cas 53179-13-8, Pirfenidone | Articles data

Articles about 53179-13-8Total 42 be found

Article title
Article abstract
Author
Journal number and time
Download

Manganese-Promoted Regioselective Direct C3-Phosphinoylation of 2-Pyridones
A highly efficient and regioselective manganese-induced radical oxidative direct C?P bond formation between 2-pyridones and secondary phosphine oxides was developed. The C3-selective phosphinoylation was conveniently achieved through a combination of substoichiometric manganese and persulfate oxidant under mild conditions. Various 3-phosphinoylated pyridone products can be obtained in moderate to high yields. Preliminary mechanistic studies suggest that the reaction is likely to involve a radical pathway induced by catalytically active Mn3+ species.
Chantarojsiri, Teera,Kittikool, Tanakorn,Phakdeeyothin, Kunita,Yotphan, Sirilata
supporting information
p. 3071 - 3078
(2021/07/22)

Synthetic method of pirfenidone
The invention belongs to the technical field of medicine synthesis, and particularly relates to a synthetic method of pirfenidone. The synthesis method comprises the following steps of adding a solvent A, aniline, 2-methyl-1, 3-malondialdehyde and a condensing agent A into a reactor 1 to obtain a solution of an intermediate 1, cooling the solution of the intermediate 1, and adding an acid-bindingagent A, a catalyst A and an acylating agent A to obtain a solution of an intermediate 2, drying the obtained solution of the intermediate 2 by distillation under reduced pressure, adding a solvent B,transferring to a reactor 2, adding a condensing agent B to obtain a pirfenidone crude product, and finally purifying the crude product. Compared with the disclosed synthesis technical route, the pirfenidone synthesis method provided by the invention has the advantages of cheap and easily available raw materials, simple and feasible method, good reaction selectivity, high total yield of the synthesis route and easy purification of the product, and is suitable for industrial production and application of medicines.
-
Paragraph 0044; 0067-0072; 0074

(2021/01/29)

Synthetic method of pirfenidone
The invention relates to a process for synthesizing pirfenidone (1) by taking 5-methyl-3, 4-dihydro-2-pyridone and halogenated benzene (chlorobenzene, bromobenzene or iodobenzene) as raw materials inthe presence of a catalytic system consisting of a copper salt and an organic ligand and in the presence of an alkali. Compared with the 5-methylpyridine-2 (1H)-ketone, the 5-methyl-3, 4-dihydro-2-pyridone has the advantages that the 5-methyl-3, 4-dihydro-2-pyridone is easier to obtain and the cost is lower. According to the process, the high efficiency of the catalytic system consisting of copper(1) salt and an organic ligand in coupling of 5-methyl-3, 4-dihydro-2-pyridone and halogenated benzene is also utilized.
-
Paragraph 0022; 0036-0041

(2020/11/12)

N - And O -arylation of pyridin-2-ones with diaryliodonium salts: Base-dependent orthogonal selectivity under metal-free conditions
Metal-free N- and O-arylation reactions of pyridin-2-ones as ambident nucleophiles have been achieved with diaryliodonium salts on the basis of base-dependent chemoselectivity. In the presence of N,N-diethylaniline in fluorobenzene, pyridin-2-ones were very selectively converted to N-arylated products in high yields. On the other hand, the O-arylation reactions smoothly proceeded with the use of quinoline in chlorobenzene, leading to high yields and selectivities. In these methods, a variety of pyridin-2-ones in addition to pyridin-4-one and a set of diaryliodonium salts were accepted as suitable reaction partners.
Abe, Yusuke,Hanazawa, Natsumi,Katagiri, Kotone,Kuriyama, Masami,Ono, Shimpei,Onomura, Osamu,Yamamoto, Kosuke
p. 8295 - 8300
(2020/09/09)

