CH493496A - Thionosalicylic acid anilides and salts thereof antibacterial antifung - al antiprotozoal parasiticidal - Google Patents

Abstract

(A) Thionosalicylic acid anilides where R = H or an acid radical R1 = H, lower alkyl, lower alkoxy R2 = H, halogen, lower alkyl, lower alkoxy. R3, R4, and R5 are the same or diff. and = H, OH, lower alkyl, lower alkoxy, halogen, nitro, haloalkyl, alkylmercapto or acyloxy. X and Y are the same or diff. and = H, halogen or nitro with the proviso that X and Y cannot both be hydrogen at the same time and in the case where X is hydrogen, Y can only be Cl or Br when each of R3, R4 and R5 is different. Compounds (I) and their salts have parasiticidal activity in sheep and cattle particularly against liver flukes. They are also active antibacterial, antifungal and antiprotozoal agents. Compounds (IV) have similar uses.

Description

  

  
 



  Process for the preparation of thionosalicylic anilides or their esters
A number of thionosalicylic anilides with substituents in the aromatic nucleus of the acid component are known [see H. Rivier, S. Kunz, Helv.Chim. Acta 15 (1932) 376; E. Schraufstätter, W. Meiser, R.Gönnert, Z.Naturforsch. 16b (1961), 95; G. Wagner, D. Singer, Z. Chemie 3 (163) 148; German patent specification 1 045 717].



   However, these known compounds are ineffective against trematodes, in particular against the liver fluke, e.g. Fasciola hepatica.



   It has now been found that thionosalicylic acid anilides of the formula
EMI1.1
 have valuable chemotherapeutic and biological properties.



   In the above formula I, R stands for hydrogen or an acyl radical, R1 stands for hydrogen, a lower alkyl radical or lower alkoxy radical, R2 is hydrogen, halogen, a lower alkyl radical or lower alkoxy radical, R3, R4 and R are identical or different and mean hydrogen, lower alkyl radicals , Hydroxyl, lower alkoxy groups, halogen, nitro groups, halogenated alkyl groups, alkyl mercapto or acyloxy groups, X and Y for halogen or nitro groups and Y in addition also for hydrogen.



   As such or in the form of their salts with non-toxic inorganic or organic bases, the new compounds destroy internal parasites such as cestodes or trematodes, of the latter in particular the liver fluke. In addition, the new compounds or their salts have a very good molluscididal, bactericidal and nematocidal action. The new compounds also have a good effect against fungi which are pathogenic to humans and plants, e.g. Trichophyton mentagrophytes, Microsporium felineum, Aspergillus niger, Penicillium commune, etc.



   Bases suitable for salt formation are e.g. Caustic soda, potassium hydroxide, ethanolamine, diethanolamine, piperazine, etc.



   The new compounds are prepared according to the invention by adding substituted phenols of the formula
EMI2.1
 with substituted aromatic mustard oils of the formula
EMI2.2
 in the presence of Friedel-Crafts catalysts.



   Example I 3,5,3'-trichlorothionosalicylic acid unilide
16.3 g (0.1 mol) of 2,4-dichlorophenol and 16.9 g of 3 chlorophenyl mustard oil are mixed, 25 g of finely powdered aluminum chloride are added and the mixture is then heated to 60 ° C. for 24 hours. After cooling, it is broken down with ice and hydrochloric acid, the excess water is decanted and the semi-solid residue is worked through again with dilute hydrochloric acid. This is followed by stirring with dilute sodium hydroxide solution, filtering off and acidifying the filtrate with acetic acid. The precipitate is filtered off, washed with water and recrystallized from 80 percent alcohol.

 

   F. 1340C. The following compounds are obtained analogously.



   Example 2
From 2,4-dichlorophenol and 3,4-dichlorophenyl mustard oil, 3,5,3 ', 4'-tetrachlorothionosalicylic anilide is obtained.



  F. 1360C.



   Example 3
3,5,4'-tribromothionosalicylic acid anilide is obtained from 3,5-dibromophenol and 4-bromophenyl mustard oil.



  F. 1320C.

 

Claims (1)

PATENT CLAIM Process for the preparation of compounds of the formula EMI2.3 where: R is hydrogen or an acyl radical, R1 is hydrogen, a lower alkyl radical or an alkoxy radical, R3 is hydrogen, halogen, a lower alkyl radical or a lower alkoxy radical, R3, R4, Rs are hydrogen, lower alkyl radicals, hydroxyl groups, lower alkoxy groups, Halogen, nitro groups, halogenated alkyl groups, alkyl mercapto or acyloxy radicals, where R3, R4 and R5 are identical or different, X is halogen or the nitro group and Y is hydrogen, Halogen or the nitro group, characterized in that substituted phenols of the formula EMI2.4 with aromatic mustard oils of the formula EMI2.5 in the presence of Friedel-Crafts catalysts. SUBClaim Process according to patent claim, characterized in that the compounds of the formula I are converted into their salts with non-toxic bases. Paint factories Bayer Aktiengesellschaft Representative: E. Blum & Co., Zurich Note from the Federal Office for Intellectual Property: If parts of the description are not in accordance with the definition of the invention given in the patent claim, it should be remembered that according to Art. 51 of the Patent Act, the patent claim is decisive for the material scope of the patent.