5-methyl-2(1H)pyridone derivatives, preparation method and applications thereof

A technology of pyridone and derivatives, applied in the field of 5-methyl-2 pyridone derivatives and preparation thereof, can solve the problem of the preparation of 5-methyl-2(1H) pyridone derivatives that have not been seen or seen methods and uses to achieve the effect of simple steps, low cost and high efficiency

Inactive Publication Date: 2015-12-09
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] At present, there are no reports of 5-methyl-2 (1H) pyridone derivatives shown in formula I of the present inv

Method used

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  • 5-methyl-2(1H)pyridone derivatives, preparation method and applications thereof
  • 5-methyl-2(1H)pyridone derivatives, preparation method and applications thereof
  • 5-methyl-2(1H)pyridone derivatives, preparation method and applications thereof

Examples

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Example Embodiment

[0080] Example 1

[0081]

[0082] Among them, "rf" is the abbreviation of reflux, and its Chinese meaning is "reflux".

[0083] In the 25ml reaction flask, first add 3.4ml from 17mlH 2 A solution (50%, volume fraction) composed of O and 17ml concentrated sulfuric acid, then add 1g (0.01mol) 2-amino-5-methylpyridine, cool to below 10℃ with an ice salt bath, stir for a few minutes, the reaction solution It becomes milky white. Then slowly drop by (1.72gNaNO 2 With 3mLH 2 O) The mixed solution produces irritating gas when dripping. After the dripping is completed, the reaction solution turns into a light yellow solution. TCL (Thin Layer Chromatography) monitors until the reaction is completed (about 40 min). Then add 8mLH 2 O, reflux and stir for 15min, cool, add anhydrous Na under stirring 2 CO 3 , Make the reaction liquid neutral (yellow-brown solid), filter, spin-dry the obtained filtrate, and then dissolve and filter with absolute ethanol, and spin-dry the filtrate again to obta...

Example Embodiment

[0092] Example 2

[0093]

[0094] According to the method described in Example 1, replacing "p-methylacetophenone" with "p-chloroacetophenone", the compound represented by formula Ib was obtained.

[0095] Compound represented by formula Ib: yellow solid, melting point (mp) 66-67°C;

[0096] 1 HNMR(400MHz,DMSO-d6)δ: 8.02(d,J=8.8Hz,4H,ArH), 7.62(d,J=8.4Hz,4H,ArH), 7.51(d,J=8.4Hz,2H,ArH ), 7.37~7.40(m,2H,CH),7.30(d,J=8.4Hz,2H,ArH),6.43(d,J=10.0Hz,1H,CH),3.97~4.03(m,2H,CH ),3.55(d,J=6.8Hz,4H,CH 2 ),2.06(s,6H,CH 3 );

[0097] 13 CNMR(100MHz,DMSO-d6)197.40,160.34,143.95,139.04,136.02,135.26,129.84,129.76,126.31,120.11,113.91,44.21,39.53,35.53,16.23; IR(KBr,n,cm -1 ): 3429,1673,1590,1400,1262,1091,804,590;

[0098] HRMS(ESI)calcdforC 29 H 23 Cl 2 NO 3 [M+Na] + 503.1055found526.0963.

Example Embodiment

[0099] Example 3

[0100]

[0101] According to the method described in Example 1, replacing "p-methylacetophenone" with "p-fluoroacetophenone", the compound represented by formula Ic is obtained.

[0102] Compound represented by formula Ic: gray solid, melting point (mp) is 60-62°C;

[0103] 1 HNMR(400MHz,DMSO-d6)δ: 8.06(dd,J1=6.0Hz,J2=8.4Hz,4H,ArH),7.48(d,J=8.4Hz,2H,CH),7.26~7.35(m,8H ,ArH),6.40(d,J=10.0Hz,1H,CH),3.97~4.04(m,1H,CH),3.52(d,J=6.8Hz,4H,CH 2 ),2.02(s,6H,CH 3 );

[0104] 13 CNMR(100MHz,DMSO-d6)196.93,166.24,163.74,160.35,144.06,142.81,139.02,136.01,133.37,130.95,128.14,126.30,120.11,115.73,113.91,44.17,39.11,35.87,16.21; IR(KBr, n,cm -1 ): 2925,1675,1596,1506,1410,1364,1277,1230,1156,990,832,586;

[0105] HRMS(ESI)calcdforC 29 H 23 F 2 NO 3 [M+Na] + 471.1646found494.1549.

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Abstract

The invention discloses 5-methyl-2(1H)pyridone derivatives represented by the formula (I), crystal form, pharmaceutically-acceptable salts, hydrates, solvates, or prodrugs thereof. In the formula (I), the R1 represents a hydrogen atom, a halogen element, a C1-C6 alkyl group, a C1-C6 alkyloxy group, a C2-C6 amido group, a C2-C6 aminoacyl group, and a C3-C6 heterocyclic group. The provided derivatives have a prominent inhibiting effect on the proliferation and fibronectin (FN) secretion of fibroblast, so the derivatives can be used to prepare drugs for preventing or treating fibrotic diseases and tumors. The provided preparation method has the advantages of few and simple steps, mild reaction conditions, low energy consumption, high efficiency, low cost, and environment-friendliness, and is suitable for industry.

Description

technical field [0001] The invention relates to a 5-methyl-2(1H) pyridone derivative and its preparation method and application. Background technique [0002] 5-Methyl-2(1H)pyridone, alias: 5-methylpyridin-2-ol, 2-hydroxy-5-methylpyridine, CAS number: 1003-68-5, its chemical structure is shown in Formula A It is mainly used in fields such as organic synthesis. [0003] [0004] U.S. Patent No. 3,839,346A discloses pyridone compounds shown in formula B, which have anti-inflammatory, antipyretic, lower serum uric acid levels, and analgesic effects; wherein, the number of substituents R is 0 or 1, and R represents nitro, chlorine, etc. atom, alkyl, methoxy; when R is 0, the compound shown in formula B is 1-phenyl-5-methyl-2-(1H)pyridone (ie pirfenidone). US Patent No. 4,052,509A also discloses pirfenidone, which has good anti-inflammatory and analgesic effects. [0005] [0006] Chinese patent CN1386737A discloses an anti-fibrosis pyridone drug represented by formula C...

Claims

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Application Information

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IPC IPC(8): C07D213/64A61K31/44A61P35/00A61P11/00A61P9/00A61P19/08A61P1/00A61P9/10A61P3/10A61P9/12A61P13/12A61P1/16A61P31/14A61P37/06A61P17/00A61P17/02
CPCC07D213/64
Inventor 尹述凡黎勇曹婷婷袁丽宋长伟
Owner SICHUAN UNIV
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