PURPOSE: To obtain a new prostaglandin E1 analogue (salt) having triple bond at 13 and 14 position and having multiple bond at 2 and 3 position, exhibiting selective and strong antiulcer property, excellent in long acting property and reduced in side effects and useful as a therapeutic agent for peptic ulcer.
CONSTITUTION: A cyclopentenone derivative expressed by formula I (R5 is protecting group of hydroxyl group; Et is ethyl) is made to react with an organoaluminum compound expressed by formula II [R2 is H, halogen, trifluoromethyl, 1-4C alkyl, (substituted)phenyl, etc.; R3 and R4 are H, halogen, 1-4C alkyl, etc.; R6 is the same as R5] and then, the reactional product is made to react with an organocopper compound expressed by formula III (A is vinylene or ethynylene; R7 is 1-8C alkyl, etc.) an chlorotrimethylsilane to afford a compound of the formula IV (Me is methyl). Then, this compound is hydrolyzed and then deprotected to provide the objective new prostaglandmn E1 analogue (salt) expressed by formula V (R1 is H or same as R7), having antiulcer property and reduced in side effects.
AMANO TAKEHIRO
KAMEO KAZUYA
TANAMI TOORU
MUTO MASARU
ONO NAOYA
GOTO JUN
SATO FUMIE