Preparation method of pirfenidone
The invention discloses a preparation method of pirfenidone. The method comprises the following steps: carrying out reflux on diethyl malonate (or methyl ester) as an initial raw material and 1, 1, 1,3, 3-tetraethoxy-2-methyl propane in the presence of a catalyst zinc chloride and a solvent acetic anhydride for a reaction to obtain diethyl (or methyl) 2-(3-ethoxy-2-methylallyl)malonate, performing cyclization with aniline to obtain ethyl (or methyl) 5-methyl-2-oxo-1-phenyl-1, 2-dihydropyridin-3-formate, performing alkaline hydrolysis to obtain 5-methyl-2-oxo-1-phenyl-1, 2-dihydropyridine-3-formic acid, and finally performing heating decarboxylation to obtain pirfenidone. Starting materials are cheap and easily available, and the structure is stable, although the synthesis steps comprise four steps, the synthesis process is simple to operate, the reaction process and the final product quality control can be effectively guaranteed, the product yield is high, and the method is suitable for large-scale industrial production requirements of bulk drugs.
-
(2020/07/28)

Preparation method of high-purity pirfenidone
The invention relates to the technical field of drug synthesis, and discloses a preparation method of high-purity pirfenidone. The preparation method at least comprises the following steps: (1) uniformly mixing 2-amino-5-methylpyridine, a diazotization reagent and water, cooling to a temperature of -4 DEG C to 3 DEG C, adding an acid solution, and carrying out a thermal insulation reaction; heating for hydrolysis after the reaction is completed, cooling, then adjusting the pH value to 6.5-7.5 by using a sodium hydroxide solution with the mass fraction of 30%, extracting an organic phase by using a first solvent, drying, and concentrating under reduced pressure to obtain a 2-hydroxy 5-methylpyridine crude product; (2) adding a second solvent into the 2-hydroxy 5-methylpyridine crude productfor recrystallization to obtain a 2-hydroxy 5-methylpyridine pure product; (3) uniformly mixing the 2-hydroxy 5-methylpyridine pure product, iodobenzene, a catalyst and anhydrous potassium carbonate,heating and reacting, carrying out suction filtration, and carrying out vacuum concentration to obtain a pirfenidone crude product; and (4) adding a third solvent into the pirfenidone crude product,heating to dissolve, cooling to -5 to 5 DEG C, crystallizing for 1 to 1.5 hours, carrying out suction filtration, and drying to obtain a pirfenidone pure product.
-
Paragraph 0062-0246

(2020/05/02)

C-H Pyridonation of (Hetero-)Arenes by Pyridinium Radical Cations
Pyridones are important heteroaromatic scaffolds found in natural products and pharmaceuticals and are, therefore, of major interest in organic synthetic chemistry. Here we report the first C-H pyridonation of unactivated (hetero-)arenes, providing a methodology to directly access N-aryl-2- and 4-pyridones. Generation of pyridinium radical cations through single-electron reduction allows for the synthesis of pyridones on structurally complex molecules.
Hillenbrand, Julius,Ham, Won Seok,Ritter, Tobias
p. 5363 - 5367
(2019/09/06)

Method for preparing anti-fibrotic drug
The invention relates to a method for preparing an anti-fibrotic drug. The method for preparing pirfenidone is characterized by comprising the following steps of: hydrolyzing a starting material 2-amino-5-methylpyridine by adopting a reverse diazotization hydrolysis method, extracting by using an extraction solvent and recrystallizing by using a recrystallization solvent to obtain 2-hydroxy-5-methylpyridine; in the presence of anhydrous potassium carbonate and active copper, mixing with iodobenzene and heating to carry out nucleophilic substitution reaction to produce a target compound: pirfenidone crude product; and sequentially carrying out recrystallization and purification by using a recrystallization solvent: ethyl acetate and absolute ethanol to finally obtain a pirfenidone pure product. The method disclosed by the invention has the following characteristics that: the initial raw material: the 2-amino-5-methylpyridine is a commercially available chemical product which is cheap and easy to obtain; the reverse diazotization is adopted to replace conventional diazotization reaction and the operation is simple and convenient; the purification methods of the 2-hydroxy-5-methylpyridine and the final product pirfenidone are easy to operate and high in yield; and the processing method is low in energy consumption and the production cost is reduced.
-
Paragraph 0016-0019

(2019/04/27)

