Imidazole [4,5-c] pyridine-7-methanamide derivative as well as preparation method and medical application thereof

A technique of pharmacy, methylation, applied in the field of medicinal chemistry

Active Publication Date: 2013-04-24
HEFEI IND PHARMA INST +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Radiotherapy and many anti-tumor drugs achieve the purpose of killing tumor cells by damaging DNA, but tumor cells can activate their own DNA

Method used

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  • Imidazole [4,5-c] pyridine-7-methanamide derivative as well as preparation method and medical application thereof
  • Imidazole [4,5-c] pyridine-7-methanamide derivative as well as preparation method and medical application thereof
  • Imidazole [4,5-c] pyridine-7-methanamide derivative as well as preparation method and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Synthesis of 4,5-diaminonicotinamide (b)

[0036] Add 5.0 g of 4-amino-5-nitronicotinamide to 100 ml of methanol in a 50 ml one-necked flask, add 0.25 g of 10% Pd-C, and hydrogenate at normal temperature and pressure. TLC tracking detection, after the reaction of the raw materials was complete, the hydrogenation was stopped, suction filtered, and the filtrate was spin-dried to obtain 3.6 g of a yellow solid with a yield of 85.7%.

Embodiment 2

[0038] Synthesis of 2-(N-Cbz-2-pyrrolyl)-7-carboxamidoimidazo[4,5-c]pyridine (d-1)

[0039] In a 100ml three-neck flask, dissolve N-Cbz proline (3.6g, 14.4mmol) in 50ml of dichloromethane, add 5.0ml of thionyl chloride, and heat to reflux. After reacting for 2 h, the solvent was distilled off, and the residue was dissolved in 50 ml of tetrahydrofuran for use.

[0040]Add 4,5-diaminonicotinamide (1.0g, 6.58mmol) into a 50ml three-necked flask and dissolve it in 10ml of DMF, add 1.2ml of pyridine, add the tetrahydrofuran solution of the above acid chloride dropwise under ice bath, and add dropwise After the completion, place it at room temperature and stir overnight. After the reaction of the raw materials is detected by TLC, the tetrahydrofuran and pyridine are evaporated under reduced pressure, and the residue is poured into ice water under heat. 2 CO 3 The pH value of the solution was adjusted to be alkaline, and a solid precipitated out. The solid was filtered, washed with...

Embodiment 3

[0044] Synthesis of 2-(2-pyrrolyl)-7-carboxamide imidazo[4,5-c]pyridine (e-1)

[0045] Add 2-(N-Cbz-2-pyrrolyl)-7-carboxamide imidazol[4,5-c]pyridine (1.0g, 2.7mmol) into 20ml of methanol in a 50ml one-necked flask, add 0.1g10 %Pd-C, hydrogenated under normal temperature and pressure. TLC tracking detection, after the reaction of the raw materials was complete, the hydrogenation was stopped, suction filtered, and the filtrate was spin-dried to obtain 0.56 g of white solid, yield: 90.0%. Melting point: 120-122°C.

[0046] 1 H-NMR(300MHz,DMSO),δ(ppm):8.87(s,1H),8.75(s,1H),7.75(s,1H),4.57(dd,J 1 =8.0Hz,J 2 =6.2Hz,1H),4.04(m,2H),2.27(m,1H),2.03(m,1H),1.93(m,2H)

[0047] MS(ESI(+)70V)m / z:232[M+H] + .

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Abstract

The invention relates to the field of medicinal chemistry and in particular relates to an imidazole [4,5-c] pyridine-7-methanamide derivative (I), wherein R is defined in the specification. Pharmacodynamic tests proof that the derivative compound provided by the invention can serve as a tumour therapeutic agent and especially the derivative compound has extremely strong anti-tumour effect when being combined with cis-platinum. The invention also discloses a preparation method of the derivative compound and a pharmaceutical composition comprising the derivative compound.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and specifically relates to a class of imidazo[4,5-c]pyridine-7-carboxamide derivatives, a preparation method thereof, a medical application as a tumor therapeutic agent, and a pharmaceutical composition containing the compound. Background technique [0002] The main treatment methods for cancer are divided into three categories, surgery, radiation therapy and chemotherapy. Among them, surgical treatment and radiotherapy are both local therapies. Early non-metastatic cancer can often be cured after surgery, but in advanced cancer, the cancer cells have spread in the body, and it is easy to relapse at this time after surgery. Radiation therapy is primarily used for localized cancers that are difficult to treat surgically. The disadvantage of radiation therapy is that the radiation used kills not only cancer cells, but also normal cells, which can easily induce infection and other complications...

Claims

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Application Information

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IPC IPC(8): C07D471/04A61K31/437A61K31/4545A61P35/00
Inventor 徐云根何广卫朱启华王旭艳吴强曹喆
Owner HEFEI IND PHARMA INST
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