公开(公告)号：US3449325A

公开(公告)日：1969-06-10

申请号：US3449325D

申请日：1964-10-13

Applicant: HOECHST AG

Inventor： NAHM HELMUT ,  SIEDEL WALTER ,  LUDING EDGAR

IPC: C07D499/00 ,  C07D499/60 ,  C07D99/16 ,  A61K21/00

CPC classification number: C07D499/00

公开(公告)号：CA755624A

公开(公告)日：1967-03-28

申请号：CA755624D

Applicant: HOECHST AG

Inventor： NAHM HELMUT ,  SIEDEL WALTER ,  LUDING EDGAR

公开(公告)号：DE1253714B

公开(公告)日：1967-11-09

申请号：DEF0041025

申请日：1963-10-18

Applicant: HOECHST AG

Inventor： NAHM DR HELMUT ,  SIEDEL DR WALTER ,  LUDING EDGAR

IPC: C07D499/00 ,  C07D499/60

Abstract: Penicillin derivatives of the formula wherein R1 represents a straight or branched chain alkyl, cycloalkyl, aralkyl, hydroxyalkyl, epoxyalkyl, alkylaminoalkyl, dialkylaminoalkyl, a group of the formula XN-A-in which A represents an alkylene group and X represents an alkylene or oxygen-interrupted alkylene group of at least two carbon atoms, phenyl, nitrophenyl, dinitrophenyl, halogenonitrophenyl, alkenylalkyl, aralkenylalkyl, alkylnitrophenyl or halogenoalkyl-nitrophenyl; R2 represents an alkyl group containing 1 to 4 carbon atoms, hydrogen or a halogen; R3 represents hydrogen, an alkyl group containing 1 to 4 carbon atoms, a hydroxy or alkoxy group or a halogen and R4 represents hydrogen, or a straight or branched chain alkyl group containing 1 to 4 carbon atoms or a benzyloxymethyl, alkoxyalkyl, phenyl or halogenophenyl are prepared by reacting 6-amino-penicillanic acid in the presence of a proton acceptor with a derivative (e.g. the halide, anhydride, azide or an activated ester) of an a -phenoxy fatty acid of the formula wherein R1, R2, R3 and R4 have the meaning given above. Certain compounds disclosed in Specification 1,077,465 are disclaimed. The reaction may be performed at pH 6-9 with the use of buffer solutions (e.g. sodium bicarbonate or di-sodium phosphate) and at 0-30 DEG C. The compounds are generally isolated as salts with alkali metal, alkaline earth metal or ammonium compounds or organic bases or salts thereof which are added to the reaction mixture as solutions or suspensions and the salt is isolated by precipitation or lyophilization. The Specification contains many examples of penicillin derivatives having the above formula. Pharmaceutical compositions comprise the above penicillin derivatives or salts thereof in admixture or conjunction with a physiologically tolerable carrier.