IMPROVED PROCESS FOR THE PREPARATION OF PURE 5-METHYL-1-PHENYL-2-1 (H)-PYRIDONE
The present invention relates to improved process for the preparation of pure 5-methyl-1-phenyl-2( I H)-pyridone of formula I.
-
Page/Page column 8; 9

(2018/05/24)

Substituent Effects of 2-Pyridones on Selective O-Arylation with Diaryliodonium Salts: Synthesis of 2-Aryloxypyridines under Transition-Metal-Free Conditions
An efficient transition-metal-free strategy to synthesize 2-aryloxypyridine derivatives has been developed by a selective O-arylation of 2-pyridones with diaryliodonium salts. The reaction was compatible with a series of functional groups for 2-pyridones and diaryliodonium salts such as halides, nitro, cyano, and ester groups. The substituents at the C6-position of 2-pyridones favored O-arylation products because of steric hindrance. The reaction was easily performed on a gram-scale and 6-chloro-2-pyridone was a good precursor to access various unsubstituted 2-aryloxypyridines by dehalogenation. A P2Y 1 lead compound analogue could be prepared in good yield over two steps.
Li, Xiao-Hua,Ye, Ai-Hui,Liang, Cui,Mo, Dong-Liang
p. 1699 - 1710
(2018/02/06)

Pirfenidone synthesizing method
The invention discloses a pirfenidone synthesizing method, relates to the field of chemical engineering and specifically relates to the pirfenidone synthesizing method. The pirfenidone synthesizing method comprises the following steps: adding 20g 5-methyl-2-aminopyridine and 66mL 50% sulfuric acid solution into a 500mL three-necked bottle, cooling by ice salt bath to be 5 DEG C or below, adding 34.5g sodium nitrite which is dissolved into 50mL water while stirring, continuing stirring to react for 3 hours under 0 to 5 DEG C after adding the sodium nitrite, then heating and boiling until no gasis generated, stopping heating, adjusting an obtained settled solution to be neutral by anhydrous sodium carbonate, concentrating to be dry to obtain yellowish brown solid, reflux extracting by 400mLmethyl alcohol, decoloring an extracting solution by activated carbon, concentrating to be dry to obtain yellow solid and recrystallizing by absolute ethyl alcohol to obtain 16.2g white crystal. Thepirfenidone synthesizing method disclosed by the invention has the advantages that a technology is simple, the reaction is safe, a reaction temperature is low, a use amount of a reagent iodobenzene issmall, a use amount of a catalyst is also greatly reduced, an actual requirement of medicine production is more met, and industrial prospect is very good.
-
Paragraph 0008; 0009

(2018/03/26)

METHOD FOR PREPARING AN ANTIFIBROTIC AGENT
The present invention relates to a process for the preparation of pirfenidone, an immunosuppressive drug developed for the treatment of idiopathic pulmonary fibrosis.
-
Paragraph 0067-0068

(2018/02/21)

IMPROVED PROCESS FOR THE PREPARATION OF PIRFENIDONE
The present invention relates to improved process for the production of Pirfenidone which is comprises reacting the compound of 5-methyl-2(1H)-pyridone of formula (III) with bromobenzene (IV) in polar solvent, in presence of base and activated Cu powder to obtain the compound of formula (I). The present invention is also related to purification of Pirfenidone.
-
Page/Page column 6

(2018/10/25)

