Phenyl-imidazolyl-fatty acid derivatives for treating mycotic infections

Abstract

Abstract PHENYL-IMIDAZOLYL-FATTY ACIDS DERIVATIVES OF THE FORMULA: 1-(X-(CH2)M-C(-R5)((R4)N-PHENYL)-),2-R2,4-R3,5-R1-IMIDA ZOLE WHEREIN R1, R2, AND R3 ARE THE SAME OR DIFFERENT, AND ARE HYDROGEN OR LOWER AKYL; R4 IS HYDROGEN, ALKYL, LOWER ALKOXY, ALKYLMERCAPTO, OR AN ELECTRO NEGATIVE MOIETY; R5 IS BENZENE, BENZENE SUBSTTITUTED BY ALKYL, LOWER ALKOXY, ALKYLMERCAPTO OR AN ELECTRO NEGATIVE MOIETY, OR R5 IS AN ALIPHATIC MOIETY; X IS A CARBOXYL MOIETY OR A GROUPING OF AFUNCTIONAL CARBOXYLIC ACID DERIVATIVE; M IS 0, 1, 2, 3, 4, 5 OR 6; AND N IS 0, 1 OR 2, AND PHARMACEUTICALLY ACCEPTABLE NON-TOXIC SALTS THEREOF ARE PRODUCED BY REACTTING A HALOGEN DERIVATIVE OF THE FOLMULA: ((R4)N-PHENYL)-C(-HAL)(-R5)-(CH2)M-X WHEREIN R4, R5, X, M AND N ARE AS ABOVE DEFINED, AND HAL IS HALOGEN, WITH AN OPTIONALLY ALKYL SUBSTITUTED IMIDAZOLE IN THE PRESENCE OF ACID-BINDING BASE OR AN EXCESS OF IMIDAZOLE, PREFERABLY IN AN INERT POLAR SOLVENT AT A TEMPERATURE OF FROM ABOUT 20*C. TO ABOUT 180*C., OR REACTING THE ABOVE HALOGEN DERIVATIVE WITH AN ALKALI METAL OR SILVER SALT OF AN OPTIONALLY ALKYL SUBSTITUTED IMIDAZOLE IN AN INERT SOLVENT AT A TEMPERATURE OF FROM ABOUT 20*C. TO ABOUT 200*C., OR REACTING A HYDROXYL COMPOUND OF THE FORMULA: ((R4)N-PHENYL)-C(-OH)(-R5)-(CH2)M-X WHEREIN R4, R5, X, M AND N ARE AS ABOVE DEFINED, WITH AN OPTIONALLY ALKYL-SUBSTITUTED IMIDAZOLE. THESE PHEYL-IMIDAZOLYL-FATTY ACID DERIVATIVES EXHIBIT ANTIMYCOTIC ACTIVITY.

Inventors

• 👤 M Plempel
• 👤 C Metzger
• 👤 K Buchel
• 👤 W Meiser

Bibliographic Details