135048-32-7

Basic information

• Product Name: 4-Pyridinecarboxylicacid,2-cyano-,hydrazide(9CI)
• Synonyms: 4-Pyridinecarboxylicacid,2-cyano-,hydrazide(9CI);2-Cyanoisonicotinohydrazide;4-Pyridinecarboxylicacid,2-cyano-,hydrazide;2-Cyano-4-pyridinecarboxylic acid hydrazide;Topiroxostat impurity M
• CAS NO: 135048-32-7
• Molecular Formula: C₇H₆N₄O
• Molecular Weight: 162.15
• Product Categories: AMIDE
• Mol File: 135048-32-7.mol

Chemical Properties

• Appearance: /
• Density: 1.37±0.1 g/cm3(Predicted)
• PKA: 10.38±0.10(Predicted)
• CAS DataBase Reference: 4-Pyridinecarboxylicacid,2-cyano-,hydrazide(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Pyridinecarboxylicacid,2-cyano-,hydrazide(9CI)(135048-32-7)
• EPA Substance Registry System: 4-Pyridinecarboxylicacid,2-cyano-,hydrazide(9CI)(135048-32-7)

Safety Data

• Hazardous Substances Data: 135048-32-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
4-Pyridinecarboxylic acid, 2-cyano-, hydrazide (9CI) is used as an intermediate in the synthesis of various pharmaceuticals. Its role in the creation of heterocyclic compounds makes it a crucial component in the development of new drugs, contributing to the advancement of medicine.
Used in Organic Chemistry:
In the field of organic chemistry, 4-Pyridinecarboxylic acid, 2-cyano-, hydrazide (9CI) serves as a valuable building block for the synthesis of a wide range of organic compounds. Its versatility in chemical reactions allows for the creation of diverse chemical entities with potential applications in various industries.
Used in Antimicrobial Applications:
4-Pyridinecarboxylic acid, 2-cyano-, hydrazide (9CI) has been studied for its antimicrobial properties, making it a potential candidate for use in applications aimed at combating microbial infections. Its effectiveness in this area could lead to the development of new antimicrobial agents.
Used in Antioxidant Applications:
The antioxidant properties of 4-Pyridinecarboxylic acid, 2-cyano-, hydrazide (9CI) have also been investigated, suggesting its potential use in applications that require protection against oxidative stress. This could include applications in the food industry, cosmetics, or even pharmaceuticals where antioxidant activity is beneficial.

Upstream product

• 58481-14-4 2-cyano-isonicotinic acid ethyl ester 
• 3783-38-8 methyl isonicotinate N-oxide 
• 161233-97-2 2-cyanopyridine-4-carboxylic acid 
• 94413-64-6 2-Cyano-4-carbomethoxypyridine 

Relevant articles and documents

Preparation method of medicine for treating chronic hyperuricemia

The invention discloses a preparation method of a medicine for treating chronic hyperuricemia. The method comprises the following steps: using methyl 2-cyanoisonicotinate and 4-cyanopyridine as initial raw materials, and carrying out hydrazinolysis reaction, condensation reaction, cyclization reaction and purification to obtain topiroxostat. On one hand, by using a hydrochloric acid alcohol solution, the energy consumption of the process is reduced, and the problem of poor safety is improved; and on the other hand, topiroxostat hydrochloride is refined and concentrated in alcohol water and then subjected to a salt dissolving process, so that the solubility of the topiroxostat in an alkaline solution is increased, the problem that chloride exceeds the standard is preliminarily solved, the salt dissolving process is more thorough, and the reaction proceeding degree is increased. Finally, in the purification process, the amount of chlorides in the product is further reduced by a method of hot melting the crude product in alcohol water, and the product quality is ensured; and the purity of the product is improved by selecting a purification solvent.

Preparation method of topiroxostat intermediate

The invention discloses a preparation method of a topiroxostat intermediate. The intermediate is 2-cyanoisoniazide. The method comprises the step of performing substitution reaction on 2-cyanoisonicotinic acid R ester and hydrazine acid salt under the action of alkali to produce the intermediate 2-cyanoisoniazide of the topiroxostat. The method provided by the invention has the beneficial effectsof convenience in operation, cheap and easily available raw materials, high yield and high purity.

Preparation method of topiroxostat

The invention provides a preparation method of topiroxostat. The preparation method comprises the steps that 2-cyano methyl isonicotinate is used as raw materials; hydrazinolysis is performed at -10 DEG C to -20 DEG C to obtain an intermediate; the intermediate and 4-cyanopyridine react under the conditions with sodium ethoxide and the pH being 4 to 6 to obtain the topiroxostat. The preparation method has the advantages that the 2-cyano methyl isonicotinate is used as a starting material; the 2-cyano methyl isonicotinate and hydrazine hydrate take condensation reaction at low temperature to prepare the intermediate; the intermediate and the 4-cyanopyridine are subjected to condensation and loop closing under the acid condition with sodium ethoxide to prepare the topiroxostat. The raw materials can be easily obtained; the reaction conditions are mild and are easy to control; a reagent with high toxicity is not used in the reaction process; the released toxic substances are few; the sidereaction products are few; the reaction safety is high; the pollution is small; the obtained purity is high; the preparation method is suitable for industrial production.