A highly efficient Suzuki-Miyaura methylation of pyridines leading to the drug pirfenidone and its CD3 version (SD-560)
Efficient introduction of methyl or methyl-d3 into aromatic and heteroaromatic systems still presents a synthetic challenge. In particular, we were in search of a non-cryogenic synthesis of the 5-CD3 version of pirfenidone (4d, also known as Pirespa, Esbriet or Pirfenex), one of the two drugs approved to date for retarding idiopathic pulmonary fibrosis (IPF), a serious, rare and fatal lung disease, with a life expectancy of 3-5 years. The methyl-deuterated version of pirfenidone (4e, also known as SD-560) was designed with the objective of attenuating the rate of drug metabolism, and our goal was to find a green methylation route to avoid the environmental and economic impact of employing alkyllithium at cryogenic temperatures. The examination of several cross-coupling strategies for the introduction of methyl or methyl-d3 into methoxypyridine and pyridone systems culminated in two green and nearly quantitative Suzuki-Miyaura cross-coupling routes in the presence of RuPhos ligand: the first, using commercially available methyl boronic acid or its CD3 analog and the second, employing potassium methyl trifluoroborate or CD3BF3K, the latter obtained by a new route in 88% yield. This led, on a scale of tens of grams, to the synthesis of pirfenidone (4d) and its d3 analog, SD-560 (4e), at 99% isotopic purity.
Falb, Eliezer,Ulanenko, Konstantin,Tor, Andrey,Gottesfeld, Ronen,Weitman, Michal,Afri, Michal,Gottlieb, Hugo,Hassner, Alfred
supporting information
p. 5046 - 5053
(2017/11/09)

An unusual rearrangement involving 5-bromo-1-phenylpyridone during its methyl cross coupling with turbo-Grignard reagent, leading to a 5-bromopyridone-fused seven-membered carbocyclic ring
[Figure not available: see fulltext.] The structure of a cyclohepta[c]pyridin-1-one, a product of an unusual transformation, isolated during a turbo-Grignard reagentpromoted methyl cross coupling to 5-bromo-1-phenyl-2-pyridone, was determined by 1H and 13C NMR, COSY and high-resolution MS, as well as computer modeling. Its formation suggests a remarkable nucleophilic attack at the α-position to the pyridone carbonyl group. A rational pathway is presented.
Falb, Eliezer,Ulanenko, Konstantin,Tor, Andrey,Afri, Michal,Gottlieb, Hugo,Hassner, Alfred
p. 979 - 984
(2017/11/16)

PROCESS FOR THE SYNTHESIS OF PIRFENIDONE
Disclosed is a process for the synthesis of Pirfenidone (1) from 5-methyl- 2(1H)-pyridinone and chlorobenzene in the presence of a catalytic system consisting of a copper salt and an organic ligand, in thepresence of a base. The process exploits the high efficiency of the catalytic system consisting of copper(I) salt and an organic ligandin the presence of an inorganic base in the N-amidation reaction of chlorobenzene, a cheap reagent also usable as solvent in this case; reaction conditions at high temperatures, at atmosphere pressureor higher, produce a reaction with good yields.
-
Page/Page column 9

(2017/05/21)

AN IMPROVED PROCESS FOR THE PREPARATION OF HIGHLY PURE ANTI-FIBROTIC DRUG
The present invention relates to improved process for the preparation of highly pure Pirfenidone (I). Pirfenidone (I) is an anti-fibrotic drug for the treatment of idiopathic pulmonary fibrosis (IPF).
-
Page/Page column 21; 22

(2017/08/21)

AN IMPROVED PROCESS FOR THE PREPARATION OF PIRFENIDONE
The present invention is relates to an improved process for the preparation of pure pirfenidone. The present invention also relates to a crystalline form of pirfenidone and its pharmaceutical composition thereof.
-
Page/Page column 9; 10

(2017/08/07)

Pirfenidone derivative and preparation method thereof
The invention discloses a compound shown in a formula I or pharmaceutically acceptable salt, crystal form, hydrate or solvate thereof, wherein R1, R2, R3, R4 and R5 are respectively or simultaneously selected from H, halogen, hydroxyl, nitryl, carbonyl or C1-C8 alkyl; R6 and R7 are respectively or simultaneously selected from H, O=C-NH2, S=C-NH2, phenyl, methyl substituted phenyl, ethyl substituted phenyl, methoxy substituted phenyl and ethyoxyl substituted phenyl. Compared with pirfenidone, the new compound disclosed by the invention is of a specific C=N-N structure, and the anti-fibrosis activity of the new compound is obviously better than that of pirfenidone, especially, inhibition rate of the new compound on fibroblast proliferation is improved by at least 50% compared with pirfenidone; meanwhile, the inhibitory effect of the new compound on fibronectin secretion of the fibroblast is also obviously better than that of pirfenidone, so that the compound disclosed by the invention has a good industrial prospect.
-
(2017/04/12)

