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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

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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 invention; there is no preparation of 5-methyl-2 (1H) pyridone derivatives shown in formula I Methods and Uses Reported

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

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081]

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

[0083] In a 25ml reaction bottle, first add 3.4ml from 17mlH 2 O and the solution (50%, volume fraction) that 17ml concentrated sulfuric acid forms, then add 1g (0.01mol) 2-amino-5-picoline, cool to below 10 ℃ with ice-salt bath, after stirring several minutes, reaction solution Turned milky white. Then slowly drop by (1.72gNaNO 2 with 3mLH 2 O) the mixed solution, during dropwise addition, produces irritating gas, after dropwise addition, the reaction solution turns into a light yellow solution, and TCL (thin layer chromatography) monitors until the reaction is complete (about 40min). Then add 8mLH 2 O, reflux stirring reaction 15min, cooling, add anhydrous Na under stirring 2 CO 3 , make the reaction solution neutral (produce yellow-brown solid), filter, the gained filtrate is spin-dried, then dissolve and filter with absolute ethanol, and the gained filtrate is sp...

Embodiment 2

[0093]

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

[0095] Compound represented by formula Ib: yellow solid (yellow solid), melting point (mp) is 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.

Embodiment 3

[0100]

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

[0102] Compound represented by formula Ic: gray solid (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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