51234-28-7

Usage

Uses

Used in Pharmaceutical Industry:
Uniprofen was used as a non-steroidal anti-inflammatory drug (NSAID) for its anti-inflammatory and analgesic properties. However, due to its associated health risks, it was discontinued from the market.
Used in Ophthalmic Applications:
Uniprofen was also utilized as a non-steroidal anti-inflammatory ophthalmic agent, specifically designed for treating ocular inflammation and related conditions. Its use in this context was aimed at reducing inflammation and providing relief from discomfort in the eyes.

Originator

Opren,Dista Lilly,UK,1980

Manufacturing Process

The 6-benzoxazolyl analog of the 5-benzoxazolyl product is prepared as follows: (a) Ethyl 2-(2-p-chlorophenyl-6-benzoxazolyl)propionate: A solution of ethyl 2-(3-hydroxy-4-aminophenyl)propionate (2.5 g) in pyridine (15 ml) was treated with p-chlorobenzoyl chloride (1.65 ml) at 5°C. After stirring for 2 hours at room temperature the solution was evaporated to dryness. The residue was heated at 220°C until no more water was evolved, then was allowed to cool. This yielded ethyl 2-(2-p-Chlorophenyl-6- benzoxazolyl)propionate. (b) 2-(2-p-Chlorophenyl-6-benzoxazolyl)propionic acid: A solution of ethyl 2- (2-chlorophenyl-6-benzoxazolyl)propionate (4 g) in aqueous sodium hydroxide (30 ml) was heated on a steam bath for one-half hour. On cooling the black solution was washed with chloroform. On acidification of the black solution with hydrochloric acid the mixture was extracted with chloroform. This solution on evaporation yielded 2-(2-p-chlorophenyl-6-benzoxazolyl)propionic acid, MP 196°C.

Therapeutic Function

Antiinflammatory, Analgesic

World Health Organization (WHO)

Benoxaprofen, a nonsteroidal antiinflammatory agent, was introduced in 1980 for the treatment of rheumatic disorders. Following reports of serious adverse effects, some of which were fatal, it was withdrawn in several countries prior to worldwide withdrawal by the manufacturer in 1982.

Safety Profile

Poison by ingestion, subcutaneous, and intraperitoneal routes. Moderately toxic to humans by ingestion.Human systemic effects by ingestion: jaundice and gynecomastia (excessive development of the male mammary glands), changes in kidney tubules, decreased

InChI:InChI=1/C16H12ClNO3/c1-9(16(19)20)11-4-7-14-13(8-11)18-15(21-14)10-2-5-12(17)6-3-10/h2-9H,1H3,(H,19,20)

Upstream product

• 51234-41-4 2-[2-(4-chloro-phenyl)-benzooxazol-5-yl]-propionic acid ethyl ester 
• 51234-36-7 2-(2-p-chlorophenyl-5-benzoxazolyl)propionitrile 
• 51234-43-6 3-amino-4-hydroxyphenyl-2-methylacetic acid 
• 122-01-0 4-chloro-benzoyl chloride 
• 51234-23-2 2-(3-amino-4-hydroxyphenyl)-propionitrile 
• 87498-09-7 benoxaprofen methyl ester 
• 21850-61-3 2-(4-hydroxyphenyl)propanenitrile 
• 51234-22-1 3-nitro-4-hydroxyphenyl-α-methyl-acetonitrile 
• 28694-90-8 2-(4-aminophenyl)-propionitrile 

Downstream Products

• 51234-41-4 2-[2-(4-chloro-phenyl)-benzooxazol-5-yl]-propionic acid ethyl ester 
• 92977-76-9 benoxaprofen chloride 
• 70280-67-0 (S)-(+)-benoxaprofen 
• 70280-67-0 (R)-(-)-benoxaprofen 

Relevant academic research and scientific papers

AN IMPROVED PROCESS FOR THE PREPARATION OF BENOXAPROFEN

The present invention relates to an improved process for the preparation of Benoxaprofen of formula (I) and its intermediate compounds of (II) and (IV) thereof.

Derivatives of antiphlogistically effective carboxylic acids, their preparation and medicinal use

Compounds of Formula I STR1 wherein R1 is the residue of an antiphlogistically effective carboxylic acid of the formula R1 COOH, n is an integer 1, 2, or 3, and X is oxygen, sulfur, or optionally alkylated nitrogen have valuable antiinflammatory activity.

Esters and amides containing the 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetyl moiety

Compounds of the formula STR1 wherein each X, which may be identical or different from the other X, is oxygen or imino; R1 is hydrogen, fluorine, chlorine or bromine; R2 and R3, which may be identical or different from each other, are each hydrogen; unsubstituted or mono-substituted alkyl of 1 to 6 carbon atoms, where the substituent is phenyl or dialkylamino with 1 to 3 carbon atoms in each alkyl moiety; pyridyl; or cycloalkyl of 5 to 7 carbon atoms; R2 and R3, together with each other and the nitrogen atoms to which they are attached, are pyrrolidino, piperidino, hexamethyleneimino, morpholino, N-aryl-piperazino or N-(alkyl of 1 to 3 carbon atoms)-piperazino; A is cycloalkylene of 5 to 7 carbon atoms; unsubstituted or substituted alkylene of 2 to 10 carbon atoms, where the substituents are one to two alkyls of 1 to 3 carbon atoms each, one to two carbalkoxys of 2 to 4 carbon atoms each, one to two phenyls, one to four hydroxyls, one halomethyl, one hydroxymethyl, one alkanoyloxy of 1 to 18 carbon atoms, one alkanoyloxymethyl of 1 to 18 carbon atoms in the alkanoyl moiety or one STR2 where R1, R2 and R3 have the meanings previously defined; or alkylene of 2 to 10 carbon atoms interrupted by oxygen, sulfur, sulfoxide, sulfonyl, phenyl, cyclohexyl, pyridyl, piperazino or unsubstituted or substituted imino, where the substituent on the imino group is alkyl of 1 to 6 carbon atoms, phenyl or phenylalkyl of 1 to 3 carbon atoms in the alkyl moiety; B is the acyl residue of an antiphlogistic carboxylic acid; and their non-toxic, pharmacologically acceptable acid addition salts. The compounds as well as their salts are useful as anti-inflammatories.

Benzoxazole derivatives in treating inflammation, pain and fever

The invention provides novel 5- and 6-benzoxazolyl alkanoic acids, optionally substituted in the 2-position, and derivatives thereof which possess anti-inflammatory, anti-pyretic and analgesic activity. Also provided is a process for preparing such compounds by cyclising an appropriately substituted o-aminophenol and, if necessary, converting the resultant benzoxazole to the desired compound.

Anti-inflammatory 1,2-benzisoxazole derivatives

3-Phenyl substituted 1,2-benzisoxazole acetic and propionic acid derivatives with anti-inflammatory activity.