Pirfenidone derivative and preparation method thereof
The invention discloses a compound shown in the formula I or pharmaceutically acceptable salt or a pharmaceutically acceptable crystal form or pharmaceutically acceptable hydrate or pharmaceutically acceptable solvate thereof. R1, R2, R3, R4 and R5 are selected from H, halogen, hydroxyl, nitryl and carbonyl or C1-C8 alkyl respectively or simultaneously; R6 and R7 are selected from H or C1-C8 alkyl respectively or simultaneously, and R6 and R7 are connected to form a five-membered ring or a six-membered ring containing 3-17 carbon atoms. Compared with pirfenidone, the novel compound has different ring structures, the anti-fibrosis activity of the novel compound is remarkably superior to that of pirfenidone, and especially, the inhibition ratio of the novel compound for fibroblast proliferation is increased by at least 30% compared with pirfenidone; meanwhile, the inhibition effect of the novel compound on fibroblast secretory fibronectin is remarkably superior to that of pirfenidone, and good industrial prospects are achieved. The formula I is shown in the specification.
-
(2017/04/19)

Application of pirfenidone derivative to pharmacy
The invention discloses application of a compound as shown in a formula (I) (the formula can be seen in specification) or medically acceptable salt, the crystal form, aquo-complex or solvent thereof to preparation of anti-fibrosis drugs and/or antineoplastic drugs; wherein R1, R2, R3, R4 and R5 are separately or simultaneously selected from H, halogen, hydroxyl, nitro, carbonyl or a C1 alkyl group, a C2 alkyl group, a C3 alkyl group, a C4 alkyl group, a C5 alkyl group, a C6 alkyl group, a C7 alkyl group or a C8 alkyl group; R6 and R7 are separately or simultaneously selected from H, O=C-NH, S=C-NH, phenyl, methyl-substituted phenyl, ethyl-substituted phenyl, methoxyl-substituted phenyl and ethyoxyl-substituted phenyl. The invention provides application of the novel compound as shown in the formula (I) (the formula can be seen in specification) or medically acceptable salt, the crystal form, aquo-complex or solvent thereof to preparation of anti-fibrosis drugs and/or antineoplastic drugs, compared with pirfenidone, the novel compound has a specific C=N-N structure, anti-fibrosis activity of the novel compound is remarkably better than that of pirfenidone, and the novel compound has good industrialized prospect.
-
(2017/06/10)

Preparing method for pirfenidone
The invention relates to a preparing method for pirfenidone. The method includes the steps that under the action of an acid catalyst, 2-pentenenitrile is used for reacting with trimethyl/triethyl orthoformate to generate 2-methyl-1-alkoxy-4-cyano-1,3-butadiene (II), and 2-methyl-1-alkoxy-4-cyano-1,3-butadiene (II) and aniline are condensed and then hydrolyzed to obtain pirfenidone. The used raw materials are low in price and easy to obtain, the process flow is short, and the preparing method is easy to operate, environmentally friendly, high in reaction selectivity and high in product yield and purity.
-
Paragraph 0034; 0035

(2017/01/09)

AN IMPROVED METHOD FOR THE SYNTHESIS AND PURIFICATION OF PIRFENIDONE
The present invention provides a process for the synthesis of pirferidone by reacting 5-methyl-2-pyridone with a low quantity of bromobenzene in a low quantity of polar aprotic solvent in the presence of a copper catalyst and a base. The present invention also provides a method for purification of pirfenidone by initially synthesizing an acid adduct of pirfenidone from crude pirfenidone and then recovering pirfenidone with increased purity.
-
Page/Page column 7-8

(2016/08/23)

Pirfenidone derivative and preparation method and use thereof
The invention relates to a pirfenidone derivative and a preparation method and use thereof and discloses a compound shown as in formula I or its pharmaceutically acceptable salt, crystal, hydrate or solvate, wherein R1 is selected from H or C1-C8 alkyl, R2, R3, R4, R5 and R6 are selected respectively or all from H or halogen, and at least one of the R2, R3, R4, R5 and R6 is halogen. The novel compound of the invention is significantly better than pirfenidone in anti-fibrosis activity and has an inhibitory rate of higher than 42% for fibroblast proliferation, as much as 5 times higher than 8.15% of pirfenidone, and the derivative has good industrial prospect.
-
Paragraph 0072; 0073; 0074; 0075; 0076

