- MANUFACTURING PROCESS FOR 3,5-DICHLOROPICOLINONITRILE FOR SYNTHESIS OF VADADUSTAT
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Disclosed herein are methods and processes of preparing vadadustat or a pharmaceutically acceptable salts thereof, and intermediates (e.g., a compound of Formula (I), (I-F), (II), or (IV), or a pharmaceutically acceptable salts thereof) useful for the syn
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- NOVEL CRYSTALLINE COMPOUND OF VADADUSTAT
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The present invention relates to a novel crystalline compound of Vadadustat, to processes for its preparation, to pharmaceutical compositions containing it and to its use in therapy.
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Page/Page column 11
(2021/12/31)
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- Development of a Robust and Scalable Process for the Large-Scale Preparation of Vadadustat
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A novel and scalable process is developed for the industrial synthesis of vadadustat. The four-step process is one step shorter compared to the reported routes with an increase in total yield to 49.1%. Detailed optimizations furnish vadadustat with a purity of >99.5% through cross-coupling, aromatic substitution and nitrile hydrolysis, amidation, and ester-ether deprotection. The process is also robust and was demonstrated in a kilogram laboratory. Meanwhile, the corresponding impurity profile was thus studied in detail and well documented.
- Lin, Biyue,Kou, Jingping,Wu, Shuming,Cai, Xuerong,Xiao, Qingbo,Li, Yinglong,Hu, Jian,Li, Jianbing,Wang, Zhongqing
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p. 960 - 968
(2021/04/05)
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- Preparation method of valduxostat and intermediate thereof
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The invention relates to a preparation method of valduxostat and an intermediate thereof, and belongs to the field of medicinal chemistry. The preparation method comprises the following steps: taking 3-chloro-5-(3-chlorphenyl)-2-cyanopyridine as a starting material, carrying out hydrolysis reaction, and then carrying out condensation reaction to obtain a compound, namely the intermediate; and further reacting the intermediate compound to obtain vadadustat. The method has the advantages of short route, simple and easily available raw materials, low cost and mild reaction conditions, and is suitable for industrial large-scale production.
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Paragraph 0067-0076
(2021/09/15)
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- Preparation method of pyridine cyclic compound
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The invention provides a preparation method of a pyridine cyclic compound, and belongs to the field of pharmaceutical chemicals. The method comprises the steps: mixing 3,5-dihydroxypicolinic acid, concentrated sulfuric acid and an alcohol solvent, and performing esterification reaction to obtain 3,5-dihydroxypicolinic acid methyl ester; then sequentially carrying out protection group feeding and ammoniation to obtain {[5-(3-chlorphenyl)-3-hydroxypyridin-2-yl]amino}acetic acid. The product produced by the method has the characteristics of high purity, high yield, low cost, simple operation andstable process.
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Paragraph 0041; 0054-0057; 0064-0065
(2020/06/16)
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- Preparation method and application of phenylpyridine compound
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The invention relates to a preparation method and application of a phenylpyridine compound, and belongs to the field of pharmaceutical chemicals. The method disclosed by the invention comprises the following steps: mixing 5-(3-chlorphenyl)-2-cyano-3-chloropyridine, alkali and an organic solvent to obtain 5-(3-chlorphenyl)-3-hydroxyl-pyridine formamide; and then sequentially carrying out a reactionwith sulfuric acid and glycine so as to obtain {[5-(3-chlorphenyl)-3-hydroxypyridine-2-yl] amino} acetic acid. The product produced by the method is high in purity, high in yield, low in process cost, simple to operate and stable in process.
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Paragraph 0039; 0059-0066
(2020/07/28)
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- Preparation method and application of picolinamide
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The invention provides a preparation method of a picolinamide compound, and belongs to the field of pharmaceutical and chemical industry. According to the preparation method, 3,5-dihydroxypicolinic acid methyl ester, hydroxylamine hydrochloride, an alkali
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Paragraph 0047; 0068-0072
(2020/07/12)
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- Preparation method of vadadustat
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The invention provides a preparation method of vadadustat, and belongs to the field of pharmaceutical chemical industry. The method comprises the following steps: mixing 3,5-dichloro-2-picolinic acid,methanol and sulfuric acid at a certain temperature, and carrying out a reaction to obtain 3,5-dichloro-2-picolinic acid methyl ester; adding 3-chlorophenylboronic acid, and carrying out a catalyticreaction to obtain 5-(3-chlorphenyl)-3-chloropyridine-methyl formate; and adding glycine into the 5-(3-chlorphenyl)-3-chloropyridine-methyl formate, and carrying out a reaction to obtain the 5-(3-chlorphenyl)-3-chloropyridine-methyl formate. The method has the characteristics of high product purity, high yield, low cost, simple operation and stable process.