Preparation method of topiroxostat crystal form I

The invention relates to a preparation method of a topiroxostat crystal form I and belongs to the technical field of medicine. The invention provides the topiroxostat crystal form I suitable for preparing preparation and provides a preparation method of the topiroxostat crystal form I with environmental friendliness and suitability for industrial operation. According to the technical scheme of thepreparation method disclosed by the invention, 4-methyl formate pyridine is utilized as a starting material, and the topiroxostat crystal form I is prepared by the steps of introducing acylamino, dehydrating, performing nucleophilic substitution, performing nucleophilic addition, condensation salifying and the like. According to the technical scheme of the preparation method disclosed by the invention, a telescoping technology is utilized, so that solvent use and energy consumption are reduced; meanwhile, reasonable salifying can prevent genotoxic impurities from being generated.

4 - [5 - (pyridin-4-yl) - 1H-[ 1, 2, 4] triazol-3-yl] pyridine-2-carbonitrile method for the preparation of (by machine translation)

The invention relates to a preparation of 4-[5-(pyridine-4-yl)-1H-[1,2,4]triazole-3-yl]pyridine-2-formonitrile. The method includes following steps: preparing a compound methyl 2-cyanoisonicotinate represented as the formula (4) with a compound methylisonicotinic-N-oxide (5) being a starting raw material in the presence of a copper catalyst (CuX), a metal cyanide and dimethylcarbamyl chloride; performing hydrazinolysis to the methyl 2-cyanoisonicotinate to obtain a compound 2-cyanoisoniazide represented as the formula (3); and finally performing condensation with a compound 4-cyanopyridine represented as the formula (2) to obtain a compound topiroxostat represented as the formula (1). The method only comprises three steps and is simple in operation and post-treatment. By means of the copper catalyst, a usage amount of the metal cyanide is greatly reduced so that reaction conditions are milder. The method is high in purity of the prepared product and is suitable for industrial production.

Topiroxostat preparation technology

The invention discloses a topiroxostat preparation method. According to the method, 2-chloroisonicotinic acid which is cheap and easy to obtain serves as an initial material, potassium ferrocyanide serves as a green cyanogens source, AgI-KI-PEG generates 2-cyanoisonicotinate through cyanation of a mixed catalysis system and then directly acts with hydrazine hydrate to obtain 2-cyanoisonicotinate hydrazide under the action of an amide condensing agent phenyl dichlorophosphate (PDCP), and the product and 4-cyanopyridine are condensed to obtain topiroxostat. Through technological improvement of the reaction, reaction steps are shortened, the reaction yield is obviously increased by 90% or above, and the technological cost is obviously reduced. Meanwhile, a 2-chloroisonicotinic acid raw material which is cheaper and easy to obtain is used, use of corrosive thionyl chloride and other chlorinating agents is avoided, and the technology is suitable for industrial production. The method is short in synthesis step, easy to operate, mild in reaction condition, economical, environmentally friendly and suitable for industrial production, and the yield is obviously increased.

Discovery of 3-(3-cyano-4-pyridyl)-5-(4-pyridyl)-1,2,4-triazole, FYX-051-a xanthine oxidoreductase inhibitor for the treatment of hyperuricemia

Our previous study identified 2-[2-(2-methoxy-ethoxy)-ethoxy]-5-[5-(2-methyl-4-pyridyl)-1H-[1,2,4]triazol-3-yl]-benzonitrile (2) as a safe and potent xanthine oxidoreductase (XOR) inhibitor for the treatment of hyperuricemia. Here, we synthesized a series of 3,5-dipyridyl-1,2,4-triazole derivatives and, in particular, examined their in vivo activity in lowering the serum uric acid levels in rats. As a result, we identified 3-(3-cyano-4-pyridyl)-5-(4-pyridyl)-1,2,4-triazole (FYX-051, compound 39) to be one of the most potent XOR inhibitors; it exhibited an extremely potent in vivo activity, weak CYP3A4-inhibitory activity and a better pharmacokinetic profile than compound 2. Compound 39 is currently being evaluated in a phase 2 clinical trial.

NOVEL 1,2,4-TRIAZOLE COMPOUND

A novel 1,2,4-triazole compound which is useful as a therapeutic agent for hyperuricemia and gout due to hyperuricemia is provided. A compound is represented by the following general formula (1): wherein R2 represents an unsubstituted or substituted pyridyl group, R1 represents a similar pyridyl group, a pyridine-N-oxide group corresponding to these pyridyl groups, or a phenyl group, and R3 represents hydrogen or a lower alkyl group substituted with pivaloyloxy group and R3 bonds to a nitrogen atom in the ring. A process for production of a compound by reacting a nitrile and a hydrazide, and a therapeutic agent, particularly a xanthine oxidase inhibitor are also provided.