1003-68-5Relevant articles and documents
Manganese-Promoted Regioselective Direct C3-Phosphinoylation of 2-Pyridones
Chantarojsiri, Teera,Kittikool, Tanakorn,Phakdeeyothin, Kunita,Yotphan, Sirilata
, p. 3071 - 3078 (2021)
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.
Preparation method of high-purity pirfenidone
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Paragraph 0062-0242, (2020/05/02)
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.
A process for preparing 2 - chloro -5 - methyl pyridine method (by machine translation)
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Paragraph 0012; 0017-0019; 0025; 0028; 0032; 0036, (2019/07/04)
The invention belongs to the technical field of organic chemical industry, relates to 2 - chloro - 5 - methyl pyridine preparation method, more specifically, relates to a 5 - methyl - 3, 4 - dihydro pyridine - 2 (1 H) - one (hereinafter referred to as the: pyridone) and chlorine gas, first synthesis of 2 - hydroxy - 5 - methyl pyridine (hereinafter referred to as: synthetic azo), re-chlorinated preparing 2 - chloro - 5 - methyl pyridine. (by machine translation)
Method for preparing anti-fibrotic drug
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Paragraph 0016; 0018, (2019/04/27)
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.
5-alkyl-N-substituted aryl pyridone derivative, preparation method thereof and application of derivative
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Paragraph 0082; 0085-0087; 0100-0101, (2019/10/04)
The invention provides a compound as shown in a formula I, or pharmacologically acceptable salt of the compound, or a prodrug of the compound, or a hydrate or solvate of the compound or a crystal form of the compound. The invention further provides a preparation method and an application of the compound. The structurally novel 5-methyl-2(1H) pyridone derivative as shown in the formula I has an obvious inhibiting effect on fibroblast proliferation and fibroblast secretory fiber binding protein (Fn), and the inhibiting effect is more significant than that of a positive drug pirfenidone (PF). The compound has an excellent application prospect in preparation of drugs for treating or preventing diseases such as fibrosis diseases and tumors.
5 - Methyl - 2 (1 H) pyridone derivative and its preparation and use
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Paragraph 0076-0079, (2018/04/03)
The invention discloses 5-methyl-2(1H)pyridone derivatives represented by the formula (I), crystal form, pharmaceutically-acceptable salt, hydrate, solvate, or prodrug thereof, wherein in the formula (I), the R represents a hydrogen atom, a halogen atom,
IMPROVED PROCESS FOR THE PREPARATION OF PIRFENIDONE
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Page/Page column 5, (2018/10/25)
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.
A highly efficient Suzuki-Miyaura methylation of pyridines leading to the drug pirfenidone and its CD3 version (SD-560)
Falb, Eliezer,Ulanenko, Konstantin,Tor, Andrey,Gottesfeld, Ronen,Weitman, Michal,Afri, Michal,Gottlieb, Hugo,Hassner, Alfred
supporting information, p. 5046 - 5053 (2017/11/09)
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.
5-methyl-2(1H) pyridone derivative and preparation method and application thereof
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Paragraph 0077; 0078; 0079, (2017/04/12)
The invention discloses a 5-methyl-2(1H) pyridone derivative shown in the formula I or salt, a hydrate, a solvate or a pro-drug thereof, which are pharmaceutically acceptable and have the same crystal form. In the formula I, X is selected from S or NH; R1
5 - methyl - 2 (1 H) pyridone derivative and its preparation and use
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Paragraph 0078-0080, (2017/09/12)
The invention discloses 5-methyl-2(1H)pyridone derivatives disclosed as Formula I, or crystal forms, pharmaceutically acceptable salts, hydrates, solvates or pro-drugs thereof. In the formula I, R is selected from hydroxy group, mercapto group, amino grou
