Phenyl-imidazolyl acetic or propionic acid derivatives

Abstract

Abstract WHEREIN R4, R5, X, M AND N ARE AS ABOVE DEFINED, WITH AN OPTIONALLY ALKYL-SUBSTITUTED IMIDAZOLE. THESE PHENYL-IMIDAZOLYL-FATTY ACID DERIVATIVES EXHIBIT ANTIMYCOTIC ACTIVITY. ((R4)N-PHENYL)-C(-OH)(-R5)-(CH2)M-X WHEREIN R1, R2, AND R3 ARE THE SAME OR DIFFERENT, AND ARE HYDROGEN OR LOWER ALKYL, R4 IS HYDROGEN, ALKYL, LOWER ALKOXY, ALKYLMERCAPTO, OR AN ELECTRO NEGATIVE MOIETY, R5 IS BENZENE, BENZENE SUBSTITUTED 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 A FUNCTIONAL 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 REACTING A HALOGEN DERIVATIVE OF THE FORMULA: ((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 HYDROXY COMPOUND OF THE FORMULA: 1-((R4)N-C6H4-C(-R5)(-(CH2)M-X)-),2-R2,4-R3,5-R1- PHENYL-IMIDAZOLYL-FATTY ACID DERIVATIVES OF THE FORMULA:

Inventors

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

Bibliographic Details