473927-64-9

Basic information

• Product Name: 1-(4-Methoxyphenyl)-6-(4-iodophenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester
• Synonyms: 1-(4-Methoxyphenyl)-6-(4-iodophenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester;Ethyl 6-(4-iodophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate;Apixaban IV;6-(4-iodophenyl)-1-(4-Methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate;Ethyl 6-(4-iodophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-;ethyl 6-(4-iodophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5-dihydropyrazolo[3,4-c]pyridine-3-carboxylate;Ethyl 6-(4-iodophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine;1-(4-Methoxyphenyl)-6-(4-iodophenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl este
• CAS NO: 473927-64-9
• Molecular Formula: C₂₂H₂₀IN₃O₄
• Molecular Weight: 517.31637
• EINECS: 200-258-5
• Mol File: 473927-64-9.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 649.4±55.0 °C(Predicted)
• Appearance: /
• Density: 1.60
• Storage Temp.: 2-8°C(protect from light)
• PKA: -0.78±0.20(Predicted)
• CAS DataBase Reference: 1-(4-Methoxyphenyl)-6-(4-iodophenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-Methoxyphenyl)-6-(4-iodophenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester(473927-64-9)
• EPA Substance Registry System: 1-(4-Methoxyphenyl)-6-(4-iodophenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester(473927-64-9)

Safety Data

• Hazardous Substances Data: 473927-64-9(Hazardous Substances Data)

Usage

Description

1-(4-Methoxyphenyl)-6-(4-iodophenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester, also known as Ethyl 6-(4-Iodophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate, is a chemical compound with a complex structure. It is an intermediate in the synthesis of Apixaban (A726700), a potent and selective inhibitor of coagulation factor Xa.

Uses

Used in Pharmaceutical Industry:
1-(4-Methoxyphenyl)-6-(4-iodophenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester is used as an intermediate for the synthesis of Apixaban, a potent, direct, selective, and orally active inhibitor of coagulation factor Xa. 1-(4-Methoxyphenyl)-6-(4-iodophenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester plays a crucial role in the development of new oral anticoagulants for the prevention of venous thromboembolism in total hip and knee replacement orthopedic surgeries, as well as in the treatment of patients with venous thromboembolic disorder or atrial fibrillation.
Used in Orthopedic Surgery:
In the field of orthopedic surgery, 1-(4-Methoxyphenyl)-6-(4-iodophenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester contributes to the development of Apixaban, which is a potential new oral coagulant useful for preventing venous thromboembolism in patients undergoing total hip and knee replacement surgeries.
Used in Stroke Treatment:
1-(4-Methoxyphenyl)-6-(4-iodophenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester is also used in the development of Apixaban for stroke treatment, as it helps in the management of patients with venous thromboembolic disorder or atrial fibrillation, reducing the risk of stroke and other thromboembolic events.

Upstream product

• 473927-69-4 1-(4-iodo-phenyl)-3-morpholin-4-yl-5,6-dihydro-1H-pyridin-2-one 
• 473927-63-8 ethyl (2Z)-chloro[2-(4-methoxyphenyl)hydrazinylidene]ethanoate 
• 104-94-9 4-methoxy-aniline 
• 1415831-80-9 1-(4-iodophenyl)-3-trimethylsilyloxy-5,6-dihydro-1H-pyridin-2-one 
• 27143-07-3 ethyl 2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate 
• 1415831-82-1 1-(4-iodophenyl)piperidine-2,3-dione 
• 385425-15-0 1-(2-oxopiperidin-1-yl)-4-iodobenzene 
• 545445-10-1 3,3-dichloro-1-(4-iodophenyl)-piperidin-2-one 
• 540-37-4 p-aminoiodobenzene 
• 4509-90-4 5-bromovaleroyl chloride 
• 2067-33-6 5-bromopentanoic acid 

Downstream Products

• 959426-35-8 6-(4-iodophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid 
• 503614-91-3 1-(4-methoxy-phenyl)-7-oxo-6-[4-(2-oxo-piperidin-1-yl)-phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester 
• 543744-69-0 6-(2'-formyl-biphenyl-4-yl)-1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester 
• 959426-36-9 6-(4-iodophenyl)-1-(4-methoxyphenyl)-N-methyl-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide 
• 473927-65-0 6-(4-iodophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide 
• 503614-92-4 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid 
• 503614-35-5 3-(bromomethyl)-6-(4-iodophenyl)-1-(4-methoxyphenyl)-5,6-dihydro-1H-pyrazolo[3,4-c]pyridin-7(4H)-one 
• 503612-80-4 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxo-1-piperazinyl)phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide 
• 503612-82-6 1-(4-methoxyphenyl)-3-(4-methyloxazol-2-yl)-6-[4-(2-oxopiperidin-1-yl)phenyl]-1,4,5,6-tetrahydropyrazolo[3,4-c]pyridin-7-one 
• 503612-83-7 1-(4-methoxyphenyl)-3-(4-methyloxazol-2-yl)-6-[4-(2-oxo-2H-pyridin-1-yl)phenyl]-1,4,5,6-tetrahydropyrazolo[3,4-c]pyridin-7-one 
• 503612-88-2 1-(4-methoxyphenyl)-3-methyl-6-[4-(2-oxopiperidin-1-yl)-phenyl]-1,4,5,6-tetrahydropyrazolo[3,4-c]pyridin-7-one 

Relevant articles and documents

Pyrazolo[3,4-c]pyridine derivative

The invention relates to a pyrazolo[3,4-c]pyridine derivative. The invention relates to a compound represented by a formula (I), a tautomer thereof, an optical isomer thereof or a pharmaceutically acceptable salt thereof, wherein the formula (I) is shown in the description, and Z, X, RNc, RNd, RNe and RNf are defined according to the claim 1. The invention further relates to the pharmaceutical composition contain the compound. The invention further relates to use of the compound or the pharmaceutical composition in preparing a drug for preventing and/or treating a disease which inhibits positive influence of an Xa factor, particularly use in preparing the drug for preventing and/or treating the disease which inhibits positive influence of the Xa factor under the condition of low hemorrhage risk.

Novel intermediate and polymorphs of 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5,6,7-tetra hydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide and process thereof

The present invention provides a novel intermediate as well as novel polymorphs of 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide compound represented by the following structural formula-1 and processes for their preparation.

A METHOD OF PREPARING APIXABAN

The object of the present solution provides a method preparing apixaban of formula (I) in which ethyl 6-(4-iodophenyl)- 1 -(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo [3,4- c]pyridine-3-carboxylate of formula (III) is reacted with piperidin-2-one of formula (IV) in the presence of a base and a ligand and under catalysis by copper or by copper (II) ions, wherein a phosphoric acid salt is used as the base and an amine from the group of 1,2-diamines is used as the ligand in an aprotic solvent, and ethyl 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxo-1- piperidin-1-yl)phenyl] -4, 5,6,7-tetrahydro-1H-pyrazol-[3,4-c]pyridine-3-carbvoxylate is prepared, which is converted, by reaction with ammonia in a suitable solvent, to apixaban of formula (I), which is isolated and optionally crystallized.