(2016/10/24)

Crystal form of pirfenidone and preparation method of crystal form
The invention discloses a crystal form of pirfenidone. The crystal form is characterized in that an X-ray powder diffraction pattern of the crystal form comprises characteristic diffraction peaks at the positions of which 2 theta values are 8.8 to 9.2 degrees, 14.3 to 14.7 degrees, 14.9 to 15.3 degrees, 18.4 to 18.8 degrees, 18.7 to 19.1 degrees, 21.0 to 21.4 degrees, 22.7 to 23.1 degrees, 22.9 to 23.3 degrees, 24.3 to 24.7 degrees, 26.7 to 27.1 degrees, and 27.2 to 27.6 degrees. The invention further discloses a preparation method of the crystal form of pirfenidone.
-
Paragraph 0017

(2017/01/09)

Copper-Catalyzed N-Arylation of 2-Pyridones Employing Diaryliodonium Salts at Room Temperature
A new and mild synthetic approach for the N-arylation of 2-pyridones with diaryliodonium salts has been developed. Most reactions proceed readily at room temperature in the presence of 10 mol % of copper chloride. As a result, a wide range of N-arylpyridine-2-ones were synthesized in yields of 23% to 99%. With this method, an antifibrotic drug, Pirfenidone, was successfully synthesized in 99% yield within 30 min at room temperature.
Jung, Seo-Hee,Sung, Dan-Bi,Park, Cho-Hee,Kim, Won-Suk
p. 7717 - 7724
(2016/09/12)

A copper-based metal-organic framework as an efficient and reusable heterogeneous catalyst for ullmann and goldberg type C-N coupling reactions
A highly porous metal-organic framework (Cu-TDPAT), constructed from a paddle-wheel type dinuclear copper cluster and 2,4,6-tris(3,5-dicarboxylphenylamino)-1,3,5-triazine (H6TDPAT), has been tested in Ullmann and Goldberg type C-N coupling reactions of a wide range of primary and secondary amines with halobenzenes, affording the corresponding N-arylation compounds in moderate to excellent yields. The Cu-TDPAT catalyst could be easily separated from the reaction mixtures by simple filtration, and could be reused at least five times without any significant degradation in catalytic activity.
Long, Wei,Qiu, Wenge,Guo, Chongwei,Li, Chuanqiang,Song, Liyun,Bai, Guangmei,Zhang, Guizhen,He, Hong,Kuznetsov, Maxim L.
p. 21178 - 21192
(2016/01/25)

ANTI-FIBROTIC PYRIDINONES
This application relates to polycyclic compounds with a pyridinone or pyridinone derivative core including, substituted pyridinones, 5,6- and 6,6- bicyclic heterocycles and substituted pyridine-thiones. This application also discloses methods of preparing these polycyclic compounds, pharmaceutical compositions and medicaments comprising said compounds and methods to treat, prevent or diagnose diseases, disorders or conditions associated with fibrosis.
-
Paragraph 0363; 0673

(2015/11/02)

Synthesis of highly functionalized diaryl ethers by copper-mediated O-arylation of phenols using trivalent arylbismuth reagents
Highly functionalized diaryl ethers were prepared by copper(II) acetate mediated O-arylation reaction of phenols using trivalent organobismuthanes. The reaction is performed under simple conditions and tolerates a wide diversity of functional groups on the phenol and on the organobismuth reagent. Substoichiometric amounts of catalyst can be used by performing the reaction under an oxygen atmosphere. The N-arylation of pyridones is also reported. Highly functionalized diaryl ethers were prepared by a copper(II) acetate mediated O-arylation reaction of phenols using trivalent organobismuthanes (see scheme). The reaction is performed under simple conditions and tolerates a wide diversity of functional groups on the phenol and on the organobismuth reagent. Substoichiometric amounts of catalyst can be used by performing the reaction under an oxygen atmosphere. The N-arylation of pyridones is also reported. FG=functional group.
Crifar, Cynthia,Petiot, Pauline,Ahmad, Tabinda,Gagnon, Alexandre
supporting information
p. 2755 - 2760
(2014/03/21)

