CH527209A - Anti-inflammatory analgesic antipyretic oxazole - Google Patents

Abstract

Oxazole derivatives - (I) Y = phenyl-, benzyl- which may be subst. by up to 2 hal- or CF3 - Z = -CR1R2R3 - R1 = H-, C1-3 alkyl- - R2 = H-, C1-3 alkyl-, C2-6 alkoxycarbonyl- - R3 = CO2R4 or -CONHR5 - R4 = H-, alkyl-, dialkylaminoalkyl-, benzyl-, phenyl-, R5 = H-, -OH, -NH2, dialkylaminoalkyl-, alkoxycarbonylalkyl-, carboxyalkyl-particularly aluminium 2-(4-chlorophenyl) oxazol-4-acetate. - Anti-inflammatory, analgesic, antipyretic. - A mixture of 2(4-chlorophenyl)-4-cyanomethyl-oxazole, dry ethanol and conc. H2SO4 is heated for 10 hours at 100 deg.C. The solution is poured into ice-water and the mixture filtered to yield solid ethyl 2-(4-chlorophenyl)oxazol-4-yl acetate.

Description

  

  Process for the production of oxazolylalkanecarboxamides The invention relates to a process for the production of new oxazolylalkanecarboxamides with anti-inflammatory, analgesic and antipyretic properties.



  According to the invention, oxazolyl-alkanecarboxylic acid amides of the formula
EMI0001.0002
    and their salts are prepared in which Y is a phenyl or benzy radical, which is optionally substituted in the benzene ring by one or two halogen atoms or the trifluoromethyl radical, and R1 and R2, which can be the same or different, are hydrogen or an alkyl radical mean at most 3 carbon atoms.



  The oxazole nucleus is numbered as follows:
EMI0001.0007
    It is readily apparent from the above formula that the group -CR1R1-CONH2 is in the 4-position when Y is in the 2-position and in the 2-position when Y is in the 4-position.



  The substituents optionally present in Y can e.g. can be selected from fluorine, chlorine and bromine atoms. If R1 or R2 represents an alkyl radical with a maximum of 3 carbon atoms, this can e.g. the methyl will be radical. As examples of salts there can be used pharmaceutically acceptable acid addition salts, e.g. Mention hydrochlorides, hydrobromides, sulfates or phosphates.



  The inventive method consists in that one compound of the formula
EMI0001.0011
    in which Y, R1 and R2 have the above meaning, hydrolyzed.



  The hydrolysis of the nitrile can be carried out by means of an acid such as an inorganic acid, e.g. Sulfuric acid.



  The products of the process can be converted into pharmaceutically acceptable acid addition salts by methods known per se.



  The invention is explained in more detail below with reference to exemplary embodiments from, the amounts given being based on weight.



  <I> Example 1 </I> A solution of 1 part 2- (4-chlorophenyl) -4-cyano-methyloxazole in 8 parts concentrated sulfuric acid is kept at ambient temperature for 4 hours. The solution is then poured into 50 parts of water and the resulting mixture is filtered. The solid residue is recrystallized from aqueous methanol. This gives 2- (4-chlorophenyl) oxazol-4-ylacetamide, m.p. 193-1941> C.



  2-Phenyloxazol-4-yl-acetamide, melting point 184-185 ° C., is obtained in the same way from 4-cyanomethyl-2-phenyloxazole. <I> Example 2 </I> When the process according to Example 1 is repeated with 2- (3-chlorophenyl) -4-cyanomethyloxazole as the starting material, 2- (3-chlorophenyl) -oxazol-4-ylacetamide, m.p. . 175 - 177 C.

 

Claims (1)

PATENT CLAIM Process for the preparation of oxazolyl-alkanecarboxamides of the formula EMI0002.0004 in which Y is a phenyl or benzyl radical, which are optionally substituted in the benzene ring by one or two halogen atoms or the trifluoromethyl radical and R1 and R2, which may be the same or different from one another, are hydrogen or an alkyl radical with at most 3 carbon atoms, and their salts, characterized in that one is a nitrile of the formula EMI0002.0005 in which Y, R1 and R2 have the above meanings, hydrolyzed. SUBCLAIMS 1. Process according to claim, characterized in that the halogen atoms in the phenyl or benzyl radical Y, if present, are selected from fluorine, chlorine and bromine atoms. A method according to claim or sub-claim 1, characterized in that the hydrolysis is carried out by means of an acid such as an inorganic acid, e.g. Sulfuric acid. 3. The method according to claim or sub-claim 1 or 2, characterized in that the process products are converted into pharmaceutically acceptable acid addition salts.