Prepn. of 1-carba-1-de:thia-2-mercapto-3-carboxy-2-penem(s) - from corresp. 2-oxo-penam(s) and mercaptan (PT 4.6.81)

• Main Authors: BURTON G. CHRISTENSEN, RONALD W. RATCLIFFE
• Format: Patent
• Language: English
• Published: 01.06.1980
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

(A) Prepn. of 1-carba-1-dethia -2-mercapto-3-carboxy -2-penems of formula (I) and their salts, esters and amides comprises activating and treating a 1-carba-1-dethia-2-oxo-3- carboxypenam deriv. of formula (II) with R8-SH. (X is Sr8; R6-8 are H; alkyl, alkenyl or alkynyl having up to 10C; cycloalkyl, cycloalkylalkyl or alkylcycloalkyl having 3-6 ring C and 1-6C in the alkyls; Ph, aralkyl, aralkenyl or aralkynyl, the aryl being Ph and the aliphatic gp. having up to 6C; heteroaryl, heteroaralkyl, heterocyclyl or heterocyclylalkyl; with all the above gps. opt. being substd. by Cl, F, Br, R1, OH, OR1, O-CONR1R2, CONR1R2, NR1R2, NH2, NHR1, C(NR1)NR1R2, SO2NR1R2, NH-CONR1R2, R2N-COR1, COOH, COOR1, COR1, O-COR1, SH, SOR1, SO2R1, CN, N3, NO2 SR1, N(R1)3(+) or CR1:NOR2; R1 and R2 are H or a gp. R6 as defined above, provided (1) that the R6 gp. is unsubstd. and (2) in the heterocyclic gps. 1-4 N, O or S atoms are present and the alkyl associated with the heterocyclyl has 1-6 C; and R3 is a protecting gp. or an ester residue. Provided that when R6/R7 is H and R7/R6 is MeCH(OH), then R8 is not (CH2)2NH2). (B) Cpds. (II) are new, provided that when R6/R7 is H, then R7/R6 is not MeCH(OH). (C) Cpds. (I) in which X is a leaving gp. are new, provided that when R6/R7 is H, then R7/R6 is not MeCH(OH). Cpds. (I: X is SR8) are known broad-spectrum antibacterials useful as therapeutic agents in man and animals, as animal feed additives, preservatives for food, disinfectants, and industrial bactericides, e.g. for use in water-based paints and in the white water or paper mills. Cpds. (I; X is a leaving gp.) and (II) are intermediates in the final stages of a total synthesis of cpds. (I; X is SR8). Dose of (I) is 5-600 mg/kg. daily. Cpds. (I) having a 3-COSR3 gp. have similar activity. (152).