ANTI-FIBROTIC PYRIDINONES
Disclosed are pyridinone compounds, method for preparing these compounds, and methods for treating fibrotic disorders.
-
Paragraph 0878-0879

(2014/04/17)

Synthesis, pharmacophores, and mechanism study of pyridin-2(1H)-one derivatives as regulators of translation initiation factor 3A
Twenty-seven 1,5-disubstituted-pyridin-2(1H)-one derivatives were synthesized and evaluated for their anti-cancer and anti-fibrosis activity by A549 and NIH3T3 cell viability assays, respectively. To study the selectivity between the cancer and fibrosis cell lines, pharmacophore models (F 1-F4) were built in advance for compounds with pyridin-2(1H)-one scaffold, which revealed the relationship between the occupation of the aromatic sub-site F4 and potent anti-cancer activity. The relationship between structure and anti-cancer activity for all target compounds is also reported herein: 1-Phenyl-5-((m-tolylamino)methyl) pyridine-2(1H)-one (22) displayed both potency and selectivity (IC50 = 0.13 mM) toward the A549 cell line through the inhibition of translation initiation, especially by eIF3a suppression, and can be treated as a lead for the design of novel eIF3a regulators and anti-lung cancer agents. A series of pyridin-2(1H)-one derivatives were synthesized. Elucidation of their pharmacophores and mechanism of action suggested that structures with F 4 occupation displayed more selective anti-cancer than anti-fibrosis activity and that they interrupt the initiation phase of translation by acting on the eukaryotic translation initiation factor 3, subunit A.
Zhu, Weixing,Shen, Jie,Li, Qianbin,Pei, Qi,Chen, Jun,Chen, Zhuo,Liu, Zhaoqian,Hu, Gaoyun
p. 654 - 666
(2013/09/24)

Pirfenidone structural isosteres: Design, synthesis and spectral study
Series of 5-substituted arylpyridin-2(1 H )-ones and arylpyrimidin-4(3 H )-ones were designed and synthesized based on pirfenidone, a compound which shows promising therapeutic effects for treatment of fibrosis. The compounds 1a - c , 2a - c and 3a - c were obtained under mild conditions by arylation of the appropriate heterocyclic amines with arylboronic acids under Chan-Lam- Evans conditions. The synthesis of the useful synthon N -(4-methoxyphenyl)-5-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan- 2-yl)-(1 H )-pyridin-2-one ( 4 ) is also reported. All compounds were characterized by spectral and elemental analysis and structural elucidation by 1 H and 13 C NMR is discussed herein.
Kader, Kamelia F. Abd El,Bialy, Serry A.A. El,El-Ashmawy, Mahmoud B.,Boykin, David W.
p. 193 - 197
(2013/01/16)

SUBSTITUTED N-ARYL PYRIDINONES
Disclosed herein are methods of administering deuterated pirfenidone and kits thereof.
-
Page/Page column 62

(2012/09/22)

ADHESIVE MATERIAL CONTAINING 5-METHYL-1-PHENYL-2-(1H)-PYRIDONE
There is provided an adhesive preparation containing 5-methyl-1-phenyl-2-(1H)-pyridone. The adhesive preparation is a 5-methyl-1-phenyl-2-(1H)-pyridone-containing adhesive preparation including an active medicinal ingredient-containing layer, characterized in that the active medicinal ingredient-containing layer contains an lipophilic base, a dissolving agent (except glycerin and a medium-chain aliphatic acid triglyceride), and 5-methyl-1-phenyl-2-(1H)-pyridone or medically acceptable salts thereof.
-
(2011/09/15)

