Lipophilic quaternary ammonium salicylates

摘要

A lipophilic quaternary ammonium salicylate of formula:


in which

  (i) R1, R2, R3 and R4 each denotes a C1 to C22 saturated or unsaturated alkyl or alkylcycloalkyl radical which can optionally contain, in its chain, at least one ether, thioether, sulphoxide, ester, amide, sulphonamide, carbamate or ureido group and/or which can bear, at the end of the chain or on the chain, at least one hydroxyl or halogen group;
  (ii) R3 and/or R4 each denotes a group of formula:


in which
    0     R8 denotes hydrogen or a C1 to C18 alkyl, alkenyl, alkylcycloalkyl or alkylaryl radical, the aliphatic or aromatic rings optionally bearing at least one C1 to C4 alkyl or alkoxy substituent,
    R7 denotes hydrogen or a CH3 or CH2OH group, the group OC2H3R7 denotes either or both of:


with the provisos that when R7 denotes a CH2OH group, R6 is other than hydrogen and p is 1 and that otherwise p is 0,
and
    R7 and R2 are as defined in paragraph (i);
  (iii) R4 denotes a group of formula:


in which
    n is 0 or 1,
    R6denotes hydrogen, a hydroxyl group, a halogen, an alkyl or hydroxyalkyl group or a C1 to C18 acyl residue; and
    R1, R2 and R3 are as defined in paragraph (i);
  (iv) R1, R2 and R3, together with the nitrogen to which they are attached, form an aromatic heterocycle of formula:


in which R4 is as defined in any one of paragraphs (i), (ii) or (iii);
  (v) R1 and R2 denote a saturated or unsaturated non-aromatic heterocycle, optionally containing a ring oxygen, nitrogen or sulphur,
    R4 is as defined in paragraph (i), (ii) or (iii), and
    R3 is as defined in paragraph (i); or
  (vi) R1, R2 and R3 form, together with one or more nitrogen atoms to which they are attached, polycyclic derivatives,
    R4 is as defined in paragraph (i) or (iii), and
    R5 denotes a group of formula:


in which n is from 0 to 10. have useful pharmaceutical and cosmetic properties and may be used for example as bactericidal and keratolytic agents (e.g. in the treatment of acne).