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Novel amino pyridine compound, its preparation method, pharmaceutical composition containing compound and application thereof

A compound and mixture technology, applied in the field of medicinal chemistry and pharmacotherapeutics, can solve the problem of low correlation of tumor incidence

Inactive Publication Date: 2012-10-10
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Various Met germline and somatic mutations are less associated with tumor incidence

Method used

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  • Novel amino pyridine compound, its preparation method, pharmaceutical composition containing compound and application thereof
  • Novel amino pyridine compound, its preparation method, pharmaceutical composition containing compound and application thereof
  • Novel amino pyridine compound, its preparation method, pharmaceutical composition containing compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] Step 1: Preparation of N,N-dimethyl-1-[(2-nitropyridine-3)-oxyl]carbothioamide

[0098] Dissolve 2-nitro-3-hydroxypyridine (10.00g, 71.38mmol), N,N-dimethylaminothioformyl chloride (10.59g, 85.66mmol) in 50mL DMF, add DABCO (triethylenedi Amine) (9.61g, 85.66mmol), after stirring at room temperature for 24h, 150mL of water was added to the reaction liquid, extracted with 600mL of ethyl acetate, the organic phase was washed with 3×100mL of water and saturated brine successively, and anhydrous Na 2 SO 4 Dry, filter, and distill off the solvent under reduced pressure to obtain a yellow solid. It was directly used in the next step without purification. 1 H NMR (400MHz, CDCl 3 )δ8.47(dd, J=2.4, 4.4Hz, 1H), 7.77(dd, J=2.4, 8.0Hz, 1H), 7.70(dd, J=4.4, 8.0Hz, 1H), 3.45(s, 3 ), 3.40(s, 3H).

[0099] Step 2: Preparation of N,N-dimethyl-1-[(2-nitropyridine-3)-thio]formamide (1)

[0100] Disperse the crude N,N-dimethyl-1-[(2-nitropyridine-3)-oxyl]carbothioamide obtained in th...

Embodiment 2

[0104] Step 1: Preparation of 1-(3-fluoro-2,6-dichlorophenyl)ethanol

[0105] Dissolve 1-(3-fluoro-2,6-dichlorophenyl)ethanone (20.00 g, 96.60 mmol) in 100 mL MeOH, add NaBH in portions 4 (7.31g, 193.21mmol), after stirring at room temperature for 2h, 20mL of water was added to the reaction solution, the organic solvent was evaporated under reduced pressure, the residue was extracted with 150mL of ethyl acetate, the organic phase was washed with saturated brine, anhydrous Na 2 SO 4 After drying, filtering, and evaporating the solvent under reduced pressure, a colorless transparent oily liquid was obtained. It was directly used in the next step without purification.

[0106] Step 2: Preparation of ethyl 1-(3-fluoro-2,6-dichlorophenyl)methanesulfonyl ester (2)

[0107] Dissolve the crude 1-(3-fluoro-2,6-dichlorophenyl)ethanol obtained in the previous step in 150 mL CH 2 Cl 2 In, add Et 3 N (13.43mL, 96.60mmol) catalytic amount of DMAP, cooled to 0°C, added dropwise MsCl (7...

Embodiment 3

[0111] Step 1: Preparation of 3-{[1-(3-fluoro-2,6-dichlorophenyl)ethyl]thio}-2-nitropyridine

[0112] N,N-Dimethyl-1-[(2-nitropyridine-3)-thio]formamide (10.00g, 44.01mmol), KOH (5.43g, 96.81mmol) were placed in a 250mL eggplant-shaped flask , under argon protection, place the flask in an ice-water bath, and add MeOH / THF / H with a syringe 2 O(2 / 2 / 1, v / v / v) 100mL, after adding, remove the ice-water bath, stir at room temperature, and no N,N-dimethyl-1-[(2-nitropyridine-3 )-sulfanyl] formamide, the organic solvent was evaporated under reduced pressure, and under argon protection, 1-(3-fluoro-2,6-dichlorophenyl) methanesulfonyl ethyl ester (12.64g , 44.01mmol) THF solution 120mL, after stirring at room temperature for 24h, the organic solvent was evaporated under reduced pressure, the reaction solution was extracted with ethyl acetate 300mL, the organic phase was washed with water 3×40mL, saturated brine, and anhydrous Na 2 SO 4 Dry, filter, and evaporate the solvent under redu...

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Abstract

The present invention relates to the field of medicinal chemistry and pharmacotherapeutics, specifically to a compound which is used as a receptor tyrosine kinase MET inhibitor and is shown in the formula I, its enantiomer, diastereomer, racemate and their mixture or its pharmaceutically acceptable salt, a preparation method thereof, a pharmaceutical composition containing the compound and an application thereof.

Description

technical field [0001] The present invention relates to the fields of medicinal chemistry and pharmacotherapeutics, in particular to aminopyridine compounds as receptor tyrosine kinase MET inhibitors, a preparation method thereof, pharmaceutical compositions containing such compounds and applications. Background technique [0002] Targeted therapy has undoubtedly had a major impact on cancer treatment. Tumor occurrence, evolution, spread and tumor angiogenesis depend on various signal transduction pathways. Significant progress has been made in the treatment of tumors by targeting these signaling pathways, and many drugs have been successfully marketed. For example, the anticancer drug imatinib developed based on ABL tyrosine kinase has a good curative effect on chronic myelogenous leukemia (CML). In recent years, members of the Met proto-oncogene family have received extensive attention. The Met family includes the Met (also known as c-Met) and Ron receptors. Tyrosine p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C07D401/14C07D213/73C07D401/10C07D405/14C07D213/82A61K31/5377A61K31/506A61K31/496A61K31/4545A61K31/444A61K31/4439A61K31/4418A61P35/00A61P37/02A61P29/00
CPCC07D401/14C07D405/14C07D213/73C07D401/10C07D401/04C07D213/82A61P29/00A61P35/00A61P37/02
Inventor 柳红耿美玉罗成张登友艾菁梁中洁王英蒋华良陈凯先
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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