Chalcone derivatives

Abstract

The present invention provides chalcone derivatives of the general formulae: ##STR1## wherein R 1 is a hydroxyl, carboxylic or sulphonic acid group or a carboxyalkoxy or sulphoalkoxy radical, R 2 is an unsaturated, straight-chained or branched aliphatic hydroxycarbonyloxy radical, R 3 is a hydrogen atom, a hydroxyl group or an alkoxy radical, R 4 is an alkyl, hydroxyalkyl, alkoxy, carboxyalkoxy, sulphoalkoxy or carboxyalkylcarbonyloxyalkyl radical or a carboxylic acid or sulphonic acid group and R 5 is a hydrogen or halogen atom, with the proviso that compounds of general formula (IIa) always contain at least one carboxylic or sulphonic acid group; and the nontoxic inorganic and organic salts of those compounds containing at least one carboxylic acid or sulphonic acid group. The present invention also provides a process for the preparation of these chalcone derivatives, as well as pharmaceutical compositions containing them.

We claim: 
     
       1. A chalcone derivative of the general formulae: ##STR8## wherein R 1  is a carboxyalkyoxy radical, R 2  is an unsaturated, straight-chained or branched aliphatic hydrocarbonyloxy radical, R 3  is a hydrogen atom, a hydroxyl group or an alkoxy radical, R 4  is a carboxyalkoxy or carboxyalkylcarbonyloxyalkyl radical or a carboxylic acid group and R 5  is a hydrogen or halogen atom .Iadd.with the proviso that when R 4  is a carboxymethoxy radical R 3  is other than a hydrogen atom.Iaddend.; and the nontoxic inorganic and organic salts of those compounds containing at least one carboxylic acid .[.or sulphonic acid.]. group. 
     
     
       2. A chalcone derivative according to claim 1, wherein the carboxyalkoxy radicals R 1  and R 4  have the general formulae   --O--CH.sub.2).sub.n COOH     in which n is 1, 2 or 3.   
     
     
       3. A chalcone derivative according to claim 1, which is 1-(4-Isoprenyloxy-2-carboxymethoxyphenyl)-3-(4-carboxyphenyl)-prop-2-en-1-one and the disodium salt thereof. .[.4. A chalcone derivative according to claim 1, which is 1-(2-Carboxymethoxy-4-isoprenyloxyphenyl)-3-(4-carboxymethoxyphenyl)-prop- 
     
     
       2-en-1-one and the disodium salt thereof..]. 5. A chalcone derivative according to claim 1, which is 1-(2-Carboxymethoxy-4-isoprenyloxyphenyl)-3-(4-carboxymethoxy-3-methoxyphe 
     
     
       nyl)-prop-2-en-1-one and the disodium salt thereof. 6. A chalcone derivative according to claim 1, which is 1-(4-Isoprenyloxy-2-carboxymethoxyphenyl)-3-(3-carboxyphenyl)-prop-2-en-1- 
     
     
       one and the disodium salt thereof. 7. A chalcone derivative according to claim 1, which is 1-[2-(Prop-2-enyloxy)-4-carboxymethoxyphenyl]-3-(4-carboxyphenyl)-prop-2-e 
     
     
       n-1-one and the disodium salt thereof. 8. A chalcone derivative according to claim 1, which is 1-[4-(Prop-2-enyloxy)-2-carboxymethoxyphenyl]-3-(4-carboxyphenyl)-prop-2-e 
     
     
       n-1-one and the disodium salt thereof. 9. A chalcone derivative according to claim 1, which is 1-[4-(Prop-2-enyloxy)-2-carboxymethoxyphenyl]-3-(3-carboxyphenyl)-prop-2-e 
     
     
       n-1-one and the disodium salt thereof. 10. A chalcone derivative according to claim 1, which is 1-[4-(Prop-2-ynyloxy)-2-carboxymethoxyphenyl]-3-(4-carboxyphenyl)-prop-2-e 
     
     
       n-1-one. 11. A chalcone derivative according to claim 1, which is 1-[4-(Hex-2-enyloxy)-2-carboxymethoxyphenyl]-3-(4-carboxyphenyl)-prop-2-en 
     
     
       -1-one. 12. A chalcone derivative according to claim 1, which is 1-[4-(But-2-enyloxy)-2-carboxymethoxyphenyl]-3-(4-carboxyphenyl)-prop-2-en 
     
     
       -1-one. 13. Pharmaceutical compositions containing at least one chalcone derivative according to claim 1, in admixture with a solid or liquid pharmaceutical diluent or carrier.