IMPROVED METHOD FOR SYNTHESIZING PIRFENIDONE
A process for synthesizing pirfenidone from bromobenzene having less than about 0.15% by weight dibromobenze is disclosed. Also disclosed are processes of synthesizing pirfenidone without using ethyl acetate or n-butanol, and pirfenidone having controlled levels of ethyl acetate, n-butanol, di(5-methyl-2-pyridinone)benzenes, and other impurities having specified retention times. Also disclosed are formulated dosage forms including the disclosed pirfenidone.
-
Page/Page column 13-14

(2010/12/29)

SUBSTITUTED N-ARYL PYRIDINONES
Disclosed herein are substituted N-Aryl pyridinone fibrotic inhibitors and/or collagen infiltration modulators of Formula I, process of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.
-
Page/Page column 22

(2009/01/24)

USE OF PYRIDONE DERIVATIVES IN THE PREVENTION OR TREATMENT OF TISSUE OR ORGAN TOXICITY INDUCED BY CYTOTOXIC AGENTS AND RADIATION
The present invention is directed to a novel use of pyridone derivatives such as pirfenidone for the prevention and treatment of damages to tissues or organs induced by various cytotoxic agents, such as chemotherapeutic agents, biologics, immunosuppressants and radiation. Such prophylactic and/or therapeutic effects of the pyridone derivatives make it possible to increase therapeutic dosages of the cytotoxic agent, thereby enhancing the therapeutic efficacy of the cytotoxic agent and radiation therapy.
-
Page/Page column 8-9

(2008/12/06)

TOPICAL ANTISEPTIC COMPOSITIONS AND METHODS
In a preferred embodiment, a method of treating bacteria, fungi, and/or viruses on the surface of, or within, the layers of the dermis of skin, ears, fingernails, toenails, or hoofs of mammalian species, comprising: applying to the surface or layers a pharmaceutical substance including an effective amount of one or more 2-(1H) pyridone compound(s).
-
(2008/06/13)

Treatment of cytokine growth factor caused disorders
In preferred embodiments, a method of prevention and treatment of disorders caused by enhanced proliferation and enhanced biosynthesis caused by cytokine growth factors in humans and other animals, the method including: administering to a human or other animal an effective dose of a pharmaceutical substance including an N-substituted 2(1H) pyridone and/or an N-substituted 3(1H) pyridone; and a composition for prevention and treatment of disorders caused by enhanced proliferation and enhanced biosynthesis caused by cytokine growth factors in humans and other animals, the composition including: a pharmaceutical preparation including an effective dose of an N-substituted 2(1H) pyridone and/or an N-substituted 3(1H) pyridone.
-
(2008/06/13)

Compositions and method for treatment of lymphomas, leukemias, and leiomyomas
In a preferred embodiment, drugs having chemotherapeutic properties which are useful against certain neoplastic disorders with wide safety margins as evidenced by their low toxicity, and molecular actions. Such drugs include as active ingredient(s) one or more N-substituted 2-(1H) pyridone(s) and/or N-substituted 3-(1H) pyridone(s). The compositions of this invention are novel as anti-neoplastic drugs, namely as an agent for treating leukemias, lymphomas, and leiomyomas.
-
(2008/06/13)

Inhibition of tumor necrosis factor α
In a preferred embodiment, a method for the inhibition of the synthesis and release of tumor necrosis factor from various cells, comprising: administering to a human or other mammal an effective dose of one or more pharmaceutical substances selected from the group consisting of N-substituted 2(1H)pyridones, N-substituted 3(1H)pyridones, and pharmaceutically acceptable salts thereof.
-
(2008/06/13)

5-Methyl-1-phenyl-2-(1H)-pyridone compositions and methods of use
Novel analgesic, anti-pyretic, anti-inflammatory compositions containing as the active ingredient the compound, 5-methyl-1-phenyl-2-(1H)-pyridone are described. Such compositions have also been found to cause significant lowering of serum uric acid and glucose levels and to be effective in the treatment of a number of upper respiratory ailments in humans and other mammals. Skin conditions such as dermatitis and poison ivy are also alleviated by this agent. The compositions containing 5-methyl-1-phenyl-2-(1H)-pyridone caused no irritation on oral administration or when applied to specific target tissues showed no significant irritation or other sequelae.
-
(2008/06/13)