52549-17-4

Basic information

• Product Name: Pranoprofen
• Synonyms: PRANOPROFEN;2-(5h-[1]benzopyrano[2,3-b]pyridin-7-yl)propionic acid;(RS)-Pranoprofen;5H-[1]Benzopyrano[2,3-b]pyridine-7-acetic acid, a-methyl- (9CI);a-Methyl-5H-[1]benzopyrano[2,3-b]pyridine-7-ylacetic acid;dl-Pranoprofen;Niflan;Y 8004
• CAS NO: 52549-17-4
• Molecular Formula: C15H13NO3
• Molecular Weight: 255.27
• EINECS: 1308068-626-2
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;NIFLAN;>97%,BR
• Mol File: 52549-17-4.mol

Chemical Properties

• Melting Point: 182-183°
• Boiling Point: 398.5°C (rough estimate)
• Flash Point: 235.5 °C
• Appearance: /
• Density: 1.1654 (rough estimate)
• Vapor Pressure: 1.79E-09mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.27±0.10(Predicted)
• CAS DataBase Reference: Pranoprofen(CAS DataBase Reference)
• NIST Chemistry Reference: Pranoprofen(52549-17-4)
• EPA Substance Registry System: Pranoprofen(52549-17-4)

Safety Data

• RIDADR: UN 2811 6.1 / PGIII
• RTECS: DJ3100950
• Hazardous Substances Data: 52549-17-4(Hazardous Substances Data)

Usage

Uses

Used in Ophthalmology:
Pranoprofen is used as an anti-inflammatory agent for the treatment of various eye conditions, such as postoperative inflammation and pain. Its application in ophthalmology is due to its ability to effectively reduce inflammation and alleviate discomfort associated with ocular surgeries or other eye-related issues.

Originator

Niflan, Yoshitomi ,Japan ,1981

Manufacturing Process

A mixture of 100 g of ethyl 2-cyano-2-(5H-[1]benzopyrano[2,3-b]-pyridin-7yl)propionate, 500 ml of glacial acetic acid and 200 g of concentrated hydrochloric acid is refluxed for 48 hours. The reaction mixture is concentrated, and the residue is dissolved in hot water. The solution is adjusted to pH 2 to 3 by addition of 10% sodium hydroxide. The resulting crystalline precipitate is washed thoroughly with water, and recrystallized from aqueous dioxane to give 74 g of 2-(5H-[1]benzopyrano[2,3-b]-pyridin-7yl)propionic acid as white crystals melting at 183°C to 183.5°C.

Therapeutic Function

Analgesic, Antiinflammatory

Biochem/physiol Actions

Pranoprofen is used in eyes to treat chronic allergic conjunctivitis. It is also used as an anti-inflammatory and analgesic drug after strabismus surgery.

InChI:InChI=1/C15H13NO3/c1-9(15(17)18)10-4-5-13-12(7-10)8-11-3-2-6-16-14(11)19-13/h2-7,9H,8H2,1H3,(H,17,18)

Upstream product

• 144-55-8 sodium hydrogencarbonate 
• 261-27-8 5H-[1]-chromeno[2,3-b]pyridine 
• 56355-15-8 2-(4-hydroxyphenyl)propionic acid ethylester 
• 36404-90-7 2-fluoropyridine-3-carboxaldehyde 
• 86618-09-9 ethyl 2-(5H-chromeno[2,3-b]pyridin-7-yl)propanoate 
• 53944-31-3 7-ethyl-5H-[1]-benzopyrano [2,3-b] pyridin-5-one 
• 123-07-9 4-Ethylphenol 
• 2942-59-8 2-chloronicotinic acid 
• 124-38-9 carbon dioxide 
• 52549-19-6 2-(5-oxo-5H-chromeno[2,3-b]pyridin-7-yl)-propionic acid 

Downstream Products

• 52549-19-6 2-(5-oxo-5H-chromeno[2,3-b]pyridin-7-yl)-propionic acid 

Relevant articles and documents

Formation and Disproportionation of Xanthenols to Xanthenes and Xanthones and Their Use in Synthesis

A facile and versatile strategy employing TiCl4-mediated cyclization followed by a Cannizzaro reaction has been developed for the synthesis of various xanthene derivatives. The reaction proceeded smoothly to afford both xanthenes/xanthones or their sulfur derivatives and tolerated a wide range of electronically diverse substrates. Using this methodology, pranoprofen was synthesized in three steps in 59% overall yield from commercially available starting materials.

Novel preparation method of pranoprofen

The invention discloses a novel preparation method of pranoprofen. The novel preparation method of the pranoprofen has the advantages of being high in yield, having less impurities, and being safe andenvironmentally friendly. The novel preparation method of the pranoprofen comprises the following steps that step 1, 5H-[1]-benzopyran[2,3-b]pyridine and propionyl chloride are directly acylated; step 2, bromination is carried out; step 3, potassium tert-butoxide or sodium tert-butoxide is used for hydrolysis, and finally, rearrangement is carried out to obtain the pranoprofen.

pula Luo river fragrance synthetic method

The invention provides a synthetic method for pranoprofen and a novel compound structure which can be used for preparation of pranoprofen. More specifically, 2-chloronicotinic acid and paraethyl phenol are used as raw materials, and nucleophilic substitution, ring closure, halogenation, carbonyl group reduction, hydroxyl group elimination, a Grignard reaction and CO2 carbonyl group insertion are carried out so as to prepare pranoprofen.

Substituted alkanoic acids and derivatives

Substituted alkanoic acids and derivatives thereof of the formula: SPC1 Wherein each of X1 and X2 is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms; each of R1 and R2 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; A is a carbonyl group, a methylene group or an alkylidene group having 2 to 4 carbon atoms; Y is --O--, --S-- or --N(R)-- [wherein R is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms]; Z is OH or Q--B--N(R3)(R4) [wherein Q is O (oxygen atom) or NH, B is an alkylene group having 1 to 4 carbon atoms and each of R3 and R4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, or R3 and R4 together with the adjacent nitrogen atom form a saturated heterocycle selected from the group consisting of pyrrolidine, piperidine, morpholine, piperazine and piperazine substituted by an alkyl group having 1 to 4 carbon atoms at the 4-position]; and ring P represents a pyridine or a pyridine N-oxide ring; and pharmaceutically acceptable salts thereof are useful as antirheumatics, analgesics, antipyretics and anti-inflammatory agents.