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Paragraph 0047; 0060-0065
(2020/04/02)
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- Preparation method of vardoxostat intermediate
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The invention relates to a preparation method of a vardoxostat intermediate, and belongs to the field of medicinal chemistry. The preparation method comprises the following steps: taking 3-methoxy-5-(3-chlorphenyl)-2-cyanopyridine as a starting material, carrying out hydrolysis reaction and condensation reaction to obtain an intermediate of a compound; the intermediate compound can be subjected toa further reaction to obtain vadustat (vardoxostat); the method has the advantages of short route, simple and accessible raw materials, lower cost and mild reaction conditions, and is suitable for industrial large-scale production.
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Paragraph 0057-0059
(2020/11/12)
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- PROCESS FOR PREPARING 2-[[5-(3-CHLOROPHENYL)-3-HYDROXYPYRIDINE-2-CARBONYL]AMINO]ACETIC ACID
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Disclosed herein are methods and processes of preparing vadadustat and pharmaceutically acceptable salts thereof, and intermediates of formula (I) and their salts useful for the synthesis of vadadustat.
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Paragraph 0071
(2019/11/28)
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- DEUTERIUM-ENRICHED HYPOXIA-INDUCIBLE FACTOR PROLYL HYDROXYLASE ENZYME INHIBITORS
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Provided herein are deuterium-enriched compounds of Formula (I), Formula (II), Formula (III), Formula (IV), Formula (V), and Formula (VI). Pharmaceutical compositions comprising the isotope-enriched compounds, and methods of using such compounds are also provided.
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Paragraph 0092
(2016/10/11)
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- A method for synthesizing Vadadustat (by machine translation)
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The invention discloses a method for synthesizing Vadadustat. The method 3, the 5 [...] two chloro -2 the pyridine [...] formic acid and glycine methyl ester hydrochloride for a condensation reaction; the obtained N-(3,5 the [...] two chloro pyridine -2 the carbonyl [...] ) glycine methyl ester and 3 the chlorobenzene [...] catalytic coupling reaction of the borate; the obtained N-[ 5 the [...] (3 the [...] chlorolphenyl) - 3 the [...] pyridine -2 the carbonyl [...] ] glycine methyl acetate and methanol sodium to methoxy substitution reaction; the obtained N-[ 5 the [...] (3 the [...] chlorolphenyl) - 3 the [...] methoxy pyridine -2 the carbonyl [...] ] glycine to perform hydrolysis reaction, obtaining the finished product Vadadustat. The synthetic method steps is relatively short, the operation is simplified, the cost is low, is an environmentally-friendly method, it is suitable for industrial production. (by machine translation)
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- PROCESS FOR PREPARING [(3-HYDROXYPYRIDINE-2-CARBONYL)AMINO]ALKANOIC ACIDS, ESTERS AND AMIDES
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Disclosed are processes for preparing [(3-hydroxypyridine-2-carbonyl)amino]-alkanoic acids, derivatives, inter alia, 5-aryl substituted and 5-heteroaryl substituted [(3-hydroxypyridine-2-carbonyl]aminolacetic acids. Further disclosed are methods for making prodrugs of [(3-hydroxypyridine-2-carbonyl)-amino]acetic acids, for example, [(3-hydroxypyridine-2-carbonyl]amino}acetic acid esters and {[3-hydroxypyridine-2-carbonyl]amino}acetic acid amides. The disclosed compounds are useful as prolyl hydroxylase inhibitors or for treating conditions wherein prolyl hydroxylase inhibition is desired.
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Page/Page column 22
(2012/12/14)
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- Prolyl hydroxylase inhibitors and methods of use
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The present disclosure relates to HIF-1α prolyl hydroxylase inhibitors, compositions which comprise the HIF-1α prolyl hydroxylase inhibitors described herein and to methods for controlling, inter alia, Peripheral Vascular Disease (PVD), Coronary Artery Disease (CAD), heart failure, ischemia, and anemia.
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Page/Page column 14
(2008/06/13)
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