] 1 H-NMR (300MHz, CDCl 3 ):δ6.05(d,2H),5.63(br,1H),3.21(m,4H),2.00(m,4H),1.48(s,9H)

[0296]

[0297] 4.56...

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Abstract

One aspect of the present invention provides a compound selected from among a compound of chemical formula 1 having lysine-specific demethylase-1 (LSD1) inhibitory activity, and a tautomer, a stereoisomer, and a solvate thereof, and pharmaceutically acceptable salts of the aforementioned components, and said compound is effective in the prevention or treatment of diseases caused by abnormal activation of LSD1.

Description

technical field [0001] The present disclosure relates to an imidazopyridine derivative compound and its application, and more specifically, to an imidazopyridine derivative compound having inhibitory activity on lysine-specific histone demethylase-1 (LSD1) or its Tautomers, stereoisomers or solvates and a pharmaceutical composition comprising said imidazopyridine derivative compound. Background technique [0002] Cancer stem or cancer-initiating cells possess some pluripotent stem cell properties that contribute to the heterogeneity of cancer cells. These properties can make cancer cells more resistant to traditional therapies such as chemotherapy or radiation, thus leading to relapse after treatment. Therefore, efforts continue to develop anticancer drugs that are more advanced than traditional chemotherapy or radiation therapy. [0003] Epigenetics is the study of the phenomenon that the gene expression pattern and activity are changed, and the gene expression pattern an...

Claims

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Application Information

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IPC IPC(8): C07D471/04A61K31/4545A61P35/00
CPCA61P35/00C07D471/04C07D519/00A61K45/06A61K31/4439
Inventor 裵仁焕金元政金知淑宋芝英崔载律金敃廷南廷秀安永吉
Owner HANMI PHARMA
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